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id="toc-Occurrence" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Occurrence</span> </div> </a> <button aria-controls="toc-Occurrence-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 Occurrence subsection</span> </button> <ul id="toc-Occurrence-sublist" class="vector-toc-list"> <li id="toc-On_Titan" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#On_Titan"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>On Titan</span> </div> </a> <ul id="toc-On_Titan-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-On_the_young_Earth" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#On_the_young_Earth"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>On the young Earth</span> </div> </a> <ul id="toc-On_the_young_Earth-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_mammals" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_mammals"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>In mammals</span> </div> </a> <ul id="toc-In_mammals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-HCN_and_the_origin_of_life" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#HCN_and_the_origin_of_life"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>HCN and the origin of life</span> </div> </a> <ul id="toc-HCN_and_the_origin_of_life-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_space" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_space"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.5</span> <span>In space</span> </div> </a> <ul id="toc-In_space-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-As_a_poison_and_chemical_weapon" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#As_a_poison_and_chemical_weapon"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>As a poison and chemical weapon</span> </div> </a> <ul id="toc-As_a_poison_and_chemical_weapon-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">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 vector-toc-list-item-expanded"> <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">Hydrogen 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 70 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-70" 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">70 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/Blousuur" title="Blousuur – Afrikaans" lang="af" hreflang="af" data-title="Blousuur" 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_%D8%A7%D9%84%D9%87%D9%8A%D8%AF%D8%B1%D9%88%D8%AC%D9%8A%D9%86" title="سيانيد الهيدروجين – Arabic" lang="ar" hreflang="ar" data-title="سيانيد الهيدروجين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Sianid_tur%C5%9Fusu" title="Sianid turşusu – Azerbaijani" lang="az" hreflang="az" data-title="Sianid turşusu" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%87%DB%8C%D8%AF%D8%B1%D9%88%DA%98%D9%86_%D8%B3%DB%8C%D8%A7%D9%86%DB%8C%D8%AF" title="هیدروژن سیانید – South Azerbaijani" lang="azb" hreflang="azb" data-title="هیدروژن سیانید" 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%B9%E0%A6%BE%E0%A6%87%E0%A6%A1%E0%A7%8D%E0%A6%B0%E0%A7%8B%E0%A6%9C%E0%A7%87%E0%A6%A8_%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="হাইড্রোজেন সায়ানাইড – Bangla" lang="bn" hreflang="bn" data-title="হাইড্রোজেন সায়ানাইড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Cyan-ho%C3%A0_ch%C3%BAi-s%C3%B2%CD%98" title="Cyan-hoà chúi-sò͘ – Minnan" lang="nan" hreflang="nan" data-title="Cyan-hoà chúi-sò͘" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A1%D1%96%D0%BD%D1%96%D0%BB%D1%8C%D0%BD%D0%B0%D1%8F_%D0%BA%D1%96%D1%81%D0%BB%D0%B0%D1%82%D0%B0" title="Сінільная кіслата – Belarusian" lang="be" hreflang="be" data-title="Сінільная кіслата" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%A6%D1%8B%D1%8F%D0%BD%D0%B0%D0%B2%D0%B0%D0%B4%D0%B0%D1%80%D0%BE%D0%B4%D0%BD%D0%B0%D1%8F_%D0%BA%D1%96%D1%81%D1%8C%D0%BB%D1%8F" title="Цыянавадародная кісьля – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Цыянавадародная кісьля" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</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%BE%D0%B2%D0%BE%D0%B4%D0%BE%D1%80%D0%BE%D0%B4" title="Циановодород – Bulgarian" lang="bg" hreflang="bg" data-title="Циановодород" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Cianur_d%27hidrogen" title="Cianur d'hidrogen – Catalan" lang="ca" hreflang="ca" data-title="Cianur d'hidrogen" 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%A1%D0%B8%D0%BD%D0%B8%D0%BB%D1%8C_%D0%B9%D3%B3%C3%A7%D0%B5%D0%BA%C4%95" title="Синиль йӳçекĕ – Chuvash" lang="cv" hreflang="cv" data-title="Синиль йӳçекĕ" 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/Kyanovod%C3%ADk" title="Kyanovodík – Czech" lang="cs" hreflang="cs" data-title="Kyanovodík" 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/Bl%C3%A5syre" title="Blåsyre – Danish" lang="da" hreflang="da" data-title="Blåsyre" 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/Cyanwasserstoff" title="Cyanwasserstoff – German" lang="de" hreflang="de" data-title="Cyanwasserstoff" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Sinihape" title="Sinihape – Estonian" lang="et" hreflang="et" data-title="Sinihape" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A5%CE%B4%CF%81%CE%BF%CE%BA%CF%85%CE%AC%CE%BD%CE%B9%CE%BF" title="Υδροκυάνιο – Greek" lang="el" hreflang="el" data-title="Υδροκυάνιο" 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_de_hidr%C3%B3geno" title="Cianuro de hidrógeno – Spanish" lang="es" hreflang="es" data-title="Cianuro de hidrógeno" 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/Hidrogena_cianido" title="Hidrogena cianido – Esperanto" lang="eo" hreflang="eo" data-title="Hidrogena 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/Azido_zianhidriko" title="Azido zianhidriko – Basque" lang="eu" hreflang="eu" data-title="Azido zianhidriko" 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/%D9%87%DB%8C%D8%AF%D8%B1%D9%88%DA%98%D9%86_%D8%B3%DB%8C%D8%A7%D9%86%DB%8C%D8%AF" title="هیدروژن سیانید – Persian" lang="fa" hreflang="fa" data-title="هیدروژن سیانید" 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_d%27hydrog%C3%A8ne" title="Cyanure d'hydrogène – French" lang="fr" hreflang="fr" data-title="Cyanure d'hydrogène" 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/Aig%C3%A9ad_hidricianach" title="Aigéad hidricianach – Irish" lang="ga" hreflang="ga" data-title="Aigéad hidricianach" 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_de_hidr%C3%B3xeno" title="Cianuro de hidróxeno – Galician" lang="gl" hreflang="gl" data-title="Cianuro de hidróxeno" 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_%EC%88%98%EC%86%8C" title="사이안화 수소 – Korean" lang="ko" hreflang="ko" data-title="사이안화 수소" 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%A1%D5%AF%D5%A1%D5%B6_%D5%A9%D5%A9%D5%B8%D6%82" title="Ցիանական թթու – Armenian" lang="hy" hreflang="hy" data-title="Ցիանական թթու" 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%B9%E0%A4%BE%E0%A4%87%E0%A4%A1%E0%A5%8D%E0%A4%B0%E0%A5%8B%E0%A4%9C%E0%A4%A8_%E0%A4%B8%E0%A4%BE%E0%A4%AF%E0%A4%A8%E0%A4%BE%E0%A4%87%E0%A4%A1" title="हाइड्रोजन सायनाइड – Hindi" lang="hi" hreflang="hi" data-title="हाइड्रोजन 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/Cijanovodi%C4%8Dna_kiselina" title="Cijanovodična kiselina – Croatian" lang="hr" hreflang="hr" data-title="Cijanovodična kiselina" 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/Hidrogen_sianida" title="Hidrogen sianida – Indonesian" lang="id" hreflang="id" data-title="Hidrogen 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-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Bl%C3%A1s%C3%BDra" title="Blásýra – Icelandic" lang="is" hreflang="is" data-title="Blásýra" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acido_cianidrico" title="Acido cianidrico – Italian" lang="it" hreflang="it" data-title="Acido cianidrico" 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%9E%D7%99%D7%9E%D7%9F_%D7%A6%D7%99%D7%90%D7%A0%D7%99%D7%93%D7%99" title="מימן ציאנידי – Hebrew" lang="he" hreflang="he" data-title="מימן ציאנידי" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9A%D3%A9%D0%B3%D0%B5%D1%80%D1%82%D0%BA%D1%96%D1%88_%D2%9B%D1%8B%D1%88%D2%9B%D1%8B%D0%BB" title="Көгерткіш қышқыл – Kazakh" lang="kk" hreflang="kk" data-title="Көгерткіш қышқыл" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A1%D0%B8%D0%BD%D0%B8%D0%BB_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0%D1%81%D1%8B" title="Синил кислотасы – Kyrgyz" lang="ky" hreflang="ky" data-title="Синил кислотасы" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Acidum_hydrocyanicum" title="Acidum hydrocyanicum – Latin" lang="la" hreflang="la" data-title="Acidum hydrocyanicum" 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/Ci%C4%81n%C5%ABde%C5%86radis" title="Ciānūdeņradis – Latvian" lang="lv" hreflang="lv" data-title="Ciānūdeņradis" 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/Ciano_vandenilis" title="Ciano vandenilis – Lithuanian" lang="lt" hreflang="lt" data-title="Ciano vandenilis" 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/Hidrog%C3%A9n-cianid" title="Hidrogén-cianid – Hungarian" lang="hu" hreflang="hu" data-title="Hidrogén-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%BE%D0%B2%D0%BE%D0%B4%D0%BE%D1%80%D0%BE%D0%B4" title="Цијановодород – Macedonian" lang="mk" hreflang="mk" data-title="Цијановодород" 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%B9%E0%B5%88%E0%B4%A1%E0%B5%8D%E0%B4%B0%E0%B4%9C%E0%B5%BB_%E0%B4%B8%E0%B4%AF%E0%B4%A8%E0%B5%88%E0%B4%A1%E0%B5%8D" title="ഹൈഡ്രജൻ സയനൈഡ് – Malayalam" lang="ml" hreflang="ml" data-title="ഹൈഡ്രജൻ സയനൈഡ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-mr mw-list-item"><a href="https://mr.wikipedia.org/wiki/%E0%A4%B9%E0%A4%BE%E0%A4%AF%E0%A4%A1%E0%A5%8D%E0%A4%B0%E0%A5%8B%E0%A4%9C%E0%A4%A8_%E0%A4%B8%E0%A4%BE%E0%A4%AF%E0%A4%A8%E0%A4%BE%E0%A4%87%E0%A4%A1" title="हायड्रोजन सायनाइड – Marathi" lang="mr" hreflang="mr" data-title="हायड्रोजन सायनाइड" data-language-autonym="मराठी" data-language-local-name="Marathi" class="interlanguage-link-target"><span>मराठी</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Hidrogen_sianida" title="Hidrogen sianida – Malay" lang="ms" hreflang="ms" data-title="Hidrogen 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-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Waterstofcyanide" title="Waterstofcyanide – Dutch" lang="nl" hreflang="nl" data-title="Waterstofcyanide" 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%E6%B0%B4%E7%B4%A0" title="シアン化水素 – Japanese" lang="ja" hreflang="ja" data-title="シアン化水素" 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%BCanweederstoofs%C3%BCren" title="Tsüanweederstoofsüren – Northern Frisian" lang="frr" hreflang="frr" data-title="Tsüanweederstoofsüren" 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/Hydrogencyanid" title="Hydrogencyanid – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Hydrogencyanid" 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/Hydrogencyanid" title="Hydrogencyanid – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Hydrogencyanid" 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_d%27idrog%C3%A8n" title="Cianur d'idrogèn – Occitan" lang="oc" hreflang="oc" data-title="Cianur d'idrogèn" 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/Sianid" title="Sianid – Uzbek" lang="uz" hreflang="uz" data-title="Sianid" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Cyjanowod%C3%B3r" title="Cyjanowodór – Polish" lang="pl" hreflang="pl" data-title="Cyjanowodór" 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_de_hidrog%C3%AAnio" title="Cianeto de hidrogênio – Portuguese" lang="pt" hreflang="pt" data-title="Cianeto de hidrogênio" 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/Acid_cianhidric" title="Acid cianhidric – Romanian" lang="ro" hreflang="ro" data-title="Acid cianhidric" 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%A1%D0%B8%D0%BD%D0%B8%D0%BB%D1%8C%D0%BD%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Синильная кислота – Russian" lang="ru" hreflang="ru" data-title="Синильная кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Hydrogen_cyanide" title="Hydrogen cyanide – Simple English" lang="en-simple" hreflang="en-simple" data-title="Hydrogen 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/Kyanovod%C3%ADk" title="Kyanovodík – Slovak" lang="sk" hreflang="sk" data-title="Kyanovodík" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Cianovodikova_kislina" title="Cianovodikova kislina – Slovenian" lang="sl" hreflang="sl" data-title="Cianovodikova kislina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Cijanovodoni%C4%8Dna_kiselina" title="Cijanovodonična kiselina – Serbian" lang="sr" hreflang="sr" data-title="Cijanovodonična kiselina" 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/Cijanovodoni%C4%8Dna_kiselina" title="Cijanovodonična kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cijanovodonična kiselina" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Vetysyanidi" title="Vetysyanidi – Finnish" lang="fi" hreflang="fi" data-title="Vetysyanidi" 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/V%C3%A4tecyanid" title="Vätecyanid – Swedish" lang="sv" hreflang="sv" data-title="Vätecyanid" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%90%E0%AE%A4%E0%AE%B0%E0%AE%9A%E0%AE%A9%E0%AF%8D_%E0%AE%9A%E0%AE%AF%E0%AE%A9%E0%AF%88%E0%AE%9F%E0%AF%81" title="ஐதரசன் சயனைடு – Tamil" lang="ta" hreflang="ta" data-title="ஐதரசன் சயனைடு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%A1%D0%B8%D0%BD%D0%B8%D0%BB_%D3%99%D1%87%D0%B5%D0%BB%D0%B5%D0%B3%D0%B5" title="Синил әчелеге – Tatar" lang="tt" hreflang="tt" data-title="Синил әчелеге" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%84%E0%B8%AE%E0%B9%82%E0%B8%94%E0%B8%A3%E0%B9%80%E0%B8%88%E0%B8%99%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="ไฮโดรเจนไซยาไนด์ – Thai" lang="th" hreflang="th" data-title="ไฮโดรเจนไซยาไนด์" 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/Hidrojen_siyan%C3%BCr" title="Hidrojen siyanür – Turkish" lang="tr" hreflang="tr" data-title="Hidrojen 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%A1%D0%B8%D0%BD%D0%B8%D0%BB%D1%8C%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Синильна кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Синильна кислота" 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/%DB%81%D8%A7%D8%A6%DB%8C%DA%88%D8%B1%D9%88%D8%AC%D9%86_%D8%B3%D8%A7%DB%8C%D8%A7%D9%86%D8%A7%D8%A6%DB%8C%DA%88" title="ہائیڈروجن سایانائیڈ – Urdu" lang="ur" hreflang="ur" data-title="ہائیڈروجن سایانائیڈ" 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/Acid_hydrocyanic" title="Acid hydrocyanic – Vietnamese" lang="vi" hreflang="vi" data-title="Acid hydrocyanic" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E6%B0%AB%E6%B0%B0%E9%85%B8" title="氫氰酸 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="氫氰酸" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Acid_hydrocyanic" title="Acid hydrocyanic – Waray" lang="war" hreflang="war" data-title="Acid hydrocyanic" 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/%E6%B0%B0%E5%8C%96%E6%B0%AB" title="氰化氫 – Cantonese" lang="yue" hreflang="yue" data-title="氰化氫" 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%E6%B0%A2" title="氰化氢 – Chinese" lang="zh" hreflang="zh" data-title="氰化氢" data-language-autonym="中文" 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id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Highly toxic chemical with the formula HCN</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"Cyanane" redirects here. For a class of synthetic dyes, see <a href="/wiki/Cyanine" title="Cyanine">Cyanine</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">"Cyanide gas" redirects here. For other gaseous cyanides, see <a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">Cyanogen chloride</a>, <a href="/wiki/Cyanogen_fluoride" title="Cyanogen fluoride">Cyanogen fluoride</a>, and <a href="/wiki/Cyanogen" title="Cyanogen">Cyanogen</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>Hydrogen cyanide </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Hydrogen-cyanide-2D.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Hydrogen-cyanide-2D.svg/220px-Hydrogen-cyanide-2D.svg.png" decoding="async" width="220" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Hydrogen-cyanide-2D.svg/330px-Hydrogen-cyanide-2D.