JWH-424

JWH-424
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B; US: Schedule I;
Identifiers
	IUPAC name 1-Pentyl-3-(8-bromo-1-naphthoyl)indole;
CAS Number	1366068-04-3 ;
PubChem CID	57458937;
ChemSpider	28645324;
UNII	O4Q3AIP6BJ;
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;
	(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 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]

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]

References

^ 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.
^ 21 U.S.C. § 812: Schedules of controlled substances

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[pmid22341572-1] 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

[1]

[2]

Legal status

Legal status	CA: Schedule II DE: NpSG (Industrial and scientific use only) UK: Class B US: Schedule I
Identifiers
IUPAC name 1-Pentyl-3-(8-bromo-1-naphthoyl)indole
CAS Number	1366068-04-3^Y
PubChem CID	57458937
ChemSpider	28645324
UNII	O4Q3AIP6BJ
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
(verify)

See also

References