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ADB-FUBINACA

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
ADB-FUBINACA
Legal status
Legal status
Identifiers
  • N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H23FN4O2
Molar mass382.439 g·mol−1
3D model (JSmol)
  • O=C(NC(C(N)=O)C(C)(C)C)C1=NN(CC2=CC=C(F)C=C2)C3=C1C=CC=C3
  • InChI=InChI=1S/C21H23FN4O2/c1-21(2,3)18(19(23)27)24-20(28)17-15-6-4-5-7-16(15)26(25-17)12-13-8-10-14(22)11-9-13/h4-11,18H,12H2,1-3H3,(H2,23,27)(H,24,28)/t18-/m1/s1
  • Key:ZSSGCSINPVBLQD-GOSISDBHSA-N

ADB-FUBINACA (ADMB-FUBINACA[2]) is adesigner drug identified insynthetic cannabis blends in Japan in 2013.[3][4] In 2018, it was the third-most common synthetic cannabinoid identified in drugs seized by theDrug Enforcement Administration.[5]

The name is an acronym for N-(1-Amino-3,3-Dimethyl-1-oxoButan-2-yl)-1-(4-FlUoroBenzyl)-1H-INdAzole-3-CarboxAmide.

The (S)-enantiomer of ADB-FUBINACA is described in a 2009Pfizerpatent[6] and has been reported to be a potentagonist of theCB1 receptor and theCB2 receptor withEC50 values of 1.2 nM and 3.5 nM, respectively.[6][7] ADB-FUBINACA features a carboxamide group at the 3-indazole position, likeSDB-001 andSTS-135. ADB-FUBINACA appears to be the product of rational drug design, since it differs fromAB-FUBINACA only by the replacement of theisopropyl group with atert-butyl group.

An analogue of ADB-FUBINACA,ADSB-FUB-187, containing a more functionalized carboxamide substituent was recently reported.

Side effects

[edit]

One death through coronaryarterial thrombosis has been linked to ADB-FUBINACA intoxication.[8]

Metabolism

[edit]

Twenty-three ADB-FUBINACA major metabolites were identified in several incubations with cryopreserved human hepatocytes. Major metabolic pathways were alkyl and indazole hydroxylation, terminal amide hydrolysis, subsequent glucuronide conjugations, and dehydrogenation.[9]

Legality

[edit]

In the United States, ADB-FUBINACA is aSchedule I controlled substance.[10]

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. ^Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (July 2013). "Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products".Forensic Toxicology.31 (2):223–240.doi:10.1007/s11419-013-0182-9.S2CID 1279637.
  4. ^Lobato-Freitas C, Brito-da-Costa AM, Dinis-Oliveira RJ, Carmo H, Carvalho F, Silva JP, et al. (February 2021)."Overview of Synthetic Cannabinoids ADB-FUBINACA and AMB-FUBINACA: Clinical, Analytical, and Forensic Implications".Pharmaceuticals (Basel, Switzerland).14 (3): 186.doi:10.3390/ph14030186.PMC 7996508.PMID 33669071.
  5. ^"Emerging Threat Report: Annual 2018"(PDF). Special Testing and Research Laboratory, Drug Enforcement Administration.
  6. ^abWO 2009106982, "Indazole Derivatives" 
  7. ^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.
  8. ^Shanks KG, Clark W, Behonick G (April 2016)."Death Associated With the Use of the Synthetic Cannabinoid ADB-FUBINACA".Journal of Analytical Toxicology.40 (3):236–9.doi:10.1093/jat/bkv142.PMC 4885918.PMID 26755539.
  9. ^Carlier J, Diao X, Wohlfarth A, Scheidweiler K, Huestis MA (July 2017)."In Vitro Metabolite Profiling of ADB-FUBINACA, A New Synthetic Cannabinoid".Current Neuropharmacology.15 (5):682–691.doi:10.2174/1570159X15666161108123419.PMC 5771045.PMID 29403341.
  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. Archived fromthe original on 2019-10-17. Retrieved2017-03-17.
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