{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,6]],"date-time":"2026-05-06T12:49:36Z","timestamp":1778071776611,"version":"3.51.4"},"reference-count":39,"publisher":"Oxford University Press (OUP)","issue":"9","license":[{"start":{"date-parts":[[2023,9,25]],"date-time":"2023-09-25T00:00:00Z","timestamp":1695600000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003945","name":"Link\u00f6pings Universitet","doi-asserted-by":"publisher","award":["Styrkeomradet forensiska vetenskaper"],"award-info":[{"award-number":["Styrkeomradet forensiska vetenskaper"]}],"id":[{"id":"10.13039\/501100003945","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Eurostars-3","award":["E! 2297"],"award-info":[{"award-number":["E! 2297"]}]},{"name":"Eurostars-2","award":["E! 113377"],"award-info":[{"award-number":["E! 113377"]}]},{"DOI":"10.13039\/501100001858","name":"VINNOVA","doi-asserted-by":"publisher","award":["2019-03566"],"award-info":[{"award-number":["2019-03566"]}],"id":[{"id":"10.13039\/501100001858","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000275","name":"Leverhulme Trust","doi-asserted-by":"publisher","award":["RC-2015-01"],"award-info":[{"award-number":["RC-2015-01"]}],"id":[{"id":"10.13039\/501100000275","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003945","name":"Link\u00f6pings Universitet","doi-asserted-by":"publisher","award":["Styrkeomradet forensiska vetenskaper"],"award-info":[{"award-number":["Styrkeomradet forensiska vetenskaper"]}],"id":[{"id":"10.13039\/501100003945","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Eurostars-3","award":["E! 2297"],"award-info":[{"award-number":["E! 2297"]}]},{"name":"Eurostars-2","award":["E! 113377"],"award-info":[{"award-number":["E! 113377"]}]},{"DOI":"10.13039\/501100001858","name":"VINNOVA","doi-asserted-by":"publisher","award":["2019-03566"],"award-info":[{"award-number":["2019-03566"]}],"id":[{"id":"10.13039\/501100001858","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000275","name":"Leverhulme Trust","doi-asserted-by":"publisher","award":["RC-2015-01"],"award-info":[{"award-number":["RC-2015-01"]}],"id":[{"id":"10.13039\/501100000275","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2023,12,12]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:p>Synthetic cannabinoid receptor agonists (SCRAs) remain a major public health concern, with their use implicated in intoxications and drug-related deaths worldwide. Increasing our systematic understanding of SCRA metabolism supports clinical and forensic toxicology casework, facilitating the timely identification of analytical targets for toxicological screening procedures and confirmatory analysis. This is particularly important as new SCRAs continue to emerge on the illicit drug market. In this work, the metabolism of ADB-HEXINACA (ADB-HINACA, N-[1-amino-3,3-dimethyl-1-oxobutan-2-yl]-1-hexyl-1H-indazole-3-carboxamide), which has increased in prevalence in the United Kingdom and other jurisdictions, was investigated using in vitro techniques. The (S)-enantiomer of ADB-HEXINACA was incubated with pooled human hepatocytes over 3 hours to identify unique and abundant metabolites using liquid chromatography\u2013quadrupole time-of-flight mass spectrometry. In total, 16 metabolites were identified, resulting from mono-hydroxylation, di-hydroxylation, ketone formation (mono-hydroxylation then dehydrogenation), carboxylic acid formation, terminal amide hydrolysis, dihydrodiol formation, glucuronidation and combinations thereof. The majority of metabolism took place on the hexyl tail, forming ketone and mono-hydroxylated products. The major metabolite was the 5-oxo-hexyl product (M9), while the most significant mono-hydroxylation product was the 4-hydroxy-hexyl product (M8), both of which were confirmed by comparison to in-house synthesized reference standards. The 5-hydroxy-hexyl (M6) and 6-hydroxy-hexyl (M7) metabolites were not chromatographically resolved, and the 5-hydroxy-hexyl product was the second largest mono-hydroxylated metabolite. The structures of the terminal amide hydrolysis products without (M16, third largest metabolite) and with the 5-positioned ketone (M13) were also confirmed by comparison to synthesized reference standards, along with the 4-oxo-hexyl metabolite (M11). The 5-oxo-hexyl and 4-hydroxy-hexyl metabolites are suggested as biomarkers for ADB-HEXINACA consumption.