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Pseudoephedrine - Wikipedia
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<li id="toc-Nasal_congestion" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nasal_congestion"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Nasal congestion</span> </div> </a> <ul id="toc-Nasal_congestion-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Other uses</span> </div> </a> <ul id="toc-Other_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Available_forms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Available_forms"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Available forms</span> </div> </a> <ul id="toc-Available_forms-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Contraindications" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Contraindications"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Contraindications</span> </div> </a> <ul id="toc-Contraindications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Side effects</span> </div> </a> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Overdose" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Overdose"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Overdose</span> </div> </a> <ul id="toc-Overdose-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Interactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Interactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Interactions</span> </div> </a> <ul id="toc-Interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1"> <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-Elimination" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Elimination"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.4</span> <span>Elimination</span> </div> </a> <ul id="toc-Elimination-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Chemistry</span> </div> </a> <button aria-controls="toc-Chemistry-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 Chemistry subsection</span> </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Nomenclatures" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nomenclatures"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Nomenclatures</span> </div> </a> <ul id="toc-Nomenclatures-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Detection_in_body_fluids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Detection_in_body_fluids"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Detection in body fluids</span> </div> </a> <ul id="toc-Detection_in_body_fluids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Manufacturing" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Manufacturing"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Manufacturing</span> </div> </a> <ul id="toc-Manufacturing-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Society and culture</span> </div> </a> <button aria-controls="toc-Society_and_culture-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 Society and culture subsection</span> </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Generic_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Generic_names"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.1</span> <span>Generic names</span> </div> </a> <ul id="toc-Generic_names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Brand_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Brand_names"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.2</span> <span>Brand names</span> </div> </a> <ul id="toc-Brand_names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Recreational_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Recreational_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.3</span> <span>Recreational use</span> </div> </a> <ul id="toc-Recreational_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Use_in_exercise_and_sports" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Use_in_exercise_and_sports"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.4</span> <span>Use in exercise and sports</span> </div> </a> <ul id="toc-Use_in_exercise_and_sports-sublist" class="vector-toc-list"> <li id="toc-List_of_doping_cases" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#List_of_doping_cases"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.4.1</span> <span>List of doping cases</span> </div> </a> <ul id="toc-List_of_doping_cases-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Manufacture_of_amphetamines" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Manufacture_of_amphetamines"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.5</span> <span>Manufacture of amphetamines</span> </div> </a> <ul id="toc-Manufacture_of_amphetamines-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Legal_status" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Legal_status"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6</span> <span>Legal status</span> </div> </a> <ul id="toc-Legal_status-sublist" class="vector-toc-list"> <li id="toc-Australia" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Australia"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.1</span> <span>Australia</span> </div> </a> <ul id="toc-Australia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Belgium" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Belgium"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.2</span> <span>Belgium</span> </div> </a> <ul id="toc-Belgium-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Canada" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Canada"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.3</span> <span>Canada</span> </div> </a> <ul id="toc-Canada-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Colombia" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Colombia"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.4</span> <span>Colombia</span> </div> </a> <ul id="toc-Colombia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Estonia" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Estonia"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.5</span> <span>Estonia</span> </div> </a> <ul id="toc-Estonia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Finland" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Finland"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.6</span> <span>Finland</span> </div> </a> <ul id="toc-Finland-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-France" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#France"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.7</span> <span>France</span> </div> </a> <ul id="toc-France-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Germany" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Germany"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.8</span> <span>Germany</span> </div> </a> <ul id="toc-Germany-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Japan" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Japan"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.9</span> <span>Japan</span> </div> </a> <ul id="toc-Japan-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mexico" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Mexico"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.10</span> <span>Mexico</span> </div> </a> <ul id="toc-Mexico-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Netherlands" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Netherlands"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.11</span> <span>Netherlands</span> </div> </a> <ul id="toc-Netherlands-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-New_Zealand" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#New_Zealand"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.12</span> <span>New Zealand</span> </div> </a> <ul id="toc-New_Zealand-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Switzerland" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Switzerland"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.13</span> <span>Switzerland</span> </div> </a> <ul id="toc-Switzerland-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Turkey" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Turkey"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.14</span> <span>Turkey</span> </div> </a> <ul id="toc-Turkey-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-United_Kingdom" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#United_Kingdom"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.15</span> <span>United Kingdom</span> </div> </a> <ul id="toc-United_Kingdom-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-United_States" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#United_States"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.16</span> <span>United States</span> </div> </a> <ul id="toc-United_States-sublist" class="vector-toc-list"> <li id="toc-Federal" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Federal"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.16.1</span> <span>Federal</span> </div> </a> <ul id="toc-Federal-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-State" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#State"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6.16.2</span> <span>State</span> </div> </a> <ul id="toc-State-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Research</span> </div> </a> <ul id="toc-Research-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>References</span> </div> </a> <ul id="toc-References-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" title="Table of Contents" > <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">Pseudoephedrine</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 36 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-36" 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">36 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%B3%D9%88%D8%AF%D9%88%D8%A5%D9%81%D9%8A%D8%AF%D8%B1%D9%8A%D9%86" title="سودوإفيدرين – Arabic" lang="ar" hreflang="ar" data-title="سودوإفيدرين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Psevdoefedrin" title="Psevdoefedrin – Azerbaijani" lang="az" hreflang="az" data-title="Psevdoefedrin" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%D9%88%D8%AF%D9%88%D8%A7%D9%81%D8%AF%D8%B1%DB%8C%D9%86" title="سودوافدرین – South Azerbaijani" lang="azb" hreflang="azb" data-title="سودوافدرین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B8%E0%A6%BF%E0%A6%89%E0%A6%A1%E0%A7%8B%E0%A6%AB%E0%A7%87%E0%A6%A1%E0%A7%8D%E0%A6%B0%E0%A6%BF%E0%A6%A8" title="সিউডোফেড্রিন – Bangla" lang="bn" hreflang="bn" data-title="সিউডোফেড্রিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Pseudoefedrina" title="Pseudoefedrina – Catalan" lang="ca" hreflang="ca" data-title="Pseudoefedrina" 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/Pseudoefedrin" title="Pseudoefedrin – Czech" lang="cs" hreflang="cs" data-title="Pseudoefedrin" 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/Ffugeffedrin" title="Ffugeffedrin – Welsh" lang="cy" hreflang="cy" data-title="Ffugeffedrin" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Pseudoephedrin" title="Pseudoephedrin – German" lang="de" hreflang="de" data-title="Pseudoephedrin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Pseudoefedrina" title="Pseudoefedrina – Spanish" lang="es" hreflang="es" data-title="Pseudoefedrina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%D9%88%D8%AF%D9%88%D8%A7%D9%81%D8%AF%D8%B1%DB%8C%D9%86" title="سودوافدرین – Persian" lang="fa" hreflang="fa" data-title="سودوافدرین" 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/Pseudo%C3%A9ph%C3%A9drine" title="Pseudoéphédrine – French" lang="fr" hreflang="fr" data-title="Pseudoéphédrine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%8A%88%EB%8F%84%EC%97%90%ED%8E%98%EB%93%9C%EB%A6%B0" title="슈도에페드린 – Korean" lang="ko" hreflang="ko" data-title="슈도에페드린" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Pseudoefedrin" title="Pseudoefedrin – Croatian" lang="hr" hreflang="hr" data-title="Pseudoefedrin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Pseudoefedrin" title="Pseudoefedrin – Indonesian" lang="id" hreflang="id" data-title="Pseudoefedrin" 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/Pseudoefedrina" title="Pseudoefedrina – Italian" lang="it" hreflang="it" data-title="Pseudoefedrina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A4%D7%A1%D7%90%D7%95%D7%93%D7%95%D7%90%D7%A4%D7%93%D7%A8%D7%99%D7%9F" title="פסאודואפדרין – Hebrew" lang="he" hreflang="he" data-title="פסאודואפדרין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Pszeudoefedrin" title="Pszeudoefedrin – Hungarian" lang="hu" hreflang="hu" data-title="Pszeudoefedrin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Pseudo-efedrine" title="Pseudo-efedrine – Dutch" lang="nl" hreflang="nl" data-title="Pseudo-efedrine" 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%97%E3%82%BD%E3%82%A4%E3%83%89%E3%82%A8%E3%83%95%E3%82%A7%E3%83%89%E3%83%AA%E3%83%B3" title="プソイドエフェドリン – Japanese" lang="ja" hreflang="ja" data-title="プソイドエフェドリン" 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/Pseudoefedrin" title="Pseudoefedrin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Pseudoefedrin" 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%B8%E0%AD%81%E0%AC%A1%E0%AD%8B%E0%AC%8F%E0%AC%AB%E0%AD%87%E0%AC%A1%E0%AD%8D%E0%AC%B0%E0%AC%BF%E0%AC%A8" title="ସୁଡୋଏଫେଡ୍ରିନ – Odia" lang="or" hreflang="or" data-title="ସୁଡୋଏଫେଡ୍ରିନ" 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/Pseudoefedryna" title="Pseudoefedryna – Polish" lang="pl" hreflang="pl" data-title="Pseudoefedryna" 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/Pseudoefedrina" title="Pseudoefedrina – Portuguese" lang="pt" hreflang="pt" data-title="Pseudoefedrina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9F%D1%81%D0%B5%D0%B2%D0%B4%D0%BE%D1%8D%D1%84%D0%B5%D0%B4%D1%80%D0%B8%D0%BD" title="Псевдоэфедрин – Russian" lang="ru" hreflang="ru" data-title="Псевдоэфедрин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Pseudoephedrine" title="Pseudoephedrine – Simple English" lang="en-simple" hreflang="en-simple" data-title="Pseudoephedrine" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Psevdoefedrin" title="Psevdoefedrin – Slovenian" lang="sl" hreflang="sl" data-title="Psevdoefedrin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Pseudoefedrin" title="Pseudoefedrin – Serbian" lang="sr" hreflang="sr" data-title="Pseudoefedrin" 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/Pseudoefedrin" title="Pseudoefedrin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Pseudoefedrin" 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/Pseudoefedriini" title="Pseudoefedriini – Finnish" lang="fi" hreflang="fi" data-title="Pseudoefedriini" 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/Pseudoefedrin" title="Pseudoefedrin – Swedish" lang="sv" hreflang="sv" data-title="Pseudoefedrin" 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%B8%E0%B1%82%E0%B0%A1%E0%B1%8B%E0%B0%8E%E0%B0%AB%E0%B0%BF%E0%B0%A1%E0%B1%8D%E0%B0%B0%E0%B0%BF%E0%B0%A8%E0%B1%8D" title="సూడోఎఫిడ్రిన్ – Telugu" lang="te" hreflang="te" data-title="సూడోఎఫిడ్రిన్" 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%8B%E0%B8%B9%E0%B9%82%E0%B8%94%E0%B8%AD%E0%B8%B5%E0%B9%80%E0%B8%9F%E0%B8%94%E0%B8%A3%E0%B8%B5%E0%B8%99" title="ซูโดอีเฟดรีน – Thai" lang="th" hreflang="th" data-title="ซูโดอีเฟดรีน" 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/Ps%C3%B6doefedrin" title="Psödoefedrin – Turkish" lang="tr" hreflang="tr" data-title="Psödoefedrin" 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%9F%D1%81%D0%B5%D0%B2%D0%B4%D0%BE%D0%B5%D1%84%D0%B5%D0%B4%D1%80%D0%B8%D0%BD" title="Псевдоефедрин – Ukrainian" lang="uk" hreflang="uk" data-title="Псевдоефедрин" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Pseudoephedrine" title="Pseudoephedrine – Vietnamese" lang="vi" hreflang="vi" data-title="Pseudoephedrine" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%BC%AA%E9%BA%BB%E9%BB%84%E7%A2%B1" title="伪麻黄碱 – Chinese" lang="zh" hreflang="zh" data-title="伪麻黄碱" 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 wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q263958#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div 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.hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"Sudafed" redirects here. For Sudafed PE, see <a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a>.</div> <p class="mw-empty-elt"> </p> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <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): Pseudoephedrine">Pseudoephedrine</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Pseudoephedrine_S,S_ephedrine_comparison.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Pseudoephedrine_S%2CS_ephedrine_comparison.png/200px-Pseudoephedrine_S%2CS_ephedrine_comparison.png" decoding="async" width="200" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Pseudoephedrine_S%2CS_ephedrine_comparison.png/300px-Pseudoephedrine_S%2CS_ephedrine_comparison.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Pseudoephedrine_S%2CS_ephedrine_comparison.png/400px-Pseudoephedrine_S%2CS_ephedrine_comparison.png 2x" data-file-width="884" data-file-height="578" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:(1S,2S)-Pseudoephedrine_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/%281S%2C2S%29-Pseudoephedrine_molecule_ball.png/200px-%281S%2C2S%29-Pseudoephedrine_molecule_ball.png" decoding="async" width="200" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/%281S%2C2S%29-Pseudoephedrine_molecule_ball.png/300px-%281S%2C2S%29-Pseudoephedrine_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/84/%281S%2C2S%29-Pseudoephedrine_molecule_ball.png/400px-%281S%2C2S%29-Pseudoephedrine_molecule_ball.png 2x" data-file-width="2000" data-file-height="1301" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data"><span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˌ/: secondary stress follows">ˌ</span><span title="'s' in 'sigh'">s</span><span title="/uː/: 'oo' in 'goose'">uː</span><span title="'d' in 'dye'">d</span><span title="/oʊ/: 'o' in 'code'">oʊ</span><span title="/./: syllable break">.</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'f' in 'find'">f</span><span title="/ɛ/: 'e' in 'dress'">ɛ</span><span title="'d' in 'dye'">d</span><span title="'r' in 'rye'">r</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'n' in 'nigh'">n</span></span>,<span class="wrap"> </span>-<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="/ɛ/: 'e' in 'dress'">ɛ</span><span title="'f' in 'find'">f</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'d' in 'dye'">d</span><span title="'r' in 'rye'">r</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span> </td></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">Afrinol, Sudafed, Sinutab, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">PSE; PDE; (+)-ψ-Ephedrine; ψ-Ephedrine; d-Isoephedrine; (1<i>S</i>,2<i>S</i>)-Pseudoephedrine; d-Pseudoephedrine; (+)-Pseudoephedrine; <small>L</small>(+)-Pseudoephedrine; Isoephedrine; (1<i>S</i>,2<i>S</i>)-α,<i>N</i>-Dimethyl-β-hydroxyphenethylamine; (1<i>S</i>,2<i>S</i>)-<i>N</i>-Methyl-β-hydroxyamphetamine</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/pseudoephedrine.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/a682619.html">a682619</a></span></td></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">License data</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="European Union">EU</abbr></small> <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">EMA</a>: <span title="www.ema.europa.eu: 'pseudoephedrine sulfate'"><a rel="nofollow" class="external text" href="https://www.ema.europa.eu/en/medicines/search_api_aggregation_ema_active_substance_and_inn_common_name/pseudoephedrine+sulfate">by pseudoephedrine sulfate</a></span></li> <li><small><abbr class="country-name" title="United States">US</abbr></small> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Pseudoephedrine">Pseudoephedrine</a></span></li></ul></div> </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"><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> B2</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/By_mouth" class="mw-redirect" title="By mouth">By mouth</a><sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-0" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-0" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Norepinephrine_releasing_agent" title="Norepinephrine releasing agent">Norepinephrine releasing agent</a>; <a href="/wiki/Nasal_decongestant" class="mw-redirect" title="Nasal decongestant">Nasal decongestant</a>; <a href="/wiki/Stimulant" title="Stimulant">Stimulant</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_R01" title="ATC code R01">R01BA02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=R01BA02">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">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_3" title="Standard for the Uniform Scheduling of Medicines and Poisons">S3</a> (Pharmacist only) Largely tracked nationwide via “Project STOP” to avoid purchases in large quantities.<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> Use of Project STOP is mandatory in all states and territories except Victoria and Tasmania<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> <li><small><abbr class="country-name" title="Brazil">BR</abbr>:</small> <a href="/wiki/Brazilian_Controlled_Drugs_and_Substances_Act#Class_D1" title="Brazilian Controlled Drugs and Substances Act">Class D1</a> (Drug precursors)<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><small><abbr class="country-name" title="Canada">CA</abbr></small>: <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">OTC</a> Removed from the <abbr title="National Drug Schedule">NDS</abbr> in 2024, for both combination and single ingredient preparations, on 1 Mar & 10 Jun 2024, respectively.<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><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/Over-the-counter_drug" title="Over-the-counter drug">OTC</a></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><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%<sup id="cite_ref-BruntonLazoParker2006_8-0" class="reference"><a href="#cite_note-BruntonLazoParker2006-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></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">21–29% (<a href="/wiki/Alpha-1-acid_glycoprotein" class="mw-redirect" title="Alpha-1-acid glycoprotein"><abbr title="alpha-1-acid glycoprotein">AGP</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 alpha-1-acid glycoprotein</span>, <a href="/wiki/Human_serum_albumin" title="Human serum albumin"><abbr title="Human serum albumin">HSA</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 Human serum albumin</span>)<sup id="cite_ref-VolppHolzgrabe2019_9-0" class="reference"><a href="#cite_note-VolppHolzgrabe2019-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Schmidt2023_10-0" class="reference"><a href="#cite_note-Schmidt2023-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></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">Not extensively <a href="/wiki/Metabolism" title="Metabolism">metabolized</a><sup id="cite_ref-ChuaBenrimojTriggs1989_11-2" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-6" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-3" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></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">• <a href="/wiki/Cathine" title="Cathine">Norpseudoephedrine</a><sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-1" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Onset_of_action" title="Onset of action">Onset of action</a></th><td class="infobox-data">30<span class="nowrap"> </span>minutes<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-2" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></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">5.4<span class="nowrap"> </span>hours (range 3–16<span class="nowrap"> </span>hours dependent on <a href="/wiki/Urine" title="Urine">urine</a> <a href="/wiki/PH" title="PH">pH</a>)<sup id="cite_ref-Eccles2007_2-1" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-3" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ChuaBenrimojTriggs1989_11-0" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pharmacodynamics#Duration_of_action" title="Pharmacodynamics">Duration of action</a></th><td class="infobox-data">4–12<span class="nowrap"> </span>hours<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-4" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Aaron1990_12-0" class="reference"><a href="#cite_note-Aaron1990-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Urine" title="Urine">Urine</a>: 43–96% (unchanged)<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-5" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ChuaBenrimojTriggs1989_11-1" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-2" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BruntonLazoParker2006_8-1" class="reference"><a href="#cite_note-BruntonLazoParker2006-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">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<i>S</i>,2<i>S</i>)-2-(methylamino)-1-phenylpropan-1-ol</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=90-82-4">90-82-4</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><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/7028">7028</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/DB00852">DB00852</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.6761.html">6761</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/7CUC9DDI9F">7CUC9DDI9F</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/D08449">D08449</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:51209">CHEBI:51209</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/chembl/explore/compound/ChEMBL1590">ChEMBL1590</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/DTXSID0023537">DTXSID0023537</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q263958#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/100.001.835">100.001.835</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q263958#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;color:inherit;">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>10</sub><span title="Hydrogen">H</span><sub>15</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span></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="7002165236000000000♠"></span>165.236</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=O%5BC%40%40H%5D%28c1ccccc1%29%5BC%40%40H%5D%28NC%29C">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%;">O[C@@H](c1ccccc1)[C@@H](NC)C</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/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1<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:KWGRBVOPPLSCSI-WCBMZHEXSA-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=464375838&page2=Pseudoephedrine">(verify)</a></span></span></td></tr></tbody></table> <p><b>Pseudoephedrine</b>, sold under the brand name <b>Sudafed</b> among others, is a <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic</a> medication which is used as a <a href="/wiki/Nasal_decongestant" class="mw-redirect" title="Nasal decongestant">decongestant</a> to treat <a href="/wiki/Nasal_congestion" title="Nasal congestion">nasal congestion</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-7" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LaccourreyeWernerGiroud2015_13-0" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-4" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It has also been used <a href="/wiki/Off-label_use" title="Off-label use">off-label</a> for certain other indications, like treatment of <a href="/wiki/Hypotension" title="Hypotension">low blood pressure</a>.<sup id="cite_ref-FreemanKaufmann2007_14-0" class="reference"><a href="#cite_note-FreemanKaufmann2007-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-VanBerkelFuller2015_15-0" class="reference"><a href="#cite_note-VanBerkelFuller2015-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fedorowski2019_16-0" class="reference"><a href="#cite_note-Fedorowski2019-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> At higher doses, it may produce various additional effects including <a href="/wiki/Psychostimulant" class="mw-redirect" title="Psychostimulant">stimulant</a>,<sup id="cite_ref-SchifanoChiappiniMiuli2021_17-0" class="reference"><a href="#cite_note-SchifanoChiappiniMiuli2021-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-8" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Appetite_suppressant" class="mw-redirect" title="Appetite suppressant">appetite suppressant</a>,<sup id="cite_ref-MunafòFraraPerico2021_18-0" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Performance-enhancing_drug" class="mw-redirect" title="Performance-enhancing drug">performance-enhancing</a> effects.<sup id="cite_ref-TrinhKimRitsma2015_19-0" class="reference"><a href="#cite_note-TrinhKimRitsma2015-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GheorghievHosseiniMoran2018_20-0" class="reference"><a href="#cite_note-GheorghievHosseiniMoran2018-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> In relation to this, non-medical use of pseudoephedrine has been encountered.<sup id="cite_ref-SchifanoChiappiniMiuli2021_17-1" class="reference"><a href="#cite_note-SchifanoChiappiniMiuli2021-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-9" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MunafòFraraPerico2021_18-1" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TrinhKimRitsma2015_19-1" class="reference"><a href="#cite_note-TrinhKimRitsma2015-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GheorghievHosseiniMoran2018_20-1" class="reference"><a href="#cite_note-GheorghievHosseiniMoran2018-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The medication is taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-10" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-5" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Side effects of pseudoephedrine include <a href="/wiki/Insomnia" title="Insomnia">insomnia</a>, elevated <a href="/wiki/Heart_rate" title="Heart rate">heart rate</a>, increased <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>, <a href="/wiki/Psychomotor_agitation" title="Psychomotor agitation">restlessness</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, <a href="/wiki/Anxiety" title="Anxiety">anxiety</a>, and <a href="/wiki/Dry_mouth" class="mw-redirect" title="Dry mouth">dry mouth</a>, among others.<sup id="cite_ref-TavernerLatte2007_21-0" class="reference"><a href="#cite_note-TavernerLatte2007-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-6" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-11" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SalernoJackson2005_22-0" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Rarely, pseudoephedrine has been associated with serious <a href="/wiki/Cardiovascular_complication" class="mw-redirect" title="Cardiovascular complication">cardiovascular complications</a> like <a href="/wiki/Heart_attack" class="mw-redirect" title="Heart attack">heart attack</a> and <a href="/wiki/Hemorrhagic_stroke" class="mw-redirect" title="Hemorrhagic stroke">hemorrhagic stroke</a>.