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Characterization and Differentiation of Geometric Isomers of 3‐methylfentanyl Analogs by Gas Chromatography/Mass Spectrometry, Liquid Chromatography/Mass Spectrometry, and Nuclear Magnetic Resonance Spectroscopy
Author(s) -
Kanamori Tatsuyuki,
Iwata Yuko T.,
Segawa Hiroki,
Yamamuro Tadashi,
Kuwayama Kenji,
Tsujikawa Kenji,
Inoue Hiroyuki
Publication year - 2017
Publication title -
journal of forensic sciences
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.715
H-Index - 96
eISSN - 1556-4029
pISSN - 0022-1198
DOI - 10.1111/1556-4029.13395
Subject(s) - chemistry , mass spectrometry , derivatization , trimethylsilyl , gas chromatography , chromatography , gas chromatography–mass spectrometry , nuclear magnetic resonance spectroscopy , hydrochloride , organic chemistry
The cis and trans isomers of 3‐methylfentanyl and its three analogs were chemically synthesized, and these compounds were characterized and differentiated by gas chromatography/mass spectrometry ( GC / MS ), liquid chromatography/mass spectrometry ( LC / MS ), and nuclear magnetic resonance ( NMR ) spectroscopy. The cis and trans isomers of the 3‐methylfentanyl analogs were completely separated by GC / MS . Although the high temperature of the GC injection port caused thermal degradation of β‐hydroxy‐3‐methylfentanyl, the degradation was completely suppressed by trimethylsilyl derivatization. The isomers were also well separated by LC / MS on an octadecylsilyl column with 10 mM ammonium acetate and methanol as the mobile phase. The proton NMR signals were split when the hydrochloride salts of the 3‐methylfentanyl 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‐methylfentanyl analogs.