Vincamine

Vincamine
Clinical data
Trade names	Oxybral SR
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
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 Y;
PubChem CID	15376;
IUPHAR/BPS	349;
DrugBank	DB13374 Y;
ChemSpider	14635 N;
UNII	996XVD0JHT;
KEGG	D08677 Y;
ChEMBL	ChEMBL1165342 N;
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 N; Key:RXPRRQLKFXBCSJ-GIVPXCGWSA-N N;
	NY (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.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.

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 addictive⁵ and antidiabetic⁶ agents.

Research

It may have nootropic effects.³ It has been investigated as novel anticancer drug.⁷

Concerns over long-term use have been documented by the US National Toxicology Program.⁸

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. Archived from the original (PDF) on September 9, 2015.
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.
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.
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.
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.
"Vincamine Dietary Supplements 1617-90-9 - National Toxicology Program" (PDF). National Institute of Environmental Health Sciences. Retrieved 4 December 2023.

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 from the original (PDF) 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. Archived from the original (PDF) on September 9, 2015.

[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.

[pmid31913038-5] 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.

[pmid31918073-6] 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.

[pmid33450545-7] 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.

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