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subsection</span> </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Properties" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Properties</span> </div> </a> <ul id="toc-Properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Synthesis</span> </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Structural_relationships" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Structural_relationships"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Structural relationships</span> </div> </a> <ul id="toc-Structural_relationships-sublist" 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href="https://bs.wikipedia.org/wiki/Sinefrin" title="Sinefrin – Bosnian" lang="bs" hreflang="bs" data-title="Sinefrin" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Synefrin" title="Synefrin – Czech" lang="cs" hreflang="cs" data-title="Synefrin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Synephrin" title="Synephrin – German" lang="de" hreflang="de" data-title="Synephrin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Sinefrino" title="Sinefrino – Esperanto" lang="eo" hreflang="eo" data-title="Sinefrino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%DB%8C%D9%86%D9%81%D8%B1%DB%8C%D9%86" title="سینفرین – Persian" lang="fa" hreflang="fa" data-title="سینفرین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Sinefrina" title="Sinefrina – Italian" lang="it" hreflang="it" data-title="Sinefrina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B7%E3%83%8D%E3%83%95%E3%83%AA%E3%83%B3" title="シネフリン – Japanese" lang="ja" hreflang="ja" data-title="シネフリン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Synefryna" title="Synefryna – Polish" lang="pl" hreflang="pl" data-title="Synefryna" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Sinefrin" title="Sinefrin – Serbian" lang="sr" hreflang="sr" data-title="Sinefrin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Sinefrin" title="Sinefrin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Sinefrin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Synefriini" title="Synefriini – Finnish" lang="fi" hreflang="fi" data-title="Synefriini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Synefrin" title="Synefrin – Swedish" lang="sv" hreflang="sv" data-title="Synefrin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A1%D0%B8%D0%BD%D0%B5%D1%84%D1%80%D1%96%D0%BD" title="Синефрін – Ukrainian" lang="uk" 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</nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article will focus, insofar as possible, on synephrine itself, rather than on the drug mixtures containing it.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Synephrine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center skin-invert" typeof="mw:File"><a href="/wiki/File:Synephrine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Synephrine.svg/220px-Synephrine.svg.png" decoding="async" width="220" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Synephrine.svg/330px-Synephrine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Synephrine.svg/440px-Synephrine.svg.png 2x" data-file-width="512" data-file-height="283" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Synephrine_Ball_and_Stick.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/Synephrine_Ball_and_Stick.png/250px-Synephrine_Ball_and_Stick.png" decoding="async" width="220" height="139" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/Synephrine_Ball_and_Stick.png/330px-Synephrine_Ball_and_Stick.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/57/Synephrine_Ball_and_Stick.png/500px-Synephrine_Ball_and_Stick.png 2x" data-file-width="3157" data-file-height="2000" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">4-[1-Hydroxy-2-(methylamino)ethyl]phenol</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><i>p</i>-Synephrine; Oxedrine; 4,β-Dihydroxy-<i>N</i>-methylphenethylamine</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=94-07-5">94-07-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CNCC%28O%29c1ccc%28O%29cc1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=29081">CHEBI:29081</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL33720">ChEMBL33720</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.6904.html">6904</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.002.092">100.002.092</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q421351#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D07148">D07148</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/7172">7172</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/PEG5DP7434">PEG5DP7434</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID0030588">DTXSID0030588</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q421351#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: YRCWQPVGYLYSOX-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: YRCWQPVGYLYSOX-UHFFFAOYAW</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CNCC(O)c1ccc(O)cc1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C<sub>9</sub>H<sub>13</sub>NO<sub>2</sub>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>167.21 g/mol    </td></tr> <tr> <td>Appearance </td> <td>colorless solid </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>162 to 164 °C (324 to 327 °F; 435 to 437 K) (R-(−)-enantiomer); 184 to 185 °C (racemate) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>soluble </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_C01" title="ATC code C01">C01CA08</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=C01CA08">WHO</a></span>) <a href="/wiki/ATC_code_S01" title="ATC code S01">S01GA06</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=S01GA06">WHO</a></span>), <a href="/wiki/ATC_code_S01" title="ATC code S01">QS01FB90</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QS01FB90">WHO</a></span>) </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Synephrine</b>, or, more specifically, <b><i>p</i>-synephrine</b>, is an <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a>, occurring naturally in some plants and animals, and also in approved drugs products as its <i>m</i>-substituted analog known as neo-synephrine.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> <i>p</i>-Synephrine (or formerly <b>Sympatol</b> and <b>oxedrine</b> [<a href="/wiki/British_Approved_Name" title="British Approved Name">BAN</a>]) and <i>m</i>-synephrine are known for their longer acting <a href="/wiki/Adrenergic" title="Adrenergic">adrenergic</a> effects compared to <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a> and <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>. This substance is present at very low concentrations in common foodstuffs such as <a href="/wiki/Orange_juice" title="Orange juice">orange juice</a> and other orange (<i><a href="/wiki/Citrus" title="Citrus">Citrus</a></i> species) products, both of the "sweet" and "bitter" variety. The preparations used in <a href="/wiki/Traditional_Chinese_medicine" title="Traditional Chinese medicine">traditional Chinese medicine</a> (<b>TCM</b>), also known as Zhi Shi (枳实), are the immature and dried whole oranges from <i><a href="/wiki/Citrus_aurantium" class="mw-redirect" title="Citrus aurantium">Citrus aurantium</a></i> (<i>Fructus Aurantii Immaturus</i>). Extracts of the same material or purified synephrine are also marketed in the US, sometimes in combination with <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>, as a weight-loss-promoting <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a> for oral consumption. While the traditional preparations have been in use for millennia as a component of TCM-formulas, synephrine itself is not an approved <a href="/wiki/Over_the_counter_drug" class="mw-redirect" title="Over the counter drug">over the counter drug</a>. As a pharmaceutical, <i>m</i>-synephrine (<a href="/wiki/Phenylephrine" title="Phenylephrine">phenylephrine</a>) is still used as a <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic</a> (i.e. for its <a href="/wiki/Hypertensive" class="mw-redirect" title="Hypertensive">hypertensive</a> and <a href="/wiki/Vasoconstrictor" class="mw-redirect" title="Vasoconstrictor">vasoconstrictor</a> properties), mostly by injection for the treatment of emergencies such as <a href="/wiki/Shock_(circulatory)" title="Shock (circulatory)">shock</a>, and rarely orally for the treatment of bronchial problems associated with <a href="/wiki/Asthma" title="Asthma">asthma</a> and <a href="/wiki/Hay-fever" class="mw-redirect" title="Hay-fever">hay-fever</a>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>a<span class="cite-bracket">]</span></a></sup> </p><p>There is a difference between studies concerning synephrine as a single chemical entity (synephrine can exist in the form of either of two <a href="/wiki/Stereoisomers" class="mw-redirect" title="Stereoisomers">stereoisomers</a>, d- and l-synephrine, which are chemically and pharmacologically distinct), and synephrine which is mixed with other drugs and/or botanical extracts in a "supplement", as well as synephrine which is present as only one chemical component in a naturally-occurring mixture of <a href="/wiki/Phytochemicals" class="mw-redirect" title="Phytochemicals">phytochemicals</a> such as the rind or fruit of a bitter orange. Mixtures containing synephrine as only one of their chemical components (regardless of whether these are of synthetic or natural origin) should not be assumed to produce exactly the same biological effects as synephrine alone.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>In physical appearance, synephrine is a colorless, crystalline solid and is water-soluble. Its molecular structure is based on a <a href="/wiki/Phenethylamine" title="Phenethylamine">phenethylamine</a> skeleton and is related to those of many other drugs and to the major <a href="/wiki/Neurotransmitters" class="mw-redirect" title="Neurotransmitters">neurotransmitters</a> epinephrine and norepinephrine. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrences">Natural occurrences</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=1" title="Edit section: Natural occurrences"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Synephrine, although already known as a synthetic <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a>, was first isolated as a <a href="/wiki/Natural_product" title="Natural product">natural product</a> from the leaves of various <i><a href="/wiki/Citrus" title="Citrus">Citrus</a></i> trees, and its presence noted in different <i>Citrus</i> juices, by Stewart and co-workers in the early 1960s.<sup id="cite_ref-Stew_4-0" class="reference"><a href="#cite_note-Stew-4"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Stew2_5-0" class="reference"><a href="#cite_note-Stew2-5"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> A survey of the distribution of synephrine amongst the higher plants was published in 1970 by Wheaton and Stewart.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It has subsequently been detected in <i><a href="/wiki/Evodia" class="mw-redirect" title="Evodia">Evodia</a></i><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> and <i><a href="/wiki/Zanthoxylum" title="Zanthoxylum">Zanthoxylum</a></i> species,<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> all plants of the family Rutaceae. </p><p>Trace levels (0.003%) of synephrine have also been detected in the dried leaves of <i><a href="/wiki/Pogostemon_cablin" class="mw-redirect" title="Pogostemon cablin">Pogostemon cablin</a></i> (<a href="/wiki/Patchouli" title="Patchouli">patchouli</a>, Lamiaceae).<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It is also found in certain cactus species of the genera <i><a href="/wiki/Coryphantha" title="Coryphantha">Coryphantha</a></i> and <i><a href="/wiki/Dolichothele" title="Dolichothele">Dolichothele</a></i>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>However, this compound is found predominantly in a number of <i>Citrus</i> species, including "bitter" orange varieties. </p> <div class="mw-heading mw-heading3"><h3 id="In_Citrus">In <i>Citrus</i></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=2" title="Edit section: In Citrus"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Extracts of unripe fruit from Asian cultivars of <i><a href="/wiki/Citrus_aurantium" class="mw-redirect" title="Citrus aurantium">Citrus aurantium</a></i> (commonly known as "bitter" orange), collected in China, were reported to contain synephrine levels of about 0.1–0.3%, or ~1–3 mg/g;<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Analysis of dried fruit of <i>C. aurantium</i> grown in Italy showed a concentration of synephrine of ~1 mg/g, with peel containing over three times more than the pulp.<sup id="cite_ref-Pellat_12-0" class="reference"><a href="#cite_note-Pellat-12"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Sweet oranges of the Tarocco, Naveline and Navel varieties, bought on the Italian market, were found to contain ~13–34 μg/g (corresponding to 13–34 mg/kg) synephrine (with roughly equal concentrations in juice and separated pulp); from these results, it was calculated that eating one "average" Tarocco orange would result in the consumption of ~6 mg of synephrine.<sup id="cite_ref-Mat_13-0" class="reference"><a href="#cite_note-Mat-13"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>An analysis of 32 different orange "jams", originating mostly in the US and UK, but including samples from France, Italy, Spain, or Lebanon, showed synephrine levels ranging from 0.05 mg/g–0.0009 mg/g<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>b<span class="cite-bracket">]</span></a></sup> in those jams made from bitter oranges, and levels of 0.05 mg/g–0.006 mg/g<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>c<span class="cite-bracket">]</span></a></sup> of synephrine in jams made from sweet oranges.<sup id="cite_ref-Av_16-0" class="reference"><a href="#cite_note-Av-16"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Synephrine has been found in <a href="/wiki/Marmalade" title="Marmalade">marmalade</a> made from <i><a href="/wiki/Citrus_unshiu" title="Citrus unshiu">Citrus unshiu</a></i> (Satsuma mandarin)<sup id="cite_ref-XRef_17-0" class="reference"><a href="#cite_note-XRef-17"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> obtained in Japan, at a concentration of ~0.12 mg/g (or about 2.4 mg/20g serving).<sup id="cite_ref-Kusu_18-0" class="reference"><a href="#cite_note-Kusu-18"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Most of the orange marmalades made in the US are produced using "sweet" oranges (<i><a href="/wiki/Citrus_sinensis" class="mw-redirect" title="Citrus sinensis">C. sinensis</a></i>), whereas "bitter" or Seville oranges (<i>C. aurantium</i>) are used for making the more traditional, bitterer marmalades in the United Kingdom.<sup id="cite_ref-Blum_19-0" class="reference"><a href="#cite_note-Blum-19"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>A sample of commercial Japanese <i>C. unshiu</i> juice was found to contain ~0.36 mg/g synephrine (or roughly 360 mg/L),<sup id="cite_ref-Kusu_18-1" class="reference"><a href="#cite_note-Kusu-18"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> while in juice products obtained from a Satsuma mandarin variety grown in California, levels of synephrine ranged from 55 to 160 mg/L .<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Juices from "sweet" oranges purchased in Brazilian markets were found to contain ~10–22 mg/L synephrine; commercial orange soft drinks obtained on the Brazilian market had an average synephrine content of ~1 mg/L.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Commercial Italian orange juices contained ~13–32 mg/L of synephrine<sup id="cite_ref-Mat_13-1" class="reference"><a href="#cite_note-Mat-13"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>In a survey of over 50 citrus fruit juices, either commercially-prepared or hand-squeezed from fresh fruit, obtained on the US market, Avula and co-workers found synephrine levels ranging from ~4–60 mg/L;<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>d<span class="cite-bracket">]</span></a></sup> no synephrine was detected in juices from grapefruit, lime, or lemon.<sup id="cite_ref-Av_16-1" class="reference"><a href="#cite_note-Av-16"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>An analysis of the synephrine levels in a range of different citrus fruits, carried out on juices that had been extracted from fresh, peeled fruit, was reported by Uckoo and co-workers, with the following results: Marrs sweet orange (<i>C. sinensis</i> Tan.): ~85 mg/L; Nova tangerine (<i><a href="/wiki/Citrus_reticulata" class="mw-redirect" title="Citrus reticulata">C. reticulata</a></i> Tan.): ~78 mg/L; clementine (<i>C. clementina</i> Tan.): ~115 mg/L; Meyer lemon (<i>C. limon</i> Tan.) ~3 mg/kg; Ugli tangelo (<i>C. reticulata</i> × <i>C. paradisi</i>) ~47 mg/kg. No synephrine was detected in: Rio Red grapefruit (<i>C. paradisi</i> Macf.); Red-fleshed pummelo (<i>C. grandis</i> Tan.); or Wekiwa tangelo (<i>C. reticulata</i> × <i>C. paradisi</i>).<sup id="cite_ref-XRef_17-1" class="reference"><a href="#cite_note-XRef-17"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Numerous additional comparable analyses of the synephrine content of <i>Citrus</i> fruits and products derived from them may be found in the research literature. </p> <div class="mw-heading mw-heading3"><h3 id="In_humans_and_other_animals">In humans and other animals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=3" title="Edit section: In humans and other animals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Low levels of synephrine have been found in normal human urine,<sup id="cite_ref-Ib_24-0" class="reference"><a href="#cite_note-Ib-24"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> as well as in other mammalian tissue.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> To reduce the likelihood that the synephrine detected in urine had a dietary origin, the subjects tested by Ibrahim and co-workers abstained from the consumption of any citrus products for 48 hours prior to providing urine samples.<sup id="cite_ref-Ib_24-1" class="reference"><a href="#cite_note-Ib-24"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>A 2006 study of synephrine in human <a href="/wiki/Blood_platelets" class="mw-redirect" title="Blood platelets">blood platelets</a> by D'Andrea and co-workers showed increased levels in platelets from patients suffering from aura-associated migraine (0.72 ng/10<sup>8</sup> platelets, compared to 0.33 ng/10<sup>8</sup> platelets in control subjects).<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Earlier, the same research group had reported a normal human <a href="/wiki/Blood_plasma" title="Blood plasma">blood plasma</a> level of synephrine of 0.90–13.69 ng/mL.<sup id="cite_ref-Andrea_29-0" class="reference"><a href="#cite_note-Andrea-29"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Stereoisomers">Stereoisomers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=4" title="Edit section: Stereoisomers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Since synephrine exists as either of two <a href="/wiki/Enantiomers" class="mw-redirect" title="Enantiomers">enantiomers</a> (see Chemistry section below for further discussion), which do not produce identical biological effects (see Pharmacology section below) some researchers have examined the <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomeric</a> composition of synephrine extracted from natural sources. Although it seems clear that synephrine is found in those <i>Citrus</i> species which have been studied predominantly as the l-isomer,<sup id="cite_ref-Kusu_18-2" class="reference"><a href="#cite_note-Kusu-18"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Pel_30-0" class="reference"><a href="#cite_note-Pel-30"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> low levels of d-synephrine have been detected in juice and marmalade made from <i>C. unshiu</i>,<sup id="cite_ref-Kusu_18-3" class="reference"><a href="#cite_note-Kusu-18"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> and low levels (0.002%) have been reported in fresh fruit from <i>C. aurantium</i>.<sup id="cite_ref-Pel_30-1" class="reference"><a href="#cite_note-Pel-30"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> There are indications that some d-synephrine may be formed by the <a href="/wiki/Racemization" title="Racemization">racemization</a> of l-synephrine as a result of the processing of fresh fruit, although this matter has not been completely clarified.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> However, regardless of the situation in <i>Citrus</i> species, Ranieri and McLaughlin reported the <i>isolation</i> of <a href="/wiki/Racemic" class="mw-redirect" title="Racemic">racemic</a> (i.e. a mixture of equal amounts of d- and l- stereoisomers) synephrine from a cactus of the genus <i>Dolichothele</i>, under conditions that would be unlikely to cause a significant amount of racemization.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=5" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The biosynthesis of synephrine in <i>Citrus</i> species is believed to follow the pathway: <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a> → <a href="/wiki/Tyramine" title="Tyramine">tyramine</a> → <a href="/wiki/N-methyltyramine" class="mw-redirect" title="N-methyltyramine"><i>N</i>-methyltyramine</a> → synephrine, involving the enzymes <a href="/wiki/Tyrosine_decarboxylase" title="Tyrosine decarboxylase">tyrosine decarboxylase</a> in the first step, <a href="/wiki/Tyramine_N-methyltransferase" title="Tyramine N-methyltransferase">tyramine <i>N</i>-methyltransferase</a> in the second, and <i>N</i>-methyl-tyramine-β-hydroxylase in the third.<sup id="cite_ref-Wheat_34-0" class="reference"><a href="#cite_note-Wheat-34"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> This pathway differs from that thought to occur in animals, involving <a href="/wiki/Octopamine" title="Octopamine">octopamine</a>: tyramine → octopamine → synephrine, where the conversion of tyramine to octopamine is mediated by <a href="/wiki/Dopamine-%CE%B2-hydroxylase" class="mw-redirect" title="Dopamine-β-hydroxylase">dopamine-β-hydroxylase</a>, and the conversion of octopamine to synephrine by <a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">phenylethanolamine <i>N</i>-methyltransferase</a>.