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class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Inhoud</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">naar zijbalk verplaatsen</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">verbergen</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">Top</div> </a> </li> <li id="toc-Geschiedenis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Geschiedenis"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Geschiedenis</span> </div> </a> <ul id="toc-Geschiedenis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthese" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthese"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Synthese</span> </div> </a> <ul id="toc-Synthese-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toepassingen" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toepassingen"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Toepassingen</span> </div> </a> <ul id="toc-Toepassingen-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Werkingsmechanisme" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Werkingsmechanisme"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Werkingsmechanisme</span> </div> </a> <ul id="toc-Werkingsmechanisme-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicologie_en_veiligheid" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicologie_en_veiligheid"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Toxicologie en veiligheid</span> </div> </a> <button aria-controls="toc-Toxicologie_en_veiligheid-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toxicologie en veiligheid-subkopje inklappen</span> </button> <ul id="toc-Toxicologie_en_veiligheid-sublist" class="vector-toc-list"> <li id="toc-Inhalatie" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Inhalatie"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Inhalatie</span> </div> </a> <ul id="toc-Inhalatie-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dermaal_contact" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dermaal_contact"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Dermaal contact</span> </div> </a> <ul id="toc-Dermaal_contact-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oogcontact" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oogcontact"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Oogcontact</span> </div> </a> <ul id="toc-Oogcontact-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chronische_effecten_op_de_gezondheid" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chronische_effecten_op_de_gezondheid"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Chronische effecten op de gezondheid</span> </div> </a> <ul id="toc-Chronische_effecten_op_de_gezondheid-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Toxicologische_studies" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicologische_studies"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Toxicologische studies</span> </div> </a> <button aria-controls="toc-Toxicologische_studies-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toxicologische studies-subkopje inklappen</span> </button> <ul id="toc-Toxicologische_studies-sublist" class="vector-toc-list"> <li id="toc-Toxicologische_studie_bij_de_rat" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Toxicologische_studie_bij_de_rat"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Toxicologische studie bij de rat</span> </div> </a> <ul id="toc-Toxicologische_studie_bij_de_rat-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ontwikkelingstoxicologie" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ontwikkelingstoxicologie"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Ontwikkelingstoxicologie</span> </div> </a> <ul id="toc-Ontwikkelingstoxicologie-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mutageniteit" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mutageniteit"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Mutageniteit</span> </div> </a> <ul id="toc-Mutageniteit-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Carcinogeniteit" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carcinogeniteit"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Carcinogeniteit</span> </div> </a> <ul id="toc-Carcinogeniteit-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Opslag_en_transport" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Opslag_en_transport"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Opslag en transport</span> </div> </a> <ul id="toc-Opslag_en_transport-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Externe_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Externe_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Externe links</span> </div> </a> <ul id="toc-Externe_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header 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</div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Chlooracetofenon</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="Ga naar een artikel in een andere taal. Beschikbaar in 25 talen" > <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-25" 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">25 talen</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%83%D9%84%D9%88%D8%B1%D9%8A%D8%AF_%D8%A7%D9%84%D9%81%D9%8A%D9%86%D8%A7%D8%B3%D9%8A%D9%84" title="كلوريد الفيناسيل – Arabisch" lang="ar" hreflang="ar" data-title="كلوريد الفيناسيل" data-language-autonym="العربية" data-language-local-name="Arabisch" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Xlorasetonfenon" title="Xlorasetonfenon – Azerbeidzjaans" lang="az" hreflang="az" data-title="Xlorasetonfenon" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbeidzjaans" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%DA%A9%D9%88%D9%84%D9%88%D8%B1%DB%8C%D8%AF_%D9%81%D9%86%D8%A7%D8%B3%DB%8C%D9%84" title="کولورید فناسیل – South Azerbaijani" lang="azb" hreflang="azb" data-title="کولورید فناسیل" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/%CE%A9-Chloracetophenon" title="Ω-Chloracetophenon – Duits" lang="de" hreflang="de" data-title="Ω-Chloracetophenon" data-language-autonym="Deutsch" data-language-local-name="Duits" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Phenacyl_chloride" title="Phenacyl chloride – Engels" lang="en" hreflang="en" data-title="Phenacyl chloride" data-language-autonym="English" data-language-local-name="Engels" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Fenacila_klorido" title="Fenacila klorido – Esperanto" lang="eo" hreflang="eo" data-title="Fenacila klorido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Cloruro_de_fenacilo" title="Cloruro de fenacilo – Spaans" lang="es" hreflang="es" data-title="Cloruro de fenacilo" data-language-autonym="Español" data-language-local-name="Spaans" 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/%DA%A9%D9%84%D8%B1%DB%8C%D8%AF_%D9%81%D9%86%D8%A7%D8%B3%DB%8C%D9%84" title="کلرید فناسیل – Perzisch" lang="fa" hreflang="fa" data-title="کلرید