JWH-193

JWH-193

Systematic (IUPAC) name
(1-(2-morpholin-4-ylethyl)indol-3-yl)-4-methylnaphthalen-1-ylmethanone
Clinical data
Legal status	CA: Schedule II
Identifiers
CAS Number	133438-58-1
PubChem	CID 10250276
ChemSpider	8425762
UNII	WB1TIJ1IO9
Chemical data
Formula	C26H26N2O2
Molar mass	398.496 g/mol
SMILES c3cccc1c3c(ccc1C)C(=O)c5c2ccccc2n(c5)CCN4CCOCC4
InChI InChI=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 Key:ICKWPPYMDARCKJ-UHFFFAOYSA-N
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JWH-193 is a drug from the aminoalkylindole family 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 6nM, 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. 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.^[2][3]

6-Methyl-JWH-200

See also

• JWH-122
• JWH-198

References

1. Huffman JW, Padgett LW. Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes. Current Medicinal Chemistry, 2005; 12: 1395-1411.
2. Eissenstat MA, 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.
3. Shim JY, et al. (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.