JWH-019

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[[]]

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.

See also

• JWH-007
• JWH-018
• JWH-073
• JWH-200