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MDMB-FUBINACA

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
MDMB-FUBINACA
Legal status
Legal status
Identifiers
  • Methyl (2S)-2-{[1-(4-fluorobenzyl)indazole-3-carbonyl]amino}-3,3-dimethylbutanoate
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC22H24FN3O3
Molar mass397.450 g·mol−1
3D model (JSmol)
  • O=C(N[C@H](C(OC)=O)C(C)(C)C)C1=NN(CC2=CC=C(F)C=C2)C3=C1C=CC=C3
  • InChI=1S/C22H24FN3O3/c1-22(2,3)19(21(28)29-4)24-20(27)18-16-7-5-6-8-17(16)26(25-18)13-14-9-11-15(23)12-10-14/h5-12,19H,13H2,1-4H3,(H,24,27)/t19-/m1/s1
  • Key:RFCDVEHNYDVCMU-LJQANCHMSA-N

MDMB-FUBINACA (also known as MDMB(N)-Bz-F andFUB-MDMB) is anindazole-basedsynthetic cannabinoid that is a potentagonist forcannabinoid receptors and that has been sold online as adesigner drug.[1][2] The structure of MDMB-FUBINACA contains theamino acid, 3-methylvaline[citation needed], also known as l-tert-leucine.[3] MDMB-FUBINACA hasKi values of 1.14nM atCB1 and 0.1228nM atCB2 andEC50 values of 0.2668nM at CB1 and 0.1411nM at CB2.[4]

Side effects

[edit]

There have been a large number of reported cases of deaths and hospitalizations in relation to this synthetic cannabinoid, mainly inRussia andBelarus. MDMB-FUBINACA was first reported in 2014 and quickly gained a reputation as the most deadly synthetic cannabinoid drug sold by 2015.[5] Up to 700 hospitalisations and 25 deaths were initially linked to MDMB-FUBINACA in media and government reports, and subsequent testing confirmed that at least 1000 hospitalisations and 40 deaths had occurred as a consequence of intoxication by MDMB-FUBINACA as of March 2015.[6][7]

Legal status

[edit]

In theUnited States, MDMB-FUBINACA is aSchedule I controlled substance.[8]

As of October 2015, MDMB-FUBINACA is a controlled substance inBelarus,Russia,[9] andChina.[10]

In July 2021, it was included in Table II-A in the list ofprohibited drugs ofPortugal.[citation needed]

See also

[edit]

References

[edit]
  1. ^"MDMB-FUBINACA". Cayman Chemical. Retrieved13 July 2015.
  2. ^Lee JH, Park HN, Leem TS, Jeon JH, Cho S, Lee J, Baek SY (2016). "Identification of new synthetic cannabinoid analogue APINAC (adamantan-1-yl 1-pentyl-1H-indazole-3-carboxylate) with other synthetic cannabinoid MDMB(N)-Bz-F in illegal products".Forensic Toxicology.35:45–55.doi:10.1007/s11419-016-0331-z.ISSN 1860-8973.S2CID 20136837.
  3. ^PubChem."3-Methyl-l-valine".pubchem.ncbi.nlm.nih.gov. Retrieved2025-02-24.
  4. ^Gamage TF, Farquhar CE, Lefever TW, Marusich JA, Kevin RC, McGregor IS, et al. (May 2018)."Molecular and Behavioral Pharmacological Characterization of Abused Synthetic Cannabinoids MMB- and MDMB-FUBINACA, MN-18, NNEI, CUMYL-PICA, and 5-Fluoro-CUMYL-PICA".The Journal of Pharmacology and Experimental Therapeutics.365 (2):437–446.doi:10.1124/jpet.117.246983.PMC 5932312.PMID 29549157.
  5. ^Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, Lebedev AT (August 2015). "Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group".Analytical and Bioanalytical Chemistry.407 (21):6301–15.doi:10.1007/s00216-015-8612-7.PMID 25893797.S2CID 31838655.
  6. ^"Выступление председателя ГАК, директора ФСКН России В.П. Иванова на заседании ГАК 6 октября 2014 г." (in Russian). Federal Drug Control Service of the Russian Federation. 6 October 2014. Archived fromthe original on 9 July 2015. Retrieved24 June 2015.
  7. ^I. Bulygina (21 October 2014)."Clinical presentations of intoxication by new psychoactive compound MDMB(N)-Bz-F. Thesis of The II Scientific and Practical Seminar 'Methodical, Organizational and Law Problems of Chemical and Toxicological Laboratories of Narcological Services', Moscow" (in Russian). Retrieved13 July 2015.
  8. ^"Schedules of Controlled Substances: Temporary Placement of Six Synthetic Cannabinoids (5F-ADB, 5F-AMB, 5F-APINACA, ADB-FUBINACA, MDMB-CHMICA and MDMB-FUBINACA) Into Schedule I".Drug Enforcement Administration. Archived fromthe original on 2019-10-17. Retrieved2017-03-17.
  9. ^"Очередная жертва спайса" (in Russian). Federal Drug Control Service of the Russian Federation. 17 March 2015. Archived fromthe original on 14 July 2015. Retrieved13 July 2015.
  10. ^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe original on 1 October 2015. Retrieved1 October 2015.
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