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Sodium nitroprusside - Wikipedia

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<span>Overdose</span> </div> </a> <ul id="toc-Overdose-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicology" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Toxicology"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Toxicology</span> </div> </a> <ul id="toc-Toxicology-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Mechanism of action</span> </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Structure_and_properties" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Structure_and_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Structure and properties</span> </div> </a> <ul id="toc-Structure_and_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Preparation" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Preparation"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Preparation</span> </div> </a> <ul id="toc-Preparation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Other_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Other uses</span> </div> </a> <button aria-controls="toc-Other_uses-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Other uses subsection</span> </button> <ul id="toc-Other_uses-sublist" class="vector-toc-list"> <li id="toc-Analytical_reagent" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Analytical_reagent"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Analytical reagent</span> </div> </a> <ul id="toc-Analytical_reagent-sublist" class="vector-toc-list"> <li id="toc-Ketones" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Ketones"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1.1</span> <span>Ketones</span> </div> </a> <ul id="toc-Ketones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Thiols_and_cysteine" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Thiols_and_cysteine"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1.2</span> <span>Thiols and cysteine</span> </div> </a> <ul id="toc-Thiols_and_cysteine-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Amines" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Amines"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1.3</span> <span>Amines</span> </div> </a> <ul id="toc-Amines-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Sodium nitroprusside</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 22 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-22" 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">22 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/%D9%86%D8%AA%D8%B1%D9%88%D8%A8%D8%B1%D9%88%D8%B3%D9%8A%D8%AF_%D8%A7%D9%84%D8%B5%D9%88%D8%AF%D9%8A%D9%88%D9%85" title="نتروبروسيد الصوديوم – Arabic" lang="ar" hreflang="ar" data-title="نتروبروسيد الصوديوم" 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/%D9%86%DB%8C%D8%AA%D8%B1%D9%88%D9%BE%D8%B1%D9%88%D8%B3%D8%A7%DB%8C%D8%AF_%D8%B3%D8%AF%DB%8C%D9%85" title="نیتروپروساید سدیم – South Azerbaijani" lang="azb" hreflang="azb" data-title="نیتروپروساید سدیم" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cv mw-list-item"><a href="https://cv.wikipedia.org/wiki/%D0%9D%D0%B0%D1%82%D1%80%D0%B8%D0%B9_%D0%BD%D0%B8%D1%82%D1%80%D0%BE%D0%BF%D1%80%D1%83%D1%81%D1%81%D0%B8%D1%87%C4%95" title="Натрий нитропруссичĕ – Chuvash" lang="cv" hreflang="cv" data-title="Натрий нитропруссичĕ" data-language-autonym="Чӑвашла" data-language-local-name="Chuvash" class="interlanguage-link-target"><span>Чӑвашла</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Nitroprussid" title="Nitroprussid – German" lang="de" hreflang="de" data-title="Nitroprussid" 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/Nitroprusiato" title="Nitroprusiato – Spanish" lang="es" hreflang="es" data-title="Nitroprusiato" 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%D8%AF%DB%8C%D9%85_%D9%86%DB%8C%D8%AA%D8%B1%D9%88%D9%BE%D8%B1%D9%88%D8%B3%D8%A7%DB%8C%D8%AF" title="سدیم نیتروپروساید – Persian" lang="fa" hreflang="fa" data-title="سدیم نیتروپروساید" 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/Nitroprussiate_de_sodium" title="Nitroprussiate de sodium – French" lang="fr" hreflang="fr" data-title="Nitroprussiate de sodium" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Nitroprusid" title="Nitroprusid – Croatian" lang="hr" hreflang="hr" data-title="Nitroprusid" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Natrium_nitroprusida" title="Natrium nitroprusida – Indonesian" lang="id" hreflang="id" data-title="Natrium nitroprusida" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Nitroprussiato_di_sodio" title="Nitroprussiato di sodio – Italian" lang="it" hreflang="it" data-title="Nitroprussiato di sodio" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A0%D7%AA%D7%A8%D7%9F_%D7%A0%D7%99%D7%98%D7%A8%D7%95%D7%A4%D7%A8%D7%95%D7%A1%D7%99%D7%93%D7%99" title="נתרן ניטרופרוסידי – Hebrew" lang="he" hreflang="he" data-title="נתרן ניטרופרוסידי" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%8B%E3%83%88%E3%83%AD%E3%83%97%E3%83%AB%E3%82%B7%E3%83%89" title="ニトロプルシド – Japanese" lang="ja" hreflang="ja" data-title="ニトロプルシド" 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-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%B8%E0%AD%8B%E0%AC%A1%E0%AC%BC%E0%AC%BF%E0%AC%85%E0%AC%AE_%E0%AC%A8%E0%AC%BE%E0%AC%87%E0%AC%9F%E0%AD%8D%E0%AC%B0%E0%AD%8B%E0%AC%AA%E0%AD%83%E0%AC%B8%E0%AC%BE%E0%AC%87%E0%AC%A1" title="ସୋଡ଼ିଅମ ନାଇଟ୍ରୋପୃସାଇଡ – Odia" lang="or" hreflang="or" data-title="ସୋଡ଼ିଅମ ନାଇଟ୍ରୋପୃସାଇଡ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Nitroprusydek_sodu" title="Nitroprusydek sodu – Polish" lang="pl" hreflang="pl" data-title="Nitroprusydek sodu" 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/Nitroprussiato_de_s%C3%B3dio" title="Nitroprussiato de sódio – Portuguese" lang="pt" hreflang="pt" data-title="Nitroprussiato de sódio" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Nitroprusiat_de_sodiu" title="Nitroprusiat de sodiu – Romanian" lang="ro" hreflang="ro" data-title="Nitroprusiat de sodiu" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Natrijum_nitroprusid" title="Natrijum nitroprusid – Serbian" lang="sr" hreflang="sr" data-title="Natrijum nitroprusid" 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/Natrijum_nitroprusid" title="Natrijum nitroprusid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Natrijum nitroprusid" 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/Nitroprussidi" title="Nitroprussidi – Finnish" lang="fi" hreflang="fi" data-title="Nitroprussidi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9D%D0%B0%D1%82%D1%80%D1%96%D0%B9_%D0%BD%D1%96%D1%82%D1%80%D0%BE%D0%BF%D1%80%D1%83%D1%81%D0%B8%D0%B4" title="Натрій нітропрусид – Ukrainian" lang="uk" hreflang="uk" data-title="Натрій нітропрусид" 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/Natri_nitroprusside" title="Natri nitroprusside – Vietnamese" lang="vi" hreflang="vi" data-title="Natri nitroprusside" 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%A1%9D%E6%99%AE%E9%92%A0" title="硝普钠 – Chinese" lang="zh" hreflang="zh" data-title="硝普钠" data-language-autonym="中文" data-language-local-name="Chinese" 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<div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=Sodium_Nitroprusside&amp;redirect=no" class="mw-redirect" title="Sodium Nitroprusside">Sodium Nitroprusside</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Medication for lowering blood pressure</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Sodium nitroprusside">Sodium nitroprusside</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Sodium-nitroprusside-2D.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Sodium-nitroprusside-2D.png/225px-Sodium-nitroprusside-2D.png" decoding="async" width="225" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Sodium-nitroprusside-2D.png/338px-Sodium-nitroprusside-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Sodium-nitroprusside-2D.png/450px-Sodium-nitroprusside-2D.png 2x" data-file-width="1100" data-file-height="771" /></a></span></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Sodium-nitroprusside-sample.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Sodium-nitroprusside-sample.jpg/300px-Sodium-nitroprusside-sample.jpg" decoding="async" width="300" height="225" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Sodium-nitroprusside-sample.jpg/450px-Sodium-nitroprusside-sample.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Sodium-nitroprusside-sample.jpg/600px-Sodium-nitroprusside-sample.jpg 2x" data-file-width="1861" data-file-height="1396" /></a></span><div class="infobox-caption">Molecular structure of this compound (top), and a picture of a sample (bottom).</div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Nipride, Nitropress, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">SNP</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/sodium-nitroprusside.html">Monograph</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</a></th><td class="infobox-data"><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><small><abbr class="country-name" title="United States">US</abbr></small>&#160;<span title="www.accessdata.fda.gov"><a href="/wiki/U.S._Food_and_Drug_Administration" class="mw-redirect" title="U.S. Food and Drug Administration">FDA</a>:&#160;<a rel="nofollow" class="external text" href="https://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.SearchAction&amp;SearchTerm=Nitroprusside&amp;SearchType=BasicSearch">Nitroprusside</a></span></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small>&#x20;C</li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">Intravenous</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/ATC_code_C02" title="ATC code C02">C02DD01</a>&#x20;(<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=C02DD01">WHO</a></span>)&#x20;QC02DD01 (vet)</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small>&#x20;<a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_4" title="Standard for the Uniform Scheduling of Medicines and Poisons">S4</a> (Prescription only)<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup></li> <li><small><abbr class="country-name" title="Canada">CA</abbr></small>:&#x20;<a href="/wiki/Prescription_drug" title="Prescription drug"> ℞-only</a></li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small>&#x20;<a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)</li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small>&#x20;<a href="/wiki/Prescription_drug" title="Prescription drug">℞-only</a></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">100% (intravenous)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data">By haemoglobin being converted to cyanmethaemoglobin and cyanide ions</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Onset_of_action" title="Onset of action">Onset of action</a></th><td class="infobox-data">nearly immediate<sup id="cite_ref-AHFS2016_3-0" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">&lt;2 minutes (3 days for thiocyanate metabolite)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pharmacodynamics#Duration_of_action" title="Pharmacodynamics">Duration of action</a></th><td class="infobox-data">1 to 10 minutes<sup id="cite_ref-AHFS2016_3-1" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Kidney" title="Kidney">kidney</a> (100%; as thiocyanate)<sup id="cite_ref-GG_4-0" class="reference"><a href="#cite_note-GG-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</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; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">Sodium pentacyanidonitrosylferrate(III)</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=13755-38-9">13755-38-9</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><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/11953895">11953895</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00325">DB00325</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a 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href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL136478">ChEMBL136478</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><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></th><td class="infobox-data"><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/DTXSID7041126">DTXSID7041126</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q27108300#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" 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typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q27108300#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><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>5</sub><span title="Iron">Fe</span><span title="Nitrogen">N</span><sub>6</sub><span title="Sodium">Na</span><sub>2</sub><span title="Oxygen">O</span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002261921000000000♠"></span>261.921</span>&#160;g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><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=%5BNa%2B%5D.