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</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">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-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 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mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 18 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-18" 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">18 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%A8%D8%B1%D9%88%D8%AF%D9%8A%D9%81%D8%A7%D9%83%D9%88%D9%85" title="بروديفاكوم – Arabic" lang="ar" hreflang="ar" data-title="بروديفاكوم" 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%A8%D8%B1%D9%88%D8%AF%DB%8C%D9%81%D8%A7%DA%A9%D9%88%D9%85" title="برودیفاکوم – South Azerbaijani" lang="azb" hreflang="azb" data-title="برودیفاکوم" 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/Brodifacoum" title="Brodifacoum – Catalan" lang="ca" hreflang="ca" data-title="Brodifacoum" 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/Brodifakum" title="Brodifakum – Czech" lang="cs" hreflang="cs" data-title="Brodifakum" 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/Brodifacoum" title="Brodifacoum – German" lang="de" hreflang="de" data-title="Brodifacoum" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A8%D8%B1%D9%88%D8%AF%DB%8C%D9%81%D8%A7%DA%A9%D9%88%D9%85" title="برودیفاکوم – Persian" lang="fa" hreflang="fa" data-title="برودیفاکوم" 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/Brodifacoum" title="Brodifacoum – French" lang="fr" hreflang="fr" data-title="Brodifacoum" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Brodifacoum" title="Brodifacoum – Italian" lang="it" hreflang="it" data-title="Brodifacoum" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Brodifakum" title="Brodifakum – Hungarian" lang="hu" hreflang="hu" data-title="Brodifakum" 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/Brodifacoum" title="Brodifacoum – Dutch" lang="nl" hreflang="nl" data-title="Brodifacoum" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Brodifacoum" title="Brodifacoum – Portuguese" lang="pt" hreflang="pt" data-title="Brodifacoum" 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%91%D1%80%D0%BE%D0%B4%D0%B8%D1%84%D0%B0%D0%BA%D1%83%D0%BC" title="Бродифакум – Russian" lang="ru" hreflang="ru" data-title="Бродифакум" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Brodifakum" title="Brodifakum – Slovenian" lang="sl" hreflang="sl" data-title="Brodifakum" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Brodifakum" title="Brodifakum – Serbian" lang="sr" hreflang="sr" data-title="Brodifakum" 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/Brodifakum" title="Brodifakum – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Brodifakum" 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/Brodifakumi" title="Brodifakumi – Finnish" lang="fi" hreflang="fi" data-title="Brodifakumi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%91%D1%80%D0%BE%D0%B4%D0%B8%D1%84%D0%B0%D0%BA%D1%83%D0%BC" title="Бродифакум – Ukrainian" lang="uk" hreflang="uk" data-title="Бродифакум" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%BA%B4%E9%BC%A0%E7%81%B5" title="溴鼠灵 – Chinese" lang="zh" hreflang="zh" data-title="溴鼠灵" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q421203#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div 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th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Brodifacoum<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Brodifacoum.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Brodifacoum.svg/220px-Brodifacoum.svg.png" decoding="async" width="220" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Brodifacoum.svg/330px-Brodifacoum.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Brodifacoum.svg/440px-Brodifacoum.svg.png 2x" data-file-width="542" data-file-height="300" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">3-[3-[4-(4-Bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-2-hydroxychromen-4-one</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;">Bromfenacoum</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=56073-10-0">56073-10-0</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=Brc1ccc%28cc1%29c2ccc%28cc2%29C4Cc3ccccc3C%28C4%29C%5C5%3DC%28%2FO%29c6ccccc6OC%2F5%3DO">Interactive image</a></span></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/chembldb/index.php/compound/inspect/ChEMBL233451">ChEMBL233451</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.10444663.html">10444663</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/100.054.509">100.054.509</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q421203#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><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/41736">41736</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>GN4934750</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/A25P3CP5S7">A25P3CP5S7</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/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/DTXSID5032529">DTXSID5032529</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q421203#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/C31H23BrO3/c32-24-15-13-20(14-16-24)19-9-11-21(12-10-19)23-17-22-5-1-2-6-25(22)27(18-23)29-30(33)26-7-3-4-8-28(26)35-31(29)34/h1-16,23,27,33H,17-18H2<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: VEUZZDOCACZPRY-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/C31H23BrO3/c32-24-15-13-20(14-16-24)19-9-11-21(12-10-19)23-17-22-5-1-2-6-25(22)27(18-23)29-30(33)26-7-3-4-8-28(26)35-31(29)34/h1-16,23,27,33H,17-18H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: VEUZZDOCACZPRY-UHFFFAOYAI</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%;">Brc1ccc(cc1)c2ccc(cc2)C4Cc3ccccc3C(C4)C\5=C(/O)c6ccccc6OC/5=O</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>31</sub><span title="Hydrogen">H</span><sub>23</sub><span title="Bromine">Br</span><span title="Oxygen">O</span><sub>3</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="7002523426000000000♠"></span>523.426</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>228 to 230 °C (442 to 446 °F; 501 to 503 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>Insoluble </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></div> </td> <td>Oral; dermal; inhalation (dusts) (for poisoning) </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetics</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></div> </td> <td>100% </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Metabolism" title="Metabolism">Metabolism</a></div> </td> <td>slow, incomplete, hepatic </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Biological_half-life" title="Biological half-life">Biological half-life</a></div> </td> <td>Slow; 20—130 days </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></div> </td> <td>faeces; very slow </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>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>270 μg/kg (rat, oral) </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=443426826&page2=Brodifacoum">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>Brodifacoum</b> is a highly lethal <a href="/wiki/4-Hydroxycoumarins" title="4-Hydroxycoumarins">4-hydroxycoumarin</a> <a href="/wiki/Vitamin_K_antagonist" title="Vitamin K antagonist">vitamin K antagonist</a> <a href="/wiki/Anticoagulant" title="Anticoagulant">anticoagulant</a> <a href="/wiki/Poison" title="Poison">poison</a>. In recent years, it has become one of the world's most widely used <a href="/wiki/Pesticides" class="mw-redirect" title="Pesticides">pesticides</a>. It is typically used as a <a href="/wiki/Rodenticide" title="Rodenticide">rodenticide</a>, but is also used to control larger pests such as <a href="/wiki/Common_brushtail_possum" title="Common brushtail possum">possums</a>.<sup id="cite_ref-DoCManual_2-0" class="reference"><a href="#cite_note-DoCManual-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Brodifacoum has an especially long half-life in the body, which ranges up to nine months, requiring prolonged treatment with antidotal <a href="/wiki/Vitamin_K" title="Vitamin K">vitamin K</a> for both human and pet poisonings. It has one of the highest risks of <a href="/wiki/Secondary_poisoning" title="Secondary poisoning">secondary poisoning</a> to both mammals and birds.<sup id="cite_ref-NPICRodenticides_3-0" class="reference"><a href="#cite_note-NPICRodenticides-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Significant experience in brodifacoum poisonings has been gained in many human cases where it has been used in attempted suicides, necessitating long periods of vitamin K treatment. In March 2018, cases of severe <a href="/wiki/Coagulopathy" title="Coagulopathy">coagulopathy</a> and bleeding associated with <a href="/wiki/Synthetic_cannabinoid" class="mw-redirect" title="Synthetic cannabinoid">synthetic cannabinoid</a> use contaminated with brodifacoum were reported in five states of the US. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Chemical_synthesis">Chemical synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Brodifacoum&action=edit&section=1" title="Edit section: Chemical synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Brodifacoum is a derivative of the 4-hydroxy-coumarin group. Compounds numbers are found next to their respective compounds in the image below. Compound 1 is the starting ester needed to synthesize brodifacoum. To obtain this starting Compound 1, a simple <a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig condensation</a> of <a href="/wiki/Ethyl_chloroacetate" title="Ethyl chloroacetate">ethyl chloroacetate</a> with 4’-bromobiphenylcarboxaldehyde is accomplished. Compound 1 is transformed into Compound 2 by consecutive <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a>, <a href="/wiki/Halogenation" title="Halogenation">halogenation</a> to form an <a href="/wiki/Acid_chloride" class="mw-redirect" title="Acid chloride">acid chloride</a>, and then reacted with the required <a href="/wiki/Lithium" title="Lithium">lithium</a> <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a>. This is done using KOH and EtOH for hydrolysis, and then adding SOCl<sub>2</sub> for chlorination to form the <a href="/wiki/Acid_chloride" class="mw-redirect" title="Acid chloride">acid chloride</a> which reacts with the addition of lithium anion. Compound 2 is then transformed using <a href="/wiki/Organocopper_compound" class="mw-redirect" title="Organocopper compound">organocopper</a> chemistry to yield Compound 3 with good <a href="/wiki/Stereoselectivity" title="Stereoselectivity">stereoselectivity</a> of about 98%. Typically, a <a href="/wiki/Friedel-Crafts" class="mw-redirect" title="Friedel-Crafts">Friedel-Crafts</a> type cyclization would then be used to obtain the two-ring system portion of Compound 4, but this results in low yield. Instead, <a href="/wiki/Trifluoromethanesulfonic_acid" class="mw-redirect" title="Trifluoromethanesulfonic acid">trifluoromethanesulfonic acid</a> in dry <a href="/wiki/Benzene" title="Benzene">benzene</a> catalyzes the cyclization with good yield. The <a href="/wiki/Ketone" title="Ketone">ketone</a> is then reduced with <a href="/wiki/Sodium_borohydride" title="Sodium borohydride">sodium borohydride</a> yielding a <a href="/wiki/Benzyl_alcohol" title="Benzyl alcohol">benzyl alcohol</a>. Condensation with 4-hydroxycoumarin under HCl yields Compound 5, brodifacoum.<sup id="cite_ref-Synthesis_of_stereospecific_Brodifacoum_4-0" class="reference"><a href="#cite_note-Synthesis_of_stereospecific_Brodifacoum-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Synthesis_of_Brodifacoum.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Synthesis_of_Brodifacoum.png/220px-Synthesis_of_Brodifacoum.png" decoding="async" width="220" height="446" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Synthesis_of_Brodifacoum.png/330px-Synthesis_of_Brodifacoum.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/Synthesis_of_Brodifacoum.png/440px-Synthesis_of_Brodifacoum.png 2x" data-file-width="2204" data-file-height="4472" /></a><figcaption>Stereospecific formation of Brodifacoum using an asymmetric organocopper compound.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Toxicology">Toxicology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Brodifacoum&action=edit&section=2" title="Edit section: Toxicology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Brodifacoum is a <a href="/wiki/4-hydroxycoumarin" class="mw-redirect" title="4-hydroxycoumarin">4-hydroxycoumarin</a> anticoagulant, with a similar mode of action to its historical predecessors <a href="/wiki/Dicoumarol" title="Dicoumarol">dicoumarol</a> and <a href="/wiki/Warfarin" title="Warfarin">warfarin</a>. However, due to very high potency and long duration of action (elimination <a href="/wiki/Half-life" title="Half-life">half-life</a> of 20 – 130 days), it is characterised as a "second-generation" or "<a href="/wiki/Superwarfarin" title="Superwarfarin">superwarfarin</a>" anticoagulant.<sup id="cite_ref-autogenerated1_5-0" class="reference"><a href="#cite_note-autogenerated1-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Brodifacoum inhibits the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Vitamin_K_epoxide_reductase" title="Vitamin K epoxide reductase">vitamin K epoxide reductase</a>, which is needed for the reconstitution of the vitamin K in its cycle from vitamin K-epoxide, so brodifacoum steadily decreases the level of active vitamin K in the blood. Vitamin K is required for the synthesis of important substances including <a href="/wiki/Prothrombin" class="mw-redirect" title="Prothrombin">prothrombin</a>, which is involved in <a href="/wiki/Blood_clotting" class="mw-redirect" title="Blood clotting">blood clotting</a>. This disruption becomes increasingly severe until the blood effectively loses any ability to clot. </p><p>In addition, brodifacoum (as with other anticoagulants in toxic doses) increases <a href="/wiki/Vascular_permeability" title="Vascular permeability">permeability</a> of blood capillaries; the blood plasma and blood itself begin to leak from the smallest blood vessels. A poisoned animal suffers progressively worsening internal bleeding, leading to <a href="/wiki/Shock_(circulatory)" title="Shock (circulatory)">shock</a>, loss of consciousness, and eventually <a href="/wiki/Death" title="Death">death</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2019)">citation needed</span></a></i>]</sup> </p><p>Brodifacoum is highly lethal to mammals and birds, and extremely lethal to fish. It is a highly <a href="/wiki/Bioaccumulation" title="Bioaccumulation">cumulative</a> poison, due to its high <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilicity</a> and extremely slow <a href="/wiki/Clearance_(medicine)" class="mw-redirect" title="Clearance (medicine)">elimination</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2019)">citation needed</span></a></i>]</sup> </p><p>Following are acute <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a> values for a variety of animals: </p> <table> <tbody><tr> <td>* rats (oral)</td> <td>0.27 mg/kg b.w.<sup id="cite_ref-who#57_6-0" class="reference"><a href="#cite_note-who#57-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>* mice (oral)</td> <td>0.40 mg/kg b.w.