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The impact of different oxidation processes on the maprotiline degradation pathways was investigated by liquid chromatography-high resolution mass spectrometry (LC/HRMS) experiments. The in-house SPIX software was used to process HRMS data allowing to ensure the potential singular species formed. Semiconductors photocatalysts, namely Fe-ZnO, Ce-ZnO and TiO₂, proved to be more efficient than heterogeneous photo-Fenton processes in the presence of hydrogen peroxide and persulfate. No significant differences were observed in the degradation pathways in the presence of photocatalysis, while the SO₄⁻ mediated process promote the formation of different transformation products (TPs). Species resulting from ring-openings were observed with higher persistence in the presence of SO₄⁻. In-silico tests on mutagenicity, developmental/reproductive toxicity, Fathead minnow LC₅₀, D. magna LC₅₀, fish acute LC₅₀ were carried out to estimate the toxicity of the identified transformation products. Low toxicant properties were estimated for TPs resulting from hydroxylation onto bridge rather than onto aromatic rings, as well as those resulting from the ring-opening.