Tropane alkaloid
Tropane alkaloids are a class of alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...

s and secondary metabolite
Secondary metabolite
Secondary metabolites are organic compounds that are not directly involved in the normal growth, development, or reproduction of an organism. Unlike primary metabolites, absence of secondary metabolities does not result in immediate death, but rather in long-term impairment of the organism's...

s that contain a tropane
Tropane is a nitrogenous bicyclic organic compound. It is mainly known for a group of alkaloids derived from it , which include, among others, atropine and cocaine. Both alkaloids contain tropinone from which tropane is a derivate...

 ring in their chemical structure
Chemical structure
A chemical structure includes molecular geometry, electronic structure and crystal structure of molecules. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together. Molecular geometry can range from the very simple, such as...

 (see the picture to the right). Tropane alkaloids occur naturally in many members of the plant family Solanaceae
Solanaceae are a family of flowering plants that include a number of important agricultural crops as well as many toxic plants. The name of the family comes from the Latin Solanum "the nightshade plant", but the further etymology of that word is unclear...


The main classes of tropane alkaloids are anticholinergics and stimulants, although a few others exist.


Anticholinergic drugs and deliriant
The deliriants are a special class of acetylcholine-inhibitor hallucinogen. The term was introduced by David F. Duncan and Robert S...

  • Atropine
    Atropine is a naturally occurring tropane alkaloid extracted from deadly nightshade , Jimson weed , mandrake and other plants of the family Solanaceae. It is a secondary metabolite of these plants and serves as a drug with a wide variety of effects...

    , racemic hyoscyamine, from the deadly nightshade
    Deadly nightshade
    Atropa belladonna or Atropa bella-donna, commonly known as Belladonna, Devil's Berries, Death Cherries or Deadly Nightshade, is a perennial herbaceous plant in the family Solanaceae, native to Europe, North Africa, and Western Asia. The foliage and berries are extremely toxic, containing tropane...

     (Atropa belladonna)
  • Hyoscyamine
    Hyoscyamine is a tropane alkaloid. It is a secondary metabolite found in certain plants of the Solanaceae family, including henbane , mandrake , jimsonweed , tomato and deadly nightshade...

    , the levo-isomer
    In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...

     of atropine, from henbane
    Henbane , also known as stinking nightshade or black henbane, is a plant of the family Solanaceae that originated in Eurasia, though it is now globally distributed.-Toxicity and historical usage:...

     (Hyoscamus niger) and mandrake
    Mandrake (plant)
    Mandrake is the common name for members of the plant genus Mandragora, particularly the species Mandragora officinarum, belonging to the nightshades family...

     (Mandragora officinalis)
  • Scopolamine
    Scopolamine, also known as levo-duboisine, and hyoscine, is a tropane alkaloid drug with muscarinic antagonist effects. It is among the secondary metabolites of plants from Solanaceae family of plants, such as henbane, jimson weed and Angel's Trumpets , and corkwood...

    , from henbane and Datura
    Datura is a genus of nine species of vespertine flowering plants belonging to the family Solanaceae. Its precise and natural distribution is uncertain, owing to its extensive cultivation and naturalization throughout the temperate and tropical regions of the globe...

    species (Jimson weed)

All three acetylcholine
The chemical compound acetylcholine is a neurotransmitter in both the peripheral nervous system and central nervous system in many organisms including humans...

-inhibiting chemicals can be found in the leaves, stems, and flowers in varying, unknown amounts in the tree-cousin of Datura, (Brugmansia
Brugmansia is a genus of seven species of flowering plants in the family Solanaceae, native to subtropical regions of South America, along the Andes from Colombia to northern Chile, and also in southeastern Brazil. They are known as Angel's Trumpets, sharing that name with the closely related genus...

e) more commonly known as Angel Trumpets or Devil's Weed.


Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...

s and cocaine-related alkaloids:
  • Cocaine
    Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" in addition to the alkaloid suffix -ine, forming cocaine. It is a stimulant of the central nervous system, an appetite suppressant, and a topical anesthetic...

    , from Erythroxylum coca
  • Ecgonine
    Ecgonine is an organic chemical and tropane alkaloid found naturally in coca leaves. It has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance, as are all known substances which can be used as precursors to ecgonine...

    , a precursor and metabolite of cocaine
  • Benzoylecgonine
    Benzoylecgonine is a topical analgesic and the main metabolite of cocaine.-History:Benzoylecgonine is used as the main pharmaceutical ingredient in the prescription drug Esterom, a topical solution used for the relief of muscle pain....

    , a metabolite of cocaine
  • Hydroxytropacocaine
    Hydroxytropacocaine is a tropane alkaloid found in Erythroxylum coca....

    , from Erythroxylum coca
  • Methylecgonine cinnamate
    Methylecgonine cinnamate
    Methylecgonine cinnamate is a natural tropane alkaloid found within the Erythroxylum coca plant. Its more common name, cinnamoylcocaine, reflects its close structural similarity to cocaine. It is said to be pharmacologically inactive.-See also:*Cocaine...

    , from Erythroxylum coca


  • Catuabine
    Catuabines are a group of tropane alkaloids, isolated from Erythroxylum vacciniifolium, which are used in the preparation of the drug Catuaba. While catuabine A, B and C were isolated and characterized by Graf and Lude , catuabine D was recently isolated by Zanolari et al...

    s, found in the drug catuaba
    The name catuaba is used for the infusions of the bark of a number of trees native to Brazil. The most widely used barks are derived from the trees Trichilia catigua and Erythroxylum vacciniifolium...

    , from Erythroxylum vacciniifolium

Non-natural tropanes

There exist some synthetic analogs of tropane alkaloids, see
  • Phenyltropane
    Phenyltropanes were originally developed to reduce cocaine addiction and dependency. In general these compounds act as inhibitors of the plasmalemmal monoamine reuptake transporters. Although RTI holds a strong position in this field, they are not the only researchers that have prepared these...


They are not considered to be alkaloids per definition.
The source of this article is wikipedia, the free encyclopedia.  The text of this article is licensed under the GFDL.