<sup id="cite_ref-who#57_6-1" class="reference"><a href="#cite_note-who#57-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>* rabbits (oral)</td> <td>0.30 mg/kg b.w.<sup id="cite_ref-who#57_6-2" class="reference"><a href="#cite_note-who#57-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>* guinea-pigs (oral)</td> <td>0.28 mg/kg b.w.<sup id="cite_ref-who#57_6-3" class="reference"><a href="#cite_note-who#57-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>* squirrels (oral)</td> <td>0.13 mg/kg b.w.<sup id="cite_ref-matschke1883_7-0" class="reference"><a href="#cite_note-matschke1883-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>* cats (oral)<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></td> <td>0.25 mg/kg b.w.<sup id="cite_ref-inchem_9-0" class="reference"><a href="#cite_note-inchem-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-who#57_6-4" class="reference"><a href="#cite_note-who#57-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> — 25 mg/kg b.w.<sup id="cite_ref-KAUKEINEN_10-0" class="reference"><a href="#cite_note-KAUKEINEN-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-cornell_11-0" class="reference"><a href="#cite_note-cornell-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-orica_12-0" class="reference"><a href="#cite_note-orica-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-vetguide_13-0" class="reference"><a href="#cite_note-vetguide-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-who#57_6-5" class="reference"><a href="#cite_note-who#57-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><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> </td></tr> <tr> <td>* dogs (oral)</td> <td>0.25 — 3.6 mg/kg b.w.<sup id="cite_ref-who#57_6-6" class="reference"><a href="#cite_note-who#57-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-inchem_9-1" class="reference"><a href="#cite_note-inchem-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KAUKEINEN_10-1" class="reference"><a href="#cite_note-KAUKEINEN-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-cornell_11-1" class="reference"><a href="#cite_note-cornell-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-orica_12-1" class="reference"><a href="#cite_note-orica-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-vetguide_13-1" class="reference"><a href="#cite_note-vetguide-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>* birds</td> <td>LD<sub>50</sub> values for various birds vary from about 1 mg/kg b.w. — 20 mg/kg b.w.<sup id="cite_ref-autogenerated1_5-1" class="reference"><a href="#cite_note-autogenerated1-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>* fish — LC<sub>50</sub> for fish: </td></tr> <tr> <td>** trout (96 hours exposure)</td> <td>0.04 ppm<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> </td></tr> </tbody></table> <p>As brodifacoum is not selective and can cause secondary poisoning of predators,<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> its outdoor use is either banned or not recommended; the only exception is use for rodent eradication from islands (where it is feasible), because invasive rodents can be destructive for seabirds.<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> Biological resistance to Brodifacoum has been indicated in some species of rats in sample studies <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="Brand_names">Brand names</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Brodifacoum&action=edit&section=3" title="Edit section: Brand names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Brodifacoum_notice.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Brodifacoum_notice.jpg/220px-Brodifacoum_notice.jpg" decoding="async" width="220" height="293" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Brodifacoum_notice.jpg/330px-Brodifacoum_notice.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Brodifacoum_notice.jpg/440px-Brodifacoum_notice.jpg 2x" data-file-width="3000" data-file-height="4000" /></a><figcaption>Notice about laying of brodifacoum baits in New Zealand</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Ratpoison_Bait_Box.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Ratpoison_Bait_Box.JPG/220px-Ratpoison_Bait_Box.JPG" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Ratpoison_Bait_Box.JPG/330px-Ratpoison_Bait_Box.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Ratpoison_Bait_Box.JPG/440px-Ratpoison_Bait_Box.JPG 2x" data-file-width="922" data-file-height="691" /></a><figcaption>Baitbox containing brodifacoum in Finland</figcaption></figure> <p>Brodifacoum is marketed under many trade names, including Arakus (Advansia), Biosnap, <a href="/wiki/D-CON" title="D-CON">d-CON</a>, Finale, Fologorat, Havoc, Jaguar, Klerat, Matikus, Mouser, Pestoff, Rakan, Ratak+, Rataquill Colombia, Ratshot Red, Rattex, Rodend, Rodenthor, Ratsak, Talon,<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> Volak, Vertox, and Volid.