فناسیل" data-language-autonym="فارسی" data-language-local-name="Perzisch" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Fenasyylikloridi" title="Fenasyylikloridi – Fins" lang="fi" hreflang="fi" data-title="Fenasyylikloridi" data-language-autonym="Suomi" data-language-local-name="Fins" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Chloroac%C3%A9toph%C3%A9none" title="Chloroacétophénone – Frans" lang="fr" hreflang="fr" data-title="Chloroacétophénone" data-language-autonym="Français" data-language-local-name="Frans" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Kloracetofenon" title="Kloracetofenon – Kroatisch" lang="hr" hreflang="hr" data-title="Kloracetofenon" data-language-autonym="Hrvatski" data-language-local-name="Kroatisch" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Gas_CN" title="Gas CN – Italiaans" lang="it" hreflang="it" data-title="Gas CN" data-language-autonym="Italiano" data-language-local-name="Italiaans" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AF%E3%83%AD%E3%83%AD%E3%82%A2%E3%82%BB%E3%83%88%E3%83%95%E3%82%A7%E3%83%8E%E3%83%B3" title="クロロアセトフェノン – Japans" lang="ja" hreflang="ja" data-title="クロロアセトフェノン" data-language-autonym="日本語" data-language-local-name="Japans" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A5%D0%BB%D0%BE%D1%80%D0%B0%D1%86%D0%B5%D1%82%D0%BE%D1%84%D0%B5%D0%BD%D0%BE%D0%BD" title="Хлорацетофенон – Kazachs" lang="kk" hreflang="kk" data-title="Хлорацетофенон" data-language-autonym="Қазақша" data-language-local-name="Kazachs" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Chloracetofenonas" title="Chloracetofenonas – Litouws" lang="lt" hreflang="lt" data-title="Chloracetofenonas" data-language-autonym="Lietuvių" data-language-local-name="Litouws" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Chloroacetofenon" title="Chloroacetofenon – Pools" lang="pl" hreflang="pl" data-title="Chloroacetofenon" data-language-autonym="Polski" data-language-local-name="Pools" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Cloroacetofenona" title="Cloroacetofenona – Portugees" lang="pt" hreflang="pt" data-title="Cloroacetofenona" data-language-autonym="Português" data-language-local-name="Portugees" 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%A5%D0%BB%D0%BE%D1%80%D0%B0%D1%86%D0%B5%D1%82%D0%BE%D1%84%D0%B5%D0%BD%D0%BE%D0%BD" title="Хлорацетофенон – Russisch" lang="ru" hreflang="ru" data-title="Хлорацетофенон" data-language-autonym="Русский" data-language-local-name="Russisch" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Fenacil_hlorid" title="Fenacil hlorid – Servo-Kroatisch" lang="sh" hreflang="sh" data-title="Fenacil hlorid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Servo-Kroatisch" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Kloracetofenon" title="Kloracetofenon – Sloveens" lang="sl" hreflang="sl" data-title="Kloracetofenon" data-language-autonym="Slovenščina" data-language-local-name="Sloveens" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Fenacil_hlorid" title="Fenacil hlorid – Servisch" lang="sr" hreflang="sr" data-title="Fenacil hlorid" data-language-autonym="Српски / srpski" data-language-local-name="Servisch" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Fenacylklorid" title="Fenacylklorid – Zweeds" lang="sv" hreflang="sv" data-title="Fenacylklorid" data-language-autonym="Svenska" data-language-local-name="Zweeds" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%81%E0%B8%81%E0%B9%8A%E0%B8%AA%E0%B8%8B%E0%B8%B5%E0%B9%80%E0%B8%AD%E0%B9%87%E0%B8%99" title="แก๊สซีเอ็น – Thai" lang="th" hreflang="th" data-title="แก๊สซีเอ็น" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A5%D0%BB%D0%BE%D1%80%D0%B0%D1%86%D0%B5%D1%82%D0%BE%D1%84%D0%B5%D0%BD%D0%BE%D0%BD" title="Хлорацетофенон – Oekraïens" lang="uk" hreflang="uk" data-title="Хлорацетофенон" data-language-autonym="Українська" data-language-local-name="Oekraïens" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/2-%E6%B0%AF%E8%8B%AF%E4%B9%99%E9%85%AE" title="2-氯苯乙酮 – Chinees" lang="zh" hreflang="zh" data-title="2-氯苯乙酮" data-language-autonym="中文" data-language-local-name="Chinees" 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/Q284209#sitelinks-wikipedia" title="Taalkoppelingen bewerken" class="wbc-editpage">Koppelingen bewerken</a></span></div> </div> </div> </div> </header> <div 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font-size:120%;" colspan="3">2-chlooracetofenon </th></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit; text-align:center;" colspan="3">Structuurformule en molecuulmodel </th></tr> <tr> <td style="text-align:center; padding:0;" colspan="3"><span typeof="mw:File"><a href="/wiki/Bestand:Chlooracetofenon.png" class="mw-file-description"><img alt="Structuurformule van 2-chlooracetofenon" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Chlooracetofenon.png/170px-Chlooracetofenon.png" decoding="async" width="170" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Chlooracetofenon.png/255px-Chlooracetofenon.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/84/Chlooracetofenon.png/340px-Chlooracetofenon.png 2x" data-file-width="599" data-file-height="418" /></a></span> </td></tr> <tr> <td style="text-align:center;" colspan="3"><div style="font-size:90%"><a href="/wiki/Structuurformule" title="Structuurformule">Structuurformule</a> van 2-chlooracetofenon</div> </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit; text-align:center;" colspan="3">Algemeen </th></tr> <tr> <th><a href="/wiki/Molecuulformule" title="Molecuulformule">Molecuulformule</a> </th> <td colspan="2">C<sub>8</sub>H<sub>7</sub>ClO </td></tr> <tr> <th><a href="/wiki/IUPAC-nomenclatuur" title="IUPAC-nomenclatuur">IUPAC-naam</a> </th> <td colspan="2">2-chlooracetofenon </td></tr> <tr> <th><a href="/wiki/Nomenclatuur" title="Nomenclatuur">Andere namen</a> </th> <td colspan="2">chloormethylfenylketon, fenacylchloride, CN-gas </td></tr> <tr> <th><a href="/wiki/Molaire_massa" title="Molaire massa">Molmassa</a> </th> <td colspan="2">154,59358 <a href="/wiki/Gram_(eenheid)" title="Gram (eenheid)">g</a>/<a href="/wiki/Mol_(eenheid)" title="Mol (eenheid)">mol</a> </td></tr> <tr> <th><a href="/wiki/SMILES" title="SMILES">SMILES</a> </th> <td colspan="2"><div style="word-wrap:break-word; width:127px;">C1CCC(CC1)C(=O)CCl</div> </td></tr> <tr> <th><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a> </th> <td colspan="2"><div style="word-wrap:break-word; width:127px;">1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2</div> </td></tr> <tr> <th><a href="/wiki/CAS-nummer" title="CAS-nummer">CAS-nummer</a> </th> <td colspan="2"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=532-27-4">532-27-4</a> </td></tr> <tr> <th><a href="/wiki/EG-nummer" title="EG-nummer">EG-nummer</a> </th> <td colspan="2"><a rel="nofollow" class="external text" href="http://echa.europa.eu/web/guest/information-on-chemicals/cl-inventory-database/-/cl-inventory/search-clinventory-by-other-identifier/208-531-1">208-531-1</a> </td></tr> <tr> <th><a href="/wiki/PubChem" title="PubChem">PubChem</a> </th> <td colspan="2"><a rel="nofollow" class="external text" href="http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10757">10757</a> </td></tr> <tr> <th><a href="/wiki/Wikidata" title="Wikidata">Wikidata</a> </th> <td colspan="2"><a href="https://www.wikidata.org/wiki/Q284209" class="extiw" title="d:Q284209">Q284209</a> </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit;" colspan="3">Waarschuwingen en veiligheidsmaatregelen </th></tr> <tr> <td class="ta-center" colspan="3"><table align="center" style="border-style:none;"><tbody><tr><td style="margin-left:auto;margin-right:auto;vertical-align:top;text-align:center;border-style:none;cell-padding:2px"><span typeof="mw:File"><a href="/wiki/Bestand:GHS-pictogram-acid.svg" class="mw-file-description" title="Corrosief"><img alt="Corrosief" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/60px-GHS-pictogram-acid.