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class="vector-toc-numb">3.1</span> <span>Agricultural use</span> </div> </a> <ul id="toc-Agricultural_use-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Environmental_aspects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Environmental_aspects"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Environmental aspects</span> </div> </a> <ul id="toc-Environmental_aspects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyanamide_functional_group" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Cyanamide_functional_group"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Cyanamide functional group</span> </div> </a> <ul id="toc-Cyanamide_functional_group-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyanamide_in_space" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Cyanamide_in_space"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Cyanamide in space</span> </div> </a> <ul id="toc-Cyanamide_in_space-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-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" title="Table of Contents" > <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 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Available in 31 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-31" 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">31 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B3%D9%8A%D8%A7%D9%86%D8%A7%D9%85%D9%8A%D8%AF" title="سياناميد – Arabic" lang="ar" hreflang="ar" data-title="سياناميد" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%DB%8C%D8%A7%D9%86%D8%A7%D9%85%DB%8C%D8%AF" title="سیانامید – South Azerbaijani" lang="azb" hreflang="azb" data-title="سیانامید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Cianamida" title="Cianamida – Catalan" lang="ca" hreflang="ca" data-title="Cianamida" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Kyanamid" title="Kyanamid – Czech" lang="cs" hreflang="cs" data-title="Kyanamid" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Cyanamid" title="Cyanamid – German" lang="de" hreflang="de" data-title="Cyanamid" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CF%85%CE%B1%CE%BD%CE%B1%CE%BC%CE%AF%CE%B4%CE%B9%CE%BF" title="Κυαναμίδιο – Greek" lang="el" hreflang="el" data-title="Κυαναμίδιο" 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/Cianamida" title="Cianamida – Spanish" lang="es" hreflang="es" data-title="Cianamida" 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/Cianamido" title="Cianamido – Esperanto" lang="eo" hreflang="eo" data-title="Cianamido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%DB%8C%D8%A7%D9%86%D8%A7%D9%85%DB%8C%D8%AF" title="سیانامید – Persian" lang="fa" hreflang="fa" data-title="سیانامید" 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/Cyanamide_hydrog%C3%A8ne" title="Cyanamide hydrogène – French" lang="fr" hreflang="fr" data-title="Cyanamide hydrogène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</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%EC%95%84%EB%A7%88%EC%9D%B4%EB%93%9C" title="사이안아마이드 – Korean" lang="ko" hreflang="ko" data-title="사이안아마이드" 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%B4%D5%AB%D5%A4" title="Ցիանամիդ – Armenian" lang="hy" hreflang="hy" data-title="Ցիանամիդ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B8%E0%A4%BE%E0%A4%AF%E0%A4%A8%E0%A5%87%E0%A4%AE%E0%A4%BE%E0%A4%87%E0%A4%A1" title="सायनेमाइड – Hindi" lang="hi" hreflang="hi" data-title="सायनेमाइड" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Cianammide" title="Cianammide – Italian" lang="it" hreflang="it" data-title="Cianammide" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A6%D0%B8%D0%B0%D0%BD%D0%B0%D0%BC%D0%B8%D0%B4" title="Цианамид – Kyrgyz" lang="ky" hreflang="ky" data-title="Цианамид" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Ci%C3%A1namid" title="Ciánamid – Hungarian" lang="hu" hreflang="hu" data-title="Ciánamid" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cyaanamide" title="Cyaanamide – Dutch" lang="nl" hreflang="nl" data-title="Cyaanamide" 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%8A%E3%83%9F%E3%83%89" title="シアナミド – Japanese" lang="ja" hreflang="ja" data-title="シアナミド" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Hydrogencyanamid" title="Hydrogencyanamid – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Hydrogencyanamid" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Cyjanamid" title="Cyjanamid – Polish" lang="pl" hreflang="pl" data-title="Cyjanamid" 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/Cianamida" title="Cianamida – Portuguese" lang="pt" hreflang="pt" data-title="Cianamida" 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/Cianamid%C4%83" title="Cianamidă – Romanian" lang="ro" hreflang="ro" data-title="Cianamidă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A6%D0%B8%D0%B0%D0%BD%D0%B0%D0%BC%D0%B8%D0%B4" title="Цианамид – Russian" lang="ru" hreflang="ru" data-title="Цианамид" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Ky%C3%A1namid" title="Kyánamid – Slovak" lang="sk" hreflang="sk" data-title="Kyánamid" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Cijanamid" title="Cijanamid – Serbian" lang="sr" hreflang="sr" data-title="Cijanamid" 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/Cijanamid" title="Cijanamid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cijanamid" 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/Syanamidi" title="Syanamidi – Finnish" lang="fi" hreflang="fi" data-title="Syanamidi" 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/Cyanamid" title="Cyanamid – Swedish" lang="sv" hreflang="sv" data-title="Cyanamid" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A6%D1%96%D0%B0%D0%BD%D0%B0%D0%BC%D1%96%D0%B4" title="Ціанамід – Ukrainian" lang="uk" hreflang="uk" data-title="Ціанамід" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Cyanamide" title="Cyanamide – Vietnamese" lang="vi" hreflang="vi" data-title="Cyanamide" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%B0%A8%E5%9F%BA%E6%B0%B0" title="氨基氰 – Chinese" lang="zh" hreflang="zh" data-title="氨基氰" data-language-autonym="中文" data-language-local-name="Chinese" 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound featuring a nitrile group attached to an amino group</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">Not to be confused with <a href="/wiki/Cyanogen" title="Cyanogen">cyanogen</a> or <a href="/wiki/American_Cyanamid" title="American Cyanamid">American Cyanamid</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.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%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Cyanamide </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cyanamide.svg" class="mw-file-description"><img alt="Full skeletal formulas of cyanamide, both tautomers" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/Cyanamide.svg/250px-Cyanamide.svg.png" decoding="async" width="250" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/Cyanamide.svg/375px-Cyanamide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/37/Cyanamide.svg/500px-Cyanamide.svg.png 2x" data-file-width="620" data-file-height="176" /></a><figcaption></figcaption></figure> </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:Cyanamide_(nitrile)_3D_spacefill.png" class="mw-file-description"><img alt="Space-filling model of the cyanamide molecule, nitrile tautomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Cyanamide_%28nitrile%29_3D_spacefill.png/110px-Cyanamide_%28nitrile%29_3D_spacefill.png" decoding="async" width="110" height="81" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Cyanamide_%28nitrile%29_3D_spacefill.png/165px-Cyanamide_%28nitrile%29_3D_spacefill.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/Cyanamide_%28nitrile%29_3D_spacefill.png/220px-Cyanamide_%28nitrile%29_3D_spacefill.png 2x" data-file-width="2000" data-file-height="1481" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cyanamide_(diimide)_3D_spacefill.png" class="mw-file-description"><img alt="Space-filling model of the cyanamide molecule, diimide tautomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Cyanamide_%28diimide%29_3D_spacefill.png/120px-Cyanamide_%28diimide%29_3D_spacefill.png" decoding="async" width="120" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Cyanamide_%28diimide%29_3D_spacefill.png/180px-Cyanamide_%28diimide%29_3D_spacefill.