ADB-FUBINACA

ADB-FUBINACA is a designer drug identified in synthetic cannabis blends in Japan in 2013.[1][2] In 2018, it was the third-most common synthetic cannabinoid identified in drugs seized by the Drug Enforcement Administration.[3]

ADB-FUBINACA
Legal status
Legal status
  • CA: Schedule II
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
Identifiers
IUPAC name
  • N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H23FN4O2
Molar mass382.439 g·mol−1
3D model (JSmol)
SMILES
  • O=C(NC(C(N)=O)C(C)(C)C)C1=NN(CC2=CC=C(F)C=C2)C3=C1C=CC=C3
InChI
  • 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

The (S)-enantiomer of ADB-FUBINACA is described in a 2009 Pfizer patent[4] 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.[4][5] 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.[6]

At least an additional 8 deaths in Hungary in 2015 are linked to the usage of this material, all deaths were youngsters below 21.

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.[7]

Legality

In the United States, ADB-FUBINACA is a Schedule I controlled substance.[8]

See also

References
  1. 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.
  2. Lobato-Freitas C, Brito-da-Costa AM, Dinis-Oliveira RJ, Carmo H, Carvalho F, Silva JP, Dias-da-Silva D (February 2021). "Overview of Synthetic Cannabinoids ADB-FUBINACA and AMB-FUBINACA: Clinical, Analytical, and Forensic Implications". Pharmaceuticals (Basel, Switzerland). 14 (3). doi:10.3390/ph14030186. PMC 7996508. PMID 33669071.
  3. "Emerging Threat Report: Annual 2018" (PDF). Special Testing and Research Laboratory, Drug Enforcement Administration.
  4. WO 2009106982, "Indazole Derivatives"
  5. 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.
  6. 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.
  7. 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.
  8. "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.
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