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class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>α-Naphthylthiourea </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:1-(naphthalen-1-yl)thiourea_200.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/1-%28naphthalen-1-yl%29thiourea_200.svg/220px-1-%28naphthalen-1-yl%29thiourea_200.svg.png" decoding="async" width="220" height="196" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/1-%28naphthalen-1-yl%29thiourea_200.svg/330px-1-%28naphthalen-1-yl%29thiourea_200.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/56/1-%28naphthalen-1-yl%29thiourea_200.svg/440px-1-%28naphthalen-1-yl%29thiourea_200.svg.png 2x" data-file-width="159" data-file-height="142" /></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;">Naphthalen-1-ylthiourea</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;">ANTU<br />1-(1-Naphthyl)-2-thiourea<br />1-(1-Naphthyl)thiourea<br />1-Naphthylthiourea<br />α-Naphthylthiocarbamide<br />1-(Naphthalen-1-yl)thiourea<br />Dirax<br />Anturat<br />Rattrack<br />Smeesana<br />Alrato</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=86-88-4">86-88-4</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=C1%3DCC%3DC2C%28%3DC1%29C%3DCC%3DC2NC%28%3DS%29N">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=S%3DC%28N%29Nc2cccc1ccccc12">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>Abbreviations </td> <td>ANTU </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.643492.html">643492</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/100.001.552">100.001.552</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q413532#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/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/C19136">C19136</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><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/736366">736366</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/UKY0H6XJ4J">UKY0H6XJ4J</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/DTXSID8020919">DTXSID8020919</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q413532#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/C11H10N2S/c12-11(14)13-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,(H3,12,13,14)<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: PIVQQUNOTICCSA-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/C11H10N2S/c12-11(14)13-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,(H3,12,13,14)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: PIVQQUNOTICCSA-UHFFFAOYAV</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%;">C1=CC=C2C(=C1)C=CC=C2NC(=S)N</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%;">S=C(N)Nc2cccc1ccccc12</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>11</sub><span title="Hydrogen">H</span><sub>10</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Sulfur">S</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002202280000000000♠"></span>202.28</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>White solid,<sup id="cite_ref-PGCH_1-0" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> crystallizes in prisms from alcohol<sup id="cite_ref-O'Neil,_M.J._2001._p._122_2-0" class="reference"><a href="#cite_note-O'Neil,_M.J._2001._p._122-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Colorless, solid. White.<sup id="cite_ref-Mackison,_F._W._1981._p._1-2_3-0" class="reference"><a href="#cite_note-Mackison,_F._W._1981._p._1-2-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> White, crystalline or gray powder.<sup id="cite_ref-ReferenceA_4-0" class="reference"><a href="#cite_note-ReferenceA-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>197.8 °C (388.0 °F; 470.9 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>Decomposes </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>600 mg/L </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in other solvents </td> <td>2.43 g/100mL (acetone) <br />8.6 g/100mL (triethylene glycol) <sup id="cite_ref-O'Neil,_M.J._2001._p._122_2-1" class="reference"><a href="#cite_note-O'Neil,_M.J._2001._p._122-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>1.65 <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> </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>6.6x10<sup>−6</sup> mmHg <sup id="cite_ref-epa.gov_6-0" class="reference"><a