The Alkaloids Pharmacology

399 Pages·1955·20.92 MB·English

by  Manske

THE ALKALOIDS
Chemistry and Physiology
VOLUME V
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THE ALKALOIDS
Chemistry and Physiology
Iddited by
R. H. F. MANSKE
Dominion Rubber Research Laborator!/
Guelph, Ontario
VOLUME V
PHARMACOLOGY
1955
ACADEMIC PRESS INC., PUBLISHERS
NEW YORIC
Copyright, 1955, by
ACADEMIC PRESS INC.
125 EAST2 3 ST~RE~ET
NEWY ORK1 0, N. Y.
All Rights Reserved
NO PART OF THIS BOOK MAY BE REPRODUCED IN ANY FORM, BY PHOTOSTAT, MICROFILM,
OR ANY OTHER MEANS, WITHOUT WRITTEN PERMISSION FROM THE PUBLISHERS.
Library of Congress Catalog Card Number: (50-5522)
Printed in the United States of America
PREFACE
The present volume is the last in a series of five dealing with the chemistry
arid pharmacology of the alkaloids, thereby climaxing the ambitious scheme
outlined in the preface to the first volume. In the pharmacological chap-
ters, of which there are nine, a t,reatment based rather on action than one
based on chemical structure has been adopted. The result is that chemical
affinities and botanical relationships have been ignored when many
different alkaloids having similar pharmacological actions have been
brought together in one chapter. Consequently many of the alkaloids are
discussed in a number of chapters because of the multiplicity of responses
which they elicit.
Also included is a chapter dealing with the chemistry of the Lycopodium
alkaloids and one treating a group of miscellaneous alkaloids. Many of
the latter are as yet not relegated to a particular type, although on some
of them considerable work has been done in the interval following the pub-
lication of the first volume, while in several the structures have been en-
tirely or almost entirely elucidated.
It is hoped that chemists and pharmacologists will continue to send sug-
gestions and reprints so that a future supplement will be as thorough and
satisfactory as possible.
The Editor is most grateful to the contributors who have labored so
conscientiously and to chemists throughout t,he world who have so gen-
erously received the past volumes.
September, i955 R. H. F. M.
V
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CONTENTS
Preface . . . . . . . . . . . . . . . . . . . . . v
Narcotics and Analgesics
By HUGOK RUEGERO. regon State College. Corvallis. Oregon
I . Introduction . . . . . . . . . . . . . . . . . . . . 2
I1 . General Pharmacology of Morphine . . . . . . . . . . . . 3
I11 . Analgesia . . . . . . . . . . . . . . . . . . . . . 10
IV. Addiction and Withdrawal Phenomena . . . . . . . . . . . 2 5
V . Morphine Derivatives and Related Analgesics . . . . . . . . . 3 7
VI . Fate of Morphine . . . . . . . . . . . . . . . . . . 6 1
VII. References . . . . . . . . . . . . . . . . . . . . 74
Cardioactive Alkaloids
By E . L . MCCAWLEYD. epartment of Pharmacology. University of Oregon Medical
School. Portland. Oregon
I . Introduction . . . . . . . . . . . . . . . . . . . . 79
I1 . Cinchona Alkaloids . . . . . . . . . . . . . . . . . . 8 4
I11 . Cryptopine-like Compounds . . . . . . . . . . . . . . . 8 8
IV . Sparteine and Related Substances . . . . . . . . . . . . . 9 3
V . RauwolJia Alkaloids . . . . . . . . . . . . . . . . . . 9 7
VI . Toad Poisons (Bufotoxins) . . . . . . . . . . . . . . . 9 8
VII. Erythrophleum Alkaloids . . . . . . . . . . . . . . . . 10 1
VIII . References . . . . . . . . . . . . . . . . . . . . 104
Respiratory Stimulants
By MARCELJ . DALLEMAGNInEst.i tute of Experimental Therapeutics. University of
Liege. Belgium. and C . HEYMANJS .. F . Heymans Institute of Pharmacology and
Therapeutics. University of Ghent. Belgium
I . Introduction . . . . . . . . . . . . . . . . . . . . 109
I1 . Choline Group . . . . . . . . . . . . . . . . . . . 1 10
I11 . Veratrine Group . . . . . . . . . . . . . . . . . . . 11 1
IV . Nicotine Group . . . . . . . . . . . . . . . . . . .113
V . Tropane Group . . . . . . . . . . . . . . . . . . . 12 6
VI . Sympathomimetic Group . . . . . . . . . . . . . . . . 1 28
VII . Purine bases . . . . . . . . . . . . . . . . . . . . 132
