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Incubation of 5-hydroxytryptamine (1) with L-cysteine and pig or bovine brain microsomes and an NADPH-generating system or with synaptosomes results in the rapid formation of the (2R,4R)- and (2S,4R)-epimers of 2-[(5-hydroxy-1H-indol-3-yl)methyl]thiazolidine. Incubation of 1 and glutathione under the same experimental conditions yields the (2R,4R)- and (2S,4R)-epimers of alpha-amino-4-[[(carboxymethyl)amino]carbonyl]-2-[(5-hydroxy-1H- indol-3-yl)methyl]-delta-oxo-3-thiazolidinepentanoic acid. These various thiazolidine derivatives are formed by nucleophilic addition of the thiol residues of cysteine or glutathione to the aldehyde group of 5-hydroxyindole-3-acetaldehyde (2), the primary product of the monoamine oxidase-mediated oxidative deamination of 1. The facile reaction of cysteine and glutathione with 2 might represent a mechanism designed to scavenge the biogenic aldehyde and therefore to prevent its alkylation of key intraneuronal protein nucleophiles.

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