Tropane alkaloid

The chemical structure of tropane

Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure.^[1] Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Some tropane alkaloids have pharmacological properties and can act as anticholinergics or stimulants.

Anticholinergics

Anticholinergic drugs^[2] and deliriants:

• Atropine, racemic hyoscyamine, from the deadly nightshade (Atropa belladonna)
• Hyoscyamine, the levo-isomer of atropine, from henbane (Hyoscyamus niger) and mandrake (Mandragora officinarum)
• Scopolamine, from henbane and Datura species (Jimson weed)

All three acetylcholine-inhibiting chemicals can also be found in the leaves, stems, and flowers in varying, unknown amounts in Brugmansia (angel trumpets), a relative of Datura. The same is true of most plants found within the Solanaceae, particularly concentrated in leaves and seeds. However, the concentration of alkaloids can vary so greatly, even from leaf to leaf and seed to seed.

Stimulants

Stimulants and cocaine-related alkaloids:

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

Others

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

Non-natural tropanes

There exist some synthetic analogs of tropane alkaloids, see

• Phenyltropanes

They are not considered to be alkaloids per definition.

See also

• Alkaloid
• Tropane

References