tropane alkaloids - wordpress.com · • introduction • occurence • chemistry and biogenesis...
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Tropane AlkaloidsMohammed N. Sabir
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Lecture overview• Introduction
• Occurence
• Chemistry and biogenesis
• Medicinal values
• Belladonna alkaloids
• Cocaine
• lecture review
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Introduction to tropane alkaloids
• Historical background • Atropa belladonna
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Occurence
• These alkaloids are abundant
in Nightshade family
(Solanaceae)
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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.
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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.
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Medicinal valuesVarious medications obtained from tropane alkaloids used for:-
• CNS
• PNS
• GIT
• Heart
• Eye
• Pulmonary
• Kidneys
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Plants that contain belladonna alkaloids…
Atropa belladonna Hyoscyamus niger H. muticus H. albus Datura stramonium
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Belladonna alkaloids
(-)-Hyoscyamine Atropine [(+)-Hyoscyamine] Scopolamine Belladonine
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Belladonine
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Coca and cocaine…
Erythroxyllum coca E. truxilence
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Cocaine
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Crack
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Lecture review
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Thanks for listening… Any questions?