{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,10]],"date-time":"2026-09-10T12:57:34Z","timestamp":1789045054616,"version":"build-2803163510"},"reference-count":33,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2023,4,19]],"date-time":"2023-04-19T00:00:00Z","timestamp":1681862400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2023,8]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Phenyltetrahydroimidazothiazole (PTHIT, tetramisole) is a common adulterant in cocaine samples. Little is known about its human metabolism.\n                    <jats:italic>p<\/jats:italic>\n                    \u2010hydroxy\u2010PTHIT has long been the only proven phase\u2010I\u2010metabolite. Another putative metabolite is the stimulant aminorex. However, data on its analytical proof is rare and contradictory. Even less known is its constitutional isomer 4\u2010phenyl\u20102\u2010imidazolidinone which has only been proven in animal samples so far. The aim of the study was to get insight into the metabolism of PTHIT after controlled nasal uptake of PTHIT and in real forensic cocaine\/benzoylecgonine\u2010positive samples.\n                  <\/jats:p>\n                  <jats:p>\n                    A liquid chromatography\u2013tandem mass spectrometry (LC\u2013MS\/MS) method was validated for quantification of 4\u2010phenyl\u20102\u2010imidazolidinone and\n                    <jats:italic>p<\/jats:italic>\n                    \u2010hydroxy\u2010PTHIT (LOQ 0.05\u2009ng\/ml each). Selectivity was ensured for 4\u2010phenyl\u20102\u2010imidazolidinone and aminorex (LOD 0.05\u2009ng\/ml). After controlled nasal uptake of tetramisole (10\u00a0mg, n\u2009=\u20093) a shorter half\u2010life for\n                    <jats:italic>p<\/jats:italic>\n                    \u2010hydroxy\u2010PTHIT (3.4\u20135.8\u00a0h) was determined than for 4\u2010phenyl\u20102\u2010imidazolidinone (14.0\u201315.9\u00a0h).\n                    <jats:italic>p<\/jats:italic>\n                    \u2010hydroxy\u2010PTHIT (33%) and 4\u2010phenyl\u20102\u2010imidazolidinone (51%) were also detected in serum samples from cocaine users tested previously positive for PTHIT (n\u2009=\u200973). Aminorex was never detected.\n                  <\/jats:p>\n                  <jats:p>The potential of misinterpreting 4\u2010phenyl\u20102\u2010imidazolidinone as aminorex was tested using a gas chromatography\u2013mass spectrometry (GC\u2013MS) method used in the literature and an in\u2010house liquid chromatography\u2010time\u2010of\u2010flight mass spectrometry (LC\u2010QTOF) screening\u2010method. Using GC\u2013MS the analysed bis\u2010trimethylsilyl\u2010derivatives cannot be differentiated due to co\u2010elution. Both substances were chromatographically separated using the LC\u2010QTOF method, but library comparison workflows misinterpreted 4\u2010phenyl\u20102\u2010imidazolidinone as aminorex.<\/jats:p>\n                  <jats:p>It seems likely that aminorex, which was allegedly identified as a metabolite of PTHIT in samples of cocaine users in previous studies, is in fact 4\u2010phenyl\u20102\u2010imidazolidinone.<\/jats:p>","DOI":"10.1002\/dta.3482","type":"journal-article","created":{"date-parts":[[2023,4,14]],"date-time":"2023-04-14T00:48:46Z","timestamp":1681433326000},"page":"865-878","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Analysis of tetramisole metabolites \u2013 Is \u201cAminorex\u201d found in forensic samples of cocaine users actually 4\u2010phenyl\u20102\u2010imidazolidinone?"],"prefix":"10.1002","volume":"15","author":[{"ORCID":"https:\/\/orcid.org\/0009-0008-7261-6628","authenticated-orcid":false,"given":"Marica","family":"Hundertmark","sequence":"first","affiliation":[{"name":"Department of Forensic Toxicology Institute of Legal Medicine, University Medical Center Mainz  Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8405-4417","authenticated-orcid":false,"given":"Cornelius","family":"Hess","sequence":"additional","affiliation":[{"name":"Department of Forensic Toxicology Institute of Legal Medicine, University Medical Center Mainz  Mainz Germany"},{"name":"MVZ Dr. Stein und Kollegen M\u00f6nchengladbach, Forensic toxicology  M\u00f6nchengladbach Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J\u00f6rg","family":"R\u00f6hrich","sequence":"additional","affiliation":[{"name":"Department of Forensic Toxicology Institute of Legal Medicine, University Medical Center Mainz  Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5150-268X","authenticated-orcid":false,"given":"Cora","family":"Wunder","sequence":"additional","affiliation":[{"name":"Department of Forensic Toxicology Institute of Legal Medicine, University Medical Center Mainz  Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8880-1512","authenticated-orcid":false,"given":"Moritz","family":"Losacker","sequence":"additional","affiliation":[{"name":"Department of Forensic Toxicology Institute of Legal Medicine, University Medical Center Mainz  Mainz Germany"},{"name":"MVZ Laboratory Krone, Forensic and clinical toxicology  Bad Salzuflen 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