Histamine and Anti-Histaminics: Part 1: Histamine. Its Chemistry, Metabolism and Physiological and Pharmacological Actions

1026 Pages·1966·31.1 MB·English

by  Reuben G. Jones (auth.)

Handbuch der
experimentellen Pharmakologie
Handbook of
Experimental Pharmacology
Heffter-Heubner New Series
Herausgegeben von/Edited by
O. Eichler A. Farah
Heidelberg Syracuse, N. Y.
Beirat / Advisory Board
G. Acheson' E. J. Ariens . Z. M. Bacq . F. von Brucke . V. Erspamer
U. S. von Euler· W. Feldberg· R. Furchgott . A. Goldstein' G. B. Koelle
O. Krayer . K. Repke . M. Rocha e Silva' P. Waser . W. Wilbrandt
Vol. XVIII/1
Springer-Verlag Berlin Heidelberg GmbH 1966
Histamine and Anti-Histaminics
Part 1
Histamine. Its Chemistry,
Metabolism and Physiological and
Pharmacological Actions
Contributors
S. G. A. Alivisatos . W. H. Bachrach· W. T. Beraldo . H. H. Dale
W. Dias da Silva· N. Emmelin . U. S. von Euler. H. Giertz
F. Hahn. R. D. Higginbotham. A. C. Ivy. R. G. Jones
C. Laborde-Burtin . S. E. Lindell. L. A. J. Lison . F. C. McIntire
E. Mendes . M. Mordelet-Dambrine . 1. Mota· H. Moussatche
P. Naranjo· G. Nicot . J. L. Parrot· H. W. Raudonat . J. F. Riley
M. Rocha e Silva· A. M. Rothschild· A. Saindelle . R. W. Schayer
U. Serafini· P. Stern· H. Tabor· J. Thouvenot . B. Vasseur
1. Vugman . G. B. West· H. Westling· T. White
Sub-Editor
Mauricio Rocha e Silva
In Collaboration with Hanna A. Rothschild
With 175 Figures
Springer-Verlag Berlin Heidelberg GmbH 1966
ISBN 978-3-662-12018-7 ISBN 978-3-662-12016-3 (eBook)
DOI 10.1007/978-3-662-12016-3
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ten permission from Springer-Verlag Berlin Heidelberg GmbH.
© by Springer-Verlag Berlin Heidelberg 1966
Originally published by Springer-Verlag· Berlin -Heidelberg· New York in 1966
Softcover reprint of the hardcover 1st edition 1966
Library of Congress Catalog Card Number AGR 25-699
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may accordingly be freely used by anyone.
Title No. 5723
Preface
It was an agreable, though strenuous task to edit a book with so many distin
guished contributors, on a subject to which I have given half of my life. In 1959,
when Prof. O. EICHLER invited me to edit a book on "Histamine and Anti
histaminics", as a supplement to HEFFTER'S Handbuch, I thought the task could be
done in three years. Now, five years are gone and only half is fulfilled. Though,
so far as the "Histamine" part of the book is concerned, the initial plan has been
followed very closely, we had to leave the Anti-histaminics for another volume of
unpredictable dimensions. In 1924, eight pages inserted in a Chapter on M utterkorn,
by ARTHUR R. CUSHING were considered enough, in vol. II, Part II, pg. 1319-1326,
of the Handbuch. Now, 922 pages did not suffice to cover all the aspects of the
subject. Especially in the last few years the subject has expanded in so many
directions, that the antihistaminic part had to be excluded from the present
volume. Possibly, another thousand pages will be necessary to cover what
remains of the subject.
In planning the book we made great use of the excellent and classical mono
graph by W. FELDBERG and E. SCHILF on Histamin, published by Julius Springer,
in 1930. With the invitation to edit the present volume, the recommendation was
made that "anything still valid in that book should appear in the volume to be
edited". This was the most agreable recommendation I could receive from the
Editors of the Handbuch, as it gave me a free hand to explore once more the
inexhaustible source of historical and fundamental knowledge about histamine
contained in FELDBERG and SCRILF'S monograph. If making a book of such propor
tions can be compared to the work of bnilding up a skyscraper, this historical and
fundamental knowledge resembles the concrete foundation of the new structure.