%5BNa%2B%5D.O%3DN%5BFe--%5D%28C%23N%29%28C%23N%29%28C%23N%29%28C%23N%29C%23N">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Density" title="Density">Density</a></th><td class="infobox-data">1.72&#160;g/cm<sup>3</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></th><td class="infobox-data">100&#160;mg/mL (20&#160;°C)</td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><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="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">[Na+].[Na+].O=N[Fe--](C#N)(C#N)(C#N)(C#N)C#N</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><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="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/5CN.Fe.NO.2Na/c5*1-2;;1-2;;/q;;;;;2*-1;2*+1</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:FPWUWQVZUNFZQM-UHFFFAOYSA-N</div></li></ul> </div></td></tr></tbody></table> <p><b>Sodium nitroprusside</b> (<b>SNP</b>), sold under the brand name <b>Nitropress</b> among others, is a medication used to lower <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>.<sup id="cite_ref-AHFS2016_3-2" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> This may be done if the <a href="/wiki/Hypertensive_emergency" title="Hypertensive emergency">blood pressure is very high and resulting in symptoms</a>, in certain types of <a href="/wiki/Heart_failure" title="Heart failure">heart failure</a>, and during surgery to decrease <a href="/wiki/Bleeding" title="Bleeding">bleeding</a>.<sup id="cite_ref-AHFS2016_3-3" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> It is used by <a href="/wiki/Intravenous_infusion" class="mw-redirect" title="Intravenous infusion">continuous injection into a vein</a>.<sup id="cite_ref-AHFS2016_3-4" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> Onset is nearly immediate and effects last for up to ten minutes.<sup id="cite_ref-AHFS2016_3-5" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p><p>It is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Side_effects_and_mechanism">Side effects and mechanism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=1" title="Edit section: Side effects and mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Common side effects include <a href="/wiki/Low_blood_pressure" class="mw-redirect" title="Low blood pressure">low blood pressure</a> and <a href="/wiki/Cyanide_toxicity" class="mw-redirect" title="Cyanide toxicity">cyanide toxicity</a>.<sup id="cite_ref-AHFS2016_3-6" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> Other serious side effects include <a href="/wiki/Methemoglobinemia" title="Methemoglobinemia">methemoglobinemia</a>.<sup id="cite_ref-AHFS2016_3-7" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> It is not generally recommended during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> due to concerns of side effects.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> High doses are not recommended for more than ten minutes.<sup id="cite_ref-WHO2008_7-0" class="reference"><a href="#cite_note-WHO2008-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> It works by increasing <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> levels in the blood, which increases <a href="/wiki/Cyclic_guanosine_monophosphate" title="Cyclic guanosine monophosphate">cGMP</a> levels in cells, and causes <a href="/wiki/Dilation_of_blood_vessels" class="mw-redirect" title="Dilation of blood vessels">dilation of blood vessels</a>.<sup id="cite_ref-Hist1995_8-0" class="reference"><a href="#cite_note-Hist1995-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-AHFS2016_3-8" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History,_society_and_culture"><span id="History.2C_society_and_culture"></span>History, society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=2" title="Edit section: History, society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium nitroprusside was discovered as early as 1850 and found to be useful in medicine in 1928.<sup id="cite_ref-Hist1995_8-1" class="reference"><a href="#cite_note-Hist1995-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> It is on the <a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">World Health Organization's List of Essential Medicines</a>.<sup id="cite_ref-WHO21st_10-0" class="reference"><a href="#cite_note-WHO21st-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-WHO22nd_11-0" class="reference"><a href="#cite_note-WHO22nd-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup> Sodium nitroprusside is light sensitive, so it needs to be shielded from light to prevent degradation.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Medical_use">Medical use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=3" title="Edit section: Medical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium nitroprusside is <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenously</a> infused in cases of acute <a href="/wiki/Hypertensive_crises" class="mw-redirect" title="Hypertensive crises">hypertensive crises</a>.<sup id="cite_ref-DM_13-0" class="reference"><a href="#cite_note-DM-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-BNF_14-0" class="reference"><a href="#cite_note-BNF-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> Its effects are usually seen within a few minutes.<sup id="cite_ref-GG_4-1" class="reference"><a href="#cite_note-GG-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> </p><p>Nitric oxide reduces both total peripheral resistance and venous return, thus decreasing both <a href="/wiki/Preload_(cardiology)" title="Preload (cardiology)">preload</a> and <a href="/wiki/Afterload" title="Afterload">afterload</a>. So, it can be used in severe <a href="/wiki/Congestive_heart_failure" class="mw-redirect" title="Congestive heart failure">congestive heart failure</a> where this combination of effects can act to increase <a href="/wiki/Cardiac_output" title="Cardiac output">cardiac output</a>. In situations where cardiac output is normal, the effect is to reduce <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>.<sup id="cite_ref-DM_13-1" class="reference"><a href="#cite_note-DM-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-TGA_15-0" class="reference"><a href="#cite_note-TGA-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> It is sometimes also used to induce hypotension (to reduce bleeding) for surgical procedures (for which it is also <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">FDA</a>, <a href="/wiki/Therapeutic_Goods_Administration" title="Therapeutic Goods Administration">TGA</a>, and <a href="/wiki/Medicines_and_Healthcare_products_Regulatory_Agency" title="Medicines and Healthcare products Regulatory Agency">MHRA</a> labelled).<sup id="cite_ref-DM_13-2" class="reference"><a href="#cite_note-DM-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-BNF_14-1" class="reference"><a href="#cite_note-BNF-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-AMH_16-0" class="reference"><a href="#cite_note-AMH-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup> </p><p>The medication is extremely beneficial for use in medical patients because the effects of the medication will directly stop the second that it stops being infused. This is due to the metabolism of the drug, and the rapid inactivation to thiocyanate once conversion of the drug stops. </p><p>This compound has also been used as a treatment for <a href="/wiki/Aortic_valve_stenosis" class="mw-redirect" title="Aortic valve stenosis">aortic valve stenosis</a>,<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Oesophageal_varices" class="mw-redirect" title="Oesophageal varices">oesophageal varices</a>,<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a>,<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Pulmonary_hypertension" title="Pulmonary hypertension">pulmonary hypertension</a>,<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Infant_respiratory_distress_syndrome" title="Infant respiratory distress syndrome">respiratory distress syndrome in the newborn</a>,<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">&#91;</span>23<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-PD_24-0" class="reference"><a href="#cite_note-PD-24"><span class="cite-bracket">&#91;</span>24<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Shock_(circulatory)" title="Shock (circulatory)">shock</a>,<sup id="cite_ref-PD_24-1" class="reference"><a href="#cite_note-PD-24"><span class="cite-bracket">&#91;</span>24<span class="cite-bracket">&#93;</span></a></sup> and <a href="/wiki/Ergotism" title="Ergotism">ergot toxicity</a>.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">&#91;</span>25<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects">Adverse effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=4" title="Edit section: Adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><b><big>Adverse effects by incidence and severity</big></b><sup id="cite_ref-DM_13-3" class="reference"><a href="#cite_note-DM-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-TGA_15-1" class="reference"><a href="#cite_note-TGA-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MSR_26-0" class="reference"><a href="#cite_note-MSR-26"><span class="cite-bracket">&#91;</span>26<span class="cite-bracket">&#93;</span></a></sup> </p><p><b>Common</b> </p> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col"> <ul><li><a href="/wiki/Bradyarrhythmia" class="mw-redirect" title="Bradyarrhythmia">Bradyarrhythmia</a> (low heart rate)</li> <li><a href="/wiki/Hypotension" title="Hypotension">Hypotension</a> (low blood pressure)</li> <li>Palpitations</li> <li><a href="/wiki/Tachyarrhythmia" class="mw-redirect" title="Tachyarrhythmia">Tachyarrhythmia</a> (high heart rate)</li> <li>Apprehension</li> <li>Restlessness</li> <li>Confusion</li> <li>Dizziness</li> <li>Headache</li> <li><a href="/wiki/Somnolence" title="Somnolence">Somnolence</a></li> <li>Rash</li> <li>Sweating</li> <li>Thyroid suppression</li> <li>Muscle twitch</li> <li><a href="/wiki/Oliguria" title="Oliguria">Oliguria</a></li> <li>Renal <a href="/wiki/Azotemia" title="Azotemia">azotemia</a></li></ul> </div> <p><b>Unknown frequency</b> </p> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1184024115"><div class="div-col"> <ul><li>Nausea</li> <li>Retching</li> <li>Anxiety</li> <li>Chest discomfort</li> <li>Paraesthesial warmth</li> <li>Abdominal pain</li> <li>Orthostatic hypotension</li> <li>ECG changes</li> <li>Skin irritation</li> <li>Flushing</li> <li>Injection site erythema</li> <li>Injection site streaking</li></ul> </div> <p><b>Serious</b> </p> <ul><li><a href="/wiki/Ileus" title="Ileus">Ileus</a></li> <li>Reduced platelet aggregation</li> <li><a href="/wiki/Haemorrhage" class="mw-redirect" title="Haemorrhage">Haemorrhage</a></li> <li><a href="/wiki/Increased_intracranial_pressure" class="mw-redirect" title="Increased intracranial pressure">Increased intracranial pressure</a></li> <li><a href="/wiki/Metabolic_acidosis" title="Metabolic acidosis">Metabolic acidosis</a></li> <li><a href="/wiki/Methaemoglobinaemia" class="mw-redirect" title="Methaemoglobinaemia">Methaemoglobinaemia</a></li> <li><a href="/wiki/Cyanide_poisoning" title="Cyanide poisoning">Cyanide poisoning</a></li> <li><a href="/wiki/Thiocyanate" title="Thiocyanate">Thiocyanate</a> toxicity</li></ul> <div class="mw-heading mw-heading3"><h3 id="Contraindications">Contraindications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=5" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium nitroprusside should not be used for compensatory hypertension (e.g. due to an arteriovenous stent or coarctation of the aorta).