href="#cite_note-epa.gov-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Henry%27s_law" title="Henry's law">Henry's law<br />constant</a> (<i>k</i><sub>H</sub>)</div> </td> <td>8.51x10<sup>−9</sup> atm-cu m/mol <sup id="cite_ref-epa.gov_6-1" class="reference"><a href="#cite_note-epa.gov-6"><span class="cite-bracket">[</span>6<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>Toxic </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_8a72be159ebe5ef6" /></span><map name="ImageMap_8a72be159ebe5ef6"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" title="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 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 4: Very short exposure could cause death or major residual injury. E.g. VX gas" class="notheme mw-no-invert">4</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 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>noncombustible<sup id="cite_ref-PGCH_1-1" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>0.38 mg/kg (dog, oral)<br />6 mg/kg (rat, oral)<br />4250 mg/kg (monkey, oral)<br />5 mg/kg (mouse, oral)<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 0.3 mg/m<sup>3</sup><sup id="cite_ref-PGCH_1-2" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>TWA 0.3 mg/m<sup>3</sup><sup id="cite_ref-PGCH_1-3" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>100 mg/m<sup>3</sup><sup id="cite_ref-PGCH_1-4" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477319544&page2=%CE%91-Naphthylthiourea">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>α-Naphthylthiourea</b> (<b>ANTU</b>) is an <a href="/wiki/Organosulfur_compound" class="mw-redirect" title="Organosulfur compound">organosulfur compound</a> with the formula C<sub>10</sub>H<sub>7</sub>NHC(S)NH<sub>2</sub>. This a white, crystalline powder although commercial samples may be off-white.<sup id="cite_ref-Mackison,_F._W._1981._p._1-2_3-1" class="reference"><a href="#cite_note-Mackison,_F._W._1981._p._1-2-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-O'Neil,_M.J._2001._p._122_2-2" class="reference"><a href="#cite_note-O'Neil,_M.J._2001._p._122-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ReferenceA_4-1" class="reference"><a href="#cite_note-ReferenceA-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is used as a <a href="/wiki/Rodenticide" title="Rodenticide">rodenticide</a> and as such is fairly toxic. Naphthylthiourea is available as 10% active baits in suitable protein- or carbohydrate-rich materials and as a 20% tracking powder.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <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=%CE%91-Naphthylthiourea&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Like other <a href="/wiki/Thiourea" title="Thiourea">thioureas</a>, ANTU can be prepared by several routes. The usual method is the reaction of <a href="/wiki/1-naphthylamine" class="mw-redirect" title="1-naphthylamine">1-naphthylamine</a> hydrochloride with <a href="/wiki/Ammonium_thiocyanate" title="Ammonium thiocyanate">ammonium thiocyanate</a>:<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>[C<sub>10</sub>H<sub>7</sub>NH<sub>3</sub>]Cl + NH<sub>4</sub>SCN → C<sub>10</sub>H<sub>7</sub>NHC(S)NH<sub>2</sub> + NH<sub>3</sub> + HCl</dd></dl> <p>It is produced from the reaction of <a href="/wiki/1-Naphthyl_isothiocyanate" title="1-Naphthyl isothiocyanate">1-naphthyl isothiocyanate</a> with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>. </p> <dl><dd>C<sub>10</sub>H<sub>7</sub>NCS + NH<sub>3</sub> → C<sub>10</sub>H<sub>7</sub>NHC(S)NH<sub>2</sub></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91-Naphthylthiourea&action=edit&section=2" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>ANTU is specifically toxic in lung cells due to its conversion to a short-lived active metabolite to which it is converted in the liver, not ANTU acting directly. This damage is focused on the <a href="/wiki/Endothelium" title="Endothelium">endothelium</a> of pulmonary capillaries and venules, it will lead to the formation of irreversible gaps in the endothelium of pulmonary vessels. This damage can lead to pulmonary edema. In ANTU poisoning plasma, carbon and <a href="/wiki/Ferritin" title="Ferritin">ferritin</a> escape through a gap in the thick part of the pulmonary capillary into the interstitial tissues of the lung<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91-Naphthylthiourea&action=edit&section=3" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alpha-Naphthylthiourea is toxic to inhalation, ingestion, or skin contact, although the intoxication may be delayed. According to the U.S. