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class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Natural_occurrences" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Natural_occurrences"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Natural occurrences</span> </div> </a> <ul id="toc-Natural_occurrences-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Pharmacology</span> </div> </a> <button aria-controls="toc-Pharmacology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Pharmacology subsection</span> </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Pharmacodynamics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Pharmacodynamics</span> </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> <li id="toc-Absorption" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Absorption"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.1</span> <span>Absorption</span> </div> </a> <ul id="toc-Absorption-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Distribution" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Distribution"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.2</span> <span>Distribution</span> </div> </a> <ul id="toc-Distribution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.3</span> <span>Metabolism</span> </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Excretion" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Excretion"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.4</span> <span>Excretion</span> </div> </a> <ul id="toc-Excretion-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>History</span> </div> </a> <ul id="toc-History-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">8</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">9</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">10</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">Theophylline</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 39 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-39" 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">39 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AB%D9%8A%D9%88%D9%81%D9%8A%D9%84%D9%8A%D9%86" title="ثيوفيلين – Arabic" lang="ar" hreflang="ar" data-title="ثيوفيلين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%AA%D8%A6%D9%88%D9%81%DB%8C%D9%84%DB%8C%D9%86" title="تئوفیلین – South Azerbaijani" lang="azb" hreflang="azb" data-title="تئوفیلین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A2%D0%B5%D0%BE%D1%84%D0%B8%D0%BB%D0%B8%D0%BD" title="Теофилин – Bulgarian" lang="bg" hreflang="bg" data-title="Теофилин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Teofil%C2%B7lina" title="Teofil·lina – Catalan" lang="ca" hreflang="ca" data-title="Teofil·lina" 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/Theofylin" title="Theofylin – Czech" lang="cs" hreflang="cs" data-title="Theofylin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Theoffylin" title="Theoffylin – Welsh" lang="cy" hreflang="cy" data-title="Theoffylin" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://de.wikipedia.org/wiki/Theophyllin" title="Theophyllin – German" lang="de" hreflang="de" data-title="Theophyllin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%98%CE%B5%CE%BF%CF%86%CF%85%CE%BB%CE%BB%CE%AF%CE%BD%CE%B7" title="Θεοφυλλίνη – Greek" lang="el" hreflang="el" data-title="Θεοφυλλίνη" 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/Teofilina" title="Teofilina – Spanish" lang="es" hreflang="es" data-title="Teofilina" 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/Teofilino" title="Teofilino – Esperanto" lang="eo" hreflang="eo" data-title="Teofilino" 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/Teofilina" title="Teofilina – Basque" lang="eu" hreflang="eu" data-title="Teofilina" 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/%D8%AA%D8%A6%D9%88%D9%81%DB%8C%D9%84%DB%8C%D9%86" title="تئوفیلین – Persian" lang="fa" hreflang="fa" data-title="تئوفیلین" 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/Th%C3%A9ophylline" title="Théophylline – French" lang="fr" hreflang="fr" data-title="Théophylline" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Teofilina" title="Teofilina – Galician" lang="gl" hreflang="gl" data-title="Teofilina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%85%8C%EC%98%A4%ED%95%84%EB%A6%B0" title="테오필린 – Korean" lang="ko" hreflang="ko" data-title="테오필린" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Teofilin" title="Teofilin – Indonesian" lang="id" hreflang="id" data-title="Teofilin" 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/Teofillina" title="Teofillina – Italian" lang="it" hreflang="it" data-title="Teofillina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Theophyllinum" title="Theophyllinum – Latin" lang="la" hreflang="la" data-title="Theophyllinum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Teofillin" title="Teofillin – Hungarian" lang="hu" hreflang="hu" data-title="Teofillin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A2%D0%B5%D0%BE%D1%84%D0%B8%D0%BB%D0%B8%D0%BD" title="Теофилин – Macedonian" lang="mk" hreflang="mk" data-title="Теофилин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Teofilina" title="Teofilina – Malay" lang="ms" hreflang="ms" data-title="Teofilina" 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/Theofylline" title="Theofylline – Dutch" lang="nl" hreflang="nl" data-title="Theofylline" 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%86%E3%82%AA%E3%83%95%E3%82%A3%E3%83%AA%E3%83%B3" title="テオフィリン – Japanese" lang="ja" hreflang="ja" data-title="テオフィリン" 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/Teofyllin" title="Teofyllin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Teofyllin" 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-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%A5%E0%AC%BF%E0%AC%93%E0%AC%AB%E0%AC%BE%E0%AC%87%E0%AC%B2%E0%AC%BF%E0%AC%A8" title="ଥିଓଫାଇଲିନ – Odia" lang="or" hreflang="or" data-title="ଥିଓଫାଇଲିନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Teofilina" title="Teofilina – Polish" lang="pl" hreflang="pl" data-title="Teofilina" 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/Teofilina" title="Teofilina – Portuguese" lang="pt" hreflang="pt" data-title="Teofilina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Teofilin%C4%83" title="Teofilină – Romanian" lang="ro" hreflang="ro" data-title="Teofilină" 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%A2%D0%B5%D0%BE%D1%84%D0%B8%D0%BB%D0%BB%D0%B8%D0%BD" title="Теофиллин – Russian" lang="ru" hreflang="ru" data-title="Теофиллин" 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/Teofyl%C3%ADn" title="Teofylín – Slovak" lang="sk" hreflang="sk" data-title="Teofylín" 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/Teofilin" title="Teofilin – Serbian" lang="sr" hreflang="sr" data-title="Teofilin" 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/Teofilin" title="Teofilin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Teofilin" 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/Teofylliini" title="Teofylliini – Finnish" lang="fi" hreflang="fi" data-title="Teofylliini" 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/Teofyllin" title="Teofyllin – Swedish" lang="sv" hreflang="sv" data-title="Teofyllin" 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%A5%E0%B0%BF%E0%B0%AF%E0%B1%8B%E0%B0%AB%E0%B0%BF%E0%B0%B2%E0%B0%BF%E0%B0%A8%E0%B1%8D" title="థియోఫిలిన్ – Telugu" lang="te" hreflang="te" data-title="థియోఫిలిన్" 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%98%E0%B8%B5%E0%B9%82%E0%B8%AD%E0%B8%9F%E0%B8%B4%E0%B8%A5%E0%B8%A5%E0%B8%B5%E0%B8%99" title="ธีโอฟิลลีน – Thai" lang="th" hreflang="th" data-title="ธีโอฟิลลีน" 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/Teofilin" title="Teofilin – Turkish" lang="tr" hreflang="tr" data-title="Teofilin" 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%A2%D0%B5%D0%BE%D1%84%D1%96%D0%BB%D1%96%D0%BD" title="Теофілін – Ukrainian" lang="uk" hreflang="uk" data-title="Теофілін" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%8C%B6%E7%A2%B1" title="茶碱 – Chinese" lang="zh" hreflang="zh" data-title="茶碱" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Drug used to treat respiratory diseases</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Theophylline">Theophylline</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Theophylline.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Theophylline.svg/150px-Theophylline.svg.png" decoding="async" width="150" height="146" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Theophylline.svg/225px-Theophylline.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/27/Theophylline.svg/300px-Theophylline.svg.png 2x" data-file-width="512" data-file-height="497" /></a></span></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Theophylline_3D_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Theophylline_3D_ball.png/180px-Theophylline_3D_ball.png" decoding="async" width="180" height="153" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Theophylline_3D_ball.png/270px-Theophylline_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Theophylline_3D_ball.png/360px-Theophylline_3D_ball.png 2x" data-file-width="2000" data-file-height="1695" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Theolair, Slo-Bid</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/theophyllines.html">Monograph</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><span title="medlineplus.gov"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a681006.html">a681006</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><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><small><abbr class="country-name" title="Australia">AU</abbr>:</small> A<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (April 2015)">citation needed</span></a></i>]</sup></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">oral</a>, <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">IV</a>, <a href="/wiki/Rectal_administration" title="Rectal administration">rectal</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/ATC_code_R03" title="ATC code R03">R03DA04</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=R03DA04">WHO</a></span>) R03DB04</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_4" title="Standard for the Uniform Scheduling of Medicines and Poisons">S4</a> (Prescription only)</li> <li><small><abbr class="country-name" title="Canada">CA</abbr></small>: <a href="/wiki/Prescription_drug" title="Prescription drug"> ℞-only</a></li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> P (<a href="/wiki/Pharmacy_medicines" class="mw-redirect" title="Pharmacy medicines">Pharmacy medicines</a>)</li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">℞-only</a></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">100% (<a href="/wiki/Oral_administration" title="Oral administration">oral</a>)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">40% (primarily to albumin)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Hepatic</a>: <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a>, <a href="/wiki/CYP2E1" title="CYP2E1">CYP2E1</a>, <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data">• 1,3-Dimethyluric acid <br /> • 1-Methyixanthine<br /> • 3-Methylxanthine</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">5–8 hours</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</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; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">1,3-dimethyl-7H-purine-2,6-dione</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=58-55-9">58-55-9</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><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><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/2153">2153</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=413">413</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><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/DB00277">DB00277</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><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><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.2068.html">2068</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><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><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/0I55128JYK">0I55128JYK</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><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/D00371">D00371</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><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28177">CHEBI:28177</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><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><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/ChEMBL190">ChEMBL190</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><th scope="row" class="infobox-label" style="line-height:1.2em;"><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></th><td class="infobox-data"><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/DTXSID5021336">DTXSID5021336</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q407308#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><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.350">100.000.350</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q407308#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><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>7</sub><span title="Hydrogen">H</span><sub>8</sub><span title="Nitrogen">N</span><sub>4</sub><span title="Oxygen">O</span><sub>2</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002180167000000000♠"></span>180.167</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><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=Cn1c2c%28c%28%3DO%29n%28c1%3DO%29C%29%5BnH%5Dcn2">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><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="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Cn1c2c(c(=O)n(c1=O)C)[nH]cn2</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><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="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)<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></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:ZFXYFBGIUFBOJW-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></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=470606142&page2=Theophylline">(verify)</a></span></span></td></tr></tbody></table> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Cylmin_100mg_by_Tsuruhara.