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]

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
CAS Number
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H25NO
Molar mass355.471 g/mol g·mol−1
3D model (JSmol)
  (verify)

China

As of October 2015 JWH-019 is a controlled substance in China.[5]

Poland

In Poland, JWH-019 is I-N (Poland).[1]

Sweden

JWH-019 is illegal in Sweden.

United Kingdom

JWH-019 is Class B in the United Kingdom.

United States

JWH-019 is a Schedule I controlled substance, controlled federally in the United States.[6]

See also

References
  1. "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. Retrieved 12 June 2011.
  2. Aung MM, 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. PMID 10940540.
  3. Poso A, Huffman JW (January 2008). "Targeting the cannabinoid CB2 receptor: modelling and structural determinants of CB2 selective ligands". British Journal of Pharmacology. 153 (2): 335–46. doi:10.1038/sj.bjp.0707567. PMC 2219524. PMID 17982473.
  4. 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. PMID 18537620.
  5. "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. Retrieved 1 October 2015.
  6. Controlled Substances listed by the DEA
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