<sup id="cite_ref-MunafòFraraPerico2021_18-2" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CantuArauzMurillo-Bonilla2003_23-0" class="reference"><a href="#cite_note-CantuArauzMurillo-Bonilla2003-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-VanBerkelFuller2015_15-1" class="reference"><a href="#cite_note-VanBerkelFuller2015-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Some people may be more sensitive to its <a href="/wiki/Cardiovascular" class="mw-redirect" title="Cardiovascular">cardiovascular</a> effects.<sup id="cite_ref-SalernoJackson2005_22-1" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-12" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Pseudoephedrine acts as a <a href="/wiki/Norepinephrine_releasing_agent" title="Norepinephrine releasing agent">norepinephrine releasing agent</a>, thereby indirectly activating <a href="/wiki/Adrenergic_receptor" title="Adrenergic receptor">adrenergic receptors</a>.<sup id="cite_ref-RothmanVuPartilla2003_24-0" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-7" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ODonnell1995_25-0" class="reference"><a href="#cite_note-ODonnell1995-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-13" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> As such, it is an indirectly acting <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic</a>.<sup id="cite_ref-RothmanVuPartilla2003_24-1" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-8" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ODonnell1995_25-1" class="reference"><a href="#cite_note-ODonnell1995-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-14" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Pseudoephedrine significantly crosses into the <a href="/wiki/Brain" title="Brain">brain</a>, but has some <a href="/wiki/Peripherally_selective_drug" title="Peripherally selective drug">peripheral selectivity</a> due to its <a href="/wiki/Hydrophilicity" class="mw-redirect" title="Hydrophilicity">hydrophilicity</a>.<sup id="cite_ref-ODonnell1995_25-2" class="reference"><a href="#cite_note-ODonnell1995-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BouchardWeberGeiger2002_26-0" class="reference"><a href="#cite_note-BouchardWeberGeiger2002-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Chemically, pseudoephedrine is a <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">substituted amphetamine</a> and is closely related to <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>, <a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">phenylpropanolamine</a>, and <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-15" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LaccourreyeWernerGiroud2015_13-1" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-9" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It is the (1<i>S</i>,2<i>S</i>)-<a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a> of <a href="/wiki/Hydroxymethylamphetamine" title="Hydroxymethylamphetamine">β-hydroxy-<i>N</i>-methylamphetamine</a>.<sup id="cite_ref-PubChem_27-0" class="reference"><a href="#cite_note-PubChem-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>Along with ephedrine, pseudoephedrine occurs <a href="/wiki/Natural_product" title="Natural product">naturally</a> in <a href="/wiki/Ephedra_(plant)" title="Ephedra (plant)">ephedra</a>, which has been used for thousands of years in <a href="/wiki/Traditional_Chinese_medicine" title="Traditional Chinese medicine">traditional Chinese medicine</a>.<sup id="cite_ref-LaccourreyeWernerGiroud2015_13-2" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AbourashedEl-AlfyKhan2003_28-0" class="reference"><a href="#cite_note-AbourashedEl-AlfyKhan2003-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> It was first <a href="/wiki/Chemical_isolate" class="mw-redirect" title="Chemical isolate">isolated</a> from ephedra in 1889.<sup id="cite_ref-AbourashedEl-AlfyKhan2003_28-1" class="reference"><a href="#cite_note-AbourashedEl-AlfyKhan2003-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LaccourreyeWernerGiroud2015_13-3" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ChenKao1926_29-0" class="reference"><a href="#cite_note-ChenKao1926-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Subsequent to its <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesis</a> in the 1920s, pseudoephedrine was introduced for medical use as a decongestant.<sup id="cite_ref-LaccourreyeWernerGiroud2015_13-4" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Pseudoephedrine is widely available <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">over-the-counter</a> (OTC) in both single-drug and <a href="/wiki/Combination_drug" title="Combination drug">combination</a> <a href="/wiki/Dosage_form" title="Dosage form">preparations</a>.<sup id="cite_ref-Drugs@FDA_30-0" class="reference"><a href="#cite_note-Drugs@FDA-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SalernoJackson2005_22-2" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LaccourreyeWernerGiroud2015_13-5" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-10" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Availability of pseudoephedrine has been restricted starting in 2005 as it can be used to synthesize <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>.<sup id="cite_ref-LaccourreyeWernerGiroud2015_13-6" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-11" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a> has replaced pseudoephedrine in many over-the-counter <a href="/wiki/Oral_administration" title="Oral administration">oral</a> decongestant products.<sup id="cite_ref-Eccles2007_2-12" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> However, oral phenylephrine appears to be ineffective as a decongestant.<sup id="cite_ref-Hatton2022_31-0" class="reference"><a href="#cite_note-Hatton2022-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HendelesHatton2006_32-0" class="reference"><a href="#cite_note-HendelesHatton2006-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> In 2022, the combination with <a href="/wiki/Brompheniramine" title="Brompheniramine">brompheniramine</a> and <a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a> was the 265th most commonly prescribed medication in the United States, with more than 1<span class="nowrap"> </span>million prescriptions.<sup id="cite_ref-Top_300_of_2022_33-0" class="reference"><a href="#cite_note-Top_300_of_2022-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Top_300_of_2022_33-1" class="reference"><a href="#cite_note-Top_300_of_2022-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> In 2022, the combination with <a href="/wiki/Loratadine" title="Loratadine">loratadine</a> was the 289th most commonly prescribed medication in the United States, with more than 500,000 prescriptions.<sup id="cite_ref-Top_300_of_2022_33-2" class="reference"><a href="#cite_note-Top_300_of_2022-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><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> </p> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <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=Pseudoephedrine&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Nasal_congestion">Nasal congestion</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=2" title="Edit section: Nasal congestion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-More_citations_needed_section plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Pseudoephedrine" title="Special:EditPage/Pseudoephedrine">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a> in this section. Unsourced material may be challenged and removed.</span> <span class="date-container"><i>(<span class="date">December 2011</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <p>Pseudoephedrine is a <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic</a> and is well-known for shrinking swollen nasal mucous membranes, so it is often used as a <a href="/wiki/Decongestant" title="Decongestant">decongestant</a>. It reduces tissue <a href="/wiki/Hyperemia" class="mw-redirect" title="Hyperemia">hyperemia</a>, <a href="/wiki/Edema" title="Edema">edema</a>, and <a href="/wiki/Nasal_congestion" title="Nasal congestion">nasal congestion</a> commonly associated with <a href="/wiki/Common_cold" title="Common cold">colds</a> or <a href="/wiki/Allergy" title="Allergy">allergies</a>. Other beneficial effects may include increasing the drainage of <a href="/wiki/Paranasal_sinus" class="mw-redirect" title="Paranasal sinus">sinus</a> secretions, and opening of obstructed <a href="/wiki/Eustachian_tube" title="Eustachian tube">Eustachian tubes</a>. The same <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstriction</a> action can also result in <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, which is a noted side effect of pseudoephedrine. </p><p>Pseudoephedrine can be used either as oral or as <a href="/wiki/Topical_decongestant" title="Topical decongestant">topical decongestant</a>. Due to its <a href="/wiki/Psychostimulant" class="mw-redirect" title="Psychostimulant">stimulating</a> qualities, however, the oral preparation is more likely to cause adverse effects, including <a href="/wiki/Urinary_retention" title="Urinary retention">urinary retention</a>.<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><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> According to one study, pseudoephedrine may show effectiveness as an <a href="/wiki/Antitussive" class="mw-redirect" title="Antitussive">antitussive</a> drug (suppression of <a href="/wiki/Cough_medicine" class="mw-redirect" title="Cough medicine">cough</a>).<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine is <a href="/wiki/Indicated" class="mw-redirect" title="Indicated">indicated</a> for the treatment of nasal congestion, sinus congestion, and Eustachian tube congestion.<sup id="cite_ref-Bicopoulos_39-0" class="reference"><a href="#cite_note-Bicopoulos-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Pseudoephedrine is also indicated for <a href="/wiki/Vasomotor_rhinitis" class="mw-redirect" title="Vasomotor rhinitis">vasomotor rhinitis</a> and as an adjunct to other agents in the optimum treatment of <a href="/wiki/Allergic_rhinitis" title="Allergic rhinitis">allergic rhinitis</a>, <a href="/wiki/Croup" title="Croup">croup</a>, <a href="/wiki/Sinusitis" title="Sinusitis">sinusitis</a>, <a href="/wiki/Otitis_media" title="Otitis media">otitis media</a>, and <a href="/wiki/Tracheobronchitis" title="Tracheobronchitis">tracheobronchitis</a>.<sup id="cite_ref-Bicopoulos_39-1" class="reference"><a href="#cite_note-Bicopoulos-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_uses">Other uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=3" title="Edit section: Other uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Amphetamine-type_stimulant" class="mw-redirect" title="Amphetamine-type stimulant">Amphetamine-type stimulants</a> and other <a href="/wiki/Catecholaminergic" title="Catecholaminergic">catecholaminergic</a> agents are known to have <a href="/wiki/Wakefulness-promoting_agent" title="Wakefulness-promoting agent">wakefulness-promoting effects</a> and are used in the treatment of <a href="/wiki/Hypersomnia" title="Hypersomnia">hypersomnia</a> and <a href="/wiki/Narcolepsy" title="Narcolepsy">narcolepsy</a>.<sup id="cite_ref-SakaiChikahisaNishino2010_40-0" class="reference"><a href="#cite_note-SakaiChikahisaNishino2010-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TakenoshitaNishino2020_41-0" class="reference"><a href="#cite_note-TakenoshitaNishino2020-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BoutrelKoob2004_42-0" class="reference"><a href="#cite_note-BoutrelKoob2004-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Pseudoephedrine at therapeutic doses does not appear to improve or worsen daytime <a href="/wiki/Sleepiness" class="mw-redirect" title="Sleepiness">sleepiness</a>, daytime <a href="/wiki/Fatigue_(medical)" class="mw-redirect" title="Fatigue (medical)">fatigue</a>, or <a href="/wiki/Sleep_quality" class="mw-redirect" title="Sleep quality">sleep quality</a> in people with <a href="/wiki/Allergic_rhinitis" title="Allergic rhinitis">allergic rhinitis</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-16" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SherkatSardanaSafaee2011_43-0" class="reference"><a href="#cite_note-SherkatSardanaSafaee2011-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Likewise, <a href="/wiki/Somnolence" title="Somnolence">somnolence</a> was not lower in children with the <a href="/wiki/Common_cold" title="Common cold">common cold</a> treated with pseudoephedrine for nasal congestion.<sup id="cite_ref-GelotteAlbrechtHynson2019_44-0" class="reference"><a href="#cite_note-GelotteAlbrechtHynson2019-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> In any case, <a href="/wiki/Insomnia" title="Insomnia">insomnia</a> is a known <a href="/wiki/Side_effect" title="Side effect">side effect</a> of pseudoephedrine, although the incidence is low.<sup id="cite_ref-TavernerLatte2007_21-1" class="reference"><a href="#cite_note-TavernerLatte2007-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> In addition, doses of pseudoephedrine above the normal therapeutic range have been reported to produce <a href="/wiki/Psychostimulant" class="mw-redirect" title="Psychostimulant">stimulant</a> effects including insomnia and fatigue resistance.<sup id="cite_ref-SchifanoChiappiniMiuli2021_17-2" class="reference"><a href="#cite_note-SchifanoChiappiniMiuli2021-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>There has been interest in pseudoephedrine as an <a href="/wiki/Appetite_suppressant" class="mw-redirect" title="Appetite suppressant">appetite suppressant</a> for the treatment of <a href="/wiki/Obesity" title="Obesity">obesity</a>.<sup id="cite_ref-MunafòFraraPerico2021_18-3" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> However, due to lack of clinical data and potential cardiovascular side effects, this use is not recommended.<sup id="cite_ref-MunafòFraraPerico2021_18-4" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Only a single <a href="/wiki/Placebo" title="Placebo">placebo</a>-<a href="/wiki/Controlled_trial" class="mw-redirect" title="Controlled trial">controlled</a> study of pseudoephedrine for <a href="/wiki/Weight_loss" title="Weight loss">weight loss</a> exists (120<span class="nowrap"> </span>mg/day <a href="/wiki/Slow-release" class="mw-redirect" title="Slow-release">slow-release</a> for 12<span class="nowrap"> </span>weeks) and found no significant difference in weight lost compared to placebo (-4.6<span class="nowrap"> </span>kg vs. -4.5<span class="nowrap"> </span>kg).<sup id="cite_ref-MunafòFraraPerico2021_18-5" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GreenwayHerberRaum1999_45-0" class="reference"><a href="#cite_note-GreenwayHerberRaum1999-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> This was in contrast to <a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">phenylpropanolamine</a>, which has been found to be more effective at promoting weight loss compared to placebo and has been more widely studied and used in the treatment of obesity.<sup id="cite_ref-CoulterRebelloGreenway2018_46-0" class="reference"><a href="#cite_note-CoulterRebelloGreenway2018-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ioannides-DemosProiettoMcNeil2005_47-0" class="reference"><a href="#cite_note-Ioannides-DemosProiettoMcNeil2005-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GreenwayHerberRaum1999_45-1" class="reference"><a href="#cite_note-GreenwayHerberRaum1999-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine has been used limitedly in the treatment of <a href="/wiki/Orthostatic_intolerance" title="Orthostatic intolerance">orthostatic intolerance</a> including <a href="/wiki/Orthostatic_hypotension" title="Orthostatic hypotension">orthostatic hypotension</a><sup id="cite_ref-FreemanKaufmann2007_14-1" class="reference"><a href="#cite_note-FreemanKaufmann2007-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Postural_orthostatic_tachycardia_syndrome" title="Postural orthostatic tachycardia syndrome">postural orthostatic tachycardia syndrome</a> (POTS).<sup id="cite_ref-Fedorowski2019_16-1" class="reference"><a href="#cite_note-Fedorowski2019-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FedorowskiMelander2013_48-0" class="reference"><a href="#cite_note-FedorowskiMelander2013-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AbedBallWang2012_49-0" class="reference"><a href="#cite_note-AbedBallWang2012-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> However, its effectiveness in the treatment of POTS is controversial.<sup id="cite_ref-Fedorowski2019_16-2" class="reference"><a href="#cite_note-Fedorowski2019-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FedorowskiMelander2013_48-1" class="reference"><a href="#cite_note-FedorowskiMelander2013-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> Pseudoephedrine has also been used limitedly in the treatment of refractory <a href="/wiki/Hypotension" title="Hypotension">hypotension</a> in <a href="/wiki/Intensive_care_unit" title="Intensive care unit">intensive care units</a>.<sup id="cite_ref-VanBerkelFuller2015_15-2" class="reference"><a href="#cite_note-VanBerkelFuller2015-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> However, data on this use are limited to <a href="/wiki/Case_report" title="Case report">case reports</a> and <a href="/wiki/Case_series" title="Case series">case series</a>.<sup id="cite_ref-VanBerkelFuller2015_15-3" class="reference"><a href="#cite_note-VanBerkelFuller2015-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine is also used as a first-line prophylactic for recurrent <a href="/wiki/Priapism" title="Priapism">priapism</a>.<sup id="cite_ref-MuneerMinhasArya2008_50-0" class="reference"><a href="#cite_note-MuneerMinhasArya2008-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Erection" title="Erection">Erection</a> is largely a <a href="/wiki/Autonomic_nervous_system" title="Autonomic nervous system">parasympathetic</a> response, so the sympathetic action of pseudoephedrine may serve to relieve this condition. Data for this use are however <a href="/wiki/Anecdotal" class="mw-redirect" title="Anecdotal">anecdotal</a> and effectiveness has been described as variable.<sup id="cite_ref-MuneerMinhasArya2008_50-1" class="reference"><a href="#cite_note-MuneerMinhasArya2008-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p><p>Treatment of <a href="/wiki/Urinary_incontinence" title="Urinary incontinence">urinary incontinence</a> is an <a href="/wiki/Off-label_use" title="Off-label use">off-label use</a> for pseudoephedrine and related medications.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=4" title="Edit section: Available forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Azatadine/pseudoephedrine" title="Azatadine/pseudoephedrine">Azatadine/pseudoephedrine</a>, <a href="/wiki/Carbinoxamine/pseudoephedrine" title="Carbinoxamine/pseudoephedrine">Carbinoxamine/pseudoephedrine</a>, <a href="/wiki/Cetirizine/pseudoephedrine" title="Cetirizine/pseudoephedrine">Cetirizine/pseudoephedrine</a>, <a href="/wiki/Dexbrompheniramine/pseudoephedrine" title="Dexbrompheniramine/pseudoephedrine">Dexbrompheniramine/pseudoephedrine</a>, <a href="/wiki/Fexofenadine/pseudoephedrine" title="Fexofenadine/pseudoephedrine">Fexofenadine/pseudoephedrine</a>, <a href="/wiki/Pseudoephedrine/loratadine" title="Pseudoephedrine/loratadine">Pseudoephedrine/loratadine</a>, and <a href="/wiki/Naproxen/pseudoephedrine" title="Naproxen/pseudoephedrine">Naproxen/pseudoephedrine</a></div> <p>Pseudoephedrine is available by itself <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">over-the-counter</a> in the form of 30 and 60<span class="nowrap"> </span>mg <a href="/wiki/Immediate-release" class="mw-redirect" title="Immediate-release">immediate-release</a> and 120 and 240<span class="nowrap"> </span>mg <a href="/wiki/Extended-release" class="mw-redirect" title="Extended-release">extended-release</a> <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a> in the <a href="/wiki/United_States" title="United States">United States</a>.<sup id="cite_ref-Drugs@FDA_30-1" class="reference"><a href="#cite_note-Drugs@FDA-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KiziorHodgson2014_53-0" class="reference"><a href="#cite_note-KiziorHodgson2014-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Braun2012_54-0" class="reference"><a href="#cite_note-Braun2012-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Berry2001_55-0" class="reference"><a href="#cite_note-Berry2001-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine is also available over-the-counter and <a href="/wiki/Prescription_drug" title="Prescription drug">prescription-only</a> <a href="/wiki/Combination_drug" title="Combination drug">in combination</a> with numerous other drugs, including <a href="/wiki/Antihistamine" title="Antihistamine">antihistamines</a> (<a href="/wiki/Acrivastine" title="Acrivastine">acrivastine</a>, <a href="/wiki/Azatadine" title="Azatadine">azatadine</a>, <a href="/wiki/Brompheniramine" title="Brompheniramine">brompheniramine</a>, <a href="/wiki/Cetirizine" title="Cetirizine">cetirizine</a>, <a href="/wiki/Chlorpheniramine" class="mw-redirect" title="Chlorpheniramine">chlorpheniramine</a>, <a href="/wiki/Clemastine" title="Clemastine">clemastine</a>, <a href="/wiki/Desloratadine" title="Desloratadine">desloratadine</a>, <a href="/wiki/Dexbrompheniramine" title="Dexbrompheniramine">dexbrompheniramine</a>, <a href="/wiki/Diphenhydramine" title="Diphenhydramine">diphenhydramine</a>, <a href="/wiki/Fexofenadine" title="Fexofenadine">fexofenadine</a>, <a href="/wiki/Loratadine" title="Loratadine">loratadine</a>, <a href="/wiki/Triprolidine" title="Triprolidine">triprolidine</a>), <a href="/wiki/Analgesic" title="Analgesic">analgesics</a> (<a href="/wiki/Acetaminophen" class="mw-redirect" title="Acetaminophen">acetaminophen</a>, <a href="/wiki/Codeine" title="Codeine">codeine</a>, <a href="/wiki/Hydrocodone" title="Hydrocodone">hydrocodone</a>, <a href="/wiki/Ibuprofen" title="Ibuprofen">ibuprofen</a>, <a href="/wiki/Naproxen" title="Naproxen">naproxen</a>), <a href="/wiki/Cough_suppressant" class="mw-redirect" title="Cough suppressant">cough suppressants</a> (<a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a>), and <a href="/wiki/Expectorant" class="mw-redirect" title="Expectorant">expectorants</a> (<a href="/wiki/Guaifenesin" title="Guaifenesin">guaifenesin</a>).<sup id="cite_ref-Drugs@FDA_30-2" class="reference"><a href="#cite_note-Drugs@FDA-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KiziorHodgson2014_53-1" class="reference"><a href="#cite_note-KiziorHodgson2014-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine has been used in the form of the <a href="/wiki/Hydrochloride" title="Hydrochloride">hydrochloride</a> and <a href="/wiki/Sulfate" title="Sulfate">sulfate</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> and in a polistirex form.<sup id="cite_ref-Drugs@FDA_30-3" class="reference"><a href="#cite_note-Drugs@FDA-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> The drug has been used in more than 135 over-the-counter and prescription formulations.<sup id="cite_ref-SalernoJackson2005_22-3" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Many prescription formulations containing pseudoephedrine have been discontinued over time.<sup id="cite_ref-Drugs@FDA_30-4" class="reference"><a href="#cite_note-Drugs@FDA-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=5" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine is <a href="/wiki/Contraindication" title="Contraindication">contraindicated</a> in patients with <a href="/wiki/Diabetes_mellitus" class="mw-redirect" title="Diabetes mellitus">diabetes mellitus</a>, <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular disease</a>, severe or uncontrolled <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, severe <a href="/wiki/Coronary_artery_disease" title="Coronary artery disease">coronary artery disease</a>, <a href="/wiki/Prostatic_hypertrophy" class="mw-redirect" title="Prostatic hypertrophy">prostatic hypertrophy</a>, <a href="/wiki/Hyperthyroidism" title="Hyperthyroidism">hyperthyroidism</a>, <a href="/wiki/Closed_angle_glaucoma" class="mw-redirect" title="Closed angle glaucoma">closed-angle glaucoma</a>, or by <a href="/wiki/Pregnancy" title="Pregnancy">pregnant</a> women.<sup id="cite_ref-Rossi_56-0" class="reference"><a href="#cite_note-Rossi-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> The safety and effectiveness of nasal decongestant use in children is unclear.<sup id="cite_ref-Deckx2016_57-0" class="reference"><a href="#cite_note-Deckx2016-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=6" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Common side effects with pseudoephedrine therapy may include <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> (CNS) <a href="/wiki/Psychostimulant" class="mw-redirect" title="Psychostimulant">stimulation</a>, <a href="/wiki/Insomnia" title="Insomnia">insomnia</a>, <a href="/wiki/Psychomotor_agitation" title="Psychomotor agitation">restlessness</a>, <a href="/wiki/Stimulation" title="Stimulation">excitability</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, and <a href="/wiki/Anxiety" title="Anxiety">anxiety</a>.<sup id="cite_ref-MunafòFraraPerico2021_18-6" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-VanBerkelFuller2015_15-4" class="reference"><a href="#cite_note-VanBerkelFuller2015-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HughesEmpeyLand1983_58-0" class="reference"><a href="#cite_note-HughesEmpeyLand1983-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> Infrequent side effects include <a href="/wiki/Tachycardia" title="Tachycardia">tachycardia</a> or <a href="/wiki/Palpitation" class="mw-redirect" title="Palpitation">palpitations</a>.<sup id="cite_ref-MunafòFraraPerico2021_18-7" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Rarely, pseudoephedrine therapy may be associated with <a href="/wiki/Mydriasis" title="Mydriasis">mydriasis</a> (dilated pupils), <a href="/wiki/Hallucination" title="Hallucination">hallucinations</a>, <a href="/wiki/Heart_arrhythmia" class="mw-redirect" title="Heart arrhythmia">arrhythmias</a>, <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, <a href="/wiki/Seizure" title="Seizure">seizures</a>, and <a href="/wiki/Ischemic_colitis" title="Ischemic colitis">ischemic colitis</a>; as well as severe <a href="/wiki/Skin_reaction" class="mw-redirect" title="Skin reaction">skin reactions</a> known as recurrent pseudo-scarlatina, <a href="/wiki/Systemic_contact_dermatitis" class="mw-redirect" title="Systemic contact dermatitis">systemic contact dermatitis</a>, and non-pigmenting <a href="/wiki/Fixed_drug_eruption" class="mw-redirect" title="Fixed drug eruption">fixed drug eruption</a>.<sup id="cite_ref-MunafòFraraPerico2021_18-8" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rossi_56-1" class="reference"><a href="#cite_note-Rossi-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> Pseudoephedrine, particularly when combined with other drugs including <a href="/wiki/Narcotic" title="Narcotic">narcotics</a>, may also play a role in the precipitation of episodes of <a href="/wiki/Psychosis" title="Psychosis">psychosis</a>.<sup id="cite_ref-MunafòFraraPerico2021_18-9" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> It has also been reported that pseudoephedrine, among other <a href="/wiki/Sympathomimetics" class="mw-redirect" title="Sympathomimetics">sympathomimetic</a> agents, may be associated with the occurrence of <a href="/wiki/Hemorrhagic_stroke" class="mw-redirect" title="Hemorrhagic stroke">hemorrhagic stroke</a> and other <a href="/wiki/Cardiovascular_complication" class="mw-redirect" title="Cardiovascular complication">cardiovascular complications</a>.<sup id="cite_ref-MunafòFraraPerico2021_18-10" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CantuArauzMurillo-Bonilla2003_23-1" class="reference"><a href="#cite_note-CantuArauzMurillo-Bonilla2003-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-VanBerkelFuller2015_15-5" class="reference"><a href="#cite_note-VanBerkelFuller2015-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>Due to its sympathomimetic effects, pseudoephedrine is a <a href="/wiki/Vasoconstrictor" class="mw-redirect" title="Vasoconstrictor">vasoconstrictor</a> and <a href="/wiki/Antihypotensive_agent" class="mw-redirect" title="Antihypotensive agent">pressor agent</a> (increases <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>), a <a href="/wiki/Chronotropic#Positive_chronotropes" title="Chronotropic">positive chronotrope</a> (increases <a href="/wiki/Heart_rate" title="Heart rate">heart rate</a>), and a <a href="/wiki/Inotrope#Positive_inotropic_agents" title="Inotrope">positive inotrope</a> (increases <a href="/wiki/Myocardial_contractility" title="Myocardial contractility">force of heart contractions</a>).<sup id="cite_ref-MunafòFraraPerico2021_18-11" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-17" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SalernoJackson2005_22-4" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TrinhKimRitsma2015_19-2" class="reference"><a href="#cite_note-TrinhKimRitsma2015-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GheorghievHosseiniMoran2018_20-2" class="reference"><a href="#cite_note-GheorghievHosseiniMoran2018-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The influence of pseudoephedrine on blood pressure at clinical doses is controversial.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-18" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SalernoJackson2005_22-5" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> A closely related sympathomimetic and decongestant, <a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">phenylpropanolamine</a>, was <a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">withdrawn</a> due to associations with markedly increased blood pressure and incidence of hemorrhagic stroke.<sup id="cite_ref-SalernoJackson2005_22-6" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> There has been concern that pseudoephedrine may likewise dangerously increase blood pressure and thereby increase the risk of stroke, whereas others have contended that the risks are exaggerated.