JWH-149

JWH-149
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B; US: Schedule I;
Identifiers
	IUPAC name (4-Methyl-1-naphthalenyl)(2-methyl-1-pentyl-1H-indol-3-yl)methanone;
CAS Number	548461-82-1 ;
PubChem CID	45267820;
ChemSpider	24627235;
UNII	AWD731Y25Z;
CompTox Dashboard (EPA)	DTXSID40203331 ;
Chemical and physical data
Formula	C26H27NO
Molar mass	369.508 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c4cccc1c4c(ccc1C)C(=O)c3c2ccccc2n(c3C)CCCCC;
	InChI InChI=1S/C26H27NO/c1-4-5-10-17-27-19(3)25(23-13-8-9-14-24(23)27)26(28)22-16-15-18(2)20-11-6-7-12-21(20)22/h6-9,11-16H,4-5,10,17H2,1-3H3; Key:JTJAMXUOXJGSCW-UHFFFAOYSA-N;

JWH-149 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is the N-pentyl analog of JWH-148. It is a potent but only moderately selective ligand for the CB₂ receptor, with a binding affinity of K_i = 0.73 ± 0.03 nM at this subtype, and more than six 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-149 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

[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 (4-Methyl-1-naphthalenyl)(2-methyl-1-pentyl-1H-indol-3-yl)methanone
CAS Number	548461-82-1^Y
PubChem CID	45267820
ChemSpider	24627235
UNII	AWD731Y25Z
CompTox Dashboard (EPA)	DTXSID40203331
Chemical and physical data
Formula	C₂₆H₂₇NO
Molar mass	369.508 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c4cccc1c4c(ccc1C)C(=O)c3c2ccccc2n(c3C)CCCCC
InChI InChI=1S/C26H27NO/c1-4-5-10-17-27-19(3)25(23-13-8-9-14-24(23)27)26(28)22-16-15-18(2)20-11-6-7-12-21(20)22/h6-9,11-16H,4-5,10,17H2,1-3H3 Key:JTJAMXUOXJGSCW-UHFFFAOYSA-N

JWH-149

See also

References

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