Analytical and behavioral characterization of N-ethyl-N-isopropyllysergamide (EIPLA), an isomer of N 6 -ethylnorlysergic acid N,N-diethylamide (ETH-LAD).

Autor: Brandt SD; School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Liverpool, UK., Kavanagh PV; Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences, St. James Hospital, Dublin 8, Ireland., Westphal F; State Bureau of Criminal Investigation Schleswig-Holstein, Section Narcotics/Toxicology, Kiel, Germany., Pulver B; State Bureau of Criminal Investigation Schleswig-Holstein, Section Narcotics/Toxicology, Kiel, Germany.; Institute of Forensic Medicine, Forensic Toxicology, Medical Center, Faculty of Medicine, University of Freiburg, Freiburg, Germany.; Hermann Staudinger Graduate School, University of Freiburg, Freiburg, Germany., Schwelm HM; Institute of Forensic Medicine, Forensic Toxicology, Medical Center, Faculty of Medicine, University of Freiburg, Freiburg, Germany.; Hermann Staudinger Graduate School, University of Freiburg, Freiburg, Germany., Stratford A; Synex Synthetics BV, Maastricht, The Netherlands., Auwärter V; State Bureau of Criminal Investigation Schleswig-Holstein, Section Narcotics/Toxicology, Kiel, Germany., Halberstadt AL; Department of Psychiatry, University of California San Diego, La Jolla, California, USA.; Research Service, VA San Diego Healthcare System, San Diego, California, USA.
Jazyk: angličtina
Zdroj: Drug testing and analysis [Drug Test Anal] 2024 Feb; Vol. 16 (2), pp. 187-198. Date of Electronic Publication: 2023 Jun 15.
DOI: 10.1002/dta.3530
Abstrakt: Preclinical investigations have shown that N-ethyl-N-isopropyllysergamide (EIPLA) exhibits lysergic acid diethylamide (LSD)-like properties, which suggests that it might show psychoactive effects in humans. EIPLA is also an isomer of N 6 -ethylnorlysergic acid N,N-diethylamide (ETH-LAD), a lysergamide known to produce psychedelic effects in humans that emerged as a research chemical. EIPLA was subjected to analysis by various forms of mass spectrometry, chromatography (GC, LC), nuclear magnetic resonance (NMR) spectroscopy, and GC condensed-phase infrared spectroscopy. The most straightforward differentiation between EIPLA and ETH-LAD included the evaluation of mass spectral features that reflected the structural differences (EIPLA: N 6 -methyl and N-ethyl-N-isopropylamide group; ETH-LAD: N 6 -ethyl and N,N-diethylamide group). Proton NMR analysis of blotter extracts suggested that EIPLA was detected as the base instead of a salt, and two blotter extracts suspected to contain EIPLA revealed the detection of 96.9 ± 0.5 μg (RSD: 0.6%) and 85.8 ± 2.8 μg base equivalents based on LC-MS analysis. The in vivo activity of EIPLA was evaluated using the mouse head-twitch response (HTR) assay. Similar to LSD and other serotonergic psychedelics, EIPLA induced the HTR (ED 50  = 234.6 nmol/kg), which was about half the potency of LSD (ED 50  = 132.8 nmol/kg). These findings are consistent with the results of previous studies demonstrating that EIPLA can mimic the effects of known psychedelic drugs in rodent behavioral models. The dissemination of analytical data for EIPLA was deemed justifiable to aid future forensic and clinical investigations.
(© 2023 The Authors. Drug Testing and Analysis published by John Wiley & Sons Ltd.)
Databáze: MEDLINE
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