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Digoxin
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== History == Derivatives of plants of the genus ''Digitalis'' have a long history of medical use. [[Nicholas Culpeper]] referred to various medical uses for foxglove in his 1652 publication ''The English physician''.<ref>{{cite book | vauthors = Culpeper N |title=The English Physician, Etc |date=1652 |publisher=William Bentley |location=London |pages=97β98 |edition=1st |url=https://books.google.com/books?id=WuyUw_5Hd8cC&pg=RA1-PA173 |access-date=22 January 2023 |language=en}}</ref> [[William Withering]] is credited with the first published description of the systematic use of ''Digitalis'' derivatives in his 1785 book ''An Account of the Foxglove and some of its Medical Uses With Practical Remarks on [[Edema|Dropsy]] and Other Diseases''.<ref>{{cite book| vauthors = Withering W |title=An Account of the Foxglove and some of its Medical Uses With Practical Remarks on Dropsy and Other Diseases|year=1785|url=http://www.gutenberg.org/ebooks/24886|url-status=live|archive-url=https://web.archive.org/web/20170908000000/http://www.gutenberg.org/ebooks/24886|archive-date=2017-09-08}}</ref> Its use was somewhat sporadic until [[James_Mackenzie_(cardiologist)|Sir James Mackenzie]] identified the phenomenon of [[atrial fibrillation]], and the actions of digitalis on this.<ref>{{cite book | vauthors = Aronson JK |title=An Account of the Foxglove and its Medical Uses 1785β1985 |date=1985 |publisher=Oxford University Press |location=London |isbn=0192615017 |pages=Chapters 5β7 |edition=1st}}</ref> Its effects were first explained by [[Arthur Robertson Cushny]].<ref>{{cite journal | vauthors = Cushny AR |title=The Action and Uses in Medicine of Digitalis and its Allies |journal=Nature |date=1925 |volume=116 |issue=2905 |pages=8β9 |publisher=Longmans, Green and Co |location=London |doi=10.1038/116008a0 |bibcode=1925Natur.116....8. |hdl=2027/uc1.b3846609 |s2cid=9025850 |edition=1st |url=https://www.nature.com/articles/116008a0 |language=en|hdl-access=free }}</ref> The name is a [[portmanteau]], derived from ''Digitalis lanata'' and ''toxin''.<ref>{{cite web |title=digoxin |url=https://en.wiktionary.org/wiki/digoxin |website=Wiktionary |publisher=Wikimedia |access-date=21 January 2023 |language=en |date=16 January 2023}}</ref> In 1930, digoxin was first isolated by Dr. Sydney Smith from the foxglove plant, ''Digitalis lanata''.<ref name=cartwright/><ref name=hollman/><ref name=smith>{{cite journal| vauthors = Smith S |date=1930|publisher=The Royal Society of Chemistry|title=LXXII.βDigoxin, a new digitalis glucoside|url=https://pubs.rsc.org/en/content/articlepdf/1930/jr/jr9300000508|journal=J. Chem. Soc.|pages=508β510|doi=10.1039/JR9300000508|access-date=2020-10-22|archive-date=2021-06-02|archive-url=https://web.archive.org/web/20210602212903/https://pubs.rsc.org/en/content/articlelanding/1930/jr/jr9300000508/unauth|url-status=live|url-access=subscription}}</ref> Initially, the digoxin was purified by dissolving the dried plant material in acetone and boiling the solution in chloroform. The solution was then reacted with [[acetic acid]] and small amount of [[ferric chloride]] and [[sulfuric acid]] ([[Keller's reagent (organic)|Keller reaction]]). Digoxin was distinguishable from other [[glucosides]] by the olive-green colored solution produced from this reaction, completely free of red.<ref name=smith/>
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