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1.5 Low blood pressure </div> </a> <ul id="toc-Low_blood_pressure-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"> 1.6 Other uses </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"> 1.7 Available forms </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 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Contraindications"> <div class="vector-toc-text"> 2 Contraindications </div> </a> <ul id="toc-Contraindications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item 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<div class="vector-toc-text"> 5.2 Pharmacokinetics </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"> 5.2.1 Absorption </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"> 5.2.2 Distribution </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"> 5.2.3 Metabolism </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"> 5.2.4 Elimination </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 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> 6 Chemistry </div> </a> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> 7 History </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 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> 8 Society and culture </div> </a> <button aria-controls="toc-Society_and_culture-sublist" class="cdx-button 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class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Toggle the table of contents </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">Phenylephrine</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 26 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-26" aria-hidden="true" > 26 languages </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%8A%D9%86%D9%8A%D9%84%D9%8A%D9%81%D8%B1%D9%8A%D9%86" title="فينيليفرين – Arabic" lang="ar" hreflang="ar" data-title="فينيليفرين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%81%D9%86%DB%8C%D9%84_%D8%A7%D9%81%D8%B1%DB%8C%D9%86" title="فنیل افرین – South Azerbaijani" lang="azb" hreflang="azb" data-title="فنیل افرین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Ffenyleffrin" title="Ffenyleffrin – Welsh" lang="cy" hreflang="cy" data-title="Ffenyleffrin" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target">Cymraeg</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Phenylephrin" title="Phenylephrin – German" lang="de" hreflang="de" data-title="Phenylephrin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Fenilefrina" title="Fenilefrina – Spanish" lang="es" hreflang="es" data-title="Fenilefrina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Fenilefrina" title="Fenilefrina – Basque" lang="eu" hreflang="eu" data-title="Fenilefrina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target">Euskara</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%D9%86%DB%8C%D9%84%E2%80%8C%D8%A7%D9%81%D8%B1%DB%8C%D9%86" title="فنیل‌افرین – Persian" lang="fa" hreflang="fa" data-title="فنیل‌افرین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Ph%C3%A9nyl%C3%A9phrine" title="Phényléphrine – French" lang="fr" hreflang="fr" data-title="Phényléphrine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Fenilefrin" title="Fenilefrin – Indonesian" lang="id" hreflang="id" data-title="Fenilefrin" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Fenilefrina" title="Fenilefrina – Italian" lang="it" hreflang="it" data-title="Fenilefrina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A4%D7%A0%D7%99%D7%9C%D7%90%D7%A4%D7%A8%D7%99%D7%9F" title="פנילאפרין – Hebrew" lang="he" hreflang="he" data-title="פנילאפרין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Fenilefrin" title="Fenilefrin – Hungarian" lang="hu" hreflang="hu" data-title="Fenilefrin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%82%A7%E3%83%8B%E3%83%AC%E3%83%95%E3%83%AA%E3%83%B3" title="フェニレフリン – Japanese" lang="ja" hreflang="ja" data-title="フェニレフリン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%AB%E0%AC%BF%E0%AC%A8%E0%AC%BE%E0%AC%87%E0%AC%B2%E0%AD%87%E0%AC%AB%E0%AD%8D%E0%AC%B0%E0%AC%BF%E0%AC%A8" title="ଫିନାଇଲେଫ୍ରିନ – Odia" lang="or" hreflang="or" data-title="ଫିନାଇଲେଫ୍ରିନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target">ଓଡ଼ିଆ</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Fenylefryna" title="Fenylefryna – Polish" lang="pl" hreflang="pl" data-title="Fenylefryna" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Fenilefrina" title="Fenilefrina – Portuguese" lang="pt" hreflang="pt" data-title="Fenilefrina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B8%D0%BB%D1%8D%D1%84%D1%80%D0%B8%D0%BD" title="Фенилэфрин – Russian" lang="ru" hreflang="ru" data-title="Фенилэфрин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Phenylephrin" title="Phenylephrin – Albanian" lang="sq" hreflang="sq" data-title="Phenylephrin" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target">Shqip</a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Fenilefrin" title="Fenilefrin – Slovenian" lang="sl" hreflang="sl" data-title="Fenilefrin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Fenilefrin" title="Fenilefrin – Serbian" lang="sr" hreflang="sr" data-title="Fenilefrin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Fenilefrin" title="Fenilefrin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Fenilefrin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Fenylefrin" title="Fenylefrin – Swedish" lang="sv" hreflang="sv" data-title="Fenylefrin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Fenilefrin" title="Fenilefrin – Turkish" lang="tr" hreflang="tr" data-title="Fenilefrin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D1%96%D0%BB%D0%B5%D1%84%D1%80%D0%B8%D0%BD" title="Фенілефрин – Ukrainian" lang="uk" hreflang="uk" data-title="Фенілефрин" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Phenylephrine" title="Phenylephrine – Vietnamese" lang="vi" hreflang="vi" data-title="Phenylephrine" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%8B%AF%E7%A6%8F%E6%9E%97" title="苯福林 – Chinese" lang="zh" hreflang="zh" data-title="苯福林" data-language-autonym="中文" data-language-local-name="Chinese" 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.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">Phenylephrine</caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Phenylephrine_Structural_Formula_V1.svg" class="mw-file-description"><img alt="Skeletal formula of phenylephrine" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Phenylephrine_Structural_Formula_V1.svg/220px-Phenylephrine_Structural_Formula_V1.svg.png" decoding="async" width="220" height="97" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Phenylephrine_Structural_Formula_V1.svg/330px-Phenylephrine_Structural_Formula_V1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/27/Phenylephrine_Structural_Formula_V1.svg/440px-Phenylephrine_Structural_Formula_V1.svg.png 2x" data-file-width="381" data-file-height="168" /></a></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:(R)-Phenylephrine_molecule_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of the phenylephrine molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/%28R%29-Phenylephrine_molecule_ball.png/220px-%28R%29-Phenylephrine_molecule_ball.png" decoding="async" width="220" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/%28R%29-Phenylephrine_molecule_ball.png/330px-%28R%29-Phenylephrine_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/%28R%29-Phenylephrine_molecule_ball.png/440px-%28R%29-Phenylephrine_molecule_ball.png 2x" data-file-width="2000" data-file-height="1114" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˌfɛnəlˈɛfriːn, fiː-, -ɪn/</a> </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">Neosynephrine, Sudafed PE, others<a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-IndexNominum2000-2">[2]</a><a href="#cite_note-DrugBank-3">[3]</a><a href="#cite_note-Drugs.com-International-4">[4]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Phenephrine; Fenefrine; L-m-Synephrine; Metaoxedrine; Neo-Oxedrine; Mesatonum; Neosynephrine; Adrianol; (R)-β,3-Dihydroxy-N-methylphenethylamine<a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-IndexNominum2000-2">[2]</a><a href="#cite_note-Drugs.com-International-4">[4]</a></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"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/phenylephrine.html">Monograph</a></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><abbr class="country-name" title="European Union">EU</abbr> <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">EMA</a>: <a rel="nofollow" class="external text" href="https://www.ema.europa.eu/en/medicines/search_api_aggregation_ema_active_substance_and_inn_common_name/Phenylephrine">by INN</a></li> <li><abbr class="country-name" title="United States">US</abbr> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Phenylephrine">Phenylephrine</a></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 administration</a></th><td class="infobox-data"><a href="/wiki/By_mouth" class="mw-redirect" title="By mouth">By mouth</a>, <a href="/wiki/Intranasal" class="mw-redirect" title="Intranasal">intranasal</a>, <a href="/wiki/Ophthalmic" class="mw-disambig" title="Ophthalmic">ophthalmic</a>, <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenous</a>, <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular</a>, <a href="/wiki/Rectal_administration" title="Rectal administration">rectal</a><a href="#cite_note-RichardsLopezMaani2023-5">[5]</a><a href="#cite_note-Drugs@FDA-6">[6]</a><a href="#cite_note-DailyMed-7">[7]</a></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/Alpha-adrenergic_agonist#α1_agonist" title="Alpha-adrenergic agonist">α1-adrenergic receptor agonist</a>; <a href="/wiki/Vasopressor" class="mw-redirect" title="Vasopressor">vasopressor</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_C01" title="ATC code C01">C01CA06</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=C01CA06">WHO</a>) <a href="/wiki/ATC_code_R01" title="ATC code R01">R01AA04</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=R01AA04">WHO</a>), <a href="/wiki/ATC_code_R01" title="ATC code R01">R01AB01</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=R01AB01">WHO</a>) (combinations), <a href="/wiki/ATC_code_R01" title="ATC code R01">R01BA03</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=R01BA03">WHO</a>), <a href="/wiki/ATC_code_S01" title="ATC code S01">S01FB01</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=S01FB01">WHO</a>), <a href="/wiki/ATC_code_S01" title="ATC code S01">S01GA05</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=S01GA05">WHO</a>), <a href="/wiki/ATC_code_C05" title="ATC code C05">C05AX06</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=C05AX06">WHO</a>)</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><abbr class="country-name" title="Australia">AU</abbr>: <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_2" title="Standard for the Uniform Scheduling of Medicines and Poisons">S2</a> (Pharmacy medicine)</li> <li><abbr class="country-name" title="United Kingdom">UK</abbr>: <a href="/wiki/General_sales_list" class="mw-redirect" title="General sales list">General sales list</a> (GSL, OTC)</li> <li><abbr class="country-name" title="United States">US</abbr>: <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">OTC</a> / Rx-only</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a>: conflicting—38%<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-DrugBank-3">[3]</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a><a href="#cite_note-Medsafe2004-10">[10]</a> or 0.003%<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">95%[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>]</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a> and <a href="/wiki/Intestine" class="mw-redirect" title="Intestine">intestines</a> (via <a href="/wiki/Oxidative_deamination" title="Oxidative deamination">oxidative deamination</a> by <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>; <a href="/wiki/Sulfation" title="Sulfation">sulfation</a>; <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a>)<a href="#cite_note-RichardsLopezMaani2023-5">[5]</a><a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-DrugBank-3">[3]</a><a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data">• <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/3-Hydroxymandelic-acid">meta-Hydroxymandelic acid</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a><a href="#cite_note-DrugBank-3">[3]</a> • <a href="/wiki/Sulfate" title="Sulfate">Sulfate</a> <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugates</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a><a href="#cite_note-DrugBank-3">[3]</a> • <a href="/wiki/Glucuronide" title="Glucuronide">Glucuronide</a> <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugates</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a></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">IV: Very rapid<a href="#cite_note-AHFS2022-12">[12]</a> Oral: 15–20 min<a href="#cite_note-AHFS2022-12">[12]</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> Intranasal: <2 min<a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> Eye drop: <30 min<a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a></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 half-life</a></th><td class="infobox-data">2–3 hours<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-RichardsLopezMaani2023-5">[5]</a><a href="#cite_note-DrugBank-3">[3]</a><a href="#cite_note-KanferDowseVuma1993-13">[13]</a></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">IV: 20 min–5 h<a href="#cite_note-AHFS2022-12">[12]</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> Oral: 2–4 h<a href="#cite_note-AHFS2022-12">[12]</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> Intranasal: 0.5–4 h<a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> Eye drop: 3–7 h<a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a></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>: 86% (3–16% unchanged)<a