<?xml version="1.0"?>
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	<id>https://chemwiki.ch.ic.ac.uk/api.php?action=feedcontributions&amp;feedformat=atom&amp;user=Mr406</id>
	<title>ChemWiki - User contributions [en]</title>
	<link rel="self" type="application/atom+xml" href="https://chemwiki.ch.ic.ac.uk/api.php?action=feedcontributions&amp;feedformat=atom&amp;user=Mr406"/>
	<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/wiki/Special:Contributions/Mr406"/>
	<updated>2026-07-11T01:34:27Z</updated>
	<subtitle>User contributions</subtitle>
	<generator>MediaWiki 1.43.8</generator>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=List_of_S-phrases&amp;diff=14202</id>
		<title>List of S-phrases</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=List_of_S-phrases&amp;diff=14202"/>
		<updated>2007-12-07T17:57:26Z</updated>

		<summary type="html">&lt;p&gt;Mr406: New page: http://www.sigmaaldrich.com/Help_Pages/Help_Welcome/Product_Search/Risk___Safety_Statements.html#Safety Phrases&lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;http://www.sigmaaldrich.com/Help_Pages/Help_Welcome/Product_Search/Risk___Safety_Statements.html#Safety Phrases&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=List_of_R-phrases&amp;diff=14201</id>
		<title>List of R-phrases</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=List_of_R-phrases&amp;diff=14201"/>
		<updated>2007-12-07T17:56:09Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;http://www.sigmaaldrich.com/Help_Pages/Help_Welcome/Product_Search/Risk___Safety_Statements.html#Risk Phrases&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Trinitrotoluene_(data_page)&amp;diff=14199</id>
		<title>It07:Trinitrotoluene (data page)</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Trinitrotoluene_(data_page)&amp;diff=14199"/>
		<updated>2007-12-07T17:52:45Z</updated>

		<summary type="html">&lt;p&gt;Mr406: New page: http://ptcl.chem.ox.ac.uk/MSDS/TR/2,4,6-trinitrotoluene.html&lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;http://ptcl.chem.ox.ac.uk/MSDS/TR/2,4,6-trinitrotoluene.html&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Trinitrotoluene&amp;diff=14197</id>
		<title>It07:Trinitrotoluene</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Trinitrotoluene&amp;diff=14197"/>
		<updated>2007-12-07T17:46:20Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:Trinitrotoluene.gif]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| 2-Methyl-1,3,5-trinitrobenzene&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| 2,4,6-Trinitrotoluene Trotyl; 2,4,6-Trinitromethylbenzene&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C6H2(NO2)3CH3 Point group = C&amp;lt;sub&amp;gt;2h&amp;lt;/sub&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| Cc1c(cc(cc1N(=O)=O)N(=O)=O)N(=O)=O&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 227.131 g/mol&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| Yellow(Needle Shaped)&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 118-96-7&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density]&lt;br /&gt;
| 1.654 g/cm³&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| 130 mg/L of H2O (20 °C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in other solvent]&lt;br /&gt;
| ether;acetone;benzene;pyridine&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| 353.35K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 568K&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| 0.98 [[Debye|D]] at 25&amp;lt;sup&amp;gt;o&amp;lt;/sup&amp;gt;C tetrachloromethane solvent&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| {{{Hazards}}} &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: R2 R23 R24 R25 R33 &amp;lt;br /&amp;gt; [[List of S-phrases|S:S35 S44]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| {{{RTECS}}}&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&lt;br /&gt;
==2,4,6-Trinitrotoluene (TNT)==&lt;br /&gt;
&lt;br /&gt;
===3D structure and crystal unit cell===&lt;br /&gt;
&amp;lt;sup&amp;gt;1&amp;lt;/sup&amp;gt;&lt;br /&gt;
&lt;br /&gt;
Interactive 3D representation of TNT.&lt;br /&gt;
&amp;lt;p&amp;gt;Right click on molecule to explore&amp;lt;/p&amp;gt;&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
&amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
&amp;lt;size&amp;gt;250&amp;lt;/size&amp;gt;&lt;br /&gt;
&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
&amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
&amp;lt;inlineContents&amp;gt;TNT.PDB&lt;br /&gt;
HEADER    NONAME 23-Oct-07                                              NONE   1&lt;br /&gt;
TITLE                                                                   NONE   2&lt;br /&gt;
AUTHOR    WWW daemon apache                                             NONE   3&lt;br /&gt;
REVDAT   1  23-Oct-07     0                                             NONE   4&lt;br /&gt;
ATOM      1  C           0       2.704  -0.001  -0.016  0.00  0.00           C+0&lt;br /&gt;
ATOM      2  C           0       1.197  -0.001  -0.006  0.00  0.00           C+0&lt;br /&gt;
ATOM      3  C           0       0.507   1.197  -0.002  0.00  0.00           C+0&lt;br /&gt;
ATOM      4  N           0       1.247   2.478  -0.007  0.00  0.00           N+1&lt;br /&gt;
ATOM      5  O           0       0.645   3.529  -0.136  0.00  0.00           O-1&lt;br /&gt;
ATOM      6  O           0       2.459   2.482   0.117  0.00  0.00           O+0&lt;br /&gt;
ATOM      7  C           0      -0.876   1.198   0.006  0.00  0.00           C+0&lt;br /&gt;
ATOM      8  C           0      -1.567   0.001   0.011  0.00  0.00           C+0&lt;br /&gt;
ATOM      9  N           0      -3.048   0.002   0.021  0.00  0.00           N+1&lt;br /&gt;
ATOM     10  O           0      -3.656   1.057   0.024  0.00  0.00           O-1&lt;br /&gt;
ATOM     11  O           0      -3.657  -1.053   0.025  0.00  0.00           O+0&lt;br /&gt;
ATOM     12  C           0      -0.877  -1.197   0.007  0.00  0.00           C+0&lt;br /&gt;
ATOM     13  C           0       0.505  -1.197  -0.007  0.00  0.00           C+0&lt;br /&gt;
ATOM     14  N           0       1.245  -2.480  -0.011  0.00  0.00           N+1&lt;br /&gt;
ATOM     15  O           0       0.639  -3.532  -0.108  0.00  0.00           O-1&lt;br /&gt;
ATOM     16  O           0       2.459  -2.483   0.081  0.00  0.00           O+0&lt;br /&gt;
ATOM     17  H           0       3.074  -0.062   1.008  0.00  0.00           H+0&lt;br /&gt;
ATOM     18  H           0       3.063  -0.860  -0.583  0.00  0.00           H+0&lt;br /&gt;
ATOM     19  H           0       3.065   0.917  -0.478  0.00  0.00           H+0&lt;br /&gt;
ATOM     20  H           0      -1.415   2.133   0.009  0.00  0.00           H+0&lt;br /&gt;
ATOM     21  H           0      -1.417  -2.132   0.011  0.00  0.00           H+0&lt;br /&gt;
CONECT    1    2   17   18   19                                         NONE  26&lt;br /&gt;
CONECT    2    1   13    3    0                                         NONE  27&lt;br /&gt;
CONECT    3    2    4    7    0                                         NONE  28&lt;br /&gt;
CONECT    4    3    5    6    0                                         NONE  29&lt;br /&gt;
CONECT    5    4    0    0    0                                         NONE  30&lt;br /&gt;
CONECT    6    4    0    0    0                                         NONE  31&lt;br /&gt;
CONECT    7    3    8   20    0                                         NONE  32&lt;br /&gt;
CONECT    8    7    9   12    0                                         NONE  33&lt;br /&gt;
CONECT    9    8   10   11    0                                         NONE  34&lt;br /&gt;
CONECT   10    9    0    0    0                                         NONE  35&lt;br /&gt;
CONECT   11    9    0    0    0                                         NONE  36&lt;br /&gt;
CONECT   12    8   13   21    0                                         NONE  37&lt;br /&gt;
CONECT   13   12    2   14    0                                         NONE  38&lt;br /&gt;
CONECT   14   13   15   16    0                                         NONE  39&lt;br /&gt;
CONECT   15   14    0    0    0                                         NONE  40&lt;br /&gt;
CONECT   16   14    0    0    0                                         NONE  41&lt;br /&gt;
END                                                                     NONE  42&lt;br /&gt;
&lt;br /&gt;
&amp;lt;/inlineContents&amp;gt;&lt;br /&gt;
&amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
3D crystal unit cell representation of TNT. &lt;br /&gt;
&amp;lt;p&amp;gt;Right click on molecule to explore.&amp;lt;/p&amp;gt;&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
&amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
&amp;lt;size&amp;gt;350&amp;lt;/size&amp;gt;&lt;br /&gt;
&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
&amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
&amp;lt;inlineContents&amp;gt;TNT.PDB&lt;br /&gt;
HEADER    CSD ENTRY ZZZMUC09&lt;br /&gt;
CRYST1  14.9100   6.0341  19.6800  90.00  90.00  90.00     Pca21&lt;br /&gt;
SCALE1      0.067069 -0.000000 -0.000000       0.000000&lt;br /&gt;
SCALE2      0.000000  0.165725 -0.000000       0.000000&lt;br /&gt;
SCALE3      0.000000  0.000000  0.050813       0.000000&lt;br /&gt;
HETATM    1  O1  UNK     1       9.405  -1.586  10.086  1.00  0.00           O  &lt;br /&gt;
HETATM    2  O2  UNK     1      11.020  -0.192   9.675  1.00  0.00           O  &lt;br /&gt;
HETATM    3  O3  UNK     1      11.218   2.818  13.774  1.00  0.00           O  &lt;br /&gt;
HETATM    4  O4  UNK     1       9.907   4.482  13.277  1.00  0.00           O  &lt;br /&gt;
HETATM    5  O5  UNK     1       5.418   3.032  11.216  1.00  0.00           O  &lt;br /&gt;
HETATM    6  O6  UNK     1       5.190   1.027  12.013  1.00  0.00           O  &lt;br /&gt;
HETATM    7  N1  UNK     1       9.938  -0.482  10.171  1.00  0.00           N  &lt;br /&gt;
HETATM    8  N2  UNK     1      10.245   3.310  13.206  1.00  0.00           N  &lt;br /&gt;
HETATM    9  N3  UNK     1       5.866   1.954  11.587  1.00  0.00           N  &lt;br /&gt;
HETATM   10  C1  UNK     1       9.233   0.569  10.926  1.00  0.00           C  &lt;br /&gt;
HETATM   11  C2  UNK     1      10.035   1.383  11.709  1.00  0.00           C  &lt;br /&gt;
HETATM   12  C3  UNK     1       9.428   2.414  12.383  1.00  0.00           C  &lt;br /&gt;
HETATM   13  C4  UNK     1       8.070   2.660  12.300  1.00  0.00           C  &lt;br /&gt;
HETATM   14  C5  UNK     1       7.330   1.770  11.555  1.00  0.00           C  &lt;br /&gt;
HETATM   15  C6  UNK     1       7.848   0.698  10.818  1.00  0.00           C  &lt;br /&gt;
HETATM   16  C7  UNK     1       6.981  -0.160   9.942  1.00  0.00           C  &lt;br /&gt;
HETATM   17  H1  UNK     1      11.018   1.207  11.751  1.00  0.00           H  &lt;br /&gt;
HETATM   18  H2  UNK     1       7.619   3.301  12.833  1.00  0.00           H  &lt;br /&gt;
HETATM   19  H3  UNK     1       7.366  -0.392   9.135  1.00  0.00           H  &lt;br /&gt;
HETATM   20  H4  UNK     1       6.754  -1.068  10.411  1.00  0.00           H  &lt;br /&gt;
HETATM   21  H5  UNK     1       6.158   0.332   9.712  1.00  0.00           H  &lt;br /&gt;
HETATM   22  O1  UNK     1       5.505   7.620   0.246  1.00  0.00           O  &lt;br /&gt;
HETATM   23  O2  UNK     1       3.890   6.227  -0.165  1.00  0.00           O  &lt;br /&gt;
HETATM   24  O3  UNK     1       3.692   3.216   3.934  1.00  0.00           O  &lt;br /&gt;
HETATM   25  O4  UNK     1       5.003   1.552   3.437  1.00  0.00           O  &lt;br /&gt;
HETATM   26  O5  UNK     1       9.492   3.002   1.376  1.00  0.00           O  &lt;br /&gt;
HETATM   27  O6  UNK     1       9.720   5.007   2.173  1.00  0.00           O  &lt;br /&gt;
HETATM   28  N1  UNK     1       4.972   6.516   0.331  1.00  0.00           N  &lt;br /&gt;
HETATM   29  N2  UNK     1       4.665   2.724   3.366  1.00  0.00           N  &lt;br /&gt;
HETATM   30  N3  UNK     1       9.044   4.080   1.747  1.00  0.00           N  &lt;br /&gt;
HETATM   31  C1  UNK     1       5.677   5.465   1.086  1.00  0.00           C  &lt;br /&gt;
HETATM   32  C2  UNK     1       4.875   4.651   1.869  1.00  0.00           C  &lt;br /&gt;
HETATM   33  C3  UNK     1       5.482   3.620   2.543  1.00  0.00           C  &lt;br /&gt;
HETATM   34  C4  UNK     1       6.840   3.374   2.460  1.00  0.00           C  &lt;br /&gt;
HETATM   35  C5  UNK     1       7.580   4.264   1.715  1.00  0.00           C  &lt;br /&gt;
HETATM   36  C6  UNK     1       7.062   5.336   0.978  1.00  0.00           C  &lt;br /&gt;
HETATM   37  C7  UNK     1       7.929   6.194   0.102  1.00  0.00           C  &lt;br /&gt;
HETATM   38  H1  UNK     1       3.892   4.827   1.911  1.00  0.00           H  &lt;br /&gt;
HETATM   39  H2  UNK     1       7.291   2.733   2.993  1.00  0.00           H  &lt;br /&gt;
HETATM   40  H3  UNK     1       7.544   6.426  -0.705  1.00  0.00           H  &lt;br /&gt;
HETATM   41  H4  UNK     1       8.156   7.102   0.571  1.00  0.00           H  &lt;br /&gt;
HETATM   42  H5  UNK     1       8.752   5.702  -0.128  1.00  0.00           H  &lt;br /&gt;
HETATM   43  O1  UNK     1      12.960  -1.586   0.246  1.00  0.00           O  &lt;br /&gt;
HETATM   44  O2  UNK     1      11.345  -0.192  -0.165  1.00  0.00           O  &lt;br /&gt;
HETATM   45  O3  UNK     1      11.147   2.818   3.934  1.00  0.00           O  &lt;br /&gt;
HETATM   46  O4  UNK     1      12.458   4.482   3.437  1.00  0.00           O  &lt;br /&gt;
HETATM   47  O5  UNK     1      16.947   3.032   1.376  1.00  0.00           O  &lt;br /&gt;
HETATM   48  O6  UNK     1      17.175   1.027   2.173  1.00  0.00           O  &lt;br /&gt;
HETATM   49  N1  UNK     1      12.427  -0.482   0.331  1.00  0.00           N  &lt;br /&gt;
HETATM   50  N2  UNK     1      12.120   3.310   3.366  1.00  0.00           N  &lt;br /&gt;
HETATM   51  N3  UNK     1      16.499   1.954   1.747  1.00  0.00           N  &lt;br /&gt;
HETATM   52  C1  UNK     1      13.132   0.569   1.086  1.00  0.00           C  &lt;br /&gt;
HETATM   53  C2  UNK     1      12.330   1.383   1.869  1.00  0.00           C  &lt;br /&gt;
HETATM   54  C3  UNK     1      12.937   2.414   2.543  1.00  0.00           C  &lt;br /&gt;
HETATM   55  C4  UNK     1      14.295   2.660   2.460  1.00  0.00           C  &lt;br /&gt;
HETATM   56  C5  UNK     1      15.035   1.770   1.715  1.00  0.00           C  &lt;br /&gt;
HETATM   57  C6  UNK     1      14.517   0.698   0.978  1.00  0.00           C  &lt;br /&gt;
HETATM   58  C7  UNK     1      15.384  -0.160   0.102  1.00  0.00           C  &lt;br /&gt;
HETATM   59  H1  UNK     1      11.347   1.207   1.911  1.00  0.00           H  &lt;br /&gt;
HETATM   60  H2  UNK     1      14.746   3.301   2.993  1.00  0.00           H  &lt;br /&gt;
HETATM   61  H3  UNK     1      14.999  -0.392  -0.705  1.00  0.00           H  &lt;br /&gt;
HETATM   62  H4  UNK     1      15.611  -1.068   0.571  1.00  0.00           H  &lt;br /&gt;
HETATM   63  H5  UNK     1      16.207   0.332  -0.128  1.00  0.00           H  &lt;br /&gt;
HETATM   64  O1  UNK     1       1.950   7.620  10.086  1.00  0.00           O  &lt;br /&gt;
HETATM   65  O2  UNK     1       3.565   6.227   9.675  1.00  0.00           O  &lt;br /&gt;
HETATM   66  O3  UNK     1       3.763   3.216  13.774  1.00  0.00           O  &lt;br /&gt;
HETATM   67  O4  UNK     1       2.452   1.552  13.277  1.00  0.00           O  &lt;br /&gt;
HETATM   68  O5  UNK     1      -2.037   3.002  11.216  1.00  0.00           O  &lt;br /&gt;
HETATM   69  O6  UNK     1      -2.265   5.007  12.013  1.00  0.00           O  &lt;br /&gt;
HETATM   70  N1  UNK     1       2.483   6.516  10.171  1.00  0.00           N  &lt;br /&gt;
HETATM   71  N2  UNK     1       2.790   2.724  13.206  1.00  0.00           N  &lt;br /&gt;
HETATM   72  N3  UNK     1      -1.589   4.080  11.587  1.00  0.00           N  &lt;br /&gt;
HETATM   73  C1  UNK     1       1.778   5.465  10.926  1.00  0.00           C  &lt;br /&gt;
HETATM   74  C2  UNK     1       2.580   4.651  11.709  1.00  0.00           C  &lt;br /&gt;
HETATM   75  C3  UNK     1       1.973   3.620  12.383  1.00  0.00           C  &lt;br /&gt;
HETATM   76  C4  UNK     1       0.615   3.374  12.300  1.00  0.00           C  &lt;br /&gt;
HETATM   77  C5  UNK     1      -0.125   4.264  11.555  1.00  0.00           C  &lt;br /&gt;
HETATM   78  C6  UNK     1       0.393   5.336  10.818  1.00  0.00           C  &lt;br /&gt;
HETATM   79  C7  UNK     1      -0.474   6.194   9.942  1.00  0.00           C  &lt;br /&gt;
HETATM   80  H1  UNK     1       3.563   4.827  11.751  1.00  0.00           H  &lt;br /&gt;
HETATM   81  H2  UNK     1       0.164   2.733  12.833  1.00  0.00           H  &lt;br /&gt;
HETATM   82  H3  UNK     1      -0.089   6.426   9.135  1.00  0.00           H  &lt;br /&gt;
HETATM   83  H4  UNK     1      -0.701   7.102  10.411  1.00  0.00           H  &lt;br /&gt;
HETATM   84  H5  UNK     1      -1.297   5.702   9.712  1.00  0.00           H  &lt;br /&gt;
HETATM   85  O7  UNK     1       1.825  -0.115  16.559  1.00  0.00           O  &lt;br /&gt;
HETATM   86  O8  UNK     1       1.471   1.953  16.023  1.00  0.00           O  &lt;br /&gt;
HETATM   87  O9  UNK     1       6.165  -1.339  14.286  1.00  0.00           O  &lt;br /&gt;
HETATM   88  O10 UNK     1       7.654   0.231  14.142  1.00  0.00           O  &lt;br /&gt;
