Four types of cannabimimetic indazole and indole derivatives, ADB-BINACA, AB-FUBICA, ADB-FUBICA, and AB-BICA, identified as new psychoactive substances

Abstract

We identified four cannabimimetic indazole and indole derivatives in new illegal psychoactive substances seized from a clandestine laboratory in China. These four derivatives included <i>N</i>-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-benzyl-1<i>H</i>-indazole-3-carboxamide (ADB-BINACA, <b>1</b>), <i>N</i>-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1<i>H</i>-indole-3-carboxamide (AB-FUBICA, <b>2</b>), <i>N</i>-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1<i>H</i>-indole-3-carboxamide (ADB-FUBICA, <b>3</b>), and <i>N</i>-(1-amino-3-methyl-1-oxobutan-2-yl)-1-benzyl-1<i>H</i>-indole-3-carboxamide (AB-BICA, <b>4</b>). These compounds were identified by liquid chromatography-high-resolution mass spectrometry, gas chromatography-mass spectrometry, and nuclear magnetic resonance spectroscopy. No chemical or pharmacological data about compound <b>4</b> has appeared until now, making this the first report on this compound. Compounds <b>1</b>, <b>2</b>, and <b>3</b> have previously been reported to have a high affinity for cannabinoid CB₁ and CB₂ receptors, but this is the first report of their presence in illegal products.