Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Letter
  • Published:

Reduction of Adrenochrome with Ascorbic Acid

Nature volume 182, pages 526–527 (1958)Cite this article

An Erratum to this article was published on 13 September 1958

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.

This is a preview of subscription content, access via your institution

Access options

Buy this article

  • Purchase on Springer Link
  • Instant access to full article PDF
Buy now

Prices may be subject to local taxes which are calculated during checkout

Similar content being viewed by others

References

  1. Green, D. E., and Richter, D., Biochem. J., 31, 596 (1937). Bergel, F., and Morrison, A. L., J. Chem. Soc., 48 (1943). Fischer, P., and Lecomte, J., Bull. Soc. chim. biol., 33, 569 (1951).

    Article  CAS  Google Scholar 

  2. Harley-Mason, J., Experientia, 4, 307 (1948); J. Chem. Soc., 1276 (1950).

    Article  CAS  Google Scholar 

  3. Harley-Mason, J., and Bu'Lock, J., J. Chem. Soc., 2248 (1951).

  4. Beauvillain, A., and Sarradin, J., Bull. Soc. chim. biol., 30, 478 (1948).

    CAS  Google Scholar 

  5. Fischer, P., Bull. Soc. chim. Belg., 58, 205 (1949).

    Article  CAS  Google Scholar 

  6. Benedict, S. R., J. Biol. Chem., 6, 51 (1909).

    CAS  Google Scholar 

  7. Heacock, R. A., Nerenberg, C., and Payza, A., Can. J. Chem., 36, 853 (1958).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Psychiatric Research Unit, University Hospital, Saskatoon, Saskatchewan

    R. A. HEACOCK & B. D. LAIDLAW

Authors
  1. R. A. HEACOCK
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. B. D. LAIDLAW
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

HEACOCK, R., LAIDLAW, B. Reduction of Adrenochrome with Ascorbic Acid. Nature 182, 526–527 (1958). https://doi.org/10.1038/182526a0

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1038/182526a0

This article is cited by

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

Search

Advanced search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing