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Available in 20 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-20" 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">20 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Etielkarbamaat" title="Etielkarbamaat – Afrikaans" lang="af" hreflang="af" data-title="Etielkarbamaat" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%83%D8%B1%D8%A8%D8%A7%D9%85%D8%A7%D8%AA_%D8%A7%D9%84%D8%A5%D9%8A%D8%AB%D9%8A%D9%84" title="كربامات الإيثيل – Arabic" lang="ar" hreflang="ar" data-title="كربامات الإيثيل" 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%A7%D8%AA%DB%8C%D9%84_%DA%A9%D8%B1%D8%A8%D8%A7%D9%85%D8%A7%D8%AA" title="اتیل کربامات – South Azerbaijani" lang="azb" hreflang="azb" data-title="اتیل کربامات" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Ethyl-karbam%C3%A1t" title="Ethyl-karbamát – Czech" lang="cs" hreflang="cs" data-title="Ethyl-karbamát" 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/Urethan" title="Urethan – German" lang="de" hreflang="de" data-title="Urethan" 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%CE%B1%CF%81%CE%B2%CE%B1%CE%BC%CE%B9%CE%BA%CF%8C%CF%82_%CE%B1%CE%B9%CE%B8%CF%85%CE%BB%CE%B5%CF%83%CF%84%CE%AD%CF%81%CE%B1%CF%82" title="Καρβαμικός αιθυλεστέρας – Greek" lang="el" hreflang="el" data-title="Καρβαμικός αιθυλεστέρας" 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/Uretano" title="Uretano – Spanish" lang="es" hreflang="es" data-title="Uretano" 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/Etila_karbamato" title="Etila karbamato – Esperanto" lang="eo" hreflang="eo" data-title="Etila karbamato" 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%A7%D8%AA%DB%8C%D9%84_%DA%A9%D8%B1%D8%A8%D8%A7%D9%85%D8%A7%D8%AA" title="اتیل کربامات – Persian" lang="fa" hreflang="fa" data-title="اتیل کربامات" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Ethylcarbamaat" title="Ethylcarbamaat – Dutch" lang="nl" hreflang="nl" data-title="Ethylcarbamaat" 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%AB%E3%83%AB%E3%83%90%E3%83%9F%E3%83%B3%E9%85%B8%E3%82%A8%E3%83%81%E3%83%AB" title="カルバミン酸エチル – Japanese" lang="ja" hreflang="ja" data-title="カルバミン酸エチル" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Karbaminian_etylu" title="Karbaminian etylu – Polish" lang="pl" hreflang="pl" data-title="Karbaminian etylu" 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/Carbamato_de_etila" title="Carbamato de etila – Portuguese" lang="pt" hreflang="pt" data-title="Carbamato de etila" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%AD%D1%82%D0%B8%D0%BB%D1%83%D1%80%D0%B5%D1%82%D0%B0%D0%BD" title="Этилуретан – Russian" lang="ru" hreflang="ru" data-title="Этилуретан" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Etil_karbamat" title="Etil karbamat – Serbian" lang="sr" hreflang="sr" data-title="Etil karbamat" 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/Etil_karbamat" title="Etil karbamat – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Etil karbamat" 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/Etyylikarbamaatti" title="Etyylikarbamaatti – Finnish" lang="fi" hreflang="fi" data-title="Etyylikarbamaatti" 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/Uretan" title="Uretan – Swedish" lang="sv" hreflang="sv" data-title="Uretan" data-language-autonym="Svenska" data-language-local-name="Swedish" 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data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Ethyl carbamate </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Ethyl_carbamate_v2.svg" class="mw-file-description" title="Structural formula of ethyl carbamate"><img alt="Structural formula of ethyl carbamate" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Ethyl_carbamate_v2.svg/121px-Ethyl_carbamate_v2.svg.png" decoding="async" width="121" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Ethyl_carbamate_v2.svg/182px-Ethyl_carbamate_v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/79/Ethyl_carbamate_v2.svg/242px-Ethyl_carbamate_v2.svg.png 2x" data-file-width="153" data-file-height="79" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Ethyl_Carbamate_3D_Balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Ethyl_Carbamate_3D_Balls.png/150px-Ethyl_Carbamate_3D_Balls.png" decoding="async" width="150" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Ethyl_Carbamate_3D_Balls.png/225px-Ethyl_Carbamate_3D_Balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Ethyl_Carbamate_3D_Balls.png/300px-Ethyl_Carbamate_3D_Balls.png 2x" data-file-width="1832" data-file-height="918" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Ethyl