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/32/Cyanamide_%28diimide%29_3D_spacefill.png/240px-Cyanamide_%28diimide%29_3D_spacefill.png 2x" data-file-width="2000" data-file-height="1260" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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;">Cyanamide</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;">Amidocyanogen, carbamonitrile, carbimide, carbodiimide, cyanoamine, cyanoazane, N-cyanoamine, cyanogenamide, cyanogen amide, cyanogen nitride, diiminomethane, hydrogen cyanamide, methanediimine</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=420-04-2">420-04-2</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=N%23CN">Interactive image</a></span></li><li><a href="/wiki/Carbodiimide" title="Carbodiimide">carbodiimide</a> isomer: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=N%3DC%3DN">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=16698">CHEBI:16698</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/ChEMBL" title="ChEMBL">ChEMBL</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/chembl/explore/compound/ChEMBL56279">ChEMBL56279</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/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.9480.html">9480</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/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB02679">DB02679</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.006.358">100.006.358</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q414555#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>206-992-3</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>784 </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/D00123">D00123</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/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/9864">9864</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>GS5950000</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/21CP7826LC">21CP7826LC</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>2811 </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/DTXSID9034490">DTXSID9034490</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q414555#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;"><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/CH2N2/c2-1-3/h2H2<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XZMCDFZZKTWFGF-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/CH2N2/c2-1-3/h2H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XZMCDFZZKTWFGF-UHFFFAOYAW</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;"><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%;">N#CN</div></li><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%;"><a href="/wiki/Carbodiimide" title="Carbodiimide">carbodiimide</a> isomer: N=C=N</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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>CH<sub>2</sub>N<sub>2</sub>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>42.040 g/mol    </td></tr> <tr> <td>Appearance </td> <td>Crystalline solid </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.28 g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>44 °C (111 °F; 317 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>260 °C (500 °F; 533 K) (decomposes)<br />83 °C at 6.7 Pa<br />140 °C at 2.5 kPa </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>85 g/100 ml (25 °C) </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in organic solvents </td> <td>soluble </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>−0.82 </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>10.3<sup id="cite_ref-chemsrc_1-0" class="reference"><a href="#cite_note-chemsrc-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-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-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><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> </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="H301: Toxic if swallowed">H301</abbr>, <abbr class="abbr" title="H311: Toxic in contact with skin">H311</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr>, <abbr class="abbr" title="H317: May cause an allergic skin reaction">H317</abbr>, <abbr class="abbr" title="H351: Suspected of causing cancer">H351</abbr>, <abbr class="abbr" title="H361: Suspected of damaging fertility or the unborn child">H361</abbr>, <abbr class="abbr" title="H373: May cause damage to organs through prolonged or repeated exposure">H373</abbr>, <abbr class="abbr" title="H412: Harmful to aquatic life with long lasting effects">H412</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="P201: Obtain special instructions before use.">P201</abbr>, <abbr class="abbr" title="P202: Do not handle until all safety precautions have been read and understood.">P202</abbr>, <abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P270: Do not eat, drink or smoke when using this product.">P270</abbr>, <abbr class="abbr" title="P272: Contaminated work clothing should not be allowed out of the workplace.">P272</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P281: Use personal protective equipment as required.">P281</abbr>, <abbr class="abbr" title="P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.">P301+P310</abbr>, <abbr class="abbr" title="P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.">P301+P330+P331</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P308+P313: IF exposed or concerned: Get medical advice/attention.">P308+P313</abbr>, <abbr class="abbr" title="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P314: Get Medical advice/attention if you feel unwell.">P314</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P322: Specific measures (see ... on this label).">P322</abbr>, <abbr class="abbr" title="P330: Rinse mouth.">P330</abbr>, <abbr class="abbr" title="P333+P313: If skin irritation or a rash occurs: Get medical advice/attention.">P333+P313</abbr>, <abbr class="abbr" title="P361: Remove/Take off immediately all contaminated clothing.">P361</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</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_00435942dc03bf4e" /></span><map name="ImageMap_00435942dc03bf4e"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><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 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</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>141 °C (286 °F; 414 K) </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><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>none<sup id="cite_ref-NIOSH_2-0" class="reference"><a href="#cite_note-NIOSH-2"><span class="cite-bracket">[</span>2<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>TWA 2 mg/m<sup>3</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>N.D.<sup id="cite_ref-NIOSH_2-1" class="reference"><a href="#cite_note-NIOSH-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0424.htm">ICSC 0424</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Calcium_cyanamide" title="Calcium cyanamide">Calcium cyanamide</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; 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="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443679323&page2=Cyanamide">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>Cyanamide</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <a href="/wiki/Carbon" title="Carbon">C</a><a href="/wiki/Nitrogen" title="Nitrogen">N</a><sub>2</sub><a href="/wiki/Hydrogen" title="Hydrogen">H</a><sub>2</sub>. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an <a href="/wiki/Alcohol-deterrent_drug" class="mw-redirect" title="Alcohol-deterrent drug">alcohol-deterrent drug</a>. The molecule features a <a href="/wiki/Nitrile" title="Nitrile">nitrile</a> group attached to an <a href="/wiki/Amino" class="mw-redirect" title="Amino">amino</a> group. Derivatives of this compound are also referred to as cyanamides, the most common being <a href="/wiki/Calcium_cyanamide" title="Calcium cyanamide">calcium cyanamide</a> (CaCN<sub>2</sub>).<sup id="cite_ref-Ullmann_3-0" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Tautomers_and_self-condensations">Tautomers and self-condensations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanamide&action=edit&section=1" title="Edit section: Tautomers and self-condensations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Containing both a nucleophilic and electrophilic site within the same molecule, cyanamide undergoes various reactions with itself. Cyanamide exists as two <a href="/wiki/Tautomer" title="Tautomer">tautomers</a>, one with the connectivity N≡C–NH<sub>2</sub> and the other with the formula HN=C=NH ("<a href="/wiki/Carbodiimide" title="Carbodiimide">carbodiimide</a>" tautomer). The N≡C–NH<sub>2</sub> form dominates, but in a few reactions (e.g. <a href="/wiki/Silylation" title="Silylation">silylation</a>) the diimide form appears to be important.<sup id="cite_ref-Ullmann_3-1" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Cyanamide dimerizes to give <a href="/wiki/2-Cyanoguanidine" title="2-Cyanoguanidine">2-cyanoguanidine</a> (dicyandiamide). This dimerization is hindered or reversed by acids and is inhibited by low temperatures. The cyclic <a href="/wiki/Trimer_(chemistry)" title="Trimer (chemistry)">trimer</a> is called <a href="/wiki/Melamine" title="Melamine">melamine</a>.