JWH-019

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JWH-019
JWH019.svg
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 209414-08-4 YesY
ATC code ?
ChemSpider 24598813
Chemical data
Formula C25H25NO 
Mol. mass 355.471 g/mol
 YesY (what is this?)  (verify)

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[edit]

Poland[edit]

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

Sweden[edit]

JWH-019 is illegal in Sweden

UK[edit]

JWH-019 is Class B in the United Kingdom.

USA[edit]

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[edit]

References[edit]

  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. 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. ^ http://crimlaw.blogspot.com/2011/04/no-more-synthetic-cannabinoid.html