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Cylmin_100mg_by_Tsuruhara.jpg/170px-Cylmin_100mg_by_Tsuruhara.jpg" decoding="async" width="170" height="283" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Cylmin_100mg_by_Tsuruhara.jpg/255px-Cylmin_100mg_by_Tsuruhara.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Cylmin_100mg_by_Tsuruhara.jpg/340px-Cylmin_100mg_by_Tsuruhara.jpg 2x" data-file-width="720" data-file-height="1200" /></a><figcaption>Theophylline extended-release tablets in Japan</figcaption></figure> <p><b>Theophylline</b>, also known as <b>1,3-dimethylxanthine</b>, is a drug that inhibits <a href="/wiki/Phosphodiesterase" title="Phosphodiesterase">phosphodiesterase</a> and blocks <a href="/wiki/Adenosine_receptors" class="mw-redirect" title="Adenosine receptors">adenosine receptors</a>.<sup id="cite_ref-pubchem_1-0" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It is used to treat <a href="/wiki/Chronic_obstructive_pulmonary_disease" title="Chronic obstructive pulmonary disease">chronic obstructive pulmonary disease</a> (COPD) and <a href="/wiki/Asthma" title="Asthma">asthma</a>.<sup id="cite_ref-barnes_2-0" class="reference"><a href="#cite_note-barnes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Its pharmacology is similar to other <a href="/wiki/Xanthine" title="Xanthine">methylxanthine</a> drugs (e.g., <a href="/wiki/Theobromine" title="Theobromine">theobromine</a> and <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>).<sup id="cite_ref-pubchem_1-1" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Trace amounts of theophylline are naturally present in <a href="/wiki/Tea" title="Tea">tea</a>, <a href="/wiki/Coffee" title="Coffee">coffee</a>, <a href="/wiki/Chocolate" title="Chocolate">chocolate</a>, <a href="/wiki/Mate_(drink)" class="mw-redirect" title="Mate (drink)">yerba maté</a>, <a href="/wiki/Guarana" title="Guarana">guarana</a>, and <a href="/wiki/Kola_nut" title="Kola nut">kola nut</a>.<sup id="cite_ref-pubchem_1-2" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>The name 'theophylline' derives from "Thea"—the former genus name for <a href="/wiki/Camellia_sinensis" title="Camellia sinensis">tea</a> + Legacy Greek φύλλον (phúllon, "leaf") + -ine. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The main actions of theophylline involve:<sup id="cite_ref-barnes_2-1" class="reference"><a href="#cite_note-barnes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <ul><li>relaxing bronchial <a href="/wiki/Smooth_muscle" title="Smooth muscle">smooth muscle</a></li> <li>increasing heart muscle contractility and efficiency (positive <a href="/wiki/Inotrope" title="Inotrope">inotrope</a>)</li> <li>increasing heart rate (positive <a href="/wiki/Chronotropic" title="Chronotropic">chronotropic</a>)</li> <li>increasing <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a></li> <li>increasing <a href="/wiki/Kidney" title="Kidney">renal</a> blood flow</li> <li><a href="/wiki/Anti-inflammatory" title="Anti-inflammatory">anti-inflammatory</a> effects</li> <li><a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> stimulatory effect, mainly on the medullary <a href="/wiki/Respiratory_center" title="Respiratory center">respiratory center</a><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li></ul> <p>The main therapeutic uses of theophylline are for treating:<sup id="cite_ref-barnes_2-2" class="reference"><a href="#cite_note-barnes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Chronic_obstructive_pulmonary_disease" title="Chronic obstructive pulmonary disease">Chronic obstructive pulmonary disease</a> (COPD)<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Asthma" title="Asthma">Asthma</a></li> <li><a href="/wiki/Apnea_of_prematurity" title="Apnea of prematurity">infant apnea</a><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></li> <li>Blocks the action of <a href="/wiki/Adenosine" title="Adenosine">adenosine</a>; an inhibitory neurotransmitter that induces sleep, contracts the smooth muscles and relaxes the cardiac muscle.</li> <li>Treatment of post-dural puncture headache.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Performance_enhancement_in_sports">Performance enhancement in sports</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=2" title="Edit section: Performance enhancement in sports"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Theophylline and other methylxanthines are often used for their performance-enhancing effects in sports, as these drugs increase alertness, bronchodilation, and increase the rate and force of heart contraction.<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> There is conflicting information about the value of theophylline and other methylxanthines as prophylaxis against <a href="/wiki/Exercise-induced_bronchoconstriction" title="Exercise-induced bronchoconstriction"> exercise-induced asthma</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> </p> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects">Adverse effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=3" title="Edit section: Adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The use of theophylline is complicated by its interaction with various drugs and by the fact that it has a narrow <a href="/wiki/Therapeutic_window" class="mw-redirect" title="Therapeutic window">therapeutic window</a> (<20 mcg/mL).<sup id="cite_ref-barnes_2-3" class="reference"><a href="#cite_note-barnes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Its use must be monitored by direct measurement of serum theophylline levels to avoid <a href="/wiki/Toxicity" title="Toxicity">toxicity</a>. It can also cause nausea, diarrhea, increase in heart rate, <a href="/wiki/Heart_arrhythmia" class="mw-redirect" title="Heart arrhythmia">abnormal heart rhythms</a>, and CNS excitation (headaches, <a href="/wiki/Insomnia" title="Insomnia">insomnia</a>, irritability, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a> and <a href="/wiki/Lightheadedness" title="Lightheadedness">lightheadedness</a>).<sup id="cite_ref-barnes_2-4" class="reference"><a href="#cite_note-barnes-2"><span class="cite-bracket">[</span>2<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> <a href="/wiki/Seizure" title="Seizure">Seizures</a> can also occur in severe cases of toxicity, and are considered to be a neurological emergency.<sup id="cite_ref-barnes_2-5" class="reference"><a href="#cite_note-barnes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Its toxicity is increased by <a href="/wiki/Erythromycin" title="Erythromycin">erythromycin</a>, cimetidine, and <a href="/wiki/Fluoroquinolones" class="mw-redirect" title="Fluoroquinolones">fluoroquinolones</a>, such as <a href="/wiki/Ciprofloxacin" title="Ciprofloxacin">ciprofloxacin</a>. Some lipid-based formulations of theophylline can result in toxic theophylline levels when taken with fatty meals, an effect called <a href="/wiki/Dose_dumping" title="Dose dumping">dose dumping</a>, but this does not occur with most formulations of theophylline.<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> Theophylline toxicity can be treated with <a href="/wiki/Beta_blocker" title="Beta blocker">beta blockers</a>. In addition to seizures, tachyarrhythmias are a major concern.<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> Theophylline should not be used in combination with the <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">SSRI</a> <a href="/wiki/Fluvoxamine" title="Fluvoxamine">fluvoxamine</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><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Spectroscopy">Spectroscopy</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=4" title="Edit section: Spectroscopy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="UV-visible">UV-visible</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=5" title="Edit section: UV-visible"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Theophylline is soluble in 0.1N NaOH and absorbs maximally at 277 nm with an extinction coefficient of 10,200 (cm<sup>−1</sup> M<sup>−1</sup>).<sup id="cite_ref-pmid15392550_17-0" class="reference"><a href="#cite_note-pmid15392550-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Proton_NMR">Proton NMR</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=6" title="Edit section: Proton NMR"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The characteristic signals, distinguishing theophylline from related methylxanthines, are approximately 3.23δ and 3.41δ, corresponding to the unique methylation possessed by theophylline. The remaining proton signal, at 8.01δ, corresponds to the proton on the imidazole ring, not transferred between the nitrogen. The transferred proton between the nitrogen is a variable proton and only exhibits a signal under certain conditions.<sup id="cite_ref-pmid27320965_18-0" class="reference"><a href="#cite_note-pmid27320965-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="13C-NMR"><sup>13</sup>C-NMR</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=7" title="Edit section: 13C-NMR"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The unique methylation of theophylline corresponds to the following signals: 27.7δ and 29.9δ. The remaining signals correspond to carbons characteristic of the xanthine backbone.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrences">Natural occurrences</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=8" title="Edit section: Natural occurrences"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Theophylline is naturally found in <a href="/wiki/Cocoa_bean" title="Cocoa bean">cocoa beans</a>. Amounts as high as 3.7 mg/g have been reported in <a href="/wiki/Criollo_(cocoa_bean)" class="mw-redirect" title="Criollo (cocoa bean)">Criollo</a> cocoa beans.<sup id="cite_ref-ApgarTarka_20-0" class="reference"><a href="#cite_note-ApgarTarka-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Trace amounts of theophylline are also found in brewed <a href="/wiki/Tea" title="Tea">tea</a>, although brewed tea provides only about 1 mg/L,<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> which is significantly less than a therapeutic dose. </p><p>Trace amounts of theophylline are also found in guarana (<i><a href="/wiki/Paullinia_cupana" class="mw-redirect" title="Paullinia cupana">Paullinia cupana</a></i>) and in <a href="/wiki/Cola_(plant)" title="Cola (plant)">kola nuts</a>.<sup id="cite_ref-pmid4013524_22-0" class="reference"><a href="#cite_note-pmid4013524-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=9" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=10" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Like other methylated <a href="/wiki/Xanthine" title="Xanthine">xanthine derivatives</a>, theophylline is both a </p> <ol><li>competitive nonselective <a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">phosphodiesterase inhibitor</a> which increases intracellular levels of <a href="/wiki/Cyclic_adenosine_monophosphate" title="Cyclic adenosine monophosphate">cAMP</a> and <a href="/wiki/Cyclic_adenosine_monophosphate" title="Cyclic adenosine monophosphate">cGMP</a>,<sup id="cite_ref-barnes_2-6" class="reference"><a href="#cite_note-barnes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PDEs-Essayan_23-0" class="reference"><a href="#cite_note-PDEs-Essayan-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> activates <a href="/wiki/CAMP-dependent_protein_kinase" class="mw-redirect" title="CAMP-dependent protein kinase">PKA</a>, <a href="/wiki/TNF_inhibitor" title="TNF inhibitor">inhibits TNF-alpha</a><sup id="cite_ref-PTX-Deree_24-0" class="reference"><a href="#cite_note-PTX-Deree-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid9927365_25-0" class="reference"><a href="#cite_note-pmid9927365-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> and inhibits <a href="/wiki/Leukotriene" title="Leukotriene">leukotriene</a><sup id="cite_ref-LT-Peters-Golden_26-0" class="reference"><a href="#cite_note-LT-Peters-Golden-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> synthesis, and <a href="/wiki/Anti-inflammatory" title="Anti-inflammatory">reduces inflammation</a> and <a href="/wiki/Innate_immunity" class="mw-redirect" title="Innate immunity">innate immunity</a><sup id="cite_ref-LT-Peters-Golden_26-1" class="reference"><a href="#cite_note-LT-Peters-Golden-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup></li> <li>nonselective <a href="/wiki/Adenosine_receptor" title="Adenosine receptor">adenosine receptor</a> antagonist, antagonizing A1, A2, and A3 receptors almost equally, which explains many of its cardiac effects.