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-19" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SalernoJackson2005_22-7" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Besides hemorrhagic stroke, <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a>, <a href="/wiki/Coronary_vasospasm" title="Coronary vasospasm">coronary vasospasm</a>, and <a href="/wiki/Cardiac_arrest" title="Cardiac arrest">sudden death</a> have also rarely been reported with sympathomimetic <a href="/wiki/Ephedra_(plant)" title="Ephedra (plant)">ephedra</a> compounds like pseudoephedrine and <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>.<sup id="cite_ref-MunafòFraraPerico2021_18-12" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-VanBerkelFuller2015_15-6" class="reference"><a href="#cite_note-VanBerkelFuller2015-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>A 2005 <a href="/wiki/Meta-analysis" title="Meta-analysis">meta-analysis</a> found that pseudoephedrine at recommended doses had no meaningful effect on <a href="/wiki/Systolic_blood_pressure" class="mw-redirect" title="Systolic blood pressure">systolic</a> or <a href="/wiki/Diastolic_blood_pressure" class="mw-redirect" title="Diastolic blood pressure">diastolic blood pressure</a> in healthy individuals or people with controlled <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-20" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SalernoJackson2005_22-8" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Systolic blood pressure was found to slightly increase by 0.99<span class="nowrap"> </span>mm<span class="nowrap"> </span>Hg on average and heart rate was found to slightly increase by 2.83<span class="nowrap"> </span>bpm on average.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-21" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SalernoJackson2005_22-9" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Conversely, there was no significant influence on diastolic blood pressure, which increased by 0.63<span class="nowrap"> </span>mg<span class="nowrap"> </span>Hg.<sup id="cite_ref-SalernoJackson2005_22-10" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> In people with controlled hypertension, systolic hypertension increased by a similar degree of 1.20<span class="nowrap"> </span>mm<span class="nowrap"> </span>Hg.<sup id="cite_ref-SalernoJackson2005_22-11" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Immediate-release" class="mw-redirect" title="Immediate-release">Immediate-release</a> preparations, higher doses, being male, and shorter duration of use were all associated with greater cardiovascular effects.<sup id="cite_ref-SalernoJackson2005_22-12" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> A small subset of individuals with <a href="/wiki/Dysautonomia" title="Dysautonomia">autonomic instability</a>, perhaps in turn resulting in greater adrenergic receptor sensitivity, may be substantially more sensitive to the cardiovascular effects of sympathomimetics.<sup id="cite_ref-SalernoJackson2005_22-13" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Subsequent to the 2005 meta-analysis, a 2015 <a href="/wiki/Systematic_review" title="Systematic review">systematic review</a> and a 2018 meta-analysis found that pseudoephedrine at high doses (>170<span class="nowrap"> </span>mg) could increase heart rate and physical performance with larger <a href="/wiki/Effect_size" title="Effect size">effect sizes</a> than lower doses.<sup id="cite_ref-TrinhKimRitsma2015_19-3" class="reference"><a href="#cite_note-TrinhKimRitsma2015-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GheorghievHosseiniMoran2018_20-3" class="reference"><a href="#cite_note-GheorghievHosseiniMoran2018-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>A 2007 <a href="/wiki/Cochrane_review" class="mw-redirect" title="Cochrane review">Cochrane review</a> assessed the side effects of short-term use of pseudoephedrine at recommended doses as a nasal decongestant.<sup id="cite_ref-TavernerLatte2007_21-2" class="reference"><a href="#cite_note-TavernerLatte2007-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> It found that pseudoephedrine had a small risk of <a href="/wiki/Insomnia" title="Insomnia">insomnia</a> and this was the only side effect that occurred at rates significantly different from placebo.<sup id="cite_ref-TavernerLatte2007_21-3" class="reference"><a href="#cite_note-TavernerLatte2007-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Insomnia occurred at a rate of 5% and had an <a href="/wiki/Odds_ratio" title="Odds ratio">odds ratio</a> (OR) of 6.18.<sup id="cite_ref-TavernerLatte2007_21-4" class="reference"><a href="#cite_note-TavernerLatte2007-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Other side effects, including <a href="/wiki/Headache" title="Headache">headache</a> and <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, occurred at rates of less than 4% and were not different from placebo.<sup id="cite_ref-TavernerLatte2007_21-5" class="reference"><a href="#cite_note-TavernerLatte2007-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Tachyphylaxis" title="Tachyphylaxis">Tachyphylaxis</a> is known to develop with prolonged use of pseudoephedrine, especially when it is re-administered at short intervals.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-22" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MunafòFraraPerico2021_18-13" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>There is a case report of temporary <a href="/wiki/Depression_(mood)" title="Depression (mood)">depressive symptoms</a> upon <a href="/wiki/Drug_discontinuation" class="mw-redirect" title="Drug discontinuation">discontinuation</a> and <a href="/wiki/Drug_withdrawal" title="Drug withdrawal">withdrawal</a> from pseudoephedrine.<sup id="cite_ref-MunafòFraraPerico2021_18-14" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WebbDubose2013_61-0" class="reference"><a href="#cite_note-WebbDubose2013-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> The withdrawal symptoms included worsened <a href="/wiki/Mood_(psychology)" title="Mood (psychology)">mood</a> and <a href="/wiki/Sadness" title="Sadness">sadness</a>, profoundly decreased <a href="/wiki/Mental_energy" title="Mental energy">energy</a>, a worsened view of oneself, decreased concentration, <a href="/wiki/Psychomotor_retardation" title="Psychomotor retardation">psychomotor retardation</a>, increased <a href="/wiki/Appetite" title="Appetite">appetite</a>, and increased need for <a href="/wiki/Sleep" title="Sleep">sleep</a>.<sup id="cite_ref-MunafòFraraPerico2021_18-15" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WebbDubose2013_61-1" class="reference"><a href="#cite_note-WebbDubose2013-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine has psychostimulant effects at high doses and is a <a href="/wiki/Positive_reinforcement" class="mw-redirect" title="Positive reinforcement">positive reinforcer</a> with <a href="/wiki/Amphetamine-type_stimulant" class="mw-redirect" title="Amphetamine-type stimulant">amphetamine</a>-like effects in animals including rats and monkeys.<sup id="cite_ref-FreemanWangWoolverton2010_62-0" class="reference"><a href="#cite_note-FreemanWangWoolverton2010-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WeeOrdwayWoolverton2004_63-0" class="reference"><a href="#cite_note-WeeOrdwayWoolverton2004-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TongjaroenbuangamMeksuriyenGovitrapong1998_64-0" class="reference"><a href="#cite_note-TongjaroenbuangamMeksuriyenGovitrapong1998-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AkibaSatohMastumura1982_65-0" class="reference"><a href="#cite_note-AkibaSatohMastumura1982-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> However, it is substantially less <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> than <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a> or <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>.<sup id="cite_ref-FreemanWangWoolverton2010_62-1" class="reference"><a href="#cite_note-FreemanWangWoolverton2010-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WeeOrdwayWoolverton2004_63-1" class="reference"><a href="#cite_note-WeeOrdwayWoolverton2004-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TongjaroenbuangamMeksuriyenGovitrapong1998_64-1" class="reference"><a href="#cite_note-TongjaroenbuangamMeksuriyenGovitrapong1998-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=7" title="Edit section: Overdose"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The maximum total daily dose of pseudoephedrine is 240<span class="nowrap"> </span>mg.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-23" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Symptoms of <a href="/wiki/Drug_overdose" title="Drug overdose">overdose</a> may include <a href="/wiki/Sedation" title="Sedation">sedation</a>, <a href="/wiki/Apnea" title="Apnea">apnea</a>, impaired concentration, <a href="/wiki/Cyanosis" title="Cyanosis">cyanosis</a>, <a href="/wiki/Coma" title="Coma">coma</a>, <a href="/wiki/Circulatory_collapse" class="mw-redirect" title="Circulatory collapse">circulatory collapse</a>, <a href="/wiki/Insomnia" title="Insomnia">insomnia</a>, <a href="/wiki/Hallucination" title="Hallucination">hallucinations</a>, <a href="/wiki/Tremor" title="Tremor">tremors</a>, <a href="/wiki/Convulsion" title="Convulsion">convulsions</a>, <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, <a href="/wiki/Anxiety" title="Anxiety">anxiety</a>, <a href="/wiki/Euphoria" title="Euphoria">euphoria</a>, <a href="/wiki/Tinnitus" title="Tinnitus">tinnitus</a>, <a href="/wiki/Blurred_vision" title="Blurred vision">blurred vision</a>, <a href="/wiki/Ataxia" title="Ataxia">ataxia</a>, <a href="/wiki/Chest_pain" title="Chest pain">chest pain</a>, <a href="/wiki/Tachycardia" title="Tachycardia">tachycardia</a>, <a href="/wiki/Palpitation" class="mw-redirect" title="Palpitation">palpitations</a>, <a href="/wiki/Hypertension" title="Hypertension">increased blood pressure</a>, <a href="/wiki/Hypotension" title="Hypotension">decreased blood pressure</a>, <a href="/wiki/Thirst" title="Thirst">thirstiness</a>, <a href="/wiki/Sweating" class="mw-redirect" title="Sweating">sweating</a>, difficulty with <a href="/wiki/Urination" title="Urination">urination</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, and <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-24" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> In children, symptoms have more often included <a href="/wiki/Dry_mouth" class="mw-redirect" title="Dry mouth">dry mouth</a>, <a href="/wiki/Pupil_dilation" class="mw-redirect" title="Pupil dilation">pupil dilation</a>, <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>, <a href="/wiki/Fever" title="Fever">fever</a>, and <a href="/wiki/Gastrointestinal_disorder" class="mw-redirect" title="Gastrointestinal disorder">gastrointestinal dysfunction</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-25" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Pseudoephedrine may produce <a href="/wiki/Toxicity" title="Toxicity">toxic</a> effects both with use of supratherapeutic doses but also in people who are more sensitive to the effects of sympathomimetics.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-26" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Drug_misuse" class="mw-redirect" title="Drug misuse">Misuse</a> of the drug has been reported in one case at massive doses of 3,000 to 4,500<span class="nowrap"> </span>mg (100–150<span class="nowrap"> </span>×<span class="nowrap"> </span>30-mg tablets) per day, with the doses gradually increased over time by this individual.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-27" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DiazWiseSemchyshyn1979_66-0" class="reference"><a href="#cite_note-DiazWiseSemchyshyn1979-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> No fatalities due to pseudoephedrine misuse have been reported as of 2021.<sup id="cite_ref-SchifanoChiappiniMiuli2021_17-3" class="reference"><a href="#cite_note-SchifanoChiappiniMiuli2021-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> However, death with pseudoephedrine has been reported generally.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-28" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LaccourreyeWernerGiroud2015_13-7" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MunafòFraraPerico2021_18-16" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=8" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Concomitant or recent (previous 14<span class="nowrap"> </span>days) <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">monoamine oxidase inhibitor</a> (MAOI) use can lead to <a href="/wiki/Hypertension" title="Hypertension">hypertensive reactions</a>, including <a href="/wiki/Hypertensive_crisis" title="Hypertensive crisis">hypertensive crisis</a>, and should be avoided.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-29" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rossi_56-2" class="reference"><a href="#cite_note-Rossi-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> Clinical studies have found minimal or no influence of certain MAOIs like the weak non-selective MAOI <a href="/wiki/Linezolid" title="Linezolid">linezolid</a> and the potent selective MAO-B inhibitor <a href="/wiki/Selegiline" title="Selegiline">selegiline</a> (as a <a href="/wiki/Transdermal_patch" title="Transdermal patch">transdermal patch</a>) on the <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> of pseudoephedrine.<sup id="cite_ref-StalkerJungbluth2003_67-0" class="reference"><a href="#cite_note-StalkerJungbluth2003-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JacobWagnerSage2003_68-0" class="reference"><a href="#cite_note-JacobWagnerSage2003-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HendershotAntalWelshman2001_69-0" class="reference"><a href="#cite_note-HendershotAntalWelshman2001-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AzzaroVanDenBergZiemniak2007_70-0" class="reference"><a href="#cite_note-AzzaroVanDenBergZiemniak2007-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> This is in accordance with the fact that pseudoephedrine is not <a href="/wiki/Drug_metabolism" title="Drug metabolism">metabolized</a> by <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidase</a> (MAO).<sup id="cite_ref-ODonnell1995_25-3" class="reference"><a href="#cite_note-ODonnell1995-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ChuaBenrimojTriggs1989_11-3" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JohnsonHricik1993_71-0" class="reference"><a href="#cite_note-JohnsonHricik1993-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> However, pseudoephedrine <a href="/wiki/Norepinephrine_releasing_agent" title="Norepinephrine releasing agent">induces the release of norepinephrine</a>, which MAOIs inhibit the metabolism of, and as such, MAOIs can still potentiate the effects of pseudoephedrine.<sup id="cite_ref-Broadley2010_72-0" class="reference"><a href="#cite_note-Broadley2010-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-30" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JacobWagnerSage2003_68-1" class="reference"><a href="#cite_note-JacobWagnerSage2003-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> No significant pharmacodynamic interactions have been found with selegiline,<sup id="cite_ref-JacobWagnerSage2003_68-2" class="reference"><a href="#cite_note-JacobWagnerSage2003-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AzzaroVanDenBergZiemniak2007_70-1" class="reference"><a href="#cite_note-AzzaroVanDenBergZiemniak2007-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> but linezolid potentiated <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a> increases with pseudoephedrine.<sup id="cite_ref-StalkerJungbluth2003_67-1" class="reference"><a href="#cite_note-StalkerJungbluth2003-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HendershotAntalWelshman2001_69-1" class="reference"><a href="#cite_note-HendershotAntalWelshman2001-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> However, this was deemed to be without clinical significance in the case of linezolid, though it was noted that some individuals may be more sensitive to the <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic</a> effects of pseudoephedrine and related agents.<sup id="cite_ref-StalkerJungbluth2003_67-2" class="reference"><a href="#cite_note-StalkerJungbluth2003-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HendershotAntalWelshman2001_69-2" class="reference"><a href="#cite_note-HendershotAntalWelshman2001-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> Pseudoephedrine is <a href="/wiki/Contraindication" title="Contraindication">contraindicated</a> with MAOIs like <a href="/wiki/Phenelzine" title="Phenelzine">phenelzine</a>, <a href="/wiki/Tranylcypromine" title="Tranylcypromine">tranylcypromine</a>, <a href="/wiki/Isocarboxazid" title="Isocarboxazid">isocarboxazid</a>, and <a href="/wiki/Moclobemide" title="Moclobemide">moclobemide</a> due to the potential for synergistic sympathomimetic effects and hypertensive crisis.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-31" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MunafòFraraPerico2021_18-17" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> It is also considered to be contraindicated with linezolid and selegiline as some individuals may react more sensitively to coadministration.<sup id="cite_ref-StalkerJungbluth2003_67-3" class="reference"><a href="#cite_note-StalkerJungbluth2003-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HendershotAntalWelshman2001_69-3" class="reference"><a href="#cite_note-HendershotAntalWelshman2001-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JacobWagnerSage2003_68-3" class="reference"><a href="#cite_note-JacobWagnerSage2003-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AzzaroVanDenBergZiemniak2007_70-2" class="reference"><a href="#cite_note-AzzaroVanDenBergZiemniak2007-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> </p><p>Concomitant use of pseudoephedrine with other <a href="/wiki/Vasoconstrictor" class="mw-redirect" title="Vasoconstrictor">vasoconstrictors</a>, including <a href="/wiki/Ergot_alkaloid" class="mw-redirect" title="Ergot alkaloid">ergot alkaloids</a> like <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a> and <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Linezolid" title="Linezolid">linezolid</a>, <a href="/wiki/Oxytocin_(medication)" title="Oxytocin (medication)">oxytocin</a>, <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>, <a href="/wiki/Phenylephrine" title="Phenylephrine">phenylephrine</a>, and <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, among others, is not recommended due to the possibility of greater increases in blood pressure and risk of <a href="/wiki/Hemorrhagic_stroke" class="mw-redirect" title="Hemorrhagic stroke">hemorrhagic stroke</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-32" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Sympathomimetic effects and cardiovascular risks of pseudoephedrine may also be increased with <a href="/wiki/Cardiac_glycoside" title="Cardiac glycoside">digitalis glycosides</a>, <a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">tricyclic antidepressants</a>, <a href="/wiki/Appetite_suppressant" class="mw-redirect" title="Appetite suppressant">appetite suppressants</a>, and <a href="/wiki/Inhalational_anesthetic" title="Inhalational anesthetic">inhalational anesthetics</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-33" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Likewise, greater sympathomimetic effects of pseudoephedrine may occur when it is combined with other sympathomimetic agents.<sup id="cite_ref-MunafòFraraPerico2021_18-18" class="reference"><a href="#cite_note-MunafòFraraPerico2021-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Rare but serious cardiovascular complications have been reported with the combination of pseudoephedrine and <a href="/wiki/Bupropion" title="Bupropion">bupropion</a>.<sup id="cite_ref-LaccourreyeWernerGiroud2015_13-8" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Marcucci2015_73-0" class="reference"><a href="#cite_note-Marcucci2015-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PedersonKuntzGarbe2001_74-0" class="reference"><a href="#cite_note-PedersonKuntzGarbe2001-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> Increase of <a href="/wiki/Ectopic_pacemaker" title="Ectopic pacemaker">ectopic pacemaker</a> activity can occur when pseudoephedrine is used concomitantly with <a href="/wiki/Digitalis" title="Digitalis">digitalis</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-34" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Antihypertensive" title="Antihypertensive">antihypertensive</a> effects of <a href="/wiki/Methyldopa" title="Methyldopa">methyldopa</a>, <a href="/wiki/Guanethidine" title="Guanethidine">guanethidine</a>, <a href="/wiki/Mecamylamine" title="Mecamylamine">mecamylamine</a>, <a href="/wiki/Reserpine" title="Reserpine">reserpine</a>, and <a href="/wiki/Veratrum_alkaloids" class="mw-redirect" title="Veratrum alkaloids">veratrum alkaloids</a> may be reduced by sympathomimetics like pseudoepehdrine.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-35" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> like <a href="/wiki/Labetalol" title="Labetalol">labetalol</a> may reduce the effects of pseudoephedrine.<sup id="cite_ref-Mariani1986_75-0" class="reference"><a href="#cite_note-Mariani1986-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MoresCampiaNavarra1999_76-0" class="reference"><a href="#cite_note-MoresCampiaNavarra1999-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Acidifier" title="Acidifier">Urinary acidifying agents</a> like <a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">ascorbic acid</a> and <a href="/wiki/Ammonium_chloride" title="Ammonium chloride">ammonium chloride</a> can increase the <a href="/wiki/Excretion" title="Excretion">excretion</a> of and thereby reduce exposure to <a href="/wiki/Amphetamine-type_stimulant" class="mw-redirect" title="Amphetamine-type stimulant">amphetamines</a> including pseudoephedrine, whereas <a href="/wiki/Alkalinizing_agent" title="Alkalinizing agent">urinary alkalinizing agents</a> including <a href="/wiki/Antacid" title="Antacid">antacids</a> like <a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate">sodium bicarbonate</a> as well as <a href="/wiki/Acetazolamide" title="Acetazolamide">acetazolamide</a> can reduce the excretion of these agents and thereby increase exposure to them.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-36" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ChuaBenrimojTriggs1989_11-4" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PatrickMarkowitz1997_77-0" class="reference"><a href="#cite_note-PatrickMarkowitz1997-77"><span class="cite-bracket">[</span>77<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=Pseudoephedrine&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=Pseudoephedrine&action=edit&section=10" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine is a <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic agent</a> which acts primarily or exclusively by <a href="/wiki/Norepinephrine_releasing_agent" title="Norepinephrine releasing agent">inducing the release of norepinephrine</a>.<sup id="cite_ref-Abraham2003_78-0" class="reference"><a href="#cite_note-Abraham2003-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ODonnell1995_25-4" class="reference"><a href="#cite_note-ODonnell1995-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-13" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RothmanVuPartilla2003_24-2" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Hence, it is an indirectly acting sympathomimetic.<sup id="cite_ref-Abraham2003_78-1" class="reference"><a href="#cite_note-Abraham2003-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ODonnell1995_25-5" class="reference"><a href="#cite_note-ODonnell1995-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-14" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Some sources state that pseudoephedrine has a mixed <a href="/wiki/Mechanism_of_action" title="Mechanism of action">mechanism of action</a> consisting of both indirect and direct effects by binding to and acting as an <a href="/wiki/Agonist" title="Agonist">agonist</a> of <a href="/wiki/Adrenergic_receptor" title="Adrenergic receptor">adrenergic receptors</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-37" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-VanBerkelFuller2015_15-7" class="reference"><a href="#cite_note-VanBerkelFuller2015-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> However, the <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> of pseudoephedrine for adrenergic receptors is described as very low or negligible.<sup id="cite_ref-Abraham2003_78-2" class="reference"><a href="#cite_note-Abraham2003-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Animal_study" class="mw-redirect" title="Animal study">Animal studies</a> suggest that the sympathomimetic effects of pseudoephedrine are exclusively due to norepinephrine release.<sup id="cite_ref-GadAzabKhattab2021_79-0" class="reference"><a href="#cite_note-GadAzabKhattab2021-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KobayashiEndouSakuraya2003_80-0" class="reference"><a href="#cite_note-KobayashiEndouSakuraya2003-80"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable sortable floatright" style="font-size:small;"> <caption>Monoamine release by pseudoephedrine and related agents (<a href="/wiki/Half_maximal_effective_concentration" class="mw-redirect" title="Half maximal effective concentration"><abbr title="half maximal effective concentration">EC<sub>50</sub></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 half maximal effective concentration</span>, nM)<sup id="cite_ref-RothmanBaumann2003_81-0" class="reference"><a href="#cite_note-RothmanBaumann2003-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RothmanBaumann2006_82-0" class="reference"><a href="#cite_note-RothmanBaumann2006-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th>Compound</th> <th data-sort-type="number"><a href="/wiki/Norepinephrine" title="Norepinephrine"><abbr title="Norepinephrine">NE</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 Norepinephrine</span></th> <th data-sort-type="number"><a href="/wiki/Dopamine" title="Dopamine"><abbr title="Dopamine">DA</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 Dopamine</span></th> <th data-sort-type="number"><a href="/wiki/Serotonin" title="Serotonin"><abbr title="Serotonin">5-HT</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 Serotonin</span></th> <th>Ref </th></tr> <tr> <td><a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a> (<i>S</i>(+)-amphetamine)</td> <td>6.6–7.2</td> <td>5.8–24.8</td> <td>698–1765</td> <td><sup id="cite_ref-RothmanBaumannDersch2001_83-0" class="reference"><a href="#cite_note-RothmanBaumannDersch2001-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BaumannPartillaLehner2013_84-0" class="reference"><a href="#cite_note-BaumannPartillaLehner2013-84"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Cathinone" title="Cathinone"><i>S</i>(–)-Cathinone</a></td> <td>12.4</td> <td>18.5</td> <td>2366</td> <td><sup id="cite_ref-RothmanVuPartilla2003_24-3" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a> ((–)-ephedrine)</td> <td>43.1–72.4</td> <td>236–1350</td> <td>>10000</td> <td><sup id="cite_ref-RothmanBaumannDersch2001_83-1" class="reference"><a href="#cite_note-RothmanBaumannDersch2001-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>(+)-Ephedrine</td> <td>218</td> <td>2104</td> <td>>10000</td> <td><sup id="cite_ref-RothmanBaumannDersch2001_83-2" class="reference"><a href="#cite_note-RothmanBaumannDersch2001-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RothmanVuPartilla2003_24-4" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a> (<i>S</i>(+)-methamphetamine)</td> <td>12.3–13.8</td> <td>8.5–24.5</td> <td>736–1291.7</td> <td><sup id="cite_ref-RothmanBaumannDersch2001_83-3" class="reference"><a href="#cite_note-RothmanBaumannDersch2001-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BaumannAyestasPartilla2012_85-0" class="reference"><a href="#cite_note-BaumannAyestasPartilla2012-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a> (<i>R</i>(–)-methamphetamine)</td> <td>28.5</td> <td>416</td> <td>4640</td> <td><sup id="cite_ref-RothmanBaumannDersch2001_83-4" class="reference"><a href="#cite_note-RothmanBaumannDersch2001-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">(+)-Phenylpropanolamine</a> ((+)-norephedrine)</td> <td>42.1</td> <td>302</td> <td>>10000</td> <td><sup id="cite_ref-RothmanVuPartilla2003_24-5" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">(–)-Phenylpropanolamine</a> ((–)-norephedrine)</td> <td>137</td> <td>1371</td> <td>>10000</td> <td><sup id="cite_ref-RothmanVuPartilla2003_24-6" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Cathine" title="Cathine">Cathine</a> ((+)-norpseudoephedrine)</td> <td>15.0</td> <td>68.3</td> <td>>10000</td> <td><sup id="cite_ref-RothmanVuPartilla2003_24-7" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/L-Norpseudoephedrine" title="L-Norpseudoephedrine">(–)-Norpseudoephedrine</a></td> <td>30.1</td> <td>294</td> <td>>10000</td> <td><sup id="cite_ref-RothmanVuPartilla2003_24-8" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>(–)-Pseudoephedrine</td> <td>4092</td> <td>9125</td> <td>>10000</td> <td><sup id="cite_ref-RothmanVuPartilla2003_24-9" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>Pseudoephedrine ((+)-pseudoephedrine)</td> <td>224</td> <td>1988</td> <td>>10000</td> <td><sup id="cite_ref-RothmanVuPartilla2003_24-10" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="7" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Notes:</b> The smaller the value, the more strongly the substance releases the neurotransmitter. See also <a href="/wiki/Monoamine_releasing_agent#Activity_profiles" title="Monoamine releasing agent">Monoamine releasing agent § Activity profiles</a> for a larger table with more compounds. </td></tr> </tbody></table> <p>Pseudoephedrine <a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">induces monoamine release</a> <i><a href="/wiki/In_vitro" title="In vitro">in vitro</a></i> with an <a href="/wiki/Half_maximal_effective_concentration" class="mw-redirect" title="Half maximal effective concentration"><abbr title="half maximal effective concentration">EC<sub>50</sub></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 half maximal effective concentration</span> of 224<span class="nowrap"> </span>nM for <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a> and 1,988<span class="nowrap"> </span>nM for <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, whereas it is inactive for <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>.