Identification of two lysergic acid diethylamide analogs, 1-(3-(trimethylsilyl) propionyl) lysergic acid diethylamide (1S-LSD) and 1-(2-thienoyl)-6-allyl-nor-d-lysergic acid diethylamide (1T-AL-LAD), in paper sheet products distributed on the internet.

Two new LSD analogs, 1S-LSD and 1T-AL-LAD, were identified in sheet products sold in Japan. Their structures were determined using gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, and nuclear magnetic resonance. A trace amount of iso-1S-LSD, a C8-epimerization product, was also suggested in one product. This is the first report of these compounds in sheet products in Japan. The metabolic pathways and biological activities of 1S-LSD and 1T-AL-LAD remain unexplored, and further investigation into their possible in vivo deacylation and conversion into LSD or AL-LAD is needed.

Study at a glance

Abstract

Recently, numerous lysergic acid diethylamide (LSD) analogs have emerged as designer drugs globally. These compounds are mainly distributed as sheet products. In this study, two new LSD analogs were identified from sheet products. The structures of the compounds were determined by gas chromatography-mass spectrometry, liquid chromatography-photodiode array-mass spectrometry, liquid chromatography with hybrid quadrupole time-of-flight mass spectrometry and nuclear magnetic resonance (NMR) measurement. From the NMR analysis, two compounds in the products were identified as N,N-diethyl-7-methyl-4-(3-(trimethylsilyl)propanoyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (1S-LSD) and 7-allyl-N,N-diethyl-4-(thiophene-2-carbonyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (1T-AL-LAD). In the product where 1S-LSD was detected, the presence of a trace amount of iso-1S-LSD, a C8-epimerization product of 1S-LSD, was suggested. This paper is the first to report the detection of 1S-LSD and 1T-AL-LAD in sheet products in Japan. Notably, the metabolic pathways and biological activities of 1S-LSD and 1T-AL-LAD are not explored. The possibility of the in vivo deacylation and conversion of the compoundsinto LSD or AL-LAD should be further investigated.