4F-MDMB-BINACA
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| IUPAC_name = Methyl (S)-2-(1-(4-fluorobutyl)-1H-indazole-3-carboxamido)-3,3-dimethylbutanoate
| image = 4F-MDMB-BINACA.svg
| image_class = skin-invert-image
| CAS_number = 2390036-46-9
| ATC_prefix =
| ATC_suffix =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ZH38UTM145
| PubChem = 145707216
| DrugBank =
| 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
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category=
| legal_AU =
| 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}}
| legal_CA = Schedule II
| legal_DE = Anlage II
| legal_UK = Class B
| legal_US =
| legal_UN = P II
| legal_status =
| routes_of_administration =
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4F-MDMB-BINACA (also known as MDMB-4F-BINACA using systematic EMCDDA nomenclature{{cite journal |vauthors=Pulver B, Fischmann S, Gallegos A, Christie R |date=March 2023 |title=EMCDDA framework and practical guidance for naming synthetic cannabinoids |url=https://www.euda.europa.eu/drugs-library/emcdda-framework-and-practical-guidance-naming-synthetic-cannabinoids_en |journal=Drug Testing and Analysis |volume=15 |issue=3 |pages=255–276 |doi=10.1002/dta.3403 |pmid=36346325|url-access=subscription }} or 4F-MDMB-BUTINACA) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family.{{cite journal | vauthors = Krotulski AJ, Mohr AL, Kacinko SL, Fogarty MF, Shuda SA, Diamond FX, Kinney WA, Menendez MJ, Logan BK | title = 4F-MDMB-BINACA: A New Synthetic Cannabinoid Widely Implicated in Forensic Casework | journal = Journal of Forensic Sciences | volume = 64 | issue = 5 | pages = 1451–1461 | date = September 2019 | pmid = 31260580 | doi = 10.1111/1556-4029.14101 | s2cid = 195770459 }} 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.{{cite journal | vauthors = Tokarczyk B, Jurczyk A, Krupińska J, Adamowicz P | title = Fatal intoxication with new synthetic cannabinoids 5F-MDMB-PICA and 4F-MDMB-BINACA-parent compounds and metabolite identification in blood, urine and cerebrospinal fluid | journal = Forensic Science, Medicine, and Pathology | volume = 18 | issue = 4 | pages = 393–402 | date = December 2022 | pmid = 35699867 | pmc = 9194349 | doi = 10.1007/s12024-022-00492-3 }}{{cite journal | vauthors = Wagmann L, Stiller RG, Fischmann S, Westphal F, Meyer MR | title = Going deeper into the toxicokinetics of synthetic cannabinoids: in vitro contribution of human carboxylesterases | journal = Archives of Toxicology | volume = 96 | issue = 10 | pages = 2755–2766 | date = October 2022 | pmid = 35788413 | pmc = 9352624 | doi = 10.1007/s00204-022-03332-z | bibcode = 2022ArTox..96.2755W }} 4F-MDMB-BINACA is an agonist of the CB1 receptor (EC50 = 7.39 nM),{{cite journal | vauthors = Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, Ellison R, Gerona R, Banister SD, Stove CP | title = 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 | journal = ACS Chemical Neuroscience | volume = 11 | issue = 24 | pages = 4434–4446 | date = December 2020 | pmid = 33253529 | doi = 10.1021/acschemneuro.0c00644 | s2cid = 227246346 }} though it is unclear whether it is selective for this target.{{Cite web|url=https://www.deadiversion.usdoj.gov/drug_chem_info/4F-MDMB-BINACA.pdf|title=4F-MDMB-BINACA(4F-MDMB-BUTINACA)|access-date=15 April 2023}} In December 2019, the UNODC announced scheduling recommendations placing 4F-MDMB-BINACA into Schedule II throughout the world.{{Cite web|url=https://www.unodc.org/LSS/Announcement/Details/021820a0-8746-42a4-9ee3-47ce50b30ca3|title=News: December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling|website=www.unodc.org|access-date=15 April 2023}}
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.{{cite web | url = https://www.policija.si/apps/nfl_response_web/0_Analytical_Reports_final/4F-MDMB-BICA-ID-HIFS-020.pdf | title = Analytical data for 4F-MDMB-BICA. | work = Hungarian Institute for Forensic Sciences. | date = 28 May 2020 }}
Image:4F-MDMB-BICA_structure.png{{clear left}}
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.
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.{{cite web | title = Indictment: Gordon III F, Gilreath | work = In the United States District Court for the Northern District of Ohio Eastern Division | url = https://www.justice.gov/media/1126421/dl?inline= }}
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.{{cite web| title=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 | website=Federal Register | date=4 April 2023 | url=https://www.federalregister.gov/documents/2023/04/04/2023-06893/schedules-of-controlled-substances-temporary-placement-of-mdmb-4en-pinaca-4f-mdmb-butica | access-date=15 April 2023}}
North Dakota has placed 4F-MDMB-BINACA 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}}
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