The structure of adrenochrome and its reduction products

J. Harley-Mason

Experientia volume 4, pages307–308 (1948)

https://link.springer.com/article/10.1007/BF02164461

Summary

For adrenochrome, based on the physical properties and the behavior during reduction, a zwitterion structure is proposed. Two reduction products, namely 5,6-dihydroxy-N-methylindole and 2,3,5,6-tetrahydroxy-N-methyldihydroindol, were isolated and characterized. The expected reduction stage, leuko-adrenochrome, could not be obtained.

A reduction mechanism is proposed in which a semiquinone is involved as an intermediate stage. This intermediate body is likely to play a role in biological oxidations affecting adrenochrome.

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