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JWH-149

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Chemical compound Pharmaceutical compound
JWH-149
Legal status
Legal status
Identifiers
IUPAC name
  • (4-Methyl-1-naphthalenyl)(2-methyl-1-pentyl-1H-indol-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H27NO
Molar mass369.508 g·mol
3D model (JSmol)
SMILES
  • c4cccc1c4c(ccc1C)C(=O)c3c2ccccc2n(c3C)CCCCC
InChI
  • InChI=1S/C26H27NO/c1-4-5-10-17-27-19(3)25(23-13-8-9-14-24(23)27)26(28)22-16-15-18(2)20-11-6-7-12-21(20)22/h6-9,11-16H,4-5,10,17H2,1-3H3
  • Key:JTJAMXUOXJGSCW-UHFFFAOYSA-N

JWH-149 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is the N-pentyl analog of JWH-148. It is a potent but only moderately selective ligand for the CB2 receptor, with a binding affinity of Ki = 0.73 ± 0.03 nM at this subtype, and more than six times selectivity over the CB1 subtype.

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-149 are Schedule I Controlled Substances.

See also

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. 21 U.S.C. § 812: Schedules of controlled substances
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