4F-MDMB-BINACA explained

Iupac Name:Methyl (S)-2-(1-(4-fluorobutyl)-1H-indazole-3-carboxamido)-3,3-dimethylbutanoate
Cas Number:2390036-46-9
Unii:ZH38UTM145
Pubchem:145707216
Kegg:C22799
Chemspiderid:71117201
C:19
H:26
F:1
N:3
O:3
Smiles:O=C(N[C@H](C(OC)=O)C(C)(C)C)C1=NN(CCCCF)C2=C1C=CC=C2
Stdinchi:1S/C19H26FN3O3/c1-19(2,3)16(18(25)26-4)21-17(24)15-13-9-5-6-10-14(13)23(22-15)12-8-7-11-20/h5-6,9-10,16H,7-8,11-12H2,1-4H3,(H,21,24)/t16-/m1/s1
Stdinchikey:GZGKSDAMWRWYOZ-MRXNPFEDSA-N
Legal Br:F2
Legal Br Comment:[1]
Legal Ca:Schedule II
Legal De:Anlage II
Legal Uk:Class B
Legal Un:P II
4F-MDMB-BINACA (also known as MDMB-4F-BINACA,[2] 4F-MDMB-BUTINACA or 4F-ADB) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family.[3] It has been used as an active ingredient in synthetic cannabis products and sold as a designer drug since late 2018.[4] [5] 4F-MDMB-BINACA is an agonist of the CB1 receptor (EC50 = 7.39 nM),[6] though it is unclear whether it is selective for this target.[7] In December 2019, the UNODC announced scheduling recommendations placing 4F-MDMB-BINACA into Schedule II throughout the world.[8]

Related compounds

The corresponding indole core analogue, 4F-MDMB-BICA (4F-MDMB-BUTICA), has also been widely sold as a designer drug by chemical providers on the internet, first being identified in May 2020.[9]

Legal Status

United Kingdom

It is illegal to sell, distribute, supply, transport or trade the pharmaceutical drug under the Psychoactive Substances Act 2016.

United States

4F-MDMB-BINACA is considered a Schedule I controlled substance as a positional isomer of the Schedule I compound 5F-AMB (5F-MMB-PINACA / 5F-AMB-PINACA). There has been charges brought against individuals for possession and distribution of 4F-MDMB-BINACA due to it being a positional isomer of 5F-AMB.[10]

The DEA has temporarily placed 4F-MDMB-BUTICA (the indole core analog of 4F-MDMB-BINACA) into Schedule I status starting on December 12th, 2023, for up to 2 years, during which it's possible the DEA could file for permanent scheduling within those 2 years. If the DEA does not file to permanent placement the temporary Schedule I order will expire on December 12th, 2025.[11]

North Dakota has placed 4F-MDMB-BINACA into Schedule I on 04/27/2023.[12]

See also

Notes and References

  1. Web site: Anvisa . Brazilian Health Regulatory Agency . 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. live . 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 . 2023-08-27 . 2023-08-27 . . pt-BR . 2023-07-25.
  2. Pulver B, Fischmann S, Gallegos A, Christie R . EMCDDA framework and practical guidance for naming synthetic cannabinoids . Drug Testing and Analysis . 15 . 3 . 255–276 . March 2023 . 36346325 . 10.1002/dta.3403 . 253396419 .
  3. Krotulski AJ, Mohr AL, Kacinko SL, Fogarty MF, Shuda SA, Diamond FX, Kinney WA, Menendez MJ, Logan BK . 4F-MDMB-BINACA: A New Synthetic Cannabinoid Widely Implicated in Forensic Casework . Journal of Forensic Sciences . 64 . 5 . 1451–1461 . September 2019 . 31260580 . 10.1111/1556-4029.14101 . 195770459 .
  4. Tokarczyk B, Jurczyk A, Krupińska J, Adamowicz P . Fatal intoxication with new synthetic cannabinoids 5F-MDMB-PICA and 4F-MDMB-BINACA-parent compounds and metabolite identification in blood, urine and cerebrospinal fluid . Forensic Science, Medicine, and Pathology . 18 . 4 . 393–402 . December 2022 . 35699867 . 9194349 . 10.1007/s12024-022-00492-3 .
  5. Wagmann L, Stiller RG, Fischmann S, Westphal F, Meyer MR . Going deeper into the toxicokinetics of synthetic cannabinoids: in vitro contribution of human carboxylesterases . Archives of Toxicology . 96 . 10 . 2755–2766 . October 2022 . 35788413 . 9352624 . 10.1007/s00204-022-03332-z .
  6. Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, Ellison R, Gerona R, Banister SD, Stove CP . Synthesis and in Vitro Cannabinoid Receptor 1 Activity of Recently Detected Synthetic Cannabinoids 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA . ACS Chemical Neuroscience . 11 . 24 . 4434–4446 . December 2020 . 33253529 . 10.1021/acschemneuro.0c00644 . 227246346 .
  7. Web site: 4F-MDMB-BINACA(4F-MDMB-BUTINACA). 15 April 2023.
  8. Web site: News: December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling. www.unodc.org. 15 April 2023.
  9. Web site: Analytical data for 4F-MDMB-BICA. . Hungarian Institute for Forensic Sciences. . 28 May 2020 .
  10. Web site: Indictment: Gordon III F, Gilreath . In the United States District Court for the Northern District of Ohio Eastern Division .
  11. Web site: Schedules of Controlled Substances: Temporary Placement of MDMB-4en-PINACA, 4F-MDMB-BUTICA, ADB-4en-PINACA, CUMYL-PEGACLONE, 5F-EDMB-PICA, and MMB-FUBICA in Schedule I . Federal Register . 4 April 2023 . 15 April 2023.
  12. Web site: 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. . Sixty-eighth Legislative Assembly of North Dakota in Regular Session . 3 January 2023 .

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