Skip to main content

Chemical analysis of indolealkylamines and related compounds

  • Chapter
5-Hydroxytryptamine and Related Indolealkylamines

Abstract

A close parallel between methodology and understanding has been recognized throughout modern scientific research, and is germane to the topics of indolealkylamines and related compounds. Although 5-hydroxytryptamine was first isolated from biological material by Erspamer in 1937, further developments in this field were sparse until the early 1950’s, when more advanced analytical techniques were employed. Within the past ten years, isolation, identification, and quantitation of indole compounds has rapidly proliferated, and the metabolic pathways, physiological roles, and pharmacological effects of these compounds have been increasingly understood. Of crucial importance to this progress has been the application of three analytical techniques: paper chromatography, spectrophotometry, and spectrophotofluorometry.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Anderson, J. A., M. R. Ziegler, and D. Doeden: Banana feeding and urinary excretion of 5-hydroxyindoleacetic acid. Science 127, 236–238 (1958).

    Article  PubMed  CAS  Google Scholar 

  • Armstrong, M. D., K. N. F. Shaw, M. J. Gortatowski, and H. Singer: The indole acids of human urine. Paper chromatography of indole acids. J. biol. Chem. 232, 17–30 (1958).

    PubMed  CAS  Google Scholar 

  • Armstrong, M. D., K. N. F. Shaw, and P. E. Wall: The phenolic acids of human urine. J. biol. Chem. 218, 293–303 (1956).

    PubMed  CAS  Google Scholar 

  • Axelrod, J., R. O. Brady, B. Witkop, and E. V. Evarts: The distribution and metabolism of lysergic acid diethylamide. Ann. N.Y. Acad. Sci. 66, 444–435 (1957).

    Article  Google Scholar 

  • Axelrod, J., and H. Weissbach: Purification and properties of hydroxyindole-O-methyl transferase. J. biol. Chem. 236, 211–213 (1961).

    PubMed  CAS  Google Scholar 

  • Blau, K.: Chromatographic methods for the study of amines from biological material. Biochem. J. 80, 193–200 (1961).

    PubMed  CAS  Google Scholar 

  • Block, R. J., E. L. Durrum, and G. Zweig: A manual of paper chromatography and paper electrophoresis. New York 1958.

    Google Scholar 

  • Boardman, N. K.: Molecular sieving other than dialysis. In: H. F. Linskens and M. V. Tracey (eds.), Modern methods of plant analysis, vol. 5, p. 205–213. Berlin-Göttingen-Heidelberg: Springer 1962.

    Chapter  Google Scholar 

  • Bobbit, J. M.: Thin-layer chromatography. New York 1963.

    Google Scholar 

  • Bogdanski, D. F., A. Pletscher, B. B. Brodie, and S. Udenfriend: Identification and assay of serotonin in brain. J. Pharmacol, exp. Ther. 117, 82–88 (1956).

    CAS  Google Scholar 

  • Bowman, R. L., P. A. Caulfield, and S. Udenfriend: Spectrophotofluorometric assay in the visible and ultraviolet. Science 122, 32–33 (1955).

    Article  PubMed  CAS  Google Scholar 

  • Bruce, D. W.: Serotonin in pineapple. Nature (Lond.) 188, 147 (1960).

    Article  CAS  Google Scholar 

  • Bumpus, F. M., and I. H. Page: Serotonin and its methylated derivatives in human urine. J. biol. Chem. 212, 111–116 (1955).

    PubMed  CAS  Google Scholar 

  • Burchfield, H. P., and E. E. Storrs: Biochemical applications of gas chromatography. New York 1962.

    Google Scholar 

  • Cais, M.: The spectrofluorometric assay of serotonin and histamine in tissues following a common extraction procedure. Med. exp. (Basel) 5, 73–76 (1961).

    Article  CAS  Google Scholar 

  • Carcasona, A., J. Cervos-Navarro u. F. Unterharnscheidt: Untersuchungen zur quantitativen Bestimmung von 5-Hydroxytryptamin und 5-Hydroxyindolessigsäure mit dem Spektralphotometer. Klin. Wschr. 37, 253–254 (1959a).

    Article  PubMed  CAS  Google Scholar 

  • Carcasona, A., F. Unterharnscheidt u. J. Cervos-Navarro: Die quantitative Bestimmung von 5-Hydroxytryptophan, 5-Hydroxytryptamin und 5-Hydroxyindolessigsäure mit der Papierchromatographie. Klin. Wschr. 37, 761–763 (1959b).

    Article  PubMed  CAS  Google Scholar 

  • Carcasona, A., F. Unterharnscheidt u. J. Cervos-Navarro, u. W. Geller: Untersuchungen zur quantitativen Bestimmung von 5-Hydroxytryptophan, 5-Hydroxytryptamin und 5-Hydroxyindolessigsäure mit Hilfe der Papier-elektrophorese. Klin. Wschr. 38, 457–460 (1960).