<sup id="cite_ref-TGA_15-2" class="reference"><a href="#cite_note-TGA-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> It should not be used in patients with inadequate cerebral circulation or in patients who are near death. It should not be used in patients with <a href="/wiki/Vitamin_B12" title="Vitamin B12">vitamin B<sub>12</sub></a> deficiency, anaemia, severe renal disease, or hypovolaemia.<sup id="cite_ref-TGA_15-3" class="reference"><a href="#cite_note-TGA-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> Patients with conditions associated with a higher cyanide/thiocyanate ratio (e.g. congenital (Leber's) optic atrophy, tobacco amblyopia) should only be treated with sodium nitroprusside with great caution.<sup id="cite_ref-TGA_15-4" class="reference"><a href="#cite_note-TGA-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> Its use in patients with acute congestive heart failure associated with reduced peripheral resistance is also not recommended.<sup id="cite_ref-TGA_15-5" class="reference"><a href="#cite_note-TGA-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> Its use in hepatically impaired individuals is also not recommended, as is its use in cases of pre-existing <a href="/wiki/Hypothyroidism" title="Hypothyroidism">hypothyroidism</a>.<sup id="cite_ref-DM_13-4" class="reference"><a href="#cite_note-DM-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup> </p><p>Its use in pregnant women is advised against, although the available evidence suggests it may be safe, provided maternal pH and cyanide levels are closely monitored.<sup id="cite_ref-TGA_15-6" class="reference"><a href="#cite_note-TGA-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">&#91;</span>27<span class="cite-bracket">&#93;</span></a></sup> Some evidence suggests sodium nitroprusside use in critically ill children may be safe, even without monitoring of <a href="/wiki/Cyanide" title="Cyanide">cyanide</a> level.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">&#91;</span>28<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Interactions">Interactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=6" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The only known drug interactions are <a href="/wiki/Pharmacodynamic" class="mw-redirect" title="Pharmacodynamic">pharmacodynamic</a> in nature, that is it is possible for other antihypertensive drugs to reduce the threshold for dangerous hypotensive effects to be seen.<sup id="cite_ref-TGA_15-7" class="reference"><a href="#cite_note-TGA-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Overdose">Overdose</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=7" title="Edit section: Overdose"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Due to its cyanogenic nature, overdose may be particularly dangerous. Treatment of sodium nitroprusside overdose includes the following:<sup id="cite_ref-TGA_15-8" class="reference"><a href="#cite_note-TGA-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">&#91;</span>29<span class="cite-bracket">&#93;</span></a></sup> </p> <ul><li>Discontinuing sodium nitroprusside administration</li> <li>Buffering the cyanide by using <a href="/wiki/Sodium_nitrite" title="Sodium nitrite">sodium nitrite</a> to convert haemoglobin to methaemoglobin as much as the patient can safely tolerate</li> <li>Infusing <a href="/wiki/Sodium_thiosulfate" title="Sodium thiosulfate">sodium thiosulfate</a> to convert the cyanide to thiocyanate.</li></ul> <p><a href="/wiki/Haemodialysis" class="mw-redirect" title="Haemodialysis">Haemodialysis</a> is ineffective for removing cyanide from the body but it can be used to remove most of the thiocyanate produced from the above procedure.<sup id="cite_ref-TGA_15-9" class="reference"><a href="#cite_note-TGA-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Toxicology">Toxicology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=8" title="Edit section: Toxicology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The cyanide can be detoxified by reaction with a <a href="/wiki/Sulfur" title="Sulfur">sulfur</a>-donor such as <a href="/wiki/Sodium_thiosulfate" title="Sodium thiosulfate">thiosulfate</a>, catalysed by the enzyme <a href="/wiki/Rhodanese" title="Rhodanese">rhodanese</a>.<sup id="cite_ref-RXL_30-0" class="reference"><a href="#cite_note-RXL-30"><span class="cite-bracket">&#91;</span>30<span class="cite-bracket">&#93;</span></a></sup> In the absence of sufficient thiosulfate, cyanide ions can quickly reach toxic levels.<sup id="cite_ref-RXL_30-1" class="reference"><a href="#cite_note-RXL-30"><span class="cite-bracket">&#91;</span>30<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a> can be administered to reduce the risk of thiocyanate toxicity induced by nitroprusside.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">&#91;</span>31<span class="cite-bracket">&#93;</span></a></sup> </p> <table class="wikitable"> <tbody><tr> <th>Species</th> <th>LD<sub>50</sub> (mg/kg) for oral administration<sup id="cite_ref-MSDS_32-0" class="reference"><a href="#cite_note-MSDS-32"><span class="cite-bracket">&#91;</span>32<span class="cite-bracket">&#93;</span></a></sup></th> <th>LD<sub>50</sub> (mg/kg) for <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">IV</a> administration<sup id="cite_ref-TGA_15-10" class="reference"><a href="#cite_note-TGA-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup></th> <th>LD<sub>50</sub> (mg/kg) for skin administration<sup id="cite_ref-MSDS_32-1" class="reference"><a href="#cite_note-MSDS-32"><span class="cite-bracket">&#91;</span>32<span class="cite-bracket">&#93;</span></a></sup> </th></tr> <tr> <td>Mouse</td> <td>43</td> <td>8.4</td> <td>? </td></tr> <tr> <td>Rat</td> <td>300</td> <td>11.2</td> <td>&gt;2000 </td></tr> <tr> <td>Rabbit</td> <td>?</td> <td>2.8</td> <td>? </td></tr> <tr> <td>Dog</td> <td>?</td> <td>5</td> <td>? </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=9" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As a result of its breakdown to nitric oxide (NO), sodium nitroprusside has potent <a href="/wiki/Vasodilation" title="Vasodilation">vasodilating</a> effects on <a href="/wiki/Arterioles" class="mw-redirect" title="Arterioles">arterioles</a> and <a href="/wiki/Venule" title="Venule">venules</a> (arterial more than venous), whereas other nitrates exhibit more selectivity for veins (e.g. <a href="/wiki/Nitroglycerin_(medication)" title="Nitroglycerin (medication)">nitroglycerin</a>).<sup id="cite_ref-DM_13-5" class="reference"><a href="#cite_note-DM-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-TGA_15-11" class="reference"><a href="#cite_note-TGA-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MSR_26-1" class="reference"><a href="#cite_note-MSR-26"><span class="cite-bracket">&#91;</span>26<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">&#91;</span>33<span class="cite-bracket">&#93;</span></a></sup> </p><p>Sodium nitroprusside breaks down in circulation to release <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> (NO).<sup id="cite_ref-Hist1995_8-2" class="reference"><a href="#cite_note-Hist1995-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> It does this by binding to oxyhaemoglobin to release cyanide, methaemoglobin and nitric oxide.<sup id="cite_ref-Hist1995_8-3" class="reference"><a href="#cite_note-Hist1995-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> NO activates <a href="/wiki/Guanylate_cyclase" title="Guanylate cyclase">guanylate cyclase</a> in vascular smooth muscle and increases intracellular production of <a href="/wiki/Cyclic_guanosine_monophosphate" title="Cyclic guanosine monophosphate">cGMP</a>. cGMP activates <a href="/wiki/Protein_kinase_G" class="mw-redirect" title="Protein kinase G">protein kinase G</a> which activates phosphatases which inactivate myosin light chains.<sup id="cite_ref-NO1986_34-0" class="reference"><a href="#cite_note-NO1986-34"><span class="cite-bracket">&#91;</span>34<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Myosin" title="Myosin">Myosin</a> light chains are involved in smooth muscle contraction. The result is vascular smooth muscle relaxation, which allow vessels to dilate.<sup id="cite_ref-NO1986_34-1" class="reference"><a href="#cite_note-NO1986-34"><span class="cite-bracket">&#91;</span>34<span class="cite-bracket">&#93;</span></a></sup> This mechanism is similar to that of <a href="/w/index.php?title=Phosphodiesterase_5_(PDE5)_inhibitor&amp;action=edit&amp;redlink=1" class="new" title="Phosphodiesterase 5 (PDE5) inhibitor (page does not exist)">phosphodiesterase 5 (PDE5) inhibitors</a> such as <a href="/wiki/Sildenafil" title="Sildenafil">sildenafil</a> (Viagra) and <a href="/wiki/Tadalafil" title="Tadalafil">tadalafil</a> (Cialis), which elevate cGMP concentration by inhibiting its degradation by PDE5.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">&#91;</span>35<span class="cite-bracket">&#93;</span></a></sup> </p><p>A role for NO in various common psychiatric disorders including <a href="/wiki/Schizophrenia" title="Schizophrenia">schizophrenia</a>,<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">&#91;</span>36<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">&#91;</span>37<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Schiz_38-0" class="reference"><a href="#cite_note-Schiz-38"><span class="cite-bracket">&#91;</span>38<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">&#91;</span>39<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Bipolar_disorder" title="Bipolar disorder">bipolar disorder</a><sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">&#91;</span>40<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">&#91;</span>41<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">&#91;</span>42<span class="cite-bracket">&#93;</span></a></sup> and <a href="/wiki/Major_depressive_disorder" title="Major depressive disorder">major depressive disorder</a><sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">&#91;</span>43<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Dep_44-0" class="reference"><a href="#cite_note-Dep-44"><span class="cite-bracket">&#91;</span>44<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">&#91;</span>45<span class="cite-bracket">&#93;</span></a></sup> has been proposed and supported by several clinical findings. These findings may also implicate the potential of drugs that alter NO signalling such as SNP in their treatment.<sup id="cite_ref-Schiz_38-1" class="reference"><a href="#cite_note-Schiz-38"><span class="cite-bracket">&#91;</span>38<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Dep_44-1" class="reference"><a href="#cite_note-Dep-44"><span class="cite-bracket">&#91;</span>44<span class="cite-bracket">&#93;</span></a></sup> Such a role is also supported by the findings of the recent SNP clinical trial.<sup id="cite_ref-SZ_46-0" class="reference"><a href="#cite_note-SZ-46"><span class="cite-bracket">&#91;</span>46<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Structure_and_properties">Structure and properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=10" title="Edit section: Structure and properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Sodium-nitroprusside-xtal-3D-balls-A.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Sodium-nitroprusside-xtal-3D-balls-A.png/220px-Sodium-nitroprusside-xtal-3D-balls-A.png" decoding="async" width="220" height="149" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Sodium-nitroprusside-xtal-3D-balls-A.png/330px-Sodium-nitroprusside-xtal-3D-balls-A.