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Syntheses and analytical characterizations of the research chemical 1-[1-(2-fluorophenyl)-2-phenylethyl]pyrrolidine (fluorolintane) and five of its isomers

Dybek, M, Wallach, J, Kavanagh, PV, Colestock, T, Filbman, N, Dowling, G, Westphal, F, Elliott, SP, Adejare, A and Brandt, SD (2019) Syntheses and analytical characterizations of the research chemical 1-[1-(2-fluorophenyl)-2-phenylethyl]pyrrolidine (fluorolintane) and five of its isomers. Drug Testing and Analysis, 11 (8). pp. 1144-1161. ISSN 1942-7611

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Abstract

A number of substances based on the 1,2-diarylethylamine template have been investigated for various potential clinical applications whereas others have been encountered as research chemicals sold for non-medical use. Some of these substances have transpired to function as NMDA receptor antagonists that elicit dissociative effects in people who use these substances recreationally. 1-[1-(2-Fluorophenyl)-2-phenylethyl]pyrrolidine (fluorolintane, 2-F-DPPy) has recently appeared as a research chemical, which users report has dissociative effects. One common difficulty encountered by stakeholders confronting the appearance of new psychoactive substances is the presence of positional isomers. In the case of fluorolintane, the presence of the fluorine substituent on either the phenyl and benzyl moieties of the 1,2-diarylethylamine structure results in a total number of six possible racemic isomers, namely 2-F-, 3-F-, and 4-F-DPPy (phenyl ring substituents) and 2’’-F-, 3’’-F-, and 4’’-F-DPPy (benzyl ring substituents). The present study reports the chemical syntheses and comprehensive analytical characterizations of the two sets of three positional isomers. These studies included various low- and high-resolution mass spectrometry platforms, gas- and liquid chromatography (GC and LC), nuclear magnetic resonance spectroscopy (NMR) and GC-condensed phase and attenuated total reflection infrared spectroscopy analyses. The differentiation between each set of three isomers was possible under a variety of experimental conditions including GC chemical ionization triple quadrupole tandem mass spectrometric analysis of the [M + H – HF]+ species. The latter MS method was particularly helpful as it revealed distinct formation of product ions for each of the six investigated substances.

Item Type: Article
Additional Information: This is the peer reviewed version of the following article: Dybek, M, Wallach, J, Kavanagh, PV, et al. Syntheses and analytical characterizations of the research chemical 1‐[1‐(2‐fluorophenyl)‐2‐phenylethyl]pyrrolidine (fluorolintane) and five of its isomers. Drug Test Anal. 2019; 11: 1144– 1161, which has been published in final form at https://dx.doi.org/10.1002/dta.2608. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Uncontrolled Keywords: 0301 Analytical Chemistry, 1115 Pharmacology and Pharmaceutical Sciences
Subjects: R Medicine > RM Therapeutics. Pharmacology
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Wiley
Date Deposited: 24 Apr 2019 10:05
Last Modified: 10 Jul 2020 00:50
DOI or Identification number: 10.1002/dta.2608
URI: https://researchonline.ljmu.ac.uk/id/eprint/10591

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