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Available in 24 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-24" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">24 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B3%D9%81%D8%B1%D8%A7%D9%86%D9%8A%D9%86" title="سفرانين – Arabic" lang="ar" hreflang="ar" data-title="سفرانين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%D9%81%D8%B1%D8%A7%D9%86%DB%8C%D9%86" title="سفرانین – South Azerbaijani" lang="azb" hreflang="azb" data-title="سفرانین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B8%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%AB%E0%A7%8D%E0%A6%B0%E0%A6%BE%E0%A6%A8%E0%A6%BF%E0%A6%A8" title="স্যাফ্রানিন – Bangla" lang="bn" hreflang="bn" data-title="স্যাফ্রানিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Safranina" title="Safranina – Catalan" lang="ca" hreflang="ca" data-title="Safranina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Safranin" title="Safranin – Czech" lang="cs" hreflang="cs" data-title="Safranin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Safranin_T" title="Safranin T – German" lang="de" hreflang="de" data-title="Safranin T" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Safranina" title="Safranina – Spanish" lang="es" hreflang="es" data-title="Safranina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%D9%81%D8%B1%D8%A7%D9%86%DB%8C%D9%86" title="سفرانین – Persian" lang="fa" hreflang="fa" data-title="سفرانین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Safranine" title="Safranine – French" lang="fr" hreflang="fr" data-title="Safranine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Safranina" title="Safranina – Galician" lang="gl" hreflang="gl" data-title="Safranina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%82%AC%ED%94%84%EB%9D%BC%EB%8B%8C" title="사프라닌 – Korean" lang="ko" hreflang="ko" data-title="사프라닌" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Safranin" title="Safranin – Croatian" lang="hr" hreflang="hr" data-title="Safranin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Safranine" title="Safranine – Dutch" lang="nl" hreflang="nl" data-title="Safranine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B5%E3%83%95%E3%83%A9%E3%83%8B%E3%83%B3" title="サフラニン – Japanese" lang="ja" hreflang="ja" data-title="サフラニン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Safranina" title="Safranina – Polish" lang="pl" hreflang="pl" data-title="Safranina" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Safranina" title="Safranina – Portuguese" lang="pt" hreflang="pt" data-title="Safranina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A1%D0%B0%D1%84%D1%80%D0%B0%D0%BD%D0%B8%D0%BD" title="Сафранин – Russian" lang="ru" hreflang="ru" data-title="Сафранин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Safranin" title="Safranin – Serbian" lang="sr" hreflang="sr" data-title="Safranin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Safranin" title="Safranin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Safranin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Safraniini" title="Safraniini – Finnish" lang="fi" hreflang="fi" data-title="Safraniini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Safranin" title="Safranin – Swedish" lang="sv" hreflang="sv" data-title="Safranin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A1%D0%B0%D1%84%D1%80%D0%B0%D0%BD%D1%96%D0%BD" title="Сафранін – Ukrainian" lang="uk" hreflang="uk" data-title="Сафранін" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Safranin" title="Safranin – Vietnamese" lang="vi" hreflang="vi" data-title="Safranin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%95%AA%E7%B4%85" title="番紅 – Chinese" lang="zh" hreflang="zh" data-title="番紅" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q413672#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div 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colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Safranin_Cl.svg" class="mw-file-description" title="Safranin"><img alt="Safranin" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Safranin_Cl.svg/200px-Safranin_Cl.svg.png" decoding="async" width="200" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Safranin_Cl.svg/300px-Safranin_Cl.