JWH-424
{{Short description|Chemical compound}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 433533861
| IUPAC_name = 1-Pentyl-3-(8-bromo-1-naphthoyl)indole
| image = JWH-424.svg
| width = 150
| tradename =
| pregnancy_AU =
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| pregnancy_category =
| legal_AU =
| legal_CA = Schedule II
| legal_DE = NpSG
| legal_UK = Class B
| legal_US = Schedule I
| legal_status =
| routes_of_administration =
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| CAS_number = 1366068-04-3
| CAS_number_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O4Q3AIP6BJ
| ATC_prefix =
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| PubChem = 57458937
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID = 28645324
| C=24 | H=22 | Br=1 | N=1 | O=1
| smiles = c4cccc1c4n(CCCCC)cc1C(=O)c(c2c3Br)cccc2ccc3
| StdInChI = 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
| StdInChIKey = QXZYVJRMQVOOEQ-UHFFFAOYSA-N
}}
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.{{cite journal | vauthors = Wiley JL, Smith VJ, Chen J, Martin BR, Huffman JW | title = Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: steric and electronic effects of 4- and 8-halogenated naphthoyl substituents | journal = Bioorganic & Medicinal Chemistry | volume = 20 | issue = 6 | pages = 2067–81 | date = March 2012 | pmid = 22341572 | pmc = 3298571 | doi = 10.1016/j.bmc.2012.01.038 }}
In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-424 are Schedule I Controlled Substances.{{UnitedStatesCode2|21|812|Schedules of controlled substances}}