Electrochemical Characterization of Central Action Tricyclic Drugs by Voltammetric Techniques and Density Functional Theory Calculations

Pharmaceuticals doi: 10.3390/ph12030116

Authors: Edson Silvio Batista Rodrigues Isaac Yves Lopes de Macêdo Larissa Lesley da Silva Lima Douglas Vieira Thomaz Carlos Eduardo Peixoto da Cunha Mayk Teles de Oliveira Nara Ballaminut Morgana Fernandes Alecrim Murilo Ferreira de Carvalho Bruna Guimarães Isecke Karla Carneiro de Siqueira Leite Fabio Bahls Machado Freddy Fernandes Guimarães Ricardo Menegatti Vernon Somerset Eric de Souza Gil

This work details the study of the redox behavior of the drugs cyclobenzaprine (CBP), amitriptyline (AMP) and nortriptyline (NOR) through voltammetric methods and computational chemistry. Results obtained in this study show that the amine moiety of each compound is more likely to undergo oxidation at 1a at Ep1a ≈ 0.69, 0.79, 0.93 V (vs. Ag/AgCl/KClsat) for CBP, AMP and NOR, respectively. Moreover, CBP presented a second peak, 2a at Ep2a ≈ 0.98 V (vs. Ag/AgCl/KClsat) at pH 7.0. Furthermore, the electronic structure calculation results corroborate the electrochemical assays regarding the HOMO energies of the lowest energy conformers of each molecule. The mechanism for each anodic process is proposed according to electroanalytical and computational chemistry findings, which show evidence that the methods herein employed may be a valuable alternative to study the redox behavior of structurally similar drugs.