<\/jats:p>","DOI":"10.1093\/jat\/bkad065","type":"journal-article","created":{"date-parts":[[2023,9,25]],"date-time":"2023-09-25T17:34:37Z","timestamp":1695663277000},"page":"826-834","source":"Crossref","is-referenced-by-count":14,"title":["The metabolic profile of\u00a0the synthetic cannabinoid receptor agonist ADB-HEXINACA using human hepatocytes, LC\u2013QTOF-MS and\u00a0synthesized reference standards"],"prefix":"10.1093","volume":"47","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5615-1199","authenticated-orcid":false,"given":"Steven R","family":"Baginski","sequence":"first","affiliation":[{"name":"Leverhulme Research Centre for Forensic Science, School of Science and Engineering, University of Dundee , Fleming Laboratory, Small\u2019s Wynd, Dundee DD1 4HN, UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0857-6261","authenticated-orcid":false,"given":"Tobias","family":"Rautio","sequence":"additional","affiliation":[{"name":"Department of Physics, Chemistry and Biology, Link\u00f6ping University , Link\u00f6ping 581 83, Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8789-9113","authenticated-orcid":false,"given":"Lorna A","family":"Nisbet","sequence":"additional","affiliation":[{"name":"Leverhulme Research Centre for Forensic Science, School of Science and Engineering, University of Dundee , Fleming Laboratory, Small\u2019s Wynd, Dundee DD1 4HN, UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Karin","family":"Lindbom","sequence":"additional","affiliation":[{"name":"Division of Clinical Chemistry and Pharmacology, Department of Biomedical and Clinical Sciences, Faculty of Medicine and Health Sciences, Link\u00f6ping University , Link\u00f6ping 581 83, Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6756-2276","authenticated-orcid":false,"given":"Xiongyu","family":"Wu","sequence":"additional","affiliation":[{"name":"Department of Physics, Chemistry and Biology, Link\u00f6ping University , Link\u00f6ping 581 83, Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Johan","family":"Dahl\u00e9n","sequence":"additional","affiliation":[{"name":"Department of Physics, Chemistry and Biology, Link\u00f6ping University , Link\u00f6ping 581 83, Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7244-5779","authenticated-orcid":false,"given":"Craig","family":"McKenzie","sequence":"additional","affiliation":[{"name":"Leverhulme Research Centre for Forensic Science, School of Science and Engineering, University of Dundee , Fleming Laboratory, Small\u2019s Wynd, Dundee DD1 4HN, UK"},{"name":"Chiron AS , Stiklestadveien 1, Trondheim 7041, Norway"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8015-5728","authenticated-orcid":false,"given":"Henrik","family":"Gr\u00e9en","sequence":"additional","affiliation":[{"name":"Division of Clinical Chemistry and Pharmacology, Department of Biomedical and Clinical Sciences, Faculty of Medicine and Health Sciences, Link\u00f6ping University , Link\u00f6ping 581 83, Sweden"},{"name":"Department of Forensic Genetics and Forensic Toxicology, National Board of Forensic Medicine , Artillerigatan 12, Link\u00f6ping 587 58, Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"286","published-online":{"date-parts":[[2023,9,25]]},"reference":[{"key":"2023121213572198100_R1","article-title":"Synthetic cannabinoid receptor agonists (SCRA): An updated harms assessment and\u00a0a review of\u00a0classification and\u00a0scheduling under the Misuse of\u00a0Drugs Act 1971 and\u00a0its Regulations","author":"Advisory Council on the Misuse of