JWH-203: Difference between revisions

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Updating {{drugbox}} (changes to watched fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'DrugBank_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID
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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
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| verifiedrevid = 451554581
| Watchedfields = changed
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| IUPAC_name = 2-(2-Chlorophenyl)-1-(1-pentylindol-3-yl)ethanone
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| verifiedrevid = 441470884
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| image = JWH-203.svg
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| IUPAC_name = 2-(2-chlorophenyl)-1-(1-pentylindol-3-yl)ethanone
| width = 150
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| image = JWH-203_structure.png


<!--Clinical data-->
<!--Clinical data-->
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| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA = Schedule II
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_UK = Class B
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_US = Schedule I
| legal_DE = Anlage II
| legal_status = I-N (Poland)<ref>{{cite web | title = Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 ) | url = http://isap.sejm.gov.pl/DetailsServlet?id = WDU20111050614 | publisher = Internetowy System Aktów Prawnych | accessdate = 17 June 2011}}</ref>
| legal_status = I-N (Poland)<ref>{{cite web | title = Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 ) | url = http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614 | publisher = Internetowy System Aktów Prawnych | access-date = 17 June 2011 }}</ref>


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 864445-54-5
| CAS_number = 864445-54-5
| CAS_supplemental = (JWH-203)<BR>864445-55-6 (JWH-204)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 52CP80V8FY
| PubChem = 44397500
| PubChem = 44397500
| ChemSpiderID = 23256082


<!--Chemical data-->
<!--Chemical data-->
| C=21 | H=22 | Cl=1 | N=1 | O=1
| C=21 | H=22 | Cl=1 | N=1 | O=1
| molecular_weight = 339.858 g/mol
| smiles = Clc2ccccc2CC(=O)c1cn(CCCCC)c3ccccc13
| smiles = Clc2ccccc2CC(=O)c1cn(CCCCC)c3ccccc13
| StdInChI = 1S/C21H22ClNO/c1-2-3-8-13-23-15-18(17-10-5-7-12-20(17)23)21(24)14-16-9-4-6-11-19(16)22/h4-7,9-12,15H,2-3,8,13-14H2,1H3
| StdInChIKey = YDINKDBAZJOSLV-UHFFFAOYSA-N
}}
}}


