{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T19:54:03Z","timestamp":1760385243224,"version":"build-2065373602"},"reference-count":21,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2012,7,12]],"date-time":"2012-07-12T00:00:00Z","timestamp":1342051200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2012,9]]},"abstract":"<jats:p>Prenylamine is a vasodilator of phenylalkylamine structure and was used for the treatment of angina pectoris, until reports of undesirable effects including ventricular tachycardia led to a decreasing use of the drug in the 1980s. Metabolic <jats:italic>N<\/jats:italic>\u2010dealkylation of orally ingested prenylamine can liberate amphetamine in humans and cause positive findings for amphetamine in doping and forensic analysis. In 2010, the World Anti\u2010Doping Agency (WADA) classified prenylamine as a non\u2010specified stimulant according to the 2010 Prohibited List, thus banning its use in sports in\u2010competition. Supporting the development of a liquid chromatography\u2010tandem mass spectrometry (LC\u2010MS\/MS) based detection method, a post\u2010administration urine sample following a single oral prenylamine ingestion (Segontin\u00ae 60\u2009mg) was analyzed for urinary metabolites. The LC\u2010separated analytes were ionized in positive electrospray ionization (ESI) mode and detected as protonated ions using an AB Sciex TripleTOF 5600 quadrupole\u2010time\u2010of\u2010flight hybrid mass spectrometer. Over 40 phase I metabolites were detected, including previously unknown mono\u2010 bis\u2010, tris\u2010 and tetra\u2010hydroxylated prenylamine, several hydroxylated and methoxylated prenylamine metabolites and (hydroxylated) diphenylpropylamine. Investigation of the collision\u2010induced dissociation behaviours of the metabolites by high resolution\/high accuracy mass spectrometry allowed for the assignment of the nature and the site of observed metabolic transformations. The most abundant phase I metabolite was confirmed as <jats:italic>p<\/jats:italic>\u2010hydroxy\u2010prenlyamine by chemical synthesis and stable isotope labelling of reference material. An existing routine screening assay based on direct injection and LC\u2010MS\/MS analysis of urine was modified and validated according to common guidelines, in order to allow for the detection of <jats:italic>p<\/jats:italic>\u2010hydroxy\u2010prenylamine in sports drug testing. The assay demonstrated the ability to detect the target metabolite at 0.1\u2009ng\/ml at intra\u2010 and inter\u2010day imprecisions below 10%. Copyright \u00a9 2012 John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/dta.1388","type":"journal-article","created":{"date-parts":[[2012,7,12]],"date-time":"2012-07-12T02:27:41Z","timestamp":1342060061000},"page":"701-716","source":"Crossref","is-referenced-by-count":5,"title":["Identification and characterization of urinary prenylamine metabolites by means of liquid chromatography\u2010tandem mass spectrometry"],"prefix":"10.1002","volume":"4","author":[{"given":"S.","family":"Beuck","sequence":"first","affiliation":[{"name":"Institute of Biochemistry German Sport University Cologne  Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"G.","family":"Sigmund","sequence":"additional","affiliation":[{"name":"Institute of Biochemistry German Sport University Cologne  Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"A.","family":"Koch","sequence":"additional","affiliation":[{"name":"Institute of Biochemistry German Sport University Cologne  Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"W.","family":"Sch\u00e4nzer","sequence":"additional","affiliation":[{"name":"Institute of Biochemistry German Sport University Cologne  Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"A.","family":"Pokrywka","sequence":"additional","affiliation":[{"name":"Department of Anti\u2010Doping Research Institute of Sport  Warsaw Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"D.","family":"Kwiatkowska","sequence":"additional","affiliation":[{"name":"Department of Anti\u2010Doping Research Institute of Sport  Warsaw Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"M.","family":"Thevis","sequence":"additional","affiliation":[{"name":"Institute of Biochemistry German Sport University Cologne  Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2012,7,12]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1136\/hrt.36.10.1001"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1136\/pgmj.56.661.753"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1136\/bmj.2.6087.608"},{"key":"e_1_2_6_5_1","unstructured":"WADA (World Anti\u2010Doping Agency).The 2010 prohibited list. 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Available at:http:\/\/www.wada\u2010ama.org\/Documents\/World_Anti\u2010Doping_Program\/WADP\u2010IS\u2010Laboratories\/WADA_TD2010MRPLv1.0_Minimum%20Required%20Performance%20Levels_Sept%2001%202010_EN.pdf[16 April2012]."},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1044-0305(03)00574-9"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac020361s"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00216-010-4589-4"}],"container-title":["Drug Testing and Analysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fdta.1388","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.1388","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T18:28:20Z","timestamp":1760380100000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/dta.1388"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,7,12]]},"references-count":21,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2012,9]]}},"alternative-id":["10.1002\/dta.1388"],"URL":"https:\/\/doi.org\/10.1002\/dta.1388","archive":["Portico"],"relation":{},"ISSN":["1942-7603","1942-7611"],"issn-type":[{"type":"print","value":"1942-7603"},{"type":"electronic","value":"1942-7611"}],"subject":[],"published":{"date-parts":[[2012,7,12]]}}}