<sup id="cite_ref-Andrea_29-1" class="reference"><a href="#cite_note-Andrea-29"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wheat_34-1" class="reference"><a href="#cite_note-Wheat-34"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <table role="presentation" cellpadding="0" style="border-spacing:0; margin-left: auto; margin-right: auto; border: none;"> <tbody><tr> <td><div class="thumb center" style="margin: 1em auto;"> <div class="thumbinner" style="width:592px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: light-dark(#F0F8FF,var(--background-color-neutral)); color:var(--color-base,light-dark(#202122,#eaecf0)); margin-bottom:3px;">Biosynthetic pathways for <a href="/wiki/Catecholamine" title="Catecholamine">catecholamines</a> and <a href="/wiki/Trace_amine" title="Trace amine">trace amines</a> in the <a href="/wiki/Human_brain" title="Human brain">human brain</a><sup id="cite_ref-Trace_amine_template_1_36-0" class="reference"><a href="#cite_note-Trace_amine_template_1-36"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Trace_amine_template_2_37-0" class="reference"><a href="#cite_note-Trace_amine_template_2-37"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CYP2D6_tyramine-dopamine_metabolism_38-0" class="reference"><a href="#cite_note-CYP2D6_tyramine-dopamine_metabolism-38"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup></div> <div class="skin-invert-image" style="position:relative; width:590px; height:465px; overflow:hidden; border:solid #ccc 1px; background-color:light-dark(white,transparent);"> <div style="left:5px; top:0px; width:580px; position:absolute"> <span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/File:Catecholamine_and_trace_amine_biosynthesis.svg" title="commons:File:Catecholamine and trace amine biosynthesis.svg"><img alt="Graphic of catecholamine and trace amine biosynthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/580px-Catecholamine_and_trace_amine_biosynthesis.svg.png" decoding="async" width="580" height="458" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/870px-Catecholamine_and_trace_amine_biosynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/1160px-Catecholamine_and_trace_amine_biosynthesis.svg.png 2x" data-file-width="512" data-file-height="404" /></a></span> </div> <div style="text-align:center; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:var(--color-base,#202122)"><div id="annotation_40x60" style="position:absolute; left:40px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylalanine" title="Phenylalanine"><small>L</small>-Phenylalanine</a></span></div> <div id="annotation_50x185" style="position:absolute; left:50px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Tyrosine" title="Tyrosine"><small>L</small>-Tyrosine</a></span></div> <div id="annotation_60x315" style="position:absolute; left:60px; top:315px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/L-DOPA" title="L-DOPA"><small>L</small>-DOPA</a></span></div> <div id="annotation_50x445" style="position:absolute; left:50px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Adrenaline" title="Adrenaline">Epinephrine</a></span></div> <div id="annotation_245x60" style="position:absolute; left:245px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></span></div> <div id="annotation_245x185" style="position:absolute; left:245px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></span></div> <div id="annotation_245x315" style="position:absolute; left:245px; top:315px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></span></div> <div id="annotation_245x445" style="position:absolute; left:245px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></span></div> <div id="annotation_415x60" style="position:absolute; left:415px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></span></div> <div id="annotation_440x138" style="position:absolute; left:440px; top:138px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/N-Methyltyramine" title="N-Methyltyramine"><i>N</i>-Methyltyramine</a></span></div> <div id="annotation_440x228" style="position:absolute; left:440px; top:228px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></span></div> <div id="annotation_455x350" style="position:absolute; left:455px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><span style="color:black;background:yellow"><b>Synephrine</b></span></span></div> <div id="annotation_445x445" style="position:absolute; left:445px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></span></div> <div id="annotation_167x16" style="position:absolute; left:167px; top:16px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></span></div> <div id="annotation_167x145" style="position:absolute; left:167px; top:145px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></span></div> <div id="annotation_167x275" style="position:absolute; left:167px; top:275px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></span></div> <div id="annotation_164x295" style="position:absolute; left:164px; top:295px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;">primary<br />pathway</span></div> <div id="annotation_370x17" style="position:absolute; left:370px; top:17px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_360x120" style="position:absolute; left:360px; top:120px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_445x255" style="position:absolute; left:445px; top:255px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_176x407" style="position:absolute; left:176px; top:407px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_40x90" style="position:absolute; left:40px; top:90px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Biopterin-dependent_aromatic_amino_acid_hydroxylase" title="Biopterin-dependent aromatic amino acid hydroxylase">AAAH</a></span></div> <div id="annotation_40x220" style="position:absolute; left:40px; top:220px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Biopterin-dependent_aromatic_amino_acid_hydroxylase" title="Biopterin-dependent aromatic amino acid hydroxylase">AAAH</a></span></div> <div id="annotation_225x215" style="position:absolute; left:225px; top:215px; line-height:110%;"><span style="background-color:transparent; color:inherit;">brain<br /><a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a></span></div> <div id="annotation_291x217" style="position:absolute; left:291px; top:217px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;">minor<br />pathway</span></div> <div id="annotation_325x350" style="position:absolute; left:325px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Catechol-O-methyltransferase" title="Catechol-O-methyltransferase">COMT</a></span></div> <div id="annotation_250x350" style="position:absolute; left:250px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">DBH</a></span></div> <div id="annotation_360x185" style="position:absolute; left:360px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">DBH</a></span></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><span typeof="mw:File"><span title="The image above contains clickable links"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/20px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/40px-Interactive_icon.svg.png 1.5x" data-file-width="133" data-file-height="200" /></span></span></div>In humans, catecholamines and phenethylaminergic trace amines are produced from the amino acid phenylalanine. Abbreviations: DBH: Dopamine β-hydroxylase; AADC: Aromatic <small>L</small>-amino acid decarboxylase; AAAH: (Biopterin-dependent) aromatic amino acid hydroxylase; COMT: Catechol <i>O</i>-methyltransferase; PNMT: Phenylethanolamine <i>N</i>-methyltransferase</div> </div> </div> </td></tr></tbody></table> <p><br /> </p> <div class="mw-heading mw-heading2"><h2 id="Presence_in_nutritional/dietary_supplements"><span id="Presence_in_nutritional.2Fdietary_supplements"></span>Presence in nutritional/dietary supplements</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=6" title="Edit section: Presence in nutritional/dietary supplements"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some dietary supplements, sold for the purposes of promoting weight-loss or providing energy, contain synephrine as one of several constituents. Usually, the synephrine is present as a natural component of <i>Citrus aurantium</i> ("bitter orange"), bound up in the plant matrix, but could also be of synthetic origin, or a purified phytochemical (i.e. extracted from a plant source and purified to chemical homogeneity).<sup id="cite_ref-Blum_19-1" class="reference"><a href="#cite_note-Blum-19"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sant_39-0" class="reference"><a href="#cite_note-Sant-39"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> The concentration range found by Santana and co-workers in five different supplements purchased in the US was about 5–14 mg/g.<sup id="cite_ref-Sant_39-1" class="reference"><a href="#cite_note-Sant-39"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmaceutical_use">Pharmaceutical use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=7" title="Edit section: Pharmaceutical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As a synthetic drug, synephrine first appeared in Europe in the late 1920s, under the name of <i>Sympatol</i>. One of the earliest papers describing its pharmacological and toxicological properties was written by Lasch, who obtained it from the Viennese company Syngala.<sup id="cite_ref-Las_41-0" class="reference"><a href="#cite_note-Las-41"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> By 1930, <i>Sympatol</i> was referred to as a Boehringer product,<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> while one of the first US Patents describing its preparation and use was assigned to Frederick Stearns & Co. in 1933.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Despite the date of this patent, clinical and pharmacological research on synephrine obtained from Frederick Stearns & Co was being carried out in the US by 1930.<sup id="cite_ref-Stock_44-0" class="reference"><a href="#cite_note-Stock-44"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Tain_45-0" class="reference"><a href="#cite_note-Tain-45"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Writing in 1931, Hartung reported that in 1930 the Council on Pharmacy and Chemistry of the American Medical Association had accepted synephrine for inclusion in its list of “New and Non-Official Remedies” as an agent for the treatment, by either oral or parenteral administration, "of attacks of hay fever, asthma, coughing, spasms of asthma and pertussis (whooping cough)."<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hart_47-0" class="reference"><a href="#cite_note-Hart-47"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> However, synephrine was dropped from the council's list in 1934, and its apparent re-advertising as a new drug by the Stearns company ten years later elicited a scathing comment from the Editors of the Journal of the American Medical Association.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> The third edition (1965) of <i>Drill's Pharmacology in Medicine</i> stated, with reservations, that synephrine was "advertised as an antihistaminic to be used in the treatment of the common cold...", under the trade name of "Synephrin Tartrate", and indicated that the dose was 100 mg, given intramuscularly, or subcutaneously.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> Published in 1966, the <i>Textbook of Organic Medicinal and Pharmaceutical Chemistry</i> described synephrine (in the form of its racemic tartrate) as a sympathomimetic agent that was "less effective than epinephrine", and which had been used for the treatment of chronic <a href="/wiki/Hypotension" title="Hypotension">hypotension</a>, collapse due to shock, and other conditions leading to <a href="/wiki/Hypotension" title="Hypotension">hypotension</a>.<sup id="cite_ref-Wil_50-0" class="reference"><a href="#cite_note-Wil-50"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> In a later (1972) textbook, synephrine was described as a drug, sold in Europe, that was administered in situations involving shock, such as surgical or <a href="/wiki/Bacteremic" class="mw-redirect" title="Bacteremic">bacteremic</a> shock, and <a href="/wiki/Spinal_anesthesia" class="mw-redirect" title="Spinal anesthesia">spinal anesthesia</a>-related shock. The recommended dose was given here as 25–50 mg, by intravenous, intramuscular or subcutaneous administration.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p><p>There is no mention of synephrine in editions of <i>Drill's Pharmacology in Medicine</i> later than the 3rd, nor is there any reference to synephrine in the 2012 <i><a href="/wiki/Physicians%27_Desk_Reference" title="Physicians' Desk Reference">Physicians' Desk Reference</a></i>, nor in the current <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">FDA</a> <a href="/wiki/Approved_Drug_Products_with_Therapeutic_Equivalence_Evaluations" title="Approved Drug Products with Therapeutic Equivalence Evaluations">"Orange Book"</a>. </p><p>One current reference source describes synephrine as a vasoconstrictor that has been given to hypotensive patients, orally or by injection, in doses of 20–100 mg.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>One website from a healthcare media company, accessed in February, 2013, refers to oxedrine as being indicated for <a href="/wiki/Hypotensive" class="mw-redirect" title="Hypotensive">hypotensive</a> states, in oral doses of 100–150 mg <a href="/wiki/List_of_abbreviations_used_in_medical_prescriptions" title="List of abbreviations used in medical prescriptions">tid</a>, and as a "<a href="/wiki/Conjunctiva" title="Conjunctiva">conjunctival</a> decongestant" to be topically applied as a 0.5% solution.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> However, no supporting references are provided. </p> <div class="mw-heading mw-heading2"><h2 id="Names">Names</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=8" title="Edit section: Names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There has been some confusion about the biological effects of synephrine because of the similarity of this un-prefixed name to the names <i>m-synephrine</i>, <i>Meta-synephrine</i> and <i>Neosynephrine</i>, all of which refer to a related drug and naturally-occurring <a href="/wiki/Amine" title="Amine">amine</a> more commonly known as <a href="/wiki/Phenylephrine" title="Phenylephrine">phenylephrine</a>. Although there are chemical and pharmacological similarities between synephrine and phenylephrine, they are nevertheless different substances. The confusion is compounded by the fact that synephrine has been marketed as a drug under numerous different names, including <i>Sympatol</i>, <i>Sympathol</i>, <i>Synthenate</i>, and <i>oxedrine</i>, while phenylephrine has also been called <i>m-Sympatol</i>. The synephrine with which this article deals is sometimes referred to as <i>p-synephrine</i> in order to distinguish it from its positional isomers, <i>m</i>-synephrine and <i>o</i>-synephrine. A comprehensive listing of alternative names for synephrine may be found in the ChemSpider entry (see Chembox, at right). Confusion exists over the distinctions between <i>p</i>- and <i>m</i>-synephrine.<sup id="cite_ref-G._Rossato,_V._M_2011_54-0" class="reference"><a href="#cite_note-G._Rossato,_V._M_2011-54"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> However, an examination of the references cited in support of this statement show that all the evidence for the presence of <i>m</i>-synephrine in <i>C. aurantium</i> derives from a report by Penzak and co-workers,<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> whose Abstract states that <i>m</i>-synephrine was found in <i>C. aurantium</i>, whereas a close reading of the text of the paper itself reveals that the authors (although apparently uncertain about which synephrine regio-isomer had been found in the plant by earlier investigators) were aware that their analytical technique could not distinguish between <i>m</i>- and <i>p</i>-synephrine, and did <i>not</i> claim that <i>m</i>-synephrine was present. Thus the Abstract is at variance with the experimental findings given in the full text of the paper, but this error has propagated through subsequent publications. Even the name "<i>p</i>-synephrine" is not unambiguous, since it does not specify stereochemistry. The only completely unambiguous names for synephrine are: (<i>R</i>)-(−)-4-[1-hydroxy-2-(methylamino)ethyl]phenol (for the l-enantiomer); (<i>S</i>)-(+)-4-[1-hydroxy-2-(methylamino)ethyl]phenol (for the d-enantiomer); and (<i>R</i>,<i>S</i>)-4-[1-hydroxy-2-(methylamino)ethyl]phenol (for the racemate, or d,l-synephrine) (see <a href="#Chemistry">Chemistry</a> section). </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=9" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Properties">Properties</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=10" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In terms of molecular structure, synephrine has a <a href="/wiki/Phenethylamine" title="Phenethylamine">phenethylamine</a> skeleton, with a <a href="/wiki/Phenol" title="Phenol">phenolic</a> <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxy</a>- group, an <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcoholic</a> hydroxy- group, and an <i>N</i>-methylated <a href="/wiki/Amino" class="mw-redirect" title="Amino">amino</a>-group. Alternatively, synephrine might be described as a <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">phenylethanolamine</a> with an <i>N</i>-methyl and <i>p</i>-hydroxy substituent. The amino-group confers basic properties on the molecule, whereas the phenolic –OH group is weakly acidic: the apparent (see original article for discussion) pK<sub>a</sub>s for protonated synephrine are 9.55 (phenolic H) and 9.79 (ammonium H).<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p><p>Common salts of <a href="/wiki/Racemic" class="mw-redirect" title="Racemic">racemic</a> synephrine are its <a href="/wiki/Hydrochloride" title="Hydrochloride">hydrochloride</a>, C<sub>9</sub>H<sub>13</sub>NO<sub>2</sub>.HCl, m.p. 150–152°,<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> the <a href="/wiki/Oxalate" title="Oxalate">oxalate</a> (C<sub>9</sub>H<sub>13</sub>NO<sub>2</sub>)<sub>2</sub>.C<sub>2</sub>H<sub>2</sub>O<sub>4</sub>, m.p. 221–222 °C,<sup id="cite_ref-Stew_4-1" class="reference"><a href="#cite_note-Stew-4"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> and the <a href="/wiki/Tartrate" title="Tartrate">tartrate</a> (Sympatol), (C<sub>9</sub>H<sub>13</sub>NO<sub>2</sub>)<sub>2</sub>.C<sub>4</sub>H<sub>6</sub>O<sub>6</sub>, m.p. 188–190 °C.<sup id="cite_ref-Wil_50-1" class="reference"><a href="#cite_note-Wil-50"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p><p>The presence of the hydroxy-group on the <a href="/wiki/Benzylic" class="mw-redirect" title="Benzylic">benzylic</a> C of the synephrine molecule creates a <a href="/wiki/Chiral_center" class="mw-redirect" title="Chiral center">chiral center</a>, so the compound exists in the form of two <a href="/wiki/Enantiomers" class="mw-redirect" title="Enantiomers">enantiomers</a>, d- and l- synephrine, or as the <a href="/wiki/Racemic_mixture" title="Racemic mixture">racemic mixture</a>, d,l- synephrine. The <a href="/wiki/Dextrorotatory" class="mw-redirect" title="Dextrorotatory">dextrorotatory</a> d-isomer corresponds to the <a href="/wiki/Cahn%E2%80%93Ingold%E2%80%93Prelog_priority_rules" title="Cahn–Ingold–Prelog priority rules">(<i>S</i>)-configuration</a>, and the <a href="/wiki/Levorotatory" class="mw-redirect" title="Levorotatory">levorotatory</a> l-isomer to the <a href="/wiki/Cahn%E2%80%93Ingold%E2%80%93Prelog_priority_rules" title="Cahn–Ingold–Prelog priority rules">(<i>R</i>)-configuration</a>.<sup id="cite_ref-Midg_59-0" class="reference"><a href="#cite_note-Midg-59"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p>Racemic synephrine has been resolved using ammonium 3-bromo-camphor-8-sulfonate.<sup id="cite_ref-Pellat_12-1" class="reference"><a href="#cite_note-Pellat-12"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Midg_59-1" class="reference"><a href="#cite_note-Midg-59"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> The enantiomers were not characterized as their free bases, but converted to the hydrochloride salts, with the following properties:<sup id="cite_ref-Midg_59-2" class="reference"><a href="#cite_note-Midg-59"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p>(<i>S</i>)-(+)-C<sub>9</sub>H<sub>13</sub>NO<sub>2</sub>.HCl: m.p. 178 °C; [α] = +42.0°, c 0.1 (H<sub>2</sub>O); (<i>R</i>)-(−)-C<sub>9</sub>H<sub>13</sub>NO<sub>2</sub>.HCl: m.p. 176 °C; [α] = −39.0°, c 0.2 (H<sub>2</sub>O) </p><p>(−)-Synephrine, as the free base isolated from a <i>Citrus</i> source, has m.p. 162–164 °C (with decomposition).<sup id="cite_ref-Stew_4-2" class="reference"><a href="#cite_note-Stew-4"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Stew2_5-1" class="reference"><a href="#cite_note-Stew2-5"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged December 2013">dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup> </p><p>The <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray structure</a> for synephrine has been determined.<sup id="cite_ref-Midg_59-3" class="reference"><a href="#cite_note-Midg-59"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=11" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Early and seemingly inefficient syntheses of synephrine were discussed by Priestley and Moness, writing in 1940.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> These chemists optimized a route beginning with the <i>O</i>-benzoylation of <i>p</i>-hydroxy-phenacyl chloride, followed by reaction of the resulting <i>O</i>-protected chloride with <i>N</i>-methyl-benzylamine to give an amino-ketone. This intermediate was then hydrolyzed with HCl/alcohol to the <i>p</i>-hydroxy-aminoketone, and the product then reduced catalytically to give (racemic) synephrine. </p><p>A later synthesis, due to Bergmann and Sulzbacher, began with the <i>O</i>-benzylation of <i>p</i>-hydroxy-benzaldehyde, followed by a <a href="/wiki/Reformatsky_reaction" title="Reformatsky reaction">Reformatskii reaction</a> of the protected aldehyde with ethyl bromoacetate/Zn to give the expected β-hydroxy ester. This intermediate was converted to the corresponding acylhydrazide with hydrazine, then the acylhydrazide reacted with HNO<sub>2</sub>, ultimately yielding the <i>p</i>-benzyloxy-phenyloxazolidone. This was <i>N</i>-methylated using <a href="/wiki/Dimethyl_sulfate" title="Dimethyl sulfate">dimethyl sulfate</a>, then hydrolyzed and <i>O</i>-debenzylated by heating with HCl, to give racemic synephrine.