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/90px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/120px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span></td><td style="margin-left:auto;margin-right:auto;vertical-align:top;text-align:center;border-style:none;cell-padding:2px"><span typeof="mw:File"><a href="/wiki/Bestand:GHS-pictogram-skull.svg" class="mw-file-description" title="Toxisch"><img alt="Toxisch" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/60px-GHS-pictogram-skull.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/90px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/120px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span></td><td style="margin-left:auto;margin-right:auto;vertical-align:top;text-align:center;border-style:none;cell-padding:2px"><span typeof="mw:File"><a href="/wiki/Bestand:GHS-pictogram-silhouette.svg" class="mw-file-description" title="Schadelijk voor de gezondheid"><img alt="Schadelijk voor de gezondheid" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/60px-GHS-pictogram-silhouette.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/90px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/120px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span></td></tr></tbody></table><b>Gevaar</b> </td></tr> <tr> <th><a href="/wiki/H-_en_P-zinnen" title="H- en P-zinnen">H-zinnen</a> </th> <td colspan="2"><abbr title="Dodelijk bij inslikken.">H300</abbr> - <abbr title="Giftig bij contact met de huid.">H311</abbr> - <abbr title="Veroorzaakt huidirritatie.">H315</abbr> - <abbr title="Veroorzaakt ernstig oogletsel.">H318</abbr> - <abbr title="Giftig bij inademing.">H331</abbr> - <abbr title="Kan bij inademing allergie- of astmasymptomen of ademhalingsmoeilijkheden veroorzaken.">H334</abbr> - <abbr title="Kan irritatie van de luchtwegen veroorzaken.">H335</abbr> </td></tr> <tr> <th><span class="nowrap"><a href="/wiki/H-_en_P-zinnen" title="H- en P-zinnen">EUH-zinnen</a></span> </th> <td colspan="2"><i>geen</i> </td></tr> <tr> <th><a href="/wiki/H-_en_P-zinnen" title="H- en P-zinnen">P-zinnen</a> </th> <td colspan="2"><abbr title="Inademing van stof/rook/gas/nevel/damp/spuitnevel vermijden.">P261</abbr> - <abbr title="Na het werken met dit product ... grondig wassen.">P264</abbr>-<abbr title="Beschermende handschoenen/beschermende kleding/oogbescherming/gelaatsbescherming dragen.">P280</abbr>-<abbr title="Na inslikken: onmiddellijk een antigifcentrum of een arts raadplegen.">P301+P310</abbr>-<br /><abbr title="Bij contact met de ogen: voorzichtig afspoelen met water gedurende een aantal minuten; contactlenzen verwijderen, indien mogelijk; blijven spoelen.">P305+P351+P338</abbr>-<abbr title="Een antigifcentrum of een arts raadplegen.">P311</abbr> </td></tr> <tr> <th><a href="/wiki/Stofidentificatienummer" title="Stofidentificatienummer">VN-nummer</a> </th> <td colspan="2">1697 </td></tr> <tr> <th><a href="/wiki/ADR-gevarenklassen_en_-labels" title="ADR-gevarenklassen en -labels">ADR-klasse</a> </th> <td colspan="2">Gevarenklasse 6.1 </td></tr> <tr> <th><a href="/wiki/LD50" title="LD50">LD<sub>50</sub></a> (ratten) </th> <td colspan="2">(oraal) 127 mg/kg </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit;" colspan="3">Fysische eigenschappen </th></tr> <tr> <th><a href="/wiki/Aggregatietoestand" title="Aggregatietoestand">Aggregatietoestand</a> </th> <td colspan="2">vast </td></tr> <tr> <th><a href="/wiki/Kleur_(hoofdbetekenis)" class="mw-redirect" title="Kleur (hoofdbetekenis)">Kleur</a> </th> <td colspan="2">kleurloos-grijs </td></tr> <tr> <th><a href="/wiki/Massadichtheid" title="Massadichtheid">Dichtheid</a> </th> <td colspan="2">1,3 g/cm³ </td></tr> <tr> <th><a href="/wiki/Smeltpunt" title="Smeltpunt">Smeltpunt</a> </th> <td colspan="2">54-59 °C </td></tr> <tr> <th><a href="/wiki/Kookpunt" title="Kookpunt">Kookpunt</a> </th> <td colspan="2">244-245 °C </td></tr> <tr> <th><a href="/wiki/Vlampunt" title="Vlampunt">Vlampunt</a> </th> <td colspan="2">118 °C </td></tr> <tr> <th><a href="/wiki/Dampdruk" title="Dampdruk">Dampdruk</a> </th> <td colspan="2">(bij 20°C) 0,7 Pa </td></tr> <tr> <th><a href="/wiki/Oplosbaarheid" title="Oplosbaarheid">Oplosbaarheid</a> in <a href="/wiki/Water" title="Water">water</a> </th> <td colspan="2">16,4 g/L </td></tr> <tr> <th>Goed oplosbaar in </th> <td colspan="2">aceton </td></tr> <tr> <th>Slecht oplosbaar in </th> <td colspan="2">water </td></tr> <tr> <th><a href="/wiki/Octanol-water-partitieco%C3%ABffici%C3%ABnt" title="Octanol-water-partitiecoëfficiënt">log(<i>P</i><sub>ow</sub>)</a> </th> <td colspan="2">2,08 </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit;" colspan="3"><small>Tenzij anders vermeld zijn <a href="/wiki/Standaardomstandigheden" title="Standaardomstandigheden">standaardomstandigheden</a> gebruikt (298,15 <a href="/wiki/Kelvin_(eenheid)" title="Kelvin (eenheid)">K</a> of 25 <a href="/wiki/Celsius" title="Celsius">°C</a>, 1 <a href="/wiki/Bar_(druk)" title="Bar (druk)">bar</a>).</small> </th></tr> <tr> <td class="infobox-kop notheme center" style="background-color:#DDEEFF; color:inherit;" colspan="3"> <table cellspacing="0" cellpadding="0"> <tbody><tr> <td style="vertical-align:middle;"><b>Portaal</b>  <span class="noviewer" typeof="mw:File"><a href="/wiki/Bestand:Portal.svg" class="mw-file-description" title="Portaalicoon"><img alt="Portaalicoon" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/22px-Portal.svg.png" decoding="async" width="22" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/33px-Portal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/44px-Portal.svg.png 2x" data-file-width="36" data-file-height="32" /></a></span>   </td> <td class="ta-left"><b><a href="/wiki/Portaal:Scheikunde" title="Portaal:Scheikunde">Scheikunde</a> </b> </td></tr></tbody></table> </td></tr> </tbody></table> <p><b>Chlooracetofenon</b> of <b>CN-gas</b> is een <a href="/wiki/Organische_verbinding" title="Organische verbinding">organische verbinding</a> met als <a href="/wiki/Brutoformule" title="Brutoformule">brutoformule</a> C<sub>8</sub>H<sub>7</sub>ClO. De zuivere stof komt voor als een kleurloze tot grijze <a href="/wiki/Vaste_stof" title="Vaste stof">vaste stof</a>, die slecht oplosbaar is in water. De schadelijke effecten die de stof op ogen, huid en het <a href="/wiki/Ademhalingsstelsel" title="Ademhalingsstelsel">ademhalingsstelsel</a> heeft, maken dit een uitermate geschikt middel voor gebruik in <a href="/wiki/Traangas" title="Traangas">traangasgranaten</a> voor bijvoorbeeld het bestrijden van rellen. Chlooracetofenon is de actieve stof in <a href="/wiki/Foelie" title="Foelie">foelie</a> (het vlezige omhulsel van de <a href="/wiki/Nootmuskaat" title="Nootmuskaat">muskaatnoot</a>).