<sup id="cite_ref-barnes_2-7" class="reference"><a href="#cite_note-barnes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AR-Daly_27-0" class="reference"><a href="#cite_note-AR-Daly-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> Theophylline activates <a href="/wiki/Histone_deacetylase" title="Histone deacetylase">histone deacetylases</a>.<sup id="cite_ref-barnes_2-8" class="reference"><a href="#cite_note-barnes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ol> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=11" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Absorption">Absorption</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=12" title="Edit section: Absorption"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When theophylline is administered <a href="/wiki/Intravenously" class="mw-redirect" title="Intravenously">intravenously</a>, <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> is 100%.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Distribution">Distribution</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=13" title="Edit section: Distribution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Theophylline is distributed in the extracellular fluid, in the placenta, in the mother's milk and in the central nervous system. The volume of distribution is 0.5 L/kg. The protein binding is 40%.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (September 2023)">medical citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading4"><h4 id="Metabolism">Metabolism</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=14" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Theophylline is metabolized extensively in the liver.<sup id="cite_ref-barnes_2-9" class="reference"><a href="#cite_note-barnes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It undergoes <a href="/wiki/N-demethylation" class="mw-redirect" title="N-demethylation"><i>N</i>-demethylation</a> via <a href="/wiki/Cytochrome" title="Cytochrome">cytochrome</a> P450 <a href="/wiki/CYP1A2" title="CYP1A2">1A2</a>. It is metabolized by parallel <a href="/wiki/Order_of_reaction" class="mw-redirect" title="Order of reaction">first order</a> and <a href="/wiki/Michaelis-Menten_kinetics" class="mw-redirect" title="Michaelis-Menten kinetics">Michaelis-Menten</a> pathways. Metabolism may become saturated (non-linear), even within the therapeutic range. Small dose increases may result in disproportionately large increases in serum concentration. <a href="/wiki/Methylation" title="Methylation">Methylation</a> to caffeine is also important in the infant population. Smokers and people with hepatic (liver) impairment metabolize it differently.<sup id="cite_ref-barnes_2-10" class="reference"><a href="#cite_note-barnes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Cigarette and marijuana smoking induces metabolism of theophylline, increasing the drug's metabolic clearance.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Excretion">Excretion</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=15" title="Edit section: Excretion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Theophylline is excreted unchanged in the urine (up to 10%). Clearance of the drug is increased in children (age 1 to 12), teenagers (12 to 16), adult smokers, elderly smokers, as well as in <a href="/wiki/Cystic_fibrosis" title="Cystic fibrosis">cystic fibrosis</a>, and <a href="/wiki/Hyperthyroidism" title="Hyperthyroidism">hyperthyroidism</a>. Clearance of the drug is decreased in these conditions: elderly, acute congestive heart failure, cirrhosis, hypothyroidism and febrile viral illnesses.<sup id="cite_ref-barnes_2-11" class="reference"><a href="#cite_note-barnes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>The elimination <a href="/wiki/Half-life" title="Half-life">half-life</a> varies: 30 hours for premature neonates, 24 hours for neonates, 3.5 hours for children ages 1 to 9, 8 hours for adult non-smokers, 5 hours for adult smokers, 24 hours for those with <a href="/wiki/Hepatic_impairment" class="mw-redirect" title="Hepatic impairment">hepatic impairment</a>, 12 hours for those with congestive heart failure <a href="/wiki/NYHA" class="mw-redirect" title="NYHA">NYHA</a> class I-II, 24 hours for those with congestive heart failure NYHA class III-IV, 12 hours for the elderly.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (February 2022)">medical citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=16" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Theophylline was first extracted from tea leaves and chemically identified around 1888 by the German biologist <a href="/wiki/Albrecht_Kossel" title="Albrecht Kossel">Albrecht Kossel</a>.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Seven years later, a <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">chemical synthesis</a> starting with 1,3-dimethyluric acid was described by <a href="/wiki/Hermann_Emil_Fischer" class="mw-redirect" title="Hermann Emil Fischer">Emil Fischer</a> and <a href="/w/index.php?title=Lorenz_Ach&action=edit&redlink=1" class="new" title="Lorenz Ach (page does not exist)">Lorenz Ach</a>.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Traube_purine_synthesis" class="mw-redirect" title="Traube purine synthesis">Traube purine synthesis</a>, an alternative method to synthesize theophylline, was introduced in 1900 by another German scientist, <a href="/wiki/Wilhelm_Traube" title="Wilhelm Traube">Wilhelm Traube</a>.<sup id="cite_ref-Traube2_34-0" class="reference"><a href="#cite_note-Traube2-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Theophylline's first clinical use came in 1902 as a <a href="/wiki/Diuretic" title="Diuretic">diuretic</a>.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> It took an additional 20 years until it was first reported as an asthma treatment.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> The drug was prescribed in a <a href="/wiki/Syrup" title="Syrup">syrup</a> up to the 1970s as Theostat 20 and Theostat 80, and by the early 1980s in a tablet form called Quibron. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theophylline&action=edit&section=17" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Theophylline/ephedrine" title="Theophylline/ephedrine">Theophylline/ephedrine</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=Theophylline&action=edit&section=18" 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 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a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" 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"Über das Theophyllin, einen neuen Bestandtheil des Thees" [On theophylline, a new component of tea]. <i>Hoppe-Seyler's Zeitschrift für Physiologische Chemie</i> [<i>Hoppe-Seyler's Journal of Physiological Chemistry</i>] (in German). <b>13</b>: 298–308.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Hoppe-Seyler%27s+Zeitschrift+f%C3%BCr+Physiologische+Chemie&rft.atitle=%C3%9Cber+das+Theophyllin%2C+einen+neuen+Bestandtheil+des+Thees&rft.volume=13&rft.pages=298-308&rft.date=1889&rft.aulast=Kossel&rft.aufirst=A&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATheophylline" class="Z3988"></span></span> </li> <li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFischerAch1895" class="citation journal cs1 cs1-prop-foreign-lang-source">Fischer E, Ach L (1895). "Synthese des Caffeins" [Synthesis of caffeine]. <i>Berichte der Deutschen Chemischen Gesellschaft</i> [<i>Reports of the German Chemical Society</i>] (in German). <b>28</b> (3): 3139. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.189502803156">10.1002/cber.189502803156</a>.</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=Synthese+des+Caffeins&rft.volume=28&rft.issue=3&rft.pages=3139&rft.date=1895&rft_id=info%3Adoi%2F10.1002%2Fcber.189502803156&rft.aulast=Fischer&rft.aufirst=E&rft.au=Ach%2C+L&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATheophylline" class="Z3988"></span></span> </li> <li id="cite_note-Traube2-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-Traube2_34-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTraube1900" class="citation journal cs1 cs1-prop-foreign-lang-source">Traube W (1900). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1425990">"Der synthetische Aufbau der Harnsäure, des Xanthins, Theobromins, Theophyllins und Caffeïns aus der Cyanessigsäure"</a> [The synthetic structure of uric acid, xanthine, theobromine, theophylline and caffeine from cyanoacetic acid]. <i>Berichte der Deutschen Chemischen Gesellschaft</i> [<i>Reports of the German Chemical Society</i>] (in German). <b>33</b> (3): 3035–3056. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.19000330352">10.1002/cber.19000330352</a>.</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=Der+synthetische+Aufbau+der+Harns%C3%A4ure%2C+des+Xanthins%2C+Theobromins%2C+Theophyllins+und+Caffe%C3%AFns+aus+der+Cyanessigs%C3%A4ure&rft.volume=33&rft.issue=3&rft.pages=3035-3056&rft.date=1900&rft_id=info%3Adoi%2F10.1002%2Fcber.19000330352&rft.aulast=Traube&rft.aufirst=W&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1425990&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATheophylline" class="Z3988"></span></span> </li> <li id="cite_note-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-35">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMinkowski1902" class="citation journal cs1 cs1-prop-foreign-lang-source">Minkowski O (1902). "Über Theocin (Theophyllin) als Diureticum" [About theocine (theophylline) as a diuretic]. <i>Therapie der Gegenwart</i> [<i>Therapy of the Present</i>] (in German). <b>43</b>: 490–493.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Therapie+der+Gegenwart&rft.atitle=%C3%9Cber+Theocin+%28Theophyllin%29+als+Diureticum&rft.volume=43&rft.pages=490-493&rft.date=1902&rft.aulast=Minkowski&rft.aufirst=O&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATheophylline" class="Z3988"></span></span> </li> <li id="cite_note-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-36">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchultze-WerninghausMeier-Sydow1982" class="citation journal cs1">Schultze-Werninghaus G, Meier-Sydow J (March 1982). "The clinical and pharmacological history of theophylline: first report on the bronchospasmolytic action in man by S. R. Hirsch in Frankfurt (Main) 1922". <i>Clinical Allergy</i>. <b>12</b> (2): 211–215. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1365-2222.1982.tb01641.x">10.1111/j.1365-2222.1982.tb01641.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7042115">7042115</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:38178598">38178598</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Allergy&rft.atitle=The+clinical+and+pharmacological+history+of+theophylline%3A+first+report+on+the+bronchospasmolytic+action+in+man+by+S.+R.+Hirsch+in+Frankfurt+%28Main%29+1922&rft.volume=12&rft.issue=2&rft.pages=211-215&rft.date=1982-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A38178598%23id-name%3DS2CID&rft_id=info%3Apmid%2F7042115&rft_id=info%3Adoi%2F10.1111%2Fj.1365-2222.1982.tb01641.x&rft.aulast=Schultze-Werninghaus&rft.aufirst=G&rft.au=Meier-Sydow%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATheophylline" class="Z3988"></span></span> </li> </ol></div></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 href="/w/index.php?title=Theophylline&action=edit&section=19" title="Edit section: External links"><span>edit</span></a><span 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title="Asthma">asthma</a>/<a href="/wiki/Chronic_obstructive_pulmonary_disease" title="Chronic obstructive pulmonary disease">COPD</a> (<a href="/wiki/ATC_code_R03" title="ATC code R03">R03</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adrenergic_drug" class="mw-redirect" title="Adrenergic drug">Adrenergics</a>, <a href="/wiki/Inhalant" title="Inhalant">inhalants</a></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:1%"><a href="/wiki/Beta2-adrenergic_agonist#Short-acting_.CE.B22_agonists" title="Beta2-adrenergic agonist">Short-acting β<sub>2</sub> agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bitolterol" title="Bitolterol">Bitolterol</a></li> <li><a href="/wiki/Carbuterol" title="Carbuterol">Carbuterol</a></li> <li><a href="/wiki/Fenoterol" title="Fenoterol">Fenoterol</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/Pirbuterol" title="Pirbuterol">Pirbuterol</a></li> <li><a href="/wiki/Procaterol" title="Procaterol">Procaterol</a></li> <li><a href="/wiki/Reproterol" title="Reproterol">Reproterol</a></li> <li><a href="/wiki/Rimiterol" title="Rimiterol">Rimiterol</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol (albuterol)</a><sup>#</sup>/<a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol (levalbuterol)</a></li> <li><a href="/wiki/Terbutaline" title="Terbutaline">Terbutaline</a></li> <li><a href="/wiki/Tulobuterol" title="Tulobuterol">Tulobuterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Long-acting_beta-adrenoceptor_agonist" title="Long-acting beta-adrenoceptor agonist">Long-acting β<sub>2</sub> agonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bambuterol" title="Bambuterol">Bambuterol</a></li> <li><a href="/wiki/Clenbuterol" title="Clenbuterol">Clenbuterol</a></li> <li><a