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Revision as of 05:31, 31 August 2011 editBogBot (talk | contribs)Bots53,132 edits populated new fields in {{drugbox}} and reordered per bot approval. Report errors and suggestions to User_talk:BogBot← Previous edit		Latest revision as of 00:44, 4 March 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,043 edits Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. Alter: journal, title. Added s2cid. | Use this tool. Report bugs. | #UCB_Gadget
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			{{Short description|Chemical compound}}
			{{cs1 config|name-list-style=vanc}}
	{{Drugbox		{{Drugbox
	| Verifiedfields = changed		| Verifiedfields = changed
			| Watchedfields = changed
	| verifiedrevid = 409095900		| verifiedrevid = 447608674
	| IUPAC_name = (3α,14β,16α)-14,15-dihydro-<br>14-hydroxyeburnamenine-14-carboxylic acid methyl ester<br />OR<br />methyl (15''R'',17''S'',19''R'')-15-ethyl-17-hydroxy-1,11-diazapentacyclononadeca-2(7),3,5,8(18)-tetraene-17-carboxylate		| IUPAC_name = (3α,14β,16α)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester<br />or<br />Methyl (15''R'',17''S'',19''R'')-15-ethyl-17-hydroxy-1,11-diazapentacyclononadeca-2(7),3,5,8(18)-tetraene-17-carboxylate
	| image = Vincamine.svg		| image = (+)-Vincamine Structural Formula V2.svg
			| width = 175
	<!--Clinical data-->		<!--Clinical data-->
	| tradename =		| tradename = Oxybral SR
	| Drugs.com = {{drugs.com|international|vincamine}}		| Drugs.com = {{drugs.com|international|vincamine}}
	| pregnancy_category =		| pregnancy_category =
	| legal_status =		| legal_status =
	| routes_of_administration =		| routes_of_administration = Oral
	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
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	<!--Identifiers-->		<!--Identifiers-->
			| CAS_number_Ref = {{cascite|correct|??}}
	| CAS_number = 1617-90-9		| CAS_number = 1617-90-9
	| ATC_prefix = C04		| ATC_prefix = C04
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	| IUPHAR_ligand = 349		| IUPHAR_ligand = 349
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank =		| DrugBank = DB13374
	| UNII_Ref = {{fdacite|changed|FDA}}		| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 1165342
			| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 996XVD0JHT		| UNII = 996XVD0JHT
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D08677		| KEGG = D08677
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 14635
			| smiles = O=C(OC)3(O)n1c4c(c2ccccc12)CCN5CCC(C3)(CC)45
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| 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 = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = RXPRRQLKFXBCSJ-GIVPXCGWSA-N
	<!--Chemical data-->		<!--Chemical data-->
	| C=21 | H=26 | N=2 | O=3		| C=21 | H=26 | N=2 | O=3
	| molecular_weight = 354.44 g/mol
	}}		}}
	'''Vincamine''' is a peripheral ] that increases blood flow to the brain (sold under the trademark '''Oxybral''') . It is an ] ] (specifically a ]) found in the leaves of '']'', comprising about 25-65% of the indole alkaloids found in ''Vinca minor'' by weight. It is also found in the species '']''.{{Ref|Cook}} It can be synthesized from related alkaloids.{{Ref|Ullmann}}		'''Vincamine''' is a monoterpenoid ] found in the leaves of '']'' (lesser periwinkle), comprising about 25–65% of its indole alkaloids by weight. It can also be ] from related alkaloids.<ref>{{ cite encyclopedia | title = Indole Alkaloids | encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry | edition = Fifth | page = 393 | publisher = Wiley-VCH | year = 1985 | isbn = 3-527-20100-9 }}</ref>
			==Uses==
	Vincamine is often used as a ] agent to combat the effects of aging, or in conjunction with other nootropics (such as ]) for a variety of purposes.
			Vincamine is sold in Europe as a prescription medicine for the treatment of primary degenerative and vascular dementia.{{cn|date=July 2019}} 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.<ref>{{cite web | url = https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/vincamine_508.pdf | title = Summary of Data for Chemical Selection: Vincamine | work = National Toxicology Program | publisher = U.S. Department of Health and Human Services }}</ref> Most common preparations are in the ] tablet forms.
