Caffeine a legal psychoactive and representative purine alkaloid found in the leaves of the Coffea arabica form xanthine and uric acid metabolites in the body with only 3% of caffeine being excreted unchanged. These diverse caffeine metabolites enter the water environment and have implications for ecopharmacovigilance. Although the electrochemical behaviour of caffeine has been studied for uses including as sensors and determination of caffeine concentration, to the best of our knowledge no structure electro-activity relationships (SeAR) of metabolite formation nor single step synthesis of major caffeine metabolitesparaxanthine and theophylline have been developed. The primary human metabolism of caffeine (Scheme 1) proceeds predominantly through N3demethylation to paraxanthine via CYP1A2 in the liver (70-80% of metabolites). . Secondary metabolic pathways proceed via C8-oxidation of caffeine to afford 1,3,7trimethyluric acids (15% of metabolites). Tertiary metabolic pathways are via demethylation at the N1-position of caffeine to theobromine and N7-position to theophylline (both account for 7-8% of metabolites). . Furthermore, minor metabolites of caffeine include: 1-methylxanthine (1X), 1-methyluric acid (1U), 5-acetylamino-6-formylamino-3-methyluracil (AFMU), and 1,7-dimethyluric acid (17U) via CYP1A2, CYP2A6, N-acetyltransferase-2, and xanthine dehydrogenase (XDH). Caffeine metabolites have been biosynthesised, synthesised via multi-step chemical procedures, or via genetic engineering. The use of electrochemistry to generate information on drug metabolites is a rapidly developing method of importance for establishing environmental fate. In this study, we considered whether the application of electrochemistry would achieve the single step synthesis of authentic caffeine metabolites and a predictive structure electroactivity relationship (SeAR) model for metabolism.