JWH-007

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JWH-007
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Legal status
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Identifiers
  • 1-Pentyl-2-methyl-3-(1-naphthoyl)indole
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Chemical and physical data
FormulaC25H25NO
Molar mass355.481 g·mol−1
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  • c14ccccc4cccc1C(=O)c3c2ccccc2n(c3C)CCCCC
  • 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
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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]

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]

JWH-007 has been classified under the German BtMG as Anlage II.[12]

See also

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Huffman JW, Dai D, Martin BR, Compton DR (1994). "Design, Synthesis and Pharmacology of Cannabimimetic Indoles". Bioorganic & Medicinal Chemistry Letters. 4 (4): 563–566. doi:10.1016/s0960-894x(01)80155-4.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Pertwee RG, Griffin G, Lainton JA, Huffman JW (September 1995). "Pharmacological characterization of three novel cannabinoid receptor agonists in the mouse isolated vas deferens". European Journal of Pharmacology. 284 (3): 241–247. doi:10.1016/0014-2999(95)00318-f. PMID 8666005.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR (December 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. doi:10.1016/S0022-3565(25)10448-5. PMID 1335057.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, et al. (January 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. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry. 12 (12): 1395–1411. doi:10.2174/0929867054020864. PMID 15974991.
  6. ^ Page Module:Citation/CS1/styles.css has no content.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): 133–140. doi:10.1016/S0376-8716(99)00152-0. PMID 10940540.
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  8. ^ Swedish Code of Statutes Regulation (2010:1086).
  9. ^ Page Module:Citation/CS1/styles.css has no content."Swedish Code of Statutes Regulation (2010:1086). (pdf)" (PDF). Archived from the original (PDF) on 2011-07-28. Retrieved 2011-01-10.
  10. ^ Page Module:Citation/CS1/styles.css has no content."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. ^ Page Module:Citation/CS1/styles.css has no content."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 中文). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  12. ^ Page Module:Citation/CS1/styles.css has no content."Stoffe gem. Anlagen zum BtMG". Retrieved 2024-11-23.

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