The new book was planned in such a way that each Chapter represents a
complete survey of a broad sector of the histamine problem.
Chapter I is entirely devoted to the chemistry, isolation and occurrence of
histamine. It is subdivided into six sections with a complete survey on the methods
of synthesis of histamine and analogs, the relationships between structure and
activity and the methods of isolation for biological and chemical estimation in
tissues and body fluids; the last two sections give an extensive view of the histo
chemical aspects of EHRLICH'S mast cells, as well as on the association of histamine
and heparin in cells and tissues.
Chapter II is entirely devoted to the pharmacology of histamine and is subdi
vided into eight sections dealing with absorption and toxicity of histamine, actions
upon smooth muscles and the cardio-vascular system, on salivary and gastric
secretion, and its relationships with the autonomous nervous system.
Chapter III treats in a most exhaustive way the problem of histamine release
by venoms and toxins, by physical and chemical agents, by basic compounds, in
anaphylaxis, and by macromolecular releasers, such as anaphylatoxin, dextran,
egg white, and so forth. The enzymatic mechanism of histamine release in its
relationships with respiration, carbohydrate metabolism and phosphorylation is
authoritatively discussed in connection with the practical problem of histamine
release in anaphylaxis and allergy.
VI Preface
Chapter IV is concerned with the metabolism of histamine and is again subdivid
ed into seven sections dealing with in vivo and in vitro formation and catabolism of
histamine in different species of animals and in man. A special section draws atten
tion to the relationship between histamine and the brain.
Chapter V is subdivided into five sections and is intended to give a survey of
the importance of histamine in normal physiology, with an extensive discussion
of its possible significance as a normal stimulant of gastric secretion. Small sections
are dedicated to the controversial participation of histamine in vascular reflexes,
in chronic inflammation. The last two sections deal with the role played by
histamine in human and experimental allergy.
In a book to which 38 collaborators contributed to different aspects of the
subject, some overlapping was inevitable, but desirable. The diversity of view
points on any growing subject of research can be of great advantage to anyone
working in the field, opening up new pathways to explore the unknown. Only
limitations of space should prevent an editor from giving free hand to authors to
expand their subjects as desired. Though this authority was exerted during the
editing of this book, it was to an astonishingly small extent that any limitation had
to be imposed to the contributors. Another factor to diversify the treatments given
to the different subjects, was the selection of the authors from different countries:
Brazil, Ecuador, France, Germany, Great Britain, Italy, Sweden, the United States
and Yugoslavia. This diversity of nationalities adds a new dimension to the dis
cussion of any scientific subject and, combined with the overlapping of individual
contributions tends to eliminate cultural fads or local customs that lead to a
stereotyped treatment of the subject. I believe that almost every aspect of the
histamine problem has been dealt with adequately.
The presentation of some personal views of the problem was even encouraged
by the invitation to authors to present short papers on their own work, to a certain
extent at the margin of the main lines of the subject. These small contributions
were introduced among the main papers as flowers to be gathered en pa8sant. This
procedure deviates somehow from the style ofthe great text-books and is more on
the line of a Symposium. In so doing, we intended to insufflate fresh air in the
dense atmosphere of a massive textbook.
It is a great pleasure to acknowledge the collaboration given by so many
distinguished contributors of this volume for their exact and excellent cooperation
in bringing the work to its final present form.
The task for editing this volume would be beyond my forces without the
collaboration of Dr. HANNA A. ROTHSCHILD, in every phase of the preparatory
work and especially in checking every single word and name appearing in this
volume. To Miss ODETE PIZARRO and MARIA LETICIA FERNANDES, we are indebted
to most of the typing of our own contributions and of the indexes at the end of the
volume.
This book is dedicated to all investigators whose work has contributed to the
advance of our knowledge of the histamine problem. Two of them, however,
deserve a special and honourable mention, namely Sir HENRY H. DALE, of London,
and Prof. DANKWART ACKERMANN, of Wiirzburg. By a fortunate coincidence this
is the year of Sir HENRY'S ninetieth anniversary, and we are happy to have his
Foreword to this book.
