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Tropane AlkaloidsMohammed N. Sabir

Lecture overview• Introduction

• Occurence

• Chemistry and biogenesis

• Medicinal values

• Belladonna alkaloids

• Cocaine

• lecture review

Introduction to tropane alkaloids

• Historical background • Atropa belladonna

Occurence

• These alkaloids are abundant

in Nightshade family

(Solanaceae)

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.

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.

Medicinal valuesVarious medications obtained from tropane alkaloids used for:-

• CNS

• PNS

• GIT

• Heart

• Eye

• Pulmonary

• Kidneys

Plants that contain belladonna alkaloids…

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

Belladonna alkaloids

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

Belladonine

Coca and cocaine…

Erythroxyllum coca E. truxilence

Cocaine

Crack

Lecture review

Thanks for listening… Any questions?