JWH-424

JWH-424

Systematic (IUPAC) name
1-pentyl-3-(8-bromo-1-naphthoyl)indole
Clinical data
Legal status	CA: Schedule II
Identifiers
ChemSpider	28645324
Chemical data
Formula	C24H22BrNO
Molar mass	420.341 g/mol
SMILES c4cccc1c4n(CCCCC)cc1C(=O)c(c2c3Br)cccc2ccc3
InChI InChI=1S/C24H22BrNO/c1-2-3-6-15-26-16-20(18-11-4-5-14-22(18)26)24(27)19-12-7-9-17-10-8-13-21(25)23(17)19/h4-5,7-14,16H,2-3,6,15H2,1H3 Key:QXZYVJRMQVOOEQ-UHFFFAOYSA-N
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JWH-424 is a drug from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB₁ and CB₂ receptors, but with moderate selectivity for CB₂, having a K_i of 5.44nM at CB₂ vs 20.9nM at CB₁. The heavier 8-iodo analogue is even more CB₂ selective, with its 2-methyl derivative having 40x selectivity for CB₂. However the 1-propyl homologues in this series showed much lower affinity at both receptors, reflecting a generally reduced affinity for the 8-substituted naphthoylindoles overall.^[1][2]

See also

• JWH-018
• JWH-398

References

1. Valerie Smith, John Huffman, Jenny Wiley and Billy Martin. EFFECTS OF HALOGEN SUBSTITUENTS UPON CB1 AND CB2 RECEPTOR AFFINITIES IN THE SERIES OF N-ALKYL-3-(8-HALO-1-NAPTHOYL)INDOLES. (2007) 17th Annual Symposium on the Cannabinoids, Burlington, Vermont, International Cannabinoid Research Society, Page 72.
2. John W. Huffman, et al. STRUCTURE-ACTIVITY RELATIONSHIPS AT THE CB1 AND CB2 RECEPTORS FOR 1-ALKYL-3-(1-NAPHTHOYL-4 AND 8-HALOGEN SUBSTITUTED) INDOLES (2009) 19th Annual Symposium on the Cannabinoids, Burlington, Vermont, International Cannabinoid Research Society, Page 2.