<sup id="cite_ref-Ullmann_3-2" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanamide&action=edit&section=2" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanamide is produced by hydrolysis of <a href="/wiki/Calcium_cyanamide" title="Calcium cyanamide">calcium cyanamide</a>, which in turn is prepared from <a href="/wiki/Calcium_carbide" title="Calcium carbide">calcium carbide</a> via the <a href="/wiki/Frank%E2%80%93Caro_process" title="Frank–Caro process">Frank–Caro process</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>CaCN<sub>2</sub> + H<sub>2</sub>O + CO<sub>2</sub> → CaCO<sub>3</sub> + H<sub>2</sub>NCN</dd></dl> <p>The conversion is conducted on slurries. </p> <div class="mw-heading mw-heading2"><h2 id="Reactions_and_uses">Reactions and uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanamide&action=edit&section=3" title="Edit section: Reactions and uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanamide can be regarded as a functional single carbon fragment which can react as an <a href="/wiki/Electrophile" title="Electrophile">electrophile</a> or <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a>. The main reaction exhibited by cyanamide involves additions of compounds containing an acidic proton. Water, hydrogen sulfide, and hydrogen selenide react with cyanamide to give <a href="/wiki/Urea" title="Urea">urea</a>, <a href="/wiki/Thiourea" title="Thiourea">thiourea</a>, and <a href="/wiki/Selenourea" title="Selenourea">selenourea</a>, respectively: </p> <dl><dd>H<sub>2</sub>NCN + H<sub>2</sub>E → H<sub>2</sub>NC(E)NH<sub>2</sub> (E = O, S, Se)</dd></dl> <p>In this way, cyanamide behaves as a dehydration agent and thus can induce condensation reactions. Alcohols, thiols, and amines react analogously to give alkylisoureas, isothioureas, and <a href="/wiki/Guanidine" title="Guanidine">guanidines</a>. The anti-ulcer drug <a href="/wiki/Cimetidine" title="Cimetidine">cimetidine</a> is generated using such reactivity. Related reactions exploit the bifunctionality of cyanamide to give <a href="/wiki/Heterocycle" class="mw-redirect" title="Heterocycle">heterocycles</a>, and this latter reactivity is the basis of several pharmaceutical syntheses such as the aminopyrimidine <a href="/wiki/Imatinib" title="Imatinib">imatinib</a>, and agrichemicals <a href="/wiki/Amitrol" class="mw-redirect" title="Amitrol">Amitrol</a> and <a href="/wiki/Hexazinone" title="Hexazinone">hexazinone</a>. The hair-loss treatment <a href="/wiki/Minoxidil" title="Minoxidil">minoxidil</a> and the <a href="/wiki/Anthelmintic" title="Anthelmintic">anthelmintics</a> <a href="/wiki/Albendazole" title="Albendazole">albendazole</a>, <a href="/wiki/Flubendazole" title="Flubendazole">flubendazole</a>, and <a href="/wiki/Mebendazole" title="Mebendazole">mebendazole</a> feature 2-aminoimidazole substructures derived from cyanamide.<sup id="cite_ref-Ullmann_3-3" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Cyanamide is also used in the synthesis of other pharmaceutical drugs including <a href="/wiki/Tirapazamine" title="Tirapazamine">tirapazamine</a>, <a href="/wiki/Etravirine" title="Etravirine">etravirine</a>, <a href="/wiki/Revaprazan" title="Revaprazan">revaprazan</a>, and dasantafil. </p><p>The cyanamide <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a> has the character of a pseudo <a href="/wiki/Chalcogen" title="Chalcogen">chalcogen</a>, cyanamide can therefore be regarded as analogue to <a href="/wiki/Water" title="Water">water</a> or <a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">hydrogen sulfide</a>. </p><p>A convenient method for the preparation of secondary amines which are not contaminated with primary or tertiary amines is the reaction of cyanamide with alkyl halides to <i>N,N</i>-dialkylcyanamides which can easily be hydrolyzed to dialkylamines and then decarboxylated.<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> Cyanamide adds itself in the presence of N-bromosuccinimide to olefinic double bonds. The addition product is converted by bases to N-Cyanaziridine,<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> cyclized in the presence of acids to imidazolines, which can be further reacted to vicinal diamines by alkaline cleavage.<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> </p><p>Cyanamide is also a versatile synthetic building block for <a href="/wiki/Heterocyclic_compound" title="Heterocyclic compound">heterocycles</a>: it forms 2-aminobenzimidazole with <a href="/wiki/O-Phenylenediamine" title="O-Phenylenediamine">1,2-diaminobenzene</a><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> and it forms with the readily available cyclic <a href="/wiki/Enamine" title="Enamine">enamine</a> 4-(1-cyclohexenyl)morpholine<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> and with elemental <a href="/wiki/Sulfur" title="Sulfur">sulfur</a> a 2-aminothiazole in good yields.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Sodium dicyanamide is available in good yield and high purity from cyanamid and <a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">cyanogen chloride</a>,<sup id="cite_ref-allyl_11-0" class="reference"><a href="#cite_note-allyl-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><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> which is suitable as an <a href="/wiki/Reaction_intermediate#Chemical_Processing_Industry" title="Reaction intermediate">intermediate</a> for the synthesis of active pharmaceutical ingredients.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> A guanidino group is introduced by reaction of cyanamide with <a href="/wiki/Sarcosine" title="Sarcosine">sarcosine</a> In the industrial synthesis of <a href="/wiki/Creatine" title="Creatine">creatine</a>:.<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> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Creatine_synthesis.svg" class="mw-file-description" title="reaction equation"><img alt="reaction equation" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Creatine_synthesis.svg/650px-Creatine_synthesis.svg.png" decoding="async" width="650" height="115" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Creatine_synthesis.svg/975px-Creatine_synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Creatine_synthesis.svg/1300px-Creatine_synthesis.svg.png 2x" data-file-width="1035" data-file-height="183" /></a><figcaption>reaction equation</figcaption></figure> <p>This synthesis route mostly avoids problematic impurities like <a href="/wiki/Chloroacetic_acid" title="Chloroacetic acid">chloroacetic acid</a>, <a href="/wiki/Iminodiacetic_acid" title="Iminodiacetic acid">iminodiacetic acid</a>, or <a href="/w/index.php?title=Dihydrotriazine&action=edit&redlink=1" class="new" title="Dihydrotriazine (page does not exist)">dihydrotriazine</a> that occur in other routes. The physiological precursor <a href="/wiki/Glycocyamine" title="Glycocyamine">guanidinoacetic</a> is obtained analogously by reacting cyanamide with <a href="/wiki/Glycine" title="Glycine">glycine</a>. </p><p>Methods to <a href="/wiki/Stabilizer_(chemistry)" title="Stabilizer (chemistry)">stabilize</a> cyanamide make it available on an industrial scale. Due to the strong affinity towards self-condensation in alkaline media (see above) solutions of cyanamide are stabilized by the addition of 0.5 wt% of <a href="/wiki/Monosodium_phosphate" title="Monosodium phosphate">monosodium phosphate</a> as buffer. Solid cyanamide is produced by careful evaporation of the solvent and subsequent addition of a hydrolysis-labile <a href="/wiki/Ester" title="Ester">ester</a> of <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>. The ester absorbs traces of moisture (suppression of urea formation), neutralizes alkalinity (ammonia) and continually releases small amounts of formic acid.<sup id="cite_ref-Wehrstedt_15-0" class="reference"><a href="#cite_note-Wehrstedt-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Agricultural_use">Agricultural use</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanamide&action=edit&section=4" title="Edit section: Agricultural use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanamide, under the trade name Dormex, is a common agricultural <a href="/w/index.php?title=Rest-breaking_agent&action=edit&redlink=1" class="new" title="Rest-breaking agent (page does not exist)">rest-breaking agent</a> applied in spring to stimulate uniform opening of <a href="/wiki/Bud" title="Bud">buds</a>, early foliation and bloom. Cyanamide can effectively compensate for the moderate lack of <a href="/wiki/Chilling_unit" class="mw-redirect" title="Chilling unit">chilling units</a> accumulated in the previous autumn and save the harvest that would otherwise be lost. It is particularly effective for woody plants such as blueberries, grapes, apples, peaches and kiwifruit. Most recently the product was approved for use on almonds and pistachios in the USA. Overdosage, high concentration and error in timing of application can damage the buds (especially of <a href="/wiki/Peach" title="Peach">peach</a> trees).<sup id="cite_ref-PO_16-0" class="reference"><a href="#cite_note-PO-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Growers may avoid damage by applying 30 days prior to bud break according to the label. </p><p>A 50% aqueous solution of cyanamide is also used as a <a href="/wiki/Biocide" title="Biocide">biocide</a> (disinfectant) particularly in <a href="/wiki/Pig_farming" title="Pig farming">pig farming</a>, because it effectively kills salmonella and shigella and fights <a href="/wiki/Fly" title="Fly">flies</a> in all stages of development.<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> <div class="mw-heading mw-heading2"><h2 id="Environmental_aspects">Environmental aspects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanamide&action=edit&section=5" title="Edit section: Environmental aspects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanamide degrades via hydrolysis to urea, an excellent fertilizer. <a href="/wiki/Fungi" class="mw-redirect" title="Fungi">Fungi</a>, like <i><a href="/wiki/Myrothecium_verrucaria" title="Myrothecium verrucaria">Myrothecium verrucaria</a></i>, accelerate this process utilizing the enzyme <a href="/wiki/Cyanamide_hydratase" title="Cyanamide hydratase">cyanamide hydratase</a>.