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vector-toc-level-2"> <a class="vector-toc-link" href="#Pyrolysis_and_combustion_product"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Pyrolysis and combustion product</span> </div> </a> <ul id="toc-Pyrolysis_and_combustion_product-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Organic_derivatives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Organic_derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Organic derivatives</span> </div> </a> <ul id="toc-Organic_derivatives-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-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 Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Protonation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Protonation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Protonation</span> </div> </a> <ul id="toc-Protonation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydrolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydrolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Hydrolysis</span> </div> </a> <ul id="toc-Hydrolysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alkylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alkylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Alkylation</span> </div> </a> <ul id="toc-Alkylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Redox" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Redox"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Redox</span> </div> </a> <ul id="toc-Redox-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metal_complexation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metal_complexation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Metal complexation</span> </div> </a> <ul id="toc-Metal_complexation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Manufacture" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Manufacture"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Manufacture</span> </div> </a> <ul id="toc-Manufacture-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Toxicity</span> </div> </a> <button aria-controls="toc-Toxicity-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 Toxicity subsection</span> </button> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> <li id="toc-Antidote" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Antidote"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Antidote</span> </div> </a> <ul id="toc-Antidote-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Sensitivity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sensitivity"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Sensitivity</span> </div> </a> <ul id="toc-Sensitivity-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Applications</span> </div> </a> <button aria-controls="toc-Applications-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 Applications subsection</span> </button> <ul id="toc-Applications-sublist" class="vector-toc-list"> <li id="toc-Mining" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mining"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Mining</span> </div> </a> <ul id="toc-Mining-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Industrial_organic_chemistry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Industrial_organic_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Industrial organic chemistry</span> </div> </a> <ul id="toc-Industrial_organic_chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Medical_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Medical_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Medical uses</span> </div> </a> <ul id="toc-Medical_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Illegal_fishing_and_poaching" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Illegal_fishing_and_poaching"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Illegal fishing and poaching</span> </div> </a> <ul id="toc-Illegal_fishing_and_poaching-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pest_control" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pest_control"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.5</span> <span>Pest control</span> </div> </a> <ul id="toc-Pest_control-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Niche_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Niche_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.6</span> <span>Niche uses</span> </div> </a> <ul id="toc-Niche_uses-sublist" class="vector-toc-list"> <li id="toc-Human_poisoning" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Human_poisoning"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.6.1</span> <span>Human poisoning</span> </div> </a> <ul id="toc-Human_poisoning-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Food_additive" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Food_additive"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.6.2</span> <span>Food additive</span> </div> </a> <ul id="toc-Food_additive-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Chemical_tests_for_cyanide" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemical_tests_for_cyanide"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Chemical tests for cyanide</span> </div> </a> <button aria-controls="toc-Chemical_tests_for_cyanide-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 Chemical tests for cyanide subsection</span> </button> <ul id="toc-Chemical_tests_for_cyanide-sublist" class="vector-toc-list"> <li id="toc-Qualitative_tests" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Qualitative_tests"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Qualitative tests</span> </div> </a> <ul id="toc-Qualitative_tests-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>External links</span> </div> </a> <ul id="toc-External_links-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">Cyanide</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 66 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-66" 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">66 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Sianied" title="Sianied – Afrikaans" lang="af" hreflang="af" data-title="Sianied" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B3%D9%8A%D8%A7%D9%86%D9%8A%D8%AF" title="سيانيد – Arabic" lang="ar" hreflang="ar" data-title="سيانيد" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%DB%8C%D8%A7%D9%86%D9%88%D8%B1" title="سیانور – South Azerbaijani" lang="azb" hreflang="azb" data-title="سیانور" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B8%E0%A6%BE%E0%A6%AF%E0%A6%BC%E0%A6%BE%E0%A6%A8%E0%A6%BE%E0%A6%87%E0%A6%A1" title="সায়ানাইড – Bangla" lang="bn" hreflang="bn" data-title="সায়ানাইড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A6%D0%B8%D0%B0%D0%BD%D0%B8%D0%B4" title="Цианид – Bulgarian" lang="bg" hreflang="bg" data-title="Цианид" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Cijanid" title="Cijanid – Bosnian" lang="bs" hreflang="bs" data-title="Cijanid" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Cianur" title="Cianur – Catalan" lang="ca" hreflang="ca" data-title="Cianur" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cv mw-list-item"><a href="https://cv.wikipedia.org/wiki/%D0%A6%D0%B8%D0%B0%D0%BD%D0%B8%D0%B4" title="Цианид – Chuvash" lang="cv" hreflang="cv" data-title="Цианид" data-language-autonym="Чӑвашла" data-language-local-name="Chuvash" class="interlanguage-link-target"><span>Чӑвашла</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Kyanidy" title="Kyanidy – Czech" lang="cs" hreflang="cs" data-title="Kyanidy" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Cyanid" title="Cyanid – Danish" lang="da" hreflang="da" data-title="Cyanid" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Cyanide" title="Cyanide – German" lang="de" hreflang="de" data-title="Cyanide" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CF%85%CE%B1%CE%BD%CE%AF%CE%B4%CE%B9%CE%BF" title="Κυανίδιο – Greek" lang="el" hreflang="el" data-title="Κυανίδιο" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Cianuro" title="Cianuro – Spanish" lang="es" hreflang="es" data-title="Cianuro" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Cianido" title="Cianido – Esperanto" lang="eo" hreflang="eo" data-title="Cianido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Zianuro" title="Zianuro – Basque" lang="eu" hreflang="eu" data-title="Zianuro" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%DB%8C%D8%A7%D9%86%D9%88%D8%B1" title="سیانور – Persian" lang="fa" hreflang="fa" data-title="سیانور" 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/Cyanure" title="Cyanure – French" lang="fr" hreflang="fr" data-title="Cyanure" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Ciain%C3%ADd" title="Ciainíd – Irish" lang="ga" hreflang="ga" data-title="Ciainíd" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Cianuro" title="Cianuro – Galician" lang="gl" hreflang="gl" data-title="Cianuro" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%82%AC%EC%9D%B4%EC%95%88%ED%99%94%EB%AC%BC" title="사이안화물 – Korean" lang="ko" hreflang="ko" data-title="사이안화물" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%91%D5%AB%D5%A1%D5%B6%D5%AB%D5%A4" title="Ցիանիդ – Armenian" lang="hy" hreflang="hy" data-title="Ցիանիդ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B8%E0%A4%BE%E0%A4%AF%E0%A4%A8%E0%A4%BE%E0%A4%87%E0%A4%A1" title="सायनाइड – Hindi" lang="hi" hreflang="hi" data-title="सायनाइड" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Cijanid" title="Cijanid – Croatian" lang="hr" hreflang="hr" data-title="Cijanid" 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/Sianida" title="Sianida – Indonesian" lang="id" hreflang="id" data-title="Sianida" 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/Cianuro" title="Cianuro – Italian" lang="it" hreflang="it" data-title="Cianuro" 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%A6%D7%99%D7%90%D7%A0%D7%99%D7%93" title="ציאניד – Hebrew" lang="he" hreflang="he" data-title="ציאניד" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Sianida" title="Sianida – Javanese" lang="jv" hreflang="jv" data-title="Sianida" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%AA%E1%83%98%E1%83%90%E1%83%9C%E1%83%98%E1%83%93%E1%83%98" title="ციანიდი – Georgian" lang="ka" hreflang="ka" data-title="ციანიდი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Cyanidum" title="Cyanidum – Latin" lang="la" hreflang="la" data-title="Cyanidum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Cian%C4%ABdi" title="Cianīdi – Latvian" lang="lv" hreflang="lv" data-title="Cianīdi" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Cianidas" title="Cianidas – Lithuanian" lang="lt" hreflang="lt" data-title="Cianidas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Cianid" title="Cianid – Hungarian" lang="hu" hreflang="hu" data-title="Cianid" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A6%D0%B8%D1%98%D0%B0%D0%BD%D0%B8%D0%B4" title="Цијанид – Macedonian" lang="mk" hreflang="mk" data-title="Цијанид" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B8%E0%B4%AF%E0%B4%A8%E0%B5%88%E0%B4%A1%E0%B5%8D" title="സയനൈഡ് – Malayalam" lang="ml" hreflang="ml" data-title="സയനൈഡ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Sianida" title="Sianida – Malay" lang="ms" hreflang="ms" data-title="Sianida" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%86%E1%80%AD%E1%80%AF%E1%80%84%E1%80%BA%E1%80%9A%E1%80%AC%E1%80%94%E1%80%AD%E1%80%AF%E1%80%80%E1%80%BA" title="ဆိုင်ယာနိုက် – Burmese" lang="my" hreflang="my" data-title="ဆိုင်ယာနိုက်" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cyanide" title="Cyanide – Dutch" lang="nl" hreflang="nl" data-title="Cyanide" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B7%E3%82%A2%E3%83%B3%E5%8C%96%E7%89%A9" title="シアン化物 – Japanese" lang="ja" hreflang="ja" data-title="シアン化物" 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-frr mw-list-item"><a href="https://frr.wikipedia.org/wiki/Ts%C3%BCaniid" title="Tsüaniid – Northern Frisian" lang="frr" hreflang="frr" data-title="Tsüaniid" data-language-autonym="Nordfriisk" data-language-local-name="Northern Frisian" class="interlanguage-link-target"><span>Nordfriisk</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Cyanid" title="Cyanid – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Cyanid" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Cyanid" title="Cyanid – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Cyanid" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Cianur" title="Cianur – Occitan" lang="oc" hreflang="oc" data-title="Cianur" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Siyanid" title="Siyanid – Uzbek" lang="uz" hreflang="uz" data-title="Siyanid" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-km mw-list-item"><a href="https://km.wikipedia.org/wiki/%E1%9E%9F%E1%9F%8A%E1%9E%B8%E1%9E%99%E1%9F%89%E1%9E%B6%E1%9E%89%E1%9E%BD%E1%9E%9A" title="ស៊ីយ៉ាញួរ – Khmer" lang="km" hreflang="km" data-title="ស៊ីយ៉ាញួរ" data-language-autonym="ភាសាខ្មែរ" data-language-local-name="Khmer" class="interlanguage-link-target"><span>ភាសាខ្មែរ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Cyjanki" title="Cyjanki – Polish" lang="pl" hreflang="pl" data-title="Cyjanki" 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/Cianeto" title="Cianeto – Portuguese" lang="pt" hreflang="pt" data-title="Cianeto" 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/Cianur%C4%83" title="Cianură – Romanian" lang="ro" hreflang="ro" data-title="Cianură" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A6%D0%B8%D0%B0%D0%BD%D0%B8%D0%B4%D1%8B" title="Цианиды – Russian" lang="ru" hreflang="ru" data-title="Цианиды" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Cianidi" title="Cianidi – Albanian" lang="sq" hreflang="sq" data-title="Cianidi" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Cyanide" title="Cyanide – Simple English" lang="en-simple" hreflang="en-simple" data-title="Cyanide" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kyanid" title="Kyanid – Slovak" lang="sk" hreflang="sk" data-title="Kyanid" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A6%D0%B8%D1%98%D0%B0%D0%BD%D0%B8%D0%B4" title="Цијанид – Serbian" lang="sr" hreflang="sr" data-title="Цијанид" 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/Cijanid" title="Cijanid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cijanid" 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-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Sianida" title="Sianida – Sundanese" lang="su" hreflang="su" data-title="Sianida" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Syanidi" title="Syanidi – Finnish" lang="fi" hreflang="fi" data-title="Syanidi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Cyanider" title="Cyanider – Swedish" lang="sv" hreflang="sv" data-title="Cyanider" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Siyanuro" title="Siyanuro – Tagalog" lang="tl" hreflang="tl" data-title="Siyanuro" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%9A%E0%AE%AF%E0%AE%A9%E0%AF%88%E0%AE%9F%E0%AF%81" title="சயனைடு – Tamil" lang="ta" hreflang="ta" data-title="சயனைடு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%84%E0%B8%8B%E0%B8%A2%E0%B8%B2%E0%B9%84%E0%B8%99%E0%B8%94%E0%B9%8C" title="ไซยาไนด์ – Thai" lang="th" hreflang="th" data-title="ไซยาไนด์" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Siyan%C3%BCr" title="Siyanür – Turkish" lang="tr" hreflang="tr" data-title="Siyanür" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A6%D1%96%D0%B0%D0%BD%D1%96%D0%B4%D0%B8" title="Ціаніди – Ukrainian" lang="uk" hreflang="uk" data-title="Ціаніди" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%B3%DB%8C%D8%A7%D9%86%D8%A7%D8%A6%DA%88" title="سیانائڈ – Urdu" lang="ur" hreflang="ur" data-title="سیانائڈ" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Cyanide" title="Cyanide – Vietnamese" lang="vi" hreflang="vi" data-title="Cyanide" 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-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Syanuro" title="Syanuro – Waray" lang="war" hreflang="war" data-title="Syanuro" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E5%B1%B1%E5%9F%83" title="山埃 – Cantonese" lang="yue" hreflang="yue" data-title="山埃" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%B0%B0%E5%8C%96%E7%89%A9" title="氰化物 – Chinese" lang="zh" hreflang="zh" data-title="氰化物" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q55076544#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div 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For other uses, see <a href="/wiki/Cyanide_(disambiguation)" class="mw-disambig" title="Cyanide (disambiguation)">Cyanide (disambiguation)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Nitrile" title="Nitrile">Nitrile</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Cyanide </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Cyanide-montage.png" class="mw-file-description"><img alt="Space-filling model of the cyanide anion: carbon bound to smaller nitrogen atom" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Cyanide-montage.png/220px-Cyanide-montage.png" decoding="async" width="220" height="499" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Cyanide-montage.png/330px-Cyanide-montage.