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id="toc-Au_nanoparticle_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Au_nanoparticle_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Au nanoparticle synthesis</span> </div> </a> <ul id="toc-Au_nanoparticle_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mesoporous_materials" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mesoporous_materials"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Mesoporous materials</span> </div> </a> <ul id="toc-Mesoporous_materials-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Toxicity</span> </div> </a> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">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 vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Cetrimonium bromide</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 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-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%D8%AA%D8%B1%DB%8C%D9%88%D9%85%DB%8C%D8%AF_-_%D8%B3%DB%8C" title="ستریومید - سی – South Azerbaijani" lang="azb" hreflang="azb" data-title="ستریومید - سی" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Cetrimoniumbromid" title="Cetrimoniumbromid – Czech" lang="cs" hreflang="cs" data-title="Cetrimoniumbromid" 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/Cetyltrimethylammoniumbromid" title="Cetyltrimethylammoniumbromid – German" lang="de" hreflang="de" data-title="Cetyltrimethylammoniumbromid" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Bromuro_de_hexadeciltrimetilamonio" title="Bromuro de hexadeciltrimetilamonio – Spanish" lang="es" hreflang="es" data-title="Bromuro de hexadeciltrimetilamonio" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%D8%AA%D8%B1%DB%8C%D9%85%DB%8C%D8%AF_-_%D8%B3%DB%8C" title="ستریمید - سی – Persian" lang="fa" hreflang="fa" data-title="ستریمید - سی" 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/Bromure_de_c%C3%A9tyltrim%C3%A9thylammonium" title="Bromure de cétyltriméthylammonium – French" lang="fr" hreflang="fr" data-title="Bromure de cétyltriméthylammonium" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%B8%8C%EB%A1%9C%EB%AF%BC%ED%99%94_%EC%84%B8%ED%8A%B8%EB%A6%AC%EB%AA%A8%EB%8A%84" title="브로민화 세트리모늄 – Korean" lang="ko" hreflang="ko" data-title="브로민화 세트리모늄" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Setiltrimetilamonium_bromida" title="Setiltrimetilamonium bromida – Indonesian" lang="id" hreflang="id" data-title="Setiltrimetilamonium bromida" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Bromuro_di_cetil-trimetilammonio" title="Bromuro di cetil-trimetilammonio – Italian" lang="it" hreflang="it" data-title="Bromuro di cetil-trimetilammonio" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cetrimoniumbromide" title="Cetrimoniumbromide – Dutch" lang="nl" hreflang="nl" data-title="Cetrimoniumbromide" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E8%87%AD%E5%8C%96%E3%83%98%E3%82%AD%E3%82%B5%E3%83%87%E3%82%B7%E3%83%AB%E3%83%88%E3%83%AA%E3%83%A1%E3%83%81%E3%83%AB%E3%82%A2%E3%83%B3%E3%83%A2%E3%83%8B%E3%82%A6%E3%83%A0" title="臭化ヘキサデシルトリメチルアンモニウム – Japanese" lang="ja" hreflang="ja" data-title="臭化ヘキサデシルトリメチルアンモニウム" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/CTAB" title="CTAB – Portuguese" lang="pt" hreflang="pt" data-title="CTAB" 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%A6%D0%B5%D1%82%D0%B8%D0%BB%D1%82%D1%80%D0%B8%D0%BC%D0%B5%D1%82%D0%B8%D0%BB%D0%B0%D0%BC%D0%BC%D0%BE%D0%BD%D0%B8%D1%8F_%D0%B1%D1%80%D0%BE%D0%BC%D0%B8%D0%B4" title="Цетилтриметиламмония бромид – Russian" lang="ru" hreflang="ru" data-title="Цетилтриметиламмония бромид" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Cetrimonijum_bromid" title="Cetrimonijum bromid – Serbian" lang="sr" hreflang="sr" data-title="Cetrimonijum bromid" 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/Cetrimonijum_bromid" title="Cetrimonijum bromid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cetrimonijum bromid" 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/Setrimoniumbromidi" title="Setrimoniumbromidi – Finnish" lang="fi" hreflang="fi" data-title="Setrimoniumbromidi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Setrimid" title="Setrimid – Turkish" lang="tr" hreflang="tr" data-title="Setrimid" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%BA%B4%E5%8C%96%E5%8D%81%E5%85%AD%E7%83%B7%E5%9F%BA%E4%B8%89%E7%94%B2%E9%93%B5" title="溴化十六烷基三甲铵 – Chinese" lang="zh" hreflang="zh" data-title="溴化十六烷基三甲铵" 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/Q416077#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div 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class="infobox ib-chembox"> <caption>Cetrimonium bromide </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Cetyltrimethyl_ammonium_bromide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Cetyltrimethyl_ammonium_bromide.svg/220px-Cetyltrimethyl_ammonium_bromide.svg.png" decoding="async" width="220" height="43" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Cetyltrimethyl_ammonium_bromide.svg/330px-Cetyltrimethyl_ammonium_bromide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/45/Cetyltrimethyl_ammonium_bromide.svg/440px-Cetyltrimethyl_ammonium_bromide.svg.png 2x" data-file-width="512" data-file-height="99" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:(C16)(C1)3NBr.