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Structural_relationships">Structural relationships</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=12" title="Edit section: Structural relationships"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Much reference has been made in the literature (both lay and professional) of the structural kinship of synephrine with <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>, or with <a href="/wiki/Phenylephrine" title="Phenylephrine">phenylephrine</a>, often with the implication that the perceived similarities in structure should result in similarities in pharmacological properties. However, from a chemical perspective, synephrine is also related to a very large number of other drugs whose structures are based on the phenethylamine skeleton, and although some properties are common, others are not, making unqualified comparisons and generalizations inappropriate. </p><p>Thus, replacement of the <i>N</i>-<a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> group in synephrine with a hydrogen atom gives <a href="/wiki/Octopamine" title="Octopamine">octopamine</a>; replacement of the β-<a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxy</a> group in synephrine by a H atom gives <a href="/wiki/N-methyltyramine" class="mw-redirect" title="N-methyltyramine"><i>N</i>-methyltyramine</a>; replacement of the synephrine <a href="/wiki/Phenol" title="Phenol">phenolic</a> 4-OH group by a –H gives <a href="/wiki/Halostachine" title="Halostachine">halostachine</a>. </p><p>If the synephrine phenolic 4-OH group is shifted to the <i>meta</i>-, or 3-position on the benzene ring, the compound known as phenylephrine (or <i>m</i>-synephrine, or "Neo-synephrine") results; if the same group is shifted to the <i>ortho</i>-, or 2-position on the ring, <i>o</i>-synephrine results. </p><p>Addition of another phenolic –OH group to the 3-position of the benzene ring produces the <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a>; addition of a <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> group to the α-position in the side-chain of synephrine gives <a href="/wiki/Oxilofrine" title="Oxilofrine">oxilofrine</a> (methylsynephrine). Four stereoisomers (two pairs of enantiomers) are possible for this substance. </p><p>Extension of the synephrine <i>N</i>-methyl substituent by one <a href="/wiki/Methylene_bridge" title="Methylene bridge">methylene</a> unit to an <i>N</i>-<a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a> gives the <a href="/wiki/Hypotensive" class="mw-redirect" title="Hypotensive">hypotensive</a> experimental drug "Sterling #573"/"Aethyl-Sympatol".<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </p><p>The above structural relationships all involve a change at <i>one</i> position in the synephrine molecule, and numerous other similar changes, many of which have been explored, are possible. However, the structure of ephedrine differs from that of synephrine at <i>two</i> different positions: ephedrine has no substituent on the phenyl ring where synephrine has a 4-OH group, and ephedrine has a methyl group on the position α- to the N in the side-chain, where syneprine has only a H atom. Furthermore, "synephrine" exists as either of two enantiomers, while "ephedrine" exists as one of four different enantiomers; there are, in addition, racemic mixtures of these enantiomers. </p><p>The main differences of the synephrine isomers compared for example to the <a href="/wiki/Ephedrine" title="Ephedrine">ephedrines</a> are the hydroxy-substitutions on the benzene ring. Synephrines are direct sympathomimetic drugs while the ephedrines are both direct and indirect sympathomimetics. One of the main reasons for these differential effects is the obviously increased polarity of the hydroxy-substituted phenyl ethyl amines which renders them less able to penetrate the blood-brain barrier as illustrated in the examples for tyramine and the amphetamine analogs.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=13" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Synopsis">Synopsis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=14" title="Edit section: Synopsis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Classical pharmacological studies on animals and isolated animal tissues showed that the principal actions of parenterally-administered synephrine included raising blood-pressure, dilating the pupil, and constricting peripheral blood vessels. </p><p>There is now ample evidence<sup>(what evidence?)</sup> that synephrine produces most of its biological effects by acting as an <a href="/wiki/Agonist" title="Agonist">agonist</a> (i.e. stimulating) at adrenergic receptors, with a distinct preference for the α<sub>1</sub> over the α<sub>2</sub> sub-type. However, the potency of synephrine at these receptors is relatively low (i.e. relatively large concentrations of the drug are required to activate them). The potency of synephrine at adrenergic receptors of the β-class (regardless of sub-type) is much lower than at α-receptors. There is some evidence that synephrine also has weak activity at <a href="/wiki/5-HT_receptors" class="mw-redirect" title="5-HT receptors">5-HT receptors</a>, and that it interacts with <a href="/wiki/TAAR1" title="TAAR1">TAAR1</a> (trace amine-associated receptor 1). </p><p>In common with virtually all other simple phenylethanolamines (β-hydroxy-phenethylamines), the (<i>R</i>)-(−)-, or l-, enantiomer of synephrine is more potent than the (<i>S</i>)-(+)-, or d-, enantiomer in most, but not all preparations studied. However, the majority of studies have been conducted with a racemic mixture of the two enantiomers. </p><p>Since the details regarding such variables as test species, receptor source, route of administration, drug concentration, and stereochemical composition are important but often incomplete in other Reviews and Abstracts of research publications, many are provided in the more technical review below, in order to support as fully as possible the broad statements made in this Synopsis. </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacology_research">Pharmacology research</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=15" title="Edit section: Pharmacology research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pharmacological studies on synephrine date back to the late 1920s, when it was observed that injected synephrine raised blood pressure, constricted peripheral blood vessels, dilated pupils, stimulated the uterus, and relaxed the intestines in experimental animals.<sup id="cite_ref-Las_41-1" class="reference"><a href="#cite_note-Las-41"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> Representative of this early work is the paper by Tainter and Seidenfeld, who were the first researchers to systematically compare the different effects of the two synephrine enantiomers, d- and l- synephrine, as well as of the racemate, d,l-synephrine, in various animal assays.<sup id="cite_ref-Tain_45-1" class="reference"><a href="#cite_note-Tain-45"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> In experiments on anesthetized cats, Tainter and Seidenfeld confirmed earlier reports of the increase in blood pressure produced by intravenous doses of synephrine, showing that the median <a href="/wiki/Pressor" class="mw-redirect" title="Pressor">pressor</a> doses for the isomers were: l-synephrine: 0.5 mg/kg; d,l-synephrine: 1.0 mg/kg; and d-synephrine: 2–20 mg/kg. These effects lasted 2–3 minutes, peaking at ~30 seconds after administration. l-Synephrine was thus the more potent enantiomer, with about 1/60x the potency of the standard pressor l-epinephrine in the same assay. A later study, by Lands and Grant, showed that a dose of ~0.6 mg/kg of racemic synephrine, given intravenously to anesthetized dogs, produced a rise in blood pressure of 34 mmHg lasting 5–10 minutes, and estimated that this pressor activity was about 1/300x that of epinephrine.<sup id="cite_ref-Lands_67-0" class="reference"><a href="#cite_note-Lands-67"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p><p>Using cats and dogs, Tainter and Seidenfeld observed that neither d- nor l-synephrine caused any changes in the tone of normal <a href="/wiki/Bronchi" class="mw-redirect" title="Bronchi">bronchi</a>, <i>in situ</i>, even at "maximum" doses. Furthermore, the marked brocho-constriction produced by injections of <a href="/wiki/Histamine" title="Histamine">histamine</a> was not reversed by either l-synephrine or d,l-synephrine.<sup id="cite_ref-Tain_45-2" class="reference"><a href="#cite_note-Tain-45"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>In experiments with isolated sheep <a href="/wiki/Carotid" class="mw-redirect" title="Carotid">carotid</a> artery, d-, l- and d,l-synephrine all showed some <a href="/wiki/Vasoconstrictor" class="mw-redirect" title="Vasoconstrictor">vasoconstrictor</a> activity: l-synephrine was the most potent, producing strong contractions at a concentration of 1:10000.<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>e<span class="cite-bracket">]</span></a></sup> d-Synephrine was about 1/2 as potent as the l-isomer, but d,l-synephrine (which would have been expected to have a potency of 1/2 that of l-synephrine even if the d-isomer were completely inactive) did not produce significant and irregular contractions until a concentration of 1:2500<sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span class="cite-bracket">[</span>f<span class="cite-bracket">]</span></a></sup>had been reached, implying an inhibitory interaction between the two enantiomers.<sup id="cite_ref-Tain_45-3" class="reference"><a href="#cite_note-Tain-45"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>Qualitatively similar results were obtained in a rabbit ear preparation: 25 mg l-synephrine produced significant (50%) vasoconstriction, while the same concentration of d-synephrine elicited essentially no response. In contrast, d,l-synephrine did not produce any constriction up to 25 mg, but 25 – 50 mg caused a relaxation of the blood vessels, which again suggested that the d-isomer might be inhibiting the action of the l-isomer.<sup id="cite_ref-Tain_45-4" class="reference"><a href="#cite_note-Tain-45"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>Experiments on strips of rabbit <a href="/wiki/Duodenum" title="Duodenum">duodenum</a> showed that l-synephrine caused a modest reduction in contractions at a concentration of 1:17000,<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>g<span class="cite-bracket">]</span></a></sup> but that the effects of the d- and d,l- forms were much weaker.<sup id="cite_ref-Tain_45-5" class="reference"><a href="#cite_note-Tain-45"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>Racemic synephrine, given intramuscularly, or by instillation, was found to significantly reduce the inflammation caused by instillation of <a href="/wiki/Mustard_oil" title="Mustard oil">mustard oil</a> into the eyes of rabbits.<sup id="cite_ref-Tain_45-6" class="reference"><a href="#cite_note-Tain-45"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>Subcutaneous injection of racemic synephrine into rabbits was reported to cause a large rise in <a href="/wiki/Blood_sugar" class="mw-redirect" title="Blood sugar">blood sugar</a>.<sup id="cite_ref-Hart_47-1" class="reference"><a href="#cite_note-Hart-47"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p><p>In experiments on anesthetized cats, Papp and Szekeres found that synephrine (stereochemistry unspecified) raised the thresholds for auricular and ventricular <a href="/wiki/Fibrillation" title="Fibrillation">fibrillation</a>, an indication of <a href="/wiki/Anti-arrhythmic" class="mw-redirect" title="Anti-arrhythmic">anti-arrhythmic</a> properties.<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p><p>Evidence that synephrine might have some <a href="/wiki/Central_nervous_system" title="Central nervous system">central</a> effects comes from the research of Song and co-workers, who studied the effects of synephrine in mouse models<sup id="cite_ref-72" class="reference"><a href="#cite_note-72"><span class="cite-bracket">[</span>h<span class="cite-bracket">]</span></a></sup> of anti-depressant activity.<sup id="cite_ref-73" class="reference"><a href="#cite_note-73"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> These researchers observed that oral doses of 0.3 – 10 mg/kg of racemic synephrine were effective in shortening the duration of immobility<sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span class="cite-bracket">[</span>i<span class="cite-bracket">]</span></a></sup> produced in the assays, but did not cause any changes in spontaneous motor activity in separate tests. This characteristic immobility could be counteracted by the pre-administration of <a href="/wiki/Prazosin" title="Prazosin">prazosin</a>.<sup id="cite_ref-75" class="reference"><a href="#cite_note-75"><span class="cite-bracket">[</span>j<span class="cite-bracket">]</span></a></sup> Subsequent experiments using the individual enanatiomers of synephrine revealed that although the d-isomer significantly reduced the duration of immobility in the tail suspension test, at an oral dose of 3 mg/kg, the l-isomer had no effect at the same dose. In mice pre-treated with <a href="/wiki/Reserpine" title="Reserpine">reserpine</a>,<sup id="cite_ref-76" class="reference"><a href="#cite_note-76"><span class="cite-bracket">[</span>k<span class="cite-bracket">]</span></a></sup> an oral dose of 0.3 mg/kg d-synephrine significantly reversed the <a href="/wiki/Hypothermia" title="Hypothermia">hypothermia</a>, while l-synephrine required a dose of 1 mg/kg to be effective. Experiments with slices of <a href="/wiki/Cerebral_cortex" title="Cerebral cortex">cerebral cortex</a> taken from rat brain showed that d-synephrine inhibited the uptake of [<sup>3</sup>H]-norepinephrine with an IC<sub>50</sub> = 5.8 μM; l-synephrine was less potent (IC<sub>50</sub> = 13.5 μM). d-Synephrine also competitively inhibited the binding of <a href="/wiki/Nisoxetine" title="Nisoxetine">nisoxetine</a><sup id="cite_ref-77" class="reference"><a href="#cite_note-77"><span class="cite-bracket">[</span>l<span class="cite-bracket">]</span></a></sup> to rat brain cortical slices, with a K<sub>i</sub> = 4.5 μM; l-synephrine was less potent (K<sub>i</sub> = 8.2 μM). In experiments on the release of [<sup>3</sup>H]-norepinephrine from rat brain cortical slices, however, the l-isomer of synephrine was a more potent enhancer of the release (EC<sub>50</sub> = 8.2 μM) than the d-isomer (EC<sub>50</sub> = 12.3 μM). This enhanced release by l-synephrine was blocked by nisoxetine.<sup id="cite_ref-78" class="reference"><a href="#cite_note-78"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> </p><p>Burgen and Iversen, examining the effect of a broad range of phenethylamine-based drugs on [<sup>14</sup>C]-norepinephrine-uptake in the isolated rat heart, observed that racemic synephrine<sup id="cite_ref-79" class="reference"><a href="#cite_note-79"><span class="cite-bracket">[</span>m<span class="cite-bracket">]</span></a></sup> was a relatively weak inhibitor (IC<sub>50</sub> = 0.12 μM) of the uptake.<sup id="cite_ref-80" class="reference"><a href="#cite_note-80"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> </p><p>Another receptor-oriented study by Wikberg revealed that synephrine (<a href="/wiki/Stereochemistry" title="Stereochemistry">stereochemistry</a> unspecified) was a more potent agonist at guinea pig <a href="/wiki/Aorta" title="Aorta">aorta</a> α<sub>1</sub> receptors (pD<sub>2</sub> = 4.81) than at <a href="/wiki/Ileum" title="Ileum">ileum</a> α<sub>2</sub> receptors (pD<sub>2</sub> = 4.48), with a relative affinity ratio of α<sub>2</sub>/α<sub>1</sub> = 0.10. Although clearly indicating a selectivity of synephrine for α<sub>1</sub> receptors, its potency at this receptor sub-class is still relatively low, in comparison with that of phenylephrine (pD<sub>2</sub> at α<sub>1</sub> = 6.32).<sup id="cite_ref-81" class="reference"><a href="#cite_note-81"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p><p>Brown and co-workers examined the effects of the individual enantiomers of synephrine on α<sub>1</sub> receptors in rat <a href="/wiki/Aorta" title="Aorta">aorta</a>, and on α<sub>2</sub> receptors in rabbit <a href="/wiki/Great_saphenous_vein" title="Great saphenous vein">saphenous</a> vein. In the aorta preparation, l-synephrine gave a pD<sub>2</sub> = 5.38 (potency relative to norepinephrine = 1/1000), while d-synephrine had a pD<sub>2</sub> = 3.50 (potency relative to norepinephrine = 1/50000); in comparison, l-phenylephrine had pD<sub>2</sub> = 7.50 (potency relative to norepinephrine ≃ 1/6). No antagonism of norepinephrine was produced by concentrations of l-synephrine up to 10<sup>−6</sup> M. In the rabbit saphenous assay, the pD<sub>2</sub> of l-synephrine was 4.36 (potency relative to norepinephrine ≃ 1/1700), and that of d-synephrine was < 3.00; in comparison, l-phenylephrine had pD<sub>2</sub> = 5.45 (potency relative to norepinephrine ≃ 1/140). No antagonism of norepinephrine was produced by concentrations of l-synephrine up to 10<sup>−5</sup> M.<sup id="cite_ref-Brown_82-0" class="reference"><a href="#cite_note-Brown-82"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> </p><p>A study of the effects of synephrine (stereochemistry unspecified) on strips of guinea pig aorta and on the field-stimulated guinea pig <a href="/wiki/Ileum" title="Ileum">ileum</a> showed that synephrine had an agonist potency of −logK<sub>a</sub> = 3.75 in the aorta assay. In comparison, epinephrine had a potency of −logK<sub>a</sub> = 5.70. There was no significant effect on the ileum at synephrine concentrations up to about 2 × 10<sup>−4</sup> M, indicating selectivity for the α<sub>1</sub> receptor, but relatively low potency.<sup id="cite_ref-83" class="reference"><a href="#cite_note-83"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> </p><p>In binding experiments with central adrenergic receptors, using a preparation from rat cerebral cortex, l-synephrine had pIC<sub>50</sub> = 3.35, and d-synephrine had pIC<sub>50</sub> = 2.42 in competition against [<sup>3</sup>H]-<a href="/wiki/Prazosin" title="Prazosin">prazosin</a> (standard α<sub>1</sub> ligand); against [<sup>3</sup>H]-<a href="/wiki/Yohimbine" title="Yohimbine">yohimbine</a> (standard α<sub>2</sub> ligand), l-synephrine showed a pIC<sub>50</sub> = 5.01, and d-synephrine showed a pIC<sub>50</sub> = 4.17.<sup id="cite_ref-Brown_82-1" class="reference"><a href="#cite_note-Brown-82"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> </p><p>Experiments conducted by Hibino and co-workers also showed that synephrine (stereochemistry unspecified) produced a dose-dependent constriction of isolated rat aorta strips, in the concentration range 10<sup>−5</sup>–3 × 10<sup>−6</sup> M. This constriction was found to be competitively antagonized by prazosin (a standard α<sub>1</sub> antagonist) and <a href="/wiki/Ketanserin" title="Ketanserin">ketanserin</a>,<sup id="cite_ref-84" class="reference"><a href="#cite_note-84"><span class="cite-bracket">[</span>n<span class="cite-bracket">]</span></a></sup> with prazosin being the more potent antagonist (pA<sub>2</sub> = 9.38, vs pA<sub>2</sub> = 8.23 for ketanserin). Synephrine constrictions were also antagonized by <a href="/wiki/BRL-15,572" title="BRL-15,572">BRL-15,572</a>,<sup id="cite_ref-85" class="reference"><a href="#cite_note-85"><span class="cite-bracket">[</span>o<span class="cite-bracket">]</span></a></sup> but not by <a href="/wiki/SB-216,641" class="mw-redirect" title="SB-216,641">SB-216,641</a> (used here as a selective 5-HT<sub>1B</sub> antagonist), or by <a href="/wiki/Propranolol" title="Propranolol">propranolol</a> (a common β antagonist).<sup id="cite_ref-86" class="reference"><a href="#cite_note-86"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> </p><p>In studies on guinea pig <a href="/wiki/Atrium_(heart)" title="Atrium (heart)">atria</a> and <a href="/wiki/Vertebrate_trachea" class="mw-redirect" title="Vertebrate trachea">trachea</a>, Jordan and co-workers also found that synephrine had negligible activity on β<sub>1</sub> and β<sub>2</sub> receptors, being about 40000x less potent than norepinephrine.<sup id="cite_ref-87" class="reference"><a href="#cite_note-87"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> </p><p>Experiments with cultured <a href="/wiki/Adipocytes" class="mw-redirect" title="Adipocytes">white fat cells</a> from several animal species, including human, by Carpéné and co-workers showed that racemic synephrine produced <a href="/wiki/Lipolysis" title="Lipolysis">lipolytic</a> effects, but only at high concentrations (0.1-1 mM). The potency, expressed in terms of pD<sub>2</sub> of synephrine in these species was as follows: rat: 4.38; hamster: 5.32; guinea pig: 4.31; human: 4.94. In comparison, <a href="/wiki/Isoprenaline" title="Isoprenaline">isoprenaline</a> had a pD<sub>2</sub> = 8.29 and norepinephrine had pD<sub>2</sub> = 6.80 in human white fat cells. The lipolytic effect of 1 mM/L of synephrine on rat white fat cells was antagonized by various β-antagonists with the following inhibitory concentrations (IC<sub>50</sub>): <a href="/wiki/Bupranolol" title="Bupranolol">bupranolol</a>:<sup id="cite_ref-88" class="reference"><a href="#cite_note-88"><span class="cite-bracket">[</span>p<span class="cite-bracket">]</span></a></sup> 0.11 μM; CGP-20,712A (β<sub>1</sub> antagonist): 6.09 μM; ICI-118,551 (β<sub>2</sub> antagonist): 3.58 μM; SR-5923A (β<sub>3</sub> antagonist): 17 μM.<sup id="cite_ref-89" class="reference"><a href="#cite_note-89"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> </p><p>The binding of racemic synephrine to cloned human adrenergic receptors has been examined: Ma and co-workers found that synephrine bound to α<sub>1A</sub>, α<sub>2A</sub> and α<sub>2C</sub> with low affinity (pK<sub>i</sub> = 4.11 for α<sub>1A</sub>; 4.44 for α<sub>2A</sub>; 4.61 for α<sub>2C</sub>). Synephrine behaved as a <a href="/wiki/Partial_agonist" title="Partial agonist">partial agonist</a> at α<sub>1A</sub> receptors, but as an antagonist at α<sub>2A</sub> and α<sub>2C</sub> sub-types.