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Cyanamide_functional_group">Cyanamide functional group</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanamide&action=edit&section=6" title="Edit section: Cyanamide functional group"><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/Inorganic_cyanamide" class="mw-redirect" title="Inorganic cyanamide">Inorganic cyanamide</a></div> <p>Cyanamide is the name for a functional group with the formula <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">R<sup class="template-chem2-sup">1</sup>R<sup class="template-chem2-sup">2</sup>N−C≡N</span> where R<sup>1</sup> and R<sup>2</sup> can be a variety of groups. These compounds are called <b>cyanamides</b>. One example is naphthylcyanamide, C<sub>10</sub>H<sub>7</sub>N(CH<sub>3</sub>)CN, which has been produced by the <a href="/wiki/Von_Braun_reaction" title="Von Braun reaction">von Braun reaction</a>,<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> a general method for the conversion of <a href="/wiki/Tertiary_amine" class="mw-redirect" title="Tertiary amine">tertiary amines</a> to cyanamides using <a href="/wiki/Cyanogen_bromide" title="Cyanogen bromide">cyanogen bromide</a> as reagent.<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> Alternatively, secondary amines can attack an aryl <a href="/wiki/Cyanate_ester" title="Cyanate ester">cyanate</a> to give a carbamimidate; heating then eliminates the arenol to give a cyanamide. A similar reaction occurs with sulfonyl cyanides, but thiocyanates require a thiophilic metal to induce elimination.<sup id="cite_ref-Rev_21-0" class="reference"><a href="#cite_note-Rev-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 1389">: 1389 </span></sup> </p><p>Some cyanamides where R<sup>1</sup> and R<sup>2</sup> are identical alkyl groups are prepared directly by <a href="/wiki/Alkylation" title="Alkylation">alkylation</a> of a <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> of the parent cyanamide.<sup id="cite_ref-allyl_11-1" class="reference"><a href="#cite_note-allyl-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Likewise, <a href="/wiki/Acyl" class="mw-redirect" title="Acyl">acyl</a> cyanamides can be formed from an <a href="/wiki/Acyl_chloride" title="Acyl chloride">acyl chloride</a> and cyanamide, often with a base.<sup id="cite_ref-Rev_21-1" class="reference"><a href="#cite_note-Rev-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 1388">: 1388 </span></sup> </p><p>Alternatively, dehydration of <a href="/wiki/Ureas" title="Ureas">ureas</a> or dehydrosulfurization of thioureas can produce cyanamides, sometimes with rearrangement.<sup id="cite_ref-Rev_21-2" class="reference"><a href="#cite_note-Rev-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 1390–1392">: 1390–1392 </span></sup> <a href="/wiki/Isonitrile_dichloride" class="mw-redirect" title="Isonitrile dichloride">Isonitrile dichlorides</a> react with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> to give cyanamides.<sup id="cite_ref-Rev_21-3" class="reference"><a href="#cite_note-Rev-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 1392">: 1392 </span></sup> As a stabler valence isomer of <a href="/wiki/Carbodiimide" title="Carbodiimide">carbodiimides</a>, cyanamides form when carbodiimides are heated or undergo electrophilic substitution.<sup id="cite_ref-Rev_21-4" class="reference"><a href="#cite_note-Rev-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 1393">: 1393 </span></sup> </p><p>Secondary cyanamides are stable, but primary cyanamides trimerize to the corresponding <a href="/wiki/Triazine" title="Triazine">triazine</a>.<sup id="cite_ref-Rev_21-5" class="reference"><a href="#cite_note-Rev-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 1398">: 1398 </span></sup> </p><p>Cyanamides are more acidic and less basic than alkylamines, protonating at the terminal nitrogen. However, nickel(0) complexes are known in which nickel coordinates to both nitrogen atoms. When protonated, the central carbon is very electrophilic, and will add a variety of nucleophiles.<sup id="cite_ref-Rev_21-6" class="reference"><a href="#cite_note-Rev-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 1393–1395, 1399">: 1393–1395, 1399 </span></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Cyanamide_in_space">Cyanamide in space</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanamide&action=edit&section=7" title="Edit section: Cyanamide in space"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Due to its high permanent dipole moment (i.e., 4.32 ± 0.08 D),<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> cyanamide was detected in <a href="/wiki/Spectral_emission" class="mw-redirect" title="Spectral emission">spectral emissions</a> coming from the <a href="/wiki/Sgr_B2" class="mw-redirect" title="Sgr B2">Sgr B2</a> <a href="/wiki/Molecular_cloud" title="Molecular cloud">molecular cloud</a> (T < 100 K) through its microwave transitions as the first known interstellar molecule containing the NCN frame.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanamide&action=edit&section=8" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It is used as an <a href="/wiki/Alcohol-deterrent_drug" class="mw-redirect" title="Alcohol-deterrent drug">alcohol-deterrent drug</a> in Canada, Europe, and Japan.<sup id="cite_ref-Ullmann_3-4" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Cyanamide has a modest toxicity in humans.<sup id="cite_ref-Schep_24-0" class="reference"><a href="#cite_note-Schep-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Workplace exposure to hydrogen cyanamide sprays or exposure in people living in the vicinity of spraying have been reported as causing <a href="/wiki/Respiratory" class="mw-redirect" title="Respiratory">respiratory</a> irritation, <a href="/wiki/Contact_dermatitis" title="Contact dermatitis">contact dermatitis</a>, <a href="/wiki/Headache" title="Headache">headache</a>, and <a href="/wiki/Gastrointestinal_symptom" class="mw-redirect" title="Gastrointestinal symptom">gastrointestinal symptoms</a> of nausea, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, or <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>.<sup id="cite_ref-Schep_24-1" class="reference"><a href="#cite_note-Schep-24"><span class="cite-bracket">[</span>24<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=Cyanamide&action=edit&section=9" 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 reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-chemsrc-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-chemsrc_1-0">^</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" 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Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230160&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0160.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanamide" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ullmann_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Ullmann_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Ullmann_3-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite 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"Synthesis and chemical transformations of mono- and disubstituted cyanamides". <i>Russian Journal of Organic Chemistry (Zhurnal Organicheskoi Khimii)</i>. <b>40</b> (10). <a href="/wiki/Nauka_(publisher)" title="Nauka (publisher)">Nauka</a>: <span class="nowrap">1387–</span>1402. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs11178-005-0030-4">10.1007/s11178-005-0030-4</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Russian+Journal+of+Organic+Chemistry+%28Zhurnal+Organicheskoi+Khimii%29&rft.atitle=Synthesis+and+chemical+transformations+of+mono-+and+disubstituted+cyanamides&rft.volume=40&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1387-%3C%2Fspan%3E1402&rft.date=2004&rft_id=info%3Adoi%2F10.1007%2Fs11178-005-0030-4&rft.aulast=Nekrasov&rft.aufirst=D.+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanamide" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTylerSheridanCostain1972" class="citation journal cs1">Tyler, J.K.; Sheridan, J.; Costain, C.C. 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"The microwave spectra of cyanamide". <i>Journal of Molecular Spectroscopy</i>. <b>43</b> (2): <span class="nowrap">248–</span>261. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0022-2852%2872%2990021-5">10.1016/0022-2852(72)90021-5</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Molecular+Spectroscopy&rft.atitle=The+microwave+spectra+of+cyanamide&rft.volume=43&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E248-%3C%2Fspan%3E261&rft.date=1972-08&rft_id=info%3Adoi%2F10.1016%2F0022-2852%2872%2990021-5&rft.aulast=Tyler&rft.aufirst=J.K.&rft.au=Sheridan%2C+J.&rft.au=Costain%2C+C.C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanamide" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTurnerLisztKaifuKisliakov1975" class="citation journal cs1">Turner, B. E.; Liszt, H. S.; Kaifu, N.; Kisliakov, A. G. (November 1975). "Microwave detection of interstellar cyanamide". <i>The Astrophysical Journal</i>. <b>201</b>: L149. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1975ApJ...201L.149T">1975ApJ...201L.149T</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1086%2F181963">10.1086/181963</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Astrophysical+Journal&rft.atitle=Microwave+detection+of+interstellar+cyanamide&rft.volume=201&rft.pages=L149&rft.date=1975-11&rft_id=info%3Adoi%2F10.1086%2F181963&rft_id=info%3Abibcode%2F1975ApJ...201L.149T&rft.aulast=Turner&rft.aufirst=B.