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id="toc-pH_indicator" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#pH_indicator"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>pH indicator</span> </div> </a> <ul id="toc-pH_indicator-sublist" class="vector-toc-list"> <li id="toc-Carbonation_of_concrete" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Carbonation_of_concrete"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.1</span> <span>Carbonation of concrete</span> </div> </a> <ul id="toc-Carbonation_of_concrete-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Education" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Education"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.2</span> <span>Education</span> </div> </a> <ul id="toc-Education-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Entertainment" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Entertainment"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.3</span> <span>Entertainment</span> </div> </a> <ul id="toc-Entertainment-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Detection_of_blood" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Detection_of_blood"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.4</span> <span>Detection of blood</span> </div> </a> <ul id="toc-Detection_of_blood-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Laxative" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Laxative"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Laxative</span> </div> </a> <ul id="toc-Laxative-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Synthesis</span> </div> </a> <ul id="toc-Synthesis-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">3</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">4</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>External links</span> </div> </a> <ul id="toc-External_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 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">Phenolphthalein</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 54 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-54" 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">54 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Fenolftale%C3%AFen" title="Fenolftaleïen – Afrikaans" lang="af" hreflang="af" data-title="Fenolftaleïen" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%8A%D9%86%D9%88%D9%84_%D9%81%D8%AB%D8%A7%D9%84%D9%8A%D9%86" title="فينول فثالين – Arabic" lang="ar" hreflang="ar" data-title="فينول فثالين" data-language-autonym="العربية" data-language-local-name="Arabic" 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/Ftaleinl%C9%99r" title="Ftaleinlər – Azerbaijani" lang="az" hreflang="az" data-title="Ftaleinlər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" 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/%D9%81%D9%86%D9%88%D9%84_%D9%81%D8%AA%D8%A7%D9%84%D8%A6%DB%8C%D9%86" title="فنول فتالئین – South Azerbaijani" lang="azb" hreflang="azb" data-title="فنول فتالئین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AB%E0%A7%87%E0%A6%A8%E0%A6%AB%E0%A6%A5%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B2%E0%A6%BF%E0%A6%A8" title="ফেনফথ্যালিন – Bangla" lang="bn" hreflang="bn" data-title="ফেনফথ্যালিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB%D1%84%D1%82%D0%B0%D0%BB%D0%B5%D1%96%D0%BD" title="Фенолфталеін – Belarusian" lang="be" hreflang="be" data-title="Фенолфталеін" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB%D1%84%D1%82%D0%B0%D0%BB%D0%B5%D0%B8%D0%BD" title="Фенолфталеин – Bulgarian" lang="bg" hreflang="bg" data-title="Фенолфталеин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Fenolftalein" title="Fenolftalein – Bosnian" lang="bs" hreflang="bs" data-title="Fenolftalein" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Fenolftale%C3%AFna" title="Fenolftaleïna – Catalan" lang="ca" hreflang="ca" data-title="Fenolftaleïna" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Fenolftalein" title="Fenolftalein – Czech" lang="cs" hreflang="cs" data-title="Fenolftalein" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Fenolftalein" title="Fenolftalein – Danish" lang="da" hreflang="da" data-title="Fenolftalein" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Phenolphthalein" title="Phenolphthalein – German" lang="de" hreflang="de" data-title="Phenolphthalein" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Fenoolftaleiin" title="Fenoolftaleiin – Estonian" lang="et" hreflang="et" data-title="Fenoolftaleiin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A6%CE%B1%CE%B9%CE%BD%CE%BF%CE%BB%CE%BF%CF%86%CE%B8%CE%B1%CE%BB%CE%B5%CE%90%CE%BD%CE%B7" title="Φαινολοφθαλεΐνη – Greek" lang="el" hreflang="el" data-title="Φαινολοφθαλεΐνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Fenolftale%C3%ADna" title="Fenolftaleína – Spanish" lang="es" hreflang="es" data-title="Fenolftaleína" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Fenolftaleino" title="Fenolftaleino – Esperanto" lang="eo" hreflang="eo" data-title="Fenolftaleino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Fenolftaleina" title="Fenolftaleina – Basque" lang="eu" hreflang="eu" data-title="Fenolftaleina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%D9%86%D9%84%E2%80%8C%D9%81%D8%AA%D8%A7%D9%84%D8%A6%DB%8C%D9%86" title="فنل‌فتالئین – Persian" lang="fa" hreflang="fa" data-title="فنل‌فتالئین" 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/Ph%C3%A9nolphtal%C3%A9ine" title="Phénolphtaléine – French" lang="fr" hreflang="fr" data-title="Phénolphtaléine" 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/%ED%8E%98%EB%86%80%ED%94%84%ED%83%88%EB%A0%88%EC%9D%B8" title="페놀프탈레인 – Korean" lang="ko" hreflang="ko" data-title="페놀프탈레인" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%96%D5%A5%D5%B6%D5%B8%D5%AC%D6%86%D5%A9%D5%A1%D5%AC%D5%A5%D5%AB%D5%B6" title="Ֆենոլֆթալեին – Armenian" lang="hy" hreflang="hy" data-title="Ֆենոլֆթալեին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AB%E0%A5%87%E0%A4%A8%E0%A5%89%E0%A4%AB%E0%A5%8D%E0%A4%A5%E0%A4%B2%E0%A5%80%E0%A4%A8" title="फेनॉफ्थलीन – Hindi" lang="hi" hreflang="hi" data-title="फेनॉफ्थलीन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Fenolftalein" title="Fenolftalein – Croatian" lang="hr" hreflang="hr" data-title="Fenolftalein" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Fenolftalein" title="Fenolftalein – Indonesian" lang="id" hreflang="id" data-title="Fenolftalein" 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/Fenolftaleina" title="Fenolftaleina – Italian" lang="it" hreflang="it" data-title="Fenolftaleina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A4%D7%A0%D7%95%D7%9C%D7%A4%D7%AA%D7%9C%D7%90%D7%99%D7%9F" title="פנולפתלאין – Hebrew" lang="he" hreflang="he" data-title="פנולפתלאין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%A4%E1%83%94%E1%83%9C%E1%83%9D%E1%83%9A%E1%83%A4%E1%83%97%E1%83%90%E1%83%9A%E1%83%94%E1%83%98%E1%83%9C%E1%83%98" title="ფენოლფთალეინი – Georgian" lang="ka" hreflang="ka" data-title="ფენოლფთალეინი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB%D1%84%D1%82%D0%B0%D0%BB%D0%B5%D0%B9%D0%BD" title="Фенолфталейн – Kazakh" lang="kk" hreflang="kk" data-title="Фенолфталейн" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB%D1%84%D1%82%D0%B0%D0%BB%D0%B5%D0%B8%D0%BD" title="Фенолфталеин – Kyrgyz" lang="ky" hreflang="ky" data-title="Фенолфталеин" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Fenolftale%C4%ABns" title="Fenolftaleīns – Latvian" lang="lv" hreflang="lv" data-title="Fenolftaleīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Fenolftaleina" title="Fenolftaleina – Lombard" lang="lmo" hreflang="lmo" data-title="Fenolftaleina" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Fenolftalein" title="Fenolftalein – Hungarian" lang="hu" hreflang="hu" data-title="Fenolftalein" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Fenolftalein" title="Fenolftalein – Malay" lang="ms" hreflang="ms" data-title="Fenolftalein" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Fenolftale%C3%AFne" title="Fenolftaleïne – Dutch" lang="nl" hreflang="nl" data-title="Fenolftaleïne" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%82%A7%E3%83%8E%E3%83%BC%E3%83%AB%E3%83%95%E3%82%BF%E3%83%AC%E3%82%A4%E3%83%B3" title="フェノールフタレイン – Japanese" lang="ja" hreflang="ja" data-title="フェノールフタレイン" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Fenolftalein" title="Fenolftalein – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Fenolftalein" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Fenolftalein" title="Fenolftalein – Uzbek" lang="uz" hreflang="uz" data-title="Fenolftalein" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%AB%E0%A8%BF%E0%A8%A8%E0%A9%8C%E0%A8%B2%E0%A8%AA%E0%A8%A5%E0%A8%BE%E0%A8%B2%E0%A9%80%E0%A8%A8" title="ਫਿਨੌਲਪਥਾਲੀਨ – Punjabi" lang="pa" hreflang="pa" data-title="ਫਿਨੌਲਪਥਾਲੀਨ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Fenoloftaleina" title="Fenoloftaleina – Polish" lang="pl" hreflang="pl" data-title="Fenoloftaleina" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Fenolftale%C3%ADna" title="Fenolftaleína – Portuguese" lang="pt" hreflang="pt" data-title="Fenolftaleína" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-kaa mw-list-item"><a href="https://kaa.wikipedia.org/wiki/Fenolftalein" title="Fenolftalein – Kara-Kalpak" lang="kaa" hreflang="kaa" data-title="Fenolftalein" data-language-autonym="Qaraqalpaqsha" data-language-local-name="Kara-Kalpak" class="interlanguage-link-target"><span>Qaraqalpaqsha</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Fenolftalein%C4%83" title="Fenolftaleină – Romanian" lang="ro" hreflang="ro" data-title="Fenolftaleină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB%D1%84%D1%82%D0%B0%D0%BB%D0%B5%D0%B8%D0%BD" title="Фенолфталеин – Russian" lang="ru" hreflang="ru" data-title="Фенолфталеин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Fenolftale%C3%ADn" title="Fenolftaleín – Slovak" lang="sk" hreflang="sk" data-title="Fenolftaleín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB%D1%84%D1%82%D0%B0%D0%BB%D0%B5%D0%B8%D0%BD" title="Фенолфталеин – Serbian" lang="sr" hreflang="sr" data-title="Фенолфталеин" 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/Fenolftalein" title="Fenolftalein – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Fenolftalein" 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/Fenoliftaleiini" title="Fenoliftaleiini – Finnish" lang="fi" hreflang="fi" data-title="Fenoliftaleiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Fenolftalein" title="Fenolftalein – Swedish" lang="sv" hreflang="sv" data-title="Fenolftalein" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%AB%E0%B0%BF%E0%B0%A8%E0%B0%BE%E0%B0%AA%E0%B1%8D%E0%B0%A4%E0%B0%B2%E0%B1%80%E0%B0%A8%E0%B1%8D" title="ఫినాప్తలీన్ – Telugu" lang="te" hreflang="te" data-title="ఫినాప్తలీన్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%9F%E0%B8%B5%E0%B8%99%E0%B8%AD%E0%B8%A5%E0%B9%8C%E0%B8%9F%E0%B8%97%E0%B8%B2%E0%B8%A5%E0%B8%B5%E0%B8%99" title="ฟีนอล์ฟทาลีน – Thai" lang="th" hreflang="th" data-title="ฟีนอล์ฟทาลีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Fenolftalein" title="Fenolftalein – Turkish" lang="tr" hreflang="tr" data-title="Fenolftalein" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB%D1%84%D1%82%D0%B0%D0%BB%D0%B5%D1%97%D0%BD" title="Фенолфталеїн – Ukrainian" lang="uk" hreflang="uk" data-title="Фенолфталеїн" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Phenolphthalein" title="Phenolphthalein – Vietnamese" lang="vi" hreflang="vi" data-title="Phenolphthalein" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%85%9A%E9%85%9E" title="酚酞 – Chinese" lang="zh" hreflang="zh" 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<div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">pH indicator that turns pink in basic solution</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about Phenolphthalein. For other related dyes in the phthalein family, see <a href="/wiki/Phthalein_dye" title="Phthalein dye">Phthalein dye</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Phenolphthalein </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Phenolphthalein.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Phenolphthalein.svg/220px-Phenolphthalein.svg.png" decoding="async" width="220" height="214" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Phenolphthalein.svg/330px-Phenolphthalein.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Phenolphthalein.svg/440px-Phenolphthalein.svg.png 2x" data-file-width="365" data-file-height="355" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Sample_of_solid_phenolphthalein.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Sample_of_solid_phenolphthalein.jpg/250px-Sample_of_solid_phenolphthalein.jpg" decoding="async" width="250" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Sample_of_solid_phenolphthalein.jpg/375px-Sample_of_solid_phenolphthalein.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/da/Sample_of_solid_phenolphthalein.jpg/500px-Sample_of_solid_phenolphthalein.jpg 2x" data-file-width="4903" data-file-height="2709" /></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;">3,3-Bis(4-hydroxyphenyl)-2-benzofuran-1(3<i>H</i>)-one</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;">3,3-Bis(4-hydroxyphenyl)isobenzofuran-1(3<i>H</i>)-one</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=77-09-8">77-09-8</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC1OC%28C2%3DC1C%3DCC%3DC2%29%28C3%3DCC%3DC%28C%3DC3%29O%5BH%5D%29C4%3DCC%3DC%28C%3DC4%29O%5BH%5D">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL63857">ChEMBL63857</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4600.html">4600</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB04824">DB04824</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/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/100.000.914">100.000.914</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q187921#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/D05456">D05456</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/4764">4764</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/6QK969R2IF">6QK969R2IF</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/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/DTXSID0021125">DTXSID0021125</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q187921#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/C20H14O4/c21-15-9-5-13(6-10-15)20(14-7-11-16(22)12-8-14)18-4-2-1-3-17(18)19(23)24-20/h1-12,21-22H<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: KJFMBFZCATUALV-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C20H14O4/c21-15-9-5-13(6-10-15)20(14-7-11-16(22)12-8-14)18-4-2-1-3-17(18)19(23)24-20/h1-12,21-22H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KJFMBFZCATUALV-UHFFFAOYAH</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%;">O=C1OC(C2=C1C=CC=C2)(C3=CC=C(C=C3)O[H])C4=CC=C(C=C4)O[H]</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>20</sub><span title="Hydrogen">H</span><sub>14</sub><span title="Oxygen">O</span><sub>4</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002318328000000000♠"></span>318.328</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>White powder </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.277 g/cm<sup>3</sup> (32 °C (90 °F)) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>258–263 °C (496–505 °F; 531–536 K)<sup id="cite_ref-sigma_1-1" class="reference"><a href="#cite_note-sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>400 mg/l </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in other solvents </td> <td>Insoluble in benzene and hexane; very soluble in ethanol and ether; slightly soluble in DMSO </td></tr> <tr> <td><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-vis</a> (λ<sub>max</sub>) </td> <td>552 nm (1st)<br /> 374 nm (2nd)<sup id="cite_ref-sigma_1-0" class="reference"><a href="#cite_note-sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </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_A06" title="ATC code A06">A06AB04</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=A06AB04">WHO</a></span>)  </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><sup id="cite_ref-sigma_1-2" class="reference"><a href="#cite_note-sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H341: Suspected of causing genetic defects">H341</abbr>, <abbr class="abbr" title="H350: May cause cancer">H350</abbr>, <abbr class="abbr" title="H361: Suspected of damaging fertility or the unborn child">H361</abbr><sup id="cite_ref-sigma_1-3" class="reference"><a href="#cite_note-sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P201: Obtain special instructions before use.">P201</abbr>, <abbr class="abbr" title="P281: Use personal protective equipment as required.">P281</abbr>, <abbr class="abbr" title="P308+P313: IF exposed or concerned: Get medical advice/attention.">P308+P313</abbr><sup id="cite_ref-sigma_1-4" class="reference"><a href="#cite_note-sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_9a02d12247c3a88a" /></span><map name="ImageMap_9a02d12247c3a88a"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td 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=408953309&page2=Phenolphthalein">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>Phenolphthalein</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="'f' in 'find'">f</span><span title="/ɛ/: 'e' in 'dress'">ɛ</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'n' in 'nigh'">n</span><span title="/ɒ/: 'o' in 'body'">ɒ</span><span title="'l' in 'lie'">l</span></span>(<span style="border-bottom:1px dotted"><span title="'f' in 'find'">f</span></span>)<span style="border-bottom:1px dotted"><span title="/θ/: 'th' in 'thigh'">θ</span><span title="/ə/: 'a' in 'about'">ə</span><span title="'l' in 'lie'">l</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span><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. (June 2022)">citation needed</span></a></i>]</sup> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key"><i title="English pronunciation respelling">feh-<span style="font-size:90%">NOL(F)</span>-thə-leen</i></a>) is a <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <a href="/wiki/Carbon" title="Carbon">C</a><sub>20</sub><a href="/wiki/Hydrogen" title="Hydrogen">H</a><sub>14</sub><a href="/wiki/Oxygen" title="Oxygen">O</a><sub>4</sub> and is often written as "<b>HIn</b>", "<b>HPh</b>", "<b>phph</b>" or simply "<b>Ph</b>" in shorthand notation. Phenolphthalein is often used as an indicator in <a href="/wiki/Acid%E2%80%93base_titration" title="Acid–base titration">acid–base titrations</a>. For this application, it turns colorless in <a href="/wiki/Acid" title="Acid">acidic</a> solutions and pink in <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">basic</a> solutions. It belongs to the class of dyes known as <a href="/wiki/Phthalein_dyes" class="mw-redirect" title="Phthalein dyes">phthalein dyes</a>. </p><p>Phenolphthalein is slightly soluble in <a href="/wiki/Water" title="Water">water</a> and usually is dissolved in <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> in <a href="/wiki/Experiment" title="Experiment">experiments</a>. It is a weak acid, which can lose H<sup>+</sup> ions in solution. The nonionized phenolphthalein molecule is colorless and the double deprotonated phenolphthalein ion is <a href="/wiki/Fuchsia_(color)" title="Fuchsia (color)">fuchsia</a>. Further proton loss in higher pH occurs slowly and leads to a colorless form. Phenolphthalein ion in concentrated <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> is orange red due to <a href="/wiki/Sulfonation" class="mw-redirect" title="Sulfonation">sulfonation</a>.