    Article  PubMed  CAS  Google Scholar 

  • Chadwick, B. T., and J. H. Wilkinson: The effects of phenothiazine drugs on the determination of urinary 5-hydroxyindolylacetic acid. Clin. chim. Acta 5, 879–886 (1960).

    Article  PubMed  CAS  Google Scholar 

  • Cheronis, N. D., and J. B. Entrikin: Semimicro qualitative organic analysis, p. 730. New York 1957.

    Google Scholar 

  • Clotten, R., u. A. Clotten: Hochspannungs-Elektrophorese. Stuttgart 1962.

    Google Scholar 

  • Consden, R.: Paper chromatography. In C. Long (ed.), Biochemists’ Handbook, p. 127–160. London 1961.

    Google Scholar 

  • Cooper, J. R., and I. Melcer: The enzymic oxidation of tryptophan to 5-hydroxytrypto-phan in the biosynthesis of serotonin. J. Pharmacol. exp. Ther. 132, 265–268 (1961).

    PubMed  CAS  Google Scholar 

  • Correale, P.: Colorimetric and spectrophotometric titration of 5-hydroxyindoleacetic acid. Experientia (Basel) 11, 315 (1955).

    Article  CAS  Google Scholar 

  • Craig, L. C.: Countercurrent distribution. In: C. Long (ed.), Biochemists’ Handbook, p. 98–105. London 1961.

    Google Scholar 

  • Craig, L. C.,and D. Craig: Extraction and distribution. In: A. Weissberger (ed.), Technique of organic chemistry, vol. 3, p. 171–311. New York 1956.

    Google Scholar 

  • Crawford, N., and B. T. Rudd: A spectrophotofluorometric method for the determination of serotonin (5-hydroxytryptamine) in plasma. Clin. chim. Acta 7, 114–121 (1962).

    Article  PubMed  CAS  Google Scholar 

  • Crout, J. R., and A. Sjoerdsma: The clinical and laboratory significance of serotonin and catecholamines in bananas. New Engl. J. Med. 261, 23–26 (1959).

    Article  PubMed  CAS  Google Scholar 

  • Curzon, G.: A rapid Chromatographie test for high urinary 5-hydroxy-indole-acetic acid and 5-hydroxytryptamine. Lancet 1955 II, 1361–1362.

    Article  Google Scholar 

  • Dalgliesh, C. E.: Isolation and examination of urinary metabolites containing an aromatic system. J. clin. Path. 8, 73–78 (1955).

    Article  PubMed  CAS  Google Scholar 

  • Dalgliesh, C. E.: Two-dimensional paper chromatography of urinary indoles and related substances. Biochem. J. 64, 481–485 (1956).

    PubMed  CAS  Google Scholar 

  • Dalgliesh, C. E.: The 5-hydroxyindoles. Advance, clin. Chem. 1, 193–235 (1958).

    Article  CAS  Google Scholar 

  • Dalgliesh, C. E., and R. W. Dutton: Biogenesis of 5-hydroxytryptophan. Brit. J. Cancer 11, 296–309 (1957).

    Article  PubMed  CAS  Google Scholar 

  • Davis, V. E., and J. Awapara: A method for the determination of some amino acid decarboxylases. J. biol. Chem. 235, 124–127 (1960).

    PubMed  CAS  Google Scholar 

  • Deaver, G. L., W. E. Crisp, and W. J. Frajola: Use of ionophoretic mobility equilibria in fractionation of mixtures containing indoles. Proc. Soc. exp. Biol. (N.Y.) 98, 632–635 (1958).

    CAS  Google Scholar 

  • Degkwitz, R., R. Frowein, E. Kirberger, C. Kulenkampff u. U. Mohs: Über Normalwerte der stündlichen 5-HIES-Ausscheidung im Urin beim Menschen und die Messungen störende Faktoren. Klin. Wschr. 40, 285–289 (1962).

    Article  PubMed  CAS  Google Scholar 

  • Demole, E.: Chromatostrips and chromatoplates. Chromatogr. Rev. 1, 1–10 (1959).

    Article  Google Scholar 

  • Denffer, D. Yon, M. Behrens u. A. Fischer: Papierelektrophoretische Trennung von Indolderivaten aus Pflanzenextrakten. Naturwissenschaften 39, 258–259 (1952).

    Article  CAS  Google Scholar 

  • Dengler, H.: Atypisches Carcinoidsyndrom mit vermehrter Ausscheidung von 5-Hydroxy-indolessigsäure bei Pankreascarcinom. Klin. Wschr. 37, 1245–1248 (1959).

