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:

Synthesis of Vomipyrine

Abstract

AN outstanding result of Wieland‘s long series of investigations of vomicine was the degradation of the alkaloid to a base, C15H16N2, termed vomipyrine1. This afforded yellow salts, and the spectrochemical behaviour clearly indicated its constitution as an alkylated pyrroquinoline, C11H7N2.C4H9, although the position of fusion of the rings and the position and distribution of the alkyl group or groups (2Et, Me, Pr, Bu, etc.) was unknown. Guesses based on the earlier strychnine formulæ were disproved by synthesis2.

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

Access options

Rent or buy this article

Prices vary by article type

from$1.95

to$39.95

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

Similar content being viewed by others

References

  1. Wieland, H., and Horner, L., Annalen, 528, 73 (1937).

    Article  CAS  Google Scholar 

  2. Horner, L., Annalen, 540, 73 (1939); cf. ref. 9.

    Article  CAS  Google Scholar 

  3. Robinson, R., Experientia, 2, 28 (1946). Openshaw, H. T., and Robinson, R., Nature, 157, 438 (1946). Chakravarti, R. N., and Robinson, R., Nature, 160, 18 (1947).

    Article  CAS  Google Scholar 

  4. Pausacker, K. H., and Robinson, R., J. Chem. Soc. (in the press, 1948).

  5. Perkin, W. H., Robinson, R., and Smith, J. C., J. Chem. Soc., 1239 (1932).

  6. Bailey, A. S., and Robinson, R., Nature, 161, 433 (1948).

    Article  ADS  CAS  Google Scholar 

  7. Bradford, L., Elliott, T. J., and Rowe, F. M., J. Chem. Soc., 437 (1947).

  8. Kyker, G. C., and Bost, R. W., J. Amer. Chem. Soc., 61, 2469 (1939).

    Article  CAS  Google Scholar 

  9. Wieland, H., and Horner, L., Annalen, 536, 89 (1938); cf. ref. 2.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

ROBINSON, R., STEPHEN, A. Synthesis of Vomipyrine. Nature 162, 177–178 (1948). https://doi.org/10.1038/162177a0

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1038/162177a0

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

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