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Cyanide-montage.png/440px-Cyanide-montage.png 2x" data-file-width="1000" data-file-height="2269" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Nitridocarbonate(II)</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=57-12-5">57-12-5</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=%5BC-%5D%23N">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17514">CHEBI:17514</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5755.html">5755</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5975">5975</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/OXN4E7L11K">OXN4E7L11K</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/CN/c1-2/q-1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XFXPMWWXUTWYJX-UHFFFAOYSA-N</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">[C-]#N</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">CN<sup class="template-chem2-sup">−</sup></span>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001260180000000000♠"></span>26.018</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">Conjugate acid</a> </td> <td><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>The cyanide ion <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CN<sup class="template-chem2-sup">−</sup></span> is one of the most poisonous chemicals. It may cause death in minutes. </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, <b>cyanide</b> (from <a href="/wiki/Greek_language" title="Greek language">Greek</a> <i> kyanos</i> '<a href="/wiki/Prussian_blue" title="Prussian blue">dark blue</a>') is a <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> that contains a <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C≡N</span> <a href="/wiki/Functional_group" title="Functional group">functional group</a>. This group, known as the <b>cyano group</b>, consists of a <a href="/wiki/Carbon" title="Carbon">carbon</a> atom <a href="/wiki/Triple-bond" class="mw-redirect" title="Triple-bond">triple-bonded</a> to a <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> atom.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>In <a href="/wiki/Inorganic_compound" title="Inorganic compound">inorganic</a> cyanides, the cyanide group is present as the cyanide anion <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><sup class="template-chem2-sup">−</sup>C≡N</span>. This anion is <a href="/wiki/Cyanide_poisoning" title="Cyanide poisoning">extremely poisonous</a>. Soluble <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> such as <a href="/wiki/Sodium_cyanide" title="Sodium cyanide">sodium cyanide</a> (NaCN) and <a href="/wiki/Potassium_cyanide" title="Potassium cyanide">potassium cyanide</a> (KCN) are highly toxic.<sup id="cite_ref-CMC_2-0" class="reference"><a href="#cite_note-CMC-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Hydrocyanic_acid" class="mw-redirect" title="Hydrocyanic acid">Hydrocyanic acid</a>, also known as hydrogen cyanide, or HCN, is a highly <a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">volatile</a> liquid that is produced on a large scale industrially. It is obtained by acidification of cyanide salts. </p><p><a href="/wiki/Organic_compound" title="Organic compound">Organic</a> cyanides are usually called <a href="/wiki/Nitrile" title="Nitrile">nitriles</a>. In nitriles, the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C≡N</span> group is linked by a single <a href="/wiki/Covalent_bond" title="Covalent bond">covalent bond</a> to carbon. For example, in <a href="/wiki/Acetonitrile" title="Acetonitrile">acetonitrile</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−C≡N</span>), the cyanide group is bonded to <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">3</sub></span>). Although nitriles generally do not release cyanide ions, the <a href="/wiki/Cyanohydrin" title="Cyanohydrin">cyanohydrins</a> do and are thus toxic. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Bonding">Bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=1" title="Edit section: Bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The cyanide ion <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><sup class="template-chem2-sup">−</sup>C≡N</span> is <a href="/wiki/Isoelectronic" class="mw-redirect" title="Isoelectronic">isoelectronic</a> with <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><sup class="template-chem2-sup">−</sup>C≡O<sup class="template-chem2-sup">+</sup></span> and with molecular <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> N≡N. A triple bond exists between C and N. The negative charge is concentrated on <a href="/wiki/Carbon" title="Carbon">carbon</a> C.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=2" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="In_nature">In nature</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=3" title="Edit section: In nature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Removal_of_cyanide_poison_from_cassava.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Removal_of_cyanide_poison_from_cassava.jpg/220px-Removal_of_cyanide_poison_from_cassava.jpg" decoding="async" width="220" height="148" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Removal_of_cyanide_poison_from_cassava.jpg/330px-Removal_of_cyanide_poison_from_cassava.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Removal_of_cyanide_poison_from_cassava.jpg/440px-Removal_of_cyanide_poison_from_cassava.jpg 2x" data-file-width="2896" data-file-height="1944" /></a><figcaption>Removal of cyanide from <a href="/wiki/Cassava" title="Cassava">cassava</a> in <a href="/wiki/Nigeria" title="Nigeria">Nigeria</a>.</figcaption></figure> <p>Cyanides are produced by certain <a href="/wiki/Bacterium" class="mw-redirect" title="Bacterium">bacteria</a>, <a href="/wiki/Fungi" class="mw-redirect" title="Fungi">fungi</a>, and <a href="/wiki/Algae" title="Algae">algae</a>. It is an <a href="/wiki/Antifeedant" title="Antifeedant">antifeedant</a> in a number of plants. Cyanides are found in substantial amounts in certain seeds and fruit stones, e.g., those of <a href="/wiki/Bitter_almond" class="mw-redirect" title="Bitter almond">bitter almonds</a>, <a href="/wiki/Apricot" title="Apricot">apricots</a>, <a href="/wiki/Apple" title="Apple">apples</a>, and <a href="/wiki/Peach" title="Peach">peaches</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Chemical compounds that can release cyanide are known as cyanogenic compounds. In plants, cyanides are usually bound to <a href="/wiki/Sugar" title="Sugar">sugar</a> molecules in the form of cyanogenic <a href="/wiki/Glycoside" title="Glycoside">glycosides</a> and defend the plant against <a href="/wiki/Herbivore" title="Herbivore">herbivores</a>. <a href="/wiki/Cassava" title="Cassava">Cassava</a> roots (also called manioc), an important <a href="/wiki/Potato" title="Potato">potato</a>-like food grown in tropical countries (and the base from which <a href="/wiki/Tapioca" title="Tapioca">tapioca</a> is made), also contain cyanogenic glycosides.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-jones_7-0" class="reference"><a href="#cite_note-jones-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Madagascar" title="Madagascar">Madagascar</a> bamboo <i><a href="/wiki/Cathariostachys_madagascariensis" title="Cathariostachys madagascariensis">Cathariostachys madagascariensis</a></i> produces cyanide as a deterrent to grazing. In response, the <a href="/wiki/Golden_bamboo_lemur" title="Golden bamboo lemur">golden bamboo lemur</a>, which eats the bamboo, has developed a high tolerance to cyanide. </p><p>The <a href="/wiki/Hydrogenase" title="Hydrogenase">hydrogenase</a> enzymes contain cyanide <a href="/wiki/Ligand" title="Ligand">ligands</a> attached to iron in their active sites. The biosynthesis of cyanide in the <a href="/wiki/NiFe_hydrogenase" title="NiFe hydrogenase">NiFe hydrogenases</a> proceeds from <a href="/wiki/Carbamoyl_phosphate" title="Carbamoyl phosphate">carbamoyl phosphate</a>, which converts to <a href="/wiki/Cystein" class="mw-redirect" title="Cystein">cysteinyl</a> <a href="/wiki/Thiocyanate" title="Thiocyanate">thiocyanate</a>, the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CN<sup class="template-chem2-sup">−</sup></span> donor.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Interstellar_medium">Interstellar medium</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=4" title="Edit section: Interstellar medium"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Cyanide_radical" class="mw-redirect" title="Cyanide radical">cyanide radical</a> <sup>•</sup>CN has been identified in <a href="/wiki/Interstellar_space" class="mw-redirect" title="Interstellar space">interstellar space</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Cyanogen" title="Cyanogen">Cyanogen</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CN)<sub class="template-chem2-sub">2</sub></span>, is used to measure the temperature of <a href="/wiki/Molecular_cloud" title="Molecular cloud">interstellar gas clouds</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pyrolysis_and_combustion_product">Pyrolysis and combustion product</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=5" title="Edit section: Pyrolysis and combustion product"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydrogen cyanide is produced by the combustion or <a href="/wiki/Pyrolysis" title="Pyrolysis">pyrolysis</a> of certain materials under oxygen-deficient conditions. For example, it can be detected in the <a href="/wiki/Exhaust_gas" title="Exhaust gas">exhaust</a> of <a href="/wiki/Internal_combustion_engine" title="Internal combustion engine">internal combustion engines</a> and <a href="/wiki/Tobacco" title="Tobacco">tobacco</a> smoke. Certain <a href="/wiki/Plastic" title="Plastic">plastics</a>, especially those derived from <a href="/wiki/Acrylonitrile" title="Acrylonitrile">acrylonitrile</a>, release hydrogen cyanide when heated or burnt.<sup id="cite_ref-CDC_11-0" class="reference"><a href="#cite_note-CDC-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Organic_derivatives">Organic derivatives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=6" title="Edit section: Organic derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Nitriles" class="mw-redirect" title="Nitriles">Nitriles</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Isocyanide" title="Isocyanide">Isocyanide</a></div> <p>In <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">IUPAC nomenclature</a>, <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> that have a <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C≡N</span> <a href="/wiki/Functional_group" title="Functional group">functional group</a> are called <a href="/wiki/Nitrile" title="Nitrile">nitriles</a>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> An example of a nitrile is <a href="/wiki/Acetonitrile" title="Acetonitrile">acetonitrile</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−C≡N</span>. Nitriles usually do not release cyanide ions. A functional group with a hydroxyl <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−OH</span> and cyanide <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CN</span> bonded to the same carbon atom is called <a href="/wiki/Cyanohydrin" title="Cyanohydrin">cyanohydrin</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">2</sub>C(OH)CN</span>). Unlike nitriles, cyanohydrins do release poisonous <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=7" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Protonation">Protonation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=8" title="Edit section: Protonation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanide is basic. The p<i>K</i><sub>a</sub> of hydrogen cyanide is 9.21. Thus, addition of <a href="/wiki/Acids" class="mw-redirect" title="Acids">acids</a> stronger than hydrogen cyanide to solutions of cyanide salts releases <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Hydrolysis">Hydrolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=9" title="Edit section: Hydrolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanide is unstable in water, but the reaction is slow until about 170 °C. It undergoes <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> to give <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> and <a href="/wiki/Formate" title="Formate">formate</a>, which are far less toxic than cyanide:<sup id="cite_ref-Ullmann_14-0" class="reference"><a href="#cite_note-Ullmann-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CN<sup class="template-chem2-sup">−</sup> + 2 H<sub class="template-chem2-sub">2</sub>O → HCO<span class="template-chem2-su"><span>−</span><span>2</span></span> + NH<sub class="template-chem2-sub">3</sub></span></dd></dl> <p><a href="/w/index.php?title=Cyanide_hydrolase&action=edit&redlink=1" class="new" title="Cyanide hydrolase (page does not exist)">Cyanide hydrolase</a> is an <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> that catalyzes this reaction. </p> <div class="mw-heading mw-heading3"><h3 id="Alkylation">Alkylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=10" title="Edit section: Alkylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because of the cyanide anion's high <a href="/wiki/Nucleophile" title="Nucleophile">nucleophilicity</a>, cyano groups are readily introduced into organic molecules by displacement of a <a href="/wiki/Halide" title="Halide">halide</a> group (e.g., the <a href="/wiki/Chloride" title="Chloride">chloride</a> on <a href="/wiki/Methyl_chloride" class="mw-redirect" title="Methyl chloride">methyl chloride</a>). In general, organic cyanides are called nitriles. In organic synthesis, cyanide is a C-1 <a href="/wiki/Synthon" title="Synthon">synthon</a>; i.e., it can be used to lengthen a carbon chain by one, while retaining the ability to be <a href="https://en.wiktionary.org/wiki/functionalize" class="extiw" title="wiktionary:functionalize">functionalized</a>.