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Chemical compound
JWH-185
Legal status
3-[(4-Methoxy-1-naphthalenyl)methyl]-1-pentyl-1H -indole
CAS Number
ChemSpider
UNII
Formula C 25 H 27 N O
Molar mass 357.497 g·mol−1 3D model (
JSmol )
CCCCCn1cc(c2c1cccc2)Cc3ccc(c4c3cccc4)OC
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 Ki = 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]
See also
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
Phytocannabinoids (
comparison )
Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabiphorols Cannabinols Cannabitriols Cannabivarins Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols Delta-10-Tetrahydrocannabinols Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols
Eicosanoids
Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles
Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Tetramethylcyclo- propylindoles Others
Allosteric
CBR Tooltip Cannabinoid receptor
ligands
Endocannabinoid enhancers (inactivation inhibitors)
Anticannabinoids (antagonists/inverse agonists/antibodies)