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
China
As of October 2015 JWH-019 is a controlled substance in China.[5]
^Aung MM, Griffin G, Huffman JW, Wu M, Keel C, Yang B, et al. (August 2000). "Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding". Drug and Alcohol Dependence. 60 (2): 133–40.
doi:
10.1016/S0376-8716(99)00152-0.
PMID10940540.
^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.
doi:
10.2174/092986708784567716.
PMID18537620.
^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from
the original on 1 October 2015. Retrieved 1 October 2015.