JWH-019

JWH-019

Systematic (IUPAC) name
1-hexyl-3-(naphthalen-1-oyl)indole
Clinical data
Legal status	CA: Schedule II DE: Anlage II (Prohibited) UK: Class B US: Schedule I Illegal in Sweden, I-N (Poland)
Identifiers
CAS Number	209414-08-4 Y
ChemSpider	24598813
Chemical data
Formula	C25H25NO
Molecular mass	355.471 g/mol
SMILES c3cccc2c3cccc2C(=O)c1cn(CCCCCC)c4c1cccc4
InChI InChI=1S/C25H25NO/c1-2-3-4-9-17-26-18-23(21-14-7-8-16-24(21)26)25(27)22-15-10-12-19-11-5-6-13-20(19)22/h5-8,10-16,18H,2-4,9,17H2,1H3 Key:PALJPGHWDUHUPO-UHFFFAOYSA-N
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JWH-019 is an analgesic chemical from the naphthoylindole family that 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.

Legal Status

China

As of October 2015 JWH-019 is a controlled substance in China.

Poland

In Poland, JWH-019 is I-N (Poland)

Sweden

JWH-019 is illegal in Sweden

UK

JWH-019 is Class B in the United Kingdom.

USA

JWH-019 is a C-I substance, controlled federally in the United States, and it is not intended for human consumption.

JWH-019 is illegal in Virginia.

See also

• JWH-007
• JWH-018
• JWH-073
• JWH-200
• List of JWH cannabinoids