AB-FUBINACA

AB-FUBINACA
Legal status
Legal status
Identifiers
  • N-[(2S)-1-Amino-3-methyl-1-oxobutan-2-yl]-1-[(4-fluorophenyl)methyl]indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H21FN4O2
Molar mass368.412 g·mol−1
3D model (JSmol)
  • CC(C)[C@H](NC(=O)c1nn(Cc2ccc(F)cc2)c3ccccc13)C(N)=O
  • InChI=1S/C20H21FN4O2/c1-12(2)17(19(22)26)23-20(27)18-15-5-3-4-6-16(15)25(24-18)11-13-7-9-14(21)10-8-13/h3-10,12,17H,11H2,1-2H3,(H2,22,26)(H,23,27)/t17-/m0/s1
  • Key:AKOOIMKXADOPDA-KRWDZBQOSA-N

AB-FUBINACA (AMB-FUBINACA[2]) is a psychoactive drug that acts as a potent agonist for the cannabinoid receptors, with Ki values of 0.9 nM at CB1 and 23.2 nM at CB2 and EC50 values of 1.8 nM at CB1 and 3.2 nM at CB2.[3][4][5] It was originally developed by Pfizer in 2009 as an analgesic medication[6] but was never pursued for human use. In 2012, it was discovered as an ingredient in synthetic cannabinoid blends in Japan,[7] along with a related compound AB-PINACA, which had not previously been reported.

Its use has been linked to hospitalizations and deaths.[8][9]

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID 36346325.
  3. ^ Banister SD, Moir M, Stuart J, Kevin RC, Wood KE, Longworth M, et al. (September 2015). "Pharmacology of Indole and Indazole Synthetic Cannabinoid Designer Drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, and 5F-ADBICA". ACS Chemical Neuroscience. 6 (9): 1546–59. doi:10.1021/acschemneuro.5b00112. PMID 26134475.
  4. ^ Hsin-Hung Chen M, Dip A, Ahmed M, Tan ML, Walterscheid JP, Sun H, et al. (April 2016). "Detection and Characterization of the Effect of AB-FUBINACA and Its Metabolites in a Rat Model". Journal of Cellular Biochemistry. 117 (4): 1033–43. doi:10.1002/jcb.25421. PMC 5063098. PMID 26517302.
  5. ^ Vikingsson S, Gréen H, Brinkhagen L, Mukhtar S, Josefsson M (September 2016). "Identification of AB-FUBINACA metabolites in authentic urine samples suitable as urinary markers of drug intake using liquid chromatography quadrupole tandem time of flight mass spectrometry". Drug Testing and Analysis. 8 (9): 950–6. doi:10.1002/dta.1896. PMID 26560240.
  6. ^ WO 2009/106982, Buchler IP et al., "Indazole Derivatives" 
  7. ^ Uchiyama N, Matsuda S, Wakana D, Kikura-Hanajiri R, Goda Y (January 2013). "New cannabimimetic indazole derivatives, N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA) identified as designer drugs in illegal products". Forensic Toxicology. 31 (1): 93–100. doi:10.1007/s11419-012-0171-4. S2CID 25242453.
  8. ^ Trecki J, Gerona RR, Schwartz MD (July 2015). "Synthetic Cannabinoid-Related Illnesses and Deaths". The New England Journal of Medicine. 373 (2): 103–7. doi:10.1056/NEJMp1505328. PMID 26154784.
  9. ^ Klavž J, Gorenjak M, Marinšek M (August 2016). "Suicide attempt with a mix of synthetic cannabinoids and synthetic cathinones: Case report of non-fatal intoxication with AB-CHMINACA, AB-FUBINACA, alpha-PHP, alpha-PVP and 4-CMC". Forensic Science International. 265: 121–4. doi:10.1016/j.forsciint.2016.01.018. PMID 26890319.