MDMB-5Br-INACA
{{Short description|Chemical compound}}
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{{Drugbox
| IUPAC_name = methyl (2S)-2-[(5-bromo-1H-indazole-3-carbonyl)amino]-3,3-dimethylbutanoate
| image = MDMB-5Br-INACA_structure.png
| width = 200px
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| legal_BR = F2
| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}
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| PubChem = 165362085
| ChemSpiderID = 114952001
| UNII = 2Q2FVJ9CFN
| smiles = O=C(OC)[C@@H](NC(=O)c1n[NH]c2ccc(Br)cc21)C(C)(C)C
| C=15 | H=18 | Br=1 | N=3 | O=3
| StdInChI = 1S/C15H18BrN3O3/c1-15(2,3)12(14(21)22-4)17-13(20)11-9-7-8(16)5-6-10(9)18-19-11/h5-7,12H,1-4H3,(H,17,20)(H,18,19)/t12-/m1/s1
| StdInChIKey = QGEVEXPJOKFMAN-GFCCVEGCSA-N
}}
MDMB-5Br-INACA is an indazole-3-carboxamide derivative which has been sold as a designer drug.{{cite web | url = https://www.npsdiscovery.org/wp-content/uploads/2022/05/MDMB-5Br-INACA_051722_CFSRE-Chemistry_Report.pdf | title = CFSRE Analysis Report | work = Indianapolis-Marion County Forensic Services Agency | date = 17 May 2022 }} Surprisingly it has been reported to produce psychoactive activity despite the lack of a "tail" group at the indazole 1-position, but is likely of relatively low potency as a CB1 agonist and has been encountered being misrepresented as other illicit drugs such as MDMA.{{cite web | url = https://www.nzherald.co.nz/nz/drug-testers-warn-of-new-synthetic-cannabinoid-being-sold-as-mdma/T35763CVQZHPV6LBZEQQ6FPX3U/ | title = Drug testers warn of new synthetic cannabinoid being sold as MDMA | work = New Zealand Herald | date = 5 August 2022 }}{{cite journal | vauthors = Deventer MH, Persson M, Norman C, Liu H, Connolly MJ, Daéid NN, McKenzie C, Gréen H, Stove CP | title = In vitro cannabinoid activity profiling of generic ban-evading brominated synthetic cannabinoid receptor agonists and their analogs | journal = Drug Testing and Analysis | volume = | issue = | pages = | date = October 2023 | pmid = 37903509 | doi = 10.1002/dta.3592 | s2cid = 264671035 }} This reported psychoactive activity has been limitedly reported on but could be related to activity beyond the cannabinoid receptors due to vague structural relation to compounds like 1Z2MAP1O.
Use as a precursor
MDMB-5Br-INACA is believed to be used as a precursor in the synthesis of synthetic cannabinoids. It has been sold online as a "chemistry kit" with other compounds required to complete the reaction. This reaction would complete MDMB-5Br-INACA by giving it a "tail" group required for high cannabinoid activity. Other precursors lacking a tail chain have also been marketed such as (ADB-5-Br-INACA),{{cite journal | vauthors = Choi H, Kim S, Jang H, Kim HJ, Choe S | title = Identification of a novel bromoindazole synthetic cannabinoid analogue in seized e-cigarette liquid: ADB-BRINACA | journal = Forensic Science International | volume = 338 | issue = | pages = 111385 | date = September 2022 | pmid = 35863161 | doi = 10.1016/j.forsciint.2022.111385 }} (CH-IATA), (ADB-IACA), and (ADB-5’Br-EZO-CA). This may be due to increasing legality changes worldwide on synthetic cannabinoids.{{cite web | url = https://assets.publishing.service.gov.uk/government/uploads/system/uploads/attachment_data/file/1159142/Cumyl-pegalone_and_other_uncontrolled_SCRA_report-FINAL.pdf | title = Cumyl-PeGaClone and other recently encountered synthetic cannabinoid receptor agonists. A review of the evidence on their use and harms. | work = Advisory Council on the Misuse of Drugs | date = 2022 }}{{cite journal | vauthors = Andrews R, Jorge R, Christie R, Gallegos A | title = From JWH-018 to OXIZIDS: Structural evolution of synthetic cannabinoids in the European Union from 2008 to present day | journal = Drug Testing and Analysis | volume = 15 | issue = 4 | pages = 378–387 | date = April 2023 | pmid = 36507715 | doi = 10.1002/dta.3422 }}
Legality
In the United States, MDMB-5Br-INACA is unscheduled at the federal level as of May 22nd, 2023.
North Dakota has placed MDMB-5Br-INACA (along with ADB-5'Br-BINACA, ADB-5'Br-BUTINACA and ADB-5-Br-INACA) into Schedule I on 04/27/2023.{{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 }}
See also
References
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{{Cannabinoids}}
{{Cannabinoidergics}}
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