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RX + CN<sup class="template-chem2-sup">−</sup> → RCN + X<sup class="template-chem2-sup">−</sup></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Redox">Redox</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=11" title="Edit section: Redox"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The cyanide ion is a <a href="/wiki/Reducing_agent" title="Reducing agent">reductant</a> and is <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidized</a> by strong <a href="/wiki/Oxidizing_agent" title="Oxidizing agent">oxidizing agents</a> such as molecular <a href="/wiki/Chlorine" title="Chlorine">chlorine</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cl<sub class="template-chem2-sub">2</sub></span>), <a href="/wiki/Hypochlorite" title="Hypochlorite">hypochlorite</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">ClO<sup class="template-chem2-sup">−</sup></span>), and <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">2</sub></span>). These oxidizers are used to destroy cyanides in <a href="/wiki/Effluent" title="Effluent">effluents</a> from <a href="/wiki/Gold_mining" title="Gold mining">gold mining</a>.<sup id="cite_ref-Young_1995_16-0" class="reference"><a href="#cite_note-Young_1995-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SRK_17-0" class="reference"><a href="#cite_note-SRK-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Botz_18-0" class="reference"><a href="#cite_note-Botz-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metal_complexation">Metal complexation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=12" title="Edit section: Metal complexation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The cyanide anion reacts with <a href="/wiki/Transition_metals" class="mw-redirect" title="Transition metals">transition metals</a> to form <a href="/wiki/Cyanometalate" title="Cyanometalate">M-CN bonds</a>. This reaction is the basis of cyanide's toxicity.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The high affinities of metals for this <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a> can be attributed to its negative charge, compactness, and ability to engage in π-bonding. </p><p>Among the most important cyanide coordination compounds are the <a href="/wiki/Potassium_ferrocyanide" title="Potassium ferrocyanide">potassium ferrocyanide</a> and the pigment <a href="/wiki/Prussian_blue" title="Prussian blue">Prussian blue</a>, which are both essentially nontoxic due to the tight binding of the cyanides to a central iron atom.<sup id="cite_ref-Holl_20-0" class="reference"><a href="#cite_note-Holl-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Prussian blue was first accidentally made around 1706, by heating substances containing iron and carbon and nitrogen, and other cyanides made subsequently (and named after it). Among its many uses, Prussian blue gives the blue color to <a href="/wiki/Blueprints" class="mw-redirect" title="Blueprints">blueprints</a>, <a href="/wiki/Bluing_(fabric)" title="Bluing (fabric)">bluing</a>, and <a href="/wiki/Cyanotype" title="Cyanotype">cyanotypes</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Manufacture">Manufacture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=13" title="Edit section: Manufacture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Hydrogen_cyanide#Production_and_synthesis" title="Hydrogen cyanide">Hydrogen cyanide § Production and synthesis</a></div> <p>The principal process used to manufacture cyanides is the <a href="/wiki/Andrussow_process" title="Andrussow process">Andrussow process</a> in which gaseous <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a> is produced from <a href="/wiki/Methane" title="Methane">methane</a> and <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> in the presence of <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> and a <a href="/wiki/Platinum" title="Platinum">platinum</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">2 CH<sub class="template-chem2-sub">4</sub> + 2 NH<sub class="template-chem2-sub">3</sub> + 3 O<sub class="template-chem2-sub">2</sub> → 2 HCN + 6 H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>Sodium cyanide, the precursor to most cyanides, is produced by treating <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a> with <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a>:<sup id="cite_ref-Ullmann_14-1" class="reference"><a href="#cite_note-Ullmann-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HCN + NaOH → NaCN + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=14" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cyanide_poisoning" title="Cyanide poisoning">Cyanide poisoning</a></div> <p>Among the most toxic cyanides are hydrogen cyanide (HCN), sodium cyanide (NaCN), potassium cyanide (KCN), and calcium cyanide (Ca(CN)₂). These compounds are extremely poisonous and require careful handling to avoid severe health risks. The cyanide anion is an <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitor</a> of the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Cytochrome_c_oxidase" title="Cytochrome c oxidase">cytochrome c oxidase</a> (also known as aa<sub>3</sub>), the fourth complex of the <a href="/wiki/Electron_transport_chain" title="Electron transport chain">electron transport chain</a> found in the <a href="/wiki/Inner_mitochondrial_membrane" title="Inner mitochondrial membrane">inner membrane</a> of the <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a> of <a href="/wiki/Eukaryote" title="Eukaryote">eukaryotic</a> cells. It attaches to the iron within this protein. The binding of cyanide to this enzyme prevents transport of electrons from <a href="/wiki/Cytochrome_c" title="Cytochrome c">cytochrome c</a> to oxygen. As a result, the electron transport chain is disrupted, meaning that the cell can no longer aerobically produce <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> for energy.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Tissues that depend highly on <a href="/wiki/Aerobic_respiration" class="mw-redirect" title="Aerobic respiration">aerobic respiration</a>, such as the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> and the <a href="/wiki/Heart" title="Heart">heart</a>, are particularly affected. This is an example of <a href="/wiki/Histotoxic_hypoxia" title="Histotoxic hypoxia">histotoxic hypoxia</a>.<sup id="cite_ref-Biller_24-0" class="reference"><a href="#cite_note-Biller-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>The most hazardous compound is <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a>, which is a gas and kills by inhalation. For this reason, an air respirator supplied by an external oxygen source must be worn when working with hydrogen cyanide.<sup id="cite_ref-CDC_11-1" class="reference"><a href="#cite_note-CDC-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Hydrogen cyanide is produced by adding acid to a solution containing a cyanide salt. Alkaline solutions of cyanide are safer to use because they do not evolve hydrogen cyanide gas. Hydrogen cyanide may be produced in the combustion of <a href="/wiki/Polyurethane" title="Polyurethane">polyurethanes</a>; for this reason, polyurethanes are not recommended for use in domestic and aircraft furniture. Oral ingestion of a small quantity of solid cyanide or a cyanide solution of as little as 200 mg, or exposure to airborne cyanide of 270 <a href="/wiki/Parts_per_million" class="mw-redirect" title="Parts per million">ppm</a>, is sufficient to cause death within minutes.<sup id="cite_ref-Biller_24-1" class="reference"><a href="#cite_note-Biller-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Organic <a href="/wiki/Nitrile" title="Nitrile">nitriles</a> do not readily release cyanide ions, and so have low toxicities. By contrast, compounds such as <a href="/wiki/Trimethylsilyl_cyanide" title="Trimethylsilyl cyanide">trimethylsilyl cyanide</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>SiCN</span> readily release HCN or the cyanide ion upon contact with water.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Antidote">Antidote</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=15" title="Edit section: Antidote"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a> reacts with cyanide to form <a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">cyanocobalamin</a>, which can be safely eliminated by the kidneys. This method has the advantage of avoiding the formation of methemoglobin (see below). This antidote kit is sold under the brand name Cyanokit and was approved by the U.S. FDA in 2006.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>An older cyanide antidote kit included administration of three substances: <a href="/wiki/Amyl_nitrite" title="Amyl nitrite">amyl nitrite</a> pearls (administered by inhalation), <a href="/wiki/Sodium_nitrite" title="Sodium nitrite">sodium nitrite</a>, and <a href="/wiki/Sodium_thiosulfate" title="Sodium thiosulfate">sodium thiosulfate</a>. The goal of the antidote was to generate a large pool of <a href="/wiki/Ferric" title="Ferric">ferric</a> iron (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Fe<sup>3+</sup></span>) to compete for cyanide with cytochrome a<sub>3</sub> (so that cyanide will bind to the antidote rather than the enzyme). The <a href="/wiki/Nitrite" title="Nitrite">nitrites</a> <a href="/wiki/Oxidize" class="mw-redirect" title="Oxidize">oxidize</a> <a href="/wiki/Hemoglobin" title="Hemoglobin">hemoglobin</a> to <a href="/wiki/Methemoglobin" title="Methemoglobin">methemoglobin</a>, which competes with cytochrome oxidase for the cyanide ion. Cyanmethemoglobin is formed and the <a href="/wiki/Cytochrome_oxidase" class="mw-redirect" title="Cytochrome oxidase">cytochrome oxidase</a> enzyme is restored. The major mechanism to remove the cyanide from the body is by enzymatic conversion to <a href="/wiki/Thiocyanate" title="Thiocyanate">thiocyanate</a> by the <a href="/wiki/Mitochondrial" class="mw-redirect" title="Mitochondrial">mitochondrial</a> enzyme <a href="/wiki/Rhodanese" title="Rhodanese">rhodanese</a>. Thiocyanate is a relatively non-toxic molecule and is excreted by the kidneys. To accelerate this detoxification, sodium thiosulfate is administered to provide a sulfur donor for <a href="/wiki/Rhodanese" title="Rhodanese">rhodanese</a>, needed in order to produce thiocyanate.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Sensitivity">Sensitivity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=16" title="Edit section: Sensitivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Minimum risk levels (MRLs) may not protect for delayed health effects or health effects acquired following repeated sublethal exposure, such as hypersensitivity, <a href="/wiki/Asthma" title="Asthma">asthma</a>, or <a href="/wiki/Bronchitis" title="Bronchitis">bronchitis</a>. MRLs may be revised after sufficient data accumulates.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=17" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Mining">Mining</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=18" title="Edit section: Mining"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Gold_cyanidation" title="Gold cyanidation">Gold cyanidation</a></div> <p>Cyanide is mainly produced for the <a href="/wiki/Mining" title="Mining">mining</a> of <a href="/wiki/Silver" title="Silver">silver</a> and <a href="/wiki/Gold" title="Gold">gold</a>: It helps dissolve these metals allowing separation from the other solids. In the <i><a href="/wiki/Cyanide_process" class="mw-redirect" title="Cyanide process">cyanide process</a></i>, finely ground high-grade ore is mixed with the cyanide (at a ratio of about 1:500 parts NaCN to ore); low-grade ores are stacked into heaps and sprayed with a cyanide solution (at a ratio of about 1:1000 parts NaCN to ore). The precious metals are complexed by the cyanide <a href="/wiki/Anion" class="mw-redirect" title="Anion">anions</a> to form soluble derivatives, e.g., <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[Ag(CN)<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup">−</sup></span> (dicyanoargentate(I)) and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[Au(CN)<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup">−</sup></span> (dicyanoaurate(I)).<sup id="cite_ref-Ullmann_14-2" class="reference"><a href="#cite_note-Ullmann-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Silver is less <a href="/wiki/Noble_metal" title="Noble metal">"noble"</a> than gold and often occurs as the sulfide, in which case redox is not invoked (no <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O<sub class="template-chem2-sub">2</sub></span> is required). Instead, a displacement reaction occurs: </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="{\displaystyle {\ce {Ag2S + 4 NaCN + H2O -> 2 Na[Ag(CN)2] + NaSH + NaOH}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>Ag</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>S</mtext> <mo>+</mo> <mn>4</mn> <mspace width="thinmathspace" /> <mtext>NaCN</mtext> <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 stretchy="false">⟶</mo> <mn>2</mn> <mspace width="thinmathspace" /> <mtext>Na</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mtext>Ag</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>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">]</mo> </mrow> <mo>+</mo> <mtext>NaSH</mtext> <mo>+</mo> <mtext>NaOH</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {Ag2S + 4 NaCN + H2O -> 2 Na[Ag(CN)2] + NaSH + NaOH}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/fdb057d86c43d8885c7802a16b185d6927372a71" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:61.529ex; height:3.009ex;" alt="{\displaystyle {\ce {Ag2S + 4 NaCN + H2O -> 2 Na[Ag(CN)2] + NaSH + NaOH}}}"></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="{\displaystyle {\ce {4 Au + 8 NaCN + O2 + 2 H2O -> 4 Na[Au(CN)2] + 4 NaOH}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> <mspace width="thinmathspace" /> <mtext>Au</mtext> <mo>+</mo> <mn>8</mn> <mspace width="thinmathspace" /> <mtext>NaCN</mtext> <mo>+</mo> <msubsup> <mtext>O</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> <mn>2</mn> <mspace width="thinmathspace" /> <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 stretchy="false">⟶</mo> <mn>4</mn> <mspace width="thinmathspace" /> <mtext>Na</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mtext>Au</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>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">]</mo> </mrow> <mo>+</mo> <mn>4</mn> <mspace width="thinmathspace" /> <mtext>NaOH</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {4 Au + 8 NaCN + O2 + 2 H2O -> 4 Na[Au(CN)2] + 4 NaOH}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/52060e78e1dcc4a241c0759c4d733887e658ce3b" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:61.012ex; height:3.009ex;" alt="{\displaystyle {\ce {4 Au + 8 NaCN + O2 + 2 H2O -> 4 Na[Au(CN)2] + 4 NaOH}}}"></span></dd></dl> <p>The "pregnant liquor" containing these ions is separated from the solids, which are discarded to a <a href="/wiki/Tailing_pond" class="mw-redirect" title="Tailing pond">tailing pond</a> or spent heap, the recoverable gold having been removed. The metal is recovered from the "pregnant solution" by reduction with <a href="/wiki/Zinc" title="Zinc">zinc</a> dust or by <a href="/wiki/Adsorption" title="Adsorption">adsorption</a> onto <a href="/wiki/Activated_carbon" title="Activated carbon">activated carbon</a>. This process can result in environmental and health problems. A number of <a href="/wiki/List_of_gold_mining_disasters" title="List of gold mining disasters">environmental disasters</a> have followed the overflow of tailing ponds at gold mines. Cyanide contamination of waterways has resulted in numerous cases of human and aquatic species mortality.