Trimipramine (TMP) is an antidepressant drug used for the treatment of a variety of depressive states and other psychiatric disorders. It has been already detected in the aquatic environment. Currently, no further knowledge is available on fate and effects of TMP in the aquatic environment. Therefore, we studied the biodegradability of TMP and of its photolysis transformation products (PTPs) generated by irradiation with polychromatic UV light in aqueous solution. Different conditions including initial drug concentration, pH, and temperature were applied during TMP photolysis. Subsequently, the time courses of TMP and dissolved organic carbon (DOC) concentrations were monitored throughout the whole photo-degradation process. Then, high-resolution mass spectrometry was used to identify and elucidate the structures of the resulting PTPs. After that, the two standardized biodegradation tests, Closed Bottle test (CBT; OECD 301 D) and Manometric Respirometry test (MRT; OECD 301 F), were performed for TMP and its photolytic mixtures to assess the biodegradability of TMP and its PTPs. Finally, the toxicity of TMP and its photolytic mixtures was predicted using different quantitative structure activity relationship (QSAR) software. It was found that after 128 min of UV-irradiation, 91.8% of TMP at the initial concentration of 100 mg L(-1) was eliminated with only 23.9% removal in the DOC. So, it can be pointed out that more than 65% of the degraded TMP is transformed to new non-mineralized PTPs. 14 new PTPs were detected in TMP's photolytic mixtures. Their supposed structures indicate that the proposed photo-transformation pathway is mainly by hydroxylation. The statistical analysis confirms that the differences in the degradation rates of TMP as a function of concentration, pH, and temperature are statistically significant in most cases investigated here. In biodegradation testing, TMP and its PTPs are classified as not readily biodegradable, while LC-MS analysis revealed some PTPs to be eliminated more than TMP itself. Results from QSAR analysis confirmed that some of the PTPs could be biodegradable, and revealed that some of the non-biodegradable PTPs may be human and/or eco-toxic, posing a risk to the environment. Our findings show that TMP under UV-irradiation could lead to the formation of some more easily biodegradable PTPs and some others toxic and non-biodegradable PTPs. Therefore, further studies should be conducted regarding the fate and effects of TMP and its PTPs elucidated in this study on human health and on the environment.