JWH-424

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 20.9 nM at CB₁. The heavier 8-iodo analogue is even more CB₂ selective, with its 2-methyl derivative having 40 times 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]

JWH-424

Legal status
Legal status	CA: Schedule II DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act US: Schedule I
Identifiers
IUPAC name 1-Pentyl-3-(8-bromo-1-naphthoyl)indole
CAS Number	1366068-04-3
PubChem CID	57458937
ChemSpider	28645324
CompTox Dashboard (EPA)	DTXSID50159855
Chemical and physical data
Formula	C24H22BrNO
Molar mass	420.350 g·mol^−1
3D model (JSmol)	Interactive image
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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In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-424 are Schedule I Controlled Substances.[2]

See also

• JWH-018
• JWH-398

References

1. Wiley JL, Smith VJ, Chen J, Martin BR, Huffman JW (March 2012). "Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: steric and electronic effects of 4- and 8-halogenated naphthoyl substituents". Bioorganic & Medicinal Chemistry. 20 (6): 2067–81. doi:10.1016/j.bmc.2012.01.038. PMC 3298571. PMID 22341572.
2. 21 U.S.C. § 812: Schedules of controlled substances