JWH-120

JWH-120
Legal status
Legal status	US: Schedule I;
Identifiers
	IUPAC name (4-Methyl-1-naphthalenyl)(1-propyl-1H-indol-3-yl)methanone;
CAS Number	824955-98-8 ;
PubChem CID	11461586;
ChemSpider	9636426;
UNII	J6M7L6J6PN;
ChEMBL	ChEMBL497811;
CompTox Dashboard (EPA)	DTXSID20466689 ;
Chemical and physical data
Formula	C23H21NO
Molar mass	327.427 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;
	InChI InChI=1S/C23H21NO/c1-3-14-24-15-21(19-10-6-7-11-22(19)24)23(25)20-13-12-16(2)17-8-4-5-9-18(17)20/h4-13,15H,3,14H2,1-2H3; Key:DUBUGSKBMMXSOU-UHFFFAOYSA-N;

JWH-120 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is the N-propyl analog of JWH-122. It is a potent and selective ligand for the CB₂ receptor, but a weaker ligand for the CB₁ receptor. It has a binding affinity of K_i = 6.1 ± 0.7 nM at the CB₂ subtype and 173 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-120 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