{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:41:47Z","timestamp":1786977707943,"version":"build-2736575974"},"reference-count":19,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2019,3,20]],"date-time":"2019-03-20T00:00:00Z","timestamp":1553040000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100000780","name":"European Commission","doi-asserted-by":"publisher","award":["JUST\/2013\/ISEC\/DRUGS\/AG\/6421"],"award-info":[{"award-number":["JUST\/2013\/ISEC\/DRUGS\/AG\/6421"]}],"id":[{"id":"10.13039\/501100000780","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":[[2019,7]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Pharmaceutical research not only provides the basis for the development of new medicinal products but also for the synthesis of new drugs of abuse. 3\u2010Fluorophenmetrazine (3\u2010FPM), a fluorinated derivative of the anorectic phenmetrazine, was first patented in 2011 and appeared on the drug market in 2014. Though invented for potential medical purposes, pharmacokinetic data on this compound, crucial for interpreting forensic as well as clinical cases, are not available. Therefore, a liquid chromatography\u2212electrospray ionization\u2212tandem mass spectrometry (LC\u2212ESI\u2212MS\/MS) method for the detection of 3\u2010FPM in serum, urine, and oral fluid was developed, validated for urine and serum, and used to quantify 3\u2010FPM in samples obtained during a controlled self\u2010experiment. The method proved to be linear, selective and sufficiently sensitive. The limits of detection (LODs) were 0.1\u00a0ng\/mL, 0.2\u00a0ng\/mL, and 0.05\u00a0ng\/mL in serum, urine, and oral fluid. Inter\u2010day precision and intra\u2010day precision (RSD) in serum samples were below 6.3% and below 8.5%, respectively. The highest serum concentration (c\n                    <jats:sub>max<\/jats:sub>\n                    ) of 210\u00a0ng\/mL was reached 2.5\u00a0hours (t\n                    <jats:sub>max<\/jats:sub>\n                    ) after ingestion. The elimination half\u2010life and the volume of distribution were calculated to be approx. 8.8\u00a0hours and 400\u00a0L (5.3\u00a0L\/kg). 3\u2010FPM could be detected in serum and urine up to 82\u00a0hours and 116\u00a0hours, respectively. It was still detected in the last oral fluid sample taken 55\u00a0hours after ingestion. 3\u2010FPM was mainly excreted unchanged. Main metabolic reactions were aryl\u2010hydroxylation and\n                    <jats:italic>N<\/jats:italic>\n                    \u2010hydroxylation. Interestingly, the product of oxidative ring opening (2\u2010amino\u20101\u2010(3\u2010fluorophenyl)propan\u20101\u2010ol) showed the largest window of detection in the self\u2010experiment.\n                  <\/jats:p>","DOI":"10.1002\/dta.2577","type":"journal-article","created":{"date-parts":[[2019,2,20]],"date-time":"2019-02-20T01:45:22Z","timestamp":1550627122000},"page":"1009-1017","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Method validation and preliminary pharmacokinetic studies on the new designer stimulant 3\u2010fluorophenmetrazine (3\u2010FPM)"],"prefix":"10.1002","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3240-1848","authenticated-orcid":false,"given":"Christina","family":"Grumann","sequence":"first","affiliation":[{"name":"Institute of Forensic Medicine, Forensic Toxicology, Medical Center \u2013 University of Freiburg, Faculty of Medicine, University of Freiburg  Freiburg Germany"},{"name":"Hermann Staudinger Graduate School University of Freiburg  Freiburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4190-5469","authenticated-orcid":false,"given":"Laura M.","family":"Huppertz","sequence":"additional","affiliation":[{"name":"Institute of Forensic Medicine, Forensic Toxicology, Medical Center \u2013 University of Freiburg, Faculty of Medicine, University of Freiburg  Freiburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Philippe","family":"Bisel","sequence":"additional","affiliation":[{"name":"Institute for Pharmaceutical Sciences, University of Freiburg  Freiburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3081-4609","authenticated-orcid":false,"given":"Verena","family":"Angerer","sequence":"additional","affiliation":[{"name":"Institute of Forensic Medicine, Forensic Toxicology, Medical Center \u2013 University of Freiburg, Faculty of Medicine, University of Freiburg  Freiburg Germany"},{"name":"Forensic Toxicology Institute of Forensic Medicine  St. Gallen Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1883-2804","authenticated-orcid":false,"given":"Volker","family":"Auw\u00e4rter","sequence":"additional","affiliation":[{"name":"Institute of Forensic Medicine, Forensic Toxicology, Medical Center \u2013 University of Freiburg, Faculty of Medicine, University of Freiburg  Freiburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2019,3,20]]},"reference":[{"key":"e_1_2_6_2_1","unstructured":"Boehringer EB A LiebrechtI LiebrechtJ.Improvements in or relating to a method of preparing n\u2010substituted morpholines. GB 773780 C.H.B. Sohn Ingelheim Germany;1957."},{"key":"e_1_2_6_3_1","unstructured":"Boehringer EB A LiebrechtI LiebrechtJ Mayer\u2010ListW.Improvements in or relating to the production of substituted tetrahydrooxazines. GB 791416 (A) C.H.B. Sohn Ingelheim Germany;1958."},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00409112"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(59)90562-8"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1136\/bmj.1.5016.460-b"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0015-7368(73)70827-6"},{"key":"e_1_2_6_8_1","unstructured":"BloughBE RothmanR LandavazoA PageKM DeckerAM.Phenylmorpholines and analogues thereof. Patent No. WO2011146850 A1 Research Triangle Institute;2011."},{"key":"e_1_2_6_9_1","first-page":"418","article-title":"3\u2010Fluorophenmetrazine \u2010 a new psychoactive substance on the polish drug market","volume":"105","author":"Adamowicz P","year":"2016","journal-title":"Probl Forensic Sci"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1080\/15563650.2016.1211288"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.1945"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.neuropharm.2017.10.006"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jpba.2016.06.011"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1093\/jat\/bkx060"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00216-009-3394-4"},{"issue":"3","key":"e_1_2_6_16_1","first-page":"185","article-title":"Appendix B to the GTFCh guidelines for quality assurance in forensic\u2010toxicological analyses \u2010 requirements for the validation of analytical methods","volume":"76","author":"Peters FT","year":"2009","journal-title":"Toxichem Krimtech"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac020361s"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.2371"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1080\/00498254.2018.1482509"},{"key":"e_1_2_6_20_1","volume-title":"Disposition of toxic drugs and chemicals in man","author":"Baselt RC","year":"2017"}],"container-title":["Drug Testing and Analysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fdta.2577","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.2577","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/dta.2577","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.2577","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T20:18:05Z","timestamp":1760386685000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/dta.2577"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,3,20]]},"references-count":19,"journal-issue":{"issue":"7","published-print":{"date-parts":[[2019,7]]}},"alternative-id":["10.1002\/dta.2577"],"URL":"https:\/\/doi.org\/10.1002\/dta.2577","archive":["Portico"],"relation":{},"ISSN":["1942-7603","1942-7611"],"issn-type":[{"value":"1942-7603","type":"print"},{"value":"1942-7611","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,3,20]]},"assertion":[{"value":"2019-01-09","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-02-17","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-03-20","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}