ADB-FUBINACA

ADB-FUBINACA
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); 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	1185282-00-1 ;
PubChem CID	70969086;
ChemSpider	29763706;
UNII	05235E1S2O;
KEGG	C22699 ;
CompTox Dashboard (EPA)	DTXSID701009981 ;
Chemical and physical data
Formula	C21H23FN4O2
Molar mass	382.439 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

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]

References

^ 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.

[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.

[pmid33669071-4] 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.

[Pfizer-6] 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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Side effects

Metabolism

Legality

See also

References