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>Aqueous cyanide is hydrolyzed rapidly, especially in sunlight. It can mobilize some heavy metals such as mercury if present. Gold can also be associated with arsenopyrite (FeAsS), which is similar to <a href="/wiki/Iron_pyrite" class="mw-redirect" title="Iron pyrite">iron pyrite</a> (fool's gold), wherein half of the sulfur atoms are replaced by <a href="/wiki/Arsenic" title="Arsenic">arsenic</a>. Gold-containing arsenopyrite ores are similarly reactive toward inorganic cyanide.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Industrial_organic_chemistry">Industrial organic chemistry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=19" title="Edit section: Industrial organic chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The second major application of alkali metal cyanides (after mining) is in the production of CN-containing compounds, usually nitriles. <a href="/wiki/Acyl_cyanide" title="Acyl cyanide">Acyl cyanides</a> are produced from acyl chlorides and cyanide. <a href="/wiki/Cyanogen" title="Cyanogen">Cyanogen</a>, <a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">cyanogen chloride</a>, and the trimer <a href="/wiki/Cyanuric_chloride" title="Cyanuric chloride">cyanuric chloride</a> are derived from alkali metal cyanides. </p> <div class="mw-heading mw-heading3"><h3 id="Medical_uses">Medical uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=20" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The cyanide compound <a href="/wiki/Sodium_nitroprusside" title="Sodium nitroprusside">sodium nitroprusside</a> is used mainly in <a href="/wiki/Clinical_chemistry" title="Clinical chemistry">clinical chemistry</a> to measure <a href="/wiki/Urine" title="Urine">urine</a> <a href="/wiki/Ketone_bodies" title="Ketone bodies">ketone bodies</a> mainly as a follow-up to <a href="/wiki/Diabetic" class="mw-redirect" title="Diabetic">diabetic</a> patients. On occasion, it is used in emergency medical situations to produce a rapid decrease in <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a> in humans; it is also used as a <a href="/wiki/Vasodilator" class="mw-redirect" title="Vasodilator">vasodilator</a> in vascular research. The cobalt in artificial <a href="/wiki/Vitamin_B12" title="Vitamin B12">vitamin B<sub>12</sub></a> contains a cyanide ligand as an artifact of the purification process; this must be removed by the body before the vitamin molecule can be activated for biochemical use. During <a href="/wiki/World_War_I" title="World War I">World War I</a>, a copper cyanide compound was briefly used by <a href="/wiki/Japan" title="Japan">Japanese</a> physicians for the treatment of <a href="/wiki/Tuberculosis" title="Tuberculosis">tuberculosis</a> and <a href="/wiki/Leprosy" title="Leprosy">leprosy</a>.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Illegal_fishing_and_poaching">Illegal fishing and poaching</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=21" title="Edit section: Illegal fishing and poaching"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cyanide_fishing" title="Cyanide fishing">Cyanide fishing</a></div> <p>Cyanides are illegally used to capture live fish near <a href="/wiki/Coral_reef" title="Coral reef">coral reefs</a> for the <a href="/wiki/Aquarium" title="Aquarium">aquarium</a> and seafood markets. The practice is controversial, dangerous, and damaging but is driven by the lucrative exotic fish market.<sup id="cite_ref-crc_33-0" class="reference"><a href="#cite_note-crc-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>Poachers in Africa have been known to use cyanide to poison waterholes, to kill elephants for their ivory.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pest_control">Pest control</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=22" title="Edit section: Pest control"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/M44_(cyanide_device)" title="M44 (cyanide device)">M44 cyanide devices</a> are used in the United States to kill <a href="/wiki/Coyote" title="Coyote">coyotes</a> and other canids.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Cyanide is also used for pest control in <a href="/wiki/New_Zealand" title="New Zealand">New Zealand</a>, particularly for <a href="/wiki/Common_Brushtail_Possum_in_New_Zealand" class="mw-redirect" title="Common Brushtail Possum in New Zealand">possums</a>, an <a href="/wiki/Invasive_species_in_New_Zealand" title="Invasive species in New Zealand">introduced marsupial that threatens the conservation of native species</a> and spreads <a href="/wiki/Tuberculosis" title="Tuberculosis">tuberculosis</a> amongst cattle. Possums can become bait shy but the use of pellets containing the cyanide reduces bait shyness. Cyanide has been known to kill native birds, including the endangered <a href="/wiki/Kiwi_(bird)" title="Kiwi (bird)">kiwi</a>.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Cyanide is also effective for controlling the <a href="/wiki/Dama_wallaby" class="mw-redirect" title="Dama wallaby">dama wallaby</a>, another introduced marsupial pest in New Zealand.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> A licence is required to store, handle and use cyanide in New Zealand. </p><p>Cyanides are used as <a href="/wiki/Insecticide" title="Insecticide">insecticides</a> for fumigating ships.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Cyanide salts are used for killing ants,<sup id="cite_ref-EPAReg1994_39-0" class="reference"><a href="#cite_note-EPAReg1994-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> and have in some places been used as rat poison<sup id="cite_ref-TariffInfo1921_40-0" class="reference"><a href="#cite_note-TariffInfo1921-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> (the less toxic poison <a href="/wiki/Arsenic" title="Arsenic">arsenic</a> is more common).<sup id="cite_ref-PlanetDeadly2013_41-0" class="reference"><a href="#cite_note-PlanetDeadly2013-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Niche_uses">Niche uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=23" title="Edit section: Niche uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Potassium_ferrocyanide" title="Potassium ferrocyanide">Potassium ferrocyanide</a> is used to achieve a blue color on cast <a href="/wiki/Bronze_sculpture" title="Bronze sculpture">bronze sculptures</a> during the final finishing stage of the sculpture. On its own, it will produce a very dark shade of blue and is often mixed with other chemicals to achieve the desired tint and hue. It is applied using a torch and paint brush while wearing the standard safety equipment used for any patina application: rubber gloves, safety glasses, and a respirator. The actual amount of cyanide in the mixture varies according to the recipes used by each foundry. </p><p>Cyanide is also used in <a href="/wiki/Jewelry" class="mw-redirect" title="Jewelry">jewelry</a>-making and certain kinds of <a href="/wiki/Photography" title="Photography">photography</a> such as <a href="/wiki/Sepia_toning" class="mw-redirect" title="Sepia toning">sepia toning</a>. </p><p>Although usually thought to be toxic, cyanide and cyanohydrins increase germination in various plant species.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Human_poisoning">Human poisoning</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=24" title="Edit section: Human poisoning"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cyanide_poisoning" title="Cyanide poisoning">Cyanide poisoning</a></div> <p>Deliberate cyanide poisoning of humans has occurred many times throughout history.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> Common salts such as <a href="/wiki/Sodium_cyanide" title="Sodium cyanide">sodium cyanide</a> are involatile but water-soluble, so are poisonous by ingestion. <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> is a gas, making it more indiscriminately dangerous, however it is lighter than air and rapidly disperses up into the atmosphere, which makes it ineffective as a <a href="/wiki/Chemical_weapon" title="Chemical weapon">chemical weapon</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Food_additive">Food additive</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=25" title="Edit section: Food additive"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because of the high stability of their complexation with <a href="/wiki/Iron" title="Iron">iron</a>, ferrocyanides (<a href="/wiki/Sodium_ferrocyanide" title="Sodium ferrocyanide">Sodium ferrocyanide</a> E535, <a href="/wiki/Potassium_ferrocyanide" title="Potassium ferrocyanide">Potassium ferrocyanide</a> E536, and Calcium ferrocyanide E538<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup>) do not decompose to lethal levels in the human body and are used in the food industry as, e.g., an <a href="/wiki/Anticaking_agent" title="Anticaking agent">anticaking agent</a> in <a href="/wiki/Table_salt" class="mw-redirect" title="Table salt">table salt</a>.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_tests_for_cyanide">Chemical tests for cyanide</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=26" title="Edit section: Chemical tests for cyanide"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanide is quantified by <a href="/wiki/Potentiometric_titration" title="Potentiometric titration">potentiometric titration</a>, a method widely used in gold mining. It can also be determined by titration with silver ion. Some analyses begin with an air-purge of an acidified boiling solution, sweeping the vapors into a basic absorber solution. The cyanide salt absorbed in the basic solution is then analyzed.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Qualitative_tests">Qualitative tests</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=27" title="Edit section: Qualitative tests"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because of the notorious toxicity of cyanide, many methods have been investigated. Benzidine gives a blue coloration in the presence of <a href="/wiki/Ferricyanide" title="Ferricyanide">ferricyanide</a>.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Iron(II)_sulfate" title="Iron(II) sulfate">Iron(II) sulfate</a> added to a solution of cyanide, such as the filtrate from the <a href="/wiki/Sodium_fusion_test" title="Sodium fusion test">sodium fusion test</a>, gives <a href="/wiki/Prussian_blue" title="Prussian blue">prussian blue</a>. A solution of <a href="/wiki/1,4-Benzoquinone" title="1,4-Benzoquinone"><i>para</i>-benzoquinone</a> in <a href="/wiki/Dimethyl_sulfoxide" title="Dimethyl sulfoxide">DMSO</a> reacts with inorganic cyanide to form a cyano<a href="/wiki/Phenol" title="Phenol">phenol</a>, which is <a href="/wiki/Fluorescent" class="mw-redirect" title="Fluorescent">fluorescent</a>. Illumination with a <a href="/wiki/UV_light" class="mw-redirect" title="UV light">UV light</a> gives a green/blue glow if the test is positive.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=28" 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 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.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 journal 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New York: <a href="/wiki/Worth_Publishers" class="mw-redirect" title="Worth Publishers">Worth Publishers</a>. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/lehningerprincip01lehn/page/668">668, 670–71, 676</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-57259-153-0" title="Special:BookSources/978-1-57259-153-0"><bdi>978-1-57259-153-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lehniger+Principles+of+Biochemistry&rft.place=New+York&rft.pages=668%2C+670-71%2C+676&rft.edition=3rd&rft.pub=Worth+Publishers&rft.date=2000&rft.isbn=978-1-57259-153-0&rft.aulast=Nelson&rft.aufirst=David+L.&rft.au=Cox%2C+Michael+M.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Flehningerprincip01lehn%2Fpage%2F668&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span> </li> <li id="cite_note-Biller-24"><span class="mw-cite-backlink">^ <a href="#cite_ref-Biller_24-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Biller_24-1"><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="CITEREFBiller2007" class="citation book cs1">Biller, José (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=SRIvmTVcYBwC&pg=PA939">"163"</a>. <i>Interface of neurology and internal medicine</i> (illustrated ed.). 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Retrieved <span class="nowrap">2 September</span> 2016</span>. <q>Another field in which cyanide is used in growing quantity is the eradication of rats and other vermin – especially in the fight against typhus.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=AbeBooks.com&rft.atitle=Tariff+Information%2C+1921%3A+Hearings+on+General+Tariff+Revision+Before+the+Committee+on+Ways+and+Means%2C+House+of+Representatives&rft.pages=3987&rft.date=1921&rft_id=http%3A%2F%2Fwww.abebooks.com%2Fservlet%2FSearchResults%3Ftn%3DTariff%2BInformation%2C%2B1921&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span> </li> <li id="cite_note-PlanetDeadly2013-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-PlanetDeadly2013_41-0">^</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://web.archive.org/web/20160511033535/http://www.planetdeadly.com/human/deadliest-poisons-man">"Deadliest Poisons Used by Man"</a>. <i>PlanetDeadly.com</i>. 18 November 2013. 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Retrieved <span class="nowrap">2 September</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PlanetDeadly.com&rft.atitle=Deadliest+Poisons+Used+by+Man&rft.date=2013-11-18&rft_id=http%3A%2F%2Fwww.planetdeadly.com%2Fhuman%2Fdeadliest-poisons-man&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span> </li> <li id="cite_note-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-42">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTaylorsonHendricks1973" class="citation journal cs1">Taylorson, R.; Hendricks, SB (1973). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC366431">"Promotion of Seed Germination by Cyanide"</a>. <i>Plant Physiol</i>. <b>52</b> (1): 23–27. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1104%2Fpp.52.1.23">10.1104/pp.52.1.23</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC366431">366431</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16658492">16658492</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Plant+Physiol.&rft.atitle=Promotion+of+Seed+Germination+by+Cyanide&rft.volume=52&rft.issue=1&rft.pages=23-27&rft.date=1973&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC366431%23id-name%3DPMC&rft_id=info%3Apmid%2F16658492&rft_id=info%3Adoi%2F10.1104%2Fpp.52.1.23&rft.aulast=Taylorson&rft.aufirst=R.&rft.au=Hendricks%2C+SB&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC366431&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span> </li> <li id="cite_note-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-43">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMullickChatterji1967" class="citation journal cs1">Mullick, P.; Chatterji, U. N. (1967). "Effect of sodium cyanide on germination of two leguminous seeds". <i>Plant Systematics and Evolution</i>. <b>114</b>: 88–91. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF01373937">10.1007/BF01373937</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:2533762">2533762</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Plant+Systematics+and+Evolution&rft.atitle=Effect+of+sodium+cyanide+on+germination+of+two+leguminous+seeds&rft.volume=114&rft.pages=88-91&rft.date=1967&rft_id=info%3Adoi%2F10.1007%2FBF01373937&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A2533762%23id-name%3DS2CID&rft.aulast=Mullick&rft.aufirst=P.&rft.au=Chatterji%2C+U.+N.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBernan2008" class="citation book cs1">Bernan (2008). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=oiw2ZzsBvsoC"><i>Medical Management of Chemical Casualties Handbook</i></a> (4th ed.). Government Printing Off. p. 41. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-16-081320-7" title="Special:BookSources/978-0-16-081320-7"><bdi>978-0-16-081320-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Medical+Management+of+Chemical+Casualties+Handbook&rft.pages=41&rft.edition=4th&rft.pub=Government+Printing+Off&rft.date=2008&rft.isbn=978-0-16-081320-7&rft.au=Bernan&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Doiw2ZzsBvsoC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span>, <a rel="nofollow" class="external text" href="https://books.google.com/books?id=oiw2ZzsBvsoC&pg=PA41">Extract p. 41</a></span> </li> <li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBenderBender1997" class="citation book cs1">Bender, David A.; Bender, Arnold Eric (1997). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=IrYfDEl7XPYC"><i>Benders' dictionary of nutrition and food technology</i></a> (7th ed.). Woodhead Publishing. p. 459. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-85573-475-3" title="Special:BookSources/978-1-85573-475-3"><bdi>978-1-85573-475-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Benders%27+dictionary+of+nutrition+and+food+technology&rft.pages=459&rft.edition=7th&rft.pub=Woodhead+Publishing&rft.date=1997&rft.isbn=978-1-85573-475-3&rft.aulast=Bender&rft.aufirst=David+A.&rft.au=Bender%2C+Arnold+Eric&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DIrYfDEl7XPYC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span> <a rel="nofollow" class="external text" href="https://books.google.com/books?id=IrYfDEl7XPYC&pg=PA459">Extract of page 459</a></span> </li> <li id="cite_note-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-46">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchulzHadelerDeutsche_Forschungsgemeinschaft2003" class="citation book cs1">Schulz, Horst D.; Hadeler, Astrid; Deutsche Forschungsgemeinschaft (2003). <a rel="nofollow" class="external text" href="http://onlinelibrary.wiley.com/doi/10.1002/9783527609703"><i>Geochemical processes in soil and groundwater: measurement – modelling – upscaling</i></a>. Wiley-VCH. p. 67. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9783527609703">10.1002/9783527609703</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-27766-7" title="Special:BookSources/978-3-527-27766-7"><bdi>978-3-527-27766-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Geochemical+processes+in+soil+and+groundwater%3A+measurement+%E2%80%93+modelling+%E2%80%93+upscaling&rft.pages=67&rft.pub=Wiley-VCH&rft.date=2003&rft_id=info%3Adoi%2F10.1002%2F9783527609703&rft.isbn=978-3-527-27766-7&rft.aulast=Schulz&rft.aufirst=Horst+D.&rft.au=Hadeler%2C+Astrid&rft.au=Deutsche+Forschungsgemeinschaft&rft_id=http%3A%2F%2Fonlinelibrary.wiley.com%2Fdoi%2F10.1002%2F9783527609703&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span> </li> <li id="cite_note-47"><span class="mw-cite-backlink"><b><a href="#cite_ref-47">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGailGosKulzerLorösch2004" class="citation encyclopaedia cs1">Gail, Ernst; Gos, Stephen; Kulzer, Rupprecht; Lorösch, Jürgen; Rubo, Andreas; Sauer, Manfred (2004). "Cyano Compounds, Inorganic". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a08_159.pub2">10.1002/14356007.a08_159.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Cyano+Compounds%2C+Inorganic&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2004&rft_id=info%3Adoi%2F10.1002%2F14356007.a08_159.pub2&rft.isbn=978-3527306732&rft.aulast=Gail&rft.aufirst=Ernst&rft.au=Gos%2C+Stephen&rft.au=Kulzer%2C+Rupprecht&rft.au=Lor%C3%B6sch%2C+J%C3%BCrgen&rft.au=Rubo%2C+Andreas&rft.au=Sauer%2C+Manfred&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span> </li> <li id="cite_note-48"><span class="mw-cite-backlink"><b><a href="#cite_ref-48">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchwenecke,_H.Mayer,_D.2005" class="citation encyclopaedia cs1">Schwenecke, H.; Mayer, D. (2005). "Benzidine and Benzidine Derivatives". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a03_539">10.1002/14356007.a03_539</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Benzidine+and+Benzidine+Derivatives&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2005&rft_id=info%3Adoi%2F10.1002%2F14356007.a03_539&rft.isbn=978-3527306732&rft.au=Schwenecke%2C+H.&rft.au=Mayer%2C+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span> </li> <li id="cite_note-49"><span class="mw-cite-backlink"><b><a href="#cite_ref-49">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGanjelooIsomMorganWay1980" class="citation journal cs1">Ganjeloo, A; Isom, GE; Morgan, RL; Way, JL (1980). "Fluorometric determination of cyanide in biological fluids with p-benzoquinone*1". <i><a href="/wiki/Toxicology_and_Applied_Pharmacology" title="Toxicology and Applied Pharmacology">Toxicology and Applied Pharmacology</a></i>. <b>55</b> (1): 103–107. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0041-008X%2880%2990225-2">10.1016/0041-008X(80)90225-2</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7423496">7423496</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Toxicology+and+Applied+Pharmacology&rft.atitle=Fluorometric+determination+of+cyanide+in+biological+fluids+with+p-benzoquinone%2A1&rft.volume=55&rft.issue=1&rft.pages=103-107&rft.date=1980&rft_id=info%3Adoi%2F10.1016%2F0041-008X%2880%2990225-2&rft_id=info%3Apmid%2F7423496&rft.aulast=Ganjeloo&rft.aufirst=A&rft.au=Isom%2C+GE&rft.au=Morgan%2C+RL&rft.au=Way%2C+JL&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanide&action=edit&section=29" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox 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href="/wiki/Wikisource" title="Wikisource">Wikisource</a> has the text of the <a href="/wiki/Encyclop%C3%A6dia_Britannica_Eleventh_Edition" title="Encyclopædia Britannica Eleventh Edition">1911 <i>Encyclopædia Britannica</i></a> article "<span style="font-weight:bold;"><a href="https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Cyanide" class="extiw" title="wikisource:1911 Encyclopædia Britannica/Cyanide">Cyanide</a></span>".</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735"><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Cyanides" class="extiw" title="commons:Category:Cyanides">Cyanides</a></span>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20100528070140/http://www.atsdr.cdc.gov/MMG/MMG.asp?id=1073&tid=19">ATSDR medical management guidelines for cyanide poisoning (US)</a></li> <li><a rel="nofollow" class="external text" href="http://www.hse.gov.uk/pubns/firindex.htm">HSE recommendations for first aid treatment of cyanide poisoning (UK)</a></li> <li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/cicads/cicads/cicad61.htm">Hydrogen cyanide and cyanides</a> (<a href="/wiki/CICAD" class="mw-redirect" title="CICAD">CICAD</a> 61)</li> <li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/antidote/antidote/ant02.htm#SubSectionNumber:1.13.1">IPCS/CEC Evaluation of antidotes for poisoning by cyanides</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20060517035532/http://www.npi.gov.au/database/substance-info/profiles/29.html">National Pollutant Inventory – Cyanide compounds fact sheet</a></li> <li><a rel="nofollow" class="external text" href="http://www.snopes.com/food/warnings/apples.asp#add">Eating apple seeds is safe despite the small amount of cyanide</a></li> <li><a rel="nofollow" class="external text" href="https://www.atsdr.cdc.gov/toxprofiles/tp8.pdf">Toxicological Profile for Cyanide, U.S. Department of Health and Human Services, July 2006</a></li></ul> <dl><dt>Safety data (French)</dt></dl> <ul><li>Institut national de recherche et de sécurité (1997). "<a rel="nofollow" class="external text" href="https://web.archive.org/web/20060220084315/http://www.inrs.fr/inrs-pub/inrs01.nsf/inrs01_ftox_view/860430FE710FCFD7C1256CE8004F67CB/$File/ft4.pdf">Cyanure d'hydrogène et solutions aqueuses</a>". <i>Fiche toxicologique n° 4</i>, Paris: INRS, 5 pp. (PDF file, <span class="languageicon">(in French)</span>)</li> <li>Institut national de recherche et de sécurité (1997). "<a rel="nofollow" class="external text" href="https://web.archive.org/web/20060220084330/http://www.inrs.fr/inrs-pub/inrs01.nsf/inrs01_ftox_view/48145297F4EF18BBC1256CE8005A9FC2/$File/ft111.pdf">Cyanure de sodium. Cyanure de potassium</a>". <i>Fiche toxicologique n° 111</i>, Paris: INRS, 6 pp. (PDF file, <span class="languageicon">(in French)</span>)</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist 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style="font-size:114%;margin:0 4em">Salts and covalent derivatives of the <a class="mw-selflink selflink">cyanide</a> ion</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;border-width:0;"><div style="padding:0"><div class="mw-collapsible-content" style="overflow-x:auto"> <table class="center"> <tbody><tr style="background-color:mistyrose"> <td><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">HCN</a> </td> <td style="background-color:white;border:none"> </td> <td style="background-color:white;border:none" colspan="11" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="5"> </td> <td>He </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Lithium_cyanide" title="Lithium cyanide">LiCN</a> </td> <td><a href="/w/index.php?title=Beryllium_cyanide&action=edit&redlink=1" class="new" title="Beryllium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Be(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Boron_cyanide&action=edit&redlink=1" class="new" title="Boron cyanide (page does not exist)">B(CN)<sub>3</sub></a> </td> <td><a href="/wiki/Tetracyanomethane" title="Tetracyanomethane">C(CN)<sub>4</sub></a><br /><a href="/wiki/Dicyanoacetylene" title="Dicyanoacetylene">C<sub>2</sub>(CN)<sub>2</sub></a> </td> <td><a href="/wiki/Ammonium_cyanide" title="Ammonium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NH<sub class="template-chem2-sub">4</sub>CN</span></a><br /><a href="/wiki/Nitrosyl_cyanide" title="Nitrosyl cyanide">ONCN</a><br /><a href="/wiki/Nitryl_cyanide" title="Nitryl cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O<sub class="template-chem2-sub">2</sub>NCN</span></a><br /><a href="/wiki/Cyanogen_azide" title="Cyanogen azide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N<sub class="template-chem2-sub">3</sub>CN</span></a> </td> <td><a href="/wiki/Cyanate" title="Cyanate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">OCN<sup class="template-chem2-sup">−</sup></span></a><br /><a href="/wiki/Isocyanate" title="Isocyanate">-NCO</a><br /><a href="/w/index.php?title=Dicyanoether&action=edit&redlink=1" class="new" title="Dicyanoether (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Cyanogen_fluoride" title="Cyanogen fluoride">FCN</a> </td> <td>Ne </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">NaCN</a> </td> <td><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Mg(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Aluminium_cyanide" title="Aluminium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Al(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Silicon_tetracyanide&action=edit&redlink=1" class="new" title="Silicon tetracyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Si(CN)<sub class="template-chem2-sub">4</sub></span></a><br /><a href="/wiki/Trimethylsilyl_cyanide" title="Trimethylsilyl cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>SiCN</span></a> </td> <td><a href="/wiki/Phosphorus_tricyanide" title="Phosphorus tricyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">P(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/wiki/Thiocyanate" title="Thiocyanate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">SCN<sup class="template-chem2-sup">−</sup></span></a><br /><a href="/wiki/Isothiocyanate" title="Isothiocyanate">-NCS</a><br /><a href="/wiki/Thiocyanogen" title="Thiocyanogen"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(SCN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/wiki/Sulfur_dicyanide" title="Sulfur dicyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">S(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">ClCN</a> </td> <td>Ar </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">KCN</a> </td> <td><a href="/wiki/Calcium_cyanide" title="Calcium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ca(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td style="background-color:white;border:none"> </td> <td><a href="/w/index.php?title=Scandium_cyanide&action=edit&redlink=1" class="new" title="Scandium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sc(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Ti </td> <td>V </td> <td><a href="/wiki/Potassium_hexacyanochromate(III)" title="Potassium hexacyanochromate(III)">Cr(CN)<sub>6</sub><sup>3−</sup></a> </td> <td>Mn </td> <td><a href="/wiki/Iron(II)_cyanide" title="Iron(II) cyanide">Fe(CN)<sub>2</sub></a><br /><a href="/wiki/Ferrocyanide" title="Ferrocyanide">Fe(CN)<sub>6</sub><sup>4−</sup></a><br /><a href="/wiki/Ferricyanide" title="Ferricyanide">Fe(CN)<sub>6</sub><sup>3−</sup></a> </td> <td><a href="/wiki/Cobalt(II)_cyanide" title="Cobalt(II) cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Co(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/wiki/Pentacyanocobaltate" title="Pentacyanocobaltate">Co(CN)<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">3−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span></a> </td> <td><a href="/wiki/Nickel_dicyanide" title="Nickel dicyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ni(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/wiki/Cyanonickelate" title="Cyanonickelate">Ni(CN)<sub>4</sub><sup>2−</sup></a><br /><a href="/w/index.php?title=Cyanonickelate(0)&action=edit&redlink=1" class="new" title="Cyanonickelate(0) (page does not exist)">Ni(CN)<sub>4</sub><sup>4−</sup></a> </td> <td><a href="/wiki/Copper(I)_cyanide" title="Copper(I) cyanide">CuCN</a> </td> <td><a href="/wiki/Zinc_cyanide" title="Zinc cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Zn(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Gallium(III)_cyanide" title="Gallium(III) cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ga(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Germanium_dicyanide&action=edit&redlink=1" class="new" title="Germanium dicyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ge(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/w/index.php?title=Germanium_tetracyanide&action=edit&redlink=1" class="new" title="Germanium tetracyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ge(CN)<sub class="template-chem2-sub">4</sub></span></a> </td> <td><a href="/w/index.php?title=Arsenic_tricyanide&action=edit&redlink=1" class="new" title="Arsenic tricyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">As(CN)<sub