carbamate</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Carbamic acid ethyl ester, Urethane, Ethylurethane</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=51-79-6">51-79-6</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CCOC%28N%29%3DO">Interactive image</a></span></li><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28OCC%29N">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B00312">B00312</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=17967">CHEBI:17967</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/ChEMBL462547">ChEMBL462547</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.5439.html">5439</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/DB04827">DB04827</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/100.000.113">100.000.113</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q422884#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-123-1</li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C01537">C01537</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/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Urethane">Urethane</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5641">5641</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>FA8400000</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/3IN71E75Z5">3IN71E75Z5</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/DTXSID9021427">DTXSID9021427</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q422884#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)<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: JOYRKODLDBILNP-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/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: JOYRKODLDBILNP-UHFFFAOYAY</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CCOC(N)=O</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%;">O=C(OCC)N</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>3</sub><span title="Hydrogen">H</span><sub>7</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001890940000000000♠"></span>89.094</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>White crystals </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.056 g cm<sup>−3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>46 to 50 °C (115 to 122 °F; 319 to 323 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>182 to 185 °C (360 to 365 °F; 455 to 458 K) </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>0.480 g cm<sup>−3</sup> at 15 °C </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>-0.190(4) </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>1.3 kPa at 78 °C </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>13.58 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>2.59 D<sup id="cite_ref-Exner_pp._1–92_1-0" class="reference"><a href="#cite_note-Exner_pp._1–92-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Harmful if swallowed<br />May cause cancer </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>:<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td 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-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="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H350: May cause cancer">H350</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="P301+P312+P330: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth.">P301+P312+P330</abbr>, <abbr class="abbr" title="P308+P313: IF exposed or concerned: Get medical advice/attention.">P308+P313</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_53fa73bec90f7290" /></span><map name="ImageMap_53fa73bec90f7290"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" class="notheme mw-no-invert">1</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 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>92 °C (198 °F; 365 K) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Methyl_carbamate" title="Methyl carbamate">Methyl carbamate</a><br /><a href="/w/index.php?title=Propyl_carbamate&action=edit&redlink=1" class="new" title="Propyl carbamate (page does not exist)">Propyl carbamate</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="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=414047867&page2=Ethyl+carbamate">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>Ethyl carbamate</b> (also called <b>urethane</b>) is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the formula CH<sub>3</sub>CH<sub>2</sub>OC(O)NH<sub>2</sub>. It is an <a href="/wiki/Ester" title="Ester">ester</a> of <a href="/wiki/Carbamic_acid" title="Carbamic acid">carbamic acid</a> and a white solid. Despite its name, it is not a component of <a href="/wiki/Polyurethane" title="Polyurethane">polyurethanes</a>. Because it is a <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>, it is rarely used, but naturally forms in low quantities in many types of fermented foods and drinks. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethyl_carbamate&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It is produced by organically heating <a href="/wiki/Urea" title="Urea">urea</a> and <a href="/wiki/Ethanol" title="Ethanol">ethyl alcohol</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> It also arises by the action of <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> on <a href="/wiki/Ethyl_chloroformate" title="Ethyl chloroformate">ethyl chloroformate</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-left" typeof="mw:File/Frameless"><a href="/wiki/File:Synthesis_of_ethyl_carbamate.tif" class="mw-file-description" title="Synthesis of ethyl carbamate"><img alt="Synthesis of ethyl carbamate" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Synthesis_of_ethyl_carbamate.tif/lossy-page1-450px-Synthesis_of_ethyl_carbamate.tif.jpg" decoding="async" width="450" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Synthesis_of_ethyl_carbamate.tif/lossy-page1-675px-Synthesis_of_ethyl_carbamate.tif.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Synthesis_of_ethyl_carbamate.tif/lossy-page1-900px-Synthesis_of_ethyl_carbamate.tif.jpg 2x" data-file-width="1364" data-file-height="237" /></a><figcaption>Synthesis of ethyl carbamate</figcaption></figure> <div style="clear:left;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethyl_carbamate&action=edit&section=2" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Biomedical_applications">Biomedical applications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethyl_carbamate&action=edit&section=3" title="Edit section: Biomedical applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ethyl carbamate has been used as an <a href="/wiki/Antineoplastic" class="mw-redirect" title="Antineoplastic">antineoplastic</a> agent and for other medicinal purposes, but this application ended after it was discovered to be <a href="/wiki/Carcinogenic" class="mw-redirect" title="Carcinogenic">carcinogenic</a> in 1943. However, Japanese usage in medical injections continued and from 1950 to 1975 an estimated 100 million 2 ml ampules of 7-to-15% solutions of ethyl carbamate were injected into patients as a co-solvent in water for dissolving water-insoluble analgesics used for post-operation pain. These doses were estimated to be at levels that are carcinogenic in mice.<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> This practice was stopped in 1975. "This regrettable medical situation appears to have involved the largest number (millions) of humans exposed to the largest doses of a pure carcinogen that is on record".<sup id="cite_ref-Miller1991_7-0" class="reference"><a href="#cite_note-Miller1991-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The author, U.S. cancer researcher James A. Miller, called for studies to determine the effects on Japanese cancer rates to be performed but apparently none were ever done.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (April 2021)">citation needed</span></a></i>]</sup> </p><p>Prior to World War II, ethyl carbamate saw relatively heavy use in the treatment of <a href="/wiki/Multiple_myeloma" title="Multiple myeloma">multiple myeloma</a> before it was found to be toxic, carcinogenic, and largely ineffective.<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> By US FDA regulations, ethyl carbamate has been withdrawn from pharmaceutical use. However, small quantities of ethyl carbamate are also used in laboratories as an anesthetic for animals.<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> </p><p>Ethyl carbamate was reclassified as a Group 2A carcinogen by IARC in 2007. </p><p>Ethyl carbamate is used as an <a href="/wiki/Anaesthetic" class="mw-redirect" title="Anaesthetic">anaesthetic</a> in <a href="/wiki/Animal_experimentation" class="mw-redirect" title="Animal experimentation">animal experiments</a>, with more than 100 animal studies using ethyl carbamate published each year.<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> One advantage of using ethyl carbamate is that it has a very long duration of action, with some adult rats remaining anaesthetised 24 hours after administration of the drug.