<sup id="cite_ref-emedicine.medscape.com_1-0" class="reference"><a href="#cite_note-emedicine.medscape.com-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ReferenceA_2-0" class="reference"><a href="#cite_note-ReferenceA-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Geschiedenis">Geschiedenis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=1" title="Bewerk dit kopje: Geschiedenis" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=1" title="De broncode bewerken van de sectie: Geschiedenis"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Traangasachtige stoffen werden al in de <a href="/wiki/5e_eeuw_v.Chr." title="5e eeuw v.Chr.">5e eeuw v.Chr.</a> gebruikt door de <a href="/wiki/Sparta_(Griekenland)" title="Sparta (Griekenland)">Spartanen</a>. Zij gebruikten een combinatie van brandende <a href="/wiki/Was_(substantie)" title="Was (substantie)">was</a> en <a href="/wiki/Sulfide" title="Sulfide">sulfiden</a>. In de <a href="/wiki/Eerste_Wereldoorlog" title="Eerste Wereldoorlog">Eerste Wereldoorlog</a> werd voor het eerst gebruikgemaakt van chemische wapens.<sup id="cite_ref-emedicine.medscape.com_1-1" class="reference"><a href="#cite_note-emedicine.medscape.com-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ReferenceA_2-1" class="reference"><a href="#cite_note-ReferenceA-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Deze chemische stoffen werden toegepast om een tegenstander tijdelijk uit te schakelen. De ontdekking van chlooracetofenon stamt uit 1869, toen de Duitse onderzoeker <a href="/w/index.php?title=Carl_Graebe&action=edit&redlink=1" class="new" title="Carl Graebe (de pagina bestaat niet)">Carl Graebe</a> de stof voor het eerst beschreef. Chlooracetofenon werd voor het eerst gebruikt in 1877, maar nog niet voor grote doelen.<sup id="cite_ref-ReferenceA_2-2" class="reference"><a href="#cite_note-ReferenceA-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Dit gebeurde pas in 1920 in <a href="/wiki/Frankrijk" title="Frankrijk">Frankrijk</a>, waar chlooracetofenon gebruikt werd om opstanden te stoppen. Vanaf toen zijn meerdere landen de stof gaan gebruiken. </p><p>Gedurende vele jaren was chlooracetofenon het meest gebruikte reagens door het leger, maar wegens de instabiliteit van de stof zijn militaire onderzoekers verder gaan zoeken naar alternatieven, zoals <a href="/wiki/CS-gas" title="CS-gas">CS-gas</a>, dat gebruikt wordt in <a href="/wiki/Pepperspray" title="Pepperspray">peppersprays</a>. CS-gas is echter minder <a href="/wiki/Vergif" title="Vergif">toxisch</a> en veroorzaakt minder langdurige effecten dan chlooracetofenon. Doordat het een vaste stof is dient het verspreid te worden in de vorm van een <a href="/wiki/Aerosol" title="Aerosol">aerosol</a> (een oplossing van chlooracetofenon die in de lucht verstoven wordt). Pepperspray en traangas vallen in Nederland en België onder de <a href="/w/index.php?title=Verboden_wapens&action=edit&redlink=1" class="new" title="Verboden wapens (de pagina bestaat niet)">verboden wapens</a>, en mogen dus niet worden gebruikt door particulieren. </p><p>De tweeletterige code van chlooracetofenon (CN) en andere traangassen is ingevoerd door de <a href="/wiki/Noord-Atlantische_Verdragsorganisatie" title="Noord-Atlantische Verdragsorganisatie">NAVO</a>.<sup id="cite_ref-emedicine.medscape.com_1-2" class="reference"><a href="#cite_note-emedicine.medscape.com-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Chlooracetofenon was een van de primaire stoffen bekend na de Eerste Wereldoorlog die inwerken op - en klachten veroorzaken aan - de luchtwegen. Het wordt al sinds 1920 gebruikt als een persoonlijk verdedigingsmiddel.<sup id="cite_ref-thetartan.org_4-0" class="reference"><a href="#cite_note-thetartan.org-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Corson en Stoughton ontwikkelde in 1928 CS-gas, wat een tienmaal krachtiger traanverwekkend effect heeft dan chlooracetofenon, maar een stuk minder toxisch is. Rond 1959 werd chlooracetofenon vervangen door CS-gas als een primair middel van overheden om agressieve mensenmassa's onder controle te houden.<sup id="cite_ref-emedicine.medscape.com_1-3" class="reference"><a href="#cite_note-emedicine.medscape.com-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Tijdens de <a href="/wiki/Vietnamoorlog" title="Vietnamoorlog">Vietnamoorlog</a> zouden de Amerikanen chlooracetofenon en CS-gas ingezet hebben ter ondersteuning van de militaire operaties in <a href="/wiki/Zuid-Vietnam" title="Zuid-Vietnam">Zuid-Vietnam</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthese">Synthese</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=2" title="Bewerk dit kopje: Synthese" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=2" title="De broncode bewerken van de sectie: Synthese"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chlooracetofenon wordt gesynthetiseerd door middel van de <a href="/wiki/Friedel-Craftsacylering" title="Friedel-Craftsacylering">Friedel-Craftsacylering</a> tussen <a href="/wiki/Benzeen" title="Benzeen">benzeen</a> en <a href="/wiki/Chlooracetylchloride" title="Chlooracetylchloride">chlooracetylchloride</a>. De reactie wordt gekatalyseerd door <a href="/wiki/Aluminiumchloride" title="Aluminiumchloride">aluminiumchloride</a>. </p> <dl><dd><figure class="mw-halign-left" typeof="mw:File"><a href="/wiki/Bestand:Synthese_chlooracetofenon.png" class="mw-file-description" title="Synthese van chlooracetofenon"><img alt="Synthese van chlooracetofenon" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Synthese_chlooracetofenon.png/550px-Synthese_chlooracetofenon.png" decoding="async" width="550" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Synthese_chlooracetofenon.png/825px-Synthese_chlooracetofenon.