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

Since late 2023, a substance sold as "1D-AL-LAD" has appeared online, but chemical analysis suggests it is actually 1-(2-thienoyl)-6-allyl-nor-LSD (1T-AL-LAD), not the claimed 1-(1,2-dimethylcyclobutanecarbonyl)-6-allyl-nor-LSD. To aid forensic identification, researchers synthesized 1T-AL-LAD and characterized it with nuclear magnetic resonance spectroscopy, Fourier transform-infrared spectroscopy, liquid chromatography/high-resolution mass spectrometry, and gas chromatography/mass spectrometry. The compound was easily distinguished from previously reported lysergamides. Detectability differences in GC/MS and fragmentation patterns in LC/HRMS were noted and explained. This information will help identify the substance in seized materials should it emerge on the market.

Study at a glance

Abstract

Lysergic 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.