Transcript
Page 1: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Tropane AlkaloidsMohammed N. Sabir

Page 2: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Lecture overview• Introduction

• Occurence

• Chemistry and biogenesis

• Medicinal values

• Belladonna alkaloids

• Cocaine

• lecture review

Page 3: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Introduction to tropane alkaloids

• Historical background • Atropa belladonna

Page 4: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Occurence

• These alkaloids are abundant

in Nightshade family

(Solanaceae)

Page 5: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Biosynthesis…

• They are derived from two basic compounds:-

1. L-Ornithine and consequent biotransformation to N-Methylpyrrolinium ion.

2. L-Phenyl alanine and its transformation to (+)-Tropic acid.

• Esterification of both molecules.

Page 6: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

SAR…

• The tertiary amine group that is protonated at physiologic pH.

• The aryl (benzene ring) [hydrophobic bonding to the receptor site].

• The hydroxyl group [hydrogen bonding].

• Ethylene bridge.

• Resemblance to acetylcholine.

Page 7: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction
Page 8: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Medicinal valuesVarious medications obtained from tropane alkaloids used for:-

• CNS

• PNS

• GIT

• Heart

• Eye

• Pulmonary

• Kidneys

Page 9: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Plants that contain belladonna alkaloids…

Atropa belladonna Hyoscyamus niger H. muticus H. albus Datura stramonium

Page 10: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Belladonna alkaloids

(-)-Hyoscyamine Atropine [(+)-Hyoscyamine] Scopolamine Belladonine

Page 11: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction
Page 12: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Belladonine

Page 13: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction
Page 14: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction
Page 15: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction
Page 16: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction
Page 17: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction
Page 18: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Coca and cocaine…

Erythroxyllum coca E. truxilence

Page 19: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Cocaine

Page 20: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction
Page 21: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction
Page 22: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction
Page 23: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction
Page 24: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction
Page 25: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction
Page 26: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Crack

Page 27: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Lecture review

Page 28: Tropane alkaloids - WordPress.com · • Introduction • Occurence • Chemistry and biogenesis • Medicinal values • Belladonna alkaloids • Cocaine • lecture review. Introduction

Thanks for listening… Any questions?


Recommended