    Article  PubMed  CAS  Google Scholar 

  • Dickman, S. R., and A. L. Crockett: Reactions of xanthydrol. IV. Determination of trypto-phan in blood plasma and in proteins. J. biol. Chem. 220, 957–965 (1956).

    PubMed  CAS  Google Scholar 

  • Dickman, S. R., and W. L. Wescott: Reactions of xanthydrol. 1. Amino acids. J. biol. Chem. 210, 481–489 (1954).

    PubMed  CAS  Google Scholar 

  • Dietrich, L. S.: A rapid method for the determination of dihydroxyphenylalanine decarboxylase in animal tissues. J. biol. Chem. 204, 587–591 (1953).

    PubMed  CAS  Google Scholar 

  • Dillard, G. H. P., G. Brecher, and E. P. Cronkite: Separation, concentration, and transfusion of platelets. Proc. Soc. exp. Biol. (N.Y.) 78, 796–799 (1951).

    CAS  Google Scholar 

  • Duggan, D. E., and S. Udenfriend: The spectrophotofluorometric determination of tryptophan in plasma and of trvptophan and tvrosine in protein hvdrolvsates. J. biol. Chem. 223, 313–319 (1956).

    PubMed  CAS  Google Scholar 

  • Dunn, M.S., H. F. Schott, W. Frankl, and L. B. Rockland: Investigations of amino acids, peptides, and proteins: determination of apparent free tryptophan in blood by microbiological method. J. biol. Chem. 157, 387–394 (1945).

    CAS  Google Scholar 

  • Eble, J. X., and R. M. Brooker: A novel quantitative application of thin layer chromato-graphy: Assay of tryptamine. Experientia (Basel) 18, 524 (1962).

    Article  CAS  Google Scholar 

  • Efron, M.: High voltage paper electrophoresis. In: I. Smith (ed.), Chromatographic and electrophoretic techniques, p. 158–189. London 1960.

    Google Scholar 

  • Egelhaaf, A.: Der Gehalt an freiem Tryptophan und Kynurenin bei den Genotypen a+ und a von Ephestia kühniella während der Entwicklung. Z. Naturforsch. 12b, 465–472 (1957).

    CAS  Google Scholar 

  • Erspamer, V.: The enterochromaffin cell system and enteramin (5-hydroxytryptamin). R. C. sci. Farmitalia 1, 1–193 (1954).

    Google Scholar 

  • Erspamer, V.: Observations on the fate of indolalkylamines in the organism. J. Phvsiol. (Lond.) 127, 118–133 (1955).

    CAS  Google Scholar 

  • Erspamer, V.: Some observations on the fate of exogeneous 5-hydroxytryptamine (enteramine) in the rat. J. Physiol. (Lond.) 133, 1–9 (1956).

    CAS  Google Scholar 

  • Erspamer, V., and G. Bertaccini: Observations on the antidiuretic action and the fate of 5-hydroxy-DL-tryptophan in the rat organism. Arch. int. Pharmacodyn. 137, 6–23 (1962).

    PubMed  CAS  Google Scholar 

  • Erspamer, V., and G. Boretti: Identification and characterization, by paper chromatography, of enteramine, octopamine, tyramine, histamine and allied substances in extracts of posterior salivary glands of octopoda and in other tissue extracts of vertebrates and invertebrates. Arch. int. Pharmacodyn. 88, 296–332 (1951).

    PubMed  CAS  Google Scholar 

  • Erspamer, V., and M. B. Nobili: Observations on the fate of 4-hydroxy-DL-tryptophan in the organism of the rat and man. Arch. int. Pharmacodyn. 137, 24–38 (1962 a).

    PubMed  CAS  Google Scholar 

  • Erspamer, V., and M. B. Nobili: Observations on the fate of DL-5-hydroxy-N-acetyltryptophan and DL-5-acetoxy-N-acetyltryptophan in the rat organism. Arch. int. Pharmacodyn. 139, 433–446 (1962b).

    CAS  Google Scholar 

  • Falck, B.: Observations on the possibilities of the cellular localization of monoamines by a fluorescence method. Acta physiol. scand. 56, Suppl. 197 (1962).

    Google Scholar 

  • Fales, H. M., and J. J. Pisano: Gas chromatography of biologically important amines. Analyt. Biochem. 3, 337–342 (1962).

    Article  PubMed  CAS  Google Scholar 

  • Fearon, W. R., and W. A. Boggust: Pigments derived from tryptophan: (1) Urorosein, (2) Tryptochrome. Biochem. J. 46, 62–67 (1950).

    PubMed  CAS  Google Scholar 

  • Flodin, P., and J. Porath: Molecular sieve processes. In: E. Heftmann (ed.), Chromatography, p. 328–343. New York 1961.