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Safranin_Cl.svg/400px-Safranin_Cl.svg.png 2x" data-file-width="345" data-file-height="207" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Safranin-3D-balls.png" class="mw-file-description" title="Safranin"><img alt="Safranin" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Safranin-3D-balls.png/200px-Safranin-3D-balls.png" decoding="async" width="200" height="185" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Safranin-3D-balls.png/300px-Safranin-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Safranin-3D-balls.png/400px-Safranin-3D-balls.png 2x" data-file-width="1050" data-file-height="972" /></a></span> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Sample_of_Safranin_O.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Sample_of_Safranin_O.jpg/130px-Sample_of_Safranin_O.jpg" decoding="async" width="130" height="172" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Sample_of_Safranin_O.jpg/195px-Sample_of_Safranin_O.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Sample_of_Safranin_O.jpg/260px-Sample_of_Safranin_O.jpg 2x" data-file-width="1880" data-file-height="2488" /></a><figcaption></figcaption></figure><div style="text-align:center">Solid safranin</div> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Safranin_O_in_aqueous_solution.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Safranin_O_in_aqueous_solution.jpg/130px-Safranin_O_in_aqueous_solution.jpg" decoding="async" width="130" height="172" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Safranin_O_in_aqueous_solution.jpg/195px-Safranin_O_in_aqueous_solution.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Safranin_O_in_aqueous_solution.jpg/260px-Safranin_O_in_aqueous_solution.jpg 2x" data-file-width="1880" data-file-height="2488" /></a><figcaption></figcaption></figure><div style="text-align:center">Safranin in aqueous solution</div> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">3,7-Diamino-2,8-dimethyl-5-phenylphenazin-5-ium chloride</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=477-73-6">477-73-6</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=%5BCl-%5D.n1c4c%28%5Bn%2B%5D%28c2c1cc%28c%28N%29c2%29C%29c3ccccc3%29cc%28c%28c4%29C%29N">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=197447">CHEBI:197447</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.2005991.html">2005991</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.006.836">100.006.836</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q413672#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/2723800">2723800</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/XTX0YXU2HV">XTX0YXU2HV</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID60874047">DTXSID60874047</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q413672#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C20H18N4.ClH/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17;/h3-11H,1-2H3,(H3,21,22);1H<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: OARRHUQTFTUEOS-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C20H18N4.ClH/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17;/h3-11H,1-2H3,(H3,21,22);1H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: OARRHUQTFTUEOS-UHFFFAOYAR</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C20H18N4/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17/h3-11H,1-2H3,(H3,21,22)/p+1</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">[Cl-].n1c4c([n+](c2c1cc(c(N)c2)C)c3ccccc3)cc(c(c4)C)N</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>20</sub><span title="Hydrogen">H</span><sub>19</sub><span title="Chlorine">Cl</span><span title="Nitrogen">N</span><sub>4</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002350850000000000♠"></span>350.85</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Soluble </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><sup id="cite_ref-labchem_1-0" class="reference"><a href="#cite_note-labchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b><sup id="cite_ref-labchem_1-1" class="reference"><a href="#cite_note-labchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H318: Causes serious eye damage">H318</abbr><sup id="cite_ref-labchem_1-2" class="reference"><a href="#cite_note-labchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr>, <abbr class="abbr" title="P332+P313: If skin irritation occurs: Get medical advice/attention.">P332+P313</abbr>, <abbr class="abbr" title="P362: Take off contaminated clothing.">P362</abbr><sup id="cite_ref-labchem_1-3" class="reference"><a href="#cite_note-labchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_b27845110d7e52b0" /></span><map name="ImageMap_b27845110d7e52b0"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 0: Will not burn. E.g. water" title="Flammability 0: Will not burn. E.g. water" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 0: Will not burn. E.g. water" class="notheme mw-no-invert">0</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464386081&page2=Safranin">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Safranin</b> (<b>Safranin O</b> or <b>basic red 2</b>) is a <a href="/wiki/Staining" title="Staining">biological stain</a> used in <a href="/wiki/Histology" title="Histology">histology</a> and <a href="/wiki/Cell_biology" title="Cell biology">cytology</a>. Safranin is used as a counterstain in some staining protocols, colouring <a href="/wiki/Cell_nucleus" title="Cell nucleus">cell nuclei</a> red. This is the classic <a href="/wiki/Counterstain" title="Counterstain">counterstain</a> in both <a href="/wiki/Gram_stain" title="Gram stain">Gram stains</a> and <a href="/wiki/Endospore_staining" title="Endospore staining">endospore staining</a>. It can also be used for the detection of <a href="/wiki/Cartilage" title="Cartilage">cartilage</a>,<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Mucin" title="Mucin">mucin</a> and <a href="/wiki/Mast_cell" title="Mast cell">mast cell</a> granules. </p><p>Safranin typically has the chemical structure shown at right (sometimes described as <b>dimethyl safranin</b>). There is also <b>trimethyl safranin</b>, which has an added <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> in the <i>ortho-</i> position (see <a href="/wiki/Arene_substitution_pattern" title="Arene substitution pattern">Arene substitution pattern</a>) of the lower ring. Both compounds behave essentially identically in biological staining applications, and most manufacturers of safranin do not distinguish between the two. Commercial safranin preparations often contain a blend of both types. </p><p>Safranin is also used as <a href="/wiki/Redox_indicator" title="Redox indicator">redox indicator</a> in <a href="/wiki/Analytical_chemistry" title="Analytical chemistry">analytical chemistry</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Safranines">Safranines</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Safranin&action=edit&section=1" title="Edit section: Safranines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><b>Safranines</b> are the azonium <a href="/wiki/Chemical_compound" title="Chemical compound">compounds</a> of <a href="/wiki/Symmetrical" class="mw-redirect" title="Symmetrical">symmetrical</a> 2,8-dimethyl-3,7-diaminophenazine. They are obtained by the joint <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of one <a href="/wiki/Molecule" title="Molecule">molecule</a> of a <i>para</i>-diamine with two molecules of a <a href="/wiki/Primary_amine" class="mw-redirect" title="Primary amine">primary amine</a>; by the condensation of <i>para</i>-aminoazo compounds with primary amines, and by the action of <i>para</i>-nitrosodialkylanilines with secondary <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">bases</a> such as diphenylmetaphenylenediamine. They are <a href="/wiki/Crystalline" class="mw-redirect" title="Crystalline">crystalline</a> solids showing a characteristic green metallic <a href="/wiki/Lustre_(mineralogy)" title="Lustre (mineralogy)">lustre</a>; they are readily soluble in water and <a href="/wiki/Dye" title="Dye">dye</a> red or violet. They are strong bases and form stable monacid <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a>. Their <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcoholic</a> solution shows a yellow-red <a href="/wiki/Fluorescence" title="Fluorescence">fluorescence</a>.