M. ROCHA E SILVA
Ribeirao Preto, Sao Paulo, February, 1965.
Contributors
S. G. A. ALIVISATOS, Professor Dr., Division of Enzymology and Experimental
Hypersensitivity, Institute of Medical Research, The Chicago Medical School,
2020 West Ogden Avenue, Chicago Ill., 60612/USA.
WILLIAM HARRIS BACHRACH, Dr., 8733 Beverly Blvd., Los Angeles 48. Calif./USA.
WILSON TEIXEIRA BERALDO, Professor Dr., Departamento de Fisiologia, Facul
dade de Medicina, Universidade de Minas Gerais, Belo Horizonte, Minas Gerais/
Brasil.
SIR HENRY HALLETT DALE, The Wellcome Trust, 52, Queen Anne Street, London,
W.l./England.
WILMAR DIAS DA SILVA, Dr., Departamento de Fisiologia, Faculdade de Medicina,
Universidade de Minas Gerais, Belo Horizonte, Minas Gerais/Brasil.
NILS EMMELIN, Professor Dr., Department of Physiology, University of Lund,
Lund/Sweden.
ULF S. VON EULER, Professor Dr., Department of Physiology, Karolinska Insti
tutet, Solnavagen 1, Stockholm 60/Sweden.
H. GIERTZ, Dozent Dr., Pharmakologisches Institut der Universitat, 78 Freiburg
i. Br./Deutschland, KatharinenstraBe 29.
FRITZ HAHN, Professor Dr., Pharmakologisches Institut der Universitat, 78 Frei
burg i. Br./Deutschland, KatharinenstraBe 29.
ROBERT D. HIGGINBOTHAM, Professor Dr., Department of Microbiology, The Uni
versity of Texas-Medical Branch, Galveston, Texas/USA.
ANDREW CONWAY Ivy, Professor Dr., Roosevelt University, 430 So. Michigan
Avenue, Chicago 60605, Ill./USA.
REUBEN G. JONES, Dr., Organic Chemical Division, The Lilly Research Labora
tories, Eli Lilly and Co., Indianapolis 6, Ind./USA.
CLAUDE LABORDE-BuRTIN, Dr. (Madame), Laboratoire de Physiologie patholo
gique de l'Ecole pratique des Hautes Etudes, Hopital Boucicaut, 78, Rue de
la Convention, Paris XVe/France.
SVEN ERIC LINDELL, Dr., Almanna Sjukhuset, Department of Clinical Physiology,
Malmo/Sweden.
LUCIEN A. J. LISON, Professor Dr., Departamento de Morfologia, Faculdade de
Medicina, Universidade de Sao Paulo, Ribeirao Preto, Sao Paulo/Brasil.
FLOYD C. McINTIRE, Dr., Head Biochemical Research, Abbott Laboratories,
Scientific Divisions, North Chicago, Ill./USA.
ERNESTO MENDES, Dr., Departamento de Microbiologia e Immunologia, Faculdade
de Medicina, Avenida Dr. Arnaldo, Sao Paulo/Brasil.
VIII Contributors
MADELEINE MORDELET-DAMBRINE, Dr., Laboratoire de Physiologie pathologique
de l'Ecole pratique des Hautes Etudes, Hopital Boucicaut, 78, Rue de la
Convention, Paris XVe/France.
IVAN MOTA, Dr., Laborat6rio de Fisiologia Celular, Departamento de Histologia,
Faculdade de Medicina, Avenida Dr. Arnaldo, Sao Paulo/Brasil.
HAITY MOUSSATCHE, Professor Dr., Divisao de Fisiologia e Farmacologia, Insti
tuto Oswaldo Cruz, Rio de Janeiro, Estado da Guanabara/Brasil.
PLUTARCO NARANJO, Professor Dr., Laboratorios "Life", Quito/Ecuador.
GEORGES NICOT, Dr., Ecole de Medecine de Limoges, Limoges (Haute-Viennel/
France.