<sup id="cite_ref-90" class="reference"><a href="#cite_note-90"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> </p><p>Racemic synephrine has been shown to be an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Trace_amine-associated_receptor_1" class="mw-redirect" title="Trace amine-associated receptor 1">TAAR1</a>,<sup id="cite_ref-pmid15860375_91-0" class="reference"><a href="#cite_note-pmid15860375-91"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> although its potency at the human TAAR1 is relatively low (EC<sub>50</sub> = 23700 nM; E<sub>max</sub> = 81.2%).<sup id="cite_ref-92" class="reference"><a href="#cite_note-92"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacokinetics">Pharmacokinetics</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=16" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The pharmacokinetics of synephrine were studied by Hengstmann and Aulepp, who reported a peak plasma concentration at 1–2 hours, with an elimination half-life (T<sub>1/2</sub>) of ~ 2 hours.<sup id="cite_ref-93" class="reference"><a href="#cite_note-93"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Metabolism">Metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=17" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Studies of the metabolism of synephrine by <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidases</a> derived from rat brain <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a> showed that synephrine was a substrate for <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>, with K<sub>m</sub> = 250 μM and V<sub>max</sub> = 32.6 nM/mg protein/30 minutes; there was some evidence for preferential deamination by MAO-A.<sup id="cite_ref-94" class="reference"><a href="#cite_note-94"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Effects_in_humans">Effects in humans</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=18" title="Edit section: Effects in humans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Medical_citations_needed plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/40px-Ambox_important.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/60px-Ambox_important.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/80px-Ambox_important.svg.png 2x" data-file-width="40" data-file-height="40" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs more <a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">reliable medical references</a> for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a> or relies too heavily on <a href="/wiki/Wikipedia:Primary_sources" class="mw-redirect" title="Wikipedia:Primary sources">primary sources</a></b>.<span class="hide-when-compact"> Please review the contents of the section and <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Synephrine&action=edit">add the appropriate references</a> if you can. Unsourced or poorly sourced material may be challenged and <a href="/wiki/Wikipedia:Verifiability#Burden_of_evidence" title="Wikipedia:Verifiability">removed</a>. <small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22Synephrine%22">"Synephrine"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22Synephrine%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22Synephrine%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22Synephrine%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Synephrine%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Synephrine%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">January 2014</span>)</i></span></div></td><td class="mbox-imageright"><div class="mbox-image-div"><span typeof="mw:File"><span><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Star_of_life.svg/60px-Star_of_life.svg.png" decoding="async" width="52" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Star_of_life.svg/120px-Star_of_life.svg.png 1.5x" data-file-width="198" data-file-height="192" /></span></span></div></td></tr></tbody></table> <p>A number of studies of the effects of synephrine in humans, most of them focusing on its cardiovascular properties, have been performed since its introduction as a synthetic drug around 1930.<sup id="cite_ref-Stock_44-1" class="reference"><a href="#cite_note-Stock-44"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-95" class="reference"><a href="#cite_note-95"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-96" class="reference"><a href="#cite_note-96"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-97" class="reference"><a href="#cite_note-97"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-98" class="reference"><a href="#cite_note-98"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hoff_99-0" class="reference"><a href="#cite_note-Hoff-99"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> The paper by Stockton and co-workers is representative, describing the effects of racemic synephrine in humans with particular attention to differences resulting from different routes of administration. Thus, it was shown by these investigators that <i>intramuscular</i> injections (average effective dose = 200 mg) of the drug produced an increase in <a href="/wiki/Systole_(medicine)" class="mw-redirect" title="Systole (medicine)">systolic</a> blood pressure and pulse rate, without affecting the <a href="/wiki/Diastolic" class="mw-redirect" title="Diastolic">diastolic</a> pressure. The blood pressure increase reached a maximum (~25 mmHg) in 5 minutes following the injection, then gradually returned to normal over the course of 1 hour. Doses of drug greater than 200 mg caused side-effects such as heart palpitations, headache, sweating, and feelings of apprehension. When given <i>intravenously</i>, doses of 25–50 mg sufficed to produce a mean maximum increase in the blood pressure of 29 mmHg in 2 minutes, and a return to baseline within 30 minutes. Respiration was generally not affected during these experiments. <i>Subcutaneous</i> administration of synephrine in doses ≤ 200 mg had no effects on blood pressure or pulse rate. <i>Oral</i> doses of 500–1500 mg of the drug did not affect blood pressure or respiration, but pulse rate was increased by ~12%, and the highest doses caused nausea and vomiting.<sup id="cite_ref-Stock_44-2" class="reference"><a href="#cite_note-Stock-44"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>The i.m. administration of 75–500 mg of synephrine did not relieve acute <a href="/wiki/Asthma" title="Asthma">asthma</a> attacks, contradicting an earlier claim.<sup id="cite_ref-100" class="reference"><a href="#cite_note-100"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> However, the topical application of 1–3% solutions of the drug to the <a href="/wiki/Mucous_membrane_of_nose" class="mw-redirect" title="Mucous membrane of nose">nasal mucosa</a> of patients with <a href="/wiki/Sinusitis" title="Sinusitis">sinusitis</a> did produce a beneficial constriction without local irritation.<sup id="cite_ref-Stock_44-3" class="reference"><a href="#cite_note-Stock-44"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>Administration of synephrine by continuous intravenous infusion, at the rate of 4 mg/minute, significantly increased mean arterial and <a href="/wiki/Systole_(medicine)" class="mw-redirect" title="Systole (medicine)">systolic</a> pressure, but <a href="/wiki/Diastole" title="Diastole">diastolic</a> pressure and heart rate were unaltered.;<sup id="cite_ref-Hoff_99-1" class="reference"><a href="#cite_note-Hoff-99"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> further details of this investigation are summarized in a review by Fugh-Berman and Myers.<sup id="cite_ref-101" class="reference"><a href="#cite_note-101"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> </p><p>There are a number of studies, references to many of which may be found in the review by Stohs and co-workers<sup id="cite_ref-Stohs_102-0" class="reference"><a href="#cite_note-Stohs-102"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup> dealing with the effects produced by dietary supplements and herbal medications that contain synephrine as only one of many different chemical ingredients. These are outside the scope of the present article (see also the "<a href="#Safety/Efficacy/Controversy">Safety/Efficacy/Controversy</a>" sub-section). </p> <div class="mw-heading mw-heading2"><h2 id="Toxicology">Toxicology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=19" title="Edit section: Toxicology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The acute toxicities of racemic synephrine in different animals, reported in terms of "maximum tolerated dose" after s.c administration, were as follows: mouse: 300 mg/kg; rat: 400 mg/kg; guinea pig: 400 mg/kg. "Lethal doses", given s.c., were found to be: mouse: 400 mg/kg; rat: 500 mg/kg; guinea pig: 500 mg/kg.<sup id="cite_ref-Las_41-2" class="reference"><a href="#cite_note-Las-41"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> Another study of this compound,<sup id="cite_ref-103" class="reference"><a href="#cite_note-103"><span class="cite-bracket">[</span>q<span class="cite-bracket">]</span></a></sup> administered i.v. in mice, gave an LD<sub>50</sub> = 270 mg/kg.<sup id="cite_ref-Lands_67-1" class="reference"><a href="#cite_note-Lands-67"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p><p>The "subchronic toxicity" of synephrine was judged to be low in mice, after administration of oral doses of 30 and 300 mg/kg over a period of 28 days. Generally, this treatment did not result in significant alterations in biochemical or hematological parameters, nor in relative organ weights, but some changes were noted in <a href="/wiki/Glutathione" title="Glutathione">glutathione</a> (GSH) concentration, and in the activity of <a href="/wiki/Glutathione_peroxidase" title="Glutathione peroxidase">glutathione peroxidase</a> (GPx).<sup id="cite_ref-104" class="reference"><a href="#cite_note-104"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety/efficacy/controversy"><span id="Safety.2Fefficacy.2Fcontroversy"></span>Safety/efficacy/controversy</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=20" title="Edit section: Safety/efficacy/controversy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There exists considerable controversy about the safety and/or efficacy of <i>synephrine-containing preparations</i>, which are often confused with synephrine alone, sometimes with <i>m</i>-synephrine.<sup id="cite_ref-Blum_19-2" class="reference"><a href="#cite_note-Blum-19"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-G._Rossato,_V._M_2011_54-1" class="reference"><a href="#cite_note-G._Rossato,_V._M_2011-54"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Stohs_102-1" class="reference"><a href="#cite_note-Stohs-102"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-105" class="reference"><a href="#cite_note-105"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-106" class="reference"><a href="#cite_note-106"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-107" class="reference"><a href="#cite_note-107"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-108" class="reference"><a href="#cite_note-108"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-109" class="reference"><a href="#cite_note-109"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-110" class="reference"><a href="#cite_note-110"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-111" class="reference"><a href="#cite_note-111"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-112" class="reference"><a href="#cite_note-112"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-113" class="reference"><a href="#cite_note-113"><span class="cite-bracket">[</span>96<span class="cite-bracket">]</span></a></sup> Furthermore, this body of literature deals with mixtures containing synephrine as only one of several biologically active components, even, in some cases, without explicit confirmation of the presence of synephrine. </p> <div class="mw-heading mw-heading2"><h2 id="Invertebrates">Invertebrates</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=21" title="Edit section: Invertebrates"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In insects, synephrine has been found to be a very potent agonist at many invertebrate <a href="/wiki/Octopamine" title="Octopamine">octopamine</a> receptor preparations, and is even more potent than octopamine at a <a href="/wiki/Locust" title="Locust">locust</a> (<i><a href="/wiki/Schistocerca" title="Schistocerca">Schistocerca</a> americana gregaria</i>) nerve-muscle preparation.<sup id="cite_ref-114" class="reference"><a href="#cite_note-114"><span class="cite-bracket">[</span>97<span class="cite-bracket">]</span></a></sup> Synephrine (racemic) is also more potent than octopamine (racemic) at inducing light-emission in the <a href="/wiki/Firefly" title="Firefly">firefly</a> (<i><a href="/wiki/Photinus" title="Photinus">Photinus</a></i> species) light organ.<sup id="cite_ref-115" class="reference"><a href="#cite_note-115"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup> Synephrine exhibits similarly high potency in stimulating <a href="/wiki/Adenylate_cyclase" class="mw-redirect" title="Adenylate cyclase">adenylate cyclase</a> activity and in decreasing clotting time in <a href="/wiki/Lobster" title="Lobster">lobster</a> (<i><a href="/wiki/Homarus_americanus" class="mw-redirect" title="Homarus americanus">Homarus americanus</a></i>) hematocytes.<sup id="cite_ref-116" class="reference"><a href="#cite_note-116"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup> Racemic synephrine was found to increase <a href="/wiki/Cyclic_adenosine_monophosphate" title="Cyclic adenosine monophosphate">cAMP</a> in the abdominal epidermis of the blood-sucking bug, <i><a href="/wiki/Rhodnius_prolixus" title="Rhodnius prolixus">Rhodnius prolixus</a></i>.<sup id="cite_ref-117" class="reference"><a href="#cite_note-117"><span class="cite-bracket">[</span>100<span class="cite-bracket">]</span></a></sup> Rachinsky reported that synephrine was equipotent with octopamine in stimulating JH (<a href="/wiki/Juvenile_hormone" title="Juvenile hormone">juvenile hormone</a>) release in the <a href="/wiki/Corpora_allata" class="mw-redirect" title="Corpora allata">corpora allata</a> of <a href="/wiki/Honey_bee" title="Honey bee">honey bee</a> (<i><a href="/wiki/Apis_mellifera" class="mw-redirect" title="Apis mellifera">Apis mellifera</a></i>),<sup id="cite_ref-118" class="reference"><a href="#cite_note-118"><span class="cite-bracket">[</span>101<span class="cite-bracket">]</span></a></sup> but Woodring and Hoffmann found that synephrine had no effect on the synthesis of <a href="/wiki/Juvenile_hormone" title="Juvenile hormone">JH III</a>, in <i>in vitro</i> preparations from the cricket, <i><a href="/wiki/Gryllus_bimaculatus" title="Gryllus bimaculatus">Gryllus bimaculatus</a></i>.<sup id="cite_ref-119" class="reference"><a href="#cite_note-119"><span class="cite-bracket">[</span>102<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Footnotes">Footnotes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=22" title="Edit section: Footnotes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-lower-alpha"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text">Synephrine does however not appear in the current FDA <a href="/wiki/Approved_Drug_Products_with_Therapeutic_Equivalence_Evaluations" title="Approved Drug Products with Therapeutic Equivalence Evaluations">"Orange Book"</a> or the 2012 <i><a href="/wiki/Physicians%27_Desk_Reference" title="Physicians' Desk Reference">Physicians' Desk Reference</a></i>.</span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text">About 1.0–0.02 mg/serving, based on a serving size of ~20g.</span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text">About 1.0–0.1 mg/serving.</span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text">Corresponding to roughly 1–15 mg/serving, assuming a 1-cup or 250 mL serving size.</span> </li> <li id="cite_note-68"><span class="mw-cite-backlink"><b><a href="#cite_ref-68">^</a></b></span> <span class="reference-text">~ 5 x 10<sup>−4</sup>M.</span> </li> <li id="cite_note-69"><span class="mw-cite-backlink"><b><a href="#cite_ref-69">^</a></b></span> <span class="reference-text">~ 2 x 10<sup>−3</sup>M.</span> </li> <li id="cite_note-70"><span class="mw-cite-backlink"><b><a href="#cite_ref-70">^</a></b></span> <span class="reference-text">~ 3 × 10<sup>−4</sup>M.</span> </li> <li id="cite_note-72"><span class="mw-cite-backlink"><b><a href="#cite_ref-72">^</a></b></span> <span class="reference-text">Tail suspension and enforced swimming.</span> </li> <li id="cite_note-74"><span class="mw-cite-backlink"><b><a href="#cite_ref-74">^</a></b></span> <span class="reference-text">Ostensibly correlated to anti-depressant activity.</span> </li> <li id="cite_note-75"><span class="mw-cite-backlink"><b><a href="#cite_ref-75">^</a></b></span> <span class="reference-text">An adrenergic antagonist selective for α<sub>1</sub> receptors.</span> </li> <li id="cite_note-76"><span class="mw-cite-backlink"><b><a href="#cite_ref-76">^</a></b></span> <span class="reference-text">Reversal of reserpine-induced hypothermia by a drug is a classical test for potential anti-depressant properties.</span> </li> <li id="cite_note-77"><span class="mw-cite-backlink"><b><a href="#cite_ref-77">^</a></b></span> <span class="reference-text">A selective inhibitor of the <a href="/wiki/Norepinephrine_transporter" title="Norepinephrine transporter">norepinephrine transporter</a>.</span> </li> <li id="cite_note-79"><span class="mw-cite-backlink"><b><a href="#cite_ref-79">^</a></b></span> <span class="reference-text">Referred to here as "oxedrine".</span> </li> <li id="cite_note-84"><span class="mw-cite-backlink"><b><a href="#cite_ref-84">^</a></b></span> <span class="reference-text">A drug often used as a selective 5-HT<sub>2A</sub> antagonist.</span> </li> <li id="cite_note-85"><span class="mw-cite-backlink"><b><a href="#cite_ref-85">^</a></b></span> <span class="reference-text">Used here as a selective 5-HT<sub>1D</sub> antagonist.</span> </li> <li id="cite_note-88"><span class="mw-cite-backlink"><b><a href="#cite_ref-88">^</a></b></span> <span class="reference-text">Used as a non-selective β-antagonist</span> </li> <li id="cite_note-103"><span class="mw-cite-backlink"><b><a href="#cite_ref-103">^</a></b></span> <span class="reference-text">Referred to as "Sympathol".</span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=23" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Halostachine" title="Halostachine">Halostachine</a></li> <li><a href="/wiki/Deterenol" title="Deterenol">Deterenol</a></li> <li><a href="/wiki/Octopamine" title="Octopamine">Octopamine</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Synephrine&action=edit&section=24" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626" /><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFSA" class="citation web cs1">SA, HCI Solutions. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200725033715/https://compendium.ch/fr/product/1092556-neo-synephrine-hcl-inj-los-10-mg-ml/mpro">"Neo-Synephrine HCl - compendium.ch"</a>. <i>compendium.ch</i>. Archived from <a rel="nofollow" class="external text" href="https://compendium.ch/mpro/mnr/22158/html/fr?Platform=Desktop">the original</a> on 2020-07-25<span class="reference-accessdate">. Retrieved <span class="nowrap">2016-03-06</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=compendium.ch&rft.atitle=Neo-Synephrine+HCl+-+compendium.ch&rft.aulast=SA&rft.aufirst=HCI+Solutions&rft_id=https%3A%2F%2Fcompendium.ch%2Fmpro%2Fmnr%2F22158%2Fhtml%2Ffr%3FPlatform%3DDesktop&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWagner_H.,_Ulrich-Merzenich_G.2009" class="citation journal cs1">Wagner H., Ulrich-Merzenich G. (2009). "Synergy research: approaching a new generation of phytopharmaceuticals". <i>Phytomedicine</i>. <b>16</b> (<span class="nowrap">2–</span>3): <span class="nowrap">97–</span>110. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.phymed.2008.12.018">10.1016/j.phymed.2008.12.018</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/19211237">19211237</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:25766699">25766699</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Phytomedicine&rft.atitle=Synergy+research%3A+approaching+a+new+generation+of+phytopharmaceuticals&rft.volume=16&rft.issue=%3Cspan+class%3D%22nowrap%22%3E2%E2%80%93%3C%2Fspan%3E3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E97-%3C%2Fspan%3E110&rft.date=2009&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A25766699%23id-name%3DS2CID&rft_id=info%3Apmid%2F19211237&rft_id=info%3Adoi%2F10.1016%2Fj.phymed.2008.12.018&rft.au=Wagner+H.%2C+Ulrich-Merzenich+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-Stew-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Stew_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Stew_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Stew_4-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFStewart_I.,_Newhall_W._F.,_Edwards_G._J.1964" class="citation journal cs1">Stewart I., Newhall W. F., Edwards G. J. (1964). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2951679-3">"The isolation and identification of synephrine in the leaves and fruit of Citrus"</a>. <i>J. Biol. Chem</i>. <b>239</b> (3): <span class="nowrap">930–</span>932. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2951679-3">10.1016/S0021-9258(18)51679-3</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Biol.+Chem.&rft.atitle=The+isolation+and+identification+of+synephrine+in+the+leaves+and+fruit+of+Citrus&rft.volume=239&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E930-%3C%2Fspan%3E932&rft.date=1964&rft_id=info%3Adoi%2F10.1016%2FS0021-9258%2818%2951679-3&rft.au=Stewart+I.%2C+Newhall+W.+F.%2C+Edwards+G.+J.&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252FS0021-9258%252818%252951679-3&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-Stew2-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-Stew2_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Stew2_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external autonumber" href="http://www.fshs.org/Proceedings/Password%20Protected/1963%20Vol.