HETATM   89  O11 UNK     1       7.323   3.201  18.208  1.00  0.00           O  &lt;br /&gt;
HETATM   90  O12 UNK     1       5.758   4.622  17.696  1.00  0.00           O  &lt;br /&gt;
HETATM   91  N4  UNK     1       2.207   1.015  16.292  1.00  0.00           N  &lt;br /&gt;
HETATM   92  N5  UNK     1       6.591  -0.215  14.546  1.00  0.00           N  &lt;br /&gt;
HETATM   93  N6  UNK     1       6.265   3.502  17.663  1.00  0.00           N  &lt;br /&gt;
HETATM   94  C8  UNK     1       3.668   1.252  16.274  1.00  0.00           C  &lt;br /&gt;
HETATM   95  C9  UNK     1       4.408   0.387  15.492  1.00  0.00           C  &lt;br /&gt;
HETATM   96  C10 UNK     1       5.766   0.642  15.404  1.00  0.00           C  &lt;br /&gt;
HETATM   97  C11 UNK     1       6.376   1.665  16.096  1.00  0.00           C  &lt;br /&gt;
HETATM   98  C12 UNK     1       5.569   2.452  16.894  1.00  0.00           C  &lt;br /&gt;
HETATM   99  C13 UNK     1       4.184   2.311  17.018  1.00  0.00           C  &lt;br /&gt;
HETATM  100  C14 UNK     1       3.331   3.152  17.928  1.00  0.00           C  &lt;br /&gt;
HETATM  101  H6  UNK     1       4.041  -0.416  15.022  1.00  0.00           H  &lt;br /&gt;
HETATM  102  H7  UNK     1       7.278   1.834  16.053  1.00  0.00           H  &lt;br /&gt;
HETATM  103  H8  UNK     1       3.847   3.421  18.698  1.00  0.00           H  &lt;br /&gt;
HETATM  104  H9  UNK     1       2.520   2.697  18.230  1.00  0.00           H  &lt;br /&gt;
HETATM  105  H10 UNK     1       3.086   3.989  17.431  1.00  0.00           H  &lt;br /&gt;
HETATM  106  O7  UNK     1      13.085   6.149   6.719  1.00  0.00           O  &lt;br /&gt;
HETATM  107  O8  UNK     1      13.439   4.081   6.183  1.00  0.00           O  &lt;br /&gt;
HETATM  108  O9  UNK     1       8.745   7.373   4.446  1.00  0.00           O  &lt;br /&gt;
HETATM  109  O10 UNK     1       7.256   5.803   4.302  1.00  0.00           O  &lt;br /&gt;
HETATM  110  O11 UNK     1       7.587   2.833   8.368  1.00  0.00           O  &lt;br /&gt;
HETATM  111  O12 UNK     1       9.152   1.413   7.856  1.00  0.00           O  &lt;br /&gt;
HETATM  112  N4  UNK     1      12.703   5.019   6.452  1.00  0.00           N  &lt;br /&gt;
HETATM  113  N5  UNK     1       8.319   6.249   4.706  1.00  0.00           N  &lt;br /&gt;
HETATM  114  N6  UNK     1       8.645   2.532   7.823  1.00  0.00           N  &lt;br /&gt;
HETATM  115  C8  UNK     1      11.242   4.782   6.434  1.00  0.00           C  &lt;br /&gt;
HETATM  116  C9  UNK     1      10.502   5.647   5.652  1.00  0.00           C  &lt;br /&gt;
HETATM  117  C10 UNK     1       9.144   5.392   5.564  1.00  0.00           C  &lt;br /&gt;
HETATM  118  C11 UNK     1       8.534   4.369   6.256  1.00  0.00           C  &lt;br /&gt;
HETATM  119  C12 UNK     1       9.341   3.582   7.054  1.00  0.00           C  &lt;br /&gt;
HETATM  120  C13 UNK     1      10.726   3.723   7.178  1.00  0.00           C  &lt;br /&gt;
HETATM  121  C14 UNK     1      11.579   2.882   8.088  1.00  0.00           C  &lt;br /&gt;
HETATM  122  H6  UNK     1      10.869   6.450   5.182  1.00  0.00           H  &lt;br /&gt;
HETATM  123  H7  UNK     1       7.632   4.200   6.213  1.00  0.00           H  &lt;br /&gt;
HETATM  124  H8  UNK     1      11.063   2.613   8.858  1.00  0.00           H  &lt;br /&gt;
HETATM  125  H9  UNK     1      12.390   3.337   8.390  1.00  0.00           H  &lt;br /&gt;
HETATM  126  H10 UNK     1      11.824   2.046   7.591  1.00  0.00           H  &lt;br /&gt;
HETATM  127  O7  UNK     1       5.630  -0.115   6.719  1.00  0.00           O  &lt;br /&gt;
HETATM  128  O8  UNK     1       5.984   1.953   6.183  1.00  0.00           O  &lt;br /&gt;
HETATM  129  O9  UNK     1       1.290  -1.339   4.446  1.00  0.00           O  &lt;br /&gt;
HETATM  130  O10 UNK     1      -0.199   0.231   4.302  1.00  0.00           O  &lt;br /&gt;
HETATM  131  O11 UNK     1       0.132   3.201   8.368  1.00  0.00           O  &lt;br /&gt;
HETATM  132  O12 UNK     1       1.697   4.622   7.856  1.00  0.00           O  &lt;br /&gt;
HETATM  133  N4  UNK     1       5.248   1.015   6.452  1.00  0.00           N  &lt;br /&gt;
HETATM  134  N5  UNK     1       0.864  -0.215   4.706  1.00  0.00           N  &lt;br /&gt;
HETATM  135  N6  UNK     1       1.190   3.502   7.823  1.00  0.00           N  &lt;br /&gt;
HETATM  136  C8  UNK     1       3.787   1.252   6.434  1.00  0.00           C  &lt;br /&gt;
HETATM  137  C9  UNK     1       3.047   0.387   5.652  1.00  0.00           C  &lt;br /&gt;
HETATM  138  C10 UNK     1       1.689   0.642   5.564  1.00  0.00           C  &lt;br /&gt;
HETATM  139  C11 UNK     1       1.079   1.665   6.256  1.00  0.00           C  &lt;br /&gt;
HETATM  140  C12 UNK     1       1.886   2.452   7.054  1.00  0.00           C  &lt;br /&gt;
HETATM  141  C13 UNK     1       3.271   2.311   7.178  1.00  0.00           C  &lt;br /&gt;
HETATM  142  C14 UNK     1       4.124   3.152   8.088  1.00  0.00           C  &lt;br /&gt;
HETATM  143  H6  UNK     1       3.414  -0.416   5.182  1.00  0.00           H  &lt;br /&gt;
HETATM  144  H7  UNK     1       0.177   1.834   6.213  1.00  0.00           H  &lt;br /&gt;
HETATM  145  H8  UNK     1       3.608   3.421   8.858  1.00  0.00           H  &lt;br /&gt;
HETATM  146  H9  UNK     1       4.935   2.697   8.390  1.00  0.00           H  &lt;br /&gt;
HETATM  147  H10 UNK     1       4.369   3.989   7.591  1.00  0.00           H  &lt;br /&gt;
HETATM  148  O7  UNK     1       9.280   6.149  16.559  1.00  0.00           O  &lt;br /&gt;
HETATM  149  O8  UNK     1       8.926   4.081  16.023  1.00  0.00           O  &lt;br /&gt;
HETATM  150  O9  UNK     1      13.620   7.373  14.286  1.00  0.00           O  &lt;br /&gt;
HETATM  151  O10 UNK     1      15.109   5.803  14.142  1.00  0.00           O  &lt;br /&gt;
HETATM  152  O11 UNK     1      14.778   2.833  18.208  1.00  0.00           O  &lt;br /&gt;
HETATM  153  O12 UNK     1      13.213   1.413  17.696  1.00  0.00           O  &lt;br /&gt;
HETATM  154  N4  UNK     1       9.662   5.019  16.292  1.00  0.00           N  &lt;br /&gt;
HETATM  155  N5  UNK     1      14.046   6.249  14.546  1.00  0.00           N  &lt;br /&gt;
HETATM  156  N6  UNK     1      13.720   2.532  17.663  1.00  0.00           N  &lt;br /&gt;
HETATM  157  C8  UNK     1      11.123   4.782  16.274  1.00  0.00           C  &lt;br /&gt;
HETATM  158  C9  UNK     1      11.863   5.647  15.492  1.00  0.00           C  &lt;br /&gt;
HETATM  159  C10 UNK     1      13.221   5.392  15.404  1.00  0.00           C  &lt;br /&gt;
HETATM  160  C11 UNK     1      13.831   4.369  16.096  1.00  0.00           C  &lt;br /&gt;
HETATM  161  C12 UNK     1      13.024   3.582  16.894  1.00  0.00           C  &lt;br /&gt;
HETATM  162  C13 UNK     1      11.639   3.723  17.018  1.00  0.00           C  &lt;br /&gt;
HETATM  163  C14 UNK     1      10.786   2.882  17.928  1.00  0.00           C  &lt;br /&gt;
HETATM  164  H6  UNK     1      11.496   6.450  15.022  1.00  0.00           H  &lt;br /&gt;
HETATM  165  H7  UNK     1      14.733   4.200  16.053  1.00  0.00           H  &lt;br /&gt;
HETATM  166  H8  UNK     1      11.302   2.613  18.698  1.00  0.00           H  &lt;br /&gt;
HETATM  167  H9  UNK     1       9.975   3.337  18.230  1.00  0.00           H  &lt;br /&gt;
HETATM  168  H10 UNK     1      10.541   2.046  17.431  1.00  0.00           H  &lt;br /&gt;
CONECT    1    7&lt;br /&gt;
CONECT    2    7&lt;br /&gt;
CONECT    3    8&lt;br /&gt;
CONECT    4    8&lt;br /&gt;
CONECT    5    9&lt;br /&gt;
CONECT    6    9&lt;br /&gt;
CONECT    7    1    2   10&lt;br /&gt;
CONECT    8    3    4   12&lt;br /&gt;
CONECT    9    5    6   14&lt;br /&gt;
CONECT   10    7   11   15&lt;br /&gt;
CONECT   11   10   12   17&lt;br /&gt;
CONECT   12    8   11   13&lt;br /&gt;
CONECT   13   12   14   18&lt;br /&gt;
CONECT   14    9   13   15&lt;br /&gt;
CONECT   15   10   14   16&lt;br /&gt;
CONECT   16   15   19   20   21&lt;br /&gt;
CONECT   17   11&lt;br /&gt;
CONECT   18   13&lt;br /&gt;
CONECT   19   16&lt;br /&gt;
CONECT   20   16&lt;br /&gt;
CONECT   21   16&lt;br /&gt;
CONECT   22   28&lt;br /&gt;
CONECT   23   28&lt;br /&gt;
CONECT   24   29&lt;br /&gt;
CONECT   25   29&lt;br /&gt;
CONECT   26   30&lt;br /&gt;
CONECT   27   30&lt;br /&gt;
CONECT   28   22   23   31&lt;br /&gt;
CONECT   29   24   25   33&lt;br /&gt;
CONECT   30   26   27   35&lt;br /&gt;
CONECT   31   28   32   36&lt;br /&gt;
CONECT   32   31   33   38&lt;br /&gt;
CONECT   33   29   32   34&lt;br /&gt;
CONECT   34   33   35   39&lt;br /&gt;
CONECT   35   30   34   36&lt;br /&gt;
CONECT   36   31   35   37&lt;br /&gt;
CONECT   37   36   40   41   42&lt;br /&gt;
CONECT   38   32&lt;br /&gt;
CONECT   39   34&lt;br /&gt;
CONECT   40   37&lt;br /&gt;
CONECT   41   37&lt;br /&gt;
CONECT   42   37&lt;br /&gt;
CONECT   43   49&lt;br /&gt;
CONECT   44   49&lt;br /&gt;
CONECT   45   50&lt;br /&gt;
CONECT   46   50&lt;br /&gt;
CONECT   47   51&lt;br /&gt;
CONECT   48   51&lt;br /&gt;
CONECT   49   43   44   52&lt;br /&gt;
CONECT   50   45   46   54&lt;br /&gt;
CONECT   51   47   48   56&lt;br /&gt;
CONECT   52   49   53   57&lt;br /&gt;
CONECT   53   52   54   59&lt;br /&gt;
CONECT   54   50   53   55&lt;br /&gt;
CONECT   55   54   56   60&lt;br /&gt;
CONECT   56   51   55   57&lt;br /&gt;
CONECT   57   52   56   58&lt;br /&gt;
CONECT   58   57   61   62   63&lt;br /&gt;
CONECT   59   53&lt;br /&gt;
CONECT   60   55&lt;br /&gt;
CONECT   61   58&lt;br /&gt;
CONECT   62   58&lt;br /&gt;
CONECT   63   58&lt;br /&gt;
CONECT   64   70&lt;br /&gt;
CONECT   65   70&lt;br /&gt;
CONECT   66   71&lt;br /&gt;
CONECT   67   71&lt;br /&gt;
CONECT   68   72&lt;br /&gt;
CONECT   69   72&lt;br /&gt;
CONECT   70   64   65   73&lt;br /&gt;
CONECT   71   66   67   75&lt;br /&gt;
CONECT   72   68   69   77&lt;br /&gt;
CONECT   73   70   74   78&lt;br /&gt;
CONECT   74   73   75   80&lt;br /&gt;
CONECT   75   71   74   76&lt;br /&gt;
CONECT   76   75   77   81&lt;br /&gt;
CONECT   77   72   76   78&lt;br /&gt;
CONECT   78   73   77   79&lt;br /&gt;
CONECT   79   78   82   83   84&lt;br /&gt;
CONECT   80   74&lt;br /&gt;
CONECT   81   76&lt;br /&gt;
CONECT   82   79&lt;br /&gt;
CONECT   83   79&lt;br /&gt;
CONECT   84   79&lt;br /&gt;
CONECT   85   91&lt;br /&gt;
CONECT   86   91&lt;br /&gt;
CONECT   87   92&lt;br /&gt;
CONECT   88   92&lt;br /&gt;
CONECT   89   93&lt;br /&gt;
CONECT   90   93&lt;br /&gt;
CONECT   91   85   86   94&lt;br /&gt;
CONECT   92   87   88   96&lt;br /&gt;
CONECT   93   89   90   98&lt;br /&gt;
CONECT   94   91   95   99&lt;br /&gt;
CONECT   95   94   96  101&lt;br /&gt;
CONECT   96   92   95   97&lt;br /&gt;
CONECT   97   96   98  102&lt;br /&gt;
CONECT   98   93   97   99&lt;br /&gt;
CONECT   99   94   98  100&lt;br /&gt;
CONECT  100   99  103  104  105&lt;br /&gt;
CONECT  101   95&lt;br /&gt;
CONECT  102   97&lt;br /&gt;
CONECT  103  100&lt;br /&gt;
CONECT  104  100&lt;br /&gt;
CONECT  105  100&lt;br /&gt;
CONECT  106  112&lt;br /&gt;
CONECT  107  112&lt;br /&gt;
CONECT  108  113&lt;br /&gt;
CONECT  109  113&lt;br /&gt;
CONECT  110  114&lt;br /&gt;
CONECT  111  114&lt;br /&gt;
CONECT  112  106  107  115&lt;br /&gt;
CONECT  113  108  109  117&lt;br /&gt;
CONECT  114  110  111  119&lt;br /&gt;
CONECT  115  112  116  120&lt;br /&gt;
CONECT  116  115  117  122&lt;br /&gt;
CONECT  117  113  116  118&lt;br /&gt;
CONECT  118  117  119  123&lt;br /&gt;
CONECT  119  114  118  120&lt;br /&gt;
CONECT  120  115  119  121&lt;br /&gt;
CONECT  121  120  124  125  126&lt;br /&gt;
CONECT  122  116&lt;br /&gt;
CONECT  123  118&lt;br /&gt;
CONECT  124  121&lt;br /&gt;
CONECT  125  121&lt;br /&gt;
CONECT  126  121&lt;br /&gt;
CONECT  127  133&lt;br /&gt;
CONECT  128  133&lt;br /&gt;
CONECT  129  134&lt;br /&gt;
CONECT  130  134&lt;br /&gt;
CONECT  131  135&lt;br /&gt;
CONECT  132  135&lt;br /&gt;
CONECT  133  127  128  136&lt;br /&gt;
CONECT  134  129  130  138&lt;br /&gt;
CONECT  135  131  132  140&lt;br /&gt;
CONECT  136  133  137  141&lt;br /&gt;
CONECT  137  136  138  143&lt;br /&gt;
CONECT  138  134  137  139&lt;br /&gt;
CONECT  139  138  140  144&lt;br /&gt;
CONECT  140  135  139  141&lt;br /&gt;
CONECT  141  136  140  142&lt;br /&gt;
CONECT  142  141  145  146  147&lt;br /&gt;
CONECT  143  137&lt;br /&gt;
CONECT  144  139&lt;br /&gt;
CONECT  145  142&lt;br /&gt;
CONECT  146  142&lt;br /&gt;
CONECT  147  142&lt;br /&gt;
CONECT  148  154&lt;br /&gt;
CONECT  149  154&lt;br /&gt;
CONECT  150  155&lt;br /&gt;
CONECT  151  155&lt;br /&gt;
CONECT  152  156&lt;br /&gt;
CONECT  153  156&lt;br /&gt;
CONECT  154  148  149  157&lt;br /&gt;
CONECT  155  150  151  159&lt;br /&gt;
CONECT  156  152  153  161&lt;br /&gt;
CONECT  157  154  158  162&lt;br /&gt;
CONECT  158  157  159  164&lt;br /&gt;
CONECT  159  155  158  160&lt;br /&gt;
CONECT  160  159  161  165&lt;br /&gt;
CONECT  161  156  160  162&lt;br /&gt;
CONECT  162  157  161  163&lt;br /&gt;
CONECT  163  162  166  167  168&lt;br /&gt;
CONECT  164  158&lt;br /&gt;
CONECT  165  160&lt;br /&gt;
CONECT  166  163&lt;br /&gt;
CONECT  167  163&lt;br /&gt;
CONECT  168  163&lt;br /&gt;
MASTER    0    0    0    0    0    0    0    0    3  168    0  168    0&lt;br /&gt;
END&lt;br /&gt;
                                                            NONE  38&lt;br /&gt;
&amp;lt;/inlineContents&amp;gt;&lt;br /&gt;
&amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
Unit cell paramters in Å&lt;br /&gt;
&lt;br /&gt;
&amp;lt;p&amp;gt;[[Image:&amp;quot;screen_cap_TNT_crystal.jpg&amp;quot; ALIGN=RIGHT]]&amp;lt;/p&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==About 2,4,6-Trinitrotoluene (TNT)==&lt;br /&gt;
&lt;br /&gt;
TNT was originally used as a yellow dye by the german chemist Joseph Wilbrand in 1863. Nowadays, the main use for TNT is in explosives. In chemical synthesis it is also used to make charge transfer salts. At the time of its discovery the explosive properties of TNT were not used because it was difficult to detonate and was significantly weaker than other explosives available at the time. TNT is a relatively stable explosive and as a result it can be poured in shell cases when it’s in its liquid phase given that the melting point of TNT is below the one which makes it detonate spontaneously.  TNT’s ability to not be affected by water (doesn’t dissolve in water or absorb water) means that it can be effectively utilised underwater. TNT is used as a booster or as a bursting charge for high-explosive shells and bombs &amp;lt;sup&amp;gt;2&amp;lt;/sup&amp;gt; .Although pure tnt can be purchased commercially, it is more commonly purchased as a mixture with other compounds such as octol and torpex.&lt;br /&gt;
TNT decomposes at 295&amp;lt;sup&amp;gt;o&amp;lt;/sup&amp;gt;C to produce nitrogen, carbon monoxide, water and carbon.&lt;br /&gt;
The reaction has a high activation energy but is very exothermic. The high activation energy is due to the stabilising delocalisation effect involved throughout the whole molecule.&lt;br /&gt;
&lt;br /&gt;
*Enthalpy of fusion = 23948.47 jmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;   &amp;lt;sup&amp;gt;(5)&amp;lt;/sup&amp;gt;&lt;br /&gt;
*Enthalpy of vapourisation = 71175.57 jmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt; &amp;lt;sup&amp;gt;(6)&amp;lt;/sup&amp;gt;&lt;br /&gt;
*Enthalpy of sublimation= 102283.45 jmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;   &amp;lt;sup&amp;gt;(7)&amp;lt;/sup&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;i&amp;gt;A TNT explosion. Video clip showing an exploding caravan:&amp;lt;/i&amp;gt;  http://www.youtube.com/watch?v=625OsObNXRc&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
[[Image:tnt_table.jpg]]&lt;br /&gt;
&lt;br /&gt;
&amp;lt;sup&amp;gt;3&amp;lt;/sup&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:isotopic_tnt.jpg]]&lt;br /&gt;
&lt;br /&gt;
==Spectra==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;b&amp;gt;13C NMR spectrum&amp;lt;/b&amp;gt;  (dimethyl sulfixode solvent at 27&amp;lt;sup&amp;gt;o&amp;lt;/sup&amp;gt;C)  &amp;lt;sup&amp;gt;8&amp;lt;/sup&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:tnt13nmr.jpg]]&lt;br /&gt;
&lt;br /&gt;
&amp;lt;b&amp;gt;Proton NMR &amp;lt;/b&amp;gt;( acetonitrile solvent at 25&amp;lt;sup&amp;gt;o&amp;lt;/sup&amp;gt;C)&amp;lt;sup&amp;gt;10&amp;lt;/sup&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:tntprotonnmr.jpg]]&lt;br /&gt;
&lt;br /&gt;
&amp;lt;b&amp;gt;IR spectrum&amp;lt;/b&amp;gt; &amp;lt;sup&amp;gt;9&amp;lt;/sup&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:tntir.jpg]]&lt;br /&gt;
&lt;br /&gt;
&amp;lt;b&amp;gt;Mass spec&amp;lt;/b&amp;gt; &amp;lt;sup&amp;gt;11&amp;lt;/sup&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:tntmassspec.jpg]]&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;i&amp;gt;General overview&amp;lt;/i&amp;gt;&lt;br /&gt;
&lt;br /&gt;
TNT can be synthesised by refluxing toluene with aqua regia (a mixture of concentrated sulphuric acid and concentrated nitric acid) to make dinitrotoluene. Further nitration with nitric acid and 15% oleum leads to successful synthesis of TNT. Using this method, with toluene as the reactant, produces a typical yield of approximately 26% TNT.&lt;br /&gt;
&lt;br /&gt;
&amp;lt;i&amp;gt; Detailed synthesis method&amp;lt;/i&amp;gt; &amp;lt;sup&amp;gt;12&amp;lt;/sup&amp;gt;&lt;br /&gt;
&lt;br /&gt;
Cool 75ml of sulphuric acid (15% oleum) to 273K. Add dropwise 27ml concentrated nitric acid.  Warm the acid mixture to room temperature. Add 35.4g of 2,4-dinitrotoluene while gently stirring. Slowly raise the temperature to 363K in a 60 min period. Maintain this temperature for 2 hours. Cool the reaction overnight at 298K. Extract the mixture with 800ml methylene chloride. Neutralise the chloride layer with 500ml with saturated sodium carbonate solution and wash twice with 500ml water. Remove the chloride layer using a rotatory evaporator and recrystallise the solid tnt with ethanol and tetrachloromethane. A yield of 62% can be obtained using this method.&lt;br /&gt;
&lt;br /&gt;
==Hazards==&lt;br /&gt;
&amp;lt;sup&amp;gt;4&amp;lt;/sup&amp;gt;&lt;br /&gt;
&lt;br /&gt;
*carcinogen&lt;br /&gt;
*cardiovascular or blood toxicant&lt;br /&gt;
*neurotoxicant&lt;br /&gt;
*respiratory toxicant&lt;br /&gt;
*skin or sense organ toxicant&lt;br /&gt;
*Toxic to aquatic organisms &lt;br /&gt;
*Harmful to aquatic organisms &lt;br /&gt;
*May cause long-term adverse effects in the aquatic environment &lt;br /&gt;
*Avoid release to the environment&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
*1){{doi-inline|doi:10.1021/cg0340704|DOI reference}}&lt;br /&gt;
*2)http://www.ordnance.org/tnt.htm&lt;br /&gt;
*3)http://www.chemcalc.org/&lt;br /&gt;
*4)http://www.scorecard.org/chemical-profiles/summary.tcl?edf_substance_id=118-96-7#hazards&lt;br /&gt;
*5)Nitta et al, Chem abstr, vol 71, 1951, pg 6448&lt;br /&gt;
*6)Beljajew, Chem abstr, vol 22, 1948, pg 5227&lt;br /&gt;
*7)Lenchitz Velicky, J chem eng data, vol 15, 1970, pg401-403&lt;br /&gt;
*8)ycka, Antonin; Machacek, Vladimir; Jirman, Josef.    Res. Inst. Org. Synth.,  Pardubice-Rybitvi,  Czech.    Collection of Czechoslovak Chemical Communications  (1987),  52(12),  2946-52.  CODEN: CCCCAK  ISSN: 0366-547X.  Journal  written in English.    CAN 109:148794    AN 1988:548794    CAPLUS&lt;br /&gt;
*9)eelenbinder, John A.; Brown, Chris W.    Department of Chemistry and Partnership for Sensors and Surface Technology,  University of Rhode Island,  Kingston,  RI,  USA.    Applied Spectroscopy  (2002),  56(3),  295-299.  Publisher: Society for Applied Spectroscopy,  CODEN: APSPA4  ISSN: 0003-7028.  Journal  written in English.    CAN 137:33057    AN 137:33057    CAPLUS&lt;br /&gt;
*10)Soojhawon, I.; Lokhande, P. D.; Kodam, K. M.; Gawai, K. R.    Department of Chemistry,  University of Pune,  Pune,  India.    Enzyme and Microbial Technology  (2005),  37(5),  527-533.  Publisher: Elsevier B.V.,  CODEN: EMTED2  ISSN: 0141-0229.  Journal  written in English.    CAN 143:433829    AN 143:433829    CAPLUS &lt;br /&gt;
*11) Sharma, S. P.; Lahiri, S. C.    Central Forensic Science Laboratory,  Government of India,  Kolkata,  India.    Journal of Energetic Materials  (2005),  23(4),  239-264.  Publisher: Taylor &amp;amp; Francis, Inc.,  CODEN: JOEMDK  ISSN: 0737-0652.  Journal  written in English.    CAN 143:340765    AN 143:340765    CAPLUS&lt;br /&gt;
*12){{doi-inline|doi:10.1021/je00035a030|DOI reference}}&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Ozone&amp;diff=14182</id>
		<title>It07:Ozone</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Ozone&amp;diff=14182"/>
		<updated>2007-12-07T17:39:00Z</updated>

		<summary type="html">&lt;p&gt;Mr406: /* About */&lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Ozone=&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:OzoneMolecule.jpg|130px|Ozone]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| Ozone&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| Trioxygen&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| O3&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 47.998 g·mol−1&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| Gas (293K)&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 10028-15-6]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| 2.144 g·L−1 (0 °C), gas&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| 0.105 g·100mL−1 (0 °C)&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| 80.7 K, −192.5 °C&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 161.3 K, −111.9 °C&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
==About==&lt;br /&gt;
Ozone is a well known molecule consisting of three oxygen atoms bonded in a bent arrangement, with a positive charge on the central atom and a partial distrubuted negative charge across the terminal oxygen atoms and bonds. It is found in the upper atmosphere and protects the earth&#039;s surface from intense UV radiation, although ozone itself is a pollutant. Also ozone is a by-product produced from photocopying machines. This is why it is recommended for photocopying from a photocopying machine to be done in a well ventilated area.&lt;br /&gt;
&lt;br /&gt;
==Uses==&lt;br /&gt;
Ozone can be used in organic synthesis in a process called &#039;&#039;Ozonolysis&#039;&#039;. This synthesis takes a alkene to molozonide and can be further converted to two aldehydes. RC=CR&#039; get converted to RC=O and R&#039;C=O. The mechanism involves the formation of a primary 5 membered ring structure followed by a rearrangement of the ring, then on addition of say PPh3 the ring is attacked and the two R aldehydes form.&lt;br /&gt;
[[Image:Ozonolysis.jpg|centre|200|Mechanism of ozonolysis]]&lt;br /&gt;
&lt;br /&gt;
==Structure of ozone==&lt;br /&gt;
&lt;br /&gt;
===2D structure===&lt;br /&gt;
[[Image:ozone.gif|left|ozone]]&lt;br /&gt;
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Ozone is a triatomic bent molecule, with C&amp;lt;sub&amp;gt;2V&amp;lt;/sub&amp;gt; symmetry. It can be drawn as a central sp&amp;lt;sup&amp;gt;2&amp;lt;/sup&amp;gt; hybridised central oxygen atom, bound to two oxygen atoms with one double bond and one single bond. The signally bonded oxygen carries a single formal negative charge whilst the central oxygen carries a single formal positive charge. Resonance structures can be drawn by swapping the double and single bonds over, both resonance structures contribute equally to the overall structure. In reality, ozone has a delocalised structure where the central oxygen carries a formal positive charge and the other two oxygens have half negative charges. Both bond lengths are equal at 1.28Å.&lt;br /&gt;
&lt;br /&gt;
===3D structure===&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Methamphetamine&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;navy&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Ozone123.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Ozone in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Ozone123.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Ozone reactions==&lt;br /&gt;
&lt;br /&gt;
Mostly ozone reactions occur in the atomsphere. It acts as an unstable reactant in the sunlight. These reactions are described in high ozone layer (stratosphere) and low ozone layer (tropospheric ozone).&lt;br /&gt;
&lt;br /&gt;
High ozone layer:&lt;br /&gt;
&lt;br /&gt;
Stratosphere layer is 10km and 50 km above the earth surface. &lt;br /&gt;
&lt;br /&gt;
[[Image:high123.gif|left|ozone in high layer]]&lt;br /&gt;
It then filters out the UV lights with shorter wavelength (from 270nm to 440nm),which is harmful to mamy things. Ozone in the high layer is alomost produced by oxygens and UV light. The above reaction is the formation of ozone. Ozone is a 3-atoms molecule, which is in higher energy than the 2-atoms oxygens. In order to create this higher energy molecule, we need a large amount of energy to do this. This energy is then provided by the UV photons with high energy. The photon reacts with the oxygen molecule to give to 2 oxygen atoms. After the formation of 2 oxygen atoms,one of them then react with oxygen to give ozone.&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
Low ozone layer:&lt;br /&gt;
&lt;br /&gt;
tropospheric ozone layer is about 10km and 18km above the earth surface. The ozone within this region is reacting with chemical compounds produced mainly by human. The occuring of these depleting reactions are due to the strong oxidising property of ozone and the presence of the catalytes. &lt;br /&gt;
Ozone depleting reactins can be readily catalysed by bromine or chlorine. These bromine and chlorine are contained in many oganic compounds produced by human, such as brominated halons or chlorofluorocarbons (CFC&#039;s).&lt;br /&gt;
&lt;br /&gt;
For the CFC&#039;s:&lt;br /&gt;
[[Image:low1.gif|left|ozone in low layer]]&lt;br /&gt;
The CFC is photolyzed by UV light that breaks the weakest bond, usually a C-Cl bond. The Cl radical is formed and then reacts with ozone.&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
Brominated halons follow the similar above reation, but its C-Br bond is broken by the UV light.&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
Oxdising reaction:&lt;br /&gt;
&lt;br /&gt;
Since ozone can act as a strong oxiding agent, it can react the following reaction.&lt;br /&gt;
[[Image:low2.gif|left|ozone in low layer]]&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
http://www.princeton.edu/~chm333/2002/spring/Ozone/chemistry_formation.htm&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=14160</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=14160"/>
		<updated>2007-12-07T17:25:21Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt;  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
==Terbutaline Sulphate==&lt;br /&gt;
==Structure==&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
==Crystal Structure==&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;TESU.cif&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;TESU.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]like [http://www.ch.ic.ac.uk/wiki/index.php/It07:Salbutamol salbutamol]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref name=&amp;quot;Perry&amp;quot;&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma &amp;lt;ref name=&amp;quot;Perry&amp;quot;/&amp;gt;&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness &amp;lt;ref&amp;gt;http://www.drugs.com/pdr/terbutaline-sulfate.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &amp;lt;ref&amp;gt;Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 &lt;br /&gt;
Effenberger, F.; Jager, J.&lt;br /&gt;
J. Org. Chem.; (Article); 1997; 62(12); 3867-3873.  DOI: 10.1021/jo970032d &amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
Image taken from Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 Effenberger, F.; Jager, J. J. Org. Chem.; (Article); 1997; 62(12); 3867-3873. DOI: 10.1021/jo970032d&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Real Life Product==&lt;br /&gt;
Below is a Bricanyl inhaler, which contains terbutaline sulphate.&lt;br /&gt;
[[Image:Bricanyl_Terbutaline_sulphate.JPG|center|350px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=14158</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=14158"/>
		<updated>2007-12-07T17:23:14Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt;  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
==Terbutaline Sulphate==&lt;br /&gt;
==Structure==&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
==Crystal Structure==&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;TESU.cif&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;TESU.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]like [http://www.ch.ic.ac.uk/wiki/index.php/It07:Salbutamol salbutamol]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref name=&amp;quot;Perry&amp;quot;&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma &amp;lt;ref name=&amp;quot;Perry&amp;quot;/&amp;gt;&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness &amp;lt;ref&amp;gt;http://www.drugs.com/pdr/terbutaline-sulfate.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &amp;lt;ref&amp;gt;Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 &lt;br /&gt;
Effenberger, F.; Jager, J.&lt;br /&gt;
J. Org. Chem.; (Article); 1997; 62(12); 3867-3873.  DOI: 10.1021/jo970032d &amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
&lt;br /&gt;
==Real Life Product==&lt;br /&gt;
Below is a Bricanyl inhaler, which contains terbutaline sulphate.&lt;br /&gt;
[[Image:Bricanyl_Terbutaline_sulphate.JPG|center|350px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=13003</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=13003"/>
		<updated>2007-12-05T11:26:58Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt;  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
==Terbutaline Sulphate==&lt;br /&gt;
==Structure==&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
==Crystal Structure==&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;TESU.cif&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;TESU.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]like [http://www.ch.ic.ac.uk/wiki/index.php/It07:Salbutamol salbutamol]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref name=&amp;quot;Perry&amp;quot;&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma &amp;lt;ref name=&amp;quot;Perry&amp;quot;/&amp;gt;&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness &amp;lt;ref&amp;gt;http://www.drugs.com/pdr/terbutaline-sulfate.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &amp;lt;ref&amp;gt;Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 &lt;br /&gt;
Effenberger, F.; Jager, J.&lt;br /&gt;
J. Org. Chem.; (Article); 1997; 62(12); 3867-3873.  DOI: 10.1021/jo970032d &amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
&lt;br /&gt;
[[Image:Bricanyl_Terbutaline_sulphate.JPG|center|350px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=12982</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=12982"/>
		<updated>2007-12-05T11:15:05Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC, Dronabinol, Marinol, Deltanyne, Tetranabinex, Compassia, delta9-THC, delta1-THC, delta(sup 1)-Thc,delta(sup 9)-THC.&amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==Introduction==&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocannabinol (commonly known as cannabis) is obtained by harvesting the resin of Cannabis sativa (marijuana, hashish). It is one of the oldest hallucigens in the world.It is a psychoactive compound, which triggers characteristic mood and perceptual changes in the user. There are many isomers, but the most active form is delta-9-tetrahydrocannabinol (THC), creating the most intense effects when used. &amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt; THC belongs to a sub-class of compounds called [http://en.wikipedia.org/wiki/Cannabinoids cannabinoids], which in turn belong to the class of molecules called [http://en.wikipedia.org/wiki/Terpenoids terpenoids]. Related to THC are [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Menthol menthol],[http://en.wikipedia.org/wiki/Turpentine turpentine] and [http://en.wikipedia.org/wiki/Camphor camphor]&amp;lt;ref&amp;gt;http://www.ch.ic.ac.uk/vchemlib/mim/bristol/thc/thc_text.htm&amp;lt;/ref&amp;gt;.&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|tetrahydrocannabinol 3D]]Image was taken from http://en.wikipedia.org/wiki/Tetrahydrocannabinol&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
==Effects on the brain==&lt;br /&gt;
&lt;br /&gt;
THC effects the brain by binding to receptors in the brain which promote the release of Acetyl Choline&amp;lt;ref&amp;gt;A. Pisanu, E. Acquas, S. Fenu and G. Di Chiara, Neuropharmacology, 2006, 50, 661-670. {{DOI|10.1016/j.neuropharm.2005.11.023}}&amp;lt;/ref&amp;gt; &lt;br /&gt;
and Dopamine. There are various cannabinoid G protein-coupled receptors in the form of CB1 and CB2 as well as unusual receptors GPR55 and GPR119 which are needed to explain some of the other unexplainable pharmalogical effects of cannabinoids such as THC &amp;lt;ref&amp;gt;A. J. Brown, Br J Pharmacol, 2007, 152, 567-575.{{DOI|10.1038/sj.bjp.0707481}}&amp;lt;/ref&amp;gt;. THC works to effect the brain in various ways as described next.&lt;br /&gt;
&lt;br /&gt;
THC can cause change in levels of cAMP which in turn effect hyperpolarization-activated cyclic nucleotide-gated channels which then effects the ability of communication of brain cells.&lt;br /&gt;
&lt;br /&gt;
&amp;lt;ref&amp;gt;Serendip: http://serendip.brynmawr.edu/bb/neuro/neuro04/web1/aejelonu.html&amp;lt;/ref&amp;gt;THC acts by binding to cannabinoid receptors and then causing the release or uptake of various neurotransmitters. Cannabinoid receptors are responsible for the control of thought, memory, concentration and movement. In the hippocampus there are a lot of THC receptors and the way information is taken in by this part of the brain is effected. The hippocampus is responsible for memory and so THC can lead to short term memory problems. Also the binding to the receptors causes damage to the nerve cells and so decreases their activities.  &lt;br /&gt;
&lt;br /&gt;
THC can also effects the emotions of the consumer by effecting the brains limbic system which controls behaviour and emotions. It is responsible for the characteristic laughing and/or paranoia associated with the intake of cannabis. Taking 14mg or more of THC at one time can have dramatic effects on the emotions and bodily functions of the person involved.&lt;br /&gt;
&lt;br /&gt;
THC also gives the &amp;quot;feel good factor&amp;quot; which is made by the interaction of drug with the part of the brain which acts on reward. To do this the THC encourages the release of dopamine by the brain cells.&lt;br /&gt;
Coordination is effected by the tetrahydrocannabinol by its binding with the receptors in the brain (cerebellum and basal ganglia). This has not been proven to cause accidents because any found THC levels in people that cause accidents are also usually accompanied with alcohol as well.&lt;br /&gt;