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Hydrogen-cyanide-2D.svg/440px-Hydrogen-cyanide-2D.svg.png 2x" data-file-width="512" data-file-height="140" /></a></span> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Hydrogen-cyanide-3D-balls.svg" class="mw-file-description" title="Ball and stick model of hydrogen cyanide"><img alt="Ball and stick model of hydrogen cyanide" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Hydrogen-cyanide-3D-balls.svg/110px-Hydrogen-cyanide-3D-balls.svg.png" decoding="async" width="110" height="49" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Hydrogen-cyanide-3D-balls.svg/165px-Hydrogen-cyanide-3D-balls.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/Hydrogen-cyanide-3D-balls.svg/220px-Hydrogen-cyanide-3D-balls.svg.png 2x" data-file-width="1102" data-file-height="492" /></a><figcaption>Ball and stick model of hydrogen cyanide</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Hydrogen-cyanide-3D-vdW.svg" class="mw-file-description" title="Spacefill model of hydrogen cyanide"><img alt="Spacefill model of hydrogen cyanide" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Hydrogen-cyanide-3D-vdW.svg/110px-Hydrogen-cyanide-3D-vdW.svg.png" decoding="async" width="110" height="79" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Hydrogen-cyanide-3D-vdW.svg/165px-Hydrogen-cyanide-3D-vdW.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Hydrogen-cyanide-3D-vdW.svg/220px-Hydrogen-cyanide-3D-vdW.svg.png 2x" data-file-width="1100" data-file-height="789" /></a><figcaption>Spacefill model of hydrogen cyanide</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Hydrogen_cyanide.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Hydrogen_cyanide.jpg/220px-Hydrogen_cyanide.jpg" decoding="async" width="220" height="151" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Hydrogen_cyanide.jpg/330px-Hydrogen_cyanide.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/22/Hydrogen_cyanide.jpg/440px-Hydrogen_cyanide.jpg 2x" data-file-width="944" data-file-height="648" /></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" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Formonitrile<sup id="cite_ref-pubchem_2-0" class="reference"><a href="#cite_note-pubchem-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></div> </td></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;">Methanenitrile<sup id="cite_ref-pubchem_2-1" class="reference"><a href="#cite_note-pubchem-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><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>Formic anammonide</li><li>Hydridonitridocarbon<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></li><li>Hydrocyanic acid <i>(aqueous)</i></li><li>Hydrogen cyanide <i>(gas form)</i></li><li>Prussic acid</li><li>Cyanane</li></ul></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><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=74-90-8">74-90-8</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%23N">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B00275">B00275</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=18407">CHEBI:18407</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.748.html">748</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.747">100.000.747</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q26075#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-821-6</li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C01326">C01326</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Hydrogen+Cyanide">Hydrogen+Cyanide</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/768">768</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>MW6825000</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/2WTB3V159F">2WTB3V159F</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>1051 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID9024148">DTXSID9024148</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q26075#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/CHN/c1-2/h1H<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: LELOWRISYMNNSU-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></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>HCN  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>27.0253 g/mol    </td></tr> <tr> <td>Appearance </td> <td>Colorless liquid or gas </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td><a href="/wiki/Almond#Sweet_and_bitter_almonds" title="Almond">bitter almond</a>-like<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> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.6876 g/cm<sup>3</sup><sup id="cite_ref-Haynes_4-0" class="reference"><a href="#cite_note-Haynes-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−13.29 °C (8.08 °F; 259.86 K)<sup id="cite_ref-Haynes_4-3" class="reference"><a href="#cite_note-Haynes-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>26 °C (79 °F; 299 K)<sup id="cite_ref-Haynes_4-4" class="reference"><a href="#cite_note-Haynes-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 4.67">: 4.67 </span></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Miscible </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> </td> <td>Miscible </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>100 kPa (25 °C)<sup id="cite_ref-Haynes_4-1" class="reference"><a href="#cite_note-Haynes-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 6.94">: 6.94 </span></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Henry%27s_law" title="Henry's law">Henry's law<br />constant</a> (<i>k</i><sub>H</sub>)</div> </td> <td>75 μmol Pa<sup>−1</sup> kg<sup>−1</sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>9.21 (in water), <p>12.9 (in DMSO)<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Basicity</a> (p<i>K</i><sub>b</sub>) </td> <td>4.79 (cyanide anion) </td></tr> <tr> <td><a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">Conjugate acid</a> </td> <td><a href="/wiki/Hydrocyanonium" class="mw-redirect" title="Hydrocyanonium">Hydrocyanonium</a> </td></tr> <tr> <td><a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">Conjugate base</a> </td> <td><a href="/wiki/Cyanide" title="Cyanide">Cyanide</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.2675<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> </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>0.183 mPa·s (25 °C)<sup id="cite_ref-Haynes_4-2" class="reference"><a href="#cite_note-Haynes-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 6.231">: 6.231 </span></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Crystal_structure" title="Crystal structure">Crystal structure</a></div> </td> <td>tetragonal (>170 K)<br />orthorhombic (<170 K)<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_symmetry" title="Molecular symmetry">Point group</a></div> </td> <td>C<sub>∞v</sub> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular shape</a></div> </td> <td>Linear </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>2.98 D </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>35.9 J K<sup>−1</sup> mol<sup>−1</sup> (gas)<sup id="cite_ref-Haynes_4-5" class="reference"><a href="#cite_note-Haynes-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 5.19">: 5.19 </span></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>201.8 J K<sup>−1</sup> mol<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>135.1 kJ mol<sup>−1</sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/50px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/75px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/100px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-pollu.svg" class="mw-file-description" title="GHS09: Environmental hazard"><img alt="GHS09: Environmental hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/50px-GHS-pictogram-pollu.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/75px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/100px-GHS-pictogram-pollu.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H225: Highly flammable liquid and vapour">H225</abbr>, <abbr class="abbr" title="H300+H310+H330: Fatal if swallowed, in contact with skin or if inhaled">H300+H310+H330</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H336: May cause drowsiness or dizziness">H336</abbr>, <abbr class="abbr" title="H370: Causes damage to organs">H370</abbr>, <abbr class="abbr" title="H410: Very toxic to aquatic life with long lasting effects">H410</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_25b70a921cc7b5c6" /></span><map name="ImageMap_25b70a921cc7b5c6"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" title="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" title="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus" title="Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" class="notheme mw-no-invert">4</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" class="notheme mw-no-invert">4</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus" class="notheme mw-no-invert">2</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>−17.8 °C (0.0 °F; 255.3 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>538 °C (1,000 °F; 811 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>5.6% – 40.0%<sup id="cite_ref-PGCH_8-0" class="reference"><a href="#cite_note-PGCH-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>50</sub> (<a href="/wiki/Lethal_dose#LC50" title="Lethal dose">median concentration</a>)</div> </td> <td>501 ppm (rat, 5 min)<br />323 ppm (mouse, 5 min)<br />275 ppm (rat, 15 min)<br />170 ppm (rat, 30 min)<br />160 ppm (rat, 30 min)<br />323 ppm (rat, 5 min)<sup id="cite_ref-IDLH_9-0" class="reference"><a href="#cite_note-IDLH-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>Lo</sub> (<a href="/wiki/Lethal_dose#LCLo" title="Lethal dose">lowest published</a>)</div> </td> <td>200 ppm (mammal, 5 min)<br />36 ppm (mammal, 2 hr)<br />107 ppm (human, 10 min)<br />759 ppm (rabbit, 1 min)<br />759 ppm (cat, 1 min)<br />357 ppm (human, 2 min)<br />179 ppm (human, 1 hr)<sup id="cite_ref-IDLH_9-1" class="reference"><a href="#cite_note-IDLH-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 10 ppm (11 mg/m<sup>3</sup>) [skin]<sup id="cite_ref-PGCH_8-1" class="reference"><a href="#cite_note-PGCH-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>ST 4.7 ppm (5 mg/m<sup>3</sup>) [skin]<sup id="cite_ref-PGCH_8-2" class="reference"><a href="#cite_note-PGCH-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>50 ppm<sup id="cite_ref-PGCH_8-3" class="reference"><a href="#cite_note-PGCH-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related alkanenitriles</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a></li><li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li><li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li><li><a href="/wiki/Cyanogen_iodide" title="Cyanogen iodide">Cyanogen iodide</a></li><li><a href="/wiki/Cyanogen_bromide" title="Cyanogen bromide">Cyanogen bromide</a></li><li><a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">Cyanogen chloride</a></li><li><a href="/wiki/Cyanogen_fluoride" title="Cyanogen fluoride">Cyanogen fluoride</a></li><li><a href="/wiki/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li><li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li><li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li><li><a href="/wiki/Cyanogen" title="Cyanogen">Cyanogen</a></li></ul></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=476999282&page2=Hydrogen+cyanide">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Hydrogen cyanide</b> (formerly known as <b>prussic acid</b>) is a <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> HCN and <a href="/wiki/Structural_formula" title="Structural formula">structural formula</a> <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">H−C≡N</span>. It is a highly <a href="/wiki/Toxic" class="mw-redirect" title="Toxic">toxic</a> and <a href="/wiki/Flammable" class="mw-redirect" title="Flammable">flammable</a> liquid that <a href="/wiki/Boiling" title="Boiling">boils</a> slightly above <a href="/wiki/Room_temperature" title="Room temperature">room temperature</a>, at 25.6 °C (78.1 °F). HCN is produced on an industrial scale and is a highly valued <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursor</a> to many chemical compounds ranging from <a href="/wiki/Polymers" class="mw-redirect" title="Polymers">polymers</a> to pharmaceuticals. Large-scale applications are for the production of <a href="/wiki/Potassium_cyanide" title="Potassium cyanide">potassium cyanide</a> and <a href="/wiki/Adiponitrile" title="Adiponitrile">adiponitrile</a>, used in mining and plastics, respectively.<sup id="cite_ref-Ullmann_10-0" class="reference"><a href="#cite_note-Ullmann-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is more toxic than solid cyanide compounds due to its <a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">volatile</a> nature. A solution of hydrogen cyanide in <a href="/wiki/Water_(molecule)" class="mw-redirect" title="Water (molecule)">water</a>, represented as HCN, is called <i>hydrocyanic acid</i>. The <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> of the cyanide anion are known as <a href="/wiki/Cyanide" title="Cyanide">cyanides</a>. </p><p>Whether hydrogen cyanide is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> or not is a topic of debate among chemists, and opinions vary from author to author. Traditionally, it is considered <a href="/wiki/Inorganic_compound" title="Inorganic compound">inorganic</a> by a significant number of authors. Contrary to this view, it is considered organic by other authors, because hydrogen cyanide belongs to the class of organic compounds known as <a href="/wiki/Nitriles" class="mw-redirect" title="Nitriles">nitriles</a> which have the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C≡N</span>, where R is typically <a href="/wiki/Organyl_group" title="Organyl group">organyl group</a> (e.g., <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> or <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a>) or <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> In the case of hydrogen cyanide, the R group is hydrogen H, so the other names of hydrogen cyanide are methanenitrile and formonitrile.<sup id="cite_ref-pubchem_2-2" class="reference"><a href="#cite_note-pubchem-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_general_properties">Structure and general properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_cyanide&action=edit&section=1" title="Edit section: Structure and general properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydrogen cyanide is a <a href="/wiki/Linear_molecular_geometry" title="Linear molecular geometry">linear molecule</a>, with a <a href="/wiki/Triple_bond" title="Triple bond">triple bond</a> between <a href="/wiki/Carbon" title="Carbon">carbon</a> and <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>. The <a href="/wiki/Tautomer" title="Tautomer">tautomer</a> of HCN is HNC, <a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">hydrogen isocyanide</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2023)">citation needed</span></a></i>]</sup> </p><p>HCN has a faint <a href="/wiki/Almond#Sweet_and_bitter_almonds" title="Almond">bitter almond</a>-like <a href="/wiki/Odor" title="Odor">odor</a> that some people are unable to <a href="/wiki/Olfactory_system" title="Olfactory system">detect</a> owing to a recessive <a href="/wiki/Gene" title="Gene">genetic</a> <a href="/wiki/Trait_(biological)" class="mw-redirect" title="Trait (biological)">trait</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> The <a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">volatile</a> compound has been used as inhalation <a href="/wiki/Rodenticide" title="Rodenticide">rodenticide</a> and human poison, as well as for killing whales.<sup id="cite_ref-irons_13-0" class="reference"><a href="#cite_note-irons-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Cyanide ions interfere with iron-containing respiratory enzymes.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2023)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_properties">Chemical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_cyanide&action=edit&section=2" title="Edit section: Chemical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydrogen cyanide is weakly <a href="/wiki/Acidic" class="mw-redirect" title="Acidic">acidic</a> with a <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">p<i>K</i><sub>a</sub></a> of 9.2. It partially <a href="/wiki/Ionization" title="Ionization">ionizes</a> in <a href="/wiki/Aqueous_solution" title="Aqueous solution">water</a> to give the <a href="/wiki/Cyanide" title="Cyanide">cyanide</a> anion, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CN<sup class="template-chem2-sup">−</sup></span>. HCN forms hydrogen bonds with its conjugate base, species such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CN<sup class="template-chem2-sup">−</sup>)(HCN)<sub class="template-chem2-sub">n</sub></span>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Hydrogen cyanide reacts with <a href="/wiki/Alkene" title="Alkene">alkenes</a> to give nitriles. The conversion, which is called <a href="/wiki/Hydrocyanation" title="Hydrocyanation">hydrocyanation</a>, employs nickel complexes as catalysts.