JWH-007

JWH-007

Legal status
Legal status	CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible)
Identifiers
IUPAC name 1-pentyl-2-methyl-3-(1-naphthoyl)indole
CAS Number	155471-10-6 Y
PubChem CID	10360860
ChemSpider	8536309
Chemical and physical data
Formula	C25H25NO
Molar mass	355.471 g/mol
3D model (JSmol)	Interactive image
SMILES c14ccccc4cccc1C(=O)c3c2ccccc2n(c3C)CCCCC
InChI InChI=1S/C25H25NO/c1-3-4-9-17-26-18(2)24(22-14-7-8-16-23(22)26)25(27)21-15-10-12-19-11-5-6-13-20(19)21/h5-8,10-16H,3-4,9,17H2,1-2H3 Key:IBBNKINXTRKICJ-UHFFFAOYSA-N
(verify)

JWH-007 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB₁ and CB₂ receptors. It was the most active of the first group of N-alkyl naphoylindoles discovered by the team led by John W Huffman, several years after the family was initially described with the discovery of the N-morpholinylethyl compounds pravadoline (WIN 48,098), WIN 55,225 (JWH-200) and WIN 55,212-2 by the Sterling Winthrop group.^[1] Several other N-alkyl substituents were found to be active by Huffman's team including the n-butyl, n-hexyl, 2-heptyl and cyclohexylethyl groups,^[2] but it was subsequently determined that the 2-methyl group on the indole ring is not required for CB₁ binding, and tends to increase affinity for CB₂ instead.^[3][4] Consequently, the 2-desmethyl derivative of JWH-007, JWH-018 has slightly higher binding affinity for CB₁, with an optimum binding of 9.00nM at CB₁ and 2.94nM at CB₂, and JWH-007 displayed optimum binding of 9.50nM at CB₁ and 2.94nM at CB₂.^[5]

Another drug similarly named JHW-007 (not JWH) is a cocaine analogue (the di-para-fluoro benztropine, being essentially a hybrid between benzatropine & difluoropine; with fluorine groups in the former or being descarbmethoxy in the latter) and atypical dopamine reuptake inhibitor,^[6] but is distinct from and not the same as this JWH-007.^[7]

Law

JWH-007 was banned in Sweden on 1 October 2010 as a hazardous good harmful to health, after being identified as an ingredient in "herbal" synthetic cannabis products.^[8][9]

JWH-007 is illegal in Poland since 08.06.2010 on the basis of 'Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii' published in Dz.U. 2011 nr 105 poz. 614^[10]

As of October 2015 JWH-007 is a controlled substance in China.^[11]

See also

• JWH-015
• JWH-018
• JWH-019
• JWH-073
• List of JWH cannabinoids

References

1. ↑ Compton, D. R.; et al. (1992). "Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol". The Journal of Pharmacology and Experimental Therapeutics. 263 (3): 1118–1126. PMID 1335057. 
2. ↑ Huffman, JW; Dong, D (1994). "Design, Synthesis and Pharmacology of Cannabimimetic Indoles". Bioorganic and Medicinal Chemistry Letters. 4 (4): 563–566. doi:10.1016/s0960-894x(01)80155-4. 
3. ↑ Huffman, J.; et al. (2005). "Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists.". Bioorganic & Medicinal Chemistry. 13 (1): 89–112. PMID 15582455. doi:10.1016/j.bmc.2004.09.050. 
4. ↑ Huffman, J. W.; Padgett, L. W. (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current medicinal chemistry. 12 (12): 1395–1411. PMID 15974991. doi:10.2174/0929867054020864. 
5. ↑ Aung, M. M.; et al. (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): 133–140. PMID 10940540. doi:10.1016/S0376-8716(99)00152-0. 
6. ↑ Rothman, Richard B.; Baumann, Michael H.; Prisinzano, Thomas E.; Newman, Amy Hauck (2008). "Dopamine transport inhibitors based on GBR12909 and benztropine as potential medications to treat cocaine addiction". Biochemical Pharmacology. 75 (1): 2–16. ISSN 0006-2952. PMC 2225585 . PMID 17897630. doi:10.1016/j.bcp.2007.08.007. 
7. ↑ Velázquez-Sánchez, Clara; García-Verdugo, José M.; Murga, Juan; Canales, Juan J. (2013). "The atypical dopamine transport inhibitor, JHW 007, prevents amphetamine-induced sensitization and synaptic reorganization within the nucleus accumbens". Progress in Neuro-Psychopharmacology and Biological Psychiatry. 44: 73–80. ISSN 0278-5846. doi:10.1016/j.pnpbp.2013.01.016. 
8. ↑ Swedish Code of Statutes Regulation (2010:1086).
9. ↑ Swedish Code of Statutes Regulation (2010:1086). (pdf)
10. ↑ "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". ISAP. Retrieved 12 June 2011. 
11. ↑ "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.