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/Synthese_chlooracetofenon.png/1100px-Synthese_chlooracetofenon.png 2x" data-file-width="2199" data-file-height="418" /></a><figcaption>Synthese van chlooracetofenon</figcaption></figure></dd></dl> <div style="clear:left;"></div> <p>Een alternatieve syntheseroute betreft de <a href="/wiki/Ketonhalogenering" title="Ketonhalogenering">ketonhalogenering</a> van <a href="/wiki/Acetofenon" title="Acetofenon">acetofenon</a> met <a href="/wiki/Dichloor" title="Dichloor">dichloor</a> en een katalytische hoeveelheid <a href="/wiki/Waterstofchloride" title="Waterstofchloride">waterstofchloride</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Toepassingen">Toepassingen</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=3" title="Bewerk dit kopje: Toepassingen" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=3" title="De broncode bewerken van de sectie: Toepassingen"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chlooracetofenon is een krachtig middel om agressieve mensenmassa's in bedwang te houden. Het werd in 1965 in de vorm van een spray op de markt gebracht door de General Ordinance and Equipment Company<sup id="cite_ref-thetartan.org_4-1" class="reference"><a href="#cite_note-thetartan.org-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> als een verdedigingsmiddel, onder de merknaam <i>Mace</i>.<sup id="cite_ref-thetartan.org_4-2" class="reference"><a href="#cite_note-thetartan.org-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Jason_Smith_2002._p._595_6-0" class="reference"><a href="#cite_note-Jason_Smith_2002._p._595-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> De term <i>Mace</i> wordt tegenwoordig al snel incorrect gebruikt voor alle verdedigingssprays (traangassen) terwijl dit eigenlijk alleen chlooracetofenon betreft. </p><p>Chlooracetofenon wordt tegenwoordig minder frequent gebruikt omdat het zeer schadelijk is; er wordt dan gekozen voor CS-gas.<sup id="cite_ref-Jason_Smith_2002._p._595_6-1" class="reference"><a href="#cite_note-Jason_Smith_2002._p._595-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Werkingsmechanisme">Werkingsmechanisme</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=4" title="Bewerk dit kopje: Werkingsmechanisme" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=4" title="De broncode bewerken van de sectie: Werkingsmechanisme"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Het <a href="/wiki/Toxicologie" title="Toxicologie">toxicologisch</a> werkingsmechanisme van chlooracetofenon is voornamelijk te verklaren door het <a href="/wiki/Alkylering" title="Alkylering">alkylerend</a> karakter van de stof. Het aanwezige <a href="/wiki/Chloor_(element)" title="Chloor (element)">chlooratoom</a> dient daarbij als <a href="/wiki/Leaving_group" title="Leaving group">leaving group</a>. Door deze alkylering zouden <a href="/wiki/Hydroxylgroep" title="Hydroxylgroep">hydroxyl-</a> en <a href="/wiki/Thiol" title="Thiol">thiolbevattende</a> <a href="/wiki/Enzym" title="Enzym">enzymen</a> kunnen worden <a href="/wiki/Inhibitie_van_enzymen" title="Inhibitie van enzymen">geïnhibiteerd</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Het is bekend dat chlooracetofenon <a href="/wiki/Cholinesterase" title="Cholinesterase">cholinesterases</a> remt,<sup id="cite_ref-Castro,_J.A._1966._p._49-56_8-0" class="reference"><a href="#cite_note-Castro,_J.A._1966._p._49-56-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> alsook enzymen die betrokken zijn bij de synthese van <a href="/wiki/Fosfolipide" title="Fosfolipide">fosfolipiden</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> Verder treedt ook verstoring van het <a href="/wiki/Glucose" title="Glucose">glucosemetabolisme</a> op.<sup id="cite_ref-Castro,_J.A._1966._p._49-56_8-1" class="reference"><a href="#cite_note-Castro,_J.A._1966._p._49-56-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Rutledge en Deitrich ontdekten in 1971 dat de activiteit van het enzym <a href="/wiki/Aldehydedehydrogenase" title="Aldehydedehydrogenase">aldehydedehydrogenase</a> geremd wordt door chlooracetofenon, omdat zij een verandering waarnamen in het <a href="/wiki/Noradrenaline" title="Noradrenaline">noradrenalinemetabolisme</a> in de <a href="/wiki/Hersenen" title="Hersenen">hersenen</a> van <a href="/wiki/Konijn_(dier)" class="mw-redirect" title="Konijn (dier)">konijnen</a>. De pijn en irritatie die daarbij optreden worden veroorzaakt door het vrijgekomen chloride-ion. </p> <div class="mw-heading mw-heading2"><h2 id="Toxicologie_en_veiligheid">Toxicologie en veiligheid</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=5" title="Bewerk dit kopje: Toxicologie en veiligheid" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=5" title="De broncode bewerken van de sectie: Toxicologie en veiligheid"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Inhalatie">Inhalatie</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=6" title="Bewerk dit kopje: Inhalatie" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=6" title="De broncode bewerken van de sectie: Inhalatie"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Inademing van chlooracetofenon heeft een brandend gevoel in de longen tot gevolg. De getroffen persoon kan hierdoor moeilijk ademen, moet hoesten, en wordt misselijk. Als een persoon bewusteloos is geraakt moet hij kunstmatig beademd worden en dient een dokter te worden gewaarschuwd. Voorkomen van inhalatie kan door lokale afzuiging of door bescherming met een mondkapje.<sup id="cite_ref-actrav.itcilo.org_10-0" class="reference"><a href="#cite_note-actrav.itcilo.org-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Dermaal_contact">Dermaal contact</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=7" title="Bewerk dit kopje: Dermaal contact" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=7" title="De broncode bewerken van de sectie: Dermaal contact"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Wanneer chlooracetofenon in contact komt met de huid, treden roodheid en pijnlijke irritatie op. Huidcontact kan vermeden worden door aangepaste kledij en handschoenen te dragen. </p><p>De <a href="/wiki/Permeabiliteit_(materiaal)" title="Permeabiliteit (materiaal)">permeabiliteit</a> van de huid wordt in het geval van chlooracetofenon veroorzaakt doordat de stof een gehalogeneerde koolwaterstof is.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Oogcontact">Oogcontact</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=8" title="Bewerk dit kopje: Oogcontact" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=8" title="De broncode bewerken van de sectie: Oogcontact"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Contact met de ogen kan aanleiding geven tot roodheid, pijn, troebel zicht en soms zelfs permanent (partieel) verlies van het zicht. Chlooracetofenon is een <a href="/wiki/Lacrimator" title="Lacrimator">lacrimator</a>, hetgeen betekent dat het de ogen doet tranen. </p><p>Het dragen van <a href="/w/index.php?title=Gezichtsbescherming&action=edit&redlink=1" class="new" title="Gezichtsbescherming (de pagina bestaat niet)">gezichtsbescherming</a>, zoals een <a href="/wiki/Veiligheidsbril" title="Veiligheidsbril">veiligheidsbril</a>, kan oogcontact voorkomen.