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The Pineal Gland and its Endocrine Role pp 331–348Cite as

The 5-Methoxyindoles Different from Melatonin: Their Effects on the Sexual Axis

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Part of the book series: NATO Advanced Science Institutes Series ((NSSA,volume 65))

Abstract

From the time of Lerner’s discovery of melatonin (Lerner et al., 1958) to the present, much pineal research has been centered on the study of the effects of melatonin, and to date this 5-methoxyindole is considered by many authors as the pineal hormone responsible for inhibiting the reproductive system (details and references in Reiter, 1980) or the pineal factor conveying the photoperiodic message (see details and references in Hoffmann, 1981.

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References

  • Alexander, B., 1969, The synthesis and effects of pineal gland 5-methoxyindoles in relation to sexual maturation in the Japanese quail, Coturnix coturnix, japonica. Ph.D. Thesis, Northwestern University, Evanston, III., U.S.A.

    Google Scholar 

  • Axelrod, J., and Lauber, J.K., 1968, Hydroxyindole-O-methyltransferase in several avian species, Biochem. Pharmacol. 17: 828.

    Article  PubMed  CAS  Google Scholar 

  • Axelrod, J., and Weissbach, H., 1960, Enzymatic 0-methylation of N-acetylserotonin to melatonin, Science 131: 1312.

    CAS  Google Scholar 

  • Axelrod, J., and Weissbach, H., 1961, Purification and properties of hydroxyindole-O-methyltransferase activity in the rat pineal gland by environmental lighting, J. Biol. Chem. 236:211.

    Google Scholar 

  • Balemans, M.G.M., 1972, Age-dependent effects of 5-methoxytryptophol and melatonin on testes and comb growth of the white leghorn (Gallus domesticus, L.), J. Neural Transm. 33: 179.

    Article  PubMed  CAS  Google Scholar 

  • Balemans, M.G.M., Bary, F.A.M., Legerstee, W.C., and Van Benthem, J., 1980a, Seasonal variations in HIOMT activity during the night in the pineal gland of 21-day old male Wistar rats, J. Neural Transm. 49:107.

    Google Scholar 

  • Balemans, M.G.M., Collin, J.P., Legerstee, W.C., and Juillard, M.T., 1981, Preliminary investigations on the circadian rhythmicity of the methylation of 5hydroxyindoles in the pineal gland of the parakeet, Biol. Cell. 42:167.

    Google Scholar 

  • Balemans, M.G.M., Noordegraaf, E.M., Bary, F.A.M. and Van

    Google Scholar 

  • Berlo, M.F., 1978, Estimation of the methylating capacity of the pineal gland. With special reference to indole metabolism, Experientia 34: 887.

    Google Scholar 

  • Balemans, M.G.M., Pévet, P., Legerstee, W.C., and Nevo, E., 1980b, Melatonin and 5-methoxytryptophol synthesis in the pineal, the retina and the Harderian gland of the mole-rat (Spalax ehrenbergi,Nehring) and in the pineal of the mouse “eyeless”, J. Neural Transm. 49:225.

    Google Scholar 

  • Balemans„ M.G.M., Pévet, P., Van Benthem, J., HaldarMisra, C., Smith, I., and Hendriks, H., 1982, Seasonal rhythmicity in the capacity of HIOMT to synthesize different 5-methoxyindoles in the pineal, the retina and the Harderian gland of the golden hamster (Mesocricetus auratus) (submitted).

    Google Scholar 

  • Balemans, M.G.M., Van der Veerdonk, F.C.G., and Van de Kamer, J.C., 1977a, Effect of injecting 5-methoxyindoles on testicular weight of white leghorn cockerels, J. Neural Transm. 41:47.

    Google Scholar 

  • Balemans, M.G.M., Van der Veerdonk, F.C.G., and Van de Kamer, J.C., 1977b, The influence of 5-methoxytryptophol, a pineal compound, on comb growth, ovarian weight, follicular growth and egg production of juvenile and maturing adult white leghorn hens. J. Neural Transm. 41: 37.

    Article  PubMed  CAS  Google Scholar 

  • Beck, O., and Jonsson, G., 1981, In vivo formation of 5methoxytryptamine from melatonin in rat, J. Neurochem., 36: 2013.

    CAS  Google Scholar 

  • Beck, O., Jonsson, G., and Lundman, A., 1981, 5-Methoxyindoles in pineal gland of cow, pig, sheep and rat. Arch. Pharmacol. 318:49.

