Identification and Analysis of Lysergic Acid Diethylamide Analogs, 4-Benzoyl-N,N-Diethyl-7-Methyl-4,6,6a,7,8,9-Hexahydroindolo[4,3-fg]quinoline-9-Carboxamide (1Bz-LSD) and N,N-Diethyl-7-Methyl-4-(4-(Trimethylsilyl)Benzoyl)-4,6,6a,7,8,9-Hexahydroindolo[4,3-fg]quinoline-9-Carboxamide (1-TMSBz-LSD), in tablet or paper sheet products available online in Japan.

Abstract

Recently, many lysergic acid diethylamide (LSD) analogs have emerged as designer drugs worldwide. In Japan, these compounds are distributed as paper sheet or tablet products and are available online. Even after these compounds were regulated, new compounds with modified structures continued to appear. In the present study, two LSD analogs were identified from tablet or paper sheet products. 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 were used to determine the structures of the compounds. Based on these analyses, 4-benzoyl-N,N-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (1Bz-LSD) and N,N-diethyl-7-methyl-4-(4-(trimethylsilyl)benzoyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (1-TMSBz-LSD) were detected and identified in the tablet and paper sheet products, respectively. This paper is the first to report the detection of 1Bz-LSD and 1-TMSBz-LSD in tablet and paper sheet products in Japan.

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