Drugs","year":"2020"},{"key":"2023121213572198100_R2","doi-asserted-by":"crossref","DOI":"10.1016\/j.drugpo.2021.103396","article-title":"\u2018Synthetic cannabis\u2019: A dangerous misnomer","volume":"98","author":"Darke","year":"2021","journal-title":"International Journal of Drug Policy"},{"key":"2023121213572198100_R3","doi-asserted-by":"crossref","first-page":"S163","DOI":"10.1038\/sj.bjp.0706406","article-title":"Cannabinoid pharmacology: The first 66 years","volume":"147","author":"Pertwee","year":"2006","journal-title":"British Journal of Pharmacology"},{"key":"2023121213572198100_R4","doi-asserted-by":"crossref","DOI":"10.3389\/fpsyt.2020.00464","article-title":"Post-mortem toxicology: A systematic review of\u00a0death cases involving synthetic cannabinoid receptor agonists","volume":"11","author":"Giorgetti","year":"2020","journal-title":"Frontiers in Psychiatry"},{"key":"2023121213572198100_R5","article-title":"New psychoactive substances: 25 years of\u00a0early warning and\u00a0response in\u00a0Europe","author":"European Monitoring Centre for Drugs and Drug Addiction","year":"2022"},{"key":"2023121213572198100_R6","doi-asserted-by":"crossref","first-page":"628","DOI":"10.1002\/dta.2965","article-title":"Shape matters: The application of\u00a0activity-based in\u00a0vitro bioassays and\u00a0chiral profiling to the pharmacological evaluation of\u00a0synthetic cannabinoid receptor agonists in\u00a0drug-infused papers seized in\u00a0prisons","volume":"13","author":"Antonides","year":"2021","journal-title":"Drug Testing and Analysis"},{"key":"2023121213572198100_R7","doi-asserted-by":"crossref","first-page":"1546","DOI":"10.1021\/acschemneuro.5b00112","article-title":"Pharmacology of\u00a0indole and\u00a0indazole synthetic cannabinoid designer drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, and\u00a05F-ADBICA","volume":"6","author":"Banister","year":"2015","journal-title":"ACS Chemical Neuroscience"},{"key":"2023121213572198100_R8","doi-asserted-by":"crossref","first-page":"4434","DOI":"10.1021\/acschemneuro.0c00644","article-title":"Synthesis and\u00a0in vitro cannabinoid receptor 1 activity of\u00a0recently 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\u00a05F-AP7AICA","volume":"11","author":"Cannaert","year":"2020","journal-title":"ACS Chemical Neuroscience"},{"key":"2023121213572198100_R9","doi-asserted-by":"crossref","first-page":"1402","DOI":"10.1002\/dta.3035","article-title":"Systematic evaluation of\u00a0a panel of\u00a030 synthetic cannabinoid receptor agonists structurally related to MMB-4en-PICA, MDMB-4en-PINACA, ADB-4en-PINACA, and\u00a0MMB-4CN-BUTINACA using a combination of\u00a0binding and\u00a0different CB1 receptor activation assays\u2014Part II: Structure activity relationship assessment via a \u03b2-arrestin recruitment assay","volume":"13","author":"Grafinger","year":"2021","journal-title":"Drug Testing and Analysis"},{"key":"2023121213572198100_R10","doi-asserted-by":"crossref","DOI":"10.1016\/j.forsciint.2019.110106","article-title":"Effects of\u00a0lipophilicity and\u00a0functional groups of\u00a0synthetic cannabinoids on\u00a0their blood concentrations and\u00a0urinary excretion","volume":"307","author":"Kakehashi","year":"2020","journal-title":"Forensic Science International"},{"key":"2023121213572198100_R11","doi-asserted-by":"crossref","DOI":"10.3390\/molecules26051396","article-title":"A systematic study of\u00a0the in\u00a0vitro pharmacokinetics and\u00a0estimated human in\u00a0vivo clearance of\u00a0indole and\u00a0indazole-3-carboxamide synthetic cannabinoid receptor agonists detected on\u00a0the illicit drug 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inhalation","volume":"150","author":"Toennes","year":"2018","journal-title":"Journal of Pharmaceutical and Biomedical Analysis"},{"key":"2023121213572198100_R15","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1016\/j.jpba.2017.03.043","article-title":"Pharmacokinetic properties of\u00a0the