    Google Scholar 

  • Bosin, T.R., and Beck, 0., 1979, 5-Methoxytryptamine in the human pineal gland: identification and quantification by mass fragmentography, J. Neurochem. 32: 1853.

    Google Scholar 

  • Bosin, T.R., Jonsson, G., and Beck, 0., 1979, On the occurrence of 5-methoxytryptamine in brain, Brain Res. 173:79.

    Google Scholar 

  • Bradley, P.B., and Briggs, L., 1974, Further studies on the mode of action of psychomimetic drugs: antagonism of the excitatory actions of 5-hydroxytryptamine by methylated derivatives of tryptamine, Brit. J. Pharmacol. 50:345.

    Google Scholar 

  • Cardinali, D.P., and Wurtman, R.J., 1972, Hydroxyindole0-methyltransferase in rat pineal, retina and Harderian gland, Endocrinology 91: 247.

    CAS  Google Scholar 

  • Carter, S.J., Laud, C.A., Smith, I., Leone, R.M., Silman, R.E., Hooper, R.J.L., Larson-Carter, D.L., Finnie, M.D.A., and Mullen, P.E., 1979, 5-Methoxytryptophol in rat pineal glands and other tissues, in: “The Pineal Gland of Vertebrates including Man”, J.Ariëns Kappers and P.Pévet, eds., Prog. Brain Res., 52, Elsevier, Amsterdam.

    Google Scholar 

  • Cattabeni, F., Koslow, S.H., and Costa, E., 1972, Gas chromatographic-mass spectrometric assay of four indole alkylamines of rat pineal. Science 178: 166.

    CAS  Google Scholar 

  • Debeljuk, L., Feder, V.M., and Paulucci, D.A., 1970, Effect of treatment with melatonin on the pituitary-testicular axis of the male rat, J. Reprod. Fertil. 21:363.

    Google Scholar 

  • Delvigs, P., Mclsaac, W.M., and Taborsky, R.G., 1965, The metabolism of 5-methoxytryptophol, J. biol. Chem. 240:348.

    Google Scholar 

  • De Montigny, C., and Aghajanian, G.K., 1977, Preferential action of 5-methoxytryptamine and 5-methoxydimethyltryptamine on presynaptic serotonin receptors; a comparative iontophoretic study with LSD and serotonin, Neuropharmacology 15: 811.

    Google Scholar 

  • Farrel, G., Powers, D., and Otani, T., 1968, Inhibition of ovulation in the rabbit: seasonal variation and the effects of indoles, Endocrinology 83: 599.

    Google Scholar 

  • Fiske, V.M., and Huppert, L.C., 1968, Melatonin action on pineal varies with photoperiod, Science 162: 279.

    CAS  Google Scholar 

  • Franzen, F., and Gross, H., 1965, Tryptamine, N,N-Dimethyltryptamine, N,N-Dimethyl-5-hydroxytryptamine and 5-methoxytryptamine in human blood and urine, Nature 206: 1052.

    CAS  Google Scholar 

  • Fraschini, F. 1969, The pineal gland and the control of LH and FSH secretion, in: “Progress in Endocrinology”, C.Gual, ed., Excerpta Medica, Amsterdam.

    Google Scholar 

  • Fraschini, F., and Martini, L., 1970, Rhythmic phenomena and pineal principles, in: “The Hypothalamus”, L. Martini and F.Fraschini, eds., Academic Press, New York, London.

    Google Scholar 

  • Fraschini, F., Collu, R., and Martini, L., 1971, Mechanisms of inhibitory action of pineal principles on gonadotropin secretion, in: “The Pineal Gland”, G.E. W. Wolstenholm and J.Knight, eds., Churchill, New York.

    Google Scholar 

  • Guchhait, R.B., 1976, Biogenesis of 5-methoxy-N,N-dimeth-yltryptamine in human pineal gland, J. Neurochem. 26:187.

    Google Scholar 

  • Haddox, C.H., and Saslaw, M.S., 1963, Urinary 5-methoxytryptamine in patients with rheumatic fever, J. clin. Invest. 42:435.

    Google Scholar 

  • Herbert, J., 1971, The role of the pineal gland in the control by light of the reproductive cycle of the ferret, in: “The Pineal Gland”, G.E.W.Wolstenholm and J.Knight, eds., Churchill Livingston, Edinburgh, U.K.

    Google Scholar 

  • Hoagland, R.E., and Graf, G., 1971, Nitroacetanilides as chromogenic substrate for assaying de-acetylating activity: The isolation and partial purification of aryl acylamidases from erepsin and tulip, Enzymologia 41: 313.