+E.&rft.au=Liszt%2C+H.+S.&rft.au=Kaifu%2C+N.&rft.au=Kisliakov%2C+A.+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanamide" class="Z3988"></span></span> </li> <li id="cite_note-Schep-24"><span class="mw-cite-backlink">^ <a href="#cite_ref-Schep_24-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Schep_24-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSchepTempleBeasley2009" class="citation journal cs1">Schep L, Temple W, Beasley M (January 2009). "The adverse effects of hydrogen cyanamide on human health: an evaluation of inquiries to the New Zealand National Poisons Centre". <i><a href="/wiki/Clinical_Toxicology" title="Clinical Toxicology">Clinical Toxicology</a></i>. <b>47</b> (1). Philadelphia, PA: <span class="nowrap">58–</span>60. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F15563650802459254">10.1080/15563650802459254</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18951270">18951270</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:6961576">6961576</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Toxicology&rft.atitle=The+adverse+effects+of+hydrogen+cyanamide+on+human+health%3A+an+evaluation+of+inquiries+to+the+New+Zealand+National+Poisons+Centre&rft.volume=47&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E58-%3C%2Fspan%3E60&rft.date=2009-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A6961576%23id-name%3DS2CID&rft_id=info%3Apmid%2F18951270&rft_id=info%3Adoi%2F10.1080%2F15563650802459254&rft.aulast=Schep&rft.aufirst=L&rft.au=Temple%2C+W&rft.au=Beasley%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanamide" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanamide&action=edit&section=10" title="Edit section: External links"><span>edit</span></a><span 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title="Pruno">Pruno</a></li></ul></li> <li><a href="/wiki/Public_intoxication" title="Public intoxication">Public intoxication</a></li> <li><a href="/wiki/Rum-running" title="Rum-running">Rum-running</a></li> <li><a href="/wiki/Sly-grog_shop" title="Sly-grog shop">Sly-grog shop</a></li> <li><a href="/wiki/Wine_fraud" title="Wine fraud">Wine fraud</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcoholism" title="Alcoholism">Alcoholism</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/Alcohol_and_Native_Americans" title="Alcohol and Native Americans">Alcohol and Native Americans</a></li> <li><a href="/wiki/Alcoholism_in_adolescence" title="Alcoholism in adolescence">Alcoholism in adolescence</a></li> <li><a href="/wiki/Alcoholism_in_family_systems" title="Alcoholism in family systems">Alcoholism in family systems</a></li> <li><a href="/wiki/Alcoholism_in_rural_Australia" title="Alcoholism in rural Australia">Alcoholism in rural Australia</a></li> <li><a href="/wiki/Collaborative_Study_on_the_Genetics_of_Alcoholism" title="Collaborative Study on the Genetics of Alcoholism">Collaborative Study on the Genetics of Alcoholism</a></li> <li><a href="/wiki/Disease_theory_of_alcoholism" title="Disease theory of alcoholism">Disease theory of alcoholism</a></li> <li><a href="/wiki/High-functioning_alcoholic" title="High-functioning alcoholic">High-functioning alcoholic</a> (HFA)</li> <li><a href="/wiki/Seeing_pink_elephants" title="Seeing pink elephants">Seeing pink elephants</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Chemistry</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Beverage-specific <ul><li><a href="/wiki/Beer_chemistry" title="Beer chemistry">Beer chemistry</a></li> <li><a href="/wiki/Wine_chemistry" title="Wine chemistry">Wine chemistry</a></li></ul></li> <li><a href="/wiki/Comparison_of_psychoactive_alcohols_in_alcoholic_drinks" title="Comparison of psychoactive alcohols in alcoholic drinks">Comparison of psychoactive alcohols in alcoholic drinks</a></li> <li><a href="/wiki/Congener_(beverages)" title="Congener (beverages)">Congener</a> <ul><li><a href="/wiki/Alcohol_congener_analysis" title="Alcohol congener analysis">Alcohol congener analysis</a></li></ul></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a> <ul><li><a href="/wiki/Blood_alcohol_content" title="Blood alcohol content">Blood alcohol content</a></li></ul></li> <li><a href="/wiki/Fusel_alcohol" title="Fusel alcohol">Fusel alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Effects</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/Short-term_effects_of_alcohol_consumption" title="Short-term effects of alcohol consumption">Short-term effects of alcohol consumption</a></li> <li><a href="/wiki/Long-term_effects_of_alcohol" title="Long-term effects of alcohol">Long-term effects of alcohol</a></li> <li><a href="/wiki/Pharmacology_of_ethanol" title="Pharmacology of ethanol">Pharmacology of ethanol</a></li> <li><a href="/wiki/Subjective_response_to_alcohol" title="Subjective response to alcohol">Subjective response to alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Adverse effects</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/Hangxiety" title="Hangxiety">Anxiety</a></li> <li><a href="/wiki/Impact_of_alcohol_on_aging" title="Impact of alcohol on aging">Aging</a></li> <li><a href="/wiki/Long-term_impact_of_alcohol_on_the_brain" title="Long-term impact of alcohol on the brain">Brain</a></li> <li><a href="/wiki/Alcohol_and_cancer" title="Alcohol and cancer">Cancer</a> <ul><li><a href="/wiki/Alcohol_and_breast_cancer" title="Alcohol and breast cancer">breast cancer</a></li></ul></li> <li><a href="/wiki/Alcohol_and_cortisol" title="Alcohol and cortisol">Cortisol</a></li> <li><a href="/wiki/Effects_of_alcohol_on_memory" title="Effects of alcohol on memory">Memory</a></li> <li><a href="/wiki/Alcohol_and_pregnancy" class="mw-redirect" title="Alcohol and pregnancy">Pregnancy</a></li> <li><a href="/wiki/Alcohol_use_and_sleep" title="Alcohol use and sleep">Sleep</a></li> <li><a href="/wiki/Alcohol_tolerance" title="Alcohol tolerance">Tolerance</a>/<a href="/wiki/Alcohol_intolerance" title="Alcohol intolerance">intolerance</a></li> <li><a href="/wiki/Alcohol_and_weight" title="Alcohol and weight">Weight</a></li> <li>Beverage-specific <ul><li>Beer: <a href="/wiki/Potomania" title="Potomania">Potomania</a></li> <li>Wine: <a href="/wiki/Red_wine_headache" title="Red wine headache">Red wine headache</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Social_issues" class="mw-redirect" title="Social issues">Social issues</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>Adulterated alcohol <ul><li><a href="/wiki/Moonshine#Adulterated_moonshine" title="Moonshine">Adulterated moonshine</a></li> <li><a href="/wiki/Denatured_alcohol" title="Denatured alcohol">Denatured alcohol</a> (<a href="/wiki/List_of_methanol_poisoning_incidents" title="List of methanol poisoning incidents">List of methanol poisoning incidents</a>)</li> <li><a href="/wiki/Surrogate_alcohol" title="Surrogate alcohol">Surrogate alcohol</a></li></ul></li> <li><a href="/wiki/Alcohol_abuse" title="Alcohol abuse">Alcohol abuse</a></li> <li><a href="/wiki/Alcohol_advertising" title="Alcohol advertising">Alcohol advertising</a> <ul><li><a href="/wiki/Alcohol_advertising_on_college_campuses" title="Alcohol advertising on college campuses">on college campuses</a></li></ul></li> <li><a href="/wiki/Alcohol_and_sex" title="Alcohol and sex">Sex</a> <ul><li><a href="/wiki/Beer_goggles" title="Beer goggles">Beer goggles</a></li></ul></li> <li><a href="/wiki/Alcohol_myopia" title="Alcohol myopia">Alcohol myopia</a></li> <li><a href="/wiki/Alcohol_in_association_football" title="Alcohol in association football">Alcohol in association football</a></li> <li><a href="/wiki/Alcohol_use_among_college_students" title="Alcohol use among college students">Alcohol use among college students</a></li> <li><a href="/wiki/Binge_drinking" title="Binge drinking">Binge drinking</a> <ul><li><a href="/wiki/Austrian_syndrome" title="Austrian syndrome">Austrian syndrome</a></li> <li><a href="/wiki/Alcohol_intoxication" title="Alcohol intoxication">Alcohol intoxication</a></li> <li><a href="/wiki/Epidemiology_of_binge_drinking" title="Epidemiology of binge drinking">Epidemiology of binge drinking</a></li> <li><a href="/wiki/Holiday_heart_syndrome" title="Holiday heart syndrome">Holiday heart syndrome</a></li> <li>Problematic alcoholic products <ul><li><a href="/wiki/Alcohol_powder" title="Alcohol powder">Alcohol powder</a></li> <li><a href="/wiki/Alcopop" title="Alcopop">Alcopop</a></li> <li><a href="/wiki/Borg_(drink)" title="Borg (drink)">Borg</a></li> <li>Low-cost alcohol <ul><li><a href="/wiki/Flavored_fortified_wine" title="Flavored fortified wine">Flavored fortified wine</a></li></ul></li> <li><a href="/wiki/Alcohol_(drug)#Stimulants" title="Alcohol (drug)">Polysubstance alcoholic drinks</a> <ul><li><a href="/wiki/Caffeinated_alcoholic_drink" title="Caffeinated alcoholic drink">Caffeinated alcoholic drink</a></li> <li><a href="/wiki/Coca_wine" title="Coca wine">Coca wine</a></li> <li><a href="/wiki/Nicotini" title="Nicotini">Nicotini</a></li></ul></li></ul></li> <li><a href="/wiki/Zapoy" title="Zapoy">Zapoy</a></li></ul></li> <li><a href="/wiki/Blackout_(drug-related_amnesia)" title="Blackout (drug-related amnesia)">Blackout</a></li> <li><a href="/wiki/Blackout_Wednesday" title="Blackout