AB-FUBINACA

AB-FUBINACA is a 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.[1][2][3] It was originally developed by Pfizer in 2009 as an analgesic medication[4] but was never pursued for human use. In 2012, it was discovered as an ingredient in synthetic cannabinoid blends in Japan,[5] along with a related compound AB-PINACA, which had not previously been reported.

AB-FUBINACA
Legal status
Legal status
  • CA: Schedule II
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
  • UN: Psychotropic Schedule II
  • Illegal in China
Identifiers
IUPAC name
  • N-[(2S)-1-Amino-3-methyl-1-oxobutan-2-yl]-1-[(4-fluorophenyl)methyl]indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H21FN4O2
Molar mass368.412 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)[C@H](NC(=O)c1nn(Cc2ccc(F)cc2)c3ccccc13)C(N)=O
InChI
  • 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

Its use has been linked to hospitalizations and deaths.[6][7]

Legality

It was designated as a Schedule I controlled substance in the United States in January 2014.[8]

It is an Anlage II controlled substance in Germany as of November 2014.[9]

Since October 2015 AB-FUBINACA is a controlled substance in China .[10]

In December 2019, the UNODC announced scheduling recommendations placing AB-FUBINACA as a controlled research chemical into Schedule II.[11] 101789

Mass overdoses due to adulterated K2

On August 15th, 2018, 70 people within the city of New Haven, Connecticut started overdosing near Yale University campus.[12] By the end of the week, the total number of overdosed had risen to over 100 people needing transport to local emergency rooms. Three men were arrested, charged as drug dealers selling synthetic cannabis which contained AB-FUBINACA.[13][14][15] First responders concluded that the overdoses were caused by opiate adulterants, as victims responded to Narcan.[16] Almost all of the overdoses occurred on the New Haven Green, a large downtown park that is heavily traveled and very popular with the homeless population. There have been no deaths associated with these overdoses; however, several victims were in critical or life-threatening condition for a period of time.[17]

See also

References
  1. 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.
  2. 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.
  3. 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.
  4. WO 2009/106982, Buchler IP et al., "Indazole Derivatives"
  5. 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.
  6. 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.
  7. 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.
  8. "Schedules of Controlled Substances: Temporary Placement of Four Synthetic Cannabinoids Into Schedule I". Drug Enforcement Administration, Department of Justice. 10 January 2014. Retrieved 21 July 2015.
  9. "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)" (in German). Retrieved 22 June 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 from the original on 1 October 2015. Retrieved 30 September 2015.
  11. "December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling".
  12. Winston A (2018-08-15). "New Haven Overdoses Tied to Laced K2". The New York Times.
  13. "Police Arrest Third Suspect In New Haven Synthetic Marijuana Overdose Case". NPR. 17 August 2018. Retrieved 20 August 2018.
  14. "Dozens Overdose In Connecticut Park On Tainted Synthetic Marijuana". NPR. 16 August 2018. Retrieved 20 August 2018.
  15. "New Haven police make arrest after more than 100 K2 overdose calls". CNN. 18 August 2018. Retrieved 18 August 2018.
  16. Winston A (2018-08-15). "New Haven Overdoses Tied to Laced K2". The New York Times.
  17. "Police Arrest Third Suspect In New Haven Synthetic Marijuana Overdose Case". NPR. 17 August 2018. Retrieved 20 August 2018.
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