Photodegradation is widely known as a changer of both the quality and the quantity of several chemical compounds. In this study, we sought to examine the photochemical behavior of triprolidine (TRP), which is a member of the first-generation antihistamine and utilized for a relief of an allergic conditions, in an aqueous media. There are no reports focused on its potential photoproducts and photodegradation pathways in detail to the best of our knowledge. TRP photodegradation induced by ultraviolet light (UV) irradiation was monitored utilizing high-performance liquid chromatography (HPLC), and structural elucidation of the TRP photoproduct was performed by electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS) and nuclear magnetic resonance (NMR). Finally, the mechanism of TRP photodegradation was speculated based on the identified photoproduct. TRP was photodegraded dependent on the irradiation time of UV in proportion to the generation of one TRP photoproduct (TRP-P). Structural determination by LC-ESI-MS/MS and NMR clarified that TRP-P was the geometrical isomer of TRP, which was formed by the cis-trans conversion of double bond. UV irradiation experiment for TRP-P revealed the conversion from it to TRP. It is clarified that cis-trans conversion between TRP and TRP-P is photo-equilibrium reaction and TRP-P is predominant under the condition as this experiment. Toxicological potencies of TRP and TRP-P might not be observed by ProTox-II in silico toxicity evaluation. This is the first study evaluating the photochemical behavior of TRP.
Keywords: HPLC; LC-ESI-MS/MS; NMR; Photoisomerization; Photoproduct; Triprolidine.
© 2023. The Author(s), under exclusive licence to The Japan Society for Analytical Chemistry.