&lt;br /&gt;
Brain areas in which cannabinoid receptors are abundant and hence effect to some extent:&amp;lt;ref&amp;gt;National Institute of Drug Abuse: http://www.nida.nih.gov/ResearchReports/Marijuana/Marijuana3.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
*Cerebellum (movement)&lt;br /&gt;
*Hippocampus (Memory)&lt;br /&gt;
*Cerebral cortex (Higher thought)&lt;br /&gt;
*Nucleus accumbens (Rewards)&lt;br /&gt;
*Basal ganglia (control of movement)&lt;br /&gt;
&lt;br /&gt;
Less abundant(but still present) in:&lt;br /&gt;
&lt;br /&gt;
*Hypothalamus (Regulation)&lt;br /&gt;
*Amygdala (Emotions)&lt;br /&gt;
*Spinal cord (Peripheral sensing)&lt;br /&gt;
&lt;br /&gt;
==Medicinal Uses==&lt;br /&gt;
The delta-trans form of THC (also known as [http://en.wikipedia.org/wiki/Dronabinol dronabinol]) has anti-emetic effects (inhibits vomiting), thus making it a useful substance for cancer patients on chemotherapy. Also as well as reducing the vomiting response, it increases the appetite, thus making it a treatment for anorexia and other eating disorders &amp;lt;ref&amp;gt;http://www.ch.ic.ac.uk/vchemlib/mim/bristol/thc/thc_text.htm&amp;lt;/ref&amp;gt;. Recent research has shown that this form of THC is a useful anti-[http://en.wikipedia.org/wiki/Glaucoma glaucoma] agent&amp;lt;ref&amp;gt;http://biotech.icmb.utexas.edu/botany/thc.html&amp;lt;/ref&amp;gt;.&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10872</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10872"/>
		<updated>2007-11-08T14:44:01Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt;  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
==Terbutaline Sulphate==&lt;br /&gt;
==Structure==&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
==Crystal Structure==&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;TESU.cif&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;TESU.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref name=&amp;quot;Perry&amp;quot;&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma &amp;lt;ref name=&amp;quot;Perry&amp;quot;/&amp;gt;&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness &amp;lt;ref&amp;gt;http://www.drugs.com/pdr/terbutaline-sulfate.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &amp;lt;ref&amp;gt;Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 &lt;br /&gt;
Effenberger, F.; Jager, J.&lt;br /&gt;
J. Org. Chem.; (Article); 1997; 62(12); 3867-3873.  DOI: 10.1021/jo970032d &amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
&lt;br /&gt;
[[Image:Bricanyl_Terbutaline_sulphate.JPG|center|350px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10805</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10805"/>
		<updated>2007-11-08T11:12:11Z</updated>

		<summary type="html">&lt;p&gt;Mr406: /* Medicinal Uses */&lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC, Dronabinol, Marinol, Deltanyne, Tetranabinex, Compassia, delta9-THC, delta1-THC, delta(sup 1)-Thc,delta(sup 9)-THC.&amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==Introduction==&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocannabinol (commonly known as cannabis) is obtained by harvesting the resin of Cannabis sativa (marijuana, hashish). It is one of the oldest hallucigens in the world.It is a psychoactive compound, which triggers characteristic mood and perceptual changes in the user. There are many isomers, but the most active form is delta-9-tetrahydrocannabinol (THC), creating the most intense effects when used. &amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt; THC belongs to a sub-class of compounds called [http://en.wikipedia.org/wiki/Cannabinoids cannabinoids], which in turn belong to the class of molecules called [http://en.wikipedia.org/wiki/Terpenoids terpenoids]. Related to THC are [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Menthol menthol],[http://en.wikipedia.org/wiki/Turpentine turpentine] and [http://en.wikipedia.org/wiki/Camphor camphor]&amp;lt;ref&amp;gt;http://www.ch.ic.ac.uk/vchemlib/mim/bristol/thc/thc_text.htm&amp;lt;/ref&amp;gt;.&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|tetrahydrocannabinol 3D]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
==Effects on the brain==&lt;br /&gt;
&lt;br /&gt;
THC effects the brain by binding to receptors in the brain which promote the release of Acetyl Choline&amp;lt;ref&amp;gt;A. Pisanu, E. Acquas, S. Fenu and G. Di Chiara, Neuropharmacology, 2006, 50, 661-670. {{DOI|10.1016/j.neuropharm.2005.11.023}}&amp;lt;/ref&amp;gt; &lt;br /&gt;
and Dopamine. There are various cannabinoid G protein-coupled receptors in the form of CB1 and CB2 as well as unusual receptors GPR55 and GPR119 which are needed to explain some of the other unexplainable pharmalogical effects of cannabinoids such as THC &amp;lt;ref&amp;gt;A. J. Brown, Br J Pharmacol, 2007, 152, 567-575.{{DOI|10.1038/sj.bjp.0707481}}&amp;lt;/ref&amp;gt;. THC works to effect the brain in various ways as described next.&lt;br /&gt;
&lt;br /&gt;
THC can cause change in levels of cAMP which in turn effect hyperpolarization-activated cyclic nucleotide-gated channels which then effects the ability of communication of brain cells.&lt;br /&gt;
&lt;br /&gt;
&amp;lt;ref&amp;gt;Serendip: http://serendip.brynmawr.edu/bb/neuro/neuro04/web1/aejelonu.html&amp;lt;/ref&amp;gt;THC acts by binding to cannabinoid receptors and then causing the release or uptake of various neurotransmitters. Cannabinoid receptors are responsible for the control of thought, memory, concentration and movement. In the hippocampus there are a lot of THC receptors and the way information is taken in by this part of the brain is effected. The hippocampus is responsible for memory and so THC can lead to short term memory problems. Also the binding to the receptors causes damage to the nerve cells and so decreases their activities.  &lt;br /&gt;
&lt;br /&gt;
THC can also effects the emotions of the consumer by effecting the brains limbic system which controls behaviour and emotions. It is responsible for the characteristic laughing and/or paranoia associated with the intake of cannabis. Taking 14mg or more of THC at one time can have dramatic effects on the emotions and bodily functions of the person involved.&lt;br /&gt;
&lt;br /&gt;
THC also gives the &amp;quot;feel good factor&amp;quot; which is made by the interaction of drug with the part of the brain which acts on reward. To do this the THC encourages the release of dopamine by the brain cells.&lt;br /&gt;
Coordination is effected by the tetrahydrocannabinol by its binding with the receptors in the brain (cerebellum and basal ganglia). This has not been proven to cause accidents because any found THC levels in people that cause accidents are also usually accompanied with alcohol as well.&lt;br /&gt;
&lt;br /&gt;
Brain areas in which cannabinoid receptors are abundant and hence effect to some extent:&amp;lt;ref&amp;gt;National Institute of Drug Abuse: http://www.nida.nih.gov/ResearchReports/Marijuana/Marijuana3.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
*Cerebellum (movement)&lt;br /&gt;
*Hippocampus (Memory)&lt;br /&gt;
*Cerebral cortex (Higher thought)&lt;br /&gt;
*Nucleus accumbens (Rewards)&lt;br /&gt;
*Basal ganglia (control of movement)&lt;br /&gt;
&lt;br /&gt;
Less abundant(but still present) in:&lt;br /&gt;
&lt;br /&gt;
*Hypothalamus (Regulation)&lt;br /&gt;
*Amygdala (Emotions)&lt;br /&gt;
*Spinal cord (Peripheral sensing)&lt;br /&gt;
&lt;br /&gt;
==Medicinal Uses==&lt;br /&gt;
The delta-trans form of THC (also known as [http://en.wikipedia.org/wiki/Dronabinol dronabinol]) has anti-emetic effects (inhibits vomiting), thus making it a useful substance for cancer patients on chemotherapy. Also as well as reducing the vomiting response, it increases the appetite, thus making it a treatment for anorexia and other eating disorders &amp;lt;ref&amp;gt;http://www.ch.ic.ac.uk/vchemlib/mim/bristol/thc/thc_text.htm&amp;lt;/ref&amp;gt;. Recent research has shown that this form of THC is a useful anti-[http://en.wikipedia.org/wiki/Glaucoma glaucoma] agent&amp;lt;ref&amp;gt;http://biotech.icmb.utexas.edu/botany/thc.html&amp;lt;/ref&amp;gt;.&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10804</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10804"/>
		<updated>2007-11-08T11:10:52Z</updated>

		<summary type="html">&lt;p&gt;Mr406: /* Medicinal Uses */&lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC, Dronabinol, Marinol, Deltanyne, Tetranabinex, Compassia, delta9-THC, delta1-THC, delta(sup 1)-Thc,delta(sup 9)-THC.&amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==Introduction==&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocannabinol (commonly known as cannabis) is obtained by harvesting the resin of Cannabis sativa (marijuana, hashish). It is one of the oldest hallucigens in the world.It is a psychoactive compound, which triggers characteristic mood and perceptual changes in the user. There are many isomers, but the most active form is delta-9-tetrahydrocannabinol (THC), creating the most intense effects when used. &amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt; THC belongs to a sub-class of compounds called [http://en.wikipedia.org/wiki/Cannabinoids cannabinoids], which in turn belong to the class of molecules called [http://en.wikipedia.org/wiki/Terpenoids terpenoids]. Related to THC are [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Menthol menthol],[http://en.wikipedia.org/wiki/Turpentine turpentine] and [http://en.wikipedia.org/wiki/Camphor camphor]&amp;lt;ref&amp;gt;http://www.ch.ic.ac.uk/vchemlib/mim/bristol/thc/thc_text.htm&amp;lt;/ref&amp;gt;.&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|tetrahydrocannabinol 3D]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
==Effects on the brain==&lt;br /&gt;
&lt;br /&gt;
THC effects the brain by binding to receptors in the brain which promote the release of Acetyl Choline&amp;lt;ref&amp;gt;A. Pisanu, E. Acquas, S. Fenu and G. Di Chiara, Neuropharmacology, 2006, 50, 661-670. {{DOI|10.1016/j.neuropharm.2005.11.023}}&amp;lt;/ref&amp;gt; &lt;br /&gt;
and Dopamine. There are various cannabinoid G protein-coupled receptors in the form of CB1 and CB2 as well as unusual receptors GPR55 and GPR119 which are needed to explain some of the other unexplainable pharmalogical effects of cannabinoids such as THC &amp;lt;ref&amp;gt;A. J. Brown, Br J Pharmacol, 2007, 152, 567-575.{{DOI|10.1038/sj.bjp.0707481}}&amp;lt;/ref&amp;gt;. THC works to effect the brain in various ways as described next.&lt;br /&gt;
&lt;br /&gt;
THC can cause change in levels of cAMP which in turn effect hyperpolarization-activated cyclic nucleotide-gated channels which then effects the ability of communication of brain cells.&lt;br /&gt;
&lt;br /&gt;
&amp;lt;ref&amp;gt;Serendip: http://serendip.brynmawr.edu/bb/neuro/neuro04/web1/aejelonu.html&amp;lt;/ref&amp;gt;THC acts by binding to cannabinoid receptors and then causing the release or uptake of various neurotransmitters. Cannabinoid receptors are responsible for the control of thought, memory, concentration and movement. In the hippocampus there are a lot of THC receptors and the way information is taken in by this part of the brain is effected. The hippocampus is responsible for memory and so THC can lead to short term memory problems. Also the binding to the receptors causes damage to the nerve cells and so decreases their activities.  &lt;br /&gt;
&lt;br /&gt;
THC can also effects the emotions of the consumer by effecting the brains limbic system which controls behaviour and emotions. It is responsible for the characteristic laughing and/or paranoia associated with the intake of cannabis. Taking 14mg or more of THC at one time can have dramatic effects on the emotions and bodily functions of the person involved.&lt;br /&gt;
&lt;br /&gt;
THC also gives the &amp;quot;feel good factor&amp;quot; which is made by the interaction of drug with the part of the brain which acts on reward. To do this the THC encourages the release of dopamine by the brain cells.&lt;br /&gt;
Coordination is effected by the tetrahydrocannabinol by its binding with the receptors in the brain (cerebellum and basal ganglia). This has not been proven to cause accidents because any found THC levels in people that cause accidents are also usually accompanied with alcohol as well.&lt;br /&gt;
&lt;br /&gt;
Brain areas in which cannabinoid receptors are abundant and hence effect to some extent:&amp;lt;ref&amp;gt;National Institute of Drug Abuse: http://www.nida.nih.gov/ResearchReports/Marijuana/Marijuana3.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
*Cerebellum (movement)&lt;br /&gt;
*Hippocampus (Memory)&lt;br /&gt;
*Cerebral cortex (Higher thought)&lt;br /&gt;
*Nucleus accumbens (Rewards)&lt;br /&gt;
*Basal ganglia (control of movement)&lt;br /&gt;
&lt;br /&gt;
Less abundant(but still present) in:&lt;br /&gt;
&lt;br /&gt;
*Hypothalamus (Regulation)&lt;br /&gt;
*Amygdala (Emotions)&lt;br /&gt;
*Spinal cord (Peripheral sensing)&lt;br /&gt;
&lt;br /&gt;
==Medicinal Uses==&lt;br /&gt;
The delta-trans form of THC (also known as [http://en.wikipedia.org/wiki/Dronabinol dronabinol]) has anti-emetic effects (inhibits vomiting), thus making it a useful substance for cancer patients on chemotherapy. Also as well as reducing the vomiting response, it increases the appetite, thus making it a treatment for anorexia and other eating disorders &amp;lt;ref&amp;gt;http://www.ch.ic.ac.uk/vchemlib/mim/bristol/thc/thc_text.htm&amp;lt;/ref&amp;gt;. Recent research has shown that this form of THC is a useful anti-[http://en.wikipedia.org/wiki/Glaucoma glaucoma] agent.&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10803</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10803"/>
		<updated>2007-11-08T10:51:13Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC, Dronabinol, Marinol, Deltanyne, Tetranabinex, Compassia, delta9-THC, delta1-THC, delta(sup 1)-Thc,delta(sup 9)-THC.&amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==Introduction==&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocannabinol (commonly known as cannabis) is obtained by harvesting the resin of Cannabis sativa (marijuana, hashish). It is one of the oldest hallucigens in the world.It is a psychoactive compound, which triggers characteristic mood and perceptual changes in the user. There are many isomers, but the most active form is delta-9-tetrahydrocannabinol (THC), creating the most intense effects when used. &amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt; THC belongs to a sub-class of compounds called [http://en.wikipedia.org/wiki/Cannabinoids cannabinoids], which in turn belong to the class of molecules called [http://en.wikipedia.org/wiki/Terpenoids terpenoids]. Related to THC are [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Menthol menthol],[http://en.wikipedia.org/wiki/Turpentine turpentine] and [http://en.wikipedia.org/wiki/Camphor camphor]&amp;lt;ref&amp;gt;http://www.ch.ic.ac.uk/vchemlib/mim/bristol/thc/thc_text.htm&amp;lt;/ref&amp;gt;.&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|tetrahydrocannabinol 3D]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
==Effects on the brain==&lt;br /&gt;
&lt;br /&gt;
THC effects the brain by binding to receptors in the brain which promote the release of Acetyl Choline&amp;lt;ref&amp;gt;A. Pisanu, E. Acquas, S. Fenu and G. Di Chiara, Neuropharmacology, 2006, 50, 661-670. {{DOI|10.1016/j.neuropharm.2005.11.023}}&amp;lt;/ref&amp;gt; &lt;br /&gt;
and Dopamine. There are various cannabinoid G protein-coupled receptors in the form of CB1 and CB2 as well as unusual receptors GPR55 and GPR119 which are needed to explain some of the other unexplainable pharmalogical effects of cannabinoids such as THC &amp;lt;ref&amp;gt;A. J. Brown, Br J Pharmacol, 2007, 152, 567-575.{{DOI|10.1038/sj.bjp.0707481}}&amp;lt;/ref&amp;gt;. THC works to effect the brain in various ways as described next.&lt;br /&gt;
&lt;br /&gt;
THC can cause change in levels of cAMP which in turn effect hyperpolarization-activated cyclic nucleotide-gated channels which then effects the ability of communication of brain cells.&lt;br /&gt;
&lt;br /&gt;
&amp;lt;ref&amp;gt;Serendip: http://serendip.brynmawr.edu/bb/neuro/neuro04/web1/aejelonu.html&amp;lt;/ref&amp;gt;THC acts by binding to cannabinoid receptors and then causing the release or uptake of various neurotransmitters. Cannabinoid receptors are responsible for the control of thought, memory, concentration and movement. In the hippocampus there are a lot of THC receptors and the way information is taken in by this part of the brain is effected. The hippocampus is responsible for memory and so THC can lead to short term memory problems. Also the binding to the receptors causes damage to the nerve cells and so decreases their activities.  &lt;br /&gt;
&lt;br /&gt;
THC can also effects the emotions of the consumer by effecting the brains limbic system which controls behaviour and emotions. It is responsible for the characteristic laughing and/or paranoia associated with the intake of cannabis. Taking 14mg or more of THC at one time can have dramatic effects on the emotions and bodily functions of the person involved.&lt;br /&gt;
&lt;br /&gt;
