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JWH-015
Legal status
Legal status	CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule I;
Identifiers
	IUPAC name (2-Methyl-1-propyl-1H-indol-3-yl)-1-naphthalenylmethanone;
CAS Number	155471-08-2 ;
PubChem CID	4273754;
IUPHAR/BPS	5558;
ChemSpider	3480676 ;
UNII	W4FL204T10;
CompTox Dashboard (EPA)	DTXSID60165902 ;
ECHA InfoCard	100.161.912
Chemical and physical data
Formula	C23H21NO
Molar mass	327.427 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCN1C(=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43)C;
	InChI InChI=1S/C23H21NO/c1-3-15-24-16(2)22(20-12-6-7-14-21(20)24)23(25)19-13-8-10-17-9-4-5-11-18(17)19/h4-14H,3,15H2,1-2H3 ; Key:LJSBBBWQTLXQEN-UHFFFAOYSA-N ;
	(what is this?) (verify)

JWH-015 is a chemical from the naphthoylindole family that acts as a subtype-selective cannabinoid agonist. Its affinity for CB₂ receptors is 13.8 nM, while its affinity for CB₁ is 383 nM, meaning that it binds almost 28 times more strongly to CB₂ than to CB₁.^[1] However, it still displays some CB₁ activity, and in some model systems can be very potent and efficacious at activating CB₁ receptors,^[2] and therefore it is not as selective as newer drugs such as JWH-133.^[3] It has been shown to possess immunomodulatory effects,^[4]^[5] and CB₂ agonists may be useful in the treatment of pain and inflammation.^[6]^[7] It was discovered and named after John W. Huffman.

Metabolism

JWH-015 has been shown in vitro to be metabolized primarily by hydroxylation and N-dealkylation, and also by epoxidation of the naphthalene ring,^[8] similar to the metabolic pathways seen for other aminoalkylindole cannabinoids such as WIN 55,212-2.^[9] Epoxidation of polycyclic aromatic hydrocarbons (see for example benzo(a)pyrene toxicity) can produce carcinogenic metabolites, although there is no evidence to show that JWH-015 or other aminoalkylindole cannabinoids are actually carcinogenic in vivo. JWH-015 may signal certain cancers to shrink through a process called apoptosis.^[10]

Legal status

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-015 are Schedule I Controlled Substances.^[11]

As of October 2015 JWH-015 is a controlled substance in China.^[12]

JWH-015 has been classified under the German BtMG as Anlage II.^[13]

References

^ 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 CB₁ and CB₂)receptor binding". Drug and Alcohol Dependence. 60 (2): 133–140. doi:10.1016/S0376-8716(99)00152-0. PMID 10940540.
^ Murataeva N, Mackie K, Straiker A (November 2012). "The CB2-preferring agonist JWH015 also potently and efficaciously activates CB1 in autaptic hippocampal neurons". Pharmacological Research. 66 (5): 437–442. doi:10.1016/j.phrs.2012.08.002. PMC 3601544. PMID 22921769.
^ Marriott KS, Huffman JW (2008). "Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor". Current Topics in Medicinal Chemistry. 8 (3): 187–204. doi:10.2174/156802608783498014. PMID 18289088.
^ Ghosh S, Preet A, Groopman JE, Ganju RK (July 2006). "Cannabinoid receptor CB2 modulates the CXCL12/CXCR4-mediated chemotaxis of T lymphocytes". Molecular Immunology. 43 (14): 2169–2179. doi:10.1016/j.molimm.2006.01.005. PMID 16503355.
^ Montecucco F, Burger F, Mach F, Steffens S (March 2008). "CB2 cannabinoid receptor agonist JWH-015 modulates human monocyte migration through defined intracellular signaling pathways". American Journal of Physiology. Heart and Circulatory Physiology. 294 (3): H1145 – H1155. doi:10.1152/ajpheart.01328.2007. PMID 18178718. S2CID 5896815.
^ Balter MB, Uhlenhuth EH (1992). "Prescribing and use of benzodiazepines: an epidemiologic perspective". Journal of Psychoactive Drugs. 24 (1): 63–64. doi:10.1080/02791072.1992.10471620. PMID 1352348.
^ Romero-Sandoval A, Eisenach JC (April 2007). "Spinal cannabinoid receptor type 2 activation reduces hypersensitivity and spinal cord glial activation after paw incision". Anesthesiology. 106 (4): 787–794. doi:10.1097/01.anes.0000264765.33673.6c. PMID 17413917.
^ Zhang Q, Ma P, Cole RB, Wang G (November 2006). "Identification of in vitro metabolites of JWH-015, an aminoalkylindole agonist for the peripheral cannabinoid receptor (CB2) by HPLC-MS/MS". Analytical and Bioanalytical Chemistry. 386 (5): 1345–1355. doi:10.1007/s00216-006-0717-6. PMID 16955257. S2CID 9116612.
^ Zhang Q, Ma P, Iszard M, Cole RB, Wang W, Wang G (October 2002). "In vitro metabolism of R(+)-[2,3-dihydro-5-methyl-3-[(morpholinyl)methyl]pyrrolo [1,2,3-de]1,4-benzoxazinyl]-(1-naphthalenyl) methanone mesylate, a cannabinoid receptor agonist". Drug Metabolism and Disposition. 30 (10): 1077–1086. doi:10.1124/dmd.30.10.1077. PMID 12228183. S2CID 10848076.
^ Olea-Herrero N, Vara D, Malagarie-Cazenave S, Díaz-Laviada I (September 2009). "Inhibition of human tumour prostate PC-3 cell growth by cannabinoids R(+)-Methanandamide and JWH-015: involvement of CB2". British Journal of Cancer. 101 (6): 940–950. doi:10.1038/sj.bjc.6605248. PMC 2743360. PMID 19690545.
^ 21 U.S.C. § 812: Schedules of controlled substances
^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" [Notice on Issuing the Measures for the Listing and Control of Non-Medicinal Narcotic Drugs and Psychotropic Substances] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
^ "Stoffe gem. Anlagen zum BtMG". Retrieved 2024-11-23.