Wednesday">Blackout Wednesday</a></li> <li><a href="/wiki/Drinking_game" title="Drinking game">Drinking game</a> <ul><li><a href="/wiki/List_of_drinking_games" title="List of drinking games">list</a></li> <li><a href="/wiki/Pregaming" title="Pregaming">Pregaming</a></li></ul></li> <li><a href="/wiki/Drinking_in_public" title="Drinking in public">Drinking in public</a></li> <li><a href="/wiki/Drunk_walking" title="Drunk walking">Drunk walking</a></li> <li><a href="/wiki/Drunkorexia" title="Drunkorexia">Drunkorexia</a></li> <li><a href="/wiki/Dry_drunk" title="Dry drunk">Dry drunk</a></li> <li><a href="/wiki/Dutch_courage" title="Dutch courage">Dutch courage</a></li> <li><a href="/wiki/Flaming_drink" title="Flaming drink">Flaming drink</a></li> <li><a href="/wiki/Hair_of_the_dog" title="Hair of the dog">Hair of the dog</a></li> <li><a href="/wiki/Hurtful_communication#Alcohol" title="Hurtful communication">Hurtful communication</a> <ul><li><a href="/wiki/Drunk_dialing" title="Drunk dialing">Drunk dialing</a></li> <li><a href="/wiki/In_vino_veritas" title="In vino veritas"><i>In vino veritas</i></a></li></ul></li> <li><a href="/wiki/Nightcap_(drink)" title="Nightcap (drink)">Nightcap</a></li> <li><a href="/wiki/Pantsdrunk" title="Pantsdrunk">Pantsdrunk</a></li> <li><a href="/wiki/Passive_drinking" title="Passive drinking">Passive drinking</a></li> <li>Binge drinking devices <ul><li><a href="/wiki/Beer_bong" title="Beer bong">Beer bong</a></li> <li><a href="/wiki/Yard_of_ale" title="Yard of ale">Yard of ale</a></li></ul></li> <li>Routes of administration <ul><li><a href="/wiki/Alcohol_enema" title="Alcohol enema">Alcohol enema</a></li> <li><a href="/wiki/Alcohol_inhalation" title="Alcohol inhalation">Alcohol inhalation</a></li> <li><a href="/wiki/Vodka_eyeballing" title="Vodka eyeballing">Vodka eyeballing</a></li></ul></li> <li><a href="/wiki/Sconcing" title="Sconcing">Sconcing</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">History</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/Andrew_Johnson_alcoholism_debate" title="Andrew Johnson alcoholism debate">Andrew Johnson alcoholism debate</a></li> <li><a href="/wiki/Dionysian_Mysteries" title="Dionysian Mysteries">Dionysian Mysteries</a></li> <li><a href="/wiki/Dipsomania" title="Dipsomania">Dipsomania</a></li> <li><a href="/wiki/Gilbert_Paul_Jordan" title="Gilbert Paul Jordan">Gilbert Paul Jordan</a></li> <li><a href="/wiki/Gin_Craze" title="Gin Craze">Gin Craze</a></li> <li><a href="/wiki/List_of_deaths_through_alcohol" title="List of deaths through alcohol">List of deaths through alcohol</a></li> <li><a href="/wiki/Rum_ration" title="Rum ration">Rum ration</a></li> <li><a href="/wiki/Rum_Rebellion" title="Rum Rebellion">Rum Rebellion</a></li> <li><a href="/wiki/Shebeen" title="Shebeen">Shebeen</a></li> <li><a href="/wiki/Six_o%27clock_swill" title="Six o'clock swill">Six o'clock swill</a></li> <li>Illegal drinking establishments <ul><li><a href="/wiki/Nip_joint" title="Nip joint">Nip joint</a></li> <li><a href="/wiki/Speakeasy" title="Speakeasy">Speakeasy</a></li></ul></li> <li><a href="/wiki/Whiskey_Rebellion" title="Whiskey Rebellion">Whiskey Rebellion</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">General</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/Alcoholic_beverage" title="Alcoholic beverage">Alcoholic beverage</a></li> <li>Beer <ul><li><a href="/wiki/Beer_mile" title="Beer mile">Beer mile</a></li> <li><a href="/wiki/International_Beer_Day" title="International Beer Day">International Beer Day</a></li> <li><a href="/wiki/International_Women%27s_Collaboration_Brew_Day" title="International Women's Collaboration Brew Day">International Women's Collaboration Brew Day</a></li> <li><a href="/wiki/Women_in_brewing" title="Women in brewing">Women in brewing</a></li></ul></li> <li><a href="/wiki/Drinking_culture" title="Drinking culture">Drinking culture</a> <ul><li><a href="/wiki/Ap%C3%A9ritif_and_digestif" title="Apéritif and digestif">Apéritif and digestif</a></li> <li><a href="/wiki/Hangover_remedies" title="Hangover remedies">Hangover remedies</a></li> <li><a href="/wiki/Health_effects_of_wine" title="Health effects of wine">Health effects of wine</a> <ul><li><a href="/wiki/Wine_and_food_pairing" title="Wine and food pairing">Wine and food pairing</a></li></ul></li></ul></li> <li><a href="/wiki/Drunken_monkey_hypothesis" title="Drunken monkey hypothesis">Drunken monkey hypothesis</a></li> <li><a href="/wiki/Ladies%27_night" title="Ladies' night">Ladies' night</a></li> <li><a href="/wiki/List_of_countries_by_alcohol_consumption_per_capita" title="List of countries by alcohol consumption per capita">List of countries by alcohol consumption per capita</a> <ul><li><a href="/wiki/Alcohol_consumption_by_youth_in_the_United_States" title="Alcohol consumption by youth in the United States">Alcohol consumption by youth in the United States</a></li></ul></li> <li><a href="/wiki/List_of_substances_used_in_rituals#Alcohol" title="List of substances used in rituals">Ritual use of alcohol</a></li> <li>Whiskey <ul><li><a href="/wiki/International_whisk(e)y_day" title="International whisk(e)y day">International whisk(e)y day</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Alcohol <br />control</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohol_law" title="Alcohol law">Alcohol law</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/Administrative_License_Suspension" title="Administrative License Suspension">Administrative License Suspension</a> (ALS)</li> <li><a href="/wiki/Alcohol_(Minimum_Pricing)_(Scotland)_Act_2012" title="Alcohol (Minimum Pricing) (Scotland) Act 2012">Alcohol (Minimum Pricing) (Scotland) Act 2012</a></li> <li><a href="/wiki/Alcohol_exclusion_laws" title="Alcohol exclusion laws">Alcohol exclusion laws</a></li> <li><a href="/wiki/Alcohol_monopoly" title="Alcohol monopoly">Alcohol monopoly</a> <ul><li><a href="/wiki/Alcoholic_beverage_control_state" title="Alcoholic beverage control state">Alcoholic beverage control state</a></li></ul></li> <li><a href="/wiki/Alcohol_packaging_warning_messages" title="Alcohol packaging warning messages">Alcohol packaging warning messages</a></li> <li><a href="/wiki/Ban_on_caffeinated_alcoholic_drinks_in_the_United_States" title="Ban on caffeinated alcoholic drinks in the United States">Ban on caffeinated alcoholic drinks in the United States</a></li> <li><a href="/wiki/Drunk_driving_law_by_country" title="Drunk driving law by country">Drunk driving law by country</a> <ul><li><a href="/wiki/DWI_court" title="DWI court">DWI court</a></li> <li><a href="/wiki/Field_sobriety_testing" title="Field sobriety testing">Field sobriety testing</a></li> <li><a href="/wiki/Hip_flask_defence" title="Hip flask defence">Hip flask defence</a></li> <li><a href="/wiki/Ignition_interlock_device" title="Ignition interlock device">Ignition interlock device</a></li></ul></li> <li><a href="/wiki/Dry_county" title="Dry county">Dry county</a> <ul><li><a href="/wiki/List_of_dry_communities_by_U.S._state" title="List of dry communities by U.S. state">List of dry communities by U.S. state</a></li></ul></li> <li><a href="/wiki/Last_call" title="Last call">Last call</a></li> <li><a href="/wiki/Legal_drinking_age" title="Legal drinking age">Legal drinking age</a> <ul><li><a href="/wiki/Legal_drinking_age_in_the_United_States" title="Legal drinking age in the United States">Legal drinking age in the United States</a></li> <li><a href="/wiki/Shoulder_tap_(alcohol)" title="Shoulder tap (alcohol)">Shoulder tap</a></li></ul></li> <li><a href="/wiki/List_of_alcohol_laws_of_the_United_States" title="List of alcohol laws of the United States">List of alcohol laws of US</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Prohibition" title="Prohibition">Alcohol prohibition</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/List_of_countries_with_alcohol_prohibition" title="List of countries with alcohol prohibition">List of countries with alcohol prohibition</a></li> <li><a href="/wiki/Neo-prohibitionism" title="Neo-prohibitionism">Neo-prohibitionism</a></li> <li><a href="/wiki/Temperance_movement" title="Temperance movement">Temperance movement</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sobriety" title="Sobriety">Sobriety</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/Alcohol_detoxification" title="Alcohol detoxification">Alcohol detoxification</a></li> <li><a href="/wiki/Alcohol-free_zone" title="Alcohol-free zone">Alcohol-free zone</a> <ul><li><a href="/wiki/Dry_campus" title="Dry campus">Dry campus</a></li> <li><a href="/wiki/Open-container_law" title="Open-container law">Open-container law</a></li></ul></li> <li><a href="/wiki/Brief_intervention" title="Brief intervention">Brief intervention</a></li> <li><a href="/wiki/Designated_driver" title="Designated driver">Designated driver</a></li> <li><a href="/wiki/Drug_rehabilitation" title="Drug rehabilitation">Alcohol rehabilitation</a></li> <li><a href="/wiki/Drunk_tank" title="Drunk tank">Drunk tank</a></li> <li><a href="/wiki/Managed_alcohol_program" title="Managed alcohol program">Managed alcohol program</a></li> <li><a href="/wiki/Non-alcoholic_drink" title="Non-alcoholic drink">Non-alcoholic drink</a> <ul><li><a href="/wiki/List_of_non-alcoholic_cocktails" class="mw-redirect" title="List of non-alcoholic cocktails">List of cocktails</a></li> <li><a href="/wiki/List_of_non-alcoholic_mixed_drinks" title="List