The Alkaloids

Preface

The Morphine Alkaloids. I

I. Introduction

II. Elucidation of the Structure of Morphine, Codeine, and Thebaine

III. The Reactions of Morphine, Codeine, and Related Products

IV. The Reactions of Thebaine and Related Products

V. Synthetic Hydrophenanthrenes Related to the Morphine Alkaloids

VI. Table of Physical Constants

VII. References

The Morphine Alkaloids. II

I. Introduction

II. The Reactions of Morphine, Codeine and Neopine

III. The Reactions of Thebaine and Related Products

IV. The Stereochemistry of the Morphine Alkaloids and Sinomenine

V. Rearrangement and Elimination Reactions

VI. The Synthesis of Related Products

VII. Tables of Physical Constants

VIII. References

Sinomenine

I. Physiological Action, Isolation and Color Reactions

II. Elucidation of the Constitution of Sinomenine

III. Reactions of Sinomenine and Related Products

IV. Partial Synthesis of the Antipode of 1-Bromosinomeninone

V. Table of Physical Constants

VI. References

Colchicine

I. Chemistry of Colchicine

II. Biological Effects of Colchicine

III. References

Alkaloids of the Amaryllidaceae

I. Occurrence and General History

II. Chemistry of Individual Alkaloids

III. References

Acridine Alkaloids

I. Introduction

II. Degradation

III. Conclusion

IV. References

The Indole Alkaloids

I. Introduction

II. The Simple Bases

III. The Ergot Alkaloids

IV. The Alkaloids of Peganum harmala

V. Alkaloids of Evodia rutaecarpa

VI. The Alkaloids of Yohimbe

VII. The Quebracho Alkaloids

VIII. Alkaloids of Rauwolfia Species

IX. Alkaloids of Gelsemium Species

X. The Alkaloids of Calycanthaceae

XI. Alkaloids of Calabar Bean

XII. The Iboga Alkaloids

XIII. Alkaloids of Alstonia Species

XIV. Alkaloids of Geissospermum vellosii

XV. Quinamine and Cinchonamine

XVI. C-Dihydrotoxiferine-I

XVII. Tables

XVIII. References

The Erythrina Alkaloids

I. Introduction

II. Distribution

III. Isolation of the Alkaloids

IV. The Free Alkaloids

V. The Combined Alkaloids

VI. The Liberated Alkaloids

VII. Table of Physical Constants

VIII. References

The Strychnos Alkaloids. Part II

I. Introduction

II. Elucidation of the Structure of Strychnine and Brucine

III. Vomicine and Vomipyrine (425-436)

IV. The Structure and Stereochemistry of Strychnine

V. Tables of Physical Constants

VI. References

Author Index

Subject Index

Chapter VIII

Part I The Morphine Alkaloids. I


1. Introduction

II. Elucidation of the Structure of Morphine, Codeine, and Thebaine


1. The Phenanthrene Nucleus of Morphine


2. Oxazine and Isoquinoline Formulas for Morphine


3. Pyridine Formulas for Morphine


4. Transitional Formulas


5. The Camphane and Modern Formulas


6. Problems Remaining

III. The Reactions of Morphine, Codeine, and Related Products


1. Reduction


2. Oxidation


3. Substitution in the Benzene Nucleus


4. Fission around the Nitrogen Atom


5. The Action of Organometallic Compounds


6. The Codides and Morphides


7. The Desoxycodeines

IV. The Reactions of Thebaine and Related Products


1. Reduction


2. Oxidation


3. The Action of Organometallic Compounds


4. Fission Around the Nitrogen Atom


5. Rearrangements

V. Synthetic Hydrophenanthrenes Related to the Morphine Alkaloids

VI. Table of Physical Constants

VII. References