:JWH-193
{{Short description|Chemical compound}}
{{Drugbox
| verifiedrevid = 451605875
| IUPAC_name = (1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methylnaphthalen-1-ylmethanone
| image = JWH-193.svg
| width = 150
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA = Schedule II
| legal_DE = NpSG
| legal_UK = Class B
| legal_US = Schedule I
| legal_status =
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 133438-58-1
| ATC_prefix =
| ATC_suffix =
| PubChem = 10250276
| UNII = WB1TIJ1IO9
| UNII_Ref = {{fdacite|correct|FDA}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID = 8425762
| C=26 | H=26 | N=2 | O=2
| smiles = c3cccc1c3c(ccc1C)C(=O)c5c2ccccc2n(c5)CCN4CCOCC4
| StdInChI = 1S/C26H26N2O2/c1-19-10-11-23(21-7-3-2-6-20(19)21)26(29)24-18-28(25-9-5-4-8-22(24)25)13-12-27-14-16-30-17-15-27/h2-11,18H,12-17H2,1H3
| StdInChIKey = ICKWPPYMDARCKJ-UHFFFAOYSA-N
}}
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,{{cite journal | vauthors = Huffman JW, Padgett LW | title = Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes | journal = Current Medicinal Chemistry | volume = 12 | issue = 12 | pages = 1395–411 | date = 2005 | pmid = 15974991 | doi = 10.2174/0929867054020864 }} 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.{{UnitedStatesCode2|21|812|Schedules of controlled substances}}
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.{{cite journal | vauthors = Eissenstat MA, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, Gruett MD, Kumar V, Estep KG, Olefirowicz EM | display-authors = 6 | title = Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics | journal = Journal of Medicinal Chemistry | volume = 38 | issue = 16 | pages = 3094–105 | date = August 1995 | pmid = 7636873 | doi = 10.1021/jm00016a013 }}{{cite journal | vauthors = Shim JY, Collantes ER, Welsh WJ, Subramaniam B, Howlett AC, Eissenstat MA, Ward SJ | title = Three-dimensional quantitative structure-activity relationship study of the cannabimimetic (aminoalkyl)indoles using comparative molecular field analysis | journal = Journal of Medicinal Chemistry | volume = 41 | issue = 23 | pages = 4521–32 | date = November 1998 | pmid = 9804691 | doi = 10.1021/jm980305c }}
Image:6-methyl-JWH-200.png{{clear-left}}
See also
References
{{Reflist}}
{{Cannabinoids}}
Category:4-Morpholinyl compounds
Category:CB1 receptor antagonists
{{cannabinoid-stub}}