{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,4]],"date-time":"2026-07-04T05:32:34Z","timestamp":1783143154255,"version":"3.54.6"},"reference-count":16,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2017,6,26]],"date-time":"2017-06-26T00:00:00Z","timestamp":1498435200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["15K08895"],"award-info":[{"award-number":["15K08895"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Journal of Forensic Sciences"],"published-print":{"date-parts":[[2017,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The <jats:italic>cis<\/jats:italic> and <jats:italic>trans<\/jats:italic> isomers of 3\u2010methylfentanyl and its three analogs were chemically synthesized, and these compounds were characterized and differentiated by gas chromatography\/mass spectrometry (<jats:styled-content style=\"fixed-case\">GC<\/jats:styled-content>\/<jats:styled-content style=\"fixed-case\">MS<\/jats:styled-content>), liquid chromatography\/mass spectrometry (<jats:styled-content style=\"fixed-case\">LC<\/jats:styled-content>\/<jats:styled-content style=\"fixed-case\">MS<\/jats:styled-content>), and nuclear magnetic resonance (<jats:styled-content style=\"fixed-case\">NMR<\/jats:styled-content>) spectroscopy. The <jats:italic>cis<\/jats:italic> and <jats:italic>trans<\/jats:italic> isomers of the 3\u2010methylfentanyl analogs were completely separated by <jats:styled-content style=\"fixed-case\">GC<\/jats:styled-content>\/<jats:styled-content style=\"fixed-case\">MS<\/jats:styled-content>. Although the high temperature of the <jats:styled-content style=\"fixed-case\">GC<\/jats:styled-content> injection port caused thermal degradation of \u03b2\u2010hydroxy\u20103\u2010methylfentanyl, the degradation was completely suppressed by trimethylsilyl derivatization. The isomers were also well separated by <jats:styled-content style=\"fixed-case\">LC<\/jats:styled-content>\/<jats:styled-content style=\"fixed-case\">MS<\/jats:styled-content> on an octadecylsilyl column with 10\u00a0mM ammonium acetate and methanol as the mobile phase. The proton <jats:styled-content style=\"fixed-case\">NMR<\/jats:styled-content> signals were split when the hydrochloride salts of the 3\u2010methylfentanyl analogs were dissolved in deuterated chloroform because stereoisomers were formed by the coordination of the hydrochloride proton to the nitrogen of the piperidine ring of the 3\u2010methylfentanyl analogs.<\/jats:p>","DOI":"10.1111\/1556-4029.13395","type":"journal-article","created":{"date-parts":[[2017,6,26]],"date-time":"2017-06-26T07:44:39Z","timestamp":1498463079000},"page":"1472-1478","source":"Crossref","is-referenced-by-count":21,"title":["Characterization and Differentiation of Geometric Isomers of 3\u2010methylfentanyl Analogs by Gas Chromatography\/Mass Spectrometry, Liquid Chromatography\/Mass Spectrometry, and Nuclear Magnetic Resonance Spectroscopy"],"prefix":"10.1111","volume":"62","author":[{"given":"Tatsuyuki","family":"Kanamori","sequence":"first","affiliation":[{"name":"National Research Institute of Police Science 6\u20103\u20101, Kashiwanoha Kashiwa Chiba 277\u20100882 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuko T.","family":"Iwata","sequence":"additional","affiliation":[{"name":"National Research Institute of Police Science 6\u20103\u20101, Kashiwanoha Kashiwa Chiba 277\u20100882 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroki","family":"Segawa","sequence":"additional","affiliation":[{"name":"National Research Institute of Police Science 6\u20103\u20101, Kashiwanoha Kashiwa Chiba 277\u20100882 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tadashi","family":"Yamamuro","sequence":"additional","affiliation":[{"name":"National Research Institute of Police Science 6\u20103\u20101, Kashiwanoha Kashiwa Chiba 277\u20100882 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kenji","family":"Kuwayama","sequence":"additional","affiliation":[{"name":"National Research Institute of Police Science 6\u20103\u20101, Kashiwanoha Kashiwa Chiba 277\u20100882 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kenji","family":"Tsujikawa","sequence":"additional","affiliation":[{"name":"National Research Institute of Police Science 6\u20103\u20101, Kashiwanoha Kashiwa Chiba 277\u20100882 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroyuki","family":"Inoue","sequence":"additional","affiliation":[{"name":"National Research Institute of Police Science 6\u20103\u20101, Kashiwanoha Kashiwa Chiba 277\u20100882 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2017,6,26]]},"reference":[{"key":"e_1_2_5_2_1","unstructured":"JanssenPAJ inventor. 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