Electron Transfer-Mediated Photodegradation of Phototoxic Antipsychotic Drug Quetiapine

Anamika Gupta; Yogesh Kumar; Mohd Rehan Zaheer; Roohi; Safia Iqbal; Jawaid Iqbal

doi:10.1021/acsomega.1c05302

Electron Transfer-Mediated Photodegradation of Phototoxic Antipsychotic Drug Quetiapine

ACS Omega. 2021 Nov 3;6(45):30834-30840. doi: 10.1021/acsomega.1c05302. eCollection 2021 Nov 16.

Authors

Anamika Gupta¹, Yogesh Kumar², Mohd Rehan Zaheer³, Roohi⁴, Safia Iqbal¹, Jawaid Iqbal¹

Affiliations

¹ Department of Chemistry, Aligarh Muslim University, Aligarh 202002, Uttar Pradesh, India.
² Department of Chemistry, Indian Institute of Technology IIT, Patna 801103, Bihar, India.
³ Department of Chemistry, Gagan College of Management and Technology, Aligarh 202001, Uttar Pradesh, India.
⁴ Protein Research Laboratory, Department of Bioengineering, Integral University, Lucknow 226026, India.

Abstract

Quetiapine (QTP) (1), a psychotropic agent belonging to a chemical class, dibenzothiazepine derivatives, is photosensitive and photolabile. Its photochemistry was studied in the presence of an electron donor N,N-dimethylaniline (DMA) and an electron acceptor 1,4-dicyanobenzene (DCB) under anaerobic conditions. This resulted in photoinduced electron transfer-mediated transformation of drug QTP. Irradiation of Quetiapine (QTP, 1) in the presence of electron donor N,N-dimethylaniline (DMA) under anaerobic conditions in a photochemical reactor afforded one major photoproduct 2 when irradiation of QTP (1) was carried out in the presence of electron acceptor 1,4-dicyanobenzene (DCB) under similar conditions; it afforded 3 as a major photoproduct. These photoproducts were isolated and characterized on the basis of their spectral (IR, UV, ¹H NMR, ¹³C NMR, and mass spectra) studies. The photophysical properties of Quetiapine were also determined in several solvents to investigate the relevance of the molecular structure in their photophysics and consequently in their photochemistry.