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?