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH), the recommended workplace airborne exposure limit is 0.3 mg/m<sup>3</sup> averaged over a 10-hour workshift. Exposure to 100 mg/m<sup>3</sup> is immediately dangerous to life and health. The lethal dose in humans is approximately 4 g/kg.<sup id="cite_ref-NJ_11-0" class="reference"><a href="#cite_note-NJ-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>It is classified as an <a href="/wiki/List_of_extremely_hazardous_substances" class="mw-redirect" title="List of extremely hazardous substances">extremely hazardous substance</a> in the United States as defined in Section 302 of the U.S. <a href="/wiki/Emergency_Planning_and_Community_Right-to-Know_Act" title="Emergency Planning and Community Right-to-Know Act">Emergency Planning and Community Right-to-Know Act</a> (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.<sup id="cite_ref-gov-right-know_12-0" class="reference"><a href="#cite_note-gov-right-know-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Effects_on_animals">Effects on animals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91-Naphthylthiourea&action=edit&section=4" title="Edit section: Effects on animals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An oral dose of 3 mg per kilogram of body weight causes the death of 50% of the rats exposed (<a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a>), showing a very high selectivity when compared for example to monkeys ( 4000 mg per kilogram of body weight).<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> However other studies have shown a much higher efficacy for dogs (a <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a> of 0.38 mg/kg).<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>The mortality of rats caused by 5 mg/kg of ANTU is reduced when <a href="/w/index.php?title=Allylthiourea&action=edit&redlink=1" class="new" title="Allylthiourea (page does not exist)">allylthiourea</a>, <a href="/w/index.php?title=Isopropylthiourea&action=edit&redlink=1" class="new" title="Isopropylthiourea (page does not exist)">isopropylthiourea</a>, <a href="/wiki/Ethylenethiourea" class="mw-redirect" title="Ethylenethiourea">ethylenethiourea</a>, or <a href="/w/index.php?title=Ethylidenethiourea&action=edit&redlink=1" class="new" title="Ethylidenethiourea (page does not exist)">ethylidenethiourea</a> are administered simultaneously with ANTU.<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> <a href="/wiki/Superoxide_dismutase" title="Superoxide dismutase">Superoxide dismutase</a>, <a href="/wiki/Catalase" title="Catalase">catalase</a> and <a href="/wiki/Dimethylsulfoxide" class="mw-redirect" title="Dimethylsulfoxide">dimethylsulfoxide</a> all protect against the lung damage by ANTU (although the results are diverse). This indicates that <a href="/wiki/OH_radical" class="mw-redirect" title="OH radical">OH radicals</a> are responsible for this type of lung injury. Given <a href="/wiki/Hydroxyurea" class="mw-redirect" title="Hydroxyurea">hydroxyurea</a> over two days does not block the ANTU damage when <a href="/wiki/Neutrophil" title="Neutrophil">neutrophils</a> are decreased or when administered acutely. <a href="/w/index.php?title=Cyclooxygenase_pathway&action=edit&redlink=1" class="new" title="Cyclooxygenase pathway (page does not exist)">Cyclooxygenase pathway</a> may generate the free radicals since <a href="/wiki/Ibuprofen" title="Ibuprofen">ibuprofen</a> blocked as well the ANTU damage.