title: Indirect chiral separation of 8 novel amphetamine derivatives as potential new psychoactive compounds by GC-MS and HPLC.
abstract: Amphetamine and its derivatives gained high popularity on the illegal drug market. In the last few years, a lot of new psychoactive compounds structurally related to amphetamine, such as 4-fluoroamphetamine and 4-fluoromethamphetamine swamped the drug market. They were designed to circumvent prohibition of amphetamine and N-methylamphetamine and are distributed via the Internet. Often, a halogen atom is introduced into the phenyl ring of amphetamine to turn the illegal amphetamine legal. Since amphetamines possess a chiral centre, two enantiomers are available, which might differ in activity. Since most of them are partially not commercially available to date, synthesis and characterisation of amphetamine derivatives might help authorities to identify these substances of abuse. The aim of this study was to investigate self-synthesized amphetamines concerning their identity and their enantiomeric status either by GC-MS or by HPLC. For GC-MS, derivatization with (R)-(+)-α-methoxy-α-trifluoromethylphenylacetic acid (MTPA) or (1R)-(-)-menthylchloroformate prior to analysis on a HP-5MS column was done. For chiral separation by HPLC a LiChrospher 100 RP-18e column and sulfated beta-cyclodextrin added to the mobile phase as chiral selector were used. Enantioseparation was accomplished successfully by both methods. Furthermore, simultaneous chiral separation of three positions isomers, namely 2-fluoroamphetamine, 3-fluoroamphetamine and 4-fluoroamphetamine, was shown successfully by HPLC.
authors.affiliation: Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Sciences, University of Graz, Universitaetsplatz 1, A-8010 Graz, Austria. Electronic address: jennifer.weiss@uni-graz.at.
authors.forename: Jennifer A
authors.initials: JA
authors.lastname: Weiß
authors.affiliation: Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Sciences, University of Graz, Universitaetsplatz 1, A-8010 Graz, Austria. Electronic address: kian.kadkhodaei@edu.uni-graz.at.
authors.forename: Kian
authors.initials: K
authors.lastname: Kadkhodaei
authors.affiliation: Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Sciences, University of Graz, Universitaetsplatz 1, A-8010 Graz, Austria. Electronic address: martin.schmid@uni-graz.at.
authors.forename: Martin G
authors.initials: MG
authors.lastname: Schmid
mesh_terms: D000662:Amphetamines / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D053593:Forensic Toxicology; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D006801:Humans; D013287:Illicit Drugs / Q000737:chemistry
chemical_list: D000662:Amphetamines; D013287:Illicit Drugs; C040639:4-fluoroamphetamine
keywords: Chiral derivatization agents; Enantioseparation; Indirect chiral separation; Phenylethylamine derivatives; Position isomers; “Legal Highs”