Available online www.jocpr.com Journal of Chemical and Pharmaceutical Research, 2015, 7(5):330-334 Research Article ISSN : 0975-7384 CODEN(USA) : JCPRC5 330 Photosensitized oxidation of fluvoxamine, a phototoxic antidepressant drug Anamika Gupta, Waseem Ahmad, Jawaid Iqbal and Mohd. Rehan Zaheer Department of Chemistry, Aligarh Muslim University, Aligarh, UP, India _____________________________________________________________________________________________ ABSTRACT The phototoxic antidepressant drug fluvoxamine is photolabile under aerobic condition in UV-A light. Irradiation of air-saturated solution of fluvoxamine (1) (210, 0.66 mM) in methanol with methylene blue as sensitizer produces two photoproducts, 5-Methoxy-1-(4-(trifluoromethyl) phenyl) pentan-1-one (2) and 2-nitroethanamine (3). The Photoproducts are formed by the reaction of drug with singlet oxygen produced through type II photodynamic action. The role of singlet oxygen during photolysis was confirmed by singlet oxygen scavenger 1, 4-diazabicyclo [2.2.2] octane (DABCO). Keywords: Fluvoxamine, photooxidation, phototoxicity, Singlet Oxygen, Rose Bengal. _____________________________________________________________________________________________ INTRODUCTION Over the past decade there has been a considerable amount of research toward understanding both the unimolecular deactivation pathway of photo excited pharmaceutical product and their photosensitizing capability in the presence of biological substrate [1, 2]. According to the results, the primary event in any photosensitization process is the absorption of a photon, and the following free radical (Type I reaction) and singlet oxygen generation (Type II reaction) by photo-excited drug molecules [3, 4]. This may appear to be the principal intermediate species in the phototoxic response [5]. Thus, photochemical studies of photosensitizing drugs are important for understanding the key early events resulting in phototoxicity. Oximes and their derivatives have found widespread use in synthetic organic chemistry as protecting groups for carbonyl compounds [6, 7]. In addition to their synthetic utility, many oximes are commonly used as pesticides [8] (including the structurally related carbamates) as photo-initiators [9] and as drugs e.g., as antidotes for organ phosphorus poisoning [10, 11]. The photochemical reactions of oximes have received considerable attention [12- 14]. A number of pathways are available to oximes in the excited state and oximes may form a range of reactive intermediates in these reactions such as excited-state oximes (singlet or triplet), oxime radical cations, or reactive species (radicals) derived from these such as iminoxyl radicals, which have the potential to cause cell and tissue damage [15,16]. Photooxidation is major a tool to generate these reactive intermediates hence photochemical oxidations of oxime direct or sensitized, by energy or electron transfer, has attracted ever-growing interest. Fluvoxamine (FXM); (E)-5-methoxy-4′-trifluromethylvalerophenone O-2-aminoethyl-oxime is a new generation antidepressant drug, [17, 18] demonstrates phototoxicity [19]. It exerts its antidepressant effect through a selective inhibition for the reuptake of the neurotransmitter serotonin by the presynaptic receptors hence it group of selective serotonin reuptake inhibitors (SSRIs) [20, 21]. They are replacing the older tricyclic antidepressants (TCAs) and because the efficacy of the SSRIs does not differ significantly from that of the TCAs and the SSRIs do not show