<sup id="cite_ref-Tamura1996_2-0" class="reference"><a href="#cite_note-Tamura1996-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolphthalein&action=edit&section=1" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="pH_indicator">pH indicator</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolphthalein&action=edit&section=2" title="Edit section: pH indicator"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="toccolours" style="width: 15em; margin: 0 0 0.5em 0.5em; text-align: center; float: right"> <tbody><tr> <td colspan="3" style="background-color: #ddd; padding"><b>Phenolphthalein</b> <span class="nowrap">(<a href="/wiki/PH_indicator" title="PH indicator">pH indicator</a>)</span> </td></tr> <tr> <td><i>below pH 8.3</i> </td> <td> </td> <td><i>above pH 10.0</i> </td></tr> <tr> <td style="text-align: right; padding-right:0.2em; background-color: white; color: black"><b>8.3</b> </td> <td style="text-align: left; padding-left:0.2em; background-color: {{{middle_pH_color}}}; color: black"><b>⇌</b> </td> <td style="text-align: left; padding-left:0.2em; background-color: magenta; color: white"><b>10.0</b> </td></tr></tbody></table> <p>Phenolphthalein's common use is as an indicator in acid-base titrations. It also serves as a component of <a href="/wiki/Universal_indicator" title="Universal indicator">universal indicator</a>, together with <a href="/wiki/Methyl_red" title="Methyl red">methyl red</a>, <a href="/wiki/Bromothymol_blue" title="Bromothymol blue">bromothymol blue</a>, and <a href="/wiki/Thymol_blue" title="Thymol blue">thymol blue</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Phenolphthalein adopts different forms in aqueous solution depending on the pH of the solution.<sup id="cite_ref-wittke1983_4-0" class="reference"><a href="#cite_note-wittke1983-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Tamura1996_2-1" class="reference"><a href="#cite_note-Tamura1996-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Abdel-Hamid_5-0" class="reference"><a href="#cite_note-Abdel-Hamid-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kunimoto2001_6-0" class="reference"><a href="#cite_note-Kunimoto2001-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Inconsistency exists in the literature about hydrated forms of the compounds and the color of sulfuric acid. Wittke reported in 1983 that it exists in protonated form (H<sub>3</sub>In<sup>+</sup>) under strongly acidic conditions, providing an orange coloration. However, a later paper suggested that this color is due to sulfonation to <a href="/wiki/Phenolsulfonphthalein" class="mw-redirect" title="Phenolsulfonphthalein">phenolsulfonphthalein</a>.<sup id="cite_ref-Tamura1996_2-2" class="reference"><a href="#cite_note-Tamura1996-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>The lactone form (H<sub>2</sub>In) is colorless between strongly acidic and slightly basic conditions. The doubly deprotonated (In<sup>2-</sup>) phenolate form (the <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a> form of phenol) gives the familiar pink color. In strongly basic solutions, phenolphthalein is converted to its In(OH)<sup>3−</sup> form, and its pink color undergoes a rather slow fading reaction<sup id="cite_ref-Kunimoto2001_6-1" class="reference"><a href="#cite_note-Kunimoto2001-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> and becomes completely colorless when pH is greater than 13. </p><p>The <a href="/wiki/PKa" class="mw-redirect" title="PKa">p<i>K</i><sub>a</sub></a> values of phenolphthalein were found to be 9.05, 9.50 and 12 while those of phenolsulfonphthalein are 1.2 and 7.70.<sup id="cite_ref-Tamura1996_2-3" class="reference"><a href="#cite_note-Tamura1996-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable" style="margin: 1em auto 1em auto; text-align: center;"> <tbody><tr> <th>Species </th> <td>H<sub>3</sub>In<sup>+</sup></td> <td>H<sub>2</sub>In</td> <td>In<sup>2−</sup></td> <td>In(OH)<sup>3−</sup> </td></tr> <tr> <th>Structure </th> <td><span typeof="mw:File"><a href="/wiki/File:Phenolphthalein-very-low-pH-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Phenolphthalein-very-low-pH-2D-skeletal.svg/100px-Phenolphthalein-very-low-pH-2D-skeletal.svg.png" decoding="async" width="100" height="65" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Phenolphthalein-very-low-pH-2D-skeletal.svg/150px-Phenolphthalein-very-low-pH-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Phenolphthalein-very-low-pH-2D-skeletal.svg/200px-Phenolphthalein-very-low-pH-2D-skeletal.svg.png 2x" data-file-width="459" data-file-height="300" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Phenolphthalein-low-pH-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Phenolphthalein-low-pH-2D-skeletal.svg/80px-Phenolphthalein-low-pH-2D-skeletal.svg.png" decoding="async" width="80" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Phenolphthalein-low-pH-2D-skeletal.svg/120px-Phenolphthalein-low-pH-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Phenolphthalein-low-pH-2D-skeletal.svg/160px-Phenolphthalein-low-pH-2D-skeletal.svg.png 2x" data-file-width="370" data-file-height="350" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Phenolphthalein-mid-pH-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Phenolphthalein-mid-pH-2D-skeletal.svg/80px-Phenolphthalein-mid-pH-2D-skeletal.svg.png" decoding="async" width="80" height="59" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Phenolphthalein-mid-pH-2D-skeletal.svg/120px-Phenolphthalein-mid-pH-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Phenolphthalein-mid-pH-2D-skeletal.svg/160px-Phenolphthalein-mid-pH-2D-skeletal.svg.png 2x" data-file-width="410" data-file-height="300" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Phenolphthalein-high-pH-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Phenolphthalein-high-pH-2D-skeletal.svg/80px-Phenolphthalein-high-pH-2D-skeletal.svg.png" decoding="async" width="80" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Phenolphthalein-high-pH-2D-skeletal.svg/120px-Phenolphthalein-high-pH-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Phenolphthalein-high-pH-2D-skeletal.svg/160px-Phenolphthalein-high-pH-2D-skeletal.svg.png 2x" data-file-width="370" data-file-height="350" /></a></span> </td></tr> <tr> <th>Model </th> <td><span typeof="mw:File"><a href="/wiki/File:Phenolphthalein-orange-very-low-pH-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Phenolphthalein-orange-very-low-pH-3D-balls.png/80px-Phenolphthalein-orange-very-low-pH-3D-balls.png" decoding="async" width="80" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Phenolphthalein-orange-very-low-pH-3D-balls.png/120px-Phenolphthalein-orange-very-low-pH-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Phenolphthalein-orange-very-low-pH-3D-balls.png/160px-Phenolphthalein-orange-very-low-pH-3D-balls.png 2x" data-file-width="1100" data-file-height="981" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Phenolphthalein-colourless-low-pH-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Phenolphthalein-colourless-low-pH-3D-balls.png/80px-Phenolphthalein-colourless-low-pH-3D-balls.png" decoding="async" width="80" height="82" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Phenolphthalein-colourless-low-pH-3D-balls.png/120px-Phenolphthalein-colourless-low-pH-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Phenolphthalein-colourless-low-pH-3D-balls.png/160px-Phenolphthalein-colourless-low-pH-3D-balls.png 2x" data-file-width="1077" data-file-height="1100" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Phenolphthalein-red-mid-pH-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Phenolphthalein-red-mid-pH-3D-balls.png/80px-Phenolphthalein-red-mid-pH-3D-balls.png" decoding="async" width="80" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Phenolphthalein-red-mid-pH-3D-balls.png/120px-Phenolphthalein-red-mid-pH-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Phenolphthalein-red-mid-pH-3D-balls.png/160px-Phenolphthalein-red-mid-pH-3D-balls.png 2x" data-file-width="1100" data-file-height="973" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Phenolphthalein-colourless-high-pH-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Phenolphthalein-colourless-high-pH-3D-balls.png/80px-Phenolphthalein-colourless-high-pH-3D-balls.png" decoding="async" width="80" height="82" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Phenolphthalein-colourless-high-pH-3D-balls.png/120px-Phenolphthalein-colourless-high-pH-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/86/Phenolphthalein-colourless-high-pH-3D-balls.png/160px-Phenolphthalein-colourless-high-pH-3D-balls.png 2x" data-file-width="1077" data-file-height="1100" /></a></span> </td></tr> <tr> <th>pH </th> <td><−1 in H<sub>2</sub>SO<sub>4</sub><sup id="cite_ref-wittke1983_4-1" class="reference"><a href="#cite_note-wittke1983-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></td> <td>0–8.3</td> <td>8.3–10.0<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></td> <td>>12 </td></tr> <tr> <th>Conditions </th> <td>strongly acidic</td> <td>acidic or near-neutral</td> <td>basic</td> <td>strongly basic </td></tr> <tr> <th>Color </th> <td>orange</td> <td>colorless</td> <td>pink to fuchsia</td> <td>colorless </td></tr> <tr> <th>Image </th> <td><span typeof="mw:File"><a href="/wiki/File:Phenolphthalein-in-conc-sulfuric-acid.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Phenolphthalein-in-conc-sulfuric-acid.jpg/100px-Phenolphthalein-in-conc-sulfuric-acid.jpg" decoding="async" width="100" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Phenolphthalein-in-conc-sulfuric-acid.jpg/150px-Phenolphthalein-in-conc-sulfuric-acid.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/Phenolphthalein-in-conc-sulfuric-acid.jpg/200px-Phenolphthalein-in-conc-sulfuric-acid.jpg 2x" data-file-width="1972" data-file-height="1504" /></a></span></td> <td></td> <td><span typeof="mw:File"><a href="/wiki/File:Phenolphthalein-at-pH-9.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Phenolphthalein-at-pH-9.jpg/100px-Phenolphthalein-at-pH-9.jpg" decoding="async" width="100" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Phenolphthalein-at-pH-9.jpg/150px-Phenolphthalein-at-pH-9.