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Sodium-nitroprusside-xtal-3D-balls-A.png/440px-Sodium-nitroprusside-xtal-3D-balls-A.png 2x" data-file-width="1100" data-file-height="747" /></a><figcaption>Structure of sodium nitroprusside in the solid state, obtained by <a href="/wiki/Neutron_diffraction" title="Neutron diffraction">neutron diffraction</a></figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Nitroprusside-anion-from-xtal-3D-vdW.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Nitroprusside-anion-from-xtal-3D-vdW.png/220px-Nitroprusside-anion-from-xtal-3D-vdW.png" decoding="async" width="220" height="243" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Nitroprusside-anion-from-xtal-3D-vdW.png/330px-Nitroprusside-anion-from-xtal-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Nitroprusside-anion-from-xtal-3D-vdW.png/440px-Nitroprusside-anion-from-xtal-3D-vdW.png 2x" data-file-width="997" data-file-height="1100" /></a><figcaption>Space filling model of sodium nitroprusside</figcaption></figure> <p>Nitroprusside is an <a href="/wiki/Inorganic_compound" title="Inorganic compound">inorganic compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> Na<sub>2</sub>[Fe(CN)<sub>5</sub>NO], usually encountered as the <a href="/wiki/Water_of_crystallization" title="Water of crystallization">dihydrate</a>, Na<sub>2</sub>[Fe(CN)<sub>5</sub>NO]·2H<sub>2</sub>O.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">&#91;</span>47<span class="cite-bracket">&#93;</span></a></sup> This red-colored sodium salt dissolves in water or ethanol to give solutions containing the free <a href="/wiki/Coordination_complex" title="Coordination complex">complex</a> dianion [Fe(CN)<sub>5</sub>NO]<sup>2−</sup>. </p><p>Nitroprusside is a complex <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a> that features an <a href="/wiki/Octahedral_molecular_geometry" title="Octahedral molecular geometry">octahedral</a> iron(II) centre surrounded by five tightly bound <a href="/wiki/Cyanide" title="Cyanide">cyanide</a> ligands and one linear <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> ligand (Fe-N-O angle = 176.2 °<sup id="cite_ref-navaza_48-0" class="reference"><a href="#cite_note-navaza-48"><span class="cite-bracket">&#91;</span>48<span class="cite-bracket">&#93;</span></a></sup>). The anion possesses idealized <a href="/wiki/Point_group" title="Point group"><i>C</i><sub>4v</sub>symmetry</a>. </p><p>Due to the linear Fe-N-O angle, the relatively short N-O distance of 113 pm<sup id="cite_ref-navaza_48-1" class="reference"><a href="#cite_note-navaza-48"><span class="cite-bracket">&#91;</span>48<span class="cite-bracket">&#93;</span></a></sup> and the relatively high stretching frequency of 1947&#160;cm<sup>−1</sup>, the complex is formulated as containing an NO<sup>+</sup> ligand.<sup id="cite_ref-InorgChem_49-0" class="reference"><a href="#cite_note-InorgChem-49"><span class="cite-bracket">&#91;</span>49<span class="cite-bracket">&#93;</span></a></sup> Consequently, iron is assigned an oxidation state of 2+. The iron center has a diamagnetic <a href="/wiki/Crystal_field_theory" title="Crystal field theory">low-spin</a> d<sup>6</sup> electron configuration, although a paramagnetic long-lived metastable state has been observed by <a href="/wiki/EPR_spectroscopy" class="mw-redirect" title="EPR spectroscopy">EPR spectroscopy</a>.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">&#91;</span>50<span class="cite-bracket">&#93;</span></a></sup> </p><p>The chemical reactions of sodium nitroprusside are mainly associated with the NO ligand.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">&#91;</span>51<span class="cite-bracket">&#93;</span></a></sup> For example, addition of <a href="/wiki/Sulfide" title="Sulfide">S<sup>2−</sup></a> ion to [Fe(CN)<sub>5</sub>(NO)]<sup>2−</sup> produces the violet colour [Fe(CN)<sub>5</sub>(NOS)]<sup>4−</sup> ion, which is the basis for a sensitive test for S<sup>2−</sup> ions. An analogous reaction also exists with OH<sup>−</sup> ions, giving [Fe(CN)<sub>5</sub>(NO<sub>2</sub>)]<sup>4−</sup>.<sup id="cite_ref-InorgChem_49-1" class="reference"><a href="#cite_note-InorgChem-49"><span class="cite-bracket">&#91;</span>49<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Roussin%27s_red_salt" title="Roussin&#39;s red salt">Roussin's red salt</a> (K<sub>2</sub>[Fe<sub>2</sub>S<sub>2</sub>(NO)<sub>4</sub>]) and <a href="/wiki/Roussin%27s_black_salt" title="Roussin&#39;s black salt">Roussin's black salt</a> (NaFe<sub>4</sub>S<sub>3</sub>(NO)<sub>7</sub>) are related iron nitrosyl complexes. The former was first prepared by treating nitroprusside with sulfur.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">&#91;</span>52<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=11" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium nitroprusside can be synthesized by digesting a solution of <a href="/wiki/Potassium_ferrocyanide" title="Potassium ferrocyanide">potassium ferrocyanide</a> in water with <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a>, followed by neutralization with <a href="/wiki/Sodium_carbonate" title="Sodium carbonate">sodium carbonate</a>:<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">&#91;</span>53<span class="cite-bracket">&#93;</span></a></sup> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\textstyle {\ce {K4[Fe(CN)6] + 6 HNO3 -&gt; H2[Fe(CN)5(NO)] + CO2 + NH4NO3 + 4 KNO3}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="false" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>K</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mtext>Fe</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>CN</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">]</mo> </mrow> <mo>+</mo> <mn>6</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>HNO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">&#x27F6;<!-- ⟶ --></mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mtext>Fe</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>CN</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>NO</mtext> <mo stretchy="false">)</mo> </mrow> <mo stretchy="false">]</mo> </mrow> <mo>+</mo> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>NO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <mn>4</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>KNO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\textstyle {\ce {K4[Fe(CN)6] + 6 HNO3 -&gt; H2[Fe(CN)5(NO)] + CO2 + NH4NO3 + 4 KNO3}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/0a63cdd7e432d159e3320beea41733371b5e9d5b" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:77.283ex; height:3.009ex;" alt="{\textstyle {\ce {K4[Fe(CN)6] + 6 HNO3 -&gt; H2[Fe(CN)5(NO)] + CO2 + NH4NO3 + 4 KNO3}}}"></span></dd> <dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\textstyle {\ce {H2[Fe(CN)5NO] + Na2CO3 -&gt; Na2[Fe(CN)5(NO)] + CO2 + H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="false" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mtext>Fe</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>CN</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>NO</mtext> <mo stretchy="false">]</mo> </mrow> <mo>+</mo> <msubsup> <mtext>Na</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">&#x27F6;<!-- ⟶ --></mo> <msubsup> <mtext>Na</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mtext>Fe</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>CN</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>NO</mtext> <mo stretchy="false">)</mo> </mrow> <mo stretchy="false">]</mo> </mrow> <mo>+</mo> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\textstyle {\ce {H2[Fe(CN)5NO] + Na2CO3 -&gt; Na2[Fe(CN)5(NO)] + CO2 + H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/e9cc17d013ff3cdb27a1bb68787ad41bc85c0277" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:67.189ex; height:3.009ex;" alt="{\textstyle {\ce {H2[Fe(CN)5NO] + Na2CO3 -&gt; Na2[Fe(CN)5(NO)] + CO2 + H2O}}}"></span></dd></dl> <p>Alternatively, the nitrosyl ligand can be introduced using <a href="/wiki/Nitrite" title="Nitrite">nitrite</a>:<sup id="cite_ref-InorgChem_49-2" class="reference"><a href="#cite_note-InorgChem-49"><span class="cite-bracket">&#91;</span>49<span class="cite-bracket">&#93;</span></a></sup> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\textstyle {\ce {[Fe(CN)6]^4- + H2O + NO_2^- -&gt; [Fe(CN)5(NO)]^2- + CN- + 2OH-}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="false" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mtext>Fe</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>CN</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">]</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> <mo>&#x2212;<!-- − --></mo> </mrow> </msup> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> <mo>+</mo> <msubsup> <mtext>NO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>&#x2212;<!-- − --></mo> </mrow> </msubsup> <mo stretchy="false">&#x27F6;<!-- ⟶ --></mo> <msup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mtext>Fe</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>CN</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>NO</mtext> <mo stretchy="false">)</mo> </mrow> <mo stretchy="false">]</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mo>&#x2212;<!-- − --></mo> </mrow> </msup> <mo>+</mo> <msup> <mtext>CN</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>&#x2212;<!-- − --></mo> </mrow> </msup> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <msup> <mtext>OH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>&#x2212;<!-- − --></mo> </mrow> </msup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\textstyle {\ce {[Fe(CN)6]^4- + H2O + NO_2^- -&gt; [Fe(CN)5(NO)]^2- + CN- + 2OH-}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/1d3083964acaa6daec4f4a0963bf353be4a08794" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:67.952ex; height:3.509ex;" alt="{\textstyle {\ce {[Fe(CN)6]^4- + H2O + NO_2^- -&gt; [Fe(CN)5(NO)]^2- + CN- + 2OH-}}}"></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Other_uses">Other uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=12" title="Edit section: Other uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Sodium_nitroprusside_M%C3%B6ssbauer_spectrum.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Sodium_nitroprusside_M%C3%B6ssbauer_spectrum.svg/220px-Sodium_nitroprusside_M%C3%B6ssbauer_spectrum.svg.png" decoding="async" width="220" height="176" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Sodium_nitroprusside_M%C3%B6ssbauer_spectrum.svg/330px-Sodium_nitroprusside_M%C3%B6ssbauer_spectrum.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/79/Sodium_nitroprusside_M%C3%B6ssbauer_spectrum.svg/440px-Sodium_nitroprusside_M%C3%B6ssbauer_spectrum.svg.png 2x" data-file-width="600" data-file-height="480" /></a><figcaption>Sodium nitroprusside spectrum is used to calibrate Mössbauer spectrometers</figcaption></figure> <p>Sodium nitroprusside is often used as a reference compound for the calibration of <a href="/wiki/M%C3%B6ssbauer_spectrometer" class="mw-redirect" title="Mössbauer spectrometer">Mössbauer spectrometers</a>.<sup id="cite_ref-nbs_54-0" class="reference"><a href="#cite_note-nbs-54"><span class="cite-bracket">&#91;</span>54<span class="cite-bracket">&#93;</span></a></sup> Sodium nitroprusside crystals are also of interest for optical storage. For this application, sodium nitroprusside can be reversibly promoted to a metastable excited state by blue-green light, and de-excited by heat or red light.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">&#91;</span>55<span class="cite-bracket">&#93;</span></a></sup> </p><p>In physiology research, sodium nitroprusside is frequently used to test endothelium-independent vasodilation. <a href="/wiki/Iontophoresis" title="Iontophoresis">Iontophoresis</a>, for example, allows local administration of the drug, preventing the systemic effects listed above but still inducing local microvascular vasodilation. Sodium nitroprusside is also used in microbiology, where it has been linked with the dispersal of <i><a href="/wiki/Pseudomonas_aeruginosa" title="Pseudomonas aeruginosa">Pseudomonas aeruginosa</a></i> <a href="/wiki/Biofilm" title="Biofilm">biofilms</a> by acting as a nitric oxide donor.