Vincamine

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
CompTox Dashboard (EPA)
ECHA InfoCard100.015.070 Edit this at Wikidata
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 X markN
  • Key:RXPRRQLKFXBCSJ-GIVPXCGWSA-N X markN
 X markNcheckY (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.

Uses

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. Most common preparations are in the sustained release tablet forms.

Chemistry

Synthesis

Tabersonine can be used for semi-synthesis of vincamine.

Derivatives

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

Research

It may have nootropic effects. It has been investigated as novel anticancer drug.

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

See also

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. Archived from the original (PDF) on September 9, 2015.
  3. 1 2 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. S2CID 210133217.
  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. S2CID 231624167.
  8. ↑ "Vincamine Dietary Supplements 1617-90-9 - National Toxicology Program" (PDF). National Institute of Environmental Health Sciences. Retrieved 4 December 2023.[dead link]