class="template-chem2-sub">3</sub></span></a><br /><a href="/wiki/Cacodyl_cyanide" title="Cacodyl cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>AsCN</span></a><br /><a href="/wiki/Diphenylcyanoarsine" title="Diphenylcyanoarsine"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>AsCN</span></a> </td> <td><a href="/wiki/Selenocyanate" title="Selenocyanate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">SeCN<sup class="template-chem2-sup">−</sup></span></a><br /><a href="/w/index.php?title=Selenocyanogen&action=edit&redlink=1" class="new" title="Selenocyanogen (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(SeCN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/w/index.php?title=Selenium_dicyanide&action=edit&redlink=1" class="new" title="Selenium dicyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Se(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Cyanogen_bromide" title="Cyanogen bromide">BrCN</a> </td> <td>Kr </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Rubidium_cyanide" title="Rubidium cyanide">RbCN</a> </td> <td><a href="/w/index.php?title=Strontium_cyanide&action=edit&redlink=1" class="new" title="Strontium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sr(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td style="background-color:white;border:none"> </td> <td><a href="/w/index.php?title=Yttrium_cyanide&action=edit&redlink=1" class="new" title="Yttrium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Y(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Zr </td> <td>Nb </td> <td><a href="/wiki/Potassium_octacyanomolybdate(IV)" title="Potassium octacyanomolybdate(IV)">Mo(CN)<sub>8</sub><sup>4−</sup></a> </td> <td>Tc </td> <td>Ru </td> <td>Rh </td> <td><a href="/wiki/Palladium_dicyanide" title="Palladium dicyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pd(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Silver_cyanide" title="Silver cyanide">AgCN</a> </td> <td><a href="/wiki/Cadmium_cyanide" title="Cadmium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cd(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Indium_cyanide&action=edit&redlink=1" class="new" title="Indium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">In(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Tin(II)_cyanide&action=edit&redlink=1" class="new" title="Tin(II) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sn(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Antimony_cyanide&action=edit&redlink=1" class="new" title="Antimony cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sb(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Tellurium_dicyanide&action=edit&redlink=1" class="new" title="Tellurium dicyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Te(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/w/index.php?title=Tellurium_tetracyanide&action=edit&redlink=1" class="new" title="Tellurium tetracyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Te(CN)<sub class="template-chem2-sub">4</sub></span></a> </td> <td><a href="/wiki/Cyanogen_iodide" title="Cyanogen iodide">ICN</a> </td> <td>Xe </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Caesium_cyanide" title="Caesium cyanide">CsCN</a> </td> <td><a href="/wiki/Barium_cyanide" title="Barium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ba(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td style="background-color:white;border:none">* </td> <td><a href="/w/index.php?title=Lutetium(III)_cyanide&action=edit&redlink=1" class="new" title="Lutetium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Lu(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Hf </td> <td>Ta </td> <td><a href="/w/index.php?title=Potassium_octacyanotungstate(IV)&action=edit&redlink=1" class="new" title="Potassium octacyanotungstate(IV) (page does not exist)">W(CN)<sub>8</sub><sup>4−</sup></a> </td> <td>Re </td> <td>Os </td> <td>Ir </td> <td><a href="/wiki/Platinocyanide" title="Platinocyanide">Pt(CN)<sub>4</sub><sup>2-</sup></a><br /><a href="/w/index.php?title=Platinicyanide&action=edit&redlink=1" class="new" title="Platinicyanide (page does not exist)">Pt(CN)<sub>6</sub><sup>4-</sup></a><br /> </td> <td><a href="/wiki/Gold(I)_cyanide" title="Gold(I) cyanide">AuCN</a><br /><a href="/wiki/Potassium_dicyanoaurate" title="Potassium dicyanoaurate">Au(CN)<sub>2</sub><sup>-</sup></a> </td> <td><a href="/w/index.php?title=Mercury(I)_cyanide&action=edit&redlink=1" class="new" title="Mercury(I) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Hg<sub class="template-chem2-sub">2</sub>(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/wiki/Mercury(II)_cyanide" title="Mercury(II) cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Hg(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Thallium(I)_cyanide&action=edit&redlink=1" class="new" title="Thallium(I) cyanide (page does not exist)">TlCN</a> </td> <td><a href="/w/index.php?title=Lead_cyanide&action=edit&redlink=1" class="new" title="Lead cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pb(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Bismuth(III)_cyanide&action=edit&redlink=1" class="new" title="Bismuth(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Bi(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Po </td> <td>At </td> <td>Rn </td></tr> <tr style="background-color:mistyrose"> <td>Fr </td> <td>Ra </td> <td style="background-color:white;border:none">** </td> <td>Lr </td> <td>Rf </td> <td>Db </td> <td>Sg </td> <td>Bh </td> <td>Hs </td> <td>Mt </td> <td>Ds </td> <td>Rg </td> <td>Cn </td> <td>Nh </td> <td>Fl </td> <td>Mc </td> <td>Lv </td> <td>Ts </td> <td>Og </td></tr> <tr> <td style="background-color:white;border:none" colspan="2" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="20">  </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">* </td> <td><a href="/w/index.php?title=Lanthanum_cyanide&action=edit&redlink=1" class="new" title="Lanthanum cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">La(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Cerium(III)_cyanide&action=edit&redlink=1" class="new" title="Cerium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ce(CN)<sub class="template-chem2-sub">3</sub></span></a><br /> <a href="/w/index.php?title=Cerium(IV)_cyanide&action=edit&redlink=1" class="new" title="Cerium(IV) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ce(CN)<sub class="template-chem2-sub">4</sub></span></a> </td> <td><a href="/w/index.php?title=Praseodymium(III)_cyanide&action=edit&redlink=1" class="new" title="Praseodymium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pr(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Nd </td> <td>Pm </td> <td><a href="/w/index.php?title=Samarium(III)_cyanide&action=edit&redlink=1" class="new" title="Samarium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sm(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Europium(III)_cyanide&action=edit&redlink=1" class="new" title="Europium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Eu(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Gadolinium(III)_cyanide&action=edit&redlink=1" class="new" title="Gadolinium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Gd(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Tb </td> <td><a href="/w/index.php?title=Dysprosium(III)_cyanide&action=edit&redlink=1" class="new" title="Dysprosium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Dy(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Holmium(III)_cyanide&action=edit&redlink=1" class="new" title="Holmium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ho(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Er </td> <td>Tm </td> <td><a href="/wiki/Ytterbium(III)_cyanide" title="Ytterbium(III) cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Yb(CN)<sub class="template-chem2-sub">3</sub></span></a> </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">** </td> <td><a href="/w/index.php?title=Actinium(III)_cyanide&action=edit&redlink=1" class="new" title="Actinium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ac(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Thorium(IV)_cyanide&action=edit&redlink=1" class="new" title="Thorium(IV) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Th(CN)<sub class="template-chem2-sub">4</sub></span></a> </td> <td>Pa </td> <td><a href="/w/index.php?title=Uranyl_cyanide&action=edit&redlink=1" class="new" title="Uranyl cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">UO<sub class="template-chem2-sub">2</sub>(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td>Np </td> <td>Pu </td> <td>Am </td> <td>Cm </td> <td>Bk </td> <td>Cf </td> <td>Es </td> <td>Fm </td> <td>Md </td> <td>No </td></tr></tbody></table></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="Inorganic_compounds_of_carbon_and_related_ions" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse 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:Inorganic_compounds_of_carbon" title="Template:Inorganic compounds of carbon"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Inorganic_compounds_of_carbon" title="Template talk:Inorganic compounds of carbon"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Inorganic_compounds_of_carbon" title="Special:EditPage/Template:Inorganic compounds of carbon"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Inorganic_compounds_of_carbon_and_related_ions" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_inorganic_compounds" title="List of inorganic compounds">Inorganic compounds of</a> <a href="/wiki/Carbon" title="Carbon">carbon</a> and related ions</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Compounds</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/Carbon_monofluoride" title="Carbon monofluoride">CF</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">CO</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></li> <li><a href="/wiki/Carbon_trioxide" title="Carbon trioxide">CO<sub>3</sub></a></li> <li><a href="/wiki/Carbon_tetroxide" title="Carbon tetroxide">CO<sub>4</sub></a></li> <li><a href="/wiki/Carbon_pentoxide" title="Carbon pentoxide">CO<sub>5</sub></a></li> <li><a href="/wiki/Carbon_hexoxide" title="Carbon hexoxide">CO<sub>6</sub></a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">COS</a></li> <li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">CS</a></li> <li><a href="/wiki/Ethenedithione" title="Ethenedithione">C<sub>2</sub>S<sub>2</sub></a></li> <li><a href="/wiki/Carbon_disulfide" title="Carbon disulfide">CS<sub>2</sub></a></li> <li><a href="/wiki/Carbon_diselenide" title="Carbon diselenide">CSe<sub>2</sub></a></li> <li><a href="/wiki/Carbon_suboxide" title="Carbon suboxide">C<sub>3</sub>O<sub>2</sub></a></li> <li><a href="/wiki/Carbon_subsulfide" title="Carbon subsulfide">C<sub>3</sub>S<sub>2</sub></a></li> <li><a href="/wiki/Silicon_carbide" title="Silicon carbide">SiC</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Carbon ions</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/Carbide" title="Carbide">Carbides</a> [:C≡C:]<sup>2−</sup>, [::C::]<sup>4−</sup>, [:C=C=C:]<sup>4−</sup></li> <li><a class="mw-selflink selflink">Cyanide</a> [:C≡N:]<sup>−</sup></li> <li><a href="/wiki/Cyanate" title="Cyanate">Cyanate</a> [:O−C≡N:]<sup>−</sup></li> <li><a href="/wiki/Thiocyanate" title="Thiocyanate">Thiocyanate</a> [:S−C≡N:]<sup>−</sup></li> <li><a href="/wiki/Fulminate" title="Fulminate">Fulminate</a> [:C≡N−O:]<sup>−</sup></li> <li><a href="https://www.wikidata.org/wiki/Q27110079" class="extiw" title="wikidata:Q27110079">Thiofulminate</a> [:C≡N−S:]<sup>−</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nanostructures</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/Graphite_intercalation_compounds" class="mw-redirect" title="Graphite intercalation compounds">Graphite intercalation compounds</a></li> <li><a href="/wiki/Fulleride" title="Fulleride">Fullerides</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Oxides and related</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/Oxocarbon" title="Oxocarbon">Oxides</a></li> <li><a href="/wiki/Carbon_nitride" title="Carbon nitride">Nitrides</a></li> <li><a href="/wiki/Metal_carbonyl" title="Metal carbonyl">Metal carbonyls</a></li> <li><a href="/wiki/Carbonic_acid" title="Carbonic acid">Carbonic acid</a></li> <li><a href="/wiki/Bicarbonate" title="Bicarbonate">Bicarbonates</a></li> <li><a href="/wiki/Carbonate" title="Carbonate">Carbonates</a></li></ul> </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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"></div><div role="navigation" class="navbox" aria-labelledby="Nitrogen_species" 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:Nitrogen_compounds" title="Template:Nitrogen compounds"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nitrogen_compounds" title="Template talk:Nitrogen compounds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nitrogen_compounds" title="Special:EditPage/Template:Nitrogen compounds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nitrogen_species" style="font-size:114%;margin:0 4em"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> species</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Hydrides</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/Ammonia" title="Ammonia">NH<sub>3</sub></a></li> <li><a href="/wiki/Ammonium" title="Ammonium"><span class="chemf nowrap">NH<span class="template-chem2-su"><span>+</span><span>4</span></span></span></a></li> <li><a href="/wiki/Metal_amides#Alkali_metal_amides" title="Metal amides"><span class="chemf nowrap">NH<span class="template-chem2-su"><span>−</span><span>2</span></span></span></a></li> <li><a href="/wiki/Nitride" title="Nitride">N<sup>3−</sup></a></li> <li><a href="/wiki/Hydroxylamine" title="Hydroxylamine">NH<sub>2</sub>OH</a></li> <li><a href="/wiki/Hydrazine" title="Hydrazine">N<sub>2</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Hydrazoic_acid" title="Hydrazoic acid">HN<sub>3</sub></a></li> <li><a href="/wiki/Azide" title="Azide"><span class="chemf nowrap">N<span class="template-chem2-su"><span>−</span><span>3</span></span></span></a></li> <li><a href="/wiki/Nitrogen_pentahydride" title="Nitrogen pentahydride"><i>NH<sub>5</sub></i></a> (?)