JEAN-LoUIS PARROT, Professor Dr., Laboratoire de Physiologie pathologique de
l'Ecole pratique des Hautes Etudes, Hopital Boucicaut, 78, Rue de la Con
vention, Paris XVe/France.
HEINZ-WALTER RAUDONAT, Dr. Wissenschaftlicher Rat, Institut fur gerichtliche
und soziale Medizin der Universitat, 6 Frankfurt a/Main/Deutschland,Kennedy
Allee 104.
JAMES F. RILEY, Professor Dr., Department of Radiotherapy, Royal Infirmary,
Dundee/Scotland.
MAURICIO ROCHA E SILVA, Professor Dr., Departamento de Farmacologia, Facul
dade de Medicina, Universidade de Sao Paulo, Ribeirao Preto, Sao Paulo/
Brasil.
ADOLFO MAX ROTHSCHILD, Dr., Departamento de Farmacologia, Faculdade de
Medicina, Universidade de Sao Paulo, Ribeirao Preto, Sao Paulo/Brasil.
ANATOLE SAINDELLE, Dr., Laboratoire de Physiologie pathologique de l'Ecole
pratique des Hautes Etudes, Hopital Boucicaut, 78, Rue de la Convention,
Paris XVe/France.
RICHARD W. SCHAYER, Dr., The Merck Institute for Therapeutic Research, Rahway,
New Jersey/USA. Present address: Laboratory of Chemical Pharmacology,
National Heart Institute, Bethesda, Maryland 20014/USA.
UMBERTO SERAFINI, Professor Dr., Istituto di Patologia Speciale Medica e Metodo
logia Clinica, Universita di Sassari, Viale San Pietro 8, Sassari/Italia.
PAUL STERN, Professor Dr., Institute of Pharmacology, Faculty of Medicine,
Saraj evo /Y ugosla via.
HERBERT TABOR, Dr., Department of Health Education and Welfare, Public
Health Service, National Instional Institutes of Health, Bethesda, Md. 20014/
USA.
JOSEPH THOUVENOT, Professor Dr., Faculte de Medecine et de Pharmacie, Chaire
de Physiologie, Tours/France.
BERNARD VASSEUR, Dr., Departement de Physiologie, FaculM de Medecine, 45,
Rue des Saint-Peres, Paris VIe/France.
ITAMAR VUGMAN, Dr., Departamento de Farmacologia, Faculdade de Medicina,
Universidade de Sao Paulo, Ribeirao Preto, Sao Paulo/Brasil.
GEOFFREY B. WEST, Professor Dr., Department of Pharmacology, School of
Pharmacy, University of London, 29/39 Brunswick Square, London W. C. 1/
England.
HAKAN WESTLING, Dr., Department of Clinical Physiology, Lasarettet, Lund/
Sweden.
THOMAS WHITE, Dr., Institute of Physiology, University of Lund, Lund/Sweden.
Contents
Foreword by Sir HENRY H. DALE. . XXVI
Chapter 1: Chemistry, isolation and occurrence 01 histamine
Section A: Chemistry of histamine and analogs. Relationship between structure and pharma.
