Naunyn-Schmiedeberg's Archives of Pharmacology

, Volume 318, Issue 1, pp 49–55 | Cite as

5-Methoxyindoles in pineal gland of cow, pig, sheep and rat

  • O. Beck
  • G. Jonsson
  • A. Lundman


The occurrence and concentration of the four 5-methoxyindoles: 5-methoxytryptamine, 5-methoxytryptophol, 5-methoxyindole-3-acetic acid and melatonin in the pineal gland of pig, cow, sheep and rat was investigated. The analytical method involved the use of deuterated analogues as internal standards and capillary column gas chromatography — mass spectrometry. The analyses of pineal glands obtained during the morning hours revealed the presence of 5-methoxyindole-3-acetic acid and melatonin in nmoles/g and 5-methoxytryptophol and 5-methoxytryptamine in pmoles/g amounts in pig, cow and sheep. In Wistar and Sprague-Dawley strain of rat, melatonin was present at a concentration of about 0.5 pmoles/pineal, a level which was elevated more than five times by treatment with a monoamine oxidase inhibitor. 5-methoxytryptamine was found at a concentration of about 0.03 pmoles/pineal, and was elevated by monoamine oxidase inhibition.

Key words

Indole Tryptamine Pineal gland Gas chromatography-mass spectrometry 


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  1. Axelrod J, Weissbach H (1960) Enzymatic O-methylation of N-acetylserotonin to melatonin. Science 131:1312Google Scholar
  2. Beck O, Bosin RT (1979) Analysis of 5-methoxytryptamine in brain by gas chromatography mass spectrometry. Biomed Mass Spectrom 6:19–22Google Scholar
  3. Beck O, Jonsson G (1981) In vivo formation of 5-methoxytryptamine from melatonin in rat. J Neurochem 36:2013–2018Google Scholar
  4. Blau K, King GS, Sandler M (1977) Mass spectrometric and nuclear magnetic resonance confirmation of a 3,3-spirocyclic indole derivative formed from melatonin and related acyl tryptamines. Biomed Mass Spectrom 4:232–236Google Scholar
  5. Bosin TR, Jonsson G, Beck O (1979) On the occurrence of 5-methoxytryptamine in brain. Brain Res 173:79–88Google Scholar
  6. Carter SJ, Laud CA, Smith I, Leone RM, Hooper RJL, Silman RE, Finnie MDA, Mullen PE, Larson-Carter DL (1979) Concentration of 5-methoxytryptophol in pineal gland and plasma of the rat. J Endoer 83:35–40Google Scholar
  7. Cattabeni F, Koslow SH, Costa E (1972) Gas chromatographic-mass spectrometric assay of four indole alkylamines of rat pineal. Science 178:166–168Google Scholar
  8. Dewhurst WG, McKim HR (1979) Is 5-methoxytryptamine the B-type fluorophore in rat brain. Neuropsychobiology 5:156–159Google Scholar
  9. Green AR, Koslow SH, Costa E (1973) Identification and quantitation of a new indolealkylamine in rat hypothalamus Brain Res 51:371–374Google Scholar
  10. Hesselgren T, Beck O (1979) Synthesis of six specifically deuterated indoles of biological interest. J Labelled Comp Radiopharmac 27:411–419Google Scholar
  11. Klein DC (1978) The Pineal Gland: A model of neuroendocrine regulation. In: Reichlin S, Baldessarini RJ Martin JB (eds) The hypothalamus. Raven Press, New York pp 303–327Google Scholar
  12. Kveder S, McIsaac WM (1961) The metabolism of melatonin (N-acetyl-5-methoxytryptamine) and 5-methoxytryptamine. J Biol Chem 235:3214–3220Google Scholar
  13. Lerner AB, Case JD, Takahashi YJ (1960) Isolation of melatonin and 5-methoxyindole-3-acetic acid from bovine pineal gland. Biol Chem 235 (7):1992–1997Google Scholar
  14. cIsaac WM, Farrell G, Taborsky RG, Taylor AN (1965) Indole compounds: Isolation from pineal, tissue. Science 148:102–103Google Scholar
  15. Meek JL, Neckers LM (1977) Studies of serotonin turnover in discrete nuclei using HPLC. Mod Pharmacol Toxicol 10:799–809Google Scholar
  16. Miller FR, Maickel RP (1970) Fluorometric determination of indole derivatives. Life Sci 9:747–752Google Scholar
  17. Narasimhachari N, Kempster E, Anbar M (1980) 5-Methoxytryptamine in rat hypothalamus and human CSF. A fact or artifact? Biomed Mass Spectrom 7:231–235Google Scholar
  18. Prozialeck WC, Boehme DH, Vogel WH (1978) The fluorometric determination of 5-methoxytryptamine in mammalian tissues and fluids. J Neurochem 30:1471–1477Google Scholar
  19. Quay WB (1974) In: Pineal chemistry. Thomas C C, IL, pp 252–259Google Scholar
  20. Shaw GJ, Wright GJ, Milne GWA (1977) Mass spectra of some specifically deuterated tryptamines. Biomed Mass Spectrom 4:348–353Google Scholar
  21. Smith I, Francis P, Leone RM, Mullen PE (1980) Identification of O-acetyl-5-methoxytryptophenol in, the pineal gland by gas chromatography — mass spectrometry. Biochem J 185:537–540Google Scholar
  22. Wilson BW (1978) The application of mass spectrometry to the study of the pineal gland. J Neural Transm (Suppl) 13:279–288Google Scholar

Copyright information

© Springer-Verlag 1981

Authors and Affiliations

  • O. Beck
    • 1
  • G. Jonsson
    • 1
  • A. Lundman
    • 1
  1. 1.Departments of Toxicology and HistologyKarolinska InstitutetStockholmSweden

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