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> It also does not depress neuronal activity in the <a href="/wiki/Cerebral_cortex" title="Cerebral cortex">cortex</a> to the same extent as <a href="/wiki/Isoflurane" title="Isoflurane">isoflurane</a>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_uses">Other uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethyl_carbamate&action=edit&section=4" title="Edit section: Other uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formerly, ethyl carbamate was used as a chemical intermediate in the preparation of amino resins, that were in turn used as crosslinking agents for permanent-press textile treatments to create "wash-and-wear" fabrics. Other uses included as solvent or intermediary in the manufacture of pesticides, cosmetics and pharmaceuticals.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence_in_beverages_and_food">Occurrence in beverages and food</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethyl_carbamate&action=edit&section=5" title="Edit section: Occurrence in beverages and food"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The widespread presence of ethyl carbamate in <a href="/wiki/Alcoholic_beverage" title="Alcoholic beverage">alcoholic beverages</a> was discovered during the mid-1980s. To raise public awareness of this issue, the U.S. Center for Science in the Public Interest published, in 1987, <i>Tainted Booze: The Consumer's Guide to Urethane in Alcoholic Beverages</i>. Studies have shown that most, if not all, yeast-fermented <a href="/wiki/Alcoholic_beverages" class="mw-redirect" title="Alcoholic beverages">alcoholic beverages</a> contain traces of ethyl carbamate (15 ppb to 12 ppm).<sup id="cite_ref-Segal_14-0" class="reference"><a href="#cite_note-Segal-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Other foods and beverages prepared by means of fermentation also contain ethyl carbamate. For example, bread has been found to contain 2 ppb;<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> as much as 20 ppb has been found in some samples of soy sauce.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Amounts of both ethyl carbamate and <a href="/wiki/Methyl_carbamate" title="Methyl carbamate">methyl carbamate</a> have also been found in wines, sake, beer, brandy, whiskey and other fermented alcoholic beverages. </p><p>It has been shown that ethyl carbamate forms from the reaction of <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> with <a href="/wiki/Urea" title="Urea">urea</a>: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Ethanol_urea_reaction.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Ethanol_urea_reaction.tif/lossy-page1-498px-Ethanol_urea_reaction.tif.jpg" decoding="async" width="498" height="97" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Ethanol_urea_reaction.tif/lossy-page1-747px-Ethanol_urea_reaction.tif.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Ethanol_urea_reaction.tif/lossy-page1-996px-Ethanol_urea_reaction.tif.jpg 2x" data-file-width="1264" data-file-height="246" /></a></span></dd></dl> <p>This reaction occurs much faster at higher temperatures, and therefore higher concentrations of ethyl carbamate are found in beverages that are heated during processing, such as brandy, whiskey, and other <a href="/wiki/Distilled_beverages" class="mw-redirect" title="Distilled beverages">distilled beverages</a>. Additionally, heating after bottling either during shipping or in preparation will cause ethyl carbamate levels to rise further. </p><p>The urea in wines results from the metabolism of <a href="/wiki/Arginine" title="Arginine">arginine</a> or <a href="/wiki/Citrulline" title="Citrulline">citrulline</a> by <a href="/wiki/Yeast_(wine)" class="mw-redirect" title="Yeast (wine)">yeast</a> or other organisms. The urea waste product is initially metabolised inside the yeast cell until it builds up to a certain level. At that point, it is excreted externally where it is able to react with the alcohol to create ethyl carbamate. </p><p>In 1988, wine and other alcoholic beverage manufacturers in the <a href="/wiki/United_States" title="United States">United States</a> agreed to control the level of ethyl carbamate in wine to less than 15 ppb (parts per billion), and in stronger alcoholic drinks to less than 125 ppb.<sup id="cite_ref-Segal_14-1" class="reference"><a href="#cite_note-Segal-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Although the urea cannot be eliminated, it can be minimized by controlling the fertilization of grape vines, minimizing their heat exposure, using self-cloning yeast<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> and other actions.<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> Furthermore, some strains of yeast have been developed to help reduce ethyl carbamate during commercial production of alcoholic beverages.