<sup id="cite_ref-RothmanVuPartilla2003_24-11" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RothmanBaumann2005_86-0" class="reference"><a href="#cite_note-RothmanBaumann2005-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RothmanBaumann2006_82-1" class="reference"><a href="#cite_note-RothmanBaumann2006-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup> As such, it is about 9-fold <a href="/wiki/Binding_selectivity" title="Binding selectivity">selective</a> for induction of norepinephrine release over dopamine release.<sup id="cite_ref-RothmanVuPartilla2003_24-12" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RothmanBaumann2005_86-1" class="reference"><a href="#cite_note-RothmanBaumann2005-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RothmanBaumann2006_82-2" class="reference"><a href="#cite_note-RothmanBaumann2006-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup> The drug has negligible agonistic activity at the <a href="/wiki/%CE%911-adrenergic_receptor" class="mw-redirect" title="Α1-adrenergic receptor">α<sub>1</sub>-</a> and <a href="/wiki/%CE%912-adrenergic_receptor" class="mw-redirect" title="Α2-adrenergic receptor">α<sub>2</sub>-adrenergic receptors</a> (K<sub>act</sub> >10,000<span class="nowrap"> </span>nM).<sup id="cite_ref-RothmanVuPartilla2003_24-13" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> At the <a href="/wiki/%CE%921-adrenergic_receptor" class="mw-redirect" title="Β1-adrenergic receptor">β<sub>1</sub>-</a> and <a href="/wiki/%CE%922-adrenergic_receptor" class="mw-redirect" title="Β2-adrenergic receptor">β<sub>2</sub>-adrenergic receptors</a>, it acts as a <a href="/wiki/Partial_agonist" title="Partial agonist">partial agonist</a> with relatively low <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> (β<sub>1</sub> = K<sub>act</sub> = 309<span class="nowrap"> </span>μM, <a href="/wiki/Intrinsic_activity" title="Intrinsic activity"><abbr title="intrinsic activity">IA</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 intrinsic activity</span> = 53%; β<sub>2</sub> = 10<span class="nowrap"> </span>μM; <abbr title="intrinsic activity">IA</abbr> = 47%).<sup id="cite_ref-VansalFeller1999_87-0" class="reference"><a href="#cite_note-VansalFeller1999-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> It was an <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> or very weak partial agonist of the <a href="/wiki/%CE%923-adrenergic_receptor" class="mw-redirect" title="Β3-adrenergic receptor">β<sub>3</sub>-adrenergic receptor</a> (K<sub>act</sub> = <abbr title="not determined (due to low intrinsic activity)">ND</abbr>; <abbr title="Intrinsic activity">IA</abbr> = 7%).<sup id="cite_ref-VansalFeller1999_87-1" class="reference"><a href="#cite_note-VansalFeller1999-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> It is about 30,000 to 40,000<span class="nowrap"> </span>times less potent as a β-adrenergic receptor agonist than <a href="/wiki/Isoproterenol" class="mw-redirect" title="Isoproterenol">(–)-isoproterenol</a>.<sup id="cite_ref-VansalFeller1999_87-2" class="reference"><a href="#cite_note-VansalFeller1999-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine's principal mechanism of action relies on its action on the adrenergic system.<sup id="cite_ref-American_Medical_Association,_AMA_Department_of_Drugs_1977_627_88-0" class="reference"><a href="#cite_note-American_Medical_Association,_AMA_Department_of_Drugs_1977_627-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Thomson/Micromedex_2007_2452_89-0" class="reference"><a href="#cite_note-Thomson/Micromedex_2007_2452-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstriction</a> that pseudoephedrine produces is believed to be principally an α-adrenergic receptor response.<sup id="cite_ref-drew_90-0" class="reference"><a href="#cite_note-drew-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup> Pseudoephedrine acts on α- and β<sub>2</sub>-adrenergic receptors, to cause vasoconstriction and relaxation of smooth muscle in the bronchi, respectively.<sup id="cite_ref-American_Medical_Association,_AMA_Department_of_Drugs_1977_627_88-1" class="reference"><a href="#cite_note-American_Medical_Association,_AMA_Department_of_Drugs_1977_627-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Thomson/Micromedex_2007_2452_89-1" class="reference"><a href="#cite_note-Thomson/Micromedex_2007_2452-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> α-Adrenergic receptors are located on the muscles lining the walls of blood vessels. When these receptors are activated, the muscles contract, causing the blood vessels to constrict (vasoconstriction). The constricted blood vessels now allow less fluid to leave the blood vessels and enter the nose, throat, and sinus linings, which results in decreased inflammation of nasal membranes, as well as decreased mucus production. Thus, by constriction of blood vessels, mainly those located in the nasal passages, pseudoephedrine causes a decrease in the symptoms of nasal congestion.<sup id="cite_ref-Eccles2007_2-15" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Activation of β<sub>2</sub>-adrenergic receptors produces relaxation of the smooth muscle of the bronchi,<sup id="cite_ref-American_Medical_Association,_AMA_Department_of_Drugs_1977_627_88-2" class="reference"><a href="#cite_note-American_Medical_Association,_AMA_Department_of_Drugs_1977_627-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> causing bronchial dilation and in turn decreasing congestion (although not fluid) and difficulty breathing. </p><p>Pseudoephedrine is less <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> as a sympathomimetic and <a href="/wiki/Psychostimulant" class="mw-redirect" title="Psychostimulant">psychostimulant</a> than <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-38" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HughesEmpeyLand1983_58-1" class="reference"><a href="#cite_note-HughesEmpeyLand1983-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> Clinical studies have found that pseudoephedrine is about 3.5- to 4-fold less potent than ephedrine as a sympathomimetic agent in terms of <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a> increases and 3.5- to 7.2-fold or more less potent as a <a href="/wiki/Bronchodilator" title="Bronchodilator">bronchodilator</a>.<sup id="cite_ref-HughesEmpeyLand1983_58-2" class="reference"><a href="#cite_note-HughesEmpeyLand1983-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> Pseudoephedrine is also said to have much less central effect than ephedrine and to be only a weak psychostimulant.<sup id="cite_ref-ODonnell1995_25-6" class="reference"><a href="#cite_note-ODonnell1995-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HughesEmpeyLand1983_58-3" class="reference"><a href="#cite_note-HughesEmpeyLand1983-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-16" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Abraham2003_78-3" class="reference"><a href="#cite_note-Abraham2003-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AkibaSatohMastumura1982_65-1" class="reference"><a href="#cite_note-AkibaSatohMastumura1982-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Blood_vessel" title="Blood vessel">Blood vessels</a> in the nose are around five times more sensitive than the <a href="/wiki/Heart" title="Heart">heart</a> to the actions of circulating <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a> (adrenaline), which may help to explain how pseudoephedrine at the low doses used in over-the-counter products can produce nasal decongestion with minimal effects on the heart.<sup id="cite_ref-Eccles2007_2-17" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Compared to <a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">dextroamphetamine</a>, pseudoephedrine is about 30 to 35<span class="nowrap"> </span>times less potent as a norepinephrine releasing agent and 80 to 350<span class="nowrap"> </span>times less potent as a <a href="/wiki/Dopamine_releasing_agent" title="Dopamine releasing agent">dopamine releasing agent</a> <i><a href="/wiki/In_vitro" title="In vitro">in vitro</a></i>.<sup id="cite_ref-RothmanVuPartilla2003_24-14" class="reference"><a href="#cite_note-RothmanVuPartilla2003-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RothmanBaumannDersch2001_83-5" class="reference"><a href="#cite_note-RothmanBaumannDersch2001-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BaumannPartillaLehner2013_84-1" class="reference"><a href="#cite_note-BaumannPartillaLehner2013-84"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine is a very weak <a href="/wiki/Reversible_inhibitor" class="mw-redirect" title="Reversible inhibitor">reversible inhibitor</a> of <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidase</a> (MAO) <i>in vitro</i>, including both <a href="/wiki/MAO-A" class="mw-redirect" title="MAO-A">MAO-A</a> and <a href="/wiki/MAO-B" class="mw-redirect" title="MAO-B">MAO-B</a> (K<sub>i</sub> = 1,000–5,800<span class="nowrap"> </span>μM).<sup id="cite_ref-UlusMaherWurtman2000_91-0" class="reference"><a href="#cite_note-UlusMaherWurtman2000-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> It is far less potent in this action than other agents like dextroamphetamine and <a href="/wiki/Moclobemide" title="Moclobemide">moclobemide</a>.<sup id="cite_ref-UlusMaherWurtman2000_91-1" class="reference"><a href="#cite_note-UlusMaherWurtman2000-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> </p> <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=Pseudoephedrine&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=Pseudoephedrine&action=edit&section=12" title="Edit section: Absorption"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine is <a href="/wiki/Oral_administration" title="Oral administration">orally active</a> and is readily <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorbed</a> from the <a href="/wiki/Gastrointestinal_tract" title="Gastrointestinal tract">gastrointestinal tract</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-39" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-18" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Its oral <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> is approximately 100%.<sup id="cite_ref-BruntonLazoParker2006_8-2" class="reference"><a href="#cite_note-BruntonLazoParker2006-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The drug reaches <a href="/wiki/Cmax_(pharmacology)" title="Cmax (pharmacology)">peak</a> concentrations after 1 to 4<span class="nowrap"> </span>hours (mean 1.9<span class="nowrap"> </span>hours) in the case of the <a href="/wiki/Immediate-release" class="mw-redirect" title="Immediate-release">immediate-release</a> formulation and after 2 to 6<span class="nowrap"> </span>hours in the case of the <a href="/wiki/Extended-release" class="mw-redirect" title="Extended-release">extended-release</a> formulation.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-40" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-19" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Onset_of_action" title="Onset of action">onset of action</a> of pseudoephedrine is 30<span class="nowrap"> </span>minutes.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-41" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<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=Pseudoephedrine&action=edit&section=13" title="Edit section: Distribution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine, due to its lack of <a href="/wiki/Chemical_polarity" title="Chemical polarity">polar</a> <a href="/wiki/Phenols" title="Phenols">phenolic</a> <a href="/wiki/Functional_group" title="Functional group">groups</a>, is relatively <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a>.<sup id="cite_ref-ChuaBenrimojTriggs1989_11-5" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> This is a property it shares with related sympathomimetic and decongestant agents like <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a> and <a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">phenylpropanolamine</a>.<sup id="cite_ref-ChuaBenrimojTriggs1989_11-6" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> These agents are widely <a href="/wiki/Distribution_(pharmacology)" title="Distribution (pharmacology)">distributed</a> throughout the body and cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a>.<sup id="cite_ref-ChuaBenrimojTriggs1989_11-7" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> However, it is said that pseudoephedrine and phenylpropanolamine cross the blood-brain barrier only to some extent and that pseudoephedrine has limited <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> activity, suggesting that it is partially <a href="/wiki/Peripherally_selective_drug" title="Peripherally selective drug">peripherally selective</a>.<sup id="cite_ref-ODonnell1995_25-7" class="reference"><a href="#cite_note-ODonnell1995-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BouchardWeberGeiger2002_26-1" class="reference"><a href="#cite_note-BouchardWeberGeiger2002-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> The blood-brain barrier permeability of pseudoephedrine, ephedrine, and phenylpropanolamine is reduced compared to other <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">amphetamines</a> due to the presence of a <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> at the β carbon which decreases their <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilicity</a>.<sup id="cite_ref-BouchardWeberGeiger2002_26-2" class="reference"><a href="#cite_note-BouchardWeberGeiger2002-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> As such, they have a greater ratio of peripheral cardiovascular to central psychostimulant effect.<sup id="cite_ref-BouchardWeberGeiger2002_26-3" class="reference"><a href="#cite_note-BouchardWeberGeiger2002-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Besides entering the brain, these substances also cross the <a href="/wiki/Placenta" title="Placenta">placenta</a> and enter <a href="/wiki/Breast_milk" title="Breast milk">breast milk</a>.<sup id="cite_ref-ChuaBenrimojTriggs1989_11-8" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">plasma protein binding</a> of pseudoephedrine has been reported to be approximately 21 to 29%.<sup id="cite_ref-VolppHolzgrabe2019_9-1" class="reference"><a href="#cite_note-VolppHolzgrabe2019-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Schmidt2023_10-1" class="reference"><a href="#cite_note-Schmidt2023-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is bound to <a href="/wiki/Orosomucoid" title="Orosomucoid">α<sub>1</sub>-acid glycoprotein</a> (AGP) and <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a> (HSA).<sup id="cite_ref-VolppHolzgrabe2019_9-2" class="reference"><a href="#cite_note-VolppHolzgrabe2019-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Schmidt2023_10-2" class="reference"><a href="#cite_note-Schmidt2023-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></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=Pseudoephedrine&action=edit&section=14" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine is not extensively <a href="/wiki/Drug_metabolism" title="Drug metabolism">metabolized</a> and is subjected to minimal <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first-pass metabolism</a> with oral administration.<sup id="cite_ref-ChuaBenrimojTriggs1989_11-9" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-42" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-20" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Due to its <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> at the α <a href="/wiki/Carbon" title="Carbon">carbon</a> (i.e., it is an <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">amphetamine</a>), pseudoephedrine is not a <a href="/wiki/Substrate_(biochemistry)" class="mw-redirect" title="Substrate (biochemistry)">substrate</a> for <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidase</a> (MAO) and is not metabolized by this <a href="/wiki/Enzyme" title="Enzyme">enzyme</a>.<sup id="cite_ref-ODonnell1995_25-8" class="reference"><a href="#cite_note-ODonnell1995-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ChuaBenrimojTriggs1989_11-10" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JohnsonHricik1993_71-1" class="reference"><a href="#cite_note-JohnsonHricik1993-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Broadley2010_72-1" class="reference"><a href="#cite_note-Broadley2010-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> It is also not metabolized by <a href="/wiki/Catechol_O-methyltransferase" class="mw-redirect" title="Catechol O-methyltransferase">catechol <i>O</i>-methyltransferase</a> (COMT).<sup id="cite_ref-ODonnell1995_25-9" class="reference"><a href="#cite_note-ODonnell1995-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Pseudoephedrine is <a href="/wiki/Demethylation" title="Demethylation">demethylated</a> into the <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> <a href="/wiki/Cathine" title="Cathine">norpseudoephedrine</a> to a small extent.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-43" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ChuaBenrimojTriggs1989_11-11" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Similarly to pseudoephedrine, this metabolite is <a href="/wiki/Active_metabolite" title="Active metabolite">active</a> and shows <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>-like effects.<sup id="cite_ref-ChuaBenrimojTriggs1989_11-12" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Approximately 1 to 6% of pseudoephedrine is metabolized in the <a href="/wiki/Liver" title="Liver">liver</a> via <i>N</i>-demethylation to form norpseudoephedrine.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-44" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Elimination">Elimination</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=15" title="Edit section: Elimination"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine is <a href="/wiki/Excretion" title="Excretion">excreted</a> primarily via the <a href="/wiki/Kidney" title="Kidney">kidneys</a> in <a href="/wiki/Urine" title="Urine">urine</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-45" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ChuaBenrimojTriggs1989_11-13" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Its urinary excretion is highly influenced by urinary <a href="/wiki/PH" title="PH">pH</a> and is decreased when the urine is <a href="/wiki/Acidic" class="mw-redirect" title="Acidic">acidic</a> and is increased when it is <a href="/wiki/Alkaline" class="mw-redirect" title="Alkaline">alkaline</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-46" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ChuaBenrimojTriggs1989_11-14" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HughesEmpeyLand1983_58-4" class="reference"><a href="#cite_note-HughesEmpeyLand1983-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of pseudoephedrine on average is 5.4<span class="nowrap"> </span>hours<sup id="cite_ref-Eccles2007_2-21" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and ranges from 3 to 16<span class="nowrap"> </span>hours depending on urinary pH.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-47" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ChuaBenrimojTriggs1989_11-15" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> At a pH of 5.6 to 6.0, the <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of pseudoephedrine was 5.2 to 8.0<span class="nowrap"> </span>hours.<sup id="cite_ref-ChuaBenrimojTriggs1989_11-16" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> In one study, a more acidic pH of 5.0 resulted in a half-life of 3.0 to 6.4<span class="nowrap"> </span>hours, whereas a more alkaline pH of 8.0 resulted in a half-life of 9.2 to 16.0<span class="nowrap"> </span>hours.<sup id="cite_ref-ChuaBenrimojTriggs1989_11-17" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Substances that influence urinary acidity and are known to affect the excretion of amphetamine derivatives include <a href="/wiki/Acidifier" title="Acidifier">urinary acidifying agents</a> like <a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">ascorbic acid</a> and <a href="/wiki/Ammonium_chloride" title="Ammonium chloride">ammonium chloride</a> as well as <a href="/wiki/Alkalinizing_agent" title="Alkalinizing agent">urinary alkalinizing agents</a> like <a href="/wiki/Acetazolamide" title="Acetazolamide">acetazolamide</a>.<sup id="cite_ref-PatrickMarkowitz1997_77-1" class="reference"><a href="#cite_note-PatrickMarkowitz1997-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> </p><p>A majority of an <a href="/wiki/Oral_administration" title="Oral administration">oral</a> dose of pseudoephedrine is excreted unchanged in urine within 24<span class="nowrap"> </span>hours of administration.<sup id="cite_ref-ChuaBenrimojTriggs1989_11-18" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> This has been found to range from 43 to 96%.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-48" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ChuaBenrimojTriggs1989_11-19" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-22" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The amount excreted unchanged is dependent on urinary pH similarly to the drug's half-life, as a longer half-life and duration in the body allows more time for the drug to be metabolized.<sup id="cite_ref-ChuaBenrimojTriggs1989_11-20" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">duration of action</a> of pseudoephedrine, which is dependent on its <a href="/wiki/Elimination_(pharmacology)" title="Elimination (pharmacology)">elimination</a>, is 4 to 12<span class="nowrap"> </span>hours.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-49" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Aaron1990_12-1" class="reference"><a href="#cite_note-Aaron1990-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine has been reported to accumulate in people with <a href="/wiki/Renal_impairment" class="mw-redirect" title="Renal impairment">renal impairment</a>.<sup id="cite_ref-Sequeira1998_92-0" class="reference"><a href="#cite_note-Sequeira1998-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SicaComstock1989_93-0" class="reference"><a href="#cite_note-SicaComstock1989-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LyonTurney1996_94-0" class="reference"><a href="#cite_note-LyonTurney1996-94"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=16" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine, also known structurally as (1<i>S</i>,2<i>S</i>)-α,<i>N</i>-dimethyl-β-hydroxyphenethylamine or as (1<i>S</i>,2<i>S</i>)-<i>N</i>-methyl-β-hydroxyamphetamine, is a <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">substituted phenethylamine</a>, <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">amphetamine</a>, and <a href="/wiki/Substituted_%CE%B2-hydroxyamphetamine" title="Substituted β-hydroxyamphetamine">β-hydroxyamphetamine</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-50" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LaccourreyeWernerGiroud2015_13-9" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-23" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It is a <a href="/wiki/Diastereomer" title="Diastereomer">diastereomer</a> of <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>.<sup id="cite_ref-AbourashedEl-AlfyKhan2003_28-2" class="reference"><a href="#cite_note-AbourashedEl-AlfyKhan2003-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine is a <a href="/wiki/Small_molecule" title="Small molecule">small-molecule</a> <a href="/wiki/Chemical_compound" title="Chemical compound">compound</a> with the <a href="/wiki/Molecular_formula" class="mw-redirect" title="Molecular formula">molecular formula</a> C<sub>10</sub>H<sub>15</sub>NO and a <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a> of 165.23<span class="nowrap"> </span>g/mol.<sup id="cite_ref-PubChem_27-1" class="reference"><a href="#cite_note-PubChem-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DrugBank_95-0" class="reference"><a href="#cite_note-DrugBank-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup> It has an experimental <a href="/wiki/Partition_coefficient" title="Partition coefficient">log P</a> of 0.89, while its predicted log P values range from 0.9 to 1.32.<sup id="cite_ref-PubChem_27-2" class="reference"><a href="#cite_note-PubChem-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DrugBank_95-1" class="reference"><a href="#cite_note-DrugBank-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KrilFung1990_96-0" class="reference"><a href="#cite_note-KrilFung1990-96"><span class="cite-bracket">[</span>96<span class="cite-bracket">]</span></a></sup> The compound is relatively <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a>,<sup id="cite_ref-ChuaBenrimojTriggs1989_11-21" class="reference"><a href="#cite_note-ChuaBenrimojTriggs1989-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> but is also more <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> than other amphetamines.<sup id="cite_ref-BouchardWeberGeiger2002_26-4" class="reference"><a href="#cite_note-BouchardWeberGeiger2002-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> The lipophilicity of amphetamines is closely related to their brain permeability.<sup id="cite_ref-BharateMignaniWishwakarma2018_97-0" class="reference"><a href="#cite_note-BharateMignaniWishwakarma2018-97"><span class="cite-bracket">[</span>97<span class="cite-bracket">]</span></a></sup> For comparison to pseudoephedrine, the experimental log P of <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a> is 2.1,<sup id="cite_ref-SchepSlaughterBeasley2010_98-0" class="reference"><a href="#cite_note-SchepSlaughterBeasley2010-98"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup> of <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a> is 1.8,<sup id="cite_ref-PubChem-Amphetamine_99-0" class="reference"><a href="#cite_note-PubChem-Amphetamine-99"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SchepSlaughterBeasley2010_98-1" class="reference"><a href="#cite_note-SchepSlaughterBeasley2010-98"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup> of <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a> is 1.1,<sup id="cite_ref-PubChem-Ephedrine_100-0" class="reference"><a href="#cite_note-PubChem-Ephedrine-100"><span class="cite-bracket">[</span>100<span class="cite-bracket">]</span></a></sup> of <a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">phenylpropanolamine</a> is 0.7,<sup id="cite_ref-PubChem-Phenylpropanolamine_101-0" class="reference"><a href="#cite_note-PubChem-Phenylpropanolamine-101"><span class="cite-bracket">[</span>101<span class="cite-bracket">]</span></a></sup> of <a href="/wiki/Phenylephrine" title="Phenylephrine">phenylephrine</a> is -0.3,<sup id="cite_ref-PubChem-Phenylephrine_102-0" class="reference"><a href="#cite_note-PubChem-Phenylephrine-102"><span class="cite-bracket">[</span>102<span class="cite-bracket">]</span></a></sup> and of <a href="/wiki/Norepinephrine_(medication)" title="Norepinephrine (medication)">norepinephrine</a> is -1.2.<sup id="cite_ref-PubChem-Norepinephrine_103-0" class="reference"><a href="#cite_note-PubChem-Norepinephrine-103"><span class="cite-bracket">[</span>103<span class="cite-bracket">]</span></a></sup> Methamphetamine has high brain permeability,<sup id="cite_ref-SchepSlaughterBeasley2010_98-2" class="reference"><a href="#cite_note-SchepSlaughterBeasley2010-98"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup> whereas phenylephrine and norepinephrine are <a href="/wiki/Peripherally_selective_drug" title="Peripherally selective drug">peripherally selective drugs</a>.<sup id="cite_ref-Eccles2007_2-24" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FroeseDianGomez2020_104-0" class="reference"><a href="#cite_note-FroeseDianGomez2020-104"><span class="cite-bracket">[</span>104<span class="cite-bracket">]</span></a></sup> The optimal log P for brain permeation and central activity is about 2.1 (range 1.5–2.7).<sup id="cite_ref-PajouheshLenz2005_105-0" class="reference"><a href="#cite_note-PajouheshLenz2005-105"><span class="cite-bracket">[</span>105<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine is readily <a href="/wiki/Redox" title="Redox">reduced</a> into <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a> or <a href="/wiki/Oxidized" class="mw-redirect" title="Oxidized">oxidized</a> into <a href="/wiki/Methcathinone" title="Methcathinone">methcathinone</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-51" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:(pseudo)ephedrine_enantiomers.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/%28pseudo%29ephedrine_enantiomers.svg/400px-%28pseudo%29ephedrine_enantiomers.svg.png" decoding="async" width="400" height="419" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/%28pseudo%29ephedrine_enantiomers.svg/600px-%28pseudo%29ephedrine_enantiomers.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/%28pseudo%29ephedrine_enantiomers.svg/800px-%28pseudo%29ephedrine_enantiomers.svg.png 2x" data-file-width="420" data-file-height="440" /></a><figcaption>Two pairs of <a href="/wiki/Enantiomers" class="mw-redirect" title="Enantiomers">enantiomers</a>: <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a> (top) and pseudoephedrine (bottom).</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Nomenclatures">Nomenclatures</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=17" title="Edit section: Nomenclatures"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Levorotation_and_dextrorotation" class="mw-redirect" title="Levorotation and dextrorotation">dextrorotary</a> (+)- or d- <a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a> is (1<i>S</i>,2<i>S</i>)-pseudoephedrine, whereas the levorotating (−)- or l- form is (1<i>R</i>,2<i>R</i>)-pseudoephedrine. </p><p>In the outdated <a href="/wiki/Absolute_configuration#By_relative_configuration:_D-_and_L-" title="Absolute configuration"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D/L</span></span> system</a> (+)-pseudoephedrine is also referred to as <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L-</span></span>pseudoephedrine and (−)-pseudoephedrine as <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D-</span></span>pseudoephedrine (in the <a href="/wiki/Fisher_projection" class="mw-redirect" title="Fisher projection">Fisher projection</a> then the phenyl ring is drawn at bottom).