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JWH-193

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
JWH-193
Legal status
Legal status
Identifiers
  • (1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methylnaphthalen-1-ylmethanone
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC26H26N2O2
Molar mass398.506 g·mol−1
3D model (JSmol)
  • c3cccc1c3c(ccc1C)C(=O)c5c2ccccc2n(c5)CCN4CCOCC4
  • 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
  (verify)

JWH-193 is a drug from theaminoalkylindole andnaphthoylindole families which acts as acannabinoidreceptoragonist. It was invented by the pharmaceutical company Sanofi-Winthrop in the early 1990s. JWH-193 has abinding affinity at the CB1 receptor of 6 nM, binding around seven times more tightly than the parent compoundJWH-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 areSchedule I Controlled Substances.[2]

Related compounds

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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

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References

[edit]
  1. ^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.
  2. ^21 U.S.C. § 812:Schedules of controlled substances
  3. ^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.
  4. ^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.
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