Tropane alkaloids are a class of bicyclic .2.1

alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...

s and secondary metabolites that contain a tropane ring in their

chemical structure A chemical structure of a molecule is a spatial arrangement of its atoms and their chemical bonds. Its determination includes a chemist's specifying the molecular geometry and, when feasible and necessary, the electronic structure of the target m ...

. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as

cocaine Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two South American coca plants, ''Erythroxylum coca'' and ''Erythroxylum novogranatense, E. novogranatense'', which are cultivated a ...

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 Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognitio ...

Classification

Anticholinergics

Anticholinergic drugs and

deliriant Deliriants are a subclass of hallucinogen. The term was coined in the early 1980s to distinguish these drugs from psychedelics such as LSD and dissociatives such as ketamine, due to their primary effect of causing delirium, as opposed to th ...

s: * Atropine, racemic hyoscyamine, from the deadly nightshade ('' Atropa belladonna'') * Hyoscyamine, the ''levo''-

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

of atropine, from henbane ('' Hyoscyamus niger''), mandrake ('' Mandragora officinarum'') and the sorcerers' tree ('' Latua pubiflora''). * Scopolamine, from henbane and ''

Datura ''Datura'' is a genus of nine species of highly poisonous, Vespertine (biology), vespertine-flowering plants belonging to the nightshade family (Solanaceae). They are commonly known as thornapples or jimsonweeds, but are also known as devil's t ...

'' species (Jimson weed) All three

acetylcholine Acetylcholine (ACh) is an organic compound that functions in the brain and body of many types of animals (including humans) as a neurotransmitter. Its name is derived from its chemical structure: it is an ester of acetic acid and choline. Par ...

-inhibiting chemicals can also be found in the leaves, stems, and flowers in varying, unknown amounts in '' Brugmansia'' (angel trumpets), a relative of ''

''. 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

Stimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...

s and cocaine-related alkaloids: *

Cocaine Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two South American coca plants, ''Erythroxylum coca'' and ''Erythroxylum novogranatense, E. novogranatense'', which are cultivated a ...

, 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 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. CocaineBiosyn2

References

{{Chemical classes of psychoactive drugs Deliriants