<sup id="cite_ref-106" class="reference"><a href="#cite_note-106"><span class="cite-bracket">[</span>106<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-107" class="reference"><a href="#cite_note-107"><span class="cite-bracket">[</span>107<span class="cite-bracket">]</span></a></sup> </p><p>Often the <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D/L</span></span> system (with <a href="/wiki/Small_caps" title="Small caps">small caps</a>) and the <a href="/wiki/Absolute_configuration#By_optical_rotation:_(+)-_and_(−)-_or_d-_and_l-" title="Absolute configuration">d/l system</a> (with <a href="/wiki/Lower-case" class="mw-redirect" title="Lower-case">lower-case</a>) are confused. The result is that the dextrorotary d-pseudoephedrine is wrongly named <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D-</span></span>pseudoephedrine and the levorotary l-ephedrine (the diastereomer) wrongly <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L-</span></span>ephedrine. </p><p>The IUPAC names of the two enantiomers are (1<i>S</i>,2<i>S</i>)- respectively (1<i>R</i>,2<i>R</i>)-2-methylamino-1-phenylpropan-1-ol. Synonyms for both are <i>psi</i>-ephedrine and <i>threo</i>-ephedrine. </p><p>Pseudoephedrine is the <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</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 International Nonproprietary Name</span> of the (+)-form, when used as pharmaceutical substance.<sup id="cite_ref-108" class="reference"><a href="#cite_note-108"><span class="cite-bracket">[</span>108<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Detection_in_body_fluids">Detection in body fluids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=18" title="Edit section: Detection in body fluids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine may be quantified in blood, plasma, or urine to monitor any possible performance-enhancing use by athletes, confirm a diagnosis of poisoning, or to assist in a medicolegal death investigation. Some commercial <a href="/wiki/Immunoassay" title="Immunoassay">immunoassay</a> screening tests directed at the amphetamines cross-react appreciably with pseudoephedrine, but <a href="/wiki/Chromatography" title="Chromatography">chromatographic</a> techniques can easily distinguish pseudoephedrine from other phenethylamine derivatives. Blood or plasma pseudoephedrine concentrations are typically in the 50 to 300<span class="nowrap"> </span>μg/L range in persons taking the drug therapeutically, 500 to 3,000<span class="nowrap"> </span>μg/L in people with substance use disorder involving pseudoephedrine or poisoned patients, and 10 to 70<span class="nowrap"> </span>mg/L in cases of acute fatal <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a>.<sup id="cite_ref-BolandReinLew2003_109-0" class="reference"><a href="#cite_note-BolandReinLew2003-109"><span class="cite-bracket">[</span>109<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Baselt2008_110-0" class="reference"><a href="#cite_note-Baselt2008-110"><span class="cite-bracket">[</span>110<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Manufacturing">Manufacturing</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=19" title="Edit section: Manufacturing"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although pseudoephedrine occurs naturally as an <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> in certain plant species (for example, as a constituent of extracts from the <i><a href="/wiki/Ephedra_(medicine)" title="Ephedra (medicine)">Ephedra</a></i> species, also known as <i>ma huang</i>, in which it occurs together with other isomers of <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>), the majority of pseudoephedrine produced for commercial use is derived from <a href="/wiki/Yeast" title="Yeast">yeast</a> <a href="/wiki/Fermentation" title="Fermentation">fermentation</a> of <a href="/wiki/Dextrose" class="mw-redirect" title="Dextrose">dextrose</a> in the presence of <a href="/wiki/Benzaldehyde" title="Benzaldehyde">benzaldehyde</a>. In this process, specialized strains of yeast (typically a variety of <i><a href="/wiki/Candida_utilis" class="mw-redirect" title="Candida utilis">Candida utilis</a></i> or <i><a href="/wiki/Saccharomyces_cerevisiae" title="Saccharomyces cerevisiae">Saccharomyces cerevisiae</a></i>) are added to large vats containing water, dextrose and the enzyme <a href="/wiki/Pyruvate_decarboxylase" title="Pyruvate decarboxylase">pyruvate decarboxylase</a> (such as found in <a href="/wiki/Beet" class="mw-redirect" title="Beet">beets</a> and other plants). After the yeast has begun fermenting the dextrose, the benzaldehyde is added to the vats, and in this environment, the yeast converts the ingredients to the precursor <a href="/wiki/L-phenylacetylcarbinol" class="mw-redirect" title="L-phenylacetylcarbinol">l-phenylacetylcarbinol</a> (L-PAC). L-PAC is then chemically converted to pseudoephedrine via <a href="/wiki/Reductive_amination" title="Reductive amination">reductive amination</a>.<sup id="cite_ref-111" class="reference"><a href="#cite_note-111"><span class="cite-bracket">[</span>111<span class="cite-bracket">]</span></a></sup> </p><p>The bulk of pseudoephedrine is produced by commercial <a href="/wiki/Pharmaceutical_manufacturers" class="mw-redirect" title="Pharmaceutical manufacturers">pharmaceutical manufacturers</a> in India and China, where economic and industrial conditions favor its mass production for export.<sup id="cite_ref-112" class="reference"><a href="#cite_note-112"><span class="cite-bracket">[</span>112<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=20" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine, along with <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>, occurs <a href="/wiki/Natural_product" title="Natural product">naturally</a> in <a href="/wiki/Ephedra_(plant)" title="Ephedra (plant)">ephedra</a>.<sup id="cite_ref-LaccourreyeWernerGiroud2015_13-10" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AbourashedEl-AlfyKhan2003_28-3" class="reference"><a href="#cite_note-AbourashedEl-AlfyKhan2003-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kalix1991_113-0" class="reference"><a href="#cite_note-Kalix1991-113"><span class="cite-bracket">[</span>113<span class="cite-bracket">]</span></a></sup> This herb has been used for thousands of years in <a href="/wiki/Traditional_Chinese_medicine" title="Traditional Chinese medicine">traditional Chinese medicine</a>.<sup id="cite_ref-LaccourreyeWernerGiroud2015_13-11" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AbourashedEl-AlfyKhan2003_28-4" class="reference"><a href="#cite_note-AbourashedEl-AlfyKhan2003-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kalix1991_113-1" class="reference"><a href="#cite_note-Kalix1991-113"><span class="cite-bracket">[</span>113<span class="cite-bracket">]</span></a></sup> Pseudoephedrine was first <a href="/wiki/Chemical_isolate" class="mw-redirect" title="Chemical isolate">isolated</a> and characterized in 1889 by the German chemists <a href="/wiki/Albert_Ladenburg" title="Albert Ladenburg">Ladenburg</a> and Oelschlägel, who used a sample that had been isolated from <i><a href="/wiki/Ephedra_vulgaris" class="mw-redirect" title="Ephedra vulgaris">Ephedra vulgaris</a></i> by the <a href="/wiki/Merck_Group" title="Merck Group">Merck pharmaceutical corporation</a> of <a href="/wiki/Darmstadt" title="Darmstadt">Darmstadt</a>, Germany.<sup id="cite_ref-AbourashedEl-AlfyKhan2003_28-5" class="reference"><a href="#cite_note-AbourashedEl-AlfyKhan2003-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ChenKao1926_29-1" class="reference"><a href="#cite_note-ChenKao1926-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LadenburgOelschlägel1889_114-0" class="reference"><a href="#cite_note-LadenburgOelschlägel1889-114"><span class="cite-bracket">[</span>114<span class="cite-bracket">]</span></a></sup> It was first <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesized</a> in the 1920s in <a href="/wiki/Japan" title="Japan">Japan</a>.<sup id="cite_ref-LaccourreyeWernerGiroud2015_13-12" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Subsequently, pseudoephedrine was introduced for medical use as a decongestant.<sup id="cite_ref-LaccourreyeWernerGiroud2015_13-13" class="reference"><a href="#cite_note-LaccourreyeWernerGiroud2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=21" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Generic_names">Generic names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=22" title="Edit section: Generic names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>Pseudoephedrine</i> is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of the drug and its <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</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 International Nonproprietary Name</span> and <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BAN</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 British Approved Name</span>, while <i>pseudoéphédrine</i> is its <a href="/wiki/D%C3%A9nomination_Commune_Fran%C3%A7aise" title="Dénomination Commune Française"><abbr title="Dénomination Commune Française">DCF</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 Dénomination Commune Française</span> and <i>pseudoefedrina</i> is its <a href="/wiki/Denominazione_Comune_Italiana" title="Denominazione Comune Italiana"><abbr title="Denominazione Comune Italiana">DCIT</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 Denominazione Comune Italiana</span>.<sup id="cite_ref-Elks2014_115-0" class="reference"><a href="#cite_note-Elks2014-115"><span class="cite-bracket">[</span>115<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_116-0" class="reference"><a href="#cite_note-IndexNominum2000-116"><span class="cite-bracket">[</span>116<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_117-0" class="reference"><a href="#cite_note-MortonHall2012-117"><span class="cite-bracket">[</span>117<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_118-0" class="reference"><a href="#cite_note-Drugs.com-118"><span class="cite-bracket">[</span>118<span class="cite-bracket">]</span></a></sup> <i>Pseudoephedrine hydrochloride</i> is its <a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name"><abbr title="United States Adopted Name">USAN</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 United States Adopted Name</span> and <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BANM</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 British Approved Name</span> in the case of the <a href="/wiki/Hydrochloride" title="Hydrochloride">hydrochloride</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a>; <i>pseudoephedrine sulfate</i> is its <abbr title="United States Adopted Name">USAN</abbr> in the case of the <a href="/wiki/Sulfate" title="Sulfate">sulfate</a> salt; <i>pseudoephedrine polistirex</i> its <abbr title="United States Adopted Name">USAN</abbr> in the case of the polistirex form; and <i>d-isoephedrine sulfate</i> is its <a href="/wiki/Japanese_Accepted_Name" title="Japanese Accepted Name"><abbr title="Japanese Accepted Name">JAN</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 Japanese Accepted Name</span> in the case of the sulfate salt.<sup id="cite_ref-Elks2014_115-1" class="reference"><a href="#cite_note-Elks2014-115"><span class="cite-bracket">[</span>115<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_116-1" class="reference"><a href="#cite_note-IndexNominum2000-116"><span class="cite-bracket">[</span>116<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_117-1" class="reference"><a href="#cite_note-MortonHall2012-117"><span class="cite-bracket">[</span>117<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_118-1" class="reference"><a href="#cite_note-Drugs.com-118"><span class="cite-bracket">[</span>118<span class="cite-bracket">]</span></a></sup> Pseudoephedrine is also known as <i>Ψ-ephedrine</i> and <i>isoephedrine</i>.<sup id="cite_ref-Elks2014_115-2" class="reference"><a href="#cite_note-Elks2014-115"><span class="cite-bracket">[</span>115<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_117-2" class="reference"><a href="#cite_note-MortonHall2012-117"><span class="cite-bracket">[</span>117<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=23" title="Edit section: Brand names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-List_dispute plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/40px-Ambox_important.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/60px-Ambox_important.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/80px-Ambox_important.svg.png 2x" data-file-width="40" data-file-height="40" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">The <b>inclusion or exclusion of items</b> from this list or <b>length of this list</b> is disputed.<span class="hide-when-compact"> Please discuss this issue on the <a href="/wiki/Talk:Pseudoephedrine" title="Talk:Pseudoephedrine">talk page</a>.</span></div></td></tr></tbody></table> <p>The following is a list of consumer medicines that either contain pseudoephedrine or have switched to a less-regulated alternative such as <a href="/wiki/Phenylephrine" title="Phenylephrine">phenylephrine</a>. </p> <ul><li><a href="/wiki/Actifed" title="Actifed">Actifed</a> (made by <a href="/wiki/GlaxoSmithKline" class="mw-redirect" title="GlaxoSmithKline">GlaxoSmithKline</a>) — contains 60 mg pseudoephedrine and 2.5 mg <a href="/wiki/Triprolidine" title="Triprolidine">triprolidine</a> in certain countries.</li> <li>Advil Cold & Sinus (made by Pfizer Canada Inc.) — contains 30 mg pseudoephedrine hydrochloride (also 200 mg <a href="/wiki/Ibuprofen" title="Ibuprofen">ibuprofen</a>).</li> <li><a href="/wiki/Naproxen/pseudoephedrine" title="Naproxen/pseudoephedrine">Aleve-D Sinus & Cold</a> (made by <a href="/wiki/Bayer_Healthcare" class="mw-redirect" title="Bayer Healthcare">Bayer Healthcare</a>) — contains 120 mg pseudoephedrine hydrochloride (also 220 mg <a href="/wiki/Naproxen" title="Naproxen">naproxen</a>).</li> <li><a href="/wiki/Allegra-D" class="mw-redirect" title="Allegra-D">Allegra-D</a> (made by <a href="/wiki/Sanofi_Aventis" class="mw-redirect" title="Sanofi Aventis">Sanofi Aventis</a>) — contains 120 mg of pseudoephedrine hydrochloride (also 60 mg of <a href="/wiki/Fexofenadine" title="Fexofenadine">fexofenadine</a>).</li> <li><a href="/wiki/Allerclear-D" class="mw-redirect" title="Allerclear-D">Allerclear-D</a> (made by <a href="/wiki/Kirkland_Signature" class="mw-redirect" title="Kirkland Signature">Kirkland Signature</a>) — contains 240 mg of pseudoephedrine sulfate (also 10 mg of <a href="/wiki/Loratadine" title="Loratadine">loratadine</a>).</li> <li><a href="/wiki/Benadryl" title="Benadryl">Benadryl Allergy Relief Plus Decongestant</a> (made by <a href="/wiki/McNeil_Consumer_Healthcare" title="McNeil Consumer Healthcare">McNeil Consumer Healthcare</a>, a <a href="/wiki/Kenvue" title="Kenvue">Kenvue</a> company) — contains 60 mg pseudoephedrine hydrochloride (also 8 mg <a href="/wiki/Acrivastine" title="Acrivastine">acrivastine</a>)<sup id="cite_ref-119" class="reference"><a href="#cite_note-119"><span class="cite-bracket">[</span>119<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Cetirizine/pseudoephedrine" title="Cetirizine/pseudoephedrine">Cirrus</a> (made by <a href="/wiki/UCB_(company)" title="UCB (company)">UCB</a>) — contains 120 mg pseudoephedrine hydrochloride (also 5 mg <a href="/wiki/Cetirizine" title="Cetirizine">cetirizine</a>).</li> <li><a href="/wiki/Claritin-D" class="mw-redirect" title="Claritin-D">Claritin-D</a> (made by Bayer Healthcare) — contains 120 mg of pseudoephedrine sulfate (also 5 mg of loratadine).</li> <li><a href="/wiki/Claritin-D" class="mw-redirect" title="Claritin-D">Claritin-D 24 Hour</a> (made by Bayer Healthcare) — contains 240 mg of pseudoephedrine sulfate (also 10 mg of loratadine).</li> <li>Codral (made by <a href="/wiki/Asia-Pacific" class="mw-redirect" title="Asia-Pacific">Asia-Pacific</a> subsidiary of Johnson & Johnson) — Codral Original contains pseudoephedrine, Codral New Formula substitutes phenylephrine for pseudoephedrine.</li> <li>Congestal (made by <a href="/w/index.php?title=SIGMA_Pharmaceutical_Industries&action=edit&redlink=1" class="new" title="SIGMA Pharmaceutical Industries (page does not exist)">SIGMA Pharmaceutical Industries</a>) — contains 60 mg pseudoephedrine hydrochloride (also 650 mg <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol</a> and 4 mg <a href="/wiki/Chlorpheniramine" class="mw-redirect" title="Chlorpheniramine">chlorpheniramine</a>).<sup id="cite_ref-120" class="reference"><a href="#cite_note-120"><span class="cite-bracket">[</span>120<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-121" class="reference"><a href="#cite_note-121"><span class="cite-bracket">[</span>121<span class="cite-bracket">]</span></a></sup></li> <li>Contac (made by GlaxoSmithKline) — previously contained pseudoephedrine, now contains phenylephrine. As at Nov 2014 UK version still contains 30 mg pseudoephedrine hydrochloride per tablet.</li> <li>Demazin (made by Bayer Healthcare) — contains pseudoephedrine sulfate and <a href="/wiki/Chlorpheniramine" class="mw-redirect" title="Chlorpheniramine">chlorpheniramine</a> maleate</li> <li>Eltor (made by Sanofi Aventis) — contains pseudoephedrine hydrochloride.</li> <li><a href="/wiki/Mucinex" class="mw-redirect" title="Mucinex">Mucinex-D</a> (made by <a href="/wiki/Reckitt_Benckiser" class="mw-redirect" title="Reckitt Benckiser">Reckitt Benckiser</a>) — contains 60 mg pseudoephedrine hydrochloride (also 1200 mg <a href="/wiki/Guaifenesin" title="Guaifenesin">guaifenesin</a>).</li> <li><a href="/wiki/Nexafed" title="Nexafed">Nexafed</a> (made by <a href="/wiki/Acura_Pharmaceuticals" title="Acura Pharmaceuticals">Acura Pharmaceuticals</a>) — contains 30 mg pseudoephedrine per tablet, formulated with Impede Meth-Deterrent technology.</li> <li><a href="/wiki/Nurofen" title="Nurofen">Nurofen</a> Cold & Flu (made by Reckitt Benckiser) — contains 30 mg pseudoephedrine hydrochloride (also 200 mg ibuprofen).</li> <li>Respidina – contains 120 mg of pseudoephedrine in the form of extended release tablets.</li> <li>Rhinex Flash (made by <a href="/w/index.php?title=Pharma_Product_Manufacturing&action=edit&redlink=1" class="new" title="Pharma Product Manufacturing (page does not exist)">Pharma Product Manufacturing</a>, Cambodia) — contains pseudoephedrine combined with paracetamol and triprolidine.</li> <li>Rhinos SR (made by <a href="/w/index.php?title=Dexa_Medica&action=edit&redlink=1" class="new" title="Dexa Medica (page does not exist)">Dexa Medica</a>) — contains 120 mg of pseudoephedrine hydrochloride</li> <li><a href="/wiki/Sinutab" title="Sinutab">Sinutab</a> (made by McNeil Consumer Healthcare, a Kenvue Company) — contains 500 mg paracetamol and 30 mg pseudoephedrine hydrochloride.</li> <li><b>Sudafed</b> Decongestant (made by McNeil Consumer Healthcare, a Kenvue company) — contains 60 mg of pseudoephedrine hydrochloride. Not to be confused with Sudafed PE, which contains phenylephrine.</li> <li><b>Theraflu</b> (made by <a href="/wiki/Novartis" title="Novartis">Novartis</a>) — previously contained pseudoephedrine, now contains phenylephrine</li> <li>Trima — contains 60 mg pseudoephedrine hydrochloride</li> <li>Tylol Hot (made by NOBEL İLAÇ SANAYİİ VE TİCARET A.Ş., Turkey) — a packet of 20 g contains 60 mg pseudoephedrine hydrochloride, 500 mg paracetamol and 4 mg <a href="/wiki/Chlorphenamine" title="Chlorphenamine">chlorpheniramine maleate</a></li> <li>Unifed (made by <a href="/w/index.php?title=United_Pharmaceutical_Manufacturer&action=edit&redlink=1" class="new" title="United Pharmaceutical Manufacturer (page does not exist)">United Pharmaceutical Manufacturer</a>, Jordan) — contains pseudoephedrine hydrochloride (also triprolidine and <a href="/wiki/Guaifenesin" title="Guaifenesin">guaifenesin</a>).</li> <li><a href="/wiki/Zyrtec-D" class="mw-redirect" title="Zyrtec-D">Zyrtec-D</a> 12 Hour (made by McNeil Consumer Healthcare, a Kenvue company) — contains 120 mg pseudoephedrine hydrochloride (also 5 mg of cetirizine).</li> <li>Zephrex-D (made by <a href="/w/index.php?title=Westport_Pharmaceuticals&action=edit&redlink=1" class="new" title="Westport Pharmaceuticals (page does not exist)">Westport Pharmaceuticals</a>) – a special meth-resistant form of pseudoephedrine that becomes gooey when heated.</li></ul> <div class="mw-heading mw-heading3"><h3 id="Recreational_use">Recreational use</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=24" title="Edit section: Recreational use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">Over-the-counter</a> pseudoephedrine has been <a href="/wiki/Drug_misuse" class="mw-redirect" title="Drug misuse">misused</a> as a <a href="/wiki/Psychostimulant" class="mw-redirect" title="Psychostimulant">psychostimulant</a>.<sup id="cite_ref-SchifanoChiappiniMiuli2021_17-4" class="reference"><a href="#cite_note-SchifanoChiappiniMiuli2021-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Six <a href="/wiki/Case_report" title="Case report">case reports</a> and one <a href="/wiki/Case_series" title="Case series">case series</a> of pseudoephedrine misuse have been published as of 2021.<sup id="cite_ref-SchifanoChiappiniMiuli2021_17-5" class="reference"><a href="#cite_note-SchifanoChiappiniMiuli2021-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> There is a case report of <a href="/wiki/Self-medication" title="Self-medication">self-medication</a> with pseudoephedrine in massive doses for treatment of <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>.<sup id="cite_ref-SchifanoChiappiniMiuli2021_17-6" class="reference"><a href="#cite_note-SchifanoChiappiniMiuli2021-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DiazWiseSemchyshyn1979_66-1" class="reference"><a href="#cite_note-DiazWiseSemchyshyn1979-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Use_in_exercise_and_sports">Use in exercise and sports</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=25" title="Edit section: Use in exercise and sports"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine has been used as a <a href="/wiki/Performance-enhancing_drug" class="mw-redirect" title="Performance-enhancing drug">performance-enhancing drug</a> in <a href="/wiki/Exercise" title="Exercise">exercise</a> and <a href="/wiki/Sports" class="mw-redirect" title="Sports">sports</a> due to its sympathomimetic and stimulant effects.<sup id="cite_ref-TrinhKimRitsma2015_19-4" class="reference"><a href="#cite_note-TrinhKimRitsma2015-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GheorghievHosseiniMoran2018_20-4" class="reference"><a href="#cite_note-GheorghievHosseiniMoran2018-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Because of these effects, pseudoephedrine can increase <a href="/wiki/Heart_rate" title="Heart rate">heart rate</a>, elevate <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>, improve <a href="/wiki/Mental_energy" title="Mental energy">mental energy</a>, and reduce <a href="/wiki/Fatigue_(medical)" class="mw-redirect" title="Fatigue (medical)">fatigue</a>, among other performance-enhancing effects.<sup id="cite_ref-TrinhKimRitsma2015_19-5" class="reference"><a href="#cite_note-TrinhKimRitsma2015-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GheorghievHosseiniMoran2018_20-5" class="reference"><a href="#cite_note-GheorghievHosseiniMoran2018-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SalernoJackson2005_22-14" class="reference"><a href="#cite_note-SalernoJackson2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>A 2015 <a href="/wiki/Systematic_review" title="Systematic review">systematic review</a> found that pseudoephedrine lacked performance-enhancing effects at therapeutic doses (60–120<span class="nowrap"> </span>mg) but significantly enhanced athletic performance at supratherapeutic doses (≥180<span class="nowrap"> </span>mg).<sup id="cite_ref-TrinhKimRitsma2015_19-6" class="reference"><a href="#cite_note-TrinhKimRitsma2015-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> A subsequent 2018 <a href="/wiki/Meta-analysis" title="Meta-analysis">meta-analysis</a>, which included seven additional studies, found that pseudoephedrine had a small positive effect on heart rate (<a href="/wiki/Standardized_mean_difference" class="mw-redirect" title="Standardized mean difference"><abbr title="standardized mean difference">SMD</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 standardized mean difference</span> = 0.43) but insignificant effects on time trials, perceived exertion ratings, blood <a href="/wiki/Glucose" title="Glucose">glucose</a> levels, and blood <a href="/wiki/Lactic_acid" title="Lactic acid">lactate</a> levels.<sup id="cite_ref-GheorghievHosseiniMoran2018_20-6" class="reference"><a href="#cite_note-GheorghievHosseiniMoran2018-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> However, subgroup analyses revealed that <a href="/wiki/Effect_size" title="Effect size">effect sizes</a> were larger for heart rate increases and quicker time trials in well-trained athletes and younger participants, for shorter exercise sessions with pseudoephedrine administered within 90<span class="nowrap"> </span>minutes beforehand, and with higher doses of pseudoephedrine.<sup id="cite_ref-GheorghievHosseiniMoran2018_20-7" class="reference"><a href="#cite_note-GheorghievHosseiniMoran2018-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> A <a href="/wiki/Dose%E2%80%93response_relationship" title="Dose–response relationship">dose–response relationship</a> was established, with larger doses (>170<span class="nowrap"> </span>mg) showing greater increases in heart rate and faster time trials than with smaller doses (≤170<span class="nowrap"> </span>mg) (<abbr title="standardized mean difference">SMD</abbr> = 0.85 for heart rate and <abbr title="standardized mean difference">SMD</abbr> = -0.24 for time trials, respectively).<sup id="cite_ref-GheorghievHosseiniMoran2018_20-8" class="reference"><a href="#cite_note-GheorghievHosseiniMoran2018-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> In any case, the meta-analysis concluded that the performance-enhancing effects of pseudoephedrine were marginal to small and likely to be lower in magnitude than with <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>.<sup id="cite_ref-GheorghievHosseiniMoran2018_20-9" class="reference"><a href="#cite_note-GheorghievHosseiniMoran2018-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> It is relevant in this regard that caffeine is a permitted stimulant in competitive sports.<sup id="cite_ref-GheorghievHosseiniMoran2018_20-10" class="reference"><a href="#cite_note-GheorghievHosseiniMoran2018-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine was on the <a href="/wiki/International_Olympic_Committee" title="International Olympic Committee">International Olympic Committee</a>'s (IOC) banned substances list until 2004 when the <a href="/wiki/World_Anti-Doping_Agency" title="World Anti-Doping Agency">World Anti-Doping Agency</a> (WADA) list replaced the IOC list. Although WADA initially only <i>monitored</i> pseudoephedrine, it went back onto the "banned" list on 1 January 2010.<sup id="cite_ref-122" class="reference"><a href="#cite_note-122"><span class="cite-bracket">[</span>122<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine is excreted through urine, and the concentration in urine of this drug shows a large inter-individual spread; that is, the same dose can give a vast difference in urine concentration for different individuals.<sup id="cite_ref-123" class="reference"><a href="#cite_note-123"><span class="cite-bracket">[</span>123<span class="cite-bracket">]</span></a></sup> Pseudoephedrine is approved to be taken up to 240 mg per day. In seven healthy male subjects, this dose yielded a urine concentration range of 62.8 to 294.4 microgram per milliliter (μg/mL) with mean ± standard deviation 149 ± 72 μg/mL.<sup id="cite_ref-124" class="reference"><a href="#cite_note-124"><span class="cite-bracket">[</span>124<span class="cite-bracket">]</span></a></sup> Thus, normal dosage of 240 mg pseudoephedrine per day can result in urine concentration levels exceeding the limit of 150 μg/mL set by WADA for about half of all users.<sup id="cite_ref-125" class="reference"><a href="#cite_note-125"><span class="cite-bracket">[</span>125<span class="cite-bracket">]</span></a></sup> Furthermore, hydration status does not affect the urinary concentration of pseudoephedrine.<sup id="cite_ref-126" class="reference"><a href="#cite_note-126"><span class="cite-bracket">[</span>126<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="List_of_doping_cases">List of doping cases</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=26" title="Edit section: List of doping cases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Canadian rower <a href="/wiki/Silken_Laumann" title="Silken Laumann">Silken Laumann</a> was stripped of her <a href="/wiki/1995_Pan_American_Games" title="1995 Pan American Games">1995 Pan American Games</a> team gold medal after testing positive for pseudoephedrine.<sup id="cite_ref-127" class="reference"><a href="#cite_note-127"><span class="cite-bracket">[</span>127<span class="cite-bracket">]</span></a></sup></li> <li>In February 2000, <a href="/wiki/Elena_Berezhnaya" title="Elena Berezhnaya">Elena Berezhnaya</a> and <a href="/wiki/Anton_Sikharulidze" title="Anton Sikharulidze">Anton Sikharulidze</a> won gold at the <a href="/wiki/2000_European_Figure_Skating_Championships" title="2000 European Figure Skating Championships">2000 European Figure Skating Championships</a> but were stripped of their medals after Berezhnaya tested positive. This resulted in a three-month disqualification from the date of the test, and the medal being stripped.<sup id="cite_ref-wallech_128-0" class="reference"><a href="#cite_note-wallech-128"><span class="cite-bracket">[</span>128<span class="cite-bracket">]</span></a></sup> She stated that she had taken cold medication approved by a doctor but had failed to inform the ISU as required.<sup id="cite_ref-disq_129-0" class="reference"><a href="#cite_note-disq-129"><span class="cite-bracket">[</span>129<span class="cite-bracket">]</span></a></sup> The pair missed the World Championships that year as a result of the disqualification.</li> <li>Romanian gymnast <a href="/wiki/Andreea_R%C4%83ducan" title="Andreea Răducan">Andreea Răducan</a> was stripped of her gold medal at the <a href="/wiki/2000_Summer_Olympic_Games" class="mw-redirect" title="2000 Summer Olympic Games">2000 Summer Olympic Games</a> after testing positive. She took two pills given to her by the team coach for a cold. Although she was stripped of the overall gold medal, she kept her other medals, and, unlike in most other doping cases, was not banned from competing again; only the team doctor was banned for a number of years. <a href="/wiki/Ion_%C8%9Airiac" title="Ion Țiriac">Ion Țiriac</a>, the president of the Romanian Olympic Committee, resigned over the scandal.<sup id="cite_ref-130" class="reference"><a href="#cite_note-130"><span class="cite-bracket">[</span>130<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-131" class="reference"><a href="#cite_note-131"><span class="cite-bracket">[</span>131<span class="cite-bracket">]</span></a></sup></li> <li>In the <a href="/wiki/2010_Winter_Olympic_Games" class="mw-redirect" title="2010 Winter Olympic Games">2010 Winter Olympic Games</a>, the IOC issued a reprimand against the Slovak <a href="/wiki/Ice_hockey" title="Ice hockey">ice hockey</a> player <a href="/wiki/Lubomir_Visnovsky" class="mw-redirect" title="Lubomir Visnovsky">Lubomir Visnovsky</a> for usage of pseudoephedrine.