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/%28C16%29%28C1%293NBr.jpg/220px-%28C16%29%28C1%293NBr.jpg" decoding="async" width="220" height="293" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/%28C16%29%28C1%293NBr.jpg/330px-%28C16%29%28C1%293NBr.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/67/%28C16%29%28C1%293NBr.jpg/440px-%28C16%29%28C1%293NBr.jpg 2x" data-file-width="2448" data-file-height="3264" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;"><i>N</i>,<i>N</i>,<i>N</i>-Trimethylhexadecan-1-aminium bromide</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div><ul><li>Cetyltrimethylammonium bromide</li><li>CTAB</li><li>Hexadecyltrimethylammonium bromide</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><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=57-09-0">57-09-0</a></span></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=CCCCCCCCCCCCCCCC%5BN%2B%5D%28C%29%28C%29C.%5BBr-%5D">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=3567">CHEBI:3567</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL113150">ChEMBL113150</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5754.html">5754</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.283">100.000.283</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q416077#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/D03454">D03454</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5974">5974</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/L64N7M9BWR">L64N7M9BWR</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/DTXSID5037028">DTXSID5037028</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q416077#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/C19H42N.BrH/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(2,3)4;/h5-19H2,1-4H3;1H/q+1;/p-1<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: LZZYPRNAOMGNLH-UHFFFAOYSA-M<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/C19H42N.BrH/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(2,3)4;/h5-19H2,1-4H3;1H/q+1;/p-1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: LZZYPRNAOMGNLH-REWHXWOFAU</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%;">CCCCCCCCCCCCCCCC[N+](C)(C)C.[Br-]</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>C<sub>19</sub>H<sub>42</sub>BrN  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>364.45 g/mol    </td></tr> <tr> <td>Appearance </td> <td>white powder </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>237 to 243 °C (459 to 469 °F; 510 to 516 K) (decomposes) </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/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_D08" title="ATC code D08">D08AJ02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=D08AJ02">WHO</a></span>)  </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=477162851&page2=Cetrimonium+bromide">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>Cetrimonium bromide</b>, also known with the abbreviation <b>CTAB</b>, is a <a href="/wiki/Quaternary_ammonium" class="mw-redirect" title="Quaternary ammonium">quaternary ammonium</a> <a href="/wiki/Surfactant" title="Surfactant">surfactant</a> with a <a href="/wiki/Condensed_structural_formula" class="mw-redirect" title="Condensed structural formula">condensed structural formula</a> [(C<sub>16</sub>H<sub>33</sub>)N(CH<sub>3</sub>)<sub>3</sub>]Br. </p><p>It is one of the components of the topical antiseptic <a href="/wiki/Cetrimide" title="Cetrimide">cetrimide</a>.<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> The cetrimonium (hexadecyltrimethylammonium) cation is an effective antiseptic agent against bacteria and fungi. It is also one of the main components of some buffers for the <a href="/wiki/DNA_extraction" title="DNA extraction">extraction of DNA</a>.<sup id="cite_ref-:2_2-0" class="reference"><a href="#cite_note-:2-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It has been widely used in synthesis of <a href="/wiki/Colloidal_gold" title="Colloidal gold">gold nanoparticles</a> (<i>e.g.</i>, spheres, rods, bipyramids), <a href="/wiki/Mesoporous_material" title="Mesoporous material">mesoporous</a> silica nanoparticles (<i>e.g.</i>, <a href="/wiki/MCM-41" title="MCM-41">MCM-41</a>), and <a href="/wiki/Hair_conditioner" title="Hair conditioner">hair conditioning</a> products. The closely related compounds <a href="/wiki/Cetrimonium_chloride" title="Cetrimonium chloride">cetrimonium chloride</a> and <a href="/w/index.php?title=Cetrimonium_stearate&action=edit&redlink=1" class="new" title="Cetrimonium stearate (page does not exist)">cetrimonium stearate</a> are also used as topical <a href="/wiki/Antiseptic" title="Antiseptic">antiseptics</a> and may be found in many household products such as <a href="/wiki/Shampoo" title="Shampoo">shampoos</a> and cosmetics. CTAB, due to its relatively high cost, is typically only used in select cosmetics. </p><p>As with most surfactants, CTAB forms <a href="/wiki/Micelle" title="Micelle">micelles</a> in aqueous solutions. At 303 K (30 °C) it forms micelles with <a href="/wiki/Aggregation_number" title="Aggregation number">aggregation number</a> 75–120 (depending on method of determination; average ~95) and degree of ionization, α = 0.2–0.1 (fractional charge; from low to high concentration).