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Cuscohygrine information


Cuscohygrine
Chemical structure of cuscohygrine
Names
Preferred IUPAC name
1-[(2R)-1-Methylpyrrolidin-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]propan-2-one
Identifiers
CAS Number
  • 454-14-8
3D model (JSmol)
  • Interactive image
3DMet
  • B05209
ChemSpider
  • 21864896
KEGG
  • C06521
PubChem CID
  • 1201543
UNII
  • 93FJ3823VL
CompTox Dashboard (EPA)
  • DTXSID70894079 Edit this at Wikidata
InChI
  • InChI=1S/C13H24N2O/c1-14-7-3-5-11(14)9-13(16)10-12-6-4-8-15(12)2/h11-12H,3-10H2,1-2H3/t11-,12+
    Key: ZEBIACKKLGVLFZ-TXEJJXNPSA-N
SMILES
  • CN1CCC[C@@H]1CC(=O)C[C@@H]2CCCN2C
Properties
Chemical formula
C13H24N2O
Molar mass 224.348 g·mol−1
Melting point 40–41 °C (104–106 °F; 313–314 K) (trihydrate)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cuscohygrine is a bis N-methyl pyrrolidine alkaloid found in coca plants. It can also be extracted from plants of the family Solanaceae, including Atropa belladonna (deadly nightshade) and various Datura species. Cuscohygrine usually occurs along with other, more potent alkaloids such as atropine or cocaine.

Cuscohygrine, along with the related metabolite hygrine, was first isolated by Carl Liebermann 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 trihydrate which melts at 40–41 °C.

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Cuscohygrine

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Cuscohygrine is a bis N-methyl pyrrolidine alkaloid found in coca plants. It can also be extracted from plants of the family Solanaceae, including Atropa...

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Hygrine

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first isolated by Carl Liebermann in 1889 (along with a related compound cuscohygrine) as an alkaloid accompanying cocaine in coca. Hygrine is extracted as...

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Withania somnifera

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that include withaferin A, alkaloids, steroidal lactones, tropine, and cuscohygrine. Forty withanolides, twelve alkaloids, and various sitoindosides have...

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Coca alkaloid

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Hydroxytropacocaine Methylecgonine cinnamate Tropacocaine Truxilline Cuscohygrine Dihydrocuscohygrine Hygrine Nicotine Cocaine metabolites (Human) Coca...

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Mandragora officinarum

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root included atropine, hyoscyamine, scopolamine (hyoscine), scopine, cuscohygrine, apoatropine, 3-alpha-tigloyloxytropane, 3-alpha,6-beta-ditigloyloxytropane...

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Alkaloid

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or arginine → putrescine → N-methylputrescine → N-methyl-Δ1-pyrroline Cuscohygrine, hygrine, hygroline, stachydrine Tropane derivatives Atropine group Substitution...

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Dihydrocuscohygrine

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Dihydrocuscohygrine is an alkaloid that has been isolated from coca leaves. Cuscohygrine Pseudotropine Turner, C.E.; Elsohly, M.A.; Hanus, L.; Elsohly, H.N. (1981)...

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Scopolia

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memory-inhibiting effects. Other alkaloids found in Scopolia carniolica include cuscohygrine, hyoscyamine, and atroscine. The coumarin phenylpropanoids umbelliferone...

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Methylecgonine cinnamate

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coca leaves and abuse of cocaine by hair analysis including hygrine, cuscohygrine, cinnamoylcocaine and cocaine metabolite/cocaine ratios". International...

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Scopine

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"Alkaloids in Scopolia lurida. Chromatographic analysis. Isolation of cuscohygrine". Acta Poloniae Pharmaceutica. 24 (1): 59–64. Meinwald, J.; Chapman,...

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Convolvulus arvensis

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including pseudotropine, and lesser amounts of tropine, tropinone, and meso-cuscohygrine. The alkaloids are also reported to give the plant psychoactive properties...

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List of poisonous plants

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root included atropine, hyoscyamine, scopolamine (hyoscine), scopine, cuscohygrine, apoatropine, 3-alpha-tigloyloxytropane, 3-alpha,6-beta-ditigloyloxytropane...

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Catuabine

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an active constituent of another species, Erythroxylum coca. Hygrine Cuscohygrine Glasl, S.; Presser, A.; Werner, I.; Haslinger, E.; Jurenitsch, J. (2003):...

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List of drugs by year of discovery

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Mandragora officinarum Atropine and scopolamine (antimuscarinics), scopine, cuscohygrine, apoatropine, Belladonnines and non-alkaloid constituents including sitosterol...

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Biosynthesis of cocaine

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the N-methyl-pyrrolinium cation is a precursor to nicotine, hygrine, cuscohygrine, and other natural products. The additional carbon atoms required for...

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Coca

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benzoylecgonine, truxilline, hydroxytropacocaine, tropacocaine, ecgonine, cuscohygrine, dihydrocuscohygrine, and hygrine. When chewed, coca acts as a mild stimulant...

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Mandragora autumnalis

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of M. autumnalis). Alkaloids present included hyoscyamine, hyoscine, cuscohygrine, apoatropine, 3-alpha-tigloyloxytropane, 3-alpha,6-beta-ditigloyloxytropane...

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C13H24N2O

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C13H24N2O (molar mass: 224.34 g/mol, exact mass: 224.1889 u) may refer to: Cuscohygrine Dicyclohexylurea This set index page lists chemical structure articles...

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Physochlaina

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3-O-β-D-glucopyranoside-β-sitosterol and the alkaloids atropine, scopolamine and cuscohygrine. 西藏泡囊草 (H'si-Tsang Pao-nang-ts'ao / xi zang pao nang cao = 'Tibetan Physochlaina...

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Atropanthe

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and anisodine and also the pyrrolidine alkaloid bellaradine, a.k.a. cuscohygrine, (which is not one of the tropane alkaloids, but may be biogenetically...

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List of compounds with carbon number 13

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isopropyldecalin 27193-29-9 C13H24Cl6O8P2 phosgard 2xc20 38051-10-4 C13H24N2O cuscohygrine 454-14-8 C13H24N2O N,N'-dicyclohexyl urea 2387-23-7 C13H24N2O2 cropropamide...

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