JWH-019

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);
Identifiers
	IUPAC name 1-Hexyl-3-(naphthalen-1-oyl)indole;
CAS Number	209414-08-4 ;
ChemSpider	24598813;
UNII	0Z73828O4J;
CompTox Dashboard (EPA)	DTXSID70175118 ;
Chemical and physical data
Formula	C25H25NO
Molar mass	355.481 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c3cccc2c3cccc2C(=O)c1cn(CCCCCC)c4c1cccc4;
	InChI InChI=1S/C25H25NO/c1-2-3-4-9-17-26-18-23(21-14-7-8-16-24(21)26)25(27)22-15-10-12-19-11-5-6-13-20(19)22/h5-8,10-16,18H,2-4,9,17H2,1H3; Key:PALJPGHWDUHUPO-UHFFFAOYSA-N;
	(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 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]

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]

References

^ ^a ^b "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.
^ 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. PMID 10940540.
^ 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.
^ 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.
^ "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.
^ Controlled Substances listed by the DEA

[isap.sejm-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.

[pmid10940540-2] 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. PMID 10940540.

[pmid17982473-3] 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.

[pmid18537620-4] 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. Archived from the original on 1 October 2015. Retrieved 1 October 2015.

[6] Controlled Substances listed by the DEA

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