href="#cite_note-RichardsLopezMaani2023-5">[5]</a><a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-DrugBank-3">[3]</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">3-[(1R)-1-Hydroxy-2-(methylamino)ethyl]phenol</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><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=59-42-7">59-42-7</a> <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" />Y</li><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=61-76-7">61-76-7</a></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> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6041">6041</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=485">485</a></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><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00388">DB00388</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5818.html">5818</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/1WS297W6MV">1WS297W6MV</a></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><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D08365">D08365</a> <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" />Y</li><li><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00511">D00511</a></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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8093">CHEBI:8093</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL1215">ChEMBL1215</a> <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" />Y</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> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID9023465">DTXSID9023465</a> <a href="https://www.wikidata.org/wiki/Q421910#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></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">ECHA InfoCard</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.386">100.000.386</a> <a href="https://www.wikidata.org/wiki/Q421910#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></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data">C9H13NO2</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">167.208 g·mol−1</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><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%5BC%40H%5D%28c1cc%28O%29ccc1%29CNC">Interactive image</a></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](c1cc(O)ccc1)CNC</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/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1 <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" />Y</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:SONNWYBIRXJNDC-VIFPVBQESA-N <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" />Y</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>  <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464201108&page2=Phenylephrine">(verify)</a></td></tr></tbody></table> Phenylephrine, sold under the brand names Neosynephrine and Sudafed PE among others, is a <a href="/wiki/Medication" title="Medication">medication</a> used as a <a href="/wiki/Decongestant" title="Decongestant">decongestant</a> for uncomplicated <a href="/wiki/Nasal_congestion" title="Nasal congestion">nasal congestion</a>,<a href="#cite_note-RichardsLopezMaani2023-5">[5]</a> to <a href="/wiki/Mydriasis" title="Mydriasis">dilate the pupil</a>, to increase <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a> (given <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenously</a> in cases of <a href="/wiki/Hypotension" title="Hypotension">low blood pressure</a>), and to relieve <a href="/wiki/Hemorrhoids" class="mw-redirect" title="Hemorrhoids">hemorrhoids</a> (as a <a href="/wiki/Suppository" title="Suppository">suppository</a>).<a href="#cite_note-AHFS2022-12">[12]</a><a href="#cite_note-BNF76-14">[14]</a> It can be taken <a href="/wiki/By_mouth" class="mw-redirect" title="By mouth">by mouth</a>, as a <a href="/wiki/Nasal_spray" title="Nasal spray">nasal spray</a>, given by <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection">injection into a vein</a> or <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">muscle</a>, <a href="/wiki/Transdermal_administration" class="mw-redirect" title="Transdermal administration">applied to the skin</a>, or as a <a href="/wiki/Rectal_administration" title="Rectal administration">rectal</a> <a href="/wiki/Suppository" title="Suppository">suppository</a>.<a href="#cite_note-AHFS2022-12">[12]</a><a href="#cite_note-RichardsLopezMaani2023-5">[5]</a> Common <a href="/wiki/Side_effect" title="Side effect">side effects</a> when taken by mouth or injected include <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, <a href="/wiki/Headache" title="Headache">headache</a>, and <a href="/wiki/Anxiety" title="Anxiety">anxiety</a>.<a href="#cite_note-AHFS2022-12">[12]</a> Use on hemorrhoids is generally well tolerated.<a href="#cite_note-AHFS2022-12">[12]</a> Severe side effects may include a <a href="/wiki/Bradycardia" title="Bradycardia">slow heart rate</a>, <a href="/wiki/Intestinal_ischemia" title="Intestinal ischemia">intestinal ischemia</a>, <a href="/wiki/Angina" title="Angina">chest pain</a>, <a href="/wiki/Kidney_failure" title="Kidney failure">kidney failure</a>, and <a href="/wiki/Tissue_death" class="mw-redirect" title="Tissue death">tissue death</a> at the site of injection.<a href="#cite_note-AHFS2022-12">[12]</a><a href="#cite_note-BNF76-14">[14]</a> It is unclear whether its use during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> and <a href="/wiki/Breastfeeding" title="Breastfeeding">breastfeeding</a> is safe.<a href="#cite_note-AHFS2022-12">[12]</a> Phenylephrine is a <a href="/wiki/Binding_selectivity" title="Binding selectivity">selective</a> <a href="/wiki/Alpha-1_adrenergic_receptor" title="Alpha-1 adrenergic receptor">α1-adrenergic receptor</a> <a href="/wiki/Agonist" title="Agonist">agonist</a> with minimal to no <a href="/wiki/Beta-adrenergic_receptor" class="mw-redirect" title="Beta-adrenergic receptor">β-adrenergic receptor</a> agonist activity or <a href="/wiki/Norepinephrine_releasing_agent" title="Norepinephrine releasing agent">induction of norepinephrine release</a>.<a href="#cite_note-RichardsLopezMaani2023-5">[5]</a><a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-ODonnell1995-15">[15]</a> It causes <a href="/wiki/Constriction" title="Constriction">constriction</a> of both <a href="/wiki/Arteries" class="mw-redirect" title="Arteries">arteries</a> and <a href="/wiki/Veins" class="mw-redirect" title="Veins">veins</a>.<a href="#cite_note-AHFS2022-12">[12]</a> Phenylephrine was patented in 1933<a href="#cite_note-16">[16]</a> and came into medical use in 1938.<a href="#cite_note-Fis2006-17">[17]</a> It is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a>.<a href="#cite_note-BNF76-14">[14]</a><a href="#cite_note-18">[18]</a><a href="#cite_note-19">[19]</a> Unlike <a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">pseudoephedrine</a>, abuse of phenylephrine is very uncommon.<a href="#cite_note-20">[20]</a> Its effectiveness as a nasal decongestant has been questioned.<a href="#cite_note-AHFS2022-12">[12]</a><a href="#cite_note-Hatton2022-21">[21]</a><a href="#cite_note-Lowe2022-22">[22]</a> In 2023, a U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) panel concluded that the drug was ineffective as a nasal decongestant when taken orally.<a href="#cite_note-christensen23-23">[23]</a> In November 2024, the FDA proposed to remove oral phenylephrine as an active ingredient that can be used in over-the-counter (OTC) monograph drug products for the temporary relief of nasal congestion.<a href="#cite_note-FDA_PR_20241107-24">[24]</a> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Decongestant">Decongestant</h3>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=2" title="Edit section: Decongestant">edit</a>]</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-Globalize plainlinks metadata ambox ambox-content ambox-globalize" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><img alt="Globe icon." src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Ambox_globe_content.svg/48px-Ambox_globe_content.svg.png" decoding="async" width="48" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Ambox_globe_content.svg/73px-Ambox_globe_content.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Ambox_globe_content.svg/97px-Ambox_globe_content.svg.png 2x" data-file-width="350" data-file-height="290" /></div></td><td class="mbox-text"><div class="mbox-text-span">The examples and perspective in this section deal primarily with US-centric section and do not represent a <a href="/wiki/Wikipedia:WikiProject_Countering_systemic_bias" title="Wikipedia:WikiProject Countering systemic bias">worldwide view</a> of the subject. You may <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Phenylephrine&action=edit">improve this section</a>, discuss the issue on the <a href="/wiki/Talk:Phenylephrine" title="Talk:Phenylephrine">talk page</a>, or create a new section, as appropriate. (January 2024) (<a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a>)</div></td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-Unbalanced plainlinks metadata ambox ambox-content ambox-unbalanced" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Unbalanced_scales.svg/45px-Unbalanced_scales.svg.png" decoding="async" width="45" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Unbalanced_scales.svg/68px-Unbalanced_scales.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Unbalanced_scales.svg/90px-Unbalanced_scales.svg.png 2x" data-file-width="400" data-file-height="354" /></div></td><td class="mbox-text"><div class="mbox-text-span">This section may be <a href="/wiki/Wikipedia:Neutral_point_of_view#Undue_weight" title="Wikipedia:Neutral point of view">unbalanced</a> toward certain viewpoints. Please <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Phenylephrine&action=edit">improve the article</a> by adding information on neglected viewpoints, or discuss the issue on the <a href="/wiki/Talk:Phenylephrine" title="Talk:Phenylephrine">talk page</a>. (July 2024)</div></td></tr></tbody></table> Phenylephrine is used as an alternative to <a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">pseudoephedrine</a> as a decongestant, whose availability has been restricted in some countries due to a potential for use in the illicit synthesis of <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>.<a href="#cite_note-Presley_2018-25">[25]</a> Its efficacy as an oral decongestant has been questioned, with several independent studies finding that it provided no more relief to sinus congestion than a placebo.<a href="#cite_note-danzig09-26">[26]</a><a href="#cite_note-yao09-27">[27]</a><a href="#cite_note-Hendeles2006-28">[28]</a> A 2007 meta-analysis concluded that the evidence for its effectiveness is insufficient,<a href="#cite_note-Annals-29">[29]</a> though another meta-analysis published shortly thereafter by researchers from <a href="/wiki/GlaxoSmithKline" class="mw-redirect" title="GlaxoSmithKline">GlaxoSmithKline</a> found the standard 10-mg dose to be more effective than a placebo; however, the fact that GSK markets many products containing phenylephrine has raised some speculation regarding selective publishing and other controversial techniques.<a href="#cite_note-GSK-30">[30]</a> A 2007 study by <a href="/wiki/Wyeth_Consumer_Healthcare" class="mw-redirect" title="Wyeth Consumer Healthcare">Wyeth Consumer Healthcare</a> notes that 7 studies available in 1976 support the efficacy of phenylephrine at a 10 mg dosage.<a href="#cite_note-Desjardins2007-31">[31]</a> The <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> withdrew the indication "for the temporary relief of nasal congestion associated with sinusitis" in 2007.<a href="#cite_note-AHFS2022-12">[12]</a> Two studies published in 2009, examined the effects of phenylephrine on symptoms of <a href="/wiki/Allergic_rhinitis" title="Allergic rhinitis">allergic rhinitis</a> by exposing people to pollen in a controlled, indoor environment. Neither study was able to distinguish between the effects of phenylephrine or a placebo. Pseudoephedrine and <a href="/wiki/Loratadine" title="Loratadine">loratadine</a>–<a href="/wiki/Montelukast" title="Montelukast">montelukast</a> therapy were found to be significantly more effective than both phenylephrine and placebo.<a href="#cite_note-danzig09-26">[26]</a><a href="#cite_note-yao09-27">[27]</a> Pseudoephedrine was previously much more commonly available in the United States, however, provisions 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> placed restrictions on sale in the United States of pseudoephedrine products to prevent the <a href="/wiki/Clandestine_chemistry" title="Clandestine chemistry">clandestine manufacture</a> of methamphetamine. Since 2004, phenylephrine has been increasingly marketed as a substitute for pseudoephedrine; some manufacturers have changed the active ingredients of products to avoid the restrictions on sales.<a href="#cite_note-HeraldTribune-32">[32]</a> Phenylephrine has been off-patent for some time,[<a href="/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Chronological_items" title="Wikipedia:Manual of Style/Dates and numbers">when?</a>] and many generic brands are available.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] In September 2023, an independent advisory committee to the U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) unanimously agreed that there is insufficient evidence showing that "orally administered phenylephrine is effective as a nasal decongestant".<a href="#cite_note-33">[33]</a> The committee also unanimously believes that this does not need further study. The FDA responded to the committee, stating it would take its advice under advisement.<a href="#cite_note-christensen23-23">[23]</a><a href="#cite_note-34">[34]</a> In November 2024, the FDA proposed to remove oral phenylephrine as an active ingredient that can be used in over-the-counter (OTC) monograph drug products for the temporary relief of nasal congestion.<a href="#cite_note-FDA_PR_20241107-24">[24]</a> <div class="mw-heading mw-heading3"><h3 id="Hemorrhoids">Hemorrhoids</h3>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=3" title="Edit section: Hemorrhoids">edit</a>]</div> <a href="/wiki/Hemorrhoids" class="mw-redirect" title="Hemorrhoids">Hemorrhoids</a> are caused by swollen <a href="/wiki/Veins" class="mw-redirect" title="Veins">veins</a> in the <a href="/wiki/Rectal" class="mw-redirect" title="Rectal">rectal</a> area.