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Tryptamine-4,5-dione protected as the carbamate was prepared in excellent overall yield by the oxidation of serotonin carbamate with benzeneseleninic anhydride. This o -quinone, which was potently neurotoxic, readily added sulfur nucleophiles under basic conditions including cysteine and glutathione in 1,4-fashion, a reactivity pattern which may reflect the mechanism of the neurotoxicity.
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Cai et al. (1990) studied this question.
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