Distinction of Some Dialkyl Amides of Lysergic and iso-Lysergic Acids from LSD

Abstract

The 10 lysergic and iso-lysergic acid amides described are N,N-dimethyl-, N,N-diethyl-, N-methyl-N-propyl, N-ethyl-N-propyl, and N,N-dipropyl-. Their ultraviolet spectra are insufficiently different for distinction. Mass spectra do not readily differentiate between isomers. Proton magnetic resonance spectra are distinct and provide a positive structural identification of the amide. Their infrared spectra are similar, but suitable for distinguishing these compounds from LSD. Various reference spectra are provided. Thin layer and gas-liquid chromatographic systems suitable for distinguishing these compounds from LSD are described.

Return of the lysergamides. Part II: Analytical and behavioural characterization of N6‐allyl‐6‐norlysergic acid diethylamide (AL‐LAD) and (2’S,4’S)‐lysergic acid 2,4‐dimethylazetidide (LSZ)

“…The ATR‐FTIR spectrum of AL‐LAD is shown in Figure . Key features also observed for LSD, such as the C = O and C‐N stretch or C‐H out‐of‐plane deformations suggested to be associated with the indole ring, have also been observed . The NH bands at higher wavenumbers were present as expected but this was not observed previously in the spectrum recorded for 1P‐LSD under identical conditions due to the attachment of the propionyl group .…”

“…Key features also observed for LSD, such as the C = O and C-N stretch or C-H out-of-plane deformations suggested to be associated with the indole ring, have also been observed. [36][37][38][39] The NH bands at higher wavenumbers were present as expected but this was not observed previously in the spectrum recorded for 1P-LSD under identical conditions due to the attachment of the propionyl group. [17] As already described, GC-MS analysis of LSZ revealed the detection of what appeared to be LSZ isomers.…”

Analytical profile of N‐ethyl‐N‐cyclopropyl lysergamide (ECPLA), an isomer of lysergic acid 2,4‐dimethylazetidide (LSZ)

“…However, some differences could also be observed, such as bands at 1448/1417 cm −1 (ECPLA) vs. 1448/1435 cm −1 (LSZ), 1233/1259 cm −1 (ECPLA) compared with 1237/1278 cm −1 (LSZ) and 1129 cm −1 (ECPLA) (Figure 4). Minor but distinct differences between various lysergamide homologs have been reported previously, including those detected in the region 1350–1150 cm −1 14 . Indole N‐H stretches at 3288 cm −1 (ECPLA) and 3263 cm −1 (LSZ), which are typically seen for lysergamides, were also detectable (see the Supporting Information).…”

Return of the lysergamides. Part I: Analytical and behavioural characterization of 1‐propionyl‐d‐lysergic acid diethylamide (1P‐LSD)

“…The ability to characterize and correctly identify new psychoactive substances constitutes an important part of forensic and clinical work. Aside from LSD, the analysis and analytical characterizations of lysergamide derivatives have been featured in investigations carried out in previous decades, possibly due to wider availability of LSD and greater interest at the time; examples include ALD‐52, d ‐lysergic acid N ‐methyl‐ N ‐propylamide (LAMPA) and a range of other N , N ‐dialkylated derivatives . The analytical and pharmacological characterization of 1P‐LSD reported in the present study represents the newest addition to the field of lysergamide analysis within the field of clinical study and the topic of new psychoactive substances that are available for purchase from Internet retailers …”