Tropane alkaloids - ¢â‚¬¢ Introduction ¢â‚¬¢ Occurence ¢â‚¬¢ Chemistry and biogenesis ¢â‚¬¢ Medicinal values

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Text of Tropane alkaloids - ¢â‚¬¢ Introduction ¢â‚¬¢...

  • Tropane Alkaloids Mohammed 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 values Various 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?