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Organic</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/Amine" title="Amine">NR<sub>3</sub></a></li> <li><a href="/wiki/Imine" title="Imine">>C=NR</a></li> <li><a href="/wiki/Amide" title="Amide">−CONR<sub>2</sub></a></li> <li><a href="/wiki/Nitrile" title="Nitrile">−CN</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">HCN</a></li> <li><a class="mw-selflink selflink">CN<sup>−</sup></a></li> <li><a href="/wiki/Cyanogen" title="Cyanogen">(CN)<sub>2</sub></a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">H<sub>2</sub>NCN</a></li> <li><a href="/wiki/Cyanate" title="Cyanate">HOCN</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">HNCO</a></li> <li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">HNCS</a></li> <li><a href="/wiki/Diazomethane" title="Diazomethane">CH<sub>2</sub>N<sub>2</sub></a></li> <li><a href="/wiki/Nitroso" title="Nitroso">−NO</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">−NO<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen_oxide" title="Nitrogen oxide">Oxides</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/Nitric_oxide" title="Nitric oxide">NO</a> / <a href="/wiki/Dinitrogen_dioxide" title="Dinitrogen dioxide">(NO)<sub>2</sub></a></li> <li><a href="/wiki/Dinitrogen_trioxide" title="Dinitrogen trioxide">N<sub>2</sub>O<sub>3</sub></a></li> <li><a href="/wiki/Nitrous_acid" title="Nitrous acid">HNO<sub>2</sub></a> / <a href="/wiki/Nitrite" title="Nitrite"><span class="chemf nowrap">NO<span class="template-chem2-su"><span>−</span><span>2</span></span></span></a> / <a href="/wiki/Nitrosonium" title="Nitrosonium">NO<sup>+</sup></a></li> <li><a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">NO<sub>2</sub></a> / <a href="/wiki/Dinitrogen_tetroxide" title="Dinitrogen tetroxide">(NO<sub>2</sub>)<sub>2</sub></a></li> <li><a href="/wiki/Dinitrogen_pentoxide" title="Dinitrogen pentoxide">N<sub>2</sub>O<sub>5</sub></a></li> <li><a href="/wiki/Nitric_acid" title="Nitric acid">HNO<sub>3</sub></a> / <a href="/wiki/Nitrate" title="Nitrate"><span class="chemf nowrap">NO<span class="template-chem2-su"><span>−</span><span>3</span></span></span></a> / <a href="/wiki/Nitronium" class="mw-redirect" title="Nitronium"><span class="chemf nowrap">NO<span class="template-chem2-su"><span>+</span><span>2</span></span></span></a></li> <li><a href="/wiki/Nitrate_radical" title="Nitrate radical">NO<sub>3</sub></a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">HNO</a> / <a href="/wiki/Hyponitrous_acid" title="Hyponitrous acid">(HON)<sub>2</sub></a> / <a href="/wiki/Hyponitrite" title="Hyponitrite"><span class="chemf nowrap">N<sub class="template-chem2-sub">2</sub>O<span class="template-chem2-su"><span>−</span><span>2</span></span></span></a> / <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">N<sub>2</sub>O</a></li> <li><a href="/wiki/Nitramide" title="Nitramide">H<sub>2</sub>NNO<sub>2</sub></a></li> <li><a href="/wiki/Peroxynitrous_acid" title="Peroxynitrous acid">HO<sub>2</sub>NO</a> / <a href="/wiki/Peroxynitrite" title="Peroxynitrite">ONOO<sup>−</sup></a></li> <li><a href="/wiki/Peroxynitric_acid" title="Peroxynitric acid">HO<sub>2</sub>NO<sub>2</sub></a> / <a href="/wiki/Peroxynitrate" title="Peroxynitrate">O<sub>2</sub>NOO<sup>−</sup></a></li> <li><a href="/wiki/Orthonitrate" title="Orthonitrate"><span class="chemf nowrap">NO<span class="template-chem2-su"><span>−</span><span>4</span></span></span></a></li> <li><a href="/wiki/Nitroxylic_acid" title="Nitroxylic acid">H<sub>4</sub>N<sub>2</sub>O<sub>4</sub></a> / <a href="/wiki/Angeli%27s_salt" title="Angeli's salt"><span class="chemf nowrap">N<sub class="template-chem2-sub">2</sub>O<span class="template-chem2-su"><span>2−</span><span>3</span></span></span></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Halides</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/Nitrogen_monofluoride" title="Nitrogen monofluoride">NF</a></li> <li><a href="/wiki/Nitrogen_difluoride" title="Nitrogen difluoride">NF<sub>2</sub></a></li> <li><a href="/wiki/Nitrogen_trifluoride" title="Nitrogen trifluoride">NF<sub>3</sub></a></li> <li><a href="/wiki/Nitrogen_pentafluoride" title="Nitrogen pentafluoride"><i>NF<sub>5</sub></i></a> (?)</li> <li><a href="/wiki/Nitrogen_trichloride" title="Nitrogen trichloride">NCl<sub>3</sub></a></li> <li><a href="/wiki/Nitrogen_tribromide" title="Nitrogen tribromide">NBr<sub>3</sub></a></li> <li><a href="/wiki/Nitrogen_triiodide" title="Nitrogen triiodide">NI<sub>3</sub></a></li> <li><a href="/wiki/Fluorine_azide" title="Fluorine azide">FN<sub>3</sub></a></li> <li><a href="/wiki/Chlorine_azide" title="Chlorine azide">ClN<sub>3</sub></a></li> <li><a href="/wiki/Bromine_azide" title="Bromine azide">BrN<sub>3</sub></a></li> <li><a href="/wiki/Iodine_azide" title="Iodine azide">IN<sub>3</sub></a></li> <li><a href="/wiki/Fluoroamine" title="Fluoroamine">NH<sub>2</sub>F</a></li> <li><a href="/wiki/Dinitrogen_difluoride" title="Dinitrogen difluoride">N<sub>2</sub>F<sub>2</sub></a></li> <li><a href="/wiki/Monochloramine" title="Monochloramine">NH<sub>2</sub>Cl</a></li> <li><a href="/w/index.php?title=Difluoramine&action=edit&redlink=1" class="new" title="Difluoramine (page does not exist)">NHF<sub>2</sub></a></li> <li><a href="/wiki/Dichloramine" title="Dichloramine">NHCl<sub>2</sub></a></li> <li><a href="/w/index.php?title=Dibromamine&action=edit&redlink=1" class="new" title="Dibromamine (page does not exist)">NHBr<sub>2</sub></a></li> <li><a href="/w/index.php?title=Diiodoamine&action=edit&redlink=1" class="new" title="Diiodoamine (page does not exist)">NHI<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oxidation_state" title="Oxidation state">Oxidation states</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><span style="font-size:112%;"><b><a href="/wiki/Nitride" title="Nitride">−3</a></b></span>, <a href="/wiki/Hydrazine" title="Hydrazine">−2</a>, <a href="/wiki/Hydroxylamine" title="Hydroxylamine">−1</a>, 0, <a href="/wiki/Nitroxyl" title="Nitroxyl">+1</a>, <a href="/wiki/Nitric_oxide" title="Nitric oxide">+2</a>, <span style="font-size:112%;"><b><a href="/wiki/Nitrite" title="Nitrite">+3</a></b></span>, <a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">+4</a>, <span style="font-size:112%;"><b><a href="/wiki/Nitrate" title="Nitrate">+5</a></b></span> (a strongly <a href="/wiki/Acid" title="Acid">acidic</a> oxide)</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="Pest_control:_Rodenticides" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse 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:Rodenticides" title="Template:Rodenticides"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Rodenticides" title="Template talk:Rodenticides"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Rodenticides" title="Special:EditPage/Template:Rodenticides"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Pest_control:_Rodenticides" style="font-size:114%;margin:0 4em"><a href="/wiki/Pest_control" title="Pest control">Pest control</a>: <a href="/wiki/Rodenticide" title="Rodenticide">Rodenticides</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;;line-height:1.2em;"><a href="/wiki/Anticoagulant" title="Anticoagulant">Anticoagulants</a> /<br /><a href="/wiki/Vitamin_K_antagonist" title="Vitamin K antagonist">Vitamin K antagonists</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 scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/Coumarin" title="Coumarin">Coumarins</a> /<br /><a href="/wiki/4-Hydroxycoumarins" title="4-Hydroxycoumarins">4-Hydroxycoumarins</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%;line-height:1.2em;font-weight:normal;font-size:smaller;">1st generation</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/Warfarin" title="Warfarin">Warfarin</a></li> <li><a href="/wiki/Coumatetralyl" title="Coumatetralyl">Coumatetralyl</a></li> <li><a href="/wiki/Fumarin" title="Fumarin">Fumarin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;font-size:smaller;">2nd generation (<a href="/wiki/Superwarfarin" title="Superwarfarin">Superwarfarins</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/Brodifacoum" title="Brodifacoum">Brodifacoum</a></li> <li><a href="/wiki/Bromadiolone" title="Bromadiolone">Bromadiolone</a></li> <li><a href="/wiki/Difenacoum" title="Difenacoum">Difenacoum</a></li> <li><a href="/wiki/Difethialone" title="Difethialone">Difethialone</a></li> <li><a href="/wiki/Flocoumafen" title="Flocoumafen">Flocoumafen</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/1,3-Indandione" title="1,3-Indandione">1,3-Indandiones</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="/wiki/Chlorophacinone" title="Chlorophacinone">Chlorophacinone</a></li> <li><a href="/wiki/Pindone" title="Pindone">Pindone</a></li> <li><a href="/wiki/Diphacinone" class="mw-redirect" title="Diphacinone">Diphacinone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Convulsant" title="Convulsant">Convulsants</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Crimidine" title="Crimidine">Crimidine</a></li> <li><a href="/wiki/Phenylsilatrane" title="Phenylsilatrane">Phenylsilatrane</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Tetramethylenedisulfotetramine" title="Tetramethylenedisulfotetramine">Tetramethylenedisulfotetramine</a></li> <li><a href="/wiki/Chlorophenylsilatrane" title="Chlorophenylsilatrane">Chlorophenylsilatrane</a></li> <li><a href="/wiki/RDX" title="RDX">RDX</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Vitamin_D" title="Vitamin D">Calciferols</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/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Inorganic_compound" title="Inorganic compound">Inorganic compounds</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium_phosphide" title="Aluminium phosphide">Aluminium phosphide</a></li> <li><a href="/wiki/Arsenic" title="Arsenic">Arsenic</a></li> <li><a href="/wiki/Barium_carbonate" title="Barium carbonate">Barium carbonate</a></li> <li><a href="/wiki/Calcium_phosphide" title="Calcium phosphide">Calcium phosphide</a></li> <li><a class="mw-selflink selflink">Cyanide</a></li> <li><a href="/wiki/Thallium(I)_sulfate" title="Thallium(I) sulfate">Thallium sulfate</a></li> <li><a href="/wiki/Zinc_phosphide" title="Zinc phosphide">Zinc phosphide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Organochlorine" class="mw-redirect" title="Organochlorine">Organochlorine</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/Chloralose" title="Chloralose">Chloralose</a></li> <li><a href="/wiki/Endrin" title="Endrin">Endrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Organophosphorus" class="mw-redirect" title="Organophosphorus">Organophosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosacetim" title="Phosacetim">Phosacetim</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Carbamate" title="Carbamate">Carbamates</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/Aldicarb" title="Aldicarb">Aldicarb</a></li> <li><a href="/wiki/T-1152" title="T-1152">T-1152</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;">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><a href="/wiki/Alpha-Naphthylthiourea" class="mw-redirect" title="Alpha-Naphthylthiourea">α-Naphthylthiourea</a></li> <li><a href="/wiki/Bromethalin" title="Bromethalin">Bromethalin</a></li> <li><a href="/wiki/Fluoroacetamide" title="Fluoroacetamide">Fluoroacetamide</a></li> <li><a href="/wiki/Flupropadine" title="Flupropadine">Flupropadine</a></li> <li><a href="/wiki/1,3-Difluoro-2-propanol" title="1,3-Difluoro-2-propanol">1,3-Difluoro-2-propanol (Gliftor)</a></li> <li><a href="/wiki/Norbormide" title="Norbormide">Norbormide</a></li> <li><a href="/wiki/Pyrinuron" title="Pyrinuron">Pyrinuron</a></li> <li><a href="/wiki/Scilliroside" title="Scilliroside">Scilliroside</a></li> <li><a href="/wiki/Sodium_fluoroacetate" title="Sodium fluoroacetate">Sodium fluoroacetate</a></li></ul> </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="Consumer_food_safety" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse 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:Consumer_food_safety" title="Template:Consumer food safety"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Consumer_food_safety" title="Template talk:Consumer food safety"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Consumer_food_safety" title="Special:EditPage/Template:Consumer food safety"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Consumer_food_safety" style="font-size:114%;margin:0 4em"><a href="/wiki/Food_safety" title="Food safety">Consumer food safety</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adulterant" title="Adulterant">Adulterants</a>, <a href="/wiki/Food_contaminant" title="Food contaminant">food contaminants</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="/wiki/3-MCPD" title="3-MCPD">3-MCPD</a></li> <li><a href="/wiki/Aldicarb" title="Aldicarb">Aldicarb</a></li> <li><a href="/wiki/Antibiotic_use_in_livestock" title="Antibiotic use in livestock">Antibiotic use in livestock</a></li> <li><a class="mw-selflink selflink">Cyanide</a></li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/HGH_controversies" title="HGH controversies">HGH controversies</a></li> <li><a href="/wiki/Lead_poisoning" title="Lead poisoning">Lead poisoning</a></li> <li><a href="/wiki/Melamine" title="Melamine">Melamine</a></li> <li><a href="/wiki/Mercury_in_fish" title="Mercury in fish">Mercury in fish</a></li> <li><a href="/wiki/Sudan_I" title="Sudan I">Sudan I</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Food_additive" title="Food additive">Food additives</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/Flavoring" title="Flavoring">Flavorings</a></li> <li><a href="/wiki/Monosodium_glutamate" title="Monosodium glutamate">Monosodium glutamate (MSG)</a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Salt</a></li> <li><a href="/wiki/Sugar" title="Sugar">Sugar</a> <ul><li><a href="/wiki/High-fructose_corn_syrup" title="High-fructose corn syrup">High-fructose corn syrup</a></li></ul></li> <li><a href="/wiki/Vegetable_oil" title="Vegetable oil">Vegetable oil</a> <ul><li><a href="/wiki/Seed_oil_misinformation" title="Seed oil misinformation">controversy</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intestinal_parasite_infection" title="Intestinal parasite infection">Intestinal parasites</a>, <a href="/wiki/Parasitic_disease" title="Parasitic disease">parasitic disease</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="/wiki/Amoebiasis" title="Amoebiasis">Amoebiasis</a></li> <li><a href="/wiki/Anisakiasis" class="mw-redirect" title="Anisakiasis">Anisakiasis</a></li> <li><a href="/wiki/Cryptosporidiosis" title="Cryptosporidiosis">Cryptosporidiosis</a></li> <li><a href="/wiki/Cyclosporiasis" title="Cyclosporiasis">Cyclosporiasis</a></li> <li><a href="/wiki/Diphyllobothriasis" title="Diphyllobothriasis">Diphyllobothriasis</a></li> <li><a href="/wiki/Pinworm_infection" title="Pinworm infection">Enterobiasis</a></li> <li><a href="/wiki/Fasciolopsiasis" title="Fasciolopsiasis">Fasciolopsiasis</a></li> <li><a href="/wiki/Fasciolosis" title="Fasciolosis">Fasciolosis</a></li> <li><a href="/wiki/Giardiasis" title="Giardiasis">Giardiasis</a></li> <li><a href="/wiki/Gnathostomiasis" title="Gnathostomiasis">Gnathostomiasis</a></li> <li><a href="/wiki/Paragonimiasis" title="Paragonimiasis">Paragonimiasis</a></li> <li><a href="/wiki/Toxocariasis" title="Toxocariasis">Toxocariasis</a></li> <li><a href="/wiki/Toxoplasmosis" title="Toxoplasmosis">Toxoplasmosis</a></li> <li><a href="/wiki/Trichinosis" title="Trichinosis">Trichinosis</a></li> <li><a href="/wiki/Trichuriasis" title="Trichuriasis">Trichuriasis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Microorganism" title="Microorganism">Microorganisms</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/Botulism" title="Botulism">Botulism</a></li> <li><i><a href="/wiki/Campylobacter_jejuni" title="Campylobacter jejuni">Campylobacter jejuni</a></i></li> <li><i><a href="/wiki/Clostridium_perfringens" title="Clostridium perfringens">Clostridium perfringens</a></i></li> <li><i><a href="/wiki/Cronobacter" title="Cronobacter">Cronobacter</a></i></li> <li><i><a href="/wiki/Enterovirus" title="Enterovirus">Enterovirus</a></i></li> <li><a href="/wiki/Escherichia_coli_O104:H4" title="Escherichia coli O104:H4"><i>Escherichia coli</i> O104:H4</a></li> <li><a href="/wiki/Escherichia_coli_O157:H7" title="Escherichia coli O157:H7"><i>Escherichia coli</i> O157:H7</a></li> <li><a href="/wiki/Hepatitis_A" title="Hepatitis A">Hepatitis A</a></li> <li><a href="/wiki/Hepatitis_E" title="Hepatitis E">Hepatitis E</a></li> <li><i><a href="/wiki/Listeria" title="Listeria">Listeria</a></i></li> <li><a href="/wiki/Norovirus" title="Norovirus">Norovirus</a></li> <li><a href="/wiki/Rotavirus" title="Rotavirus">Rotavirus</a></li> <li><i><a href="/wiki/Salmonella" title="Salmonella">Salmonella</a></i></li> <li><a href="/wiki/Shigatoxigenic_and_verotoxigenic_Escherichia_coli" title="Shigatoxigenic