Tropane alkaloid

Tropane alkaloids are a class of bicyclic alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as cocaine and scopolamine are notorious for their psychoactive effects, related usage and cultural associations. Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants.

Classification

Anticholinergics

s and deliriants:

Atropine, racemic hyoscyamine, from the deadly nightshade
Hyoscyamine, the levo-isomer of atropine, from henbane, mandrake and the sorcerers' tree.
Scopolamine, from henbane and Datura species

All three acetylcholine-inhibiting chemicals can also be found in the leaves, stems, and flowers in varying, unknown amounts in Brugmansia, a relative of Datura. The same is also true of many other plants belonging to subfamily Solanoideae of the Solanaceae, the alkaloids being concentrated particularly in the leaves and seeds. However, the concentration of alkaloids can vary greatly, even from leaf to leaf and seed to seed.

Stimulants

s and cocaine-related alkaloids:

Cocaine, from coca plant
Ecgonine, a precursor and metabolite of cocaine
Benzoylecgonine, a metabolite of cocaine
Hydroxytropacocaine, from coca plant
Methylecgonine cinnamate, from coca plant

Others

Catuabines, found in catuaba, an infusion or dry extract made from Erythroxylum vaccinifolium
Scopine

Synthetic analogs of tropane alkaloids also exist, such as the phenyltropanes. They are not considered to be alkaloids per definition.

Biosynthesis

The biosynthesis of the tropane alkaloids have attracted intense interest because of their high physiological activity as well as the presence of the bicyclic tropane core.