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 names	Oxybral SR
AHFS/Drugs.com	International Drug Names
ATC code	C04AX07 (WHO)
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[9.6.2.0^2,7.0^8,18.0^15,19]nonadeca-2(7),3,5,8(18)-tetraene-17-carboxylate
CAS Number	1617-90-9
PubChem CID	15376
IUPHAR/BPS	349
ChemSpider	14635
UNII	996XVD0JHT
KEGG	D08677
ChEMBL	ChEMBL1165342
CompTox Dashboard (EPA)	DTXSID9040134
ECHA InfoCard	100.015.070
Chemical and physical data
Formula	C21H26N2O3
Molar mass	354.450 g·mol^−1
3D model (JSmol)	Interactive image
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 Key:RXPRRQLKFXBCSJ-GIVPXCGWSA-N
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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.

Synthesis

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

Derivatives

Vinpocetine is a synthetic derivative of vincamine.[4]

Research

It may have nootropic effects.[3]

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.

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.