Chemistry:JWH-251

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JWH-251
JWH-251.svg
Names
Preferred IUPAC name
2-(2-Methylphenyl)-1-(1-pentyl-1H-indol-3-yl)ethan-1-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
Properties
C22H25NO
Molar mass 319.448 g·mol−1
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

JWH-251 (1-pentyl-3-(2-methylphenylacetyl)indole) is a synthetic cannabinoid from the phenylacetylindole family, which acts as a cannabinoid agonist with about five times selectivity for CB1 with a Ki of 29 nM and 146 nM at CB2. Similar to the related 2'-methoxy compound JWH-250, the 2'-chloro compound JWH-203, and the 2'-bromo compound JWH-249, JWH-251 has a phenylacetyl group in place of the naphthoyl ring used in most aminoalkylindole cannabinoid compounds.[1][2]

In the United States, all CB1 receptor agonists of the 3-phenylacetylindole class such as JWH-251 are Schedule I Controlled Substances.[3]

References

  1. "1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles". Bioorganic & Medicinal Chemistry Letters 15 (18): 4110–3. September 2005. doi:10.1016/j.bmcl.2005.06.008. PMID 16005223. 
  2. "Indoles and related compounds as cannabinoid ligands". Mini Reviews in Medicinal Chemistry 8 (4): 370–87. April 2008. doi:10.2174/138955708783955935. PMID 18473928. 
  3. 21 U.S.C. § 812: Schedules of controlled substances