Light-Induced Reactions of Chlorpromazine in the Presence of a Heterogeneous Photocatalyst: Formation of a Long-Lasting Sulfoxide

Abstract

A commercial carbon-modified titanium dioxide, KRONOClean 7000, was applied as a UV(A) and visible-light active photocatalyst to investigate the conversion of the antipsychotic pharmaceutical chlorpromazine in aqueous phase employing two monochromatic light sources emitting at wavelengths of 365 and 455 nm. Photocatalytic and photolytic conversion of chlorpromazine under both anaerobic and aerobic conditions was analyzed using a HPLC-MS technique. Depending on the irradiation wavelength and presence of oxygen, varying conversion rates and intermediates revealing different reaction pathways were observed. Upon visible light irradiation under aerobic conditions, chlorpromazine was only converted in the presence of the photocatalyst. No photocatalytic conversion of this compound under anaerobic conditions upon visible light irradiation was observed. Upon UV(A) irradiation, chlorpromazine was successfully converted into its metabolites in both presence and absence of the photocatalyst. Most importantly, chlorpromazine sulfoxide, a very persistent metabolite of chlorpromazine, was produced throughout the photolytic and photocatalytic conversions of chlorpromazine under aerobic conditions. Chlorpromazine sulfoxide was found to be highly stable under visible light irradiation even in the presence of the photocatalyst. Heterogeneous photocatalysis under UV(A) irradiation resulted in a slow decrease of the sulfoxide concentration, however, the required irradiation time for its complete removal was found to be much longer compared to the removal of chlorpromazine at the same initial concentration.