<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> </p><p>Another important mechanism for ethyl carbamate formation in alcoholic beverages is the reaction from cyanide as precursor, which causes comparably high levels in spirits derived from cyanogenic plants, such as <a href="/wiki/Rhum_agricole" title="Rhum agricole">rhum agricole</a>.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Hazards">Hazards</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethyl_carbamate&action=edit&section=6" title="Edit section: Hazards"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Text-source plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Ambox_important.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/40px-Ambox_important.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/60px-Ambox_important.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/80px-Ambox_important.svg.png 2x" data-file-width="40" data-file-height="40" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>may contain <a href="/wiki/Wikipedia:CITEBUNDLE" class="mw-redirect" title="Wikipedia:CITEBUNDLE">bundled citations</a> with poor <a href="/wiki/Wikipedia:INTEGRITY" class="mw-redirect" title="Wikipedia:INTEGRITY">text–source integrity</a>.</b><span class="hide-when-compact"> Please help <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Ethyl_carbamate&action=edit">improve this article</a> this article by <a href="/wiki/Wikipedia:VERIFY" class="mw-redirect" title="Wikipedia:VERIFY">verifying its sources</a>, moving citations closer to the claims they support, and <a href="/wiki/Wikipedia:SYNTH" class="mw-redirect" title="Wikipedia:SYNTH">removing original synthesis</a>.</span> <span class="date-container"><i>(<span class="date">May 2019</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <p>Ethyl carbamate is not acutely toxic to humans, as reflected by its use as a medicine. Acute toxicity studies show that the lowest fatal dose in rats, mice, and rabbits equals 1.2 g/kg or more. When ethyl carbamate was used medicinally, about 50% of the patients exhibited nausea and vomiting, and long-time use led to gastroenteric hemorrhages.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> The compound has almost no odor and a cooling, saline, bitter taste.<sup id="cite_ref-HSDB_2006a_22-0" class="reference"><a href="#cite_note-HSDB_2006a-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>Studies with rats, mice, and hamsters have shown that ethyl carbamate causes cancer when administered orally, injected, or applied to the skin, but no adequate studies of cancer in humans caused by ethyl carbamate has been reported due to the ethical considerations of such studies.<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> However, in 2007, the International Agency for Research on Cancer raised ethyl carbamate to a Group 2A carcinogen that is "probably carcinogenic to humans", one level below fully carcinogenic to humans. IARC has stated that ethyl carbamate can be "reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity in experimental animals".<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> In 2006, the Liquor Control Board of Ontario in Canada rejected imported cases of sherry due to excessive levels of ethyl carbamate. </p><p>Studies in Hong Kong (2009)<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> and Korea (2015)<sup id="cite_ref-Ryu_Choi_Kim_Park_pp._289–297_26-0" class="reference"><a href="#cite_note-Ryu_Choi_Kim_Park_pp._289–297-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> outline the extent of the accumulative exposure to ethyl carbamate in daily life. Fermented foods such as soy sauce, kimchi, soybean paste, breads, rolls, buns, crackers and bean curd, along with wine, sake and plum wine, were found to be the foods with the highest ethyl carbamate levels in traditional Asian diets. </p><p>In 2005, the JECFA (Joint FAO/WHO Expert Committee On Food Additives) risk-assessment evaluation of ethyl carbamate<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> concluded that the MOE intake of ethyl carbamate from daily food and alcoholic beverages combined is of concern, and mitigation measures to reduce ethyl carbamate in some alcoholic beverages should continue. There is little doubt<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> that ethyl carbamate in alcoholic beverages is very important to health authorities, while the cumulative daily exposure in the typical diet is also an issue of rising concern that merits closer observation. The Korean study concluded: "It would be desirable to closely monitor ethyl carbamate levels in Korean foods and find ways to reduce the daily intake." </p><p>The IARC evaluation has led to the following US regulatory