of non-alcoholic mixed drinks">List of mixed drinks</a></li> <li><a href="/wiki/Spritzer#Non-alcoholic_spritzer" title="Spritzer">Spritzer</a></li> <li><a href="/wiki/Malt_drink#Non-alcoholic_malt_drinks" title="Malt drink">Malt drinks</a></li></ul></li> <li><a href="/wiki/Teetotalism" title="Teetotalism">Teetotalism</a></li> <li><a href="/wiki/Temperance_bar" title="Temperance bar">Temperance bar</a></li> <li><a href="/wiki/Temperance_and_Good_Citizenship_Day" title="Temperance and Good Citizenship Day">Temperance and Good Citizenship Day</a></li> <li><a href="/wiki/List_of_twelve-step_groups" title="List of twelve-step groups">Twelve-step groups</a> <ul><li><a href="/wiki/Al-Anon/Alateen" title="Al-Anon/Alateen">Al-Anon/Alateen</a></li> <li><a href="/wiki/Alcoholics_Anonymous" title="Alcoholics Anonymous">Alcoholics Anonymous</a> (AA):</li> <li><a href="/wiki/Adult_Children_of_Alcoholics" class="mw-redirect" title="Adult Children of Alcoholics">Adult Children of Alcoholics</a> (ACA)</li></ul></li> <li><a href="/wiki/Sober_companion" title="Sober companion">Sober companion</a></li> <li><a href="/wiki/Sober_curious" title="Sober curious">Sober curious</a></li> <li><a href="/wiki/Sober_living_house" title="Sober living house">Sober living house</a></li> <li><a href="/wiki/Sobering_center" title="Sobering center">Sobering center</a></li> <li><a href="/wiki/Sobrietol" title="Sobrietol">Sobrietol</a></li> <li><a href="/wiki/Quit_lit_(alcohol_cessation)" title="Quit lit (alcohol cessation)">Quit lit</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Alcohol limitation</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/0-0-1-3" title="0-0-1-3">0-0-1-3</a></li> <li><a href="/wiki/Alcohol_consumption_recommendations" title="Alcohol consumption recommendations">Alcohol consumption recommendations</a></li> <li><a href="/wiki/Alcohol_education" title="Alcohol education">Alcohol education</a></li> <li><a href="/wiki/Alcohol_server_training" title="Alcohol server training">Alcohol server training</a></li> <li>Monitoring <ul><li><a href="/wiki/Breathalyzer" title="Breathalyzer">Breathalyzer</a></li> <li><a href="/wiki/Electronic_tagging#Sweat_alcohol_content_monitor" title="Electronic tagging">Sweat alcohol content monitor</a></li></ul></li> <li><a href="/wiki/Brief_intervention#FRAMES" title="Brief intervention">FRAMES</a></li> <li><a href="/wiki/Foundation_for_Advancing_Alcohol_Responsibility" title="Foundation for Advancing Alcohol Responsibility">Foundation for Advancing Alcohol Responsibility</a></li> <li>Campaigns <ul><li><a href="/wiki/Dry_January" title="Dry January">Dry January</a></li> <li><a href="/wiki/Dry_July" title="Dry July">Dry July</a></li> <li><a href="/wiki/Get_Your_Sexy_Back" title="Get Your Sexy Back">Get Your Sexy Back</a></li> <li><a href="/wiki/Ocsober" title="Ocsober">Ocsober</a></li></ul></li> <li><a href="/wiki/Liquor_license" title="Liquor license">Liquor license</a></li> <li>Low-alcohol drinks <ul><li><a href="/wiki/Fermented_tea" title="Fermented tea">Fermented tea</a></li> <li><a href="/wiki/Low-alcohol_beer" title="Low-alcohol beer">Low-alcohol beer</a></li> <li><a href="/wiki/Malt_drink#Low-alcoholic_malt_drinks" title="Malt drink">Low-alcoholic malt drinks</a></li> <li><a href="/wiki/Small_beer" title="Small beer">Small beer</a></li></ul></li> <li>Measurement <ul><li><a href="/wiki/Alcoholic_spirits_measure" title="Alcoholic spirits measure">Alcoholic spirits measure</a></li> <li><a href="/wiki/Standard_drink" title="Standard drink">Standard drink</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Addiction_medicine" title="Addiction medicine">Addiction medicine</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/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a> <ul><li><a href="/wiki/Chlordiazepoxide" title="Chlordiazepoxide">Chlordiazepoxide</a></li></ul></li> <li><a href="/wiki/Disulfiram-like_drug" title="Disulfiram-like drug">Disulfiram-like drugs</a> <ul><li><a href="/wiki/Disulfiram" title="Disulfiram">Disulfiram</a></li> <li><a href="/wiki/Calcium_carbimide" title="Calcium carbimide">Calcium carbimide</a></li> <li><a class="mw-selflink selflink">Cyanamide</a></li></ul></li> <li><a href="/wiki/General_anaesthetic" title="General anaesthetic">General anaesthetics</a> <ul><li><a href="/wiki/Nitrous_oxide_(medication)" title="Nitrous oxide (medication)">Nitrous oxide</a></li></ul></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acids</a> <ul><li><a href="/wiki/Acamprosate" title="Acamprosate">Acamprosate</a></li> <li><a href="/wiki/Homotaurine" title="Homotaurine">Homotaurine</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Religion_and_alcohol" title="Religion and alcohol">Religion and alcohol</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/Christian_views_on_alcohol" title="Christian views on alcohol">Christian views on alcohol</a> <ul><li><a href="/wiki/Alcohol_in_the_Bible" title="Alcohol in the Bible">Alcohol in the Bible</a></li></ul></li> <li><a href="/wiki/Khamr" title="Khamr">Islam and alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">History</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/Beer_Street_and_Gin_Lane" title="Beer Street and Gin Lane"><i>Beer Street</i> and <i>Gin Lane</i></a></li> <li><a href="/wiki/Bratt_System" title="Bratt System">Bratt System</a></li> <li><a href="/wiki/Dry_state" title="Dry state">Dry state</a></li> <li><a href="/wiki/Gin_Act_1751" title="Gin Act 1751">Gin Act 1751</a></li> <li><a href="/wiki/Medicinal_Liquor_Prescriptions_Act_of_1933" title="Medicinal Liquor Prescriptions Act of 1933">Medicinal Liquor Prescriptions Act of 1933</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Index_of_alcohol-related_articles" title="Index of alcohol-related articles">Index of alcohol-related articles</a></li> <li><a href="/wiki/Alcohol_and_spaceflight" title="Alcohol and spaceflight">Alcohol and spaceflight</a></li> <li><a href="/wiki/Gateway_drug_effect" title="Gateway drug effect">Gateway drug effect</a></li> <li><a href="/wiki/Mood_disorder" title="Mood disorder">Mood disorder</a></li> <li><a href="/wiki/Non-alcoholic_fatty_liver_disease" class="mw-redirect" title="Non-alcoholic fatty liver disease">Non-alcoholic fatty liver disease</a></li> <li><a href="/wiki/Self-medication" title="Self-medication">Self-medication</a></li> <li><a href="/wiki/Spins" title="Spins">Spins</a></li> <li><a href="/wiki/Town_drunk" title="Town drunk">Town drunk</a></li> <li><a href="/wiki/French_paradox" title="French paradox">French paradox</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow hlist" colspan="2"><div> <ul><li><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:Alcohol_and_health" title="Category:Alcohol and health">Category</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="Treatment_of_drug_dependence_(N07B)177" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Dependence_treatment" title="Template:Dependence treatment"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Dependence_treatment" title="Template talk:Dependence treatment"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Dependence_treatment" title="Special:EditPage/Template:Dependence treatment"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Treatment_of_drug_dependence_(N07B)177" style="font-size:114%;margin:0 4em">Treatment of <a href="/wiki/Substance_dependence" title="Substance dependence">drug dependence</a> (<a href="/wiki/ATC_code_N07#N07B" title="ATC code N07">N07B</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nicotine_dependence" title="Nicotine dependence">Nicotine dependence</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/Bupropion" title="Bupropion">Bupropion</a><sup>#</sup></li> <li><a href="/wiki/Cytisine" title="Cytisine">Cytisine</a></li> <li><a href="/wiki/Lobeline" title="Lobeline">Lobeline</a></li> <li><a href="/wiki/Mecamylamine" title="Mecamylamine">Mecamylamine</a></li> <li><a href="/wiki/Varenicline" title="Varenicline">Varenicline</a></li> <li><i><a href="/wiki/Adrenergic_agonist" title="Adrenergic agonist"><abbr title="Adrenergic agonist">AA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Adrenergic agonist</span></i> (<a href="/wiki/Clonidine" title="Clonidine">Clonidine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohol_dependence" title="Alcohol dependence">Alcohol dependence</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Acetaldehyde_dehydrogenase_inhibitor" class="mw-redirect" title="Acetaldehyde dehydrogenase inhibitor"><abbr title="Acetaldehyde dehydrogenase">AD</abbr> inhibitor</a></i> <ul><li><a href="/wiki/Disulfiram" title="Disulfiram">Disulfiram</a></li> <li><a href="/wiki/Acamprosate" title="Acamprosate">Acamprosate</a></li> <li><a href="/wiki/Calcium_carbimide" title="Calcium carbimide">Calcium carbimide</a></li> <li><a href="/wiki/Hydrogen_cyanamide" class="mw-redirect" title="Hydrogen cyanamide">Hydrogen cyanamide</a></li></ul></li> <li><i><a href="/wiki/General_anesthetic" class="mw-redirect" title="General anesthetic">General anesthetics</a></i> <ul><li><a href="/wiki/Nitrous_oxide_(medication)" title="Nitrous oxide (medication)">Nitrous oxide</a></li></ul></li> <li><i><a href="/wiki/Opioid_antagonist" title="Opioid antagonist">Opioid antagonists</a></i> <ul><li><a href="/wiki/Naltrexone" title="Naltrexone">Naltrexone</a></li> <li><a