<a href="#cite_note-35">[35]</a> Phenylephrine can be used topically to prevent symptoms of hemorrhoids. Phenylephrine causes the constriction of vascular smooth muscle and is often used in the treatment of hemorrhoids to narrow the swollen veins and relieve the attendant pain. However, veins contain less vascular smooth muscle in their walls than arteries. Products for treatment may also include substances that will form a protective barrier over the inflamed area, resulting in less pain when <a href="/wiki/Feces" title="Feces">feces</a> are passed.<a href="#cite_note-36">[36]</a> Phenylephrine hydrochloride at 0.25% is used as a <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstrictor</a> in <a href="/wiki/Suppository" title="Suppository">suppository</a> formulations for hemorrhoid treatment.<a href="#cite_note-Suppository-Label-37">[37]</a> <div class="mw-heading mw-heading3"><h3 id="Pupil_dilation">Pupil dilation</h3>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=4" title="Edit section: Pupil dilation">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"Prefrin" redirects here. For the iron supplement, see <a href="/wiki/Proferrin" class="mw-redirect" title="Proferrin">Proferrin</a>.</div> Phenylephrine is used as an eye drop to dilate the pupil to facilitate visualization of the retina. It is often used in combination with <a href="/wiki/Tropicamide" title="Tropicamide">tropicamide</a> as a synergist when tropicamide alone is not sufficient. Narrow-angle <a href="/wiki/Glaucoma" title="Glaucoma">glaucoma</a> is a <a href="/wiki/Contraindication" title="Contraindication">contraindication</a> to phenylephrine use. As a <a href="/wiki/Mydriasis" title="Mydriasis">mydriatic</a>, it is available in 2.5% and 10% <a href="/wiki/Eye_drop" title="Eye drop">eye drops</a>. Phenylephrine eye drops are applied to the eye after a topical anesthetic is applied.<a href="#cite_note-38">[38]</a> <div class="mw-heading mw-heading3"><h3 id="Intraocular_bleeding">Intraocular bleeding</h3>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=5" title="Edit section: Intraocular bleeding">edit</a>]</div> Phenylephrine has been used as an <a href="/wiki/Intracameral_injection" title="Intracameral injection">intracameral injection</a> into the anterior chamber of the eye to arrest <a href="/wiki/Intraocular_hemorrhage" title="Intraocular hemorrhage">intraocular bleeding</a> occurring during <a href="/wiki/Cataract" title="Cataract">cataract</a> and <a href="/wiki/Glaucoma" title="Glaucoma">glaucoma</a> <a href="/wiki/Eye_surgery" title="Eye surgery">surgery</a>.<a href="#cite_note-39">[39]</a> <div class="mw-heading mw-heading3"><h3 id="Low_blood_pressure">Low blood pressure</h3>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=6" title="Edit section: Low blood pressure">edit</a>]</div> Phenylephrine is commonly used as a <a href="/wiki/Vasopressor" class="mw-redirect" title="Vasopressor">vasopressor</a> to increase the blood pressure in unstable patients with <a href="/wiki/Hypotension" title="Hypotension">hypotension</a> (low blood pressure), especially resulting from <a href="/wiki/Septic_shock" title="Septic shock">septic shock</a>.<a href="#cite_note-MengSunZhao2024-40">[40]</a><a href="#cite_note-LarsonAndersonThomson2021-41">[41]</a> Such use is common in <a href="/wiki/Surgery" title="Surgery">surgery</a> and <a href="/wiki/Anesthesia" title="Anesthesia">anesthesia</a> or critical-care practices;<a href="#cite_note-MengSunZhao2024-40">[40]</a><a href="#cite_note-LarsonAndersonThomson2021-41">[41]</a> it is especially useful in counteracting the hypotensive effect of <a href="/wiki/Epidural" class="mw-redirect" title="Epidural">epidural</a> and <a href="/wiki/Spinal_anesthesia" class="mw-redirect" title="Spinal anesthesia">spinal anesthesia</a>, as well as the vasodilating effect of bacterial toxins and the inflammatory response in <a href="/wiki/Sepsis" title="Sepsis">sepsis</a> and <a href="/wiki/Systemic_inflammatory_response_syndrome" title="Systemic inflammatory response syndrome">systemic inflammatory response syndrome</a>. Because of its <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstrictive</a> effect, phenylephrine can cause severe <a href="/wiki/Necrosis" title="Necrosis">necrosis</a> if it infiltrates the surrounding tissues. Because of this, it should be given through a central line if at all possible. Damage may be prevented or mitigated by infiltrating the tissue with the alpha blocker <a href="/wiki/Phentolamine" title="Phentolamine">phentolamine</a> by subcutaneous injection.<a href="#cite_note-Cooper2008-42">[42]</a> In clinical studies, phenylephrine, administered <a href="/wiki/Intravenous_administration" class="mw-redirect" title="Intravenous administration">intravenously</a>, increases blood pressure, decreases <a href="/wiki/Cardiac_output" title="Cardiac output">cardiac output</a>, increases cerebral blood flow, and decreases cerebral tissue oxygen saturation.<a href="#cite_note-MengSunZhao2024-40">[40]</a><a href="#cite_note-LarsonAndersonThomson2021-41">[41]</a> The decreases in cardiac output, increases in cerebral blood flow, and decreases in cerebral tissue oxygen saturation with phenylephrine are all related to the degree of blood pressure increase.<a href="#cite_note-MengSunZhao2024-40">[40]</a> The decrease in cardiac output is primarily due to a decrease in <a href="/wiki/Heart_rate" title="Heart rate">heart rate</a> and a modest decrease in <a href="/wiki/Stroke_volume" title="Stroke volume">stroke volume</a>.<a href="#cite_note-MengSunZhao2024-40">[40]</a> The decrease in heart rate is due to activation of the <a href="/wiki/Baroreflex" title="Baroreflex">arterial baroreflex</a>, which regulates heart rate in response to changes in blood pressure.<a href="#cite_note-MengSunZhao2024-40">[40]</a><a href="#cite_note-LarsonAndersonThomson2021-41">[41]</a> Because of the decrease in cardiac output, phenylephrine is a <a href="/wiki/Inotrope#Negative_inotropic_agents" title="Inotrope">negative inotropic agent</a>.<a href="#cite_note-MengSunZhao2024-40">[40]</a> Its effects on cardiac output and cerebral oxygenation are unfavorable, and on account of this, the use of phenylephrine in the treatment of intraoperative hypotension is now being recommended against and moved away from in favor of other agents without these adverse effects like <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a> and <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>.<a href="#cite_note-MengSunZhao2024-40">[40]</a><a href="#cite_note-LarsonAndersonThomson2021-41">[41]</a> When taken orally, phenylephrine has a threshold dose of about 50 mg to affect the cardiovascular system, a dose at which the drug decreases heart rate and slightly increases arterial blood pressure.<a href="#cite_note-Eccles2007-8">[8]</a> Additionally, an <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">over-the-counter</a> dose of 60 mg produces a slight increase in heart rate with no detectable changes in blood pressure.<a href="#cite_note-Eccles2007-8">[8]</a> However, other literature reports that doses over 15 mg affect the cardiovascular system, including increases in blood pressure and decreases in heart rate.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> Higher doses, like 150 mg, more robustly affect the cardiovascular system.<a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> <div class="mw-heading mw-heading3"><h3 id="Other_uses">Other uses</h3>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=7" title="Edit section: Other uses">edit</a>]</div> Phenylephrine has been used in the treatment of <a href="/wiki/Postural_orthostatic_tachycardia_syndrome" title="Postural orthostatic tachycardia syndrome">postural orthostatic tachycardia syndrome</a> (POTS).<a href="#cite_note-LyongaNogongeNyange2024-43">[43]</a> It has been found to improve <a href="/wiki/Vascular_resistance" title="Vascular resistance">vascular resistance</a>, enhance circulatory support, and improve symptoms of <a href="/wiki/Orthostatic_intolerance" title="Orthostatic intolerance">orthostatic intolerance</a> in people with the condition.<a href="#cite_note-LyongaNogongeNyange2024-43">[43]</a> It has been described as particularly effective in people with <a href="/wiki/Neuropathy" class="mw-redirect" title="Neuropathy">neuropathic</a> POTS.<a href="#cite_note-LyongaNogongeNyange2024-43">[43]</a> However, phenylephrine has not been specifically approved for the treatment of POTS and data on this use are limited.<a href="#cite_note-LyongaNogongeNyange2024-43">[43]</a> This is also the case with other medications used in the treatment of POTS.<a href="#cite_note-LyongaNogongeNyange2024-43">[43]</a> Phenylephrine has been used in the treatment of <a href="/wiki/Priapism" title="Priapism">priapism</a>.<a href="#cite_note-JiangChristakosFam2014-44">[44]</a><a href="#cite_note-MartinCocchio2016-45">[45]</a> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=8" title="Edit section: Available forms">edit</a>]</div> Phenylephrine is available in the form of <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a> and <a href="/wiki/Syrup" title="Syrup">syrups</a> for use as a <a href="/wiki/Nasal_decongestant" class="mw-redirect" title="Nasal decongestant">nasal decongestant</a>, as an <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">intravenous</a> <a href="/wiki/Solution_(chemistry)" title="Solution (chemistry)">solution</a> to treat <a href="/wiki/Hypotension" title="Hypotension">hypotension</a>, as an <a href="/wiki/Ophthalmology" title="Ophthalmology">ophthalmic</a> solution, spray, or <a href="/wiki/Eye_drop" title="Eye drop">eye drop</a> to cause <a href="/wiki/Pupil_dilation" class="mw-redirect" title="Pupil dilation">pupil dilation</a>, and as a <a href="/wiki/Cocoa_butter" title="Cocoa butter">cocoa butter</a> <a href="/wiki/Suppository" title="Suppository">suppository</a>, among other forms.<a href="#cite_note-Drugs@FDA-6">[6]</a><a href="#cite_note-DailyMed-7">[7]</a> It was also previously available as a metered <a href="/wiki/Aerosol" title="Aerosol">aerosol</a> for <a href="/wiki/Inhalational_administration" class="mw-redirect" title="Inhalational administration">inhalation</a>, but this formulation was discontinued.<a href="#cite_note-Drugs@FDA-6">[6]</a> Phenylephrine is available both alone and in <a href="/wiki/Combination_drug" title="Combination drug">combination</a> with other drugs.<a href="#cite_note-Drugs@FDA-6">[6]</a><a href="#cite_note-DailyMed-7">[7]</a> These other drugs include <a href="/wiki/Antihistamine" title="Antihistamine">antihistamines</a> like <a href="/wiki/Chlorpheniramine" class="mw-redirect" title="Chlorpheniramine">chlorpheniramine</a>, <a href="/wiki/Doxylamine" title="Doxylamine">doxylamine</a>, <a href="/wiki/Promethazine" title="Promethazine">promethazine</a>, and <a href="/wiki/Mepyramine" title="Mepyramine">mepyramine</a> (pyrilamine); <a href="/wiki/Analgesic" title="Analgesic">analgesics</a> like <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol</a> (acetaminophen), <a href="/wiki/Ibuprofen" title="Ibuprofen">ibuprofen</a>, <a href="/wiki/Ketorolac" title="Ketorolac">ketorolac</a>, and <a href="/wiki/Codeine" title="Codeine">codeine</a>; <a href="/wiki/Cough_suppressant" class="mw-redirect" title="Cough suppressant">cough suppressants</a> like <a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a>; <a href="/wiki/Expectorant" class="mw-redirect" title="Expectorant">expectorants</a> like <a href="/wiki/Guiafenesin" class="mw-redirect" title="Guiafenesin">guiafenesin</a>; <a href="/wiki/Anticholinergic" title="Anticholinergic">anticholinergics</a> like <a href="/wiki/Cyclopentolate" title="Cyclopentolate">cyclopentolate</a> and <a href="/wiki/Tropicamide" title="Tropicamide">tropicamide</a>; and <a href="/wiki/Beta_agonist" class="mw-redirect" title="Beta agonist">β-adrenergic receptor agonists</a> like <a href="/wiki/Isoprenaline" title="Isoprenaline">isoprenaline</a> (isoproterenol).<a href="#cite_note-Drugs@FDA-6">[6]</a><a href="#cite_note-DailyMed-7">[7]</a> It is used in combination with antihistamines and analgesics in cough and cold preparations, with anticholinergics in ophthalmic formulations, and with β-adrenergic receptor agonists in inhalational forms.<a href="#cite_note-Drugs@FDA-6">[6]</a><a href="#cite_note-DailyMed-7">[7]</a> Intravenous phenylephrine is always formulated by itself.<a href="#cite_note-Drugs@FDA-6">[6]</a> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=9" title="Edit section: Contraindications">edit</a>]</div> Phenylephrine is <a href="/wiki/Contraindication" title="Contraindication">contraindicated</a> in people with <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, <a href="/wiki/Hyperthyroidism" title="Hyperthyroidism">hyperthyroidism</a>, and <a href="/wiki/Heart_disease" class="mw-redirect" title="Heart disease">heart disease</a> due to its <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstrictor</a> effects.<a href="#cite_note-Eccles2007-8">[8]</a> Relative contraindications include people with <a href="/wiki/Raynaud%27s_syndrome" class="mw-redirect" title="Raynaud's syndrome">Raynaud's syndrome</a> due to vasoconstriction, those taking <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">monoamine oxidase inhibitors</a> (MAOIs) due to inhibition of the metabolism of phenylephrine, and people with <a href="/wiki/Prostate" title="Prostate">prostate</a> problems due to potential exacerbation of <a href="/wiki/Urinary_retention" title="Urinary retention">urinary retention</a>.<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-JohnsonHricik1993-46">[46]</a> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=10" title="Edit section: Side effects">edit</a>]</div> Phenylephrine taken orally at indicated doses is usually <a href="/wiki/Tolerability" title="Tolerability">well-tolerated</a>.