actions:<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (May 2019)">citation needed</span></a></i>]</sup> </p> <ul><li><a href="/wiki/NESHAP" class="mw-redirect" title="NESHAP">NESHAP</a>: Listed as a Hazardous Air Pollutant (HAP)</li> <li>Comprehensive Environmental Response, Compensation, and Liability Act: Reportable Quantity (RQ) = 100 lb</li> <li>Emergency Planning and Community Right-To-Know Act, EPA's Toxics Release Inventory: A listed substance subject to RCRA reporting requirements</li> <li><a href="/wiki/RCRA" class="mw-redirect" title="RCRA">RCRA</a> Listed Hazardous Waste: substance - U238</li></ul> <div class="mw-heading mw-heading2"><h2 id="Detection_in_alcoholic_beverages">Detection in alcoholic beverages</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethyl_carbamate&action=edit&section=7" title="Edit section: Detection in alcoholic beverages"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The concerns raised by the toxicological aspects of EC together with the low concentration levels (μg/L) found in wines, as well as the occurrence of interferences on detection, has motivated several researchers to develop new methods to determine it in wines. Several extraction and chromatographic techniques have been used, including continuous liquid–liquid extraction (LLE) with Soxhlet apparatus, derivatization with 9-xanthydrol followed by high-performance liquid chromatography (HPLC) with fluorescence detection and even LLE after derivatization, followed by gas chromatography coupled with mass spectrometry detection (GC–MS). On the other hand, the reference method set by the International Organization of Vine and Wine (OIV) uses solid phase extraction (SPE) preceding GC–MS quantification. Other methods also make use of SPE, but use gas chromatography with mass spectrometry (MDGC/MS) and liquid chromatography with tandem mass spectrometry (LC–MS/MS) for detection. Most of the methodologies found in the literature to quantify EC use gas chromatography, using LLE and SPE as extraction techniques. Nevertheless, several efforts have also been done to develop new methodologies to determine EC without using long procedures and hard-working analyses, combining precision to high sensitivity. In this regard, headspace solid phase microextraction (HS-SPME) has been gaining great highlighting and alternative methodologies has been proposed using the most recent identification and quantification technology, such as gas chromatography with tandem mass spectrometry detection (GC–MS/MS) and two-dimensional gas chromatography with time-of-flight mass spectrometry (GC × GC–ToFMS). </p><p>Microextraction by packed sorbent (MEPS) is also feasible. MEPS/GC–MS methodology has been applied to quantify EC in wines.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p><p>Miniaturized liquid-liquid extraction (mLLE) followed by LC-MS/MS can be used to determine EC in wine, without using derivatizing agents.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Related_compounds">Related compounds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethyl_carbamate&action=edit&section=8" title="Edit section: Related compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Other carbamates include <a href="/wiki/Methyl_carbamate" title="Methyl carbamate">methyl carbamate</a>,<sup id="cite_ref-HSDB_2006b_32-0" class="reference"><a href="#cite_note-HSDB_2006b-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> <a href="/w/index.php?title=Butyl_carbamate&action=edit&redlink=1" class="new" title="Butyl carbamate (page does not exist)">butyl carbamate</a>,<sup id="cite_ref-HSDB_2006c_33-0" class="reference"><a href="#cite_note-HSDB_2006c-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> and <a href="/w/index.php?title=Phenyl_carbamate&action=edit&redlink=1" class="new" title="Phenyl carbamate (page does not exist)">phenyl carbamate</a> (m. p. 149–152 °C),<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> which can also be prepared from the corresponding <a href="/wiki/Chloroformate" title="Chloroformate">chloroformate</a> and <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>. These esters are white, crystalline solids at room temperature. Except for the phenyl carbamate, they sublime at moderate temperatures; methyl carbamate sublimes at room temperatures. The first two and ethyl carbamate are very soluble in water, benzene, and ether.