    Google Scholar 

  • Fuchs, A. R., and F. Fuchs: Urinary excretion of 5-hydroxyindoleacetic acid during the menstrual cycle. Dan. med. Bull. 9, 39–45 (1960).

    Google Scholar 

  • Gaedtke, K., u. K. Schreier: Eine Methode zur Serotoninbestimmung im Urin. Clin. Chim. Acta 1, 475–477 (1956).

    Article  PubMed  CAS  Google Scholar 

  • Gayer, J.: Zum Nachweis biogener Amine. Biochem. Z. 328, 39–43 (1956).

    PubMed  CAS  Google Scholar 

  • Gelotte, B.: Gel filtration. Sorption properties of the bed material sephadex. J. Chromatog. 3, 330–342 (1960).

    Article  CAS  Google Scholar 

  • Gerngross, O., K. Voss u. H. Herfeld: Über eine hochempfindliche, streng tyrosinspezifische Farbreaktion auf para-substituierte Phenole. Ber. dtsch. chem. Ges. 66, 435–442 (1933).

    Article  Google Scholar 

  • Gluckman, M. I., and R. Abrams: A method for serotonin determination. Fed. Proc. 18, 395 (1959).

    Google Scholar 

  • Goble, A. J., D. R. Hay, and M. Sandler: 5-Hydroxytryptamine metabolism in acquired heart-disease associated with argentaffin carcinoma. Lancet 1955 II, 1016–1017.

    Article  Google Scholar 

  • Graham, C. E., E. P. Smith, S. W. Hier, and D. Klein: An improved method for the determination of tryptophane with p-dimethylaminobenzaldehvde. J. biol. Chem. 168, 711–716 (1947).

    PubMed  CAS  Google Scholar 

  • Hais, I. M., u. K. Macek: Handbuch der Papierchromatographie, Bd. 1. Jena 1958.

    Google Scholar 

  • Hanson, A.: Unpublished results 1964.

    Google Scholar 

  • Hanson, A., and F. Serin: Determination of 5-hydroxyindoleacetic acid in urine and its excretion in patients with malignant carcinoids. Lancet 1955 II, 1359–1361.

    Article  Google Scholar 

  • Harley-Mason, J., and A. A. P. G. Archer: Use of p-dimethylaminocinnamaldehyde as a spray reagent for indole derivatives on paper chromatograms. Biochem. J. 69, 60 P (1958).

    Google Scholar 

  • Hecker, E.: Verteilungsverfahren im Laboratorium. Weinheim 1955.

    Google Scholar 

  • Heinrich, P., u. W. Schüler: Stabilisierte Diazoniumsalze als Reagenzien zur Bestimmung von Dioxybenzolderivaten. II. Über eine kolorimetrische Bestimmungsmethode des 1,2-Dioxybenzols, des Methylaminomethyl-[3,4-dioxy-phenyl]-carbinols und der α-Amino-ß-[3,4-dioxyphenyl]-propionsäure. Helv. chim. Acta 31, 320–330 (1948).

    Article  PubMed  CAS  Google Scholar 

  • Hess, S. M.: Chemical estimation of tryptamine. In: J. H. Quastel (ed.), Methods in Medical Research, vol. 9, p. 175–177. Chicago 1961.

    Google Scholar 

  • Hess, S. M., B. G. Redfield, and S. Udenrfiend: The effect of monoamine oxidase inhibitor and tryptophan on the tryptamine content of animal tissues and urine. J. Pharmacol. exp. Ther. 127, 178–181 (1959).

    PubMed  CAS  Google Scholar 

  • Hess, S. M., P. A. Shore, and B. B. Brodie: Persistence of reserpine action after the disappearance of drug from brain: effect of serotonin. J. Pharmacol. exp. Ther. 118, 85–89 (1956).

    Google Scholar 

  • Hess, S. M., and S. Udenfriend: A fluorometric procedure for the measurement of tryptamine in tissues. J. Pharmacol. exp. Ther. 127, 175–177 (1959).

    PubMed  CAS  Google Scholar 

  • Holmstedt, B., and G. Lundgren: Unpublished results 1964.

    Google Scholar 

  • Holmstedt, B., V. J. A. Vandenheuvel, W. L. Gardiner, and E. C. Horning: The separation and identification of tryptamine-related indole bases by gas Chromatographic methods. Analyt. Biochem. 8, 151–157 (1964).

    Article  PubMed  CAS  Google Scholar 

  • Hornet, J. C., T. V. Casey, and J. W. Runyan: False-positive urinary test for 5-hydroxyindoleacetic acid due to methocarbamol and mephenesin carbamate. New Engl. J. Med. 261, 188–190 (1959).

