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Syntheses and analytical characterizations of N ‐alkyl‐arylcyclohexylamines
Author(s) -
Wallach Jason,
Colestock Tristan,
Cicali Brian,
Elliott Simon P.,
Kavanagh Pierce V.,
Adejare Adeboye,
Dempster Nicola M.,
Brandt Simon D.
Publication year - 2016
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.1861
Subject(s) - alkyl , chemistry , mass spectrometry , aryl , gas chromatography , organic chemistry , chromatography
The rise in new psychoactive substances that are available as 'research chemicals’ (RCs) remains a significant forensic and legislative challenge. A number of arylcyclohexylamines have attracted attention as RCs and continue to be encountered, including 3‐MeO‐PCP, 3‐MeO‐PCE and 3‐MeO‐PCPr. These compounds are commonly perceived as ketamine‐like dissociative substances and are believed to act predominantly via antagonism of the N ‐methyl‐D‐aspartate (NMDA) receptor. To aid in the identification of newly emerging substances of abuse, the current studies were performed. The syntheses of fifteen N ‐alkyl‐arylcyclohexylamines are described. Analytical characterizations were performed via gas chromatography and high performance liquid chromatography coupled to multiple forms of mass spectrometry as well as nuclear magnetic resonance spectroscopy, ultraviolet diode array detection and infrared spectroscopy. The series consisted of the N ‐alkyl derivatives ( N ‐methyl, N ‐ethyl, N ‐propyl) of phenyl‐substituted and isomeric 2‐, 3‐ and 4‐methoxy phenylcyclohexylamines, as well as the N ‐alkyl derivatives obtained from 3‐methylphenyl and 2‐thienyl moieties. In addition to the presentation of a range of previously unreported data, it was also found that positional isomers of aryl methoxyl‐substituted arylcyclohexylamines were readily distinguishable under a variety of analytical conditions. Copyright © 2015 John Wiley & Sons, Ltd.