href="/wiki/Formoterol" title="Formoterol">Formoterol</a>/<a href="/wiki/Arformoterol" title="Arformoterol">Arformoterol</a></li> <li><a href="/wiki/Salmeterol" title="Salmeterol">Salmeterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Long-acting_beta-adrenoceptor_agonist#Ultra-LABAs" title="Long-acting beta-adrenoceptor agonist">Ultra-long-acting β<sub>2</sub> agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abediterol" title="Abediterol">Abediterol</a></li> <li><a href="/wiki/Carmoterol" title="Carmoterol">Carmoterol</a></li> <li><a href="/wiki/Indacaterol" title="Indacaterol">Indacaterol</a></li> <li><a href="/wiki/Olodaterol" title="Olodaterol">Olodaterol</a></li> <li><a href="/wiki/Vilanterol" title="Vilanterol">Vilanterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Clorprenaline" title="Clorprenaline">Clorprenaline</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a> (<a href="/wiki/Theophylline_ephedrine" class="mw-redirect" title="Theophylline ephedrine">+theophylline</a>, <a href="/wiki/Tedral" title="Tedral">+theophylline/phenobarbital</a>, <a href="/wiki/Marax" class="mw-redirect" title="Marax">theophylline/hydroxyzine</a>)</li> <li><a href="/wiki/Epinephrine_(medication)" title="Epinephrine (medication)">Epinephrine</a><sup>#</sup></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/Hexoprenaline" title="Hexoprenaline">Hexoprenaline</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline (isoproterenol)</a></li> <li><a href="/wiki/Methylephedrine" title="Methylephedrine">Methylephedrine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline (metaproterenol)</a></li> <li><a href="/wiki/Racephedrine" title="Racephedrine">Racephedrine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Glucocorticoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beclometasone_dipropionate" class="mw-redirect" title="Beclometasone dipropionate">Beclometasone</a><sup>#</sup></li> <li><a href="/wiki/Betamethasone" title="Betamethasone">Betamethasone</a><sup>#</sup></li> <li><a href="/wiki/Budesonide" title="Budesonide">Budesonide</a></li> <li><a href="/wiki/Ciclesonide" title="Ciclesonide">Ciclesonide</a></li> <li><a href="/wiki/Flunisolide" title="Flunisolide">Flunisolide</a></li> <li><a href="/wiki/Fluticasone_propionate" title="Fluticasone propionate">Fluticasone propionate</a></li> <li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone</a></li> <li><a href="/wiki/Triamcinolone" title="Triamcinolone">Triamcinolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anticholinergic" title="Anticholinergic">Anticholinergics</a>/<br /><a href="/wiki/Muscarinic_antagonist" title="Muscarinic antagonist">muscarinic antagonist</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aclidinium_bromide" title="Aclidinium bromide">Aclidinium bromide</a></li> <li><a href="/wiki/Glycopyrronium_bromide" title="Glycopyrronium bromide">Glycopyrronium bromide</a></li> <li><a href="/wiki/Ipratropium_bromide" title="Ipratropium bromide">Ipratropium bromide</a><sup>#</sup></li> <li><a href="/wiki/Oxitropium_bromide" title="Oxitropium bromide">Oxitropium bromide</a></li> <li><a href="/wiki/Tiotropium_bromide" title="Tiotropium bromide">Tiotropium bromide</a></li> <li><a href="/wiki/Umeclidinium_bromide" title="Umeclidinium bromide">Umeclidinium bromide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mast_cell_stabilizer" title="Mast cell stabilizer">Mast cell stabilizers</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cromoglicic_acid" title="Cromoglicic acid">Cromoglicate</a></li> <li><a href="/wiki/Nedocromil" title="Nedocromil">Nedocromil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Xanthine" title="Xanthine">Xanthines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acefylline" title="Acefylline">Acefylline</a></li> <li><a href="/wiki/Ambuphylline" title="Ambuphylline">Ambuphylline</a></li> <li><a href="/wiki/Aminophylline" title="Aminophylline">Aminophylline</a></li> <li><a href="/wiki/Bamifylline" title="Bamifylline">Bamifylline</a></li> <li><a href="/wiki/Choline_theophyllinate" title="Choline theophyllinate">Choline theophyllinate</a></li> <li><a href="/wiki/Doxofylline" title="Doxofylline">Doxofylline</a></li> <li><a href="/wiki/Enprofylline" title="Enprofylline">Enprofylline</a></li> <li><a href="/wiki/Etamiphylline" title="Etamiphylline">Etamiphylline</a></li> <li><a href="/wiki/Proxyphylline" title="Proxyphylline">Proxyphylline</a></li> <li><a class="mw-selflink selflink">Theophylline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Eicosanoid" title="Eicosanoid">Eicosanoid</a> inhibition</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:1%"><a href="/wiki/Leukotriene_antagonist" class="mw-redirect" title="Leukotriene antagonist">Leukotriene antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Montelukast" title="Montelukast">Montelukast</a></li> <li><a href="/wiki/Pranlukast" title="Pranlukast">Pranlukast</a></li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">Zafirlukast</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arachidonate_5-lipoxygenase_inhibitor" title="Arachidonate 5-lipoxygenase inhibitor">Arachidonate 5-lipoxygenase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Zileuton" title="Zileuton">Zileuton</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thromboxane_receptor_antagonist" class="mw-redirect" title="Thromboxane receptor antagonist">Thromboxane receptor antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ramatroban" title="Ramatroban">Ramatroban</a></li> <li><a href="/wiki/Seratrodast" title="Seratrodast">Seratrodast</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Non-xanthine <a href="/wiki/PDE4_inhibitor" title="PDE4 inhibitor">PDE4 inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ibudilast" title="Ibudilast">Ibudilast</a></li> <li><a href="/wiki/Roflumilast" title="Roflumilast">Roflumilast</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others/unknown</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amlexanox" title="Amlexanox">Amlexanox</a></li> <li><a href="/wiki/Ensifentrine" title="Ensifentrine">Ensifentrine</a></li> <li><a href="/wiki/Eprozinol" title="Eprozinol">Eprozinol</a></li> <li><a href="/wiki/Fenspiride" title="Fenspiride">Fenspiride</a><sup>‡</sup></li> <li><a href="/wiki/Omalizumab" title="Omalizumab">Omalizumab</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combination products</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aclidinium_bromide/formoterol" title="Aclidinium bromide/formoterol">Aclidinium bromide/formoterol</a></li> <li><a href="/wiki/Beclometasone/formoterol" title="Beclometasone/formoterol">Beclometasone/formoterol</a></li> <li><a href="/wiki/Beclometasone/formoterol/glycopyrronium_bromide" title="Beclometasone/formoterol/glycopyrronium bromide">Beclometasone/formoterol/glycopyrronium bromide</a></li> <li><a href="/wiki/Budesonide/formoterol" title="Budesonide/formoterol">Budesonide/formoterol</a></li> <li><a href="/wiki/Budesonide/glycopyrronium_bromide/formoterol" title="Budesonide/glycopyrronium bromide/formoterol">Budesonide/glycopyrronium bromide/formoterol</a></li> <li><a href="/wiki/Fluticasone_furoate/umeclidinium_bromide/vilanterol" title="Fluticasone furoate/umeclidinium bromide/vilanterol">Fluticasone furoate/umeclidinium bromide/vilanterol</a></li> <li><a href="/wiki/Fluticasone_furoate/vilanterol" title="Fluticasone furoate/vilanterol">Fluticasone furoate/vilanterol</a></li> <li><a href="/wiki/Fluticasone_propionate/salmeterol" class="mw-redirect" title="Fluticasone propionate/salmeterol">Fluticasone propionate/salmeterol</a></li> <li><a href="/wiki/Glycopyrronium_bromide/formoterol" title="Glycopyrronium bromide/formoterol">Glycopyrronium bromide/formoterol</a></li> <li><a href="/wiki/Indacaterol/glycopyrronium_bromide" title="Indacaterol/glycopyrronium bromide">Indacaterol/glycopyrronium bromide</a></li> <li><a href="/wiki/Indacaterol/glycopyrronium_bromide/mometasone" title="Indacaterol/glycopyrronium bromide/mometasone">Indacaterol/glycopyrronium bromide/mometasone</a></li> <li><a href="/wiki/Indacaterol/mometasone" title="Indacaterol/mometasone">Indacaterol/mometasone</a></li> <li><a href="/wiki/Ipratropium_bromide/salbutamol" title="Ipratropium bromide/salbutamol">Ipratropium bromide/salbutamol</a></li> <li><a href="/wiki/Mometasone/formoterol" title="Mometasone/formoterol">Mometasone/formoterol</a></li> <li><a href="/wiki/Salbutamol/budesonide" title="Salbutamol/budesonide">Salbutamol (albuterol)/budesonide</a></li> <li><a href="/wiki/Theophylline/ephedrine" title="Theophylline/ephedrine">Theophylline/ephedrine</a></li> <li><a href="/wiki/Marax" class="mw-redirect" title="Marax">Theophylline/ephedrine/hydroxyzine</a></li> <li><a href="/wiki/Tedral" title="Tedral">Theophylline/ephedrine/phenobarbital</a></li> <li><a href="/wiki/Umeclidinium_bromide/vilanterol" title="Umeclidinium bromide/vilanterol">Umeclidinium bromide/vilanterol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Stimulants" 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:Stimulants" title="Template:Stimulants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Stimulants" title="Template talk:Stimulants"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Stimulants" title="Special:EditPage/Template:Stimulants"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Stimulants" style="font-size:114%;margin:0 4em"><a href="/wiki/Stimulant" title="Stimulant">Stimulants</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adamantane" title="Adamantane">Adamantanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adapromine" title="Adapromine">Adapromine</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/wiki/Bromantane" title="Bromantane">Bromantane</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Rimantadine" title="Rimantadine">Rimantadine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adenosine_receptor" title="Adenosine receptor">Adenosine antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/8-Chlorotheophylline" title="8-Chlorotheophylline">8-Chlorotheophylline</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dimethylxanthine" title="8-Cyclopentyl-1,3-dimethylxanthine">8-Cyclopentyltheophylline</a></li> <li><a href="/wiki/8-Phenyltheophylline" title="8-Phenyltheophylline">8-Phenyltheophylline</a></li> <li><a href="/wiki/Aminophylline" title="Aminophylline">Aminophylline</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/CGS-15943" title="CGS-15943">CGS-15943</a></li> <li><a href="/wiki/Dimethazan" title="Dimethazan">Dimethazan</a></li> <li><a href="/wiki/Istradefylline" title="Istradefylline">Istradefylline</a></li> <li><a href="/wiki/Paraxanthine" title="Paraxanthine">Paraxanthine</a></li> <li><a href="/wiki/SCH-58261" title="SCH-58261">SCH-58261</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a class="mw-selflink selflink">Theophylline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Psychotropic_alkylamines" title="Psychotropic alkylamines">Alkylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopentamine" title="Cyclopentamine">Cyclopentamine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexaneamine</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li> <li><a href="/wiki/Tuaminoheptane" title="Tuaminoheptane">Tuaminoheptane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ampakine" title="Ampakine">Ampakines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CX-516" title="CX-516">CX-516</a></li> <li><a href="/wiki/CX-546" title="CX-546">CX-546</a></li> <li><a href="/wiki/CX-614" class="mw-redirect" title="CX-614">CX-614</a></li> <li><a href="/wiki/Farampator" title="Farampator">CX-691</a></li> <li><a href="/wiki/CX717" title="CX717">CX-717</a></li> <li><a href="/wiki/IDRA-21" title="IDRA-21">IDRA-21</a></li> <li><a href="/wiki/LY-404,187" class="mw-redirect" title="LY-404,187">LY-404,187</a></li> <li><a href="/wiki/LY-503,430" class="mw-redirect" title="LY-503,430">LY-503,430</a></li> <li><a href="/wiki/Nooglutyl" title="Nooglutyl">Nooglutyl</a></li> <li><a href="/wiki/Org_26576" class="mw-redirect" title="Org 26576">Org 26576</a></li> <li><a href="/wiki/PEPA_(drug)" title="PEPA (drug)">PEPA</a></li> <li><a href="/wiki/S-18986" title="S-18986">S-18986</a></li> <li><a href="/wiki/Sunifiram" title="Sunifiram">Sunifiram</a></li> <li><a href="/wiki/Unifiram" title="Unifiram">Unifiram</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclohexylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benocyclidine" title="Benocyclidine">Benocyclidine</a></li> <li><a href="/wiki/Dieticyclidine" title="Dieticyclidine">Dieticyclidine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Eticyclidine" title="Eticyclidine">Eticyclidine</a></li> <li><a href="/wiki/Gacyclidine" title="Gacyclidine">Gacyclidine</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Phencyclamine" class="mw-redirect" title="Phencyclamine">Phencyclamine</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Rolicyclidine" title="Rolicyclidine">Rolicyclidine</a></li> <li><a href="/wiki/Tenocyclidine" title="Tenocyclidine">Tenocyclidine</a></li> <li><a href="/wiki/Tiletamine" title="Tiletamine">Tiletamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzazepine" title="Benzazepine">Benzazepines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Br-APB" title="6-Br-APB">6-Br-APB</a></li> <li><a href="/wiki/SKF-77434" class="mw-redirect" title="SKF-77434">SKF-77434</a></li> <li><a