MDMB-FUBINACA

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MDMB-FUBINACA
MDMB-FUBINACA.svg
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC22H24FN3O3
Molar mass397.4 g/mol g·mol−1
3D model (JSmol)

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 Ki 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 (Ki = 0.14 nM, EC50 = 2.42 nM).[4][5] The structure of MDMB-FUBINACA contains the amino acid 3-methylvaline or tert-leucine methyl ester.

Side effects[edit]

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 to date.[6] 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.[7][8][9]

Legal status[edit]

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]

See also[edit]

References[edit]

  1. ^ Gamage, Thomas F.; Farquhar, Charlotte E.; Lefever, Timothy W.; Marusich, Julie A.; Kevin, Richard C.; McGregor, Iain S.; Wiley, Jenny L.; Thomas, Brian F. (April 2018). "Molecular and behavioral pharmacological characterization of abused synthetic cannabinoids MMB- and MDMB-FUBINACA, MN-18, NNEI, CUMYL-PICA, and 5-fluoro-CUMYL-PICA". Journal of Pharmacology and Experimental Therapeutics. 365 (1): 437–446. doi:10.1124/jpet.117.246983. ISSN 0022-3565. PMC 5932312. PMID 29549157.
  2. ^ "MDMB-FUBINACA". Cayman Chemical. Retrieved 13 July 2015.
  3. ^ Lee, Ji Hyun; Park, Han Na; Leem, Tan-Soon; Jeon, Joo-hyoung; Cho, Sooyeul; Lee, Jongkook; Baek, Sun Young (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.
  4. ^ Buchler IP et al, INDAZOLE DERIVATIVES. WO 2009/106982
  5. ^ Banister, Samuel D.; Longworth, Mitchell; Kevin, Richard; Sachdev, Shivani; Santiago, Marina; Stuart, Jordyn; Mack, James B. C.; Glass, Michelle; McGregor, Iain S.; Connor, Mark; Kassiou, Michael (27 July 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. ^ Shevyrin, Vadim; Melkozerov, Vladimir; Nevero, Alexander; Eltsov, Oleg; Shafran, Yuri; Morzherin, Yuri; Lebedev, AlbertT. (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): 6301–6315. doi:10.1007/s00216-015-8612-7. ISSN 1618-2642. PMID 25893797.
  7. ^ "25 killed, over 700 hospitalized: Cheap 'Spice' designer drug causes severe poisoning across Russia". 7 October 2014. Retrieved 13 July 2015.
  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. 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. 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.