JWH-203

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JWH-203
JWH-203 structure.png
Systematic (IUPAC) name
2-(2-chlorophenyl)-1-(1-pentylindol-3-yl)ethanone
Clinical data
Legal status
  • I-N (Poland)[1]
Identifiers
CAS number 864445-54-5 YesY (JWH-203)
864445-55-6 (JWH-204)
ATC code ?
PubChem CID 44397500
ChemSpider 23256082
Chemical data
Formula C21H22ClNO 
Mol. mass 339.858 g/mol
 YesY (what is this?)  (verify)

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 CB1 and CB2 receptors, having a Ki of 8.0nM at CB1 and 7.0nM at CB2. It was originally discovered by, and named after, Dr. John W. Huffman, but has subsequently been sold without his permission as an ingredient of synthetic cannabis smoking blends.[2] 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 phenylacetyl group in place of the naphthoyl ring used in most aminoalkylindole cannabinoid compounds, and has the strongest in vitro binding affinity for the cannabinoid receptors of any compound in the phenylacetyl group.[3][4][5]

Unexpectedly despite its weaker CB1 Ki 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.[6]

JWH-204

See also[edit]

References[edit]

  1. ^ = WDU20111050614 "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. Retrieved 17 June 2011. 
  2. ^ "Analytical data for identification of the Cannabimimetic Phenylacetylindole JWH-203". J Anal Toxicol 35 (6): 360–3. July 2011. doi:10.1093/anatox/35.6.360. PMID 21740693. 
  3. ^ Huffman, JW, et al. (2005). "1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles". Bioorganic & Medicinal Chemistry Letters 15 (18): 4110–3. doi:10.1016/j.bmcl.2005.06.008. PMID 16005223. 
  4. ^ Manera, C; Tuccinardi, T; Martinelli, A (2008). "Indoles and related compounds as cannabinoid ligands". Mini reviews in medicinal chemistry 8 (4): 370–87. doi:10.2174/138955708783955935. PMID 18473928. 
  5. ^ Bononi M, Belgi P, Tateo F (2011). "Analytical data for identification of the Cannabimimetic Phenylacetylindole JWH-203". Journal of Analytical Toxicology 35 (6): 360–3. doi:10.1093/anatox/35.6.360. PMID 21740693. 
  6. ^ "1-Pentyl-3-phenylacetylindoles and JWH-018 share in vivo cannabinoid profiles in mice". Drug Alcohol Depend. November 2011. doi:10.1016/j.drugalcdep.2011.11.001. PMID 22127210.