<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. (August 2021)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Human_poisoning">Human poisoning</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Brodifacoum&action=edit&section=4" title="Edit section: Human poisoning"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Treatment">Treatment</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Brodifacoum&action=edit&section=5" title="Edit section: Treatment"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The primary antidote to brodifacoum poisoning is immediate administration of <a href="/wiki/Vitamin_K" title="Vitamin K">vitamin K<sub>1</sub></a> (dosage for humans: initially slow intravenous injections of 10–25 mg repeated at 3–6 hours until normalisation of the prothrombin time; then 10 mg orally four times daily as a "maintenance dose"). It is an extremely effective antidote, provided the poisoning is caught before excessive bleeding ensues. As high doses of brodifacoum can affect the body for many months, the antidote must be administered regularly for a long period (several months, in keeping with the substance's half-life) with frequent monitoring of the <a href="/wiki/Prothrombin_time" title="Prothrombin time">prothrombin time</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><p>If unabsorbed poison is still in the digestive system, <a href="/wiki/Gastric_lavage" title="Gastric lavage">gastric lavage</a> followed by administration of <a href="/wiki/Activated_charcoal" class="mw-redirect" title="Activated charcoal">activated charcoal</a> may be required. </p><p>Further treatments to be considered include infusion of <a href="/wiki/Blood" title="Blood">blood</a> or <a href="/wiki/Blood_plasma" title="Blood plasma">plasma</a> to counteract <a href="/wiki/Hypovolemia" title="Hypovolemia">hypovolemic shock</a>, and in severe cases, infusion of <a href="/wiki/Prothrombin_complex_concentrate" title="Prothrombin complex concentrate">blood clotting factor concentrate</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Case_reports">Case reports</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Brodifacoum&action=edit&section=6" title="Edit section: Case reports"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cases of brodifacoum intoxication have been reported in the human medical literature. </p><p>In one report, a woman deliberately consumed over 1.5 kg (3 lb) of rat bait, constituting about 75 mg brodifacoum, but made a full recovery after receiving conventional medical treatment.<sup id="cite_ref-LiptonKlass_21-0" class="reference"><a href="#cite_note-LiptonKlass-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>In another case reported in 2013, a 48-year-old female patient reported 4 days of mild <a href="/wiki/Dyspnea" class="mw-redirect" title="Dyspnea">dyspnea</a>, dry cough, bilateral popliteal fossae pain, and diffuse upper abdominal pain. She had no history of liver disease or <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">alcohol</a> or <a href="/wiki/Narcotic" title="Narcotic">illicit substance</a> <a href="/wiki/Drug_abuse" class="mw-redirect" title="Drug abuse">abuse</a>. Initial physical examination was remarkable only for mildly pale <a href="/wiki/Conjunctivae" class="mw-redirect" title="Conjunctivae">conjunctivae</a> and mild abdominal tenderness and pain in the left <a href="/wiki/Popliteal_fossa" title="Popliteal fossa">popliteal fossa</a>. A complete blood count and complete metabolic panel were normal. <a href="/wiki/Prothrombin" class="mw-redirect" title="Prothrombin">Prothrombin</a> time (PT) was above 100 s, partial <a href="/wiki/Thromboplastin" title="Thromboplastin">thromboplastin</a> time (PTT) was above 200 s and international normalized ratio (INR) was reported as above 12.0. Urinalysis revealed <a href="/wiki/Hematuria" title="Hematuria">hematuria</a> (blood in the urine). Venous <a href="/wiki/Doppler_ultrasound" class="mw-redirect" title="Doppler ultrasound">Doppler ultrasound</a> of lower extremities demonstrated left popliteal vein <a href="/wiki/Thrombosis" title="Thrombosis">thrombosis</a>. Computed tomography scan of the abdomen demonstrated transmural hematoma, and a <a href="/wiki/Fecal_occult_blood_test" class="mw-redirect" title="Fecal occult blood test">fecal occult blood test</a> was positive. A full anticoagulant work-up showed critical reduction of vitamin K-dependent factors II, VII, IX, and X. PT and PTT corrected with mixing studies proving factor deficiency as the cause of the <a href="/wiki/Coagulopathy" title="Coagulopathy">coagulopathy</a>. <a href="/wiki/Lupus_anticoagulant" title="Lupus anticoagulant">Lupus anticoagulant</a> studies were negative. Superwarfarin toxicity was suspected and confirmed with an anticoagulant poison panel positive for brodifacoum. The patient was hospitalized and successfully treated with fresh frozen plasma, <a href="/wiki/Cryoprecipitate" title="Cryoprecipitate">cryoprecipitate</a>, and vitamin K. In conclusion, paradoxical thrombosis and hemorrhage should raise the suspicion for superwarfarin toxicity in the appropriate clinical setting. Concomitant presentation for thrombosis and hemorrhage with remarkably abnormal PT and PTT should raise the suspicion for brodifacoum poisoning.