Developed as a regulator of copper homeostasis in the brain of patients affected by Alzheimer's disease (AD), TDMQ20 is a specific copper(II) chelator able to restore short term memory in AD mice. To anticipate on metabolic studies of this drug-candidate, here we report the catalytic oxidation of TDMQ20 by a biomimetic system reminiscent of P450 oxidation, using a metalloporphyrin and hydrogen persulfate as oxidant. Oxidation products were mainly characterized by HPLC with UV-visible spectrometry or high-resolution mass spectrometry detection. In these conditions, TDMQ20 was readily oxidized by aromatic hydroxylation, oxidation of 1,4-diphenol or 1,4-aminophenol to 1,4-quinone or quinone-imine, respectively, or oxidative chlorination. These putative metabolites were water-soluble, suggesting that the drug-candidate might be easily metabolized and excreted in vivo.