Gutenberg Open Science: Analysis of tetramisole metabolites : is “Aminorex” found in forensic samples of cocaine users actually 4-phenyl-2-imidazolidinone?

Please use this identifier to cite or link to this item: http://doi.org/10.25358/openscience-9535

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DC Field	Value	Language
dc.contributor.author	Hundertmark, Marica	-
dc.contributor.author	Hess, Cornelius	-
dc.contributor.author	Röhrich, Jörg	-
dc.contributor.author	Wunder, Cora	-
dc.contributor.author	Losacker, Moritz	-
dc.date.accessioned	2023-09-12T10:42:48Z	-
dc.date.available	2023-09-12T10:42:48Z	-
dc.date.issued	2023	-
dc.identifier.uri	https://openscience.ub.uni-mainz.de/handle/20.500.12030/9553	-
dc.description.abstract	Phenyltetrahydroimidazothiazole (PTHIT, tetramisole) is a common adulterant in cocaine samples. Little is known about its human metabolism. p-hydroxy-PTHIT has long been the only proven phase-I-metabolite. 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-phenyl-2-imidazolidinone 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-positive samples. A liquid chromatography–tandem mass spectrometry (LC–MS/MS) method was validated for quantification of 4-phenyl-2-imidazolidinone and p-hydroxy-PTHIT (LOQ 0.05 ng/ml each). Selectivity was ensured for 4-phenyl-2-imidazolidinone and aminorex (LOD 0.05 ng/ml). After controlled nasal uptake of tetramisole (10 mg, n = 3) a shorter half-life for p-hydroxy-PTHIT (3.4–5.8 h) was determined than for 4-phenyl-2-imidazolidinone (14.0–15.9 h). p-hydroxy-PTHIT (33%) and 4-phenyl-2-imidazolidinone (51%) were also detected in serum samples from cocaine users tested previously positive for PTHIT (n = 73). Aminorex was never detected. The potential of misinterpreting 4-phenyl-2-imidazolidinone as aminorex was tested using a gas chromatography–mass spectrometry (GC–MS) method used in the literature and an in-house liquid chromatography-time-of-flight mass spectrometry (LC-QTOF) screening-method. Using GC–MS the analysed bis-trimethylsilyl-derivatives cannot be differentiated due to co-elution. Both substances were chromatographically separated using the LC-QTOF method, but library comparison workflows misinterpreted 4-phenyl-2-imidazolidinone as aminorex. 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-phenyl-2-imidazolidinone.	en_GB
dc.description.sponsorship	Deutsche Forschungsgemeinschaft (DFG)\|491381577\|Open-Access-Publikationskosten 2022–2024 Universität Mainz - Universitätsmedizin	-
dc.language.iso	eng	de
dc.rights	CC BY	*
dc.rights.uri	https://creativecommons.org/licenses/by/4.0/	*
dc.subject.ddc	610 Medizin	de_DE
dc.subject.ddc	610 Medical sciences	en_GB
dc.title	Analysis of tetramisole metabolites : is “Aminorex” found in forensic samples of cocaine users actually 4-phenyl-2-imidazolidinone?	en_GB
dc.type	Zeitschriftenaufsatz	de
dc.identifier.doi	http://doi.org/10.25358/openscience-9535	-
jgu.type.dinitype	article	en_GB
jgu.type.version	Published version	de
jgu.type.resource	Text	de
jgu.organisation.department	FB 04 Medizin	de
jgu.organisation.number	2700	-
jgu.organisation.name	Johannes Gutenberg-Universität Mainz	-
jgu.rights.accessrights	openAccess	-
jgu.journal.title	Drug testing and analysis	de
jgu.journal.volume	15	de
jgu.journal.issue	8	de
jgu.pages.start	865	de
jgu.pages.end	878	de
jgu.publisher.year	2023	-
jgu.publisher.name	Wiley	de
jgu.publisher.place	Hoboken, NJ	de
jgu.publisher.issn	1942-7611	de
jgu.organisation.place	Mainz	-
jgu.subject.ddccode	610	de
jgu.publisher.doi	10.1002/dta.3482	de
jgu.organisation.ror	https://ror.org/023b0x485	-
Appears in collections:	DFG-491381577-H

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