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">&#91;</span>56<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">&#91;</span>57<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Analytical_reagent">Analytical reagent</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=13" title="Edit section: Analytical reagent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium nitroprusside is also used as an analytical reagent under the name sodium nitroferricyanide for the detection of methyl <a href="/wiki/Ketone" title="Ketone">ketones</a>, <a href="/wiki/Amine" title="Amine">amines</a>, and thiols. It is also used as a catalyst in the quantitative determination of ammonia in water samples via the phenate method.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">&#91;</span>58<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Ketones">Ketones</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=14" title="Edit section: Ketones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The nitroprusside reaction is used for the identification of ketones in urine testing.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">&#91;</span>59<span class="cite-bracket">&#93;</span></a></sup> Sodium nitroprusside was found to give a reaction with acetone or creatine under basic conditions in 1882. Rothera refined this method by the use of ammonia in place of sodium or potassium hydroxide. The reaction was now specific for methyl ketones. Addition of ammonium salts (e.g. ammonium sulfate) improved the sensitivity of the test, too.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">&#91;</span>60<span class="cite-bracket">&#93;</span></a></sup> </p><p>In this test, known as Rothera's test, methyl ketones (CH<sub>3</sub>C(=O)-) under alkaline conditions give bright red coloration (see also <a href="/wiki/Iodoform_test" class="mw-redirect" title="Iodoform test">iodoform test</a>). Rothera's test was initially applied to detecting <a href="/wiki/Ketonuria" title="Ketonuria">ketonuria</a> (a symptom of <a href="/wiki/Diabetes" title="Diabetes">diabetes</a>) in urine samples. This reaction is now exploited in the form of <a href="/wiki/Urine_test_strips" class="mw-redirect" title="Urine test strips">urine test strips</a> (e.g. "Ketostix").<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">&#91;</span>61<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Thiols_and_cysteine">Thiols and cysteine</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=15" title="Edit section: Thiols and cysteine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <b>nitroprusside reaction</b> is a <a href="/wiki/Chemical_test" title="Chemical test">chemical test</a> used to detect the presence of <a href="/wiki/Thiol" title="Thiol">thiol</a> groups of <a href="/wiki/Cysteine" title="Cysteine">cysteine</a> in proteins. Proteins with the free thiol group give a red colour when added to a solution of sodium nitroprusside in <a href="/wiki/Aqueous_ammonia" class="mw-redirect" title="Aqueous ammonia">aqueous ammonia</a>. Some proteins test positive when denatured, indicating that thiol groups are liberated.<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">&#91;</span>62<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">&#91;</span>63<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">&#91;</span>64<span class="cite-bracket">&#93;</span></a></sup> </p><p>Sodium nitroprusside is used in a separate urinalysis test known as the cyanide nitroprusside test or Brand's test. In this test, sodium cyanide is added first to urine and let stand for about 10 minutes. In this time, <a href="/wiki/Disulfide_bond" class="mw-redirect" title="Disulfide bond">disulfide bonds</a> will be broken by the released cyanide. The destruction of disulfide bonds liberates <a href="/wiki/Cysteine" title="Cysteine">cysteine</a> from <a href="/wiki/Cystine" title="Cystine">cystine</a> as well as <a href="/wiki/Homocysteine" title="Homocysteine">homocysteine</a> from <a href="/wiki/Homocystine" title="Homocystine">homocystine</a>. Next, sodium nitroprusside is added to the solution and it reacts with the newly freed <a href="/wiki/Sulfhydryl" class="mw-redirect" title="Sulfhydryl">sulfhydryl</a> groups. The test will turn a red/purple colour if the test is positive, indicating significant amounts of amino acids were in the urine (<a href="/wiki/Aminoaciduria" title="Aminoaciduria">aminoaciduria</a>). Cysteine, cystine, homocysteine, and homocystine all react when present in the urine when this test is performed. This test can indicate inborn errors of amino acid transporters such as <a href="/wiki/Cystinuria" title="Cystinuria">cystinuria</a>, which results from pathology in the transport of dibasic amino acids.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">&#91;</span>65<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Amines">Amines</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=16" title="Edit section: Amines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium nitroprusside is also used to detect <a href="/wiki/Amine" title="Amine">amines</a>, including those in illicit drugs. This compound is thus used as a stain to indicate amines in <a href="/wiki/Thin_layer_chromatography" class="mw-redirect" title="Thin layer chromatography">thin layer chromatography</a>.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">&#91;</span>66<span class="cite-bracket">&#93;</span></a></sup> Sodium nitroprusside is similarly used as a presumptive test for the presence of <a href="/wiki/Alkaloid" title="Alkaloid">alkaloids</a> (amine-containing <a href="/wiki/Natural_products" class="mw-redirect" title="Natural products">natural products</a>) common in illicit substances.<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">&#91;</span>67<span class="cite-bracket">&#93;</span></a></sup> The test, called <a href="/wiki/Simon%27s_reagent" title="Simon&#39;s reagent">Simon's test</a>, is performed by adding 1 volume of a solution of sodium nitroprusside and <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> in <a href="/wiki/Deionized_water" class="mw-redirect" title="Deionized water">deionized water</a> to a suspected drug, followed by the addition of 2 volumes of an <a href="/wiki/Aqueous" class="mw-redirect" title="Aqueous">aqueous</a> <a href="/wiki/Sodium_carbonate" title="Sodium carbonate">sodium carbonate</a> solution. The test turns blue for some <a href="/wiki/Secondary_amines" class="mw-redirect" title="Secondary amines">secondary amines</a>. The most common secondary amines encountered in forensic chemistry include 3,4-methylenedioxymethamphetamine (<a href="/wiki/MDMA" title="MDMA">MDMA</a>, the main component in ecstasy) and <a href="/wiki/Phenethylamines" class="mw-redirect" title="Phenethylamines">phenethylamines</a> such as <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>. Sodium nitroprusside is also useful in the identification the <a href="/wiki/Mercaptan" class="mw-redirect" title="Mercaptan">mercaptans</a> (thiol groups) in the nitroprusside reaction. </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_nitroprusside&amp;action=edit&amp;section=17" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium nitroprusside is primarily used as a vasodilator. It was first used in human medicine in 1928.<sup id="cite_ref-Hist1995_8-4" class="reference"><a href="#cite_note-Hist1995-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> By 1955, data on its safety during short-term use in people with severe <a href="/wiki/Hypertension" title="Hypertension">hypertension</a> had become available.<sup id="cite_ref-Hist1995_8-5" class="reference"><a href="#cite_note-Hist1995-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> Despite this, due to difficulties in its chemical preparation, it was not finally approved by the <a href="/wiki/United_States_of_America" class="mw-redirect" title="United States of America">US</a> FDA until 1974 for the treatment of severe hypertension.<sup id="cite_ref-Hist1995_8-6" class="reference"><a href="#cite_note-Hist1995-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> By 1993, its popularity had grown such that total sales in the US had totalled <a href="/wiki/United_States_Dollar" class="mw-redirect" title="United States Dollar">US$</a>2 million.<sup id="cite_ref-Hist1995_8-7" class="reference"><a href="#cite_note-Hist1995-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> </p> <div style="clear:both;" class=""></div> <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=Sodium_nitroprusside&amp;action=edit&amp;section=18" 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 mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></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://www.tga.gov.au/resources/prescription-medicines-registrations/nitroprusside-rmb-nitroprusside-sxp-nitroprusside-tlb-southern-xp-ip-pty-ltd">"Nitroprusside Rmb, Nitroprusside Sxp, Nitroprusside Tlb (Southern XP IP Pty Ltd)"</a>. <i>Therapeutic Goods Administration (TGA)</i>. 5 December 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">9 April</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Therapeutic+Goods+Administration+%28TGA%29&amp;rft.atitle=Nitroprusside+Rmb%2C+Nitroprusside+Sxp%2C+Nitroprusside+Tlb+%28Southern+XP+IP+Pty+Ltd%29&amp;rft.date=2022-12-05&amp;rft_id=https%3A%2F%2Fwww.tga.gov.au%2Fresources%2Fprescription-medicines-registrations%2Fnitroprusside-rmb-nitroprusside-sxp-nitroprusside-tlb-southern-xp-ip-pty-ltd&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+nitroprusside" 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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.tga.gov.au/resources/prescription-medicines-registrations/sodium-nitroprusside-baxter-baxter-healthcare-pty-ltd">"Sodium nitroprusside Baxter (Baxter Healthcare Pty Ltd)"</a>. <i>Therapeutic Goods Administration (TGA)</i>. 2 June 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">10 September</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Therapeutic+Goods+Administration+%28TGA%29&amp;rft.atitle=Sodium+nitroprusside+Baxter+%28Baxter+Healthcare+Pty+Ltd%29&amp;rft.date=2023-06-02&amp;rft_id=https%3A%2F%2Fwww.tga.gov.au%2Fresources%2Fprescription-medicines-registrations%2Fsodium-nitroprusside-baxter-baxter-healthcare-pty-ltd&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+nitroprusside" class="Z3988"></span></span> </li> <li id="cite_note-AHFS2016-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-AHFS2016_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-AHFS2016_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-AHFS2016_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-AHFS2016_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-AHFS2016_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-AHFS2016_3-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-AHFS2016_3-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-AHFS2016_3-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-AHFS2016_3-8"><sup><i><b>i</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/sodium-nitroprusside.html">"Sodium Nitroprusside"</a>. The American Society of Health-System Pharmacists. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161221004712/https://www.drugs.com/monograph/sodium-nitroprusside.html">Archived</a> from the original on 21 December 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">8 December</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=Sodium+Nitroprusside&amp;rft.pub=The+American+Society+of+Health-System+Pharmacists&amp;rft_id=https%3A%2F%2Fwww.drugs.com%2Fmonograph%2Fsodium-nitroprusside.