href="/wiki/SKF-81297" class="mw-redirect" title="SKF-81297">SKF-81297</a></li> <li><a href="/wiki/SKF-82958" class="mw-redirect" title="SKF-82958">SKF-82958</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Cathinones</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-FMC" class="mw-redirect" title="3-FMC">3-FMC</a></li> <li><a href="/wiki/3-MMC" class="mw-redirect" title="3-MMC">3-MMC</a></li> <li><a href="/wiki/3,4-Dimethylmethcathinone" title="3,4-Dimethylmethcathinone">3,4-DMMC</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">4-BMC</a></li> <li><a href="/wiki/4-Chloromethcathinone" title="4-Chloromethcathinone">4-CMC</a></li> <li><a href="/wiki/4-Methylbuphedrone" title="4-Methylbuphedrone">4-Methylbuphedrone</a></li> <li><a href="/wiki/4-Methylcathinone" title="4-Methylcathinone">4-Methylcathinone</a></li> <li><a href="/wiki/4-Methyl-%CE%B1-ethylaminopentiophenone" title="4-Methyl-α-ethylaminopentiophenone">4-MEAP</a></li> <li><a href="/wiki/4-Methylpentedrone" title="4-Methylpentedrone">4-Methylpentedrone</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Benzedrone" title="Benzedrone">Benzedrone</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Dimethylcathinone" class="mw-redirect" title="Dimethylcathinone">Dimethylcathinone</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Hexedrone" title="Hexedrone">Hexedrone</a></li> <li><a href="/wiki/Isoethcathinone" title="Isoethcathinone">Isoethcathinone</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylenedioxycathinone" title="Methylenedioxycathinone">Methylenedioxycathinone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Mexedrone" title="Mexedrone">Mexedrone</a></li> <li><a href="/wiki/N-Ethylbuphedrone" title="N-Ethylbuphedrone">N-Ethylbuphedrone</a></li> <li><a href="/wiki/N-Ethylhexedrone" title="N-Ethylhexedrone">N-Ethylhexedrone</a></li> <li><a href="/wiki/Pentedrone" title="Pentedrone">Pentedrone</a></li> <li><a href="/wiki/Pentylone" title="Pentylone">Pentylone</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Acetylcholine" title="Acetylcholine">Cholinergics</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/A-84,543" title="A-84,543">A-84,543</a></li> <li><a href="/wiki/A-366,833" title="A-366,833">A-366,833</a></li> <li><a href="/wiki/ABT-202" title="ABT-202">ABT-202</a></li> <li><a href="/wiki/ABT-418" title="ABT-418">ABT-418</a></li> <li><a href="/wiki/AR-R17779" title="AR-R17779">AR-R17779</a></li> <li><a href="/wiki/Altinicline" title="Altinicline">Altinicline</a></li> <li><a href="/wiki/Anabasine" title="Anabasine">Anabasine</a></li> <li><a href="/wiki/Arecoline" title="Arecoline">Arecoline</a></li> <li><a href="/wiki/Bradanicline" title="Bradanicline">Bradanicline</a></li> <li><a href="/wiki/Cotinine" title="Cotinine">Cotinine</a></li> <li><a href="/wiki/Cytisine" title="Cytisine">Cytisine</a></li> <li><a href="/wiki/Dianicline" title="Dianicline">Dianicline</a></li> <li><a href="/wiki/Epibatidine" title="Epibatidine">Epibatidine</a></li> <li><a href="/wiki/Epiboxidine" title="Epiboxidine">Epiboxidine</a></li> <li><a href="/wiki/GTS-21" title="GTS-21">GTS-21</a></li> <li><a href="/wiki/Ispronicline" title="Ispronicline">Ispronicline</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/PHA-543,613" title="PHA-543,613">PHA-543,613</a></li> <li><a href="/wiki/PNU-120,596" title="PNU-120,596">PNU-120,596</a></li> <li><a href="/wiki/PNU-282,987" title="PNU-282,987">PNU-282,987</a></li> <li><a href="/wiki/Pozanicline" title="Pozanicline">Pozanicline</a></li> <li><a href="/wiki/Rivanicline" title="Rivanicline">Rivanicline</a></li> <li><a href="/wiki/Sazetidine_A" title="Sazetidine A">Sazetidine A</a></li> <li><a href="/wiki/SIB-1553A" title="SIB-1553A">SIB-1553A</a></li> <li><a href="/wiki/SSR-180,711" title="SSR-180,711">SSR-180,711</a></li> <li><a href="/wiki/TC-1698" title="TC-1698">TC-1698</a></li> <li><a href="/wiki/TC-1827" title="TC-1827">TC-1827</a></li> <li><a href="/wiki/TC-2216" title="TC-2216">TC-2216</a></li> <li><a href="/wiki/Tebanicline" title="Tebanicline">Tebanicline</a></li> <li><a href="/wiki/UB-165" title="UB-165">UB-165</a></li> <li><a href="/wiki/Varenicline" title="Varenicline">Varenicline</a></li> <li><a href="/wiki/WAY-317,538" class="mw-redirect" title="WAY-317,538">WAY-317,538</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Convulsion" title="Convulsion">Convulsants</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/wiki/DMCM" title="DMCM">DMCM</a></li> <li><a href="/wiki/Flurothyl" title="Flurothyl">Flurothyl</a></li> <li><a href="/wiki/Gabazine" title="Gabazine">Gabazine</a></li> <li><a href="/wiki/Pentylenetetrazol" title="Pentylenetetrazol">Pentetrazol</a></li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Thujone" title="Thujone">Thujone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Eugeroic" title="Eugeroic">Eugeroics</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adrafinil" title="Adrafinil">Adrafinil</a></li> <li><a href="/wiki/Armodafinil" title="Armodafinil">Armodafinil</a></li> <li><a href="/wiki/CRL-40,940" class="mw-redirect" title="CRL-40,940">CRL-40,940</a></li> <li><a href="/wiki/CRL-40,941" class="mw-redirect" title="CRL-40,941">CRL-40,941</a></li> <li><a href="/wiki/Fluorenol" title="Fluorenol">Fluorenol</a></li> <li><a href="/wiki/Modafinil" title="Modafinil">Modafinil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oxazoline" title="Oxazoline">Oxazolines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-Methylaminorex</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Cyclazodone" title="Cyclazodone">Cyclazodone</a></li> <li><a href="/wiki/Fenozolone" title="Fenozolone">Fenozolone</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li> <li><a href="/wiki/Pemoline" title="Pemoline">Pemoline</a></li> <li><a href="/wiki/Thozalinone" title="Thozalinone">Thozalinone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Methylphenylisobutylamine" title="4-Methylphenylisobutylamine">1-(4-Methylphenyl)-2-aminobutane</a></li> <li><a href="/wiki/1-Methylamino-1-(3,4-methylenedioxyphenyl)propane" title="1-Methylamino-1-(3,4-methylenedioxyphenyl)propane">1-Methylamino-1-(3,4-methylenedioxyphenyl)propane</a></li> <li><a href="/wiki/2-Fluoroamphetamine" title="2-Fluoroamphetamine">2-Fluoroamphetamine</a></li> <li><a href="/wiki/2-FMA" class="mw-redirect" title="2-FMA">2-Fluoromethamphetamine</a></li> <li><a href="/wiki/2-Hydroxyphenethylamine" class="mw-redirect" title="2-Hydroxyphenethylamine">2-OH-PEA</a></li> <li><a href="/wiki/2-Phenyl-3-aminobutane" title="2-Phenyl-3-aminobutane">2-Phenyl-3-aminobutane</a></li> <li><a href="/wiki/2,3-Methylenedioxyamphetamine" title="2,3-Methylenedioxyamphetamine">2,3-MDA</a></li> <li><a href="/wiki/3-FA" class="mw-redirect" title="3-FA">3-Fluoroamphetamine</a></li> <li><a href="/wiki/3-Fluoroethamphetamine" title="3-Fluoroethamphetamine">3-Fluoroethamphetamine</a></li> <li><a href="/wiki/3-Methoxyamphetamine" title="3-Methoxyamphetamine">3-Methoxyamphetamine</a></li> <li><a href="/wiki/3-Methylamphetamine" title="3-Methylamphetamine">3-Methylamphetamine</a></li> <li><a href="/wiki/4-FA" class="mw-redirect" title="4-FA">4-Fluoroamphetamine</a></li> <li><a href="/wiki/4-FMA" class="mw-redirect" title="4-FMA">4-Fluoromethamphetamine</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" class="mw-redirect" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/AL-1095" title="AL-1095">AL-1095</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Alpha-Ethylphenethylamine" class="mw-redirect" title="Alpha-Ethylphenethylamine">a-Ethylphenethylamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-Amino-1,2-dihydronaphthalene</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-Aminoindane</a></li> <li><a href="/wiki/5-(2-Aminopropyl)indole" class="mw-redirect" title="5-(2-Aminopropyl)indole">5-(2-Aminopropyl)indole</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-Aminotetralin</a></li> <li><a href="/wiki/Acridorex" title="Acridorex">Acridorex</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a>, <a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/%CE%92-Phenylmethamphetamine" title="Β-Phenylmethamphetamine">β-Phenylmethamphetamine</a></li> <li><a href="/wiki/Benfluorex" title="Benfluorex">Benfluorex</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/3-Benzhydrylmorpholine" title="3-Benzhydrylmorpholine">3-Benzhydrylmorpholine</a></li> <li><a href="/wiki/Benzofuranylpropylaminopentane" title="Benzofuranylpropylaminopentane">BPAP</a></li> <li><a href="/wiki/Camfetamine" title="Camfetamine">Camfetamine</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cilobamine" title="Cilobamine">Cilobamine</a></li> <li><a href="/wiki/Cinnamedrine" title="Cinnamedrine">Cinnamedrine</a></li> <li><a href="/wiki/Clenbuterol" title="Clenbuterol">Clenbuterol</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl"><small>D</small>-Deprenyl</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">Dimethoxyamphetamine</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">DOPA</a> (<a href="/wiki/D-DOPA" title="D-DOPA">Dextrodopa</a>, <a href="/wiki/L-DOPA" title="L-DOPA">Levodopa</a>)</li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/L-DOPS" class="mw-redirect" title="L-DOPS">Droxidopa</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li> <li><a href="/wiki/Epinine" class="mw-redirect" title="Epinine">Epinine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fencamfamin" title="Fencamfamin">Fencamfamin</a></li> <li><a href="/wiki/Fencamine" title="Fencamine">Fencamine</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a> (<a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a>)</li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Formetorex" title="Formetorex">Formetorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Gepefrine" title="Gepefrine">Gepefrine</a></li> <li><a href="/wiki/Hexapradol" title="Hexapradol">Hexapradol</a></li> <li><a href="/wiki/4-Hydroxy-3-methoxymethamphetamine" title="4-Hydroxy-3-methoxymethamphetamine">HMMA</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-Iodo-2-aminoindane</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">Indanylamphetamine</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Selegiline" title="Selegiline"><small>L</small>-Deprenyl</a> (Selegiline)</li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylbenzodioxolylbutanamine" class="mw-redirect" title="Methylbenzodioxolylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxybutylamphetamine" title="Methylenedioxybutylamphetamine">MDBU</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxypropylamphetamine" class="mw-redirect" title="Methylenedioxypropylamphetamine">MDPR</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Mesocarb" title="Mesocarb">Mesocarb</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> (<a href="/wiki/Methamphetamine" title="Methamphetamine">Dextromethamphetamine</a>, <a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a>)</li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/3-Methoxymethamphetamine" title="3-Methoxymethamphetamine">MMMA</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/N,alpha-Diethylphenylethylamine" class="mw-redirect" title="N,alpha-Diethylphenylethylamine">N,alpha-Diethylphenylethylamine</a></li> <li><a href="/wiki/N,N-Dimethylphenethylamine" title="N,N-Dimethylphenethylamine">N,N-Dimethylphenethylamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylamphetamine</a></li> <li><a href="/wiki/Nisoxetine" title="Nisoxetine">Nisoxetine</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/L-Norpseudoephedrine" title="L-Norpseudoephedrine"><small>L</small>-Norpseudoephedrine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine">Octopamine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Oxifentorex" title="Oxifentorex">Oxifentorex</a></li> <li><a href="/wiki/Oxilofrine" title="Oxilofrine">Oxilofrine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">PBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">PCA</a></li> <li><a href="/wiki/Para-Chloromethamphetamine" title="Para-Chloromethamphetamine">PCMA</a></li> <li><a href="/wiki/Norpholedrine" class="mw-redirect" title="Norpholedrine">PHA</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phenatine" title="Phenatine">Phenatine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">PIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxyethylamphetamine" class="mw-redirect" title="Para-Methoxyethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxymethamphetamine" class="mw-redirect" title="Para-Methoxymethamphetamine">PMMA</a></li> <li><a href="/wiki/Phenylpropylaminopentane" title="Phenylpropylaminopentane">PPAP</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Ropinirole" title="Ropinirole">Ropinirole</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a> (<a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a>)</li> <li><a href="/wiki/Sibutramine" title="Sibutramine">Sibutramine</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenylmorpholine" title="Substituted phenylmorpholine">Phenylmorpholines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Fluorophenmetrazine" title="3-Fluorophenmetrazine">3-Fluorophenmetrazine</a></li> <li><a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</a></li> <li><a href="/wiki/G-130" title="G-130">G-130</a></li> <li><a href="/wiki/Manifaxine" title="Manifaxine">Manifaxine</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/PD-128,907" title="PD-128,907">PD-128,907</a></li> <li><a