View source for Chemistry:ADB-BUTINACA

{{Short description|Chemical compound}}
{{Infobox drug
| IUPAC_name = ''N''-[(2''S'')-1-amino-3,3-dimethyl-1-oxobutan-2-yl]-1-butyl-1''H''-indazole-3-carboxamide
| image = ADB-BUTINACA_structure.png
| drug_name = ADB-BUTINACA

<!--Clinical data-->
| tradename =  
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category =  
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_BR = F2
| legal_CA = Schedule II
| legal_DE = NpSG
| legal_UK = Class B
| legal_US = Schedule I
| legal_UN = P II 
| legal_UN_comment = <ref>{{Cite web |title=Substance Details ADB-BUTINACA |url=https://www.unodc.org/LSS/Substance/Details/d1934790-552e-4810-b1a1-e99cd3991c49 |access-date=2024-01-22}}</ref>
| legal_status = 
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability =  
| protein_bound =  
| metabolism =  
| elimination_half-life =  
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 2682867-55-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ZJ6LS4NVM9
| ATC_prefix =  
| ATC_suffix =  
| PubChem = 155907792
| ChemSpiderID      = 81407832
| ChEMBL = 5169682
| smiles            = O=C(N[C@H](C(N)=O)C(C)(C)C)C1=NN(CCCC)C2=C1C=CC=C2
| StdInChI          = 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
| StdInChIKey       = GPWADXHYJAZPAX-OAHLLOKOSA-N

<!--Chemical data-->
| C=18 | H=26 | N=4 | O=2
}}

'''ADB-BUTINACA''' ('''ADMB-BINACA'''<ref>{{cite journal |last1=Pulver |first1=Benedikt |last2=Fischmann |first2=Svenja |last3=Gallegos |first3=Ana |last4=Christie |first4=Rachel |title=EMCDDA framework and practical guidance for naming synthetic cannabinoids |journal=Drug Testing and Analysis |date=March 2023 |volume=15 |issue=3 |pages=255–276 |doi=10.1002/dta.3403}}</ref>) is a synthetic cannabinoid compound which has been sold as a [[Chemistry:Designer drug|designer drug]].<ref>{{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 }}</ref><ref>{{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 }}</ref><ref>{{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 | display-authors = 6 | 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 }}</ref><ref>{{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 }}</ref><ref>{{cite journal | vauthors = King A, Hill SL, Pucci M, Bailey G, Keating L, Macfarlane R, Cantle F, Hudson S, Thomas SH | display-authors = 6 | 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 }}</ref> It is a potent CB<sub>1</sub> agonist, with a binding affinity of 0.29nM for CB1 and 0.91nM for CB2, and an EC<sub>50</sub> of 6.36 nM for CB1.<ref>https://cdn.who.int/media/docs/default-source/controlled-substances/45th-ecdd/adb-butinaca_draft.pdf</ref><ref>{{cite journal | vauthors = Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, Ellison R, Gerona R, Banister SD, Stove CP | display-authors = 6 | 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 }}</ref><ref>{{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 | display-authors = 6 | 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 CB<sub>1</sub> receptor activation assays: Part I-Synthesis, analytical characterization, and binding affinity for human CB<sub>1</sub> receptors | journal = Drug Testing and Analysis | volume = 13 | issue = 7 | pages = 1383–1401 | date = July 2021 | pmid = 33787091 | doi = 10.1002/dta.3037 }}</ref><ref>{{cite journal | vauthors = Sparkes E, Cairns EA, Kevin RC, Lai F, Grafinger KE, Chen S, Deventer MH, Ellison R, Boyd R, Martin LJ, McGregor IS, Gerona RR, Hibbs DE, Auwärter V, Glass M, Stove C, Banister SD | display-authors = 6 | title = Structure-activity relationships of valine, ''tert''-leucine, and phenylalanine amino acid-derived synthetic cannabinoid receptor agonists related to ADB-BUTINACA, APP-BUTINACA, and ADB-P7AICA | journal = RSC Medicinal Chemistry | volume = 13 | issue = 2 | pages = 156–174 | date = February 2022 | doi = 10.1039/D1MD00242B | pmid = 35308023 | s2cid = 239951357 | pmc = 8864554 }}</ref><ref>{{cite journal | vauthors = Fan X, Zhang J, Fu X, Zhou B, Xu Z, Huang H, Han S, Li X | display-authors = 6 | title = Analysis of synthetic cannabinoids in wastewater of major cities in China | journal = The Science of the Total Environment | volume = 827 | pages = 154267 | date = June 2022 | doi = 10.1016/j.scitotenv.2022.154267 | pmid = 35247413 | bibcode = 2022ScTEn.827o4267F | s2cid = 247244155 }}</ref><ref>{{cite journal | vauthors = Bäckberg M, Vikingsson S, Strandberg J, Wall S, Åstrand A, Karlsson H, Persson M, Kronstrand R, Green H | display-authors = 6 | title = Using in vitro receptor activity studies of synthetic cannabinoids to support the risk assessment of new psychoactive substances - A Swedish strategy to protect public health from harm | journal = Forensic Science International | volume = 348 | pages = 111691 | date = July 2023 | doi = 10.1016/j.forsciint.2023.111691 | pmid = 37116244 | s2cid = 258152652 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Tokarczyk B, Suchan M, Adamowicz P | title = New Synthetic Cannabinoid ADB-BUTINACA-Related Death of a Police Dog | journal = Journal of Analytical Toxicology | volume = 47 | issue = 2 | pages = e23–e28 | date = March 2023 | doi = 10.1093/jat/bkac097 | pmid = 36472351 }}</ref>

==See also==
* [[Chemistry:ADB-BINACA|ADB-BINACA]]
* [[Chemistry:ADB-PINACA|ADB-PINACA]]
* [[Chemistry:ADB-HEXINACA|ADB-HEXINACA]]
* [[Chemistry:ADB-5'F-BUTINACA|ADB-5'F-BUTINACA]]
* [[Chemistry:ADB-5'Br-BUTINACA|ADB-5'Br-BUTINACA]]

== References ==
{{reflist}}

{{Cannabinoids}}

[[Category:Cannabinoids]]
[[Category:Designer drugs]]
[[Category:Tert-butyl compounds]]

{{Sourceattribution|ADB-BUTINACA}}