The Isoquinoline Alkaloids Chemistry and Pharmacology
1st Edition
Secure Checkout
Personal information is secured with SSL technology.Free Shipping
Free global shippingNo minimum order.
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
Details
- No. of pages:
- 614
- Language:
- English
- Copyright:
- © Academic Press 1972
- Published:
- 1st January 1972
- Imprint:
- Academic Press
- eBook ISBN:
- 9780323144506
About the Author
Maurice Shamma
Ratings and Reviews
Request Quote
Tax Exemption
Elsevier.com visitor survey
We are always looking for ways to improve customer experience on Elsevier.com.
We would like to ask you for a moment of your time to fill in a short questionnaire, at the end of your visit.
If you decide to participate, a new browser tab will open so you can complete the survey after you have completed your visit to this website.
Thanks in advance for your time.