<sup id="cite_ref-EB1911_3-0" class="reference"><a href="#cite_note-EB1911-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Phenosafranine is not very stable in the free state<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2023)">citation needed</span></a></i>]</sup>; its <a href="/wiki/Chloride" title="Chloride">chloride</a> forms green plates<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (February 2023)">clarification needed</span></a></i>]</sup>. It can be readily diazotized, and the diazonium salt when boiled with alcohol yields aposafranine or benzene induline, C<sub>18</sub>H<sub>12</sub>N<sub>3</sub>. Friedrich Kehrmann showed that aposafranine could be diazotized in the presence of cold concentrated <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>, and the diazonium salt on boiling with alcohol yielded phenylphenazonium salts. Aposafranone, C<sub>18</sub>H<sub>12</sub>N<sub>2</sub>O, is formed by heating aposafranine with concentrated <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a>. These three compounds are perhaps to be represented as <i>ortho</i>- or as <i>para</i>-<a href="/wiki/Quinone" title="Quinone">quinones</a>. The "safranine" of commerce is an <i>ortho</i>-tolusafranine. The first <a href="/wiki/Aniline" title="Aniline">aniline</a> dye-stuff to be prepared on a manufacturing scale was <a href="/wiki/Mauveine" title="Mauveine">mauveine</a>, which was obtained by <a href="/wiki/Sir_William_Henry_Perkin" class="mw-redirect" title="Sir William Henry Perkin">Sir William Henry Perkin</a> by heating crude aniline with <a href="/wiki/Potassium_dichromate" title="Potassium dichromate">potassium dichromate</a> and sulfuric acid.<sup id="cite_ref-EB1911_3-1" class="reference"><a href="#cite_note-EB1911-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Mauveine was converted to <i>parasafranine</i> (1,8-dimethylsafranine) by Perkin in 1878 by <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidative</a>/<a href="/wiki/Redox" title="Redox">reductive</a> loss of the 7<i>N</i>-<i>para</i>-tolyl group.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Another well known safranin is phenosafranine (C.I. 50200, 3,7-diamino-5-phenylphenazinium chloride) widely used as a histological dye, photosensitizer and redox probe.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Safranin&action=edit&section=2" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-labchem-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-labchem_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-labchem_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-labchem_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-labchem_1-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20160310191854/http://www.labchem.com/tools/msds/msds/75583.pdf">"Safety Data Sheet: Safranin O"</a> <span class="cs1-format">(PDF)</span>. <i>LabChem</i>. Archived from <a rel="nofollow" class="external text" href="http://www.labchem.com/tools/msds/msds/75583.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 10 March 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">10 March</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=LabChem&rft.atitle=Safety+Data+Sheet%3A+Safranin+O&rft_id=http%3A%2F%2Fwww.labchem.com%2Ftools%2Fmsds%2Fmsds%2F75583.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASafranin" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRosenberg_L1971" class="citation journal cs1">Rosenberg L (1971). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20080417005221/http://www.ejbjs.org/cgi/content/abstract/53/1/69">"Chemical Basis for the Histological Use of Safranin O in the Study of Articular Cartilage"</a>. <i>J Bone Joint Surg Am</i>. <b>53</b> (1): 69–82. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2106%2F00004623-197153010-00007">10.2106/00004623-197153010-00007</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4250366">4250366</a>. Archived from <a rel="nofollow" class="external text" href="http://www.ejbjs.org/cgi/content/abstract/53/1/69">the original</a> <span class="cs1-format">(abstract)</span> on 2008-04-17.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Bone+Joint+Surg+Am&rft.atitle=Chemical+Basis+for+the+Histological+Use+of+Safranin+O+in+the+Study+of+Articular+Cartilage&rft.volume=53&rft.issue=1&rft.pages=69-82&rft.date=1971&rft_id=info%3Adoi%2F10.2106%2F00004623-197153010-00007&rft_id=info%3Apmid%2F4250366&rft.au=Rosenberg+L&rft_id=http%3A%2F%2Fwww.ejbjs.org%2Fcgi%2Fcontent%2Fabstract%2F53%2F1%2F69&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASafranin" class="Z3988"></span></span> </li> <li id="cite_note-EB1911-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-EB1911_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-EB1911_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><span