Skip to main content
SpringerLink
Log in

Acyltryptophols reversibly inhibit muscle contractions caused by the actions of acetylcholine and raised potassium ion concentrations

  • Published:
Journal of Neural Transmission Aims and scope Submit manuscript

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Summary

  1. 1.

    Acetylmethoxytryptophol, originally isolated from the pineal gland, inhibits both the nicotinic and muscarinic receptor stimulatory activities of acetylcholine on frog rectus muscle and guinea pig ileum.

  2. 2.

    Synthetic homologues and analogues, including the acetyl-, propionyl-, butyryl-, and valeryl-methoxytryptophols, tryptophols andα-methyltryptophols have been prepared and shown to possess similar activity on the frog muscle, with butyryl compounds being the most active. Methoxytryptophol, tryptophol,α-methyltryptophol and acetylhydroxytryptophol possess little or no activity.

  3. 3.

    All acyltryptophols tested inhibit the effect of increased potassium concentrations on frog muscle.

  4. 4.

    It is concluded that the acyltryptophols act not at the transmitter receptor level but either at the potassium ion channel or elsewhere in the cell membrane.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Balemans, M. G. M., Smith, I., De Reuver, G. F.: Changes in the Circadian Rhythmicity of N- and O-acetyltransferase activities in the pineal gland of 38 day old male Wistar rats when examined under white, red and green light. J. Neural Transm.52, 83–93 (1981).

    PubMed  Google Scholar 

  • Bartfai, T., Study, R. E., Greengard, P.: Muscarinic stimulation and cGMP Synthesis in the Nervous System. In: Cholinergic Mechanism and Psychopharmacology (Jenden, D. sJ., ed.). New York: Plenum Press. 1978.

    Google Scholar 

  • Bean, R. C., Shepherd, W. C., Chan, H.: Permeability coefficients of some indoles. J. Gen. Physiol.52, 495–501 (1968).

    PubMed  Google Scholar 

  • Edinburgh, Staff: Pharmacological experiments on isolated preparations, 2nd ed. Edinburgh: Churchill-Livingstone. 1970.

    Google Scholar 

  • Francis, P., Smith, I., Finnie, M. D. A.: Mass spectrometric and chromatographic characteristics of neutral and acidic 5-methoxyindoles and some related compounds. Biomed. Mass. Spectrom.7, 294–300 (1980).

    Google Scholar 

  • Francis, P.L., Fernando, I.N., Smith, I.: Unpublished observations (1982).

  • Fraschini, F., Collu, R., Martini, L.: Mechanisms of inhibitory action of pineal principles on gonadotropin secretion. In: The Pineal Gland (Wolstenholme, G. E. W., Knight, J., eds.), pp.259–273. London: Churchill-Livingstone. 1971.

    Google Scholar 

  • Heinzelman, R. V., Szmuszkovicz, J.: Recent studies in the field of indole compounds. Progr. Drug Res.6, 75–149 (1963).

    Google Scholar 

  • Leone, R. M., Silman, R. E., Hooper, R. J. L., Young, I. M.: The investigation of pineal indoles and their metabolites using gas chromatography-mass spectrometry. In: Pineal Function (Matthews, C. D., Seamark, R. F., eds.), pp. 13–16. Amsterdam: Elsevier/North-Holland Biomedical Press. 1981.

    Google Scholar 

  • Lerner, A. sB., Case, J. sD., Takahashi, Y.: Isolation of melatonin. J. Biol. Chem.235, 1992–1997 (1960).

    PubMed  Google Scholar 

  • Mclsaac, W. M., Farrell, G., Taborsky, R. G., Taylor, A. N.: Indole compounds: isolation from pineal tissue. Science148, 102–103 (1965).

    PubMed  Google Scholar 

  • Moshtaghfard, A., Smith, I.: Acyltryptophols reversibly inhibit the uptake of thymidine after phytohaemagglutinin transformation of human lymphocytes. J. Neural Transm.56, 43–52 (1983).

    PubMed  Google Scholar 

  • Reiter, R.J., Vaughan, M.K., Chen, H.J., Meyer, A. C., Philo, R. C.: Reproductive consequences of melatonin in mammals. In: Abstr. Int. Symp. Melatonin, Bremen, pp. 47–50. 1980.

  • Smith, I.: Concluding remarks. In: Annual Research Reviews: The Pineal6, 209–213 (1981). (Reiter, R.J., ed.) Montreal: Eden Press. See also European Pineal Study Group (EPSG) Newsletter No 8 (Pevet, P., ed.). 1982.

    Google Scholar 

  • Smith, I., Carter, D. L., Laud, C. A., Leone, R. M., Silman, R. E., Carter, S. J., Mullen, P. E., Hooper, J., Finnie, M. D. A.: O-Acetyl-5-methoxytryptophol-tentative identification in pineal glands. Progr. Brain Res.52, 259–261 (1979).

    Google Scholar 

  • Smith, I., Francis, P., Leone, R. M., Mullen, P. E.: Identification of O-acetyl-5-methoxy-tryptophol in the pineal gland by gas chromatography-mass spectrometry. Biochem. J.185, 537–540 (1980).

    PubMed  Google Scholar 

  • Taborsky, R. G., Delvigs, P.: Synthesis of some substituted tryptophols of possible physiological importance and a study with 3-(2-acetoxyethyl)-5-methoxyindole (5-methoxytryptophol-O-acetate) on sexual maturation. J. Med. Chem.9, 251–254 (1966).

    PubMed  Google Scholar 

Download references

Author information

Author notes

  1. I. Smith

    Present address: Courtauld Institute of Biochemistry, Middlesex Hospital Medical School, Mortimer Street, London, UK

Authors and Affiliations

  1. Courtauld Institute of Biochemistry, Middlesex Hospital Medical School, Mortimer Street, London, UK

    I. N. Fernando & P. L. Francis

Authors
  1. I. N. Fernando
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. L. Francis
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. Smith
    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

Fernando, I.N., Francis, P.L. & Smith, I. Acyltryptophols reversibly inhibit muscle contractions caused by the actions of acetylcholine and raised potassium ion concentrations. J. Neural Transmission 56, 33–41 (1983). https://doi.org/10.1007/BF01243372

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01243372

Keywords

Search

Navigation