%2076/242-245%20%28STEWART%29.pdf">[1]</a> <sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged December 2013">dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWheaton_T._A.,_Stewart_I.1970" class="citation journal cs1">Wheaton T. A., Stewart I. (1970). "The distribution of tyramine, N-methyltyramine, hordenine, octopamine and synephrine in higher plants". <i>Lloydia</i>. <b>33</b> (2): <span class="nowrap">244–</span>254. <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/5495514">5495514</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Lloydia&rft.atitle=The+distribution+of+tyramine%2C+N-methyltyramine%2C+hordenine%2C+octopamine+and+synephrine+in+higher+plants&rft.volume=33&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E244-%3C%2Fspan%3E254&rft.date=1970&rft_id=info%3Apmid%2F5495514&rft.au=Wheaton+T.+A.%2C+Stewart+I.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKo_H._C.,_Chen_K._T.,_Chen_C._F.,_Su_J._P.,_Chen_C._M.,_Wang_G._J.2006" class="citation journal cs1">Ko H. C., Chen K. T., Chen C. F., Su J. P., Chen C. M., Wang G. J. (2006). "Chemical and biological comparisons on <i>Evodia</i> with two related species of different locations and conditions". <i>Journal of Ethnopharmacology</i>. <b>108</b> (2): <span class="nowrap">257–</span>263. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.jep.2006.05.020">10.1016/j.jep.2006.05.020</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/16824714">16824714</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Ethnopharmacology&rft.atitle=Chemical+and+biological+comparisons+on+Evodia+with+two+related+species+of+different+locations+and+conditions&rft.volume=108&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E257-%3C%2Fspan%3E263&rft.date=2006&rft_id=info%3Adoi%2F10.1016%2Fj.jep.2006.05.020&rft_id=info%3Apmid%2F16824714&rft.au=Ko+H.+C.%2C+Chen+K.+T.%2C+Chen+C.+F.%2C+Su+J.+P.%2C+Chen+C.+M.%2C+Wang+G.+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSwinehart_J._A.,_Stermitz_F._R.1980" class="citation journal cs1">Swinehart J. A., Stermitz F. R. (1980). "Bishordeninyl terpene alkaloids and other constituents of <i>Zanthoxylum culantrillo</i> and <i>Z. coriaceum</i>". <i>Phytochemistry</i>. <b>19</b> (6): <span class="nowrap">1219–</span>1223. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1980PChem..19.1219S">1980PChem..19.1219S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0031-9422%2880%2983087-1">10.1016/0031-9422(80)83087-1</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Phytochemistry&rft.atitle=Bishordeninyl+terpene+alkaloids+and+other+constituents+of+Zanthoxylum+culantrillo+and+Z.+coriaceum&rft.volume=19&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1219-%3C%2Fspan%3E1223&rft.date=1980&rft_id=info%3Adoi%2F10.1016%2F0031-9422%2880%2983087-1&rft_id=info%3Abibcode%2F1980PChem..19.1219S&rft.au=Swinehart+J.+A.%2C+Stermitz+F.+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKim_S._P.,_Moon_E.,_Nam_S._H.,_Friedman_M.2012" class="citation journal cs1">Kim S. P., Moon E., Nam S. H., Friedman M. (2012). "Composition of Herba Pogostemonis water extract and protection of infected mice against <i>Salmonella typhimurium</i>-induced liver damage and mortality by stimulation of innate immune cells". <i>Journal of Agricultural and Food Chemistry</i>. <b>60</b> (49): <span class="nowrap">12122–</span>12130. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjf304466t">10.1021/jf304466t</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/23186318">23186318</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Agricultural+and+Food+Chemistry&rft.atitle=Composition+of+Herba+Pogostemonis+water+extract+and+protection+of+infected+mice+against+Salmonella+typhimurium-induced+liver+damage+and+mortality+by+stimulation+of+innate+immune+cells&rft.volume=60&rft.issue=49&rft.pages=%3Cspan+class%3D%22nowrap%22%3E12122-%3C%2Fspan%3E12130&rft.date=2012&rft_id=info%3Adoi%2F10.1021%2Fjf304466t&rft_id=info%3Apmid%2F23186318&rft.au=Kim+S.+P.%2C+Moon+E.%2C+Nam+S.+H.%2C+Friedman+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShulginShulgin1997" class="citation book cs1">Shulgin, Alexander; Shulgin, Ann (1997). <i>Tihkal: The Continuation</i>. Berkeley: Transform Press. p. 671. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-9630096-9-9" title="Special:BookSources/0-9630096-9-9"><bdi>0-9630096-9-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Tihkal%3A+The+Continuation&rft.place=Berkeley&rft.pages=671&rft.pub=Transform+Press&rft.date=1997&rft.isbn=0-9630096-9-9&rft.aulast=Shulgin&rft.aufirst=Alexander&rft.au=Shulgin%2C+Ann&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKusu_F.,_Li_X.-D.,_Takamura_K.1992" class="citation journal cs1">Kusu F., Li X.-D., Takamura K. (1992). <a rel="nofollow" class="external text" href="https://doi.org/10.1248%2Fcpb.40.3284">"Determination of synephrine and N-methyltyramine in Zhishi and Zhike (immature Citrus fruits) by high-performance liquid chromatography with electrochemical detection"</a>. <i>Chemical & Pharmaceutical Bulletin</i>. <b>40</b> (12): <span class="nowrap">3284–</span>3286. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1248%2Fcpb.40.3284">10.1248/cpb.40.3284</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+%26+Pharmaceutical+Bulletin&rft.atitle=Determination+of+synephrine+and+N-methyltyramine+in+Zhishi+and+Zhike+%28immature+Citrus+fruits%29+by+high-performance+liquid+chromatography+with+electrochemical+detection&rft.volume=40&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3284-%3C%2Fspan%3E3286&rft.date=1992&rft_id=info%3Adoi%2F10.1248%2Fcpb.40.3284&rft.au=Kusu+F.%2C+Li+X.-D.%2C+Takamura+K.&rft_id=https%3A%2F%2Fdoi.org%2F10.1248%252Fcpb.40.3284&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-Pellat-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-Pellat_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Pellat_12-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPellati_F.,_Benvenuti_S.,_Melegari_M.2005" class="citation journal cs1">Pellati F., Benvenuti S., Melegari M. (2005). "Enantioselective LC analysis of synephrine in natural products on a protein-based chiral stationary phase". <i>Journal of Pharmaceutical and Biomedical Analysis</i>. <b>37</b> (5): <span class="nowrap">839–</span>849. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.jpba.2004.09.008">10.1016/j.jpba.2004.09.008</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/15862657">15862657</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Pharmaceutical+and+Biomedical+Analysis&rft.atitle=Enantioselective+LC+analysis+of+synephrine+in+natural+products+on+a+protein-based+chiral+stationary+phase&rft.volume=37&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E839-%3C%2Fspan%3E849&rft.date=2005&rft_id=info%3Adoi%2F10.1016%2Fj.jpba.2004.09.008&rft_id=info%3Apmid%2F15862657&rft.au=Pellati+F.%2C+Benvenuti+S.%2C+Melegari+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-Mat-13"><span class="mw-cite-backlink">^ <a href="#cite_ref-Mat_13-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Mat_13-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMattoli_L.,_Cangi_F.,_Maidecchi_A.,_Ghiara_C.,_Tubaro_M.,_Traldi_P.2005" class="citation journal cs1">Mattoli L., Cangi F., Maidecchi A., Ghiara C., Tubaro M., Traldi P. (2005). "A rapid liquid chromatography electrospray ionization mass spectrometry method for evaluation of synephrine in <i>Citrus aurantium</i> L. samples". <i>Journal of Agricultural and Food Chemistry</i>. <b>53</b> (26): <span class="nowrap">9860–</span>9866. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjf051270%2B">10.1021/jf051270+</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/16366666">16366666</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Agricultural+and+Food+Chemistry&rft.atitle=A+rapid+liquid+chromatography+electrospray+ionization+mass+spectrometry+method+for+evaluation+of+synephrine+in+Citrus+aurantium+L.+samples&rft.volume=53&rft.issue=26&rft.pages=%3Cspan+class%3D%22nowrap%22%3E9860-%3C%2Fspan%3E9866&rft.date=2005&rft_id=info%3Adoi%2F10.1021%2Fjf051270%2B&rft_id=info%3Apmid%2F16366666&rft.au=Mattoli+L.%2C+Cangi+F.%2C+Maidecchi+A.%2C+Ghiara+C.%2C+Tubaro+M.%2C+Traldi+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-Av-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-Av_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Av_16-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAvula_B.,_Upparapalli_S._K.,_Khan_I._A.2007" class="citation journal cs1">Avula B., Upparapalli S. K., Khan I. A. (2007). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fjaoac%2F90.3.633">"Simultaneous analysis of adrenergic amines and flavonoids in citrus peel jams and fruit juices by liquid chromatography: part 2"</a>. <i>Journal of AOAC International</i>. <b>90</b> (3): <span class="nowrap">633–</span>40. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fjaoac%2F90.3.633">10.1093/jaoac/90.3.633</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17580614">17580614</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+AOAC+International&rft.atitle=Simultaneous+analysis+of+adrenergic+amines+and+flavonoids+in+citrus+peel+jams+and+fruit+juices+by+liquid+chromatography%3A+part+2&rft.volume=90&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E633-%3C%2Fspan%3E40&rft.date=2007&rft_id=info%3Adoi%2F10.1093%2Fjaoac%2F90.3.633&rft_id=info%3Apmid%2F17580614&rft.au=Avula+B.%2C+Upparapalli+S.+K.%2C+Khan+I.+A.&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fjaoac%252F90.3.633&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-XRef-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-XRef_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-XRef_17-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.plantnames.unimelb.edu.au/Sorting/Citrus.html">"Cross-reference for <i>Citrus</i> species and common names"</a>. Plantnames.unimelb.edu.au<span class="reference-accessdate">. Retrieved <span class="nowrap">2013-12-10</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Cross-reference+for+Citrus+species+and+common+names&rft.pub=Plantnames.unimelb.edu.au&rft_id=http%3A%2F%2Fwww.plantnames.unimelb.edu.au%2FSorting%2FCitrus.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-Kusu-18"><span class="mw-cite-backlink">^ <a href="#cite_ref-Kusu_18-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Kusu_18-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Kusu_18-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Kusu_18-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKusu_F.,_Matsumoto_K.,_Arai_K.,_Takamura_K.1996" class="citation journal cs1">Kusu F., Matsumoto K., Arai K., Takamura K. (1996). "Determination of synephrine enantiomers in food and conjugated synephrine in urine by high-performance liquid chromatography with electrochemical detection". <i>Analytical Biochemistry</i>. <b>235</b> (2): <span class="nowrap">191–</span>194. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1006%2Fabio.1996.0111">10.1006/abio.1996.0111</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/8833327">8833327</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Analytical+Biochemistry&rft.atitle=Determination+of+synephrine+enantiomers+in+food+and+conjugated+synephrine+in+urine+by+high-performance+liquid+chromatography+with+electrochemical+detection&rft.volume=235&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E191-%3C%2Fspan%3E194&rft.date=1996&rft_id=info%3Adoi%2F10.1006%2Fabio.1996.0111&rft_id=info%3Apmid%2F8833327&rft.au=Kusu+F.%2C+Matsumoto+K.%2C+Arai+K.%2C+Takamura+K.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-Blum-19"><span class="mw-cite-backlink">^ <a href="#cite_ref-Blum_19-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Blum_19-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Blum_19-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://abc.herbalgram.org/site/DocServer/Bitter_Orange_Peel_and_Synephrine.pdf">"American Botanical Council : Bitter Orange Peel and Synephrine"</a> <span class="cs1-format">(PDF)</span>. <i>Abc.herbalgram.org</i><span class="reference-accessdate">. Retrieved <span class="nowrap">27 January</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Abc.herbalgram.org&rft.atitle=American+Botanical+Council+%3A+Bitter+Orange+Peel+and+Synephrine&rft_id=http%3A%2F%2Fabc.herbalgram.org%2Fsite%2FDocServer%2FBitter_Orange_Peel_and_Synephrine.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDragull_K.,_Breksa_A._P.,_Cain_B.2008" class="citation journal cs1">Dragull K., Breksa A. P., Cain B. (2008). "Synephrine content of juice from Satsuma Mandarins (<i>Citrus unshiu</i> Marcovitch.)". <i>Journal of Agricultural and Food Chemistry</i>. <b>56</b> (19): <span class="nowrap">8874–</span>8878. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjf801225n">10.1021/jf801225n</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/18771270">18771270</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Agricultural+and+Food+Chemistry&rft.atitle=Synephrine+content+of+juice+from+Satsuma+Mandarins+%28Citrus+unshiu+Marcovitch.%29&rft.volume=56&rft.issue=19&rft.pages=%3Cspan+class%3D%22nowrap%22%3E8874-%3C%2Fspan%3E8878&rft.date=2008&rft_id=info%3Adoi%2F10.1021%2Fjf801225n&rft_id=info%3Apmid%2F18771270&rft.au=Dragull+K.%2C+Breksa+A.+P.%2C+Cain+B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFVieira_S._M.,_Theodoro_K._H.,_Glória_M._B._A.2007" class="citation journal cs1">Vieira S. M., Theodoro K. H., Glória M. B. A. (2007). "Profile and levels of bioactive amines in orange juice and orange soft drink". <i>Food Chemistry</i>. <b>100</b> (3): <span class="nowrap">895–</span>903. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.foodchem.2005.10.050">10.1016/j.foodchem.2005.10.050</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Food+Chemistry&rft.atitle=Profile+and+levels+of+bioactive+amines+in+orange+juice+and+orange+soft+drink&rft.volume=100&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E895-%3C%2Fspan%3E903&rft.date=2007&rft_id=info%3Adoi%2F10.1016%2Fj.foodchem.2005.10.050&rft.au=Vieira+S.+M.%2C+Theodoro+K.+H.%2C+Gl%C3%B3ria+M.+B.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFUckoo_R._M.,_Jayaprakasha_G._K.,_Nelson_S._D.,_Patil_B._S.2011" class="citation journal cs1">Uckoo R. M., Jayaprakasha G. K., Nelson S. D., Patil B. S. (2011). "Rapid simultaneous determination of amines and organic acids in citrus using high-performance liquid chromatography". <i>Talanta</i>. <b>83</b> (3): <span class="nowrap">948–</span>54. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.talanta.2010.10.063">10.1016/j.talanta.2010.10.063</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/21147342">21147342</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Talanta&rft.atitle=Rapid+simultaneous+determination+of+amines+and+organic+acids+in+citrus+using+high-performance+liquid+chromatography&rft.volume=83&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E948-%3C%2Fspan%3E54&rft.date=2011&rft_id=info%3Adoi%2F10.1016%2Fj.talanta.2010.10.063&rft_id=info%3Apmid%2F21147342&rft.au=Uckoo+R.+M.%2C+Jayaprakasha+G.+K.%2C+Nelson+S.+D.%2C+Patil+B.+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-Ib-24"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ib_24-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ib_24-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFIbrahim_K._E.,_Couch_M._W.,_Williams_C._M.,_Budd_M._B.,_Yost_R._A.,_Midgley_J._M.1984" class="citation journal cs1">Ibrahim K. E., Couch M. W., Williams C. M., Budd M. B., Yost R. A., Midgley J. M. (1984). "Quantitative measurement of octopamines and synephrines in urine using capillary column gas chromatography negative ion chemical ionization mass spectrometry". <i>Analytical Chemistry</i>. <b>56</b> (9): <span class="nowrap">1695–</span>1699. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fac00273a037">10.1021/ac00273a037</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/6435479">6435479</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Analytical+Chemistry&rft.atitle=Quantitative+measurement+of+octopamines+and+synephrines+in+urine+using+capillary+column+gas+chromatography+negative+ion+chemical+ionization+mass+spectrometry&rft.volume=56&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1695-%3C%2Fspan%3E1699&rft.date=1984&rft_id=info%3Adoi%2F10.1021%2Fac00273a037&rft_id=info%3Apmid%2F6435479&rft.au=Ibrahim+K.+E.%2C+Couch+M.+W.%2C+Williams+C.+M.%2C+Budd+M.+B.%2C+Yost+R.+A.%2C+Midgley+J.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWang_R.,_Wan_L.,_Li_Q.,_Liu_X.,_Huang_Y.2007" class="citation journal cs1">Wang R., Wan L., Li Q., Liu X., Huang Y. (2007). "Chemiluminescence of synephrine based on the cerium(IV)–rhodamine B system". <i>Luminescence</i>. <b>22</b> (2): <span class="nowrap">140–</span>146. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fbio.937">10.1002/bio.937</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/17089346">17089346</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Luminescence&rft.atitle=Chemiluminescence+of+synephrine+based+on+the+cerium%28IV%29%E2%80%93rhodamine+B+system&rft.volume=22&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E140-%3C%2Fspan%3E146&rft.date=2007&rft_id=info%3Adoi%2F10.1002%2Fbio.937&rft_id=info%3Apmid%2F17089346&rft.au=Wang+R.%2C+Wan+L.%2C+Li+Q.%2C+Liu+X.%2C+Huang+Y.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWatson_D.G.,_Midgley_J.M.,_Chen_R.N.,_Huang_W.,_Bain_G.M.,_McDonald_N.M.,_Reid_J.L.,_McGhee_C.N.J.1990" class="citation journal cs1">Watson D.G., Midgley J.M., Chen R.N., Huang W., Bain G.M., McDonald N.M., Reid J.L., McGhee C.N.J. (1990). "Analysis of biogenic amines and their metabolites in biological tissues and fluids by gas chromatography—negative ion chemical ionization mass spectrometry (GC-NICIMS)". <i>Journal of Pharmaceutical and Biomedical Analysis</i>. <b>8</b> (<span class="nowrap">8–</span>12): <span class="nowrap">899–</span>904. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0731-7085%2890%2980139-g">10.1016/0731-7085(90)80139-g</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/2100639">2100639</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Pharmaceutical+and+Biomedical+Analysis&rft.atitle=Analysis+of+biogenic+amines+and+their+metabolites+in+biological+tissues+and+fluids+by+gas+chromatography%E2%80%94negative+ion+chemical+ionization+mass+spectrometry+%28GC-NICIMS%29&rft.volume=8&rft.issue=%3Cspan+class%3D%22nowrap%22%3E8%E2%80%93%3C%2Fspan%3E12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E899-%3C%2Fspan%3E904&rft.date=1990&rft_id=info%3Adoi%2F10.1016%2F0731-7085%2890%2980139-g&rft_id=info%3Apmid%2F2100639&rft.au=Watson+D.G.%2C+Midgley+J.M.%2C+Chen+R.N.%2C+Huang+W.%2C+Bain+G.M.%2C+McDonald+N.M.%2C+Reid+J.L.%2C+McGhee+C.N.J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFIbrahim_K._E.,_Couch_M._W.,_Williams_C._M.,_Fregly_M._J.,_Midgley_J._M.1985" class="citation journal cs1">Ibrahim K. E., Couch M. W., Williams C. M., Fregly M. J., Midgley J. M. (1985). "<i>m</i>-Octopamine: normal occurrence with <i>p</i>-octopamine in mammalian sympathetic nerves". <i>Journal of Neurochemistry</i>. <b>44</b> (6): <span class="nowrap">1862–</span>1867. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1471-4159.1985.tb07180.x">10.1111/j.1471-4159.1985.tb07180.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/3921667">3921667</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:7376144">7376144</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Neurochemistry&rft.atitle=m-Octopamine%3A+normal+occurrence+with+p-octopamine+in+mammalian+sympathetic+nerves&rft.volume=44&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1862-%3C%2Fspan%3E1867&rft.date=1985&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A7376144%23id-name%3DS2CID&rft_id=info%3Apmid%2F3921667&rft_id=info%3Adoi%2F10.1111%2Fj.1471-4159.1985.tb07180.x&rft.au=Ibrahim+K.+E.%2C+Couch+M.+W.%2C+Williams+C.+M.%2C+Fregly+M.+J.%2C+Midgley+J.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFD'Andrea_G.,_Granella_F.,_Leone_M.,_Perini_F.,_Farruggio_A.,_Bussone_G.2006" class="citation journal cs1">D'Andrea G., Granella F., Leone M., Perini F., Farruggio A., Bussone G. (2006). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1468-2982.2006.01141.x">"Abnormal platelet trace amine profiles in migraine with and without aura"</a>. <i>Cephalalgia</i>. <b>26</b> (8): <span class="nowrap">968–</span>972. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1468-2982.2006.01141.x">10.1111/j.1468-2982.2006.01141.x</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16886933">16886933</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:43823090">43823090</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cephalalgia&rft.atitle=Abnormal+platelet+trace+amine+profiles+in+migraine+with+and+without+aura&rft.volume=26&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E968-%3C%2Fspan%3E972&rft.date=2006&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A43823090%23id-name%3DS2CID&rft_id=info%3Apmid%2F16886933&rft_id=info%3Adoi%2F10.1111%2Fj.1468-2982.2006.01141.x&rft.au=D%27Andrea+G.%2C+Granella+F.%2C+Leone+M.%2C+Perini+F.%2C+Farruggio+A.%2C+Bussone+G.&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fj.1468-2982.2006.01141.x&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-Andrea-29"><span class="mw-cite-backlink">^ <a href="#cite_ref-Andrea_29-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Andrea_29-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFD'Andrea_G.,_Terrazzino_S.,_Fortina_D.,_Farruggioa_A.,_Rinaldi_L.,_Leon_A.2003" class="citation journal cs1">D'Andrea G., Terrazzino S., Fortina D., Farruggioa A., Rinaldi L., Leon A. (2003). "HPLC electrochemical detection of trace amines in human plasma and platelets and expression of mRNA transcripts of trace amine receptors in circulating leukocytes". <i>Neuroscience Letters</i>. <b>346</b> (<span class="nowrap">1–</span>2): <span class="nowrap">89–</span>92. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0304-3940%2803%2900573-1">10.1016/s0304-3940(03)00573-1</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/12850555">12850555</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:1673803">1673803</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neuroscience+Letters&rft.atitle=HPLC+electrochemical+detection+of+trace+amines+in+human+plasma+and+platelets+and+expression+of+mRNA+transcripts+of+trace+amine+receptors+in+circulating+leukocytes&rft.volume=346&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E89-%3C%2Fspan%3E92&rft.date=2003&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A1673803%23id-name%3DS2CID&rft_id=info%3Apmid%2F12850555&rft_id=info%3Adoi%2F10.1016%2Fs0304-3940%2803%2900573-1&rft.au=D%27Andrea+G.