BZO-CHMOXIZID
{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name = N'-[(3Z)-1-(Cyclohexylmethyl)-2-oxo-1,2-dihydro-3H-indol-3-ylidene]benzohydrazide
| image = BZO-CHMOXIZID_structure.png
| width = 220
| pregnancy_category =
| legal_AU =
| legal_BR = F2
| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}
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| CAS_number = 1048973-67-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = W4JEN9G47K
| PubChem = 135881485
| ChemSpiderID = 24715499
| ChEMBL = 514565
| ChEBI =
| C=22 | H=23 | N=3 | O=2
| smiles = O=C(C1=CC=CC=C1)N/N=C(C2=O)/C3=CC=CC=C3N2CC4CCCCC4
| StdInChI = 1S/C22H23N3O2/c26-21(17-11-5-2-6-12-17)24-23-20-18-13-7-8-14-19(18)25(22(20)27)15-16-9-3-1-4-10-16/h2,5-8,11-14,16H,1,3-4,9-10,15H2,(H,24,26)/b23-20-
| StdInChIKey = HTPDZRIIOLCPPS-ATJXCDBQSA-N
}}
BZO-CHMOXIZID (CHM-MDA-19) is a synthetic cannabinoid compound first reported in 2008 in the same series as the better known derivative MDA-19.{{cite journal | vauthors = Diaz P, Xu J, Astruc-Diaz F, Pan HM, Brown DL, Naguib M | title = Design and synthesis of a novel series of N-alkyl isatin acylhydrazone derivatives that act as selective cannabinoid receptor 2 agonists for the treatment of neuropathic pain | journal = Journal of Medicinal Chemistry | volume = 51 | issue = 16 | pages = 4932–47 | date = August 2008 | pmid = 18666769 | doi = 10.1021/jm8002203 }} It started to be widely sold as an ingredient in grey-market synthetic cannabis blends in 2021 following the introduction of legislation in China which for the first time introduced general controls on various classes of synthetic cannabinoids,{{cite web | date = 12 May 2021 | title = 关于将合成大麻素类物质和氟胺酮等18种物质列入《非药用类麻醉药品和精神药品管制品种增补目录》的公告 | trans-title = Announcement on the inclusion of 18 substances including synthetic cannabinoids and fluamine in the "Additional Catalogue of Controlled Varieties of Non-medicinal Narcotics and Psychotropic Drugs" | language = Chinese | url = https://app.mps.gov.cn/gdnps/pc/content.jsp?id=7881703 | work = Ministry of Public Security of the People's Republic of China }} but did not include the group to which MDA-19 and BZO-CHMOXIZID belong. While BZO-CHMOXIZID is the most potent compound at CB1 from this so-called "OXAZID" series, it is still markedly CB2 selective and of relatively low potency at CB1, with an EC50 of 84.6 nM at CB1 compared to 2.21 nM at CB2.{{cite journal | vauthors = Deventer MH, Van Uytfanghe K, Vinckier IM, Reniero F, Guillou C, Stove CP | title = Cannabinoid receptor activation potential of the next generation, generic ban evading OXIZID synthetic cannabinoid receptor agonists | journal = Drug Testing and Analysis | volume = 14 | issue = 9 | pages = 1565–1575 | date = September 2022 | pmid = 35560866 | doi = 10.1002/dta.3283 | s2cid = 248777773 | url = https://biblio.ugent.be/publication/01GQ74V7ZKBG7AK8QKJWSP5FAV }}{{cite journal | vauthors = Lee KZ, Wang Z, Fong CY, Goh EM, Moy HY, Chan EC | title = Identification of Optimal Urinary Biomarkers of Synthetic Cannabinoids BZO-HEXOXIZID, BZO-POXIZID, 5F-BZO-POXIZID, and BZO-CHMOXIZID for Illicit Abuse Monitoring | journal = Clinical Chemistry | volume = 68 | issue = 11 | pages = 1436–1448 | date = November 2022 | pmid = 36175111 | doi = 10.1093/clinchem/hvac138 }}
Legality
In the United States, As of October 20, 2024 BZO-CHMOXIZID is legal at the federal level, but may be considered illegal if intended for human consumption under the federal analogue act.{{Cite web|url=https://www.law.cornell.edu/uscode/text/21/813|title = 21 U.S. Code § 813 - Treatment of controlled substance analogues}}
North Dakota has placed BZO-CHOMXIZID (CHM-MDA-19) (along with BZO-HEXOXIZID (MDA-19), BZO-POXIZID (Pentyl MDA-19), 5F-BZO-POXIZID (5F-MDA-19) and BZO-4en-POXIZID (4en-pentyl MDA-19) into Schedule I on 04/27/23.{{cite web | title = AN ACT to amend and reenact sections 19-03.1-05, 19-03.1-11, and 19-03.1-13 of the North Dakota Century Code, relating to the scheduling of controlled substances; and to declare an emergency. | url = https://www.ndlegis.gov/prod/assembly/68-2023/regular/documents/23-8099-04000.pdf | work = Sixty-eighth Legislative Assembly of North Dakota in Regular Session | date = 3 January 2023 }}
In China, the May 2021 ban on specific synthetic cannabinoid core classes does not include the class of cannabinoids BZO-CHMOXIZID belongs to.{{cite web | date = 12 May 2021 | title = 关于将合成大麻素类物质和氟胺酮等18种物质列入《非药用类麻醉药品和精神药品管制品种增补目录》的公告 | trans-title = Announcement on the inclusion of 18 substances including synthetic cannabinoids and fluamine in the "Additional Catalogue of Controlled Varieties of Non-medicinal Narcotics and Psychotropic Drugs" | language = Chinese | url = https://app.mps.gov.cn/gdnps/pc/content.jsp?id=7881703 | work = Ministry of Public Security of the People's Republic of China }}{{Cite web |url= https://www.unodc.org/LSS/Country/Details/CN |title = Details for Country CHINA }}
References
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{{Cannabinoids}}
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