<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The binding constant (K°) of Br<sup>−</sup> counterion to a CTA<sup>+</sup> micelle at 303 K (30 °C) is <i>c.</i> 400 M-1. This value is calculated from Br<sup>−</sup> and CTA<sup>+</sup> ion selective electrode measurements and <a href="/wiki/Conductometry" title="Conductometry">conductometry</a> data by using literature data for micelle size (r = ~3 nm)<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 2016)">citation needed</span></a></i>]</sup>, extrapolated to the <a href="/wiki/Critical_micelle_concentration" title="Critical micelle concentration">critical micelle concentration</a> of 1 mM<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 2016)">citation needed</span></a></i>]</sup>. However, K° varies with total surfactant concentration so it is <a href="/wiki/Extrapolation" title="Extrapolation">extrapolated</a> to the point at which micelle concentration is zero.<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 2016)">citation needed</span></a></i>]</sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cetrimonium_bromide&action=edit&section=1" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Biological">Biological</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cetrimonium_bromide&action=edit&section=2" title="Edit section: Biological"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Lysis" title="Lysis">Cell lysis</a> is a convenient tool to isolate certain <a href="/wiki/Macromolecule" title="Macromolecule">macromolecules</a> that exist primarily inside of the cell. Cell membranes consist of <a href="/wiki/Hydrophile" title="Hydrophile">hydrophilic</a> and <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilic</a> endgroups. Therefore, <a href="/wiki/Detergent" title="Detergent">detergents</a> are often used to dissolve these membranes since they interact with both <a href="/wiki/Chemical_polarity" title="Chemical polarity">polar and nonpolar</a> endgroups. CTAB has emerged as the preferred choice for biological use because it maintains the integrity of precipitated <a href="/wiki/DNA" title="DNA">DNA</a> during <a href="/wiki/DNA_extraction" title="DNA extraction">its isolation</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Cells typically have high concentrations of macromolecules, such as <a href="/wiki/Glycoprotein" title="Glycoprotein">glycoproteins</a> and <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a>, that co-precipitate with DNA during the extraction process, causing the extracted DNA to lose purity. The positive charge of the CTAB molecule allows it to denature these molecules that would interfere with this isolation.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Medical">Medical</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cetrimonium_bromide&action=edit&section=3" title="Edit section: Medical"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>CTAB has been shown to have potential use as an <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>-promoting anticancer agent for <a href="/wiki/Head_and_neck_cancer" title="Head and neck cancer">head and neck cancer</a> (HNC).<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> <i>In vitro</i>, CTAB interacted additively with <a href="/wiki/Gamma_ray" title="Gamma ray">γ radiation</a> and <a href="/wiki/Cisplatin" title="Cisplatin">cisplatin</a>, two standard HNC therapeutic agents. CTAB exhibited anticancer <a href="/wiki/Cytotoxicity" title="Cytotoxicity">cytotoxicity</a> against several HNC cell lines with minimal effects on normal <a href="/wiki/Fibroblast" title="Fibroblast">fibroblasts</a>, a selectivity that exploits cancer-specific metabolic aberrations. <i>In vivo</i>, CTAB <a href="/wiki/Ablation" title="Ablation">ablated</a> tumor-forming capacity of FaDu cells and delayed growth of established tumors. Thus, using this approach, CTAB was identified as a potential apoptogenic quaternary ammonium compound possessing <i>in vitro</i> and <i>in vivo</i> efficacy against HNC models. CTAB is also recommended by the <a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organisation</a> (WHO) as a purification agent in the downstream vaccine processing of polysaccharide vaccines.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Protein_electrophoresis">Protein electrophoresis</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cetrimonium_bromide&action=edit&section=4" title="Edit section: Protein electrophoresis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Glycoprotein" title="Glycoprotein">Glycoproteins</a> form broad, fuzzy bands in <a href="/wiki/SDS-PAGE" title="SDS-PAGE">SDS-PAGE</a> (Laemmli-electrophoresis) because of their broad distribution of negative charges. Using positively charged detergents such as CTAB will avoid issues associated with glycoproteins. Proteins can be blotted from CTAB-gels in analogy to <a href="/wiki/Western_blot" title="Western blot">western blots</a> ("eastern blot"), and <a href="/wiki/Myelin" title="Myelin">Myelin</a>-associated high hydrophobic protein can be analyzed using CTAB 2-DE.