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Phenolphthalein-at-pH-9.jpg/200px-Phenolphthalein-at-pH-9.jpg 2x" data-file-width="1524" data-file-height="1364" /></a></span></td> <td> </td></tr></tbody></table> <table class="wikitable" style="margin: 1em auto 1em auto;"> <tbody><tr> <td><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Phenolphthalein_reaction.gif" class="mw-file-description" title="PP startAnimGif"><img alt="PP startAnimGif" src="//upload.wikimedia.org/wikipedia/commons/3/35/Phenolphthalein_reaction.gif" decoding="async" width="872" height="207" class="mw-file-element" data-file-width="872" data-file-height="207" /></a></span> </td></tr> <tr> <td>An animation of the pH-dependent reaction mechanism: H<sub>3</sub>In<sup>+</sup> → H<sub>2</sub>In → In<sup>2−</sup> → In(OH)<sup>3−</sup> </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Carbonation_of_concrete">Carbonation of concrete</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolphthalein&action=edit&section=3" title="Edit section: Carbonation of concrete"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenolphthalein's pH sensitivity is exploited in other applications: concrete has naturally high pH due to the <a href="/wiki/Calcium_hydroxide" title="Calcium hydroxide">calcium hydroxide</a> formed when <a href="/wiki/Portland_cement" title="Portland cement">Portland cement</a> reacts with water. As the concrete reacts with carbon dioxide in the atmosphere, pH decreases to 8.5–9. When a 1% phenolphthalein solution is applied to normal concrete, it turns bright pink. However, if it remains colorless, it shows that the concrete has undergone <a href="/wiki/Carbonation" title="Carbonation">carbonation</a>. In a similar application, some <a href="/wiki/Spackling" class="mw-redirect" title="Spackling">spackling</a> used to repair holes in drywall contains phenolphthalein. When applied, the basic spackling material retains a pink color; when the spackling has cured by reaction with atmospheric carbon dioxide, the pink color fades.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Education">Education</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolphthalein&action=edit&section=4" title="Edit section: Education"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In a highly basic solution, phenolphthalein's slow change from pink to colorless as it is converted to its Ph(OH)<sup>3−</sup> form is used in chemistry classes for the study of <a href="/wiki/Reaction_kinetics" class="mw-redirect" title="Reaction kinetics">reaction kinetics</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Entertainment">Entertainment</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolphthalein&action=edit&section=5" title="Edit section: Entertainment"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenolphthalein is used in toys, for example as a component of disappearing inks, or disappearing dye on the "Hollywood Hair" <a href="/wiki/Barbie" title="Barbie">Barbie</a> hair. In the ink, it is mixed with <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a>, which reacts with carbon dioxide in the air. This reaction leads to the pH falling below the color change threshold as hydrogen ions are released by the reaction: </p> <dl><dd><a href="/wiki/Hydroxide" title="Hydroxide">OH<sup>−</sup></a><sub><a href="/wiki/Aqueous" class="mw-redirect" title="Aqueous">(aq)</a></sub> + <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a><sub><a href="/wiki/Gas" title="Gas">(g)</a></sub> → <a href="/wiki/Carbonate" title="Carbonate"><span class="chemf nowrap">CO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span></a><sub>(aq)</sub> + <a href="/wiki/Proton" title="Proton">H<sup>+</sup></a><sub>(aq)</sub>.</dd></dl> <p>To develop the hair and "magic" graphical patterns, the ink is sprayed with a solution of hydroxide, which leads to the appearance of the hidden graphics by the same mechanism described above for color change in alkaline solution. The pattern will eventually disappear again because of the reaction with <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>. <a href="/wiki/Thymolphthalein" title="Thymolphthalein">Thymolphthalein</a> is used for the same purpose and in the same way, when a blue color is desired.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Detection_of_blood">Detection of blood</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolphthalein&action=edit&section=6" title="Edit section: Detection of blood"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Kastle-Meyer_test" class="mw-redirect" title="Kastle-Meyer test">Kastle-Meyer test</a></div> <p>A reduced form of phenolphthalein, phenolphthalin, which is colorless, is used in a test to identify substances thought to contain blood, commonly known as the <a href="/wiki/Kastle%E2%80%93Meyer_test" title="Kastle–Meyer test">Kastle–Meyer test</a>. A dry sample is collected with a swab or filter paper. A few drops of alcohol, then a few drops of phenolphthalein, and finally a few drops of <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> are dripped onto the sample. If the sample contains <a href="/wiki/Hemoglobin" title="Hemoglobin">hemoglobin</a>, it will turn pink immediately upon addition of the peroxide, because of the generation of phenolphthalein. A positive test indicates the sample contains hemoglobin and, therefore, is likely blood. A false positive can result from the presence of substances with catalytic activity similar to hemoglobin. This test is not destructive to the sample; it can be kept and used in further tests. This test has the same reaction with blood from any animal whose blood contains hemoglobin, including almost all vertebrates; further testing would be required to determine whether it originated from a human. </p> <div class="mw-heading mw-heading3"><h3 id="Laxative">Laxative</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolphthalein&action=edit&section=7" title="Edit section: Laxative"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Phenol_red" title="Phenol red">Phenol red</a></div> <p>Phenolphthalein has been used for over a century as a <a href="/wiki/Laxative" title="Laxative">laxative</a>, but is now being removed from <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">over-the-counter</a> laxatives<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> over concerns of <a href="/wiki/Carcinogen" title="Carcinogen">carcinogenicity</a>.<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> Laxative products formerly containing phenolphthalein have often been reformulated with alternative active ingredients: Feen-a-Mint<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> switched to <a href="/wiki/Bisacodyl" title="Bisacodyl">bisacodyl</a>, and Ex-Lax<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> was switched to a <a href="/wiki/Senna_glycoside" title="Senna glycoside">senna extract</a>. </p><p><a href="/wiki/Thymolphthalein" title="Thymolphthalein">Thymolphthalein</a> is a related laxative made from <a href="/wiki/Thymol" title="Thymol">thymol</a>. </p><p>Despite concerns regarding its carcinogenicity based on rodent studies, the use of phenolphthalein as a laxative is unlikely to cause <a href="/wiki/Ovarian_cancer" title="Ovarian cancer">ovarian cancer</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> Some studies suggest a weak association with <a href="/wiki/Colon_cancer" class="mw-redirect" title="Colon cancer">colon cancer</a>, while others show none at all.<sup id="cite_ref-IARC_16-0" class="reference"><a href="#cite_note-IARC-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Phenolphthalein is described as a stimulant laxative.<sup id="cite_ref-IARC_16-1" class="reference"><a href="#cite_note-IARC-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> In addition, it has been found to inhibit human cellular calcium influx via store-operated calcium entry (SOCE, see <a href="/wiki/Calcium_release_activated_channel#Structure" title="Calcium release activated channel">Calcium release activated channel § Structure</a>) <i>in vivo</i>. This is effected by its inhibiting <a href="/wiki/Thrombin" title="Thrombin">thrombin</a> and <a href="/wiki/Thapsigargin" title="Thapsigargin">thapsigargin</a>, two activators of SOCE that increase intracellular free calcium.<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>Phenolphthalein has been added to the <a href="/wiki/European_Chemicals_Agency" title="European Chemicals Agency">European Chemicals Agency</a>'s candidate list for <a href="/wiki/Substance_of_very_high_concern" title="Substance of very high concern">substance of very high concern</a> (SVHC).<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> It is on the <a href="/wiki/IARC_group_2B" title="IARC group 2B">IARC group 2B</a> list for substances "possibly carcinogenic to humans".<sup id="cite_ref-KA_19-0" class="reference"><a href="#cite_note-KA-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>The discovery of phenolphthalein's laxative effect was due to an attempt by the Hungarian government to label<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (June 2023)">clarification needed</span></a></i>]</sup> genuine local white wine with the substance in 1900. Phenolphthalein did not change the taste of the wine and would change color when a base is added, making it a good label in principle. However, it was found that ingestion of the substance led to diarrhea. Max Kiss, a Hungarian-born pharmacist residing in New York, heard about the news and launched Ex-Lax in 1906.<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><sup id="cite_ref-KA_19-1" class="reference"><a href="#cite_note-KA-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolphthalein&action=edit&section=8" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenolphthalein can be synthesized by condensation of <a href="/wiki/Phthalic_anhydride" title="Phthalic anhydride">phthalic anhydride</a> with two equivalents of <a href="/wiki/Phenol" title="Phenol">phenol</a> under acidic conditions. It was discovered in 1871 by <a href="/wiki/Adolf_von_Baeyer" title="Adolf von Baeyer">Adolf von Baeyer</a>.