    CAS  Google Scholar 

  • Hoffmann, K., 1974, Testicular involution in short photo-periods inhibited by melatonìn, Naturwissensch.61: 364.

    Google Scholar 

  • Hoffmann, K., 1981, Photoperiodic function of the mammalian pineal organ, in: “The Pineal Organ, Photo-biology - Biochronometry - Endocrinology”, A.Oksche and P.Pévet, eds., Elsevier/North-Holland, Amsterdam.

    Google Scholar 

  • Holmstedt, B., and Lindgren, J.E., 1967, Chemical constituents and pharmacology of south american snuffs, in: “Ethnopharmacologic Search for Psychiatric Drugs”, D.H.Efron, ed., U.S.Public Health Service, Washington.

    Google Scholar 

  • Hooper, R.J.L., Silman, R.E., Leone, R.M., and Young, I. M., 1981, The development of a plasma assay for 5-methoxytryptamine using gas chromatography-mass spectrometry, in: “Pineal Function”, C.D.Matthews and R.F.Seamark, eds., Elsevier/North-Holland.

    Google Scholar 

  • Hoskins, J.A., and Pollit, R.J., 1978, The determination of 5-methoxyindole-3-acetic acid in human urine by mass fragmentography, J. Chromatography 145:285.

    Google Scholar 

  • Jequier, E., Robinson, D.S., Lovenberg, W., and Sjoerdsma, A., 1969, Further studies on tryptophan hydroxylase in rat brainstem and beef pineal. Biochem. Pharmacol. 18:1071.

    Google Scholar 

  • Klein, D.C., 1979, Circadian rhythms in the pineal gland, in: “Endocrine Rhythms”, D.T.Krieger, ed., Raven Press, New York.

    Google Scholar 

  • Kopin, I.J., Pare, C.M.B., Axelrod, J., and Weissbach, H., 1961, The fate of melatonin in animals, J. Biol. Chem. 236:3072.

    Google Scholar 

  • Krebs, H.A., Sykes, W.O., and Bartley, W.C., 1947, Acetylation and deacetylation of the p-amino group of sulphonamide drugs in animal tissues, Biochem. J. 41:622.

    Google Scholar 

  • Kveder, S., and Mclsaac, W.M., 1961, The metabolism of melatonin (N-acetyl-5-methoxytryptamine) and 5-methoxytryptamine, J. Biol. Chem. 236:3214.

    Google Scholar 

  • Lerner, A.B., and Case, J.D., 1960, Melatonin, Fed. Proc., 19: 590.

    CAS  Google Scholar 

  • Lerner, A.B., Case, J.D., Takahashi, Y., Lee, T.H., and Mori, W., 1958, Isolation of melatonin, the pineal gland factor that lightens melanocytes, J. Amer. chem. Soc. 80:2587.

    Google Scholar 

  • Lerner, A.B., Case, J.D., and Takahashi, Y., 1960, Isolation of melatonin and 5-methoxyindole-3-acetic acid from bovine pineal glands, J. Biol. Chem. 235:1992.

    Google Scholar 

  • Lerner, A.B., Case, J.D., Biermann, K., Anthony, R.V., and Krivis, A., 1959, Isolation of 5-methoxyindole-3acetic acid from bovine pineal glands, J. Amer. chem. Soc. 81:5264.

    Google Scholar 

  • Lovenberg, W., Weissbach, H., and Udenfriend, A., 1962, Aromatic 1-amino acid decarboxylase, J. Biol. Chem. 237:89.

    Google Scholar 

  • Lovenberg, A., Jequier, E., and Sjoerdsma, A., 1967, Tryptophan hydroxylation. Measurement in pineal gland, brainstem and carcinoid tumor, Science 155: 217.

    CAS  Google Scholar 

  • Maickel, R.P., and Miller, F.P., 1968, The fluorometric determination of indolealkylamines in brain and pineal gland, Adv. Pharmacol. 6a:71.

    Google Scholar 

  • Martin, J.M., Engel, J.N., and Klein, D.C., 1977, Inhibition of the in vitro pituitary response to luteinizing hormone-releasing hormone by melatonin, serotonin and 5-methoxytryptamine, Endocrinology 100: 675.

    CAS  Google Scholar 

  • Mas, M., and Oaknin, S., 1977, Effects of pineal methoxyindoles on male sex behaviour and spermatogenesis, Pineal Gland Symposium, Abstract 18, Israel.

    Google Scholar 

  • Mclssac, W.M., and Page, I., 1959, The metabolism of serotonin (5-hydroxytryptamine), J. biol. Chem. 234:858.

