Recently, lysergic acid diethylamide (LSD) analogs have appeared worldwide as designer drugs. In this study, we identified a distributed LSD analog from a paper-sheet product. Gas chromatography–mass spectrometry (GC-MS), liquid chromatography–photodiode array–mass spectrometry (LC-PDA-MS), and liquid chromatography with hybrid quadrupole time-of-flight mass spectrometry (LC-QTOF-MS) were used to analyze the sheet product. The sheet product claimed to contain 1-(1,2-dimethylcyclobutanoyl)-N,N-diethyllysergamide (1D-LSD). However, an unknown compound was detected in the product together with tryptamine and L-tryptophan methyl ester. This compound was isolated from the sheets and identified as 1-(thiophene-2-carbonyl)-N,N-diethyl-6-methyl-9,10-didehydroergoline-8β-carboxamide (1-thiophenoyl LSD; 1-(2-thienoyl)-LSD, 1T-LSD), using ¹H, ¹³C nuclear magnetic resonance (NMR) spectroscopy and various two-dimensional NMR techniques. 1T-LSD was shown to have the thiophene-2-carbonyl group at the N¹ position instead of the 1,2-dimethylcyclobutane-carbonyl group as claimed. The amount of 1T-LSD (free base) in three individual unit from one sheet was determined to be 87–100 μg per unit using a proton-specific quantitative NMR (¹H-qNMR) method. Deacylation of 1T-LSD to LSD was also observed to occur in methanol-d₄ during NMR analysis. The UV spectrum of 1T-LSD differed from that of other LSD analogs, and the fluorescence sensitivity was much lower. Because of concerns about the future distribution of products containing new LSD analogs, continued monitoring of newly detected compounds in sheet products is encouraged.

中文翻译：

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吸墨纸产品中麦角酸二乙酰胺类似物 1-(噻吩-2-羰基)-N,N-二乙基麦角酰胺 (1T-LSD) 的表征


最近，麦角酸二乙酰胺（LSD）类似物作为设计药物出现在世界范围内。在这项研究中，我们从纸质产品中鉴定出了一种分布式 LSD 类似物。采用气相色谱-质谱联用仪 (GC-MS)、液相色谱-光电二极管阵列-质谱联用仪 (LC-PDA-MS) 和液相色谱-混合四极杆飞行时间质谱联用仪 (LC-QTOF-MS)分析板材产品。该片材产品声称含有1-(1,2-二甲基环丁酰基) -N , N-二乙基麦角酰胺(1D-LSD)。然而，在产品中检测到一种未知化合物以及色胺和L-色氨酸甲酯。从片材中分离出该化合物，并鉴定为 1-(噻吩-2-羰基) -N , N-二乙基-6-甲基-9,10-二脱氢麦角林-8β-甲酰胺（1-噻吩酰基 LSD；1-(2-噻吩酰基)-LSD、1T-LSD)，使用¹ H、 ¹³ C 核磁共振 (NMR) 光谱和各种二维 NMR 技术。 1T-LSD显示在N ¹位具有噻吩-2-羰基而不是所要求的1,2-二甲基环丁烷-羰基。使用质子特异性定量 NMR ( ¹ H-qNMR) 方法测定一张纸上三个单独单元中 1T-LSD（游离碱）的含量为每个单元 87–100 μg。在 NMR 分析过程中，还观察到甲醇-d ₄中发生了 1T-LSD 脱酰为 LSD 的情况。 1T-LSD 的紫外光谱与其他 LSD 类似物不同，荧光灵敏度也低得多。 由于担心含有新 LSD 类似物的产品的未来分布，鼓励继续监测片材产品中新检测到的化合物。