Cuscohygrine is a bis N-methyl

pyrrolidine Pyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula (CH2)4NH. It is a cyclic secondary amine, also classified as a saturated heterocycle. It is a colourless liquid that is miscible with water and most ...

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 ...

found in coca plants. It can also be extracted from plants of the family

Solanaceae Solanaceae (), commonly known as the nightshades, is a family of flowering plants in the order Solanales. It contains approximately 2,700 species, several of which are used as agricultural crops, medicinal plants, and ornamental plants. Many me ...

, including ''

Atropa belladonna ''Atropa bella-donna'', commonly known as deadly nightshade or belladonna, is a toxic perennial herbaceous plant in the nightshade family Solanaceae, which also includes tomatoes, potatoes and eggplant. It is native to Europe and Western Asia, i ...

'' (deadly nightshade) and various ''

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. Cuscohygrine usually occurs along with other, more potent alkaloids such as

atropine Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically give ...

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 ...

. Cuscohygrine, along with the related

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

hygrine Hygrine is a pyrrolidine alkaloid, found mainly in coca leaves (0.2%). It was first isolated by Carl Liebermann in 1889 (along with a related compound cuscohygrine) as an alkaloid accompanying cocaine Cocaine is a tropane alkaloid a ...

, was first isolated by

Carl Liebermann Carl Theodor Liebermann (23 February 1842 – 28 December 1914) was a German chemist and student of Adolf von Baeyer. Life Liebermann first studied at the University of Heidelberg where Robert Wilhelm Bunsen was teaching. He then joined the ...

in 1889 as an alkaloid accompanying cocaine in coca leaves (also known as Cusco-leaves). Cuscohygrine is an oil that can be distilled without decomposition only in vacuum. It is soluble in water. It also forms a crystalline tri

hydrate In chemistry, a hydrate is a substance that contains water or its constituent elements. The chemical state of the water varies widely between different classes of hydrates, some of which were so labeled before their chemical structure was understo ...

which melts at 40–41 °C.

Biosynthesis

Ornithine is methylated to N-methylornithine and when decarboxylated, becomes N-methylputrescine. 4-methylaminobutanal is yielded from the oxidation of the primary amino-group. 4-methylaminobutanal then cyclizes to an N-methyl-l-pyrrolinium salt. The condensation of the pyrrolinium salt with acetoacetyl coenzyme A yields hygrine. Finally, the condensation of the hygrine molecule with another molecule of pyrrolidinium salt yields cuscohygrine. Biosynthesis of Cuscohygrine

References

* * {{cite book , author=Dr. Ame Pictet , title=The Vegetable Alkaloids. With particular reference to their chemical constitution , location=London , publisher=Chapman & Hall , year=1904 Pyrrolidine alkaloids Alkaloids found in Erythroxylum coca Alkaloids found in Solanaceae Ketones

Biosynthesis

See also

References