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Phenolphthalein_Synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Phenolphthalein_Synthesis.svg/520px-Phenolphthalein_Synthesis.svg.png" decoding="async" width="520" height="173" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Phenolphthalein_Synthesis.svg/780px-Phenolphthalein_Synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Phenolphthalein_Synthesis.svg/1040px-Phenolphthalein_Synthesis.svg.png 2x" data-file-width="600" data-file-height="200" /></a><figcaption>Synthesis of phenolphthalein<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup></figcaption></figure> <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=Phenolphthalein&action=edit&section=9" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Bromothymol_blue" title="Bromothymol blue">Bromothymol blue</a></li> <li><a href="/wiki/Litmus" title="Litmus">Litmus</a></li> <li><a href="/wiki/Methyl_orange" title="Methyl orange">Methyl orange</a></li> <li><a href="/wiki/PH_indicator" title="PH indicator">pH indicator</a></li> <li><a href="/wiki/Universal_indicator" title="Universal indicator">Universal indicator</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolphthalein&action=edit&section=10" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 31em;"> <ol class="references"> <li id="cite_note-sigma-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-sigma_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-sigma_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-sigma_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-sigma_1-3"><sup><i><b>d</b></i></sup></a> <a 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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 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Retrieved <span class="nowrap">2019-06-26</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft&rft.atitle=Ueber+die+Phenolfarbstoffe&rft.volume=4&rft.issue=2&rft.pages=658-665&rft.date=1871&rft_id=info%3Adoi%2F10.1002%2Fcber.18710040247&rft.au=Baeyer%2C+A.&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1425010&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenolphthalein" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBaeyer,_A.1871" class="citation journal cs1">Baeyer, A. (1871). <a rel="nofollow" class="external text" href="https://dingler.culture.hu-berlin.de/article/pj201/ar201089">"Ueber die Phenolfarbstoffe"</a>. <i>Polytechnisches Journal</i>. <b>201</b> (89): 358–362. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20211011061700/http://dingler.culture.hu-berlin.de/article/pj201/ar201089">Archived</a> from the original on 2021-10-11<span class="reference-accessdate">. Retrieved <span class="nowrap">2022-02-22</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Polytechnisches+Journal&rft.atitle=Ueber+die+Phenolfarbstoffe&rft.volume=201&rft.issue=89&rft.pages=358-362&rft.date=1871&rft.au=Baeyer%2C+A.&rft_id=https%3A%2F%2Fdingler.culture.hu-berlin.de%2Farticle%2Fpj201%2Far201089&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenolphthalein" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text">Max Hubacher, <span><a rel="nofollow" class="external text" href="https://patents.google.com/patent/US2192485">U.S. patent 2,192,485</a></span> (1940 to Ex Lax Inc)</span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a 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title="Ulimorelin">Ulimorelin</a></li></ul> </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="Purine_receptor_modulators" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed 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:Purine_receptor_modulators" title="Template:Purine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Purine_receptor_modulators" title="Template talk:Purine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Purine_receptor_modulators" title="Special:EditPage/Template:Purine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Purine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Purine_receptor" class="mw-redirect" title="Purine receptor">Purine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/P0_receptor" class="mw-redirect" title="P0 receptor">P0</a> (<a href="/wiki/Adenine" title="Adenine">adenine</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=8-Aminoadenine&action=edit&redlink=1" class="new" title="8-Aminoadenine (page does not exist)">8-Aminoadenine</a></li> <li><a href="/wiki/Adenine" title="Adenine">Adenine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Adenosine_receptor" title="Adenosine receptor">P1</a><br />(<a href="/wiki/Adenosine" title="Adenosine">adenosine</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=2-(1-Hexynyl)-N-methyladenosine&action=edit&redlink=1" class="new" title="2-(1-Hexynyl)-N-methyladenosine (page does not exist)">2-(1-Hexynyl)-<i>N</i>-methyladenosine</a></li> <li><a href="/w/index.php?title=2-Cl-IB-MECA&action=edit&redlink=1" class="new" title="2-Cl-IB-MECA (page does not exist)">2-Cl-IB-MECA</a></li> <li><a href="/w/index.php?title=2-Chloroadenosine&action=edit&redlink=1" class="new" title="2-Chloroadenosine (page does not exist)">2-Chloroadenosine</a></li> <li><a href="/w/index.php?title=2%27-MeCCPA&action=edit&redlink=1" class="new" title="2'-MeCCPA (page does not exist)">2'-MeCCPA</a></li> <li><a href="/w/index.php?title=4%27-O-%CE%B2-D-Glucosyl-9-O-(6%27-deoxysaccharosyl)olivil&action=edit&redlink=1" class="new" title="4'-O-β-D-Glucosyl-9-O-(6'-deoxysaccharosyl)olivil (page does not exist)">4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil</a></li> <li><a href="/w/index.php?title=5%27-N-ethylcarboxamidoadenosine&action=edit&redlink=1" class="new" title="5'-N-ethylcarboxamidoadenosine (page does not exist)">5'-<i>N</i>-ethylcarboxamidoadenosine</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/w/index.php?title=Apadenoson&action=edit&redlink=1" class="new" title="Apadenoson (page does not exist)">Apadenoson</a></li> <li><a href="/wiki/ATL-146e" class="mw-redirect" title="ATL-146e">ATL-146e</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/BAY_60%E2%80%936583" title="BAY 60–6583">BAY 60–6583</a></li> <li><a href="/w/index.php?title=Binodenoson&action=edit&redlink=1" class="new" title="Binodenoson (page does not exist)">Binodenoson</a></li> <li><a href="/w/index.php?title=Capadenoson&action=edit&redlink=1" class="new" title="Capadenoson (page does not exist)">Capadenoson</a></li> <li><a href="/wiki/CCPA_(biochemistry)" title="CCPA (biochemistry)">CCPA</a></li> <li><a href="/wiki/CGS-21680" title="CGS-21680">CGS-21680</a></li> <li><a href="/wiki/CP-532,903" title="CP-532,903">CP-532,903</a></li> <li><a href="/w/index.php?title=CV-1808&action=edit&redlink=1" class="new" title="CV-1808 (page does not exist)">CV-1808</a></li> <li><a href="/w/index.php?title=Evodenoson&action=edit&redlink=1" class="new" title="Evodenoson (page does not exist)">Evodenoson</a></li> <li><a href="/w/index.php?title=GR_79236&action=edit&redlink=1" class="new" title="GR 79236 (page does not exist)">GR 79236</a></li> <li><a href="/w/index.php?title=HENECA&action=edit&redlink=1" class="new" title="HENECA (page does not exist)">HENECA</a></li> <li><a href="/w/index.php?title=LUF-5835&action=edit&redlink=1" class="new" title="LUF-5835 (page does not exist)">LUF-5835</a></li> <li><a href="/w/index.php?title=LUF-5845&action=edit&redlink=1" class="new" title="LUF-5845 (page does not exist)">LUF-5845</a></li> <li><a href="/wiki/N6-Cyclopentyladenosine" title="N6-Cyclopentyladenosine"><i>N</i><sup>6</sup>-Cyclopentyladenosine</a></li> <li><a href="/wiki/Namodenoson" title="Namodenoson">Namodenoson</a></li> <li><a href="/w/index.php?title=NECA_(drug)&action=edit&redlink=1" class="new" title="NECA (drug) (page does not exist)">NECA</a></li> <li><a href="/w/index.php?title=Neladenoson_dalanate&action=edit&redlink=1" class="new" title="Neladenoson dalanate (page does not exist)">Neladenoson dalanate</a></li> <li><a href="/w/index.php?title=Piclidenoson&action=edit&redlink=1" class="new" title="Piclidenoson (page does not exist)">Piclidenoson</a></li> <li><a href="/wiki/Regadenoson" title="Regadenoson">Regadenoson</a></li> <li><a href="/w/index.php?title=SDZ_WAG_994&action=edit&redlink=1" class="new" title="SDZ WAG 994 (page does not exist)">SDZ WAG 994</a></li> <li><a href="/w/index.php?title=Selodenoson&action=edit&redlink=1" class="new" title="Selodenoson (page does not exist)">Selodenoson</a></li> <li><a href="/w/index.php?title=Sonedenoson&action=edit&redlink=1" class="new" title="Sonedenoson (page does not exist)">Sonedenoson</a></li> <li><a href="/w/index.php?title=Tecadenoson&action=edit&redlink=1" class="new" title="Tecadenoson (page does not exist)">Tecadenoson</a></li> <li><a href="/w/index.php?title=Trabodenoson&action=edit&redlink=1" class="new" title="Trabodenoson (page does not exist)">Trabodenoson</a></li> <li><a href="/wiki/UK-432,097" title="UK-432,097">UK-432,097</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/wiki/3-Chlorostyrylcaffeine" title="3-Chlorostyrylcaffeine">3-Chlorostyrylcaffeine (CSC)</a></li> <li><a href="/wiki/7-Methylxanthine" title="7-Methylxanthine">7-Methylxanthine</a></li> <li><a href="/wiki/8-Chlorotheophylline" title="8-Chlorotheophylline">8-Chlorotheophylline</a></li> <li><a href="/w/index.php?title=8-Phenyl-1,3-dipropylxanthine&action=edit&redlink=1" class="new" title="8-Phenyl-1,3-dipropylxanthine (page does not exist)">8-Phenyl-1,3-dipropylxanthine</a></li> <li><a href="/wiki/8-Phenyltheophylline" title="8-Phenyltheophylline">8-Phenyltheophylline</a></li> <li><a href="/wiki/Acefylline" title="Acefylline">Acefylline</a></li> <li><a href="/wiki/Aminophylline" title="Aminophylline">Aminophylline</a></li> <li><a href="/wiki/ATL-444" title="ATL-444">ATL-444</a></li> <li><a