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.

Structure–Activity Relationships of One-Ring Psychotomimetics

Abstract

Human dose-response relationships for psychotomimetic phenethylamines : an isopropylamine side chain and triple methoxy substitution provide optimum activity. Available data suggest possible structures for the hypothetical psychotogen of schizophrenia.

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

References

  1. Osmond, H., and Smythies, J. R., J. Ment. Sci., 98, 309 (1952).

    Article  CAS  Google Scholar 

  2. Jarvik, M. E., Psychopharmacology: Pharmacological Effects on Behaviour (edit. by Pennes, H. H.) (Hoeber, Inc., NY, 1958).

    Google Scholar 

  3. Hollister, L. E., Ann. NY Acad. Sci., 96, 80 (1962).

    Article  ADS  CAS  Google Scholar 

  4. Heston, L. L., Brit. J. Psychiat., 112, 819 (1962).

    Article  Google Scholar 

  5. Karlsson, J. L., The Biologic Basis of Schizophrenia (Thomas, Springfield, Illinois, 1966).

    Google Scholar 

  6. Szara, S., and Hearst, E., Ann. NY Acad. Sci., 96, 134 (1962).

    Article  ADS  CAS  Google Scholar 

  7. Naranjo, C., Ethnopharmacologic Search for Psychoactive Drugs, 385, et seq. (edit. by Efron, D. H.) (US Gov. Printing Office, 1967).

    Google Scholar 

  8. Friedhoff, A. J., and van Winkle, E., Nature, 194, 897 (1962).

    Article  ADS  CAS  Google Scholar 

  9. Hollister, L. E., and Friedhoff, A. J., Nature, 210, 1377 (1966).

    Article  ADS  CAS  Google Scholar 

  10. Shulgin, A. T., Sargent, T., and Naranjo, C., Nature, 212, 1606 (1966).

    Article  ADS  CAS  Google Scholar 

  11. Uyeno, E. T., Otis, L. S., and Mitoma, C., Comm. in Behav. Biol. A, 1, 83, (1968).

    Google Scholar 

  12. Snyder, S. H., and Merril, C. R., Proc. US Nat. Acad. Sci., 54, 258 (1965).

    Article  ADS  CAS  Google Scholar 

  13. Smythies, J. R., and Levy, C. K., J. Ment. Sci., 106, 531 (1960).

    Article  CAS  Google Scholar 

  14. Corne, S. J., and Pickering, R. W., Psychopharmacologia, 11, 65 (1967).

    Article  CAS  Google Scholar 

  15. Smythies, J. R., Johnson, V. S., Bradley, R. J., Benington, F., Morin, R. A., and Clark, L. C., Nature, 216, 218 (1967).

    Google Scholar 

  16. Dixon, A. K., Experientia, 24, 743 (1968).

    Article  CAS  Google Scholar 

  17. Alles, G. A., Neuropharmacology, Fourth Macy Foundation Conference (edit. by Abrahamson, H. A.), 1959.

    Google Scholar 

  18. Snyder, S. H., and Faillace, L., Science, 159, 1492 (1968).

    Article  ADS  CAS  Google Scholar 

  19. Shulgin, A. T., Experientia, 20, 366 (1964).

    Article  CAS  Google Scholar 

  20. Alles, G. A., J. Pharmacol. Exp. Therap., 47, 339 (1933).

    CAS  Google Scholar 

  21. Hey, P., Quart. J. Pharm. Pharmacol., 20, 129 (1947).

    CAS  Google Scholar 

  22. Peretz, D. I., Smythies, J. R., and Gibson, W. C., J. Ment. Sci., 101, 317 (1955).

    Article  CAS  Google Scholar 

  23. Shulgin, A. T., Bunnell, S., and Sargent, T., Nature, 189, 1011 (1961).

    Article  ADS  CAS  Google Scholar 

  24. Shulgin, A. T., Experientia, 17, 127 (1963).

    Article  Google Scholar 

  25. Benington, F., Morin, R. D., and Clark, L. C., J. Org. Chem., 20, 1292 (1955).

    Article  CAS  Google Scholar 

  26. Carlsson, A., Progress in Brain Research, 8 (edit. by Himwich, H. E., and Himwich, W. A.) (Elsevier, 1964).

    Google Scholar 

  27. Sargent, T., Israelstam, D. M., Shulgin, A. T., Landaw, S. A., and Finley, N. N., Biochem. Biophys. Res. Commun., 29, 126 (1967).

    Article  CAS  Google Scholar 

  28. Daly, J. W., Axelrod, J., and Witkop, B., J. Biol. Chem., 235, 1155 (1960).

    CAS  Google Scholar 

  29. Kuehl, F. A., Hichens, M., Ormond, E., Meisinger, M. A. P., Gale, P. H., Cirillo, V. J., and Brink, N. G., Nature, 203, 154 (1964).

    Article  ADS  CAS  Google Scholar 

  30. Creveling, C. R., and Daly, J. W., Nature, 216, 190 (1967).

    Article  ADS  CAS  Google Scholar 

  31. Senoh, S., Creveling, C. R., Udenfriend, S., and Witkop, B., J. Amer. Chem. Soc., 81, 6236 (1959).

    Article  CAS  Google Scholar 

  32. Daly, J., Horner, L., and Witkop, B., J. Amer. Chem. Soc., 83, 4787 (1961).

    Article  CAS  Google Scholar 

  33. Meister, A., Biochemistry of the Amino Acids, 2, 899 (Academic Press, New York, 1965).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

SHULGIN, A., SARGENT, T. & NARANJO, C. Structure–Activity Relationships of One-Ring Psychotomimetics. Nature 221, 537–541 (1969). https://doi.org/10.1038/221537a0

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1038/221537a0

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

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