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+nitroprusside" class="Z3988"></span></span> </li> <li id="cite_note-GG-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-GG_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GG_4-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBruntonChabnerKnollman2010" class="citation book cs1">Brunton L, Chabner B, Knollman B (2010). <a href="/wiki/Goodman_and_Gilman%27s_The_Pharmacological_Basis_of_Therapeutics" class="mw-redirect" title="Goodman and Gilman&#39;s The Pharmacological Basis of Therapeutics"><i>Goodman and Gilman's The Pharmacological Basis of Therapeutics</i></a> (12th&#160;ed.). New York: McGraw-Hill Professional. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-07-162442-8" title="Special:BookSources/978-0-07-162442-8"><bdi>978-0-07-162442-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Goodman+and+Gilman%27s+The+Pharmacological+Basis+of+Therapeutics&amp;rft.place=New+York&amp;rft.edition=12th&amp;rft.pub=McGraw-Hill+Professional&amp;rft.date=2010&amp;rft.isbn=978-0-07-162442-8&amp;rft.aulast=Brunton&amp;rft.aufirst=L&amp;rft.au=Chabner%2C+B&amp;rft.au=Knollman%2C+B&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+nitroprusside" 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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/first-generic-drug-approvals">"First Generic Drug Approvals"</a>. <i>U.S. Food and Drug Administration</i>. 17 October 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">28 November</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=U.S.+Food+and+Drug+Administration&amp;rft.atitle=First+Generic+Drug+Approvals&amp;rft.date=2022-10-17&amp;rft_id=https%3A%2F%2Fwww.fda.gov%2Fdrugs%2Fdrug-and-biologic-approval-and-ind-activity-reports%2Ffirst-generic-drug-approvals&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+nitroprusside" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/pregnancy/nitroprusside.html">"Nitroprusside Pregnancy and Breastfeeding Warnings"</a>. <i>Drugs.com</i>. 2018. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161221005738/https://www.drugs.com/pregnancy/nitroprusside.html">Archived</a> from the original on 21 December 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">14 December</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Drugs.com&amp;rft.atitle=Nitroprusside+Pregnancy+and+Breastfeeding+Warnings&amp;rft.date=2018&amp;rft_id=https%3A%2F%2Fwww.drugs.com%2Fpregnancy%2Fnitroprusside.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+nitroprusside" class="Z3988"></span></span> </li> <li id="cite_note-WHO2008-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-WHO2008_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWorld_Health_Organization2009" class="citation book cs1"><a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). <i>WHO Model Formulary 2008</i>. World Health Organization. p.&#160;283. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/10665%2F44053">10665/44053</a></span>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9789241547659" title="Special:BookSources/9789241547659"><bdi>9789241547659</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=WHO+Model+Formulary+2008&amp;rft.pages=283&amp;rft.pub=World+Health+Organization&amp;rft.date=2009&amp;rft_id=info%3Ahdl%2F10665%2F44053&amp;rft.isbn=9789241547659&amp;rft.au=World+Health+Organization&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+nitroprusside" class="Z3988"></span></span> </li> <li id="cite_note-Hist1995-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-Hist1995_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Hist1995_8-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Hist1995_8-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Hist1995_8-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Hist1995_8-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Hist1995_8-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Hist1995_8-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Hist1995_8-7"><sup><i><b>h</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFriederichButterworth1995" class="citation journal cs1">Friederich JA, Butterworth JF (July 1995). <a rel="nofollow" class="external text" href="https://doi.org/10.1213%2F00000539-199507000-00031">"Sodium nitroprusside: twenty years and counting"</a>. <i>Anesthesia and Analgesia</i>. <b>81</b> (1). <a href="/wiki/Lippincott_Williams_%26_Wilkins" title="Lippincott Williams &amp; Wilkins">Lippincott Williams &amp; Wilkins</a>: 152–162. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1213%2F00000539-199507000-00031">10.1213/00000539-199507000-00031</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7598246">7598246</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Anesthesia+and+Analgesia&amp;rft.atitle=Sodium+nitroprusside%3A+twenty+years+and+counting&amp;rft.volume=81&amp;rft.issue=1&amp;rft.pages=152-162&amp;rft.date=1995-07&amp;rft_id=info%3Adoi%2F10.1213%2F00000539-199507000-00031&amp;rft_id=info%3Apmid%2F7598246&amp;rft.aulast=Friederich&amp;rft.aufirst=JA&amp;rft.au=Butterworth%2C+JF&amp;rft_id=https%3A%2F%2Fdoi.org%2F10.1213%252F00000539-199507000-00031&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+nitroprusside" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNicholsGreeleyLappeUngerleider2006" class="citation book cs1">Nichols DG, Greeley WJ, Lappe DG, Ungerleider RM, Cameron DE, Spevak PJ, Wetzel RC (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=pEpgDAAAQBAJ&amp;pg=PA192"><i>Critical Heart Disease in Infants and Children</i></a> (2&#160;ed.). 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Boston: Butterworths. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9780409900774" title="Special:BookSources/9780409900774"><bdi>9780409900774</bdi></a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21250091">21250091</a> &#8211; via NCBI Bookshelf.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Chapter+140.+Ketonuria&amp;rft.btitle=Clinical+Methods%3A+The+History%2C+Physical%2C+and+Laboratory+Examinations&amp;rft.place=Boston&amp;rft.edition=3rd&amp;rft.pub=Butterworths&amp;rft.date=1990&amp;rft_id=info%3Apmid%2F21250091&amp;rft.isbn=9780409900774&amp;rft.aulast=Comstock&amp;rft.aufirst=JP&amp;rft.au=Garber%2C+AJ&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fbooks%2FNBK247%2F&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+nitroprusside" class="Z3988"></span></span> </li> <li id="cite_note-62"><span class="mw-cite-backlink"><b><a href="#cite_ref-62">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChatterjea2004" class="citation book cs1">Chatterjea MN (1 January 2004). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=p6AEfAEACAAJ"><i>Textbook of Biochemistry for Dental/Nursing/Pharmacy Students</i></a>. 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title="ATC code C02">C02</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrovasodilator" title="Nitrovasodilator">Nitrovasodilator</a> (arterioles and venules)</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 class="mw-selflink selflink">Nitroprusside</a> #</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrazinophthalazine" title="Hydrazinophthalazine">Hydrazinophthalazines</a> (arterioles)</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/Hydralazine" title="Hydralazine">Hydralazine</a> #</li> <li><a href="/wiki/Dihydralazine" title="Dihydralazine">Dihydralazine</a></li> <li><a href="/wiki/Endralazine" title="Endralazine">Endralazine</a></li> <li><a href="/wiki/Cadralazine" title="Cadralazine">Cadralazine</a></li> <li><a href="/wiki/Pildralazine" title="Pildralazine">Pildralazine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Potassium channel openers</a> (arterioles)</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/Minoxidil" title="Minoxidil">Minoxidil</a></li> <li><a href="/wiki/Diazoxide" title="Diazoxide">Diazoxide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">Calcium channel blockers</a> (arterioles)</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><i>see <a href="/wiki/Template:Calcium_channel_blockers" class="mw-redirect" title="Template:Calcium channel blockers">list</a></i></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Nitric_oxide_signaling_modulators" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Nitric_oxide_signaling_modulators" title="Template:Nitric oxide signaling modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nitric_oxide_signaling_modulators" title="Template talk:Nitric oxide signaling modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nitric_oxide_signaling_modulators" title="Special:EditPage/Template:Nitric oxide signaling modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nitric_oxide_signaling_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a> <a href="/wiki/Cell_signaling" title="Cell signaling">signaling</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Nitric_oxide" title="Nitric oxide">Forms</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/Nitroxyl" title="Nitroxyl">Nitroxyl anion (NO<sup>−</sup>; oxonitrate(1-), hyponitrite anion)</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide (NO<sup>⋅</sup>; nitrogen monoxide)</a></li> <li><a href="/wiki/Nitrosonium" title="Nitrosonium">Nitrosonium (NO<sup>+</sup>; nitrosyl cation)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Biological_target" title="Biological target">Targets</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="sGC" scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Soluble_guanylate_cyclase" class="mw-redirect" title="Soluble guanylate cyclase">sGC</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Activators/stimulators:</i> <a href="/w/index.php?title=Ataciguat&amp;action=edit&amp;redlink=1" class="new" title="Ataciguat (page does not exist)">Ataciguat</a></li> <li><a href="/w/index.php?title=BAY_41-2272&amp;action=edit&amp;redlink=1" class="new" title="BAY 41-2272 (page does not exist)">BAY 41-2272</a></li> <li><a href="/w/index.php?title=BAY_41-8543&amp;action=edit&amp;redlink=1" class="new" title="BAY 41-8543 (page does not exist)">BAY 41-8543</a></li> <li><a href="/w/index.php?title=BAY_60-4552&amp;action=edit&amp;redlink=1" class="new" title="BAY 60-4552 (page does not exist)">BAY 60-4552</a></li> <li><a href="/w/index.php?title=BI-703704&amp;action=edit&amp;redlink=1" class="new" title="BI-703704 (page does not exist)">BI-703704</a></li> <li><a href="/wiki/Cinaciguat" title="Cinaciguat">Cinaciguat (BAY 58-2667)</a></li> <li><a href="/w/index.php?title=GSK-2181236A&amp;action=edit&amp;redlink=1" class="new" title="GSK-2181236A (page does not exist)">GSK-2181236A</a></li> <li><a href="/w/index.php?title=Praliciguat&amp;action=edit&amp;redlink=1" class="new" title="Praliciguat (page does not exist)">Praliciguat</a></li> <li><a href="/wiki/Riociguat" title="Riociguat">Riociguat</a></li> <li><a href="/wiki/Vericiguat" title="Vericiguat">Vericiguat</a></li></ul> <ul><li><i>Inhibitors:</i> <a href="/w/index.php?title=1H-(1,2,4)Oxadiazolo(4,3-a)quinoxalin-1-one&amp;action=edit&amp;redlink=1" class="new" title="1H-(1,2,4)Oxadiazolo(4,3-a)quinoxalin-1-one (page does not exist)">ODQ</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/NO_donor" class="mw-redirect" title="NO donor">NO donors</a><br /><small>(<a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>)</small></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><i><a href="/wiki/Nitrate" title="Nitrate">Nitrates</a>:</i> <a href="/wiki/Diethylene_glycol_dinitrate" title="Diethylene glycol dinitrate">Diethylene glycol dinitrate (DEGDN)</a></li> <li><a href="/wiki/Erythritol_tetranitrate" title="Erythritol tetranitrate">Erythritol tetranitrate (ETN)</a></li> <li><a href="/wiki/Ethylene_glycol_dinitrate" title="Ethylene glycol dinitrate">Ethylene glycol dinitrate (EGDN; nitroglycol)</a></li> <li><a href="/wiki/Isosorbide_mononitrate" title="Isosorbide mononitrate">Isosorbide mononitrate (ISMN)</a></li> <li><a href="/wiki/Isosorbide_dinitrate" title="Isosorbide dinitrate">Isosorbide dinitrate (ISDN)</a></li> <li><a href="/wiki/Itramin_tosilate" title="Itramin tosilate">Itramin tosilate</a></li> <li><a href="/wiki/Mannitol_hexanitrate" title="Mannitol hexanitrate">Mannitol hexanitrate</a></li> <li><a href="/wiki/Naproxcinod" title="Naproxcinod">Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)</a></li> <li><a