href="/wiki/Nalmefene" title="Nalmefene">Nalmefene</a></li></ul></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><i><a href="/wiki/Adrenergic_agonist" title="Adrenergic agonist"><abbr title="Adrenergic agonist">AA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Adrenergic agonist</span></i> (<a href="/wiki/Clonidine" title="Clonidine">Clonidine</a>)</li> <li><a href="/wiki/Baclofen" title="Baclofen">Baclofen</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opioid_dependence" class="mw-redirect" title="Opioid dependence">Opioid dependence</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><i><a href="/wiki/Adrenergic_agonist" title="Adrenergic agonist"><abbr title="Adrenergic agonist">AA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Adrenergic agonist</span></i> (<a href="/wiki/Clonidine" title="Clonidine">Clonidine</a></li> <li><a href="/wiki/Lofexidine" title="Lofexidine">Lofexidine</a>)</li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><i><a href="/wiki/Opioid" title="Opioid">Opioids</a></i> <ul><li><a href="/wiki/Buprenorphine" title="Buprenorphine">Buprenorphine</a> (<a href="/wiki/Buprenorphine/naloxone" title="Buprenorphine/naloxone">+naloxone</a>)</li> <li><a href="/wiki/Levacetylmethadol" title="Levacetylmethadol">Levacetylmethadol</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Dihydrocodeine" title="Dihydrocodeine">Dihydrocodeine</a></li> <li><a href="/wiki/Dihydroetorphine" title="Dihydroetorphine">Dihydroetorphine</a></li> <li><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone (extended-release)</a></li> <li><a href="/wiki/Morphine" title="Morphine">Morphine (extended-release)</a></li></ul></li> <li><i><a href="/wiki/Opioid_antagonist" title="Opioid antagonist">Opioid antagonists</a></i> (<a href="/wiki/Naltrexone" title="Naltrexone">Naltrexone</a></li> <li><a href="/wiki/Nalmefene" title="Nalmefene">Nalmefene</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzodiazepine_dependence" title="Benzodiazepine dependence">Benzodiazepine dependence</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Adrenergic_agonist" title="Adrenergic agonist"><abbr title="Adrenergic agonist">AA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Adrenergic agonist</span></i> (<a href="/wiki/Clonidine" title="Clonidine">Clonidine</a>)</li> <li><i><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></i> (<a href="/wiki/Diazepam" title="Diazepam">Diazepam</a></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a></li> <li><a href="/wiki/Chlordiazepoxide" title="Chlordiazepoxide">Chlordiazepoxide</a></li> <li><a href="/wiki/Oxazepam" title="Oxazepam">Oxazepam</a>)</li> <li><i><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a></i> (<a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</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="Molecules_detected_in_outer_space800" style="padding:3px"><table class="nowraplinks hlist 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:Molecules_detected_in_outer_space" title="Template:Molecules detected in outer 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_space800" 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/Imidogen" title="Imidogen">Imidogen</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/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_mononitride" title="Sulfur mononitride">Sulfur mononitride</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/120px-Buckminsterfullerene-perspective-3D-balls.png 1.5x" 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 href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">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="/wiki/Iron(II)_cyanide" title="Iron(II) cyanide">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/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</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/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</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/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</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/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="/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="/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/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/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</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 class="mw-selflink selflink">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="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</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/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/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</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/Acrolein" title="Acrolein">Acrolein</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/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</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/Ethanethiol" title="Ethanethiol">Ethanethiol</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/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</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/Propionitrile" title="Propionitrile">Propionitrile</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/Butyronitrile" title="Butyronitrile">Butyronitrile</a></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/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</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> <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/Pyrimidine" title="Pyrimidine">Pyrimidine</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 href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">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/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</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/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</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/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</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/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/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</li> <li><a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></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/17px-Earth-moon.jpg" decoding="async" width="17" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/26px-Earth-moon.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/34px-Earth-moon.jpg 2x" data-file-width="3000" data-file-height="2400" /></span></span> </span><a href="/wiki/Portal:Outer_space" title="Portal:Outer space">Outer space portal</a></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/15px-Crab_Nebula.jpg" decoding="async" width="15" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/23px-Crab_Nebula.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/30px-Crab_Nebula.jpg 2x" data-file-width="3864" data-file-height="3864" /></span></span> </span><a href="/wiki/Portal:Astronomy" title="Portal:Astronomy">Astronomy portal</a></li> <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/15px-Papapishu-Lab-icon-6.svg.png" decoding="async" width="15" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/23px-Papapishu-Lab-icon-6.svg.png 1.5x, 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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_species87" 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">NH<sub>4</sub><sup>+</sup></a></li> <li><a href="/wiki/Metal_amides#Alkali_metal_amides" title="Metal amides">NH<sub>2</sub><sup>−</sup></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">N<sub>3</sub><sup>−</sup></a></li> <li><a href="/wiki/Nitrogen_pentahydride" title="Nitrogen pentahydride"><i>NH<sub>5</sub></i></a> (?)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Organic</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">NR<sub>3</sub></a></li> <li><a href="/wiki/Imine" title="Imine">>C=NR</a></li> <li><a href="/wiki/Amide" title="Amide">−CONR<sub>2</sub></a></li> <li><a href="/wiki/Nitrile" title="Nitrile">−CN</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">HCN</a></li> <li><a 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 class="mw-selflink selflink">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">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a> / <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">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></a> / <a href="/wiki/Nitronium" class="mw-redirect" title="Nitronium">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a></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">N<sub>2</sub>O<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">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></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">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">3−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></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">N<sub>2</sub>O<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">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></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" /><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319" /></div><div role="navigation" class="navbox authority-control" aria-label="Navbox1204" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a 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