href="/w/index.php?title=AZD-4635&action=edit&redlink=1" class="new" title="AZD-4635 (page does not exist)">AZD-4635</a></li> <li><a href="/wiki/Bamifylline" title="Bamifylline">Bamifylline</a></li> <li><a href="/wiki/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Caffeine_citrate" title="Caffeine citrate">Caffeine citrate</a></li> <li><a href="/wiki/Cartazolate" title="Cartazolate">Cartazolate</a></li> <li><a href="/w/index.php?title=CGH-2466&action=edit&redlink=1" class="new" title="CGH-2466 (page does not exist)">CGH-2466</a></li> <li><a href="/wiki/CGS-15943" title="CGS-15943">CGS-15943</a></li> <li><a href="/wiki/Choline_theophyllinate" title="Choline theophyllinate">Choline theophyllinate</a></li> <li><a href="/w/index.php?title=Ciforadenant&action=edit&redlink=1" class="new" title="Ciforadenant (page does not exist)">Ciforadenant</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dimethylxanthine" title="8-Cyclopentyl-1,3-dimethylxanthine">CPX</a></li> <li><a href="/w/index.php?title=CVT-6883&action=edit&redlink=1" class="new" title="CVT-6883 (page does not exist)">CVT-6883</a></li> <li><a href="/wiki/Dimethazan" title="Dimethazan">Dimethazan</a></li> <li><a href="/wiki/DMPX" title="DMPX">DMPX</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dipropylxanthine" class="mw-redirect" title="8-Cyclopentyl-1,3-dipropylxanthine">DPCPX</a></li> <li><a href="/wiki/Dyphylline" class="mw-redirect" title="Dyphylline">Dyphylline</a></li> <li><a href="/wiki/Enprofylline" title="Enprofylline">Enprofylline</a></li> <li><a href="/wiki/Etazolate" title="Etazolate">Etazolate</a></li> <li><a href="/w/index.php?title=Etrumadenant&action=edit&redlink=1" class="new" title="Etrumadenant (page does not exist)">Etrumadenant</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/IBMX" title="IBMX">IBMX</a></li> <li><a href="/w/index.php?title=Imaradenant&action=edit&redlink=1" class="new" title="Imaradenant (page does not exist)">Imaradenant</a></li> <li><a href="/w/index.php?title=Inupadenant&action=edit&redlink=1" class="new" title="Inupadenant (page does not exist)">Inupadenant</a></li> <li><a href="/wiki/ISAM-140" title="ISAM-140">ISAM-140</a></li> <li><a href="/w/index.php?title=ISAM-R316&action=edit&redlink=1" class="new" title="ISAM-R316 (page does not exist)">ISAM-R316</a></li> <li><a href="/wiki/Isovaleric_acid" title="Isovaleric acid">Isovaleric acid</a></li> <li><a href="/wiki/Istradefylline" title="Istradefylline">Istradefylline</a></li> <li><a href="/wiki/KF-26777" title="KF-26777">KF-26777</a></li> <li><a href="/wiki/Lu_AA41063" title="Lu AA41063">Lu AA41063</a></li> <li><a href="/wiki/Lu_AA47070" title="Lu AA47070">Lu AA47070</a></li> <li><a href="/wiki/MRE3008F20" class="mw-redirect" title="MRE3008F20">MRE3008F20</a></li> <li><a href="/wiki/MRS-1191" class="mw-redirect" title="MRS-1191">MRS-1191</a></li> <li><a href="/w/index.php?title=MRS-1220&action=edit&redlink=1" class="new" title="MRS-1220 (page does not exist)">MRS-1220</a></li> <li><a href="/w/index.php?title=MRS-1334&action=edit&redlink=1" class="new" title="MRS-1334 (page does not exist)">MRS-1334</a></li> <li><a href="/wiki/MRS-1523" class="mw-redirect" title="MRS-1523">MRS-1523</a></li> <li><a href="/wiki/MRS-1706" title="MRS-1706">MRS-1706</a></li> <li><a href="/w/index.php?title=MRS-1754&action=edit&redlink=1" class="new" title="MRS-1754 (page does not exist)">MRS-1754</a></li> <li><a href="/w/index.php?title=MRS-3777&action=edit&redlink=1" class="new" title="MRS-3777 (page does not exist)">MRS-3777</a></li> <li><a href="/wiki/MSX-2" title="MSX-2">MSX-2</a></li> <li><a href="/wiki/MSX-3" title="MSX-3">MSX-3</a></li> <li><a href="/wiki/MSX-4" title="MSX-4">MSX-4</a></li> <li><a href="/w/index.php?title=Muvadenant&action=edit&redlink=1" class="new" title="Muvadenant (page does not exist)">Muvadenant</a></li> <li><a href="/wiki/Paraxanthine" title="Paraxanthine">Paraxanthine</a></li> <li><a href="/wiki/Pentoxifylline" title="Pentoxifylline">Pentoxifylline</a></li> <li><a href="/wiki/Preladenant" title="Preladenant">Preladenant</a></li> <li><a href="/wiki/Propentofylline" title="Propentofylline">Propentofylline</a></li> <li><a href="/wiki/Proxyphylline" title="Proxyphylline">Proxyphylline</a></li> <li><a href="/wiki/PSB-10" title="PSB-10">PSB-10</a></li> <li><a href="/w/index.php?title=PSB-11&action=edit&redlink=1" class="new" title="PSB-11 (page does not exist)">PSB-11</a></li> <li><a href="/w/index.php?title=PSB-36&action=edit&redlink=1" class="new" title="PSB-36 (page does not exist)">PSB-36</a></li> <li><a href="/w/index.php?title=PSB-603&action=edit&redlink=1" class="new" title="PSB-603 (page does not exist)">PSB-603</a></li> <li><a href="/w/index.php?title=PSB-788&action=edit&redlink=1" class="new" title="PSB-788 (page does not exist)">PSB-788</a></li> <li><a href="/w/index.php?title=PSB-1115&action=edit&redlink=1" class="new" title="PSB-1115 (page does not exist)">PSB-1115</a></li> <li><a href="/w/index.php?title=PSB-1901&action=edit&redlink=1" class="new" title="PSB-1901 (page does not exist)">PSB-1901</a></li> <li><a href="/wiki/Reversine" title="Reversine">Reversine</a></li> <li><a href="/wiki/Rolofylline" title="Rolofylline">Rolofylline</a></li> <li><a href="/wiki/SCH-442,416" title="SCH-442,416">SCH-442,416</a></li> <li><a href="/wiki/SCH-58261" title="SCH-58261">SCH-58261</a></li> <li><a href="/w/index.php?title=Sipagladenant&action=edit&redlink=1" class="new" title="Sipagladenant (page does not exist)">Sipagladenant</a></li> <li><a href="/w/index.php?title=Taminadenant&action=edit&redlink=1" class="new" title="Taminadenant (page does not exist)">Taminadenant</a></li> <li><a href="/wiki/Theacrine" title="Theacrine">Theacrine</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li> <li><a href="/w/index.php?title=Tozadenant&action=edit&redlink=1" class="new" title="Tozadenant (page does not exist)">Tozadenant</a></li> <li><a href="/wiki/Tracazolate" title="Tracazolate">Tracazolate</a></li> <li><a href="/w/index.php?title=Vipadenant&action=edit&redlink=1" class="new" title="Vipadenant (page does not exist)">Vipadenant</a></li> <li><a href="/w/index.php?title=VUF-5574&action=edit&redlink=1" class="new" title="VUF-5574 (page does not exist)">VUF-5574</a></li> <li><a href="/wiki/ZM-241,385" title="ZM-241,385">ZM-241,385</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/P2_receptor" title="P2 receptor">P2</a><br />(<a href="/wiki/Nucleotide" title="Nucleotide">nucleotide</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:3em;;text-align:center;"><a href="/wiki/P2X_purinoreceptor" title="P2X purinoreceptor">P2X</a><br />(<a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate"><abbr title="Adenosine triphosphate">ATP</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Adenosine triphosphate</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=2-Methylthio-ATP&action=edit&redlink=1" class="new" title="2-Methylthio-ATP (page does not exist)">2-Me-SATP</a></li> <li><a href="/w/index.php?title=%CE%91,%CE%B2-Methylene-ATP&action=edit&redlink=1" class="new" title="Α,β-Methylene-ATP (page does not exist)">α,β-Me-ATP</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Diadenosine_tetraphosphate" class="mw-redirect" title="Diadenosine tetraphosphate">Ap4A</a></li> <li><a href="/w/index.php?title=Diadenosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diadenosine pentaphosphate (page does not exist)">Ap5A</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(γ-thio)-triphosphate (page does not exist)">ATPγS</a></li> <li><a href="/w/index.php?title=BzATP&action=edit&redlink=1" class="new" title="BzATP (page does not exist)">BzATP</a></li> <li><a href="/w/index.php?title=Cibacron_blue&action=edit&redlink=1" class="new" title="Cibacron blue (page does not exist)">Cibacron blue</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/w/index.php?title=D-%CE%B2,%CE%B3-Me-ATP&action=edit&redlink=1" class="new" title="D-β,γ-Me-ATP (page does not exist)">D-β,γ-Me-ATP</a></li> <li><a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a></li> <li><a href="/w/index.php?title=HT-AMP&action=edit&redlink=1" class="new" title="HT-AMP (page does not exist)">HT-AMP</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/w/index.php?title=L-%CE%B2,%CE%B3-Me-ATP&action=edit&redlink=1" class="new" title="L-β,γ-Me-ATP (page does not exist)">L-β,γ-Me-ATP</a></li> <li><a href="/w/index.php?title=MRS-2219&action=edit&redlink=1" class="new" title="MRS-2219 (page does not exist)">MRS-2219</a></li> <li><a href="/w/index.php?title=PAPET-ATP&action=edit&redlink=1" class="new" title="PAPET-ATP (page does not exist)">PAPET-ATP</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=5-BDBD&action=edit&redlink=1" class="new" title="5-BDBD (page does not exist)">5-BDBD</a></li> <li><a href="/w/index.php?title=A-317491&action=edit&redlink=1" class="new" title="A-317491 (page does not exist)">A-317491</a></li> <li><a href="/w/index.php?title=A-438079&action=edit&redlink=1" class="new" title="A-438079 (page does not exist)">A-438079</a></li> <li><a href="/w/index.php?title=A-740003&action=edit&redlink=1" class="new" title="A-740003 (page does not exist)">A-740003</a></li> <li><a href="/w/index.php?title=A-804598&action=edit&redlink=1" class="new" title="A-804598 (page does not exist)">A-804598</a></li> <li><a href="/w/index.php?title=A-839977&action=edit&redlink=1" class="new" title="A-839977 (page does not exist)">A-839977</a></li> <li><a href="/wiki/AF-353" title="AF-353">AF-353</a></li> <li><a href="/w/index.php?title=AZ-10606120&action=edit&redlink=1" class="new" title="AZ-10606120 (page does not exist)">AZ-10606120</a></li> <li><a href="/w/index.php?title=AZ-11645373&action=edit&redlink=1" class="new" title="AZ-11645373 (page does not exist)">AZ-11645373</a></li> <li><a href="/wiki/Brilliant_Blue_G" class="mw-redirect" title="Brilliant Blue G">BBG</a></li> <li><a href="/wiki/Calcium" title="Calcium">Calcium</a></li> <li><a href="/w/index.php?title=Calmidazolium&action=edit&redlink=1" class="new" title="Calmidazolium (page