{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T12:30:24Z","timestamp":1790857824712,"version":"4.1.0"},"reference-count":54,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2021,12,10]],"date-time":"2021-12-10T00:00:00Z","timestamp":1639094400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003945","name":"Link\u00f6pings Universitet","doi-asserted-by":"publisher","award":["Strategic Research Area in Forensic Sciences"],"award-info":[{"award-number":["Strategic Research Area in Forensic Sciences"]}],"id":[{"id":"10.13039\/501100003945","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000275","name":"Leverhulme Trust","doi-asserted-by":"publisher","award":["RC\u20102015\u201001"],"award-info":[{"award-number":["RC\u20102015\u201001"]}],"id":[{"id":"10.13039\/501100000275","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003945","name":"Link\u00f6pings Universitet","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003945","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001858","name":"VINNOVA","doi-asserted-by":"publisher","award":["2019\u201003566"],"award-info":[{"award-number":["2019\u201003566"]}],"id":[{"id":"10.13039\/501100001858","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000780","name":"European Commission","doi-asserted-by":"publisher","award":["E! 113377 (Eurostars\u20102)"],"award-info":[{"award-number":["E! 113377 (Eurostars\u20102)"]}],"id":[{"id":"10.13039\/501100000780","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2022,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Early warning systems detect new psychoactive substances (NPS), while dedicated monitoring programs and routine drug and toxicology testing identify fluctuations in prevalence. We report the increasing prevalence of the synthetic cannabinoid receptor agonist (SCRA) ADB\u2010BUTINACA (<jats:italic>N<\/jats:italic>\u2010[1\u2010amino\u20103,3\u2010dimethyl\u20101\u2010oxobutan\u20102\u2010yl]\u20101\u2010butyl\u20101<jats:italic>H<\/jats:italic>\u2010indazole\u20103\u2010carbox\u2010amide). ADB\u2010BUTINACA was first detected in a seizure in Sweden in 2019, and we report its detection in 13 routine Swedish forensic toxicology cases soon after. In January 2021, ADB\u2010BUTINACA was detected in SCRA\u2010infused papers seized in Scottish prisons and has rapidly increased in prevalence, being detected in 60.4% of the SCRA\u2010infused papers tested between January and July 2021. In this work, ADB\u2010BUTINACA was incubated with human hepatocytes (HHeps), and 21 metabolites were identified in vitro, 14 being detected in authentic case samples. The parent drug and metabolites B9 (mono\u2010hydroxylation on the <jats:italic>n<\/jats:italic>\u2010butyl tail) and B16 (mono\u2010hydroxylation on the indazole ring) are recommended biomarkers in blood, while metabolites B4 (dihydrodiol formation on the indazole core), B9, and B16 are suitable biomarkers in urine. ADB\u20104en\u2010PINACA (<jats:italic>N<\/jats:italic>\u2010[1\u2010amino\u20103,3\u2010dimethyl\u20101\u2010oxobutan\u20102\u2010yl]\u20101\u2010[pent\u20104\u2010en\u20101\u2010yl]\u20101<jats:italic>H<\/jats:italic>\u2010indazole\u20103\u2010carboxamide) was detected in Scottish prisons in December 2020, but, unlike ADB\u2010BUTINACA, prevalence has remained low. ADB\u20104en\u2010PINACA was incubated with HHeps, and 11 metabolites were identified. Metabolites E3 (dihydrodiol formed in the tail moiety) and E7 (hydroxylation on the linked\/head group) are the most abundant metabolites in vitro and are suggested as urinary biomarkers. The in vitro potencies of ADB\u2010BUTINACA (EC<jats:sub>50<\/jats:sub>, 11.5\u00a0nM and ADB\u20104en\u2010PINACA (EC<jats:sub>50<\/jats:sub>, 11.6\u00a0nM) are similar to that of MDMB\u20104en\u2010PINACA (EC<jats:sub>50<\/jats:sub>, 4.3\u00a0nM). A third <jats:italic>tert<\/jats:italic>\u2010leucinamide SCRA, ADB\u2010HEXINACA was also detected in prison samples and warrants further investigation.<\/jats:p>","DOI":"10.1002\/dta.3203","type":"journal-article","created":{"date-parts":[[2021,11,23]],"date-time":"2021-11-23T02:44:39Z","timestamp":1637635479000},"page":"634-652","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":74,"title":["The metabolism of the synthetic cannabinoids ADB\u2010BUTINACA and ADB\u20104en\u2010PINACA and their detection in forensic toxicology casework and infused papers seized in prisons"],"prefix":"10.1002","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4222-9597","authenticated-orcid":false,"given":"Robert","family":"Kronstrand","sequence":"first","affiliation":[{"name":"Department of Forensic Genetics and Forensic Toxicology National Board of Forensic Medicine  Link\u00f6ping Sweden"},{"name":"Division of Clinical Chemistry and Pharmacology, Department of Biomedical and Clinical Sciences, Faculty of Medicine and Health Sciences Link\u00f6ping University  Link\u00f6ping Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2322-0367","authenticated-orcid":false,"given":"Caitlyn","family":"Norman","sequence":"additional","affiliation":[{"name":"Leverhulme Research Centre for Forensic Science, School of Science and Engineering University of Dundee  Dundee UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5977-3049","authenticated-orcid":false,"given":"Svante","family":"Vikingsson","sequence":"additional","affiliation":[{"name":"Department of Forensic Genetics and Forensic Toxicology National Board of Forensic Medicine  Link\u00f6ping Sweden"},{"name":"Division of Clinical Chemistry and Pharmacology, Department of Biomedical and Clinical Sciences, Faculty of Medicine and Health Sciences Link\u00f6ping University  Link\u00f6ping Sweden"},{"name":"RTI International  Research Triangle North Carolina USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anoek","family":"Biemans","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 Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bryan","family":"Valencia Crespo","sequence":"additional","affiliation":[{"name":"Department of Physics, Chemistry and Biology Link\u00f6ping University  Link\u00f6ping Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Darren","family":"Edwards","sequence":"additional","affiliation":[{"name":"Drug Discovery Unit, Wellcome Centre for Anti\u2010Infectives Research, School of Life Sciences University of Dundee  Dundee 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