    Google Scholar 

  • Mclssac, W.M., Farrell, G., Taborsky, R.G., and Taylor, A.N., 1965, Indole compounds: isolation from pineal tissue, Science 148: 102.

    Google Scholar 

  • Mclsaac, W.M., Taborsky, R.J., and Farrell, G., 1964, 5Methoxytryptophol: effect on estrus and ovarian weight, Science 145: 63.

    Google Scholar 

  • Miller, F.P., and Maickel, R.P., 1970, Fluorometric determination of indole derivatives, Life Sci. 9: 747.

    CAS  Google Scholar 

  • Nimmo-Smith, R.H., 1970, Aromatic N-deacetylation by chick-kidney mitochondria, Biochem. J. 75:284.

    Google Scholar 

  • Pévet, P., and Haldar-Mìsra, C., 1982a, Effect of 5-methoxytryptamine on the testicular atrophy induced by experimental or natural short photoperiods in the golden hamster, J. Neural Transm. in press.

    Google Scholar 

  • Pévet, P., and Haldar-Misra, C., 1982b, Daily 5-methoxytryptamine injections inhibit short-day induced testicular atrophy in golden hamsters, J. Neural Transm. in press.

    Google Scholar 

  • Pévet, P., and Haldar-Misra, C., 1982c, Morning injections of large doses of melatonin, but not of 5-methoxytryptamine, prevent in the hamster the antigonadotropic effect of 5-methoxytryptamine administered late in the afternoon, J. Neural Transm. in press.

    Google Scholar 

  • Pévet, P., Balemans, M.G.M., Bary, F.A.M., and Noordegraaf, E.M., 1978, The pineal gland of the mole (Talpa europaea, L.). V. Activity of hydroxy-indole-Omethyltransferase (HIOMT) in the formation of melatonin/5-hydroxytryptophol in the eyes and the pineal gland, Ann. Biol. anim. Biochem. Biophys. 18: 259.

    Article  Google Scholar 

  • Pévet, P., Balemans, M.G.M., Legerstee, W.C., and VivienRoels,B., 1980, Circadian rhythmicity of the activity of hydroxyindole-O-methyltransferase (HIOMT) in the formation of melatonin and 5-methoxytryptophol in the pineal, retina and Harderian gland of the golden hamster, J. Neural Transm. 19:229.

    Google Scholar 

  • Pévet, P., Balemans, M.G.M., and De Reuver, G.F., 1981a, The pineal gland of the mole (Talpa europaea,L.). VII. Activity of hydroxyindole-0-methyltransferase (HIOMT) in the formation of 5-methoxytryptophan, 5-methoxytryptamine, 5-methoxyindole-3-acetic acid, 5-methoxytryptophol and melatonin in the eyes and the pineal, J. Neural Transm. 51:271.

    Google Scholar 

  • Pévet, P., Haldar-Misra, C., and Ocal, T., 1981b, Effect of 5-methoxytryptophan and 5-methoxytryptamine on the reproductive system of the male golden hamster, J. Neural Transm. 51: 303.

    Article  PubMed  Google Scholar 

  • Pévet, P., Haldar-Misra, C., and Ocal, T., 1981c, The independency of an intact pineal gland of the inhibition by 5-methoxytryptamine of the reproductive organ in the male hamster, J. Neural Transm. 52:95.

    Google Scholar 

  • Prozialeck, W.C., Boehme, D.H., and Vogel, W.H., 1978, The fluorometric determination of 5-methoxytryptamine in mammalian tissues and fluids, J. Neurochem. 30:1471.

    Google Scholar 

  • Quay, W.B., 1964, Circadian and estrous rhythms in pineal melatonin and 5-hydroxyindole-3-acetic acid, Proc. Soc. Exp. Biol. Med. 115:710.

    Google Scholar 

  • Reiter, R.J., 1980, The pineal and its hormones in the control of reproduction in mammals, Endocr. Rev. 1:109.

    Google Scholar 

  • Reiter, R.J., Blask, D.E., Johnson, L.Y., Rudeen, P.K., Vaughan, M.K., and Waring, P.J., 1976, Melatonin inhibition of reproduction in the male hamster: its dependency on time of day of administration and on an intact and sympathetically innervated pineal gland, Neuroendocrinol. 22: 107.

    CAS  Google Scholar 

  • Reiter, R.J., Vaughan, M.K., Blask, D.E., and Johnson, L.Y., 1974, Melatonin: its inhibition of pineal antigonadotrophic activity in male hamsters, Science 185: 1169.

