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Open AccessArticle

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

1
Faculdade de Farmácia, Universidade Federal de Goiás, Goiânia GO 74690-970, Brazil
2
Bloco IQ-1, Campus Samambaia, Avenida Esperança s/n, Instituto de Química, Universidade Federal de Goiás, Goiânia CEP 74690-900, Brazil
3
Department of Chemistry, Faculty of Applied Sciences, Cape Peninsula University of Technology, Bellville 7535, South Africa
*
Author to whom correspondence should be addressed.
Pharmaceuticals 2019, 12(3), 116; https://doi.org/10.3390/ph12030116
Received: 31 May 2019 / Revised: 16 July 2019 / Accepted: 17 July 2019 / Published: 1 August 2019
(This article belongs to the Special Issue Molecular Dynamics in Drug Design)
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Abstract

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. View Full-Text
Keywords: electrochemistry; oxidation mechanism; computational chemistry; electronic structure; cyclobenzaprine electrochemistry; oxidation mechanism; computational chemistry; electronic structure; cyclobenzaprine
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Rodrigues, E.S.B.; de Macêdo, I.Y.L.; da Silva Lima, L.L.; Thomaz, D.V.; da Cunha, C.E.P.; Teles de Oliveira, M.; Ballaminut, N.; Alecrim, M.F.; Ferreira de Carvalho, M.; Isecke, B.G.; Carneiro de Siqueira Leite, K.; Machado, F.B.; Guimarães, F.F.; Menegatti, R.; Somerset, V.; de Souza Gil, E. Electrochemical Characterization of Central Action Tricyclic Drugs by Voltammetric Techniques and Density Functional Theory Calculations. Pharmaceuticals 2019, 12, 116.

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