<sup id="cite_ref-HSDB_2006a_22-1" class="reference"><a href="#cite_note-HSDB_2006a-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HSDB_2006b_32-1" class="reference"><a href="#cite_note-HSDB_2006b-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HSDB_2006c_33-1" class="reference"><a href="#cite_note-HSDB_2006c-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> These other carbamates (<a href="/wiki/Methyl_carbamate" title="Methyl carbamate">methyl</a>, butyl, and phenyl) are only used in small quantities for research purposes. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethyl_carbamate&action=edit&section=9" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Methyl_carbamate" title="Methyl carbamate">Methyl carbamate</a></li></ul> <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=Ethyl_carbamate&action=edit&section=10" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Exner_pp._1–92-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Exner_pp._1–92_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 id="CITEREFExner1977" class="citation book cs1">Exner, Otto (1977). "Dipole moments, configurations and conformations of molecules containing X...Y groups". <i>Double-Bonded Functional Groups: Vol. 1 (1977)</i>. Chichester, UK: John Wiley & Sons, Ltd. pp. 1–92. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470771501.ch1">10.1002/9780470771501.ch1</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-77150-1" title="Special:BookSources/978-0-470-77150-1"><bdi>978-0-470-77150-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Dipole+moments%2C+configurations+and+conformations+of+molecules+containing+X...Y+groups&rft.btitle=Double-Bonded+Functional+Groups%3A+Vol.+1+%281977%29&rft.place=Chichester%2C+UK&rft.pages=1-92&rft.pub=John+Wiley+%26+Sons%2C+Ltd.&rft.date=1977&rft_id=info%3Adoi%2F10.1002%2F9780470771501.ch1&rft.isbn=978-0-470-77150-1&rft.aulast=Exner&rft.aufirst=Otto&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthyl+carbamate" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.stenutz.eu/chem/solv6.php?name=ethyl%20carbamate">"ethyl carbamate"</a>. <i>stenutz.eu</i><span class="reference-accessdate">. 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"A Sensitive Method for the Rapid Determination of Underivatized Ethyl Carbamate in Fortified Wine by Liquid Chromatography-Electrospray Tandem Mass Spectrometry". <i>Food Analytical Methods</i>. <b>11</b> (2): 327–333. <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%2Fs12161-017-1002-3">10.1007/s12161-017-1002-3</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/10400.13%2F3725">10400.13/3725</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1936-9751">1936-9751</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:102508529">102508529</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Food+Analytical+Methods&rft.atitle=A+Sensitive+Method+for+the+Rapid+Determination+of+Underivatized+Ethyl+Carbamate+in+Fortified+Wine+by+Liquid+Chromatography-Electrospray+Tandem+Mass+Spectrometry&rft.volume=11&rft.issue=2&rft.pages=327-333&rft.date=2017-08-15&rft_id=info%3Ahdl%2F10400.13%2F3725&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A102508529%23id-name%3DS2CID&rft.issn=1936-9751&rft_id=info%3Adoi%2F10.1007%2Fs12161-017-1002-3&rft.aulast=Le%C3%A7a&rft.aufirst=Jo%C3%A3o+M.&rft.au=Pereira%2C+Vanda&rft.au=Pereira%2C+Ana+C.&rft.au=Marques%2C+Jos%C3%A9+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthyl+carbamate" class="Z3988"></span></span> </li> <li id="cite_note-HSDB_2006b-32"><span class="mw-cite-backlink">^ <a href="#cite_ref-HSDB_2006b_32-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-HSDB_2006b_32-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">National Library of Medicine, Hazardous Data Bank, Methyl Carbamate 2006b, accessed May 13, 2006 at <a rel="nofollow" class="external free" href="http://toxnet.nlm.nih.gov">http://toxnet.nlm.nih.gov</a></span> </li> <li id="cite_note-HSDB_2006c-33"><span class="mw-cite-backlink">^ <a href="#cite_ref-HSDB_2006c_33-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-HSDB_2006c_33-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">National Library of Medicine, Hazardous Data Bank, Butyl Carbamate 2006c, accessed May 13, 2006 at <a rel="nofollow" class="external free" href="http://toxnet.nlm.nih.gov">http://toxnet.nlm.nih.gov</a></span> </li> <li id="cite_note-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-34">^</a></b></span> <span class="reference-text">Dean, J. A. (editor), <i>Lange's Handbook of Chemistry</i>, 13th Ed., 1985, p. 7-586, #p191.</span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethyl_carbamate&action=edit&section=11" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+@rel+51-79-6">NLM Hazardous Substances Databank – Ethyl carbamate</a></li></ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" 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