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption>Toxicity of alpha-Naphthyl thiourea in different animals </caption> <tbody><tr> <th>Organism</th> <th>Test type</th> <th>Route</th> <th>Reported dose </th></tr> <tr> <td>Cat<sup id="cite_ref-PSEBM_17-0" class="reference"><a href="#cite_note-PSEBM-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup></td> <td>LD50</td> <td>oral</td> <td>500 mg/kg </td></tr> <tr> <td>Chicken<sup id="cite_ref-PSEBM_17-1" class="reference"><a href="#cite_note-PSEBM-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup></td> <td>LD50</td> <td>intraperitoneal</td> <td>2500 mg/kg </td></tr> <tr> <td>Chicken<sup id="cite_ref-PSEBM_17-2" class="reference"><a href="#cite_note-PSEBM-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup></td> <td>LD50</td> <td>oral</td> <td>4250 mg/kg </td></tr> <tr> <td>Chicken<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></td> <td>LD50</td> <td>unreported</td> <td>700 mg/kg </td></tr> <tr> <td>Dog<sup id="cite_ref-PSEBM_17-3" class="reference"><a href="#cite_note-PSEBM-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup></td> <td>LD50</td> <td>intraperitoneal</td> <td>16 mg/kg </td></tr> <tr> <td>Dog<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></td> <td>LD50</td> <td>oral</td> <td>0.38 mg/kg </td></tr> <tr> <td>Guinea pig<sup id="cite_ref-PSEBM_17-4" class="reference"><a href="#cite_note-PSEBM-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup></td> <td>LD50</td> <td>intraperitoneal</td> <td>350 mg/kg </td></tr> <tr> <td>Man<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></td> <td>LDLo</td> <td>unreported</td> <td>588 mg/kg </td></tr> <tr> <td>Monkey<sup id="cite_ref-PSEBM_17-5" class="reference"><a href="#cite_note-PSEBM-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup></td> <td>LD50</td> <td>intraperitoneal</td> <td>175 mg/kg </td></tr> <tr> <td>Monkey<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></td> <td>LD50</td> <td>oral</td> <td>4250 mg/kg </td></tr> <tr> <td>Monkey<sup id="cite_ref-Bollettino_Chimico_Farmaceutico_1958_22-0" class="reference"><a href="#cite_note-Bollettino_Chimico_Farmaceutico_1958-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup></td> <td>LD50</td> <td>unreported</td> <td>2000 mg/kg </td></tr> <tr> <td>Mouse<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></td> <td>LD50</td> <td>intraperitoneal</td> <td>10 mg/kg </td></tr> <tr> <td>Mouse<sup id="cite_ref-Yakkyoku._Pharmacy_1977_24-0" class="reference"><a href="#cite_note-Yakkyoku._Pharmacy_1977-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup></td> <td>LD50</td> <td>oral</td> <td>5 mg/kg </td></tr> <tr> <td>Pig<sup id="cite_ref-Yakkyoku._Pharmacy_1977_24-1" class="reference"><a href="#cite_note-Yakkyoku._Pharmacy_1977-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup></td> <td>LDLo</td> <td>oral</td> <td>50 mg/kg </td></tr> <tr> <td>Rabbit<sup id="cite_ref-Bollettino_Chimico_Farmaceutico_1958_22-1" class="reference"><a href="#cite_note-Bollettino_Chimico_Farmaceutico_1958-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup></td> <td>LD50</td> <td>unreported</td> <td>200 mg/kg </td></tr> <tr> <td>Rat<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></td> <td>LD50</td> <td>intraperitoneal</td> <td>2.47 mg/ kg </td></tr> <tr> <td>Rat<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></td> <td>LD50</td> <td>oral</td> <td>6 mg/kg </td></tr></tbody></table> <p>ANTU causes local gastric irritation in animals and when it is absorbed, it increases permeability of the lung capillaries in all animals. The symptoms that the animals present after absorption of alpha-naphthyl thiourea are first weakness, <a href="/wiki/Ataxia" title="Ataxia">ataxia</a>, weak pulse and subnormal temperatures. Afterwards, they have the following symptoms: vomiting, hypersalivation, coughing and severe <a href="/wiki/Pulmonary_edema" title="Pulmonary edema">pulmonary edema</a>. In the most cases a pale, mottled liver and damaged kidneys are found in animals which have ingested ANTU. Animals with an empty stomach readily vomit after ingestion of this substance. However, when there is food in the stomach of the animals the stimulation to vomit decreases, so more quantities may be absorbed. It has been found that ANTU may cause death in some animals within 2–4 hours of ingestion, while animals that survive 12 hours may recover from the poison.<sup id="cite_ref-merckmanuals.com_27-0" class="reference"><a href="#cite_note-merckmanuals.com-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> In a long-term, ANTU may cause pulmonary edema and <a href="/wiki/Pleural_effusion" title="Pleural effusion">pleural effusion</a> in certain animals, such as rats. Mice treated with alpha-naphthyl thiourea with a dose of 10 mg/kg developed pulmonary edema which was maximal after 3 hours and was resolved by 12 hours. 35 mg/kg of ANTU was caused death to 60% of the animals. It also increases the blood sugar levels in rats.