Abstract
THE discharge of the intense red colour of aqueous solutions of adrenochrome (I) by various reducing agents has been reported by several workers1,2. The reaction apparently does not simply consist of the reduction of the orthoquinone moiety of the molecule with the production of the hypothetical ‘leuco-adrenochrome’ (2 : 3-dihydro-3 : 5 : 6-trihydroxy-N-methylindole) (II). Harley-Mason, in describing the reduction with sodium hydrosulphite or hydrogen (catalytic), postulated the initial addition of one atom of hydrogen to the molecule, with the formation of an unstable intermediate which disproportionates into (II) and a zwitterionic compound (III). The former (II) appears to be inherently unstable and readily loses water, with the formation of 5 : 6-di-hydroxy-N-methylindole (IV) ; the second substance (III) isomerizes under the influence of alkali to adrenolutin (3 : 5 : 6-trihydroxy-N-methylindole) (V)2,3.
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HEACOCK, R., LAIDLAW, B. Reduction of Adrenochrome with Ascorbic Acid. Nature 182, 526–527 (1958). https://doi.org/10.1038/182526a0
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DOI: https://doi.org/10.1038/182526a0
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