<sup id="cite_ref-actrav.itcilo.org_10-1" class="reference"><a href="#cite_note-actrav.itcilo.org-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Chronische_effecten_op_de_gezondheid">Chronische effecten op de gezondheid</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=9" title="Bewerk dit kopje: Chronische effecten op de gezondheid" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=9" title="De broncode bewerken van de sectie: Chronische effecten op de gezondheid"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Bij de mens zijn geen chronische effecten van chlooracetofenon gevonden. Onderzoeken hebben aangetoond dat chronisch blootgestelde ratten vaker een afwijking in het neusslijmvlies vertoonden.<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> Bij vrouwtjesratten is een marginale toename van <a href="/wiki/Fibroadenoom" title="Fibroadenoom">fibroadenomen</a> in het borstweefsel vastgesteld na chronische blootstelling. </p> <div class="mw-heading mw-heading2"><h2 id="Toxicologische_studies">Toxicologische studies</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=10" title="Bewerk dit kopje: Toxicologische studies" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=10" title="De broncode bewerken van de sectie: Toxicologische studies"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Toxicologische_studie_bij_de_rat">Toxicologische studie bij de rat</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=11" title="Bewerk dit kopje: Toxicologische studie bij de rat" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=11" title="De broncode bewerken van de sectie: Toxicologische studie bij de rat"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Bij onderzoeken met ratten werd de <a href="/wiki/LD50" title="LD50">LD<sub>50</sub>-waarde</a> bepaald op 127 mg per kilogram lichaamsgewicht via een orale toediening. Bij een intraperitoneale toediening ligt de LD<sub>50</sub> op 36 mg/kg en bij een intraveneuze toediening op 41 mg/kg. Bij een meer voor de hand liggende blootstelling aan chlooracetofenon via inhalatie is een LC<sub>t50</sub>-waarde bekend variërend van 3,7 mg·min/m³ tot 8,75 mg·min/m³ (250 tot 750 mg/m³ voor 15-60 minuten), afhankelijk van het onderzoek. </p><p>De sterfte van de dieren was te wijten aan <a href="/wiki/Verstikking" title="Verstikking">verstikking</a> na longschade door inwendige <a href="/wiki/Bloeding" title="Bloeding">bloedingen</a> en de accumulatie van bloed in de longen, en <a href="/wiki/Longoedeem" title="Longoedeem">longoedeem</a>. Andere effecten waren lacrimatie, vermoeidheid, abnormale hoeveelheid speekselvorming en een moeizame ademhaling. </p><p>Geschat wordt dat bij mensen de LC<sub>50</sub> ligt op 8,0 tot 11,0 mg·min/m³ bij inhalatie.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Ontwikkelingstoxicologie">Ontwikkelingstoxicologie</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=12" title="Bewerk dit kopje: Ontwikkelingstoxicologie" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=12" title="De broncode bewerken van de sectie: Ontwikkelingstoxicologie"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Bij onderzoeken waarin het effect van chlooracetofenon tijdens de <a href="/wiki/Embryo" title="Embryo">embryonale ontwikkeling</a> is gemeten, is een verhoogde kans waargenomen op het ontwikkelen van afwijkingen in het zenuwstelsel, evenals het niet volledig ontwikkelen van de hersenen. Hierbij werden kippenembryo's gedurende 15 tot 120 minuten blootgesteld aan 0,5 tot 3,0 <a href="/wiki/Molair" title="Molair">mM</a> chlooracetofenon. Er zijn geen onderzoeken bekend naar het effect van chlooracetofenon op de ontwikkeling van de mens en andere zoogdieren.<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> <div class="mw-heading mw-heading3"><h3 id="Mutageniteit">Mutageniteit</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=13" title="Bewerk dit kopje: Mutageniteit" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=13" title="De broncode bewerken van de sectie: Mutageniteit"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chlooracetofenon is niet-<a href="/wiki/Mutageen" title="Mutageen">mutageen</a> bevonden na onderzoeken naar <i><a href="/w/index.php?title=Salmonella_typhimurium&action=edit&redlink=1" class="new" title="Salmonella typhimurium (de pagina bestaat niet)">Salmonella typhimurium</a></i>-stammen TA98, TA100, TA1535 en TA1537. In CHO-cellen veroorzaakte chlooracetofenon geen uitwisseling van <a href="/wiki/Gen" title="Gen">genetisch materiaal</a> tussen twee <a href="/w/index.php?title=Zusterchromatiden&action=edit&redlink=1" class="new" title="Zusterchromatiden (de pagina bestaat niet)">zusterchromatiden</a>.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Carcinogeniteit">Carcinogeniteit</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=14" title="Bewerk dit kopje: Carcinogeniteit" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=14" title="De broncode bewerken van de sectie: Carcinogeniteit"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chlooracetofenon is niet <a href="/wiki/Carcinogeen" title="Carcinogeen">carcinogeen</a> bevonden na de <a href="/wiki/Dermaal" title="Dermaal">dermale</a> toediening van 0,003 M (0,05%) chlooracetofenon, tweemaal daags gedurende een periode van vijf maanden.<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><p>Gwynn en Salaman rapporteerden in 1953 dat chlooracetofenon wel co-carcinogeen was bevonden omdat het de kans op <a href="/w/index.php?title=Papilloom&action=edit&redlink=1" class="new" title="Papilloom (de pagina bestaat niet)">papillomen</a> in de huid verhoogde na chronische dermale toediening van chlooracetofenon aan muizen, die vooraf dermaal blootgesteld waren aan 0,3 mL van 0,15% <a href="/w/index.php?title=9,10-dimethyl-1,2-benzantraceen&action=edit&redlink=1" class="new" title="9,10-dimethyl-1,2-benzantraceen (de pagina bestaat niet)">9,10-dimethyl-1,2-benzantraceen</a> (DMBA).<sup id="cite_ref-PMID_13126392_17-0" class="reference"><a href="#cite_note-PMID_13126392-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Opslag_en_transport">Opslag en transport</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=15" title="Bewerk dit kopje: Opslag en transport" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=15" title="De broncode bewerken van de sectie: Opslag en transport"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chlooracetofenon dient opgeslagen te worden in een droge ruimte met voldoende afzuiging. Chlooracetofenon mag niet samen met etenswaren vervoerd of opgeslagen worden. De stof kan gemakkelijk opgeveegd worden en dient afgevoerd te worden in een afsluitbare container. </p> <div class="mw-heading mw-heading2"><h2 id="Externe_links">Externe links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chlooracetofenon&veaction=edit&section=16" title="Bewerk dit kopje: Externe links" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Chlooracetofenon&action=edit&section=16" title="De broncode bewerken van de sectie: Externe links"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><span typeof="mw:File"><a href="/wiki/Bestand:Nuvola_apps_important_yellow.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Nuvola_apps_important_yellow.svg/14px-Nuvola_apps_important_yellow.svg.png" decoding="async" width="14" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Nuvola_apps_important_yellow.svg/21px-Nuvola_apps_important_yellow.