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>In 2015, 19 <a href="/wiki/Inmate" class="mw-redirect" title="Inmate">inmates</a> in <a href="/wiki/New_York_City" title="New York City">New York City</a>'s <a href="/wiki/Rikers_Island" title="Rikers Island">Rikers Island</a> jail claimed that they had been poisoned with the chemical. The inmates had noticed "what appeared to be blue and green pellets in the <a href="/wiki/Meatloaf" title="Meatloaf">meatloaf</a>" they were eating on March 3, and felt ill afterwards. A sample was analyzed and tested positive for brodifacoum; the <a href="/wiki/New_York_City_Department_of_Correction" title="New York City Department of Correction">NYC Department of Correction</a> stated it was investigating the incident.<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><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>A 20-year-old female college student presented with abdominal pain and blood in urine. She was tested for <a href="/wiki/Warfarin" title="Warfarin">warfarin</a>, a common anticoagulant also used in some rodenticides, which returned a negative result. Vitamin K and fresh <a href="/wiki/Blood_plasma" title="Blood plasma">plasma</a> were administered to treat symptoms. Three weeks later, she returned with bleeding into her calf, and was subsequently tested for superwarfarin chemicals. The test showed that brodifacoum was in her bloodstream. She later admitted to consuming seven packets of <a href="/wiki/Rodenticide" title="Rodenticide">rodenticide</a>.<sup id="cite_ref-WeitzelEtAl_25-0" class="reference"><a href="#cite_note-WeitzelEtAl-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>A 48-year-old businessman was admitted with a severe nosebleed and abnormal coagulation parameters. Standard treatment of vitamin K and fresh plasma was administered to stem the nosebleed. Two weeks later, he presented again with bleeding into the calf. Continual doses of vitamin K were necessary to counteract the brodifacoum. He denied taking any of the brodifacoum found in his home contained within packages of Contrac.<sup id="cite_ref-WeitzelEtAl_25-1" class="reference"><a href="#cite_note-WeitzelEtAl-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Recreational_drug_use">Recreational drug use</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Brodifacoum&action=edit&section=7" title="Edit section: Recreational drug use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Brodifacoum has been mixed with <a href="/wiki/Synthetic_cannabinoid" class="mw-redirect" title="Synthetic cannabinoid">synthetic cannabinoids</a> such as K2 and Spice, reportedly "to extend the duration of the drug euphoria".<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>As of November 26, 2018, at least eight fatalities and 320 cases of severe coagulopathy and bleeding associated with synthetic cannabinoid use had been reported in Illinois, Wisconsin, Maryland, Missouri, Florida, North Carolina, Indiana, Pennsylvania, Kentucky, Virginia, and West Virginia.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><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> The first case occurred in Illinois on March 7, 2018.<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> Brodifacoum was suspected to be present in these products in Illinois. Products named <b>Matrix</b> and <b>Blue Giant</b> from a convenience store in Chicago have tested positive for brodifacoum and <a href="/wiki/AMB-FUBINACA" title="AMB-FUBINACA">AMB-FUBINACA</a> (FUB-AMB).<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><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>In another report, a 17-year-old boy presented to the hospital with a severe bleeding disorder. He was found to have habitually smoked a mixture of brodifacoum and <a href="/wiki/Marijuana" class="mw-redirect" title="Marijuana">marijuana</a>. Despite treatment with vitamin K, the bleeding disorder persisted for several months. He eventually recovered.<sup id="cite_ref-LaRosaEtAl_34-0" class="reference"><a href="#cite_note-LaRosaEtAl-34"><span class="cite-bracket">[</span>34<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=Brodifacoum&action=edit&section=8" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><i><a href="/wiki/Merck_Index" title="Merck Index">Merck Index</a></i>, 11th Edition, <b>1368</b></span> </li> <li id="cite_note-DoCManual-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-DoCManual_2-0">^</a></b></span> <span class="reference-text">Eason, C.T. and Wickstrom, M. <i>Vertebrate pesticide toxicology manual</i>, <a href="/wiki/New_Zealand_Department_of_Conservation" class="mw-redirect" title="New Zealand Department of Conservation">New Zealand Department of Conservation</a></span> </li> <li id="cite_note-NPICRodenticides-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-NPICRodenticides_3-0">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://npic.orst.edu/factsheets/rodenticides.html">Rodenticides: Topic Fact Sheet</a>, <a href="/wiki/National_Pesticide_Information_Center" title="National Pesticide Information Center">National Pesticide Information Center</a></span> </li> <li id="cite_note-Synthesis_of_stereospecific_Brodifacoum-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-Synthesis_of_stereospecific_Brodifacoum_4-0">^</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 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(1997), "Efficient Asymmetric Synthesis of the Four Diastereomers of Diphenacoum and Brodifacoum", <i>Tetrahedron</i>, <b>43</b> (17): 6045–6056, <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%2FS0040-4020%2897%2900254-8">10.1016/S0040-4020(97)00254-8</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=Efficient+Asymmetric+Synthesis+of+the+Four+Diastereomers+of+Diphenacoum+and+Brodifacoum&rft.volume=43&rft.issue=17&rft.pages=6045-6056&rft.date=1997&rft_id=info%3Adoi%2F10.1016%2FS0040-4020%2897%2900254-8&rft.au=van+Heerden+P.