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Ergot Alkaloids and Related Compounds

B. Berde, H.O. Schild (Herausgeber)

Buch | Hardcover
1024 Seiten
1978
Springer-Verlag Berlin and Heidelberg GmbH & Co. K
978-3-540-08475-4 (ISBN)
CHF 119,75 inkl. MwSt
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With contribution by numerous experts
Une decouverte scientifique ...n'est ja- mais l'reuvre d'un seul homme et chacun de ceux qui y ont concouru lui ont donne bien des veilles. Louis Pasteur Traditionally every volume of the Handbook of Experimental Pharmacology is expected to give a comprehensive account of the topic it is devoted to. This is a relatively easy task if the subject has a short history, but if the problems in question have been worked on for half a century or longer the feasibility of integral coverage becomes questionable. In such cases more attention is usually given to the literature of the last decades, whereas older findings are dealt with in a summary fashion - with due exception to findings which can be considered classic. The situation is particularly complex if the origin of the subject is a natural drug whose actions - proven or alleged - were first recorded several centuries ago and where medical use can be traced back at least one and a half centuries (STEARNS, 1808) - as is the case of ergot of rye.
As editors of the present volume of this Handbook, we did not have to face the full impact of these difficulties as two previous volumes have already been devoted to the pharmacologic actions of substances extracted from ergot of rye. The first of these, written by Arthur Cushny in 1914, was published in 1924 [A. R. CUSHNY: Mutterkorn. Handb. exper. Pharmakol. II, 2, 1297-1354 (1924)].

I Introduction to the Pharmacology of Ergot Alkaloids and Related Compounds as a Basis of Their Therapeutic Application.- II Chemical Background.- A. Occurrence, Biosynthesis, and Production.- 1. Presence of Ergot Alkaloids in the Plant Kingdom.- 2. Biogenesis.- 3. Production.- B. Structure and Synthesis of the Natural Alkaloids.- 1. General Structural Aspects.- 2. Structure of Ergot Alkaloids.- 3. Synthesis of Ergot Alkaloids.- C. Chemical Modifications in the Lysergic Acid Half of Ergot Alkaloids.- 1. Substitutions in Position 1.- 2. Substitutions in Position 2.- 3. Chemical Transformations in Positions 4 and 5.- 4. Replacement of the N-Methyl Group in Position 6 by Other Substituents.- 5. Reactions Involving Position 7.- 6. Modifications of the Carboxylic Acid Function of d-Lysergic Acid.- 7. Reactions at Position 8.- 8. Derivatives of 6-Methyl-8-ergolene-8-carboxylic Acid.- 9. Chemical Transformations on the Double Bond in Position 9, 10.- 10. Substitution Reactions in the Benzene Ring.- D. Chemical Modification in the Peptide Part of Ergot Alkaloids.- 1. The Aci-Rearrangement.- 2. Synthesis of Analoga of Natural Ergot Peptide Alkaloids.- 3. Substitution of l-Proline by Other Amino Acids in Ergot Peptide Alkaloids.- 4. Synthetic Ergot Peptide Alkaloids Modified in Position 5?.- E. Some Analytical Tools for the Determination of Ergot Alkaloids.- 1. Separation of Ergot Alkaloids.- 2. Assay of Ergot Alkaloids.- F. Subject Index.- G. References.- III Basic Pharmacological Properties.- A. Introduction.- Competitive Drug Antagonism.- Corollaries of Competitive Antagonism.- Affinity and Intrinsic Activity (Efficacy).- Receptor Classification.- Noncompetitive Antagonism.- B. Actions of Ergot Alkaloids at 5-HT Receptors.- 1. Actions of Ergot Alkaloids at Extraneuronal 5-HT Receptors.- 2. Effects of Ergot Alkaloids on 5-HT Metabolism.- 3. Effects of Ergot Alkaloids on Neuronal 5-HT Receptors.- 4. Effects of Ergot Alkaloids on 5-HT-Sensitive Enzyme Systems.- C. Actions of Ergot Alkaloids at Dopamine Receptors.- 1. Actions of Ergot Alkaloids at Extraneuronal Dopamine Receptors.- 2. Interaction of Ergot Alkaloids With Indirect Dopamine Effects.- 3. Actions of Ergot Alkaloids at Neuronal Dopamine Receptors.