The tropane alkaloids, which have the 8-azabicyclo octane nucleus, are commonly found in plants of three families, the Solanaceae, Erythroxylaceae and Convolvulaceae families. Tropane alkoloids are tropene derivatives. Tropane ring is composed of pyrrolidine and piperidine rings. Tropane is 3-hydroxy tropene.
TROPANE ALKALOIDS
The tropane alkaloids, which have the 8-azabicyclo octane
nucleus, are commonly found in plants of three families, the Solanaceae,
Erythroxylaceae and Convolvulaceae families. Tropane alkoloids are tropene
derivatives. Tropane ring is composed of pyrrolidine and piperidine rings.
Tropane is 3-hydroxy tropene. There are two stereoisomers of tropene, tropine
and pseudotropine. They are esters combined with acids. These esters of tropic
acid could be detected by vitali– morin reaction. The acids present are tropic
acid in atropine and atropic acid formed by the loss of water from tropic acid
in apoatropine. Other organic acids like tiglic acid, acetic acid, isobutyric
acid and isovaleric acid are also present.
The alkaloids isolated from plants of these families, while
having several legitimate medicinal uses, are probably best known for their
toxic properties. This can be a major problem since the plants produce very
attractive berries which are tempting to small children. As few as three
berries of henbane (Hyoscyamus niger) or deadly nightshade (Atropa belladonna)
can cause death in infants. Many of the plants in the Solanaceae family contain
tropane alkaloids, which are responsible for the toxic effects of the plants.
Cleopatra is reputed to have tested the effects of henbane and deadly
nightshade on her slaves to investigate the possibility of using these extracts
to commit suicide (she found the toxic effects too painful). The wives of the
Roman emperors, Augustus and Claudius, used deadly nightshade to murder large
numbers of Romans. The mandrake (Mandragora officinarum) was reputed to
possess aphrodisiac properties and was prized for these properties. However,
the roots also contain large quantities of the tropane alkaloid hyoscine
(scopolamine), making the plant highly toxic.
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