THE CHEMISTRY OF THE AMINOCHROMES: PART VI. THE REACTION OF ADRENOCHROME WITH GLUTATHIONE

The reaction between adrenochrome and glutathione has been studied. The main products result from the 1,4-addition of glutathione to the C5 unsaturated carbonyl systems in adrenochrome involving the C6—C7 and the C4—C9 double bonds, and are probably 7-S-glutathionyl-5,6-dihydroxy-N-methylindole and 9-S-glutathionyl-2,3,6,9-tetrahydro-3,5-dihydroxy-6-oxo-N-methylindole respectively. 5,6-Dihydroxy-N-methylindole is also formed during the interaction of glutathione and adrenochrome. The mechanisms by which these compounds are formed are discussed.