Tropane Alkaloids

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Chapter: Pharmacognosy and Phytochemistry : Drugs Containing 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.


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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