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> It may cause <a href="/wiki/Side_effect" title="Side effect">side effects</a> such as <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Reflex_bradycardia" title="Reflex bradycardia">reflex bradycardia</a>, <a href="/wiki/Stimulation" title="Stimulation">excitability</a>, <a href="/wiki/Psychomotor_agitation" title="Psychomotor agitation">restlessness</a>, and <a href="/wiki/Cardiac_arrhythmia" class="mw-redirect" title="Cardiac arrhythmia">cardiac arrhythmias</a>.<a href="#cite_note-AHFS2022-12">[12]</a> At higher than indicated doses, phenylephrine can increase <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a> and decrease <a href="/wiki/Heart_rate" title="Heart rate">heart rate</a>.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> A 45 mg dose of phenylephrine can increase systolic blood pressure by 20 mmHg.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> Possible <a href="/wiki/Side_effect" title="Side effect">side effects</a> of <a href="/wiki/Intravenous_administration" class="mw-redirect" title="Intravenous administration">intravenous</a> phenylephrine are <a href="/wiki/Dose_dependency" class="mw-redirect" title="Dose dependency">dose-dependent</a> and may include <a href="/wiki/Bradycardia" title="Bradycardia">bradycardia</a> and <a href="/wiki/Hypertension" title="Hypertension">reactive hypertension</a>.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> <div class="mw-heading mw-heading3"><h3 id="Heart">Heart</h3>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=11" title="Edit section: Heart">edit</a>]</div> The primary side effect of phenylephrine is <a href="/wiki/Hypertension" title="Hypertension">high blood pressure</a>. People with high blood pressure are typically advised to avoid products containing it. Because this medication is a <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic</a> amine without <a href="/wiki/%CE%92-adrenergic_receptor" class="mw-redirect" title="Β-adrenergic receptor">β-adrenergic receptor</a> <a href="/wiki/Agonist" title="Agonist">agonist</a> activity, it does not increase contractility force and output of the cardiac muscle. It may increase blood pressure resulting in a <a href="/wiki/Reflex_bradycardia" title="Reflex bradycardia">slow heart rate</a> through stimulation of vascular (likely carotid) baroreceptors. A common side effect during IV administration is reflex bradycardia.<a href="#cite_note-47">[47]</a> The low concentration eye drops do not cause blood pressure changes and the changes with the higher dose drops do not last long.<a href="#cite_note-StavertMcGuinessHarper2015-48">[48]</a> The cardiovascular effects of phenylephrine may be potentiated in people with <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> <a href="/wiki/Hypertensive_crisis" title="Hypertensive crisis">Hypertensive crisis</a> with phenylephrine <a href="/wiki/Eye_drop" title="Eye drop">eye drops</a> has been reported in people with hypertension.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> In people with underlying <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular disease</a>, phenylephrine has been found to increase blood pressure and cause associated impairment in myocardial perfusion.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> Other reported side effects of phenylephrine have included increased blood pressure, <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstriction</a> resulting in <a href="/wiki/Orthostatic_hypotension" title="Orthostatic hypotension">worsened orthostatic tolerance</a>, <a href="/wiki/Atrial_fibrillation" title="Atrial fibrillation">atrial fibrillation</a> following <a href="/wiki/Coronary_artery_bypass_surgery" title="Coronary artery bypass surgery">coronary artery bypass surgery</a>, <a href="/wiki/Cerebral_hypoxia" title="Cerebral hypoxia">decreased cerebral oxygenation</a>, bradycardia in people with <a href="/wiki/Spinal_cord_injury" title="Spinal cord injury">spinal cord injury</a>, <a href="/wiki/Cardiac_arrhythmia" class="mw-redirect" title="Cardiac arrhythmia">cardiac arrhythmias</a>, <a href="/wiki/Pulmonary_edema" title="Pulmonary edema">pulmonary edema</a>, <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a>, and <a href="/wiki/Microvascular_occlusion" title="Microvascular occlusion">microvascular occlusion syndrome</a>.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> Rarely, <a href="/wiki/Stroke" title="Stroke">stroke</a> has been reported with phenylephrine, including with the oral, topical, and intravenous forms.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> Due to increased risk of side effects in people with hypertension, phenylephrine is not suggested for use in this population.<a href="#cite_note-IV-Label-1-49">[49]</a><a href="#cite_note-Eccles2007-8">[8]</a> <div class="mw-heading mw-heading3"><h3 id="Others">Others</h3>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=12" title="Edit section: Others">edit</a>]</div> <a href="/wiki/Prostatic_hyperplasia" class="mw-redirect" title="Prostatic hyperplasia">Prostatic hyperplasia</a> can also be worsened by use, and chronic use can lead to rebound <a href="/wiki/Hyperemia" class="mw-redirect" title="Hyperemia">hyperemia</a>.<a href="#cite_note-pharmnemonics-50">[50]</a> People with a history of anxiety or panic disorders, or on anticonvulsant medication for epilepsy should not take this substance. The drug interaction might produce seizures. Some patients have been shown to have an upset stomach, severe abdominal cramping, and vomiting issues connected to taking this drug.<a href="#cite_note-IV-Label-2-51">[51]</a> Phenylephrine is pregnancy category C. Due to the lack of studies done in animals and in humans, it is not known whether there is harm to the fetus. Phenylephrine should only be given to pregnant women who have a clear need.<a href="#cite_note-IV-Label-2-51">[51]</a> Extended use may cause <a href="/wiki/Rhinitis_medicamentosa" title="Rhinitis medicamentosa">rhinitis medicamentosa</a>, a condition of <a href="/wiki/Rebound_effect" title="Rebound effect">rebound</a> <a href="/wiki/Nasal_congestion" title="Nasal congestion">nasal congestion</a>.<a href="#cite_note-nasal-52">[52]</a> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=13" title="Edit section: Interactions">edit</a>]</div> Phenylephrine is susceptible to <a href="/wiki/Drug_metabolism" title="Drug metabolism">metabolism</a> by <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidase</a>.<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> Because of this, <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">monoamine oxidase inhibitors</a> (MAOIs) can inhibit the metabolism of phenylephrine and increase exposure to the medication.<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> Whereas a 45 mg oral dose of phenylephrine alone increases <a href="/wiki/Systolic_blood_pressure" class="mw-redirect" title="Systolic blood pressure">systolic blood pressure</a> by 20 mmHg, use of this dose in people on MAOIs increases systolic blood pressure by more than 60 mmHg.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> Phenylephrine can interact with other <a href="/wiki/Adrenergic" title="Adrenergic">adrenergic</a> drugs, such as <a href="/wiki/Beta_blocker" title="Beta blocker">beta blockers</a> like <a href="/wiki/Propranolol" title="Propranolol">propranolol</a>, <a href="/wiki/Alpha-1_blocker" title="Alpha-1 blocker">α1-adrenergic receptor antagonists</a> like <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Alpha-2_agonist" class="mw-redirect" title="Alpha-2 agonist">α2-adrenergic receptor agonists</a> like <a href="/wiki/Clonidine" title="Clonidine">clonidine</a>, <a href="/wiki/Norepinephrine_reuptake_inhibitor" title="Norepinephrine reuptake inhibitor">norepinephrine reuptake inhibitors</a> like <a href="/wiki/Atomoxetine" title="Atomoxetine">atomoxetine</a> and <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, and MAOIs (which increase norepinephrine levels).<a href="#cite_note-RichardsLopezMaani2023-5">[5]</a> It can also interact with <a href="/wiki/Corticosteroid" title="Corticosteroid">corticosteroids</a> like <a href="/wiki/Prednisone" title="Prednisone">prednisone</a>, which sensitize the vasculature to sympathomimetics and augment their vasoconstrictive effects, and with <a href="/wiki/Ergot_alkaloid" class="mw-redirect" title="Ergot alkaloid">ergot alkaloids</a>, which also have <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstrictor</a> effects and can have additive or synergistic effects with phenylephrine.<a href="#cite_note-RichardsLopezMaani2023-5">[5]</a> In addition, combination of phenylephrine with other <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic</a> drugs can increase <a href="/wiki/Pressor" class="mw-redirect" title="Pressor">pressor</a> effects and the risk of hemorrhagic stroke.<a href="#cite_note-RichardsLopezMaani2023-5">[5]</a> Other drugs that may decrease the effects of phenylephrine may include <a href="/wiki/Calcium_channel_blockers" class="mw-redirect" title="Calcium channel blockers">calcium channel blockers</a>, <a href="/wiki/ACE_inhibitors" class="mw-redirect" title="ACE inhibitors">ACE inhibitors</a> and <a href="/wiki/Benzodiazepine" title="Benzodiazepine">benzodiazepines</a>.<a href="#cite_note-IV-Label-3-53">[53]</a> Patients taking these medications may need a higher dose of phenylephrine to achieve a comparable increase in blood pressure.<a href="#cite_note-IV-Label-3-53">[53]</a> Concomitant use of phenylephrine with the preceding agents may necessitate dose adjustments. <a href="/wiki/Acetaminophen" class="mw-redirect" title="Acetaminophen">Acetaminophen</a> (paracetamol) has been found to increase exposure to oral phenylephrine.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> It more than doubles phenylephrine's <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a>, reduces its <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorption</a> half-time by 50%, increases phenylephrine levels by approximately 2-fold, and increases peak phenylephrine levels by 4-fold, with substantial <a href="/wiki/Interindividual_variability" class="mw-redirect" title="Interindividual variability">interindividual variability</a>.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> Phenylephrine is widely formulated with acetaminophen in combination products.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> The combination may increase the cardiovascular effects of phenylephrine.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> The mechanism of the interaction between phenylephrine and acetaminophen is unknown, but it has been suggested that it may be due to saturation of <a href="/wiki/Sulfation" title="Sulfation">sulfation</a> <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">pathways</a> by acetaminophen that also participate in phenylephrine metabolism.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=14" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=15" title="Edit section: Pharmacodynamics">edit</a>]</div> Phenylephrine is a <a href="/wiki/Binding_selectivity" title="Binding selectivity">selective</a> <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/%CE%911-adrenergic_receptor" class="mw-redirect" title="Α1-adrenergic receptor">α1-adrenergic receptor</a>, one of the <a href="/wiki/Biological_target" title="Biological target">biological targets</a> of the <a href="/wiki/Catecholamine" title="Catecholamine">catecholamine</a> <a href="/wiki/Hormone" title="Hormone">hormones</a> and <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitters</a> <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a> (adrenaline) and <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a> (noradrenaline).<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-RichardsLopezMaani2023-5">[5]</a><a href="#cite_note-ODonnell1995-15">[15]</a> It is a <a href="/wiki/Full_agonist" class="mw-redirect" title="Full agonist">full agonist</a> of the α1-adrenergic receptor in most assessed <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a>.<a href="#cite_note-Chess-WilliamsWilliamsonBroadley1990-54">[54]</a> The drug has weak, minimal, or no agonist activity at the <a href="/wiki/%CE%912-adrenergic_receptor" class="mw-redirect" title="Α2-adrenergic receptor">α2-adrenergic receptor</a> or the <a href="/wiki/%CE%92-adrenergic_receptor" class="mw-redirect" title="Β-adrenergic receptor">β-adrenergic receptors</a>.<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-RichardsLopezMaani2023-5">[5]</a><a href="#cite_note-ODonnell1995-15">[15]</a> At the β-adrenergic receptors, it is a <a href="/wiki/Partial_agonist" title="Partial agonist">partial agonist</a>.<a href="#cite_note-Chess-WilliamsWilliamsonBroadley1990-54">[54]</a> Phenylephrine also has relatively little or no activity as a <a href="/wiki/Norepinephrine_releasing_agent" title="Norepinephrine releasing agent">norepinephrine releasing agent</a>.<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-ODonnell1995-15">[15]</a> As such, it has little activity as an indirectly acting <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic</a> and non-selective activator of <a href="/wiki/Adrenergic_receptor" title="Adrenergic receptor">adrenergic receptors</a>.<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-ODonnell1995-15">[15]</a> This is in contrast to related sympathomimetics like <a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">pseudoephedrine</a>.<a href="#cite_note-Eccles2007-8">[8]</a> However, more recent research suggests that phenylephrine may actually be more <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> as a norepinephrine releasing agent than has previously been thought.<a href="#cite_note-Al-KhrasaniKaradiGalambos2022-55">[55]</a> This might help to explain certain unexpected <a href="/wiki/Pharmacodynamics" title="Pharmacodynamics">pharmacodynamic</a> effects of the drug.<a href="#cite_note-Al-KhrasaniKaradiGalambos2022-55">[55]</a> Because of its α1-adrenergic receptor agonism, phenylephrine is a directly acting sympathomimetic <a href="/wiki/Vasoconstrictor" class="mw-redirect" title="Vasoconstrictor">vasoconstrictor</a><a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-ODonnell1995-15">[15]</a> and produces both <a href="/wiki/Vein" title="Vein">venous</a> and <a href="/wiki/Artery" title="Artery">arterial</a> <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstriction</a>.