    CAS  Google Scholar 

  • Reiter, R.J., Vaughan, M.K., Blask, D.E., and Johnson, L. Y., 1975, Pineal methoxyindoles: new evidence concerning their function in the control of pineal mediated changes in the reproductive physiology of male golden hamsters, Endocrinology 96: 206.

    CAS  Google Scholar 

  • Rogawski, M.A., Roth, R.H., and Aghajanian, G.K., 1979, Melatonin deacetylation to 5-methoxytryptamine by liver but not brain aryl acylamidase. J. Neurochem. 32:1219.

    Google Scholar 

  • Sackman, J.W., Little, J.C., Rudeen, P.K., Waring, P.J., and Reiter, R.J., 1977, The effects of pineal in-doles given late in the light period on reproductive organs and pituitary prolactin levels in male golden hamsters, Horm. Res. 8:84.

    Google Scholar 

  • Smith, I., Larson-Carter, D.L., Laud, C.A., Leone, R.M., Silman, R.E., Carter, S.J., Francis, P., Mullen, P. E., Hooper, R.J.L., and Finnie, M.D.A., 1979, O-Acetyl-5-methoxytryptophol - Tentative identification in pineal glands, in: “The Pineal Gland of Vertebrates including Man”, J.Ariëns Kappers and P. Pevet, eds., Prog. Brain Res., 52, Elsevier/NorthHolland, Amsterdam.

    Google Scholar 

  • Snyder, S.H., and Axelrod, J., 1964, A sensitive assay for 5-hydroxytryptophan decarboxylase, Biochem. Pharmacol., 13:805.

    Google Scholar 

  • Talbot, J.A., and Reiter, R.J., 1973/1974, Influence of melatonin, 5-methoxytryptophol and pinealectomy on pituitary and plasma gonadotropin and prolactin levels in castrated adult male rats, Neuroendocrinology 13: 164.

    Google Scholar 

  • Tamarkin, L., Westerom, W.K., Hamill, A.I., and Goldman, B.D., 1976, Effect of melatonin on the reproductive system of male and female Syrian hamsters: A diurnal rhythm in sensitivity of melatonin, Endocrinology 99: 1534.

    CAS  Google Scholar 

  • Trentini, G.P., De Gaetani, G.F., Criscuolo, M., Balemans, M.G.M., Vaessen, H.M.B., and Smith, I., 1982, The effect of melatonin and other indole derivatives in maintaining ovulation in rats kept in continuous light and the influence of these indoles on HIOMT activity in the pineal gland, J. Neural Transm. in press.

    Google Scholar 

  • Turek, F.W., and Pappas, P., 1980, Daily melatonin injections inhibit short-day-induced testicular regression in hamsters, Experientìa 36: 1426.

    CAS  Google Scholar 

  • Vaughan, M.K., Reiter, R.J., Vaughan, G.M., Bigelow, L., and Altschule, M.D., 1972, Inhibition of compensatory ovarian hypertrophy in the mouse and vole: a comparison of Altschules pineal extract, pineal indoles, vasopressin and oxytocin, Gen. comp. Endocr. 18:372.

    Google Scholar 

  • Vaughan, M.K., Vaughan, G.M., and Reiter, R.J., 1976, Inhibition of human chorionic gonadotrophin-induced hypertrophy of the ovaries and uterus of immature mice by some pineal indoles, 6-hydroxy-melatonin and arginine vasotocin, J. Endocr. 68:397.

    Google Scholar 

  • Weissbach, H., Redfield, B.G., and Axelrod, J., 1960, Biosynthesis of melatonin. Enzymic conversion of serotonin to N-acetylserotonin. Biochim. biophys. Acta 43:352.

    Article  Google Scholar 

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Authors and Affiliations

  1. The Netherlands Institute for Brain Research Amsterdam, The Netherlands

    Paul Pévet

  2. Dept. of Anatomy and Embryology, University of Amsterdam, The Netherlands

    Paul Pévet

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  1. Paul Pévet
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Editors and Affiliations

  1. National Institute of Mental Health, Bethesda, Maryland, USA

    J. Axelrod

  2. University of Milan, Milan, Italy

    F. Fraschini

  3. University of Verona, Verona, Italy

    G. P. Velo

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Pévet, P. (1983). The 5-Methoxyindoles Different from Melatonin: Their Effects on the Sexual Axis. In: Axelrod, J., Fraschini, F., Velo, G.P. (eds) The Pineal Gland and its Endocrine Role. NATO Advanced Science Institutes Series, vol 65. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-1451-7_18

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