108535-05-3Relevant articles and documents
Oxidation Chemistry of 5-Hydroxytryptamine. 1. Mechanism and Products Formed at Micromolar Concentrations
Wrona, Monika Z.,Dryhurst, Glenn
, p. 2817 - 2825 (2007/10/02)
The oxidation of very low concentrations (+ reaction, giving a phenoxyl radical which exists in equilibrium with aryl, C(4)., and N(1). radicals.At low potentials the latter radicals can react to give dimeric products.At higher potentials, however, the primary phenoxyl radical is further oxidized (1e,1H+) to a reactive quinone imine.The quinone imine is rapidly attacked by water to give 4,5-dihydroxytryptamine (7), which is further oxidized to tryptamine-4,5-dione (B).In aqueous solution at pH 2 B is slowly attacked by water to give 4,5,7-trihydroxytryptamine, which is further oxidized (2e,2H+) to 5-hydroxytryptamine-4,7-dione (11).Compounds B and 11 then react together to give a hydroxylated tryptamine dimer.The facile oxidation of 1 give at least two neurotoxins, 7 and 9, might provide insight into the previously proposed anomolous oxidative metabolism of 1 as an underlying cause of various mental disorders.
