From Wikipedia, the free encyclopedia
Chemical compound
JWH-193 is a drug from the
aminoalkylindole and
naphthoylindole families which acts as a
cannabinoid
receptor
agonist . It was invented by the pharmaceutical company Sanofi-Winthrop in the early 1990s. JWH-193 has a
binding affinity at the CB1 receptor of 6 nM, binding around seven times more tightly than the parent compound
JWH-200 ,
[1] though with closer to twice the potency of JWH-200 in activity tests.
In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-193 are
Schedule I Controlled Substances .
[2]
Related compounds
A structural isomer of JWH-193 with the methyl group on the indole ring instead of the naphthoyl ring, was also found to be of similarly increased potency over JWH-200.
[3]
[4]
6-Methyl-JWH-200
See also
References
^ Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry . 12 (12): 1395–411.
doi :
10.2174/0929867054020864 .
PMID
15974991 .
^
21 U.S.C.
§ 812 : Schedules of controlled substances
^ Eissenstat MA, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, et al. (August 1995). "Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics". Journal of Medicinal Chemistry . 38 (16): 3094–105.
doi :
10.1021/jm00016a013 .
PMID
7636873 .
^ Shim JY, Collantes ER, Welsh WJ, Subramaniam B, Howlett AC, Eissenstat MA, Ward SJ (November 1998). "Three-dimensional quantitative structure-activity relationship study of the cannabimimetic (aminoalkyl)indoles using comparative molecular field analysis". Journal of Medicinal Chemistry . 41 (23): 4521–32.
doi :
10.1021/jm980305c .
PMID
9804691 .
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)