JWH-196

JWH-196
Legal status
Legal status	UK: Class B; US: Schedule I;
Identifiers
	IUPAC name 2-Methyl-3-(1-naphthalenylmethyl)-1-pentyl-1H-Indole;
CAS Number	619294-41-6;
ChemSpider	35303441;
UNII	M88JKX4UVV;
Chemical and physical data
Formula	C25H27N
Molar mass	341.498 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCn1c(c(c2c1cccc2)Cc3cccc4c3cccc4)C;
	InChI InChI=1S/C25H27N/c1-3-4-9-17-26-19(2)24(23-15-7-8-16-25(23)26)18-21-13-10-12-20-11-5-6-14-22(20)21/h5-8,10-16H,3-4,9,17-18H2,1-2H3; Key:LDTJKFUAZQDSQS-UHFFFAOYSA-N;

JWH-196 is a synthetic cannabinoid receptor ligand from the naphthylmethylindole family. It is the indole 2-methyl derivative of related compound JWH-175, and the carbonyl reduced analog of JWH-007. The binding affinity of JWH-196 for the CB₁ receptor is reported as K_i = 151 ± 18 nM.^[1]

In the United States, all CB₁ receptor agonists of the 3-(1-naphthylmethane)indole class such as JWH-196 are Schedule I Controlled Substances.^[2]

References

^ Huffman JW, Mabon R, Wu MJ, Lu J, Hart R, Hurst DP, Reggio PH, Wiley JL, Martin BR (2003). "3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB1 cannabinoid receptor". Bioorg. Med. Chem. 11 (4): 539–549. doi:10.1016/s0968-0896(02)00451-0. PMID 12538019. S2CID 29107765.
^ 21 U.S.C. § 812: Schedules of controlled substances

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[Huffman_2003-1] Huffman JW, Mabon R, Wu MJ, Lu J, Hart R, Hurst DP, Reggio PH, Wiley JL, Martin BR (2003). "3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB1 cannabinoid receptor". Bioorg. Med. Chem. 11 (4): 539–549. doi:10.1016/s0968-0896(02)00451-0. PMID 12538019. S2CID 29107765.

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

[1]

[2]

Legal status

Legal status	UK: Class B US: Schedule I
Identifiers
IUPAC name 2-Methyl-3-(1-naphthalenylmethyl)-1-pentyl-1H-Indole
CAS Number	619294-41-6
ChemSpider	35303441
UNII	M88JKX4UVV
Chemical and physical data
Formula	C₂₅H₂₇N
Molar mass	341.498 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCn1c(c(c2c1cccc2)Cc3cccc4c3cccc4)C
InChI InChI=1S/C25H27N/c1-3-4-9-17-26-19(2)24(23-15-7-8-16-25(23)26)18-21-13-10-12-20-11-5-6-14-22(20)21/h5-8,10-16H,3-4,9,17-18H2,1-2H3 Key:LDTJKFUAZQDSQS-UHFFFAOYSA-N

JWH-196

See also

References