The Isoquinoline Alkaloids Chemistry and Pharmacology
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The Isoquinoline Alkaloids Chemistry and Pharmacology

1st Edition - January 1, 1972

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  • Author: Maurice Shamma
  • eBook ISBN: 9780323144506

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Description

The Isoquinoline Alkaloids: Chemistry and Pharmacology presents an overview of the chemistry, biogenesis, spectroscopy, and pharmacology of the isoquinoline alkaloids. This book examines the significant and interesting aspects of alkaloids. Organized into 32 chapters, this book starts with a discussion of the biogenesis of the isoquinolines and the various pharmacological effects of simple tetrahydroisoquinolines that have stimulant and convulsive properties. This text then explores the infrared absorptions, with emphasis on wavelength and frequency. Other chapters include topics on synthesis, degradation, reactions, absolute configuration, as well as on ultraviolet and nuclear magnetic resonance spectroscopy. This book further explores the various methods available for the preparation of simple tetrahydroisoquinolines, including the Bischler–Napieralski, Pictet–Spengler, and phenolic cyclization, as well as the Friedel–Crafts acylation. The last chapter deals with ancistrocladine, which is the first isoquinoline alkaloid found to possess a methyl group. Biochemists and biophysicists will find this book useful.

Table of Contents


  • Preface

    Chapter 1. The Simple Tetrahydroisoquinolines

    I. Introduction

    II. Degradations

    III. Some Nonbasic Isoquinolines: Peyoglutam, Mescalotam, and Related Alkaloids

    IV. Methods of Synthesis

    V. The Gigantine Problem

    VI. Some Reactions of Tetrahydroisoquinolines and Their Derivatives

    VII. Absolute Configuration

    VIII. Biosynthesis

    IX. Pharmacology

    X. The Possible Role of Tetrahydroisoquinoline Alkaloids in Alcoholism

    XI. Mass Spectroscopy

    XII. NMR Spectroscopy

    XIII. UV Spectroscopy

    References

    Chapter 2. The Benzylisoquinolines

    I. Introduction

    II. Degradation of Laudanosine, A Tetrahydro Benzylisoquinoline Alkaloid

    III. Structural Elucidation of Takatonine, A Quaternary Benzylisoquinoline Alkaloid

    IV. Petaline, A Tetrahydro Benzylisoquinoline of Unusual Substitution Pattern

    V. Two Glycosidic Tetrahydrobenzylisoquinoline Alkaloids: Latericine and Veronamine

    VI. Methods of Synthesis

    VII. Some Reactions of Benzylisoquinolines

    VIII. Absolute Configuration

    IX. Biosynthesis

    X. Pharmacology

    XI. A Possible Biochemical Basis for Alcohol Addiction: A Hypothesis and Its Critique

    XII. Mass Spectroscopy

    XIII. NMR Spectroscopy

    XIV. X-Ray Analysis

    XV. UV Spectroscopy

    References

    Chapter 3. The Isoquinolones

    I. Introduction

    II. Structural Elucidation and Synthesis

    III. An Alternate Synthesis of 3,4-Dihydroisoquinolones

    IV. Pharmacology

    References

    Chapter 4. The Pavines and Isopavines

    I. Structural Elucidation and Synthesis

    II. Absolute Configuration

    III. Biosynthesis

    IV. Mass Spectroscopy

    V. NMR Spectroscopy

    VI. UV Spectroscopy

    VII. The Differentiation between Pavine and Isopavine Bases

    References

    Chapter 5. The Bisbenzylisoquinolines

    I. Introduction

    II. A Classical Degradation of a Bisbenzylisoquinoline Alkaloid: The Structure of Berbamine

    III. Some Comments on the Sodium in Liquid Ammonia Cleavage of Bisbenzylisoquinolines

