JWH-164

JWH-164 is a synthetic cannabinoid receptor agonist from the naphthoylindole family. It has approximately equal affinity for the CB1 and CB2 receptors, with a Ki of 6.6 nM at CB1 and 6.9 nM at CB2. JWH-164 is a positional isomer of the related compound JWH-081, but with a methoxy group at the 7-position of the naphthyl ring, rather than the 4-position as in JWH-081. Its potency is intermediate between that of JWH-081 and its ring unsubstituted derivative JWH-018, demonstrating that substitution of the naphthyl 7-position can also result in increased cannabinoid receptor binding affinity.[1][2]

JWH-164
Legal status
Legal status
  • US: Schedule I
Identifiers
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H25NO2
Molar mass371.480 g·mol−1
3D model (JSmol)
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In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-164 are Schedule I Controlled Substances.[3]

References
  1. Huffman, John W.; Zengin, Gulay; Wu, Ming-Jung; Lu, Jianzhong; Hynd, George; Bushell, Kristen; Thompson, Alicia L.S.; Bushell, Simon; Tartal, Cindy; Hurst, Dow P.; Reggio, Patricia H.; Selley, Dana E.; Cassidy, Michael P.; Wiley, Jenny L.; Martin, Billy R. (2005). "Structure–activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB1 and CB2 receptors: Steric and electronic effects of naphthoyl substituents. New highly selective CB2 receptor agonists". Bioorganic & Medicinal Chemistry. 13: 89–112. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
  2. Huffman, J.; Padgett, L. (2005). "Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes". Current Medicinal Chemistry. 12 (12): 1395–1411. doi:10.2174/0929867054020864. PMID 15974991.
  3. 21 U.S.C. § 812: Schedules of controlled substances
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