Hygrine

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Hygrine
Hygrine Structural Formula V.1.svg
Hygrine ball-and-stick.png
Names
Preferred IUPAC name
1-[(2R)-1-Methylpyrrolidin-2-yl]propan-2-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.112 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C8H15NO/c1-7(10)6-8-4-3-5-9(8)2/h8H,3-6H2,1-2H3/t8-/m1/s1 Yes check.svgY
    Key: ADKXZIOQKHHDNQ-MRVPVSSYSA-N Yes check.svgY
  • InChI=1/C8H15NO/c1-7(10)6-8-4-3-5-9(8)2/h8H,3-6H2,1-2H3/t8-/m1/s1
    Key: ADKXZIOQKHHDNQ-MRVPVSSYBT
  • CC(=O)C[C@H]1CCCN1C
Properties
C8H15NO
Molar mass 141.21 g/mol
Boiling point 193 to 195 °C (379 to 383 °F; 466 to 468 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

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 in coca. Hygrine is extracted as a thick yellow oil, having a pungent taste and odor.

See also

Related Research Articles

Cocaine Tropane alkaloid and strong stimulant

Cocaine is a tropane alkaloid and strong (SNDRI) stimulant made from coca leaves of one of four species of plant in the Erythroxylaceae family. It is frequently used as a recreational drug and euphoriant. It may be snorted, inhaled as smoke, or dissolved and injected into a vein. Mental effects may include an intense feeling of happiness, sexual arousal, loss of contact with reality, or agitation. Physical symptoms may include a fast heart rate, sweating, and dilated pupils. High doses can result in high blood pressure or body temperature. Effects begin within seconds to minutes of use and last between five and ninety minutes. Cocaine's medical uses include local numbing and reduced bleeding from the nasal mucosa during nasal surgery.

Coca Group of plant varieties cultivated for coca production

Coca is any of the four cultivated plants in the family Erythroxylaceae, native to western South America. Coca is known for its psychoactive alkaloid, cocaine.

Convolvulaceae Family of flowering plants

Convolvulaceae, known commonly as the bindweed or morning glory family, is a family of about 60 genera and more than 1,650 species of mostly herbaceous vines, but also trees, shrubs and herbs, and also including the sweet potato and a few other food tubers.

Hyoscyamine Pharmaceutical drug

Hyoscyamine is a naturally occurring tropane alkaloid and plant toxin. It is a secondary metabolite found in certain plants of the family Solanaceae, including henbane, mandrake, angel's trumpets, jimsonweed, tomato, the sorcerers' tree, and deadly nightshade. It is the levorotary isomer of atropine and thus sometimes known as levo-atropine.

Methylecgonine cinnamate Chemical compound

Methylecgonine cinnamate is a natural tropane alkaloid found within the coca plant. Its more common name, cinnamoylcocaine, reflects its close structural similarity to cocaine. It is said to be pharmacologically inactive. But some studies funded by anti-drug agencies imply that it is active when smoked. Furthermore, the discovery of differing impurity products yielding methylecgonine cinnamate in confiscated cocaine have led enforcing agencies to postulate that illicit manufacturers have changed their oxidation procedures when refining cocaine from a crude form. Methylecgonine cinnamate can dimerize to the truxillic acid derivative truxilline. It is notable that methylecgonine cinnamate is given in patents of active cocaine analogue structures.

Benzoylecgonine Chemical compound

Benzoylecgonine is the main metabolite of cocaine, formed by the liver and excreted in the urine. It is the compound tested for in most cocaine urine drug screens.

On a New Organic Base in the Coca Leaves is an 1860 dissertation written by Dr. Albert Niemann. Its title in German is Über eine neue organische Base in den Cocablättern. The piece describes, in detail, how Niemann isolated cocaine, a crystalline alkaloid. It also earned Niemann his Ph.D. and is now in the British Library. He wrote of the alkaloid's "colourless transparent prisms" and said that, "Its solutions have an alkaline reaction, a bitter taste, promote the flow of saliva and leave a peculiar numbness, followed by a sense of cold when applied to the tongue." Niemann named the alkaloid "cocaine" — as with other alkaloids its name carried the "-ine" suffix.

Tropane is a nitrogenous bicyclic organic compound. It is mainly known for a group of alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families Erythroxylaceae and Solanaceae.

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 organic solvents. It has a characteristic odor that has been described as "ammoniacal, fishy, shellfish-like". In addition to pyrrolidine itself, many substituted pyrrolidines are known.

Cuscohygrine Chemical compound

Cuscohygrine is a pyrrolidine alkaloid found in coca. It can also be extracted from plants of the family Solanaceae, including Atropa belladonna, Datura innoxia and Datura stramonium. Cuscohygrine usually occurs along with other, more potent alkaloids such as atropine or cocaine.

Hydroxytropacocaine Chemical compound

Hydroxytropacocaine is a tropane alkaloid found in Erythroxylum coca.

Ecgonine Chemical compound

Ecgonine is a 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 in many jurisdictions, as are some substances which can be used as precursors to ecgonine itself.

Coca tea Infusion of coca plant leaves

Coca tea, also called mate de coca, is an herbal tea (infusion) made using the raw or dried leaves of the coca plant, which is native to South America. It is made either by submerging the coca leaf or dipping a tea bag in hot water. The tea is most commonly consumed in the Andes mountain range, particularly Argentina, Ecuador, Peru and especially in Bolivia, where it is consumed all around the country because it is the only country where coca leaves are legal. It is greenish yellow in color and has a mild bitter flavor similar to green tea with a more organic sweetness.

Catuabine

Catuabines are a group of tropane alkaloids, isolated from Erythroxylum vaccinifolium, 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. The catuabines are not known to have any physiological effects, this is in contrast to cocaine, which is an active constituent of another species, Erythroxylum coca.

Free base is the conjugate base (deprotonated) form of an amine, as opposed to its conjugate acid (protonated) form. The amine is often an alkaloid, such as nicotine, cocaine, morphine, and ephedrine, or derivatives thereof. Freebasing is a more efficient method of self-administering alkaloids via the smoking route.

Tropane alkaloid Class of chemical compounds

Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. 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.

Albert Friedrich Emil Niemann was a German chemist. In 1859 - about the same time as Paolo Mantegazza - he isolated cocaine, and he published his finding in 1860.

Biosynthesis of cocaine

The biosynthesis of cocaine has long attracted the attention of biochemists and organic chemists. This interest is partly motivated by the strong physiological effects of cocaine, but a further incentive was the unusual bicyclic structure of the molecule. The biosynthesis can be viewed as occurring in two phases, one phase leading to the N-methylpyrrolinium ring, which is preserved in the final product. The second phase incorporates a C4 unit with formation of the bicyclic tropane core.

Coca alkaloids are the alkaloids found in the coca plant, Erythroxylum coca. They are predominantly of either the pyrrolidine or the tropane types.

Apparicine Chemical compound

Apparicine is a monoterpenoid indole alkaloid. It is named after Apparicio Duarte, a Brazilian botanist who studied the Aspidosperma species from which apparicine was first isolated. It was the first member of the vallesamine group of alkaloids to be isolated and have its structure established, which was first published in 1965. It has also been known by the synonyms gomezine, pericalline, and tabernoschizine.

References