Vincamine

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[9.6.2.02,7.08,18.015,19]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 ;
	(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. 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

^ "Indole Alkaloids". Ullmann's Encyclopedia of Industrial Chemistry (Fifth ed.). Wiley-VCH. 1985. p. 393. ISBN 3-527-20100-9.
^ "Summary of Data for Chemical Selection: Vincamine" (PDF). National Toxicology Program. U.S. Department of Health and Human Services.
^ ^a ^b Leeuwenberg AJ (1985). "Voacanga, (Apocynaceae), a review of taxonomy, phytochemistry, ethnobotany and pharmacology". Agricultural University Wageningen papers. 85 (3). ISSN 0169-345X.
^ "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.

[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.

[Leeuwenberg_1985-3] 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.

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