    Article  Google Scholar 

  • Jepson, J. B.: Paper chromatography of urinary indoles. Lancet 1955 II, 1009–1011.

    Article  Google Scholar 

  • Jepson, J. B.: Indoles and related Ehrlich reactors. In: I. Smith (ed.), Chromatographic and electro-phoretic techniques, vol. 1, p. 183–211. London 1960.

    Google Scholar 

  • Jepson, J. B., and B.J. Stevens: A fluorescence test for serotonin and other tryptamines. Nature (Lond.) 172, 772 (1953).

    Article  CAS  Google Scholar 

  • Jepson, J. B., P. Zaltzman, and S. Udenfriend: Microsomal hydroxylation of tryptamine, indole-acetic acid and related compounds, to 6-hydroxy derivatives. Biochim. biophys. Acta (Amst.) 62, 91–102 (1962).

    Article  CAS  Google Scholar 

  • Kakimoto, Y., and M. D. Armstrong: The phenolic amines of human urine. J. biol. Chem. 237, 208–214 (1962).

    PubMed  CAS  Google Scholar 

  • Kettlemans, A. I. M.: Gas chromatography, 2 ed. New York 1959.

    Google Scholar 

  • Kirberger, E.: Differentialdiagnostische Überlegungen bei vermehrter 5-Hydroxyindol-essigsäure-Ausscheidung im Harn. Dtsch. med. Wschr. 87, 829–834 (1962).

    Article  Google Scholar 

  • Kirberger, E., u. L. Braun: Über das Vorkommen von 5-Hydroxytryptamin in der Walnuβ. Biochim. biophys. Acta (Amst.) 49, 391 (1961).

    Article  CAS  Google Scholar 

  • Langemann, H., u. J. Kägi: Oxytryptamin-und Oxyindolessigsäurebestimmungen bei einem Fall von Carcinoidsyndrom, nebst einigen anderen Untersuchungen über Oxytryptamin. Klin. Wschr. 34, 237–241 (1956).

    Article  PubMed  CAS  Google Scholar 

  • Lederer, M.: A introduction to paper electrophoresis and related methods. Amsterdam 1955.

    Google Scholar 

  • Lerner, A. B., J. D. Case, K. Biemann, R. V. Heinzelman, J. J. Szmuszkovicz, W. C. Anthony, and A. Krivis: Isolation of 5-methoxyindole-3-acetic acid from bovine pineal glands. J. Amer. chem. Soc. 81, 5264 (1959a).

    Article  Google Scholar 

  • Lerner, A. B., J. D. Case, and R. V. Heinzelman: Structure of melatonin. J. Amer. chem. Soc. 81, 6084 (1959b).

    Article  CAS  Google Scholar 

  • Linskens, H. F.: Papierchromatographie in der Botanik. Berlin-Göttingen-Heidelberg 1959.

    Google Scholar 

  • Lovenberg, W., H. Weissbach, and S. Udenfriend: Aromatic L-amino acid decarboxylase. J. biol. Chem. 237, 89–94 (1962).

    PubMed  CAS  Google Scholar 

  • Macek, K.: Techniques of liquid-liquid partition chromatography. In: E. Heftmann (ed.), Chromatography, p. 112–163. New York 1961.

    Google Scholar 

  • Macfarlane, P. S., C. E. Dalgliesh, R. W. Dutton, B. Lennox, L. M. Nyhus, and A. N. Smith: Endocrine aspects of argentaffinoma, with special reference to the use of the urinary 5-hydroxyindoleacetic acid estimations in diagnosis. Scot. med. J. 1, 148–155 (1956).

    PubMed  CAS  Google Scholar 

  • Mcilwain, H., and R. Rodnight: Practical neurochemistry. London 1962.

    Google Scholar 

  • Mcisaac., W. M., and I. H. Page: The metabolism of serotonin (5-hydroxytryptamine). J. biol. Chem. 234, 858–864 (1959).

    PubMed  CAS  Google Scholar 

  • Mead, J. A., and K. F. Finger: A simple extraction method for the determination of both norepinephrine and serotonin in brain. Biochem. Pharmacol. 6, 52–53 (1961).

    Article  PubMed  CAS  Google Scholar 

  • Mohler, D. N.: Evaluation of the urine test for serotonin metabolites. J. Amer. med. Ass. 163, 1138 (1957).

    Article  CAS  Google Scholar 

  • Morris, C. J. O. R., and P. Morris: Separation Methods in Biochemistry. London 1963.

    Google Scholar 

  • Müller, R.: Zur quantitativen Bestimmung von Indolylessigsäure mittels Papierchromatographie und Papierelektrophorese. Beitr. Biol. Pflanzen 30, 1–32 (1953).