<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">RCH=CH<sub class="template-chem2-sub">2</sub> + HCN → RCH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">2</sub>CN</span></dd></dl> <p>Four molecules of HCN will tetramerize into <a href="/wiki/Diaminomaleonitrile" title="Diaminomaleonitrile">diaminomaleonitrile</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Metal_cyanide" class="mw-redirect" title="Metal cyanide">Metal cyanides</a> are typically prepared by <a href="/wiki/Salt_metathesis" class="mw-redirect" title="Salt metathesis">salt metathesis</a> from alkali metal cyanide salts, but <a href="/wiki/Mercuric_cyanide" class="mw-redirect" title="Mercuric cyanide">mercuric cyanide</a> is formed from aqueous hydrogen cyanide:<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<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">HgO + 2 HCN → Hg(CN)<sub class="template-chem2-sub">2</sub> + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="History_of_discovery">History of discovery</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_cyanide&action=edit&section=3" title="Edit section: History of discovery"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydrogen cyanide was first isolated in 1752 by French chemist <a href="/wiki/Pierre_Macquer" title="Pierre Macquer">Pierre Macquer</a> who converted <a href="/wiki/Prussian_blue" title="Prussian blue">Prussian blue</a> to an <a href="/wiki/Iron_oxide" title="Iron oxide">iron oxide</a> plus a volatile component and found that these could be used to reconstitute it.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> The new component was what is now known as hydrogen cyanide. It was subsequently prepared from Prussian blue by the Swedish chemist <a href="/wiki/Carl_Wilhelm_Scheele" title="Carl Wilhelm Scheele">Carl Wilhelm Scheele</a> in 1782,<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> and was eventually given the German name <i>Blausäure</i> (<i>lit</i>. "Blue acid") because of its acidic nature in water and its derivation from Prussian blue. In English, it became known popularly as <i>prussic acid.</i> </p><p>In 1787, the French chemist <a href="/wiki/Claude_Louis_Berthollet" title="Claude Louis Berthollet">Claude Louis Berthollet</a> showed that prussic acid did not contain oxygen,<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> an important contribution to acid theory, which had hitherto postulated that acids must contain oxygen<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> (hence the name of <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> itself, which is derived from Greek elements that mean "acid-former" and are likewise <a href="/wiki/Calque" title="Calque">calqued</a> into German as <i>Sauerstoff</i>). In 1811, <a href="/wiki/Joseph_Louis_Gay-Lussac" title="Joseph Louis Gay-Lussac">Joseph Louis Gay-Lussac</a> prepared pure, liquified hydrogen cyanide.<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> In 1815, Gay-Lussac deduced Prussic acid's chemical formula.<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> The radical <i>cyanide</i> in hydrogen cyanide was given its name from <a href="/wiki/Cyan" title="Cyan">cyan</a>, not only an English word for a shade of blue but the Greek word for blue (<a href="/wiki/Ancient_Greek_language" class="mw-redirect" title="Ancient Greek language">Ancient Greek</a>: <span lang="grc">κύανος</span>), again owing to its derivation from Prussian blue. </p> <div class="mw-heading mw-heading2"><h2 id="Production_and_synthesis">Production and synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_cyanide&action=edit&section=4" title="Edit section: Production and synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The most important process is the <a href="/wiki/Andrussow_oxidation" class="mw-redirect" title="Andrussow oxidation">Andrussow oxidation</a> invented by <a href="/wiki/Leonid_Andrussow" title="Leonid Andrussow">Leonid Andrussow</a> at <a href="/wiki/IG_Farben" title="IG Farben">IG Farben</a> in which <a href="/wiki/Methane" title="Methane">methane</a> and <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> react in the presence of <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> at about 1,200 °C (2,190 °F) over a <a href="/wiki/Platinum" title="Platinum">platinum</a> catalyst:<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<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>In 2006, between 500 million and 1 billion pounds (between 230,000 and 450,000 t) were produced in the US.<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> Hydrogen cyanide is produced in large quantities by several processes and is a recovered waste product from the manufacture of <a href="/wiki/Acrylonitrile" title="Acrylonitrile">acrylonitrile</a>.<sup id="cite_ref-Ullmann_10-1" class="reference"><a href="#cite_note-Ullmann-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Of lesser importance is the <a href="/wiki/Degussa" class="mw-redirect" title="Degussa">Degussa</a> process (<a href="/wiki/BMA_process" title="BMA process">BMA process</a>) in which no oxygen is added and the energy must be transferred indirectly through the reactor wall:<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> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">4</sub> + NH<sub class="template-chem2-sub">3</sub> → HCN + 3H<sub class="template-chem2-sub">2</sub></span></dd></dl> <p>This reaction is akin to <a href="/wiki/Steam_reforming" title="Steam reforming">steam reforming</a>, the reaction of <a href="/wiki/Methane" title="Methane">methane</a> and water to give <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> and <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>. </p><p>In the Shawinigan Process, <a href="/wiki/Hydrocarbons" class="mw-redirect" title="Hydrocarbons">hydrocarbons</a>, e.g. <a href="/wiki/Propane" title="Propane">propane</a>, are reacted with ammonia. </p><p>In the laboratory, small amounts of HCN are produced by the addition of acids to cyanide salts of <a href="/wiki/Alkali_metals" class="mw-redirect" title="Alkali metals">alkali metals</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sup class="template-chem2-sup">+</sup> + CN<sup class="template-chem2-sup">−</sup> → HCN</span></dd></dl> <p>This reaction is sometimes the basis of accidental poisonings because the acid converts a nonvolatile cyanide salt into the gaseous HCN. </p><p>Hydrogen cyanide could be obtained from <a href="/wiki/Potassium_ferricyanide" title="Potassium ferricyanide">potassium ferricyanide</a> and acid: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">6 H<sup class="template-chem2-sup">+</sup> + [Fe(CN)<sub class="template-chem2-sub">6</sub>]<span class="template-chem2-su"><span>−</span><span>3</span></span> → 6 HCN + Fe<span class="template-chem2-su"><span>+</span><span>3</span></span></span><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><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></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Historical_methods_of_production">Historical methods of production</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_cyanide&action=edit&section=5" title="Edit section: Historical methods of production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The large demand for cyanides for mining operations in the 1890s was met by <a href="/wiki/George_Thomas_Beilby" class="mw-redirect" title="George Thomas Beilby">George Thomas Beilby</a>, who patented a method to produce hydrogen cyanide by passing <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> over glowing <a href="/wiki/Coal" title="Coal">coal</a> in 1892. This method was used until <a href="/wiki/Hamilton_Castner" title="Hamilton Castner">Hamilton Castner</a> in 1894 developed a synthesis starting from coal, ammonia, and <a href="/wiki/Sodium" title="Sodium">sodium</a> yielding <a href="/wiki/Sodium_cyanide" title="Sodium cyanide">sodium cyanide</a>, which reacts with acid to form gaseous HCN. </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=Hydrogen_cyanide&action=edit&section=6" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>HCN is the precursor to <a href="/wiki/Sodium_cyanide" title="Sodium cyanide">sodium cyanide</a> and <a href="/wiki/Potassium_cyanide" title="Potassium cyanide">potassium cyanide</a>, which are used mainly in <a href="/wiki/Gold" title="Gold">gold</a> and <a href="/wiki/Silver" title="Silver">silver</a> mining and for the <a href="/wiki/Electroplating" title="Electroplating">electroplating</a> of those metals. Via the intermediacy of <a href="/wiki/Cyanohydrin" title="Cyanohydrin">cyanohydrins</a>, a variety of useful organic compounds are prepared from HCN including the <a href="/wiki/Monomer" title="Monomer">monomer</a> <a href="/wiki/Methyl_methacrylate" title="Methyl methacrylate">methyl methacrylate</a>, from <a href="/wiki/Acetone" title="Acetone">acetone</a>, the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Methionine" title="Methionine">methionine</a>, via the <a href="/wiki/Strecker_synthesis" class="mw-redirect" title="Strecker synthesis">Strecker synthesis</a>, and the chelating agents <a href="/wiki/EDTA" class="mw-redirect" title="EDTA">EDTA</a> and <a href="/wiki/Nitrilotriacetic_acid" title="Nitrilotriacetic acid">NTA</a>. Via the <a href="/wiki/Hydrocyanation" title="Hydrocyanation">hydrocyanation</a> process, HCN is added to <a href="/wiki/Butadiene" title="Butadiene">butadiene</a> to give <a href="/wiki/Adiponitrile" title="Adiponitrile">adiponitrile</a>, a precursor to <a href="/wiki/Nylon" title="Nylon">Nylon-6,6</a>.<sup id="cite_ref-Ullmann_10-2" class="reference"><a href="#cite_note-Ullmann-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>HCN is used globally as a <a href="/wiki/Fumigant" class="mw-redirect" title="Fumigant">fumigant</a> against many species of pest insects that infest food production facilities. Both its efficacy and method of application lead to very small amounts of the fumigant being used compared to other toxic substances used for the same purpose.<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> Using HCN as a fumigant also has less environmental impact, compared to some other fumigants such as <a href="/wiki/Sulfuryl_fluoride" title="Sulfuryl fluoride">sulfuryl fluoride</a>,<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> and <a href="/wiki/Methyl_bromide" class="mw-redirect" title="Methyl bromide">methyl bromide</a>.<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-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_cyanide&action=edit&section=7" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div><p> HCN is obtainable from <a href="/wiki/Fruit" title="Fruit">fruits</a> that have a <a href="/wiki/Endocarp" class="mw-redirect" title="Endocarp">pit</a>, such as <a href="/wiki/Cherry" title="Cherry">cherries</a>, <a href="/wiki/Apricot" title="Apricot">apricots</a>, <a href="/wiki/Apple" title="Apple">apples</a>, and nuts such as <a href="/wiki/Bitter_almonds" class="mw-redirect" title="Bitter almonds">bitter almonds</a>, from which almond oil and extract is made. Many of these pits contain small amounts of <a href="/wiki/Cyanohydrin" title="Cyanohydrin">cyanohydrins</a> such as <a href="/wiki/Mandelonitrile" title="Mandelonitrile">mandelonitrile</a> and <a href="/wiki/Amygdalin" title="Amygdalin">amygdalin</a>, which slowly release hydrogen cyanide.<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><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> One hundred grams of crushed apple seeds can yield about 70 mg of HCN.<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> The roots of <a href="/wiki/Cassava" title="Cassava">cassava</a> plants contain <a href="/wiki/Cyanogenic_glycosides" class="mw-redirect" title="Cyanogenic glycosides">cyanogenic glycosides</a> such as <a href="/wiki/Linamarin" title="Linamarin">linamarin</a>, which decompose into HCN in yields of up to 370 mg per kilogram of fresh root.<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> Some <a href="/wiki/Millipede" title="Millipede">millipedes</a>, such as <i><a href="/wiki/Harpaphe_haydeniana" title="Harpaphe haydeniana">Harpaphe haydeniana</a></i>, <i><a href="/wiki/Desmoxytes_purpurosea" title="Desmoxytes purpurosea">Desmoxytes purpurosea</a></i>, and <i><a href="/wiki/Apheloria" title="Apheloria">Apheloria</a></i> release hydrogen cyanide as a defense mechanism,<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> as do certain insects, such as <a href="/wiki/Zygaenidae" title="Zygaenidae">burnet moths</a> and the larvae of <i><a href="/wiki/Paropsisterna" title="Paropsisterna">Paropsisterna eucalyptus</a></i>.<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> Hydrogen cyanide is contained in the exhaust of vehicles, and in smoke from burning nitrogen-containing <a href="/wiki/Plastic" title="Plastic">plastics</a>.</p><figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:PIA18431-SaturnMoon-Titan-SouthPoleVortex-Cloud-20121129.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c1/PIA18431-SaturnMoon-Titan-SouthPoleVortex-Cloud-20121129.jpg/220px-PIA18431-SaturnMoon-Titan-SouthPoleVortex-Cloud-20121129.jpg" decoding="async" width="220" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c1/PIA18431-SaturnMoon-Titan-SouthPoleVortex-Cloud-20121129.jpg/330px-PIA18431-SaturnMoon-Titan-SouthPoleVortex-Cloud-20121129.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c1/PIA18431-SaturnMoon-Titan-SouthPoleVortex-Cloud-20121129.jpg/440px-PIA18431-SaturnMoon-Titan-SouthPoleVortex-Cloud-20121129.jpg 2x" data-file-width="1203" data-file-height="774" /></a><figcaption>The South Pole Vortex of Saturn's moon <a href="/wiki/Titan_(moon)" title="Titan (moon)">Titan</a> is a giant swirling cloud of HCN (November 29, 2012)</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="On_Titan">On Titan</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_cyanide&action=edit&section=8" title="Edit section: On Titan"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>HCN has been measured in <a href="/wiki/Atmosphere_of_Titan" title="Atmosphere of Titan">Titan's atmosphere</a> by four instruments on the <a href="/wiki/Cassini%E2%80%93Huygens" title="Cassini–Huygens">Cassini space probe</a>, one instrument on <a href="/wiki/Voyager_1" title="Voyager 1">Voyager</a>, and one instrument on Earth.<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> One of these measurements was <i>in situ</i>, where the Cassini spacecraft dipped between 1,000 and 1,100 km (620 and 680 mi) above Titan's surface to collect atmospheric gas for <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a> analysis.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> HCN initially forms in Titan's atmosphere through the reaction of photochemically produced methane and nitrogen radicals which proceed through the H<sub>2</sub>CN intermediate, e.g., (CH<sub>3</sub> + N → H<sub>2</sub>CN + H → HCN + H<sub>2</sub>).<sup id="cite_ref-pearce2020_40-0" class="reference"><a href="#cite_note-pearce2020-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Ultraviolet radiation breaks HCN up into CN + H; however, CN is efficiently recycled back into HCN via the reaction CN + CH<sub>4</sub> → HCN + CH<sub>3</sub>.<sup id="cite_ref-pearce2020_40-1" class="reference"><a href="#cite_note-pearce2020-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="On_the_young_Earth">On the young Earth</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_cyanide&action=edit&section=9" title="Edit section: On the young Earth"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It has been postulated that carbon from a cascade of asteroids (known as the <a href="/wiki/Late_Heavy_Bombardment" title="Late Heavy Bombardment">Late Heavy Bombardment</a>), resulting from interaction of Jupiter and Saturn, blasted the surface of young Earth and reacted with nitrogen in Earth's atmosphere to form HCN.