Characterization of Three Novel 4-Methylaminorex Derivatives Applied as Designer Drugs

Abstract

The ongoing development of more and more new psychoactive substances continues to be a huge problem in 2022 affecting the European and international drug market. Through slight alterations in the structure of illicit drugs, a way to circumvent the law is created, as the created derivatives serve as legal alternatives with similar effects. A common way of structure modification is the induction of a halogen residue. Recently, halogenated derivatives of the well-known designer drug 4-methylaminorex appeared on the market and are available in various online shops. In this study, three novel halogenated 4-methylaminorex derivatives, namely 4′-fluoro-4-methylaminorex, 4′-chloro-4-methylaminorex, and 4′-bromo-4-methylaminorex, were purchased online and characterized using nuclear magnetic resonance (NMR) spectroscopy, liquid chromatography-high-resolution mass spectrometry (LC-HRMS), and chiral high-performance liquid chromatography with ultraviolet detection (HPLC-UV). These derivatives possess two stereogenic centers, and analyses revealed that all of them were present as a racemic mixture of the trans diastereomeric form.

Keywords

• halogenated 4-methylaminorex derivatives
• chiral separation
• NMR
• LC-HRMS
• HPLC-UV
• 4′-fluoro-4-methylaminorex