{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T00:14:03Z","timestamp":1791850443256,"version":"4.3.4"},"reference-count":29,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2024,4,3]],"date-time":"2024-04-03T00:00:00Z","timestamp":1712102400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2025,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>1\u2010Acetyl\u2010<jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010diethyllysergamide (1A\u2010LSD, ALD\u201052) was first synthesized in the 1950s and found to produce psychedelic effects similar to those of LSD. Evidence suggests that ALD\u201052 serves as a prodrug in vivo and hydrolysis to LSD is likely responsible for its activity. Extension of the <jats:italic>N<\/jats:italic><jats:sup>1<\/jats:sup>\u2010alkylcarbonyl chain gives rise to novel lysergamides, which spurred further investigations into their structure\u2013activity relationships. At the same time, ALD\u201052 and numerous homologues have emerged as recreational drugs (\u201cresearch chemicals\u201d) that are available from online vendors. In the present study, 1\u2010dodecanoyl\u2010LSD (1DD\u2010LSD), a novel <jats:italic>N<\/jats:italic><jats:sup>1<\/jats:sup>\u2010acylated LSD derivative, was subjected to analytical characterization and was also tested in the mouse head\u2010twitch response (HTR) assay to assess whether it produces LSD\u2010like effects in vivo. When tested in C57BL\/6J mice, 1DD\u2010LSD induced the HTR with a median effective dose (ED<jats:sub>50<\/jats:sub>) of 2.17\u2009mg\/kg, which was equivalent to 3.60\u2009\u03bcmol\/kg. Under similar experimental conditions, LSD has 27\u2010fold higher potency than 1DD\u2010LSD in the HTR assay. Previous work has shown that other homologues such as ALD\u201052 and 1\u2010propanoyl\u2010LSD also have considerably higher potency than 1DD\u2010LSD in mice, which suggests that hydrolysis of the 1\u2010dodecanoyl moiety may be comparatively less efficient in vivo. Further investigations are warranted to determine whether the increased lipophilicity of 1DD\u2010LSD causes it to be sequestered in fat, thereby reducing its exposure to enzymatic hydrolysis in plasma and tissues. Further clinical studies are also required to assess its activity in humans and to test the prediction that it could potentially serve as a long\u2010acting prodrug for LSD.<\/jats:p>","DOI":"10.1002\/dta.3691","type":"journal-article","created":{"date-parts":[[2024,4,3]],"date-time":"2024-04-03T19:25:36Z","timestamp":1712172336000},"page":"101-109","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Analytical and behavioral characterization of 1\u2010dodecanoyl\u2010LSD (1DD\u2010LSD)"],"prefix":"10.1002","volume":"17","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1613-3305","authenticated-orcid":false,"given":"Pierce V.","family":"Kavanagh","sequence":"first","affiliation":[{"name":"Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences St. James Hospital  Dublin 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"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5219-1687","authenticated-orcid":false,"given":"Simon P.","family":"Elliott","sequence":"additional","affiliation":[{"name":"Elliott Forensic Consulting  Birmingham UK"},{"name":"Department of Analytical, Environmental and Forensic Sciences King's College London  London UK"}],"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\/0000-0001-5096-5829","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"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8632-5372","authenticated-orcid":false,"given":"Simon D.","family":"Brandt","sequence":"additional","affiliation":[{"name":"School of Pharmacy and Biomolecular Sciences Liverpool John Moores University  Liverpool UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,4,3]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19570400619"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1749\u20106632.1957.tb40756.x"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1080\/00223980.1959.9916341"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1001\/archneurpsyc.1959.02340170081008"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00408108"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF01562113"},{"key":"e_1_2_6_8_1","first-page":"169","volume-title":"Drugs Affecting the Central Nervous System","author":"Hofmann A","year":"1968"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.neuropharm.2019.107856"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00216\u2010018\u20101558\u20109"},{"key":"e_1_2_6_11_1","unstructured":"European Monitoring Centre for Drugs and Drug Addiction (EMCDDA).EMCDDA\u2010Europol 2016 annual report on the implementation of council decision 2005\/387\/JHA. 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