			==Chemistry==
			===Synthesis===
			] can be used for semi-synthesis of vincamine.<ref name = "Leeuwenberg_1985">{{cite journal|url=https://www.erowid.org/plants/voacanga_africana/voacanga_africana_info1.shtml|journal=Agricultural University Wageningen Papers|issn=0169-345X|volume=85|issue=3|year=1985|title=Voacanga, (Apocynaceae), a review of taxonomy, phytochemistry, ethnobotany and pharmacology| vauthors = Leeuwenberg AJ |author1-link=Anthonius Josephus Maria Leeuwenberg}}</ref>
			===Derivatives===
			] is a synthetic ] of vincamine used for cerebrovascular diseases and as dietary supplement.<ref>{{Cite journal | url=https://www.fda.gov/Food/DietarySupplements/ProductsIngredients/ucm518478.htm |title = Vinpocetine in Dietary Supplements|journal = FDA|date = 2019-06-03}}</ref> Vincamine derivatives have been also studied as anti addictive<ref name="pmid31913038">{{cite journal |vauthors=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 |title=Preventing Morphine-Seeking Behavior through the Re-Engineering of Vincamine's Biological Activity |journal=] |volume=63 |issue=10 |pages=5119–5138 |date=May 2020 |pmid=31913038 |pmc=7324933 |doi=10.1021/acs.jmedchem.9b01924 |url= |issn=}}</ref> and antidiabetic<ref name="pmid31918073">{{cite journal |vauthors=Wang J, Lv X, Xu J, Liu X, Du T, Sun G, Chen J, Shen X, Wang J, Hu L |title=Design, synthesis and biological evaluation of vincamine derivatives as potential pancreatic β-cells protective agents for the treatment of type 2 diabetes mellitus |journal=] |volume=188 |issue= |pages=111976 |date=February 2020 |pmid=31918073 |doi=10.1016/j.ejmech.2019.111976 |s2cid=210133217 |url= |issn=}}</ref> agents.
			==Research==
			It may have ] effects.<ref name = "Leeuwenberg_1985" /> It has been investigated as novel anticancer drug.<ref name="pmid33450545">{{cite journal |vauthors=Al-Rashed S, Baker A, Ahmad SS, Syed A, Bahkali AH, Elgorban AM, Khan MS |title=Vincamine, a safe natural alkaloid, represents a novel anticancer agent |journal=] |volume=107 |issue= |pages=104626 |date=February 2021 |pmid=33450545 |doi=10.1016/j.bioorg.2021.104626 |s2cid=231624167 |url= |issn=}}</ref>
			Concerns over long-term use have been documented by the US ].<ref>{{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}}</ref>
		⚫	== See also ==
			*]
			*]
	==References==		==References==
			{{reflist}}
	#{{Note|Cook}}{{cite journal
	| doi = 10.1056/NEJM198112243052604
	| author = Cook, P; James, I
	| title = Cerebral vasodilators
	| journal = N Engl J Med.
	| volume = 305
	| issue = 26
	| pages = 1560–1564
	| date = Dec. 24, 1981
	| pmid = 7031468
	}}
	#{{Note|Ullmann}}{{cite encyclopedia
	| title = Indole Alkaloids
	| encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry, Fifth Edition
	| volume =
	| pages = 393
	| publisher = Wiley-VCH
	| year = 1985
	| id = ISBN 3-527-20100-9
	| accessdate =
	}}
	==External links==		==External links==
	*		* {{cite web | url = http://www.mpbio.com/includes/msds/ansi/en/158295-EN-ANSI.pdf | title = Vincamine MSDS | access-date = 2012-01-30 | archive-url = https://web.archive.org/web/20150608110220/http://www.mpbio.com/includes/msds/ansi/en/158295-EN-ANSI.pdf | archive-date = 2015-06-08 | url-status = dead }}
			* {{cite web | url = https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/vincamine_508.pdf | work = Summary of Data for Chemical Selection | title = Vincamine - 1617-90-9 | author = Chemical Selection Working Group | publisher = NIH - United States National Institutes of Health | access-date = 2007-04-23 | archive-url = https://web.archive.org/web/20111021222436/http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/Vincamine.pdf | archive-date = 2011-10-21 | url-status = live }}
	*
⚫	==See also==
	* ]
	{{Peripheral vasodilators}}		{{Peripheral vasodilators}}
	]		]
			]
	]		]
	]		]
	]		]
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	{{cardiovascular-drug-stub}}
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