JWH-019

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JWH-019
File:JWH-019 structure.png
Systematic (IUPAC) name
1-hexyl-3-(naphthalen-1-oyl)indole
Legal status
Legal status
  • Class B (UK)
Identifiers
CAS Number 209414-08-4
Chemical data
Formula C25H25NO
Molar mass 355.471 g/mol[[Script error: No such module "String".]]
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JWH-019 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It is the N1-hexyl homologue of the more common synthetic cannabinoid compound JWH-018. Unlike the butyl homologue JWH-073 which is several times weaker than JWH-018, the hexyl homologue is only slightly less potent, although extending the chain one carbon longer to the heptyl homologue JWH-020 results in dramatic loss of activity. These results show that the optimum side chain length for CB1 binding in the naphthoylindole series is the five-carbon pentyl chain, shorter than in the classical cannabinoids where a seven-carbon heptyl chain produces the most potent compounds. This difference is thought to reflect a slightly different binding conformation adopted by the naphthoylindole compounds as compared to the classical cannabinoids, and may be useful in characterising the active site of the CB1 and CB2 receptors.[1][2][3]

See also

References

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  2. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  3. ↑ Ashton JC, Wright JL, McPartland JM, Tyndall JD (2008). "Cannabinoid CB1 and CB2 receptor ligand specificity and the development of CB2-selective agonists". Current Medicinal Chemistry. 15 (14): 1428–43. PMID 18537620. 
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