+S.&rft.au=Bezuidenhoudt+B.+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABrodifacoum" class="Z3988"></span></span> </li> <li id="cite_note-autogenerated1-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-autogenerated1_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-autogenerated1_5-1"><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 class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/hsg/hsg/hsg093.htm">"Brodifacoum (HSG 93, 1995)"</a>. 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Retrieved <span class="nowrap">2017-12-05</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Brodifacoum+%28PDS%29&rft.pub=Inchem.org&rft_id=http%3A%2F%2Fwww.inchem.org%2Fdocuments%2Fpims%2Fchemical%2Fpim077.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABrodifacoum" class="Z3988"></span></span> </li> <li id="cite_note-matschke1883-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-matschke1883_7-0">^</a></b></span> <span class="reference-text"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMatschkeBaril,_Steve_F.Blaskiewicz,_Raymond_W.1983" class="citation journal cs1">Matschke, George H.; Baril, Steve F.; Blaskiewicz, Raymond W. (December 1983). <a rel="nofollow" class="external text" href="http://digitalcommons.unl.edu/cgi/viewcontent.cgi?article=1281&context=gpwdcwp">"Population Reduction of Richardson's Ground Squirrels Using a Brodifacoum Bait"</a>. <i>Great Plains Wildlife Damage Control Workshop Proceedings --- University of Nebraska-Lincoln</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Great+Plains+Wildlife+Damage+Control+Workshop+Proceedings+---+University+of+Nebraska-Lincoln&rft.atitle=Population+Reduction+of+Richardson%27s+Ground+Squirrels+Using+a+Brodifacoum+Bait&rft.date=1983-12&rft.aulast=Matschke&rft.aufirst=George+H.&rft.au=Baril%2C+Steve+F.&rft.au=Blaskiewicz%2C+Raymond+W.&rft_id=http%3A%2F%2Fdigitalcommons.unl.edu%2Fcgi%2Fviewcontent.cgi%3Farticle%3D1281%26context%3Dgpwdcwp&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABrodifacoum" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text">Published LD50 values of brodifacoum for cats vary widely, from 25 mg kg-1(Rammell et al., 1984;Godfrey, 1985) to 0.25 mg kg-1(Haydock and Eason, 1997)</span> </li> <li id="cite_note-inchem-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-inchem_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-inchem_9-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/pims/chemical/pim077.htm">Brodifacoum at InChem.com</a></span> </li> <li id="cite_note-KAUKEINEN-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-KAUKEINEN_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-KAUKEINEN_10-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">KAUKEINEN, D.E. 1979. Experimental rodenticide (Talon) passes lab tests; moving to field trials in pest control industry. Pest Control 46(1):19-21.</span> </li> <li id="cite_note-cornell-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-cornell_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-cornell_11-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://pmep.cce.cornell.edu/profiles/rodent/rodent_A_L/brodifacoum/brodif_prf_0185.html">Brodifacoum (Talon, Havoc) - Chemical Profile 1/85</a></span> </li> <li id="cite_note-orica-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-orica_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-orica_12-1"><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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20090914151114/http://msds.orica.com/pdf/shess-en-cds-010-000000020872.pdf">"MSDS Data Sheet for TALON RAT AND MOUSE KILLER"</a> <span class="cs1-format">(PDF)</span>. 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Retrieved <span class="nowrap">2016-08-20</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=The+Veterinarian%27s+Guide+to+accidental+rodenticideingestion+by+dogs+%26+cats&rft_id=http%3A%2F%2Fwww.liphatech.com%2Fuploads%2Ffiles%2Fpdf%2FUS%2FLiterature%2Fvet_guide_pmd.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABrodifacoum" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://newzealandecology.org/nzje/free_issues/NZJEcol23_2_207.pdf">Brodifacoum residues in target and non-target species following an aerial poisoning operation on Motuihe Island, Hauraki Gulf, NEW ZEALAND</a> Pdf</span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</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.wil-kil.com/public/2005-06_labels-msds/WeatherBlok%20XT%20M.pdf#search=%22LC50%2Bbrodifacoum%22">"Pest Control Product Labels And MSDS"</a> <span class="cs1-format">(PDF)</span>. 