Structural analysis of an lysergic acid diethylamide (LSD) analogue N-methyl-N-isopropyllysergamide (MiPLA): Insights from Rotamers in NMR spectra.
Drug testing and analysis June 1, 2024 Takuji Shoda, Genichiro Tsuji, Maiko Kawamura et al. 1 citation
Lysergic 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.