    Google Scholar 

  • Nöller, H. G.,u. P. Stelgens: Die hochspannungselektrophoretische Abtrennung des Sero-tonins von den übrigen xanthydrolpositiven Substanzen. Clin. chim. Acta 2, 304–306 (1957).

    Article  PubMed  Google Scholar 

  • Oates, J. A.: Measurement of urinary tryptamine, tyramine, and serotonin. In: J. H. Quastel (ed.), Methods in medical research, vol. 9, p. 169–174. Chicago 1961.

    Google Scholar 

  • Pitkänen, E., M. M. Airaksinen, O. O. Mustala, and J. Paloheimo: Observations on the specificity of the urinary 5-hydroxyindoleacetic acid determination with l-nitroso-2-naphtol. Scand. J. clin. Lab. Invest. 14, 571–577 (1962).

    Article  PubMed  Google Scholar 

  • Prochazka, Z., 1953: Cited after Prochazka (1958).

    Google Scholar 

  • Prochazka, Z., Indolderivate. In: I. M. Hais u. K. Macek (eds.), Handbuch der Papierchromatographie, vol. 1, p. 585–592. Jena 1958.

    Google Scholar 

  • Quay, W. B.: Differential extractions for the spectrophotofluorometric measurement of diverse 5-hydroxy-and 5-methoxyindoles. Analyt. Biochem. 5, 51–59 (1963).

    Article  PubMed  CAS  Google Scholar 

  • Randerath, K.: Dünnschicht-Chromatographie. Weinheim 1962.

    Google Scholar 

  • Rapport, M. M., A. A. Green, and I. H. Page: Serum vasoconstrictor (serotonin). IV. Isolation and characterization. J. biol. Chem. 176, 1243–1251 (1948).

    PubMed  CAS  Google Scholar 

  • Ribeiro, L. P., E. Mitidieri, and O. R. Affonso: Paper Electrophoresis. Amsterdam 1961.

    Google Scholar 

  • Robertson, J. I. S., and T.M. Andrews: Free serotonin in human plasma. Qualitative and quantitative estimation. Lancet 1961 I, 578–580.

    Article  Google Scholar 

  • Rodnight, R.: Separation and characterization of urinary indoles resembling 5-hydroxy-tryptamine and tryptamine. Biochem. J. 64, 621–626 (1956).

    PubMed  CAS  Google Scholar 

  • Ross, G., I. B. Weinstein, and B. Kabakow: The influence of phenothiazine and some of its derivatives on the determination of 5-hydroxyindoleacetic acid in urine. Clin. Chem. 4, 65–76 (1958).

    Google Scholar 

  • Sandler, M.: The determination of hydroxyindoles in biological materials. In: H. Varley and A. H. Gowenlock (eds.), The clinical chemistry of monoamines, p. 116–130. Amsterdam 1963.

    Google Scholar 

  • Sandler, M., P. J. Scheuer, and P. J. Watt: 5-Hydroxytryptophan-secreting bronchial carcinoid tumour. Lancet 1961 II, 1067–1069.

    Article  Google Scholar 

  • Sandler, M., and P. J. D. Snow: An atypical carcinoid tumour secreting 5-hydroxv-trvptophan. Lancet 1958 I, 137–139.

    Article  Google Scholar 

  • Schanberg, S. M.: A study of the transport of 5-hydroxytryptophan and 5-hydroxytryptamin (serotonin) into brain. J. Pharmacol, exp. Ther. 139, 191–200 (1963).

    CAS  Google Scholar 

  • Schlossberger, H. G., u. H. Kuch: Synthese von 5,6-Dihydroxytryptophan und verwandten Verbindungen. Justus Liebigs Ann. Chem. 662, 132–138 (1963).

    Article  CAS  Google Scholar 

  • Schlossberger, H. G., u. I. Buhrow: Abtrennung von Indol-Derivaten aus Urin mittels Sephadex G 25. Hoppe-Seylers Z. physiol. Chem. 333, 152–153 (1963).

    Article  PubMed  CAS  Google Scholar 

  • Schön, H., W. Ordnung u. E. Schmid: Zum Nachweis der 5-Hydroxyindolessigsäure im Harn. Klin. Wschr. 38, 405–406 (1960).

    Article  Google Scholar 

  • Schreier, K., u. K. Gaedtke: Über die papierchromatographische Bestimmung von Serotonin und anderen Indolkörpern. Naturwissenschaften 43, 130 (1956).

    Article  CAS  Google Scholar 

  • Schweigert, B. S., H. E. Sauberlich, C. A. Elvehjem, and C. A. Baumann: Free tryptophan in blood and urine. J. biol. Chem. 164, 213–221 (1946).

