ADB-BINACA

ADB-BINACA is a cannabinoid designer drug that has been found as an ingredient in some synthetic cannabis products.[1] It was originally developed by Pfizer as a potential analgesic, and is a potent agonist of the CB1 receptor with a binding affinity (Ki) of 0.33 nM and an EC50 of 14.7 nM.[2]

ADB-BINACA
Legal status
Legal status
Identifiers
IUPAC name
  • N-[(2S)-1-amino-3,3-dimethyl-1-oxobutan-2-yl]-1-benzyl-1H-indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC21H24N4O2
Molar mass364.449 g·mol−1
3D model (JSmol)
SMILES
  • O=C(NC(C(N)=O)C(C)(C)C)C1=NN(CC2=CC=CC=C2)C3=C1C=CC=C3
InChI
  • InChI=1S/C21H24N4O2/c1-21(2,3)18(19(22)26)23-20(27)17-15-11-7-8-12-16(15)25(24-17)13-14-9-5-4-6-10-14/h4-12,18H,13H2,1-3H3,(H2,22,26)(H,23,27)
  • Key:IUFIUAWRCUVUCQ-UHFFFAOYSA-N

ADB-BUTINACA
ADB-BUTINACA
Legal status
Legal status
Identifiers
IUPAC name
  • N-[(2S)-1-amino-3,3-dimethyl-1-oxobutan-2-yl]-1-butyl-1H-indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC18H26N4O2
Molar mass330.432 g·mol−1
3D model (JSmol)
SMILES
  • O=C(N[C@H](C(N)=O)C(C)(C)C)C1=NN(CCCC)C2=C1C=CC=C2
InChI
  • InChI=1S/C18H26N4O2/c1-5-6-11-22-13-10-8-7-9-12(13)14(21-22)17(24)20-15(16(19)23)18(2,3)4/h7-10,15H,5-6,11H2,1-4H3,(H2,19,23)(H,20,24)/t15-/m1/s1
  • Key:GPWADXHYJAZPAX-OAHLLOKOSA-N

The analogue with a 1-butyl substitution on the indazole ring rather than 1-benzyl has also been sold as a designer drug under the name ADB-BINACA, but is now more commonly referred to as ADB-BUTINACA to avoid confusion with the benzyl compound.[3][4][5][6][7] It is a similarly potent CB1 agonist, with an EC50 of 6.36 nM.[8][9]

See also

References
  1. Qian Z, Hua Z, Liu C, Jia W (2016). "Four types of cannabimimetic indazole and indole derivatives, ADB-BINACA, AB-FUBICA, ADB-FUBICA, and AB-BICA, identified as new psychoactive substances". Forensic Toxicology. 34: 133–143. doi:10.1007/s11419-015-0297-2. PMC 4705129. PMID 26793280.
  2. WO 2009106982, "Indazole Derivatives"
  3. Kavanagh P, Pechnikov A, Nikolaev I, Dowling G, Kolosova M, Grigoryev A (August 2021). "Detection of ADB-BUTINACA Metabolites in Human Urine, Blood, Kidney and Liver". Journal of Analytical Toxicology. doi:10.1093/jat/bkab088. PMID 34341821.
  4. Sia CH, Wang Z, Goh EM, Tan YL, Fong CY, Moy HY, Chan EC (November 2021). "Urinary Metabolite Biomarkers for the Detection of Synthetic Cannabinoid ADB-BUTINACA Abuse". Clinical Chemistry. 67 (11): 1534–1544. doi:10.1093/clinchem/hvab134. PMID 34387654.
  5. Kronstrand R, Norman C, Vikingsson S, Biemans A, Valencia Crespo B, Edwards D, et al. (November 2021). "The metabolism of the synthetic cannabinoids ADB-BUTINACA and ADB-4en-PINACA and their detection in forensic toxicology casework and infused papers seized in prisons". Drug Testing and Analysis. doi:10.1002/dta.3203. PMID 34811926. S2CID 244490343.
  6. Wang, Yue; Pan, Yefei; Yang, Hongkun; Liu, Jinlei; Wurita, Amin; Hasegawa, Koutaro (2022). "Quantification of MDMB-4en-PINACA and ADB-BUTINACA in human hair by gas chromatography–tandem mass spectrometry". Forensic Toxicology. doi:10.1007/s11419-022-00615-z. ISSN 1860-8973.
  7. King, A.; Hill, S. L.; Pucci, M.; Bailey, G.; Keating, L.; Macfarlane, R.; Cantle, F.; Hudson, S.; Thomas, S. H. L. (August 2022). "Clinical features associated with ADB-BUTINACA exposure in patients attending emergency departments in England". Clinical Toxicology: 1–5. doi:10.1080/15563650.2022.2101469. ISSN 1556-3650. PMID 35943421.
  8. Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, et al. (December 2020). "Synthesis and in Vitro Cannabinoid Receptor 1 Activity of Recently Detected Synthetic Cannabinoids 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA". ACS Chemical Neuroscience. 11 (24): 4434–4446. doi:10.1021/acschemneuro.0c00644. PMID 33253529. S2CID 227246346.
  9. Pike E, Grafinger KE, Cannaert A, Ametovski A, Luo JL, Sparkes E, et al. (July 2021). "Systematic evaluation of a panel of 30 synthetic cannabinoid receptor agonists structurally related to MMB-4en-PICA, MDMB-4en-PINACA, ADB-4en-PINACA, and MMB-4CN-BUTINACA using a combination of binding and different CB1 receptor activation assays: Part I-Synthesis, analytical characterization, and binding affinity for human CB1 receptors". Drug Testing and Analysis. 13 (7): 1383–1401. doi:10.1002/dta.3037. PMID 33787091.
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