4F-MDMB-BINACA

4F-MDMB-BINACA (also known as 4F-MDMB-BUTINACA or 4F-ADB) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family.[1] It has been used as an active ingredient in synthetic cannabis products and sold as a designer drug since late 2018.[2][3] 4F-MDMB-BINACA is an agonist of the CB1 receptor (EC50 = 7.39 nM),[4] though it is unclear whether it is selective for this target.[5] In December 2019, the UNODC announced scheduling recommendations placing 4F-MDMB-BINACA into Schedule II throughout the world.[6]

4F-MDMB-BINACA
Legal status
Legal status
  • CA: Schedule II
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • UN: Psychotropic Schedule II
Identifiers
IUPAC name
  • Methyl (S)-2-(1-(4-fluorobutyl)-1H-indazole-3-carboxamido)-3,3-dimethylbutanoate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC19H26FN3O3
Molar mass363.433 g·mol−1
3D model (JSmol)
SMILES
  • O=C(N[C@H](C(OC)=O)C(C)(C)C)C1=NN(CCCCF)C2=C1C=CC=C2
InChI
  • 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

The corresponding indole core analogue, 4F-MDMB-BICA or 4F-MDMB-BUTICA has also been widely sold as a designer drug by chemical providers on the net, first being identified in May 2020.[7]

4F-MDMB-BICA

United Kingdom

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

United States

The DEA has filed a notice for its intent to temporarily place 4F-MDMB-BUTICA (but not 4F-MDMB-BINACA itself) into Schedule I status starting on or after May 4, 2023, for up to 2 years, during which it's possible the DEA could file for permanent scheduling within those 2 years. If it is filed on May 4, 2023, and the DEA does not file to permanent placement the temporary Schedule I order will expire on May 4, 2025.[8]

North Dakota has placed 4F-MDMB-BINACA into Schedule I on 04/27/2023.[9]

See also

References
  1. 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.
  2. 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.
  3. 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. doi:10.1007/s00204-022-03332-z. PMC 9352624. PMID 35788413.
  4. 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.
  5. "4F-MDMB-BINACA(4F-MDMB-BUTINACA)" (PDF). Retrieved 15 April 2023.
  6. "News: December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling". www.unodc.org. Retrieved 15 April 2023.
  7. "Analytical data for 4F-MDMB-BICA" (PDF). Hungarian Institute for Forensic Sciences. 28 May 2020.
  8. "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.
  9. "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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