href="/wiki/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/2-Phenyl-3,6-dimethylmorpholine" title="2-Phenyl-3,6-dimethylmorpholine">2-Phenyl-3,6-dimethylmorpholine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/1-(3-chlorophenyl)-4-(2-phenylethyl)piperazine" class="mw-redirect" title="1-(3-chlorophenyl)-4-(2-phenylethyl)piperazine">3C-PEP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/CM156" title="CM156">CM156</a></li> <li><a href="/wiki/DBL-583" title="DBL-583">DBL-583</a></li> <li><a href="/wiki/GBR-12783" title="GBR-12783">GBR-12783</a></li> <li><a href="/wiki/GBR-12935" title="GBR-12935">GBR-12935</a></li> <li><a href="/wiki/GBR-13069" title="GBR-13069">GBR-13069</a></li> <li><a href="/wiki/GBR-13098" title="GBR-13098">GBR-13098</a></li> <li><a href="/wiki/GBR-13119" title="GBR-13119">GBR-13119</a></li> <li><a href="/wiki/JJC8-088" title="JJC8-088">JJC8-088</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Piperidine" title="Piperidine">Piperidines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine" title="1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine">1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine</a></li> <li><a href="/wiki/2-Benzylpiperidine" title="2-Benzylpiperidine">2-Benzylpiperidine</a></li> <li><a href="/wiki/2-Methyl-3-phenylpiperidine" title="2-Methyl-3-phenylpiperidine">2-Methyl-3-phenylpiperidine</a></li> <li><a href="/wiki/3,4-Dichloromethylphenidate" title="3,4-Dichloromethylphenidate">3,4-Dichloromethylphenidate</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-Benzylpiperidine</a></li> <li><a href="/wiki/4-Fluoromethylphenidate" title="4-Fluoromethylphenidate">4-Fluoromethylphenidate</a></li> <li><a href="/wiki/4-Methylmethylphenidate" title="4-Methylmethylphenidate">4-Methylmethylphenidate</a></li> <li><a href="/wiki/Desoxypipradrol" title="Desoxypipradrol">Desoxypipradrol</a></li> <li><a href="/wiki/Difemetorex" title="Difemetorex">Difemetorex</a></li> <li><a href="/wiki/Diphenylpyraline" title="Diphenylpyraline">Diphenylpyraline</a></li> <li><a href="/wiki/HDEP-28" title="HDEP-28">Ethylnaphthidate</a></li> <li><a href="/wiki/Ethylphenidate" title="Ethylphenidate">Ethylphenidate</a></li> <li><a href="/wiki/HDMP-28" title="HDMP-28">Methylnaphthidate</a></li> <li><a href="/wiki/Isopropylphenidate" title="Isopropylphenidate">Isopropylphenidate</a></li> <li><a href="/wiki/JZ-IV-10" title="JZ-IV-10">JZ-IV-10</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a> (<a href="/wiki/Dexmethylphenidate" title="Dexmethylphenidate">Dexmethylphenidate</a>)</li> <li><a href="/wiki/(%2B)-CPCA" title="(+)-CPCA">Nocaine</a></li> <li><a href="/wiki/Levophacetoperane" title="Levophacetoperane">Phacetoperane</a></li> <li><a href="/wiki/Pipradrol" title="Pipradrol">Pipradrol</a></li> <li><a href="/wiki/Propylphenidate" title="Propylphenidate">Propylphenidate</a></li> <li><a href="/wiki/Serdexmethylphenidate" title="Serdexmethylphenidate">Serdexmethylphenidate</a></li> <li><a href="/wiki/SCH-5472" title="SCH-5472">SCH-5472</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrrolidine" title="Pyrrolidine">Pyrrolidines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Diphenylmethylpyrrolidine" title="2-Diphenylmethylpyrrolidine">2-Diphenylmethylpyrrolidine</a></li> <li><a href="/wiki/4-Chloro-alpha-pyrrolidinovalerophenone" class="mw-redirect" title="4-Chloro-alpha-pyrrolidinovalerophenone">4-Cl-PVP</a></li> <li><a href="/wiki/5-DBFPV" title="5-DBFPV">5-DBFPV</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopropiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopropiophenone">α-PPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinobutiophenone" class="mw-redirect" title="Alpha-Pyrrolidinobutiophenone">α-PBP</a></li> <li><a href="/wiki/%CE%91-PCYP" title="Α-PCYP">α-PCYP</a></li> <li><a href="/wiki/%CE%91-PHiP" title="Α-PHiP">α-PHiP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinohexiophenone" class="mw-redirect" title="Alpha-Pyrrolidinohexiophenone">α-PHP</a></li> <li><a href="/wiki/%CE%91-Pyrrolidinoheptaphenone" title="Α-Pyrrolidinoheptaphenone">α-PHPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiophenone">α-PVP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiothiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiothiophenone">α-PVT</a></li> <li><a href="/wiki/Diphenylprolinol" title="Diphenylprolinol">Diphenylprolinol</a></li> <li><a href="/wiki/3%27,4%27-Dimethoxy-%CE%B1-Pyrrolidinopentiophenone" class="mw-redirect" title="3',4'-Dimethoxy-α-Pyrrolidinopentiophenone">DMPVP</a></li> <li><a href="/wiki/4%27-Fluoro-%CE%B1-Pyrrolidinooctanophenone" class="mw-redirect" title="4'-Fluoro-α-Pyrrolidinooctanophenone">FPOP</a></li> <li><a href="/wiki/4%27-Fluoro-%CE%B1-Pyrrolidinopentiophenone" class="mw-redirect" title="4'-Fluoro-α-Pyrrolidinopentiophenone">FPVP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinopropiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinopropiophenone">MDPPP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinobutiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinobutiophenone">MDPBP</a></li> <li><a href="/wiki/4%27-Methyl-a-pyrrolidinobutiophenone" class="mw-redirect" title="4'-Methyl-a-pyrrolidinobutiophenone">MPBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">MPHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">MPPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-Pyrrolidinopentiophenone" class="mw-redirect" title="4'-Methoxy-α-Pyrrolidinopentiophenone">MOPVP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopropiophenone" title="4'-Methoxy-α-pyrrolidinopropiophenone">MOPPP</a></li> <li><a href="/wiki/Indapyrophenidone" title="Indapyrophenidone">Indapyrophenidone</a></li> <li><a href="/wiki/Methylenedioxypyrovalerone" title="Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">PEP</a></li> <li><a href="/wiki/Picilorex" title="Picilorex">Picilorex</a></li> <li><a href="/wiki/Prolintane" title="Prolintane">Prolintane</a></li> <li><a href="/wiki/Pyrovalerone" title="Pyrovalerone">Pyrovalerone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Racetam" title="Racetam">Racetams</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Oxiracetam" title="Oxiracetam">Oxiracetam</a></li> <li><a href="/wiki/Phenylpiracetam" title="Phenylpiracetam">Phenylpiracetam</a></li> <li><a href="/wiki/Phenylpiracetam_hydrazide" title="Phenylpiracetam hydrazide">Phenylpiracetam hydrazide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tropane" title="Tropane">Tropanes</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-fluorotropacocaine" class="mw-redirect" title="4-fluorotropacocaine">4-fluorotropacocaine</a></li> <li><a href="/wiki/4%27-Fluorococaine" class="mw-redirect" title="4'-Fluorococaine">4'-Fluorococaine</a></li> <li><a href="/wiki/Altropane" title="Altropane">Altropane (IACFT)</a></li> <li><a href="/wiki/Brasofensine" title="Brasofensine">Brasofensine</a></li> <li><a href="/wiki/WIN_35428" class="mw-redirect" title="WIN 35428">CFT (WIN 35,428)</a></li> <li><a href="/wiki/RTI-55" title="RTI-55">β-CIT (RTI-55)</a></li> <li><a href="/wiki/Cocaethylene" title="Cocaethylene">Cocaethylene</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Dichloropane" title="Dichloropane">Dichloropane (RTI-111)</a></li> <li><a href="/wiki/Difluoropine" title="Difluoropine">Difluoropine</a></li> <li><a href="/wiki/FE-%CE%B2-CPPIT" title="FE-β-CPPIT">FE-β-CPPIT</a></li> <li><a href="/wiki/FP-%CE%B2-CPPIT" title="FP-β-CPPIT">FP-β-CPPIT</a></li> <li><a href="/wiki/Ioflupane_(123I)" title="Ioflupane (123I)">Ioflupane (<sup>123</sup>I)</a></li> <li><a href="/wiki/Norcocaine" title="Norcocaine">Norcocaine</a></li> <li><a href="/wiki/2-Propanoyl-3-(4-isopropylphenyl)-tropane" title="2-Propanoyl-3-(4-isopropylphenyl)-tropane">PIT</a></li> <li><a href="/wiki/2%CE%B2-Propanoyl-3%CE%B2-(4-tolyl)-tropane" title="2β-Propanoyl-3β-(4-tolyl)-tropane">PTT</a></li> <li><a href="/wiki/RTI-31" title="RTI-31">RTI-31</a></li> <li><a href="/wiki/RTI-32" title="RTI-32">RTI-32</a></li> <li><a href="/wiki/RTI-51" title="RTI-51">RTI-51</a></li> <li><a href="/wiki/RTI-112" title="RTI-112">RTI-112</a></li> <li><a href="/wiki/RTI-113" title="RTI-113">RTI-113</a></li> <li><a href="/wiki/RTI-120" title="RTI-120">RTI-120</a></li> <li><a href="/wiki/RTI-121" title="RTI-121">RTI-121 (IPCIT)</a></li> <li><a href="/wiki/RTI-126" title="RTI-126">RTI-126</a></li> <li><a href="/wiki/RTI-150" title="RTI-150">RTI-150</a></li> <li><a href="/wiki/RTI-177" title="RTI-177">RTI-177</a></li> <li><a href="/wiki/RTI-229" title="RTI-229">RTI-229</a></li> <li><a href="/wiki/(-)-2%CE%B2-(3-(4-Methylphenyl)isoxazol-5-yl)-3%CE%B2-(4-chlorophenyl)tropane" class="mw-redirect" title="(-)-2β-(3-(4-Methylphenyl)isoxazol-5-yl)-3β-(4-chlorophenyl)tropane">RTI-336</a></li> <li><a href="/wiki/RTI-354" class="mw-redirect" title="RTI-354">RTI-354</a></li> <li><a href="/wiki/RTI-371" title="RTI-371">RTI-371</a></li> <li><a href="/wiki/RTI-386" class="mw-redirect" title="RTI-386">RTI-386</a></li> <li><a href="/wiki/Salicylmethylecgonine" title="Salicylmethylecgonine">Salicylmethylecgonine</a></li> <li><a href="/wiki/Tesofensine" title="Tesofensine">Tesofensine</a></li> <li><a href="/wiki/Troparil" title="Troparil">Troparil (β-CPT, WIN 35,065-2)</a></li> <li><a href="/wiki/Tropoxane" title="Tropoxane">Tropoxane</a></li> <li><a href="/wiki/2%CE%B2-Propanoyl-3%CE%B2-(2-naphthyl)-tropane" title="2β-Propanoyl-3β-(2-naphthyl)-tropane">WF-23</a></li> <li><a href="/wiki/2%CE%B1-(Propanoyl)-3%CE%B2-(2-(6-methoxynaphthyl))-tropane" title="2α-(Propanoyl)-3β-(2-(6-methoxynaphthyl))-tropane">WF-33</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-HO-%CE%B1MT" title="4-HO-αMT">4-HO-αMT</a></li> <li><a href="/wiki/4-Methyl-%CE%B1ET" class="mw-redirect" title="4-Methyl-αET">4-Methyl-αET</a></li> <li><a href="/wiki/4-Methyl-%CE%B1MT" class="mw-redirect" title="4-Methyl-αMT">4-Methyl-αMT</a></li> <li><a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Chloro-αMT</a></li> <li><a href="/wiki/5-Fluoro-%CE%B1MT" class="mw-redirect" title="5-Fluoro-αMT">5-Fluoro-αMT</a></li> <li><a href="/wiki/5-MeO-%CE%B1ET" class="mw-redirect" title="5-MeO-αET">5-MeO-αET</a></li> <li><a href="/wiki/5-MeO-%CE%B1MT" class="mw-redirect" title="5-MeO-αMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DIPT</a></li> <li><a href="/wiki/6-Fluoro-%CE%B1MT" class="mw-redirect" title="6-Fluoro-αMT">6-Fluoro-αMT</a></li> <li><a href="/wiki/7-Methyl-%CE%B1ET" class="mw-redirect" title="7-Methyl-αET">7-Methyl-αET</a></li> <li><a href="/wiki/%CE%91-Ethyltryptamine" title="Α-Ethyltryptamine">αET</a></li> <li><a href="/wiki/%CE%91-Methyltryptamine" title="Α-Methyltryptamine">αMT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">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><a href="/wiki/2-MDP" title="2-MDP">2-MDP</a></li> <li><a href="/wiki/3,3-Diphenylcyclobutanamine" title="3,3-Diphenylcyclobutanamine">3,3-Diphenylcyclobutanamine</a></li> <li><a href="/wiki/Amfonelic_acid" title="Amfonelic acid">Amfonelic acid</a></li> <li><a href="/wiki/Amineptine" title="Amineptine">Amineptine</a></li> <li><a href="/wiki/Amiphenazole" title="Amiphenazole">Amiphenazole</a></li> <li><a href="/wiki/Atipamezole" title="Atipamezole">Atipamezole</a></li> <li><a href="/wiki/Atomoxetine" title="Atomoxetine">Atomoxetine</a></li> <li><a href="/wiki/Bemegride" title="Bemegride">Bemegride</a></li> <li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Butyltolylquinuclidine" title="Butyltolylquinuclidine">BTQ</a></li> <li><a href="/wiki/BTS_74,398" title="BTS 74,398">BTS 74,398</a></li> <li><a href="/wiki/Centanafadine" title="Centanafadine">Centanafadine</a></li> <li><a href="/wiki/Ciclazindol" title="Ciclazindol">Ciclazindol</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <li><a href="/wiki/Cropropamide" class="mw-redirect" title="Cropropamide">Cropropamide</a></li> <li><a href="/wiki/Crotetamide" class="mw-redirect" title="Crotetamide">Crotetamide</a></li> <li><a href="/wiki/D-161" title="D-161">D-161</a></li> <li><a href="/wiki/Desipramine" title="Desipramine">Desipramine</a></li> <li><a href="/wiki/Diclofensine" title="Diclofensine">Diclofensine</a></li> <li><a href="/wiki/Dimethocaine" title="Dimethocaine">Dimethocaine</a></li> <li><a href="/wiki/Efaroxan" title="Efaroxan">Efaroxan</a></li> <li><a href="/wiki/Etamivan" title="Etamivan">Etamivan</a></li> <li><a href="/wiki/Fenisorex" title="Fenisorex">Fenisorex</a></li> <li><a href="/wiki/Fenpentadiol" title="Fenpentadiol">Fenpentadiol</a></li> <li><a href="/wiki/Gamfexine" title="Gamfexine">Gamfexine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/GSK1360707F" title="GSK1360707F">GSK1360707F</a></li> <li><a href="/wiki/GYKI-52895" class="mw-redirect" title="GYKI-52895">GYKI-52895</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Idazoxan" title="Idazoxan">Idazoxan</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Indatraline" title="Indatraline">Indatraline</a></li> <li><a href="/wiki/JNJ-7925476" title="JNJ-7925476">JNJ-7925476</a></li> <li><a href="/wiki/Lazabemide" title="Lazabemide">Lazabemide</a></li> <li><a href="/wiki/Leptacline" title="Leptacline">Leptacline</a></li> <li><a href="/wiki/Lomevactone" title="Lomevactone">Lomevactone</a></li> <li><a href="/wiki/LR-5182" title="LR-5182">LR-5182</a></li> <li><a href="/wiki/Mazindol" title="Mazindol">Mazindol</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Mefexamide" title="Mefexamide">Mefexamide</a></li> <li><a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/Methastyridone" title="Methastyridone">Methastyridone</a></li> <li><a