JWH-019

JWH-019

JWH-019
Systematic (IUPAC) name
1-hexyl-3-(naphthalen-1-oyl)indole
Clinical data
Legal status
  • Class B (UK), illegal in Sweden, I-N (Poland)[1]
Identifiers
CAS number  YesY
ATC code ?
ChemSpider
Chemical data
Formula C25H25NO 
Mol. mass 355.471 g/mol
 YesY   

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.[2][3][4]

Legal Status

Poland

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

Sweden

JWH-019 is illegal in Sweden

UK

JWH-019 is Class B in the United Kingdom.

USA

JWH-019 is not controlled federally in the United States, however if intended for human consumption, possession or sales could possibly be prosecuted under the Federal Analog Act.

JWH-019 is illegal in Virginia.[5]

See also

References

  1. ^ a b = WDU20111050614 "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.  
  3. ^ Poso A, Huffman JW (January 2008). "Targeting the cannabinoid CB2 receptor: modelling and structural determinants of CB2 selective ligands".  
  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.  
  5. ^ http://crimlaw.blogspot.com/2011/04/no-more-synthetic-cannabinoid.html