THC also gives the &amp;quot;feel good factor&amp;quot; which is made by the interaction of drug with the part of the brain which acts on reward. To do this the THC encourages the release of dopamine by the brain cells.&lt;br /&gt;
Coordination is effected by the tetrahydrocannabinol by its binding with the receptors in the brain (cerebellum and basal ganglia). This has not been proven to cause accidents because any found THC levels in people that cause accidents are also usually accompanied with alcohol as well.&lt;br /&gt;
&lt;br /&gt;
Brain areas in which cannabinoid receptors are abundant and hence effect to some extent:&amp;lt;ref&amp;gt;National Institute of Drug Abuse: http://www.nida.nih.gov/ResearchReports/Marijuana/Marijuana3.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
*Cerebellum (movement)&lt;br /&gt;
*Hippocampus (Memory)&lt;br /&gt;
*Cerebral cortex (Higher thought)&lt;br /&gt;
*Nucleus accumbens (Rewards)&lt;br /&gt;
*Basal ganglia (control of movement)&lt;br /&gt;
&lt;br /&gt;
Less abundant(but still present) in:&lt;br /&gt;
&lt;br /&gt;
*Hypothalamus (Regulation)&lt;br /&gt;
*Amygdala (Emotions)&lt;br /&gt;
*Spinal cord (Peripheral sensing)&lt;br /&gt;
&lt;br /&gt;
==Medicinal Uses==&lt;br /&gt;
The delta-trans form of THC (also known as [http://en.wikipedia.org/wiki/Dronabinol dronabinol]) has anti-emetic effects (inhibits vomiting), thus making it a useful substance for cancer patients on chemotherapy. Also as well as reducing the vomiting response, it increases the appetite, thus making it a treatment for anorexia and other eating disorders &amp;lt;ref&amp;gt;http://www.ch.ic.ac.uk/vchemlib/mim/bristol/thc/thc_text.htm&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10603</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10603"/>
		<updated>2007-11-01T16:19:24Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC, Dronabinol, Marinol, Deltanyne, Tetranabinex, Compassia, delta9-THC, delta1-THC, delta(sup 1)-Thc,delta(sup 9)-THC.&amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==Introduction==&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocannabinol (commonly known as cannabis) is obtained by harvesting the resin of Cannabis sativa (marijuana, hashish). It is one of the oldest hallucigens in the world.It is a psychoactive compound, which triggers characteristic mood and perceptual changes in the user. There are many isomers, but the most active form is delta-9-tetrahydrocannabinol (THC), creating the most intense effects when used. &amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt; THC belongs to a sub-class of compounds called [http://en.wikipedia.org/wiki/Cannabinoids cannabinoids], which in turn belong to the class of molecules called [http://en.wikipedia.org/wiki/Terpenoids terpenoids]. Related to THC are [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Menthol menthol],[http://en.wikipedia.org/wiki/Turpentine turpentine] and [http://en.wikipedia.org/wiki/Camphor camphor]&amp;lt;ref&amp;gt;http://www.ch.ic.ac.uk/vchemlib/mim/bristol/thc/thc_text.htm&amp;lt;/ref&amp;gt;.&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|tetrahydrocannabinol 3D]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
==Effects on the brain==&lt;br /&gt;
&lt;br /&gt;
THC effects the brain by binding to receptors in the brain which promote the release of Acetyl Choline&amp;lt;ref&amp;gt;A. Pisanu, E. Acquas, S. Fenu and G. Di Chiara, Neuropharmacology, 2006, 50, 661-670. {{DOI|10.1016/j.neuropharm.2005.11.023}}&amp;lt;/ref&amp;gt; &lt;br /&gt;
and Dopamine. There are various cannabinoid G protein-coupled receptors in the form of CB1 and CB2 as well as unusual receptors GPR55 and GPR119 which are needed to explain some of the other unexplainable pharmalogical effects of cannabinoids such as THC &amp;lt;ref&amp;gt;A. J. Brown, Br J Pharmacol, 2007, 152, 567-575.{{DOI|10.1038/sj.bjp.0707481}}&amp;lt;/ref&amp;gt;. THC works to effect the brain in various ways as described next.&lt;br /&gt;
&lt;br /&gt;
THC can cause change in levels of cAMP which in turn effect hyperpolarization-activated cyclic nucleotide-gated channels which then effects the ability of communication of brain cells.&lt;br /&gt;
&lt;br /&gt;
&amp;lt;ref&amp;gt;Serendip: http://serendip.brynmawr.edu/bb/neuro/neuro04/web1/aejelonu.html&amp;lt;/ref&amp;gt;THC acts by binding to cannabinoid receptors and then causing the release or uptake of various neurotransmitters. Cannabinoid receptors are responsible for the control of thought, memory, concentration and movement. In the hippocampus there are a lot of THC receptors and the way information is taken in by this part of the brain is effected. The hippocampus is responsible for memory and so THC can lead to short term memory problems. Also the binding to the receptors causes damage to the nerve cells and so decreases their activities.  &lt;br /&gt;
&lt;br /&gt;
THC can also effects the emotions of the consumer by effecting the brains limbic system which controls behaviour and emotions. It is responsible for the characteristic laughing and/or paranoia associated with the intake of cannabis. Taking 14mg or more of THC at one time can have dramatic effects on the emotions and bodily functions of the person involved.&lt;br /&gt;
&lt;br /&gt;
THC also gives the &amp;quot;feel good factor&amp;quot; which is made by the interaction of drug with the part of the brain which acts on reward. To do this the THC encourages the release of dopamine by the brain cells.&lt;br /&gt;
Coordination is effected by the tetrahydrocannabinol by its binding with the receptors in the brain (cerebellum and basal ganglia). This has not been proven to cause accidents because any found THC levels in people that cause accidents are also usually accompanied with alcohol as well.&lt;br /&gt;
&lt;br /&gt;
Brain areas in which cannabinoid receptors are abundant and hence effect to some extent:&amp;lt;ref&amp;gt;National Institute of Drug Abuse: http://www.nida.nih.gov/ResearchReports/Marijuana/Marijuana3.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
*Cerebellum (movement)&lt;br /&gt;
*Hippocampus (Memory)&lt;br /&gt;
*Cerebral cortex (Higher thought)&lt;br /&gt;
*Nucleus accumbens (Rewards)&lt;br /&gt;
*Basal ganglia (control of movement)&lt;br /&gt;
&lt;br /&gt;
Less abundant(but still present) in:&lt;br /&gt;
&lt;br /&gt;
*Hypothalamus (Regulation)&lt;br /&gt;
*Amygdala (Emotions)&lt;br /&gt;
*Spinal cord (Peripheral sensing)&lt;br /&gt;
&lt;br /&gt;
==Medicinal Uses==&lt;br /&gt;
THC has anti-emetic effects (inhibits vomiting), thus making it a useful substance for cancer patients on chemotherapy. Also as well as reducing the vomiting response, it increases the appetite, thus making it a treatment for anorexia and other eating disorders &amp;lt;ref&amp;gt;http://www.ch.ic.ac.uk/vchemlib/mim/bristol/thc/thc_text.htm&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10600</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10600"/>
		<updated>2007-11-01T16:12:37Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC, Dronabinol, Marinol, Deltanyne, Tetranabinex, Compassia, delta9-THC, delta1-THC, delta(sup 1)-Thc,delta(sup 9)-Thc.&amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==Introduction==&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocannabinol (commonly known as cannabis) is obtained by harvesting the resin of Cannabis sativa (marihuana, hashish). It is one of the oldest hallucigens in the world.It is a psychoactive compound, which triggers characteristic mood and perceptual changes in the user. There are many isomers, but the most active form is delta-9-tetrahydrocannabinol (THC), creating the most intense effects when used. &amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt; THC belongs to a sub-class of compounds called [http://en.wikipedia.org/wiki/Cannabinoids cannabinoids], which in turn belong to the class of molecules called [http://en.wikipedia.org/wiki/Terpenoids terpenoids]. Related to THC are [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Menthol menthol],[http://en.wikipedia.org/wiki/Turpentine turpentine] and [http://en.wikipedia.org/wiki/Camphor camphor].&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|tetrahydrocannabinol 3D]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
==Effects on the brain==&lt;br /&gt;
&lt;br /&gt;
THC effects the brain by binding to receptors in the brain which promote the release of Acetyl Choline&amp;lt;ref&amp;gt;A. Pisanu, E. Acquas, S. Fenu and G. Di Chiara, Neuropharmacology, 2006, 50, 661-670. {{DOI|10.1016/j.neuropharm.2005.11.023}}&amp;lt;/ref&amp;gt; &lt;br /&gt;
and Dopamine. There are various cannabinoid G protein-coupled receptors in the form of CB1 and CB2 as well as unusual receptors GPR55 and GPR119 which are needed to explain some of the other unexplainable pharmalogical effects of cannabinoids such as THC &amp;lt;ref&amp;gt;A. J. Brown, Br J Pharmacol, 2007, 152, 567-575.{{DOI|10.1038/sj.bjp.0707481}}&amp;lt;/ref&amp;gt;. THC works to effect the brain in various ways as described next.&lt;br /&gt;
&lt;br /&gt;
THC can cause change in levels of cAMP which in turn effect hyperpolarization-activated cyclic nucleotide-gated channels which then effects the ability of communication of brain cells.&lt;br /&gt;
&lt;br /&gt;
&amp;lt;ref&amp;gt;Serendip: http://serendip.brynmawr.edu/bb/neuro/neuro04/web1/aejelonu.html&amp;lt;/ref&amp;gt;THC acts by binding to cannabinoid receptors and then causing the release or uptake of various neurotransmitters. Cannabinoid receptors are responsible for the control of thought, memory, concentration and movement. In the hippocampus there are a lot of THC receptors and the way information is taken in by this part of the brain is effected. The hippocampus is responsible for memory and so THC can lead to short term memory problems. Also the binding to the receptors causes damage to the nerve cells and so decreases their activities.  &lt;br /&gt;
&lt;br /&gt;
THC can also effects the emotions of the consumer by effecting the brains limbic system which controls behaviour and emotions. It is responsible for the characteristic laughing and/or paranoia associated with the intake of cannabis. Taking 14mg or more of THC at one time can have dramatic effects on the emotions and bodily functions of the person involved.&lt;br /&gt;
&lt;br /&gt;
THC also gives the &amp;quot;feel good factor&amp;quot; which is made by the interaction of drug with the part of the brain which acts on reward. To do this the THC encourages the release of dopamine by the brain cells.&lt;br /&gt;
Coordination is effected by the tetrahydrocannabinol by its binding with the receptors in the brain (cerebellum and basal ganglia). This has not been proven to cause accidents because any found THC levels in people that cause accidents are also usually accompanied with alcohol as well.&lt;br /&gt;
&lt;br /&gt;
Brain areas in which cannabinoid receptors are abundant and hence effect to some extent:&amp;lt;ref&amp;gt;National Institute of Drug Abuse: http://www.nida.nih.gov/ResearchReports/Marijuana/Marijuana3.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
*Cerebellum (movement)&lt;br /&gt;
*Hippocampus (Memory)&lt;br /&gt;
*Cerebral cortex (Higher thought)&lt;br /&gt;
*Nucleus accumbens (Rewards)&lt;br /&gt;
*Basal ganglia (control of movement)&lt;br /&gt;
&lt;br /&gt;
Less abundant(but still present) in:&lt;br /&gt;
&lt;br /&gt;
*Hypothalamus (Regulation)&lt;br /&gt;
*Amygdala (Emotions)&lt;br /&gt;
*Spinal cord (Peripheral sensing)&lt;br /&gt;
&lt;br /&gt;
==Medicinal Uses==&lt;br /&gt;
THC has anti-emetic effects (inhibits vomiting), thus making it a useful substance for cancer patients on chemotherapy. Also as well as reducing the vomiting response, it increases the appetite, thus making it a treatment for anorexia and other eating disorders &amp;lt;ref&amp;gt;http://www.ch.ic.ac.uk/vchemlib/mim/bristol/thc/thc_text.htm&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10597</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10597"/>
		<updated>2007-11-01T16:06:21Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC, Dronabinol, Marinol, Deltanyne, Tetranabinex, Compassia, delta9-THC, delta1-THC, delta(sup 1)-Thc,delta(sup 9)-Thc.&amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==Introduction==&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocannabinol (commonly known as cannabis) is obtained by harvesting the resin of Cannabis sativa (marihuana, hashish). It is one of the oldest hallucigens in the world.It is a psychoactive compound, which triggers characteristic mood and perceptual changes in the user. There are many isomers, but the most active form is delta-9-tetrahydrocannabinol (THC), creating the most intense effects when used. &amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt; THC belongs to a sub-class of compounds called [http://en.wikipedia.org/wiki/Cannabinoids cannabinoids], which in turn belong to the class of molecules called [http://en.wikipedia.org/wiki/Terpenoids terpenoids]. Related to THC are [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Menthol menthol],[http://en.wikipedia.org/wiki/Turpentine turpentine] and [http://en.wikipedia.org/wiki/Camphor camphor].&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|tetrahydrocannabinol 3D]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
==Effects on the brain==&lt;br /&gt;
&lt;br /&gt;
THC effects the brain by binding to receptors in the brain which promote the release of Acetyl Choline&amp;lt;ref&amp;gt;A. Pisanu, E. Acquas, S. Fenu and G. Di Chiara, Neuropharmacology, 2006, 50, 661-670. {{DOI|10.1016/j.neuropharm.2005.11.023}}&amp;lt;/ref&amp;gt; &lt;br /&gt;
and Dopamine. There are various cannabinoid G protein-coupled receptors in the form of CB1 and CB2 as well as unusual receptors GPR55 and GPR119 which are needed to explain some of the other unexplainable pharmalogical effects of cannabinoids such as THC &amp;lt;ref&amp;gt;A. J. Brown, Br J Pharmacol, 2007, 152, 567-575.{{DOI|10.1038/sj.bjp.0707481}}&amp;lt;/ref&amp;gt;. THC works to effect the brain in various ways as described next.&lt;br /&gt;
&lt;br /&gt;
THC can cause change in levels of cAMP which in turn effect hyperpolarization-activated cyclic nucleotide-gated channels which then effects the ability of communication of brain cells.&lt;br /&gt;
&lt;br /&gt;
&amp;lt;ref&amp;gt;Serendip: http://serendip.brynmawr.edu/bb/neuro/neuro04/web1/aejelonu.html&amp;lt;/ref&amp;gt;THC acts by binding to cannabinoid receptors and then causing the release or uptake of various neurotransmitters. Cannabinoid receptors are responsible for the control of thought, memory, concentration and movement. In the hippocampus there are a lot of THC receptors and the way information is taken in by this part of the brain is effected. The hippocampus is responsible for memory and so THC can lead to short term memory problems. Also the binding to the receptors causes damage to the nerve cells and so decreases their activities.  &lt;br /&gt;
&lt;br /&gt;
THC can also effects the emotions of the consumer by effecting the brains limbic system which controls behaviour and emotions. It is responsible for the characteristic laughing and/or paranoia associated with the intake of cannabis. Taking 14mg or more of THC at one time can have dramatic effects on the emotions and bodily functions of the person involved.&lt;br /&gt;
&lt;br /&gt;
THC also gives the &amp;quot;feel good factor&amp;quot; which is made by the interaction of drug with the part of the brain which acts on reward. To do this the THC encourages the release of dopamine by the brain cells.&lt;br /&gt;
Coordination is effected by the tetrahydrocannabinol by its binding with the receptors in the brain (cerebellum and basal ganglia). This has not been proven to cause accidents because any found THC levels in people that cause accidents are also usually accompanied with alcohol as well.&lt;br /&gt;
&lt;br /&gt;
Brain areas in which cannabinoid receptors are abundant and hence effect to some extent:&amp;lt;ref&amp;gt;National Institute of Drug Abuse: http://www.nida.nih.gov/ResearchReports/Marijuana/Marijuana3.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
*Cerebellum (movement)&lt;br /&gt;
*Hippocampus (Memory)&lt;br /&gt;
*Cerebral cortex (Higher thought)&lt;br /&gt;
*Nucleus accumbens (Rewards)&lt;br /&gt;
*Basal ganglia (control of movement)&lt;br /&gt;
&lt;br /&gt;
Less abundant(but still present) in:&lt;br /&gt;
&lt;br /&gt;
*Hypothalamus (Regulation)&lt;br /&gt;
*Amygdala (Emotions)&lt;br /&gt;
*Spinal cord (Peripheral sensing)&lt;br /&gt;
&lt;br /&gt;
==Medicinal Uses==&lt;br /&gt;
THC has anti-emetic effects (inhibits vomiting), thus making it a useful substance for cancer patients on chemotherapy. Also as well as reducing the vomiting response, it increases the appetite&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10582</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10582"/>