href="/wiki/Methiopropamine" title="Methiopropamine">Methiopropamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/Nikethamide" title="Nikethamide">Nikethamide</a></li> <li><a href="/wiki/Nomifensine" title="Nomifensine">Nomifensine</a></li> <li><a href="/wiki/O-2172" title="O-2172">O-2172</a></li> <li><a href="/wiki/Oxaprotiline" title="Oxaprotiline">Oxaprotiline</a></li> <li><a href="/wiki/PNU-99,194" title="PNU-99,194">PNU-99,194</a></li> <li><a href="/wiki/PRC200" class="mw-redirect" title="PRC200">PRC200-SS</a></li> <li><a href="/wiki/Rasagiline" title="Rasagiline">Rasagiline</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Rubidium_chloride" title="Rubidium chloride">Rubidium chloride</a></li> <li><a href="/wiki/Setazindol" title="Setazindol">Setazindol</a></li> <li><a href="/wiki/Tametraline" title="Tametraline">Tametraline</a></li> <li><a href="/wiki/Tandamine" title="Tandamine">Tandamine</a></li> <li><a href="/wiki/Thiopropamine" title="Thiopropamine">Thiopropamine</a></li> <li><a href="/wiki/Thiothinone" title="Thiothinone">Thiothinone</a></li> <li><a href="/wiki/Trazium" title="Trazium">Trazium</a></li> <li><a href="/wiki/UH-232" title="UH-232">UH-232</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-style:italic"><div><a href="/wiki/ATC_code" class="mw-redirect" title="ATC code">ATC code</a>: <a href="/wiki/ATC_code_N06#N06B" title="ATC code N06">N06B</a></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"></div><div role="navigation" class="navbox" aria-labelledby="Chocolate" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background: #7B3F00; color: white;"><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:Chocolate" title="Template:Chocolate"><abbr title="View this template" style="color: white">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chocolate" title="Template talk:Chocolate"><abbr title="Discuss this template" style="color: white">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chocolate" title="Special:EditPage/Template:Chocolate"><abbr title="Edit this template" style="color: white">e</abbr></a></li></ul></div><div id="Chocolate" style="font-size:114%;margin:0 4em"><a href="/wiki/Chocolate" title="Chocolate"><span style="color:white">Chocolate</span></a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;"><a href="/wiki/Cocoa_bean" title="Cocoa bean"><span style="color:white">Cocoa bean</span></a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chocolate_liquor" title="Chocolate liquor">Chocolate liquor</a></li> <li><a href="/wiki/Cocoa_butter" title="Cocoa butter">Cocoa butter</a></li> <li><a href="/wiki/Cocoa_solids" title="Cocoa solids">Cocoa solids</a></li> <li><i><a href="/wiki/Theobroma_cacao" title="Theobroma cacao">Theobroma cacao</a></i></li> <li><a href="/wiki/Types_of_cocoa_beans" title="Types of cocoa beans">Types</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Components</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Endorphins" title="Endorphins">Endorphins</a></li> <li><a href="/wiki/Enkephalin" title="Enkephalin">Enkephalin</a></li> <li><a href="/wiki/Flavan-3-ol" title="Flavan-3-ol">Flavan-3-ol</a></li> <li><a href="/wiki/Lecithin" title="Lecithin">Lecithin</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li> <li><a href="/wiki/Salsolinol" title="Salsolinol">Salsolinol</a></li> <li><a href="/wiki/Tetramethylpyrazine" title="Tetramethylpyrazine">Tetramethylpyrazine</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a class="mw-selflink selflink">Theophylline</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li> <li><a href="/wiki/Valeric_acid" title="Valeric acid">Valeric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;"><a href="/wiki/Types_of_chocolate" title="Types of chocolate"><span style="color:white">Types</span></a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Baking_chocolate" title="Baking chocolate">Baking</a></li> <li><a href="/wiki/Dark_chocolate" title="Dark chocolate">Dark</a></li> <li><a href="/wiki/Gianduja_(chocolate)" title="Gianduja (chocolate)">Gianduja</a></li> <li><a href="/wiki/Milk_chocolate" title="Milk chocolate">Milk</a></li> <li><a href="/wiki/Organic_chocolate" title="Organic chocolate">Organic</a></li> <li><a href="/wiki/Raw_chocolate" title="Raw chocolate">Raw</a></li> <li><a href="/wiki/Ruby_chocolate" title="Ruby chocolate">Ruby</a></li> <li><a href="/wiki/White_chocolate" title="White chocolate">White</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Products</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Caff%C3%A8_mocha" title="Caffè mocha">Caffè mocha</a></li> <li><a href="/wiki/Chocolate_bar" title="Chocolate bar">Chocolate bar</a> <ul><li><a href="/wiki/List_of_chocolate_bar_brands" title="List of chocolate bar brands">Brands</a></li></ul></li> <li><a href="/wiki/Chocolate_biscuit" title="Chocolate biscuit">Chocolate biscuit</a></li> <li><a href="/wiki/Chocolate_brownie" title="Chocolate brownie">Chocolate brownie</a></li> <li><a href="/wiki/Chocolate_cake" title="Chocolate cake">Chocolate cake</a></li> <li><a href="/wiki/Chocolate_chip_cookie" title="Chocolate chip cookie">Chocolate chip cookie</a></li> <li><a href="/wiki/Chocolate_chip" title="Chocolate chip">Chocolate chip</a></li> <li><a href="/wiki/Chocolate_coin" title="Chocolate coin">Chocolate coins</a></li> <li><a href="/wiki/Chocolate_crackles" title="Chocolate crackles">Chocolate crackles</a></li> <li><a href="/wiki/Chocolate_gravy" title="Chocolate gravy">Chocolate gravy</a></li> <li><a href="/wiki/Chocolate_ice_cream" title="Chocolate ice cream">Chocolate ice cream</a></li> <li><a href="/wiki/Chocolate_liqueur" title="Chocolate liqueur">Chocolate liqueur</a></li> <li><a href="/wiki/Chocolate_milk" title="Chocolate milk">Chocolate milk</a></li> <li><a href="/wiki/Chocolate_pudding" title="Chocolate pudding">Chocolate pudding</a></li> <li><a href="/wiki/Chocolate_spread" title="Chocolate spread">Chocolate spread</a></li> <li><a href="/wiki/Chocolate_syrup" title="Chocolate syrup">Chocolate syrup</a></li> <li><a href="/wiki/Chocolate_truffle" title="Chocolate truffle">Chocolate truffle</a></li> <li><a href="/wiki/Cioccolato_di_Modica" title="Cioccolato di Modica">Cioccolato di Modica</a></li> <li><a href="/wiki/Fudge" title="Fudge">Fudge</a></li> <li><a href="/wiki/Ganache" title="Ganache">Ganache</a></li> <li><a href="/wiki/Hot_chocolate" title="Hot chocolate">Hot chocolate</a></li> <li><a href="/wiki/List_of_chocolate_drinks" title="List of chocolate drinks">Other beverages</a></li> <li><a href="/wiki/List_of_chocolate-covered_foods" title="List of chocolate-covered foods">Chocolate-covered foods</a></li> <li><a href="/wiki/Mint_chocolate" title="Mint chocolate">Mint chocolate</a></li> <li><a href="/wiki/Mole_(sauce)" title="Mole (sauce)">Mole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Processes</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aerated_chocolate" title="Aerated chocolate">Aerated chocolate</a></li> <li><a href="/wiki/Broma_process" title="Broma process">Broma process</a></li> <li><a href="/wiki/Conching" title="Conching">Conching</a></li> <li><a href="/wiki/Dutch_process_cocoa" title="Dutch process cocoa">Dutch process</a></li> <li><a href="/wiki/Enrober" title="Enrober">Enrober</a></li> <li><a href="/wiki/Sugar_crust" title="Sugar crust">Sugar crust</a></li> <li><a href="/wiki/Tempered_chocolate" title="Tempered chocolate">Tempering</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Industry</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bean-to-bar" title="Bean-to-bar">Bean-to-bar</a> <ul><li><a href="/wiki/List_of_bean-to-bar_chocolate_manufacturers" title="List of bean-to-bar chocolate manufacturers">Manufacturers</a></li></ul></li> <li><a href="/wiki/Big_Chocolate" title="Big Chocolate">Big Chocolate</a></li> <li><a href="/wiki/Chocolaterie" title="Chocolaterie">Chocolaterie</a></li> <li><a href="/wiki/Chocolatier" title="Chocolatier">Chocolatier</a></li> <li><a href="/wiki/C%C3%B4te_d%27Ivoire%E2%80%93Ghana_Cocoa_Initiative" title="Côte d'Ivoire–Ghana Cocoa Initiative">Côte d'Ivoire–Ghana Cocoa Initiative</a></li> <li><i><a href="/wiki/The_Dark_Side_of_Chocolate" title="The Dark Side of Chocolate">The Dark Side of Chocolate</a></i></li> <li><a href="/wiki/Environmental_impact_of_cocoa_production" title="Environmental impact of cocoa production">Environmental impact</a></li> <li><a href="/wiki/European_Cocoa_and_Chocolate_Directive" title="European Cocoa and Chocolate Directive">European Cocoa and Chocolate Directive</a></li> <li><a href="/wiki/Fair_trade_cocoa" title="Fair trade cocoa">Fair trade cocoa</a> <ul><li><a href="/wiki/Child_labour_in_cocoa_production" title="Child labour in cocoa production">Child labour in cocoa production</a></li></ul></li> <li><a href="/wiki/Harkin%E2%80%93Engel_Protocol" title="Harkin–Engel Protocol">Harkin–Engel Protocol</a></li> <li><a href="/wiki/International_Cocoa_Organization" title="International Cocoa Organization">International Cocoa Organization</a></li> <li><a href="/wiki/International_Cocoa_Quarantine_Centre" title="International Cocoa Quarantine Centre">International Cocoa Quarantine Centre</a></li> <li><a href="/wiki/Chocolate_industry_in_the_Philippines" title="Chocolate industry in the Philippines">Philippine chocolate industry</a></li> <li><a href="/wiki/Cocoa_production_in_Ghana" title="Cocoa production in Ghana">Production in Ghana</a> <ul><li><a href="/wiki/Ghana_Cocoa_Board" title="Ghana Cocoa Board">Ghana Cocoa Board</a></li></ul></li> <li><a href="/wiki/Cocoa_production_in_Ivory_Coast" title="Cocoa production in Ivory Coast">Production in Ivory Coast</a></li> <li><a href="/wiki/Cocoa_production_in_Nigeria" title="Cocoa production in Nigeria">Production in Nigeria</a></li> <li><a href="/wiki/Cocoa_production_in_S%C3%A3o_Tom%C3%A9_and_Pr%C3%ADncipe" title="Cocoa production in São Tomé and Príncipe">Production in São Tomé and Príncipe</a></li> <li><a href="/wiki/World_Cocoa_Foundation" title="World Cocoa Foundation">World Cocoa Foundation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">By country</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Belgian_chocolate" title="Belgian chocolate">Belgium</a></li> <li><a href="/wiki/French_chocolate" title="French chocolate">France</a></li> <li><a href="/wiki/Swiss_chocolate" title="Swiss chocolate">Switzerland</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Other topics</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chocolate_addiction" title="Chocolate addiction">Chocolate addiction</a></li> <li><a href="/wiki/Chocolate_bloom" title="Chocolate bloom">Chocolate bloom</a></li> <li><a href="/wiki/Chocolate_fountain" title="Chocolate fountain">Chocolate fountain</a></li> <li><a href="/wiki/List_of_chocolate_museums" title="List of chocolate museums">Chocolate museums</a></li> <li><a href="/wiki/List_of_chocolatiers" title="List of chocolatiers">Chocolatiers</a></li> <li><a href="/wiki/Cocoa_smuggling" title="Cocoa smuggling">Cocoa smuggling</a></li> <li><a href="/wiki/History_of_chocolate" title="History of chocolate">History</a></li> <li><a href="/wiki/Chocolate_in_savory_cooking" title="Chocolate in savory cooking">In savory cooking</a></li> <li>Military chocolate <ul><li><a href="/wiki/Military_chocolate_(Switzerland)" title="Military chocolate (Switzerland)">Switzerland</a></li> <li><a href="/wiki/Military_chocolate_(United_States)" title="Military chocolate (United States)">United States</a></li></ul></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: #7B3F00; color: white;"><div><div class="plainlist"> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Chocolate" title="Category:Chocolate"><span style="color:white">Category</span></a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Outline"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/10px-Global_thinking.svg.png" decoding="async" width="10" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/15px-Global_thinking.