Synthesis and analytical characterization of 1‐(2‐thienoyl)‐6‐allyl‐nor‐d‐lysergic acid diethylamide (1T‐AL‐LAD)

Abstract

AbstractLysergic acid diethylamide (LSD) analogs have emerged as new psychoactive substances (NPS) since the mid‐2010s, and new compounds continue to emerge for recreational use. Since the end of 2023, “1D‐AL‐LAD” appeared on X (formerly Twitter) and other websites. As for the compound “1D‐LSD” (which also has “1D” in the name), several studies show that the ingredient of seized blotter paper printed “1D‐LSD” was actually 1‐(2‐thienoyl)‐LSD (1T‐LSD). However, there are no reports of seizures of 1‐(1,2‐dimethylcyclobutanecarbonyl)‐LSD (1D‐LSD). Accordingly, it was considered that all or at least a certain percentage of “1D‐AL‐LAD (1‐(1,2‐dimethylcyclobutanecarbonyl)‐6‐allyl‐nor‐LSD)” is actually 1‐(2‐thienoyl)‐6‐allyl‐nor‐LSD (1T‐AL‐LAD). This compound is handled by a number of distributors as of April 2024; therefore, it should be characterized in advance if seized. In this study, 1T‐AL‐LAD was synthesized and characterized using nuclear magnetic resonance spectroscopy, Fourier transform‐infrared spectroscopy, liquid chromatography/high‐resolution mass spectrometry (LC/HRMS) and gas chromatography/MS (GC/MS). This compound was easily distinguished from previously reported lysergamides. There were some differences in the detectability of 1T‐AL‐LAD compared with other lysergamides using GC/MS and the fragmentation patterns in LC/HRMS. These differences can be reasonably explained. This information will be of help to determine this substance in seized materials should it emerge on the market.