JWH-019

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 N-hexyl homolog of the more common synthetic cannabinoid compound JWH-018. Unlike the butyl homolog JWH-073, which is several times weaker than JWH-018, the hexyl homolog is only slightly less potent, although extending the chain one carbon longer to the heptyl homolog 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 characterizing the active site of the CB₁ and CB₂ receptors.^[2][3][4]

Legal status

• CA: Schedule II
• DE: Anlage II (Authorized trade only, not prescriptible)
• UK: Class B
• US: Schedule I
• Illegal in Sweden, I-N (Poland)^[1]

CAS Number

• 209414-08-4 ^Y

ChemSpider

• 24598813

UNII

• 0Z73828O4J

Quick facts Legal status, Identifiers ...

JWH-019

Legal status
Legal status	CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I Illegal in Sweden, I-N (Poland)[1]
Identifiers
IUPAC name 1-Hexyl-3-(naphthalen-1-oyl)indole
CAS Number	209414-08-4 Y
ChemSpider	24598813
UNII	0Z73828O4J
CompTox Dashboard (EPA)	DTXSID70175118
Chemical and physical data
Formula	C25H25NO
Molar mass	355.481 g·mol−1
3D model (JSmol)	Interactive image
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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