Vincamine

Source: Wikipedia, the free encyclopedia.
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
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
 ☒NcheckY (what is this?)  (verify)

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

Vincamine is sold in Europe as a prescription medicine for the treatment of primary degenerative and vascular dementia.[

sustained release
tablet forms.

Chemistry

Synthesis

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

Derivatives

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

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

References

  1. .
  2. ^ "Summary of Data for Chemical Selection: Vincamine" (PDF). National Toxicology Program. U.S. Department of Health and Human Services.
  3. ^
    ISSN 0169-345X
    .
  4. ^ "Vinpocetine in Dietary Supplements". FDA. 2019-06-03.
  5. PMID 31913038
    .
  6. .
  7. .
  8. ^ "Vincamine Dietary Supplements 1617-90-9 - National Toxicology Program" (PDF). National Institute of Environmental Health Sciences. Retrieved 4 December 2023.

External links

  • "Vincamine MSDS" (PDF). Archived from the original (PDF) on 2015-06-08. Retrieved 2012-01-30.
  • Chemical Selection Working Group. "Vincamine - 1617-90-9" (PDF). Summary of Data for Chemical Selection. NIH - United States National Institutes of Health. Archived (PDF) from the original on 2011-10-21. Retrieved 2007-04-23.