{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,19]],"date-time":"2026-08-19T19:37:17Z","timestamp":1787168237229,"version":"build-2736575974"},"reference-count":38,"publisher":"Wiley","issue":"11-12","license":[{"start":{"date-parts":[[2020,7,15]],"date-time":"2020-07-15T00:00:00Z","timestamp":1594771200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001962","name":"World Anti-Doping Agency","doi-asserted-by":"publisher","award":["11A13CG"],"award-info":[{"award-number":["11A13CG"]}],"id":[{"id":"10.13039\/501100001962","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":[[2020,11]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Methylnortestosterone is a progestin and synthetic androgenic anabolic steroid, prohibited by WADA. Methylnortestosterone misuse is commonly detected by monitoring the parent compound and its main metabolites, 17\u03b1\u2010methyl\u20105\u03b1\u2010estrane\u20103\u03b1, 17\u03b2\u2010diol (M1) and 17\u03b1\u2010methyl\u20105\u03b2\u2010estrane\u20103\u03b1, 17\u03b2\u2010diol (M2), in the glucuronide fraction. In the current study, a direct detection of methylnortestosterone sulfo\u2010conjugated metabolites after ethyl acetate extraction and analysis by LC\/Q\/TOF\u2010MS in negative ionization mode was performed, detecting two main sulfate metabolites (S1, S2). For the characterization of metabolites, samples from the excretion study, were additionally analyzed by GC\u2013MS, after solvolysis and per TMS derivatization. RT and MS data collected, were compared with RT and MS data from metabolites of 17z\u2010methyl\u20105\u03b1\/\u03b2\u2010estrane\u20103\u03b1\/\u03b2, 17z\u2010diols structures with prefixed stereochemistry at 3 and 5 positions, synthesized through Grignard reaction from 19\u2010noretiocholanolone, 19\u2010norandrosterone and 19\u2010norepiandrosterone. Confirmed sulfate metabolites were S1, 17\u03b1\u2010methyl\u20105\u03b1\u2010estrane\u20103\u03b1, 17\u03b2\u2010diol 3\u03b1 sulfate (detected up to 72 h) and S2, 17\u03b1\u2010methyl\u20105\u03b2\u2010estrane\u20103\u03b1, 17\u03b2\u2010diol 3\u03b1 sulfate (detected up to 192 h).<\/jats:p>\n                  <jats:p>Furthermore, applying targeted analysis based on RT and MS data of the synthesized metabolites two additional metabolites M3, 17\u03b2\u2010methyl\u20105\u03b2\u2010estrane\u20103\u03b1, 17\u03b1\u2010diol and M4, 17\u03b2\u2010methyl\u20105\u03b1\u2010estrane\u20103\u03b1, 17\u03b1\u2010diol were detected in the glucuronide fraction and one more metabolite (S3) 17\u03b2\u2010methyl\u20105\u03b2\u2010estrane\u20103\u03b1, 17\u03b1\u2010diol was detected in the sulfate fraction in lower abundance until the end of the excretion study (192 h). Interestingly, S2 could also be detected after the direct analysis of non\u2010hydrolyzed steroid by GC\u2013MS\/MS as artifact, following normal ProcIV anabolic steroid procedure and using diethylether as extraction solvent.<\/jats:p>","DOI":"10.1002\/dta.2887","type":"journal-article","created":{"date-parts":[[2020,6,30]],"date-time":"2020-06-30T18:28:43Z","timestamp":1593541723000},"page":"1544-1553","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Alternative markers for Methylnortestosterone misuse in human urine"],"prefix":"10.1002","volume":"12","author":[{"given":"Panagiotis","family":"Sakellariou","sequence":"first","affiliation":[{"name":"Doping Control Laboratory of Athens Institute of Biosciences &amp; Applications, National Center for Scientific Research \"Demokritos\"  Neratziotissis &amp; Amaryssias Artemidos Str Athens 15123 Greece"},{"name":"Faculty of Biology, Schoole of Science National and Kapodistrian University of Athens  Panepistimioupolis, Zografou Athens 15771 Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0322-9519","authenticated-orcid":false,"given":"Polyxeni","family":"Kiousi","sequence":"additional","affiliation":[{"name":"Doping Control Laboratory of Athens Institute of Biosciences &amp; Applications, National Center for Scientific Research \"Demokritos\"  Neratziotissis &amp; Amaryssias Artemidos Str Athens 15123 Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9422-670X","authenticated-orcid":false,"given":"Argyro G.","family":"Fragkaki","sequence":"additional","affiliation":[{"name":"Doping Control Laboratory of Athens Institute of Biosciences &amp; Applications, National Center for Scientific Research \"Demokritos\"  Neratziotissis &amp; Amaryssias Artemidos Str Athens 15123 Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emmanouil","family":"Lyris","sequence":"additional","affiliation":[{"name":"Novartis Technical Operations, Biotechnology &amp; Aseptics, Sandoz GmbH, Schaftenau site  Biochemiestrasse 10, Bau 531, 6336 Langkampfen Langkampfen AT Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"Petrou","sequence":"additional","affiliation":[{"name":"Cyprus Anti\u2010Doping Authority Makarion Athletic Center Avenue, Engomi  Nicosia CY 2400 Cyprus"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Costas","family":"Georgakopoulos","sequence":"additional","affiliation":[{"name":"AntiDoping Lab Qatar  P.O. Box 27775 Doha Qatar"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8773-1575","authenticated-orcid":false,"given":"Yiannis S.","family":"Angelis","sequence":"additional","affiliation":[{"name":"Doping Control Laboratory of Athens Institute of Biosciences &amp; Applications, National Center for Scientific Research \"Demokritos\"  Neratziotissis &amp; Amaryssias Artemidos Str Athens 15123 Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,7,15]]},"reference":[{"key":"e_1_2_6_2_1","volume-title":"Martindale\u2010the Extra Pharmacopoeia","author":"Reynolds JEF","year":"2002"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/0003-2670(93)80274-O"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1093\/clinchem\/42.7.1001"},{"key":"e_1_2_6_5_1","unstructured":"World Anti\u2010Doping Agency (WADA) 2020Statistics.https:\/\/www.wada-ama.org\/en\/what-we-do\/anti-doping-statistics(accessed 20\/04\/2020)."},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsbmb.2006.06.024"},{"key":"e_1_2_6_7_1","unstructured":"https:\/\/www.drugs.com\/international\/normethandrone.html"},{"key":"e_1_2_6_8_1","unstructured":"World Anti\u2010Doping Agency (WADA) 2020The Prohibited List. 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