<sup id="cite_ref-NJ_11-1" class="reference"><a href="#cite_note-NJ-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Dogs and pigs are occasionally poisoned with this compound while <a href="/wiki/Ruminant" title="Ruminant">ruminants</a> are resistant.<sup id="cite_ref-merckmanuals.com_27-1" class="reference"><a href="#cite_note-merckmanuals.com-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> But when the exposure of this compound in dogs is quite long they may have gastric irritation and respiratory difficulties. Death can then be followed within 6–48 hours depending on the quantity of ANTU ingested. </p> <div class="mw-heading mw-heading2"><h2 id="Metabolism">Metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91-Naphthylthiourea&action=edit&section=5" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>α-Naphthylthiourea is metabolized by rat liver and lung <a href="/wiki/Microsome" title="Microsome">microsomes</a> to α-naphthylurea (ANU), which is essentially nontoxic to rats with an (<a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a> > 800 mg/kg). Conversion of ANTU to ANU requires <a href="/wiki/NADPH" class="mw-redirect" title="NADPH">NADPH</a>. <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a> inhibits the reaction.<sup id="cite_ref-Boyd_28-0" class="reference"><a href="#cite_note-Boyd-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> There are some evidence of <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> being responsible for the bioactivation of ANTU. Therefore, the toxicity of ANTU cannot be explained with the activity of ANU. There are subproducts of this reaction which play an important role in toxicity: atomic sulfur and a metabolic reactive containing the carbon carbonyl of ANTU.<sup id="cite_ref-Lee_29-0" class="reference"><a href="#cite_note-Lee-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>The loss of cytochrome P-450 and <a href="/wiki/Monooxygenase" title="Monooxygenase">monooxygenase</a> activity seen on incubation of liver microsomes with ANTU is likely the result of the covalent binding of atomic sulfur to cytochrome P-450. The available evidence suggests that the pulmonary toxicity of ANTU results, at least in part, from the covalent binding of a cytochrome P-450 monooxygenase catalyzed metabolite of ANTU to pulmonary macromolecules. This metabolite is most likely atomic sulfur or alternatively, the one containing the carbonyl carbon of ANTU. However, it is possible that the binding of both metabolites may be responsible for the lung toxicity.<sup id="cite_ref-Lee_29-1" class="reference"><a href="#cite_note-Lee-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91-Naphthylthiourea&action=edit&section=6" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>ANTU was developed to combat infestation of rats in the US city of <a href="/wiki/Baltimore" title="Baltimore">Baltimore</a>, where the increase in population had overwhelmed the sanitation services, causing huge rat-infested garbage piles. Baltimore was also the scene of the discovery of ANTU. In 1942 Curt Richter discovered that phenyl thiourea was lethal, yet tasteless to domesticated rats. This was interesting because a rat's defense against toxins is primarily its sense of taste. However, when Richter started testing the compound in wild rats, it was not equally tasteless for them, but had a bitter taste; Richter's lab screened over 200 thiourea compounds to find one equally tasteless and toxic to wild rats. This led to the discovery of ANTU.<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 2022)">citation needed</span></a></i>]</sup> </p><p>Next Richter set out to test the compound on a large scale. He determined rats will not cross streets and therefore city blocks were used as test areas. Local <a href="/wiki/Boy_Scouts_of_America" title="Boy Scouts of America">Boy Scouts</a> volunteered to distribute the poison. When the first tests returned large amounts of dead rats, the tests were extended to a 200-block area with poor housing. The ANTU field trials soon expanded and in 1943 Richter was asked to lead citywide rat control campaign and received funding to replace the Scouts with adult baiters and trappers. Through a joint effort of the city and volunteers about 8400 city blocks were cleaned from May 1943 to mid-1946. After the war ANTU became available to the public, being advertised as a miracle rat killer for households. Richter had however advised against the use of ANTU at a small scale, as rats get a 30-day tolerance for ANTU after a non-lethal dose and become able to detect the chemical. As the rat population returned, the popularity of ANTU decreased. It became clear that more than poisoning alone was needed to get rid of rats. The city of Baltimore soon returned to an environmental approach in rat control and ANTU disappeared from the market after a few years.