JWH-203

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 8.0 nM at CB1 and 7.0 nM at CB2. 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.[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]

JWH-203
Legal status
Legal status
  • CA: Schedule II
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
  • I-N (Poland)[1]
Identifiers
IUPAC name
  • 2-(2-Chlorophenyl)-1-(1-pentylindol-3-yl)ethanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.233.381
Chemical and physical data
FormulaC21H22ClNO
Molar mass339.86 g·mol−1
3D model (JSmol)
SMILES
  • Clc2ccccc2CC(=O)c1cn(CCCCC)c3ccccc13
InChI
  • InChI=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
  • Key:YDINKDBAZJOSLV-UHFFFAOYSA-N
  (verify)

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

In the United States, JWH-203 is a Schedule I Controlled Substance.[7]

As of October 2015, JWH-203 is a controlled substance in China.[8]

See also
  • MN-25

References
  1. "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. Bononi M, Belgi P, Tateo F (July 2011). "Analytical data for identification of the Cannabimimetic Phenylacetylindole JWH-203" (PDF). Journal of Analytical Toxicology. 35 (6): 360–3. doi:10.1093/anatox/35.6.360. PMID 21740693.
  3. Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, et al. (September 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 (April 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 (July 2011). "Analytical data for identification of the Cannabimimetic Phenylacetylindole JWH-203" (PDF). Journal of Analytical Toxicology. 35 (6): 360–3. doi:10.1093/anatox/35.6.360. PMID 21740693.
  6. Wiley JL, Marusich JA, Martin BR, Huffman JW (June 2012). "1-Pentyl-3-phenylacetylindoles and JWH-018 share in vivo cannabinoid profiles in mice". Drug and Alcohol Dependence. 123 (1–3): 148–53. doi:10.1016/j.drugalcdep.2011.11.001. PMC 3294131. PMID 22127210.
  7. "Controlled Substances" (PDF). Drug Enforcement Administration.
  8. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.

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