<sup id="cite_ref-132" class="reference"><a href="#cite_note-132"><span class="cite-bracket">[</span>132<span class="cite-bracket">]</span></a></sup></li> <li>In the <a href="/wiki/2014_Winter_Olympic_Games" class="mw-redirect" title="2014 Winter Olympic Games">2014 Winter Olympic Games</a> <a href="/wiki/Sweden_men%27s_national_ice_hockey_team" title="Sweden men's national ice hockey team">Team Sweden</a> and <a href="/wiki/Washington_Capitals" title="Washington Capitals">Washington Capitals</a> ice hockey player <a href="/wiki/Nicklas_B%C3%A4ckstr%C3%B6m" title="Nicklas Bäckström">Nicklas Bäckström</a> was prevented from playing in the final for usage of pseudoephedrine. Bäckström claimed he was using it as allergy medication.<sup id="cite_ref-133" class="reference"><a href="#cite_note-133"><span class="cite-bracket">[</span>133<span class="cite-bracket">]</span></a></sup> In March 2014, the IOC Disciplinary Commission decided that Bäckström would be awarded the silver medal.<sup id="cite_ref-IOC_134-0" class="reference"><a href="#cite_note-IOC-134"><span class="cite-bracket">[</span>134<span class="cite-bracket">]</span></a></sup> In January 2015 Bäckström, the IOC, WADA and the <a href="/wiki/International_Ice_Hockey_Federation" title="International Ice Hockey Federation">IIHF</a> agreed to a settlement in which he accepted a reprimand but was cleared of attempting to enhance his performance.<sup id="cite_ref-Washington_Post_135-0" class="reference"><a href="#cite_note-Washington_Post-135"><span class="cite-bracket">[</span>135<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Manufacture_of_amphetamines">Manufacture of amphetamines</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=27" title="Edit section: Manufacture of amphetamines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Its membership in the <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">amphetamine</a> class has made pseudoephedrine a sought-after <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">chemical precursor</a> in the <a href="/wiki/Clandestine_chemistry" title="Clandestine chemistry">illicit manufacture</a> of <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a> and <a href="/wiki/Methcathinone" title="Methcathinone">methcathinone</a>.<sup id="cite_ref-GłowackaWiela-Hojeńska2021_1-52" class="reference"><a href="#cite_note-GłowackaWiela-Hojeńska2021-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> As a result of the increasing regulatory restrictions on the sale and distribution of pseudoephedrine, pharmaceutical firms have reformulated medications to use alternative compounds, particularly <a href="/wiki/Phenylephrine" title="Phenylephrine">phenylephrine</a>, even though its efficacy as an oral decongestant has been demonstrated to be indistinguishable from placebo.<sup id="cite_ref-pmid17264159_136-0" class="reference"><a href="#cite_note-pmid17264159-136"><span class="cite-bracket">[</span>136<span class="cite-bracket">]</span></a></sup> </p><p>In the United States, federal laws control the sale of pseudoephedrine-containing products.<sup id="cite_ref-FDA_legal_137-0" class="reference"><a href="#cite_note-FDA_legal-137"><span class="cite-bracket">[</span>137<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CMEA_138-0" class="reference"><a href="#cite_note-CMEA-138"><span class="cite-bracket">[</span>138<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MPPA_139-0" class="reference"><a href="#cite_note-MPPA-139"><span class="cite-bracket">[</span>139<span class="cite-bracket">]</span></a></sup> Retailers in the US have created corporate policies restricting the sale of pseudoephedrine-containing products.<sup id="cite_ref-140" class="reference"><a href="#cite_note-140"><span class="cite-bracket">[</span>140<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-141" class="reference"><a href="#cite_note-141"><span class="cite-bracket">[</span>141<span class="cite-bracket">]</span></a></sup> Their policies restrict sales by limiting purchase quantities and requiring a minimum age and government issued photographic identification.<sup id="cite_ref-CMEA_138-1" class="reference"><a href="#cite_note-CMEA-138"><span class="cite-bracket">[</span>138<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MPPA_139-1" class="reference"><a href="#cite_note-MPPA-139"><span class="cite-bracket">[</span>139<span class="cite-bracket">]</span></a></sup> These requirements are similar to and sometimes more stringent than existing law. Internationally, pseudoephedrine is listed as a <a href="/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances#List_of_controlled_drug_precursors" title="United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances">Table I precursor</a> under the <a href="/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances" title="United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances">United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances</a>.<sup id="cite_ref-autogenerated1_142-0" class="reference"><a href="#cite_note-autogenerated1-142"><span class="cite-bracket">[</span>142<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Legal_status">Legal status</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=28" title="Edit section: Legal status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Australia">Australia</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=29" title="Edit section: Australia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:VM_0237_sale_pharmacy.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/VM_0237_sale_pharmacy.jpg/220px-VM_0237_sale_pharmacy.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/VM_0237_sale_pharmacy.jpg/330px-VM_0237_sale_pharmacy.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e5/VM_0237_sale_pharmacy.jpg/440px-VM_0237_sale_pharmacy.jpg 2x" data-file-width="1280" data-file-height="960" /></a><figcaption>A warning at an Australian pharmacy</figcaption></figure> <p>Illicit diversion of pseudoephedrine in Australia has caused significant changes to the way the products are regulated. As of 2006<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Pseudoephedrine&action=edit">[update]</a></sup>, all products containing pseudoephedrine have been rescheduled as either "Pharmacist Only Medicines" (Schedule 3) or "Prescription Only Medicines" (Schedule 4), depending on the amount of pseudoephedrine in the product. A Pharmacist Only Medicine may only be sold to the public if a pharmacist is directly involved in the transaction. These medicines must be kept behind the counter, away from public access. </p><p>Pharmacists are also encouraged (and in some states required) to log purchases with the online database Project STOP.<sup id="cite_ref-143" class="reference"><a href="#cite_note-143"><span class="cite-bracket">[</span>143<span class="cite-bracket">]</span></a></sup> </p><p>As a result, some pharmacies no longer stock Sudafed, the common brand of pseudoephedrine cold/sinus tablets, opting instead to sell Sudafed PE, a <a href="/wiki/Phenylephrine" title="Phenylephrine">phenylephrine</a> product that has not been proven effective in clinical trials.<sup id="cite_ref-pmid17264159_136-1" class="reference"><a href="#cite_note-pmid17264159-136"><span class="cite-bracket">[</span>136<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-144" class="reference"><a href="#cite_note-144"><span class="cite-bracket">[</span>144<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eccles2007_2-25" class="reference"><a href="#cite_note-Eccles2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Belgium">Belgium</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=30" title="Edit section: Belgium"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Until 2024, several formulations of pseudoephedrine were available over-the-counter in Belgium.<sup id="cite_ref-145" class="reference"><a href="#cite_note-145"><span class="cite-bracket">[</span>145<span class="cite-bracket">]</span></a></sup> However, new legislation came into effect in November 2024, banning the over-the-counter sale of all medicines containing pseudoephedrine.<sup id="cite_ref-146" class="reference"><a href="#cite_note-146"><span class="cite-bracket">[</span>146<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-147" class="reference"><a href="#cite_note-147"><span class="cite-bracket">[</span>147<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Canada">Canada</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=31" title="Edit section: Canada"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a> has investigated the risks and benefits of pseudoephedrine and <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>/<a href="/wiki/Ephedra_(medicine)" title="Ephedra (medicine)">Ephedra</a>. Near the end of the study, Health Canada issued a warning on their website stating that those who are under the age of 12, or who have heart disease and may have strokes, should avoid taking pseudoephedrine and ephedrine. Also, they warned that everyone should avoid taking ephedrine or pseudoephedrine with other stimulants like <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>. They also banned all products that contain both ephedrine (or pseudoephedrine) and caffeine.<sup id="cite_ref-148" class="reference"><a href="#cite_note-148"><span class="cite-bracket">[</span>148<span class="cite-bracket">]</span></a></sup> </p><p>Products whose only medicinal ingredient is pseudoephedrine must be kept behind the pharmacy counter. Products containing pseudoephedrine along with other medicinal ingredients may be displayed on store shelves but may be sold only in a pharmacy when a pharmacist is present.<sup id="cite_ref-149" class="reference"><a href="#cite_note-149"><span class="cite-bracket">[</span>149<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-150" class="reference"><a href="#cite_note-150"><span class="cite-bracket">[</span>150<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Colombia">Colombia</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=32" title="Edit section: Colombia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Colombian government prohibited the trade of pseudoephedrine in 2010.<sup id="cite_ref-151" class="reference"><a href="#cite_note-151"><span class="cite-bracket">[</span>151<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Estonia">Estonia</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=33" title="Edit section: Estonia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine is an over-the-counter drug in Estonia.<sup id="cite_ref-152" class="reference"><a href="#cite_note-152"><span class="cite-bracket">[</span>152<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Finland">Finland</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=34" title="Edit section: Finland"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine medicines can only be obtained with a prescription in Finland.<sup id="cite_ref-153" class="reference"><a href="#cite_note-153"><span class="cite-bracket">[</span>153<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability"><span title="The material near this tag failed verification of its source citation(s). (September 2023)">failed verification</span></a></i>]</sup> </p> <div class="mw-heading mw-heading4"><h4 id="France">France</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=35" title="Edit section: France"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine-containing combination products are available over the counter from pharmacies, most commonly with Paracetamol under the brand name "Dolihrume". Products combining pseudoephedrine and ibuprofen or certain antihistamines are also available. However, products containing pseudoephedrine as a single ingredient are not sold.<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. (December 2024)">citation needed</span></a></i>]</sup> In October 2023, the French health department officially warned against the usage of pseudoephedrine for patients with a cold. It also suggested the substance's availability could be restricted in the future, pending its pharmaceutical re-evaluation on <a href="/wiki/European_Union" title="European Union">EU</a> level.<sup id="cite_ref-154" class="reference"><a href="#cite_note-154"><span class="cite-bracket">[</span>154<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-155" class="reference"><a href="#cite_note-155"><span class="cite-bracket">[</span>155<span class="cite-bracket">]</span></a></sup> In December 2024, the government announced pseudoephedrine medicines would henceforth only be obtainable with a prescription. </p> <div class="mw-heading mw-heading4"><h4 id="Germany">Germany</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=36" title="Edit section: Germany"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Various pseudoephedrine-containing products in combination with ibuprofen, <a href="/wiki/Aspirin" title="Aspirin">aspirin</a>, or antihistamines can be obtained without a prescription upon request at a pharmacy. Common names include Aspirin Complex, Reactine Duo, and RhinoPront. Products containing pseudoephedrine as a single ingredient are not available.<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. (December 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading4"><h4 id="Japan">Japan</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=37" title="Edit section: Japan"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Medications that contain more than 10% pseudoephedrine are prohibited under the Stimulants Control Law in Japan.<sup id="cite_ref-156" class="reference"><a href="#cite_note-156"><span class="cite-bracket">[</span>156<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Mexico">Mexico</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=38" title="Edit section: Mexico"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>On 23 November 2007, the use and trade of pseudoephedrine in Mexico was made illegal as it was argued that it was extremely popular as a precursor in the synthesis of methamphetamine.<sup id="cite_ref-157" class="reference"><a href="#cite_note-157"><span class="cite-bracket">[</span>157<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Netherlands">Netherlands</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=39" title="Edit section: Netherlands"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine was withdrawn from sale in 1989 due to concerns about adverse cardiac side effects.<sup id="cite_ref-158" class="reference"><a href="#cite_note-158"><span class="cite-bracket">[</span>158<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="New_Zealand">New Zealand</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=40" title="Edit section: New Zealand"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Since April 2024, pseudoephedrine has been classified as a restricted (pharmacist-only) drug in the <a href="/wiki/Misuse_of_Drugs_Act_1975" title="Misuse of Drugs Act 1975">Misuse of Drugs Act 1975</a> which allows the purchase of medicines containing pseudoephedrine from a pharmacist without a prescription.<sup id="cite_ref-159" class="reference"><a href="#cite_note-159"><span class="cite-bracket">[</span>159<span class="cite-bracket">]</span></a></sup> </p><p>Pseudoephedrine, ephedrine, and any product containing these substances, e.g. cold and flu medicines, were first classified in October 2004 as Class C Part III (partially exempted) controlled drugs, due to being the principal ingredient in methamphetamine.<sup id="cite_ref-160" class="reference"><a href="#cite_note-160"><span class="cite-bracket">[</span>160<span class="cite-bracket">]</span></a></sup> New Zealand Customs and police officers continued to make large interceptions of precursor substances believed to be destined for <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a> production. On 9 October 2009, Prime Minister <a href="/wiki/John_Key" title="John Key">John Key</a> announced pseudoephedrine-based cold and flu tablets would become prescription-only drugs and reclassified as a class B2 drug.<sup id="cite_ref-161" class="reference"><a href="#cite_note-161"><span class="cite-bracket">[</span>161<span class="cite-bracket">]</span></a></sup> The law was amended by The Misuse of Drugs Amendment Bill 2010, which passed in August 2011.<sup id="cite_ref-162" class="reference"><a href="#cite_note-162"><span class="cite-bracket">[</span>162<span class="cite-bracket">]</span></a></sup> </p><p>On 24 November 2023, the recently formed <a href="/wiki/Sixth_National_Government_of_New_Zealand" title="Sixth National Government of New Zealand">National-led coalition government</a> announced that the sale of cold medication containing pseudoephedrine would be allowed (as part of the coalition agreement between the National and ACT parties).<sup id="cite_ref-163" class="reference"><a href="#cite_note-163"><span class="cite-bracket">[</span>163<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Switzerland">Switzerland</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=41" title="Edit section: Switzerland"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine is available without a prescription in combination (with <a href="/wiki/Aspirin" title="Aspirin">aspirin</a>) under the brand name "Aspirin Complex". There is also a preparation consisting of a single ingredient 120 mg extended-release tablet that can be obtained at pharmacies with a prescription or after consultation with a pharmacist.<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. (December 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading4"><h4 id="Turkey">Turkey</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=42" title="Edit section: Turkey"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In Turkey, medications containing pseudoephedrine are available by prescription only.<sup id="cite_ref-164" class="reference"><a href="#cite_note-164"><span class="cite-bracket">[</span>164<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="United_Kingdom">United Kingdom</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=43" title="Edit section: United Kingdom"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the UK, pseudoephedrine is available over the counter under the supervision of a qualified pharmacist, or on prescription. In 2007, the <a href="/wiki/Medicines_and_Healthcare_products_Regulatory_Agency" title="Medicines and Healthcare products Regulatory Agency">MHRA</a> reacted to concerns over the diversion of ephedrine and pseudoephedrine for the illicit manufacture of methamphetamine by introducing voluntary restrictions limiting over-the-counter sales to one box containing no more than 720 mg of pseudoephedrine in total per transaction. These restrictions became law in April 2008.<sup id="cite_ref-165" class="reference"><a href="#cite_note-165"><span class="cite-bracket">[</span>165<span class="cite-bracket">]</span></a></sup> No form of ID is required. </p> <div class="mw-heading mw-heading4"><h4 id="United_States">United States</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=44" title="Edit section: United States"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading5"><h5 id="Federal">Federal</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=45" title="Edit section: Federal"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/United_States_Congress" title="United States Congress">United States Congress</a> has recognized that pseudoephedrine is used in the illegal manufacture of methamphetamine. In 2005, the <a href="/wiki/United_States_House_Committee_on_Education_and_Labor" class="mw-redirect" title="United States House Committee on Education and Labor">Committee on Education and the Workforce</a> heard testimony concerning education programs and state legislation designed to curb this illegal practice.<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. (December 2023)">citation needed</span></a></i>]</sup> </p><p>Attempts to control the sale of the drug date back to 1986, when federal officials at the <a href="/wiki/Drug_Enforcement_Administration" title="Drug Enforcement Administration">Drug Enforcement Administration</a> (DEA) first drafted legislation, later proposed by Senator <a href="/wiki/Bob_Dole" title="Bob Dole">Bob Dole</a>, that would have placed several chemicals used in the manufacture of illicit drugs under the <a href="/wiki/Controlled_Substances_Act" title="Controlled Substances Act">Controlled Substances Act</a>. The bill would have required each transaction involving pseudoephedrine to be reported to the government, and federal approval of all imports and exports. Fearing this would limit legitimate use of the drug, lobbyists from over the counter drug manufacturing associations sought to stop this legislation from moving forward and were successful in exempting from the regulations all chemicals that had been turned into a legal final product, such as Sudafed.<sup id="cite_ref-166" class="reference"><a href="#cite_note-166"><span class="cite-bracket">[</span>166<span class="cite-bracket">]</span></a></sup> </p><p>Before the passage of the <a href="/wiki/Combat_Methamphetamine_Epidemic_Act_of_2005" title="Combat Methamphetamine Epidemic Act of 2005">Combat Methamphetamine Epidemic Act of 2005</a>, sales of the drug became increasingly regulated, as DEA regulators and pharmaceutical companies continued to fight for their respective positions. The DEA continued to make greater progress in its attempts to control pseudoephedrine as methamphetamine production skyrocketed, becoming a serious problem in the western United States. When purity dropped, so did the number of people in rehab and people admitted to emergency rooms with methamphetamine in their systems. This reduction in purity was usually short-lived, however, as methamphetamine producers eventually found a way around the new regulations.<sup id="cite_ref-167" class="reference"><a href="#cite_note-167"><span class="cite-bracket">[</span>167<span class="cite-bracket">]</span></a></sup> </p><p>Congress passed the Combat Methamphetamine Epidemic Act of 2005 (CMEA) as an amendment to the renewal of the <a href="/wiki/Patriot_Act" title="Patriot Act">USA Patriot Act</a>.<sup id="cite_ref-CMEA_138-2" class="reference"><a href="#cite_note-CMEA-138"><span class="cite-bracket">[</span>138<span class="cite-bracket">]</span></a></sup> Signed into law by President <a href="/wiki/George_W._Bush" title="George W. Bush">George W. Bush</a> on 6 March 2006,<sup id="cite_ref-FDA_legal_137-1" class="reference"><a href="#cite_note-FDA_legal-137"><span class="cite-bracket">[</span>137<span class="cite-bracket">]</span></a></sup> the act amended <a href="/wiki/Title_21_of_the_United_States_Code" title="Title 21 of the United States Code">21 U.S.C.</a> <a rel="nofollow" class="external text" href="https://www.law.cornell.edu/uscode/text/21/830">§ 830</a>, concerning the sale of pseudoephedrine-containing products. The law mandated two phases, the first needing to be implemented by 8 April 2006, and the second to be completed by 30 September 2006. The first phase dealt primarily with implementing the new buying restrictions based on the amount, while the second phase encompassed the requirements of storage, employee training, and record keeping.<sup id="cite_ref-papharmacists.com_168-0" class="reference"><a href="#cite_note-papharmacists.com-168"><span class="cite-bracket">[</span>168<span class="cite-bracket">]</span></a></sup> Though the law was mainly directed at pseudoephedrine products it also applies to all over-the-counter products containing ephedrine, pseudoephedrine, and phenylpropanolamine, their salts, optical isomers, and salts of optical isomers.<sup id="cite_ref-papharmacists.com_168-1" class="reference"><a href="#cite_note-papharmacists.com-168"><span class="cite-bracket">[</span>168<span class="cite-bracket">]</span></a></sup> Pseudoephedrine was defined as a "<a href="/wiki/DEA_list_of_chemicals" title="DEA list of chemicals">scheduled listed chemical product</a>" under <a href="/wiki/Title_21_of_the_United_States_Code" title="Title 21 of the United States Code">21 U.S.C.</a> <a rel="nofollow" class="external text" href="https://www.law.cornell.edu/uscode/text/21/802">§ 802</a>(45(A)). The act included the following requirements for merchants ("regulated sellers") who sell such products: </p> <ul><li>Required a retrievable record of all purchases, identifying the name and address of each party, to be kept for two years</li> <li>Required verification of proof of identity of all purchasers</li> <li>Required protection and disclosure methods in the collection of personal information</li> <li>Required reports to the <a href="/wiki/United_States_Attorney_General" title="United States Attorney General">Attorney General</a> of any suspicious payments or disappearances of the regulated products</li> <li>Required training of employees with regard to the requirements of the CMEA. Retailers must self-certify as to training and compliance.</li> <li>The non-liquid dose form of regulated products may only be sold in unit dose blister packs</li> <li>Regulated products must be stored behind the counter or in a locked cabinet in such a way as to restrict public access</li> <li>Sales limits (per customer): <ul><li>Daily sales limit—must not exceed 3.6 grams of pseudoephedrine base without regard to the number of transactions</li> <li>30-day (not monthly) sales limit—must not exceed 7.5 grams of pseudoephedrine base if sold by mail order or "mobile retail vendor"</li> <li>30-day purchase limit—must not exceed 9 grams of pseudoephedrine base. (A misdemeanor possession offense under <a href="/wiki/Title_21_of_the_United_States_Code" title="Title 21 of the United States Code">21 U.S.C.</a> <a rel="nofollow" class="external text" href="https://www.law.cornell.edu/uscode/text/21/844a">§ 844a</a> for the person who buys it.)</li></ul></li></ul> <p>The requirements were revised in the Methamphetamine Production Prevention Act of 2008 to require that a regulated seller of scheduled listed chemical products may not sell such a product unless the purchaser:<sup id="cite_ref-MPPA_139-2" class="reference"><a href="#cite_note-MPPA-139"><span class="cite-bracket">[</span>139<span class="cite-bracket">]</span></a></sup> </p> <ul><li>Presents a government-issued photographic identification; and</li> <li>Signs the written logbook with name, address, and time and date of the sale</li></ul> <div class="mw-heading mw-heading5"><h5 id="State">State</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=46" title="Edit section: State"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most states also have laws regulating pseudoephedrine.<sup id="cite_ref-169" class="reference"><a href="#cite_note-169"><span class="cite-bracket">[</span>169<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-170" class="reference"><a href="#cite_note-170"><span class="cite-bracket">[</span>170<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-171" class="reference"><a href="#cite_note-171"><span class="cite-bracket">[</span>171<span class="cite-bracket">]</span></a></sup> </p><p>The states of Alabama, Arizona, Arkansas, California, Colorado, Delaware, Florida, Georgia, Hawaii (as of May 1, 2009<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Pseudoephedrine&action=edit">[update]</a></sup>) Idaho, Illinois, Indiana, Iowa, Kansas, Kentucky, Louisiana (as of August 15, 2009<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Pseudoephedrine&action=edit">[update]</a></sup>), Massachusetts, Michigan, Minnesota, Mississippi, Missouri, Montana, Nebraska,<sup id="cite_ref-172" class="reference"><a href="#cite_note-172"><span class="cite-bracket">[</span>172<span class="cite-bracket">]</span></a></sup> Nevada, New Jersey, North Carolina, Ohio, Oklahoma, Oregon, Pennsylvania, South Dakota, Tennessee, Texas, Utah, Vermont, Virginia, Washington, West Virginia and Wisconsin have laws requiring pharmacies to sell pseudoephedrine "behind the counter". Though the drug can be purchased without a prescription, states can limit the number of units sold and can collect personal information from purchasers.<sup id="cite_ref-NAMSDL_173-0" class="reference"><a href="#cite_note-NAMSDL-173"><span class="cite-bracket">[</span>173<span class="cite-bracket">]</span></a></sup><i></i> </p><p>The states of Oregon and Mississippi previously required a prescription for the purchase of products containing pseudoephedrine. However, as of 1 January 2022, these restrictions have been repealed.<sup id="cite_ref-174" class="reference"><a href="#cite_note-174"><span class="cite-bracket">[</span>174<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-175" class="reference"><a href="#cite_note-175"><span class="cite-bracket">[</span>175<span class="cite-bracket">]</span></a></sup> The state of Oregon reduced the number of methamphetamine lab seizures from 448 in 2004 (the final full year before implementation of the prescription only law)<sup id="cite_ref-OregonDEC_176-0" class="reference"><a href="#cite_note-OregonDEC-176"><span class="cite-bracket">[</span>176<span class="cite-bracket">]</span></a></sup> to a new low of 13 in 2009.<sup id="cite_ref-justice.gov_177-0" class="reference"><a href="#cite_note-justice.gov-177"><span class="cite-bracket">[</span>177<span class="cite-bracket">]</span></a></sup> The decrease in <a href="/wiki/Meth_lab" class="mw-redirect" title="Meth lab">meth lab</a> incidents in Oregon occurred largely before the prescription-only law took effect, according to a NAMSDL report titled <i>Pseudoephedrine Prescription Laws in Oregon and Mississippi</i>.<sup id="cite_ref-NAMSDL_173-1" class="reference"><a href="#cite_note-NAMSDL-173"><span class="cite-bracket">[</span>173<span class="cite-bracket">]</span></a></sup> The report posits that the decline in meth lab incidents in both states may be due to other factors: "Mexican traffickers may have contributed to the decline in meth labs in Mississippi and Oregon (and surrounding states) as they were able to provide ample supply of equal or greater quality meth at competitive prices". Additionally, similar decreases in meth lab incidents were seen in surrounding states, according to the report, and meth-related deaths in Oregon have dramatically risen since 2007. Some municipalities in Missouri have enacted similar ordinances, including <a href="/wiki/Washington,_Missouri" title="Washington, Missouri">Washington</a>,<sup id="cite_ref-178" class="reference"><a href="#cite_note-178"><span class="cite-bracket">[</span>178<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Union,_Missouri" title="Union, Missouri">Union</a>,<sup id="cite_ref-179" class="reference"><a href="#cite_note-179"><span class="cite-bracket">[</span>179<span class="cite-bracket">]</span></a></sup> <a href="/wiki/New_Haven,_Missouri" title="New Haven, Missouri">New Haven</a>,<sup id="cite_ref-180" class="reference"><a href="#cite_note-180"><span class="cite-bracket">[</span>180<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Cape_Girardeau,_Missouri" title="Cape Girardeau, Missouri">Cape Girardeau</a><sup id="cite_ref-181" class="reference"><a href="#cite_note-181"><span class="cite-bracket">[</span>181<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Ozark,_Missouri" title="Ozark, Missouri">Ozark</a>.