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2023)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading4"><h4 id="DNA_extraction">DNA extraction</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cetrimonium_bromide&action=edit&section=5" title="Edit section: DNA extraction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>CTAB serves as an important surfactant in the DNA extraction buffer system to remove membrane lipids and promote cell lysis. Separation is also successful when the tissue contains high amounts of <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a>.<sup id="cite_ref-:2_2-1" class="reference"><a href="#cite_note-:2-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> CTAB binds to the polysaccharides when the salt concentration is high, thus removing polysaccharides from solution. A typical recipe can be to combine 100 mL of 1 M Tris HCl (pH 8.0), 280 mL 5 M NaCl, 40 mL of 0.5 M <a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">EDTA</a>, and 20 g of CTAB then add <a href="/wiki/Purified_water" title="Purified water">double distilled water</a> (ddH<sub>2</sub>O) to bring total volume to 1 L. </p> <div class="mw-heading mw-heading2"><h2 id="Nanoparticle_synthesis">Nanoparticle synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cetrimonium_bromide&action=edit&section=6" title="Edit section: Nanoparticle synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Surfactants play a key role in <a href="/wiki/Nanoparticle" title="Nanoparticle">nanoparticle</a> synthesis by adsorbing to the surface of the forming nanoparticle and lowering its surface energy.<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><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> Surfactants also help to prevent aggregation (<i>e.g.</i> via <a href="/wiki/DLVO_theory" title="DLVO theory">DLVO</a> mechanisms). </p> <div class="mw-heading mw-heading3"><h3 id="Au_nanoparticle_synthesis">Au nanoparticle synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cetrimonium_bromide&action=edit&section=7" title="Edit section: Au nanoparticle synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Gold" title="Gold">Gold</a> (Au) nanoparticles are interesting to researchers because of their unique properties that can be used in applications such as <a href="/wiki/Catalysis" title="Catalysis">catalysis</a>, <a href="/wiki/Optics" title="Optics">optics</a>, <a href="/wiki/Electronics" title="Electronics">electronics</a>, <a href="/wiki/Sensor" title="Sensor">sensing</a>, and <a href="/wiki/Medicine" title="Medicine">medicine</a>.<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> Control of nanoparticle size and shape is important in order to tune its properties. CTAB has been a widely used reagent to both impart stability to these nanoparticles as well as control their morphologies. CTAB may play a role in controlling nanoparticle size and shape by selectively or more strongly binding to various emerging <a href="/wiki/Facet" title="Facet">crystal facets</a>. </p><p>Some of this control originates from the reaction of CTAB with other reagents in the gold nanoparticle synthesis. For example, in aqueous gold nanoparticle syntheses, <a href="/wiki/Chlorauric_acid" class="mw-redirect" title="Chlorauric acid">chlorauric acid</a> (HAuCl<sub>4</sub>) may react with CTAB to create a CTA<sup>+</sup>-AuCl<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span> complex.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The gold complex is then reacted with <a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">ascorbic acid</a> to produce <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a>, an ascorbic acid radical, and CTA-AuCl<sub>3</sub>. The ascorbic acid radical and CTA-AuCl<sub>3</sub> react spontaneously to create metallic Au<sup>0</sup> nanoparticles and other byproducts. An alternative or simultaneous reaction is the substitution of <a href="/wiki/Chloride" title="Chloride">Cl<sup>−</sup></a> with <a href="/wiki/Bromide" title="Bromide">Br<sup>−</sup></a> about the Au(III) center. Both complexation with the <a href="/wiki/Ammonium" title="Ammonium">ammonium cation</a> and/or speciation of the Au(III) precursor influence the kinetics of the nanoparticle formation reaction and therefore influence the size, shape, and (size and shape) distributions of the resulting particles. </p><p>However, CTA<sup>+</sup>-AuCl<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span> should not be called a <a href="/wiki/Coordination_complex" title="Coordination complex">complex</a>, electrostatic interaction of <a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">quaternary ammonium cation</a> with AuCl<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span> results in formation of an <a href="/wiki/Ion_association" title="Ion association">ion pair</a> at best. CTA<sup>+</sup> does not have any donating centers which can form a coordination complex with Au(III) metal centers. </p> <div class="mw-heading mw-heading3"><h3 id="Mesoporous_materials">Mesoporous materials</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cetrimonium_bromide&action=edit&section=8" title="Edit section: Mesoporous