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Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products

PURPOSE: Many analogs of lysergic acid diethylamide (LSD) have recently appeared as designer drugs around the world. These compounds are mainly distributed as sheet products. In this study, we identified three more newly distributed LSD analogs from paper sheet products. METHODS: The structures of t...

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Autores principales: Tanaka, Rie, Kawamura, Maiko, Mizutani, Sakumi, Kikura-Hanajiri, Ruri
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Nature Singapore 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10310582/
https://www.ncbi.nlm.nih.gov/pubmed/36809464
http://dx.doi.org/10.1007/s11419-023-00661-1
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author Tanaka, Rie
Kawamura, Maiko
Mizutani, Sakumi
Kikura-Hanajiri, Ruri
author_facet Tanaka, Rie
Kawamura, Maiko
Mizutani, Sakumi
Kikura-Hanajiri, Ruri
author_sort Tanaka, Rie
collection PubMed
description PURPOSE: Many analogs of lysergic acid diethylamide (LSD) have recently appeared as designer drugs around the world. These compounds are mainly distributed as sheet products. In this study, we identified three more newly distributed LSD analogs from paper sheet products. METHODS: The structures of the compounds were determined by gas chromatography–mass spectrometry (GC–MS), liquid chromatography–photodiode array–mass spectrometry (LC–PDA–MS), liquid chromatography with hybrid quadrupole time-of-flight mass spectrometry (LC–Q-TOF-MS) and nuclear magnetic resonance (NMR) spectroscopy. RESULTS: From the NMR analysis, the compounds in the four products were identified as 4-(cyclopropanecarbonyl)-N,N-diethyl-7-(prop-2-en-1-yl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (1cP-AL-LAD), 4-(cyclopropanecarbonyl)-N-methyl-N-isopropyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo-[4,3-fg]quinoline-9-carboxamide (1cP-MIPLA), N,N-diethyl-7-methyl-4-pentanoyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (1V-LSD) and (2’S,4’S)-lysergic acid 2,4-dimethylazetidide (LSZ). In comparison with the structure of LSD, 1cP-AL-LAD was converted at the positions at N1 and N6, and 1cP-MIPLA was converted at the positions at N1 and N18. The metabolic pathways and biological activities of 1cP-AL-LAD and 1cP-MIPLA have not been reported. CONCLUSIONS: This is the first report showing that LSD analogs that were converted at multiple positions have been detected in sheet products in Japan. There are concerns about the future distribution of sheet drug products containing new LSD analogs. Therefore, the continuous monitoring for newly detected compounds in sheet products is important. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s11419-023-00661-1.
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spelling pubmed-103105822023-07-01 Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products Tanaka, Rie Kawamura, Maiko Mizutani, Sakumi Kikura-Hanajiri, Ruri Forensic Toxicol Short Communication PURPOSE: Many analogs of lysergic acid diethylamide (LSD) have recently appeared as designer drugs around the world. These compounds are mainly distributed as sheet products. In this study, we identified three more newly distributed LSD analogs from paper sheet products. METHODS: The structures of the compounds were determined by gas chromatography–mass spectrometry (GC–MS), liquid chromatography–photodiode array–mass spectrometry (LC–PDA–MS), liquid chromatography with hybrid quadrupole time-of-flight mass spectrometry (LC–Q-TOF-MS) and nuclear magnetic resonance (NMR) spectroscopy. RESULTS: From the NMR analysis, the compounds in the four products were identified as 4-(cyclopropanecarbonyl)-N,N-diethyl-7-(prop-2-en-1-yl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (1cP-AL-LAD), 4-(cyclopropanecarbonyl)-N-methyl-N-isopropyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo-[4,3-fg]quinoline-9-carboxamide (1cP-MIPLA), N,N-diethyl-7-methyl-4-pentanoyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (1V-LSD) and (2’S,4’S)-lysergic acid 2,4-dimethylazetidide (LSZ). In comparison with the structure of LSD, 1cP-AL-LAD was converted at the positions at N1 and N6, and 1cP-MIPLA was converted at the positions at N1 and N18. The metabolic pathways and biological activities of 1cP-AL-LAD and 1cP-MIPLA have not been reported. CONCLUSIONS: This is the first report showing that LSD analogs that were converted at multiple positions have been detected in sheet products in Japan. There are concerns about the future distribution of sheet drug products containing new LSD analogs. Therefore, the continuous monitoring for newly detected compounds in sheet products is important. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s11419-023-00661-1. Springer Nature Singapore 2023-02-21 2023 /pmc/articles/PMC10310582/ /pubmed/36809464 http://dx.doi.org/10.1007/s11419-023-00661-1 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Short Communication
Tanaka, Rie
Kawamura, Maiko
Mizutani, Sakumi
Kikura-Hanajiri, Ruri
Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products
title Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products
title_full Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products
title_fullStr Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products
title_full_unstemmed Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products
title_short Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products
title_sort identification of lsd analogs, 1cp-al-lad, 1cp-mipla, 1v-lsd and lsz in sheet products
topic Short Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10310582/
https://www.ncbi.nlm.nih.gov/pubmed/36809464
http://dx.doi.org/10.1007/s11419-023-00661-1
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