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Analytical characterization of three trifluoromethyl‐substituted methcathinone isomers
Author(s) -
Brandt Simon D.,
Daley Paul F.,
Cozzi Nicholas V.
Publication year - 2012
Publication title -
drug testing and analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.065
H-Index - 54
eISSN - 1942-7611
pISSN - 1942-7603
DOI - 10.1002/dta.382
Subject(s) - substituent , chemistry , context (archaeology) , cathinone , trifluoromethyl , iminium , structural isomer , stereochemistry , amphetamine , ion , psychology , organic chemistry , alkyl , paleontology , biology , dopamine , neuroscience
Cathinone derivatives display a wide range of pharmacological activities and uses; some of them are used as prescription medicines, while others are encountered within a recreational context and are available without a prescription over the Internet and in retail shops around the world. One of the difficulties involved in the unambiguous identification of these new psychoactive substances is the lack of suitable reference standards, particularly when dealing with unreported derivatives and positional isomers. In order to address this need, three trifluoromethyl analogues of the psychostimulant methcathinone, with a CF 3 substituent at the 2‐, 3‐ and 4‐position of the phenyl ring (2‐TFMAP 1, 3‐TFMAP 2 and 4‐TFMAP 3), have been prepared for analytical characterization using ATR‐FTIR, 1 H and 13 C NMR, and GC‐(EI/CI)‐ion trap‐MS. Differentiation among isomers was feasible by IR, for example when assessing the carbonyl stretch at 1711 (1), 1693 (2) and 1688 (3) cm ‐1 , respectively. In addition to the expected iminium base peak at m/z 58, EI‐MS displayed key ions at m/z 173, 145, 125, 95, and 75. Separation of isomers was possible under GC conditions. A characteristic feature under CI conditions was the loss of water from the [M + H] + yielding m/z 214 in addition to m/z 58. Studies currently underway show that the three CF 3 ‐methcathinone analogues have central nervous system effects and that the 4‐CF 3 isomer 3 is more potent as a serotonin uptake inhibitor and releasing agent than the 3‐CF 3 and 2‐CF 3 counterparts. Copyright © 2012 John Wiley & Sons, Ltd.