synthetic cannabinoid JWH-018 and\u00a0of its metabolites in\u00a0serum after inhalation","volume":"140","author":"Toennes","year":"2017","journal-title":"Journal of Pharmaceutical and Biomedical Analysis"},{"key":"2023121213572198100_R16","doi-asserted-by":"crossref","first-page":"644","DOI":"10.1002\/dta.2310","article-title":"Pharmacokinetic properties of\u00a0the synthetic cannabinoid JWH-018 in\u00a0oral fluid after inhalation","volume":"10","author":"Toennes","year":"2018","journal-title":"Drug Testing and Analysis"},{"key":"2023121213572198100_R17","doi-asserted-by":"crossref","first-page":"2659","DOI":"10.1016\/j.jchromb.2010.03.016","article-title":"Sensitive and\u00a0rapid quantification of\u00a0the cannabinoid receptor agonist naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-018) in\u00a0human serum by liquid chromatography-tandem mass spectrometry","volume":"878","author":"Teske","year":"2010","journal-title":"Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences"},{"key":"2023121213572198100_R18","doi-asserted-by":"crossref","first-page":"316","DOI":"10.1007\/s11419-018-00462-x","article-title":"Structure-metabolism relationships of\u00a0valine and\u00a0tert-leucine-derived synthetic cannabinoid receptor agonists: a systematic comparison of\u00a0the in\u00a0vitro phase I metabolism using pooled human liver microsomes and\u00a0high-resolution mass spectrometry","volume":"37","author":"Franz","year":"2019","journal-title":"Forensic Toxicology"},{"key":"2023121213572198100_R19","doi-asserted-by":"crossref","DOI":"10.1016\/j.forc.2021.100354","article-title":"Synthesis, characterisation, detection and\u00a0quantification of\u00a0a novel hexyl-substituted synthetic cannabinoid receptor agonist: (S)-N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-hexyl-1H-indazole-3-carboxamide (ADB-HINACA)","volume":"26","author":"Gilbert","year":"2021","journal-title":"Forensic 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(MAB-CHMINACA) metabolites in\u00a0human hepatocytes","volume":"19","author":"Carlier","year":"2017","journal-title":"The AAPS Journal"},{"key":"2023121213572198100_R27","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1007\/s00204-018-2330-9","article-title":"Correlations between metabolism and\u00a0structural elements of\u00a0the alicyclic fentanyl analogs cyclopropyl fentanyl,cyclobutyl fentanyl,cyclopentyl fentanyl,cyclohexyl fentanyl and\u00a02,2,3,3-tetramethylcyclopropyl fentanyl studied by human hepatocytes and\u00a0LC-QTOF-MS","volume":"93","author":"\u00c5strand","year":"2019","journal-title":"Archives of Toxicology"},{"key":"2023121213572198100_R28","doi-asserted-by":"crossref","DOI":"10.1208\/s12248-019-0381-3","article-title":"Biotransformation of\u00a0the new synthetic cannabinoid with an alkene, MDMB-4en-PINACA, by human hepatocytes, human liver microsomes, and\u00a0human urine and\u00a0blood","volume":"22","author":"Watanabe","year":"2020","journal-title":"The 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in\u00a0urine Forensic Toxicology","volume":"406","author":"Kronstrand","year":"2014","journal-title":"Analytical and Bioanalytical Chemistry"},{"key":"2023121213572198100_R37","doi-asserted-by":"crossref","first-page":"500","DOI":"10.1002\/dta.1661","article-title":"Signal enhancement of\u00a0glucuronide conjugates in\u00a0LC-MS\/MS by derivatization with the phosphonium propylamine cation tris(trimethoxyphenyl) phosphonium propylamine, for\u00a0forensic purposes","volume":"6","author":"Turfus","year":"2014","journal-title":"Drug Testing and Analysis"},{"key":"2023121213572198100_R38","doi-asserted-by":"crossref","first-page":"1433","DOI":"10.1002\/rcm.1071","article-title":"Cone voltage induced in-source dissociation of\u00a0glucuronides in electrospray and\u00a0implications in\u00a0biological analyses","volume":"17","author":"Yan","year":"2003","journal-title":"Rapid Communications in Mass 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