<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> </p> <div class="mw-heading mw-heading3"><h3 id="In_mammals">In mammals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_cyanide&action=edit&section=10" title="Edit section: In mammals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some authors<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Manual_of_Style/Words_to_watch#Unsupported_attributions" title="Wikipedia:Manual of Style/Words to watch"><span title="The material near this tag possibly uses too-vague attribution or weasel words. (December 2020)">who?</span></a></i>]</sup> have shown that <a href="/wiki/Neuron" title="Neuron">neurons</a> can produce hydrogen cyanide upon activation of their <a href="/wiki/Opioid" title="Opioid">opioid</a> <a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">receptors</a> by endogenous or exogenous opioids. They have also shown that neuronal production of HCN activates <a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDA receptors</a> and plays a role in <a href="/wiki/Signal_transduction" title="Signal transduction">signal transduction</a> between neuronal cells (<a href="/wiki/Neurotransmission" title="Neurotransmission">neurotransmission</a>). Moreover, increased endogenous neuronal HCN production under opioids was seemingly needed for adequate opioid <a href="/wiki/Analgesia" class="mw-redirect" title="Analgesia">analgesia</a>, as analgesic action of opioids was attenuated by HCN scavengers. They considered endogenous HCN to be a <a href="/wiki/Neuromodulator" class="mw-redirect" title="Neuromodulator">neuromodulator</a>.<sup id="cite_ref-pmid9369328_43-0" class="reference"><a href="#cite_note-pmid9369328-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p><p>It has also been shown that, while stimulating <a href="/wiki/Muscarinic" class="mw-redirect" title="Muscarinic">muscarinic</a> <a href="/wiki/Cholinergic" title="Cholinergic">cholinergic</a> receptors in cultured <a href="/wiki/Pheochromocytoma" title="Pheochromocytoma">pheochromocytoma</a> cells <i>increases</i> HCN production, in a living organism (<i>in vivo</i>) muscarinic cholinergic stimulation actually <i>decreases</i> HCN production.<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> </p><p><a href="/wiki/Leukocyte" class="mw-redirect" title="Leukocyte">Leukocytes</a> generate HCN during <a href="/wiki/Phagocytosis" title="Phagocytosis">phagocytosis</a>, and can kill <a href="/wiki/Bacteria" title="Bacteria">bacteria</a>, <a href="/wiki/Fungi" class="mw-redirect" title="Fungi">fungi</a>, and other pathogens by generating several different toxic chemicals, one of which is hydrogen cyanide.<sup id="cite_ref-pmid9369328_43-1" class="reference"><a href="#cite_note-pmid9369328-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Vasodilatation" class="mw-redirect" title="Vasodilatation">vasodilatation</a> caused by <a href="/wiki/Sodium_nitroprusside" title="Sodium nitroprusside">sodium nitroprusside</a> has been shown to be mediated not only by NO generation, but also by endogenous cyanide generation, which adds not only toxicity, but also some additional antihypertensive efficacy compared to <a href="/wiki/Nitroglycerine" class="mw-redirect" title="Nitroglycerine">nitroglycerine</a> and other non-cyanogenic nitrates which do not cause blood cyanide levels to rise.<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> </p><p>HCN is a constituent of <a href="/wiki/Tobacco_smoke" title="Tobacco smoke">tobacco smoke</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-heading3"><h3 id="HCN_and_the_origin_of_life">HCN and the origin of life</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_cyanide&action=edit&section=11" title="Edit section: HCN and the origin of life"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydrogen cyanide has been discussed as a precursor to amino acids and nucleic acids, and is proposed to have played a part in the <a href="/wiki/Abiogenesis" title="Abiogenesis">origin of life</a>.<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> Although the relationship of these chemical reactions to the origin of life theory remains speculative, studies in this area have led to discoveries of new pathways to organic compounds derived from the condensation of HCN (e.g. <a href="/wiki/Adenine" title="Adenine">Adenine</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> </p> <div class="mw-heading mw-heading3"><h3 id="In_space">In space</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_cyanide&action=edit&section=12" title="Edit section: In space"><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">See also: <a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a></div> <p>HCN has been detected in the <a href="/wiki/Interstellar_medium" title="Interstellar medium">interstellar medium</a><sup id="cite_ref-Snyder,_Lewis_E.;_Buhl,_David_1971_L47_49-0" class="reference"><a href="#cite_note-Snyder,_Lewis_E.;_Buhl,_David_1971_L47-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> and in the atmospheres of <a href="/wiki/Carbon_star" title="Carbon star">carbon stars</a>.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> Since then, extensive studies have probed formation and destruction pathways of HCN in various environments and examined its use as a tracer for a variety of astronomical species and processes. HCN can be <a href="/wiki/Observation" title="Observation">observed</a> from ground-based <a href="/wiki/Telescope" title="Telescope">telescopes</a> through a number of <a href="/wiki/Atmosphere" title="Atmosphere">atmospheric</a> windows.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> The J=1→0, J=3→2, J= 4→3, and J=10→9 pure <a href="/wiki/Rotational_transition" title="Rotational transition">rotational transitions</a> have all been observed.<sup id="cite_ref-Snyder,_Lewis_E.;_Buhl,_David_1971_L47_49-1" class="reference"><a href="#cite_note-Snyder,_Lewis_E.;_Buhl,_David_1971_L47-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p>HCN is formed in <a href="/wiki/Interstellar_medium" title="Interstellar medium">interstellar</a> clouds through one of two major pathways:<sup id="cite_ref-Boger,_G._I._and_Sternberg,_A._2005_302_54-0" class="reference"><a href="#cite_note-Boger,_G._I._and_Sternberg,_A._2005_302-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> via a neutral-neutral reaction (CH<sub>2</sub> + N → HCN + H) and via <a href="/wiki/Dissociative_recombination" title="Dissociative recombination">dissociative recombination</a> (HCNH<sup>+</sup> + e<sup>−</sup> → HCN + H). The dissociative recombination pathway is dominant by 30%; however, the <a href="/wiki/HCNH%2B" class="mw-redirect" title="HCNH+">HCNH<sup>+</sup></a> must be in its linear form. Dissociative recombination with its structural isomer, H<sub>2</sub>NC<sup>+</sup>, exclusively produces <a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">hydrogen isocyanide</a> (HNC). </p><p>HCN is destroyed in interstellar clouds through a number of mechanisms depending on the location in the cloud.<sup id="cite_ref-Boger,_G._I._and_Sternberg,_A._2005_302_54-1" class="reference"><a href="#cite_note-Boger,_G._I._and_Sternberg,_A._2005_302-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> In <a href="/wiki/Photon-dominated_region" class="mw-redirect" title="Photon-dominated region">photon-dominated regions</a> (PDRs), photodissociation dominates, producing <a href="/wiki/Cyanide" title="Cyanide">CN</a> (HCN + ν → CN + H). At further depths, photodissociation by cosmic rays dominate, producing CN (HCN + cr → CN + H). In the dark core, two competing mechanisms destroy it, forming HCN<sup>+</sup> and HCNH<sup>+</sup> (HCN + H<sup>+</sup> → HCN<sup>+</sup> + H; HCN + HCO<sup>+</sup> → HCNH<sup>+</sup> + CO). The reaction with HCO<sup>+</sup> dominates by a factor of ~3.5. HCN has been used to analyze a variety of species and processes in the interstellar medium. It has been suggested as a tracer for dense molecular gas<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> and as a tracer of stellar inflow in high-mass star-forming regions.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> Further, the HNC/HCN ratio has been shown to be an excellent method for distinguishing between PDRs and X-ray-dominated regions (XDRs).<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p><p>On 11 August 2014, astronomers released studies, using the <a href="/wiki/Atacama_Large_Millimeter_Array" title="Atacama Large Millimeter Array">Atacama Large Millimeter/Submillimeter Array (ALMA)</a> for the first time, that detailed the distribution of HCN, <a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">HNC</a>, <a href="/wiki/Formaldehyde" title="Formaldehyde">H<sub>2</sub>CO</a>, and <a href="/wiki/Dust" title="Dust">dust</a> inside the <a href="/wiki/Coma_(cometary)" class="mw-redirect" title="Coma (cometary)">comae</a> of <a href="/wiki/Comet" title="Comet">comets</a> <a href="/wiki/C/2012_F6_(Lemmon)" title="C/2012 F6 (Lemmon)">C/2012 F6 (Lemmon)</a> and <a href="/wiki/Comet_ISON" title="Comet ISON">C/2012 S1 (ISON)</a>.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p><p>In February 2016, it was announced that traces of hydrogen cyanide were found in the atmosphere of the hot <a href="/wiki/Super-Earth" title="Super-Earth">Super-Earth</a> <a href="/wiki/55_Cancri_e" title="55 Cancri e">55 Cancri e</a> with NASA's <a href="/wiki/Hubble_Space_Telescope" title="Hubble Space Telescope">Hubble Space Telescope</a>.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p><p>On 14 December 2023, astronomers reported the first time discovery, in the <a href="/wiki/Plume_(fluid_dynamics)" title="Plume (fluid dynamics)">plumes</a> of <a href="/wiki/Enceladus" title="Enceladus">Enceladus</a>, moon of the planet <a href="/wiki/Saturn" title="Saturn">Saturn</a>, of hydrogen cyanide, a possible chemical essential for <a href="/wiki/Life" title="Life">life</a><sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> as we know it, as well as other <a href="/wiki/Organic_molecule" class="mw-redirect" title="Organic molecule">organic molecules</a>, some of which are yet to be better identified and understood. According to the researchers, "these [newly discovered] compounds could potentially support extant <a href="/wiki/Microorganism" title="Microorganism">microbial communities</a> or drive complex <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a> leading to the <a href="/wiki/Origin_of_life" class="mw-redirect" title="Origin of life">origin of life</a>."<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="As_a_poison_and_chemical_weapon">As a poison and chemical weapon</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_cyanide&action=edit&section=13" title="Edit section: As a poison and chemical weapon"><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>In <a href="/wiki/World_War_I" title="World War I">World War I</a>, hydrogen cyanide was used by the French from 1916 as a chemical weapon against the <a href="/wiki/Central_Powers" title="Central Powers">Central Powers</a>, and by the United States and <a href="/wiki/Kingdom_of_Italy" title="Kingdom of Italy">Italy</a> in 1918. It was not found to be effective enough due to weather conditions.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> The gas is lighter than air and rapidly disperses up into the atmosphere. Rapid dilution made its use in the field impractical. In contrast, denser agents such as <a href="/wiki/Phosgene" title="Phosgene">phosgene</a> or <a href="/wiki/Chlorine" title="Chlorine">chlorine</a> tended to remain at ground level and sank into the <a href="/wiki/Trench_warfare" title="Trench warfare">trenches</a> of the Western Front's battlefields. Compared to such agents, hydrogen cyanide had to be present in higher concentrations in order to be fatal. </p><p>A hydrogen cyanide concentration of 100–200 <a href="/wiki/Parts_per_million" class="mw-redirect" title="Parts per million">ppm</a> in breathing air will kill a human within 10 to 60 minutes.<sup id="cite_ref-cyanidecode1_67-0" class="reference"><a href="#cite_note-cyanidecode1-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> A hydrogen cyanide concentration of 2000 ppm (about 2380 mg/m<sup>3</sup>) will kill a human in about one minute.<sup id="cite_ref-cyanidecode1_67-1" class="reference"><a href="#cite_note-cyanidecode1-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> The toxic effect is caused by the action of the cyanide ion, which halts <a href="/wiki/Cellular_respiration" title="Cellular respiration">cellular respiration</a>. It acts as a <a href="/wiki/Non-competitive_inhibitor" class="mw-redirect" title="Non-competitive inhibitor">non-competitive inhibitor</a> for an enzyme in mitochondria called <a href="/wiki/Cytochrome_c_oxidase" title="Cytochrome c oxidase">cytochrome c oxidase</a>. As such, hydrogen cyanide is commonly listed among <a href="/wiki/Chemical_weapons" class="mw-redirect" title="Chemical weapons">chemical weapons</a> as a <a href="/wiki/Blood_agent" title="Blood agent">blood agent</a>.<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Chemical_Weapons_Convention" title="Chemical Weapons Convention">Chemical Weapons Convention</a> lists it under <a href="/wiki/List_of_Schedule_3_substances_(CWC)" title="List of Schedule 3 substances (CWC)">Schedule 3</a> as a potential weapon which has large-scale industrial uses. Signatory countries must declare manufacturing plants that produce more than 30 metric tons per year, and allow inspection by the <a href="/wiki/Organisation_for_the_Prohibition_of_Chemical_Weapons" title="Organisation for the Prohibition of Chemical Weapons">Organisation for the Prohibition of Chemical Weapons</a>. </p><p>Perhaps its most infamous use is <span title="German-language text"><i lang="de"><a href="/wiki/Zyklon_B" title="Zyklon B">Zyklon B</a></i></span> (German: <i>Cyclone B</i>, with the <b>B</b> standing for <span title="German-language text"><i lang="de">Blausäure</i></span> – prussic acid; also, to distinguish it from an earlier product later known as Zyklon A),<sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> used in <a href="/wiki/Nazi_Germany" title="Nazi Germany">Nazi German</a> <a href="/wiki/Extermination_camps" class="mw-redirect" title="Extermination camps">extermination camps</a> during <a href="/wiki/World_War_II" title="World War II">World War II</a> to kill Jews and other persecuted minorities <i>en masse</i> as part of their <a href="/wiki/Final_Solution" title="Final Solution">Final Solution</a> genocide program. Hydrogen cyanide was also used in the camps for delousing clothing in attempts to eradicate diseases carried by lice and other parasites. One of the original Czech producers continued making Zyklon B under the trademark "Uragan D2"<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> until around 2015.<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> </p><p>During <a href="/wiki/World_War_II" title="World War II">World War II</a>, the US considered using it, along with <a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">cyanogen chloride</a>, as part of <a href="/wiki/Operation_Downfall" title="Operation Downfall">Operation Downfall</a>, the planned invasion of Japan, but President <a href="/wiki/Harry_Truman" class="mw-redirect" title="Harry Truman">Harry Truman</a> decided against it, instead using the atomic bombs developed by the secret <a href="/wiki/Manhattan_Project" title="Manhattan Project">Manhattan Project</a>.<sup id="cite_ref-72" class="reference"><a href="#cite_note-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> </p><p>Hydrogen cyanide was also the agent employed in judicial <a href="/wiki/Capital_punishment_in_the_United_States" title="Capital punishment in the United States">execution</a> in some <a href="/wiki/U.S._state" title="U.S. state">U.S. states</a>, where it was produced during the execution by the action of <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> on <a href="/wiki/Sodium_cyanide" title="Sodium cyanide">sodium cyanide</a> or <a href="/wiki/Potassium_cyanide" title="Potassium cyanide">potassium cyanide</a>.<sup id="cite_ref-73" class="reference"><a href="#cite_note-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> </p><p>Under the name <i>prussic acid</i>, HCN has been used as a killing agent in <a href="/wiki/Whaling" title="Whaling">whaling</a> harpoons, although it proved quite dangerous to the crew deploying it, and it was quickly abandoned.<sup id="cite_ref-irons_13-1" class="reference"><a href="#cite_note-irons-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> From the middle of the 18th century it was used in a number of poisoning murders and suicides.<sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> </p><p>Hydrogen cyanide gas in air is explosive at concentrations above 5.6%.<sup id="cite_ref-75" class="reference"><a href="#cite_note-75"><span class="cite-bracket">[</span>75<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=Hydrogen_cyanide&action=edit&section=14" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=18407">"hydrogen cyanide (CHEBI:18407)"</a>. <i>Chemical Entities of Biological Interest</i>. 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World Health Organization. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9241530618" title="Special:BookSources/9241530618"><bdi>9241530618</bdi></a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1020-6167">1020-6167</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=report&rft.btitle=Hydrogen+cyanide+and+cyanides+%3A+human+health+aspects&rft.pub=World+Health+Organization&rft.date=2004&rft.issn=1020-6167&rft.isbn=9241530618&rft.aulast=Simeonova&rft.aufirst=Fina+Petrova&rft.au=Fishbein%2C+Lawrence&rft_id=https%3A%2F%2Firis.who.int%2Fhandle%2F10665%2F42942&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrogen+cyanide" class="Z3988"></span></span> </li> <li id="cite_note-Haynes-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Haynes_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Haynes_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Haynes_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Haynes_4-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Haynes_4-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Haynes_4-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHaynes,_William_M.2011" class="citation book cs1">Haynes, William M., ed. (2011). <a href="/wiki/CRC_Handbook_of_Chemistry_and_Physics" title="CRC Handbook of Chemistry and Physics"><i>CRC Handbook of Chemistry and Physics</i></a> (92nd ed.). <a href="/wiki/CRC_Press" title="CRC Press">CRC Press</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1439855119" title="Special:BookSources/978-1439855119"><bdi>978-1439855119</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&rft.edition=92nd&rft.pub=CRC+Press&rft.date=2011&rft.isbn=978-1439855119&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrogen+cyanide" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEvans" class="citation web cs1">Evans DA. <a rel="nofollow" class="external text" href="http://ccc.chem.pitt.edu/wipf/MechOMs/evans_pKa_table.pdf">"pKa's of Inorganic and Oxo-Acids"</a> <span class="cs1-format">(PDF)</span>. <a rel="nofollow" class="external text" href="https://ghostarchive.org/archive/20221009/http://ccc.chem.pitt.edu/wipf/MechOMs/evans_pKa_table.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 2022-10-09<span class="reference-accessdate">. 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"<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, 5pp. (PDF file, <i>in French</i>)</li> <li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0492.htm">International Chemical Safety Card 0492</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="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="https://www.cdc.gov/niosh/npg/npgd0333.html">NIOSH Pocket Guide to Chemical Hazards</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110607130633/http://www.hpa.org.uk/infections/topics_az/deliberate_release/chemicals/cyanide.pdf#search=%22%22dicobalt%20edetate%22%22">Department of health review</a></li> <li><a rel="nofollow" class="external text" href="https://www.aqua-calc.com/page/density-table/substance/hydrogen-blank-cyanide-coma-and-blank-gas">Density of Hydrogen Cyanide gas</a></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 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space"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Molecules_detected_in_outer_space" title="Template talk:Molecules detected in outer space"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Molecules_detected_in_outer_space" title="Special:EditPage/Template:Molecules detected in outer space"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Molecules_detected_in_outer_space" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules" title="List of interstellar and circumstellar molecules">Molecules detected in outer space</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecule" title="Molecule">Molecules</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%"><a href="/wiki/Diatomic_molecule" title="Diatomic molecule">Diatomic</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/Aluminium_monochloride" title="Aluminium monochloride">Aluminium monochloride</a></li> <li><a href="/wiki/Aluminium_monofluoride" title="Aluminium monofluoride">Aluminium monofluoride</a></li> <li><a href="/wiki/Aluminium(II)_oxide" title="Aluminium(II) oxide">Aluminium(II) oxide</a></li> <li><a href="/wiki/Argonium" title="Argonium">Argonium</a></li> <li><a href="/wiki/Carbon_cation" class="mw-redirect" title="Carbon cation">Carbon cation</a></li> <li><a href="/wiki/Carbon_monophosphide" title="Carbon monophosphide">Carbon monophosphide</a></li> <li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">Carbon monosulfide</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Cyano_radical" title="Cyano radical">Cyano radical</a></li> <li><a href="/wiki/Diatomic_carbon" title="Diatomic carbon">Diatomic carbon</a></li> <li><a href="/w/index.php?title=Fluoromethylidynium&action=edit&redlink=1" class="new" title="Fluoromethylidynium (page does not exist)">Fluoromethylidynium</a></li> <li><a href="/wiki/Helium_hydride_ion" title="Helium hydride ion">Helium hydride ion</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">Hydrogen chloride</a></li> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">Hydrogen fluoride</a></li> <li><a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a> (molecular)</li> <li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">Hydroxyl radical</a></li> <li><a href="/wiki/Iron(II)_oxide" title="Iron(II) oxide">Iron(II) oxide</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">Magnesium monohydride</a></li> <li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">Methylidyne radical</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> (molecular)</li> <li><a href="/wiki/Imidogen" title="Imidogen">Imidogen</a></li> <li><a href="/wiki/Sulfur_mononitride" title="Sulfur mononitride">Sulfur mononitride</a></li> <li><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a> (molecular)</li> <li><a href="/wiki/Phosphorus_monoxide" title="Phosphorus monoxide">Phosphorus monoxide</a></li> <li><a href="/wiki/Phosphorus_mononitride" title="Phosphorus mononitride">Phosphorus mononitride</a></li> <li><a href="/wiki/Potassium_chloride" title="Potassium chloride">Potassium chloride</a></li> <li><a href="/wiki/Silicon_carbide" title="Silicon carbide">Silicon carbide</a></li> <li><a href="/wiki/Silicon_monoxide" title="Silicon monoxide">Silicon monoxide</a></li> <li><a href="/wiki/Silicon_monosulfide" title="Silicon monosulfide">Silicon monosulfide</a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Sodium chloride</a></li> <li><a href="/wiki/Sodium_iodide" title="Sodium iodide">Sodium iodide</a></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">Sulfanyl</a></li> <li><a href="/wiki/Sulfur_monoxide" title="Sulfur monoxide">Sulfur monoxide</a></li> <li><a href="/wiki/Titanium(II)_oxide" title="Titanium(II) oxide">Titanium(II) oxide</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="9" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/Nitrous_oxide" title="Nitrous oxide"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/60px-Nitrous-oxide-3D-balls.png" decoding="async" width="60" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/90px-Nitrous-oxide-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/120px-Nitrous-oxide-3D-balls.png 2x" data-file-width="1100" data-file-height="441" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Ethanol" title="Ethanol"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/60px-Ethanol-3D-balls.png" decoding="async" width="60" height="41" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/90px-Ethanol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/120px-Ethanol-3D-balls.png 2x" data-file-width="1100" data-file-height="754" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/60px-Buckminsterfullerene-perspective-3D-balls.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/90px-Buckminsterfullerene-perspective-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 2x" data-file-width="1056" data-file-height="1100" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triatomic_molecule" title="Triatomic molecule">Triatomic</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/Aluminium(I)_hydroxide" class="mw-redirect" title="Aluminium(I) hydroxide">Aluminium(I) hydroxide</a></li> <li><a href="/w/index.php?title=Aluminium_isocyanide&action=edit&redlink=1" class="new" title="Aluminium isocyanide (page does not exist)">Aluminium isocyanide</a></li> <li><a href="/wiki/Amino_radical" title="Amino radical">Amino radical</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide</a></li> <li><a href="/w/index.php?title=CCP_radical&action=edit&redlink=1" class="new" title="CCP radical (page does not exist)">CCP radical</a></li> <li><a href="/wiki/Halonium_ion" title="Halonium ion">Chloronium</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">Diazenylium</a></li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">Dicarbon monoxide</a></li> <li><a href="/w/index.php?title=Disilicon_carbide&action=edit&redlink=1" class="new" title="Disilicon carbide (page does not exist)">Disilicon carbide</a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">Ethynyl radical</a></li> <li><a href="/w/index.php?title=Formyl_radical&action=edit&redlink=1" class="new" title="Formyl radical (page does not exist)">Formyl radical</a></li> <li><a class="mw-selflink selflink">Hydrogen cyanide</a> (HCN)</li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a> (HNC)</li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">Hydroperoxyl</a></li> <li><a href="/w/index.php?title=Iron_cyanide&action=edit&redlink=1" class="new" title="Iron cyanide (page does not exist)">Iron cyanide</a></li> <li><a href="/w/index.php?title=Isoformyl&action=edit&redlink=1" class="new" title="Isoformyl (page does not exist)">Isoformyl</a></li> <li><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide">Magnesium cyanide</a></li> <li><a href="/w/index.php?title=Magnesium_isocyanide&action=edit&redlink=1" class="new" title="Magnesium isocyanide (page does not exist)">Magnesium isocyanide</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>H<sup>+</sup></a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl</a></li> <li><a href="/wiki/Ozone" title="Ozone">Ozone</a></li> <li><a href="/wiki/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li> <li><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">Sodium cyanide</a></li> <li><a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">Sodium hydroxide</a></li> <li><a href="/w/index.php?title=Silicon_carbonitride&action=edit&redlink=1" class="new" title="Silicon carbonitride (page does not exist)">Silicon carbonitride</a></li> <li><a href="/w/index.php?title=C-Silicon_dicarbide&action=edit&redlink=1" class="new" title="C-Silicon dicarbide (page does not exist)">c-Silicon dicarbide</a></li> <li><a href="/w/index.php?title=SiNC&action=edit&redlink=1" class="new" title="SiNC (page does not exist)">SiNC</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/w/index.php?title=Thioformyl&action=edit&redlink=1" class="new" title="Thioformyl (page does not exist)">Thioformyl</a></li> <li><a href="/wiki/Thioxoethenylidene" title="Thioxoethenylidene">Thioxoethenylidene</a></li> <li><a href="/wiki/Titanium_dioxide" title="Titanium dioxide">Titanium dioxide</a></li> <li><a href="/wiki/Tricarbon" title="Tricarbon">Tricarbon</a></li> <li><a href="/wiki/Water" title="Water">Water</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Four<br />atoms</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/Acetylene" title="Acetylene">Acetylene</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Cyanoethynyl</a></li> <li><a href="/wiki/Interstellar_formaldehyde" title="Interstellar formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Fulminic acid</a></li> <li><a href="/w/index.php?title=HCCN&action=edit&redlink=1" class="new" title="HCCN (page does not exist)">HCCN</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/w/index.php?title=Hydromagnesium_isocyanide&action=edit&redlink=1" class="new" title="Hydromagnesium isocyanide (page does not exist)">Hydromagnesium isocyanide</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Isothiocyanic acid</a></li> <li><a href="/w/index.php?title=Ketenyl&action=edit&redlink=1" class="new" title="Ketenyl (page does not exist)">Ketenyl</a></li> <li><a href="/w/index.php?title=Methylene_amidogen&action=edit&redlink=1" class="new" title="Methylene amidogen (page does not exist)">Methylene amidogen</a></li> <li><a href="/wiki/Methyl_cation" class="mw-redirect" title="Methyl cation">Methyl cation</a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">Methyl radical</a></li> <li><a href="/wiki/Propynylidyne" title="Propynylidyne">Propynylidyne</a></li> <li><a href="/w/index.php?title=Protonated_carbon_dioxide&action=edit&redlink=1" class="new" title="Protonated carbon dioxide (page does not exist)">Protonated carbon dioxide</a></li> <li><a href="/wiki/Protonated_hydrogen_cyanide" title="Protonated hydrogen cyanide">Protonated hydrogen cyanide</a></li> <li><a href="/w/index.php?title=Silicon_tricarbide&action=edit&redlink=1" class="new" title="Silicon tricarbide (page does not exist)">Silicon tricarbide</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Five<br />atoms</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/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Polyyne" title="Polyyne">Butadiynyl</a></li> <li><a href="/wiki/Carbodiimide" title="Carbodiimide">Carbodiimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li> <li><a href="/wiki/Cyanoacetylene" title="Cyanoacetylene">Cyanoacetylene</a></li> <li><a href="/w/index.php?title=Cyanoformaldehyde&action=edit&redlink=1" class="new" title="Cyanoformaldehyde (page does not exist)">Cyanoformaldehyde</a></li> <li><a href="/wiki/Cyanomethyl" title="Cyanomethyl">Cyanomethyl</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a></li> <li><a href="/w/index.php?title=Isocyanoacetylene&action=edit&redlink=1" class="new" title="Isocyanoacetylene (page does not exist)">Isocyanoacetylene</a></li> <li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li> <li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy radical</a></li> <li><a href="/w/index.php?title=Methylenimine&action=edit&redlink=1" class="new" title="Methylenimine (page does not exist)">Methylenimine</a></li> <li><a href="/w/index.php?title=Propadienylidene&action=edit&redlink=1" class="new" title="Propadienylidene (page does not exist)">Propadienylidene</a></li> <li><a href="/w/index.php?title=Protonated_formaldehyde&action=edit&redlink=1" class="new" title="Protonated formaldehyde (page does not exist)">Protonated formaldehyde</a></li> <li><a href="/wiki/Silane" title="Silane">Silane</a></li> <li><a href="/w/index.php?title=Silicon-carbide_cluster&action=edit&redlink=1" class="new" title="Silicon-carbide cluster (page does not exist)">Silicon-carbide cluster</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Six<br />atoms</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/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/w/index.php?title=Cyanobutadiynyl_radical&action=edit&redlink=1" class="new" title="Cyanobutadiynyl radical (page does not exist)">Cyanobutadiynyl radical</a></li> <li><a href="/w/index.php?title=E-Cyanomethanimine&action=edit&redlink=1" class="new" title="E-Cyanomethanimine (page does not exist)">E-Cyanomethanimine</a></li> <li><a href="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Formamide" title="Formamide">Formamide</a></li> <li><a href="/w/index.php?title=HC4N&action=edit&redlink=1" class="new" title="HC4N (page does not exist)">HC<sub>4</sub>N</a></li> <li><a href="/wiki/Ketenimine" class="mw-redirect" title="Ketenimine">Ketenimine</a></li> <li><a href="/wiki/Methanethiol" title="Methanethiol">Methanethiol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methyl_isocyanide" title="Methyl