		<updated>2007-11-01T15:37:45Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC, Dronabinol, Marinol, Deltanyne, Tetranabinex, Compassia, delta9-THC, delta1-THC, delta(sup 1)-Thc,delta(sup 9)-Thc.&amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==Introduction==&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocannabinol (commonly known as cannabis) is obtained by harvesting the resin of Cannabis sativa (marihuana, hashish). It is one of the oldest hallucigens in the world.It is a psychoactive compound, which triggers characteristic mood and perceptual changes in the user. There are many isomers, but the most active form is delta-9-tetrahydrocannabinol (THC), creating the most intense effects when used. &amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt; THC belongs to a sub-class of compounds called [http://en.wikipedia.org/wiki/Cannabinoids cannabinoids], which in turn belong to the class of molecules called [http://en.wikipedia.org/wiki/Terpenoids terpenoids]. Related to THC are [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Menthol menthol],[http://en.wikipedia.org/wiki/Turpentine turpentine] and [http://en.wikipedia.org/wiki/Camphor camphor].&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|tetrahydrocannabinol 3D]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
==Effects on the brain==&lt;br /&gt;
&lt;br /&gt;
THC effects the brain by binding to receptors in the brain which promote the release of Acetyl Choline&amp;lt;ref&amp;gt;A. Pisanu, E. Acquas, S. Fenu and G. Di Chiara, Neuropharmacology, 2006, 50, 661-670. {{DOI|10.1016/j.neuropharm.2005.11.023}}&amp;lt;/ref&amp;gt; &lt;br /&gt;
and Dopamine. There are various cannabinoid G protein-coupled receptors in the form of CB1 and CB2 as well as unusual receptors GPR55 and GPR119 which are needed to explain some of the other unexplainable pharmalogical effects of cannabinoids such as THC &amp;lt;ref&amp;gt;A. J. Brown, Br J Pharmacol, 2007, 152, 567-575.{{DOI|10.1038/sj.bjp.0707481}}&amp;lt;/ref&amp;gt;. THC works to effect the brain in various ways as described next.&lt;br /&gt;
&lt;br /&gt;
THC can cause change in levels of cAMP which in turn effect hyperpolarization-activated cyclic nucleotide-gated channels which then effects the ability of communication of brain cells.&lt;br /&gt;
&lt;br /&gt;
&amp;lt;ref&amp;gt;Serendip: http://serendip.brynmawr.edu/bb/neuro/neuro04/web1/aejelonu.html&amp;lt;/ref&amp;gt;THC acts by binding to cannabinoid receptors and then causing the release or uptake of various neurotransmitters. Cannabinoid receptors are responsible for the control of thought, memory, concentration and movement. In the hippocampus there are a lot of THC receptors and the way information is taken in by this part of the brain is effected. The hippocampus is responsible for memory and so THC can lead to short term memory problems. Also the binding to the receptors causes damage to the nerve cells and so decreases their activities.  &lt;br /&gt;
&lt;br /&gt;
THC can also effects the emotions of the consumer by effecting the brains limbic system which controls behaviour and emotions. It is responsible for the characteristic laughing and/or paranoia associated with the intake of cannabis. Taking 14mg or more of THC at one time can have dramatic effects on the emotions and bodily functions of the person involved.&lt;br /&gt;
&lt;br /&gt;
THC also gives the &amp;quot;feel good factor&amp;quot; which is made by the interaction of drug with the part of the brain which acts on reward. To do this the THC encourages the release of dopamine by the brain cells.&lt;br /&gt;
Coordination is effected by the tetrahydrocannabinol by its binding with the receptors in the brain (cerebellum and basal ganglia). This has not been proven to cause accidents because any found THC levels in people that cause accidents are also usually accompanied with alcohol as well.&lt;br /&gt;
&lt;br /&gt;
Brain areas in which cannabinoid receptors are abundant and hence effect to some extent:&amp;lt;ref&amp;gt;National Institute of Drug Abuse: http://www.nida.nih.gov/ResearchReports/Marijuana/Marijuana3.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
*Cerebellum (movement)&lt;br /&gt;
*Hippocampus (Memory)&lt;br /&gt;
*Cerebral cortex (Higher thought)&lt;br /&gt;
*Nucleus accumbens (Rewards)&lt;br /&gt;
*Basal ganglia (control of movement)&lt;br /&gt;
&lt;br /&gt;
Less abundant(but still present) in:&lt;br /&gt;
&lt;br /&gt;
*Hypothalamus (Regulation)&lt;br /&gt;
*Amygdala (Emotions)&lt;br /&gt;
*Spinal cord (Peripheral sensing)&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10580</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10580"/>
		<updated>2007-11-01T15:36:56Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC, Dronabinol, Marinol, Deltanyne, Tetranabinex, Compassia, delta9-THC, delta1-THC, delta(sup 1)-Thc,delta(sup 9)-Thc.&amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==Introduction==&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocannabinol (commonly known as cannabis) is obtained by harvesting the resin of Cannabis sativa (marihuana, hashish). It is one of the oldest hallucigens in the world.It is a psychoactive compound, which triggers characteristic mood and perceptual changes in the user. There are many isomers, but the most active form is delta-9-tetrahydrocannabinol (THC), creating the most intense effects when used. &amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt; THC belongs to a sub-class of compounds called [http://en.wikipedia.org/wiki/Cannabinoids cannabinoids], which in turn belong to the class of molecules called terpenoids. Related to THC are [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Menthol menthol],[http://en.wikipedia.org/wiki/Turpentine turpentine] and [http://en.wikipedia.org/wiki/Camphor camphor].&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|tetrahydrocannabinol 3D]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
==Effects on the brain==&lt;br /&gt;
&lt;br /&gt;
THC effects the brain by binding to receptors in the brain which promote the release of Acetyl Choline&amp;lt;ref&amp;gt;A. Pisanu, E. Acquas, S. Fenu and G. Di Chiara, Neuropharmacology, 2006, 50, 661-670. {{DOI|10.1016/j.neuropharm.2005.11.023}}&amp;lt;/ref&amp;gt; &lt;br /&gt;
and Dopamine. There are various cannabinoid G protein-coupled receptors in the form of CB1 and CB2 as well as unusual receptors GPR55 and GPR119 which are needed to explain some of the other unexplainable pharmalogical effects of cannabinoids such as THC &amp;lt;ref&amp;gt;A. J. Brown, Br J Pharmacol, 2007, 152, 567-575.{{DOI|10.1038/sj.bjp.0707481}}&amp;lt;/ref&amp;gt;. THC works to effect the brain in various ways as described next.&lt;br /&gt;
&lt;br /&gt;
THC can cause change in levels of cAMP which in turn effect hyperpolarization-activated cyclic nucleotide-gated channels which then effects the ability of communication of brain cells.&lt;br /&gt;
&lt;br /&gt;
&amp;lt;ref&amp;gt;Serendip: http://serendip.brynmawr.edu/bb/neuro/neuro04/web1/aejelonu.html&amp;lt;/ref&amp;gt;THC acts by binding to cannabinoid receptors and then causing the release or uptake of various neurotransmitters. Cannabinoid receptors are responsible for the control of thought, memory, concentration and movement. In the hippocampus there are a lot of THC receptors and the way information is taken in by this part of the brain is effected. The hippocampus is responsible for memory and so THC can lead to short term memory problems. Also the binding to the receptors causes damage to the nerve cells and so decreases their activities.  &lt;br /&gt;
&lt;br /&gt;
THC can also effects the emotions of the consumer by effecting the brains limbic system which controls behaviour and emotions. It is responsible for the characteristic laughing and/or paranoia associated with the intake of cannabis. Taking 14mg or more of THC at one time can have dramatic effects on the emotions and bodily functions of the person involved.&lt;br /&gt;
&lt;br /&gt;
THC also gives the &amp;quot;feel good factor&amp;quot; which is made by the interaction of drug with the part of the brain which acts on reward. To do this the THC encourages the release of dopamine by the brain cells.&lt;br /&gt;
Coordination is effected by the tetrahydrocannabinol by its binding with the receptors in the brain (cerebellum and basal ganglia). This has not been proven to cause accidents because any found THC levels in people that cause accidents are also usually accompanied with alcohol as well.&lt;br /&gt;
&lt;br /&gt;
Brain areas in which cannabinoid receptors are abundant and hence effect to some extent:&amp;lt;ref&amp;gt;National Institute of Drug Abuse: http://www.nida.nih.gov/ResearchReports/Marijuana/Marijuana3.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
*Cerebellum (movement)&lt;br /&gt;
*Hippocampus (Memory)&lt;br /&gt;
*Cerebral cortex (Higher thought)&lt;br /&gt;
*Nucleus accumbens (Rewards)&lt;br /&gt;
*Basal ganglia (control of movement)&lt;br /&gt;
&lt;br /&gt;
Less abundant(but still present) in:&lt;br /&gt;
&lt;br /&gt;
*Hypothalamus (Regulation)&lt;br /&gt;
*Amygdala (Emotions)&lt;br /&gt;
*Spinal cord (Peripheral sensing)&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10579</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10579"/>
		<updated>2007-11-01T15:30:44Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC, Dronabinol, Marinol, Deltanyne, Tetranabinex, Compassia, delta9-THC, delta1-THC, delta(sup 1)-Thc,delta(sup 9)-Thc.&amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==Introduction==&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocannabinol (commonly known as cannabis) is obtained by harvesting the resin of Cannabis sativa (marihuana, hashish). It is one of the oldest hallucigens in the world.It is a psychoactive compound, which triggers characteristic mood and perceptual changes in the user. There are many isomers, but the most active form is delta-9-tetrahydrocannabinol (THC), creating the most intense effects when used. &amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt; THC belongs to a sub-class of compounds called cannabinoids, which in turn belong to the class of molecules called terpenoids. Related to THC are [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Menthol menthol],[http://en.wikipedia.org/wiki/Turpentine turpentine] and [http://en.wikipedia.org/wiki/Camphor camphor].&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|tetrahydrocannabinol 3D]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
==Effects on the brain==&lt;br /&gt;
&lt;br /&gt;
THC effects the brain by binding to receptors in the brain which promote the release of Acetyl Choline&amp;lt;ref&amp;gt;A. Pisanu, E. Acquas, S. Fenu and G. Di Chiara, Neuropharmacology, 2006, 50, 661-670. {{DOI|10.1016/j.neuropharm.2005.11.023}}&amp;lt;/ref&amp;gt; &lt;br /&gt;
and Dopamine. There are various cannabinoid G protein-coupled receptors in the form of CB1 and CB2 as well as unusual receptors GPR55 and GPR119 which are needed to explain some of the other unexplainable pharmalogical effects of cannabinoids such as THC &amp;lt;ref&amp;gt;A. J. Brown, Br J Pharmacol, 2007, 152, 567-575.{{DOI|10.1038/sj.bjp.0707481}}&amp;lt;/ref&amp;gt;. THC works to effect the brain in various ways as described next.&lt;br /&gt;
&lt;br /&gt;
THC can cause change in levels of cAMP which in turn effect hyperpolarization-activated cyclic nucleotide-gated channels which then effects the ability of communication of brain cells.&lt;br /&gt;
&lt;br /&gt;
&amp;lt;ref&amp;gt;Serendip: http://serendip.brynmawr.edu/bb/neuro/neuro04/web1/aejelonu.html&amp;lt;/ref&amp;gt;THC acts by binding to cannabinoid receptors and then causing the release or uptake of various neurotransmitters. Cannabinoid receptors are responsible for the control of thought, memory, concentration and movement. In the hippocampus there are a lot of THC receptors and the way information is taken in by this part of the brain is effected. The hippocampus is responsible for memory and so THC can lead to short term memory problems. Also the binding to the receptors causes damage to the nerve cells and so decreases their activities.  &lt;br /&gt;
&lt;br /&gt;
THC can also effects the emotions of the consumer by effecting the brains limbic system which controls behaviour and emotions. It is responsible for the characteristic laughing and/or paranoia associated with the intake of cannabis. Taking 14mg or more of THC at one time can have dramatic effects on the emotions and bodily functions of the person involved.&lt;br /&gt;
&lt;br /&gt;
THC also gives the &amp;quot;feel good factor&amp;quot; which is made by the interaction of drug with the part of the brain which acts on reward. To do this the THC encourages the release of dopamine by the brain cells.&lt;br /&gt;
Coordination is effected by the tetrahydrocannabinol by its binding with the receptors in the brain (cerebellum and basal ganglia). This has not been proven to cause accidents because any found THC levels in people that cause accidents are also usually accompanied with alcohol as well.&lt;br /&gt;
&lt;br /&gt;
Brain areas in which cannabinoid receptors are abundant and hence effect to some extent:&amp;lt;ref&amp;gt;National Institute of Drug Abuse: http://www.nida.nih.gov/ResearchReports/Marijuana/Marijuana3.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
*Cerebellum (movement)&lt;br /&gt;
*Hippocampus (Memory)&lt;br /&gt;
*Cerebral cortex (Higher thought)&lt;br /&gt;
*Nucleus accumbens (Rewards)&lt;br /&gt;
*Basal ganglia (control of movement)&lt;br /&gt;
&lt;br /&gt;
Less abundant(but still present) in:&lt;br /&gt;
&lt;br /&gt;
*Hypothalamus (Regulation)&lt;br /&gt;
*Amygdala (Emotions)&lt;br /&gt;
*Spinal cord (Peripheral sensing)&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10578</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10578"/>
		<updated>2007-11-01T15:29:22Z</updated>

		<summary type="html">&lt;p&gt;Mr406: /* Tetrahydrocannabinol */&lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC, Dronabinol, Marinol, Deltanyne, Tetranabinex, Compassia, delta9-THC, delta1-THC, delta(sup 1)-Thc,delta(sup 9)-Thc.&amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==Introduction==&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocannabinol (commonly known as cannabis) is obtained by harvesting the resin of Cannabis sativa (marihuana, hashish). It is one of the oldest hallucigens in the world.It is a psychoactive compound, which triggers characteristic mood and perceptual changes in the user. There are many isomers, but the most active form is delta-9-tetrahydrocannabinol (THC), creating the most intense effects when used. &amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt; THC belongs to a sub-class of compounds called cannabinoids, which in turn belong to the class of molecules called terpenoids. Related to THC are [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Menthol menthol],[http://en.wikipedia.org/wiki/Turpentine turpentine] and camphor.&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|tetrahydrocannabinol 3D]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
==Effects on the brain==&lt;br /&gt;
&lt;br /&gt;
THC effects the brain by binding to receptors in the brain which promote the release of Acetyl Choline&amp;lt;ref&amp;gt;A. Pisanu, E. Acquas, S. Fenu and G. Di Chiara, Neuropharmacology, 2006, 50, 661-670. {{DOI|10.1016/j.neuropharm.2005.11.023}}&amp;lt;/ref&amp;gt; &lt;br /&gt;
and Dopamine. There are various cannabinoid G protein-coupled receptors in the form of CB1 and CB2 as well as unusual receptors GPR55 and GPR119 which are needed to explain some of the other unexplainable pharmalogical effects of cannabinoids such as THC &amp;lt;ref&amp;gt;A. J. Brown, Br J Pharmacol, 2007, 152, 567-575.{{DOI|10.1038/sj.bjp.0707481}}&amp;lt;/ref&amp;gt;. THC works to effect the brain in various ways as described next.&lt;br /&gt;
&lt;br /&gt;
THC can cause change in levels of cAMP which in turn effect hyperpolarization-activated cyclic nucleotide-gated channels which then effects the ability of communication of brain cells.&lt;br /&gt;
&lt;br /&gt;
&amp;lt;ref&amp;gt;Serendip: http://serendip.brynmawr.edu/bb/neuro/neuro04/web1/aejelonu.html&amp;lt;/ref&amp;gt;THC acts by binding to cannabinoid receptors and then causing the release or uptake of various neurotransmitters. Cannabinoid receptors are responsible for the control of thought, memory, concentration and movement. In the hippocampus there are a lot of THC receptors and the way information is taken in by this part of the brain is effected. The hippocampus is responsible for memory and so THC can lead to short term memory problems. Also the binding to the receptors causes damage to the nerve cells and so decreases their activities.  &lt;br /&gt;
&lt;br /&gt;
THC can also effects the emotions of the consumer by effecting the brains limbic system which controls behaviour and emotions. It is responsible for the characteristic laughing and/or paranoia associated with the intake of cannabis. Taking 14mg or more of THC at one time can have dramatic effects on the emotions and bodily functions of the person involved.&lt;br /&gt;
&lt;br /&gt;
THC also gives the &amp;quot;feel good factor&amp;quot; which is made by the interaction of drug with the part of the brain which acts on reward. To do this the THC encourages the release of dopamine by the brain cells.&lt;br /&gt;
Coordination is effected by the tetrahydrocannabinol by its binding with the receptors in the brain (cerebellum and basal ganglia). This has not been proven to cause accidents because any found THC levels in people that cause accidents are also usually accompanied with alcohol as well.&lt;br /&gt;
&lt;br /&gt;
Brain areas in which cannabinoid receptors are abundant and hence effect to some extent:&amp;lt;ref&amp;gt;National Institute of Drug Abuse: http://www.nida.nih.gov/ResearchReports/Marijuana/Marijuana3.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
