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JWH-198

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
JWH-198
Legal status
Legal status
Identifiers
  • (1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methoxynaphthalen-1-ylmethanone
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC26H26N2O3
Molar mass414.505 g·mol−1
3D model (JSmol)
  • C4COCCN4CCn2cc(c5ccccc25)C(=O)c3c1ccccc1c(OC)cc3
  • InChI=1S/C26H26N2O3/c1-30-25-11-10-22(19-6-2-3-8-21(19)25)26(29)23-18-28(24-9-5-4-7-20(23)24)13-12-27-14-16-31-17-15-27/h2-11,18H,12-17H2,1H3 ☒N
  • Key:QWHSUXWDDKWTOG-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

JWH-198 is a drug from theaminoalkylindole andnaphthoylindole families which acts as acannabinoid receptoragonist. It was invented by the pharmaceutical company Sanofi-Winthrop in the early 1990s. JWH-198 has abinding affinity at the CB1 receptor of 10 nM, binding around four times more tightly than the parent compoundJWH-200, which has no substitution on the naphthoyl ring.[1] It has been used mainly inmolecular modelling of the cannabinoid receptors.[2][3]

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-198 areSchedule I Controlled Substances.[4]

See also

[edit]

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. ^Eissenstat MA, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, Gruett MD, Kumar V, Estep KG, Olefirowicz EM (Aug 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, Collantes ER, Welsh WJ, Subramaniam B, Howlett AC, Eissenstat MA, Ward SJ (Nov 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.
  4. ^21 U.S.C. § 812:Schedules of controlled substances
Phytocannabinoids
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AllostericCBRTooltip Cannabinoid receptorligands
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