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Nuvola_apps_important_yellow.svg/28px-Nuvola_apps_important_yellow.svg.png 2x" data-file-width="600" data-file-height="500" /></a></span> <i><a rel="nofollow" class="external text" href="https://www.ilo.org/dyn/icsc/showcard.display?p_lang=en&p_card_id=0128">chlooracetofenon</a></i> - <small><small><a href="/wiki/International_Chemical_Safety_Card" title="International Chemical Safety Card">International Chemical Safety Card</a></small></small></li> <li><style data-mw-deduplicate="TemplateStyles:r67679320">.mw-parser-output .taalaanduiding{font-family:sans-serif;font-size:85%;cursor:help;color:var(--color-subtle,#555)}.mw-parser-output .taalaanduiding span{border-bottom:1px dotted var(--color-subtle,#555)}</style><span class="taalaanduiding" title="Taal: Engels">(<span>en</span>) </span> <a rel="nofollow" class="external text" href="https://fscimage.fishersci.com/msds/05497.htm">MSDS van <i>chlooracetofenon</i></a></li></ul> <div class="toccolours appendix" role="presentation" style="font-size:90%; margin:1em 0 -0.5em; clear:both;"> <div><span style="font-weight:bold">Bronnen, noten en/of referenties</span></div> <div class="reflist" style="list-style-type: decimal;"><div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-emedicine.medscape.com-1"><span class="mw-cite-backlink">↑ <a href="#cite_ref-emedicine.medscape.com_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-emedicine.medscape.com_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-emedicine.medscape.com_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-emedicine.medscape.com_1-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text">Rega, P.P. CBRNE - Irritants - CS, CN, CNC, CA, CR, CNB, PS. 2009; Available from: <a rel="nofollow" class="external free" href="https://emedicine.medscape.com/">https://emedicine.medscape.com/</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230607211924/https://emedicine.medscape.com/">Gearchiveerd</a> op 7 juni 2023.</span> </li> <li id="cite_note-ReferenceA-2"><span class="mw-cite-backlink">↑ <a href="#cite_ref-ReferenceA_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ReferenceA_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ReferenceA_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">Tuorinsky, M.a.J.J.H., Medical Aspects of Chemical Warfare</span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text">inc, Z.i. Chloroacetophenone (CN): <a rel="nofollow" class="external free" href="https://web.archive.org/web/20090422081416/http://www.zarc.com/english/tear_gases/cn-main.html">https://web.archive.org/web/20090422081416/http://www.zarc.com/english/tear_gases/cn-main.html</a></span> </li> <li id="cite_note-thetartan.org-4"><span class="mw-cite-backlink">↑ <a href="#cite_ref-thetartan.org_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-thetartan.org_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-thetartan.org_4-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">Huang, D. How Things Work: Tear gas. 2009; Available from: <a rel="nofollow" class="external free" href="http://www.thetartan.org/2009/4/6/scitech/howthingswork">http://www.thetartan.org/2009/4/6/scitech/howthingswork</a></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">Lieutenant General John H. Hay, J., Tactical and Materiel Innovations. 1989</span> </li> <li id="cite_note-Jason_Smith_2002._p._595-6"><span class="mw-cite-backlink">↑ <a href="#cite_ref-Jason_Smith_2002._p._595_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Jason_Smith_2002._p._595_6-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Jason Smith, M., MRCP(UK), and Ian Greaves, MBBS, MRCP(UK), The Use of Chemical Incapacitant Sprays: A Review. J Trauma, 2002. 52: p. 595–600</span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text">Cucinell, S.A., et al., Biochemical interactions and metabolic fate of riot control agents. Fed Proc, 1971. 30(1): p. 86-91</span> </li> <li id="cite_note-Castro,_J.A._1966._p._49-56-8"><span class="mw-cite-backlink">↑ <a href="#cite_ref-Castro,_J.A._1966._p._49-56_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Castro,_J.A._1966._p._49-56_8-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Castro, J.A., Action of w-chloroacetophenon on several enzymes. Enzymologia, 1966. 30: p. 49-56</span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><a href="#cite_ref-9">↑</a></span> <span class="reference-text">Kageyama, K., Y. Onoyama, and E. Kano, Effects of methyl mercuric chloride and sulfhydryl inhibitors on phospholipid synthetic activity of lymphocytes. J Appl Toxicol, 1986. 6(1): p. 49-53</span> </li> <li id="cite_note-actrav.itcilo.org-10"><span class="mw-cite-backlink">↑ <a href="#cite_ref-actrav.itcilo.org_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-actrav.itcilo.org_10-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">International Chemical Safety Cards Available from: <a rel="nofollow" class="external free" href="https://web.archive.org/web/20090106021444/http://actrav.itcilo.org/">https://web.archive.org/web/20090106021444/http://actrav.itcilo.org/</a></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><a href="#cite_ref-11">↑</a></span> <span class="reference-text"><span style="font-variant:small-caps;">J. Ashby, D.A. Basketter, D. Paton & I. Kimber</span> (1995) - <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pubmed/8553361"><i>Structure activity relationships in skin sensitization using the murine local lymph node assay</i></a>, Toxicology, <b>103</b> (3), pp. 177-194</span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><a href="#cite_ref-12">↑</a></span> <span class="reference-text">NTP Toxicology and Carcinogenesis Studies of 2-chlooracetofenon (CAS No. 532-27-4) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Natl Toxicol Program Tech Rep Ser, 1990. 379: p. 1-191</span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><a href="#cite_ref-13">↑</a></span> <span class="reference-text">Punte, C.L., et al., Inhalation studies with chloracetophenone, diphenylamino-chloroarsine, and pelargonic morpholide--II. Human exposures. Am Ind Hyg Assoc J, 1962. 23: pp. 199-202</span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><a href="#cite_ref-14">↑</a></span> <span class="reference-text">Lakshmi, M.S., The effect of chloroacetophenone on chick embryos cultured in vitro. J Embryol Exp Morphol, 1962. 10: p. 373-82</span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><a href="#cite_ref-15">↑</a></span> <span class="reference-text">Zeiger, E., et al., Salmonella mutagenicity tests: III. Results from the testing of 255 chemicals. Environ Mutagen, 1987. 