*Cerebellum (movement)&lt;br /&gt;
*Hippocampus (Memory)&lt;br /&gt;
*Cerebral cortex (Higher thought)&lt;br /&gt;
*Nucleus accumbens (Rewards)&lt;br /&gt;
*Basal ganglia (control of movement)&lt;br /&gt;
&lt;br /&gt;
Less abundant(but still present) in:&lt;br /&gt;
&lt;br /&gt;
*Hypothalamus (Regulation)&lt;br /&gt;
*Amygdala (Emotions)&lt;br /&gt;
*Spinal cord (Peripheral sensing)&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10542</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10542"/>
		<updated>2007-11-01T13:55:46Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC, Dronabinol, Marinol, Deltanyne, Tetranabinex, Compassia, delta9-THC, delta1-THC, delta(sup 1)-Thc,delta(sup 9)-Thc.&amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==Introduction==&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocannabinol (commonly known as cannabis) is obtained by harvesting the resin of Cannabis sativa (marihuana, hashish). It is one of the oldest hallucigens in the world.It is a psychoactive compound, which triggers characteristic mood and perceptual changes in the user. There are many isomers, but the most active form is delta-9-tetrahydrocannabinol (THC), creating the most intense effects when used. &amp;lt;ref&amp;gt;http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16078&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|tetrahydrocannabinol 3D]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
==Effects on the brain==&lt;br /&gt;
&lt;br /&gt;
THC effects the brain by binding to receptors in the brain which promote the release of Acetyl Choline and Dopamine.&lt;br /&gt;
&amp;lt;ref&amp;gt;A. Pisanu, E. Acquas, S. Fenu and G. Di Chiara, Neuropharmacology, 2006, 50, 661-670. {{DOI|10.1016/j.neuropharm.2005.11.023  }}&amp;lt;/ref&amp;gt; THC acts by binding to cannabinoid receptors and then causing the release or uptake of various neurotransmitters. Cannabinoid receptors are responsible for the control of thought, memory, concentration and movement. In the hippocampus there are a lot of THC receptors and the way information is taken in by this part of the brain is effected. The hippocampus is responsible for memory and so THC can lead to short term memory problems. Also the binding to the receptors causes damage to the nerve cells and so decreases their activities.  &lt;br /&gt;
&lt;br /&gt;
THC can also effects the emotions of the consumer by effecting the brains limbic system which controls behaviour and emotions. It is responsible for the characteristic laughing and/or paranoia associated with the intake of cannabis. Taking 14mg or more of THC at one time can have dramatic effects on the emotions and bodily functions of the person involved.&lt;br /&gt;
&lt;br /&gt;
THC also gives the &amp;quot;feel good factor&amp;quot; which is made by the interaction of drug with the part of the brain which acts on reward. To do this the THC encourages the release of dopamine by the brain cells.&lt;br /&gt;
Coordination is effected by the tetrahydrocannabinol by its binding with the receptors in the brain (cerebellum and basal ganglia). This has not been proven to cause accidents because any found THC levels in people that cause accidents are also usually accompanied with alcohol as well.&lt;br /&gt;
&lt;br /&gt;
Brain areas in which cannabinoid receptors are abundant:.&amp;lt;ref&amp;gt;National Institute of Drug Abuse: http://www.nida.nih.gov/ResearchReports/Marijuana/Marijuana3.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
*Cerebellum (movement)&lt;br /&gt;
*Hippocampus (Memory)&lt;br /&gt;
*Cerebral cortex (Higher thought)&lt;br /&gt;
*Nucleus accumbens (Rewards)&lt;br /&gt;
*Basal ganglia (control of movement)&lt;br /&gt;
&lt;br /&gt;
less abundant in:&lt;br /&gt;
&lt;br /&gt;
*Hypothalamus (Regulation)&lt;br /&gt;
*Amygdala (Emotions)&lt;br /&gt;
*Spinal cord (Peripheral sensing)&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10379</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10379"/>
		<updated>2007-10-30T15:21:14Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|tetrahydrocannabinol 3D]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10377</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10377"/>
		<updated>2007-10-30T15:18:32Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt;  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
==Terbutaline Sulphate==&lt;br /&gt;
==Structure==&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
==Crystal Structure==&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;TESU.cif&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;TESU.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma &amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness &amp;lt;ref&amp;gt;http://www.drugs.com/pdr/terbutaline-sulfate.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &amp;lt;ref&amp;gt;Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 &lt;br /&gt;
Effenberger, F.; Jager, J.&lt;br /&gt;
J. Org. Chem.; (Article); 1997; 62(12); 3867-3873.  DOI: 10.1021/jo970032d &amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
&lt;br /&gt;
[[Image:Bricanyl_Terbutaline_sulphate.JPG|center|350px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10376</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10376"/>
		<updated>2007-10-30T15:16:59Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt;  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
==Terbutaline Sulphate==&lt;br /&gt;
==Structure==&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
==Crystal Structure==&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;TESU.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma &amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness &amp;lt;ref&amp;gt;http://www.drugs.com/pdr/terbutaline-sulfate.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &amp;lt;ref&amp;gt;Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 &lt;br /&gt;
Effenberger, F.; Jager, J.&lt;br /&gt;
J. Org. Chem.; (Article); 1997; 62(12); 3867-3873.  DOI: 10.1021/jo970032d &amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
&lt;br /&gt;
[[Image:Bricanyl_Terbutaline_sulphate.JPG|center|350px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10375</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10375"/>
		<updated>2007-10-30T15:15:46Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt;  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
==Terbutaline Sulphate==&lt;br /&gt;
==Structure==&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma &amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness &amp;lt;ref&amp;gt;http://www.drugs.com/pdr/terbutaline-sulfate.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &amp;lt;ref&amp;gt;Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 &lt;br /&gt;
Effenberger, F.; Jager, J.&lt;br /&gt;
J. Org. Chem.; (Article); 1997; 62(12); 3867-3873.  DOI: 10.1021/jo970032d &amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
&lt;br /&gt;
[[Image:Bricanyl_Terbutaline_sulphate.JPG|center|350px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10374</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10374"/>
		<updated>2007-10-30T15:13:41Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;==Terbutaline Sulphate==&lt;br /&gt;
{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt;  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma &amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness &amp;lt;ref&amp;gt;http://www.drugs.com/pdr/terbutaline-sulfate.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &amp;lt;ref&amp;gt;Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 &lt;br /&gt;
Effenberger, F.; Jager, J.&lt;br /&gt;
J. Org. Chem.; (Article); 1997; 62(12); 3867-3873.  DOI: 10.1021/jo970032d &amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
&lt;br /&gt;
[[Image:Bricanyl_Terbutaline_sulphate.JPG|center|350px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=File:TESU.cif&amp;diff=10373</id>
		<title>File:TESU.cif</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=File:TESU.cif&amp;diff=10373"/>
		<updated>2007-10-30T15:11:53Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10369</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10369"/>
		<updated>2007-10-30T15:03:23Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &amp;lt;ref&amp;gt;http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4764&amp;lt;/ref&amp;gt;&lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10366</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10366"/>
		<updated>2007-10-30T14:57:56Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10361</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10361"/>
		<updated>2007-10-30T14:21:49Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [http://nepenthes.lycaeum.org/Drugs/THC/msds.html MSDS] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocabbinol is the active biological ingredient in cannabis&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10360</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10360"/>
		<updated>2007-10-30T14:15:46Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocabbinol is the active biological ingredient in cannabis&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-36 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10358</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10358"/>
		<updated>2007-10-30T14:13:55Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| HP8225000&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocabbinol is the active biological ingredient in cannabis&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-37. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-37 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10356</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10356"/>
		<updated>2007-10-30T14:03:13Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| Extremely Flammable &lt;br /&gt;
Reacts violently with water &lt;br /&gt;
&lt;br /&gt;
Contact with water liberates extremely flammable gases &lt;br /&gt;
&lt;br /&gt;
Explosive when mixed with oxidizing substances &lt;br /&gt;
&lt;br /&gt;
Spontaneously flammable in air &lt;br /&gt;
&lt;br /&gt;
In use may form flammable/explosive vapor-air mixture &lt;br /&gt;
&lt;br /&gt;
May form explosive peroxides &lt;br /&gt;
&lt;br /&gt;
Harmful by inhalation &lt;br /&gt;
&lt;br /&gt;
Harmful in contact with skin &lt;br /&gt;
&lt;br /&gt;
Harmful if swallowed &lt;br /&gt;
&lt;br /&gt;
Toxic by inhalation &lt;br /&gt;
&lt;br /&gt;
Toxic in contact with skin &lt;br /&gt;
&lt;br /&gt;
Toxic if swallowed &lt;br /&gt;
&lt;br /&gt;
Danger of very serious irreversible effects &lt;br /&gt;
 &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| {{{RTECS}}}&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocabbinol is the active biological ingredient in cannabis&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-37. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-37 of the Original document. It is a long synthesis which has emphasis on the stereochemistry of the final product. This is because the drug has to interact with the body to have a desired effect and since the receptors are made out of chiral amino acids it must have the correct stereochemistry to interact.&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10353</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10353"/>
		<updated>2007-10-30T13:48:02Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| {{{Hazards}}} &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| {{{RTECS}}}&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|400px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocabbinol is the active biological ingredient in cannabis&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-37 of the Original document.&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10352</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10352"/>
		<updated>2007-10-30T13:45:52Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| {{{Hazards}}} &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| {{{RTECS}}}&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|350px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocabbinol is the active biological ingredient in cannabis&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
&lt;br /&gt;
There is a long synthesis root for Tetrahydrocannabinol which can be found at: [http://v3.espacenet.com/origdoc?DB=EPODOC&amp;amp;IDX=WO2005100333&amp;amp;F=0&amp;amp;QPN=WO2005100333 Synthesis]&amp;lt;ref&amp;gt;Patent: Cabaj John E et al. Methods and Intermediates for the synthesis of Delta-9 Tetrahydrocannabinol, Pub no. WO2005100333, 30-36. (find document link in article)&amp;lt;/ref&amp;gt;  Pages 30-37 of the Original document.&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10346</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10346"/>
		<updated>2007-10-30T13:38:14Z</updated>

		<summary type="html">&lt;p&gt;Mr406: /* Tetrahydrocannabinol */&lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| {{{Hazards}}} &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| {{{RTECS}}}&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|350px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
Tetrahydrocabbinol is the active biological ingredient in cannabis&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10345</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10345"/>
		<updated>2007-10-30T13:36:22Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| {{{Hazards}}} &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| {{{RTECS}}}&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Thc_pdb.gif|center|350px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=File:Thc_pdb.gif&amp;diff=10344</id>
		<title>File:Thc pdb.gif</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=File:Thc_pdb.gif&amp;diff=10344"/>
		<updated>2007-10-30T13:35:10Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10343</id>
		<title>It07:Tetrahydrocannabinol</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Tetrahydrocannabinol&amp;diff=10343"/>
		<updated>2007-10-30T13:34:44Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;=Tetrahydrocannabinol=&lt;br /&gt;
&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --&amp;gt;&lt;br /&gt;
&amp;lt;/noinclude&amp;gt;{| class=&amp;quot;toccolours&amp;quot; border=&amp;quot;1&amp;quot; style=&amp;quot;float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px&amp;quot;&lt;br /&gt;
! {{chembox header}} | {{PAGENAME}} &amp;lt;!-- replace if not identical with the article name --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| align=&amp;quot;center&amp;quot; colspan=&amp;quot;2&amp;quot; bgcolor=&amp;quot;#ffffff&amp;quot; | [[Image:THC.png]] &amp;lt;!-- replace if not identical with the pagename --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | General&lt;br /&gt;
|- &lt;br /&gt;
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]&lt;br /&gt;
| (−)-(6aR,10aR)-6,6,9-trimethyl-&lt;br /&gt;
3-pentyl-6a,7,8,10a-tetrahydro-&lt;br /&gt;
6H-benzo[c]chromen-1-ol&lt;br /&gt;
|-&lt;br /&gt;
| Other names&lt;br /&gt;
| THC&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]&lt;br /&gt;
| C&amp;lt;sub&amp;gt;21&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;30&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] &amp;lt;!-- mostly for organic compounds, omit otherwise --&amp;gt;&lt;br /&gt;
| CC1=C[C@]2([H])[C@@](C(C)(C) OC3=C2C(O)=CC(CCCCC)=C3)([H])CC1&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]&lt;br /&gt;
| 314.45 gmol&amp;lt;sup&amp;gt;-1&amp;lt;/sup&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Appearance&lt;br /&gt;
| &lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]&lt;br /&gt;
| 1972-08-3,  3556-79-4,  6087-73-6,  6465-30-1,  16849-50-6,  17766-02-8,  26906-54-7,  43009-38-7,  69855-10-3&lt;br /&gt;
&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Properties&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Density Density] &amp;amp; [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]&lt;br /&gt;
| {{{Density}}} g/cm³ &amp;lt;!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]&lt;br /&gt;
| {{{Sol_Water}}} g/100 ml (25°C) &amp;lt;!--  at least put miscible with, not soluble in --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
&amp;lt;!-- | Other solvents e.g. [[ethanol]], [[acetone]] --&amp;gt;&lt;br /&gt;
&amp;lt;!-- | solubility info on other solvents --&amp;gt;&lt;br /&gt;
&amp;lt;!-- |- --&amp;gt;&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Melting_point Melting point]&lt;br /&gt;
| {{{Mp}}} K &amp;lt;!-- (mention any decomposition) --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]&lt;br /&gt;
| 155-157°C {{DOI|10.1021/ja01062a046}} &amp;lt;ref&amp;gt;Y. Gaoni and R. Mechoulam, J. Am. Chem. Soc., 1964, 86, 1646-1647.&amp;lt;/ref&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;a&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not an acid or a base.  If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKa}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p&#039;&#039;K&#039;&#039;&amp;lt;sub&amp;gt;b&amp;lt;/sub&amp;gt;) &amp;lt;!-- omit if not a base. If several values, be clear --&amp;gt;&lt;br /&gt;
| {{{pKb}}}&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation &amp;lt;nowiki&amp;gt;[α]&amp;lt;/nowiki&amp;gt;&amp;lt;sub&amp;gt;D&amp;lt;/sub&amp;gt;] &amp;lt;!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --&amp;gt;&lt;br /&gt;