materials"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>CTAB is used as the template for the first report of ordered <a href="/wiki/Mesoporous_material" title="Mesoporous material">mesoporous materials</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Microporous_material" title="Microporous material">Microporous</a> and mesoporous inorganic solids (with pore diameters of ≤20 Å and ~20–500 Å respectively) have found great utility as catalysts and <a href="/wiki/Sorption" title="Sorption">sorption</a> media because of their large internal surface area. Typical microporous materials are crystalline framework solids, such as <a href="/wiki/Zeolite" title="Zeolite">zeolites</a>, but the largest pore dimensions are still below 2 nm which greatly limit application. Examples of mesoporous solids include <a href="/wiki/Silicon_dioxide" title="Silicon dioxide">silicas</a> and modified layered materials, but these are invariably <a href="/wiki/Amorphous_solid" title="Amorphous solid">amorphous</a> or <a href="/wiki/Paracrystalline" class="mw-redirect" title="Paracrystalline">paracrystalline</a>, with pores that are irregularly spaced and broadly distributed in size. There is a need to prepare highly ordered mesoporous material with good mesoscale crystallinity. The synthesis of mesoporous solids from the calcination of <a href="/wiki/Aluminosilicate" title="Aluminosilicate">aluminosilicate</a> gels in the presence of surfactants was reported. The material possesses regular arrays of uniform channels, the dimensions of which can be tailored (in the range of 16 Å to >100 Å) through the choice of surfactant, auxiliary chemicals, and reaction conditions. It was proposed that the formation of these materials takes place by means of a liquid-crystal 'templating' mechanism, in which the silicate material forms inorganic walls between ordered surfactant <a href="/wiki/Micelle" title="Micelle">micelles</a>. CTAB formed micelles in the solution and these micelles further formed a two dimensional <a href="/wiki/Hexagon" title="Hexagon">hexagonal</a> mesostructure. The silicon precursor began to hydrolyze between the micelles and finally filled the gap with silicon dioxide. The template could be further removed by <a href="/wiki/Calcination" title="Calcination">calcination</a> and left a pore structure behind. These pores mimicked exactly the structure of mesoscale soft template and led to highly ordered mesoporous silica materials. </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=Cetrimonium_bromide&action=edit&section=9" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>CTAB has been used for applications from nanoparticle synthesis to cosmetics. Due to its use in human products, along with other applications, it is essential to be made aware of the hazards this agent contains. The Santa Cruz Biotechnology, Inc.<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> offers a comprehensive <a href="/wiki/Safety_data_sheet" title="Safety data sheet">MSDS</a> for CTAB and should be referred to for additional questions or concerns.<sup id="cite_ref-:0_15-0" class="reference"><a href="#cite_note-:0-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Animal testing has shown ingestion of less than 150 g of the agent can lead to adverse health effects or possibly death by CTAB causing chemical burns throughout the <a href="/wiki/Esophagus" title="Esophagus">esophagus</a> and <a href="/wiki/Human_gastrointestinal_tract" class="mw-redirect" title="Human gastrointestinal tract">gastrointestinal tract</a> that can be followed by nausea and vomiting.<sup id="cite_ref-:0_15-1" class="reference"><a href="#cite_note-:0-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> If the substance continues through the gastrointestinal tract, it will be poorly absorbed in the intestines followed by excretion in feces.<sup id="cite_ref-:1_16-0" class="reference"><a href="#cite_note-:1-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Toxicity has also been tested on aquatic life including <i><a href="/wiki/Zebrafish" title="Zebrafish">Brachydanio rerio</a></i> (zebra fish) and <i><a href="/wiki/Daphnia_magna" title="Daphnia magna">Daphnia magna</a></i> (water flea). Zebra fish showed CTAB toxicity when exposed to 0.3 mg/L for 96 hours, and water fleas showed CTAB toxicity when exposed to 0.03 mg/L for 48 hours.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>CTAB along with other <a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">quaternary ammonium salts</a> have frequently been used in cosmetics at concentrations up to 10%. Cosmetics at that concentration must only be used as rinse-off types such as shampoos. Other leave-on cosmetics are considered only safe at or below 0.25% concentrations. Injections into the body cavity of pregnant mice showed <a href="/wiki/Embryo" title="Embryo">embryotoxic</a> and <a href="/wiki/Teratology" title="Teratology">teratogenic</a> effects. Only <a href="/wiki/Teratology" title="Teratology">teratogenic</a> effects were seen with 10 mg/kg doses, while both effects were seen at 35 mg/kg doses. Oral doses of 50 mg/kg/day showed embryotoxic effects as well.