<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> <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=%CE%91-Naphthylthiourea&action=edit&section=7" 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 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"Wartime rat control, rodent ecology, and the rise and fall of chemical rodenticides." <i>Endeavour</i> 29.3 (2005): 119-125</span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output 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style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;font-size:smaller;">1st generation</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Warfarin" title="Warfarin">Warfarin</a></li> <li><a href="/wiki/Coumatetralyl" title="Coumatetralyl">Coumatetralyl</a></li> <li><a href="/wiki/Fumarin" title="Fumarin">Fumarin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;font-size:smaller;">2nd generation (<a href="/wiki/Superwarfarin" title="Superwarfarin">Superwarfarins</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Brodifacoum" title="Brodifacoum">Brodifacoum</a></li> <li><a href="/wiki/Bromadiolone" title="Bromadiolone">Bromadiolone</a></li> <li><a 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title="Convulsant">Convulsants</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Crimidine" title="Crimidine">Crimidine</a></li> <li><a href="/wiki/Phenylsilatrane" title="Phenylsilatrane">Phenylsilatrane</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Tetramethylenedisulfotetramine" title="Tetramethylenedisulfotetramine">Tetramethylenedisulfotetramine</a></li> <li><a href="/wiki/Chlorophenylsilatrane" title="Chlorophenylsilatrane">Chlorophenylsilatrane</a></li> <li><a href="/wiki/RDX" title="RDX">RDX</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Vitamin_D" title="Vitamin D">Calciferols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Inorganic_compound" title="Inorganic compound">Inorganic compounds</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium_phosphide" title="Aluminium phosphide">Aluminium phosphide</a></li> <li><a href="/wiki/Arsenic" title="Arsenic">Arsenic</a></li> <li><a href="/wiki/Barium_carbonate" title="Barium carbonate">Barium carbonate</a></li> <li><a href="/wiki/Calcium_phosphide" title="Calcium phosphide">Calcium phosphide</a></li> <li><a href="/wiki/Cyanide" title="Cyanide">Cyanide</a></li> <li><a href="/wiki/Thallium(I)_sulfate" title="Thallium(I) sulfate">Thallium sulfate</a></li> <li><a href="/wiki/Zinc_phosphide" title="Zinc phosphide">Zinc phosphide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Organochlorine" class="mw-redirect" title="Organochlorine">Organochlorine</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chloralose" title="Chloralose">Chloralose</a></li> <li><a href="/wiki/Endrin" title="Endrin">Endrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Organophosphorus" class="mw-redirect" title="Organophosphorus">Organophosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosacetim" title="Phosacetim">Phosacetim</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" 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title="1,3-Difluoro-2-propanol">1,3-Difluoro-2-propanol (Gliftor)</a></li> <li><a href="/wiki/Norbormide" title="Norbormide">Norbormide</a></li> <li><a href="/wiki/Pyrinuron" title="Pyrinuron">Pyrinuron</a></li> <li><a href="/wiki/Scilliroside" title="Scilliroside">Scilliroside</a></li> <li><a href="/wiki/Sodium_fluoroacetate" title="Sodium fluoroacetate">Sodium fluoroacetate</a></li></ul> </div></td></tr></tbody></table></div>    </div><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" href="https://en.wikipedia.org/w/index.php?title=Α-Naphthylthiourea&oldid=1247689348">https://en.wikipedia.org/w/index.php?title=Α-Naphthylthiourea&oldid=1247689348</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a 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