In this study, we have comprehensively studied the electrochemical behaviour of a series of PTZ derivatives. Analysis of the cyclic voltammetry behaviour of PTZ derivatives revealed a SeAR based on scaffold characteristics and their respective influence on oxidation potential. Molecular modelling enabled the predicted of the most likely metabolites to form. Ultimately, an optimised electrochemical reaction platform for the parent scaffold and exemplar drug molecule enabling a tractable synthesis of the S-oxide and for the first time the S,S-dioxide metabolites.