<sup id="cite_ref-:1_16-1" class="reference"><a href="#cite_note-:1-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Similar tests were completed by giving rats 10, 20, and 45 mg/kg/day of CTAB in their drinking water for one year. At the 10 and 20 mg/kg/day doses, the rats did not have any toxic symptoms. At the highest dose, the rats began experiencing weight loss. The weight loss in the male rats was attributed to <a href="/wiki/Efficiency_of_food_conversion" title="Efficiency of food conversion">less efficient food conversion</a>. The tests showed no microscopic alterations to the gastrointestinal tract of the rats.<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><p>Other toxicity tests have been conducted using incubated human skin HaCaT <a href="/wiki/Keratinocyte" title="Keratinocyte">keratinocyte</a> cells. These human cells were incubated with gold <a href="/wiki/Nanorod" title="Nanorod">nanorods</a> that were synthesized using seed-mediated, surfactant-assisted growth of gold nanoparticles. Gold nanoparticles are shown to be nontoxic, however once the nanoparticles are put through the growth solutions, the newly formed nanorods are highly toxic. This large increase in toxicity is attributed to the CTAB that is used in the growth solutions to cause <a href="/wiki/Anisotropy" title="Anisotropy">anisotropic</a> growth.<sup id="cite_ref-:3_19-0" class="reference"><a href="#cite_note-:3-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Experiments also showed the toxicity of bulk CTAB and the synthesized gold nanorods to be equivalent. Toxicity tests showed CTAB remaining toxic with concentrations as low as 10 μM. The human cells show CTAB being nontoxic at concentrations less than 1 μM. Without the use of CTAB in this synthesis, the gold nanorods are not stable; they break into nanoparticles or undergo <a href="/wiki/Particle_aggregation" title="Particle aggregation">aggregation</a>.<sup id="cite_ref-:3_19-1" class="reference"><a href="#cite_note-:3-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>The mechanism for <a href="/wiki/Cytotoxicity" title="Cytotoxicity">cytotoxicity</a> has not been extensively studied, but there has been possible mechanisms proposed. One proposal showed two methods that led to the cytotoxicity in U87 and A172 <a href="/wiki/Glioblastoma_multiforme" class="mw-redirect" title="Glioblastoma multiforme">glioblastoma</a> cells. The first method showed CTAB exchanging with <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a> causing rearrangement of the membrane allowing β-<a href="/wiki/Galactoside" title="Galactoside">galactoside</a> to enter into the cell by way of cavities. At low concentrations, there are not enough cavities to cause death to the cells, but with increasing the CTAB concentration, more phospholipids are displaced causing more cavities in the membrane leading to cell death. The second proposed method is based on the dissociation of CTAB into CTA<sup>+</sup> and Br<sup>−</sup> within the <a href="/wiki/Mitochondrion" title="Mitochondrion">mitochondrial</a> membrane. The positively charged CTA<sup>+</sup> binds to the <a href="/wiki/ATP_synthase" title="ATP synthase">ATP synthase</a> not allowing H<sup>+</sup> to bind stopping the synthesis of <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> and resulting in cell death.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cetrimonium_bromide&action=edit&section=10" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Behentrimonium_chloride" title="Behentrimonium chloride">Behentrimonium chloride</a> – A C<sub>25</sub> structural analogue</li> <li><a href="/wiki/Cetrimonium_chloride" title="Cetrimonium chloride">Cetrimonium chloride</a> – The corresponding chloride salt</li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cetrimonium_bromide&action=edit&section=11" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFLaemmli1970" class="citation journal cs1">Laemmli, U. 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(2009-02-17). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2844666">"Toxicity and Environmental Risks of Nanomaterials: Challenges and Future Needs"</a>. <i>Journal of Environmental Science and Health, Part C</i>. <b>27</b> (1): 1–35. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2009JESHC..27....1R">2009JESHC..27....1R</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F10590500802708267">10.1080/10590500802708267</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1059-0501">1059-0501</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2844666">2844666</a></span>. <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/19204862">19204862</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Environmental+Science+and+Health%2C+Part+C&rft.atitle=Toxicity+and+Environmental+Risks+of+Nanomaterials%3A+Challenges+and+Future+Needs&rft.volume=27&rft.issue=1&rft.pages=1-35&rft.date=2009-02-17&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2844666%23id-name%3DPMC&rft_id=info%3Abibcode%2F2009JESHC..27....1R&rft_id=info%3Apmid%2F19204862&rft_id=info%3Adoi%2F10.1080%2F10590500802708267&rft.issn=1059-0501&rft.aulast=RAY&rft.aufirst=PARESH+CHANDRA&rft.au=YU%2C+HONGTAO&rft.au=FU%2C+PETER+P.