MDMB-FUBINACA

MDMB-FUBINACA (also known as MDMB(N)-Bz-F and FUB-MDMB) is an indazole-based synthetic cannabinoid that is a potent agonist for the cannabinoid receptors, with K_i values of 1.14 nM at CB₁ and 0.1228 nM at CB₂ and EC₅₀ values of 0.2668 nM at CB₁ and 0.1411 nM at CB₂,^[1] and has been sold online as a designer drug.^[2][3] Its benzyl analogue (instead of 4-fluorobenzyl) has been reported to be a potent agonist for the CB₁ receptor (K_i = 0.14 nM, EC₅₀ = 2.42 nM).^[4][5] The structure of MDMB-FUBINACA contains the amino acid, 3-methylvaline^[6] or tert-leucine methyl ester.

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

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.^[7] 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.^[8][9]

Legal status

In the United States, MDMB-FUBINACA is a Schedule I controlled substance.^[10]

As of October 2015, MDMB-FUBINACA is a controlled substance in Belarus, Russia,^[11] and China.^[12]

In July 2021 it was included in Table II-A of the list of prohibited drugs of Portugal.

See also

• 5F-AB-PINACA
• 5F-ADB
• 5F-AMB
• 5F-APINACA
• AB-FUBINACA
• AB-CHFUPYCA
• AB-CHMINACA
• AB-PINACA
• ADB-BINACA
• ADB-CHMINACA
• ADB-FUBINACA
• ADB-PINACA
• ADBICA
• APICA
• APINACA
• APP-FUBINACA
• MDMB-CHMICA
• MDMB-CHMINACA
• PX-3

References

1. 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.
2. "MDMB-FUBINACA". Cayman Chemical. Retrieved 13 July 2015.
3. 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.
4. WO 2009106982, Buchler IP et al, "Indazole Derivatives"
5. Banister SD, Longworth M, Kevin R, Sachdev S, Santiago M, Stuart J, et al. (September 2016). "Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues". ACS Chemical Neuroscience. 7 (9): 1241–54. doi:10.1021/acschemneuro.6b00137. PMID 27421060.
6. 3-methylvaline
7. 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.
8. "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.
9. 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.
10. "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.
11. "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.
12. "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.