{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,9]],"date-time":"2026-06-09T01:02:48Z","timestamp":1780966968602,"version":"3.54.1"},"reference-count":38,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2023,6,15]],"date-time":"2023-06-15T00:00:00Z","timestamp":1686787200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2024,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Preclinical investigations have shown that <jats:italic>N<\/jats:italic>\u2010ethyl\u2010<jats:italic>N<\/jats:italic>\u2010isopropyllysergamide (EIPLA) exhibits lysergic acid diethylamide (LSD)\u2010like properties, which suggests that it might show psychoactive effects in humans. EIPLA is also an isomer of <jats:italic>N<\/jats:italic><jats:sup>6<\/jats:sup>\u2010ethylnorlysergic acid <jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010diethylamide (ETH\u2010LAD), 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\u2010phase infrared spectroscopy. The most straightforward differentiation between EIPLA and ETH\u2010LAD included the evaluation of mass spectral features that reflected the structural differences (EIPLA: <jats:italic>N<\/jats:italic><jats:sup>6<\/jats:sup>\u2010methyl and <jats:italic>N<\/jats:italic>\u2010ethyl\u2010<jats:italic>N<\/jats:italic>\u2010isopropylamide group; ETH\u2010LAD: <jats:italic>N<\/jats:italic><jats:sup>6<\/jats:sup>\u2010ethyl and <jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010diethylamide 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\u2009\u00b1\u20090.5\u2009\u03bcg (RSD: 0.6%) and 85.8\u2009\u00b1\u20092.8\u2009\u03bcg base equivalents based on LC\u2013MS analysis. The in vivo activity of EIPLA was evaluated using the mouse head\u2010twitch response (HTR) assay. Similar to LSD and other serotonergic psychedelics, EIPLA induced the HTR (ED<jats:sub>50<\/jats:sub>\u2009=\u2009234.6\u2009nmol\/kg), which was about half the potency of LSD (ED<jats:sub>50<\/jats:sub>\u2009=\u2009132.8\u2009nmol\/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.<\/jats:p>","DOI":"10.1002\/dta.3530","type":"journal-article","created":{"date-parts":[[2023,6,15]],"date-time":"2023-06-15T19:12:20Z","timestamp":1686856340000},"page":"187-198","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Analytical and behavioral characterization of <i>N<\/i>\u2010ethyl\u2010<i>N<\/i>\u2010isopropyllysergamide (EIPLA), an isomer of <i>N<\/i><sup>6<\/sup>\u2013ethylnorlysergic acid <i>N<\/i>,<i>N<\/i>\u2010diethylamide (ETH\u2010LAD)"],"prefix":"10.1002","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8632-5372","authenticated-orcid":false,"given":"Simon D.","family":"Brandt","sequence":"first","affiliation":[{"name":"School of Pharmacy and Biomolecular Sciences Liverpool John Moores University  Liverpool UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1613-3305","authenticated-orcid":false,"given":"Pierce V.","family":"Kavanagh","sequence":"additional","affiliation":[{"name":"Department of Pharmacology and Therapeutics School of Medicine, Trinity Centre for Health Sciences, St. James Hospital  Dublin 8 Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0452-7814","authenticated-orcid":false,"given":"Folker","family":"Westphal","sequence":"additional","affiliation":[{"name":"State Bureau of Criminal Investigation Schleswig\u2010Holstein, Section Narcotics\/Toxicology  Kiel Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7772-2111","authenticated-orcid":false,"given":"Benedikt","family":"Pulver","sequence":"additional","affiliation":[{"name":"State Bureau of Criminal Investigation Schleswig\u2010Holstein, Section Narcotics\/Toxicology  Kiel Germany"},{"name":"Institute of Forensic Medicine, Forensic Toxicology, Medical Center, Faculty of Medicine University of Freiburg  Freiburg Germany"},{"name":"Hermann Staudinger Graduate School University of Freiburg  Freiburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7867-5831","authenticated-orcid":false,"given":"Hannes M.","family":"Schwelm","sequence":"additional","affiliation":[{"name":"Institute of Forensic Medicine, Forensic Toxicology, Medical Center, Faculty of Medicine University of Freiburg  Freiburg Germany"},{"name":"Hermann Staudinger Graduate School University of Freiburg  Freiburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander","family":"Stratford","sequence":"additional","affiliation":[{"name":"Synex Synthetics BV  Maastricht The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1883-2804","authenticated-orcid":false,"given":"Volker","family":"Auw\u00e4rter","sequence":"additional","affiliation":[{"name":"State Bureau of Criminal Investigation Schleswig\u2010Holstein, Section Narcotics\/Toxicology  Kiel Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5096-5829","authenticated-orcid":false,"given":"Adam L.","family":"Halberstadt","sequence":"additional","affiliation":[{"name":"Department of Psychiatry University of California San Diego  La Jolla California USA"},{"name":"Research Service, VA San Diego Healthcare System  San Diego California USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,6,15]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/cpt.557"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschemneuro.8b00043"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/7854_2017_475"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1055\/a\u20101310\u20103990"},{"key":"e_1_2_6_6_1","volume-title":"TIHKAL: the continuation","author":"Shulgin A","year":"1997"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00213\u2010018\u20105055\u20109"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cell.2020.08.024"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cell.2016.12.033"},{"key":"e_1_2_6_10_1","first-page":"240","article-title":"Psychotomimetic drugs; chemical and pharmacological aspects","volume":"8","author":"Hofmann A","year":"1959","journal-title":"Acta Physiol Pharmacol Neerl"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/0091\u20103057(94)90172\u20104"},{"key":"e_1_2_6_12_1","first-page":"52","volume-title":"Hallucinogens: an Update. 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