'''JWH-203''' ('''1-pentyl-3-(2-chlorophenylacetyl)indole''') is an [[analgesic]] chemical from the [[phenylacetylindole]] family, which acts as a [[cannabinoid]] [[agonist]] with approximately equal affinity at both the [[Cannabinoid receptor 1|CB<sub>1</sub>]] and [[Cannabinoid receptor 2 (macrophage)|CB<sub>2</sub>]] receptors, having a [[Dissociation constant|K<sub>i</sub>]] of 8.0nM at CB<sub>1</sub> and 7.0nM at CB<sub>2</sub>. Similar to the related 2'-[[methoxy]] compound [[JWH-250]], the 2'-[[bromo]] compound [[JWH-249]], and the 2'-[[methyl]] compound [[JWH-251]], JWH-203 has a [[phenyl]][[acetyl]] group in place of the [[naphthoyl]] ring used in most [[amino]][[alkyl]][[indole]] cannabinoid compounds, and is the most potent compound found in the phenylacetyl group.<ref>{{cite journal | last1 = Huffman | first1 = JW | last2 = Szklennik | first2 = PV | last3 = Almond | first3 = A | last4 = Bushell | first4 = K | last5 = Selley | first5 = DE | last6 = He | first6 = H | last7 = Cassidy | first7 = MP | last8 = Wiley | first8 = JL | last9 = Martin | first9 = BR | title = 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles | journal = Bioorganic & medicinal chemistry letters | volume = 15 | issue = 18 | pages = 4110–3 | year = 2005 | pmid = 16005223 | author-separator =, | author-name-separator= | doi = 10.1016/j.bmcl.2005.06.008 }}</ref><ref>{{cite journal | last1 = Manera | first1 = C | last2 = Tuccinardi | first2 = T | last3 = Martinelli | first3 = A | title = Indoles and related compounds as cannabinoid ligands | journal = Mini reviews in medicinal chemistry | volume = 8 | issue = 4 | pages = 370–87 | year = 2008 | pmid = 18473928 | author-separator =, | author-name-separator= }}</ref> It was discovered by, and named after, Dr. [[John W. Huffman]].
'''JWH-203''' ('''1-pentyl-3-(2-chlorophenylacetyl)indole''') is an [[analgesic]] chemical from the [[phenylacetylindole]] family that acts as a [[cannabinoid]] [[agonist]] with approximately equal affinity at both the [[Cannabinoid receptor 1|CB<sub>1</sub>]] and [[Cannabinoid receptor 2 (macrophage)|CB<sub>2</sub>]] receptors, having a [[Dissociation constant|K<sub>i</sub>]] of 8.0&nbsp;nM at CB<sub>1</sub> and 7.0&nbsp;nM at CB<sub>2</sub>. It was originally discovered by, and named after, [[John W. Huffman]], but has subsequently been sold without his permission as an ingredient of [[synthetic cannabis]] smoking blends.<ref>{{cite journal | vauthors = Bononi M, Belgi P, Tateo F | title = Analytical data for identification of the Cannabimimetic Phenylacetylindole JWH-203 | journal = Journal of Analytical Toxicology | volume = 35 | issue = 6 | pages = 360–3 | date = July 2011 | pmid = 21740693 | doi = 10.1093/anatox/35.6.360 | url = https://air.unimi.it/bitstream/2434/159566/3/JWH%20203.pdf | doi-access = free }}</ref> Similar to the related 2'-[[methoxy]] compound [[JWH-250]], the 2'-[[bromine|bromo]] compound [[JWH-249]], and the 2'-[[methyl]] compound [[JWH-251]], JWH-203 has a [[phenyl]][[acetyl]] group in place of the [[naphthoyl]] ring used in most [[amino]][[alkyl]][[indole]] cannabinoid compounds, and has the strongest ''in vitro'' binding affinity for the cannabinoid receptors of any compound in the phenylacetyl group.<ref>{{cite journal | vauthors = Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, Cassidy MP, Wiley JL, Martin BR | display-authors = 6 | title = 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles | journal = Bioorganic & Medicinal Chemistry Letters | volume = 15 | issue = 18 | pages = 4110–3 | date = September 2005 | pmid = 16005223 | doi = 10.1016/j.bmcl.2005.06.008 }}</ref><ref>{{cite journal | vauthors = Manera C, Tuccinardi T, Martinelli A | title = Indoles and related compounds as cannabinoid ligands | journal = Mini Reviews in Medicinal Chemistry | volume = 8 | issue = 4 | pages = 370–87 | date = April 2008 | pmid = 18473928 | doi = 10.2174/138955708783955935 }}</ref><ref name="pmid21740693">{{cite journal | vauthors = Bononi M, Belgi P, Tateo F | title = Analytical data for identification of the Cannabimimetic Phenylacetylindole JWH-203 | journal = Journal of Analytical Toxicology | volume = 35 | issue = 6 | pages = 360–3 | date = July 2011 | pmid = 21740693 | doi = 10.1093/anatox/35.6.360 | url = https://air.unimi.it/bitstream/2434/159566/3/JWH%20203.pdf | doi-access = free }}</ref>


Unexpectedly despite its weaker CB<sub>1</sub> K<sub>i</sub> ''in vitro'', the [[2-methylindole]] derivative JWH-204 is actually more potent than JWH-203 in animal tests for cannabinoid activity, though it is still weaker than [[JWH-249]].<ref>{{cite journal | vauthors = Wiley JL, Marusich JA, Martin BR, Huffman JW | title = 1-Pentyl-3-phenylacetylindoles and JWH-018 share in vivo cannabinoid profiles in mice | journal = Drug and Alcohol Dependence | volume = 123 | issue = 1–3 | pages = 148–53 | date = June 2012 | pmid = 22127210 | pmc = 3294131 | doi = 10.1016/j.drugalcdep.2011.11.001 }}</ref>
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==References==

[[Image:JWH-204.svg|150px|thumb|left|JWH-204]]{{clear left}}

==Legal status==

In the United States, JWH-203 is a [[Schedule I Controlled Substance]].<ref>{{cite web | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf | title = Controlled Substances | publisher = [[Drug Enforcement Administration]] }}</ref>

As of October 2015, JWH-203 is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | access-date=1 October 2015 | archive-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | url-status=dead }}</ref>

== See also ==
* [[MN-25]]

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== References ==
{{Reflist}}
{{Reflist}}


{{Cannabinoids}}
{{Cannabinoids}}
{{Cannabinoid-stub}}
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{{Use dmy dates|date=September 2010}}


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{{Use dmy dates|date=August 2019}}
{{DEFAULTSORT:Jwh-203}}

[[Category:JWH cannabinoids]]
[[Category:JWH cannabinoids]]
[[Category:Phenylacetylindoles]]
[[Category:Phenylacetylindoles]]
[[Category:Organochlorides]]
[[Category:Chloroarenes]]
[[Category:Designer drugs]]
[[Category:CB1 receptor agonists]]
[[Category:CB2 receptor agonists]]
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