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ADB-BINACA

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
ADB-BINACA
Legal status
Legal status
Identifiers
  • N-[(2S)-1-amino-3,3-dimethyl-1-oxobutan-2-yl]-1-benzyl-1H-indazole-3-carboxamide
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H24N4O2
Molar mass364.449 g·mol−1
3D model (JSmol)
  • O=C(NC(C(N)=O)C(C)(C)C)C1=NN(CC2=CC=CC=C2)C3=C1C=CC=C3
  • 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-BINACA (also known asADMB-BZINACA using EMCDDA naming standards[1]) is acannabinoiddesigner drug that has been found as an ingredient in somesynthetic cannabis products.[2] It was originally developed byPfizer as a potentialanalgesic, and is a potentagonist of theCB1 receptor with abinding affinity (Ki) of 0.33 nM and anEC50 of 14.7 nM.[3]

Adb-Butinaca

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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 asADB-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

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References

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  1. ^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.S2CID 253396419.
  2. ^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.
  3. ^WO 2009106982, "Indazole Derivatives" 
  4. ^Kavanagh P, Pechnikov A, Nikolaev I, Dowling G, Kolosova M, Grigoryev A (July 2022). "Detection of ADB-BUTINACA Metabolites in Human Urine, Blood, Kidney and Liver".Journal of Analytical Toxicology.46 (6):641–650.doi:10.1093/jat/bkab088.PMID 34341821.
  5. ^Sia CH, Wang Z, Goh EM, Tan YL, Fong CY, Moy HY, et al. (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.
  6. ^Kronstrand R, Norman C, Vikingsson S, Biemans A, Valencia Crespo B, Edwards D, et al. (April 2022)."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.doi:10.1002/dta.3203.PMID 34811926.S2CID 244490343.
  7. ^Wang Y, Pan Y, Yang H, Liu J, Wurita A, Hasegawa K (July 2022). "Quantification of MDMB-4en-PINACA and ADB-BUTINACA in human hair by gas chromatography-tandem mass spectrometry".Forensic Toxicology.40 (2):340–348.doi:10.1007/s11419-022-00615-z.PMID 36454410.S2CID 247501663.
  8. ^King A, Hill SL, Pucci M, Bailey G, Keating L, Macfarlane R, et al. (October 2022). "Clinical features associated with ADB-BUTINACA exposure in patients attending emergency departments in England".Clinical Toxicology.60 (10):1094–1098.doi:10.1080/15563650.2022.2101469.PMID 35943421.S2CID 251444625.
  9. ^Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, et al. (December 2020). "Synthesis andin 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.
  10. ^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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