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AB-FUBINACA

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
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
PubChemCID
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 apsychoactivedrug that acts as a potentagonist for thecannabinoid receptors, withKi values of 0.9 nM atCB1 and 23.2 nM atCB2 andEC50 values of 1.8 nM at CB1 and 3.2 nM at CB2.[3][4][5] It was originally developed byPfizer in 2009 as ananalgesic medication[6] but was never pursued for human use. In 2012, it was discovered as an ingredient insynthetic cannabinoid blends inJapan,[7] along with a related compoundAB-PINACA, which had not previously been reported.

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

Legality

[edit]

United States of America

[edit]

It was designated as aSchedule I controlled substance in theUnited States in January 2014.[10]

Finland

[edit]

In Finland AB-FUBINACA is scheduled in government decree on psychoactive substances banned from the consumer market as of 19 October 2017.[11]

Germany

[edit]

It is anAnlage II controlled substance inGermany as of November 2014.[12]

China

[edit]

Since October 2015 AB-FUBINACA is a controlled substance inChina.[13]

Others

[edit]

In December 2019, theUNODC announced scheduling recommendations placing AB-FUBINACA as a controlledresearch chemical into Schedule II.[14]101789

Mass overdoses due to adulterated K2

[edit]

On August 15, 2018, 70 people within the city ofNew Haven, Connecticut, started overdosing nearYale University campus.[15] 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.[16][17][18] First responders concluded that the overdoses were caused by opiate adulterants, as victims responded toNarcan.[19] 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.[20]

See also

[edit]

References

[edit]
  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. Retrieved2023-08-27.
  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.
  10. ^"Schedules of Controlled Substances: Temporary Placement of Four Synthetic Cannabinoids Into Schedule I". Drug Enforcement Administration, Department of Justice. 10 January 2014. Archived fromthe original on 28 February 2014. Retrieved21 July 2015.
  11. ^"FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 698/2017".
  12. ^"Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)" (in German). Retrieved22 June 2015.
  13. ^"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 fromthe original on 1 October 2015. Retrieved30 September 2015.
  14. ^"December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling".
  15. ^Winston A (2018-08-15)."New Haven Overdoses Tied to Laced K2".The New York Times.
  16. ^"Police Arrest Third Suspect In New Haven Synthetic Marijuana Overdose Case". NPR. 17 August 2018. Retrieved20 August 2018.
  17. ^"Dozens Overdose In Connecticut Park On Tainted Synthetic Marijuana". NPR. 16 August 2018. Retrieved20 August 2018.
  18. ^"New Haven police make arrest after more than 100 K2 overdose calls". CNN. 18 August 2018. Retrieved18 August 2018.
  19. ^Winston A (2018-08-15)."New Haven Overdoses Tied to Laced K2".The New York Times.
  20. ^"Police Arrest Third Suspect In New Haven Synthetic Marijuana Overdose Case". NPR. 17 August 2018. Retrieved20 August 2018.
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-3-tetrahydrocannabinols
Delta-4-tetrahydrocannabinols
Delta-7-tetrahydrocannabinols
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Delta-11-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
AllostericCBRTooltip Cannabinoid receptorligands
Endocannabinoid
enhancers

(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)
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