5,14-dihydro-5,7,12, 14-tetraazapentacene (5, 14-dihydro-quinoxalino[2, 3-b]phenazine) has been synthesized and studied as a model for polyazaacene with respect to the electrochemical reduction and oxidation in an aprotic electrolyte. While reduction consists of two separate one-electron steps, the oxidation is a single two-electron step. Both processes are irreversible due to chemical follow-up reactions and may be classified as ECE and EC mechanism, respectively. The reduction is followed by a self-protonation reaction. The oxidation is accompanied by proton loss. Using in situ uv/vis spectroscopy it has been proved that the intermediate products reform the pristine compound in the reverse potential scan. The influence of the self-protonation reaction on the reduction process can be restricted by lowering the concentration of the substance in solution as well as by increasing the scan rate. It can be excluded completely by addition of proton donors. In the presence of trifluoroacetic acid a complex is formed, the reduction of which is reversible. The oxidation of that complex remains irreversible at these conditions.