title: Syntheses and analytical characterizations of N-alkyl-arylcyclohexylamines.
abstract: 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.
authors.affiliation: Department of Pharmaceutical Sciences, Philadelphia College of Pharmacy, University of the Sciences, Philadelphia, PA, 19104, USA.
authors.forename: Jason
authors.initials: J
authors.lastname: Wallach
authors.affiliation: Department of Pharmaceutical Sciences, Philadelphia College of Pharmacy, University of the Sciences, Philadelphia, PA, 19104, USA.
authors.forename: Tristan
authors.initials: T
authors.lastname: Colestock
authors.affiliation: Department of Pharmaceutical Sciences, Philadelphia College of Pharmacy, University of the Sciences, Philadelphia, PA, 19104, USA.
authors.forename: Brian
authors.initials: B
authors.lastname: Cicali
authors.affiliation: ROAR Forensics, Malvern Hills Science Park, Geraldine Road, WR14 3SZ, UK.
authors.forename: Simon P
authors.initials: SP
authors.lastname: Elliott
authors.affiliation: Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences, St. James Hospital, Dublin 8, Ireland.
authors.forename: Pierce V
authors.initials: PV
authors.lastname: Kavanagh
authors.affiliation: Department of Pharmaceutical Sciences, Philadelphia College of Pharmacy, University of the Sciences, Philadelphia, PA, 19104, USA.
authors.forename: Adeboye
authors.initials: A
authors.lastname: Adejare
authors.affiliation: School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Byrom Street, Liverpool, L3 3AF, UK.
authors.forename: Nicola M
authors.initials: NM
authors.lastname: Dempster
authors.affiliation: School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Byrom Street, Liverpool, L3 3AF, UK.
authors.forename: Simon D
authors.initials: SD
authors.lastname: Brandt
mesh_terms: D000478:Alkylation; D002849:Chromatography, Gas; D003514:Cyclohexylamines / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D013287:Illicit Drugs / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation; D011619:Psychotropic Drugs / Q000138:chemical synthesis / Q000737:chemistry*; D015813:Substance Abuse Detection; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D003514:Cyclohexylamines; D013287:Illicit Drugs; D011619:Psychotropic Drugs; D013876:Thiophenes
keywords: NMDA receptors; arylcyclohexylamines; new psychoactive substances; phencyclidine; ‘research chemicals’