class="noprint"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png" decoding="async" width="12" height="13" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/18px-Wikisource-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/24px-Wikisource-logo.svg.png 2x" data-file-width="410" data-file-height="430" /></span></span> </span>One or more of the preceding sentences incorporates text from a publication now in the <a href="/wiki/Public_domain" title="Public domain">public domain</a>: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChisholm1911" class="citation encyclopaedia cs1"><a href="/wiki/Hugh_Chisholm" title="Hugh Chisholm">Chisholm, Hugh</a>, ed. (1911). "<a href="https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Safranine" class="extiw" title="s:1911 Encyclopædia Britannica/Safranine">Safranine</a>". <i><a href="/wiki/Encyclop%C3%A6dia_Britannica_Eleventh_Edition" title="Encyclopædia Britannica Eleventh Edition">Encyclopædia Britannica</a></i>. Vol. 23 (11th ed.). Cambridge University Press. p. 1000.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Safranine&rft.btitle=Encyclop%C3%A6dia+Britannica&rft.pages=1000&rft.edition=11th&rft.pub=Cambridge+University+Press&rft.date=1911&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASafranin" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFW._H._Perkin_F.R.S.1879" class="citation journal cs1"><a href="/wiki/Sir_William_Henry_Perkin" class="mw-redirect" title="Sir William Henry Perkin">W. H. Perkin F.R.S.</a> (1879). <a rel="nofollow" class="external text" href="https://zenodo.org/record/2010519">"LXXIV.—On mauveine and allied colouring matters"</a>. <i><a href="/wiki/J._Chem._Soc.,_Trans." class="mw-redirect" title="J. Chem. Soc., Trans.">J. Chem. Soc., Trans.</a></i> <b>35</b>: 717–732. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FCT8793500717">10.1039/CT8793500717</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Chem.+Soc.%2C+Trans.&rft.atitle=LXXIV.%E2%80%94On+mauveine+and+allied+colouring+matters&rft.volume=35&rft.pages=717-732&rft.date=1879&rft_id=info%3Adoi%2F10.1039%2FCT8793500717&rft.au=W.+H.+Perkin+F.R.S.&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F2010519&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASafranin" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZuccaVinciRescignoDumitriu2010" class="citation journal cs1">Zucca, Paolo; Vinci, Carla; Rescigno, Antonio; Dumitriu, Emil; Sanjust, Enrico (14 April 2010). "Is the bleaching of phenosafranine by hydrogen peroxide oxidation catalyzed by silica-supported 5,10,15,20-tetrakis-(sulfonatophenyl)porphine-Mn(III) really biomimetic?". <i>Journal of Molecular Catalysis A: Chemical</i>. <b>321</b> (1–2): 27–33. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.molcata.2010.01.015">10.1016/j.molcata.2010.01.015</a>.</cite><span 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</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lipid" title="Lipid">Lipids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sudan_stain" title="Sudan stain">Sudan stain</a> <ul><li><a href="/wiki/Sudan_II" title="Sudan II">Sudan II</a></li> <li><a href="/wiki/Sudan_III" title="Sudan III">Sudan III</a></li> <li><a href="/wiki/Sudan_IV" title="Sudan IV">Sudan IV</a></li> <li><a href="/wiki/Oil_Red_O" title="Oil Red O">Oil Red O</a></li> <li><a href="/wiki/Sudan_Black_B" class="mw-redirect" title="Sudan Black B">Sudan Black B</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbohydrate" title="Carbohydrate">Carbohydrates</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alcian_blue_stain" title="Alcian blue stain">Alcian blue</a></li> <li><a href="/wiki/Mucicarmine_stain" title="Mucicarmine stain">Mucicarmine</a></li> <li><a href="/wiki/Periodic_acid%E2%80%93Schiff_stain" title="Periodic acid–Schiff stain">Periodic acid–Schiff stain</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Amyloid" title="Amyloid">Amyloid</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Congo_red" title="Congo red">Congo red</a></li> <li><a href="/wiki/Thioflavin" title="Thioflavin">Thioflavin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bacteria" title="Bacteria">Bacteria</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gram_stain" title="Gram stain">Gram stain</a> <ul><li><a href="/wiki/Methyl_violet" title="Methyl violet">Methyl