Vincamine: Difference between revisions

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

| Watchedfields = changed

| verifiedrevid = 447608674

| 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-diazapentacyclo[9.6.2.0^2,7.0^8,18.0^15,19]nonadeca-2(7),3,5,8(18)-tetraene-17-carboxylate

| image = (+)-Vincamine Structural Formula V2.svg

| width = 175

| tradename = Oxybral SR

| routes_of_administration = Oral

| CAS_number_Ref = {{cascite|correct|??}}

| DrugBank = DB13374

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1165342

| UNII_Ref = {{fdacite|correct|FDA}}

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 14635

| smiles = O=C(OC)[C@]3(O)n1c4c(c2ccccc12)CCN5CCC[C@](C3)(CC)[C@@H]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

'''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 [[organic synthesis|synthesized]] 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 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 [[sustained release]] tablet forms.

==Chemistry==

===Synthesis===

[[Tabersonine]] 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===

[[Vinpocetine]] is a synthetic [[derivative (chemistry)|derivative]] 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=[[Journal of Medicinal Chemistry]] |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=[[European Journal of Medicinal Chemistry]] |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 [[nootropic]] 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=[[Bioorganic Chemistry]] |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 [[National Toxicology Program]].<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 ==

*[[Apparicine]]

*[[Conophylline]]

{{reflist}}

* {{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 }}

[[Category:Tertiary alcohols]]

[[Category:Tryptamine alkaloids]]

[[Category:Quinolizidine alkaloids]]

[[Category:Vinca alkaloids]]

[[Category:Heterocyclic compounds with 5 rings]]