isocyanide">Methyl isocyanide</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Pentynylidyne</a></li> <li><a href="/wiki/Propynal" class="mw-redirect" title="Propynal">Propynal</a></li> <li><a href="/w/index.php?title=Protonated_cyanoacetylene&action=edit&redlink=1" class="new" title="Protonated cyanoacetylene (page does not exist)">Protonated cyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Seven<br />atoms</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/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Acrylonitrile" title="Acrylonitrile">Acrylonitrile</a> <ul><li><a href="/wiki/Vinyl_cyanide" class="mw-redirect" title="Vinyl cyanide">Vinyl cyanide</a></li></ul></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodiacetylene</a></li> <li><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Hexatriynyl_radical" title="Hexatriynyl radical">Hexatriynyl radical</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">Vinyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Eight<br />atoms</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/Acetic_acid" title="Acetic acid">Acetic acid</a></li> <li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li> <li><a href="/w/index.php?title=Cyanoallene&action=edit&redlink=1" class="new" title="Cyanoallene (page does not exist)">Cyanoallene</a></li> <li><a href="/wiki/Ethanimine" title="Ethanimine">Ethanimine</a></li> <li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Hexapentaenylidene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Nine<br />atoms</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/Acetamide" title="Acetamide">Acetamide</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanohexatriyne</a></li> <li><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</a></li> <li><a href="/wiki/Octatetraynyl_radical" title="Octatetraynyl radical">Octatetraynyl radical</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Ten<br />atoms<br />or more</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/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Benzonitrile" title="Benzonitrile">Benzonitrile</a></li> <li><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene">Buckminsterfullerene</a> (C<sub>60</sub>, C<sub>60</sub><sup>+</sup>, fullerene, buckyball)</li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C<sub>70</sub> fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Methyl-cyano-diacetylene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyltriacetylene</a></li> <li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li> <li><a href="/wiki/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li> <li><a href="/w/index.php?title=Heptatrienyl_radical&action=edit&redlink=1" class="new" title="Heptatrienyl radical (page does not exist)">Heptatrienyl radical</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deuterium" title="Deuterium">Deuterated</a><br />molecules</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/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Interstellar_formaldehyde#Interstellar_reactions" title="Interstellar formaldehyde">Formyl radical</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">Heavy water</a></li> <li><a class="mw-selflink selflink">Hydrogen cyanide</a></li> <li><a href="/wiki/Hydrogen_deuteride" title="Hydrogen deuteride">Hydrogen deuteride</a></li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Unconfirmed</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/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</a></li> <li><a href="/wiki/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/w/index.php?title=H2NCO%2B&action=edit&redlink=1" class="new" title="H2NCO+ (page does not exist)">H<sub>2</sub>NCO<sup>+</sup></a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene cation</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Silylidyne" title="Silylidyne">Silylidyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#See_also" title="List of interstellar and circumstellar molecules">Related</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/Abiogenesis" title="Abiogenesis">Abiogenesis</a></li> <li><a href="/wiki/Astrobiology" title="Astrobiology">Astrobiology</a></li> <li><a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a></li> <li><a href="/wiki/Atomic_and_molecular_astrophysics" title="Atomic and molecular astrophysics">Atomic and molecular astrophysics</a></li> <li><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></li> <li><a href="/wiki/Circumstellar_dust" title="Circumstellar dust">Circumstellar dust</a></li> <li><a href="/wiki/Circumstellar_envelope" title="Circumstellar envelope">Circumstellar envelope</a></li> <li><a href="/wiki/Cosmic_dust" title="Cosmic dust">Cosmic dust</a></li> <li><a href="/wiki/Cosmic_ray" title="Cosmic ray">Cosmic ray</a></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a></li> <li><a href="/wiki/Diffuse_interstellar_band" class="mw-redirect" title="Diffuse interstellar band">Diffuse interstellar band</a></li> <li><a href="/wiki/Earliest_known_life_forms" title="Earliest known life forms">Earliest known life forms</a></li> <li><a href="/wiki/Extraterrestrial_life" title="Extraterrestrial life">Extraterrestrial life</a></li> <li><a href="/wiki/Extraterrestrial_liquid_water" title="Extraterrestrial liquid water">Extraterrestrial liquid water</a></li> <li><a href="/wiki/Forbidden_mechanism" title="Forbidden mechanism">Forbidden mechanism</a></li> <li><a href="/wiki/Homochirality" title="Homochirality">Homochirality</a></li> <li><a href="/wiki/Intergalactic_dust" title="Intergalactic dust">Intergalactic dust</a></li> <li><a href="/wiki/Interplanetary_medium" title="Interplanetary medium">Interplanetary medium</a></li> <li><a href="/wiki/Interstellar_medium" title="Interstellar medium">Interstellar medium</a></li> <li><a href="/wiki/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a href="/wiki/Iron%E2%80%93sulfur_world_theory" class="mw-redirect" title="Iron–sulfur world theory">Iron–sulfur world theory</a></li> <li><a href="/wiki/Kerogen" title="Kerogen">Kerogen</a></li> <li><a href="/wiki/Molecules_in_stars" title="Molecules in stars">Molecules in stars</a></li> <li><a href="/wiki/Nexus_for_Exoplanet_System_Science" title="Nexus for Exoplanet System Science">Nexus for Exoplanet System Science</a></li> <li><a href="/wiki/Organic_compound" title="Organic compound">Organic compound</a></li> <li><a href="/wiki/Outer_space" title="Outer space">Outer space</a></li> <li><a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">PAH world hypothesis</a></li> <li><a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</li> <li><a href="/wiki/RNA_world_hypothesis" class="mw-redirect" title="RNA world hypothesis">RNA world hypothesis</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Tholin" title="Tholin">Tholin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight: bold;"><div> <ul><li><b><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Astrochemistry" title="Category:Astrochemistry">Category:Astrochemistry</a></b></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/16px-Earth-moon.jpg" decoding="async" 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<li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/16px-Papapishu-Lab-icon-6.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/24px-Papapishu-Lab-icon-6.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/32px-Papapishu-Lab-icon-6.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span> </span><a href="/wiki/Portal:Chemistry" title="Portal:Chemistry">Chemistry portal</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:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Agents_used_in_chemical_warfareincapacitationriot_control" 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:Chemical_agents" title="Template:Chemical agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemical_agents" title="Template talk:Chemical agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemical_agents" title="Special:EditPage/Template:Chemical agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Agents_used_in_chemical_warfareincapacitationriot_control" style="font-size:114%;margin:0 4em"><div class="hlist"><ul><li>Agents used in <a href="/wiki/Chemical_warfare" title="Chemical warfare">chemical warfare</a></li><li><a href="/wiki/Incapacitating_agent" title="Incapacitating agent">incapacitation</a></li><li><a href="/wiki/Riot_control" title="Riot control">riot control</a></li></ul></div></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Blood_agent" title="Blood agent">Blood agents</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/Cyanogen" title="Cyanogen">Cyanogen</a></li> <li><a href="/wiki/Cyanogen_bromide" title="Cyanogen bromide">Cyanogen bromide</a></li> <li><a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">Cyanogen chloride</a> (CK)</li> <li><a class="mw-selflink selflink">Hydrogen cyanide</a> (AC)</li> <li><a href="/wiki/Arsine" title="Arsine">Arsine</a></li> <li><a href="/wiki/Cacodyl_cyanide" title="Cacodyl cyanide">Cacodyl cyanide</a></li> <li><a href="/wiki/Cacodyl_oxide" title="Cacodyl oxide">Cacodyl oxide</a></li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Phosphorus_trifluoride" title="Phosphorus trifluoride">Phosphorus trifluoride</a></li> <li><a href="/wiki/Methyl_cyanoformate" title="Methyl cyanoformate">Methyl cyanoformate</a></li> <li><a href="/wiki/Iron_pentacarbonyl" title="Iron pentacarbonyl">Iron pentacarbonyl</a></li> <li><a href="/wiki/Nickel_tetracarbonyl" title="Nickel tetracarbonyl">Nickel tetracarbonyl</a></li> <li><a href="/wiki/2,3,7,8-Tetrachlorodibenzodioxin" title="2,3,7,8-Tetrachlorodibenzodioxin">2,3,7,8-Tetrachlorodibenzodioxin</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Lactonitrile" title="Lactonitrile">Lactonitrile</a></li> <li><a href="/wiki/Acetone_cyanohydrin" title="Acetone cyanohydrin">Acetone cyanohydrin</a></li> <li><a href="/wiki/Stibine" title="Stibine">Stibine</a></li> <li><a href="/wiki/Chloral_cyanohydrin" title="Chloral cyanohydrin">Chloral cyanohydrin</a></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Blister_agent" title="Blister agent">Blister agents</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%"><a href="/wiki/Arsenical" title="Arsenical">Arsenicals</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/Ethyldichloroarsine" title="Ethyldichloroarsine">Ethyldichloroarsine</a> (ED)</li> <li><a href="/wiki/Methyldichloroarsine" title="Methyldichloroarsine">Methyldichloroarsine</a> (MD)</li> <li><a href="/wiki/Phenyldichloroarsine" title="Phenyldichloroarsine">Phenyldichloroarsine</a> (PD)</li> <li><a href="/wiki/Lewisite" title="Lewisite">Lewisite</a> (L)</li> <li><a href="/wiki/Lewisite_2" title="Lewisite 2">Lewisite 2</a> (L2)</li> <li><a href="/wiki/Lewisite_3" title="Lewisite 3">Lewisite 3</a> (L3)</li> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur_mustard" class="mw-redirect" title="Sulfur mustard">Sulfur mustards</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/Mustard_gas" title="Mustard gas">Levinstein mustard</a> (EA-229)</li> <li><a href="/wiki/O-Mustard" class="mw-redirect" title="O-Mustard">T</a></li> <li><a href="/wiki/Sesquimustard" title="Sesquimustard">Q</a></li> <li><a href="/wiki/2-Chloroethyl_ethyl_sulfide" title="2-Chloroethyl ethyl sulfide">CEES</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">Nitrogen mustards</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/HN1_(nitrogen_mustard)" title="HN1 (nitrogen mustard)">HN1</a></li> <li><a href="/wiki/Chlormethine" title="Chlormethine">HN2</a></li> <li><a href="/wiki/HN3_(nitrogen_mustard)" title="HN3 (nitrogen mustard)">HN3</a></li> <li><a href="/wiki/TL-301" title="TL-301">TL-301</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nettle_agent" title="Nettle agent">Nettle agents</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/Phosgene_oxime" title="Phosgene oxime">Phosgene oxime</a> (CX)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/KB-16" title="KB-16">KB-16</a></li> <li><a href="/wiki/Dibutylchloromethyltin_chloride" title="Dibutylchloromethyltin chloride">Dibutylchloromethyltin chloride</a></li> <li><a href="/wiki/Selenium_oxychloride" class="mw-redirect" title="Selenium oxychloride">Selenium oxychloride</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nerve_agent" title="Nerve agent">Nerve agents</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%"><a href="/wiki/Nerve_agent#G-Series" title="Nerve agent">G-agents</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/Tabun_(nerve_agent)" title="Tabun (nerve agent)">Tabun</a> (GA)</li> <li><a href="/wiki/Sarin" title="Sarin">Sarin (GB)</a></li> <li><a href="/wiki/Chlorosarin" title="Chlorosarin">Chlorosarin</a> (ClGB)</li> <li><a href="/wiki/Thiosarin" title="Thiosarin">Thiosarin</a> (SGB)</li> <li><a href="/wiki/Soman" title="Soman">Soman</a> (GD)</li> <li><a href="/wiki/Chlorosoman" title="Chlorosoman">Chlorosoman</a> (ClGD)</li> <li><a href="/wiki/Ethylsarin" title="Ethylsarin">Ethylsarin</a> (GE)</li> <li><a href="/wiki/GH_(nerve_agent)" title="GH (nerve agent)">GH</a></li> <li><a href="/wiki/Cyclosarin" title="Cyclosarin">Cyclosarin</a> (GF)</li> <li><a href="/wiki/GP_(nerve_agent)" title="GP (nerve agent)">GP</a></li> <li><a href="/wiki/Fluorotabun" title="Fluorotabun">Fluorotabun</a></li> <li><a href="/wiki/EA-1356" title="EA-1356">EA-1356</a></li> <li><a href="/wiki/EA-4352" title="EA-4352">EA-4352</a></li> <li><a href="/wiki/Crotylsarin" title="Crotylsarin">Crotylsarin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nerve_agent#V-Series" title="Nerve agent">V-agents</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/EA-2192" title="EA-2192">EA-2192</a></li> <li><a href="/wiki/EA-3148" title="EA-3148">EA-3148</a></li> <li><a href="/wiki/VE_(nerve_agent)" title="VE (nerve agent)">VE</a></li> <li><a href="/wiki/VG_(nerve_agent)" title="VG (nerve agent)">VG</a></li> <li><a href="/wiki/VM_(nerve_agent)" title="VM (nerve agent)">VM</a></li> <li><a href="/wiki/3,3,5-Trimethylcyclohexyl_3-pyridyl_methylphosphonate" title="3,3,5-Trimethylcyclohexyl 3-pyridyl methylphosphonate">VP</a></li> <li><a href="/wiki/VR_(nerve_agent)" title="VR (nerve agent)">VR</a></li> <li><a href="/wiki/VS_(nerve_agent)" title="VS (nerve agent)">VS</a></li> <li><a href="/wiki/VX_(nerve_agent)" title="VX (nerve agent)">VX</a></li> <li><a href="/wiki/EA-1763" title="EA-1763">EA-1763</a></li> <li><a href="/wiki/Chinese_VX" title="Chinese VX">Chinese VX</a></li> <li><a href="/wiki/V-sub_x" title="V-sub x">V-sub x (GD-7)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">GV agents</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/GV_(nerve_agent)" title="GV (nerve agent)">GV (EA-5365)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Novichok_agent" class="mw-redirect" title="Novichok agent">Novichok agents</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/VR_(nerve_agent)" title="VR (nerve agent)">A-208</a></li> <li><a href="/wiki/A-232" title="A-232">A-232</a></li> <li><a href="/wiki/A-234_(nerve_agent)" title="A-234 (nerve agent)">A-234</a></li> <li><a href="/wiki/A-242" title="A-242">A-242</a></li> <li><a href="/wiki/A-262" title="A-262">A-262</a></li> <li><a href="/wiki/C01-A035" title="C01-A035">C01-A035</a></li> <li><a href="/wiki/C01-A039" title="C01-A039">C01-A039</a></li> <li><a href="/wiki/C01-A042" title="C01-A042">C01-A042</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbamate" title="Carbamate">Carbamates</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/Dimethylcarbamoyl_fluoride" title="Dimethylcarbamoyl fluoride">Dimethylcarbamoyl fluoride</a></li> <li><a href="/wiki/EA-3887" title="EA-3887">EA-3887</a></li> <li><a href="/wiki/EA-3887A" class="mw-redirect" title="EA-3887A">EA-3887A</a></li> <li><a href="/wiki/EA-3966" title="EA-3966">EA-3966</a></li> <li><a href="/wiki/EA-3990" title="EA-3990">EA-3990</a></li> <li><a href="/wiki/EA-4056" title="EA-4056">EA-4056</a></li> <li><a href="/wiki/T-1123" title="T-1123">T-1123</a></li> <li><a href="/wiki/T-1152" title="T-1152">T-1152</a></li> <li><a href="/wiki/T-1194" title="T-1194">T-1194</a></li> <li><a href="/wiki/Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium_bromide)" title="Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)">Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)</a></li> <li><a href="/wiki/TL-599" title="TL-599">TL-599</a></li> <li><a href="/wiki/TL-1238" title="TL-1238">TL-1238</a></li> <li><a href="/wiki/TL-1299" class="mw-redirect" title="TL-1299">TL-1299</a></li> <li><a