Vincamine

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]

Vincamine
Clinical data
Trade namesOxybral SR
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • (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
CompTox Dashboard (EPA)
ECHA InfoCard100.015.070
Chemical and physical data
FormulaC21H26N2O3
Molar mass354.450 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OC)[C@]3(O)n1c4c(c2ccccc12)CCN5CCC[C@](C3)(CC)[C@@H]45
InChI
  • 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
 NY (what is this?)  (verify)

Uses

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

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]

See also
  • Apparicine
  • Conophylline

References
  1. "Indole Alkaloids". Ullmann's Encyclopedia of Industrial Chemistry (Fifth ed.). Wiley-VCH. 1985. p. 393. ISBN 3-527-20100-9.
  2. "Summary of Data for Chemical Selection: Vincamine" (PDF). National Toxicology Program. U.S. Department of Health and Human Services.
  3. Leeuwenberg AJ (1985). "Voacanga, (Apocynaceae), a review of taxonomy, phytochemistry, ethnobotany and pharmacology". Agricultural University Wageningen papers. 85 (3). ISSN 0169-345X.
  4. "Vinpocetine in Dietary Supplements". FDA. 2019-06-03.
  5. Norwood VM, Brice-Tutt AC, Eans SO, Stacy HM, Shi G, Ratnayake R, Rocca JR, Abboud KA, Li C, Luesch H, McLaughlin JP, Huigens RW (May 2020). "Preventing Morphine-Seeking Behavior through the Re-Engineering of Vincamine's Biological Activity". Journal of Medicinal Chemistry. 63 (10): 5119–5138. doi:10.1021/acs.jmedchem.9b01924. PMC 7324933. PMID 31913038.
  6. Wang J, Lv X, Xu J, Liu X, Du T, Sun G, Chen J, Shen X, Wang J, Hu L (February 2020). "Design, synthesis and biological evaluation of vincamine derivatives as potential pancreatic β-cells protective agents for the treatment of type 2 diabetes mellitus". European Journal of Medicinal Chemistry. 188: 111976. doi:10.1016/j.ejmech.2019.111976. PMID 31918073.
  7. Al-Rashed S, Baker A, Ahmad SS, Syed A, Bahkali AH, Elgorban AM, Khan MS (February 2021). "Vincamine, a safe natural alkaloid, represents a novel anticancer agent". Bioorganic Chemistry. 107: 104626. doi:10.1016/j.bioorg.2021.104626. PMID 33450545.
  • "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.
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