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Analytical and behavioral characterization of N-ethyl-N-isopropyllysergamide (EIPLA), an isomer of ETH-LAD

Brandt, S, Kavanagh, PV, Westphal, F, Pulver, B, Schwelm, HM, Stratford, A, Auwärter, V and Halberstadt, AL (2023) Analytical and behavioral characterization of N-ethyl-N-isopropyllysergamide (EIPLA), an isomer of ETH-LAD. Drug Testing and Analysis. ISSN 1942-7603

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Preclinical investigations have shown that N-ethyl-N-isopropyllysergamide (EIPLA) exhibits LSD-like properties, which suggests that it might show psychoactive effects in humans. EIPLA is also an isomer of N6-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 mass spectrometry, chromatography (GC, LC), nuclear magnetic resonance spectroscopy (NMR), 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: N6-methyl and N-ethyl-N-isopropylamide group; ETH-LAD: N6-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 (ED50 = 234.6 nmol/kg), which was about half the potency of LSD (ED50 = 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.

Item Type: Article
Uncontrolled Keywords: 0301 Analytical Chemistry; 0601 Biochemistry and Cell Biology; 1115 Pharmacology and Pharmaceutical Sciences; Analytical Chemistry
Subjects: R Medicine > RM Therapeutics. Pharmacology
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Wiley
SWORD Depositor: A Symplectic
Date Deposited: 05 Jun 2023 10:51
Last Modified: 20 Jun 2023 10:15
DOI or ID number: 10.1002/dta.3530
URI: https://researchonline.ljmu.ac.uk/id/eprint/19616
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