VIII . References . . . . . . . . . . . . . . . . . . . . . 134
Antimalarials
By I. . I€. Sc11~1ru.Tr.h e Christ Hospital. Institute of Medical Ilesearch.
Oineinnati. Ohio
1 . Introduction . . . . . . . . . . . . . . . . . . . . 141
I1 . Cinchona Alkaloids . . . . . . . . . . . . . . . . . . 1 42
I11 . Other Alkaloids . . . . . . . . . . . . . . . . . 15 6
IV . Appraisal of the Utility of Alkaloids ns Antimalarials . . . . . . 15 7
V . References . . . . . . . . . . . . . . . . . . . . . 158
vii
viii CONTENTS
Uterine Stimulants
By A . K . REYNOLDSD.e partment of Pharmacology. Dalhousie University. Halifax?
Nova Scotia
I . Introduction . . . . . . . . . . . . . . . . . . . . 164
I1 . Ergot Alkaloids . . . . . . . . . . . . . . . . . . . 165
I11 . Cinchona Alkaloids . . . . . . . . . . . . . . . . . . 178
IV . Sparteine and Related Alkaloids . . . . . . . . . . . . . . 179
V . Muscarine, Arecoline, Pilocarpine. and Physostigmine . . . . . . 183
VI . Isoquinoline Alkaloids . . . . . . . . . . . . . . . . . 185
VII . Miscellaneous Alkaloids . . . . . . . . . . . . . . . . 190
VIII . Discussion . . . . . . . . . . . . . . . . . . . . . 200
IX . References . . . . . . . . . . . . . . . . . . . . . 202
Alkaloids as Local Anesthetics
By THOMAPS . CARNEYE. li Lilly and Company. Indianapolis. Indiana
I . History . . . . . . . . . . . . . . . . . . . . . . 211
I1 . Derivatives of Cocaine . . . . . . . . . . . . . . . . .212
.
I11 Metabolism of Cocaine . . . . . . . . . . . . . . . . .219
IV . Other Alkaloids . . . . . . . . . . . . . . . . . . .22 1
V . Factors Affecting Cocaine Anesthesia . . . . . . . . . . . .22 3
VI. Evolution of Anesthetic Structures . . . . . . . . . . . . .22 5
VII . References . . . . . . . . . . . . . . . . . . . . . 226
Pressor Alkaloids
. .
By Ii K CHEN,T he Lilly Research Laboratories. Eli Lilly and Company,
Indianapolis. Indiana
I . Introduction . . . . . . . . . . . . . . . . . . . . 229
I1 . Aromatic Amines . . . . . . . . . . . . . . . . . .23 0
I11 . Alkyl Amines . . . . . . . . . . . . . . . . . . . . 233
.
IV Indolealkyl Amines . . . . . . . . . . . . . . . . . .23 4
.
V Synthetic Products of Medicinal Interest . . . . . . . . . . .23 5
VI . Structure-Activity Relationship . . . . . . . . . . . . . .23 6
VII . Optical Isomerism-Activity Relationship . . . . . . . . . . .23 8
VIII. References . . . . . . . . . . . . . . . . . . . . . 239
Mydriatic Alkaloids
By H . R . INGD, epartment of Pharmacology, University of Oxford, Oxford, England
I . Innervation and Musculature of the Eye . . . . . . . . . . .243
I1. Methods of Measuring Mydriatic Activity . . . . . . . . . .24 4
.
I11 Parasympathetic Blocking Agents as Mydriatics . . . . . . . . 24 5
IV. Sympathomimetic Mydriatics . . . . . . . . . . . . . .25 7
V . References . . . . . . . . . . . . . . . . . . . . . 261
Curare-like Effects
By L . E . CRAIQ,B rand River Chemical Division, Deere & Co., Pryor, Oklahoma
I . Introduction . . . . . . . . . . . . . . . . . . . . 265
.
I1 Curariform Activity . . . . . . . . . . . . . . . . . 26 6
I11 . Alkaloids Exhibiting Curariform Activity . . . . . . . . . .26 9
CONTENTS ix
.
IV Synthetic Curarizing Agents . . . . . . . . . . . . . . .287
V . References . . . . . . . . . . . . . . . . . . . . . 290
The Lycopodium Alkaloids
By R . H . F . MANSHED, ominion Rubber Company Limited, Research Laboratories.
Guelph. Ontario
I . Occurrence . . . . . . . . . . . . . . . . . . . . 295
I1 . Structure . . . . . . . . . . . . . . . . . . . . . 295
I11 . Pharmacology . . . . . . . . . . . . . . . . . . . 29 9
IV. References . . . . . . . . . . . . . . . . . . . . . 299
Minor Alkaloids of Unknown Structure
By R . H . F . MANSHED. ominion Rubber Company. Limited. Research Laboratories.
Guelph, Ontario
I . Introduction . . . . . . . . . . . . . . . . . . . . 301
I1 . Plants Containing Alkaloids of Unknown Structure . . . . . . . 30 2
I11. References . . . . . . . . . . . . . . . . . . . . . 328
Author Index-Volume V . . . . . . . . . . . . . . . .33 3
Subject Index-Volume V . . . . . . . . . . . . . . . . 35 2
Subject Index-Volumes I-IV . . . . . . . . . . . . . .36 0