Cyclic, differential pulse and square wave voltammetry of dibenzazepine derivatives and analogous compound

CHED 177

Ileana Nieves, i_nieves@uprh.edu, Juan A. Rodríguez, i_nieves@uprh.edu, Rolando Oyola, Luis E. Piñero, and Carmelo García, ca_garcia@uprh.edu. Department of Chemistry, University of Puerto Rico at Humacao, CUH Station, # 100 Road 908, Humacao, PR 00791-4300
Within the known antidepressive drugs (TCA's), the dibenzazepine derivative (DBZ), imipramine (IPA) is referred to as monoamine re-uptake inhibitor due to its principal mode of action. The chemical structure of DBZ contains a heterocyclic N–alkyl substitution with a tertiary amine functional group and is compared to the parent compound, iminodibenzyl (IMINO). Electrochemical detection of IPA shows complex electrochemistry attributed to secondary oxidation due to the formation of a dimer that is postulated (easily oxidized) as a result of the initial monomer oxidation. To understand the electrochemical results, studies comparing IMINO and an IPA analogue, [N-(4-Methyl-pentyl)- iminodibenzyl], that lack the amine functional group at the alkyl chain of the heterocyclic substitution (synthesized in our group) were performed. The structural modification may determine the role of the alkyl amine functional group in the proposed dimer formation. Solutions in different solvents were analyzed in an E-2 BASi-Epsilon Voltammetric Analyzer using Glassy Carbon. Multiple cycles show an additional species at lower reduction and the IPA analogue show only one redox pair. The results may demonstrate that the dimer formation involves an intermolecular interaction where the alkyl amine functional group is necessary for the additional oxidation products observed. (Sponsored by Advance, NSF (SBE-0123645), UPR-Humacao and FoPI-UPR-Humacao)