MDMB-5Br-INACA

MDMB-5Br-INACA

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics) [1]
Identifiers
IUPAC name methyl (2S)-2-[(5-bromo-1H-indazole-3-carbonyl)amino]-3,3-dimethylbutanoate
PubChem CID	165362085
ChemSpider	114952001
UNII	2Q2FVJ9CFN
CompTox Dashboard (EPA)	DTXSID701345242
Chemical and physical data
Formula	C15H18BrN3O3
Molar mass	368.231 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(OC)[C@@H](NC(=O)c1n[NH]c2ccc(Br)cc21)C(C)(C)C
InChI InChI=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 Key:QGEVEXPJOKFMAN-GFCCVEGCSA-N

MDMB-5Br-INACA is an indazole-3-carboxamide derivative which has been sold as a designer drug. ^[2] 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. ^{[3] [4]} 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), ^[5] (CH-IATA), (ADB-IACA), and (ADB-5’Br-EZO-CA). This may be due to increasing legality changes worldwide on synthetic cannabinoids. ^{[6] [7]}

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. ^[8]

See also

• 4F-MDMB-BINACA
• 5F-ADB
• ADB-5'Br-PINACA
• MDMB-FUBINACA
• MDMB-5'Br-BUTINACA

References

1. Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
2. "CFSRE Analysis Report" (PDF). Indianapolis-Marion County Forensic Services Agency. 17 May 2022.
3. "Drug testers warn of new synthetic cannabinoid being sold as MDMA". New Zealand Herald. 5 August 2022.
4. Deventer MH, Persson M, Norman C, Liu H, Connolly MJ, Daéid NN, et al. (October 2023). "In vitro cannabinoid activity profiling of generic ban-evading brominated synthetic cannabinoid receptor agonists and their analogs". Drug Testing and Analysis. 16 (6): 616–628. doi:10.1002/dta.3592. PMID   37903509. S2CID   264671035.
5. Choi H, Kim S, Jang H, Kim HJ, Choe S (September 2022). "Identification of a novel bromoindazole synthetic cannabinoid analogue in seized e-cigarette liquid: ADB-BRINACA". Forensic Science International. 338 111385. doi:10.1016/j.forsciint.2022.111385. PMID   35863161.
6. "Cumyl-PeGaClone and other recently encountered synthetic cannabinoid receptor agonists. A review of the evidence on their use and harms" (PDF). Advisory Council on the Misuse of Drugs. 2022.
7. Andrews R, Jorge R, Christie R, Gallegos A (April 2023). "From JWH-018 to OXIZIDS: Structural evolution of synthetic cannabinoids in the European Union from 2008 to present day". Drug Testing and Analysis. 15 (4): 378–387. doi:10.1002/dta.3422. PMID   36507715.
8. "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" (PDF). Sixty-eighth Legislative Assembly of North Dakota in Regular Session. 3 January 2023.