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JWH-193

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JWH-193
Identifiers
  • (1-(2-morpholin-4-ylethyl)indol-3-yl)-4-methylnaphthalen-1-ylmethanone
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H26N2O2
Molar mass398.496 g/mol g·mol−1
3D model (JSmol)
  • c3cccc1c3c(ccc1C)C(=O)c5c2ccccc2n(c5)CCN4CCOCC4

JWH-198 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-198 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]

See also

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, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, Gruett MD, Kumar V, Estep KG, Olefirowicz EM (1995). "Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics". Journal of Medicinal Chemistry. 38 (16): 3094–105. PMID 7636873. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. ^ Shim JY, Collantes ER, Welsh WJ, Subramaniam B, Howlett AC, Eissenstat MA, Ward SJ (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)