- 4. Effects of Ergot Alkaloids on Dopamine-Sensitive Enzyme Systems.- 5. Effects of Ergot Alkaloids on Dopamine Receptors Mediating Hormone Secretion.- D. Actions of Ergot Alkaloids at Adrenoceptors.- 1. Effects of Ergot Alkaloids Mediated by Peripheral ?-Adrenoceptors.- 2. Depletion of Noradrenaline From Tissues by Ergot Alkaloids.- 3. Effects of Ergot Alkaloids on Noradrenaline Release and Theories on the Mechanism of Noradrenaline "Overflow".- 4. Effects of Ergot Alkaloids on the Responses of Organs to Stimulation of Their Sympathetic Innervation.- 5. Actions of Ergot Alkaloids at ?-Adrenoceptors.- E. The Shape of Ergotamine and Dihydroergotamine in Relation to Their Interaction With ?-Adrenoceptors.- F. Actions of Ergot Alkaloids at Acetylcholine Receptors.- G. Actions of Ergot Alkaloids at Histamine Receptors.- H. Interaction of Ergot Alkaloids With Prostaglandins.- 1. Interference of Ergot Alkaloids With Endogenous Prostaglandin Synthesis.- 2. Interference of Ergot Alkaloids With Prostaglandin Effects.- J. Stimulation of Smooth Muscle by Ergot Alkaloids Mediated by Miscellaneous Mechanisms.- 1. Enhancement of Responses to Biogenic Amines by Ergot Alkaloids in Vascular Smooth Muscles.- 2. Enhancement of Responses to Biogenic Agents by Ergot Alkaloids in Nonvascular Smooth Muscles.- K. Biochemical Identification of Specific Binding Sites for Ergot Alkaloids.- 1. Interaction of Ergot Compounds With Specific Sites in the Central Nervous System.- 2. Peripheral Binding Sites for Ergot Compounds.- L. References.- IV Effects on the Uterus.- A. Introduction.- B. Actions on Uterine Motor Activity.- 1. Peptide Alkaloids.- 2. Dihydrogenated Peptide Alkaloids.- 3. Lysergic Acid-Amides.- C. References.- V Actions on the Heart and Circulation.- A. Actions on Systemic Blood Pressure.- 1. Nature of the Effect.- 2. Effects on Blood Pressure Control Mechanisms.- 3. Effects on the Carotid Sinus and Impulse Transmission in Sino-Aortic Nerves.- 4. Effects on Responses to Catecholamines and 5-Hydroxytryptamine.- 5. Mechanisms Involved in the Hypotensive Action.- 6. Mechanisms Involved in the Pressor Action.- B. Hemodynamic Effects.- C. Effects on Regional Hemodynamics.- 1. Effects on Limb Blood Vessels.- 2. Effects on Cranial Blood Vessels.- 3. Effects on Renal Blood Vessels.- 4. Effects on Mesenteric Blood Vessels.- 5. Effects on Coronary Blood Vessels.- 6. Effects on Uterine Blood Vessels.- D. Actions on the Heart.- 1. Effects in Mammals.- 2. Effects in Amphibia.- 3. Effects in Molluscs.- E. Pharmacologic Basis for the Clinical Use of Ergot Alkaloids.- 1. Orthostatic Hypotension.- 2. Venous Thrombosis.- 3. Shock.- 4. Migraine.- F. References.- VI Effects on the Central Nervous System.- A. Introduction.- B. Early Evidence of Central Effects.- 1. Convulsive Ergotism in Man.- 2. Early Description of Central Effects in Animals.- 3. The Question of "Toxic" versus "Therapeutic" Dose.- C. Whole-Animal Studies.- 1. Behavioral Excitation.- 2. Behavioral Depression.- 3. Interaction With Centrally Depressant Drugs.- 4. Anticonvulsant Effects.- 5. Electroencephalogram.- 6. Cerebral Blood Flow.- 7. Body Temperature.- 8. Emesis.- D. Synaptic Transmission: Catecholaminergic Mechanisms.- 1. Criteria of Catecholaminergic Stimulation and Antagonism at the Synaptic Level.- 2. Agroclavine-Type Ergot Derivatives.- 3. Ergometrine.- 4. D-LSD, 2-Br-LSD, and Methysergide.- 5. PRT 17-402.- 6. Ergocornine.- 7. Bromocriptine.- 8. Other Ergopeptine Derivatives.- 9. Efficacy of Ergot Derivatives as Antiparkinsonian Agents.- E. Synaptic Transmission: Serotoninergic Mechanisms.- 1. Criteria of Serotoninergic Stimulation and Antagonism at the Synaptic Level.- 2. D-LSD.- 3. 2-Br-LSD.- 4. Methysergide.- 5. Other Lysergic Acid Derivatives.- 6. Ergopeptine Derivatives.- F. Brain Metabolism.- 1. Brain Cyclic Adenosine Monophosphate.- 2. Adenosine Triphosphate Metabolism in the Brain.- 3. Transformation of Biosubstrates by Demethylation, Acetylation and Glucuronoconjugation.- G. References.