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2844666&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACetrimonium+bromide" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchachter2013" class="citation thesis cs1">Schachter, David (2013). <i>The source of toxicity in CTAB and CTAB-stabilized gold nanorods</i> (Thesis). No Publisher Supplied. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2013PhDT........22S">2013PhDT........22S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.7282%2Ft3x63kms">10.7282/t3x63kms</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adissertation&rft.title=The+source+of+toxicity+in+CTAB+and+CTAB-stabilized+gold+nanorods&rft.inst=No+Publisher+Supplied&rft.date=2013&rft_id=info%3Adoi%2F10.7282%2Ft3x63kms&rft_id=info%3Abibcode%2F2013PhDT........22S&rft.aulast=Schachter&rft.aufirst=David&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACetrimonium+bromide" 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=Cetrimonium_bromide&action=edit&section=12" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><i>Merck Index</i>, 11th Edition, <b>1989</b>.</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20111005023417/http://bioinf.charite.de/superdrug/fullinfo.php?cas=000057090">Drug information</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl 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style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethacridine_lactate" title="Ethacridine lactate">Ethacridine lactate</a></li> <li><a href="/wiki/9-Aminoacridine" title="9-Aminoacridine">9-Aminoacridine</a></li> <li><a href="/wiki/Euflavine" title="Euflavine">Euflavine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Biguanide" title="Biguanide">Biguanides</a> and <a href="/wiki/Amidine" title="Amidine">amidines</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/Dibrompropamidine" title="Dibrompropamidine">Dibrompropamidine</a></li> <li><a href="/wiki/Chlorhexidine" title="Chlorhexidine">Chlorhexidine</a><sup>#</sup></li> <li><a href="/wiki/Propamidine" title="Propamidine">Propamidine</a></li> <li><a href="/wiki/Hexamidine" title="Hexamidine">Hexamidine</a></li> <li><a href="/wiki/Polyhexanide" title="Polyhexanide">Polihexanide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenol" title="Phenol">Phenol</a> and derivatives</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/Hexachlorophene" title="Hexachlorophene">Hexachlorophene</a></li> <li><a href="/wiki/Policresulen" title="Policresulen">Policresulen</a></li> <li><a href="/wiki/Phenol" title="Phenol">Phenol</a></li> <li><a href="/wiki/Triclosan" title="Triclosan">Triclosan</a></li> <li><a href="/wiki/Triclocarban" title="Triclocarban">Triclocarban</a></li> <li><a href="/wiki/Chloroxylenol" title="Chloroxylenol">Chloroxylenol</a><sup>#</sup></li> <li><a href="/wiki/Biphenylol" class="mw-redirect" title="Biphenylol">Biphenylol</a></li> <li><a href="/wiki/Fenticlor" title="Fenticlor">Fenticlor</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrofuran" title="Nitrofuran">Nitrofuran</a> derivatives</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/Nitrofurazone" title="Nitrofurazone">Nitrofurazone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Iodine" title="Iodine">Iodine</a> products</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/Iodine/octylphenoxypolyglycolether" class="mw-redirect" title="Iodine/octylphenoxypolyglycolether">Iodine/octylphenoxypolyglycolether</a></li> <li><a href="/wiki/Povidone-iodine" title="Povidone-iodine">Povidone-iodine</a><sup>#</sup></li> <li><a href="/wiki/Diiodohydroxypropane" title="Diiodohydroxypropane">Diiodohydroxypropane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinoline" title="Quinoline">Quinoline</a> derivatives</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/Dequalinium" title="Dequalinium">Dequalinium</a></li> <li><a href="/wiki/Chlorquinaldol" title="Chlorquinaldol">Chlorquinaldol</a></li> <li><a href="/wiki/Oxyquinoline" class="mw-redirect" title="Oxyquinoline">Oxyquinoline</a></li> <li><a href="/wiki/Clioquinol" title="Clioquinol">Clioquinol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quaternary_ammonium_compounds" class="mw-redirect" title="Quaternary ammonium compounds">Quaternary ammonium compounds</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/Benzalkonium_chloride" title="Benzalkonium chloride">Benzalkonium</a></li> <li><a href="/wiki/Benzethonium_chloride" title="Benzethonium chloride">Benzethonium chloride</a></li> <li><a href="/wiki/Cetrimonium" title="Cetrimonium">Cetrimonium</a> (<a class="mw-selflink selflink">bromide</a>/<a href="/wiki/Cetrimonium_chloride" title="Cetrimonium chloride">chloride</a>)</li> <li><a href="/wiki/Cetylpyridinium_chloride" title="Cetylpyridinium chloride">Cetylpyridinium</a></li> <li><a href="/wiki/Cetrimide" title="Cetrimide">Cetrimide</a></li> <li><a href="/wiki/Benzoxonium_chloride" title="Benzoxonium chloride">Benzoxonium chloride</a></li> <li><a href="/wiki/Didecyldimethylammonium_chloride" title="Didecyldimethylammonium chloride">Didecyldimethylammonium chloride</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mercury_(element)" title="Mercury (element)">Mercurial</a> products</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/Mercuric_amidochloride" title="Mercuric