Journal Article

Model compounds for evaluating the reactivity of amphetamine-type stimulants

Milanovic, Mikayla M., Conlan, Xavier A., Pearson, James R., Pfeffer, Frederick M., Montagnat, Oliver D.

2024

Overview

The use of controlled precursors for reaction optimisation is not always practical. One approach to limiting the use of controlled substances is to instead use ‘model compounds’. Herein, two model compounds resembling norephedrine and ephedrine were selected based on their (i) structural similarity (i.e., presence of key functional groups) and (ii) availability from multiple suppliers without restriction. Model compounds 2-amino-1-phenylethanol and 2-(methylamino)-1-phenylethanol (halostachine), were compared to norephedrine and pseudoephedrine by firstly subjecting them to transformations known in the synthesis of amphetamines, and secondly, comparing the compounds using colourimetric spot tests, FTIR and NMR. [Display omitted] •The use of 2-amino-1-phenylethanol as a model compound for norephedrine.•The use of 2-(methylamino)-1-phenylethanol (halostachine) as a model compound for pseudoephedrine.•Advantages regarding the use of models compounds in place of controlled substances.•The synthesis of β-chloro amines and aziridines from model compounds.

• Publisher: Elsevier B.V,Elsevier Limited
• Subject: Amphetamine / Amphetamines / Amphetamines - chemistry / Central Nervous System Stimulants - chemistry / Cocaine / Colorimetry / Ephedrine / Ephedrine - chemistry / forensic sciences / Functional groups / Humans / Investigations / Magnetic Resonance Spectroscopy / Methamphetamine / Model compounds / Models, Chemical / NMR / Nuclear magnetic resonance / phenylpropanolamine / Phenylpropanolamine - chemistry / Pseudoephedrine / Pseudoephedrine - chemistry / Spectroscopy, Fourier Transform Infrared / Stimulants / Synthesis