title: Test purchase, synthesis and characterization of 3-fluorophenmetrazine (3-FPM) and differentiation from its ortho- and para-substituted isomers.
abstract: The knowledge captured in patent and scientific research literature stimulates new ideas and fosters new drug development efforts. Manufacturers and entrepreneurs dedicated to the sale of 'research chemicals' and/or new psychoactive substances (NPS) also make use of access to information to identify, prepare, and launch a range of new substances. One of the most recent compounds to appear on the NPS market is the phenmetrazine analog 3-fluorophenmetrazine (3-FPM) which represents one of many phenylmorpholines designed to explore treatment options in areas such as obesity and drug dependence. The anorectic drug analogs phenmetrazine and phendimetrazine, used as prescription medicines before they were withdrawn, feature amphetamine-like properties associated with monoamine release. Available data on 3-FPM suggest that the effects might show mechanistic overlaps. This study describes the synthesis and extensive analytical characterization of 3-FPM and its differentiation from synthesized ortho- and para- substituted isomers, 2-FPM and 4-FPM, respectively. This study was triggered by the purchase of five powdered samples advertised as 3-FPM by five different Internet vendors based in the United Kingdom. The analytical data obtained for the vendor samples were consistent with the synthesized 3-FPM standard and differentiation between all three isomers was possible. The presence of positional isomers and the absence of suitable reference material can cause difficulties in the day-to-day operation of forensic work and given the rate at which many of the newly emerging NPS appear on the market, a comprehensive approach is needed when attempting to decipher the identity of NPS arriving onto the drug market. Copyright © 2016 John Wiley & Sons, Ltd.
authors.affiliation: Department of Life and Physical Sciences, School of Science, Athlone Institute of Technology, Dublin Road, Westmeath, Ireland.|Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences, St. James's Hospital, Dublin 8, Ireland.
authors.forename: Gavin
authors.initials: G
authors.lastname: McLaughlin
authors.affiliation: Department of Life and Physical Sciences, School of Science, Athlone Institute of Technology, Dublin Road, Westmeath, Ireland.
authors.forename: Noreen
authors.initials: N
authors.lastname: Morris
authors.affiliation: Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences, St. James's Hospital, Dublin 8, Ireland.
authors.forename: Pierce V
authors.initials: PV
authors.lastname: Kavanagh
authors.affiliation: Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences, St. James's Hospital, Dublin 8, Ireland.
authors.forename: Geraldine
authors.initials: G
authors.lastname: Dowling
authors.affiliation: Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences, St. James's Hospital, Dublin 8, Ireland.|Forensic Science Laboratory, Garda HQ, Dublin 8, Ireland.
authors.forename: John D
authors.initials: JD
authors.lastname: Power
authors.affiliation: School of Chemistry, Trinity College Dublin, Dublin 2, Ireland.
authors.forename: Brendan
authors.initials: B
authors.lastname: Twamley
authors.affiliation: School of Chemistry, Trinity College Dublin, Dublin 2, Ireland.
authors.forename: John
authors.initials: J
authors.lastname: O'Brien
authors.affiliation: School of Pharmacy and Pharmaceutical Sciences, Trinity College Dublin, Dublin 2, Ireland.
authors.forename: Brian
authors.initials: B
authors.lastname: Talbot
authors.affiliation: Institute of Pharmacology, Center of Physiology and Pharmacology, Medical University Vienna, Vienna, Austria.|Center for Addiction Research and Science, Medical University Vienna, Waehringerstrasse 13A, 1090, Vienna, Austria.
authors.forename: Harald H
authors.initials: HH
authors.lastname: Sitte
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: D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D008401:Gas Chromatography-Mass Spectrometry; D054879:Halogenation; D013287:Illicit Drugs / Q000138:chemical synthesis / Q000737:chemistry*; D007536:Isomerism; D008958:Models, Molecular; D010633:Phenmetrazine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011619:Psychotropic Drugs / Q000138:chemical synthesis / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D013287:Illicit Drugs; D011619:Psychotropic Drugs; C000614515:3-fluorophenmetrazine; D010633:Phenmetrazine
keywords: chemistry; new psychoactive substances; phenmetrazine; positional isomers; psychostimulants