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 (Hyoscamus 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 or Devil's Weed), a relative of Datura.

Stimulants

Stimulants and cocaine-related alkaloids:

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

Others

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

1. O’Hagan, David (2000). "Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids (1998 to 1999)". Natural Product Reports 17 (5): 435–446. doi:10.1039/a707613d.
2. Grynkiewicz, G; Gadzikowska, M. "Tropane alkaloids as medicinally useful natural products and their synthetic derivatives as new drugs.". Pharmacological reports : PR 60 (4): 439–63. PMID 18799813.