href="/wiki/TL-1317" class="mw-redirect" title="TL-1317">TL-1317</a></li> <li><a href="/wiki/Miotine" title="Miotine">Miotine (AR-28/T-1843)</a></li> <li><a href="/wiki/3152_CT" title="3152 CT">3152 CT</a></li> <li><a href="/wiki/4-686-293-01" title="4-686-293-01">4-686-293-01 (Agent 1-10)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diisopropyl_fluorophosphate" title="Diisopropyl fluorophosphate">Diisopropyl fluorophosphate</a></li> <li><a href="/wiki/Dicyclohexyl_phosphorofluoridate" title="Dicyclohexyl phosphorofluoridate">Dicyclohexyl phosphorofluoridate</a></li> <li><a href="/wiki/EA-2012" title="EA-2012">EA-2012</a></li> <li><a href="/wiki/EA-2054" title="EA-2054">EA-2054</a></li> <li><a href="/wiki/EA-2098" title="EA-2098">EA-2098</a></li> <li><a href="/wiki/EA-2613" title="EA-2613">EA-2613</a></li> <li><a href="/wiki/2-Ethoxycarbonyl-1-methylvinyl_cyclohexyl_methylphosphonate" title="2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate">2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate</a></li> <li><a href="/wiki/Neopentylene_fluorophosphate" title="Neopentylene fluorophosphate">Neopentylene fluorophosphate</a></li> <li><a href="/wiki/Selenophos" title="Selenophos">Selenophos</a></li> <li><a href="/wiki/Phospholine" class="mw-redirect" title="Phospholine">Phospholine</a></li> <li><a href="/wiki/R-16661" title="R-16661">R-16661</a></li> <li><a href="/wiki/Ro_3-0422" title="Ro 3-0422">Ro 3-0422</a></li> <li><a href="/wiki/Methanesulfonyl_fluoride" title="Methanesulfonyl fluoride">Methanesulfonyl fluoride</a></li> <li><a href="/wiki/Dimefox" title="Dimefox">Dimefox (TL-792)</a></li> <li><a href="/wiki/MSPI_(nerve_agent)" title="MSPI (nerve agent)">MSPI</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Precursors</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/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/wiki/Arsenic_trichloride" title="Arsenic trichloride">AT</a></li> <li><a href="/wiki/Arsenic_trioxide" title="Arsenic trioxide">ATO</a></li> <li><a href="/wiki/Aluminium_phosphide" title="Aluminium phosphide">AlP</a></li> <li><a href="/wiki/Kinnear%E2%80%93Perren_reaction" title="Kinnear–Perren reaction">A.P.C. complex</a></li> <li><a href="/wiki/Chlorosarin" title="Chlorosarin">Chlorosarin</a></li> <li><a href="/wiki/Chlorosoman" title="Chlorosoman">Chlorosoman</a></li> <li><a href="/wiki/Cyclohexanol" title="Cyclohexanol">Cyclohexanol</a></li> <li><a href="/wiki/1,8-Dibromooctane" title="1,8-Dibromooctane">1,8-Dibromooctane</a></li> <li><a href="/wiki/N,N-Diisopropylaminoethanol" title="N,N-Diisopropylaminoethanol">N,N-Diisopropylaminoethanol</a> (KB)</li> <li><a href="/wiki/Diisopropyl_methylphosphonate" title="Diisopropyl methylphosphonate">EA-1250</a></li> <li><a href="/wiki/Diisopropylphosphite" title="Diisopropylphosphite">DIHP</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">ZS</a></li> <li><a href="/wiki/Diethylphosphite" title="Diethylphosphite">DEHP</a></li> <li><a href="/wiki/Dimethyl_methylphosphonate" title="Dimethyl methylphosphonate">EA-1224</a></li> <li><a href="/wiki/Dimethylamidophosphoric_dichloride" title="Dimethylamidophosphoric dichloride">Dimethylamidophosphoric dichloride</a></li> <li><a href="/wiki/Dimethylamidophosphoric_dicyanide" title="Dimethylamidophosphoric dicyanide">Dimethylamidophosphoric dicyanide</a></li> <li><a href="/wiki/Dimethylphosphite" title="Dimethylphosphite">DMHP</a></li> <li><a href="/wiki/Ethylphosphonoselenoic_dichloride" title="Ethylphosphonoselenoic dichloride">Ethylphosphonoselenoic dichloride</a></li> <li><a href="/wiki/Formaldoxime" title="Formaldoxime">Formaldoxime</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Nital</a></li> <li><a href="/wiki/4-Hydroxycoumarin" title="4-Hydroxycoumarin">4-Hydroxycoumarin</a></li> <li><a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">Isopropyl alcohol</a> (TB)</li> <li><a href="/wiki/Methyldichlorophosphine" title="Methyldichlorophosphine">Methyldichlorophosphine</a> (SW)</li> <li><a href="/wiki/Methylphosphonyl_difluoride" title="Methylphosphonyl difluoride">Methylphosphonyl difluoride (difluoro)</a> (DF)</li> <li><a href="/wiki/Methylphosphonyl_dichloride" title="Methylphosphonyl dichloride">Methylphosphonyl dichloride (dichloro)</a></li> <li><a href="/wiki/Nitromethane" title="Nitromethane">Nitromethane</a></li> <li><a href="/wiki/OPA_mixture" title="OPA mixture">OPA mixture</a></li> <li><a href="/wiki/Phosphoryl_chloride" title="Phosphoryl chloride">Phosphoryl chloride</a></li> <li><a href="/wiki/Phosphorus_pentachloride" title="Phosphorus pentachloride">Phosphorus pentachloride</a></li> <li><a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">Phosphorus trichloride</a> (TH)</li> <li><a href="/wiki/Pinacolone" title="Pinacolone">Pinacolone</a></li> <li><a href="/wiki/Pinacolyl_alcohol" title="Pinacolyl alcohol">Pinacolyl alcohol</a></li> <li><a href="/wiki/Phenacyl_chloride" title="Phenacyl chloride">Phenacyl chloride</a></li> <li><a href="/wiki/QL_(chemical)" title="QL (chemical)">QL</a></li> <li><a href="/wiki/2,4,5-Trichlorophenol" title="2,4,5-Trichlorophenol">2,4,5-Trichlorophenol</a></li> <li><a href="/wiki/3,3,5-Trimethylcyclohexanol" title="3,3,5-Trimethylcyclohexanol">3,3,5-Trimethylcyclohexanol</a></li> <li><a href="/wiki/Triethyl_phosphite" title="Triethyl phosphite">Triethyl phosphite</a></li> <li><a href="/wiki/Trimethyl_phosphite" title="Trimethyl phosphite">Trimethyl phosphite</a></li> <li><a href="/wiki/Thionyl_chloride" title="Thionyl chloride">TC</a></li> <li><a href="/wiki/Thiodiglycol" title="Thiodiglycol">TG</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neurotoxin" title="Neurotoxin">Neurotoxins</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/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/Saxitoxin" title="Saxitoxin">Saxitoxin</a> (TZ)</li> <li><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxin</a></li> <li><a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a> (BTX)</li> <li><a href="/wiki/Tetanospasmin" class="mw-redirect" title="Tetanospasmin">Tetanospasmin</a> (TeNT)</li> <li><a href="/wiki/Ryanodine" title="Ryanodine">Ryanodine</a></li> <li><a href="/wiki/Ciguatoxin" title="Ciguatoxin">Ciguatoxin</a> (CTX)</li> <li><a href="/wiki/Guanitoxin" title="Guanitoxin">Guanitoxin</a> (GTX)</li> <li><a href="/wiki/Chlorophenylsilatrane" title="Chlorophenylsilatrane">Chlorophenylsilatrane</a></li> <li><a href="/wiki/Palytoxin" title="Palytoxin">Palytoxin</a> (PTX)</li> <li><a href="/wiki/Maitotoxin" title="Maitotoxin">Maitotoxin</a> (MTX)</li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</a></li> <li><a href="/wiki/Aconitine" title="Aconitine">Aconitine</a></li> <li><a href="/wiki/Brevetoxin" title="Brevetoxin">Brevetoxin</a> (PbTX)</li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Antillatoxin" title="Antillatoxin">Antillatoxin</a> (ATX)</li> <li><a href="/wiki/Tetraethyllead" title="Tetraethyllead">Tetraethyllead</a></li> <li><a href="/wiki/Dimethylmercury" title="Dimethylmercury">Dimethylmercury</a></li> <li><a href="/wiki/HN1_(nitrogen_mustard)" title="HN1 (nitrogen mustard)">HN1 hydrochloride</a></li> <li><a href="/wiki/HN2" class="mw-redirect" title="HN2">HN2 hydrochloride</a></li> <li><a href="/wiki/Tris(2-chloroethyl)amine" class="mw-redirect" title="Tris(2-chloroethyl)amine">HN3 hydrochloride</a></li> <li><a href="/wiki/IDPN_(chemical)" title="IDPN (chemical)">A-8564</a></li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a></li> <li><a href="/wiki/Sulfuryl_fluoride" title="Sulfuryl fluoride">Sulfuryl fluoride</a></li> <li><a href="/wiki/Tremorine" title="Tremorine">Tremorine</a></li> <li><a href="/wiki/Oxotremorine" title="Oxotremorine">Oxotremorine</a></li> <li><a href="/wiki/Batrachotoxin" title="Batrachotoxin">Batrachotoxin</a></li> <li><a href="/wiki/Tetramethylenedisulfotetramine" title="Tetramethylenedisulfotetramine">Tetramethylenedisulfotetramine (TETS)</a></li> <li><a href="/wiki/Bicyclic_phosphate" title="Bicyclic phosphate">Bicyclic phosphates</a> <ul><li><a href="/wiki/IPTBO" title="IPTBO">IPTBO</a></li> <li><a href="/wiki/TBPO" title="TBPO">TBPO</a></li> <li><a href="/wiki/TBPS" title="TBPS">TBPS</a></li></ul></li> <li><a href="/wiki/Cloflubicyne" title="Cloflubicyne">Cloflubicyne</a></li> <li><a href="/wiki/Trimethylolpropane_phosphite" title="Trimethylolpropane phosphite">Trimethylolpropane phosphite</a></li> <li><a href="/wiki/Domoic_acid" title="Domoic acid">Domoic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pulmonary_agent" title="Pulmonary agent">Pulmonary/<br />choking agents</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/Chlorine" title="Chlorine">Chlorine</a></li> <li><a href="/wiki/Bromine" title="Bromine">Bromine</a></li> <li><a href="/wiki/Phosgene" title="Phosgene">Phosgene</a> (CG)</li> <li><a href="/wiki/Fluorine" title="Fluorine">Fluorine</a></li> <li><a href="/wiki/Perfluoroisobutene" title="Perfluoroisobutene">Perfluoroisobutene</a></li> <li><a href="/wiki/Chloropicrin" title="Chloropicrin">Chloropicrin</a> (PS)</li> <li><a href="/wiki/Dimethyl(trifluoromethylthio)arsine" title="Dimethyl(trifluoromethylthio)arsine">Dimethyl(trifluoromethylthio)arsine</a></li> <li><a href="/wiki/Diphosgene" title="Diphosgene">Diphosgene</a> (DP)</li> <li><a href="/wiki/Disulfur_decafluoride" title="Disulfur decafluoride">Disulfur decafluoride</a> (Z)</li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li> <li><a href="/wiki/Ethyl_bromoacetate" title="Ethyl bromoacetate">Ethyl bromoacetate</a></li> <li><a href="/wiki/Perchloromethyl_mercaptan" title="Perchloromethyl mercaptan">Perchloromethyl mercaptan</a></li> <li><a href="/wiki/Phenylcarbylamine_chloride" title="Phenylcarbylamine chloride">Phenylcarbylamine chloride</a></li> <li><a href="/wiki/Tetranitromethane" title="Tetranitromethane">Tetranitromethane</a></li> <li><a href="/wiki/Tetrachlorodinitroethane" title="Tetrachlorodinitroethane">Tetrachlorodinitroethane</a></li> <li><a href="/wiki/Chlorine_trifluoride" title="Chlorine trifluoride">Chlorine trifluoride</a></li> <li><a href="/wiki/Perchloryl_fluoride" title="Perchloryl fluoride">Perchloryl fluoride</a></li> <li><a href="/wiki/Cadmium_oxide" title="Cadmium oxide">Cadmium oxide</a></li> <li><a href="/wiki/Cadmium_chloride" title="Cadmium chloride">Cadmium chloride</a></li> <li><a href="/wiki/Mercury(II)_chloride" title="Mercury(II) chloride">Mercuric chloride</a></li> <li><a href="/wiki/Selenium_dioxide" title="Selenium dioxide">Selenium dioxide</a></li> <li><a href="/wiki/Selenoyl_fluoride" title="Selenoyl fluoride">Selenoyl fluoride</a></li> <li><a href="/wiki/Trifluoronitrosomethane" title="Trifluoronitrosomethane">Trifluoronitrosomethane</a></li> <li><a href="/wiki/Trichloronitrosomethane" title="Trichloronitrosomethane">Trichloronitrosomethane</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">Nitrogen dioxide</a></li> <li><a href="/wiki/Dinitrogen_tetroxide" title="Dinitrogen tetroxide">Dinitrogen tetroxide</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">Phosphorus trichloride</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Ethenone" title="Ethenone">Ethenone</a></li> <li><a href="/wiki/Methyl_vinyl_ketone" title="Methyl vinyl ketone">Methyl vinyl ketone</a></li> <li><a href="/wiki/Trifluoroacetyl_chloride" title="Trifluoroacetyl chloride">Trifluoroacetyl chloride</a></li> <li><a href="/wiki/Salcomine" title="Salcomine">Salcomine</a></li> <li><a href="/wiki/Fluomine" title="Fluomine">Fluomine</a></li> <li><a href="/wiki/Uranium_hexafluoride" title="Uranium hexafluoride">Uranium hexafluoride</a></li> <li><a href="/wiki/Diborane" title="Diborane">Diborane</a></li> <li><a href="/wiki/Green_Cross_(chemical_warfare)" title="Green Cross (chemical warfare)">Green Cross</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vomiting_agent" title="Vomiting agent">Vomiting agents</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/Adamsite" title="Adamsite">Adamsite</a> (DM)</li> <li><a href="/wiki/Chloropicrin" title="Chloropicrin">Chloropicrin</a></li> <li><a href="/wiki/Litharge" title="Litharge">Litharge</a>-<a href="/wiki/Glycerine" class="mw-redirect" title="Glycerine">glycerine</a></li> <li><a href="/wiki/Diphenylchlorarsine" title="Diphenylchlorarsine">Diphenylchlorarsine</a></li> <li><a href="/wiki/Diphenylcyanoarsine" title="Diphenylcyanoarsine">Diphenylcyanoarsine</a></li> <li><a href="/wiki/Cacodyl_cyanide" title="Cacodyl cyanide">Cacodyl cyanide</a></li> <li><a href="/wiki/O-Dianisidine" title="O-Dianisidine">o-Dianisidine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Incapacitating_agent" title="Incapacitating agent">Incapacitating<br />agents</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-Quinuclidinyl_benzilate" title="3-Quinuclidinyl benzilate">BZ</a> (CS-4030)</li> <li><a href="/wiki/Apomorphine" title="Apomorphine">Apomorphine</a></li> <li><a href="/wiki/Butyrophenone" title="Butyrophenone">Butyrophenone</a></li> <li><a href="/wiki/Etonitazene" title="Etonitazene">EA-4941</a> (CS-4640)</li> <li><a href="/wiki/Etorphine" title="Etorphine">Etorphine</a></li> <li><a href="/wiki/Benactyzine" title="Benactyzine">EA-2092</a></li> <li><a href="/wiki/Ditran" title="Ditran">CS-4297</a></li> <li><a href="/wiki/Etoxadrol" title="Etoxadrol">Etoxadrol</a></li> <li><a href="/wiki/Dimethylheptylpyran" title="Dimethylheptylpyran">Dimethylheptylpyran</a> (DMHP)</li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">EA-2148</a></li> <li><a href="/wiki/EA-3167" title="EA-3167">EA-3167</a></li> <li><a href="/wiki/EA-3443" title="EA-3443">EA-3443</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine</a></li> <li><a href="/wiki/EA-3580" title="EA-3580">EA-3580</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/EA-3834" title="EA-3834">EA-3834</a></li> <li><a href="/wiki/Kolokol-1" title="Kolokol-1">Kolokol-1</a></li> <li><a href="/wiki/LSD" title="LSD">LSD-25</a></li> <li><a href="/wiki/PAVA_spray" title="PAVA spray">PAVA spray</a></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">Psilocybin</a></li> <li><a href="/wiki/Incapacitating_agent#Sleeping_gas" title="Incapacitating agent">Sleeping gas</a></li> <li><a href="/wiki/Carfentanil" title="Carfentanil">Carfentanil</a></li> <li><a href="/wiki/N-Ethyl-3-piperidyl_benzilate" title="N-Ethyl-3-piperidyl benzilate">JB-318</a></li> <li><a href="/wiki/N-Methyl-3-piperidyl_benzilate" title="N-Methyl-3-piperidyl benzilate">JB-336</a></li> <li><a href="/wiki/CS-27349" title="CS-27349">CS-27349</a></li> <li><a href="/wiki/CAR-226,086" title="CAR-226,086">CAR-226,086</a></li> <li><a href="/wiki/CAR-301,060" title="CAR-301,060">CAR-301,060</a></li> <li><a href="/wiki/CAR-302,196" title="CAR-302,196">CAR-302,196</a></li> <li><a href="/wiki/CAR-302,282" title="CAR-302,282">CAR-302,282</a></li> <li><a href="/wiki/CAR-302,668" title="CAR-302,668">CAR-302,668</a></li> <li><a href="/wiki/Benperidol" title="Benperidol">Benperidol</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Procarbazine" title="Procarbazine">Procarbazine</a></li> <li><a href="/wiki/Fluphenazine" title="Fluphenazine">Fluphenazine</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tear_gas" title="Tear gas">Lachrymatory<br />agents</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/Xylyl_bromide" title="Xylyl bromide">Xylyl bromide</a></li> <li><a href="/wiki/Pepper_spray" title="Pepper spray">Pepper spray</a> (OC)</li> <li><a href="/wiki/Mace_(spray)" title="Mace (spray)">Mace (spray)</a></li> <li><a href="/wiki/Phenacyl_chloride" title="Phenacyl chloride">CN</a></li> <li><a href="/wiki/CS_gas" title="CS gas">CS</a></li> <li><a href="/wiki/CR_gas" title="CR gas">CR</a></li> <li><a href="/wiki/CNS_(chemical_weapon)" title="CNS (chemical weapon)">CNS</a></li> <li><a href="/wiki/Benzyl_chloride" title="Benzyl chloride">Benzyl chloride</a></li> <li><a href="/wiki/Benzyl_bromide" title="Benzyl bromide">Benzyl bromide</a></li> <li><a href="/wiki/Benzyl_iodide" title="Benzyl iodide">Benzyl iodide</a></li> <li><a href="/wiki/Bromobenzyl_cyanide" title="Bromobenzyl cyanide">Bromobenzyl cyanide</a></li> <li><a href="/wiki/Thiophosgene" title="Thiophosgene">Thiophosgene</a></li> <li><a href="/wiki/Chloroacetone" title="Chloroacetone">Chloroacetone</a></li> <li><a href="/wiki/Bromoacetone" title="Bromoacetone">Bromoacetone</a></li> <li><a href="/wiki/Bromomethyl_ethyl_ketone" title="Bromomethyl ethyl ketone">Bromomethyl ethyl ketone</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li> <li><a href="/wiki/Phenacyl_bromide" title="Phenacyl bromide">Phenacyl bromide</a></li> <li><a href="/wiki/Chloroacetophenone_oxime" title="Chloroacetophenone