does not exist)">Calmidazolium</a></li> <li><a href="/wiki/Chelerythrine" title="Chelerythrine">Chelerythrine</a></li> <li><a href="/wiki/Copper" title="Copper">Copper</a></li> <li><a href="/wiki/Emodin" title="Emodin">Emodin</a> (<i><a href="/wiki/Rheum_officinale" title="Rheum officinale">Rheum officinale</a></i>)</li> <li><a href="/wiki/Evans_blue_(dye)" title="Evans blue (dye)">Evans blue</a></li> <li><a href="/wiki/Gefapixant" title="Gefapixant">Gefapixant</a></li> <li><a href="/w/index.php?title=GW-791343&action=edit&redlink=1" class="new" title="GW-791343 (page does not exist)">GW-791343</a></li> <li><a href="/w/index.php?title=5-(N,N-Hexamethylene)amiloride&action=edit&redlink=1" class="new" title="5-(N,N-Hexamethylene)amiloride (page does not exist)">HMA</a></li> <li><a href="/w/index.php?title=Diinosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diinosine pentaphosphate (page does not exist)">Ip5I</a></li> <li><a href="/w/index.php?title=IsoPPADS&action=edit&redlink=1" class="new" title="IsoPPADS (page does not exist)">isoPPADS</a></li> <li><a href="/w/index.php?title=JNJ-47965567&action=edit&redlink=1" class="new" title="JNJ-47965567 (page does not exist)">JNJ-47965567</a></li> <li><a href="/w/index.php?title=KN-04&action=edit&redlink=1" class="new" title="KN-04 (page does not exist)">KN-04</a></li> <li><a href="/wiki/KN-62" title="KN-62">KN-62</a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Magnesium</a></li> <li><a href="/w/index.php?title=MRS-2159&action=edit&redlink=1" class="new" title="MRS-2159 (page does not exist)">MRS-2159</a></li> <li><a href="/w/index.php?title=NF-023&action=edit&redlink=1" class="new" title="NF-023 (page does not exist)">NF-023</a></li> <li><a href="/w/index.php?title=NF-110&action=edit&redlink=1" class="new" title="NF-110 (page does not exist)">NF-110</a></li> <li><a href="/w/index.php?title=NF-157&action=edit&redlink=1" class="new" title="NF-157 (page does not exist)">NF-157</a></li> <li><a href="/w/index.php?title=NF-279&action=edit&redlink=1" class="new" title="NF-279 (page does not exist)">NF-279</a></li> <li><a href="/w/index.php?title=NF-449&action=edit&redlink=1" class="new" title="NF-449 (page does not exist)">NF-449</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/w/index.php?title=Oxidized-ATP&action=edit&redlink=1" class="new" title="Oxidized-ATP (page does not exist)">Oxidized-ATP</a></li> <li><a href="/wiki/Phenol_Red" class="mw-redirect" title="Phenol Red">Phenol Red</a></li> <li><a class="mw-selflink selflink">Phenolphthalein</a></li> <li><a href="/wiki/PPADS" title="PPADS">PPADS</a></li> <li><a href="/w/index.php?title=PPNDS&action=edit&redlink=1" class="new" title="PPNDS (page does not exist)">PPNDS</a></li> <li><a href="/w/index.php?title=PSB-12062&action=edit&redlink=1" class="new" title="PSB-12062 (page does not exist)">PSB-12062</a></li> <li><a href="/wiki/Puerarin" title="Puerarin">Puerarin</a> (<i><a href="/wiki/Radix_puerariae" class="mw-redirect" title="Radix puerariae">Radix puerariae</a></i>)</li> <li><a href="/w/index.php?title=Purotoxin_1&action=edit&redlink=1" class="new" title="Purotoxin 1 (page does not exist)">Purotoxin 1</a></li> <li><a href="/w/index.php?title=Reactive_Blue_2&action=edit&redlink=1" class="new" title="Reactive Blue 2 (page does not exist)">RB-2</a></li> <li><a href="/w/index.php?title=Ro_0437626&action=edit&redlink=1" class="new" title="Ro 0437626 (page does not exist)">Ro 0437626</a></li> <li><a href="/w/index.php?title=Ro_51&action=edit&redlink=1" class="new" title="Ro 51 (page does not exist)">Ro 51</a></li> <li><a href="/w/index.php?title=RO-3&action=edit&redlink=1" class="new" title="RO-3 (page does not exist)">RO-3</a></li> <li><a href="/wiki/Sodium_ferulate" title="Sodium ferulate">Sodium ferulate</a> (<i><a href="/wiki/Angelica_sinensis" title="Angelica sinensis">Angelica sinensis</a></i>, <i><a href="/wiki/Ligusticum_wallichii" class="mw-redirect" title="Ligusticum wallichii">Ligusticum wallichii</a></i>)</li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/w/index.php?title=TC-P_262&action=edit&redlink=1" class="new" title="TC-P 262 (page does not exist)">TC-P 262</a></li> <li><a href="/wiki/Tetramethylpyrazine" title="Tetramethylpyrazine">Tetramethylpyrazine (ligustrazine)</a> (<i><a href="/wiki/Ligusticum_wallichii" class="mw-redirect" title="Ligusticum wallichii">Ligusticum wallichii</a></i>)</li> <li><a href="/wiki/TNP-ATP" title="TNP-ATP">TNP-ATP</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:3em;;text-align:center;"><a href="/wiki/P2Y_receptor" title="P2Y receptor">P2Y</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=2-Methylthioladenosine_diphosphate&action=edit&redlink=1" class="new" title="2-Methylthioladenosine diphosphate (page does not exist)">2-Me-SADP</a></li> <li><a href="/w/index.php?title=2-Methylthioadenosine_triphosphate&action=edit&redlink=1" class="new" title="2-Methylthioadenosine triphosphate (page does not exist)">2-Me-SATP</a></li> <li><a href="/w/index.php?title=2-Thio-UTP&action=edit&redlink=1" class="new" title="2-Thio-UTP (page does not exist)">2-Thio-UTP</a></li> <li><a href="/w/index.php?title=5-Bromouridine_5%E2%80%B2-diphosphate&action=edit&redlink=1" class="new" title="5-Bromouridine 5′-diphosphate (page does not exist)">5-Br-UDP</a></li> <li><a href="/w/index.php?title=5-OMe-UDP&action=edit&redlink=1" class="new" title="5-OMe-UDP (page does not exist)">5-OMe-UDP</a></li> <li><a href="/w/index.php?title=%CE%91,%CE%B2-Methylene-ATP&action=edit&redlink=1" class="new" title="Α,β-Methylene-ATP (page does not exist)">α,β-Me-ATP</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B2-thio)-diphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(β-thio)-diphosphate (page does not exist)">ADPβS</a></li> <li><a href="/w/index.php?title=Diadenosine_triphosphate&action=edit&redlink=1" class="new" title="Diadenosine triphosphate (page does not exist)">Ap3A</a></li> <li><a href="/w/index.php?title=AR-C_67085MX&action=edit&redlink=1" class="new" title="AR-C 67085MX (page does not exist)">AR-C 67085MX</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(γ-thio)-triphosphate (page does not exist)">ATPγS</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/Deoxyadenosine_triphosphate" title="Deoxyadenosine triphosphate">dATP</a></li> <li><a href="/wiki/Denufosol" title="Denufosol">Denufosol</a></li> <li><a href="/wiki/Diquafosol" title="Diquafosol">Diquafosol</a></li> <li><a href="/w/index.php?title=Inosine_diphosphate&action=edit&redlink=1" class="new" title="Inosine diphosphate (page does not exist)">IDP</a></li> <li><a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a></li> <li><a href="/wiki/INS-365" class="mw-redirect" title="INS-365">INS-365</a></li> <li><a href="/w/index.php?title=INS-37217&action=edit&redlink=1" class="new" title="INS-37217 (page does not exist)">INS-37217</a></li> <li><a href="/w/index.php?title=MRS-2365&action=edit&redlink=1" class="new" title="MRS-2365 (page does not exist)">MRS-2365</a></li> <li><a href="/w/index.php?title=MRS-2690&action=edit&redlink=1" class="new" title="MRS-2690 (page does not exist)">MRS-2690</a></li> <li><a href="/w/index.php?title=MRS-2693&action=edit&redlink=1" class="new" title="MRS-2693 (page does not exist)">MRS-2693</a></li> <li><a href="/w/index.php?title=MRS-2768&action=edit&redlink=1" class="new" title="MRS-2768 (page does not exist)">MRS-2768</a></li> <li><a href="/w/index.php?title=MRS-2957&action=edit&redlink=1" class="new" title="MRS-2957 (page does not exist)">MRS-2957</a></li> <li><a href="/w/index.php?title=MRS-4062&action=edit&redlink=1" class="new" title="MRS-4062 (page does not exist)">MRS-4062</a></li> <li><a href="/w/index.php?title=NF-546&action=edit&redlink=1" class="new" title="NF-546 (page does not exist)">NF-546</a></li> <li><a href="/w/index.php?title=PAPET-ATP&action=edit&redlink=1" class="new" title="PAPET-ATP (page does not exist)">PAPET-ATP</a></li> <li><a href="/w/index.php?title=PSB-0474&action=edit&redlink=1" class="new" title="PSB-0474 (page does not exist)">PSB-0474</a></li> <li><a href="/w/index.php?title=PSB-1114&action=edit&redlink=1" class="new" title="PSB-1114 (page does not exist)">PSB-1114</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li> <li><a href="/w/index.php?title=Uridine_5%C2%B4-(%CE%B2-thio)-diphosphate&action=edit&redlink=1" class="new" title="Uridine 5´-(β-thio)-diphosphate (page does not exist)">UDPβS</a></li> <li><a href="/wiki/Uridine_diphosphate_galactose" title="Uridine diphosphate galactose">UDP-galactose</a></li> <li><a href="/wiki/Uridine_diphosphate_glucose" title="Uridine diphosphate glucose">UDP-glucose</a></li> <li><a href="/wiki/Uridine_diphosphate_N-acetylglucosamine" title="Uridine diphosphate N-acetylglucosamine">UDP-N-acetylglucosamine</a></li> <li><a href="/w/index.php?title=Diuridine_triphosphate&action=edit&redlink=1" class="new" title="Diuridine triphosphate (page does not exist)">Up3U</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li> <li><a href="/w/index.php?title=Uridine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Uridine-5'-(γ-thio)-triphosphate (page does not exist)">UTPγS</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=2-Methylthioladenosine_monophosphate&action=edit&redlink=1" class="new" title="2-Methylthioladenosine monophosphate (page does not exist)">2-Me-SAMP</a></li> <li><a href="/w/index.php?title=A3P5PS&action=edit&redlink=1" class="new" title="A3P5PS (page does not exist)">A3P5PS</a></li> <li><a href="/w/index.php?title=AMP%CE%B1S&action=edit&redlink=1" class="new" title="AMPαS (page does not exist)">AMPαS</a></li> <li><a href="/wiki/Diadenosine_tetraphosphate" class="mw-redirect" title="Diadenosine tetraphosphate">Ap4A</a></li> <li><a href="/w/index.php?title=AR-C_66096&action=edit&redlink=1" class="new" title="AR-C 66096 (page does not exist)">AR-C 66096</a></li> <li><a href="/w/index.php?title=AR-C_67085MX&action=edit&redlink=1" class="new" title="AR-C 67085MX (page does not exist)">AR-C 67085MX</a></li> <li><a