JWH-098

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)

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]

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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