cological activity
By REUBEN G. JONES
1. Introduction . . 1
A. Historical background. 1
B. Nomenclature .... 1
II. Synthesis of histamine . . 2
A. Synthesis from histidine. . 2
B. From imidazolepropionic acid 3
C. From oc-aminoketones. . . . 3
D. From oc-aminoaldehydes . . . 5
E. From oc-hydroxyketones . . . 5
III. Labeled histidine and histamine . 6
A. Histidine . . . . . . . . . 6
B. Histamine. . . . . . . . . 8
IV. Physical and chemical properties of histamine. 9
A. Physical properties . 9
B. Metal complexes . . 9
C. Chemical properties . 11
V. Analogs of histamine 14
VI. Chemical constitution and pharmacological activity 34
Literature . . . . . . . . . . . . . . . . . . . . 39
Section B: Die Isolierung von Histamin aus biologischem Material
Von HEINZ WALTER RAUDONAT
A. Einleitung. . . . . . . . . . . 44
B. Allgemeine Aufarbeitungsverfahren 44
l. Extraktion . . . . . . . . . 44
2. Elektrodialyse . . . . . . . . 46
3. Papierelektrophorese . . . . . 48
4. Papierchromatographie . . . . . . 48
5. Neuere FiUlungsmittel fiir Histamin. 49
C. Spezielle Aufarbeitungsverfahren . . . 49
l. Isolierung von Histamin aus Pflanzen und Bakterien 49
a) Histamin aus Bakterien . . . . . . . . . . . 49
b) Histamin aus gefaulten Sojabohnen (Glycine hispida) 49
c) Isolierung von Histamin aus Faeces-Bakterien . . . 50
d) Verfahren zut Isolierung von Histamin aus Pflanzen. 50
e) Darstellung von Histamin aus der Lederkoralle (Aleyonium digeitatum) 51
2. Isolierung aus K6rperfiiissigkeiten und aus tierischen Geweben. . . . . . 51
a) Verfahren zur Abtrennung des Histamins aus Blut . . . . . . . . . 51
b) Verfahren zur Abtrennung des Histamins aus menschlichem Urin nach DUNER
und PERNOW. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 51
c) Extraktion von freiem und konjugiertem Histamin aus Urin nach ROBERTS und
ADAM ................................ 52
d) Verfahren zur Gewinnung von Histamin aus Hypophysen nach ABEL und Ku
BOTA sowie nach DUDLEY . . . . . . . . . . . . . . . . . . . . . . . 52
x Contents
e) Verfahren zur Abtrennung des Histamins aus DiinndarmscWeimhaut nach
BARGER und DALE . . . . . . . . . . . . . . . . . . . . . . . . . . 53
f) Verfahren zur Isolierung von Histamin aus Rinderleber nach BEST, DALE,
DUDLEY und THORPE . . . . . . . . . . . . . 54
g) Isolierung von Histamin aus Muskel nach THORPE. 55
Literatur 55
Section C: Determination of histamine by chemical means
By F. C. McINTIRE
I. Introduction . . . . . . . . 57
II. Principles of chemical methods 57
A. Diazo methods. . . . . . . . 57
B. 2,4-Dinitrofluorobenzene (DNFB) methods. 60
C. The fluorometric method. . 61
D. The radioisotope method. . . 63
E. Miscellaneous methods. . . . 63
III. Inhibitors of histamine reactions 64
IV. Purification of histamine for chemical assay 64
A. Acid hydrolysis. . . 64
B. Protein precipitants 65
C. Alcohol extraction 65
D. Ion exchangers. . . 65
E. Permutit (Decalso) . 66
F. Paper chromatography 67
G. Electroseparations . . 68
V. Procedures ...... . 68
A. The fluorometric determination of histamine 68
B. Modifications of the Shore method . . 69
C. DNFB procedures . . . . . . . . . . 72
D. The Rosenthal and Tabor diazo method . 77
E. Paper chromatography 78
Literature . . . . . . . . . . . . . . . . . 78
Section D: Biological determination of bistamine in living tissues and body fluids
By I. VUGMAN and M. ROCHA E SILVA
I. Methods of extraction suitable for the bio-assay. . 81
A. Earlier methods of extraction . . . . . . . . 83
B. Methods for extraction of histamine from blood 83
C. Methods of histamine extraction from tissues 85
II. Biological assay of histamine 86
A. Blood pressure assay .. 86
B. Guinea pig ileum . . . . 86
C. Superfusion techniques . 91
D. Bronchiolar constriction . 93
III. A four-point assay for histamine estimation. 93
IV. Histamine content of organs and body fluids 97
References . . . . . . . . . . . . . . . . . IIO
Section E: The occurrence of histamine in mast cells
By J. F. RILEY and G. B. WEST
I. Introduction. . . . . II6
II. Discovery of mast cells II6
III. Heparin in mast cells . II7
A. Normal tissues II7
B. Pathological tissues II8
C. Location of heparin. II9
D. Synthesis of heparin II9