    PubMed  CAS  Google Scholar 

  • Scott, T. A.: An enzymic method for the estimation of L-tryptophan. Biochem. J. 80, 462–464 (1961).

    PubMed  CAS  Google Scholar 

  • Shepherd, D.M., G.B. West, and V. Erspamer: Detection of 5-hydroxytryptamine by paper chromatography. Nature (Lond.) 172, 357 (1953).

    Article  CAS  Google Scholar 

  • Shore, P. A., and J. S. Olin: Identification and chemical assay of norepinephrine in brain and other tissues. J. Pharmacol. exp. Ther. 122, 295–300 (1958).

    PubMed  CAS  Google Scholar 

  • Sjoerdsma, A.: Clinical and laboratory features of malignant carcinoid. Arch. intern. Med. 102, 938–940 (1958).

    Article  Google Scholar 

  • Sjoerdsma, A., J. A. Oates, P. Zaltzman, and S. Udenfriend: Identification and assay of urinary tryptamine; application as an index of monoamine oxidase inhibition in man. J. Pharmacol. exp. Ther. 126, 217–222 (1959).

    PubMed  CAS  Google Scholar 

  • Sjoerdsma, A., J. A. Oates, P. Zaltzman, and S. Udenfriend: Serotonin synthesis in carcinoid patients. Its inhibition by α-methyl-DOPA, with measurement of associated increases in urinary 5-hydroxytryptophan. New Engl. J. Med. 263, 585–588 (1960).

    Article  PubMed  CAS  Google Scholar 

  • Sjoerdsma, A., L.L. Terry, and S. Udenfriend: Malignant carcrnoid, a new metabolic disorder. Arch. intern. med. 99, 1009–1012 (1957).

    Article  CAS  Google Scholar 

  • Sjoerdsma, A., H. Weissbach, and S. Udenfriend: Simple test for diagnosis of α-metastatic carcinoid (argentaffinoma). J. Amer. med. Ass. 159. 397 (1955).

    Article  Google Scholar 

  • Smith, I. (ed.): Chromatographie and electrophoretic techniques. London 1960.

    Google Scholar 

  • Sprince, H., G.R. Rowley, and D. Jameson: Spectrofluorometric studies of 5-hydroxy-indoles and related compounds. Science 125, 442–443 (1957).

    Article  PubMed  CAS  Google Scholar 

  • Stahl, E. (ed.): Dünnschicht-Chromatographie. Berlin-Göttingen-Heidelberg: Springer 1962.

    Google Scholar 

  • Stahl, E., u. H. Kaldewey: Spurenanalyse physiologisch aktiver einfacher Indolderivate. Hoppe-Seylers Z. physiol. Chem. 323, 182–191 (1961).

    Article  Google Scholar 

  • Strell, M., u. A. Kalojanoff: Polymethinfarbstoffe. V. Mitt. Eine Erweiterung der Ehrlichschen Reaktion. Chem. Ber. 87, 1025–1032 (1954).

    Article  CAS  Google Scholar 

  • Sturm, A.: Die Bestimmung des Serotonins in Serum mit Hilfe der Hochspannungselektrophorese. Klin. Wschr. 39, 365–367 (1961).

    Article  CAS  Google Scholar 

  • Sturm, A.: Die Bestimmung der 5-Hydroxyindolessigsäure mit Hilfe der Hochspannungselektrophorese. Clin. chim. Acta 7, 714–721 (1962).

    Article  PubMed  CAS  Google Scholar 

  • Sweeley, C. C., and C.M. Williams: Microanalytical determination of urinary aromatic acids by gas chromatography. Analyt. Biochem. 2, 83–86 (1961).

    Article  PubMed  CAS  Google Scholar 

  • Titus, E. O.: Countercurrent distribution. In: C.D. Stewart, and A. Stolman (eds.), Toxicology, vol. 1, p. 392–422. New York 1960.

    Google Scholar 

  • Titus, E. O., and S. Udenfriend: Metabolism of 5-hydroxytryptamine (serotonin). Fed. Proc. 13, 411 (1954).

    Google Scholar 

  • Truter, E.V.: Thin film chromatography. London 1963.

    Google Scholar 

  • Udenfriend, S.: Fluorescence assay in biology and medicine. New York 1962.

    Google Scholar 

  • Udenfriend, S., D. F. Bogdanski, and H. Weissbach: Fluorescence characteristics of 5-hydroxytryptamine (serotonin). Science 122, 972–973 (1955a).

    Article  PubMed  CAS  Google Scholar 

  • Udenfriend, S., D. E. Duggan, B. M. Vasta, and B.B. Brodie: A spectrophotofluorometric study of organic compounds of pharmacological interest. J. Pharmacol. exp. Ther. 120, 26–32 (1957b).

