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Structural analysis of an lysergic acid diethylamide (LSD) analogue N-methyl-N-isopropyllysergamide (MiPLA): Insights from Rotamers in NMR spectra.
Shoda, Takuji; Tsuji, Genichiro; Kawamura, Maiko; Kurohara, Takashi; Misawa, Takashi; Kikura-Hanajiri, Ruri; Demizu, Yosuke.
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  • Shoda T; Division of Organic Chemistry, National Institute of Health Sciences, Kawasaki, Japan.
  • Tsuji G; Division of Organic Chemistry, National Institute of Health Sciences, Kawasaki, Japan.
  • Kawamura M; Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Kawasaki, Japan.
  • Kurohara T; Division of Organic Chemistry, National Institute of Health Sciences, Kawasaki, Japan.
  • Misawa T; Division of Organic Chemistry, National Institute of Health Sciences, Kawasaki, Japan.
  • Kikura-Hanajiri R; Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Kawasaki, Japan.
  • Demizu Y; Division of Organic Chemistry, National Institute of Health Sciences, Kawasaki, Japan.
Drug Test Anal ; 2023 Oct 13.
Article en En | MEDLINE | ID: mdl-37830386
Lysergic acid diethylamide (LSD) is a hallucinogenic compound that binds to and activates the serotonin 2A receptor and is classified as a controlled narcotic in Japan. Recently, MiPLA, an N-methyl-N-isopropyl derivative of LSD, has been detected in paper-sheet products in several countries. This study focuses on the synthesis of MiPLA and includes a comprehensive analysis involving structural and liquid chromatography-mass spectrometry (LC-MS). Particularly, MiPLA was synthesized in three-steps starting from ergometrine maleate, which resulted in the formation of (8S)-isomer, iso-MiPLA, as a by-product. The LC-MS results showed that LSD, MiPLA, and iso-MiPLA exhibited different retention times. Their chemical structures were determined using nuclear magnetic resonance spectroscopy, which revealed the presence of rotamers involving the N-methyl-N-isopropyl groups of tertiary amides in MiPLA and iso-MiPLA.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Drug Test Anal Asunto de la revista: FARMACOLOGIA Año: 2023 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Reino Unido
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Drug Test Anal Asunto de la revista: FARMACOLOGIA Año: 2023 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Reino Unido