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Chemical compound
JWH-196
Legal status
2-Methyl-3-(1-naphthalenylmethyl)-1-pentyl-1H -Indole
CAS Number
ChemSpider
UNII
Formula C 25 H 27 N
Molar mass 341.498 g·mol−1 3D model (
JSmol )
CCCCCn1c(c(c2c1cccc2)Cc3cccc4c3cccc4)C
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 Ki = 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]
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
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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
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Anticannabinoids (antagonists/inverse agonists/antibodies)