href="/w/index.php?title=NCX-466&amp;action=edit&amp;redlink=1" class="new" title="NCX-466 (page does not exist)">NCX-466</a></li> <li><a href="/w/index.php?title=NCX-2216&amp;action=edit&amp;redlink=1" class="new" title="NCX-2216 (page does not exist)">NCX-2216</a></li> <li><a href="/w/index.php?title=NCX-4016&amp;action=edit&amp;redlink=1" class="new" title="NCX-4016 (page does not exist)">NCX-4016</a></li> <li><a href="/w/index.php?title=NCX_4040&amp;action=edit&amp;redlink=1" class="new" title="NCX 4040 (page does not exist)">NCX 4040</a></li> <li><a href="/w/index.php?title=NCX-4215&amp;action=edit&amp;redlink=1" class="new" title="NCX-4215 (page does not exist)">NCX-4215</a></li> <li><a href="/wiki/Nicorandil" title="Nicorandil">Nicorandil</a></li> <li><a href="/wiki/Nipradilol" title="Nipradilol">Nipradilol (K-351)</a></li> <li><a href="/wiki/Nitrate" title="Nitrate">Nitrate (NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>)</a></li> <li><a href="/w/index.php?title=Nitroatorvastatin&amp;action=edit&amp;redlink=1" class="new" title="Nitroatorvastatin (page does not exist)">Nitroatorvastatin (NCX-6560)</a></li> <li><a href="/w/index.php?title=Nitroflurbiprofen&amp;action=edit&amp;redlink=1" class="new" title="Nitroflurbiprofen (page does not exist)">Nitroflurbiprofen (HCT-1026)</a></li> <li><a href="/w/index.php?title=Nitrofluvastatin&amp;action=edit&amp;redlink=1" class="new" title="Nitrofluvastatin (page does not exist)">Nitrofluvastatin</a></li> <li><a href="/wiki/Nitroglycerin_(drug)" class="mw-redirect" title="Nitroglycerin (drug)">Nitroglycerin (glyceryl trinitrate (GTN))</a></li> <li><a href="/w/index.php?title=Nitropravastatin&amp;action=edit&amp;redlink=1" class="new" title="Nitropravastatin (page does not exist)">Nitropravastatin (NCX-6550)</a></li> <li><a href="/wiki/Pentaerithrityl_tetranitrate" class="mw-redirect" title="Pentaerithrityl tetranitrate">Pentaerithrityl tetranitrate (PETN)</a></li> <li><a href="/wiki/Propatylnitrate" title="Propatylnitrate">Propatylnitrate</a></li> <li><a href="/wiki/Propylene_glycol_dinitrate" title="Propylene glycol dinitrate">Propylene glycol dinitrate (PGDN)</a></li> <li><a href="/w/index.php?title=Sodium_trioxodinitrate&amp;action=edit&amp;redlink=1" class="new" title="Sodium trioxodinitrate (page does not exist)">Sodium trioxodinitrate (Angeli's salt)</a></li> <li>Tenitramine</li> <li><a href="/wiki/Trolnitrate" title="Trolnitrate">Trolnitrate</a></li></ul> <ul><li><i><a href="/wiki/Nitroso_compound" class="mw-redirect" title="Nitroso compound">Nitroso compounds</a>/<a href="/wiki/Nitrite" title="Nitrite">nitrites</a>:</i> <a href="/wiki/Nitrite" title="Nitrite">Nitrite (NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>)</a>; <i>O-Nitroso compounds (<a href="/wiki/Alkyl_nitrite" title="Alkyl nitrite">alkyl nitrites</a>):</i> <a href="/wiki/Amyl_nitrite" title="Amyl nitrite">Amyl nitrite (isoamyl nitrite, isopentyl nitrite)</a></li> <li><a href="/wiki/Cyclohexyl_nitrite" title="Cyclohexyl nitrite">Cyclohexyl nitrite</a></li> <li><a href="/wiki/Ethyl_nitrite" title="Ethyl nitrite">Ethyl nitrite</a></li> <li><a href="/wiki/Hexyl_nitrite" title="Hexyl nitrite">Hexyl nitrite</a></li> <li><a href="/wiki/Isobutyl_nitrite" title="Isobutyl nitrite">Isobutyl nitrite (2-methylpropyl nitrite)</a></li> <li><a href="/wiki/Isopropyl_nitrite" title="Isopropyl nitrite">Isopropyl nitrite</a></li> <li><a href="/wiki/Methyl_nitrite" title="Methyl nitrite">Methyl nitrite</a></li> <li><a href="/wiki/Butyl_nitrite" title="Butyl nitrite"><i>n</i>-Butyl nitrite</a></li> <li><a href="/wiki/Pentyl_nitrite" title="Pentyl nitrite">Pentyl nitrite</a></li> <li><a href="/wiki/Tert-Butyl_nitrite" title="Tert-Butyl nitrite"><i>tert</i>-Butyl nitrite</a>; <i><a href="/wiki/S-Nitrosothiol" title="S-Nitrosothiol">S-Nitroso compounds</a> (thionitrites):</i> <a href="/w/index.php?title=LA810&amp;action=edit&amp;redlink=1" class="new" title="LA810 (page does not exist)">LA810</a></li> <li><a href="/w/index.php?title=S-Nitrosoalbumin&amp;action=edit&amp;redlink=1" class="new" title="S-Nitrosoalbumin (page does not exist)">S-Nitrosoalbumin (SNALB)</a></li> <li><a href="/w/index.php?title=S-Nitrosated_AR545C&amp;action=edit&amp;redlink=1" class="new" title="S-Nitrosated AR545C (page does not exist)">S-Nitrosated AR545C</a></li> <li><a href="/w/index.php?title=S-Nitroso-N-acetylcysteine&amp;action=edit&amp;redlink=1" class="new" title="S-Nitroso-N-acetylcysteine (page does not exist)">S-Nitroso-N-acetylcysteine (SNAC)</a></li> <li><a href="/wiki/S-Nitroso-N-acetylpenicillamine" title="S-Nitroso-N-acetylpenicillamine">S-Nitroso-N-acetylpenicillamine (SNAP)</a></li> <li><a href="/w/index.php?title=S-Nitroso-N-valerylpenicillamine&amp;action=edit&amp;redlink=1" class="new" title="S-Nitroso-N-valerylpenicillamine (page does not exist)">S-Nitroso-N-valerylpenicillamine (SNVP)</a></li> <li><a href="/w/index.php?title=S-Nitrosocaptopril&amp;action=edit&amp;redlink=1" class="new" title="S-Nitrosocaptopril (page does not exist)">S-Nitrosocaptopril (SNO-Cap)</a></li> <li><a href="/w/index.php?title=S-Nitrosocysteine&amp;action=edit&amp;redlink=1" class="new" title="S-Nitrosocysteine (page does not exist)">S-Nitrosocysteine (SNC, CysNO, SNO-Cys)</a></li> <li><a href="/w/index.php?title=S-Nitrosodiclofenac&amp;action=edit&amp;redlink=1" class="new" title="S-Nitrosodiclofenac (page does not exist)">S-Nitrosodiclofenac</a></li> <li><a href="/wiki/S-Nitrosoglutathione" title="S-Nitrosoglutathione">S-Nitrosoglutathione (GSNO, SNOG)</a></li> <li><a href="/w/index.php?title=S-Nitrosated_tissue-type_plasminogen_activator&amp;action=edit&amp;redlink=1" class="new" title="S-Nitrosated tissue-type plasminogen activator (page does not exist)">SNO-t-PA</a></li> <li><a href="/w/index.php?title=S-Nitrosated_von_Willebrand_factor&amp;action=edit&amp;redlink=1" class="new" title="S-Nitrosated von Willebrand factor (page does not exist)">SNO-vWF</a>; <i>N-Nitroso compounds (e.g., <a href="/wiki/Nitrosamine" title="Nitrosamine">nitrosamines</a>):</i> <a href="/w/index.php?title=SIN-1A&amp;action=edit&amp;redlink=1" class="new" title="SIN-1A (page does not exist)">SIN-1A</a></li></ul> <ul><li><i>Nitrosyl compounds:</i> <i><a href="/wiki/Metal_nitrosyl_complex" title="Metal nitrosyl complex">Metal nitrosyl complexes</a>:</i> <a href="/wiki/Roussin%27s_black_salt" title="Roussin&#39;s black salt">Roussin's black salt</a></li> <li><a href="/wiki/Roussin%27s_red_salt" title="Roussin&#39;s red salt">Roussin's red salt</a></li> <li><a class="mw-selflink selflink">Sodium nitroprusside (SNP)</a></li></ul> <ul><li><i><a href="/wiki/NONOate" title="NONOate">NONOates</a> (diazeniumdiolates):</i> <a href="/w/index.php?title=Diethylamine/NO&amp;action=edit&amp;redlink=1" class="new" title="Diethylamine/NO (page does not exist)">Diethylamine/NO (DEA/NO)</a></li> <li><a href="/w/index.php?title=Diethylenetriamine/NO&amp;action=edit&amp;redlink=1" class="new" title="Diethylenetriamine/NO (page does not exist)">Diethylenetriamine/NO (DETA/NO)</a></li> <li><a href="/w/index.php?title=GLO/NO&amp;action=edit&amp;redlink=1" class="new" title="GLO/NO (page does not exist)">GLO/NO</a></li> <li><a href="/w/index.php?title=JS-K&amp;action=edit&amp;redlink=1" class="new" title="JS-K (page does not exist)">JS-K</a></li> <li><a href="/w/index.php?title=Methylamine_hexamethylene_methylamine/NO&amp;action=edit&amp;redlink=1" class="new" title="Methylamine hexamethylene methylamine/NO (page does not exist)">Methylamine hexamethylene methylamine/NO (MAHMA/NO)</a></li> <li><a href="/w/index.php?title=PROLI/NO&amp;action=edit&amp;redlink=1" class="new" title="PROLI/NO (page does not exist)">PROLI/NO</a></li> <li><a href="/w/index.php?title=Spermine/NO&amp;action=edit&amp;redlink=1" class="new" title="Spermine/NO (page does not exist)">Spermine/NO (SPER/NO)</a></li> <li><a href="/w/index.php?title=V-PYRRO/NO&amp;action=edit&amp;redlink=1" class="new" title="V-PYRRO/NO (page does not exist)">V-PYRRO/NO</a></li></ul> <ul><li><i>Heterocyclic compounds:</i> <i><a href="/wiki/Furoxan" title="Furoxan">Furoxans</a>:</i> <a href="/wiki/Furoxan" title="Furoxan">Furoxan</a></li> <li><a href="/w/index.php?title=REC15/2739&amp;action=edit&amp;redlink=1" class="new" title="REC15/2739 (page does not exist)">REC15/2739</a>; <i><a href="/w/index.php?title=Sydnonimine&amp;action=edit&amp;redlink=1" class="new" title="Sydnonimine (page does not exist)">Sydnonimines</a>:</i> <a href="/wiki/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Linsidomine" title="Linsidomine">Linsidomine (SIN-1)</a></li> <li><a href="/wiki/Molsidomine" title="Molsidomine">Molsidomine (SIN-10)</a></li> <li><a href="/w/index.php?title=Sydnonimine&amp;action=edit&amp;redlink=1" class="new" title="Sydnonimine (page does not exist)">Sydnonimine</a></li></ul> <ul><li><i>Unsorted:</i> <a href="/wiki/Cimlanod" title="Cimlanod">Cimlanod</a></li> <li><a href="/w/index.php?title=FK-409&amp;action=edit&amp;redlink=1" class="new" title="FK-409 (page does not exist)">FK-409</a></li> <li><a href="/w/index.php?title=FR144220&amp;action=edit&amp;redlink=1" class="new" title="FR144220 (page does not exist)">FR144220</a></li> <li><a href="/w/index.php?title=FR146881&amp;action=edit&amp;redlink=1" class="new" title="FR146881 (page does not exist)">FR146881</a></li> <li><a href="/w/index.php?title=N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide&amp;action=edit&amp;redlink=1" class="new" title="N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide (page does not exist)">N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Nitric_oxide_synthase" title="Nitric oxide synthase">NOS</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/NOS1" title="NOS1">nNOS</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=3-Bromo-7-nitroindazole&amp;action=edit&amp;redlink=1" class="new" title="3-Bromo-7-nitroindazole (page does not exist)">3-Bromo-7-nitroindazole</a></li> <li><a href="/w/index.php?title=3-Chloroindazole&amp;action=edit&amp;redlink=1" class="new" title="3-Chloroindazole (page does not exist)">3-Chloroindazole</a></li> <li><a href="/w/index.php?title=3-Chloro-5-nitroindazole&amp;action=edit&amp;redlink=1" class="new" title="3-Chloro-5-nitroindazole (page does not exist)">3-Chloro-5-nitroindazole</a></li> <li><a href="/w/index.php?title=5-Nitroindazole&amp;action=edit&amp;redlink=1" class="new" title="5-Nitroindazole (page does not exist)">5-Nitroindazole</a></li> <li><a href="/w/index.php?title=6-Nitroindazole&amp;action=edit&amp;redlink=1" class="new" title="6-Nitroindazole (page does not exist)">6-Nitroindazole</a></li> <li><a href="/wiki/7-Nitroindazole" title="7-Nitroindazole">7-Nitroindazole</a></li> <li><a href="/w/index.php?title=A-84643&amp;action=edit&amp;redlink=1" class="new" title="A-84643 (page does not exist)">A-84643</a></li> <li><a href="/wiki/Aminoguanidine" class="mw-redirect" title="Aminoguanidine">Aminoguanidine (pimagedine)</a></li> <li><a href="/w/index.php?title=ARL-17477&amp;action=edit&amp;redlink=1" class="new" title="ARL-17477 (page does not exist)">ARL-17477</a></li> <li><a href="/wiki/Indazole" title="Indazole">Indazole</a></li> <li><a href="/w/index.php?title=N5-(1-Iminoethyl)-L-ornithine&amp;action=edit&amp;redlink=1" class="new" title="N5-(1-Iminoethyl)-L-ornithine (page does not exist)">N<sup>5</sup>-(1-Iminoethyl)-L-ornithine (<small>L</small>-NIO)</a></li> <li><a href="/w/index.php?title=N%CF%89-Methyl-L-arginine&amp;action=edit&amp;redlink=1" class="new" title="Nω-Methyl-L-arginine (page does not exist)">N<sup>ω</sup>-Methyl-<small>L</small>-arginine (<small>L</small>-NMA)</a></li> <li><a href="/w/index.php?title=N%CF%89-Propyl-L-arginine&amp;action=edit&amp;redlink=1" class="new" title="Nω-Propyl-L-arginine (page does not exist)">N<sup>ω</sup>-Propyl-<small>L</small>-arginine (<small>L</small>-NPA)</a></li> <li><a href="/wiki/Nitroarginine" title="Nitroarginine">Nitroarginine (NNA, NOARG)</a></li> <li><a href="/wiki/Pentamidine_isethionate" class="mw-redirect" title="Pentamidine isethionate">Pentamidine isethionate</a></li> <li><a