and verotoxigenic Escherichia coli">Shigatoxigenic and verotoxigenic <i>E. coli</i></a></li> <li><i><a href="/wiki/Vibrio_cholerae" title="Vibrio cholerae">Vibrio cholerae</a></i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pesticide" title="Pesticide">Pesticides</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="/wiki/Chlorpyrifos" title="Chlorpyrifos">Chlorpyrifos</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a></li> <li><a href="/wiki/Lindane" title="Lindane">Lindane</a></li> <li><a href="/wiki/Malathion" title="Malathion">Malathion</a></li> <li><a href="/wiki/Methamidophos" title="Methamidophos">Methamidophos</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Preservative" title="Preservative">Preservatives</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/Benzoic_acid" title="Benzoic acid">Benzoic acid</a></li> <li><a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">Ethylenediaminetetraacetic acid (EDTA)</a></li> <li><a href="/wiki/Sodium_benzoate" title="Sodium benzoate">Sodium benzoate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sugar_substitute" title="Sugar substitute">Sugar substitutes</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="/wiki/Acesulfame_potassium" title="Acesulfame potassium">Acesulfame potassium</a></li> <li><a href="/wiki/Aspartame" title="Aspartame">Aspartame</a> <ul><li><a href="/wiki/Aspartame_controversy" title="Aspartame controversy">controversy</a></li></ul></li> <li><a href="/wiki/Saccharin" title="Saccharin">Saccharin</a></li> <li><a href="/wiki/Sodium_cyclamate" class="mw-redirect" title="Sodium cyclamate">Sodium cyclamate</a></li> <li><a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</a></li> <li><a href="/wiki/Sucralose" title="Sucralose">Sucralose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Toxin" title="Toxin">Toxins</a>, <a href="/wiki/Poison" title="Poison">poisons</a>, <a href="/wiki/Pollution" title="Pollution">environment pollution</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/Aflatoxin" title="Aflatoxin">Aflatoxin</a></li> <li><a href="/wiki/Arsenic_contamination_of_groundwater" title="Arsenic contamination of groundwater">Arsenic contamination of groundwater</a></li> <li><a href="/wiki/Benzene_in_soft_drinks" title="Benzene in soft drinks">Benzene in soft drinks</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Dioxin" title="Dioxin">Dioxin</a></li> <li><a href="/wiki/Mycotoxin" title="Mycotoxin">Mycotoxins</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Shellfish_poisoning" title="Shellfish poisoning">Shellfish poisoning</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Food_fraud" class="mw-redirect" title="Food fraud">Food fraud</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="/wiki/Bread_fraud" class="mw-redirect" title="Bread fraud">Bread</a></li> <li><a href="/wiki/Breast_milk_fraud" class="mw-redirect" title="Breast milk fraud">Breast milk</a></li> <li><a href="/wiki/Egg_fraud" class="mw-redirect" title="Egg fraud">Egg</a></li> <li><a href="/wiki/Olive_oil_fraud" class="mw-redirect" title="Olive oil fraud">Olive oil</a></li> <li><a href="/wiki/Prawn_fraud" class="mw-redirect" title="Prawn fraud">Prawn</a></li> <li><a href="/wiki/Seafood_fraud" class="mw-redirect" title="Seafood fraud">Seafood</a></li> <li><a href="/wiki/Shrimp_fraud" class="mw-redirect" title="Shrimp fraud">Shrimp</a></li> <li><a href="/wiki/Tea_fraud" class="mw-redirect" title="Tea fraud">Tea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Food_processing" title="Food processing">Food processing</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/4-Hydroxynonenal" title="4-Hydroxynonenal">4-Hydroxynonenal</a></li> <li><a href="/wiki/Acid-hydrolyzed_vegetable_protein" class="mw-redirect" title="Acid-hydrolyzed vegetable protein">Acid-hydrolyzed vegetable protein</a></li> <li><a href="/wiki/Acrylamide" title="Acrylamide">Acrylamide</a></li> <li><a href="/wiki/List_of_food_additives" title="List of food additives">Food additives</a></li> <li><a href="/wiki/Food_irradiation" title="Food irradiation">Food irradiation</a></li> <li><a href="/wiki/Heterocyclic_amine" title="Heterocyclic amine">Heterocyclic amines</a></li> <li><a href="/wiki/Modified_starch" title="Modified starch">Modified starch</a></li> <li><a href="/wiki/Nitrosamine" title="Nitrosamine">Nitrosamines</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a></li> <li><a href="/wiki/Shortening" title="Shortening">Shortening</a></li> <li><a href="/wiki/Trans_fat" title="Trans fat">Trans fat</a></li> <li><a href="/wiki/Variant_Creutzfeldt%E2%80%93Jakob_disease" title="Variant Creutzfeldt–Jakob disease">Variant Creutzfeldt–Jakob disease</a></li> <li><a href="/wiki/Water_fluoridation_controversy" title="Water fluoridation controversy">Water fluoridation controversy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_food_contamination_incidents" title="List of food contamination incidents">Food contamination incidents</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="/wiki/Devon_colic" title="Devon colic">Devon colic</a></li> <li><a href="/wiki/Swill_milk_scandal" title="Swill milk scandal">Swill milk scandal</a></li> <li><a href="/wiki/Esing_Bakery_incident" title="Esing Bakery incident">Esing Bakery incident</a></li> <li><a href="/wiki/1858_Bradford_sweets_poisoning" title="1858 Bradford sweets poisoning">1858 Bradford sweets poisoning</a></li> <li><a href="/wiki/1900_English_beer_poisoning" title="1900 English beer poisoning">1900 English beer poisoning</a></li> <li><a href="/wiki/Morinaga_Milk_arsenic_poisoning_incident" title="Morinaga Milk arsenic poisoning incident">Morinaga Milk arsenic poisoning incident</a></li> <li><a href="/wiki/Minamata_disease" title="Minamata disease">Minamata disease</a></li> <li><a href="/w/index.php?title=Moroccan_oil_poisoning_disaster_1959&action=edit&redlink=1" class="new" title="Moroccan oil poisoning disaster 1959 (page does not exist)">Moroccan oil poisoning disaster 1959</a><span class="noprint" style="font-size:85%; font-style: normal;"> [<a href="https://ar.wikipedia.org/wiki/%D9%83%D8%A7%D8%B1%D8%AB%D8%A9_%D8%A7%D9%84%D8%B2%D9%8A%D9%88%D8%AA_%D8%A7%D9%84%D9%85%D8%B3%D9%85%D9%88%D9%85%D8%A9_%D9%81%D9%8A_%D8%A7%D9%84%D9%85%D8%BA%D8%B1%D8%A8_1959" class="extiw" title="ar:كارثة الزيوت المسمومة في المغرب 1959">ar</a>]</span></li> <li><a href="/wiki/1971_Iraq_poison_grain_disaster" title="1971 Iraq poison grain disaster">1971 Iraq poison grain disaster</a></li> <li><a href="/wiki/Toxic_oil_syndrome" title="Toxic oil syndrome">Toxic oil syndrome</a></li> <li><a href="/wiki/1985_Austrian_diethylene_glycol_wine_scandal" title="1985 Austrian diethylene glycol wine scandal">1985 Austrian diethylene glycol wine scandal</a></li> <li><a href="/wiki/United_Kingdom_BSE_outbreak" title="United Kingdom BSE outbreak">United Kingdom BSE outbreak</a></li> <li><a href="/wiki/Australian_meat_substitution_scandal" title="Australian meat substitution scandal">Australian meat substitution scandal</a></li> <li><a href="/wiki/1993_Jack_in_the_Box_E._coli_outbreak" class="mw-redirect" title="1993 Jack in the Box E. coli outbreak">Jack in the Box <i>E. coli</i> outbreak</a></li> <li><a href="/wiki/1996_Odwalla_E._coli_outbreak" title="1996 Odwalla E. coli outbreak">1996 Odwalla <i>E. coli</i> outbreak</a></li> <li><a href="/wiki/2006_North_American_E._coli_O157:H7_outbreaks" title="2006 North American E. coli O157:H7 outbreaks">2006 North American <i>E. coli</i> outbreaks</a></li> <li><a href="/wiki/ICA_meat_repackaging_controversy" title="ICA meat repackaging controversy">ICA meat repackaging controversy</a></li> <li><a href="/wiki/2008_Canada_listeriosis_outbreak" title="2008 Canada listeriosis outbreak">2008 Canada listeriosis outbreak</a></li> <li><a href="/wiki/2008_Chinese_milk_scandal" title="2008 Chinese milk scandal">2008 Chinese milk scandal</a></li> <li><a href="/wiki/2008_Irish_pork_crisis" title="2008 Irish pork crisis">2008 Irish pork crisis</a></li> <li><a href="/wiki/2008_United_States_salmonellosis_outbreak" title="2008 United States salmonellosis outbreak">2008 United States salmonellosis outbreak</a></li> <li><a href="/wiki/2011_Germany_E._coli_O104:H4_outbreak" title="2011 Germany E. coli O104:H4 outbreak">2011 Germany <i>E. coli</i> outbreak</a></li> <li><a href="/wiki/2011_United_States_listeriosis_outbreak" title="2011 United States listeriosis outbreak">2011 United States listeriosis outbreak</a></li> <li><a href="/wiki/Bihar_school_meal_poisoning_incident" title="Bihar school meal poisoning incident">Bihar school meal poisoning</a></li> <li><a href="/wiki/2013_horse_meat_scandal" title="2013 horse meat scandal">2013 horse meat scandal</a></li> <li><a href="/wiki/Mozambique_funeral_beer_poisoning" title="Mozambique funeral beer poisoning">2015 Mozambique funeral beer poisoning</a></li> <li><a href="/wiki/Operation_Weak_Meat" title="Operation Weak Meat">2017 Brazil Operation Weak Meat</a></li> <li><a href="/wiki/2017%E2%80%932018_South_African_listeriosis_outbreak" title="2017–2018 South African listeriosis outbreak">2017–2018 South African listeriosis outbreak</a></li> <li><a href="/wiki/2018_Australian_strawberry_contamination" title="2018 Australian strawberry contamination">2018 Australian strawberry contamination</a></li> <li><a href="/wiki/2024_United_Kingdom_Shigatoxigenic_E._coli_outbreak" title="2024 United Kingdom Shigatoxigenic E. coli outbreak">2024 United Kingdom Shigatoxigenic E. coli outbreak</a></li> <li><a href="/wiki/Kobayashi_red_yeast_rice_scandal" title="Kobayashi red yeast rice scandal">Kobayashi red yeast rice scandal</a></li> <li><a href="/wiki/Food_safety_incidents_in_China" title="Food safety incidents in China">Food safety incidents in China</a></li> <li><a href="/wiki/Food_safety_incidents_in_Taiwan" title="Food safety incidents in Taiwan">Food safety incidents in Taiwan</a></li> <li><a href="/wiki/Foodborne_illness" title="Foodborne illness">Foodborne illness</a> <ul><li><a href="/wiki/List_of_foodborne_illness_outbreaks" title="List of foodborne illness outbreaks">outbreaks</a></li> <li><a href="/wiki/List_of_foodborne_illness_outbreaks_by_death_toll" title="List of foodborne illness outbreaks by death toll">death toll</a></li> <li><a href="/wiki/List_of_foodborne_illness_outbreaks_in_the_United_States" title="List of foodborne illness outbreaks in the United States">United States</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Regulation" title="Regulation">Regulation</a>, <a href="/wiki/Standards_organization" title="Standards organization">standards</a>, <a href="/wiki/List_of_food_safety_organisations" title="List of food safety organisations">watchdogs</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/Acceptable_daily_intake" title="Acceptable daily intake">Acceptable daily intake</a></li> <li><a href="/wiki/E_number" title="E number">E number</a></li> <li><a href="/wiki/List_of_food_labeling_regulations" title="List of food labeling regulations">Food labeling regulations</a></li> <li><a href="/wiki/Food_libel_laws" title="Food libel laws">Food libel laws</a></li> <li><a href="/wiki/Food_safety_in_Australia" title="Food safety in Australia">Food safety in Australia</a></li> <li><a href="/wiki/International_Food_Safety_Network" title="International Food Safety Network">International Food Safety Network</a></li> <li><a href="/wiki/ISO_22000" title="ISO 22000">ISO 22000</a></li> <li><a href="/wiki/Nutrition_facts_label" title="Nutrition facts label">Nutrition facts label</a></li> <li><a href="/wiki/Organic_certification" title="Organic certification">Organic certification</a></li> <li><a href="/wiki/Quality_Assurance_International" title="Quality Assurance International">Quality Assurance International</a></li> <li><a href="/wiki/United_Kingdom_food_information_regulations" title="United Kingdom food information regulations">United Kingdom food information regulations</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_food_safety_organisations" title="List of food safety organisations">Institutions</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="/wiki/Centre_for_Food_Safety" title="Centre for Food Safety">Centre for Food Safety</a> (Hong Kong)</li> <li><a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a></li> <li><a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a></li> <li><a href="/wiki/Food_Information_and_Control_Agency" title="Food Information and Control Agency">Food Information and Control Agency</a> (Spain)</li> <li><a href="/wiki/Food_Standards_Agency" title="Food Standards Agency">Food Standards Agency</a> (United Kingdom)</li> <li><a href="/wiki/Institute_for_Food_Safety_and_Health" title="Institute for Food Safety and Health">Institute for Food Safety and Health</a></li> <li><a href="/wiki/International_Food_Safety_Network" title="International Food Safety Network">International Food Safety Network</a></li> <li><a href="/wiki/Ministry_of_Food_and_Drug_Safety" title="Ministry of Food and Drug Safety">Ministry of Food and Drug Safety</a> (South Korea)</li> <li><a href="/wiki/Spanish_Agency_for_Food_Safety_and_Nutrition" title="Spanish Agency for Food Safety and Nutrition">Spanish Agency for Food Safety and Nutrition</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related topics</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/Curing_(food_preservation)" title="Curing (food preservation)">Curing (food preservation)</a></li> <li><a href="/wiki/Food_and_drink_prohibitions" title="Food and drink prohibitions">Food and drink prohibitions</a></li> <li><a href="/wiki/Food_marketing" title="Food marketing">Food marketing</a></li> <li><a href="/wiki/Food_politics" title="Food politics">Food politics</a></li> <li><a href="/wiki/Food_preservation" title="Food preservation">Food preservation</a></li> <li><a href="/wiki/Food_quality" title="Food quality">Food quality</a></li> <li><a href="/wiki/Genetically_modified_food" title="Genetically modified food">Genetically modified food</a></li> <li><a href="/wiki/Conspiracy_theories" class="mw-redirect" title="Conspiracy theories">Conspiracy theories</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight:bold;"><div> <ul><li><span class="nowrap"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Foodlogo2.svg" class="mw-file-description"><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Foodlogo2.svg/16px-Foodlogo2.svg.png" decoding="async" width="16" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Foodlogo2.svg/24px-Foodlogo2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Foodlogo2.svg/32px-Foodlogo2.svg.png 2x" data-file-width="146" data-file-height="106" /></a></span> </span><a href="/wiki/Portal:Food" title="Portal:Food">Food portal</a> <span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Goblet_Glass_%28Banquet%29.svg/9px-Goblet_Glass_%28Banquet%29.svg.png" decoding="async" width="9" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Goblet_Glass_%28Banquet%29.svg/14px-Goblet_Glass_%28Banquet%29.svg.png 1.5x, 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src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span> <a href="https://commons.wikimedia.org/wiki/Category:Food_safety" class="extiw" title="commons:Category:Food safety">Commons</a></li> <li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Wikibooks-logo.svg" class="mw-file-description" title="Wikibooks page"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikibooks-logo.svg/16px-Wikibooks-logo.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikibooks-logo.svg/24px-Wikibooks-logo.svg.png 1.5x, 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