ADB-FUBINACA

Last updated

ADB-FUBINACA
ADB-FUBINACA structure.png
Legal status
Legal status
Identifiers
  • N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
Formula C21H23FN4O2
Molar mass 382.439 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 a designer drug identified in synthetic cannabis blends in Japan in 2013. [3] [4] In 2018, it was the third-most common synthetic cannabinoid identified in drugs seized by the Drug Enforcement Administration. [5]

Contents

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 2009 Pfizer patent [6] and has been reported to be a potent agonist of the CB1 receptor and the CB2 receptor with EC50 values of 1.2 nM and 3.5 nM, respectively. [6] [7] ADB-FUBINACA features a carboxamide group at the 3-indazole position, like SDB-001 and STS-135. ADB-FUBINACA appears to be the product of rational drug design, since it differs from AB-FUBINACA only by the replacement of the isopropyl group with a tert-butyl group.

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

Side effects

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

Metabolism

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

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

See also

References

  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. ↑ 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. 1 2 WO 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 from the original on 2019-10-17. Retrieved 2017-03-17.
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