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2 deaths, 54 others cases of severe bleeding"</a>. <i>WGN-TV</i>. 2 April 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=WGN-TV&rft.atitle=3+arrested+in+Chicago+in+connection+to+synthetic+pot%3B+2+deaths%2C+54+others+cases+of+severe+bleeding&rft.date=2018-04-02&rft_id=http%3A%2F%2Fwgntv.com%2F2018%2F04%2F02%2F2-deaths-54-other-cases-of-severe-bleeding-tied-to-fake-weed-in-illinois%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABrodifacoum" class="Z3988"></span></span> </li> <li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.justice.gov/usao-ndil/press-release/file/1048041">"Masoud et al complaint - Department of Justice"</a>. <i>www.justice.gov</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.justice.gov&rft.atitle=Masoud+et+al+complaint+-+Department+of+Justice&rft_id=https%3A%2F%2Fwww.justice.gov%2Fusao-ndil%2Fpress-release%2Ffile%2F1048041&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABrodifacoum" class="Z3988"></span></span> </li> <li id="cite_note-LaRosaEtAl-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-LaRosaEtAl_34-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLa_Rosa_FClarke_SLefkowitz_J_B1997" class="citation journal cs1">La Rosa F; Clarke S; Lefkowitz J B (1997). "Brodifacoum intoxication with marijuana smoking". <i>Archives of Pathology & Laboratory Medicine</i>. <b>121</b>: 67–69.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archives+of+Pathology+%26+Laboratory+Medicine&rft.atitle=Brodifacoum+intoxication+with+marijuana+smoking&rft.volume=121&rft.pages=67-69&rft.date=1997&rft.au=La+Rosa+F&rft.au=Clarke+S&rft.au=Lefkowitz+J+B&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABrodifacoum" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Brodifacoum&action=edit&section=9" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Tasheva, M. (1995). <i>Environmental Health Criteria 175: Anticoagulant rodenticides</i>. World Health Organisation: Geneva.</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCabot_Richard_C2007" class="citation journal cs1">Cabot Richard C (2007). "Case Records of the Massachusetts General Hospital (a near fatal case of brodifacoum poisoning)". <i>New England Journal of Medicine</i>. <b>356</b> (2): 174–182. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1056%2FNEJMcpc069032">10.1056/NEJMcpc069032</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/17215536">17215536</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=New+England+Journal+of+Medicine&rft.atitle=Case+Records+of+the+Massachusetts+General+Hospital+%28a+near+fatal+case+of+brodifacoum+poisoning%29&rft.volume=356&rft.issue=2&rft.pages=174-182&rft.date=2007&rft_id=info%3Adoi%2F10.1056%2FNEJMcpc069032&rft_id=info%3Apmid%2F17215536&rft.au=Cabot+Richard+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABrodifacoum" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBell2015" class="citation journal cs1">Bell, Cathy (July 15, 2015). <a rel="nofollow" class="external text" href="http://www.allaboutbirds.org/raptors-and-rat-poison/">"Raptors and Rat Poison"</a>. <i>Living Bird Magazine</i><span class="reference-accessdate">. Retrieved <span class="nowrap">November 20,</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Living+Bird+Magazine&rft.atitle=Raptors+and+Rat+Poison&rft.date=2015-07-15&rft.aulast=Bell&rft.aufirst=Cathy&rft_id=http%3A%2F%2Fwww.allaboutbirds.org%2Fraptors-and-rat-poison%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABrodifacoum" class="Z3988"></span></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol 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title="Coumarin">Coumarins</a> /<br /><a href="/wiki/4-Hydroxycoumarins" title="4-Hydroxycoumarins">4-Hydroxycoumarins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;font-size:smaller;">1st generation</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Warfarin" title="Warfarin">Warfarin</a></li> <li><a href="/wiki/Coumatetralyl" title="Coumatetralyl">Coumatetralyl</a></li> <li><a href="/wiki/Fumarin" title="Fumarin">Fumarin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;font-size:smaller;">2nd generation (<a href="/wiki/Superwarfarin" 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title="Pindone">Pindone</a></li> <li><a href="/wiki/Diphacinone" class="mw-redirect" title="Diphacinone">Diphacinone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Convulsant" title="Convulsant">Convulsants</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Crimidine" title="Crimidine">Crimidine</a></li> <li><a href="/wiki/Phenylsilatrane" title="Phenylsilatrane">Phenylsilatrane</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Tetramethylenedisulfotetramine" title="Tetramethylenedisulfotetramine">Tetramethylenedisulfotetramine</a></li> <li><a href="/wiki/Chlorophenylsilatrane" title="Chlorophenylsilatrane">Chlorophenylsilatrane</a></li> <li><a href="/wiki/RDX" title="RDX">RDX</a></li></ul> </div></td></tr><tr><th 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