JWH-185

JWH-185
Legal status
Legal status	UK: Class B; US: Schedule I;
Identifiers
	IUPAC name 3-[(4-Methoxy-1-naphthalenyl)methyl]-1-pentyl-1H-indole;
CAS Number	619294-39-2;
ChemSpider	35303440;
UNII	T981O5QY3V;
Chemical and physical data
Formula	C25H27NO
Molar mass	357.497 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCn1cc(c2c1cccc2)Cc3ccc(c4c3cccc4)OC;
	InChI InChI=1S/C25H27NO/c1-3-4-9-16-26-18-20(22-11-7-8-13-24(22)26)17-19-14-15-25(27-2)23-12-6-5-10-21(19)23/h5-8,10-15,18H,3-4,9,16-17H2,1-2H3; Key:OTYBPWBZUDBUQS-UHFFFAOYSA-N;

JWH-185 is a synthetic cannabinoid receptor ligand from the naphthoylindole family. It is the carbonyl-reduced derivative of related compound JWH-081. The binding affinity of JWH-185 for the CB₁ receptor is reported as K_i = 17 ± 3 nM.^[1]

In the United States, all CB₁ receptor agonists of the 3-(1-naphthylmethane)indole class such as JWH-185 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 3-[(4-Methoxy-1-naphthalenyl)methyl]-1-pentyl-1H-indole
CAS Number	619294-39-2
ChemSpider	35303440
UNII	T981O5QY3V
Chemical and physical data
Formula	C₂₅H₂₇NO
Molar mass	357.497 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCn1cc(c2c1cccc2)Cc3ccc(c4c3cccc4)OC
InChI InChI=1S/C25H27NO/c1-3-4-9-16-26-18-20(22-11-7-8-13-24(22)26)17-19-14-15-25(27-2)23-12-6-5-10-21(19)23/h5-8,10-15,18H,3-4,9,16-17H2,1-2H3 Key:OTYBPWBZUDBUQS-UHFFFAOYSA-N

JWH-185

See also

References