ADB-BINACA
{{Short description|Chemical compound}}
{{Use dmy dates|date=February 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| IUPAC_name = N-[(2S)-1-amino-3,3-dimethyl-1-oxobutan-2-yl]-1-benzyl-1H-indazole-3-carboxamide
| image = ADB-BINACA_structure.png
| image_class = skin-invert-image
| tradename =
| pregnancy_AU =
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| legal_AU =
| legal_CA = Schedule II
| legal_DE = Anlage II
| legal_UK = Class B
| legal_US = Schedule I
| legal_status =
| routes_of_administration =
| bioavailability =
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| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 1185282-27-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = PUVP61SOSI
| ATC_prefix =
| ATC_suffix =
| 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{{cite journal | vauthors = Pulver B, Fischmann S, Gallegos A, Christie R | title = EMCDDA framework and practical guidance for naming synthetic cannabinoids | journal = Drug Testing and Analysis | volume = 15 | issue = 3 | pages = 255–276 | date = March 2023 | pmid = 36346325 | doi = 10.1002/dta.3403 | s2cid = 253396419 }}) is a cannabinoid designer drug that has been found as an ingredient in some synthetic cannabis products.{{cite journal | vauthors = Qian Z, Hua Z, Liu C, Jia W | title = Four types of cannabimimetic indazole and indole derivatives, ADB-BINACA, AB-FUBICA, ADB-FUBICA, and AB-BICA, identified as new psychoactive substances | journal = Forensic Toxicology | volume = 34 | pages = 133–143 | year = 2016 | pmid = 26793280 | pmc = 4705129 | doi = 10.1007/s11419-015-0297-2 }} 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.{{Cite patent | country = WO | number = 2009106982 | title = Indazole Derivatives }}
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.{{cite journal | vauthors = Kavanagh P, Pechnikov A, Nikolaev I, Dowling G, Kolosova M, Grigoryev A | title = Detection of ADB-BUTINACA Metabolites in Human Urine, Blood, Kidney and Liver | journal = Journal of Analytical Toxicology | volume = 46 | issue = 6 | pages = 641–650 | date = July 2022 | pmid = 34341821 | doi = 10.1093/jat/bkab088 }}{{cite journal | vauthors = Sia CH, Wang Z, Goh EM, Tan YL, Fong CY, Moy HY, Chan EC | title = Urinary Metabolite Biomarkers for the Detection of Synthetic Cannabinoid ADB-BUTINACA Abuse | journal = Clinical Chemistry | volume = 67 | issue = 11 | pages = 1534–1544 | date = November 2021 | pmid = 34387654 | doi = 10.1093/clinchem/hvab134 | doi-access = free }}{{cite journal | vauthors = 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 | title = 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 | journal = Drug Testing and Analysis | volume = 14 | issue = 4 | pages = 634–652 | date = April 2022 | pmid = 34811926 | doi = 10.1002/dta.3203 | s2cid = 244490343 | url = https://discovery.dundee.ac.uk/en/publications/a9c83a12-49d4-4b09-8f08-83bac57bcc24 | doi-access = free }}{{cite journal | vauthors = Wang Y, Pan Y, Yang H, Liu J, Wurita A, Hasegawa K | title = Quantification of MDMB-4en-PINACA and ADB-BUTINACA in human hair by gas chromatography-tandem mass spectrometry | journal = Forensic Toxicology | volume = 40 | issue = 2 | pages = 340–348 | date = July 2022 | pmid = 36454410 | doi = 10.1007/s11419-022-00615-z | s2cid = 247501663 }}{{cite journal | vauthors = King A, Hill SL, Pucci M, Bailey G, Keating L, Macfarlane R, Cantle F, Hudson S, Thomas SH | title = Clinical features associated with ADB-BUTINACA exposure in patients attending emergency departments in England | journal = Clinical Toxicology | volume = 60 | issue = 10 | pages = 1094–1098 | date = October 2022 | pmid = 35943421 | doi = 10.1080/15563650.2022.2101469 | s2cid = 251444625 }} 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.{{cite journal | vauthors = Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, Ellison R, Gerona R, Banister SD, Stove CP | title = 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 | journal = ACS Chemical Neuroscience | volume = 11 | issue = 24 | pages = 4434–4446 | date = December 2020 | pmid = 33253529 | doi = 10.1021/acschemneuro.0c00644 | s2cid = 227246346 }}{{cite journal | vauthors = Pike E, Grafinger KE, Cannaert A, Ametovski A, Luo JL, Sparkes E, Cairns EA, Ellison R, Gerona R, Stove CP, Auwärter V, Banister SD | title = 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 | journal = Drug Testing and Analysis | volume = 13 | issue = 7 | pages = 1383–1401 | date = July 2021 | pmid = 33787091 | doi = 10.1002/dta.3037 }}
See also
References
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{{Cannabinoids}}