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]
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| Formula | C21H23FN4O2 |
| Molar mass | 382.439 g·mol−1 |
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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
editOne death through coronary arterial thrombosis has been linked to ADB-FUBINACA intoxication.[8]
Metabolism
editTwenty-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
editIn the United States, ADB-FUBINACA is a Schedule I controlled substance.[10]
See also
editReferences
edit- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "Emerging Threat Report: Annual 2018" (PDF). Special Testing and Research Laboratory, Drug Enforcement Administration.
- ^ a b WO 2009106982, "Indazole Derivatives"
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "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.