<a href="#cite_note-IV-Label-1-49">[49]</a><a href="#cite_note-RichardsLopezMaani2023-5">[5]</a> The term sympathomimetic means that it mimics the actions of epinephrine or norepinephrine.<a href="#cite_note-CostaGrandoMilandri2022-56">[56]</a> Phenylephrine works as a <a href="/wiki/Nasal_decongestant" class="mw-redirect" title="Nasal decongestant">nasal decongestant</a> by causing local vasoconstriction in the nose.<a href="#cite_note-ODonnell1995-15">[15]</a> Whereas the related sympathomimetic decongestant <a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">pseudoephedrine</a> causes both vasoconstriction and increase of <a href="/wiki/Mucociliary_clearance" title="Mucociliary clearance">mucociliary clearance</a> through its non-specific adrenergic activity, phenylephrine's selective α1-adrenergic receptor agonism causes vasoconstriction alone, resulting in a difference in their methods of action.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=16" title="Edit section: Pharmacokinetics">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Absorption">Absorption</h4>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=17" title="Edit section: Absorption">edit</a>]</div> Phenylephrine is rapidly <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> when taken <a href="/wiki/Oral_administration" title="Oral administration">orally</a>.<a href="#cite_note-Eccles2007-8">[8]</a> However, its absorption is incomplete and erratic.<a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> Because of extensive <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first-pass metabolism</a>, phenylephrine has an oral <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of only about 38% relative to <a href="/wiki/Intravenous_administration" class="mw-redirect" title="Intravenous administration">intravenous administration</a>.<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-DrugBank-3">[3]</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a><a href="#cite_note-Medsafe2004-10">[10]</a> However, another source has stated that the bioavailability of phenylephrine is poorly documented and may actually be as low as 0.003%.<a href="#cite_note-AtkinsonPottsAnderson2015-11">[11]</a> The <a href="/wiki/Tmax_(pharmacology)" class="mw-redirect" title="Tmax (pharmacology)">time to peak</a> concentrations is 1.0 to 1.3 hours.<a href="#cite_note-Eccles2007-8">[8]</a> <div class="mw-heading mw-heading4"><h4 id="Distribution">Distribution</h4>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=18" title="Edit section: Distribution">edit</a>]</div> The <a href="/wiki/Steady-state_(pharmacokinetics)" class="mw-redirect" title="Steady-state (pharmacokinetics)">steady-state</a> <a href="/wiki/Volume_of_distribution" title="Volume of distribution">volume of distribution</a> of phenylephrine is 340 L.<a href="#cite_note-RichardsLopezMaani2023-5">[5]</a> Phenylephrine does not cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> and hence is a <a href="/wiki/Peripherally_selective_drug" title="Peripherally selective drug">peripherally selective drug</a> with no <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> activity.<a href="#cite_note-MengSunZhao2024-40">[40]</a><a href="#cite_note-LarsonAndersonThomson2021-41">[41]</a><a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-ODonnell1995-15">[15]</a> Its lack of blood–brain barrier permeability is related to its <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl groups</a> and high <a href="/wiki/Hydrophilicity" class="mw-redirect" title="Hydrophilicity">hydrophilicity</a>.<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-JohnsonHricik1993-46">[46]</a> The lack of central permeation with phenylephrine is in contrast to certain other related decongestant and sympathomimetic agents like <a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">pseudoephedrine</a>, <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>, and <a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">phenylpropanolamine</a>.<a href="#cite_note-JohnsonHricik1993-46">[46]</a><a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-ODonnell1995-15">[15]</a> <div class="mw-heading mw-heading4"><h4 id="Metabolism">Metabolism</h4>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=19" title="Edit section: Metabolism">edit</a>]</div> Phenylephrine is <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> in the <a href="/wiki/Intestine" class="mw-redirect" title="Intestine">intestines</a> and <a href="/wiki/Liver" title="Liver">liver</a> prior to reaching the systemic circulation when taken orally.<a href="#cite_note-Eccles2007-8">[8]</a> It is extensively metabolized during first-pass metabolism due to susceptibility to <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidases</a>, similarly to <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a>.<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-RichardsLopezMaani2023-5">[5]</a><a href="#cite_note-DrugBank-3">[3]</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> Phenylephrine is metabolized via <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidative</a> <a href="/wiki/Deamination" title="Deamination">deamination</a> by 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>.<a href="#cite_note-RichardsLopezMaani2023-5">[5]</a><a href="#cite_note-DrugBank-3">[3]</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> In contrast to epinephrine and <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>, phenylephrine is not a <a href="/wiki/Catecholamine" title="Catecholamine">catecholamine</a>, and is not metabolized by <a href="/wiki/Catechol_O-methyltransferase" class="mw-redirect" title="Catechol O-methyltransferase">catechol O-methyltransferase</a> (COMT).<a href="#cite_note-ODonnell1995-15">[15]</a> Besides monoamine oxidase, phenylephrine is also metabolized by <a href="/wiki/Sulfation" title="Sulfation">sulfation</a> and <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugation</a>.<a href="#cite_note-RichardsLopezMaani2023-5">[5]</a><a href="#cite_note-DrugBank-3">[3]</a> Non-oral routes of phenylephrine, like <a href="/wiki/Intranasal_administration" class="mw-redirect" title="Intranasal administration">intranasal</a>, <a href="/wiki/Ophthalmic_drug_administration" title="Ophthalmic drug administration">ophthalmic</a>, and <a href="/wiki/Parenteral_administration" class="mw-redirect" title="Parenteral administration">parenteral</a>, do not undergo first-pass metabolism in the gastrointestinal tract.<a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> The major <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> of phenylephrine is <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/3-Hydroxymandelic-acid">meta-hydroxymandelic acid</a>, which is inactive.<a href="#cite_note-DrugBank-3">[3]</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> Lesser metabolites of phenylephrine include <a href="/wiki/Sulfate" title="Sulfate">sulfate</a> and <a href="/wiki/Glucuronide" title="Glucuronide">glucuronide</a> conjugates, which are also inactive.<a href="#cite_note-DrugBank-3">[3]</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> Unlike phenylephrine, related sympathomimetics with a <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> at the α carbon (i.e., <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">amphetamines</a>), like <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>, <a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">pseudoephedrine</a>, <a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">phenylpropanolamine</a>, <a href="/wiki/Methoxamine" title="Methoxamine">methoxamine</a>, and <a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">methoxyphenamine</a>, are resistant to degradation by monoamine oxidase.<a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> <div class="mw-heading mw-heading4"><h4 id="Elimination">Elimination</h4>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=20" title="Edit section: Elimination">edit</a>]</div> Phenylephrine is primarily <a href="/wiki/Excretion" title="Excretion">excreted</a> in <a href="/wiki/Urine" title="Urine">urine</a>.<a href="#cite_note-RichardsLopezMaani2023-5">[5]</a><a href="#cite_note-DrugBank-3">[3]</a> It is recovered 86% in urine.<a href="#cite_note-DrugBank-3">[3]</a> The drug is excreted in urine 3 to 16% unchanged, 57% as <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/3-Hydroxymandelic-acid">meta-hydroxymandelic acid</a>, and 8% as <a href="/wiki/Sulfate" title="Sulfate">sulfate</a> <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugates</a>.<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-DrugBank-3">[3]</a> <a href="/wiki/Glucuronide" title="Glucuronide">Glucuronide</a> conjugates constitute a smaller portion of phenylephrine.<a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> Phenylephrine has a relatively short <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of 2.0 to 3.0 hours regardless of <a href="/wiki/Route_of_administration" title="Route of administration">route of administration</a>.<a href="#cite_note-Eccles2007-8">[8]</a><a href="#cite_note-RichardsLopezMaani2023-5">[5]</a><a href="#cite_note-DrugBank-3">[3]</a><a href="#cite_note-KanferDowseVuma1993-13">[13]</a><a href="#cite_note-ChuaBenrimojTriggs1989-9">[9]</a> Its lack of metabolism by COMT is said to be responsible for its much longer <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">duration of action</a> than related agents like <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>.<a href="#cite_note-ODonnell1995-15">[15]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=21" title="Edit section: Chemistry">edit</a>]</div> Phenylephrine is a <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">substituted phenethylamine</a> and can also be referred to <a href="/wiki/Chemical_structure" title="Chemical structure">structurally</a> as (R)-β,3-dihydroxy-N-methylphenethylamine.<a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-PubChem-57">[57]</a><a href="#cite_note-DrugBank-3">[3]</a> It is closely <a href="/wiki/Structural_analog" title="Structural analog">structurally related</a> to <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a> (adrenaline; 3,4,β-trihydroxy-N-methylphenethylamine), differing from it only in the absence of one <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> on the <a href="/wiki/Phenyl_ring" class="mw-redirect" title="Phenyl ring">phenyl ring</a>.<a href="#cite_note-Eccles2007-8">[8]</a> It is a <a href="/wiki/Chirality" title="Chirality">chiral</a> compound and is used as the <a href="/wiki/Enantiopure_drug" title="Enantiopure drug">enantiopure</a> (R)-<a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomer</a>.<a href="#cite_note-KanferDowseVuma1993-13">[13]</a><a href="#cite_note-Elks2014-1">[1]</a> The <a href="/wiki/Racemic_mixture" title="Racemic mixture">racemic</a> form has not been formally named or used.<a href="#cite_note-Elks2014-1">[1]</a> Phenylephrine is the N-<a href="/wiki/Methyl_group" title="Methyl group">methylated</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> of <a href="/wiki/Norfenefrine" title="Norfenefrine">norfenefrine</a> (3,β-dihydroxyphenethylamine).<a href="#cite_note-Elks2014-1">[1]</a> The <a href="/wiki/Racemic_mixture" title="Racemic mixture">racemic</a> N-<a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a> <a href="/wiki/Structural_analog" title="Structural analog">analogue</a> is <a href="/wiki/Etilefrine" title="Etilefrine">etilefrine</a> (ethylphenephrine).<a href="#cite_note-Elks2014-1">[1]</a> <a href="/wiki/Synephrine" title="Synephrine">Synephrine</a> (p-synephrine, oxedrine; 4,β-dihydroxyphenethylamine) is a <a href="/wiki/Positional_isomer" class="mw-redirect" title="Positional isomer">positional isomer</a> of phenylephrine.<a href="#cite_note-CostaGrandoMilandri2022-56">[56]</a> In contrast to epinephrine and <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a> (noradrenaline; 3,4,β-trihydroxyphenethylamine), phenylephrine is not a <a href="/wiki/Catecholamine" title="Catecholamine">catecholamine</a> since it does not have two hydroxyl groups on its phenyl ring.<a href="#cite_note-ODonnell1995-15">[15]</a> Besides the catecholamines, the chemical structure of phenylephrine somewhat resembles that of <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a> (α-methylphenethylamine).<a href="#cite_note-JohnsonHricik1993-46">[46]</a> However, phenylephrine does not have a <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> at the α <a href="/wiki/Carbon" title="Carbon">carbon</a> and hence is not an amphetamine itself.<a href="#cite_note-JohnsonHricik1993-46">[46]</a> Phenylephrine is a <a href="/wiki/Small_molecule" title="Small molecule">small-molecule</a> compound with the <a href="/wiki/Molecular_formula" class="mw-redirect" title="Molecular formula">molecular formula</a> C9H13NO2 and a <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a> of 167.205 g/mol.<a href="#cite_note-PubChem-57">[57]</a><a href="#cite_note-DrugBank-3">[3]</a> It is a highly <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> compound, with an experimental <a href="/wiki/Partition_coefficient" title="Partition coefficient">log P</a> of -0.3.<a href="#cite_note-Xiao2020-58">[58]</a><a href="#cite_note-PubChem-57">[57]</a><a href="#cite_note-DrugBank-3">[3]</a> Phenylephrine is used medically almost always as the <a href="/wiki/Hydrochloride" title="Hydrochloride">hydrochloride</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a>.<a href="#cite_note-IndexNominum2000-2">[2]</a><a href="#cite_note-Elks2014-1">[1]</a> However, the <a href="/wiki/Free_base" title="Free base">free base</a> form and the <a href="/wiki/Tannate" title="Tannate">tannate</a> salt have also been used pharmaceutically to a much lesser extent.<a href="#cite_note-IndexNominum2000-2">[2]</a> <a href="/wiki/Pivenfrine" title="Pivenfrine">Pivenfrine</a> is the 3-<a href="/wiki/Pivalate" class="mw-redirect" title="Pivalate">pivalate</a> <a href="/wiki/Ester" title="Ester">ester</a> of phenylephrine and has much greater <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilicity</a> in comparison.