title: Fluoxetine and norfluoxetine revisited: new insights into the electrochemical and spectroscopic properties.
abstract: The extent to which humans and wildlife are exposed to the vast array of anthropogenic chemicals and their degradation products, along with related naturally occurring compounds, is nowadays an important issue. The study of the physical-chemical properties of the compounds and/or degradation products is an important subject because some of them are intrinsically related to its resistance to degradation and/or bioaccumulation. Accordingly, the study of the electrochemical behavior of the selective serotonin reuptake inhibitor fluoxetine and its main metabolite norfluoxetine was investigated. The identification of the oxidation processes was done via two fluoxetine analogues, 1-(benzyloxy)-4-(trifluoromethyl)benzene and N-methyl-3-phenylpropan-1-amine hydrochloride. The oxidative processes occurring in fluoxetine are pH-dependent and were ascribed to the chemical moieties present in the molecule: the secondary amine group and the substituted aromatic nucleus. To perform an unequivocal ascription, the structural preferences of the drug and metabolite were also determined, by Raman spectroscopy coupled to quantum mechanical calculations (at the DFT level). The analytical data obtained in this work will allow the development of a rapid and unequivocal spectroscopic procedure suitable for fluoxetine identification, as well as to distinguish between the drug and its main metabolite.
authors.affiliation: UQFM/Departamento de Engenharia Quimica, Instituto Superior de Engenharia do Porto, 4200-072 Porto, Portugal.
authors.forename: E Manuela
authors.initials: EM
authors.lastname: Garrido
authors.forename: Jorge
authors.initials: J
authors.lastname: Garrido
authors.forename: Rita
authors.initials: R
authors.lastname: Calheiros
authors.forename: M Paula M
authors.initials: MP
authors.lastname: Marques
authors.forename: Fernanda
authors.initials: F
authors.lastname: Borges
mesh_terms: D000928:Antidepressive Agents / Q000737:chemistry*; D004563:Electrochemistry; D005473:Fluoxetine / Q000031:analogs & derivatives* / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011789:Quantum Theory; D013059:Spectrum Analysis, Raman
chemical_list: D000928:Antidepressive Agents; D005473:Fluoxetine; C036139:norfluoxetine