Tropane alkaloid
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 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
They are not considered to be alkaloids per definition.
See also
References
- ^ 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.
- ^ 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.