Structural analysis of an lysergic acid diethylamide (LSD) analogue N-methyl-N-isopropyllysergamide (MiPLA): Insights from Rotamers in NMR spectra.
Takuji Shoda, Genichiro Tsuji, Maiko Kawamura, Takashi Kurohara, Takashi Misawa, Ruri Kikura-Hanajiri, Yosuke Demizu
Drug testing and analysis June 1, 2024 DOI: 10.1002/dta.3586 via PubMed
Summary
AI-generated from the abstractLysergic acid diethylamide (LSD) is a hallucinogen that activates the serotonin 2A receptor and is a controlled substance in Japan. Recently, MiPLA, an N-methyl-N-isopropyl derivative of LSD, has appeared in paper-sheet products in several countries. This work describes the three-step synthesis of MiPLA starting from ergometrine maleate, which also produced the (8S)-isomer, iso-MiPLA, as a by-product. Liquid chromatography-mass spectrometry showed that LSD, MiPLA, and iso-MiPLA have different retention times. Nuclear magnetic resonance spectroscopy determined their chemical structures and revealed rotamers involving the N-methyl-N-isopropyl groups of tertiary amides in MiPLA and iso-MiPLA.
Study at a glance
| Characteristics | Synthesis and analytical study Peer reviewed |
|---|---|
| Topics | LSD |
| Keywords | Mipla Nmr Rotamer Tertiary amide |
| Citations | 1 |
| Key finding | MiPLA and its (8S)-isomer, iso-MiPLA, were synthesized from ergometrine maleate, and their structures were confirmed by NMR, which showed rotamers from the tertiary amide groups. |
Abstract
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.