4F-MDMB-BINACA

Last updated

4F-MDMB-BINACA
4F-MDMB-BINACA.svg
Legal status
Legal status
Identifiers
  • Methyl (S)-2-(1-(4-fluorobutyl)-1H-indazole-3-carboxamido)-3,3-dimethylbutanoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
Formula C19H26FN3O3
Molar mass 363.433 g·mol−1
3D model (JSmol)
  • O=C(N[C@H](C(OC)=O)C(C)(C)C)C1=NN(CCCCF)C2=C1C=CC=C2
  • InChI=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
  • Key:GZGKSDAMWRWYOZ-MRXNPFEDSA-N

4F-MDMB-BINACA (also known as MDMB-4F-BINACA using systematic EMCDDA nomenclature [2] or 4F-MDMB-BUTINACA) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family. [3] It should not be confused with the amantadine analogue 4F-ABINACA. 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]

Contents

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]

4F-MDMB-BICA 4F-MDMB-BICA structure.png
4F-MDMB-BICA

4F-MDMB-BINACA may be confused with a positional isomer of 5F-MDMB-PINACA called 4F-MDMB-PINACA, because of the use of the confusing names 5F-ADB and 4F-ADB. These confusing shorter names were not scientifically adopted but were used by websites selling the drugs to the public.

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

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. ↑ Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID   36346325.
  3. ↑ Krotulski AJ, Mohr AL, Kacinko SL, Fogarty MF, Shuda SA, Diamond FX, et al. (September 2019). "4F-MDMB-BINACA: A New Synthetic Cannabinoid Widely Implicated in Forensic Casework". Journal of Forensic Sciences. 64 (5): 1451–1461. doi:10.1111/1556-4029.14101. PMID   31260580. S2CID   195770459.
  4. ↑ Tokarczyk B, Jurczyk A, Krupińska J, Adamowicz P (December 2022). "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. doi:10.1007/s12024-022-00492-3. PMC   9194349 . PMID   35699867.
  5. ↑ Wagmann L, Stiller RG, Fischmann S, Westphal F, Meyer MR (October 2022). "Going deeper into the toxicokinetics of synthetic cannabinoids: in vitro contribution of human carboxylesterases". Archives of Toxicology. 96 (10): 2755–2766. Bibcode:2022ArTox..96.2755W. doi:10.1007/s00204-022-03332-z. PMC   9352624 . PMID   35788413.
  6. ↑ Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, et al. (December 2020). "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. doi:10.1021/acschemneuro.0c00644. PMID   33253529. S2CID   227246346.
  7. ↑ "4F-MDMB-BINACA(4F-MDMB-BUTINACA)" (PDF). Retrieved 15 April 2023.
  8. ↑ "News: December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling". www.unodc.org. Retrieved 15 April 2023.
  9. ↑ "Analytical data for 4F-MDMB-BICA" (PDF). Hungarian Institute for Forensic Sciences. 28 May 2020.
  10. ↑ "Indictment: Gordon III F, Gilreath". In the United States District Court for the Northern District of Ohio Eastern Division.
  11. ↑ "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. Retrieved 15 April 2023.
  12. ↑ "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.


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