JWH-019

Systematic (IUPAC) name
1-hexyl-3-(naphthalen-1-oyl)indole
Clinical data
Pregnancy cat.	?
Legal status	Class B (UK), illegal in Sweden, I-N (Poland)[1]
Identifiers
CAS number	209414-08-4 Y
ATC code	?
Chemical data
Formula	C25H25NO
Mol. mass	355.471 g/mol
SMILES	eMolecules & PubChem
Y (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 [link]

Poland [link]

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

Sweden [link]

JWH-019 is illegal in Sweden

UK [link]

JWH-019 is Class B in the United Kingdom.

USA [link]

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 the State of Virginia.^[5]

See also [link]

• JWH-007
• JWH-018
• JWH-073
• JWH-200

References [link]

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. https://isap.sejm.gov.pl/DetailsServlet?id = WDU20111050614. Retrieved 12 June 2011. 
2. ^ Aung MM, Griffin G, Huffman JW, Wu M, Keel C, Yang B, Showalter VM, Abood ME, Martin BR (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. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2219524. 
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. ^ https://crimlaw.blogspot.com/2011/04/no-more-synthetic-cannabinoid.html

This cannabinoid related article is a stub. You can help Wikipedia by expanding it. v t e