    IV. The Structures of Tubocurarine, Chondocurarine, and Chondocurine

    V. Repanduline: A Ketonic Bisbenzylisoquinoline Alkaloid

    VI. Syntheses of Bisbenzylisoquinolines

    VII. Conversion of Oxyacanthine-type Alkaloids to the Trilobine Series

    VIII. Some Reagents for Interrelating Benzylisoquinolines, Bisbenzylisoquinolines, and Other Isoquinolines

    IX. Biogenesis and Phenolic Oxidative Coupling

    X. Pharmacology

    XI. Absolute Configuration

    XII. The Isomerization of (-f-)-Oxyacanthine to (—)-Repandine

    XIII. Mass Spectroscopy

    XIV. NMR Spectroscopy

    XV. UV Spectroscopy

    References

    Chapter 6. The Cularines

    I. Introduction

    II. Cularine: Structural Determination

    III. Syntheses of Cularine and Its Analogs

    IV. Absolute Configuration

    V. NMR Spectroscopy and Conformation

    VI. Mass Spectroscopy

    VII. UV Spectroscopy

    References

    Chapter 7. The Cularine-Morphine Dimers

    I. Structural Elucidation

    II. Dehydrocancentrine A and Dehydrocancentrine Β

    III. UV Spectroscopy

    References

    Chapter 8. The Dibenzopyrrocolines

    I. Structural Elucidation

    II. Syntheses of Dibenzopyrrocolines

    III. Mass Spectroscopy

    IV. NMR Spectroscopy

    References

    Chapter 9. The Proaporphines

    I. Introduction

    II. Structural Elucidation

    III. Nonbiogenetic Syntheses

    IV. Biogenetic Studies Using Phenolic Oxidative Coupling

    V. Biogenetic Studies with Labeled Compounds

    VI. Absolute Configuration and Circular Dichroism

    VII. Pharmacology

    VIII. Mass Spectroscopy

    IX. NMR Spectroscopy

    X. UV and IR Spectroscopy

    References

    Chapter 10. The Aporphines

    I. Introduction

    II. A Classical Degradation of an Aporphine

    III. Apomorphine

    IV. Nonbiogenetic Syntheses of Aporphines

    V. Some Reactions of Aporphines

    VI. Stereochemistry and Absolute Configuration

    VII. X-Ray Crystallography

    VIII. Biosynthesis and Biogenetic Syntheses

    IX. The Relationship between the Ring D Substituents and the Absolute Configuration

    X. Pharmacology

    XI. Mass Spectroscopy

    XII. NMR Spectroscopy

    XIII. UV Spectroscopy

    XIV. Ushinsunine: A C-7 Hydroxylated Aporphine

    XV. Steporphine: A C-4 Hydroxylated Aporphine

    XVI. The Dehydroaporphines

    References

    Chapter 11. Pakistanamine: A Proaporphine-Benzylisoquinoline Dimer

    I. Structural Elucidation and Chemical Conversions

    II. Mass Spectroscopy

    III. NMR Spectroscopy

    IV. UV and IR Spectroscopy

    Reference

    Chapter 12. The Aporphine-Benzylisoquinoline Dimers

    I. Introduction

    II. Structural Elucidation and Synthesis

    III. Biosynthesis

    IV. Pharmacology

    V. Circular Dichroism

    VI. NMR Spectroscopy

    VII. UV Spectroscopy

    VIII. (H-)-Hernandaline, An Elaborated Aporphine Alkaloid 239

    IX. The Kupchan-Liepa Total Synthesis of (+)-Thalicarpine via Synthetic (+)-Hernandaline

    X. Pakistanine, A Novel Type Aporphine-Benzylisoquinoline Dimer

    References

    Chapter 13. The Oxoaporphines

    I. Introduction

    II. Liriodenine: Structural Elucidation and Synthesis

    III. The Oxidation of Aporphines and the Reduction of Oxoaporphines

    IV. An Unusual Demethoxylation Reaction

    V. Pharmacology

    VI. NMR Spectroscopy

    VII. UV Spectroscopy

    VIII. Corunnine and Pontevedrine, Two New Oxoaporphines

    References

    Chapter 14. The Phenanthrene Alkaloids

    I. Structural Elucidation and Synthesis

    II. Pharmacology

    III. Mass Spectroscopy

    IV. NMR Spectroscopy

    V. UV Spectroscopy

