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

Abstract:  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.