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JWH-098

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
JWH-098
Legal status
Legal status
Identifiers
  • 4-Methoxynaphthalen-1-yl-(1-pentyl-2-methylindol-3-yl)methanone
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC26H27NO2
Molar mass385.507 g·mol−1
3D model (JSmol)
  • CCCCCn(c1C)c2ccccc2c1C(=O)c(ccc3OC)c4ccccc34
  • 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 syntheticcannabinoid receptoragonist from thenaphthoylindole family. It is theindole 2-methyl derivative of a closely related compoundJWH-081, but has markedly different affinity for theCB1 andCB2 receptors. While JWH-081 is around tenfold 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.[2]

Legal status

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

JWH-098 is illegal in Russia,[4] Sweden,[5] and the UK,[6] although it is unclear whether it has any history of human use.

See also

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References

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  1. ^Anvisa (2023-07-24)."RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-07-25).Archived from the original on 2023-08-27. Retrieved2023-08-27.
  2. ^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.
  3. ^21 U.S.C. § 812:Schedules of controlled substances
  4. ^"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 fromthe original on 2010-09-29. Retrieved2010-09-09.
  5. ^Svensk författningssamling
  6. ^The Misuse of Drugs Act 1971 (Amendment) Order 2009Archived 2009-11-03 at theWayback Machine
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