JWH-148
JWH-148.png
Legal status
Legal status
Identifiers
  • (4-Methyl-1-naphthalenyl)(2-methyl-1-propyl-1H-indol-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H23NO
Molar mass341.454 g·mol−1
3D model (JSmol)
  • CCCN1C(=C(C2=CC=CC=C21)C(=O)C3=CC=C(C4=CC=CC=C43)C)C
  • InChI=1S/C24H23NO/c1-4-15-25-17(3)23(21-11-7-8-12-22(21)25)24(26)20-14-13-16(2)18-9-5-6-10-19(18)20/h5-14H,4,15H2,1-3H3
  • Key:WRIOMNWYCFMMEY-UHFFFAOYSA-N

JWH-148 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is the indole 2-methyl analog of JWH-120. It is a moderately selective ligand for the CB2 receptor, with a binding affinity of Ki = 14.0 ± 1.0 nM at this subtype, and more than eight times selectivity over the CB1 subtype.[1]

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-148 are Schedule I Controlled Substances.[2]

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