9 Suppl 9: p. 1-109</span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><a href="#cite_ref-16">↑</a></span> <span class="reference-text">Documentation of the Threshold Limit Values and Biological Exposure Indices, in American Conference of Governmental Industrial Hygienists 1986, Exposure Indices: Cincinnati. p. 121-122</span> </li> <li id="cite_note-PMID_13126392-17"><span class="mw-cite-backlink"><a href="#cite_ref-PMID_13126392_17-0">↑</a></span> <span class="reference-text"><span class="citation" id="CITEREFGwynn_RH,_Salaman_MH.1953"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r67679320"><span class="taalaanduiding" title="Taal: Engels">(<span>en</span>) </span><span style="font-variant:small-caps;">Gwynn RH, Salaman MH.</span> (1953). <cite><a rel="nofollow" class="external text" href="https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&id=13126392&retmode=ref&cmd=prlinks">Studies on co-carcinogenesis. SH-reactors and other substances tested for co-carcinogenic action in mouse skin.</a></cite>. <i>Br J Cancer.</i> <b>7</b> (4): 482–9. <a href="/wiki/International_Standard_Serial_Number" title="International Standard Serial Number">ISSN</a>: <a rel="nofollow" class="external text" href="https://worldcat.org/issn/0007-0920">0007-0920</a>. <a href="/wiki/PubMed" title="PubMed">PMID</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pubmed/13126392">13126392</a>. <a href="/wiki/PubMed_Central" title="PubMed Central">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2007911">2007911</a>. Geraadpleegd op <span class="mw-formatted-date" title="2015-09-11">11 september 2015</span>. </span> Dit is een <a href="/wiki/Open_access" class="mw-disambig" title="Open access">open access</a> artikel.</span> </li> </ol></div></div> </div> <style data-mw-deduplicate="TemplateStyles:r67837862">.mw-parser-output .navigatie{position:relative;clear:both;overflow:auto;margin:1em auto -0.5em;padding:2px;background-color:var(--background-color-neutral-subtle,#f8f9fa);border:1px solid var(--border-color-base,#a2a9b1);text-align:center;font-size:87%}.mw-parser-output .navigatie-bewerken{margin-left:0.5em}.mw-parser-output .navigatie-bewerken .mw-ui-icon::before{background-size:0.9em}.mw-parser-output .navigatie-afb-links,.mw-parser-output .navigatie-afb-rechts{position:absolute}.mw-parser-output .navigatie-afb-rechts{right:2px}.mw-parser-output .navigatie-afb-groot{float:right;padding-left:0.5em}.mw-parser-output .navigatie-titel{background-color:#ddeef8;padding:2px 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/></a></span></span></div></div> <div id="Chemische_wapens" class="navigatie-titel"><a href="/wiki/Chemisch_wapen" title="Chemisch wapen">Chemische wapens</a></div> <div class="navigatie-inhoud"> <style data-mw-deduplicate="TemplateStyles:r67785531">.mw-parser-output .navigatie-tabel{margin:0 auto 0 auto;text-align:left}.mw-parser-output .navigatie-tabel .links{text-align:right}.mw-parser-output .navigatie-tabel .rechts{padding-left:0.5em}@media screen and (max-width:640px){.mw-parser-output .navigatie-tabel tr{display:grid;grid-template-columns:1fr;width:100%;margin-bottom:0.5em}.mw-parser-output .navigatie-tabel tr:last-of-type{margin-bottom:0}.mw-parser-output .navigatie-tabel .links{text-align:unset}.mw-parser-output .navigatie-tabel .rechts{padding:unset}}</style><table class="navigatie-tabel vatop" cellpadding="0" cellspacing="0" style=""><tbody><tr><td class="links" style=""><span class="nowrap"><b><a href="/w/index.php?title=Zuurstofverdringend_gas&action=edit&redlink=1" class="new" title="Zuurstofverdringend gas (de pagina bestaat niet)">Zuurstofverdringend gas</a>:</b></span></td><td class="rechts"><a href="/wiki/Cyanogeenchloride" title="Cyanogeenchloride">cyanogeenchloride</a> (CK) · <a href="/wiki/Waterstofcyanide" title="Waterstofcyanide">blauwzuur</a> (AC) · <a href="/wiki/Koolstofmonoxide" title="Koolstofmonoxide">koolstofmonoxide</a></td></tr><tr><td class="links"><b><a href="/wiki/Blaartrekkend_gas" title="Blaartrekkend gas">Blaartrekkend gas</a>:</b></td><td class="rechts"><a href="/wiki/Lewisiet" title="Lewisiet">lewisiet</a> (L) · <a href="/wiki/Mosterdgas" title="Mosterdgas">zwavel-mosterdgas</a> (HD, H, HT, HL, HQ) · <a href="/wiki/Stikstofmosterd" title="Stikstofmosterd">stikstof-mosterdgas</a> (HN1, HN2, HN3)</td></tr><tr><td class="links"><b><a href="/wiki/Zenuwgas" title="Zenuwgas">Zenuwgas</a>:</b></td><td class="rechts"><i>G-agentia:</i> <a href="/wiki/Tabun" title="Tabun">tabun</a> (GA) · <a href="/wiki/Sarin_(zenuwgas)" title="Sarin (zenuwgas)">sarin</a> (GB) · <a href="/wiki/Soman" title="Soman">soman</a> (GD) · <a href="/w/index.php?title=Cyclosarin&action=edit&redlink=1" class="new" title="Cyclosarin (de pagina bestaat niet)">cyclosarin</a> (GF) · <i>V-agentia:</i> <a href="/w/index.php?title=VE_(nerve_agent)&action=edit&redlink=1" class="new" title="VE (nerve agent) (de pagina bestaat niet)">VE</a> · <a href="/w/index.php?title=VG_(zenuwgas)&action=edit&redlink=1" class="new" title="VG (zenuwgas) (de pagina bestaat niet)">VG</a> · <a href="/w/index.php?title=VM_(zenuwgas)&action=edit&redlink=1" class="new" title="VM (zenuwgas) (de pagina bestaat niet)">VM</a> · <a href="/wiki/VX" title="VX">VX</a> · <i>Novitsjok-agentia:</i> <a href="/wiki/Novitsjok" title="Novitsjok">Novitsjok</a></td></tr><tr><td class="links"><b><a href="/wiki/Verstikkend_gas" title="Verstikkend gas">Verstikkend gas</a>:</b></td><td class="rechts"><a href="/wiki/Dichloor" title="Dichloor">chloorgas</a> · <a href="/wiki/Trichloornitromethaan" title="Trichloornitromethaan">chloorpicrine</a> (PS) · <a href="/wiki/Fosgeen" title="Fosgeen">fosgeen</a> (CG) · <a href="/wiki/Difosgeen" title="Difosgeen">difosgeen</a> (DP)</td></tr><tr><td class="links"><b><a href="/wiki/Irritantia" title="Irritantia">Irritantia</a>:</b></td><td class="rechts"><a href="/w/index.php?title=Agent_15&action=edit&redlink=1" class="new" title="Agent 15 (de pagina bestaat niet)">Agent 15</a> (BZ) · <a href="/w/index.php?title=Kolokol-1&action=edit&redlink=1" class="new" title="Kolokol-1 (de pagina bestaat niet)">Kolokol-1</a></td></tr><tr><td class="links"><b><a href="/wiki/Traangas" title="Traangas">Traangas</a>:</b></td><td class="rechts"><a href="/wiki/Pepperspray" title="Pepperspray">pepperspray</a> (OC) · <a href="/wiki/CS-gas" title="CS-gas">CS-gas</a> · <a class="mw-selflink selflink">CN-gas</a> · <a href="/w/index.php?title=CR-gas&action=edit&redlink=1" class="new" title="CR-gas (de pagina bestaat niet)">CR-gas</a></td></tr></tbody></table> </div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Overgenomen van "<a dir="ltr" href="https://nl.wikipedia.org/w/index.php?title=Chlooracetofenon&oldid=64474744">https://nl.wikipedia.org/w/index.php?title=Chlooracetofenon&oldid=64474744</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Categorie:Alles" title="Categorie:Alles">Categorieën</a>: <ul><li><a href="/wiki/Categorie:Fenon" title="Categorie:Fenon">Fenon</a></li><li><a href="/wiki/Categorie:Organische_chloorverbinding" title="Categorie:Organische chloorverbinding">Organische chloorverbinding</a></li><li><a href="/wiki/Categorie:Chemisch_wapen" title="Categorie:Chemisch 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