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Updating {{drugbox}} (no changed fields - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Wikipedia:WikiProject Chemicals/Chembox validation|Chem/Dru
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{{short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
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| verifiedrevid = 407041372
| Watchedfields = changed
| IUPAC_name = 1-hexyl-2-phenyl-4-(1-naphthoyl)pyrrole
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| verifiedrevid = 443831499
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| image = JWH-147.svg
| IUPAC_name = (1-Hexyl-5-phenyl-1''H''-pyrrol-3-yl)-1-naphthalenyl-methanone
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| CAS_number = 914458-20-1
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| image = JWH-147.svg
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| ATC_prefix =

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| ATC_suffix =
<!--Clinical data-->
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| PubChem =
| tradename =
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| pregnancy_US = <!-- A / B / C / D / X -->
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| pregnancy_category =
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
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| legal_UK = class B<!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = Schedule I
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| legal_status = Illegal in Sweden
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| routes_of_administration =

<!--Pharmacokinetic data-->
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| bioavailability =
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| protein_bound =
| metabolism =
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| elimination_half-life =
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| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
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| CAS_number = 914458-20-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = MQ6N4B8QWE
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| ATC_prefix =
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| ATC_suffix =
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| PubChem =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| C=27|H=27|N=1|O=1
| ChemSpiderID = 23277882
| molecular_weight = 381.51 g/mol

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| smiles = c4ccccc4-c2cc(cn2CCCCCC)C(=O)c1cccc3c1cccc3

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| bioavailability =
<!--Chemical data-->
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| protein_bound =
| metabolism =
| C=27 | H=27 | N=1 | O=1
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| smiles = c4ccccc4-c2cc(cn2CCCCCC)C(=O)c1cccc3c1cccc3
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| elimination_half-life =
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
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| excretion =
| StdInChI = 1S/C27H27NO/c1-2-3-4-10-18-28-20-23(19-26(28)22-13-6-5-7-14-22)27(29)25-17-11-15-21-12-8-9-16-24(21)25/h5-9,11-17,19-20H,2-4,10,18H2,1H3
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
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| pregnancy_US = <!-- A / B / C / D / X -->
| StdInChIKey = FRMYAMAGHYHNKF-UHFFFAOYSA-N
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| pregnancy_category=
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
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| legal_status = Class B (UK), illegal in Sweden
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| routes_of_administration =
}}
}}


'''JWH-147''' is an [[analgesic]] drug used in scientific research, which acts as a [[cannabinoid]] agonist at both the [[cannabinoid receptor 1|CB<sub>1</sub>]] and [[cannabinoid receptor 2|CB<sub>2</sub>]] [[Receptor (biochemistry)|receptors]]. It is somewhat selective for the CB<sub>2</sub> subtype, with a [[Dissociation constant|Ki]] of 11.0nM at CB<sub>1</sub> vs 7.1nM at CB<sub>2</sub>.<ref>Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR. 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New high affinity ligands for the cannabinoid CB<sub>1</sub> and CB<sub>2</sub> receptors. ''Bioorganic & Medicinal Chemistry Letters'' 2006; 16:5432-5435.</ref> It was discovered and named after Dr. [[John W. Huffman]]. JWH-147 was banned in Sweden on 1st October 2010 as a hazardous good harmful to health, after being identified as an ingredient in "herbal" [[synthetic cannabis]] products.<ref>[http://www.riksdagen.se/webbnav/index.aspx?nid=3911&bet=1999:58 Swedish Code of Statutes Regulation (2010:1086).]</ref><ref>[http://www.lagboken.se/files/SFS/2010/101086.PDF Swedish Code of Statutes Regulation (2010:1086). (pdf)]</ref>
'''JWH-147''' is an [[analgesic]] drug used in scientific research, which acts as a [[cannabinoid]] [[agonist]] at both the [[cannabinoid receptor 1|CB<sub>1</sub>]] and [[cannabinoid receptor 2|CB<sub>2</sub>]] [[Receptor (biochemistry)|receptors]]. It is somewhat selective for the CB<sub>2</sub> subtype, with a [[Dissociation constant|K<sub>i</sub>]] of 11.0&nbsp;nM at CB<sub>1</sub> vs 7.1&nbsp;nM at CB<sub>2</sub>.<ref name="pmid16889960">{{cite journal | vauthors = Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR | title = 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB<sub>1</sub> and CB<sub>2</sub> receptors | journal = Bioorganic & Medicinal Chemistry Letters | volume = 16 | issue = 20 | pages = 5432–5 | date = October 2006 | pmid = 16889960 | doi = 10.1016/j.bmcl.2006.07.051 }}</ref> It was discovered and named after the renowned professor of organic chemistry [[John W. Huffman]].


==Legal status==
In the United States, CB<sub>1</sub> receptor agonists of the 3-(1-naphthoyl)pyrrole class such as JWH-147 are [[Schedule I Controlled Substance]]s.<ref>{{UnitedStatesCode2|21|812|Schedules of controlled substances}}</ref>

JWH-147 was banned in Sweden on 1 October 2010 as harmful to health, after being identified as an ingredient in "herbal" [[synthetic cannabis]] products.<ref>[http://www.riksdagen.se/webbnav/index.aspx?nid=3911&bet=1999:58 Swedish Code of Statutes Regulation (2010:1086).]</ref><ref>{{Cite web |url=http://www.lagboken.se/files/SFS/2010/101086.PDF |title=Swedish Code of Statutes Regulation (2010:1086). (pdf) |access-date=2011-01-10 |archive-url=https://web.archive.org/web/20110728111705/http://www.lagboken.se/files/SFS/2010/101086.PDF |archive-date=2011-07-28 |url-status=dead }}</ref>


==See also==
==See also==
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==References==
==References==
{{Reflist}}
<references/>


{{Cannabinoids}}
{{Cannabinoids}}
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{{cannabinoid-stub}}


[[Category:Naphthoylpyrroles]]
[[Category:CB1 receptor agonists]]
[[Category:JWH cannabinoids]]
[[Category:CB2 receptor agonists]]

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{{cannabinoid-stub}}
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