| {{{Rotation}}}°&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]&lt;br /&gt;
| {{{Viscosity}}} [[Poise|cP]] at 25°C &amp;lt;!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Structure&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] &amp;lt;!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) --&amp;gt;&lt;br /&gt;
| {{{Mol_Shape}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination&amp;lt;br /&amp;gt;geometry] &amp;lt;!-- for a metal complex or an ionic crystal, otherwise omit --&amp;gt;&lt;br /&gt;
| {{{Coordination}}} &amp;lt;!-- e.g. trigonal bipyramidal --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] &amp;lt;!-- omit if not a solid --&amp;gt;&lt;br /&gt;
| {{{Crystal_Structure}}} &amp;lt;!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention &amp;quot;close packed&amp;quot; or similar.  You may also cite what class it belongs to, e.g. [[Cadmium_chloride#Crystal_structure|CdCl&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]]  --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Dipole#Molecular_dipoles|Dipole moment]]&lt;br /&gt;
| {{{DM}}} [[Debye|D]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Hazards &amp;lt;!--  Summary only- MSDS entry provides more complete information --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Material safety data sheet|MSDS]]&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] &amp;lt;!-- please replace with proper link--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Main [[Worker safety and health|hazard]]s&lt;br /&gt;
| {{{Hazards}}} &amp;lt;!-- e.g. highly toxic, explosive, flammable, corrosive --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[NFPA 704]]&lt;br /&gt;
| {{{NFPA}}}&amp;lt;!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on &amp;quot;very dangerous&amp;quot; as default- adjust according to actual values --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| [[Flash point]]&lt;br /&gt;
| {{{Fp}}}°C&lt;br /&gt;
|-&lt;br /&gt;
| [[Risk and Safety Statements|R/S statement]]&lt;br /&gt;
| [[List of R-phrases|R]]: {{{R-S}}} &amp;lt;br /&amp;gt; [[List of S-phrases|S]]: ?&lt;br /&gt;
|-&lt;br /&gt;
| [[RTECS]] number&lt;br /&gt;
| {{{RTECS}}}&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]&lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and&amp;lt;br /&amp;gt;properties]] &lt;br /&gt;
| [http://en.wikipedia.org/wiki/Refractive_index &#039;&#039;n&#039;&#039;], [http://en.wikipedia.org/wiki/Dielectric_constant ε&amp;lt;sub&amp;gt;r&amp;lt;/sub&amp;gt;], etc. &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic&amp;lt;br /&amp;gt;data]] &lt;br /&gt;
| Phase behaviour&amp;lt;br /&amp;gt;Solid, liquid, gas &lt;br /&gt;
|-&lt;br /&gt;
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]&lt;br /&gt;
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]&lt;br /&gt;
|-&lt;br /&gt;
! {{chembox header}} | Related compounds&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|anion]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Other_anion}}} &amp;lt;!-- Put in related anions e.g, iron(II) fluoride &amp;amp; iron(II) bromide if compound is iron(II) chloride --&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Other [[Ion|cation]]s &amp;lt;!-- please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Ohter_cation}}} &amp;lt;!-- Put in other oxidation states of same element e.g. [[iron(III) chloride]], also for related metals such as [[manganese(II) chloride]], [[cobalt(II) chloride]], ruthenium(III) chloride--&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
| Related compounds &lt;br /&gt;
&amp;lt;!-- A miscellaneous heading - use for covalent inorganics;  e.g. for PCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; you would list PCl&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;, POCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PF&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, PBr&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;, NCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; and AsCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;. &lt;br /&gt;
Please omit if not applicable --&amp;gt;&lt;br /&gt;
| {{{Relative_Compounds}}}&lt;br /&gt;
|-&lt;br /&gt;
| {{chembox header}} | &amp;lt;small&amp;gt;Except where noted otherwise, data are given for&amp;lt;br /&amp;gt; materials in their [[standard state|standard state (at 25&amp;amp;nbsp;°C, 100&amp;amp;nbsp;kPa)]]&amp;lt;br /&amp;gt;[[wikipedia:Chemical infobox|Infobox disclaimer and references]]&amp;lt;/small&amp;gt;&lt;br /&gt;
|-&lt;br /&gt;
|}&lt;br /&gt;
{{Chem-Data_Structure}}&lt;br /&gt;
&lt;br /&gt;
==3D Structure==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Tetrahydrocannabinol&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;azure&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;200&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
    &amp;lt;jmolAppletButton&amp;gt;&lt;br /&gt;
       &amp;lt;title&amp;gt;Show Tetrahydrocannabinol in popup window&amp;lt;/title&amp;gt;&lt;br /&gt;
       &amp;lt;color&amp;gt;cyan&amp;lt;/color&amp;gt;&lt;br /&gt;
       &amp;lt;uploadedFileContents&amp;gt;Cannabis.PDB&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolAppletButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
[[Image:Bricanyl_Terbutaline_sulphate.JPG|center|350px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&lt;br /&gt;
==3D crystal structure (unit cell)==&lt;br /&gt;
&lt;br /&gt;
&#039;&#039;with (CH&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;N-CHO in lattice&#039;&#039;&lt;br /&gt;
&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;Pentahelicene&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;Cannabis.cif&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
&lt;br /&gt;
=References= &lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10229</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10229"/>
		<updated>2007-10-29T16:21:13Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;==Terbutaline Sulphate==&lt;br /&gt;
{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt;  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;[[Image:Bricanyl_Terbutaline_sulphate.JPG|center|350px|Bricanyl terbutaline sulphate inhaler]]&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma &amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness &amp;lt;ref&amp;gt;http://www.drugs.com/pdr/terbutaline-sulfate.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &amp;lt;ref&amp;gt;Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 &lt;br /&gt;
Effenberger, F.; Jager, J.&lt;br /&gt;
J. Org. Chem.; (Article); 1997; 62(12); 3867-3873.  DOI: 10.1021/jo970032d &amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=File:Bricanyl_Terbutaline_sulphate.JPG&amp;diff=10228</id>
		<title>File:Bricanyl Terbutaline sulphate.JPG</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=File:Bricanyl_Terbutaline_sulphate.JPG&amp;diff=10228"/>
		<updated>2007-10-29T16:18:09Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=File:Bricanyl_terbutaline_sulphate.JPG&amp;diff=10227</id>
		<title>File:Bricanyl terbutaline sulphate.JPG</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=File:Bricanyl_terbutaline_sulphate.JPG&amp;diff=10227"/>
		<updated>2007-10-29T16:16:40Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10183</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10183"/>
		<updated>2007-10-29T15:03:37Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;==Terbutaline Sulphate==&lt;br /&gt;
{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt;  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma &amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness &amp;lt;ref&amp;gt;http://www.drugs.com/pdr/terbutaline-sulfate.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &amp;lt;ref&amp;gt;Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 &lt;br /&gt;
Effenberger, F.; Jager, J.&lt;br /&gt;
J. Org. Chem.; (Article); 1997; 62(12); 3867-3873.  DOI: 10.1021/jo970032d &amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10180</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10180"/>
		<updated>2007-10-29T14:59:43Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;==Terbutaline Sulphate==&lt;br /&gt;
{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt; C24H40N2O10S  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma &amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness &amp;lt;ref&amp;gt;http://www.drugs.com/pdr/terbutaline-sulfate.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &amp;lt;ref&amp;gt;Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 &lt;br /&gt;
Effenberger, F.; Jager, J.&lt;br /&gt;
J. Org. Chem.; (Article); 1997; 62(12); 3867-3873.  DOI: 10.1021/jo970032d &amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10174</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10174"/>
		<updated>2007-10-29T14:43:53Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;==Terbutaline Sulphate==&lt;br /&gt;
{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt; C24H40N2O10S  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma &amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness &amp;lt;ref&amp;gt;http://www.drugs.com/pdr/terbutaline-sulfate.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &amp;lt;ref&amp;gt;http://pubs.acs.org/cgi-bin/article.cgi/joceah/1997/62/i12/pdf/jo970032d.pdf&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10172</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10172"/>
		<updated>2007-10-29T14:40:48Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;==Terbutaline Sulphate==&lt;br /&gt;
{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt; C24H40N2O10S  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma &amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness &amp;lt;ref&amp;gt;http://www.drugs.com/pdr/terbutaline-sulfate.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10166</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10166"/>
		<updated>2007-10-29T14:34:43Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;==Terbutaline Sulphate==&lt;br /&gt;
{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt; C24H40N2O10S  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&amp;lt;ref&amp;gt;http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100002557.html&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma&lt;br /&gt;
&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
&lt;br /&gt;
&amp;lt;references/&amp;gt;&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10156</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10156"/>
		<updated>2007-10-29T14:22:45Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;==Terbutaline Sulphate==&lt;br /&gt;
{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt; C24H40N2O10S  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma&lt;br /&gt;
&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
&lt;br /&gt;
[[Image:Synthesis.png|center|350px|synthesis of terbutaline sulphate]]&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10153</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10153"/>
		<updated>2007-10-29T14:19:45Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;==Terbutaline Sulphate==&lt;br /&gt;
{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt; C24H40N2O10S  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
     &amp;lt;title&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/title&amp;gt;&amp;lt;color&amp;gt;black&amp;lt;/color&amp;gt;&lt;br /&gt;
     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
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 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma&lt;br /&gt;
&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
{| border=&amp;quot;1&amp;quot;&lt;br /&gt;
|-&lt;br /&gt;
|+ &#039;&#039;Synthesis of terbutaline sulphate&#039;&#039;&lt;br /&gt;
![[Image:Synthesis.png|250px|{{Cholesterol}}]]&lt;br /&gt;
|-&lt;br /&gt;
!&amp;lt;sub&amp;gt;http://pharmalicensing.com/.../1128004281_433bfab90eaa8.JPG&amp;lt;/sub&amp;gt;&lt;br /&gt;
|}&lt;br /&gt;
[[Image:Ritter_Reaction_Scheme.png|center|350px|The Ritter reaction]]&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
	<entry>
		<id>https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10150</id>
		<title>It07:Terbutaline Sulphate</title>
		<link rel="alternate" type="text/html" href="https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Terbutaline_Sulphate&amp;diff=10150"/>
		<updated>2007-10-29T14:15:59Z</updated>

		<summary type="html">&lt;p&gt;Mr406: &lt;/p&gt;
&lt;hr /&gt;
&lt;div&gt;==Terbutaline Sulphate==&lt;br /&gt;
{{Drug-Box |&lt;br /&gt;
| Box_Name = Terbutaline Sulphate&lt;br /&gt;
| ImageFile = Terbutaline_sulphate.png &lt;br /&gt;
| IUPACName =  tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate&lt;br /&gt;
| OtherName = Bricanyl&lt;br /&gt;
| CAS_No = {{{23031-32-5}}}&lt;br /&gt;
| ATC_Code = [http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03AC03 R03AC03][http://www.whocc.no/atcddd/indexdatabase/index.php?query=R03CC03 R03CC03]&lt;br /&gt;
| PubChem = 36120&lt;br /&gt;
| SMILES = CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C)&lt;br /&gt;
[NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-&lt;br /&gt;
| Formula =(C&amp;lt;sub&amp;gt;12&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;20&amp;lt;/sub&amp;gt;NO&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt; SO&amp;lt;sub&amp;gt;4&amp;lt;/sub&amp;gt; C24H40N2O10S  &lt;br /&gt;
| MolarMass = 548.6468 &lt;br /&gt;
| Metabolism = GI tract (oral), liver; CYP450: unknown&lt;br /&gt;
| Half_life = urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h&lt;br /&gt;
| Pregnancy_cat = B&lt;br /&gt;
| Legal_status = [http://en.wikipedia.org/wiki/Prescription_drug POM]&lt;br /&gt;
| Routes = SQ, Oral, Inhaled&lt;br /&gt;
}}&lt;br /&gt;
&amp;lt;noinclude&amp;gt;&lt;br /&gt;
&amp;lt;jmol&amp;gt;&lt;br /&gt;
  &amp;lt;jmolApplet&amp;gt;&lt;br /&gt;
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     &amp;lt;size&amp;gt;300&amp;lt;/size&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;zoom 300; cpk -25;dots on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;uploadedFileContents&amp;gt;mo_terbutaline_sulphate.pdb&amp;lt;/uploadedFileContents&amp;gt;&lt;br /&gt;
  &amp;lt;/jmolApplet&amp;gt;&lt;br /&gt;
 &lt;br /&gt;
 &lt;br /&gt;
    &amp;lt;jmolMenu&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Start spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin on&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;item&amp;gt;&amp;lt;text&amp;gt;Stop spinning&amp;lt;/text&amp;gt;&amp;lt;script&amp;gt;spin off&amp;lt;/script&amp;gt;&amp;lt;/item&amp;gt;&lt;br /&gt;
     &amp;lt;menuHeight&amp;gt;-1&amp;lt;/menuHeight&amp;gt;&lt;br /&gt;
   &amp;lt;/jmolMenu&amp;gt;&lt;br /&gt;
   &amp;lt;jmolButton&amp;gt;&lt;br /&gt;
     &amp;lt;script&amp;gt;console&amp;lt;/script&amp;gt;&lt;br /&gt;
     &amp;lt;text&amp;gt;open a console window&amp;lt;/text&amp;gt;&lt;br /&gt;
    &amp;lt;/jmolButton&amp;gt;&lt;br /&gt;
&amp;lt;/jmol&amp;gt;&lt;br /&gt;
Terbutaline sulphate belongs to a class of drugs known as [http://en.wikipedia.org/wiki/Beta2-adrenergic_receptor_agonist short acting beta 2 agonists]. It is a [http://en.wikipedia.org/wiki/Bronchodilator bronchodilator] These drugs work by acting on the lungs&#039; beta 2 receptors.  Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as [http://en.wikipedia.org/wiki/Asthma asthma], [http://en.wikipedia.org/wiki/Bronchitis bronchitis] and [http://en.wikipedia.org/wiki/Emphysema emphysema]. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.&lt;br /&gt;
&lt;br /&gt;
==Conditions where the drug is used==&lt;br /&gt;
[http://en.wikipedia.org/wiki/COPD Chronic obstructive pulmonary disease] (COPD)&lt;br /&gt;
&lt;br /&gt;
[http://en.wikipedia.org/wiki/Bronchospasm Bronchospasm] (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)&lt;br /&gt;
&lt;br /&gt;
Asthma&lt;br /&gt;
&lt;br /&gt;
==Side Effects==&lt;br /&gt;
Chest discomfort&lt;br /&gt;
&lt;br /&gt;
Breathing difficulty &lt;br /&gt;
&lt;br /&gt;
Dizziness &lt;br /&gt;
&lt;br /&gt;
Drowsiness &lt;br /&gt;
&lt;br /&gt;
Fast, irregular heartbeat&lt;br /&gt;
&lt;br /&gt;
Headache &lt;br /&gt;
&lt;br /&gt;
Increased heart rate &lt;br /&gt;
&lt;br /&gt;
Nausea &lt;br /&gt;
&lt;br /&gt;
Sweating&lt;br /&gt;
&lt;br /&gt;
Tremors&lt;br /&gt;
&lt;br /&gt;
Weakness&lt;br /&gt;
&lt;br /&gt;
==Synthesis==&lt;br /&gt;
To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent [http://en.wikipedia.org/wiki/Cyanohydrin cyanohydrin]. This done via a [http://en.wikipedia.org/wiki/Ritter_reaction Ritter reaction] to convert the [http://en.wikipedia.org/wiki/Nitrile nitrile] group into an N-alkyl [http://en.wikipedia.org/wiki/Amide amide]. &lt;br /&gt;
&lt;br /&gt;
When the N-alkyl amide has been made;  treat with [http://en.wikipedia.org/wiki/Sulphuric_acid sulphuric acid] to make terbutaline sulphate.&lt;br /&gt;
{| border=&amp;quot;1&amp;quot;&lt;br /&gt;
|-&lt;br /&gt;
|+ &#039;&#039;Synthesis of terbutaline sulphate&#039;&#039;&lt;br /&gt;
![[Image:Synthesis.png|250px|{{Cholesterol}}]]&lt;br /&gt;
|-&lt;br /&gt;
!&amp;lt;sub&amp;gt;http://pharmalicensing.com/.../1128004281_433bfab90eaa8.JPG&amp;lt;/sub&amp;gt;&lt;br /&gt;
|}&lt;/div&gt;</summary>
		<author><name>Mr406</name></author>
	</entry>
</feed>