href="/w/index.php?title=AR-C_69931MX&action=edit&redlink=1" class="new" title="AR-C 69931MX (page does not exist)">AR-C 69931MX</a></li> <li><a href="/w/index.php?title=AR-C_118925XX&action=edit&redlink=1" class="new" title="AR-C 118925XX (page does not exist)">AR-C 118925XX</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=BzATP&action=edit&redlink=1" class="new" title="BzATP (page does not exist)">BzATP</a></li> <li><a href="/w/index.php?title=C1330-7&action=edit&redlink=1" class="new" title="C1330-7 (page does not exist)">C1330-7</a></li> <li><a href="/wiki/Cangrelor" title="Cangrelor">Cangrelor</a></li> <li><a href="/wiki/Clopidogrel" title="Clopidogrel">Clopidogrel</a></li> <li><a href="/wiki/Elinogrel" title="Elinogrel">Elinogrel</a></li> <li><a href="/w/index.php?title=Diinosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diinosine pentaphosphate (page does not exist)">Ip5I</a></li> <li><a href="/w/index.php?title=MRS-2179&action=edit&redlink=1" class="new" title="MRS-2179 (page does not exist)">MRS-2179</a></li> <li><a href="/w/index.php?title=MRS-2211&action=edit&redlink=1" class="new" title="MRS-2211 (page does not exist)">MRS-2211</a></li> <li><a href="/w/index.php?title=MRS-2279&action=edit&redlink=1" class="new" title="MRS-2279 (page does not exist)">MRS-2279</a></li> <li><a href="/w/index.php?title=MRS-2395&action=edit&redlink=1" class="new" title="MRS-2395 (page does not exist)">MRS-2395</a></li> <li><a href="/w/index.php?title=MRS-2500&action=edit&redlink=1" class="new" title="MRS-2500 (page does not exist)">MRS-2500</a></li> <li><a href="/w/index.php?title=MRS-2578&action=edit&redlink=1" class="new" title="MRS-2578 (page does not exist)">MRS-2578</a></li> <li><a href="/w/index.php?title=NF-157&action=edit&redlink=1" class="new" title="NF-157 (page does not exist)">NF-157</a></li> <li><a href="/w/index.php?title=NF-340&action=edit&redlink=1" class="new" title="NF-340 (page does not exist)">NF-340</a></li> <li><a href="/w/index.php?title=2,2%27-Pyridylisatogen_tosylate&action=edit&redlink=1" class="new" title="2,2'-Pyridylisatogen tosylate (page does not exist)">PIT</a></li> <li><a href="/wiki/PPADS" title="PPADS">PPADS</a></li> <li><a href="/wiki/Prasugrel" title="Prasugrel">Prasugrel</a></li> <li><a href="/w/index.php?title=PSB-0739&action=edit&redlink=1" class="new" title="PSB-0739 (page does not exist)">PSB-0739</a></li> <li><a href="/w/index.php?title=Reactive_Blue_2&action=edit&redlink=1" class="new" title="Reactive Blue 2 (page does not exist)">RB-2</a></li> <li><a href="/wiki/Regrelor" title="Regrelor">Regrelor</a></li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/wiki/Ticagrelor" title="Ticagrelor">Ticagrelor</a></li> <li><a href="/wiki/Ticlopidine" title="Ticlopidine">Ticlopidine</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Membrane_transport_protein" title="Membrane transport protein">Transporter</a><br /><small>(<a href="/wiki/Reuptake_inhibitor" title="Reuptake inhibitor">blockers</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Concentrative_nucleoside_transporters" class="mw-redirect" title="Concentrative nucleoside transporters"><abbr title="Concentrative nucleoside transporters">CNTs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Concentrative nucleoside transporters</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=6-Hydroxy-7-methoxyflavone&action=edit&redlink=1" class="new" title="6-Hydroxy-7-methoxyflavone (page does not exist)">6-Hydroxy-7-methoxyflavone</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/w/index.php?title=DMeThPmR&action=edit&redlink=1" class="new" title="DMeThPmR (page does not exist)">dMeThPmR</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/w/index.php?title=KGO-2142&action=edit&redlink=1" class="new" title="KGO-2142 (page does not exist)">KGO-2142</a></li> <li><a href="/w/index.php?title=KGO-2173&action=edit&redlink=1" class="new" title="KGO-2173 (page does not exist)">KGO-2173</a></li> <li><a href="/w/index.php?title=MeThPmR&action=edit&redlink=1" class="new" title="MeThPmR (page does not exist)">MeThPmR</a></li> <li><a href="/wiki/Phloridzin" class="mw-redirect" title="Phloridzin">Phloridzin</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Equilibrative_nucleoside_transporters" class="mw-redirect" title="Equilibrative nucleoside transporters"><abbr title="Equilibrative nucleoside transporters">ENTs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Equilibrative nucleoside transporters</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></li> <li><a href="/wiki/Cilostazol" title="Cilostazol">Cilostazol</a></li> <li><a href="/wiki/Dilazep" title="Dilazep">Dilazep</a></li> <li><a href="/wiki/Dipyridamole" title="Dipyridamole">Dipyridamole</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Hexobendine" title="Hexobendine">Hexobendine</a></li> <li><a href="/w/index.php?title=6-S-((4-Nitrophenyl)methyl)-6-thioinosine&action=edit&redlink=1" class="new" title="6-S-((4-Nitrophenyl)methyl)-6-thioinosine (page does not exist)">NBMPR</a></li> <li><a href="/wiki/Pentoxifylline" title="Pentoxifylline">Pentoxifylline</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Propentofylline" title="Propentofylline">Propentofylline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Plasma_membrane_monoamine_transporter" title="Plasma membrane monoamine transporter"><abbr title="Plasma membrane monoamine transporter">PMAT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Plasma membrane monoamine transporter</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Decynium-22" title="Decynium-22">Decynium-22</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Xanthine_oxidase" title="Xanthine oxidase"><abbr title="Xanthine oxidase">XO</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Xanthine oxidase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Allopurinol" title="Allopurinol">Allopurinol</a></li> <li><a href="/wiki/Amflutizole" title="Amflutizole">Amflutizole</a></li> <li><a href="/wiki/Benzbromarone" title="Benzbromarone">Benzbromarone</a></li> <li><a href="/wiki/Caffeic_acid" title="Caffeic acid">Caffeic acid</a></li> <li><a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">Cinnamaldehyde</a></li> <li><i><a href="/wiki/Cinnamomum_osmophloeum" title="Cinnamomum osmophloeum">Cinnamomum osmophloeum</a></i></li> <li><a href="/wiki/Febuxostat" title="Febuxostat">Febuxostat</a></li> <li><a href="/wiki/Myo-inositol" class="mw-redirect" title="Myo-inositol">Myo-inositol</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/wiki/Myricetin" title="Myricetin">Myricetin</a></li> <li><a href="/w/index.php?title=Niraxostat&action=edit&redlink=1" class="new" title="Niraxostat (page does not exist)">Niraxostat</a></li> <li><a href="/wiki/Oxipurinol" title="Oxipurinol">Oxipurinol</a></li> <li><a href="/wiki/Phytic_acid" title="Phytic acid">Phytic acid</a></li> <li><i><a href="/wiki/Pistacia_integerrima" title="Pistacia integerrima">Pistacia integerrima</a></i></li> <li><a href="/wiki/Propolis" title="Propolis">Propolis</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Tisopurine" title="Tisopurine">Tisopurine</a></li> <li><a href="/wiki/Topiroxostat" title="Topiroxostat">Topiroxostat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminopterin" title="Aminopterin">Aminopterin</a></li> <li><a href="/wiki/Azathioprine" title="Azathioprine">Azathioprine</a></li> <li><a href="/wiki/Methotrexate" title="Methotrexate">Methotrexate</a></li> <li><a href="/wiki/Mycophenolic_acid" title="Mycophenolic acid">Mycophenolic acid</a></li> <li><a href="/wiki/Pemetrexed" title="Pemetrexed">Pemetrexed</a></li> <li><a href="/wiki/Pralatrexate" title="Pralatrexate">Pralatrexate</a></li> <li><i>Many others</i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</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><b>Precursors:</b> <a href="/wiki/Adenine" title="Adenine">Adenine</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Cytosine" title="Cytosine">Cytosine</a></li> <li><a href="/wiki/Cytidine" title="Cytidine">Cytidine</a></li> <li><a href="/wiki/Cytidine_monophosphate" title="Cytidine monophosphate">CMP</a></li> <li><a href="/wiki/Cytidine_diphosphate" title="Cytidine diphosphate">CDP</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/Guanine" title="Guanine">Guanine</a></li> <li><a href="/wiki/Guanosine" title="Guanosine">Guanosine</a></li> <li><a href="/wiki/Guanosine_monophosphate" title="Guanosine monophosphate">GMP</a></li> <li><a href="/wiki/Guanosine_diphosphate" title="Guanosine diphosphate">GDP</a></li> <li><a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a></li> <li><a href="/wiki/Hypoxanthine" title="Hypoxanthine">Hypoxanthine</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/Inosine_monophosphate" class="mw-redirect" title="Inosine monophosphate">IMP</a></li> <li><a href="/w/index.php?title=Inosine_diphosphate&action=edit&redlink=1" class="new" title="Inosine diphosphate (page does not exist)">IDP</a></li> <li><a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a></li> <li><a href="/wiki/Ribose" title="Ribose">Ribose</a></li> <li><a href="/wiki/Uracil" title="Uracil">Uracil</a></li> <li><a href="/wiki/Uridine" title="Uridine">Uridine</a></li> <li><a href="/wiki/Uridine_monophosphate" title="Uridine monophosphate">UMP</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li></ul> <ul><li><b>Others:</b> <a href="/wiki/Chrysophanol" title="Chrysophanol">Chrysophanol</a> (<a href="/wiki/Rhubarb" title="Rhubarb">rhubarb</a>)</li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Phenolphthalein&oldid=1259145812">https://en.wikipedia.org/w/index.php?title=Phenolphthalein&oldid=1259145812</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:PH_indicators" title="Category:PH indicators">PH indicators</a></li><li><a href="/wiki/Category:1871_introductions" title="Category:1871 introductions">1871 introductions</a></li><li><a href="/wiki/Category:Triarylmethane_dyes" 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