    PubMed  CAS  Google Scholar 

  • Udenfriend, S., W. Lovenberg, and A. Sjoerdsma: Physiologically active amines in common fruits and vegetables. Arch. Biochem. 85, 487–490 (1959).

    Article  PubMed  CAS  Google Scholar 

  • Udenfriend, S., and R. E. Peterson: Assay of aromatic amino acids. III. Tryptophan. In: S. P. Colowick and N. O. Kaplan (eds.), Methods in enzymology, vol. 3, p. 613–614. New York 1957.

    Google Scholar 

  • Udenfriend, S., E. Titus, and H. Weissbach: The identification of 5-hydroxy-3-indoleacetic acid in normal urine and a method for its assay. J. biol. Chem. 216, 499–505 (1955c).

    PubMed  CAS  Google Scholar 

  • Udenfriend, S., and H. Weissbach: 5-Hydroxytryptophan and derivatives. In: S. P. Colowigk, and N. O. Kaplan (eds.), Method in enzymology, vol. 6, p. 598–605. New York 1963.

    Google Scholar 

  • Udenfriend, S., H. Weissbach, D. F. Bogdanski: Increase in tissue serotonin following administration of its precursor 5-hydroxytryptophan. J. biol. Chem. 224, 803–810 (1957a).

    PubMed  CAS  Google Scholar 

  • Udenfriend, S., H. Weissbach, B. B. Brodie: Assay of serotonin and related metabolites, enzymes, and drugs. In: D. Glick (ed.), Methods of Biochemical Analysis, vol. 6, p. 95–130. New York 1958.

    Google Scholar 

  • Udenfriend, S., H. Weissbach, and C. T. Clark: The estimation of 5-hydroxytryptamine (serotonin) in biological tissues. J. biol. Chem. 215, 337–344 (1955b).

    PubMed  CAS  Google Scholar 

  • Waalkes, T. P.: The determination of serotonin (5-hydroxytryptamine) in human blood. J. Lab. clin. Med. 53, 824–829 (1959).

    PubMed  CAS  Google Scholar 

  • Waalkes, T. P., A. Sjoerdsma, C. R. Creveling, H. Weissbach, and S. Udenfriend: Serotonin, norepinephrine and related compounds in banana. Science 127, 648–650 (1958).

    Article  PubMed  CAS  Google Scholar 

  • Weissbach, H., W. King, A. Sjoerdsma, and S. Udenfriend: Formation of indole-3-acetic acid and tryptamine in animals. A method for estimation of indole-3-acetic acid in tissues. J. biol. Chem. 234, 81–86 (1959).

    PubMed  CAS  Google Scholar 

  • Weissbach, H., T. P. Waalkes, and S. Udenfriend: A simplified method for measuring serotonin in tissues; simultaneous assay of serotonin and histamine. J. biol. Chem. 230, 865–871 (1958).

    PubMed  CAS  Google Scholar 

  • West, G. B.: Tryptamines in edible fruits. J. Pharm. Pharmacol. 10, 589 (1958).

    Article  CAS  Google Scholar 

  • West, G. B.: Carcinoid tumours and pineapples. J. Pharm. Pharmacol. 12, 768 (1960).

    Article  PubMed  CAS  Google Scholar 

  • Wiegand, R. G., and E. Scherfling: Determination of 5-hydroxytryptophan and serotonin. J. Neurochem. 9, 113–118 (1962).

    Article  PubMed  CAS  Google Scholar 

  • Wollish, E. G., M. Schmall, and M. Hamrylyshyn: Thin-layer chromatography. Recent development in equipment and applications. Analyt. Chem. 33, 1138–1142 (1961).

    Article  CAS  Google Scholar 

  • Zylka, W., u. T. Köhler: Anwendung verschiedener Methoden zum quantitativen Nachweis von 5-Hydroxytryptamin und 5-Hydroxyindolessigsäure bei einem Fall von metasta-sierendem Dünndarmcarcinoid. Klin. Wschr. 35, 622–626 (1957).

    Article  PubMed  CAS  Google Scholar 

Download references

Authors

Editor information

Vittorio Erspamer

Rights and permissions

Reprints and permissions

Copyright information

© 1966 Springer-Verlag, Berlin · Heidelberg

About this chapter

Cite this chapter

Hanson, A. (1966). Chemical analysis of indolealkylamines and related compounds. In: Erspamer, V. (eds) 5-Hydroxytryptamine and Related Indolealkylamines. Handbook of Experimental Pharmacology/Handbuch der experimentellen Pharmakologie, vol 19. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-85467-5_2

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-85467-5_2

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-85469-9

  • Online ISBN: 978-3-642-85467-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics