Oxidation of 5-hydroxytryptamine and 5,7-dihydroxytryptamine. A new oxidation pathway and formation of a novel neurotoxin.
The electrochemical oxidation of 5-hydroxytryptamine (5-HT) in acidic solution proceeds through a minor route leading first to 5,7-dihydroxytryptamine (5,7-DHT) then to 4,5,7-trihydroxytryptamine and finally to 5-hydroxytryptamine-4,7-dione. The latter compound is a major electrochemical oxidation product of 5,7-DHT at pH 2 and 7 and a major autoxidation product at pH greater than or equal to 6. Preliminary biological results indicate that 5-hydroxytryptamine-4,7-dione is a more potent central nervous system toxin than 5,7-DHT. These results show for the first time a chemical pathway from 5-HT to 5,7-DHT and suggest possible minor metabolic oxidative pathways for the neurotransmitter 5-HT to at least two powerful neurotoxins.
D015115:5,6-Dihydroxytryptamine / Q000633:toxicity; D015116:5,7-Dihydroxytryptamine / Q000633:toxicity; D000818:Animals; D002853:Chromatography, Liquid; D004102:Dihydroxytryptamines / Q000633:toxicity; D006863:Hydrogen-Ion Concentration; D007928:Lethal Dose 50; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D051379:Mice; D009420:Nervous System / Q000187:drug effects*; D010084:Oxidation-Reduction; D012701:Serotonin; D013055:Spectrophotometry, Infrared
D004102:Dihydroxytryptamines; D015116:5,7-Dihydroxytryptamine; D012701:Serotonin; D015115:5,6-Dihydroxytryptamine