<a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-PubChem-Pivenfrine-59">[59]</a> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=22" title="Edit section: History">edit</a>]</div> Phenylephrine was first patented in 1927 and was first introduced for medical use in 1938.<a href="#cite_note-DeolAlvarezElrabi2023-60">[60]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=23" title="Edit section: Society and culture">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Names">Names</h3>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=24" title="Edit section: Names">edit</a>]</div> Phenylephrine 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, <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, and <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, while 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 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 in the case of the <a href="/wiki/Hydrochloride" title="Hydrochloride">hydrochloride</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> are phenylephrine hydrochloride.<a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-IndexNominum2000-2">[2]</a><a href="#cite_note-MortonHall2012-61">[61]</a><a href="#cite_note-Drugs.com-International-4">[4]</a> Synonyms of phenylephrine include phenephrine, fenefrine, L-m-synephrine, metaoxedrine, neo-oxedrine, mesatonum, neosynephrine, and m-sympatol.<a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-IndexNominum2000-2">[2]</a><a href="#cite_note-Drugs.com-International-4">[4]</a> Brand names of phenylephrine include Neosynephrine or Neo-Synephrine and Sudafed PE, among numerous others.<a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-IndexNominum2000-2">[2]</a><a href="#cite_note-DrugBank-3">[3]</a><a href="#cite_note-Drugs.com-International-4">[4]</a> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=25" title="Edit section: Availability">edit</a>]</div> Phenylephrine is available worldwide as a <a href="/wiki/Prescription_drug" title="Prescription drug">prescription drug</a> in many different <a href="/wiki/Pharmaceutical_form" class="mw-redirect" title="Pharmaceutical form">formulations</a>.<a href="#cite_note-Drugs.com-International-4">[4]</a> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Phenylephrine&action=edit&section=26" title="Edit section: References">edit</a>]</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-Elks2014-1">^ <a href="#cite_ref-Elks2014_1-0">a</a> <a href="#cite_ref-Elks2014_1-1">b</a> <a href="#cite_ref-Elks2014_1-2">c</a> <a href="#cite_ref-Elks2014_1-3">d</a> <a href="#cite_ref-Elks2014_1-4">e</a> <a href="#cite_ref-Elks2014_1-5">f</a> <a href="#cite_ref-Elks2014_1-6">g</a> <a href="#cite_ref-Elks2014_1-7">h</a> <a href="#cite_ref-Elks2014_1-8">i</a> <a href="#cite_ref-Elks2014_1-9">j</a> <a href="#cite_ref-Elks2014_1-10">k</a> <a href="#cite_ref-Elks2014_1-11">l</a> <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="CITEREFElks2014" class="citation book cs1">Elks J (2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA61">The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies</a>. Springer US. pp. 61, 1001. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-2085-3" title="Special:BookSources/978-1-4757-2085-3"><bdi>978-1-4757-2085-3</bdi></a>. 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Retrieved 21 July 2024. <q>Second, having multiple polar groups on its molecular structure makes phenylephrine like to interact with water molecules as well. 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J Dent Anesth Pain Med. 23 (6): 293–302. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.17245%2Fjdapm.2023.23.6.293">10.17245/jdapm.2023.23.6.293</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10703557">10703557</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/38076507">38076507</a>. <q>Phenylephrine, a synthetic selective alpha-1 adrenergic agonist, first received its patent in 1927 and was introduced for medical use in 1938 [8].</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Dent+Anesth+Pain+Med&rft.atitle=A+comparative+review+of+epinephrine+and+phenylephrine+as+vasoconstrictors+in+dental+anesthesia%3A+exploring+the+factors+behind+epinephrine%27s+prevalence+in+the+US&rft.volume=23&rft.issue=6&rft.pages=293-302&rft.date=2023-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10703557%23id-name%3DPMC&rft_id=info%3Apmid%2F38076507&rft_id=info%3Adoi%2F10.17245%2Fjdapm.2023.23.6.293&rft.aulast=Deol&rft.aufirst=N&rft.au=Alvarez%2C+G&rft.au=Elrabi%2C+O&rft.au=Chen%2C+G&rft.au=Ferraro%2C+N&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10703557&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenylephrine" class="Z3988"> </li> <li id="cite_note-MortonHall2012-61"><a href="#cite_ref-MortonHall2012_61-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMortonHall2012" class="citation book cs1">Morton IK, Hall JM (2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA219">Concise Dictionary of Pharmacological Agents: Properties and Synonyms</a>. 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.navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .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: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)" 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 <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 class="mw-selflink selflink">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="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<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>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§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="Decongestants_and_other_nasal_preparations_(R01)" 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: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)" 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 class="mw-selflink selflink">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, 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><a href="/wiki/Histamine_antagonist" class="mw-redirect" title="Histamine antagonist">histamine antagonists</a> (<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><a href="/wiki/Mast_cell_stabilizer" title="Mast cell stabilizer">mast cell stabilizer (some are also antihistamines)</a> (<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>#</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>#</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: <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 class="mw-selflink selflink">Phenylephrine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">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="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<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>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§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="Ophthalmologicals:_mydriasis_and_cycloplegia_(S01F)" 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:Mydriatics_and_cycloplegics" title="Template:Mydriatics and cycloplegics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Mydriatics_and_cycloplegics" title="Template talk:Mydriatics and cycloplegics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Mydriatics_and_cycloplegics" title="Special:EditPage/Template:Mydriatics and cycloplegics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Ophthalmologicals:_mydriasis_and_cycloplegia_(S01F)" style="font-size:114%;margin:0 4em"><a href="/wiki/Ophthalmology" title="Ophthalmology">Ophthalmologicals</a>: <a href="/wiki/Mydriasis" title="Mydriasis">mydriasis</a> and <a href="/wiki/Cycloplegia" title="Cycloplegia">cycloplegia</a> (<a href="/wiki/ATC_code_S01#S01F" title="ATC code S01">S01F</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anticholinergic" title="Anticholinergic">Anticholinergics</a>/<a href="/wiki/Muscarinic_antagonist" title="Muscarinic antagonist">antimuscarinics</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/Atropine" title="Atropine">Atropine</a></li> <li><a href="/wiki/Hyoscine_hydrobromide" class="mw-redirect" title="Hyoscine hydrobromide">Scopolamine</a></li> <li><a href="/wiki/Methylscopolamine_bromide" title="Methylscopolamine bromide">Methylscopolamine</a></li> <li><a href="/wiki/Cyclopentolate" title="Cyclopentolate">Cyclopentolate</a></li> <li><a href="/wiki/Homatropine" title="Homatropine">Homatropine</a></li> <li><a href="/wiki/Tropicamide" title="Tropicamide">Tropicamide</a> (<a href="/wiki/Tropicamide/phenylephrine" title="Tropicamide/phenylephrine">+phenylephrine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sympathomimetic_drug" title="Sympathomimetic drug">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/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">Hydroxyamphetamine (norpholedrine)</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a class="mw-selflink selflink">Phenylephrine</a> (<a href="/wiki/Phenylephrine/ketorolac" title="Phenylephrine/ketorolac">+ketorolac</a>)</li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Adrenergic_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist 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:Adrenergic_receptor_modulators" title="Template:Adrenergic receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Adrenergic_receptor_modulators" title="Template talk:Adrenergic receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Adrenergic_receptor_modulators" title="Special:EditPage/Template:Adrenergic receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Adrenergic_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Adrenergic_receptor" title="Adrenergic receptor">Adrenergic receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alpha-1_adrenergic_receptor" title="Alpha-1 adrenergic receptor">α1</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%">Agonists</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/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/Buspirone" title="Buspirone">Buspirone</a></li> <li><a href="/wiki/Cirazoline" title="Cirazoline">Cirazoline</a></li> <li><a href="/wiki/Corbadrine" title="Corbadrine">Corbadrine</a></li> <li><a href="/wiki/Deoxyepinephrine" title="Deoxyepinephrine">Deoxyepinephrine (epinine, N-methyldopamine)</a></li> <li><a href="/wiki/Desglymidodrine" title="Desglymidodrine">Desglymidodrine</a></li> <li><a href="/w/index.php?title=Dexisometheptene&action=edit&redlink=1" class="new" title="Dexisometheptene (page does not exist)">Dexisometheptene</a></li> <li><a href="/wiki/Dipivefrine" title="Dipivefrine">Dipivefrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa (L-DOPS)</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/Etilevodopa" title="Etilevodopa">Etilevodopa</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Indanidine" title="Indanidine">Indanidine</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA (levodopa)</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">L-Phenylalanine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">L-Tyrosine</a></li> <li><a href="/wiki/Melevodopa" title="Melevodopa">Melevodopa</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/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/Midodrine" title="Midodrine">Midodrine</a></li> <li><a href="/wiki/Naphazoline" title="Naphazoline">Naphazoline</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine">Octopamine</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a class="mw-selflink selflink">Phenylephrine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Tetryzoline" title="Tetryzoline">Tetryzoline</a></li> <li><a href="/wiki/Tiamenidine" title="Tiamenidine">Tiamenidine</a></li> <li><a href="/wiki/XP21279" class="mw-redirect" title="XP21279">XP21279</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%">Antagonists</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/Abanoquil" title="Abanoquil">Abanoquil</a></li> <li><a href="/wiki/Ajmalicine" title="Ajmalicine">Ajmalicine</a></li> <li><a href="/wiki/Alfuzosin" title="Alfuzosin">Alfuzosin</a></li> <li><a href="/wiki/Anisodamine" title="Anisodamine">Anisodamine</a></li> <li><a href="/wiki/Anisodine" title="Anisodine">Anisodine</a></li> <li><a href="/wiki/Atiprosin" title="Atiprosin">Atiprosin</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>)</li> <li><a href="/wiki/Benoxathian" title="Benoxathian">Benoxathian</a></li> <li><a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> (e.g., <a href="/wiki/Adimolol" title="Adimolol">adimolol</a>, <a href="/wiki/Amosulalol" title="Amosulalol">amosulalol</a>, <a href="/wiki/Arotinolol" title="Arotinolol">arotinolol</a>, <a href="/wiki/Carvedilol" title="Carvedilol">carvedilol</a>, <a href="/wiki/Eugenodilol" title="Eugenodilol">eugenodilol</a>, <a href="/wiki/Labetalol" title="Labetalol">labetalol</a>)</li> <li><a href="/wiki/Buflomedil" title="Buflomedil">Buflomedil</a></li> <li><a href="/wiki/Bunazosin" title="Bunazosin">Bunazosin</a></li> <li><a href="/wiki/Corynanthine" title="Corynanthine">Corynanthine</a></li> <li><a href="/wiki/Dapiprazole" title="Dapiprazole">Dapiprazole</a></li> <li><a href="/wiki/Domesticine" title="Domesticine">Domesticine</a></li> <li><a href="/wiki/Doxazosin" title="Doxazosin">Doxazosin</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Acetergamine" title="Acetergamine">acetergamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Nicergoline" title="Nicergoline">nicergoline</a>, <a href="/wiki/Terguride" title="Terguride">terguride</a>)</li> <li><a href="/wiki/Etoperidone" title="Etoperidone">Etoperidone</a></li> <li><a href="/wiki/Fenspiride" title="Fenspiride">Fenspiride</a></li> <li><a href="/wiki/Hydroxyzine" title="Hydroxyzine">Hydroxyzine</a></li> <li><a href="/wiki/Indoramin" title="Indoramin">Indoramin</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/L-765,314" title="L-765,314">L-765,314</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Mepiprazole" title="Mepiprazole">Mepiprazole</a></li> <li><a href="/wiki/Metazosin" title="Metazosin">Metazosin</a></li> <li><a href="/wiki/Monatepil" title="Monatepil">Monatepil</a></li> <li><a href="/wiki/Moxisylyte" title="Moxisylyte">Moxisylyte</a></li> <li><a