[pmid10940540-1] 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 CB₁ and CB₂)receptor binding". Drug and Alcohol Dependence. 60 (2): 133–140. doi:10.1016/S0376-8716(99)00152-0. PMID 10940540.

[pmid22921769-2] Murataeva N, Mackie K, Straiker A (November 2012). "The CB2-preferring agonist JWH015 also potently and efficaciously activates CB1 in autaptic hippocampal neurons". Pharmacological Research. 66 (5): 437–442. doi:10.1016/j.phrs.2012.08.002. PMC 3601544. PMID 22921769.

[pmid18289088-3] Marriott KS, Huffman JW (2008). "Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor". Current Topics in Medicinal Chemistry. 8 (3): 187–204. doi:10.2174/156802608783498014. PMID 18289088.

[pmid16503355-4] Ghosh S, Preet A, Groopman JE, Ganju RK (July 2006). "Cannabinoid receptor CB2 modulates the CXCL12/CXCR4-mediated chemotaxis of T lymphocytes". Molecular Immunology. 43 (14): 2169–2179. doi:10.1016/j.molimm.2006.01.005. PMID 16503355.

[pmid18178718-5] Montecucco F, Burger F, Mach F, Steffens S (March 2008). "CB2 cannabinoid receptor agonist JWH-015 modulates human monocyte migration through defined intracellular signaling pathways". American Journal of Physiology. Heart and Circulatory Physiology. 294 (3): H1145 – H1155. doi:10.1152/ajpheart.01328.2007. PMID 18178718. S2CID 5896815.

[pmid1352348-6] Balter MB, Uhlenhuth EH (1992). "Prescribing and use of benzodiazepines: an epidemiologic perspective". Journal of Psychoactive Drugs. 24 (1): 63–64. doi:10.1080/02791072.1992.10471620. PMID 1352348.

[pmid17413917-7] Romero-Sandoval A, Eisenach JC (April 2007). "Spinal cannabinoid receptor type 2 activation reduces hypersensitivity and spinal cord glial activation after paw incision". Anesthesiology. 106 (4): 787–794. doi:10.1097/01.anes.0000264765.33673.6c. PMID 17413917.

[8] Zhang Q, Ma P, Cole RB, Wang G (November 2006). "Identification of in vitro metabolites of JWH-015, an aminoalkylindole agonist for the peripheral cannabinoid receptor (CB2) by HPLC-MS/MS". Analytical and Bioanalytical Chemistry. 386 (5): 1345–1355. doi:10.1007/s00216-006-0717-6. PMID 16955257. S2CID 9116612.

[pmid12228183-9] Zhang Q, Ma P, Iszard M, Cole RB, Wang W, Wang G (October 2002). "In vitro metabolism of R(+)-[2,3-dihydro-5-methyl-3-[(morpholinyl)methyl]pyrrolo [1,2,3-de]1,4-benzoxazinyl]-(1-naphthalenyl) methanone mesylate, a cannabinoid receptor agonist". Drug Metabolism and Disposition. 30 (10): 1077–1086. doi:10.1124/dmd.30.10.1077. PMID 12228183. S2CID 10848076.

[10] Olea-Herrero N, Vara D, Malagarie-Cazenave S, Díaz-Laviada I (September 2009). "Inhibition of human tumour prostate PC-3 cell growth by cannabinoids R(+)-Methanandamide and JWH-015: involvement of CB2". British Journal of Cancer. 101 (6): 940–950. doi:10.1038/sj.bjc.6605248. PMC 2743360. PMID 19690545.

[11] 21 U.S.C. § 812: Schedules of controlled substances

[12] "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" [Notice on Issuing the Measures for the Listing and Control of Non-Medicinal Narcotic Drugs and Psychotropic Substances] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.

[13] "Stoffe gem. Anlagen zum BtMG". Retrieved 2024-11-23.

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PROFILPELAJAR.COM

JWH-015

Metabolism

Legal status

References

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