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
IUPAC name
  • 7-Methoxynaphthalen-1-yl-(1-pentylindol-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H25NO2
Molar mass371.480 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCn(c4)c1ccccc1c4C(=O)c2cccc(cc3)c2cc3OC
InChI
  • InChI=1S/C25H25NO2/c1-3-4-7-15-26-17-23(20-10-5-6-12-24(20)26)25(27)21-11-8-9-18-13-14-19(28-2)16-22(18)21/h5-6,8-14,16-17H,3-4,7,15H2,1-2H3
  • Key:IJNSZBAEVYRFCH-UHFFFAOYSA-N
  (verify)

In the United States, all CB1 all receptor agonists of the 3-(1-naphthoyl)indole class, including JWH-164, are Schedule I Controlled Substances.[3]

References
  1. Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, et al. (January 2005). "Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists". Bioorganic & Medicinal Chemistry. 13 (1): 89–112. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
  2. Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry. 12 (12): 1395–411. doi:10.2174/0929867054020864. PMID 15974991.
  3. 21 U.S.C. § 812: Schedules of controlled substances
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