oxime">Chloroacetophenone oxime</a></li> <li><a href="/wiki/Ethyl_bromoacetate" title="Ethyl bromoacetate">Ethyl bromoacetate</a></li> <li><a href="/wiki/Ethyl_iodoacetate" title="Ethyl iodoacetate">Ethyl iodoacetate</a></li> <li><a href="/wiki/Iodoacetone" title="Iodoacetone">Iodoacetone</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">Allyl isothiocyanate</a></li> <li><a href="/wiki/Hexamethylene_diisocyanate" title="Hexamethylene diisocyanate">Hexamethylene diisocyanate</a></li> <li><a href="/wiki/Crotonaldehyde" title="Crotonaldehyde">Crotonaldehyde</a></li> <li><a href="/wiki/DRC-5593" title="DRC-5593">DRC-5593</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Malodorant" title="Malodorant">Malodorant</a> agents</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/Thioacetone" title="Thioacetone">Thioacetone</a></li> <li><a href="/wiki/Allicin" title="Allicin">Allicin</a></li> <li><a href="/wiki/Skatole" title="Skatole">Skatole</a></li> <li><a href="/wiki/Cadaverine" title="Cadaverine">Cadaverine</a></li> <li><a href="/wiki/Putrescine" title="Putrescine">Putrescine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Cornea-clouding agents</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/Lewisite" title="Lewisite">Lewisite</a></li> <li><a href="/wiki/Phosgene_oxime" title="Phosgene oxime">CX</a></li> <li><a href="/wiki/KB-16" title="KB-16">KB-16</a></li> <li><a href="/wiki/Methyl_cyanoacrylate" title="Methyl cyanoacrylate">Methyl cyanoacrylate</a></li> <li><a href="/wiki/N-Methylmorpholine" title="N-Methylmorpholine">N-Methylmorpholine</a></li> <li><a href="/wiki/Allyl_alcohol" title="Allyl alcohol">Allyl alcohol</a></li> <li><a href="/wiki/Osmium_tetroxide" title="Osmium tetroxide">Osmium tetroxide</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Biological toxins</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/Abrin" title="Abrin">Abrin</a></li> <li><a href="/wiki/Aconitine" title="Aconitine">Aconitine</a></li> <li><a href="/wiki/Cyclopiazonic_acid" title="Cyclopiazonic acid">Cyclopiazonic acid</a></li> <li><a href="/wiki/Histrionicotoxins" title="Histrionicotoxins">Histrionicotoxins</a></li> <li><a href="/wiki/Aflatoxins" class="mw-redirect" title="Aflatoxins">Aflatoxins</a></li> <li><a href="/wiki/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/Batrachotoxin" title="Batrachotoxin">Batrachotoxin</a></li> <li><a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a></li> <li><a href="/wiki/Brevetoxin" title="Brevetoxin">Brevetoxin</a></li> <li><a href="/wiki/Ciguatoxin" title="Ciguatoxin">Ciguatoxin</a></li> <li><a href="/wiki/Domoic_acid" title="Domoic acid">Domoic acid</a></li> <li><a href="/wiki/Enterotoxin_type_B" title="Enterotoxin type B">Enterotoxin type B</a></li> <li><a href="/wiki/Grayanotoxin" title="Grayanotoxin">Grayanotoxin</a></li> <li><a href="/wiki/Guanitoxin" title="Guanitoxin">Guanitoxin</a></li> <li><a href="/wiki/Maitotoxin" title="Maitotoxin">Maitotoxin</a></li> <li><a href="/wiki/Modeccin" title="Modeccin">Modeccin</a></li> <li><a href="/wiki/Palytoxin" title="Palytoxin">Palytoxin</a></li> <li><a href="/wiki/Ricin" title="Ricin">Ricin</a></li> <li><a href="/wiki/Saxitoxin" title="Saxitoxin">Saxitoxin</a></li> <li><a href="/wiki/Shiga_toxin" title="Shiga toxin">Shiga toxin</a></li> <li><a href="/wiki/T-2_mycotoxin" title="T-2 mycotoxin">T-2 mycotoxin</a></li> <li><a href="/wiki/Tetanospasmin" class="mw-redirect" title="Tetanospasmin">Tetanospasmin</a></li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</a></li> <li><a href="/wiki/Volkensin" title="Volkensin">Volkensin</a></li> <li><a href="/wiki/Veratridine" title="Veratridine">Veratridine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methyl_fluoroacetate" title="Methyl fluoroacetate">Methyl fluoroacetate</a></li> <li><a href="/wiki/Napalm" title="Napalm">Napalm</a> (variants and mixtures)</li> <li><a href="/wiki/Fluoroethyl_fluoroacetate" title="Fluoroethyl fluoroacetate">Fluoroethyl fluoroacetate</a></li> <li><a href="/wiki/Depleted_uranium" title="Depleted uranium">Depleted uranium</a> <ul><li>post-combustion <a href="/wiki/Uranium_oxide" title="Uranium oxide">uranium oxides</a></li></ul></li> <li><a href="/wiki/Plutonium" title="Plutonium">Plutonium</a> and <a href="/wiki/Plutonium_compounds" title="Plutonium compounds">its compounds</a></li> <li><a href="/wiki/Polonium" title="Polonium">Polonium</a></li> <li><a href="/wiki/White_phosphorus_munitions" class="mw-redirect" title="White phosphorus munitions">White phosphorus</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><a href="/wiki/List_of_chemical_warfare_agents" title="List of chemical warfare agents">List of chemical warfare agents</a></li> <li><a href="/wiki/CB_military_symbol" title="CB military symbol">CB military symbol</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="Salts_and_covalent_derivatives_of_the_cyanide_ion" style="display:table;;padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit;table-layout:fixed;"><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:Cyanides" title="Template:Cyanides"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cyanides" title="Template talk:Cyanides"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cyanides" title="Special:EditPage/Template:Cyanides"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Salts_and_covalent_derivatives_of_the_cyanide_ion" style="font-size:114%;margin:0 4em">Salts and covalent derivatives of the <a href="/wiki/Cyanide" title="Cyanide">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 class="mw-selflink selflink">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"><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 class="mw-selflink selflink">HCN</a></li> <li><a href="/wiki/Cyanide" title="Cyanide">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"><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 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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"><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"><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"><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="Hydrogen_compounds" 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:Hydrogen_compounds" title="Template:Hydrogen compounds"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hydrogen_compounds" title="Template talk:Hydrogen compounds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hydrogen_compounds" title="Special:EditPage/Template:Hydrogen compounds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Hydrogen_compounds" style="font-size:114%;margin:0 4em"><a href="/wiki/Hydrogen_compounds" title="Hydrogen compounds">Hydrogen compounds</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Arsenous_acid" title="Arsenous acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>AsO<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Arsenic_acid" title="Arsenic acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>AsO<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Argon_fluorohydride" title="Argon fluorohydride">HArF</a></li> <li><a href="/wiki/Hydrogen_astatide" title="Hydrogen astatide">HAt</a></li> <li><a href="/wiki/Fluorosulfuric_acid" title="Fluorosulfuric acid"><span class="chemf nowrap">HSO<sub class="template-chem2-sub">3</sub>F</span></a></li> <li><a href="/wiki/Fluoroboric_acid" title="Fluoroboric acid"><span class="chemf nowrap">H[BF<sub class="template-chem2-sub">4</sub>]</span></a></li> <li><a href="/wiki/Hydrogen_bromide" title="Hydrogen bromide">HBr</a></li> <li><a href="/wiki/Hypobromous_acid" title="Hypobromous acid">HBrO</a></li> <li><a href="/wiki/Bromous_acid" title="Bromous acid"><span class="chemf nowrap">HBrO<sub class="template-chem2-sub">2</sub></span></a></li> <li><a href="/wiki/Bromic_acid" title="Bromic acid"><span class="chemf nowrap">HBrO<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Perbromic_acid" title="Perbromic acid"><span class="chemf nowrap">HBrO<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">HCl</a></li> <li><a href="/wiki/Hypochlorous_acid" title="Hypochlorous acid">HClO</a></li> <li><a href="/wiki/Chlorous_acid" title="Chlorous acid"><span class="chemf nowrap">HClO<sub class="template-chem2-sub">2</sub></span></a></li> <li><a href="/wiki/Chloric_acid" title="Chloric acid"><span class="chemf nowrap">HClO<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Perchloric_acid" title="Perchloric acid"><span class="chemf nowrap">HClO<sub class="template-chem2-sub">4</sub></span></a></li> <li><a class="mw-selflink selflink">HCN</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">HCNO</a></li> <li><a href="/wiki/Chromic_acid" title="Chromic acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>CrO<sub class="template-chem2-sub">4</sub></span>/<span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>Cr<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">7</sub></span></a></li> <li><a href="/wiki/Carbonic_acid" title="Carbonic acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Thiocarbonic_acid" title="Thiocarbonic acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>CS<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">HF</a></li> <li><a href="/wiki/Hypofluorous_acid" title="Hypofluorous acid">HFO</a></li> <li><a href="/wiki/Hydrogen_iodide" title="Hydrogen iodide">HI</a></li> <li><a href="/wiki/Hypoiodous_acid" title="Hypoiodous acid">HIO</a></li> <li><a href="/wiki/Iodous_acid" title="Iodous acid"><span class="chemf nowrap">HIO<sub class="template-chem2-sub">2</sub></span></a></li> <li><a href="/wiki/Iodic_acid" title="Iodic acid"><span class="chemf nowrap">HIO<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Periodic_acid" title="Periodic acid"><span class="chemf nowrap">HIO<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Permanganic_acid" title="Permanganic acid"><span class="chemf nowrap">HMnO<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Manganic_acid" class="mw-redirect" title="Manganic acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>MnO<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Molybdic_acid" title="Molybdic acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>MoO<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">HNC</a></li> <li><a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate"><span class="chemf nowrap">NaHCO<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">HNCO</a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">HNO</a></li> <li><a href="/wiki/Nitrous_acid" title="Nitrous acid"><span class="chemf nowrap">HNO<sub class="template-chem2-sub">2</sub></span></a></li> <li><a href="/wiki/Nitric_acid" title="Nitric acid"><span class="chemf nowrap">HNO<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Hyponitrous_acid" title="Hyponitrous acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>N<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">2</sub></span></a></li> <li><a href="/wiki/Nitrosylsulfuric_acid" title="Nitrosylsulfuric acid"><span class="chemf nowrap">HNO<sub class="template-chem2-sub">5</sub>S</span></a></li> <li><a href="/wiki/Sulfamic_acid" title="Sulfamic acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>NSO<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Properties_of_water" title="Properties of water"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O</span></a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">2</sub></span></a></li> <li><a href="/wiki/Trioxidane" title="Trioxidane"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Tetraoxidane" title="Tetraoxidane"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Pentaoxidane" title="Pentaoxidane"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">5</sub></span></a></li> <li><a href="/wiki/Hypophosphorous_acid" title="Hypophosphorous acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>PO<sub class="template-chem2-sub">2</sub></span></a></li> <li><a href="/wiki/Phosphorous_acid" title="Phosphorous acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>PO<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Phosphoric_acid" title="Phosphoric acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>PO<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Pyrophosphoric_acid" title="Pyrophosphoric acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">4</sub>P<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">7</sub></span></a></li> <li><a href="/wiki/Triphosphoric_acid" title="Triphosphoric acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">5</sub>P<sub class="template-chem2-sub">3</sub>O<sub class="template-chem2-sub">10</sub></span></a></li> <li><a href="/wiki/Chloroplatinic_acid" title="Chloroplatinic acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>[PtCl<sub class="template-chem2-sub">6</sub>]</span></a></li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>S</span></a></li> <li><a href="/wiki/Hydrogen_disulfide" title="Hydrogen disulfide"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>S<sub class="template-chem2-sub">2</sub></span></a></li> <li><a href="/wiki/Hydrogen_selenide" title="Hydrogen selenide"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>Se</span></a></li> <li><a href="/wiki/Selenous_acid" title="Selenous acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>SeO<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Selenic_acid" title="Selenic acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>SeO<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Silicic_acid" title="Silicic acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">4</sub>SiO<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Hexafluorosilicic_acid" title="Hexafluorosilicic acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>[SiF<sub class="template-chem2-sub">6</sub>]</span></a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">HSCN</a></li> <li><a href="/wiki/Isothiocyanic_acid" class="mw-redirect" title="Isothiocyanic acid">HNCS</a></li> <li><a href="/wiki/Sulfurous_acid" title="Sulfurous acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>SO<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Sulfuric_acid" title="Sulfuric acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>SO<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Peroxymonosulfuric_acid" title="Peroxymonosulfuric acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>SO<sub class="template-chem2-sub">5</sub></span></a></li> <li><a href="/wiki/Thiosulfuric_acid" title="Thiosulfuric acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>S<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Trihydrogen_oxide" title="Trihydrogen oxide"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>O</span></a></li> <li><a href="/wiki/Dithionic_acid" title="Dithionic acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>S<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">6</sub></span></a></li> <li><a href="/wiki/Disulfuric_acid" title="Disulfuric acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>S<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">7</sub></span></a></li> <li><a href="/wiki/Peroxydisulfuric_acid" title="Peroxydisulfuric acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>S<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">8</sub></span></a></li> <li><a href="/wiki/Triflic_acid" title="Triflic acid"><span class="chemf nowrap">CF<sub class="template-chem2-sub">3</sub>SO<sub class="template-chem2-sub">3</sub>H</span></a></li> <li><a href="/wiki/Hydrogen_telluride" title="Hydrogen telluride"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>Te</span></a></li> <li><a href="/wiki/Tellurous_acid" title="Tellurous acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>TeO<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/Telluric_acid" title="Telluric acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">6</sub>TeO<sub class="template-chem2-sub">6</sub></span></a></li> <li><a href="/wiki/Titanic_acid" title="Titanic acid"><span class="chemf nowrap">H<sub class="template-chem2-sub">4</sub>TiO<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Polonium_hydride" title="Polonium hydride"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>Po</span></a></li> <li><a href="/wiki/Cobalt_tetracarbonyl_hydride" title="Cobalt tetracarbonyl hydride"><span class="chemf nowrap">H[Co(CO)<sub class="template-chem2-sub">4</sub>]</span></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"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" 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