    References

    Chapter 15. Taspine

    I. Structural Elucidation

    II. Biogenesis and Conversion of Magnoflorine into Taspine

    III. NMR and UV Spectroscopy

    References

    Chapter 16. The Protoberberines and Retroprotoberberines

    I. Introduction

    II. Chemical Degradation

    III. Syntheses of Protoberberines

    IV. Reactions of Protoberberines

    V. Stereochemistry

    VI. Berberastine and Thalidastine: Two Quaternary Protoberberines Hydroxylated at C-5

    VII. Mecambridine and Alkaloid PO-5, Orientalidine and Alkaloid PO-4: Four Retroprotoberberine Alkaloids

    VIII. Color Changes of Phenolic Quaternary Protoberberines

    IX. Biosynthesis

    X. Pharmacology

    XI. Mass Spectroscopy

    XII. NMR Spectroscopy

    XIII. UV Spectroscopy

    References

    Chapter 17. The Benzophenanthridines

    I. Introduction

    II. The Chemistry and Stereochemistry of Chelidonine

    III. The Chemistry of Sanguinarine and Chelerythrine

    IV. The Structures of Corynoline and Corynoloxine: Two Unusual Benzophenanthridine Alkaloids

    V. Syntheses of Benzophenanthridines

    VI. Mass Spectroscopy

    VII. NMR Spectroscopy

    VIII. The C-6-Methoxylated Aromatic Benzophenanthridines

    IX. Bocconine

    X. Bocconoline and Corynolamine

    XI. The Characterization of a Dimeric Benzophenanthridine Alkaloid

    XII. Biosynthesis

    XIII. Pharmacology

    XIV. UV Spectroscopy

    References

    Chapter 18. The Protopines

    I. Introduction

    II. Structural Elucidation of Cryptopine and Protopine

    III. Formation of Protoberberines from Protopines

    IV. The Chemistry of Anhydrocryptopine and the Conversion of Protopine to Sanguinarine

    V. The Conversion of Tetrahydroprotoberberines into Protopine Bases

    VI. Mass Spectroscopy

    VII. 13-Oxomuramine, A Protopine Base Oxygenated at C-13

    VIII. Fumaridine and Fumaramine, Two New Protopine Alkaloids?

    IX. Biosynthesis

    X. Pharmacology

    XI. NMR Spectroscopy

    XII. X-Ray Analysis

    XIII. UV Spectra

    References

    Chapter 19. The Phthalic Isoquinolines

    I. Introduction

    II. Structural Elucidation

    III. Absolute Configuration and ORD Studies

    IV. Syntheses of Phthalide Isoquinolines

    V. Some Reactions of Narcotine and Hydrastine

    VI. Biosynthesis

    VII. Pharmacology

    VIII. Mass Spectroscopy

    IX. NMR Spectroscopy

    X. UV Spectroscopy

    References

    Chapter 20. The Spiro Benzylisoquinolines

    I. Introduction and Nomenclature

    II. Structural Elucidation

    III. Syntheses of Spiro Benzylisoquinolines

    IV. The Protoberberine->Spiro Benzylisoquinoline->Dibenzo Cyclopent[b]- azepine Rearrangement

    V. Mass Spectroscopy

    VI. UV Spectroscopy

    References

    Chapter 21. The Rhoeadines and Papaver Rubines

    I. Introduction

    II. Reactions of Rhoeadine and Derivatives

    III. An Alternate Degradative Scheme

    IV. Isomerization of the Rhoeadines and Relative Stereochemistry: NMR Spectroscopy

    V. (+)-lsorhoeagenine α-D-Glucoside

    VI. Conversion of Rhoeadine to the Protoberberine Alkaloidal Salt Coptisine

    VII. Acid-Catalyzed Rearrangement of the Papaverrubines

    VIII. Some Early Preparations of Benzazepine Systems

    IX. The Conversion of a Spiro Benzylisoquinoline into (±)-Rhoea Pentanediol

    X. The Roche Nutley Conversion of Phthalide Isoquinolines into Rhoeadines

    XI. Optical Activity, ORD,CD, and Absolute Configuration

    XII. Biogenesis

    XIII. Mass Spectroscopy

    XIV. UV Spectroscopy

    References

    Chapter 22. Protostephanine

