{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T01:03:54Z","timestamp":1760403834364,"version":"build-2065373602"},"reference-count":13,"publisher":"Wiley","issue":"11-12","license":[{"start":{"date-parts":[[2015,10,20]],"date-time":"2015-10-20T00:00:00Z","timestamp":1445299200000},"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":[[2015,12]]},"abstract":"<jats:p>2\u2010Phenylethanamine (phenethylamine, PEA) represents the core structure of numerous drugs with stimulant\u2010like properties and is explicitly featured as so\u2010called specified substance on the World Anti\u2010Doping Agency (WADA) Prohibited List. Due to its natural occurrence in humans as well as its presence in dietary products, studies concerning the ability of test methods to differentiate between an illicit intake and the renal elimination of endogenously produced PEA were indicated. Following the addition of PEA to the Prohibited List in January 2015, retrospective evaluation of routine doping control data of 10 190 urine samples generated by combined gas chromatography\u2010mass spectrometry and nitrogen phosphorus\u2010specific detection (GC\u2010MS\/NPD) was performed. Signals for PEA at approximate concentrations\u2009&gt;\u2009500\u2009ng\/mL were observed in 31 cases (0.3%), which were subjected to a validated isotope\u2010dilution liquid chromatography\u2010tandem mass spectrometry (ID\u2010LC\u2010MS\/MS) test method for accurate quantification of the target analyte. Further, using elimination study urine samples collected after a single oral administration of 250\u2009mg of PEA hydrochloride to two healthy male volunteers, two tentatively identified metabolites of PEA were observed and evaluated concerning their utility as discriminative markers for PEA intake. The ID\u2010LC\u2010MS\/MS approach was extended to allow for the simultaneous detection of PEA and 2\u2010(3\u2010hydroxyphenyl)acetamide sulfate (M1), and concentration ratios of M1 and PEA were calculated for elimination study urine samples and a total of 205 doping control urine samples that returned findings for PEA at estimated concentrations of 50\u20132500\u2009ng\/mL. Urine samples of the elimination study with PEA yielded concentration ratios of M1\/PEA up to values of 9.4. Notably, the urinary concentration of PEA did increase with the intake of PEA only to a modest extent, suggesting a comprehensive metabolism of the orally administered substance. Conversely, doping control urine samples with elevated (&gt;50\u2009ng\/mL) amounts of PEA returned quantifiable concentrations of M1 only in 3 cases, which yielded maximum ratios of M1\/PEA of 0.9, indicating an origin of PEA other than an orally ingested drug formulation. Consequently, the consideration of analyte abundance ratios (e.g. M1\/PEA) is suggested as a means to identify the use of PEA by athletes, but further studies to support potential decisive criteria are warranted. Copyright \u00a9 2015 John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/dta.1909","type":"journal-article","created":{"date-parts":[[2015,10,20]],"date-time":"2015-10-20T05:35:44Z","timestamp":1445319344000},"page":"1057-1062","source":"Crossref","is-referenced-by-count":9,"title":["Monitoring 2\u2010phenylethanamine and 2\u2010(3\u2010hydroxyphenyl)acetamide sulfate in doping controls"],"prefix":"10.1002","volume":"7","author":[{"given":"Gerd","family":"Sigmund","sequence":"first","affiliation":[{"name":"Center for Preventive Doping Research \u2013 Institute of Biochemistry German Sport University Cologne  Am Sportpark M\u00fcngersdorf 6 50933 Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Josef","family":"Dib","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research \u2013 Institute of Biochemistry German Sport University Cologne  Am Sportpark M\u00fcngersdorf 6 50933 Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Laura","family":"Tretzel","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research \u2013 Institute of Biochemistry German Sport University Cologne  Am Sportpark M\u00fcngersdorf 6 50933 Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Thomas","family":"Piper","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research \u2013 Institute of Biochemistry German Sport University Cologne  Am Sportpark M\u00fcngersdorf 6 50933 Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christina","family":"Bosse","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research \u2013 Institute of Biochemistry German Sport University Cologne  Am Sportpark M\u00fcngersdorf 6 50933 Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Wilhelm","family":"Sch\u00e4nzer","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research \u2013 Institute of Biochemistry German Sport University Cologne  Am Sportpark M\u00fcngersdorf 6 50933 Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mario","family":"Thevis","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research \u2013 Institute of Biochemistry German Sport University Cologne  Am Sportpark M\u00fcngersdorf 6 50933 Cologne Germany"},{"name":"European Monitoring Center for Emerging Doping Agents (EuMoCEDA)  Cologne\/Bonn Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2015,10,20]]},"reference":[{"key":"e_1_2_6_2_1","unstructured":"World Anti\u2010Doping Agency.2015 The 2015 Prohibited List. Available at:https:\/\/wada\u2010main\u2010prod.s3.amazonaws.com\/resources\/files\/wada\u20102015\u2010prohibited\u2010list\u2010en.pdf[24 July 2015]."},{"volume-title":"PIHKAL: A Chemical Love Story","year":"1991","author":"Shulgin A.","key":"e_1_2_6_3_1"},{"volume-title":"The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds","year":"2011","author":"Shulgin A.T.","key":"e_1_2_6_4_1"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1471-4159.2004.02501.x"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1136\/bjsm.35.5.342"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00966763"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009-8981(77)90073-0"},{"key":"e_1_2_6_9_1","first-page":"149","article-title":"The metabolism of ingested deuterated b\u2010phenethylamine in a human male","volume":"1","author":"Davis B.A.","year":"1980","journal-title":"Eur. J. Mass Spectrom. Biochem. Med. Environ. Res."},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12264-013-1330-2"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(01)96571-9"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1255\/ejms.875"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.1680"},{"key":"e_1_2_6_14_1","doi-asserted-by":"crossref","first-page":"1269","DOI":"10.1016\/S0022-3565(24)36940-X","article-title":"N\u2010oxygenation of phenethylamine to the trans\u2010oxime by adult human liver flavin\u2010containing monooxygenase and retroreduction of phenethylamine hydroxylamine by human liver microsomes","volume":"282","author":"Lin J.","year":"1997","journal-title":"J. Pharmacol. Exp. Ther."}],"container-title":["Drug Testing and Analysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fdta.1909","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.1909","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T19:55:32Z","timestamp":1760385332000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/dta.1909"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,10,20]]},"references-count":13,"journal-issue":{"issue":"11-12","published-print":{"date-parts":[[2015,12]]}},"alternative-id":["10.1002\/dta.1909"],"URL":"https:\/\/doi.org\/10.1002\/dta.1909","archive":["Portico"],"relation":{},"ISSN":["1942-7603","1942-7611"],"issn-type":[{"type":"print","value":"1942-7603"},{"type":"electronic","value":"1942-7611"}],"subject":[],"published":{"date-parts":[[2015,10,20]]}}}