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Tropane alkaloids, also known as Belladonna alkaloids are a class of alkaloid
Alkaloid

Alkaloids are naturally occurring chemical compounds containing base nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base....
s and secondary metabolite
Secondary metabolite

Secondary metabolites are organic compounds that are not directly involved in the normal cell growth, Biological development or reproduction of organisms....
s that contain a tropane
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....
 ring in their chemical structure
Chemical structure

A Chemical structure includes molecular geometry, electronic structure and crystal structure of a chemical compound. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together....
. Tropane alkaloids occur naturally in many members of the plant family Solanaceae
Solanaceae

The Solanaceae is a family of flowering plants, that contains a number of important agricultural plants 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....
.

Important tropane alkaloids are:








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Tropane alkaloids, also known as Belladonna alkaloids are a class of alkaloid
Alkaloid

Alkaloids are naturally occurring chemical compounds containing base nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base....
s and secondary metabolite
Secondary metabolite

Secondary metabolites are organic compounds that are not directly involved in the normal cell growth, Biological development or reproduction of organisms....
s that contain a tropane
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....
 ring in their chemical structure
Chemical structure

A Chemical structure includes molecular geometry, electronic structure and crystal structure of a chemical compound. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together....
. Tropane alkaloids occur naturally in many members of the plant family Solanaceae
Solanaceae

The Solanaceae is a family of flowering plants, that contains a number of important agricultural plants 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....
.

Important tropane alkaloids are:

Anticholinergics


Anticholinergic drugs and deliriant
Deliriant

The deliriants are a special class of acetylcholine receptor-inhibitor dissociatives. The name comes from their primary effect of inducing a medical state of frank delirium, characterized by stupor, utter confusion, confabulation, and regression to "phantom" behaviors such as disrobing and plucking ....
s:

  • Atropine
    Atropine

    Atropine is a tropane alkaloid extracted from deadly nightshade , jimsonweed , Mandrake and other plants of the family Solanaceae. It is a secondary metabolite of these plants and serves as a hard 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 or deadly nightshade, is a perennial plant herbaceous plant in the family Solanaceae, native to Europe, North Africa, and Western Asia....
     (    Atropa belladonna)
  • Hyoscyamine
    Hyoscyamine

    Hyoscyamine, pronounced hi-oh-SYE-uh-meen, is a chemical compound, a tropane alkaloid. It is the levorotary isomer to atropine. It is a secondary metabolite found in certain plants of the Solanaceae family, including henbane, mandrake , jimsonweed , and deadly nightshade ....
    , the     levo-isomer
    Isomer

    In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
     of atropine, from henbane
    Henbane

    Henbane , also known as stinking nightshade, is a plant of the family Solanaceae that originated in Eurasia, though it is now globally distributed....
     (    Hyoscamus niger) and mandrake
    Mandrake (plant)

    Mandrake is the common name for members of the plant genus Mandragora belonging to the nightshades family . Because mandrake contains deliriant hallucinogenic tropane alkaloids such as hyoscyamine and the roots sometimes contain bifurcations causing them to resemble human figures, their roots have long been used in magic rituals, t...
     (    Mandragora officinalis)
  • Scopolamine
    Scopolamine

    Scopolamine, known by the names levo-duboisine and hyoscine, is a tropane alkaloid Medication with muscarinic antagonist effects. It is obtained from plants of the family Solanaceae , such as henbane, jimson weed and Angel's Trumpets , and corkwood ....
    , from henbane and     Datura
    Datura

    Datura is a genus of nine species of Vespertine flowering plants belonging to the family Solanaceae. Their exact natural distribution is uncertain, due to extensive cultivation and naturalisation throughout the temperate and tropical regions of the globe, but is most likely restricted to the Americas, from the United States south throug...
     species (Jimson weed)


Stimulants


Stimulant
Stimulant

Stimulant drugs are drugs that temporarily increase alertness and awareness. They usually have increased side-effects with increased effectiveness, and the more powerful variants are therefore often prescription medicines or illegal drugs....
s and cocaine-related alkaloids:

  • Cocaine
    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....
    , from     Erythroxylum coca
  • Ecgonidine
    Ecgonidine

    Ecgonidine is an alkaloid related to ecgonine and cocaine.Methylecgonidine is produced by pyrolysis in the process of smoking crack cocaine, and then subsequently metabolised to ecgonidine, and so these two compounds can be tested for as a specific biomarker for crack cocaine use....
    , and methylecgonidine
    Methylecgonidine

    Methylecgonidine is a chemical intermediate derived from ecgonine or cocaine.Methylecgonidine is a pyrolysis product formed when crack cocaine is smoked, making this substance a useful biomarker to specifically test for use of crack cocaine, as opposed to powder cocaine which does not form methylecgonidine as a metabolite....
    , pyrolysis
    Pyrolysis

    Pyrolysis is the chemical decomposition of a condensed substance by heating. The word is coined from the Greek language-derived morphemes pyro "fire" and lysys "decomposition"....
     products of cocaine
  • Ecgonine
    Ecgonine

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

    Benzoylecgonine is the primary metabolite of cocaine. It is formed in the liver by the metabolism of cocaine, catalysed by carboxylesterases, and subsequently excreted in the urine....
    , a metabolite of cocaine
  • Cocaethylene
    Cocaethylene

    Cocaethylene is the ethyl ester of benzoylecgonine. It is chemically related to cocaine, which is the corresponding methyl ester. Cocaethylene is formed in the body when cocaine and Ethanol have been taken simultaneously: the transesterification is catalysed by carboxylesterases in the liver....
    , a metabolite of cocaine
  • Hydroxytropacocaine
    Hydroxytropacocaine

    Hydroxytropacocaine is a tropane alkaloid found in Erythroxylum coca.References ...
    , from     Erythroxylum coca
  • Methylecgonine cinnamate
    Methylecgonine cinnamate

    Methylecgonine cinnamate is a natural tropane alkaloid found within the Coca plant. Its more common name, cinnamoylcocaine, reflects its close structural similarity to cocaine....
    , from     Erythroxylum coca


Others


  • Catuabine
    Catuabine

    Catuabines are a group of tropane alkaloids, isolated from Erythroxylum vacciniifolium, which are used in the preparation of the drug Catuaba....
    s, found in the drug catuaba
    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


  • Phenyltropane
    Phenyltropane

    Phenyltropanes are a class of cocaine-like psychoactive stimulants.Phenyltropane compounds comprise a large family of related molecules, developed during research into the mechanism of action of certain kinds of drugs such as cocaine and other dopamine reuptake inhibitors, which in general act as inhibitors of the monoamine reuptake Neuro...
    s

See also


  • Alkaloid
    Alkaloid

    Alkaloids are naturally occurring chemical compounds containing base nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base....
  • Tropane
    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....