href="/wiki/Naftopidil" title="Naftopidil">Naftopidil</a></li> <li><a href="/wiki/Nantenine" title="Nantenine">Nantenine</a></li> <li><a href="/wiki/Neldazosin" title="Neldazosin">Neldazosin</a></li> <li><a href="/wiki/Niaprazine" title="Niaprazine">Niaprazine</a></li> <li><a href="/wiki/Niguldipine" title="Niguldipine">Niguldipine</a></li> <li><a href="/wiki/Pardoprunox" title="Pardoprunox">Pardoprunox</a></li> <li><a href="/wiki/Pelanserin" title="Pelanserin">Pelanserin</a></li> <li><a href="/wiki/Perlapine" title="Perlapine">Perlapine</a></li> <li><a href="/wiki/Phendioxan" title="Phendioxan">Phendioxan</a></li> <li><a href="/wiki/Phenoxybenzamine" title="Phenoxybenzamine">Phenoxybenzamine</a></li> <li><a href="/wiki/Phentolamine" title="Phentolamine">Phentolamine</a></li> <li><a href="/wiki/Phenylpiperazine" title="Phenylpiperazine">Phenylpiperazine</a> <a href="/wiki/Antidepressant" title="Antidepressant">antidepressants</a> (e.g., <a href="/wiki/Hydroxynefazodone" title="Hydroxynefazodone">hydroxynefazodone</a>, <a href="/wiki/Nefazodone" title="Nefazodone">nefazodone</a>, <a href="/wiki/Trazodone" title="Trazodone">trazodone</a>, <a href="/wiki/Triazoledione" title="Triazoledione">triazoledione</a>)</li> <li><a href="/wiki/Piperoxan" title="Piperoxan">Piperoxan</a></li> <li><a href="/wiki/Prazosin" title="Prazosin">Prazosin</a></li> <li><a href="/wiki/Quinazosin" title="Quinazosin">Quinazosin</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/wiki/Silodosin" title="Silodosin">Silodosin</a></li> <li><a href="/wiki/Spegatrine" title="Spegatrine">Spegatrine</a></li> <li><a href="/wiki/Spiperone" title="Spiperone">Spiperone</a></li> <li><a href="/wiki/Talipexole" title="Talipexole">Talipexole</a></li> <li><a href="/wiki/Tamsulosin" title="Tamsulosin">Tamsulosin</a></li> <li><a href="/wiki/Terazosin" title="Terazosin">Terazosin</a></li> <li><a href="/wiki/Tiodazosin" title="Tiodazosin">Tiodazosin</a></li> <li><a href="/wiki/Tolazoline" title="Tolazoline">Tolazoline</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>)</li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Doxepin" title="Doxepin">doxepin</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>, <a href="/wiki/Trimipramine" title="Trimipramine">trimipramine</a>)</li> <li><a href="/wiki/Trimazosin" title="Trimazosin">Trimazosin</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Urapidil" title="Urapidil">Urapidil</a></li> <li><a href="/wiki/WB-4101" title="WB-4101">WB-4101</a></li> <li><a href="/wiki/Zolertine" title="Zolertine">Zolertine</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/Alpha-2_adrenergic_receptor" title="Alpha-2 adrenergic receptor">α2</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%">Agonists</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/(R)-3-Nitrobiphenyline" title="(R)-3-Nitrobiphenyline">(R)-3-Nitrobiphenyline</a></li> <li><a href="/wiki/4-NEMD" title="4-NEMD">4-NEMD</a></li> <li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/Amitraz" title="Amitraz">Amitraz</a></li> <li><a href="/wiki/Apraclonidine" title="Apraclonidine">Apraclonidine</a></li> <li><a href="/wiki/Brimonidine" title="Brimonidine">Brimonidine</a></li> <li><a href="/wiki/Clonidine" title="Clonidine">Clonidine</a></li> <li><a href="/wiki/Corbadrine" title="Corbadrine">Corbadrine</a></li> <li><a href="/wiki/Deoxyepinephrine" title="Deoxyepinephrine">Deoxyepinephrine (epinine, N-methyldopamine)</a></li> <li><a href="/wiki/Detomidine" title="Detomidine">Detomidine</a></li> <li><a href="/wiki/Dexmedetomidine" title="Dexmedetomidine">Dexmedetomidine</a></li> <li><a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">Dihydroergotamine</a></li> <li><a href="/wiki/Dipivefrine" title="Dipivefrine">Dipivefrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa (L-DOPS)</a></li> <li><a href="/wiki/Etilevodopa" title="Etilevodopa">Etilevodopa</a></li> <li><a href="/wiki/Ergotamine" title="Ergotamine">Ergotamine</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/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Guanabenz" title="Guanabenz">Guanabenz</a></li> <li><a href="/wiki/Guanfacine" title="Guanfacine">Guanfacine</a></li> <li><a href="/wiki/Guanoxabenz" title="Guanoxabenz">Guanoxabenz</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA (levodopa)</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">L-Phenylalanine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">L-Tyrosine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Lofexidine" title="Lofexidine">Lofexidine</a></li> <li><a href="/wiki/Medetomidine" title="Medetomidine">Medetomidine</a></li> <li><a href="/wiki/Melevodopa" title="Melevodopa">Melevodopa</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/Mivazerol" title="Mivazerol">Mivazerol</a></li> <li><a href="/wiki/Moxonidine" title="Moxonidine">Moxonidine</a></li> <li><a href="/wiki/Naphazoline" title="Naphazoline">Naphazoline</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Piperoxan" title="Piperoxan">Piperoxan</a></li> <li><a href="/wiki/PS75" title="PS75">PS75</a></li> <li><a href="/w/index.php?title=Rezatomidine&action=edit&redlink=1" class="new" title="Rezatomidine (page does not exist)">Rezatomidine</a></li> <li><a href="/wiki/Rilmenidine" title="Rilmenidine">Rilmenidine</a></li> <li><a href="/wiki/Romifidine" title="Romifidine">Romifidine</a></li> <li><a href="/wiki/Talipexole" title="Talipexole">Talipexole</a></li> <li><a href="/w/index.php?title=Tasipimidine&action=edit&redlink=1" class="new" title="Tasipimidine (page does not exist)">Tasipimidine</a></li> <li><a href="/wiki/Tetryzoline" title="Tetryzoline">Tetryzoline</a></li> <li><a href="/wiki/Tiamenidine" title="Tiamenidine">Tiamenidine</a></li> <li><a href="/wiki/Tizanidine" title="Tizanidine">Tizanidine</a></li> <li><a href="/wiki/Tolonidine" title="Tolonidine">Tolonidine</a></li> <li><a href="/wiki/Urapidil" title="Urapidil">Urapidil</a></li> <li><a href="/wiki/Vatinoxan" class="mw-redirect" title="Vatinoxan">Vatinoxan</a></li> <li><a href="/wiki/XP21279" class="mw-redirect" title="XP21279">XP21279</a></li> <li><a href="/wiki/Xylazine" title="Xylazine">Xylazine</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%">Antagonists</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/Pyrimidinylpiperazine" title="Pyrimidinylpiperazine">1-PP</a></li> <li><a href="/wiki/Adimolol" title="Adimolol">Adimolol</a></li> <li><a href="/wiki/Amesergide" title="Amesergide">Amesergide</a></li> <li><a href="/wiki/Aptazapine" title="Aptazapine">Aptazapine</a></li> <li><a href="/wiki/Atipamezole" title="Atipamezole">Atipamezole</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Lurasidone" title="Lurasidone">lurasidone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Paliperidone" title="Paliperidone">paliperidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Azapirone" title="Azapirone">Azapirones</a> (e.g., <a href="/wiki/Buspirone" title="Buspirone">buspirone</a>, <a href="/wiki/Gepirone" title="Gepirone">gepirone</a>, <a href="/wiki/Ipsapirone" title="Ipsapirone">ipsapirone</a>, <a href="/wiki/Tandospirone" title="Tandospirone">tandospirone</a>)</li> <li><a href="/wiki/BRL-44408" title="BRL-44408">BRL-44408</a></li> <li><a href="/wiki/Buflomedil" title="Buflomedil">Buflomedil</a></li> <li><a href="/wiki/Cirazoline" title="Cirazoline">Cirazoline</a></li> <li><a href="/wiki/Efaroxan" title="Efaroxan">Efaroxan</a></li> <li><a href="/wiki/Esmirtazapine" title="Esmirtazapine">Esmirtazapine</a></li> <li><a href="/wiki/Fenmetozole" title="Fenmetozole">Fenmetozole</a></li> <li><a href="/wiki/Fluparoxan" title="Fluparoxan">Fluparoxan</a></li> <li><a href="/wiki/Idazoxan" title="Idazoxan">Idazoxan</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li> <li><a href="/wiki/Mirtazapine" title="Mirtazapine">Mirtazapine</a></li> <li><a href="/wiki/NAN-190" title="NAN-190">NAN-190</a></li> <li><a href="/wiki/Pardoprunox" title="Pardoprunox">Pardoprunox</a></li> <li><a href="/wiki/Phentolamine" title="Phentolamine">Phentolamine</a></li> <li><a href="/wiki/Phenoxybenzamine" title="Phenoxybenzamine">Phenoxybenzamine</a></li> <li><a href="/wiki/Piperoxan" title="Piperoxan">Piperoxan</a></li> <li><a href="/wiki/Piribedil" title="Piribedil">Piribedil</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Rotigotine" title="Rotigotine">Rotigotine</a></li> <li><a href="/wiki/Setiptiline" title="Setiptiline">Setiptiline</a></li> <li><a href="/wiki/Spegatrine" title="Spegatrine">Spegatrine</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/wiki/Sunepitron" title="Sunepitron">Sunepitron</a></li> <li><a href="/wiki/Terguride" title="Terguride">Terguride</a></li> <li><a href="/wiki/Tolazoline" title="Tolazoline">Tolazoline</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</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/%CE%92-adrenergic_receptor" class="mw-redirect" title="Β-adrenergic receptor">β</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%">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abediterol" title="Abediterol">Abediterol</a></li> <li><a href="/wiki/Alifedrine" title="Alifedrine">Alifedrine</a></li> <li><a href="/wiki/Amibegron" title="Amibegron">Amibegron</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/Arformoterol" title="Arformoterol">Arformoterol</a></li> <li><a href="/wiki/Arotinolol" title="Arotinolol">Arotinolol</a></li> <li><a href="/wiki/Bromoacetylalprenololmenthane" title="Bromoacetylalprenololmenthane">BAAM</a></li> <li><a href="/wiki/Bambuterol" title="Bambuterol">Bambuterol</a></li> <li><a href="/wiki/Befunolol" title="Befunolol">Befunolol</a></li> <li><a href="/wiki/Bitolterol" title="Bitolterol">Bitolterol</a></li> <li><a href="/wiki/Broxaterol" title="Broxaterol">Broxaterol</a></li> <li><a href="/wiki/Buphenine" title="Buphenine">Buphenine</a></li> <li><a href="/wiki/Carbuterol" title="Carbuterol">Carbuterol</a></li> <li><a href="/wiki/Carmoterol" title="Carmoterol">Carmoterol</a></li> <li><a href="/wiki/Cimaterol" title="Cimaterol">Cimaterol</a></li> <li><a href="/wiki/Clenbuterol" title="Clenbuterol">Clenbuterol</a></li> <li><a href="/wiki/Colterol" title="Colterol">Colterol</a></li> <li><a href="/wiki/Corbadrine" title="Corbadrine">Corbadrine</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Deoxyepinephrine" title="Deoxyepinephrine">Deoxyepinephrine (epinine, N-methyldopamine)</a></li> <li><a href="/wiki/Dipivefrine" title="Dipivefrine">Dipivefrine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</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/Droxidopa" title="Droxidopa">Droxidopa (L-DOPS)</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Etilevodopa" title="Etilevodopa">Etilevodopa</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Eugenodilol" title="Eugenodilol">Eugenodilol</a></li> <li><a href="/wiki/Fenoterol" title="Fenoterol">Fenoterol</a></li> <li><a href="/wiki/Formoterol" title="Formoterol">Formoterol</a></li> <li><a href="/wiki/Hexoprenaline" title="Hexoprenaline">Hexoprenaline</a></li> <li><a href="/wiki/Higenamine" title="Higenamine">Higenamine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Indacaterol" title="Indacaterol">Indacaterol</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/Isoxsuprine" title="Isoxsuprine">Isoxsuprine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA (levodopa)</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">L-Phenylalanine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">L-Tyrosine</a></li> <li><a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a></li> <li><a href="/wiki/Lubabegron" title="Lubabegron">Lubabegron</a></li> <li><a href="/wiki/Mabuterol" title="Mabuterol">Mabuterol</a></li> <li><a href="/wiki/Melevodopa" title="Melevodopa">Melevodopa</a></li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/Mirabegron" title="Mirabegron">Mirabegron</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Oxyfedrine" title="Oxyfedrine">Oxyfedrine</a></li> <li><a href="/wiki/PF-610355" title="PF-610355">PF-610355</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pirbuterol" title="Pirbuterol">Pirbuterol</a></li> <li><a href="/wiki/Prenalterol" title="Prenalterol">Prenalterol</a></li> <li><a href="/wiki/Ractopamine" title="Ractopamine">Ractopamine</a></li> <li><a href="/wiki/Procaterol" title="Procaterol">Procaterol</a></li> <li><a href="/wiki/Reproterol" title="Reproterol">Reproterol</a></li> <li><a href="/wiki/Rimiterol" title="Rimiterol">Rimiterol</a></li> <li><a href="/wiki/Ritodrine" title="Ritodrine">Ritodrine</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a></li> <li><a href="/wiki/Salmeterol" title="Salmeterol">Salmeterol</a></li> <li><a href="/wiki/Solabegron" title="Solabegron">Solabegron</a></li> <li><a href="/wiki/Terbutaline" title="Terbutaline">Terbutaline</a></li> <li><a href="/wiki/Tretoquinol" title="Tretoquinol">Tretoquinol</a></li> <li><a href="/wiki/Tulobuterol" title="Tulobuterol">Tulobuterol</a></li> <li><a href="/wiki/Vibegron" title="Vibegron">Vibegron</a></li> <li><a href="/wiki/Vilanterol" title="Vilanterol">Vilanterol</a></li> <li><a href="/wiki/Xamoterol" title="Xamoterol">Xamoterol</a></li> <li><a href="/wiki/XP21279" class="mw-redirect" title="XP21279">XP21279</a></li> <li><a href="/wiki/Zilpaterol" title="Zilpaterol">Zilpaterol</a></li> <li><a href="/wiki/Zinterol" title="Zinterol">Zinterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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/Acebutolol" title="Acebutolol">Acebutolol</a></li> <li><a href="/wiki/Adaprolol" title="Adaprolol">Adaprolol</a></li> <li><a href="/wiki/Adimolol" title="Adimolol">Adimolol</a></li> <li><a href="/wiki/Afurolol" title="Afurolol">Afurolol</a></li> <li><a href="/wiki/Alprenolol" title="Alprenolol">Alprenolol</a></li> <li><a href="/wiki/Alprenoxime" title="Alprenoxime">Alprenoxime</a></li> <li><a href="/wiki/Amosulalol" title="Amosulalol">Amosulalol</a></li> <li><a href="/wiki/Ancarolol" title="Ancarolol">Ancarolol</a></li> <li><a href="/wiki/Arnolol" title="Arnolol">Arnolol</a></li> <li><a href="/wiki/Arotinolol" title="Arotinolol">Arotinolol</a></li> <li><a href="/wiki/Atenolol" title="Atenolol">Atenolol</a></li> <li><a href="/wiki/Befunolol" title="Befunolol">Befunolol</a></li> <li><a