JWH-098

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JWH-098
JWH-098.svg
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H27NO2
Molar mass385.507 g·mol−1
3D model (JSmol)
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JWH-098 is a synthetic cannabinoid receptor agonist from the naphthoylindole family. It is the indole 2-methyl derivative of a closely related compound JWH-081, but has markedly different affinity for the CB1 and CB2 receptors. While JWH-081 is around ten fold selective for CB1 over CB2, in JWH-098 this is reversed, and it is around four times weaker than JWH-081 at CB1 while being six times more potent at CB2, giving it a slight selectivity for CB2 overall. This makes JWH-098 a good example of how methylation of the indole 2-position in the naphthoylindole series tends to increase CB2 affinity, but often at the expense of CB1 binding.[1]

Legal status[edit]

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-098 are Schedule I Controlled Substances.[2]

JWH-098 is illegal in Russia,[3] Sweden,[4] and the UK,[5] although it is unclear whether it has any history of human use.

See also[edit]

References[edit]

  1. ^ Huffman, John W.; Zengin, Gulay; Wu, Ming-Jung; Lu, Jianzhong; Hynd, George; Bushell, Kristen; Thompson, Alicia L.S.; Bushell, Simon; Tartal, Cindy; Hurst, Dow P.; Reggio, Patricia H.; Selley, Dana E.; Cassidy, Michael P.; Wiley, Jenny L.; Martin, Billy R. (2005). "Structure–activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB1 and CB2 receptors: Steric and electronic effects of naphthoyl substituents. New highly selective CB2 receptor agonists". Bioorganic & Medicinal Chemistry. 13 (1): 89–112. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
  2. ^ 21 U.S.C. § 812: Schedules of controlled substances
  3. ^ "Постановление от 31 декабря 2009 г. № 1186 О внесении изменений в некоторые постановления Правительства Российской Федерации по вопросам, связанным с оборотом наркотических средств". Government.ru. Archived from the original on 2010-09-29. Retrieved 2010-09-09.
  4. ^ Svensk författningssamling
  5. ^ The Misuse of Drugs Act 1971 (Amendment) Order 2009 Archived 2009-11-03 at the Wayback Machine