JWH-098

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]

JWH-098
Legal status
Legal status
Identifiers
IUPAC name
  • 4-Methoxynaphthalen-1-yl-(1-pentyl-2-methylindol-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H27NO2
Molar mass385.507 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCn(c1C)c2ccccc2c1C(=O)c(ccc3OC)c4ccccc34
InChI
  • InChI=1S/C26H27NO2/c1-4-5-10-17-27-18(2)25(22-13-8-9-14-23(22)27)26(28)21-15-16-24(29-3)20-12-7-6-11-19(20)21/h6-9,11-16H,4-5,10,17H2,1-3H3
  • Key:CNTCHEBQQFICNR-UHFFFAOYSA-N
  (verify)

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

References
  1. Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, et al. (January 2005). "Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) 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
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