ADB-BINACA explained

Iupac Name:N-[(2''S'')-1-amino-3,3-dimethyl-1-oxobutan-2-yl]-1-benzyl-1H-indazole-3-carboxamide
Legal Ca:Schedule II
Legal De:Anlage II
Legal Uk:Class B
Legal Us:Schedule I
Cas Number:1185282-27-2
Unii:PUVP61SOSI
Pubchem:129406620
Chemspiderid:57621565
Smiles:O=C(NC(C(N)=O)C(C)(C)C)C1=NN(CC2=CC=CC=C2)C3=C1C=CC=C3
Stdinchi: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)
Stdinchikey:IUFIUAWRCUVUCQ-UHFFFAOYSA-N
C:21
H:24
N:4
O:2

ADB-BINACA (also known as ADMB-BZINACA using EMCDDA naming standards[1] ) is a cannabinoid designer drug that has been found as an ingredient in some synthetic cannabis products.[2] 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.[3]

ADB-BUTINACA

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.[4] [5] [6] [7] [8] It is a similarly potent CB1 agonist, with a binding affinity of 0.29nM for CB1 and 0.91nM for CB2, and an EC50 of 6.36 nM for CB1.[9] [10]

See also

Notes and References

  1. Pulver B, Fischmann S, Gallegos A, Christie R . EMCDDA framework and practical guidance for naming synthetic cannabinoids . Drug Testing and Analysis . 15 . 3 . 255–276 . March 2023 . 36346325 . 10.1002/dta.3403 . 253396419 .
  2. Qian Z, Hua Z, Liu C, Jia W . 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 . 2016 . 26793280 . 4705129 . 10.1007/s11419-015-0297-2 .
  3. WO . 2009106982 . Indazole Derivatives .
  4. Kavanagh P, Pechnikov A, Nikolaev I, Dowling G, Kolosova M, Grigoryev A . Detection of ADB-BUTINACA Metabolites in Human Urine, Blood, Kidney and Liver . Journal of Analytical Toxicology . 46 . 6 . 641–650 . July 2022 . 34341821 . 10.1093/jat/bkab088 .
  5. Sia CH, Wang Z, Goh EM, Tan YL, Fong CY, Moy HY, Chan EC . Urinary Metabolite Biomarkers for the Detection of Synthetic Cannabinoid ADB-BUTINACA Abuse . Clinical Chemistry . 67 . 11 . 1534–1544 . November 2021 . 34387654 . 10.1093/clinchem/hvab134 . free .
  6. Kronstrand R, Norman C, Vikingsson S, Biemans A, Valencia Crespo B, Edwards D, Fletcher D, Gilbert N, Persson M, Reid R, Semenova O, Al Teneiji F, Wu X, Dahlén J, NicDaéid N, Tarbah F, Sutcliffe OB, McKenzie C, Gréen H . 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 . 14 . 4 . 634–652 . April 2022 . 34811926 . 10.1002/dta.3203 . 244490343 . free .
  7. Wang Y, Pan Y, Yang H, Liu J, Wurita A, Hasegawa K . Quantification of MDMB-4en-PINACA and ADB-BUTINACA in human hair by gas chromatography-tandem mass spectrometry . Forensic Toxicology . 40 . 2 . 340–348 . July 2022 . 36454410 . 10.1007/s11419-022-00615-z . 247501663 .
  8. King A, Hill SL, Pucci M, Bailey G, Keating L, Macfarlane R, Cantle F, Hudson S, Thomas SH . Clinical features associated with ADB-BUTINACA exposure in patients attending emergency departments in England . Clinical Toxicology . 60 . 10 . 1094–1098 . October 2022 . 35943421 . 10.1080/15563650.2022.2101469 . 251444625 .
  9. Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, Ellison R, Gerona R, Banister SD, Stove CP . 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 . December 2020 . 33253529 . 10.1021/acschemneuro.0c00644 . 227246346 .
  10. Pike E, Grafinger KE, Cannaert A, Ametovski A, Luo JL, Sparkes E, Cairns EA, Ellison R, Gerona R, Stove CP, Auwärter V, Banister SD . 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 . July 2021 . 33787091 . 10.1002/dta.3037 .

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