- VII Clinical Pharmacology of Ergot Alkaloids in Senile Cerebral Insufficiency.- A. Introduction.- B. Terminology, Etiology, and Pathology of the Aging Process of the Brain.- 1. Terminology.- 2. Definition.- 3. Etiology and Pathology.- C. Research Techniques Used in Clinical Pharmacologic Studies of Ergot Alkaloids in Senile Cerebral Insufficiency.- 1. Methods for Measuring Cerebral Bloodflow and Metabolism.- 2. Methods for the Clinical Assessment of Brain Function.- 3. Electroencephalography.- D. Results of Clinical Pharmacology Studies With Ergot Alkaloids.- 1. Cerebral Bloodflow and Metabolic Studies.- 2. Clinical Pharmacologic Studies With Ergot Alkaloids in Senile Cerebral Insufficiency.- E. Summary.- F. References.- VIII Some Compounds With Hallucinogenic Activity.- A. Introduction.- B. Discovery of LSD.- C. Effects of LSD in Man.- 1. Somatic Actions.- 2. Psychic Actions.- 3. Effects of LSD on the Human EEG.- 4. Clinical Laboratory Investigations.- 5. Tolerance to LSD Effect.- 6. Inhibitors of LSD Reaction.- 7. Side-Effects and Complications.- 8. Illicit Use and Addiction.- D. Clinical Applications of LSD.- 1. Adjuvant to Psychotherapy.- 2. Psychedelic Therapy.- 3. Use in Psychoses.- 4. Therapeutic Use in Children.- 5. Use in Terminal Cancer Patients.- E. LSD Analogues Tested in Man.- 1. LSD Isomers.- 2. Hydrogenated Derivatives.- 3. Unsubstituted and Monosubstituted Amide Derivatives.- 4. Disubstituted Amide Derivatives.- 5. Cyclic Amide Derivatives.- 6. Ring-Substituted Derivatives.- 7. Ololiuqui.- 8. Discussion.- F. Cross-Tolerance.- G. References.- IX Influence on the Endocrine System.- A. Animal Data.- 1. Actions on Pituitary Hormones.- 2. Actions on Peripheral Endocrine Systems.- B. Human Data.- 1. Actions on Pituitary Hormones.- C. References.- X Metabolic Effects.- A. Introduction.- B. In Vitro Systems.- 1. Liver.- 2. Adipose Tissue.- 3. Various Tissues.- C. Intact Animals and Men.- 1. Influence on Catecholamine-Stimulated Carbohydrate Mobilization.- 2. Influence on Catecholamine-Stimulated Lipolysis.- 3. Influence on Other Catecholamine-Stimulated Metabolic Processes.- 4. Influence on Stress-Stimulated Metabolic Parameters.- 5. Influence on the Effects of Adrenalectomy or Sympathectomy.- 6. Influence on Glucose or Galactose Tolerance.- 7. Influence on Serotonin Effects.- 8. Interaction With Pancreas, Hypophysis, and Thyroidea.- 9. Actions of Ergot Alkaloids Alone on Metabolic Parameters.- D. Various Actions of Ergot Alkaloids.- E. References.- XI Biopharmaceutical Aspects. Analytical Methods, Pharmacokinetics, Metabolism and Bioavailability.- A. Introduction.- B. Assay of Ergot Alkaloids.- 1. Introduction.- 2. Radiotracer Methods.- 3. Nonradioisotopic Physicochemical Methods.- 4. Radioimmunoassay.- C. Pharmacokinetics.- 1. Introduction.- 2. Experiments in Animals.- 3. Experiments in Man.- 4. Interactions in Man.- 5. Physicochemical Properties of Ergot Alkaloids Which May Affect Enteral Absorption.- 6. Synopsis.- D. Metabolism.- 1. Introduction.- 2. Experiments.- 3. Biotransformation Sites in the Molecule.- 4. Interaction of Ergot Derivatives With Cytochrome P 450.- 5. Conclusions and Prospects.- E. References.- XII Toxicologic Considerations.- A. Introduction.- B. Systemic Toxicity.- 1. Animals.- 2. Man.- C. Effects on Reproductive Processes.- 1. Implantation and Early Pregnancy.- 2. Embryonic and Fetal Development.- 3. Lactation and the Offspring.- D. Potential Genetic Effects.- 1. LSD.- 2. Other Ergot Alkaloids.- 3. Conclusions.- E. Interactions Leading to Enhanced Toxicity.- 1. Disease Processes.- 2. Concomitant Medication.- F. Summary.- G. References.- Authors Index.

Reihe/Serie Handbook of Experimental Pharmacology ; 49
Zusatzinfo biography
Verlagsort Berlin
Sprache englisch
Gewicht 1970 g
Themenwelt Medizin / Pharmazie Pflege
Medizin / Pharmazie Pharmazie PTA / PKA
ISBN-10 3-540-08475-4 / 3540084754
ISBN-13 978-3-540-08475-4 / 9783540084754
Zustand Neuware
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