amidochloride">Mercuric amidochloride</a></li> <li><a href="/wiki/Phenylmercuric_borate" title="Phenylmercuric borate">Phenylmercuric borate</a></li> <li><a href="/wiki/Mercury(II)_chloride" title="Mercury(II) chloride">Mercuric chloride</a></li> <li><a href="/wiki/Merbromin" title="Merbromin">Merbromin</a></li> <li><a href="/wiki/Nitromersol" title="Nitromersol">Nitromersol</a></li> <li><a href="/wiki/Thiomersal" title="Thiomersal">Thiomersal</a></li> <li><a href="/wiki/Mercury(II)_iodide" title="Mercury(II) iodide">Mercuric iodide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silver" title="Silver">Silver</a> compounds</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/Silver_nitrate" title="Silver nitrate">Silver nitrate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohols_in_medicine" class="mw-redirect" title="Alcohols in medicine">Alcohols</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/1-Propanol" title="1-Propanol">Propanol (propyl alcohol)</a></li> <li><a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">Isopropanol (isopropyl alcohol)</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol (ethyl alcohol)</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Potassium_permanganate" title="Potassium permanganate">Potassium permanganate</a></li> <li><a href="/wiki/Sodium_hypochlorite" title="Sodium hypochlorite">Sodium hypochlorite</a></li> <li><a href="/wiki/Halazone" title="Halazone">Halazone</a></li> <li><a href="/wiki/Monalazone" title="Monalazone">Monalazone</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/wiki/Eosin" title="Eosin">Eosin</a></li> <li><a href="/wiki/Chloramine-T" title="Chloramine-T">Chloramine-T (tosylchloramide)</a></li> <li><a href="/wiki/Octenidine_dihydrochloride" title="Octenidine dihydrochloride">Octenidine dihydrochloride</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Throat_preparations_(R02)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Throat_preparations" title="Template:Throat preparations"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Throat_preparations" title="Template talk:Throat preparations"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Throat_preparations" title="Special:EditPage/Template:Throat preparations"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Throat_preparations_(R02)" style="font-size:114%;margin:0 4em"><a href="/wiki/Throat" title="Throat">Throat</a> preparations (<a href="/wiki/ATC_code_R02" title="ATC code R02">R02</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiseptic" title="Antiseptic">Antiseptics</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/Acriflavine" title="Acriflavine">Acriflavinium chloride</a></li> <li><a href="/wiki/Ambazone" title="Ambazone">Ambazone</a></li> <li><a href="/wiki/Amylmetacresol" title="Amylmetacresol">Amylmetacresol</a></li> <li><a href="/wiki/Benzalkonium_chloride" title="Benzalkonium chloride">Benzalkonium</a></li> <li><a href="/wiki/Benzethonium_chloride" title="Benzethonium chloride">Benzethonium</a></li> <li><a href="/wiki/Cetrimonium" title="Cetrimonium">Cetrimonium</a> (<a class="mw-selflink selflink">bromide</a>/<a href="/wiki/Cetrimonium_chloride" title="Cetrimonium chloride">chloride</a>)</li> <li><a href="/wiki/Cetylpyridinium_chloride" title="Cetylpyridinium chloride">Cetylpyridinium</a></li> <li><a href="/wiki/Chlorhexidine" title="Chlorhexidine">Chlorhexidine</a></li> <li><a href="/wiki/Chlorquinaldol" title="Chlorquinaldol">Chlorquinaldol</a></li> <li><a href="/wiki/Dequalinium" title="Dequalinium">Dequalinium</a></li> <li><a href="/wiki/2,4-Dichlorobenzyl_alcohol" title="2,4-Dichlorobenzyl alcohol">Dichlorobenzyl alcohol</a></li> <li><a href="/wiki/Hexamidine" title="Hexamidine">Hexamidine</a></li> <li><a href="/wiki/Hexetidine" title="Hexetidine">Hexetidine</a></li> <li><a href="/wiki/Hexylresorcinol" class="mw-redirect" title="Hexylresorcinol">Hexylresorcinol</a></li> <li><a href="/wiki/Myristyl-benzalkonium" class="mw-redirect" title="Myristyl-benzalkonium">Myristyl-benzalkonium</a></li> <li><a href="/wiki/8-Hydroxyquinoline" title="8-Hydroxyquinoline">Oxyquinoline</a></li> <li><a href="/wiki/Phenol" title="Phenol">Phenol</a></li> <li><a href="/wiki/Povidone-iodine" title="Povidone-iodine">Povidone-iodine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antibacterial" class="mw-redirect" title="Antibacterial">Antibiotics</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/Bacitracin" title="Bacitracin">Bacitracin</a></li> <li><a href="/wiki/Fusafungine" title="Fusafungine">Fusafungine</a></li> <li><a href="/wiki/Gramicidin" title="Gramicidin">Gramicidin</a></li> <li><a href="/wiki/Neomycin" title="Neomycin">Neomycin</a></li> <li><a href="/wiki/Tyrothricin" title="Tyrothricin">Tyrothricin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Local_anesthetic" title="Local anesthetic">Local anesthetics</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/Benzocaine" title="Benzocaine">Benzocaine</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Dyclonine" title="Dyclonine">Dyclonine</a></li> <li><a href="/wiki/Lidocaine" title="Lidocaine">Lidocaine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div 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