JWH-424

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JWH-424
JWH-424.svg
Legal status
Legal status
Identifiers
  • 1-Pentyl-3-(8-bromo-1-naphthoyl)indole
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H22BrNO
Molar mass420.350 g·mol−1
3D model (JSmol)
  • c4cccc1c4n(CCCCC)cc1C(=O)c(c2c3Br)cccc2ccc3
  • 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
  (verify)

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 Ki 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]

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[edit]

References[edit]

  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