violet</a>/<a href="/wiki/Crystal_violet" title="Crystal violet">Gentian violet</a></li> <li><a class="mw-selflink selflink">Safranin</a></li></ul></li> <li><a href="/wiki/Acid-fastness" title="Acid-fastness">Acid-fast</a> <ul><li><a href="/wiki/Ziehl%E2%80%93Neelsen_stain" title="Ziehl–Neelsen stain">Ziehl–Neelsen stain</a>/<a href="/wiki/Kinyoun_stain" title="Kinyoun stain">Kinyoun stain</a> <ul><li><a href="/wiki/Carbol_fuchsin" title="Carbol fuchsin">Carbol fuchsin</a>/<a href="/wiki/Fuchsine" title="Fuchsine">Fuchsine</a></li> <li><a href="/wiki/Methylene_blue" title="Methylene blue">Methylene blue</a></li></ul></li> <li><a href="/wiki/Auramine%E2%80%93rhodamine_stain" title="Auramine–rhodamine stain">Auramine–rhodamine stain</a> <ul><li><a href="/wiki/Auramine_O" title="Auramine O">Auramine O</a></li> <li><a href="/wiki/Rhodamine_B" title="Rhodamine B">Rhodamine B</a></li></ul></li> <li><a href="/wiki/Auramine_phenol_stain" title="Auramine phenol stain">Auramine phenol stain</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Connective_tissue" title="Connective tissue">Connective tissue</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Trichrome_stain" class="mw-redirect" title="Trichrome stain">trichrome stain</a>: <a href="/wiki/Masson%27s_trichrome_stain" title="Masson's trichrome stain">Masson's trichrome stain</a>/<a href="/wiki/Lillie%27s_trichrome" title="Lillie's trichrome">Lillie's trichrome</a> <ul><li><a href="/wiki/Light_Green_SF_yellowish" class="mw-redirect" title="Light Green SF yellowish">Light Green SF yellowish</a></li> <li><a href="/wiki/Biebrich_scarlet" title="Biebrich scarlet">Biebrich scarlet</a></li> <li><a href="/wiki/Phosphomolybdic_acid" title="Phosphomolybdic acid">Phosphomolybdic acid</a></li> <li><a href="/wiki/Fast_Green_FCF" title="Fast Green FCF">Fast Green FCF</a></li> <li><a href="/wiki/Sirius_Red" title="Sirius Red">Sirius Red</a></li></ul></li></ul> <ul><li><a href="/wiki/Van_Gieson%27s_stain" title="Van Gieson's stain">Van Gieson's stain</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cresyl_violet" title="Cresyl violet">Cresyl violet</a></li> <li><a href="/wiki/Cyanine" title="Cyanine">Cyanine</a></li> <li><a href="/wiki/Jaswant_Singh%E2%80%93Bhattacharji_(JSB)_stain" class="mw-redirect" title="Jaswant Singh–Bhattacharji (JSB) stain">Jaswant Singh–Bhattacharji (JSB) stain</a></li> <li><a href="/wiki/H%26E_stain" title="H&E stain">H&E stain</a> <ul><li><a href="/wiki/Haematoxylin" title="Haematoxylin">Haematoxylin</a></li> <li><a href="/wiki/Eosin_Y" title="Eosin Y">Eosin Y</a></li></ul></li> <li><a href="/wiki/Janus_Green_B" title="Janus Green B">Janus Green B</a></li> <li><a href="/wiki/Giemsa_stain" title="Giemsa stain">Giemsa stain</a></li> <li><a href="/wiki/G%C3%B6m%C3%B6ri_trichrome_stain" title="Gömöri trichrome stain">Gömöri trichrome stain</a></li> <li><a href="/wiki/Luxol_fast_blue_stain" title="Luxol fast blue stain">Luxol fast blue stain</a></li> <li><a href="/wiki/Methyl_blue" title="Methyl blue">Methyl blue</a></li> <li><a href="/wiki/Moeller_stain" title="Moeller stain">Moeller stain</a></li> <li><a href="/wiki/Movat%27s_stain" title="Movat's stain">Movat's stain</a></li> <li><a href="/wiki/Neutral_red" title="Neutral red">Neutral red</a></li> <li><a href="/wiki/Schaeffer%E2%80%93Fulton_stain" title="Schaeffer–Fulton stain">Schaeffer–Fulton stain</a></li> <li><a href="/wiki/Silver_stain" class="mw-redirect" title="Silver stain">Silver stain</a> <ul><li><a href="/wiki/Bielschowsky_stain" title="Bielschowsky stain">Bielschowsky stain</a></li> <li><a href="/wiki/Grocott%27s_methenamine_silver_stain" title="Grocott's methenamine silver stain">Grocott's methenamine silver stain</a></li> <li><a href="/wiki/Warthin%E2%80%93Starry_stain" title="Warthin–Starry stain">Warthin–Starry stain</a></li></ul></li> <li><a href="/wiki/Wright%27s_stain" title="Wright's stain">Wright's stain</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tissue stainability</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acidophile_(histology)" title="Acidophile (histology)">Acidophilic</a></li> <li><a href="/wiki/Basophilic" title="Basophilic">Basophilic</a></li> <li><a href="/wiki/Chromophobe" class="mw-redirect" title="Chromophobe">Chromophobic</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img 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