Tropane

Tropane is a bicyclic organic compound and a tertiary amine. It is the structural parent of many natural products collectively known as tropane alkaloids, which include compounds like atropine, cocaine, and scopolamine. Tropane is a key building block in the biosynthesis of these important alkaloids.

Structure and Properties

Tropane is composed of a seven-membered ring with a nitrogen atom and a three-membered ring fused together. The nitrogen atom, being a tertiary amine, carries a lone pair of electrons, which contributes to the compound's basicity. The bicyclic structure of tropane is rigid, which influences the biological activity of its derivatives.

Tropane Alkaloids

Tropane alkaloids are a class of alkaloids that contain a tropane ring in their structure. They are found in a variety of plants, particularly in the Solanaceae family, which includes species like deadly nightshade (Atropa belladonna), henbane (Hyoscyamus niger), and jimson weed (Datura stramonium).

Atropine

Atropine is a tropane alkaloid derived from the deadly nightshade plant. It is used in medicine to dilate the pupils and as an antidote for certain types of poisonings.

Cocaine

Cocaine is a tropane alkaloid derived from the coca plant. It is a powerful stimulant and is used medically as a topical anesthetic.

Scopolamine

Scopolamine is a tropane alkaloid derived from plants like henbane and jimson weed. It is used in medicine to treat motion sickness and postoperative nausea and vomiting.

Biosynthesis

The biosynthesis of tropane alkaloids involves the condensation of ornithine and acetoacetic acid to form hygrine, which is then cyclized to form tropinone. Tropinone is then reduced to form tropane.

See Also

• Alkaloid
• Atropine
• Cocaine
• Scopolamine
• Solanaceae