Vincamine

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Vincamine
Clinical data
Trade namesOxybral SR
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Identifiers
  • (3α,14β,16α)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
    or
    Methyl (15R,17S,19R)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2(7),3,5,8(18)-tetraene-17-carboxylate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC21H26N2O3
Molar mass354.450 g·mol−1
3D model (JSmol)
  • O=C(OC)[C@]3(O)n1c4c(c2ccccc12)CCN5CCC[C@](C3)(CC)[C@@H]45
  • InChI=1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+/m1/s1 ☒N
  • Key:RXPRRQLKFXBCSJ-GIVPXCGWSA-N ☒N
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Vincamine is a monoterpenoid indole alkaloid found in the leaves of Vinca minor (lesser periwinkle), comprising about 25–65% of its indole alkaloids by weight. It can also be synthesized from related alkaloids.[1]

Uses

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Vincamine is sold in Europe as a prescription medicine for the treatment of primary degenerative and vascular dementia.[citation needed] In the United States, it is permitted to be sold as a dietary supplement when labeled for use in adults for six months or less.[2] Most common preparations are in the sustained release tablet forms.

Chemistry

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Synthesis

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Tabersonine can be used for semi-synthesis of vincamine.[3]

Derivatives

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Vinpocetine is a synthetic derivative of vincamine used for cerebrovascular diseases and as dietary supplement.[4] Vincamine derivatives have been also studied as anti addictive[5] and antidiabetic[6] agents.

Research

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It may have nootropic effects.[3] It has been investigated as novel anticancer drug.[7]

Concerns over long-term use have been documented by the US National Toxicology Program.[8]

See also

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References

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