N-nitroso-melatonin releases nitric oxide in the presence of serotonin and its derivatives

A novel reaction was observed between 5-hydroxytryptophan derivatives like serotonin and N-nitroso-melatonin (NOMela). This reaction decreased the concentration of serotonin by about 50% and generated initially as detectable products nitric oxide and melatonin with stoichiometrical yields. The other expected product, a serotonin-derived radical, could not be detected by electron spin resonance (ESR) spectrometry, probably because the self-decay of phenoxyl type radicals proceed at the diffusion-controlled limit. From the facts that the decay rate of NOMela corresponded very well with the nitric oxide releasing rate and that nitrite was the only thermodynamically stable nitrogen oxide-containing product, it is concluded that the NOMela-serotonin reaction proceeded quantitatively. The observed reaction might be a possibility to counteract a pharmacologically abnormal high serotonin concentration in various diseases.