Further insights into the oxidation chemistry of 5-hydroxytryptamine.
An important product of electrochemical oxidation of 5-hydroxytryptamine (5-HT) in acid solution is the purple compound tryptamine-4,5-dione (6). However, any attempt to concentrate a solution containing 6 causes it to disappear. The most important reaction of 6 is dimerization to give another purple compound 7,7'-bi-(5-hydroxytryptamine-4-one). Dione 6 can also apparently react with 2,4'-bi-5-hydroxytryptamine to give the trimer 4-[7'-(tryptamine-4,5-dione)]-2,4''-bi-5-hydroxytryptamine. Finally, 6 and other oxidation products of 5-HT react during the concentration step to yield what appears to be a trimer or perhaps a higher oligomer. This oligomer has not been identified, but it has been shown to decompose to give, in part, the neurotoxin 5-hydroxytryptamine-4,7-dione.
Wrona
M Z
MZ
Department of Chemistry, University of Oklahoma, Norman 73019.
Dryhurst
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D055598:Chemical Phenomena; D002621:Chemistry; D004563:Electrochemistry; D008401:Gas Chromatography-Mass Spectrometry; D045563:Indolequinones; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D012701:Serotonin / Q000031:analogs & derivatives / Q000032:analysis*; D013056:Spectrophotometry, Ultraviolet
D045563:Indolequinones; C058622:7,7'-bis-(5-hydroxytryptamine-4-one); C058623:4-(7'-(tryptamine-4,5-dione))-2,4''-bis-5-hydroxytryptamine; D012701:Serotonin