MDMB-FUBINACA

MDMB-FUBINACA
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B; US: Schedule I;
Identifiers
	IUPAC name Methyl (2S)-2-{[1-(4-fluorobenzyl)indazole-3-carbonyl]amino}-3,3-dimethylbutanoate;
CAS Number	1971007-93-8;
PubChem CID	119025665;
ChemSpider	32741674;
UNII	544DR70TN4;
CompTox Dashboard (EPA)	DTXSID301355877 DTXSID501010003, DTXSID301355877 ;
Chemical and physical data
Formula	C22H24FN3O3
Molar mass	397.450 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 and FUB-MDMB) is an indazole-based synthetic cannabinoid that is a potent agonist for cannabinoid receptors and that has been sold online as a designer drug.^[1]^[2] The structure of MDMB-FUBINACA contains the amino acid, 3-methylvaline^{[citation needed]}, also known as l-tert-leucine.^[3] MDMB-FUBINACA has K_i values of 1.14nM at CB₁ and 0.1228nM at CB₂ and EC₅₀ values of 0.2668nM at CB₁ and 0.1411nM at CB_2.^[4]

Side effects

There have been a large number of reported cases of deaths and hospitalizations in relation to this synthetic cannabinoid, mainly in Russia and Belarus. 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

In the United States, MDMB-FUBINACA is a Schedule I controlled substance.^[8]

As of October 2015, MDMB-FUBINACA is a controlled substance in Belarus, Russia,^[9] and China.^[10]

In July 2021, it was included in Table II-A in the list of prohibited drugs of Portugal.^{[citation needed]}

References

^ "MDMB-FUBINACA". Cayman Chemical. Retrieved 13 July 2015.
^ 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.
^ PubChem. "3-Methyl-l-valine". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-02-24.
^ 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.
^ 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.
^ "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 from the original on 9 July 2015. Retrieved 24 June 2015.
^ 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). Retrieved 13 July 2015.
^ "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.
^ "Очередная жертва спайса" (in Russian). Federal Drug Control Service of the Russian Federation. 17 March 2015. Archived from the original on 14 July 2015. Retrieved 13 July 2015.
^ "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. Retrieved 1 October 2015.

[1] "MDMB-FUBINACA". Cayman Chemical. Retrieved 13 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. Retrieved 2025-02-24.

[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 from the original on 9 July 2015. Retrieved 24 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). Retrieved 13 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.

[9] "Очередная жертва спайса" (in Russian). Federal Drug Control Service of the Russian Federation. 17 March 2015. Archived from the original on 14 July 2015. Retrieved 13 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. Retrieved 1 October 2015.

[1]

Side effects

Legal status

See also

References