<sup id="cite_ref-182" class="reference"><a href="#cite_note-182"><span class="cite-bracket">[</span>182<span class="cite-bracket">]</span></a></sup> Certain pharmacies in <a href="/wiki/Terre_Haute,_Indiana" title="Terre Haute, Indiana">Terre Haute, Indiana</a> do so as well.<sup id="cite_ref-183" class="reference"><a href="#cite_note-183"><span class="cite-bracket">[</span>183<span class="cite-bracket">]</span></a></sup> </p><p>Another approach to controlling the drug on the state level mandated by some state governments to control the purchases of their citizens is the use of electronic tracking systems, which require the electronic submission of specified purchaser information by all retailers who sell pseudoephedrine. Thirty-two states now require the <a href="/wiki/National_Precursor_Log_Exchange" title="National Precursor Log Exchange">National Precursor Log Exchange</a> (NPLEx) to be used for every pseudoephedrine and ephedrine OTC purchase, and ten of the eleven largest pharmacy chains in the US voluntarily contribute all of their similar transactions to NPLEx. These states have seen dramatic results in reducing the number of methamphetamine laboratory seizures. Before the implementation of the system in Tennessee in 2005, methamphetamine laboratory seizures totaled 1,497 in 2004 but were reduced to 955 in 2005, and 589 in 2009.<sup id="cite_ref-justice.gov_177-1" class="reference"><a href="#cite_note-justice.gov-177"><span class="cite-bracket">[</span>177<span class="cite-bracket">]</span></a></sup> Kentucky's program was implemented statewide in 2008, and since statewide implementation, the number of laboratory seizures has significantly decreased.<sup id="cite_ref-justice.gov_177-2" class="reference"><a href="#cite_note-justice.gov-177"><span class="cite-bracket">[</span>177<span class="cite-bracket">]</span></a></sup> Oklahoma initially experienced success with its tracking system after implementation in 2006, as the number of seizures dropped in that year and again in 2007. In 2008, however, seizures began rising again, and have continued to rise in 2009.<sup id="cite_ref-justice.gov_177-3" class="reference"><a href="#cite_note-justice.gov-177"><span class="cite-bracket">[</span>177<span class="cite-bracket">]</span></a></sup> </p><p>NPLEx appears to be successful by requiring the real-time submission of transactions, thereby enabling the relevant laws to be enforced at the point of sale. By creating a multi-state database and the ability to compare all transactions quickly, NPLEx enables pharmacies to deny purchases that would be illegal based on gram limits, age, or even to convicted meth offenders in some states. NPLEx also enforces the federal gram limits across state lines, which was impossible with state-operated systems. Access to the records is by law enforcement agencies only, through an online secure portal.<sup id="cite_ref-184" class="reference"><a href="#cite_note-184"><span class="cite-bracket">[</span>184<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=47" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pseudoephedrine has been studied in the treatment of <a href="/wiki/Snoring" title="Snoring">snoring</a>.<sup id="cite_ref-AchuthanMedhi2015_185-0" class="reference"><a href="#cite_note-AchuthanMedhi2015-185"><span class="cite-bracket">[</span>185<span class="cite-bracket">]</span></a></sup> However, data are inadequate to support this use.<sup id="cite_ref-AchuthanMedhi2015_185-1" class="reference"><a href="#cite_note-AchuthanMedhi2015-185"><span class="cite-bracket">[</span>185<span class="cite-bracket">]</span></a></sup> </p><p>A study has found that pseudoephedrine can reduce <a href="/wiki/Lactation" title="Lactation">milk production</a> in <a href="/wiki/Breastfeeding" title="Breastfeeding">breastfeeding</a> women.<sup id="cite_ref-TrimeloniSpencer2016_186-0" class="reference"><a href="#cite_note-TrimeloniSpencer2016-186"><span class="cite-bracket">[</span>186<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AljazafHaleIlett2003_187-0" class="reference"><a href="#cite_note-AljazafHaleIlett2003-187"><span class="cite-bracket">[</span>187<span class="cite-bracket">]</span></a></sup> This might have been due to suppression of <a href="/wiki/Prolactin" title="Prolactin">prolactin</a> <a href="/wiki/Secretion" title="Secretion">secretion</a>.<sup id="cite_ref-AljazafHaleIlett2003_187-1" class="reference"><a href="#cite_note-AljazafHaleIlett2003-187"><span class="cite-bracket">[</span>187<span class="cite-bracket">]</span></a></sup> Pseudoephedrine might be useful for <a href="/wiki/Lactation_suppression" title="Lactation suppression">lactation suppression</a>.<sup id="cite_ref-TrimeloniSpencer2016_186-1" class="reference"><a href="#cite_note-TrimeloniSpencer2016-186"><span class="cite-bracket">[</span>186<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AljazafHaleIlett2003_187-2" class="reference"><a href="#cite_note-AljazafHaleIlett2003-187"><span class="cite-bracket">[</span>187<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pseudoephedrine&action=edit&section=48" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-GłowackaWiela-Hojeńska2021-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-13"><sup><i><b>n</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-14"><sup><i><b>o</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-15"><sup><i><b>p</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-16"><sup><i><b>q</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-17"><sup><i><b>r</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-18"><sup><i><b>s</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-19"><sup><i><b>t</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-20"><sup><i><b>u</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-21"><sup><i><b>v</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-22"><sup><i><b>w</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-23"><sup><i><b>x</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-24"><sup><i><b>y</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-25"><sup><i><b>z</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-26"><sup><i><b>aa</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-27"><sup><i><b>ab</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-28"><sup><i><b>ac</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-29"><sup><i><b>ad</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-30"><sup><i><b>ae</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-31"><sup><i><b>af</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-32"><sup><i><b>ag</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-33"><sup><i><b>ah</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-34"><sup><i><b>ai</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-35"><sup><i><b>aj</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-36"><sup><i><b>ak</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-37"><sup><i><b>al</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-38"><sup><i><b>am</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-39"><sup><i><b>an</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-40"><sup><i><b>ao</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-41"><sup><i><b>ap</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-42"><sup><i><b>aq</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-43"><sup><i><b>ar</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-44"><sup><i><b>as</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-45"><sup><i><b>at</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-46"><sup><i><b>au</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-47"><sup><i><b>av</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-48"><sup><i><b>aw</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-49"><sup><i><b>ax</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-50"><sup><i><b>ay</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-51"><sup><i><b>az</b></i></sup></a> <a href="#cite_ref-GłowackaWiela-Hojeńska2021_1-52"><sup><i><b>ba</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFGłowackaWiela-Hojeńska2021" class="citation journal cs1">Głowacka K, Wiela-Hojeńska A (May 2021). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8152226">"Pseudoephedrine—Benefits and Risks"</a>. <i>Int J Mol Sci</i>. <b>22</b> (10): 5146. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fijms22105146">10.3390/ijms22105146</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8152226">8152226</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/34067981">34067981</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Int+J+Mol+Sci&rft.atitle=Pseudoephedrine%E2%80%94Benefits+and+Risks&rft.volume=22&rft.issue=10&rft.pages=5146&rft.date=2021-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8152226%23id-name%3DPMC&rft_id=info%3Apmid%2F34067981&rft_id=info%3Adoi%2F10.3390%2Fijms22105146&rft.aulast=G%C5%82owacka&rft.aufirst=K&rft.au=Wiela-Hoje%C5%84ska%2C+A&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8152226&rfr_id=info%3Asid%2Fen.wikipedia.org%3APseudoephedrine" class="Z3988"></span></span> </li> <li id="cite_note-Eccles2007-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Eccles2007_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Eccles2007_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Eccles2007_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Eccles2007_2-3"><sup><i><b>d</b></i></sup></a> <a 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"Evaluation of the potential for pharmacodynamic and pharmacokinetic drug interactions between selegiline transdermal system and two sympathomimetic agents (pseudoephedrine and phenylpropanolamine) in healthy volunteers". <i>J Clin Pharmacol</i>. <b>47</b> (8): <span class="nowrap">978–</span>990. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F0091270007302950">10.1177/0091270007302950</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/17554106">17554106</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Clin+Pharmacol&rft.atitle=Evaluation+of+the+potential+for+pharmacodynamic+and+pharmacokinetic+drug+interactions+between+selegiline+transdermal+system+and+two+sympathomimetic+agents+%28pseudoephedrine+and+phenylpropanolamine%29+in+healthy+volunteers&rft.volume=47&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E978-%3C%2Fspan%3E990&rft.date=2007-08&rft_id=info%3Adoi%2F10.1177%2F0091270007302950&rft_id=info%3Apmid%2F17554106&rft.aulast=Azzaro&rft.aufirst=AJ&rft.au=VanDenBerg%2C+CM&rft.au=Ziemniak%2C+J&rft.au=Kemper%2C+EM&rft.au=Blob%2C+LF&rft.au=Campbell%2C+BJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3APseudoephedrine" class="Z3988"></span></span> </li> <li id="cite_note-JohnsonHricik1993-71"><span class="mw-cite-backlink">^ <a href="#cite_ref-JohnsonHricik1993_71-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-JohnsonHricik1993_71-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJohnsonHricik1993" class="citation journal cs1">Johnson DA, Hricik JG (1993). "The pharmacology of alpha-adrenergic decongestants". <i>Pharmacotherapy</i>. <b>13</b> (6 Pt 2): <span class="nowrap">110S –</span> <span class="nowrap">115S</span>, discussion 143S–146S. <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%2Fj.1875-9114.1993.tb02779.x">10.1002/j.1875-9114.1993.tb02779.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/7507588">7507588</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacotherapy&rft.atitle=The+pharmacology+of+alpha-adrenergic+decongestants&rft.volume=13&rft.issue=6+Pt+2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E110S+-%3C%2Fspan%3E+%3Cspan+class%3D%22nowrap%22%3E115S%3C%2Fspan%3E%2C+discussion+143S-146S&rft.date=1993&rft_id=info%3Adoi%2F10.1002%2Fj.1875-9114.1993.tb02779.x&rft_id=info%3Apmid%2F7507588&rft.aulast=Johnson&rft.aufirst=DA&rft.au=Hricik%2C+JG&rfr_id=info%3Asid%2Fen.wikipedia.org%3APseudoephedrine" class="Z3988"></span></span> </li> <li id="cite_note-Broadley2010-72"><span class="mw-cite-backlink">^ <a href="#cite_ref-Broadley2010_72-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Broadley2010_72-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBroadley2010" class="citation journal cs1">Broadley KJ (March 2010). "The vascular effects of trace amines and amphetamines". <i>Pharmacol Ther</i>. <b>125</b> (3): <span class="nowrap">363–</span>375. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.pharmthera.2009.11.005">10.1016/j.pharmthera.2009.11.005</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/19948186">19948186</a>. <q>It is also relevant to other sympathomimetic amines contained in over-the-counter cough and cold remedies as decongestants, such as phenylpropanolamine and pseudoephedrine. Thus, MAO inhibitors potentiate the peripheral effects of indirectly acting sympathomimetic amines. It is not often realized, however, that this potentiation occurs irrespective of whether the amine is a substrate for MAO. An α-methyl group on the side chain, as in amphetamine and ephedrine, renders the amine immune to deamination so that they are not metabolized in the gut. Similarly, β-PEA would not be deaminated in the gut as it is a selective substrate for MAO-B which is not found in the gut. However, MAO inhibition in sympathetic neurones allows the cytoplasmic pool of noradrenaline to increase. It is this pool that is released by indirectly acting sympathomimetic amines and their responses are therefore potentiated irrespective of whether they are deaminated by MAO (Youdim & Finberg, 1991).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacol+Ther&rft.atitle=The+vascular+effects+of+trace+amines+and+amphetamines&rft.volume=125&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E363-%3C%2Fspan%3E375&rft.date=2010-03&rft_id=info%3Adoi%2F10.1016%2Fj.pharmthera.2009.11.005&rft_id=info%3Apmid%2F19948186&rft.aulast=Broadley&rft.aufirst=KJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3APseudoephedrine" class="Z3988"></span></span> </li> <li id="cite_note-Marcucci2015-73"><span class="mw-cite-backlink"><b><a href="#cite_ref-Marcucci2015_73-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMarcucci2015" class="citation book cs1">Marcucci C (2015). 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Retrieved <span class="nowrap">1 July</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=healthycanadians.gc.ca&rft.atitle=Archived+%E2%80%93+Health+Canada+Reminds+Canadians+not+to+use+Ephedra%2FEphedrine+Products&rft.date=2021-08-20&rft_id=http%3A%2F%2Fhealthycanadians.gc.ca%2Frecall-alert-rappel-avis%2Fhc-sc%2F2008%2F13279a-eng.php&rfr_id=info%3Asid%2Fen.wikipedia.org%3APseudoephedrine" class="Z3988"></span></span> </li> <li id="cite_note-149"><span class="mw-cite-backlink"><b><a href="#cite_ref-149">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20151025125803/http://pharmacytechniciansletter.therapeuticresearch.com/(S(uvxrnu55cowfcdintotjyq45))/mobile/Newsletter.aspx?nidchk=1&cs=&s=PTL&vo=1&dd=271114&dt=2&vodd=3">"What ingredients are commonly found in OTC cough and cold products? 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.navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Decongestants_and_other_nasal_preparations_(R01)464" 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" 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.mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Nasal_preparations" title="Template:Nasal preparations"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nasal_preparations" title="Template talk:Nasal preparations"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nasal_preparations" title="Special:EditPage/Template:Nasal preparations"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Decongestants_and_other_nasal_preparations_(R01)464" style="font-size:114%;margin:0 4em"><a href="/wiki/Decongestant" title="Decongestant">Decongestants</a> and other nasal preparations (<a href="/wiki/ATC_code_R01" title="ATC code R01">R01</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Topical_decongestant" title="Topical decongestant">Topical</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/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">Sympathomimetics</a>, plain</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/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/Cyclopentamine" title="Cyclopentamine">Cyclopentamine</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/Fenoxazoline" title="Fenoxazoline">Fenoxazoline</a></li> <li><a href="/wiki/Iproheptine" title="Iproheptine">Iproheptine</a></li> <li><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levmetamfetamine</a></li> <li><a href="/wiki/Methylephedrine" title="Methylephedrine">Methylephedrine</a></li> <li><a href="/wiki/Metizoline" title="Metizoline">Metizoline</a></li> <li><a href="/wiki/Naphazoline" title="Naphazoline">Naphazoline</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li> <li><a href="/wiki/Tetryzoline" title="Tetryzoline">Tetryzoline</a></li> <li><a href="/wiki/Tramazoline" title="Tramazoline">Tramazoline</a></li> <li><a href="/wiki/Tuaminoheptane" title="Tuaminoheptane">Tuaminoheptane</a></li> <li><a href="/wiki/Tymazoline" title="Tymazoline">Tymazoline</a></li> <li><a href="/wiki/Xylometazoline" title="Xylometazoline">Xylometazoline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Allergen" title="Allergen">Antiallergic</a> agents,<br />excluding corticosteroids</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/Spaglumic_acid" class="mw-redirect" title="Spaglumic acid">Spaglumic acid</a></li></ul> <ul><li><i><a href="/wiki/Histamine_antagonist" class="mw-redirect" title="Histamine antagonist">histamine antagonists</a></i> (<a href="/wiki/Levocabastine" title="Levocabastine">Levocabastine</a></li> <li><a href="/wiki/Antazoline" title="Antazoline">Antazoline</a></li> <li><a href="/wiki/Thonzylamine" title="Thonzylamine">Thonzylamine</a>)</li></ul> <ul><li><i><a href="/wiki/Mast_cell_stabilizer" title="Mast cell stabilizer">mast cell stabilizer (some are also antihistamines)</a></i> (<a href="/wiki/Cromoglicate" class="mw-redirect" title="Cromoglicate">Cromoglicic acid</a></li> <li><a href="/wiki/Nedocromil" title="Nedocromil">Nedocromil</a></li> <li><a href="/wiki/Azelastine" title="Azelastine">Azelastine</a></li> <li><a href="/wiki/Olopatadine" title="Olopatadine">Olopatadine</a></li> <li><a href="/wiki/Lodoxamide" title="Lodoxamide">Lodoxamide</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Corticosteroid" title="Corticosteroid">Corticosteroids</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/Beclometasone_dipropionate" class="mw-redirect" title="Beclometasone dipropionate">Beclometasone dipropionate</a></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/Dexamethasone" title="Dexamethasone">Dexamethasone</a></li> <li><a href="/wiki/Flunisolide" title="Flunisolide">Flunisolide</a></li> <li>Fluticasone (<a href="/wiki/Fluticasone_furoate" title="Fluticasone furoate">Fluticasone furoate</a>, <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 furoate</a></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a><sup>#</sup></li> <li><a href="/wiki/Tixocortol" title="Tixocortol">Tixocortol</a></li> <li><a href="/wiki/Triamcinolone" title="Triamcinolone">Triamcinolone</a></li> <li><a href="/wiki/Triamcinolone_acetonide" title="Triamcinolone acetonide">Triamcinolone acetonide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other nasal preparations</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/Cafaminol" title="Cafaminol">Cafaminol</a></li> <li><a href="/wiki/Calcium_hexamine_thiocyanate" title="Calcium hexamine thiocyanate">Calcium hexamine thiocyanate</a></li> <li><a href="/wiki/Eucalyptus_oil" title="Eucalyptus oil">Eucalyptus oil</a></li> <li><a href="/wiki/Framycetin" class="mw-redirect" title="Framycetin">Framycetin</a></li> <li><a href="/wiki/Hexamidine" title="Hexamidine">Hexamidine</a></li> <li><a href="/wiki/Hyaluronan" class="mw-redirect" title="Hyaluronan">Hyaluronan</a></li> <li><a href="/wiki/Ipratropium_bromide" title="Ipratropium bromide">Ipratropium bromide</a></li> <li><a href="/wiki/Mupirocin" title="Mupirocin">Mupirocin</a></li> <li><a href="/wiki/Retinol" title="Retinol">Retinol</a></li> <li><a href="/wiki/Ritiometan" title="Ritiometan">Ritiometan</a></li> <li><a href="/wiki/Saline_(medicine)" title="Saline (medicine)">Saline water</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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Olopatadine/mometasone" title="Olopatadine/mometasone">Olopatadine/mometasone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Systemic use:<br /><a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">Sympathomimetics</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/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a class="mw-selflink selflink">Pseudoephedrine</a> (<a href="/wiki/Azatadine/pseudoephedrine" title="Azatadine/pseudoephedrine">+azatadine</a>, <a href="/wiki/Carbinoxamine/pseudoephedrine" title="Carbinoxamine/pseudoephedrine">+carbinoxamine</a>, <a href="/wiki/Cetirizine/pseudoephedrine" title="Cetirizine/pseudoephedrine">+cetirizine</a>, <a href="/wiki/Dexbrompheniramine/pseudoephedrine" title="Dexbrompheniramine/pseudoephedrine">+dexbrompheniramine</a>, <a href="/wiki/Fexofenadine/pseudoephedrine" title="Fexofenadine/pseudoephedrine">+fexofenadine</a>, <a href="/wiki/Pseudoephedrine/loratadine" title="Pseudoephedrine/loratadine">+loratadine</a>, <a href="/wiki/Naproxen/pseudoephedrine" title="Naproxen/pseudoephedrine">+naproxen</a>)</li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Cardiac_stimulants_excluding_cardiac_glycosides_(C01C)544" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cardiac_stimulants_excluding_cardiac_glycosides" title="Template:Cardiac stimulants excluding cardiac glycosides"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cardiac_stimulants_excluding_cardiac_glycosides" title="Template talk:Cardiac stimulants excluding cardiac glycosides"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cardiac_stimulants_excluding_cardiac_glycosides" title="Special:EditPage/Template:Cardiac stimulants excluding cardiac glycosides"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cardiac_stimulants_excluding_cardiac_glycosides_(C01C)544" style="font-size:114%;margin:0 4em"><a href="/wiki/Cardiac_stimulant" title="Cardiac stimulant">Cardiac stimulants</a> excluding cardiac glycosides (<a href="/wiki/ATC_code_C01#C01C" title="ATC code C01">C01C</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Adrenergic</a> and<br /><a href="/wiki/Dopaminergic" title="Dopaminergic">dopaminergic</a> agents</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/Adrenergic_agonist" title="Adrenergic agonist">Adrenergic agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" 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%">α</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/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Midodrine" title="Midodrine">Midodrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Oxedrine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">β</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/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Prenalterol" title="Prenalterol">Prenalterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">mixed</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/Amezinium_metilsulfate" title="Amezinium metilsulfate">Amezinium metilsulfate</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a> #</li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Norepinephrine_(medication)" title="Norepinephrine (medication)">Norepinephrine</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/Dopamine_agonist" title="Dopamine agonist">Dopamine 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/Fenoldopam" title="Fenoldopam">Fenoldopam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Both</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/Docarpamine" title="Docarpamine">Docarpamine</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/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine">Octopamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Unknown/ungrouped</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/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a href="/wiki/Dimetofrine" title="Dimetofrine">Dimetofrine</a></li> <li><a href="/wiki/Gepefrine" title="Gepefrine">Gepefrine</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</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/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">Phosphodiesterase inhibitors</a> (<a href="/wiki/PDE3_inhibitor" title="PDE3 inhibitor">PDE3I</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/Amrinone" title="Amrinone">Amrinone</a></li> <li><a href="/wiki/Bucladesine" title="Bucladesine">Bucladesine</a></li> <li><a href="/wiki/Enoximone" title="Enoximone">Enoximone</a></li> <li><a href="/wiki/Milrinone" title="Milrinone">Milrinone</a></li> <li><a href="/wiki/Vesnarinone" title="Vesnarinone">Vesnarinone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other cardiac stimulants</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/Angiotensinamide" title="Angiotensinamide">Angiotensinamide</a></li> <li><a href="/wiki/Levosimendan" title="Levosimendan">Levosimendan</a></li> <li><a href="/wiki/Omecamtiv_mecarbil" title="Omecamtiv mecarbil">Omecamtiv mecarbil</a></li> <li><a href="/wiki/Pimobendan" title="Pimobendan">Pimobendan</a></li> <li><a href="/wiki/Xamoterol" title="Xamoterol">Xamoterol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="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="Stimulants535" 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="Stimulants535" 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 href="/wiki/Theophylline" title="Theophylline">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" 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" 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" 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 class="mw-selflink selflink">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"></div><div role="navigation" class="navbox" aria-labelledby="Monoamine_releasing_agents1712" 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:Monoamine_releasing_agents" title="Template:Monoamine releasing agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoamine_releasing_agents" title="Template talk:Monoamine releasing agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoamine_releasing_agents" title="Special:EditPage/Template:Monoamine releasing agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoamine_releasing_agents1712" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">Monoamine releasing agents</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Dopamine_releasing_agents" class="mw-redirect" title="Dopamine releasing agents"><abbr title="Dopamine releasing agents">DRAs</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 Dopamine releasing agents</span></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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Morpholines:</i> <a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</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/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Oxazolines:</i> <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-MAR</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Phenethylamines:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">2-OH-PEA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</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/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><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/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Me-PEA</a></li> <li><a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" class="mw-redirect" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</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/Iofetamine_(123I)" title="Iofetamine (123I)">Iofetamine (123I)</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/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></li></ul></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/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-methylbutanamine" class="mw-redirect" title="1,3-Benzodioxolyl-N-methylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</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/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine"><i>p</i>BA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine"><i>p</i>CA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine"><i>p</i>IA</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a class="mw-selflink selflink">Pseudoephedrine</a></li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Piperazines:</i> <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Others:</i> <a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-ADN</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-AI</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-AT</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-BP</a></li> <li><a href="/wiki/5-APDI" title="5-APDI">5-APDI</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/Amineptine" title="Amineptine">Amineptine</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <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/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexanamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</a></li> <li><a href="/wiki/Phenylbiguanide" title="Phenylbiguanide">Phenylbiguanide</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</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/Norepinephrine_releasing_agents" class="mw-redirect" title="Norepinephrine releasing agents"><abbr title="Norepinephrine releasing agents">NRAs</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 Norepinephrine releasing agents</span></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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Morpholines:</i> <a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</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/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Oxazolines:</i> <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-MAR</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Phenethylamines:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">2-OH-PEA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</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/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> <ul><li><a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a></li></ul></li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Me-PEA</a></li> <li><a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" class="mw-redirect" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</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/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</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-APDI" title="5-APDI">5-APDI</a> (IAP)</li> <li><a