href="/wiki/Betaxolol" title="Betaxolol">Betaxolol</a></li> <li><a href="/wiki/Bevantolol" title="Bevantolol">Bevantolol</a></li> <li><a href="/wiki/Bisoprolol" title="Bisoprolol">Bisoprolol</a></li> <li><a href="/wiki/Bopindolol" title="Bopindolol">Bopindolol</a></li> <li><a href="/wiki/Bornaprolol" title="Bornaprolol">Bornaprolol</a></li> <li><a href="/wiki/Brefonalol" title="Brefonalol">Brefonalol</a></li> <li><a href="/wiki/Bucindolol" title="Bucindolol">Bucindolol</a></li> <li><a href="/wiki/Bucumolol" title="Bucumolol">Bucumolol</a></li> <li><a href="/wiki/Bufetolol" title="Bufetolol">Bufetolol</a></li> <li><a href="/wiki/Bufuralol" title="Bufuralol">Bufuralol</a></li> <li><a href="/wiki/Bunitrolol" title="Bunitrolol">Bunitrolol</a></li> <li><a href="/wiki/Bunolol" class="mw-redirect" title="Bunolol">Bunolol</a></li> <li><a href="/wiki/Bupranolol" title="Bupranolol">Bupranolol</a></li> <li><a href="/wiki/Butaxamine" title="Butaxamine">Butaxamine</a></li> <li><a href="/wiki/Butidrine" title="Butidrine">Butidrine</a></li> <li><a href="/wiki/Butofilolol" title="Butofilolol">Butofilolol</a></li> <li><a href="/wiki/Capsinolol" title="Capsinolol">Capsinolol</a></li> <li><a href="/wiki/Carazolol" title="Carazolol">Carazolol</a></li> <li><a href="/wiki/Carpindolol" title="Carpindolol">Carpindolol</a></li> <li><a href="/wiki/Carteolol" title="Carteolol">Carteolol</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Celiprolol" title="Celiprolol">Celiprolol</a></li> <li><a href="/wiki/Cetamolol" title="Cetamolol">Cetamolol</a></li> <li><a href="/wiki/Cicloprolol" title="Cicloprolol">Cicloprolol</a></li> <li><a href="/wiki/Cinamolol" title="Cinamolol">Cinamolol</a></li> <li><a href="/wiki/Cloranolol" title="Cloranolol">Cloranolol</a></li> <li><a href="/wiki/Cyanopindolol" title="Cyanopindolol">Cyanopindolol</a></li> <li><a href="/wiki/Dalbraminol" title="Dalbraminol">Dalbraminol</a></li> <li><a href="/wiki/Dexpropranolol" class="mw-redirect" title="Dexpropranolol">Dexpropranolol</a></li> <li><a href="/wiki/Diacetolol" title="Diacetolol">Diacetolol</a></li> <li><a href="/wiki/Dichloroisoprenaline" title="Dichloroisoprenaline">Dichloroisoprenaline</a></li> <li><a href="/wiki/Dihydroalprenolol" title="Dihydroalprenolol">Dihydroalprenolol</a></li> <li><a href="/wiki/Dilevalol" class="mw-redirect" title="Dilevalol">Dilevalol</a></li> <li><a href="/wiki/Diprafenone" title="Diprafenone">Diprafenone</a></li> <li><a href="/wiki/Draquinolol" title="Draquinolol">Draquinolol</a></li> <li><a href="/wiki/Ecastolol" title="Ecastolol">Ecastolol</a></li> <li><a href="/wiki/Epanolol" title="Epanolol">Epanolol</a></li> <li><a href="/wiki/Ericolol" title="Ericolol">Ericolol</a></li> <li><a href="/wiki/Ersentilide" title="Ersentilide">Ersentilide</a></li> <li><a href="/wiki/Esatenolol" class="mw-redirect" title="Esatenolol">Esatenolol</a></li> <li><a href="/wiki/Esprolol" class="mw-redirect" title="Esprolol">Esprolol</a></li> <li><a href="/wiki/Eugenodilol" title="Eugenodilol">Eugenodilol</a></li> <li><a href="/wiki/Exaprolol" title="Exaprolol">Exaprolol</a></li> <li><a href="/wiki/Falintolol" title="Falintolol">Falintolol</a></li> <li><a href="/wiki/Flestolol" title="Flestolol">Flestolol</a></li> <li><a href="/wiki/Flusoxolol" title="Flusoxolol">Flusoxolol</a></li> <li><a href="/wiki/Hydroxycarteolol" title="Hydroxycarteolol">Hydroxycarteolol</a></li> <li><a href="/wiki/Hydroxytertatolol" title="Hydroxytertatolol">Hydroxytertatolol</a></li> <li><a href="/wiki/ICI-118,551" title="ICI-118,551">ICI-118,551</a></li> <li><a href="/wiki/Idropranolol" class="mw-redirect" title="Idropranolol">Idropranolol</a></li> <li><a href="/wiki/Indenolol" title="Indenolol">Indenolol</a></li> <li><a href="/wiki/Indopanolol" title="Indopanolol">Indopanolol</a></li> <li><a href="/wiki/Iodocyanopindolol" title="Iodocyanopindolol">Iodocyanopindolol</a></li> <li><a href="/wiki/Iprocrolol" title="Iprocrolol">Iprocrolol</a></li> <li><a href="/wiki/Isoxaprolol" title="Isoxaprolol">Isoxaprolol</a></li> <li><a href="/wiki/Isamoltane" title="Isamoltane">Isamoltane</a></li> <li><a href="/wiki/Labetalol" title="Labetalol">Labetalol</a></li> <li><a href="/wiki/Landiolol" title="Landiolol">Landiolol</a></li> <li><a href="/wiki/Levobetaxolol" title="Levobetaxolol">Levobetaxolol</a></li> <li><a href="/wiki/Levobunolol" title="Levobunolol">Levobunolol</a></li> <li><a href="/wiki/Levomoprolol" title="Levomoprolol">Levomoprolol</a></li> <li><a href="/wiki/Medroxalol" title="Medroxalol">Medroxalol</a></li> <li><a href="/wiki/Mepindolol" title="Mepindolol">Mepindolol</a></li> <li><a href="/wiki/Metipranolol" title="Metipranolol">Metipranolol</a></li> <li><a href="/wiki/Metoprolol" title="Metoprolol">Metoprolol</a></li> <li><a href="/wiki/Moprolol" title="Moprolol">Moprolol</a></li> <li><a href="/wiki/Nadolol" title="Nadolol">Nadolol</a></li> <li><a href="/wiki/Nadoxolol" title="Nadoxolol">Nadoxolol</a></li> <li><a href="/wiki/Nebivolol" title="Nebivolol">Nebivolol</a></li> <li><a href="/wiki/Nifenalol" title="Nifenalol">Nifenalol</a></li> <li><a href="/wiki/Nipradilol" title="Nipradilol">Nipradilol</a></li> <li><a href="/wiki/Oxprenolol" title="Oxprenolol">Oxprenolol</a></li> <li><a href="/wiki/Pacrinolol" title="Pacrinolol">Pacrinolol</a></li> <li><a href="/wiki/Pafenolol" title="Pafenolol">Pafenolol</a></li> <li><a href="/wiki/Pamatolol" title="Pamatolol">Pamatolol</a></li> <li><a href="/wiki/Pargolol" title="Pargolol">Pargolol</a></li> <li><a href="/wiki/Penbutolol" title="Penbutolol">Penbutolol</a></li> <li><a href="/wiki/Pindolol" title="Pindolol">Pindolol</a></li> <li><a href="/wiki/Practolol" title="Practolol">Practolol</a></li> <li><a href="/wiki/Primidolol" title="Primidolol">Primidolol</a></li> <li><a href="/wiki/Procinolol" title="Procinolol">Procinolol</a></li> <li><a href="/wiki/Pronethalol" title="Pronethalol">Pronethalol</a></li> <li><a href="/wiki/Propafenone" title="Propafenone">Propafenone</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/Ridazolol" title="Ridazolol">Ridazolol</a></li> <li><a href="/wiki/Ronactolol" title="Ronactolol">Ronactolol</a></li> <li><a href="/wiki/Soquinolol" title="Soquinolol">Soquinolol</a></li> <li><a href="/wiki/Sotalol" title="Sotalol">Sotalol</a></li> <li><a href="/wiki/Spirendolol" title="Spirendolol">Spirendolol</a></li> <li><a href="/wiki/SR_59230A" title="SR 59230A">SR 59230A</a></li> <li><a href="/wiki/Sulfinalol" title="Sulfinalol">Sulfinalol</a></li> <li><a href="/wiki/Talinolol" title="Talinolol">Talinolol</a></li> <li><a href="/wiki/Tazolol" title="Tazolol">Tazolol</a></li> <li><a href="/wiki/Tertatolol" title="Tertatolol">Tertatolol</a></li> <li><a href="/wiki/Tienoxolol" title="Tienoxolol">Tienoxolol</a></li> <li><a href="/wiki/Tilisolol" title="Tilisolol">Tilisolol</a></li> <li><a href="/wiki/Timolol" title="Timolol">Timolol</a></li> <li><a href="/wiki/Tiprenolol" title="Tiprenolol">Tiprenolol</a></li> <li><a href="/wiki/Tolamolol" title="Tolamolol">Tolamolol</a></li> <li><a href="/wiki/Toliprolol" title="Toliprolol">Toliprolol</a></li> <li><a href="/wiki/Xibenolol" title="Xibenolol">Xibenolol</a></li> <li><a href="/wiki/Xipranolol" title="Xipranolol">Xipranolol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li>See also: <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></li> <li><a href="/wiki/Template:Dopamine_receptor_modulators" title="Template:Dopamine receptor modulators">Dopaminergics</a></li> <li><a href="/wiki/Template:Serotonin_receptor_modulators" title="Template:Serotonin receptor modulators">Serotonergics</a></li> <li><a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a></li> <li><a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">Monoamine releasing agents</a></li> <li><a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></li> <li><a href="/wiki/Template:Monoamine_neurotoxins" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Monoamine_releasing_agents" 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_agents" 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</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>Morpholines: <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>Oxazolines: <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>Phenethylamines: <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" class="mw-redirect" 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" 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">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/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 href="/wiki/Pseudoephedrine" title="Pseudoephedrine">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>Piperazines: <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>Others: <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</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>Morpholines: <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>Oxazolines: <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>Phenethylamines: <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" class="mw-redirect" 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" 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">pBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">pCA</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">pIA</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-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>Piperazines: <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>Others: <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</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>Aminoindanes: <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>Aminotetralins: <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>Oxazolines: <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>Phenethylamines: <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" 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" class="mw-redirect" 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>Piperazines: <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>Tryptamines: <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" class="mw-redirect" 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>Others: <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>DAT modulators: Agonist-like: <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>; Antagonist-like: <a href="/wiki/SoRI-20041" title="SoRI-20041">SoRI-20041</a></li></ul> <ul><li>Adrenergic release blockers: <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>See also: <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" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</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="Phenethylamines" 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: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="Phenethylamines" 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>Psychedelics: <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></ul> <ul><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="/w/index.php?title=2C-T-33&action=edit&redlink=1" class="new" title="2C-T-33 (page does not exist)">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></ul> <ul><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> Stimulants: <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a> <ul><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">m-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine">N-Methylphenethylamine</a></li> <li><a href="/wiki/O-Methylphenethylamine" class="mw-redirect" title="O-Methylphenethylamine">o-Methylphenethylamine</a></li> <li><a href="/wiki/P-Methylphenethylamine" class="mw-redirect" title="P-Methylphenethylamine">p-Methylphenethylamine</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li></ul> <ul><li>Entactogens: <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> Others: <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>Psychedelics: <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" 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> Stimulants: <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">L-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" 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 href="/wiki/Pseudoephedrine" title="Pseudoephedrine">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> Entactogens: <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" class="mw-redirect" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/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" 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> Others: <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">D-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>Stimulants: <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> Entactogens: <a href="/wiki/Methylenedioxyphentermine" class="mw-redirect" title="Methylenedioxyphentermine">MDPH</a></li> <li><a href="/wiki/Methylenedioxymethylphentermine" class="mw-redirect" title="Methylenedioxymethylphentermine">MDMPH</a> Others: <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>Stimulants: <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> Entactogens: <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>Entactogens: <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> Stimulants: <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>Stimulants: <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> (and close relatives)</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">D-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">L-DOPA</a> (Levodopa)</li> <li><a href="/wiki/L-DOPS" class="mw-redirect" title="L-DOPS">L-DOPS</a> (Droxidopa)</li> <li><a href="/wiki/L-Phenylalanine" class="mw-redirect" title="L-Phenylalanine">L-Phenylalanine</a></li> <li><a href="/wiki/L-Tyrosine" class="mw-redirect" title="L-Tyrosine">L-Tyrosine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine">m-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> (m-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">p-Octopamine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">p-Tyramine</a></li> <li><a class="mw-selflink selflink">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" 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