JWH-164

JWH-164
Legal status
Legal status	US: Schedule I;
Identifiers
	IUPAC name 7-Methoxynaphthalen-1-yl-(1-pentylindol-3-yl)methanone;
CAS Number	824961-61-7 ;
PubChem CID	45271217;
ChemSpider	24618407;
UNII	L3432L6CJJ;
CompTox Dashboard (EPA)	DTXSID70669880 ;
Chemical and physical data
Formula	C25H25NO2
Molar mass	371.480 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCn(c4)c1ccccc1c4C(=O)c2cccc(cc3)c2cc3OC;
	InChI InChI=1S/C25H25NO2/c1-3-4-7-15-26-17-23(20-10-5-6-12-24(20)26)25(27)21-11-8-9-18-13-14-19(28-2)16-22(18)21/h5-6,8-14,16-17H,3-4,7,15H2,1-2H3; Key:IJNSZBAEVYRFCH-UHFFFAOYSA-N;
	(verify)

JWH-164 is a synthetic cannabinoid receptor agonist from the naphthoylindole family. It has approximately equal affinity for the CB₁ and CB₂ receptors, with a K_i of 6.6 nM at CB₁ and 6.9 nM at CB₂. JWH-164 is a positional isomer of the related compound JWH-081, but with a methoxy group at the 7-position of the naphthyl ring, rather than the 4-position as in JWH-081. Its potency is intermediate between that of JWH-081 and its ring unsubstituted derivative JWH-018, demonstrating that substitution of the naphthyl 7-position can also result in increased cannabinoid receptor binding affinity.^[1]^[2]

In the United States, all CB₁ all receptor agonists of the 3-(1-naphthoyl)indole class, including JWH-164, are Schedule I Controlled Substances.^[3]

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.
^ Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry. 12 (12): 1395–411. doi:10.2174/0929867054020864. PMID 15974991.
^ 21 U.S.C. § 812: Schedules of controlled substances

[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] Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry. 12 (12): 1395–411. doi:10.2174/0929867054020864. PMID 15974991.

[3] 21 U.S.C. § 812: Schedules of controlled substances

[1]

[2]

[3]