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Analytical profile of N-ethyl-N-cyclopropyl lysergamide (ECPLA), an isomer of lysergic acid 2,4-dimethylazetidide (LSZ)

Brandt, SD, Kavanagh, PV, Westphal, F, Stratford, A, Elliott, SP, Dowling, G and Halberstadt, AL Analytical profile of N-ethyl-N-cyclopropyl lysergamide (ECPLA), an isomer of lysergic acid 2,4-dimethylazetidide (LSZ). Drug Testing and Analysis. ISSN 1942-7603 (Accepted)

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Abstract

Recent investigations have shown that N-ethyl-N-cyclopropyl lysergamide (ECPLA) produces LSD-like behavioral effects in mice, which suggests that it may act as a hallucinogen in humans. Although the use of ECPLA as a recreational drug has been limited, key analytical data that can be used to detect ECPLA are required for future forensic and clinical investigations. ECPLA is an isomer of (2’S,4’S)-lysergic acid 2,4-dimethylazetidide (LSZ), a lysergamide that emerged as a recreational drug in 2013. Several analytical approaches were examined, including single- and tandem mass spectrometry platforms at low and high resolution, gas- and liquid chromatography (GC, LC), nuclear magnetic resonance spectroscopy (NMR), and GC condensed-phase infrared spectroscopy (GC-sIR). ECPLA and LSZ could be differentiated by NMR, GC-sIR, GC, and LC-based methods. The electron ionization mass spectra of ECPLA and LSZ contained ion clusters typically observed with related lysergamides such as m/z 150–155, m/z 177–182, m/z 191–197, m/z 205–208, and m/z 219–224. One of the significant differences in abundance related to these clusters included ions at m/z 196 and m/z 207/208. The base peaks were detected at m/z 221 in both cases followed by the retro-Diels-Alder fragment at m/z 292. Minor but noticeable differences between the two isomers could also be seen in the relative abundance of m/z 98 and m/z 41. Electrospray ionization mass spectra included lysergamide-related ions at m/z 281, 251, 223, 208, 197, 180, and 140. LSZ (but not ECPLA) showed product ions at m/z 267 and m/z 98 under the condition used.

Item Type: Article
Uncontrolled Keywords: 0301 Analytical Chemistry, 0601 Biochemistry and Cell Biology, 1115 Pharmacology and Pharmaceutical Sciences
Subjects: R Medicine > RS Pharmacy and materia medica
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Wiley
Date Deposited: 12 Aug 2020 09:52
Last Modified: 12 Aug 2020 09:52
URI: http://researchonline.ljmu.ac.uk/id/eprint/13488

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