href="/wiki/Iofetamine_(123I)" title="Iofetamine (123I)">Iofetamine (123I)</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/1,3-Benzodioxolyl-N-methylbutanamine" class="mw-redirect" title="1,3-Benzodioxolyl-N-methylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</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/Metamfepramone" title="Metamfepramone">Metamfepramone</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/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></li></ul></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/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine"><i>p</i>BA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine"><i>p</i>CA</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</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/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine"><i>p</i>IA</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a class="mw-selflink selflink">Pseudoephedrine</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl"><span style="font-size:85%;">D</span>-Deprenyl</a>)</li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Piperazines:</i> <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Others:</i> <a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-ADN</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-AI</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-AT</a></li> <li><a href="/wiki/2-Benzylpiperidine" title="2-Benzylpiperidine">2-BP</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-BP</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <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/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexanamine</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</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></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Serotonin_releasing_agents" class="mw-redirect" title="Serotonin releasing agents"><abbr title="Serotonin releasing agents">SRAs</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 Serotonin releasing agents</span></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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Aminoindanes:</i> <a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/1-Aminomethyl-5-methoxyindane" title="1-Aminomethyl-5-methoxyindane">AMMI</a></li> <li><a href="/wiki/Ethyltrifluoromethylaminoindane" title="Ethyltrifluoromethylaminoindane">ETAI</a></li> <li><a href="/wiki/MDAI" title="MDAI">MDAI</a></li> <li><a href="/wiki/MDMAI" title="MDMAI">MDMAI</a></li> <li><a href="/wiki/MMAI" title="MMAI">MMAI</a></li> <li><a href="/wiki/Trifluoromethylaminoindane" title="Trifluoromethylaminoindane">TAI</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Aminotetralins:</i> <a href="/wiki/6-CAT" title="6-CAT">6-CAT</a></li> <li><a href="/wiki/8-OH-DPAT" title="8-OH-DPAT">8-OH-DPAT</a></li> <li><a href="/wiki/MDAT" title="MDAT">MDAT</a></li> <li><a href="/wiki/MDMAT" title="MDMAT">MDMAT</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Oxazolines:</i> <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/Fluminorex" title="Fluminorex">Fluminorex</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Phenethylamines:</i> <a href="/wiki/2-Methyl-MDA" title="2-Methyl-MDA">2-Methyl-MDA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-HA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-Methyl-MDA" title="5-Methyl-MDA">5-Methyl-MDA</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Methyl-MDA" title="6-Methyl-MDA">6-Methyl-MDA</a></li> <li><a href="/wiki/3-Methoxy-4-methyl-%CE%B1-ethylphenethylamine" class="mw-redirect" title="3-Methoxy-4-methyl-α-ethylphenethylamine">AEMMA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</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/4-Bromomethcathinone" title="4-Bromomethcathinone">Brephedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">DCA</a></li> <li><a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a></li> <li><a href="/wiki/DFMDA" title="DFMDA">DFMDA</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" class="mw-redirect" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/EDMA" title="EDMA">EDMA</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Flucetorex" title="Flucetorex">Flucetorex</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</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/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxymethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxymethamphetamine">MDHMA</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/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</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-Methoxy-4-methylmethamphetamine" class="mw-redirect" title="3-Methoxy-4-methylmethamphetamine">MMMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">NAP</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/4-Trifluoromethylamphetamine" class="mw-redirect" title="4-Trifluoromethylamphetamine">4-TFMA</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-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" title="Para-Methoxymethamphetamine">PMMA</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Piperazines:</i> <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/w/index.php?title=3-Methoxyphenylpiperazine&action=edit&redlink=1" class="new" title="3-Methoxyphenylpiperazine (page does not exist)">3-MeOPP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/3,4-Dichlorophenylpiperazine" class="mw-redirect" title="3,4-Dichlorophenylpiperazine">DCPP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Mepiprazole" title="Mepiprazole">Mepiprazole</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Para-Chlorophenylpiperazine" title="Para-Chlorophenylpiperazine">pCPP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li> <li><a href="/wiki/1-(4-Trifluoromethyl-phenyl)-piperazine" class="mw-redirect" title="1-(4-Trifluoromethyl-phenyl)-piperazine">pTFMPP</a></li> <li><a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Tryptamines:</i> <a href="/wiki/4-Methyl-AET" class="mw-redirect" title="4-Methyl-AET">4-Methyl-αET</a></li> <li><a href="/wiki/4-Methyl-AMT" class="mw-redirect" title="4-Methyl-AMT">4-Methyl-αMT</a></li> <li><a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a></li> <li><a href="/wiki/5-MeO-AMT" title="5-MeO-AMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a></li> <li><a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a></li> <li><a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Others:</i> <a href="/wiki/Indeloxazine" title="Indeloxazine">Indeloxazine</a></li> <li><a href="/wiki/Viqualine" title="Viqualine">Viqualine</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;">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><i>DAT modulators:</i> <i>Agonist-like:</i> <a href="/wiki/SoRI-9804" title="SoRI-9804">SoRI-9804</a></li> <li><a href="/w/index.php?title=SoRI-20040&action=edit&redlink=1" class="new" title="SoRI-20040 (page does not exist)">SoRI-20040</a>; <i>Antagonist-like:</i> <a href="/wiki/SoRI-20041" title="SoRI-20041">SoRI-20041</a></li></ul> <ul><li><i>Adrenergic release blockers:</i> <a href="/wiki/Bethanidine" title="Bethanidine">Bethanidine</a></li> <li><a href="/wiki/Bretylium" title="Bretylium">Bretylium</a></li> <li><a href="/wiki/Guanadrel" title="Guanadrel">Guanadrel</a></li> <li><a href="/wiki/Guanazodine" title="Guanazodine">Guanazodine</a></li> <li><a href="/wiki/Guanethidine" title="Guanethidine">Guanethidine</a></li> <li><a href="/wiki/Guanoxan" title="Guanoxan">Guanoxan</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><small><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> • <a href="/wiki/Template:Adrenergics" class="mw-redirect" title="Template:Adrenergics">Adrenergics</a> • <a href="/wiki/Template:Dopaminergics" class="mw-redirect" title="Template:Dopaminergics">Dopaminergics</a> • <a href="/wiki/Template:Serotonergics" class="mw-redirect" title="Template:Serotonergics">Serotonergics</a> • <a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a> • <a href="/wiki/Template:Monoamine_neurotoxins" class="mw-redirect" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></i></small></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="Phenethylamines352" 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:Phenethylamines" title="Template:Phenethylamines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenethylamines" title="Template talk:Phenethylamines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenethylamines" title="Special:EditPage/Template:Phenethylamines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Phenethylamines352" style="font-size:114%;margin:0 4em"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></div></th></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-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Psychedelics:</i> <a href="/wiki/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a></li> <li><a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a></li> <li><a href="/wiki/25D-NBOMe" title="25D-NBOMe">25D-NBOMe</a></li> <li><a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a></li> <li><a href="/wiki/25N-NBOMe" title="25N-NBOMe">25N-NBOMe</a></li> <li><a href="/wiki/2C-B" title="2C-B">2C-B</a></li> <li><a href="/w/index.php?title=2C-B-AN&action=edit&redlink=1" class="new" title="2C-B-AN (page does not exist)">2C-B-AN</a></li> <li><a href="/w/index.php?title=2C-Bn&action=edit&redlink=1" class="new" title="2C-Bn (page does not exist)">2C-Bn</a></li> <li><a href="/w/index.php?title=2C-Bu&action=edit&redlink=1" class="new" title="2C-Bu (page does not exist)">2C-Bu</a></li> <li><a href="/wiki/2C-C" title="2C-C">2C-C</a></li> <li><a href="/w/index.php?title=2C-CN&action=edit&redlink=1" class="new" title="2C-CN (page does not exist)">2C-CN</a></li> <li><a href="/wiki/2C-CP" title="2C-CP">2C-CP</a></li> <li><a href="/wiki/2C-D" title="2C-D">2C-D</a></li> <li><a href="/wiki/2C-E" title="2C-E">2C-E</a></li> <li><a href="/wiki/2C-EF" title="2C-EF">2C-EF</a></li> <li><a href="/wiki/2C-F" title="2C-F">2C-F</a></li> <li><a href="/wiki/2C-G" title="2C-G">2C-G</a></li> <li><a href="/wiki/2C-G-1" class="mw-redirect" title="2C-G-1">2C-G-1</a></li> <li><a href="/wiki/2C-G-2" class="mw-redirect" title="2C-G-2">2C-G-2</a></li> <li><a href="/wiki/2C-G-3" class="mw-redirect" title="2C-G-3">2C-G-3</a></li> <li><a href="/wiki/2C-G-4" class="mw-redirect" title="2C-G-4">2C-G-4</a></li> <li><a href="/wiki/2C-G-5" class="mw-redirect" title="2C-G-5">2C-G-5</a></li> <li><a href="/wiki/2C-G-6" class="mw-redirect" title="2C-G-6">2C-G-6</a></li> <li><a href="/wiki/2C-G-N" class="mw-redirect" title="2C-G-N">2C-G-N</a></li> <li><a href="/wiki/2C-H" title="2C-H">2C-H</a></li> <li><a href="/wiki/2C-I" title="2C-I">2C-I</a></li> <li><a href="/wiki/2C-iP" title="2C-iP">2C-iP</a></li> <li><a href="/wiki/2C-N" title="2C-N">2C-N</a></li> <li><a href="/w/index.php?title=2C-NH2&action=edit&redlink=1" class="new" title="2C-NH2 (page does not exist)">2C-NH2</a></li> <li><a href="/wiki/2C-O" class="mw-redirect" title="2C-O">2C-O</a></li> <li><a href="/wiki/2C-O-4" title="2C-O-4">2C-O-4</a></li> <li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li> <li><a href="/w/index.php?title=2C-Ph&action=edit&redlink=1" class="new" title="2C-Ph (page does not exist)">2C-Ph</a></li> <li><a href="/wiki/2C-SE" class="mw-redirect" title="2C-SE">2C-SE</a></li> <li><a href="/wiki/2C-T" title="2C-T">2C-T</a></li> <li><a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a></li> <li><a href="/wiki/2C-T-3" title="2C-T-3">2C-T-3</a></li> <li><a href="/wiki/2C-T-4" title="2C-T-4">2C-T-4</a></li> <li><a href="/w/index.php?title=2C-T-5&action=edit&redlink=1" class="new" title="2C-T-5 (page does not exist)">2C-T-5</a></li> <li><a href="/w/index.php?title=2C-T-6&action=edit&redlink=1" class="new" title="2C-T-6 (page does not exist)">2C-T-6</a></li> <li><a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a></li> <li><a href="/wiki/2C-T-8" title="2C-T-8">2C-T-8</a></li> <li><a href="/wiki/2C-T-9" class="mw-redirect" title="2C-T-9">2C-T-9</a></li> <li><a href="/w/index.php?title=2C-T-10&action=edit&redlink=1" class="new" title="2C-T-10 (page does not exist)">2C-T-10</a></li> <li><a href="/w/index.php?title=2C-T-11&action=edit&redlink=1" class="new" title="2C-T-11 (page does not exist)">2C-T-11</a></li> <li><a href="/w/index.php?title=2C-T-12&action=edit&redlink=1" class="new" title="2C-T-12 (page does not exist)">2C-T-12</a></li> <li><a href="/wiki/2C-T-13" title="2C-T-13">2C-T-13</a></li> <li><a href="/w/index.php?title=2C-T-14&action=edit&redlink=1" class="new" title="2C-T-14 (page does not exist)">2C-T-14</a></li> <li><a href="/wiki/2C-T-15" title="2C-T-15">2C-T-15</a></li> <li><a href="/wiki/2C-T-16" title="2C-T-16">2C-T-16</a></li> <li><a href="/wiki/2C-T-17" title="2C-T-17">2C-T-17</a></li> <li><a href="/w/index.php?title=2C-T-18&action=edit&redlink=1" class="new" title="2C-T-18 (page does not exist)">2C-T-18</a></li> <li><a href="/wiki/2C-T-19" title="2C-T-19">2C-T-19</a></li> <li><a href="/w/index.php?title=2C-T-20&action=edit&redlink=1" class="new" title="2C-T-20 (page does not exist)">2C-T-20</a></li> <li><a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a></li> <li><a href="/w/index.php?title=2C-T-22&action=edit&redlink=1" class="new" title="2C-T-22 (page does not exist)">2C-T-22</a></li> <li><a href="/w/index.php?title=2C-T-22.5&action=edit&redlink=1" class="new" title="2C-T-22.5 (page does not exist)">2C-T-22.5</a></li> <li><a href="/w/index.php?title=2C-T-23&action=edit&redlink=1" class="new" title="2C-T-23 (page does not exist)">2C-T-23</a></li> <li><a href="/w/index.php?title=2C-T-24&action=edit&redlink=1" class="new" title="2C-T-24 (page does not exist)">2C-T-24</a></li> <li><a href="/w/index.php?title=2C-T-25&action=edit&redlink=1" class="new" title="2C-T-25 (page does not exist)">2C-T-25</a></li> <li><a href="/w/index.php?title=2C-T-27&action=edit&redlink=1" class="new" title="2C-T-27 (page does not exist)">2C-T-27</a></li> <li><a href="/wiki/2C-T-28" title="2C-T-28">2C-T-28</a></li> <li><a href="/w/index.php?title=2C-T-30&action=edit&redlink=1" class="new" title="2C-T-30 (page does not exist)">2C-T-30</a></li> <li><a href="/w/index.php?title=2C-T-31&action=edit&redlink=1" class="new" title="2C-T-31 (page does not exist)">2C-T-31</a></li> <li><a href="/w/index.php?title=2C-T-32&action=edit&redlink=1" class="new" title="2C-T-32 (page does not exist)">2C-T-32</a></li> <li><a href="/wiki/2C-T-33" title="2C-T-33">2C-T-33</a></li> <li><a href="/wiki/2C-TFE" title="2C-TFE">2C-TFE</a></li> <li><a href="/wiki/2C-TFM" title="2C-TFM">2C-TFM</a></li> <li><a href="/wiki/2C-YN" title="2C-YN">2C-YN</a></li> <li><a href="/wiki/2C-V" title="2C-V">2C-V</a></li> <li><a href="/wiki/Allylescaline" title="Allylescaline">Allylescaline</a></li> <li><a href="/wiki/DESOXY" title="DESOXY">DESOXY</a></li> <li><a href="/wiki/Escaline" title="Escaline">Escaline</a></li> <li><a href="/wiki/Isoproscaline" title="Isoproscaline">Isoproscaline</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Macromerine" title="Macromerine">Macromerine</a></li> <li><a href="/wiki/3-Methoxy-4-ethoxyphenethylamine" title="3-Methoxy-4-ethoxyphenethylamine">MEPEA</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metaescaline" title="Metaescaline">Metaescaline</a></li> <li><a href="/wiki/Methallylescaline" title="Methallylescaline">Methallylescaline</a></li> <li><a href="/wiki/Proscaline" title="Proscaline">Proscaline</a></li> <li><a href="/wiki/Psi-2C-T-4" class="mw-redirect" title="Psi-2C-T-4">Psi-2C-T-4</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li></ul> <ul><li><i>Stimulants:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">α-Methylphenethylamine</a> (amphetamine)</li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/M-Methylphenethylamine" class="mw-redirect" title="M-Methylphenethylamine"><i>m</i>-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li> <li><a href="/wiki/O-Methylphenethylamine" class="mw-redirect" title="O-Methylphenethylamine"><i>o</i>-Methylphenethylamine</a></li> <li><a href="/wiki/P-Methylphenethylamine" class="mw-redirect" title="P-Methylphenethylamine"><i>p</i>-Methylphenethylamine</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li></ul> <ul><li><i>Entactogens:</i> <a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a><br /><i>Others:</i> <a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/3,4-Dimethoxyphenethylamine" title="3,4-Dimethoxyphenethylamine">DMPEA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</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><i>Psychedelics:</i> <a href="/wiki/3C-AL" title="3C-AL">3C-AL</a></li> <li><a href="/wiki/3C-BZ" title="3C-BZ">3C-BZ</a></li> <li><a href="/wiki/3C-E" title="3C-E">3C-E</a></li> <li><a href="/wiki/3C-MAL" title="3C-MAL">3C-MAL</a></li> <li><a href="/wiki/3C-P" title="3C-P">3C-P</a></li> <li><a href="/wiki/Aleph_(psychedelic)" title="Aleph (psychedelic)">Aleph</a></li> <li><a href="/wiki/Beatrice_(psychedelic)" title="Beatrice (psychedelic)">Beatrice</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/4-Methyl-2,5-methoxyphenylcyclopropylamine" class="mw-redirect" title="4-Methyl-2,5-methoxyphenylcyclopropylamine">DMCPA</a></li> <li><a href="/wiki/DMMDA" title="DMMDA">DMMDA</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-fluoroethylamphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-fluoroethylamphetamine">DOEF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-nitroamphetamine" title="2,5-Dimethoxy-4-nitroamphetamine">DON</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-propylamphetamine" title="2,5-Dimethoxy-4-propylamphetamine">DOPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-trifluoromethylamphetamine" title="2,5-Dimethoxy-4-trifluoromethylamphetamine">DOTFM</a></li> <li><a href="/wiki/Ganesha_(psychedelic)" title="Ganesha (psychedelic)">Ganesha</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDA-2" title="MMDA-2">MMDA-2</a></li> <li><a href="/wiki/Psi-DOM" class="mw-redirect" title="Psi-DOM">Psi-DOM</a></li> <li><a href="/wiki/Trimethoxyamphetamine" class="mw-redirect" title="Trimethoxyamphetamine">TMA</a></li> <li><a href="/wiki/Tetramethoxyamphetamine" class="mw-redirect" title="Tetramethoxyamphetamine">TeMA</a></li> <li><a href="/wiki/ZDCM-04" title="ZDCM-04">ZDCM-04</a><br /><i>Stimulants:</i> <a href="/wiki/2-Fluoroamphetamine" title="2-Fluoroamphetamine">2-FA</a></li> <li><a href="/wiki/2-Fluoromethamphetamine" title="2-Fluoromethamphetamine">2-FMA</a></li> <li><a href="/wiki/3-Fluoroamphetamine" title="3-Fluoroamphetamine">3-FA</a></li> <li><a href="/wiki/3-Fluoromethamphetamine" title="3-Fluoromethamphetamine">3-FMA</a></li> <li><a href="/wiki/Acridorex" title="Acridorex">Acridorex</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</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/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/Benfluorex" title="Benfluorex">Benfluorex</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</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/Flucetorex" title="Flucetorex">Flucetorex</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/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Isopropylamphetamine" title="Isopropylamphetamine">Isopropylamphetamine</a></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/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> (Dextromethamphetamine, <a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</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/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/L-Norpseudoephedrine" title="L-Norpseudoephedrine"><span style="font-size:85%;">L</span>-Norpseudoephedrine</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/Oxifentorex" title="Oxifentorex">Oxifentorex</a></li> <li><a href="/wiki/Oxilofrine" title="Oxilofrine">Oxilofrine</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</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/4-Fluoroamphetamine" title="4-Fluoroamphetamine">PFA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">PFMA</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-Methoxy-N-ethylamphetamine" title="Para-Methoxy-N-ethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxy-N-methylamphetamine" class="mw-redirect" title="Para-Methoxy-N-methylamphetamine">PMMA</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/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a class="mw-selflink selflink">Pseudoephedrine</a></li> <li><a href="/wiki/Sibutramine" title="Sibutramine">Sibutramine</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/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a><br /><i>Entactogens:</i> <a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APB" title="5-APB">5-APB</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-EAPB" title="5-EAPB">5-EAPB</a></li> <li><a href="/wiki/5-IT" class="mw-redirect" title="5-IT">5-IT</a></li> <li><a href="/wiki/5-MAPB" title="5-MAPB">5-MAPB</a></li> <li><a href="/wiki/5-MAPDB" title="5-MAPDB">5-MAPDB</a></li> <li><a href="/wiki/6-APB" title="6-APB">6-APB</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Chloro-MDMA" title="6-Chloro-MDMA">6-Chloro-MDMA</a></li> <li><a href="/wiki/6-EAPB" title="6-EAPB">6-EAPB</a></li> <li><a href="/wiki/6-IT" class="mw-redirect" title="6-IT">6-IT</a></li> <li><a href="/wiki/6-MAPB" title="6-MAPB">6-MAPB</a></li> <li><a href="/wiki/6-MAPDB" title="6-MAPDB">6-MAPDB</a></li> <li><a href="/wiki/Ethylidenedioxyamphetamine" class="mw-redirect" title="Ethylidenedioxyamphetamine">EDA</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/2,3-Methylenedioxyamphetamine" title="2,3-Methylenedioxyamphetamine">2,3-MDA</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">3,4-MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxylmethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxylmethamphetamine">MDHMA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a><br /><i>Others:</i> <a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">3,4-DCA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/DiFMDA" class="mw-redirect" title="DiFMDA">DiFMDA</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl"><span style="font-size:85%;">D</span>-Deprenyl</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phentermine" title="Phentermine">Phentermines</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><i>Stimulants:</i> <a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</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/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a><br /><i>Entactogens:</i> <a href="/wiki/Methylenedioxyphentermine" class="mw-redirect" title="Methylenedioxyphentermine">MDPH</a></li> <li><a href="/wiki/Methylenedioxymethylphentermine" class="mw-redirect" title="Methylenedioxymethylphentermine">MDMPH</a><br /><i>Others:</i> <a href="/wiki/Cericlamine" title="Cericlamine">Cericlamine</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-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/3-Fluoromethcathinone" title="3-Fluoromethcathinone">3-FMC</a></li> <li><a href="/wiki/4-Methylcathinone" title="4-Methylcathinone">4-MC</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-Ethylmethcathinone" title="4-Ethylmethcathinone">4-EMC</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">4-FMC</a></li> <li><a href="/wiki/4-Methylethcathinone" title="4-Methylethcathinone">4-MEC</a></li> <li><a href="/wiki/4-Methylbuphedrone" title="4-Methylbuphedrone">4-MeMABP</a></li> <li><a href="/wiki/4-Methylpentedrone" title="4-Methylpentedrone">4-MPD</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/Brephedrone" class="mw-redirect" title="Brephedrone">Brephedrone</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/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/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</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/N-Ethylbuphedrone" title="N-Ethylbuphedrone">NEB</a></li> <li><a href="/wiki/N-Ethylhexedrone" title="N-Ethylhexedrone">N-Ethylhexedrone</a></li> <li><a href="/wiki/N-Ethylpentedrone" title="N-Ethylpentedrone">N-Ethylpentedrone</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/Radafaxine" title="Radafaxine">Radafaxine</a><br /><i>Entactogens:</i> <a href="/wiki/3,4-Dimethylmethcathinone" title="3,4-Dimethylmethcathinone">3,4-DMMC</a></li> <li><a href="/wiki/3-Methylmethcathinone" title="3-Methylmethcathinone">3-MMC</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Methylenedioxycathinone" title="Methylenedioxycathinone">Methylenedioxycathinone</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamines</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><i>Entactogens:</i> <a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Methylphenylisobutylamine" title="4-Methylphenylisobutylamine">4-MAB</a></li> <li><a href="/wiki/Ariadne_(psychedelic)" class="mw-redirect" title="Ariadne (psychedelic)">Ariadne</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/MBDB" title="MBDB">MBDB</a><br /><i>Stimulants:</i> <a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">Phenylalkylpyrrolidines</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><i>Stimulants:</i> <a href="/wiki/Alpha-Pyrrolidinobutiophenone" class="mw-redirect" title="Alpha-Pyrrolidinobutiophenone">α-PBP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinohexiophenone" class="mw-redirect" title="Alpha-Pyrrolidinohexiophenone">α-PHP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopropiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopropiophenone">α-PPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiophenone">α-PVP</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/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinopropiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinopropiophenone">MDPPP</a></li> <li><a href="/wiki/3,4-Methylenedioxypyrovalerone" class="mw-redirect" title="3,4-Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">4-MePBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">4-MePHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">4-MePPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopropiophenone" title="4'-Methoxy-α-pyrrolidinopropiophenone">MOPPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopentiophenone" title="4'-Methoxy-α-pyrrolidinopentiophenone">MOPVP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-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/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">PEP</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/Catecholamine" title="Catecholamine">Catecholamines</a><br /><span style="font-size:85%;">(and close relatives)</span></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/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/6-Hydroxydopamine" class="mw-redirect" title="6-Hydroxydopamine">6-OHDA</a></li> <li><a href="/wiki/Alpha-Methyldopamine" class="mw-redirect" title="Alpha-Methyldopamine">a-Me-DA</a></li> <li><a href="/wiki/Alpha-Methyltyramine" class="mw-redirect" title="Alpha-Methyltyramine">a-Me-TRA</a></li> <li><a href="/wiki/Adrenochrome" title="Adrenochrome">Adrenochrome</a></li> <li><a href="/wiki/Ciladopa" title="Ciladopa">Ciladopa</a></li> <li><a href="/wiki/D-DOPA" title="D-DOPA"><span style="font-size:85%;">D</span>-DOPA</a> (Dextrodopa)</li> <li><a href="/wiki/Dimetofrine" title="Dimetofrine">Dimetofrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Epinephrine_(neurotransmitter)" class="mw-redirect" title="Epinephrine (neurotransmitter)">Epinephrine</a></li> <li><a href="/wiki/Epinine" class="mw-redirect" title="Epinine">Epinine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Fenclonine" title="Fenclonine">Fenclonine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA"><span style="font-size:85%;">L</span>-DOPA</a> (Levodopa)</li> <li><a href="/wiki/L-DOPS" class="mw-redirect" title="L-DOPS"><span style="font-size:85%;">L</span>-DOPS</a> (Droxidopa)</li> <li><a href="/wiki/L-Phenylalanine" class="mw-redirect" title="L-Phenylalanine"><span style="font-size:85%;">L</span>-Phenylalanine</a></li> <li><a href="/wiki/L-Tyrosine" class="mw-redirect" title="L-Tyrosine"><span style="font-size:85%;">L</span>-Tyrosine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</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/Metaterol" title="Metaterol">Metaterol</a></li> <li><a href="/wiki/Metirosine" class="mw-redirect" title="Metirosine">Metirosine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/N,N-Dimethyldopamine" title="N,N-Dimethyldopamine">N,N-Dimethyldopamine</a></li> <li><a href="/wiki/Nordefrin" class="mw-redirect" title="Nordefrin">Nordefrin</a> (<a href="/wiki/Levonordefrin" class="mw-redirect" title="Levonordefrin">Levonordefrin</a>)</li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a> (<i>m</i>-Octopamine)</li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Miscellaneous</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/AL-LAD" title="AL-LAD">AL-LAD</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Desvenlafaxine" title="Desvenlafaxine">Desvenlafaxine</a></li> <li><a href="/wiki/Diphenidine" title="Diphenidine">Diphenidine</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/ETH-LAD" title="ETH-LAD">ETH-LAD</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fluorolintane" title="Fluorolintane">Fluorolintane</a></li> <li><a href="/wiki/Hexapradol" title="Hexapradol">Hexapradol</a></li> <li><a href="/wiki/IP-LAD" class="mw-redirect" title="IP-LAD">IP-LAD</a></li> <li><a href="/wiki/Lysergic_acid_amide" class="mw-redirect" title="Lysergic acid amide">Lysergic acid amide</a></li> <li><a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">Lysergic acid 2-butyl amide</a></li> <li><a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">Lysergic acid 2,4-dimethylazetidide</a></li> <li><a href="/wiki/LSD" title="LSD">Lysergic acid diethylamide</a></li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Methoxphenidine" title="Methoxphenidine">Methoxphenidine</a></li> <li><a href="/wiki/MT-45" title="MT-45">MT-45</a></li> <li><a href="/wiki/PARGY-LAD" title="PARGY-LAD">PARGY-LAD</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a href="/wiki/PRO-LAD" title="PRO-LAD">PRO-LAD</a></li> <li><a href="/wiki/Pronethalol" title="Pronethalol">Pronethalol</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a> (<a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a>)</li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Thiamphenicol" title="Thiamphenicol">Thiamphenicol</a></li> <li><a href="/wiki/UWA-101" title="UWA-101">UWA-101</a></li> <li><a href="/wiki/Venlafaxine" title="Venlafaxine">Venlafaxine</a></li></ul> </div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;flex:0 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