JWH-148

JWH-148
Legal status
Legal status	US: Schedule I;
Identifiers
	IUPAC name (4-Methyl-1-naphthalenyl)(2-methyl-1-propyl-1H-indol-3-yl)methanone;
CAS Number	824955-99-9 ;
PubChem CID	45267819;
ChemSpider	24627234;
CompTox Dashboard (EPA)	DTXSID00669858 ;
Chemical and physical data
Formula	C24H23NO
Molar mass	341.454 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCN1C(=C(C2=CC=CC=C21)C(=O)C3=CC=C(C4=CC=CC=C43)C)C;
	InChI InChI=1S/C24H23NO/c1-4-15-25-17(3)23(21-11-7-8-12-22(21)25)24(26)20-14-13-16(2)18-9-5-6-10-19(18)20/h5-14H,4,15H2,1-3H3; Key:WRIOMNWYCFMMEY-UHFFFAOYSA-N;

JWH-148 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is the indole 2-methyl analog of JWH-120. It is a moderately selective ligand for the CB₂ receptor, with a binding affinity of K_i = 14.0 ± 1.0 nM at this subtype, and more than eight times selectivity over the CB₁ subtype.^[1]

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-148 are Schedule I Controlled Substances.^[2]

References

^ Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, et al. (January 2005). "Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists". Bioorganic & Medicinal Chemistry. 13 (1): 89–112. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
^ 21 U.S.C. § 812: Schedules of controlled substances

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[1] Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, et al. (January 2005). "Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists". Bioorganic & Medicinal Chemistry. 13 (1): 89–112. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.

[2] 21 U.S.C. § 812: Schedules of controlled substances

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See also

References