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/21px-Global_thinking.svg.png 2x" data-file-width="130" data-file-height="200" /></span></span> <b><a href="/wiki/Outline_of_chocolate" title="Outline of chocolate"><span style="color:white">Outline</span></a></b></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="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 class="mw-selflink selflink">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 href="/wiki/Phenolphthalein" title="Phenolphthalein">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 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="Phosphodiesterase_inhibitors" 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:Phosphodiesterase_inhibitors" title="Template:Phosphodiesterase inhibitors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phosphodiesterase_inhibitors" title="Template talk:Phosphodiesterase inhibitors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phosphodiesterase_inhibitors" title="Special:EditPage/Template:Phosphodiesterase inhibitors"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Phosphodiesterase_inhibitors" style="font-size:114%;margin:0 4em"><a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">Phosphodiesterase inhibitors</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE1" title="PDE1">PDE1</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/8-Methoxymethyl-3-isobutyl-1-methylxanthine" title="8-Methoxymethyl-3-isobutyl-1-methylxanthine">MMPX</a></li> <li><a href="/wiki/SCH-51866" title="SCH-51866">SCH-51866</a></li> <li><a href="/wiki/Vinpocetine" title="Vinpocetine">Vinpocetine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE2" class="mw-redirect" title="PDE2">PDE2</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/BAY_60-7550" title="BAY 60-7550">BAY 60-7550</a></li> <li><a href="/w/index.php?title=Carbazeran&action=edit&redlink=1" class="new" title="Carbazeran (page does not exist)">Carbazeran</a></li> <li><a href="/wiki/EHNA" title="EHNA">EHNA</a></li> <li><a href="/wiki/Oxindole" title="Oxindole">Oxindole</a></li> <li><a href="/w/index.php?title=9-(6-Phenyl-2-oxohex-3-yl)-2-(3,4-dimethoxybenzyl)-purin-6-one&action=edit&redlink=1" class="new" title="9-(6-Phenyl-2-oxohex-3-yl)-2-(3,4-dimethoxybenzyl)-purin-6-one (page does not exist)">PDP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE3_inhibitor" title="PDE3 inhibitor">PDE3</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adibendan" title="Adibendan">Adibendan</a></li> <li><a href="/wiki/Amrinone" title="Amrinone">Amrinone (inamrinone)</a></li> <li><a href="/wiki/Anagrelide" title="Anagrelide">Anagrelide</a></li> <li><a href="/w/index.php?title=Benafentrine&action=edit&redlink=1" class="new" title="Benafentrine (page does not exist)">Benafentrine</a></li> <li><a href="/wiki/Bucladesine" title="Bucladesine">Bucladesine</a></li> <li><a href="/w/index.php?title=Carbazeran&action=edit&redlink=1" class="new" title="Carbazeran (page does not exist)">Carbazeran</a></li> <li><a href="/wiki/Cilostamide" title="Cilostamide">Cilostamide</a></li> <li><a href="/wiki/Cilostazol" title="Cilostazol">Cilostazol</a></li> <li><a href="/wiki/Enoximone" title="Enoximone">Enoximone</a></li> <li><a href="/wiki/Ensifentrine" title="Ensifentrine">Ensifentrine</a></li> <li><a href="/w/index.php?title=Imazodan&action=edit&redlink=1" class="new" title="Imazodan (page does not exist)">Imazodan</a></li> <li><a href="/wiki/KMUP-1" title="KMUP-1">KMUP-1</a></li> <li><a href="/w/index.php?title=Meribendan&action=edit&redlink=1" class="new" title="Meribendan (page does not exist)">Meribendan</a></li> <li><a href="/wiki/Milrinone" title="Milrinone">Milrinone</a></li> <li><a href="/wiki/Olprinone" title="Olprinone">Olprinone</a></li> <li><a href="/w/index.php?title=Parogrelil&action=edit&redlink=1" class="new" title="Parogrelil (page does not exist)">Parogrelil</a></li> <li><a href="/wiki/Pimobendan" title="Pimobendan">Pimobendan</a></li> <li><a href="/w/index.php?title=Pumafentrine&action=edit&redlink=1" class="new" title="Pumafentrine (page does not exist)">Pumafentrine</a></li> <li><a href="/wiki/Quazinone" title="Quazinone">Quazinone</a></li> <li><a href="/wiki/RPL-554" class="mw-redirect" title="RPL-554">RPL-554</a></li> <li><a href="/wiki/Siguazodan" title="Siguazodan">Siguazodan</a></li> <li><a href="/wiki/Trequinsin" title="Trequinsin">Trequinsin</a></li> <li><a href="/wiki/Vesnarinone" title="Vesnarinone">Vesnarinone</a></li> <li><a href="/wiki/Zardaverine" title="Zardaverine">Zardaverine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE4_inhibitor" title="PDE4 inhibitor">PDE4</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apremilast" title="Apremilast">Apremilast</a></li> <li><a href="/wiki/Arofylline" title="Arofylline">Arofylline</a></li> <li><a href="/wiki/Atizoram" title="Atizoram">Atizoram</a></li> <li><a href="/w/index.php?title=Benafentrine&action=edit&redlink=1" class="new" title="Benafentrine (page does not exist)">Benafentrine</a></li> <li><a href="/w/index.php?title=Catramilast&action=edit&redlink=1" class="new" title="Catramilast (page does not exist)">Catramilast</a></li> <li><a href="/wiki/CC-1088" title="CC-1088">CC-1088</a></li> <li><a href="/w/index.php?title=CDP-840&action=edit&redlink=1" class="new" title="CDP-840 (page does not exist)">CDP-840</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/Cilomilast" title="Cilomilast">Cilomilast</a></li> <li><a href="/w/index.php?title=Cipamfylline&action=edit&redlink=1" class="new" title="Cipamfylline (page does not exist)">Cipamfylline</a></li> <li><a href="/wiki/Crisaborole" title="Crisaborole">Crisaborole</a></li> <li><a href="/w/index.php?title=Denbutylline&action=edit&redlink=1" class="new" title="Denbutylline (page does not exist)">Denbutylline</a></li> <li><a href="/w/index.php?title=Difamilast&action=edit&redlink=1" class="new" title="Difamilast (page does not exist)">Difamilast</a></li> <li><a href="/wiki/Drotaverine" title="Drotaverine">Drotaverine</a></li> <li><a href="/wiki/Ensifentrine" title="Ensifentrine">Ensifentrine</a></li> <li><a href="/wiki/Etazolate" title="Etazolate">Etazolate</a></li> <li><a href="/wiki/Filaminast" title="Filaminast">Filaminast</a></li> <li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/wiki/HT-0712" title="HT-0712">HT-0712</a></li> <li><a href="/wiki/ICI-63197" title="ICI-63197">ICI-63197</a></li> <li><a href="/w/index.php?title=Indimilast&action=edit&redlink=1" class="new" title="Indimilast (page does not exist)">Indimilast</a></li> <li><a href="/wiki/Irsogladine" title="Irsogladine">Irsogladine</a></li> <li><a href="/w/index.php?title=Lavamilast&action=edit&redlink=1" class="new" title="Lavamilast (page does not exist)">Lavamilast</a></li> <li><a href="/w/index.php?title=Lirimilast&action=edit&redlink=1" class="new" title="Lirimilast (page does not exist)">Lirimilast</a></li> <li><a href="/w/index.php?title=Lotamilast&action=edit&redlink=1" class="new" title="Lotamilast (page does not exist)">Lotamilast</a></li> <li><a href="/wiki/Luteolin" title="Luteolin">Luteolin</a></li> <li><a href="/wiki/Mesembrenone" title="Mesembrenone">Mesembrenone</a></li> <li><a href="/wiki/Mesembrine" title="Mesembrine">Mesembrine</a></li> <li><a href="/w/index.php?title=Mesopram&action=edit&redlink=1" class="new" title="Mesopram (page does not exist)">Mesopram</a></li> <li><a href="/w/index.php?title=Oglemilast&action=edit&redlink=1" class="new" title="Oglemilast (page does not exist)">Oglemilast</a></li> <li><a href="/wiki/Piclamilast" title="Piclamilast">Piclamilast</a></li> <li><a href="/w/index.php?title=Pumafentrine&action=edit&redlink=1" class="new" title="Pumafentrine (page does not exist)">Pumafentrine</a></li> <li><a href="/w/index.php?title=Revamilast&action=edit&redlink=1" class="new" title="Revamilast (page does not exist)">Revamilast</a></li> <li><a href="/w/index.php?title=Ro_20-1724&action=edit&redlink=1" class="new" title="Ro 20-1724 (page does not exist)">Ro 20-1724</a></li> <li><a href="/wiki/Roflumilast" title="Roflumilast">Roflumilast</a></li> <li><a href="/wiki/Rolipram" title="Rolipram">Rolipram</a></li> <li><a href="/w/index.php?title=Ronomilast&action=edit&redlink=1" class="new" title="Ronomilast (page does not exist)">Ronomilast</a></li> <li><a href="/wiki/RPL-554" class="mw-redirect" title="RPL-554">RPL-554</a></li> <li><a href="/w/index.php?title=RS-25344&action=edit&redlink=1" class="new" title="RS-25344 (page does not exist)">RS-25344</a></li> <li><a href="/w/index.php?title=Tetomilast&action=edit&redlink=1" class="new" title="Tetomilast (page does not exist)">Tetomilast</a></li> <li><a href="/w/index.php?title=Tofimilast&action=edit&redlink=1" class="new" title="Tofimilast (page does not exist)">Tofimilast</a></li> <li><a href="/wiki/YM-976" title="YM-976">YM-976</a></li> <li><a href="/wiki/Zardaverine" title="Zardaverine">Zardaverine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE5_inhibitor" title="PDE5 inhibitor">PDE5</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetildenafil" title="Acetildenafil">Acetildenafil</a></li> <li><a href="/wiki/Aildenafil" title="Aildenafil">Aildenafil</a></li> <li><a href="/wiki/Avanafil" title="Avanafil">Avanafil</a></li> <li><a href="/w/index.php?title=Beminafil&action=edit&redlink=1" class="new" title="Beminafil (page does not exist)">Beminafil</a></li> <li><a href="/wiki/Benzamidenafil" title="Benzamidenafil">Benzamidenafil</a></li> <li><a href="/w/index.php?title=Dasantafil&action=edit&redlink=1" class="new" title="Dasantafil (page does not exist)">Dasantafil</a></li> <li><a href="/wiki/Icariin" title="Icariin">Icariin</a></li> <li><a href="/w/index.php?title=Gisadenafil&action=edit&redlink=1" class="new" title="Gisadenafil (page does not exist)">Gisadenafil</a></li> <li><a href="/wiki/Homosildenafil" title="Homosildenafil">Homosildenafil</a></li> <li><a href="/wiki/Lodenafil" title="Lodenafil">Lodenafil</a></li> <li><a href="/wiki/Mirodenafil" title="Mirodenafil">Mirodenafil</a></li> <li><a href="/wiki/MY-5445" title="MY-5445">MY-5445</a></li> <li><a href="/wiki/Nitrosoprodenafil" title="Nitrosoprodenafil">Nitrosoprodenafil</a></li> <li><a href="/w/index.php?title=Norcarbodenafil&action=edit&redlink=1" class="new" title="Norcarbodenafil (page does not exist)">Norcarbodenafil</a></li> <li><a href="/wiki/SCH-51866" title="SCH-51866">SCH-51866</a></li> <li><a href="/wiki/Sildenafil" title="Sildenafil">Sildenafil</a></li> <li><a href="/wiki/Sulfoaildenafil" title="Sulfoaildenafil">Sulfoaildenafil</a></li> <li><a href="/wiki/T-0156" title="T-0156">T-0156</a></li> <li><a href="/wiki/Tadalafil" title="Tadalafil">Tadalafil</a></li> <li><a href="/wiki/Udenafil" title="Udenafil">Udenafil</a></li> <li><a href="/wiki/Vardenafil" title="Vardenafil">Vardenafil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE7" class="mw-redirect" title="PDE7">PDE7</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/BRL-50481" title="BRL-50481">BRL-50481</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE9" title="PDE9">PDE9</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/BAY_73-6691" title="BAY 73-6691">BAY 73-6691</a></li> <li><a href="/w/index.php?title=PF-04447943&action=edit&redlink=1" class="new" title="PF-04447943 (page does not exist)">PF-04447943</a></li> <li><a href="/wiki/Paraxanthine" title="Paraxanthine">Paraxanthine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE10" title="PDE10">PDE10</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Balipodect" title="Balipodect">Balipodect</a></li> <li><a href="/wiki/Mardepodect" title="Mardepodect">Mardepodect</a></li> <li><a href="/wiki/MK-8189" title="MK-8189">MK-8189</a></li> <li><a href="/wiki/Papaverine" title="Papaverine">Papaverine</a></li> <li><a href="/w/index.php?title=TC-E_5005&action=edit&redlink=1" class="new" title="TC-E 5005 (page does not exist)">TC-E 5005</a></li> <li><a href="/wiki/Tofisopam" title="Tofisopam">Tofisopam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE11" title="PDE11">PDE11</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/w/index.php?title=BC11-38&action=edit&redlink=1" class="new" title="BC11-38 (page does not exist)">BC11-38</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Phosphodiesterase_inhibitor#Nonselective_phosphodiesterase_inhibitors" title="Phosphodiesterase inhibitor">Non-selective</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminophylline" title="Aminophylline">Aminophylline</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Choline_theophyllinate" title="Choline theophyllinate">Choline theophyllinate</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dimethylxanthine" title="8-Cyclopentyl-1,3-dimethylxanthine">CPX</a></li> <li><a href="/wiki/Dipyridamole" title="Dipyridamole">Dipyridamole</a></li> <li><a href="/wiki/Doxofylline" title="Doxofylline">Doxofylline</a></li> <li><a href="/wiki/Enprofylline" title="Enprofylline">Enprofylline</a></li> <li><a href="/wiki/Ibudilast" title="Ibudilast">Ibudilast</a></li> <li><a href="/wiki/IBMX" title="IBMX">IBMX</a></li> <li><a href="/wiki/Luteolin" title="Luteolin">Luteolin</a></li> <li><a href="/wiki/Pentoxifylline" title="Pentoxifylline">Pentoxifylline</a></li> <li><a href="/wiki/Propentofylline" title="Propentofylline">Propentofylline</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a class="mw-selflink selflink">Theophylline</a></li> <li><a href="/wiki/Zaprinast" title="Zaprinast">Zaprinast</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Unsorted</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a></li> <li><a href="/wiki/Diprophylline" title="Diprophylline">Diprophylline</a></li> <li><a href="/wiki/Dipropylcyclopentylxanthine" title="Dipropylcyclopentylxanthine">DPCPX</a></li> <li><a href="/wiki/Furafylline" title="Furafylline">Furafylline</a></li> <li><a href="/wiki/Lisofylline" title="Lisofylline">Lisofylline</a></li> <li><a href="/w/index.php?title=MDL-12330A&action=edit&redlink=1" class="new" title="MDL-12330A (page does not exist)">MDL-12330A</a></li> <li><a href="/wiki/Moxaverine" title="Moxaverine">Moxaverine</a></li> <li><a href="/w/index.php?title=Oxagrelate&action=edit&redlink=1" class="new" title="Oxagrelate (page does not exist)">Oxagrelate</a></li> <li><a href="/wiki/Pentifylline" title="Pentifylline">Pentifylline</a></li> <li><a href="/wiki/Proxyphylline" title="Proxyphylline">Proxyphylline</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/w/index.php?title=Satigrel&action=edit&redlink=1" class="new" title="Satigrel (page does not exist)">Satigrel</a></li> <li><a href="/w/index.php?title=Tolafentrine&action=edit&redlink=1" class="new" title="Tolafentrine (page does not exist)">Tolafentrine</a></li> <li><a href="/wiki/Trapidil" title="Trapidil">Trapidil</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 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"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" 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