    I. Introduction and Structural Elucidation

    II. The Pecherer-Brossi Synthesis of Protostephanine

    III. A Suggested Biogenetic Pathway for the Formation of Protostephanine

    IV. The Synthesis of Protostephanine by a Route Related to the Biogenetic Pathway

    V. The Preparation of Protostephanine Analogs from Thebaine

    VI. Pharmacology

    VII. UV Spectroscopy

    VIII. Erybidine, An Erythrina Alkaloid Related to Protostephanine

    References

    Chapter 23. Emetine and Related Alkaloids

    I. Introduction

    II. Chemical Interrelationships between the Ipecac Bases

    III. Degradation of Emetine

    IV. The Position of the Phenolic Function in Cephaeline

    V. Protoemetine

    VI. The Stereochemistry of Emetine

    VII. Syntheses of Emetine

    VIII. Ipecoside, A Monoterpenoidal Isoquinoline Glucoside

    IX. Alangiside

    X. Biosynthesis

    XI. The Partial Synthesis of Secologanin and Ipecoside

    XII. Rubremetine Salts

    XIII. Pharmacology

    XIV. Mass Spectroscopy

    XV. NMR Spectroscopy

    XVI. UV Spectroscopy

    References

    Chapter 24. Autumnaline: A Phenethylisoquinoline

    I. Introduction

    II. Autumnaline

    III. Syntheses of Phenethylisoquinolines

    IV. Absolute Configuration

    V. Biosynthesis

    VI. Pharmacology

    VII. NMR Spectroscopy

    VIII. UV Spectroscopy

    References

    Chapter 25. Melanthioidine: A Bisphenethylisoquinoline

    I. Structural Elucidation of Melanthioidine

    II. The Battersby Synthesis of Melanthioidine

    III. Enzyme-Induced Syntheses of Analogs of Melanthioidine

    References

    Chapter 26. The Homoaporphines and Homoproaporphines

    I. Three Homoaporphine Alkaloids: Kreysigine, Multifloramine, and Floramultine

    II. The Homopro Aporphine Kreysiginone and the Dihydrohomoproaporphine Dihydrokreysiginone

    III. Syntheses of Homoaporphines and Homoproaporphines through Phenolic Oxidative Coupling

    IV. The Synthesis of Reduced Homoproaporphines through Carbonium Ion Intermediates

    V. An Alternate Synthesis of Homoproaporphines through Carbonium Ion Intermediates

    VI. Photolytic Syntheses of Homoaporphines and Homoproaporphines

    VII. A Photochemical Reaction of Kreysiginone

    VIII. Absolute Configuration

    IX. Biosynthesis of Homoaporphines

    X. Pharmacology

    XI. Mass Spectroscopy

    XII. NMR Spectroscopy

    XIII. UV Spectroscopy

    References

    Chapter 27. The Homoprotoberberines

    I. Synthesis

    II. Hydrogenolysis of Homoprotoberberines

    III. Absolute Configuration

    IV. Mass Spectroscopy

    V. NMR Spectroscopy

    VI. UV Spectroscopy

    References

    Chapter 28. The Phenyl Tetrahydroisoquinolines

    I. Cryptostyline I

    II. X-Ray Analysis and Absolute Configuration

    III. Pharmacology

    IV. NMR Spectroscopy

    V. UV Spectroscopy

    References

    Chapter 29. The N-Benzyltetrahydroisoquinolines

    I. Sendaverine

    II. Corgoine

    References

    Chapter 30. Cherylline

    Text

    References

    Chapter 31. The Naphthalene Isoquinolines

    I. Structural Elucidation

    II. Biosynthesis

    III. NMR Spectroscopy

    References

    Chapter 32. Addenda

    Text

    References

    Appendix. Occurrence of Isoquinoline Alkaloids by Plant Families

    Author Index

    Subject Index


Product details

  • No. of pages: 614
  • Language: English
  • Copyright: © Academic Press 1972
  • Published: January 1, 1972
  • Imprint: Academic Press
  • eBook ISBN: 9780323144506

About the Author

Maurice Shamma

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