Vincamine

---

title: "Vincamine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["tertiary-alcohols", "tryptamine-alkaloids", "methyl-esters", "quinolizidine-alkaloids", "vinca-alkaloids", "heterocyclic-compounds-with-5-rings"] description: "Chemical compound" topic_path: "general/tertiary-alcohols" source: "https://en.wikipedia.org/wiki/Vincamine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 447608674 | 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 | image = Vincamine.svg | image_class = skin-invert-image | width = 175

| tradename = Oxybral SR | Drugs.com = | pregnancy_category = | legal_status = | routes_of_administration = Oral

| bioavailability = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 1617-90-9 | ATC_prefix = C04 | ATC_suffix = AX07 | PubChem = 15376 | IUPHAR_ligand = 349 | DrugBank_Ref = | DrugBank = DB13374 | ChEMBL_Ref = | ChEMBL = 1165342 | UNII_Ref = | UNII = 996XVD0JHT | KEGG_Ref = | KEGG = D08677 | ChemSpiderID_Ref = | ChemSpiderID = 14635 | smiles = O=C(OC)[C@]3(O)n1c4c(c2ccccc12)CCN5CCCC@(CC)[C@@H]45 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = RXPRRQLKFXBCSJ-GIVPXCGWSA-N

| C=21 | H=26 | N=2 | O=3

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. 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.{{cite web |title=Vincamine Dietary Supplements 1617-90-9 - National Toxicology Program|url=https://ntp.niehs.nih.gov/sites/default/files/ntp/htdocs/chem_background/exsumpdf/vincamine_508.pdf |website=National Institute of Environmental Health Sciences |access-date=4 December 2023}}

References

References

1. (1985). "Indole Alkaloids". Wiley-VCH.
2. "Summary of Data for Chemical Selection: Vincamine". U.S. Department of Health and Human Services.
3. (1985). "Voacanga, (Apocynaceae), a review of taxonomy, phytochemistry, ethnobotany and pharmacology". Agricultural University Wageningen Papers.
4. (2019-06-03). "Vinpocetine in Dietary Supplements". FDA.
5. (May 2020). "Preventing Morphine-Seeking Behavior through the Re-Engineering of Vincamine's Biological Activity". [[Journal of Medicinal Chemistry]].
6. (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]].
7. (February 2021). "Vincamine, a safe natural alkaloid, represents a novel anticancer agent". [[Bioorganic Chemistry]].

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::