Chemistry:JWH-007
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| Formula | C25H25NO |
| Molar mass | 355.481 g·mol−1 |
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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 first reported in 1994 by a group including the noted cannabinoid chemist John W. Huffman.[1][2] 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), JWH-200 (WIN 55,225) and WIN 55,212-2 by the Sterling Winthrop group.[3] 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, 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.[4][5] Consequently, the 2-desmethyl derivative of JWH-007, JWH-018, has slightly higher binding affinity for CB1, with an optimum binding of 9.00 nM at CB1 and 2.94 nM at CB2, and JWH-007 displayed optimum binding of 9.50 nM at CB1 and 2.94 nM at CB2.[6]
Legal status
In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-007 are Schedule I Controlled Substances.[7]
JWH-007 was banned in Sweden on 1 October 2010 after being identified as an ingredient in "herbal" synthetic cannabis products.[8][9]
JWH-007 has been illegal in Poland since August 2010[10]
As of October 2015 JWH-007 is a controlled substance in China.[11]
See also
References
- ↑ "Design, Synthesis and Pharmacology of Cannabimimetic Indoles". Bioorganic & Medicinal Chemistry Letters 4 (4): 563–566. 1994. doi:10.1016/s0960-894x(01)80155-4.
- ↑ "Pharmacological characterization of three novel cannabinoid receptor agonists in the mouse isolated vas deferens". European Journal of Pharmacology 284 (3): 241–247. September 1995. doi:10.1016/0014-2999(95)00318-f. PMID 8666005.
- ↑ "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. December 1992. PMID 1335057.
- ↑ "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. January 2005. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
- ↑ "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry 12 (12): 1395–1411. 2005. doi:10.2174/0929867054020864. PMID 15974991.
- ↑ "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. August 2000. doi:10.1016/S0376-8716(99)00152-0. PMID 10940540.
- ↑ : Schedules of controlled substances
- ↑ Swedish Code of Statutes Regulation (2010:1086).
- ↑ "Swedish Code of Statutes Regulation (2010:1086). (pdf)". http://www.lagboken.se/files/SFS/2010/101086.PDF.
- ↑ "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". ISAP. http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614.
- ↑ "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 zh). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html.
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