href="/w/index.php?title=1-(2-Trifluoromethylphenyl)imidazole&amp;action=edit&amp;redlink=1" class="new" title="1-(2-Trifluoromethylphenyl)imidazole (page does not exist)">TRIM</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Nitric_oxide_synthase_2_(inducible)" title="Nitric oxide synthase 2 (inducible)">iNOS</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=1-Amino-2-hydroxyguanidine&amp;action=edit&amp;redlink=1" class="new" title="1-Amino-2-hydroxyguanidine (page does not exist)">1-Amino-2-hydroxyguanidine</a></li> <li><a href="/w/index.php?title=2-Ethylaminoguanidine&amp;action=edit&amp;redlink=1" class="new" title="2-Ethylaminoguanidine (page does not exist)">2-Ethylaminoguanidine</a></li> <li><a href="/w/index.php?title=2-Iminopiperidine&amp;action=edit&amp;redlink=1" class="new" title="2-Iminopiperidine (page does not exist)">2-Iminopiperidine</a></li> <li><a href="/w/index.php?title=1400W&amp;action=edit&amp;redlink=1" class="new" title="1400W (page does not exist)">1400W</a></li> <li><a href="/w/index.php?title=S-aminoethylisothiourea&amp;action=edit&amp;redlink=1" class="new" title="S-aminoethylisothiourea (page does not exist)">AEITU</a></li> <li><a href="/wiki/Aminoguanidine" class="mw-redirect" title="Aminoguanidine">Aminoguanidine (pimagedine)</a></li> <li><a href="/w/index.php?title=2-Amino-5,6-dihydro-6-methyl-4H-1,3-thiazine&amp;action=edit&amp;redlink=1" class="new" title="2-Amino-5,6-dihydro-6-methyl-4H-1,3-thiazine (page does not exist)">AMT</a></li> <li><a href="/w/index.php?title=AR-C_102222&amp;action=edit&amp;redlink=1" class="new" title="AR-C 102222 (page does not exist)">AR-C 102222</a></li> <li><a href="/w/index.php?title=BYK-191023&amp;action=edit&amp;redlink=1" class="new" title="BYK-191023 (page does not exist)">BYK-191023</a></li> <li><a href="/wiki/Canavanine" title="Canavanine">Canavanine</a></li> <li><a href="/w/index.php?title=Cindunistat&amp;action=edit&amp;redlink=1" class="new" title="Cindunistat (page does not exist)">Cindunistat (SD-6010)</a></li> <li><a href="/w/index.php?title=S-Ethylisothiourea&amp;action=edit&amp;redlink=1" class="new" title="S-Ethylisothiourea (page does not exist)">EITU</a></li> <li><a href="/w/index.php?title=S-Isopropylisothiourea&amp;action=edit&amp;redlink=1" class="new" title="S-Isopropylisothiourea (page does not exist)">IPTU</a></li> <li><a href="/w/index.php?title=S-Methylisothiourea&amp;action=edit&amp;redlink=1" class="new" title="S-Methylisothiourea (page does not exist)">MITU</a></li> <li><a href="/w/index.php?title=N5-(1-Iminoethyl)-L-ornithine&amp;action=edit&amp;redlink=1" class="new" title="N5-(1-Iminoethyl)-L-ornithine (page does not exist)">N<sup>5</sup>-(1-Iminoethyl)-<small>L</small>-ornithine (<small>L</small>-NIO)</a></li> <li><a href="/w/index.php?title=N6-(1-Iminoethyl)-L-lysine&amp;action=edit&amp;redlink=1" class="new" title="N6-(1-Iminoethyl)-L-lysine (page does not exist)">N<sup>6</sup>-(1-Iminoethyl)-<small>L</small>-lysine (<small>L</small>-NIL)</a></li> <li><a href="/w/index.php?title=N%CF%89-Methyl-L-arginine&amp;action=edit&amp;redlink=1" class="new" title="Nω-Methyl-L-arginine (page does not exist)">N<sup>ω</sup>-Methyl-<small>L</small>-arginine (<small>L</small>-NMA)</a></li> <li><a href="/w/index.php?title=Ronopterin&amp;action=edit&amp;redlink=1" class="new" title="Ronopterin (page does not exist)">Ronopterin (VAS-203)</a></li> <li><a href="/w/index.php?title=1-(2-Trifluoromethylphenyl)imidazole&amp;action=edit&amp;redlink=1" class="new" title="1-(2-Trifluoromethylphenyl)imidazole (page does not exist)">TRIM</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Endothelial_NOS" title="Endothelial NOS">eNOS</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminoguanidine" class="mw-redirect" title="Aminoguanidine">Aminoguanidine (pimagedine)</a></li> <li><a href="/w/index.php?title=N5-(1-Iminoethyl)-L-ornithine&amp;action=edit&amp;redlink=1" class="new" title="N5-(1-Iminoethyl)-L-ornithine (page does not exist)">N<sup>5</sup>-(1-Iminoethyl)-<small>L</small>-ornithine (<small>L</small>-NIO)</a></li> <li><a href="/w/index.php?title=N%CF%89-Methyl-L-arginine&amp;action=edit&amp;redlink=1" class="new" title="Nω-Methyl-L-arginine (page does not exist)">N<sup>ω</sup>-Methyl-<small>L</small>-arginine (<small>L</small>-NMA)</a></li> <li><a href="/wiki/Nitroarginine" title="Nitroarginine">Nitroarginine (NNA, NOARG)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Unsorted</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Asymmetric_dimethylarginine" title="Asymmetric dimethylarginine">Asymmetric dimethylarginine (ADMA)</a></li> <li><a href="/w/index.php?title=CKD-712&amp;action=edit&amp;redlink=1" class="new" title="CKD-712 (page does not exist)">CKD-712</a></li> <li><a href="/w/index.php?title=Guanidinoethyldisulfide&amp;action=edit&amp;redlink=1" class="new" title="Guanidinoethyldisulfide (page does not exist)">Guanidinoethyldisulfide (GED)</a></li> <li><a href="/w/index.php?title=GW-273629&amp;action=edit&amp;redlink=1" class="new" title="GW-273629 (page does not exist)">GW-273629</a></li> <li><a href="/wiki/Indospicine" title="Indospicine">Indospicine</a></li> <li><a href="/w/index.php?title=KD-7040&amp;action=edit&amp;redlink=1" class="new" title="KD-7040 (page does not exist)">KD-7040</a></li> <li><a href="/w/index.php?title=Nitroarginine_methyl_ester&amp;action=edit&amp;redlink=1" class="new" title="Nitroarginine methyl ester (page does not exist)">Nitroarginine methyl ester (NAME)</a></li> <li><a href="/w/index.php?title=NCX-456&amp;action=edit&amp;redlink=1" class="new" title="NCX-456 (page does not exist)">NCX-456</a></li> <li><a href="/w/index.php?title=NXN-462&amp;action=edit&amp;redlink=1" class="new" title="NXN-462 (page does not exist)">NXN-462</a></li> <li><a href="/w/index.php?title=ONO-1714&amp;action=edit&amp;redlink=1" class="new" title="ONO-1714 (page does not exist)">ONO-1714</a></li> <li><a href="/w/index.php?title=VAS-2381&amp;action=edit&amp;redlink=1" class="new" title="VAS-2381 (page does not exist)">VAS-2381</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Arginase" title="Arginase">Arginase</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=2S-Amino-6-boronohexonic_acid&amp;action=edit&amp;redlink=1" class="new" title="2S-Amino-6-boronohexonic acid (page does not exist)">ABH</a></li> <li><a href="/w/index.php?title=N%CF%89-Hydroxy-L-arginine&amp;action=edit&amp;redlink=1" class="new" title="Nω-Hydroxy-L-arginine (page does not exist)">N<sup>ω</sup>-Hydroxy-<small>L</small>-arginine (NOHA)</a></li> <li><a href="/wiki/Chlorogenic_acid" title="Chlorogenic acid">chlorogenic acid</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">ginseng</a></li> <li><a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a></li> <li><a href="/wiki/Ornithine" title="Ornithine">ornithine</a></li> <li><a href="/wiki/Norvaline" title="Norvaline">norvaline</a></li> <li><a href="/wiki/Lysine" title="Lysine">lysine</a></li> <li><a href="/w/index.php?title=Alpha_aminoacids&amp;action=edit&amp;redlink=1" class="new" title="Alpha aminoacids (page does not exist)">alpha aminoacids</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/CAMK" title="CAMK">CAMK</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Calmidazolium&amp;action=edit&amp;redlink=1" class="new" title="Calmidazolium (page does not exist)">Calmidazolium</a></li> <li><a href="/w/index.php?title=W-7_(drug)&amp;action=edit&amp;redlink=1" class="new" title="W-7 (drug) (page does not exist)">W-7</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</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><i>Precursors:</i> <a href="/wiki/Arginine" title="Arginine"><small>L</small>-Arginine</a></li> <li><a href="/w/index.php?title=N%CF%89-Hydroxy-L-arginine&amp;action=edit&amp;redlink=1" class="new" title="Nω-Hydroxy-L-arginine (page does not exist)">N<sup>ω</sup>-Hydroxy-<small>L</small>-arginine (NOHA)</a></li></ul> <ul><li><i>Cofactors:</i> <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NADPH</a></li> <li><a href="/wiki/Flavin_adenine_dinucleotide" title="Flavin adenine dinucleotide">FAD</a></li> <li><a href="/wiki/Flavin_mononucleotide" title="Flavin mononucleotide">FMN</a></li> <li><a href="/wiki/Heme" title="Heme">Heme</a></li> <li><a href="/wiki/Tetrahydrobiopterin" title="Tetrahydrobiopterin">BH<sub>4</sub></a></li> <li><a href="/wiki/Calmodulin" title="Calmodulin">CaM</a></li> <li><a href="/wiki/Oxygen" title="Oxygen">O<sub>2</sub></a></li> <li><a href="/wiki/Calcium" title="Calcium">Ca<sup>2+</sup></a></li></ul> <ul><li><i>Indirect/downstream NO modulators:</i> <a href="/wiki/ACE_inhibitor" title="ACE inhibitor">ACE inhibitors</a>/<a href="/wiki/Angiotensin_II_receptor_antagonist" class="mw-redirect" title="Angiotensin II receptor antagonist">AT-II receptor antagonists</a> (e.g., <a href="/wiki/Captopril" title="Captopril">captopril</a>, <a href="/wiki/Losartan" title="Losartan">losartan</a>)</li> <li><a href="/wiki/Endothelin_receptor_antagonist" title="Endothelin receptor antagonist">ET<sub>B</sub> receptor antagonists</a> (e.g., <a href="/wiki/Bosentan" title="Bosentan">bosentan</a>)</li> <li><a href="/wiki/L-Type_calcium_channel" class="mw-redirect" title="L-Type calcium channel">L-Type calcium channel</a> <a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">blockers</a> (e.g., <a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">dihydropyridines</a>: <a href="/wiki/Nifedipine" title="Nifedipine">nifedipine</a>)</li> <li><a href="/wiki/Nebivolol" title="Nebivolol">Nebivolol</a> (<a href="/wiki/Beta_blocker" title="Beta blocker">beta blocker</a>)</li> <li><a href="/wiki/PDE5_inhibitor" title="PDE5 inhibitor">PDE5 inhibitors</a> (e.g., <a href="/wiki/Sildenafil" title="Sildenafil">sildenafil</a>)</li> <li>non-selective PDE inhibitors (e.g., <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>)</li> <li>PDE9 inhibitors (e.g., <a href="/wiki/Paraxanthine" title="Paraxanthine">paraxanthine</a>)</li> <li>cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)</li> <li><a href="/wiki/Statin" title="Statin">Statins</a> (e.g., <a href="/wiki/Simvastatin" title="Simvastatin">simvastatin</a>)</li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;padding:0.15em 0;column-gap:1em;align-items:baseline;margin:0;list-style:none}.mw-parser-output .portal-bar-content-related{margin:0;list-style:none}.mw-parser-output .portal-bar-item{display:inline-block;margin:0.15em 0.2em;min-height:24px;line-height:24px}@media screen and (max-width:768px){.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;flex-flow:column wrap;align-items:baseline}.mw-parser-output .portal-bar-header{text-align:center;flex:0;padding-left:0.5em;margin:0 auto}.mw-parser-output .portal-bar-related{font-size:100%;align-items:flex-start}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;align-items:center;flex:0;column-gap:1em;border-top:1px solid #a2a9b1;margin:0 auto;list-style:none}.mw-parser-output .portal-bar-content-related{border-top:none;margin:0;list-style:none}}.mw-parser-output .navbox+link+.portal-bar,.mw-parser-output .navbox+style+.portal-bar,.mw-parser-output .navbox+link+.portal-bar-bordered,.mw-parser-output .navbox+style+.portal-bar-bordered,.mw-parser-output .sister-bar+link+.portal-bar,.mw-parser-output .sister-bar+style+.portal-bar,.mw-parser-output .portal-bar+.navbox-styles+.navbox,.mw-parser-output .portal-bar+.navbox-styles+.sister-bar{margin-top:-1px}</style><div class="portal-bar noprint metadata noviewer portal-bar-bordered" role="navigation" aria-label="Portals"><span class="portal-bar-header"><a href="/wiki/Wikipedia:Contents/Portals" title="Wikipedia:Contents/Portals">Portal</a>:</span><ul class="portal-bar-content"><li class="portal-bar-item"><span class="nowrap"><span typeof="mw:File"><span><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/8px-WHO_Rod.svg.png" decoding="async" width="8" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/12px-WHO_Rod.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/16px-WHO_Rod.svg.png 2x" data-file-width="107" 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