%2C+Terrazzino+S.%2C+Fortina+D.%2C+Farruggioa+A.%2C+Rinaldi+L.%2C+Leon+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-Pel-30"><span class="mw-cite-backlink">^ <a href="#cite_ref-Pel_30-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Pel_30-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPellati_F.,_Benvenuti_S.,_Melegari_M.,_Firenzuoli_F.2002" class="citation journal cs1">Pellati F., Benvenuti S., Melegari M., Firenzuoli F. (2002). "Determination of adrenergic agonists from extracts and herbal products of <i>Citrus aurantium</i> L. var. amara by LC". <i>Journal of Pharmaceutical and Biomedical Analysis</i>. <b>29</b> (6): <span class="nowrap">1113–</span>1119. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0731-7085%2802%2900153-x">10.1016/s0731-7085(02)00153-x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12110397">12110397</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Pharmaceutical+and+Biomedical+Analysis&rft.atitle=Determination+of+adrenergic+agonists+from+extracts+and+herbal+products+of+Citrus+aurantium+L.+var.+amara+by+LC.&rft.volume=29&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1113-%3C%2Fspan%3E1119&rft.date=2002&rft_id=info%3Adoi%2F10.1016%2Fs0731-7085%2802%2900153-x&rft_id=info%3Apmid%2F12110397&rft.au=Pellati+F.%2C+Benvenuti+S.%2C+Melegari+M.%2C+Firenzuoli+F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPellati_F.,_Cannazza_G.,_Benvenuti_S.2010" class="citation journal cs1">Pellati F., Cannazza G., Benvenuti S. (2010). "Study on the racemization of synephrine by off-column chiral high-performance liquid chromatography". <i>Journal of Chromatography A</i>. <b>1217</b> (21): <span class="nowrap">3503–</span>3510. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.chroma.2010.03.026">10.1016/j.chroma.2010.03.026</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/20399443">20399443</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chromatography+A&rft.atitle=Study+on+the+racemization+of+synephrine+by+off-column+chiral+high-performance+liquid+chromatography&rft.volume=1217&rft.issue=21&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3503-%3C%2Fspan%3E3510&rft.date=2010&rft_id=info%3Adoi%2F10.1016%2Fj.chroma.2010.03.026&rft_id=info%3Apmid%2F20399443&rft.au=Pellati+F.%2C+Cannazza+G.%2C+Benvenuti+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-32">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKusu_F.,_Matsumoto_K.,_Takamura_K.1995" class="citation journal cs1">Kusu F., Matsumoto K., Takamura K. (1995). <a rel="nofollow" class="external text" href="https://www.jstage.jst.go.jp/article/cpb1958/43/7/43_7_1158/_pdf">"Direct separation and determination of synephrine enantiomers by high-performance liquid chromatography with electrochemical detection"</a>. <i>Chemical & Pharmaceutical Bulletin</i>. <b>43</b> (7): <span class="nowrap">1158–</span>1161. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1248%2Fcpb.43.1158">10.1248/cpb.43.1158</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+%26+Pharmaceutical+Bulletin&rft.atitle=Direct+separation+and+determination+of+synephrine+enantiomers+by+high-performance+liquid+chromatography+with+electrochemical+detection&rft.volume=43&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1158-%3C%2Fspan%3E1161&rft.date=1995&rft_id=info%3Adoi%2F10.1248%2Fcpb.43.1158&rft.au=Kusu+F.%2C+Matsumoto+K.%2C+Takamura+K.&rft_id=https%3A%2F%2Fwww.jstage.jst.go.jp%2Farticle%2Fcpb1958%2F43%2F7%2F43_7_1158%2F_pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRanieri_R._L.,_McLaughlin_J._L.1976" class="citation journal cs1">Ranieri R. L., McLaughlin J. L. (1976). "Cactus alkaloids. XXVIII. β-Phenethylamine and tetrahydroisoquinoline alkaloids from the Mexican cactus <i>Dolichothele longimamma</i>". <i>The Journal of Organic Chemistry</i>. <b>41</b> (2): <span class="nowrap">319–</span>323. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00864a030">10.1021/jo00864a030</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=Cactus+alkaloids.+XXVIII.+%CE%B2-Phenethylamine+and+tetrahydroisoquinoline+alkaloids+from+the+Mexican+cactus+Dolichothele+longimamma&rft.volume=41&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E319-%3C%2Fspan%3E323&rft.date=1976&rft_id=info%3Adoi%2F10.1021%2Fjo00864a030&rft.au=Ranieri+R.+L.%2C+McLaughlin+J.+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-Wheat-34"><span class="mw-cite-backlink">^ <a href="#cite_ref-Wheat_34-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Wheat_34-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWheaton_T._A.,_Stewart_I.1969" class="citation journal cs1">Wheaton T. A., Stewart I. (1969). "Biosynthesis of synephrine in citrus". <i>Phytochemistry</i>. <b>8</b> (1): <span class="nowrap">85–</span>92. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1969PChem...8...85W">1969PChem...8...85W</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0031-9422%2800%2985799-4">10.1016/s0031-9422(00)85799-4</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Phytochemistry&rft.atitle=Biosynthesis+of+synephrine+in+citrus&rft.volume=8&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E85-%3C%2Fspan%3E92&rft.date=1969&rft_id=info%3Adoi%2F10.1016%2Fs0031-9422%2800%2985799-4&rft_id=info%3Abibcode%2F1969PChem...8...85W&rft.au=Wheaton+T.+A.%2C+Stewart+I.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-35">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBartley_A._P._Breksa_III,_Ishida_B._K.2010" class="citation journal cs1">Bartley A. P. Breksa III, Ishida B. K. (2010). "PCR amplification and cloning of tyrosine decarboxylase involved in synephrine biosynthesis in Citrus". <i>New Biotechnology</i>. <b>27</b> (4): <span class="nowrap">308–</span>316. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.nbt.2010.04.003">10.1016/j.nbt.2010.04.003</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/20403465">20403465</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=New+Biotechnology&rft.atitle=PCR+amplification+and+cloning+of+tyrosine+decarboxylase+involved+in+synephrine+biosynthesis+in+Citrus&rft.volume=27&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E308-%3C%2Fspan%3E316&rft.date=2010&rft_id=info%3Adoi%2F10.1016%2Fj.nbt.2010.04.003&rft_id=info%3Apmid%2F20403465&rft.au=Bartley+A.+P.+Breksa+III%2C+Ishida+B.+K.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-Trace_amine_template_1-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-Trace_amine_template_1_36-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBroadley2010" class="citation journal cs1">Broadley KJ (March 2010). "The vascular effects of trace amines and amphetamines". <i>Pharmacology & Therapeutics</i>. <b>125</b> (3): <span class="nowrap">363–</span>375. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.pharmthera.2009.11.005">10.1016/j.pharmthera.2009.11.005</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19948186">19948186</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacology+%26+Therapeutics&rft.atitle=The+vascular+effects+of+trace+amines+and+amphetamines&rft.volume=125&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E363-%3C%2Fspan%3E375&rft.date=2010-03&rft_id=info%3Adoi%2F10.1016%2Fj.pharmthera.2009.11.005&rft_id=info%3Apmid%2F19948186&rft.aulast=Broadley&rft.aufirst=KJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-Trace_amine_template_2-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-Trace_amine_template_2_37-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLindemannHoener2005" class="citation journal cs1">Lindemann L, Hoener MC (May 2005). "A renaissance in trace amines inspired by a novel GPCR family". <i>Trends in Pharmacological Sciences</i>. <b>26</b> (5): <span class="nowrap">274–</span>281. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.tips.2005.03.007">10.1016/j.tips.2005.03.007</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/15860375">15860375</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Trends+in+Pharmacological+Sciences&rft.atitle=A+renaissance+in+trace+amines+inspired+by+a+novel+GPCR+family&rft.volume=26&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E274-%3C%2Fspan%3E281&rft.date=2005-05&rft_id=info%3Adoi%2F10.1016%2Fj.tips.2005.03.007&rft_id=info%3Apmid%2F15860375&rft.aulast=Lindemann&rft.aufirst=L&rft.au=Hoener%2C+MC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-CYP2D6_tyramine-dopamine_metabolism-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-CYP2D6_tyramine-dopamine_metabolism_38-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWangLiDongYue2014" class="citation journal cs1">Wang X, Li J, Dong G, Yue J (February 2014). "The endogenous substrates of brain CYP2D". <i>European Journal of Pharmacology</i>. <b>724</b>: <span class="nowrap">211–</span>218. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ejphar.2013.12.025">10.1016/j.ejphar.2013.12.025</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/24374199">24374199</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Pharmacology&rft.atitle=The+endogenous+substrates+of+brain+CYP2D&rft.volume=724&rft.pages=%3Cspan+class%3D%22nowrap%22%3E211-%3C%2Fspan%3E218&rft.date=2014-02&rft_id=info%3Adoi%2F10.1016%2Fj.ejphar.2013.12.025&rft_id=info%3Apmid%2F24374199&rft.aulast=Wang&rft.aufirst=X&rft.au=Li%2C+J&rft.au=Dong%2C+G&rft.au=Yue%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-Sant-39"><span class="mw-cite-backlink">^ <a href="#cite_ref-Sant_39-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Sant_39-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSantana_J.,_Sharpless_K._E.,_Nelson_B._C.2008" class="citation journal cs1">Santana J., Sharpless K. E., Nelson B. C. (2008). "Determination of para-synephrine and meta-synephrine positional isomers in bitter orange-containing dietary supplements by LC/UV and LC/MS/MS". <i>Food Chemistry</i>. <b>109</b> (3): <span class="nowrap">675–</span>682. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.foodchem.2007.12.076">10.1016/j.foodchem.2007.12.076</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Food+Chemistry&rft.atitle=Determination+of+para-synephrine+and+meta-synephrine+positional+isomers+in+bitter+orange-containing+dietary+supplements+by+LC%2FUV+and+LC%2FMS%2FMS.&rft.volume=109&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E675-%3C%2Fspan%3E682&rft.date=2008&rft_id=info%3Adoi%2F10.1016%2Fj.foodchem.2007.12.076&rft.au=Santana+J.%2C+Sharpless+K.+E.%2C+Nelson+B.+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-40">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHallerBenowitzJacob_p2005" class="citation journal cs1">Haller, C. A.; Benowitz, N. L.; Jacob p, 3rd (2005). "Hemodynamic effects of ephedra-free weight-loss supplements in humans". <i>The American Journal of Medicine</i>. <b>118</b> (9): <span class="nowrap">998–</span>1003. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.amjmed.2005.02.034">10.1016/j.amjmed.2005.02.034</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/16164886">16164886</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Medicine&rft.atitle=Hemodynamic+effects+of+ephedra-free+weight-loss+supplements+in+humans&rft.volume=118&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E998-%3C%2Fspan%3E1003&rft.date=2005&rft_id=info%3Adoi%2F10.1016%2Fj.amjmed.2005.02.034&rft_id=info%3Apmid%2F16164886&rft.aulast=Haller&rft.aufirst=C.+A.&rft.au=Benowitz%2C+N.+L.&rft.au=Jacob+p%2C+3rd&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: numeric names: authors list (<a href="/wiki/Category:CS1_maint:_numeric_names:_authors_list" title="Category:CS1 maint: numeric names: authors list">link</a>)</span></span> </li> <li id="cite_note-Las-41"><span class="mw-cite-backlink">^ <a href="#cite_ref-Las_41-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Las_41-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Las_41-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLasch_F1927" class="citation journal cs1">Lasch F (1927). "Über die Pharmakologie des Sympathols, einer neuen adrenalinähnlichen Substanz. (Zugleich ein Beitrag zur Frage der chemischen Konstitution und pharmakodynamischen Wirkung)". <i>Naunyn-Schmiedebergs Archiv für Experimentelle Pathologie und Pharmakologie</i>. <b>124</b> (<span class="nowrap">3–</span>4): <span class="nowrap">231–</span>244. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fbf01861902">10.1007/bf01861902</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:24160900">24160900</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Naunyn-Schmiedebergs+Archiv+f%C3%BCr+Experimentelle+Pathologie+und+Pharmakologie&rft.atitle=%C3%9Cber+die+Pharmakologie+des+Sympathols%2C+einer+neuen+adrenalin%C3%A4hnlichen+Substanz.+%28Zugleich+ein+Beitrag+zur+Frage+der+chemischen+Konstitution+und+pharmakodynamischen+Wirkung%29&rft.volume=124&rft.issue=%3Cspan+class%3D%22nowrap%22%3E3%E2%80%93%3C%2Fspan%3E4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E231-%3C%2Fspan%3E244&rft.date=1927&rft_id=info%3Adoi%2F10.1007%2Fbf01861902&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24160900%23id-name%3DS2CID&rft.au=Lasch+F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-42">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHochrein_M.,_Keller_J.1930" class="citation journal cs1">Hochrein M., Keller J. (1930). "Über die Wirkung des Adrenalins und adrenalinverwandter Körper (Sympatol und Ephetonin) auf den Kreislauf". <i>Naunyn-Schmiedebergs Archiv für Experimentelle Pathologie und Pharmakologie</i>. <b>156</b>: <span class="nowrap">37–</span>63. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fbf01859312">10.1007/bf01859312</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:28747772">28747772</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Naunyn-Schmiedebergs+Archiv+f%C3%BCr+Experimentelle+Pathologie+und+Pharmakologie&rft.atitle=%C3%9Cber+die+Wirkung+des+Adrenalins+und+adrenalinverwandter+K%C3%B6rper+%28Sympatol+und+Ephetonin%29+auf+den+Kreislauf&rft.volume=156&rft.pages=%3Cspan+class%3D%22nowrap%22%3E37-%3C%2Fspan%3E63&rft.date=1930&rft_id=info%3Adoi%2F10.1007%2Fbf01859312&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A28747772%23id-name%3DS2CID&rft.au=Hochrein+M.%2C+Keller+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-43">^</a></b></span> <span class="reference-text">H. Legerlotz, US Patent 1,932,347 (October 24, 1933).</span> </li> <li id="cite_note-Stock-44"><span class="mw-cite-backlink">^ <a href="#cite_ref-Stock_44-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Stock_44-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Stock_44-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Stock_44-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFStockton_A._B.,_Pace_P._T.,_Tainter_M._L.1931" class="citation journal cs1">Stockton A. B., Pace P. T., Tainter M. L. (1931). "Some clinical actions and therapeutic uses of racemic synephrine". <i>Journal of Pharmacology and Experimental Therapeutics</i>. <b>41</b>: <span class="nowrap">11–</span>20.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Pharmacology+and+Experimental+Therapeutics&rft.atitle=Some+clinical+actions+and+therapeutic+uses+of+racemic+synephrine&rft.volume=41&rft.pages=%3Cspan+class%3D%22nowrap%22%3E11-%3C%2Fspan%3E20&rft.date=1931&rft.au=Stockton+A.+B.%2C+Pace+P.+T.%2C+Tainter+M.+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-Tain-45"><span class="mw-cite-backlink">^ <a href="#cite_ref-Tain_45-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Tain_45-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Tain_45-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Tain_45-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Tain_45-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Tain_45-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Tain_45-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTainter_M._L.,_Seidenfeld_M._A.1930" class="citation journal cs1">Tainter M. L., Seidenfeld M. A. (1930). "Comparative actions of sympathomimetic compounds: synephrine-isomers and -ketone". <i>J. Pharmacol. Exp. Ther</i>. <b>40</b>: <span class="nowrap">23–</span>42.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Pharmacol.+Exp.+Ther.&rft.atitle=Comparative+actions+of+sympathomimetic+compounds%3A+synephrine-isomers+and+-ketone&rft.volume=40&rft.pages=%3Cspan+class%3D%22nowrap%22%3E23-%3C%2Fspan%3E42&rft.date=1930&rft.au=Tainter+M.+L.%2C+Seidenfeld+M.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-46">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1">"Council on Pharmacy and Chemistry". <i>The Journal of the American Medical Association</i>. <b>94</b> (18): 1404. 1930. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1001%2Fjama.1930.02710440042013">10.1001/jama.1930.02710440042013</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+the+American+Medical+Association&rft.atitle=Council+on+Pharmacy+and+Chemistry&rft.volume=94&rft.issue=18&rft.pages=1404&rft.date=1930&rft_id=info%3Adoi%2F10.1001%2Fjama.1930.02710440042013&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-Hart-47"><span class="mw-cite-backlink">^ <a href="#cite_ref-Hart_47-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Hart_47-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHartung_W1931" class="citation journal cs1">Hartung W (1931). "Epinephrine and related compounds: influence of structure on physiological activity". <i>Chemical Reviews</i>. <b>9</b> (3): <span class="nowrap">389–</span>468. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr60034a002">10.1021/cr60034a002</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=Epinephrine+and+related+compounds%3A+influence+of+structure+on+physiological+activity&rft.volume=9&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E389-%3C%2Fspan%3E468&rft.date=1931&rft_id=info%3Adoi%2F10.1021%2Fcr60034a002&rft.au=Hartung+W&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-48"><span class="mw-cite-backlink"><b><a href="#cite_ref-48">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEditorial1944" class="citation journal cs1">Editorial (1944). "Sympatol-Stearns - A triumph of medical misinformation for physicians". <i>Journal of the American Medical Association</i>. <b>124</b> (14): 988. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1001%2Fjama.1944.02850140034013">10.1001/jama.1944.02850140034013</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Medical+Association&rft.atitle=Sympatol-Stearns+-+A+triumph+of+medical+misinformation+for+physicians&rft.volume=124&rft.issue=14&rft.pages=988&rft.date=1944&rft_id=info%3Adoi%2F10.1001%2Fjama.1944.02850140034013&rft.au=Editorial&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-49"><span class="mw-cite-backlink"><b><a href="#cite_ref-49">^</a></b></span> <span class="reference-text">J. R. DiPalma (Ed.) (1965),<i>Drill's Pharmacology in Medicine,3rd Ed.</i>, p.494, McGraw-Hill, New York.</span> </li> <li id="cite_note-Wil-50"><span class="mw-cite-backlink">^ <a href="#cite_ref-Wil_50-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Wil_50-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">C. O. Wilson, O. Gisvold, and R. F. Doerge (Eds.) (1966). <i>Textbook of Organic Medicinal and Pharmaceutical Chemistry, 5th ed.,</i> p.438, Lippincott, Philadelphia.</span> </li> <li id="cite_note-51"><span class="mw-cite-backlink"><b><a href="#cite_ref-51">^</a></b></span> <span class="reference-text">D. M. Aviado (Ed.), 1972. <i>Krantz & Carr's Pharmacologic Principles of Medical Practice, 8th Ed.</i>, p.526, Williams & Wilkins, Baltimore.</span> </li> <li id="cite_note-52"><span class="mw-cite-backlink"><b><a href="#cite_ref-52">^</a></b></span> <span class="reference-text">R. C. Baselt (2008). <i>Disposition of Toxic Drugs and Chemicals in Man (8th Ed..)</i> pp. 1471–2, Biomedical Publications, Foster City, California. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-9626523-7-0" title="Special:BookSources/978-0-9626523-7-0">978-0-9626523-7-0</a>.</span> </li> <li id="cite_note-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-53">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external free" href="https://www.mims.com/USA/drug/info/oxedrine/?type=full&mtype=generic">https://www.mims.com/USA/drug/info/oxedrine/?type=full&mtype=generic</a> <sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged January 2022">permanent dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup></span> </li> <li id="cite_note-G._Rossato,_V._M_2011-54"><span class="mw-cite-backlink">^ <a href="#cite_ref-G._Rossato,_V._M_2011_54-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-G._Rossato,_V._M_2011_54-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRossato_L._G.,_Costa_V._M.,_Limberger_R._P.,_de_Lourdes_Bastos_M.,_Remião_F.2011" class="citation journal cs1">Rossato L. G., Costa V. M., Limberger R. P., de Lourdes Bastos M., Remião F. (2011). "Synephrine: From trace concentrations to massive consumption in weight-loss". <i>Food and Chemical Toxicology</i>. <b>49</b> (1): <span class="nowrap">8–</span>16. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.fct.2010.11.007">10.1016/j.fct.2010.11.007</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/21075161">21075161</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Food+and+Chemical+Toxicology&rft.atitle=Synephrine%3A+From+trace+concentrations+to+massive+consumption+in+weight-loss&rft.volume=49&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E8-%3C%2Fspan%3E16&rft.date=2011&rft_id=info%3Adoi%2F10.1016%2Fj.fct.2010.11.007&rft_id=info%3Apmid%2F21075161&rft.au=Rossato+L.+G.%2C+Costa+V.+M.%2C+Limberger+R.+P.%2C+de+Lourdes+Bastos+M.%2C+Remi%C3%A3o+F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-55"><span class="mw-cite-backlink"><b><a href="#cite_ref-55">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPenzak_S._R.,_Jann_M._W.,_Cold_J._A.,_Hon_Y._Y.,_Desai_H._D.,_Gurley_B._J.2001" class="citation journal cs1">Penzak S. R., Jann M. W., Cold J. A., Hon Y. Y., Desai H. D., Gurley B. J. (2001). "Seville (sour) orange juice: Synephrine content and cardiovascular effects in normotensive adults". <i>The Journal of Clinical Pharmacology</i>. <b>41</b> (10): <span class="nowrap">1059–</span>1063. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F00912700122012652">10.1177/00912700122012652</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/11583473">11583473</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:32631329">32631329</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Clinical+Pharmacology&rft.atitle=Seville+%28sour%29+orange+juice%3A+Synephrine+content+and+cardiovascular+effects+in+normotensive+adults&rft.volume=41&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1059-%3C%2Fspan%3E1063&rft.date=2001&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A32631329%23id-name%3DS2CID&rft_id=info%3Apmid%2F11583473&rft_id=info%3Adoi%2F10.1177%2F00912700122012652&rft.au=Penzak+S.+R.%2C+Jann+M.+W.%2C+Cold+J.+A.%2C+Hon+Y.+Y.%2C+Desai+H.+D.%2C+Gurley+B.+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-56"><span class="mw-cite-backlink"><b><a href="#cite_ref-56">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKappe_T.,_Armstrong_M._D.1965" class="citation journal cs1">Kappe T., Armstrong M. D. (1965). "Ultraviolet absorption spectra and apparent acidic dissociation constants of some phenolic amines". <i>Journal of Medicinal Chemistry</i>. <b>8</b> (3): <span class="nowrap">368–</span>374. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjm00327a018">10.1021/jm00327a018</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/14323148">14323148</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Medicinal+Chemistry&rft.atitle=Ultraviolet+absorption+spectra+and+apparent+acidic+dissociation+constants+of+some+phenolic+amines&rft.volume=8&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E368-%3C%2Fspan%3E374&rft.date=1965&rft_id=info%3Adoi%2F10.1021%2Fjm00327a018&rft_id=info%3Apmid%2F14323148&rft.au=Kappe+T.%2C+Armstrong+M.+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-57"><span class="mw-cite-backlink"><b><a href="#cite_ref-57">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBergmann_E._D.,_Sulzbacher_M.1951" class="citation journal cs1">Bergmann E. D., Sulzbacher M. (1951). "A new synthesis of 1-(<i>m</i>- and <i>p</i>-hydroxyphenyl)-2-methylaminoethanol (<i>m</i>- and <i>p</i>-sympathol)". <i>The Journal of Organic Chemistry</i>. <b>16</b>: <span class="nowrap">84–</span>89. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo01141a013">10.1021/jo01141a013</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=A+new+synthesis+of+1-%28m-+and+p-hydroxyphenyl%29-2-methylaminoethanol+%28m-+and+p-sympathol%29&rft.volume=16&rft.pages=%3Cspan+class%3D%22nowrap%22%3E84-%3C%2Fspan%3E89&rft.date=1951&rft_id=info%3Adoi%2F10.1021%2Fjo01141a013&rft.au=Bergmann+E.+D.%2C+Sulzbacher+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-58"><span class="mw-cite-backlink"><b><a href="#cite_ref-58">^</a></b></span> <span class="reference-text">The Merck Index, 10th Ed. (1983), p. 1295, Merck & Co., Rahway, NJ.</span> </li> <li id="cite_note-Midg-59"><span class="mw-cite-backlink">^ <a href="#cite_ref-Midg_59-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Midg_59-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Midg_59-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Midg_59-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text">J. M. Midgley, C. M. Thonoor, A. F. Drake, C. M. Williams, A. E. Koziol and G. J. Palenik (1989). "The resolution and absolute configuration by X-ray crystallography of the isomeric octopamines and synephrines." <i>J. Chem. Soc., Perkin Trans. 2</i> 963-969.</span> </li> <li id="cite_note-60"><span class="mw-cite-backlink"><b><a href="#cite_ref-60">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPriestley_H._M.,_Moness_E.1940" class="citation journal cs1">Priestley H. M., Moness E. (1940). "A study of the intermediates in the preparation of sympathol". <i>J. Org. Chem</i>. <b>40</b> (4): <span class="nowrap">355–</span>361. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo01210a004">10.1021/jo01210a004</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Org.+Chem.&rft.atitle=A+study+of+the+intermediates+in+the+preparation+of+sympathol&rft.volume=40&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E355-%3C%2Fspan%3E361&rft.date=1940&rft_id=info%3Adoi%2F10.1021%2Fjo01210a004&rft.au=Priestley+H.+M.%2C+Moness+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-61"><span class="mw-cite-backlink"><b><a href="#cite_ref-61">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBergmann_E._D.,_Sulzbacher_M.1951" class="citation journal cs1">Bergmann E. D., Sulzbacher M. (1951). "A new synthesi of 1-(<i>m</i>- and <i>p</i>-hydroxyphenyl)-2-methylaminoethanol (<i>m</i>- and <i>p</i>-sympathol)". <i>The Journal of Organic Chemistry</i>. <b>16</b>: <span class="nowrap">84–</span>89. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo01141a013">10.1021/jo01141a013</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=A+new+synthesi+of+1-%28m-+and+p-hydroxyphenyl%29-2-methylaminoethanol+%28m-+and+p-sympathol%29&rft.volume=16&rft.pages=%3Cspan+class%3D%22nowrap%22%3E84-%3C%2Fspan%3E89&rft.date=1951&rft_id=info%3Adoi%2F10.1021%2Fjo01141a013&rft.au=Bergmann+E.+D.%2C+Sulzbacher+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-62"><span class="mw-cite-backlink"><b><a href="#cite_ref-62">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLands_A._M.,_Rickards_E._E.,_Nash_V._L.,_Hooper_K._Z.1947" class="citation journal cs1">Lands A. M., Rickards E. E., Nash V. L., Hooper K. Z. (1947). "The pharmacology of vasodepressor compounds structurally related to the sympathomimetic amines". <i>The Journal of Pharmacology and Experimental Therapeutics</i>. <b>89</b> (4): <span class="nowrap">297–</span>305. <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/20295509">20295509</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Pharmacology+and+Experimental+Therapeutics&rft.atitle=The+pharmacology+of+vasodepressor+compounds+structurally+related+to+the+sympathomimetic+amines&rft.volume=89&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E297-%3C%2Fspan%3E305&rft.date=1947&rft_id=info%3Apmid%2F20295509&rft.au=Lands+A.+M.%2C+Rickards+E.+E.%2C+Nash+V.+L.%2C+Hooper+K.+Z.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-63"><span class="mw-cite-backlink"><b><a href="#cite_ref-63">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFUnna_K1951" class="citation journal cs1">Unna K (1951). "Pharmakologische Untersuchungen über neue Sympatolabkömmlinge". <i>Naunyn-Schmiedebergs Archiv für Experimentelle Pathologie und Pharmakologie</i>. <b>213</b>: <span class="nowrap">207–</span>234. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fbf02432757">10.1007/bf02432757</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:30482120">30482120</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Naunyn-Schmiedebergs+Archiv+f%C3%BCr+Experimentelle+Pathologie+und+Pharmakologie&rft.atitle=Pharmakologische+Untersuchungen+%C3%BCber+neue+Sympatolabk%C3%B6mmlinge&rft.volume=213&rft.pages=%3Cspan+class%3D%22nowrap%22%3E207-%3C%2Fspan%3E234&rft.date=1951&rft_id=info%3Adoi%2F10.1007%2Fbf02432757&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A30482120%23id-name%3DS2CID&rft.au=Unna+K&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-64"><span class="mw-cite-backlink"><b><a href="#cite_ref-64">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMcCulloch_J,_Deshmukh_VD,_Harper_AM1978" class="citation journal cs1">McCulloch J, Deshmukh VD, Harper AM (1978). "Indirect sympathomimetic agents and cerebral blood flow and metabolism". <i>European Journal of Pharmacology</i>. <b>47</b> (1): <span class="nowrap">11–</span>8. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0014-2999%2878%2990368-0">10.1016/0014-2999(78)90368-0</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/412682">412682</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Pharmacology&rft.atitle=Indirect+sympathomimetic+agents+and+cerebral+blood+flow+and+metabolism&rft.volume=47&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E11-%3C%2Fspan%3E8&rft.date=1978&rft_id=info%3Adoi%2F10.1016%2F0014-2999%2878%2990368-0&rft_id=info%3Apmid%2F412682&rft.au=McCulloch+J%2C+Deshmukh+VD%2C+Harper+AM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-65"><span class="mw-cite-backlink"><b><a href="#cite_ref-65">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEhrismann_O.,_Maloff_G.1928" class="citation journal cs1">Ehrismann O., Maloff G. (1928). "Über zwei Gifte der Adrenalingruppe (<i>p</i>-Oxyphenyläthanolmethylamin und sein Keton". <i>Naunyn-Schmiedebergs Archiv für Experimentelle Pathologie und Pharmakologie</i>. <b>136</b> (<span class="nowrap">3–</span>4): <span class="nowrap">172–</span>184. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fbf01862149">10.1007/bf01862149</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:21414110">21414110</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Naunyn-Schmiedebergs+Archiv+f%C3%BCr+Experimentelle+Pathologie+und+Pharmakologie&rft.atitle=%C3%9Cber+zwei+Gifte+der+Adrenalingruppe+%28p-Oxyphenyl%C3%A4thanolmethylamin+und+sein+Keton&rft.volume=136&rft.issue=%3Cspan+class%3D%22nowrap%22%3E3%E2%80%93%3C%2Fspan%3E4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E172-%3C%2Fspan%3E184&rft.date=1928&rft_id=info%3Adoi%2F10.1007%2Fbf01862149&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A21414110%23id-name%3DS2CID&rft.au=Ehrismann+O.%2C+Maloff+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-66"><span class="mw-cite-backlink"><b><a href="#cite_ref-66">^</a></b></span> <span class="reference-text">G. Kuschinsky (1930)). "Untersuchungen über Sympatol, einen adrenalinähnlichen Körper." <i>Naunyn-Schmiedebergs Archiv für Experimentelle Pathologie und Pharmakologie</i> <b>156</b> 290 - 308.</span> </li> <li id="cite_note-Lands-67"><span class="mw-cite-backlink">^ <a href="#cite_ref-Lands_67-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Lands_67-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLands_A._M.,_Grant_J._I.1952" class="citation journal cs1">Lands A. M., Grant J. I. (1952). "The vasopressor action and toxicity of cyclohexylethylamine derivatives". <i>The Journal of Pharmacology and Experimental Therapeutics</i>. <b>106</b> (3): <span class="nowrap">341–</span>345. <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/13000630">13000630</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Pharmacology+and+Experimental+Therapeutics&rft.atitle=The+vasopressor+action+and+toxicity+of+cyclohexylethylamine+derivatives&rft.volume=106&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E341-%3C%2Fspan%3E345&rft.date=1952&rft_id=info%3Apmid%2F13000630&rft.au=Lands+A.+M.%2C+Grant+J.+I.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-71"><span class="mw-cite-backlink"><b><a href="#cite_ref-71">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPapp_L._Szekeres1968" class="citation journal cs1">Papp L. Szekeres (1968). "The arrhythmogenic action of sympathomimetic amines". <i>European Journal of Pharmacology</i>. <b>3</b> (1): <span class="nowrap">4–</span>14. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0014-2999%2868%2990042-3">10.1016/0014-2999(68)90042-3</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/4968334">4968334</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Pharmacology&rft.atitle=The+arrhythmogenic+action+of+sympathomimetic+amines&rft.volume=3&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E4-%3C%2Fspan%3E14&rft.date=1968&rft_id=info%3Adoi%2F10.1016%2F0014-2999%2868%2990042-3&rft_id=info%3Apmid%2F4968334&rft.au=Papp+L.+Szekeres&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-73"><span class="mw-cite-backlink"><b><a href="#cite_ref-73">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSong_D.-K.,_Suh_H.-W.,_Jung_J.-S.,_Wie_M.-B.,_Son_K.-H.,_Kim_Y.-H.1996" class="citation journal cs1">Song D.-K., Suh H.-W., Jung J.-S., Wie M.-B., Son K.-H., Kim Y.-H. (1996). "Antidepressant-like effects of <i>p</i>-synephrine in mouse models of immobility tests". <i>Neuroscience Letters</i>. <b>214</b> (<span class="nowrap">2–</span>3): <span class="nowrap">107–</span>110. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0304-3940%2896%2912895-0">10.1016/0304-3940(96)12895-0</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/8878095">8878095</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:28440606">28440606</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neuroscience+Letters&rft.atitle=Antidepressant-like+effects+of+p-synephrine+in+mouse+models+of+immobility+tests&rft.volume=214&rft.issue=%3Cspan+class%3D%22nowrap%22%3E2%E2%80%93%3C%2Fspan%3E3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E107-%3C%2Fspan%3E110&rft.date=1996&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A28440606%23id-name%3DS2CID&rft_id=info%3Apmid%2F8878095&rft_id=info%3Adoi%2F10.1016%2F0304-3940%2896%2912895-0&rft.au=Song+D.-K.%2C+Suh+H.-W.%2C+Jung+J.-S.%2C+Wie+M.-B.%2C+Son+K.-H.%2C+Kim+Y.-H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-78"><span class="mw-cite-backlink"><b><a href="#cite_ref-78">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKim_K.-W.,_Kim_H.-D.,_Jung_J.-S.,_Woo_R.-S.,_Kim_H.-S.,_Suh_H.-W.,_Kim_Y.-H.,_Song_D.-K.2001" class="citation journal cs1">Kim K.-W., Kim H.-D., Jung J.-S., Woo R.-S., Kim H.-S., Suh H.-W., Kim Y.-H., Song D.-K. (2001). "Characterization of antidepressant-like effects of <i>p</i>-synephrine stereoisomers". <i>Naunyn-Schmiedeberg's Archives of Pharmacology</i>. <b>364</b> (1): <span class="nowrap">21–</span>26. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs002100100416">10.1007/s002100100416</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/11485034">11485034</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:12625027">12625027</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Naunyn-Schmiedeberg%27s+Archives+of+Pharmacology&rft.atitle=Characterization+of+antidepressant-like+effects+of+p-synephrine+stereoisomers&rft.volume=364&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E21-%3C%2Fspan%3E26&rft.date=2001&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A12625027%23id-name%3DS2CID&rft_id=info%3Apmid%2F11485034&rft_id=info%3Adoi%2F10.1007%2Fs002100100416&rft.au=Kim+K.-W.%2C+Kim+H.-D.%2C+Jung+J.-S.%2C+Woo+R.-S.%2C+Kim+H.-S.%2C+Suh+H.-W.%2C+Kim+Y.-H.%2C+Song+D.-K.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-80"><span class="mw-cite-backlink"><b><a href="#cite_ref-80">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBurgen_A._S._V.,_Iversen_L._L.1964" class="citation journal cs1">Burgen A. S. V., Iversen L. L. (1964). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1510671">"The inhibition of noradrenaline uptake by sympathomimetic amines in the rat isolated heart"</a>. <i>British Journal of Pharmacology and Chemotherapy</i>. <b>25</b> (1): <span class="nowrap">34–</span>49. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1476-5381.1965.tb01754.x">10.1111/j.1476-5381.1965.tb01754.x</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1510671">1510671</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19108208">19108208</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=British+Journal+of+Pharmacology+and+Chemotherapy&rft.atitle=The+inhibition+of+noradrenaline+uptake+by+sympathomimetic+amines+in+the+rat+isolated+heart&rft.volume=25&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E34-%3C%2Fspan%3E49&rft.date=1964&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1510671%23id-name%3DPMC&rft_id=info%3Apmid%2F19108208&rft_id=info%3Adoi%2F10.1111%2Fj.1476-5381.1965.tb01754.x&rft.au=Burgen+A.+S.+V.%2C+Iversen+L.+L.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1510671&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-81"><span class="mw-cite-backlink"><b><a href="#cite_ref-81">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWikberg_J._E._S.1978" class="citation journal cs1">Wikberg J. E. S. (1978). "Pharmacological classification of adrenergic α receptors in the guinea pig". <i>Nature</i>. <b>273</b> (5658): <span class="nowrap">164–</span>166. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1978Natur.273..164W">1978Natur.273..164W</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2F273164a0">10.1038/273164a0</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/25390">25390</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:4278917">4278917</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=Pharmacological+classification+of+adrenergic+%CE%B1+receptors+in+the+guinea+pig&rft.volume=273&rft.issue=5658&rft.pages=%3Cspan+class%3D%22nowrap%22%3E164-%3C%2Fspan%3E166&rft.date=1978&rft_id=info%3Adoi%2F10.1038%2F273164a0&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4278917%23id-name%3DS2CID&rft_id=info%3Apmid%2F25390&rft_id=info%3Abibcode%2F1978Natur.273..164W&rft.au=Wikberg+J.+E.+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-Brown-82"><span class="mw-cite-backlink">^ <a href="#cite_ref-Brown_82-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Brown_82-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBrown_C.M.,_McGrath_J.C.,_Midgley_J.M.,_Muir_A.G.B.,_O'Brien_J.W.,_Thonoor_C.M.,_Williams_C.M.,_Wilson_V.G.1988" class="citation journal cs1">Brown C.M., McGrath J.C., Midgley J.M., Muir A.G.B., O'Brien J.W., Thonoor C.M., Williams C.M., Wilson V.G. (1988). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1853804">"Activities of octopamine and synephrine stereoisomers on α-adrenoceptors"</a>. <i>British Journal of Pharmacology</i>. <b>93</b> (2): <span class="nowrap">417–</span>429. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1476-5381.1988.tb11449.x">10.1111/j.1476-5381.1988.tb11449.x</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1853804">1853804</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2833972">2833972</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=British+Journal+of+Pharmacology&rft.atitle=Activities+of+octopamine+and+synephrine+stereoisomers+on+%CE%B1-adrenoceptors&rft.volume=93&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E417-%3C%2Fspan%3E429&rft.date=1988&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1853804%23id-name%3DPMC&rft_id=info%3Apmid%2F2833972&rft_id=info%3Adoi%2F10.1111%2Fj.1476-5381.1988.tb11449.x&rft.au=Brown+C.M.%2C+McGrath+J.C.%2C+Midgley+J.M.%2C+Muir+A.G.B.%2C+O%27Brien+J.W.%2C+Thonoor+C.M.%2C+Williams+C.M.%2C+Wilson+V.G.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1853804&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-83"><span class="mw-cite-backlink"><b><a href="#cite_ref-83">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRuffolo_R._R.,_Waddell_J._E.1983" class="citation journal cs1">Ruffolo R. R., Waddell J. E. (1983). "Aromatic and benzylic hydroxyl substitution of imidazolines and phenethylamines: differences in activity at alpha-1 and alpha-2 adrenergic receptors". <i>The Journal of Pharmacology and Experimental Therapeutics</i>. <b>224</b> (3): <span class="nowrap">559–</span>566. <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/6131121">6131121</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Pharmacology+and+Experimental+Therapeutics&rft.atitle=Aromatic+and+benzylic+hydroxyl+substitution+of+imidazolines+and+phenethylamines%3A+differences+in+activity+at+alpha-1+and+alpha-2+adrenergic+receptors&rft.volume=224&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E559-%3C%2Fspan%3E566&rft.date=1983&rft_id=info%3Apmid%2F6131121&rft.au=Ruffolo+R.+R.%2C+Waddell+J.+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-86"><span class="mw-cite-backlink"><b><a href="#cite_ref-86">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHibino_T.,_Yuzurihara_M.,_Kase_Y.,_Takeda_A.2009" class="citation journal cs1">Hibino T., Yuzurihara M., Kase Y., Takeda A. (2009). <a rel="nofollow" class="external text" href="https://www.jstage.jst.go.jp/article/jphs/111/1/111_09077FP/_pdf">"Synephrine, a component of Evodiae Fructus, constricts isolated rat aorta via adrenergic and serotonergic receptors"</a>. <i>Journal of Pharmacological Sciences</i>. <b>111</b> (1): <span class="nowrap">73–</span>81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1254%2Fjphs.09077fp">10.1254/jphs.09077fp</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19721332">19721332</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Pharmacological+Sciences&rft.atitle=Synephrine%2C+a+component+of+Evodiae+Fructus%2C+constricts+isolated+rat+aorta+via+adrenergic+and+serotonergic+receptors&rft.volume=111&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E73-%3C%2Fspan%3E81&rft.date=2009&rft_id=info%3Adoi%2F10.1254%2Fjphs.09077fp&rft_id=info%3Apmid%2F19721332&rft.au=Hibino+T.%2C+Yuzurihara+M.%2C+Kase+Y.%2C+Takeda+A.&rft_id=https%3A%2F%2Fwww.jstage.jst.go.jp%2Farticle%2Fjphs%2F111%2F1%2F111_09077FP%2F_pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-87"><span class="mw-cite-backlink"><b><a href="#cite_ref-87">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJordan_R.,_Midgley_J._M.,_Thonoor_C._M.,_Williams_C._M.1987" class="citation journal cs1">Jordan R., Midgley J. M., Thonoor C. M., Williams C. M. (1987). "Beta-adrenergic activities of octopamine and synephrine stereoisomers on guinea-pig isolated atria and trachea". <i>J. Pharm. Pharmacol</i>. <b>39</b> (9): <span class="nowrap">752–</span>754. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.2042-7158.1987.tb06986.x">10.1111/j.2042-7158.1987.tb06986.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2890747">2890747</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:38557968">38557968</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Pharm.+Pharmacol.&rft.atitle=Beta-adrenergic+activities+of+octopamine+and+synephrine+stereoisomers+on+guinea-pig+isolated+atria+and+trachea&rft.volume=39&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E752-%3C%2Fspan%3E754&rft.date=1987&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A38557968%23id-name%3DS2CID&rft_id=info%3Apmid%2F2890747&rft_id=info%3Adoi%2F10.1111%2Fj.2042-7158.1987.tb06986.x&rft.au=Jordan+R.%2C+Midgley+J.+M.%2C+Thonoor+C.+M.%2C+Williams+C.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-89"><span class="mw-cite-backlink"><b><a href="#cite_ref-89">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCarpéné_C.,_Galitzky_J.,_Fontana_E.,_Atgié_C.,_Lafontan_M.,_Berlan_M.1999" class="citation journal cs1">Carpéné C., Galitzky J., Fontana E., Atgié C., Lafontan M., Berlan M. (1999). "Selective activation of β3-adrenoceptors by octopamine: comparative studies in mammalian fat cells". <i>Naunyn-Schmiedeberg's Archives of Pharmacology</i>. <b>359</b> (4): <span class="nowrap">310–</span>321. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fpl00005357">10.1007/pl00005357</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/10344530">10344530</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:34370879">34370879</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Naunyn-Schmiedeberg%27s+Archives+of+Pharmacology&rft.atitle=Selective+activation+of+%CE%B23-adrenoceptors+by+octopamine%3A+comparative+studies+in+mammalian+fat+cells&rft.volume=359&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E310-%3C%2Fspan%3E321&rft.date=1999&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A34370879%23id-name%3DS2CID&rft_id=info%3Apmid%2F10344530&rft_id=info%3Adoi%2F10.1007%2Fpl00005357&rft.au=Carp%C3%A9n%C3%A9+C.%2C+Galitzky+J.%2C+Fontana+E.%2C+Atgi%C3%A9+C.%2C+Lafontan+M.%2C+Berlan+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-90"><span class="mw-cite-backlink"><b><a href="#cite_ref-90">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMa_G.,_Bavadeka_S._A.,_Schaneberg_B._T.,_Khan_I._A.,_Feller_D._R.2010" class="citation journal cs1">Ma G., Bavadeka S. A., Schaneberg B. T., Khan I. A., Feller D. R. (2010). "Effects of synephrine and beta-phenylephrine on human alpha-adrenoreceptor subtypes". <i>Planta Medica</i>. <b>76</b> (10): <span class="nowrap">981–</span>986. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-0029-1240884">10.1055/s-0029-1240884</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/20217639">20217639</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:41387315">41387315</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Planta+Medica&rft.atitle=Effects+of+synephrine+and+beta-phenylephrine+on+human+alpha-adrenoreceptor+subtypes&rft.volume=76&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E981-%3C%2Fspan%3E986&rft.date=2010&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A41387315%23id-name%3DS2CID&rft_id=info%3Apmid%2F20217639&rft_id=info%3Adoi%2F10.1055%2Fs-0029-1240884&rft.au=Ma+G.%2C+Bavadeka+S.+A.%2C+Schaneberg+B.+T.%2C+Khan+I.+A.%2C+Feller+D.+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-pmid15860375-91"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid15860375_91-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLindemannHoener2005" class="citation journal cs1">Lindemann, Lothar; Hoener, Marius C. (2005). "A renaissance in trace amines inspired by a novel GPCR family". <i>Trends in Pharmacological Sciences</i>. <b>26</b> (5): <span class="nowrap">274–</span>81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.tips.2005.03.007">10.1016/j.tips.2005.03.007</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/15860375">15860375</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Trends+in+Pharmacological+Sciences&rft.atitle=A+renaissance+in+trace+amines+inspired+by+a+novel+GPCR+family&rft.volume=26&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E274-%3C%2Fspan%3E81&rft.date=2005&rft_id=info%3Adoi%2F10.1016%2Fj.tips.2005.03.007&rft_id=info%3Apmid%2F15860375&rft.aulast=Lindemann&rft.aufirst=Lothar&rft.au=Hoener%2C+Marius+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-92"><span class="mw-cite-backlink"><b><a href="#cite_ref-92">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWainscott_D._B.,_Little_S._P.,_Yin_T.,_Tu_Y.,_Rocco_V._P.,_He_J._X.,_Nelson_D._L.2007" class="citation journal cs1">Wainscott D. B., Little S. P., Yin T., Tu Y., Rocco V. P., He J. X., Nelson D. L. (2007). "Pharmacologic characterization of the cloned human Trace Amine-Associated Receptor1 (TAAR1) and evidence for species differences with the rat TAAR1". <i>Journal of Pharmacology and Experimental Therapeutics</i>. <b>320</b> (1): <span class="nowrap">475–</span>485. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fjpet.106.112532">10.1124/jpet.106.112532</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/17038507">17038507</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:10829497">10829497</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Pharmacology+and+Experimental+Therapeutics&rft.atitle=Pharmacologic+characterization+of+the+cloned+human+Trace+Amine-Associated+Receptor1+%28TAAR1%29+and+evidence+for+species+differences+with+the+rat+TAAR1&rft.volume=320&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E475-%3C%2Fspan%3E485&rft.date=2007&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A10829497%23id-name%3DS2CID&rft_id=info%3Apmid%2F17038507&rft_id=info%3Adoi%2F10.1124%2Fjpet.106.112532&rft.au=Wainscott+D.+B.%2C+Little+S.+P.%2C+Yin+T.%2C+Tu+Y.%2C+Rocco+V.+P.%2C+He+J.+X.%2C+Nelson+D.+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-93"><span class="mw-cite-backlink"><b><a href="#cite_ref-93">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHengstmann_J._H.,_Aulepp_H.1978" class="citation journal cs1">Hengstmann J. H., Aulepp H. (1978). "Pharmacokinetics and metabolism of <sup>3</sup>H-synephphrine". <i>Arzneimittelforschung</i>. <b>28</b>: <span class="nowrap">2326–</span>2331.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Arzneimittelforschung&rft.atitle=Pharmacokinetics+and+metabolism+of+%3Csup%3E3%3C%2Fsup%3EH-synephphrine&rft.volume=28&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2326-%3C%2Fspan%3E2331&rft.date=1978&rft.au=Hengstmann+J.+H.%2C+Aulepp+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-94"><span class="mw-cite-backlink"><b><a href="#cite_ref-94">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSuzuki_O.,_Matsumoto_T.,_Oya_M.,_Katsumata_Y.1979" class="citation journal cs1">Suzuki O., Matsumoto T., Oya M., Katsumata Y. (1979). "Oxidation of synephrine by type A and type B monoamine oxidase". <i>Experientia</i>. <b>35</b> (10): <span class="nowrap">1283–</span>1284. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fbf01963957">10.1007/bf01963957</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/499398">499398</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:6129913">6129913</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Experientia&rft.atitle=Oxidation+of+synephrine+by+type+A+and+type+B+monoamine+oxidase&rft.volume=35&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1283-%3C%2Fspan%3E1284&rft.date=1979&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A6129913%23id-name%3DS2CID&rft_id=info%3Apmid%2F499398&rft_id=info%3Adoi%2F10.1007%2Fbf01963957&rft.au=Suzuki+O.%2C+Matsumoto+T.%2C+Oya+M.%2C+Katsumata+Y.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-95"><span class="mw-cite-backlink"><b><a href="#cite_ref-95">^</a></b></span> <span class="reference-text">U. von Euler and G. Liljestrand (1929). <i>Skand. Arch. Physiol.</i> <b>55</b> 1.</span> </li> <li id="cite_note-96"><span class="mw-cite-backlink"><b><a href="#cite_ref-96">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPohle_F.,_Sarre_H.1940" class="citation journal cs1">Pohle F., Sarre H. (1940). "Der Wirkungsmechanismus eines neuen peripheren Kreislaufmittels im Vergleich mit Veritol und Sympatol beim Menschen". <i>Naunyn-Schmiedebergs Archiv für Experimentelle Pathologie und Pharmakologie</i>. <b>196</b> (<span class="nowrap">2–</span>5): <span class="nowrap">408–</span>430. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fbf01861124">10.1007/bf01861124</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:34593711">34593711</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Naunyn-Schmiedebergs+Archiv+f%C3%BCr+Experimentelle+Pathologie+und+Pharmakologie&rft.atitle=Der+Wirkungsmechanismus+eines+neuen+peripheren+Kreislaufmittels+im+Vergleich+mit+Veritol+und+Sympatol+beim+Menschen&rft.volume=196&rft.issue=%3Cspan+class%3D%22nowrap%22%3E2%E2%80%93%3C%2Fspan%3E5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E408-%3C%2Fspan%3E430&rft.date=1940&rft_id=info%3Adoi%2F10.1007%2Fbf01861124&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A34593711%23id-name%3DS2CID&rft.au=Pohle+F.%2C+Sarre+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-97"><span class="mw-cite-backlink"><b><a href="#cite_ref-97">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHeim_F1948" class="citation journal cs1">Heim F (1948). "Über die Blutdruckwirksamkeit von Sympatol an Menschen nach Vorbehandlung mit Ephedrin, Veritol und Pervitin". <i>Naunyn-Schmiedebergs Archiv für Experimentelle Pathologie und Pharmakologie</i>. <b>205</b> (<span class="nowrap">4–</span>5): <span class="nowrap">470–</span>479. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fbf00246173">10.1007/bf00246173</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:25139273">25139273</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Naunyn-Schmiedebergs+Archiv+f%C3%BCr+Experimentelle+Pathologie+und+Pharmakologie&rft.atitle=%C3%9Cber+die+Blutdruckwirksamkeit+von+Sympatol+an+Menschen+nach+Vorbehandlung+mit+Ephedrin%2C+Veritol+und+Pervitin&rft.volume=205&rft.issue=%3Cspan+class%3D%22nowrap%22%3E4%E2%80%93%3C%2Fspan%3E5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E470-%3C%2Fspan%3E479&rft.date=1948&rft_id=info%3Adoi%2F10.1007%2Fbf00246173&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A25139273%23id-name%3DS2CID&rft.au=Heim+F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-98"><span class="mw-cite-backlink"><b><a href="#cite_ref-98">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNathanson_M._H.,_Miller_H.1950" class="citation journal cs1">Nathanson M. H., Miller H. (1950). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1520549">"The effect of new drugs on the rhythmic function of the heart"</a>. <i>Calif. Med</i>. <b>72</b> (4): <span class="nowrap">215–</span>221. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1520549">1520549</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18731684">18731684</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Calif.+Med.&rft.atitle=The+effect+of+new+drugs+on+the+rhythmic+function+of+the+heart&rft.volume=72&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E215-%3C%2Fspan%3E221&rft.date=1950&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1520549%23id-name%3DPMC&rft_id=info%3Apmid%2F18731684&rft.au=Nathanson+M.+H.%2C+Miller+H.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1520549&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-Hoff-99"><span class="mw-cite-backlink">^ <a href="#cite_ref-Hoff_99-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Hoff_99-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHofstetterKreudervon_Bernuth1985" class="citation journal cs1">Hofstetter, R.; Kreuder, J.; von Bernuth, G. (1985). "The effect of oxedrine on the left ventricle and peripheral vascular resistance". <i>Arzneimittel-Forschung</i>. <b>35</b> (12): <span class="nowrap">1844–</span>6. <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/4096743">4096743</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Arzneimittel-Forschung&rft.atitle=The+effect+of+oxedrine+on+the+left+ventricle+and+peripheral+vascular+resistance&rft.volume=35&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1844-%3C%2Fspan%3E6&rft.date=1985&rft_id=info%3Apmid%2F4096743&rft.aulast=Hofstetter&rft.aufirst=R.&rft.au=Kreuder%2C+J.&rft.au=von+Bernuth%2C+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-100"><span class="mw-cite-backlink"><b><a href="#cite_ref-100">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTiefensee_K1932" class="citation journal cs1">Tiefensee K (1932). "Therapy of bronchial asthma with adrenalin and the adrenalin derivatives ephedrine and sympatol". <i>Journal of Allergy</i>. <b>4</b>: 81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0021-8707%2832%2990053-7">10.1016/s0021-8707(32)90053-7</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Allergy&rft.atitle=Therapy+of+bronchial+asthma+with+adrenalin+and+the+adrenalin+derivatives+ephedrine+and+sympatol&rft.volume=4&rft.pages=81&rft.date=1932&rft_id=info%3Adoi%2F10.1016%2Fs0021-8707%2832%2990053-7&rft.au=Tiefensee+K&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-101"><span class="mw-cite-backlink"><b><a href="#cite_ref-101">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFugh-BermanMyers2004" class="citation journal cs1">Fugh-Berman, Adriane; Myers, Adam (2004). "Citrus aurantium, an Ingredient of Dietary Supplements Marketed for Weight Loss: Current Status of Clinical and Basic Research". <i>Experimental Biology and Medicine</i>. <b>229</b> (8): <span class="nowrap">698–</span>704. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F153537020422900802">10.1177/153537020422900802</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/15337824">15337824</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:35942851">35942851</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Experimental+Biology+and+Medicine&rft.atitle=Citrus+aurantium%2C+an+Ingredient+of+Dietary+Supplements+Marketed+for+Weight+Loss%3A+Current+Status+of+Clinical+and+Basic+Research&rft.volume=229&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E698-%3C%2Fspan%3E704&rft.date=2004&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A35942851%23id-name%3DS2CID&rft_id=info%3Apmid%2F15337824&rft_id=info%3Adoi%2F10.1177%2F153537020422900802&rft.aulast=Fugh-Berman&rft.aufirst=Adriane&rft.au=Myers%2C+Adam&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-Stohs-102"><span class="mw-cite-backlink">^ <a href="#cite_ref-Stohs_102-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Stohs_102-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFStohs_S._J.,_Preuss_H._G.,_Shara_M.2011" class="citation journal cs1">Stohs S. J., Preuss H. G., Shara M. (2011). "The Safety of <i>Citrus aurantium</i> (Bitter Orange) and its primary protoalkaloid <i>p</i>-synephrine". <i>Phytotherapy Research</i>. <b>25</b> (10): <span class="nowrap">1421–</span>1428. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fptr.3490">10.1002/ptr.3490</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/21480414">21480414</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:32789083">32789083</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Phytotherapy+Research&rft.atitle=The+Safety+of+Citrus+aurantium+%28Bitter+Orange%29+and+its+primary+protoalkaloid+p-synephrine&rft.volume=25&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1421-%3C%2Fspan%3E1428&rft.date=2011&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A32789083%23id-name%3DS2CID&rft_id=info%3Apmid%2F21480414&rft_id=info%3Adoi%2F10.1002%2Fptr.3490&rft.au=Stohs+S.+J.%2C+Preuss+H.+G.%2C+Shara+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-104"><span class="mw-cite-backlink"><b><a href="#cite_ref-104">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFArbo_M._D.,_Schmitt_G._C.,_Limberger_M._F.,_Charão_M._F.,_Moro_Â._M.,_Ribeiro_G._L.,_Dallegrave_E.,_Garcia_S._C.,_Leal_M._B.,_Limberger_R._P.2009" class="citation journal cs1">Arbo M. D., Schmitt G. C., Limberger M. F., Charão M. F., Moro Â. M., Ribeiro G. L., Dallegrave E., Garcia S. C., Leal M. B., Limberger R. P. (2009). "Subchronic toxicity of <i>Citrus aurantium</i> L. (Rutaceae) extract and <i>p</i>-synephrine in mice". <i>Regulatory Toxicology and Pharmacology</i>. <b>54</b> (2): <span class="nowrap">114–</span>117. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.yrtph.2009.03.001">10.1016/j.yrtph.2009.03.001</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/19275924">19275924</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Regulatory+Toxicology+and+Pharmacology&rft.atitle=Subchronic+toxicity+of+Citrus+aurantium+L.+%28Rutaceae%29+extract+and+p-synephrine+in+mice&rft.volume=54&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E114-%3C%2Fspan%3E117&rft.date=2009&rft_id=info%3Adoi%2F10.1016%2Fj.yrtph.2009.03.001&rft_id=info%3Apmid%2F19275924&rft.au=Arbo+M.+D.%2C+Schmitt+G.+C.%2C+Limberger+M.+F.%2C+Char%C3%A3o+M.+F.%2C+Moro+%C3%82.+M.%2C+Ribeiro+G.+L.%2C+Dallegrave+E.%2C+Garcia+S.+C.%2C+Leal+M.+B.%2C+Limberger+R.+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-105"><span class="mw-cite-backlink"><b><a href="#cite_ref-105">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNasir_J._M.,_Durning_S._J.,_Ferguson_M.,_Barold_H._S.,_Haigney_M._C.2004" class="citation journal cs1">Nasir J. M., Durning S. J., Ferguson M., Barold H. S., Haigney M. C. (2004). <a rel="nofollow" class="external text" href="https://doi.org/10.4065%2F79.8.1059">"Exercise-induced syncope associated with QT prolongation and Ephedra-free Xenadrine"</a>. <i>Mayo Clinic Proceedings</i>. <b>79</b> (8): <span class="nowrap">1059–</span>1062. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.4065%2F79.8.1059">10.4065/79.8.1059</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15301335">15301335</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Mayo+Clinic+Proceedings&rft.atitle=Exercise-induced+syncope+associated+with+QT+prolongation+and+Ephedra-free+Xenadrine&rft.volume=79&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1059-%3C%2Fspan%3E1062&rft.date=2004&rft_id=info%3Adoi%2F10.4065%2F79.8.1059&rft_id=info%3Apmid%2F15301335&rft.au=Nasir+J.+M.%2C+Durning+S.+J.%2C+Ferguson+M.%2C+Barold+H.+S.%2C+Haigney+M.+C.&rft_id=https%3A%2F%2Fdoi.org%2F10.4065%252F79.8.1059&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-106"><span class="mw-cite-backlink"><b><a href="#cite_ref-106">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBouchard_N.,_Hoffman_R._S.2004" class="citation journal cs1">Bouchard N., Hoffman R. S. (2004). <a rel="nofollow" class="external text" href="https://doi.org/10.4065%2F79.12.1589-b">"Synephrine is not Neo-Synephrine"</a>. <i>Mayo Clinic Proceedings</i>. <b>79</b> (12): <span class="nowrap">1589–</span>1590. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.4065%2F79.12.1589-b">10.4065/79.12.1589-b</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15595351">15595351</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Mayo+Clinic+Proceedings&rft.atitle=Synephrine+is+not+Neo-Synephrine&rft.volume=79&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1589-%3C%2Fspan%3E1590&rft.date=2004&rft_id=info%3Adoi%2F10.4065%2F79.12.1589-b&rft_id=info%3Apmid%2F15595351&rft.au=Bouchard+N.%2C+Hoffman+R.+S.&rft_id=https%3A%2F%2Fdoi.org%2F10.4065%252F79.12.1589-b&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-107"><span class="mw-cite-backlink"><b><a href="#cite_ref-107">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBent_S.,_Padula_A.,_Neuhaus_J.2004" class="citation journal cs1">Bent S., Padula A., Neuhaus J. (2004). "Safety and efficacy of <i>Citrus aurantium</i> for weight loss". <i>The American Journal of Cardiology</i>. <b>94</b> (10): <span class="nowrap">1359–</span>1361. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.amjcard.2004.07.137">10.1016/j.amjcard.2004.07.137</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/15541270">15541270</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Cardiology&rft.atitle=Safety+and+efficacy+of+Citrus+aurantium+for+weight+loss&rft.volume=94&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1359-%3C%2Fspan%3E1361&rft.date=2004&rft_id=info%3Adoi%2F10.1016%2Fj.amjcard.2004.07.137&rft_id=info%3Apmid%2F15541270&rft.au=Bent+S.%2C+Padula+A.%2C+Neuhaus+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-108"><span class="mw-cite-backlink"><b><a href="#cite_ref-108">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBouchard_N._C.,_Howland_M._A.,_Greller_H._A.,_Hoffman_R._S.,_Nelson_L._S.2005" class="citation journal cs1">Bouchard N. C., Howland M. A., Greller H. A., Hoffman R. S., Nelson L. S. (2005). <a rel="nofollow" class="external text" href="https://doi.org/10.4065%2F80.4.541">"Ischemic stroke associated with use of an Ephedra-free dietary supplement containing synephrine"</a>. <i>Mayo Clinic Proceedings</i>. <b>80</b> (4): <span class="nowrap">541–</span>545. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.4065%2F80.4.541">10.4065/80.4.541</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15819293">15819293</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Mayo+Clinic+Proceedings&rft.atitle=Ischemic+stroke+associated+with+use+of+an+Ephedra-free+dietary+supplement+containing+synephrine&rft.volume=80&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E541-%3C%2Fspan%3E545&rft.date=2005&rft_id=info%3Adoi%2F10.4065%2F80.4.541&rft_id=info%3Apmid%2F15819293&rft.au=Bouchard+N.+C.%2C+Howland+M.+A.%2C+Greller+H.+A.%2C+Hoffman+R.+S.%2C+Nelson+L.+S.&rft_id=https%3A%2F%2Fdoi.org%2F10.4065%252F80.4.541&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-109"><span class="mw-cite-backlink"><b><a href="#cite_ref-109">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFirenzuoli_F.,_Gori_L.,_Galapai_C.2005" class="citation journal cs1">Firenzuoli F., Gori L., Galapai C. (2005). "Adverse reaction to an adrenergic herbal extract (<i>Citrus aurantium</i>)". <i>Phytomedicine</i>. <b>12</b> (3): <span class="nowrap">247–</span>248. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.phymed.2004.02.005">10.1016/j.phymed.2004.02.005</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15830849">15830849</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Phytomedicine&rft.atitle=Adverse+reaction+to+an+adrenergic+herbal+extract+%28Citrus+aurantium%29&rft.volume=12&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E247-%3C%2Fspan%3E248&rft.date=2005&rft_id=info%3Adoi%2F10.1016%2Fj.phymed.2004.02.005&rft_id=info%3Apmid%2F15830849&rft.au=Firenzuoli+F.%2C+Gori+L.%2C+Galapai+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-110"><span class="mw-cite-backlink"><b><a href="#cite_ref-110">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHaaz_S.,_Fontaine_K._R.,_Cutter_G.,_Limdi_N.,_Perumean-Chaney_S.,_Allison_D._B.2006" class="citation journal cs1">Haaz S., Fontaine K. R., Cutter G., Limdi N., Perumean-Chaney S., Allison D. B. (2006). "<i>Citrus aurantium</i> and synephrine alkaloids in the treatment of overweight and obesity: an update". <i>Obesity Reviews</i>. <b>7</b> (1): <span class="nowrap">79–</span>88. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1467-789x.2006.00195.x">10.1111/j.1467-789x.2006.00195.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16436104">16436104</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:13842012">13842012</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Obesity+Reviews&rft.atitle=Citrus+aurantium+and+synephrine+alkaloids+in+the+treatment+of+overweight+and+obesity%3A+an+update&rft.volume=7&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E79-%3C%2Fspan%3E88&rft.date=2006&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A13842012%23id-name%3DS2CID&rft_id=info%3Apmid%2F16436104&rft_id=info%3Adoi%2F10.1111%2Fj.1467-789x.2006.00195.x&rft.au=Haaz+S.%2C+Fontaine+K.+R.%2C+Cutter+G.%2C+Limdi+N.%2C+Perumean-Chaney+S.%2C+Allison+D.+B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-111"><span class="mw-cite-backlink"><b><a href="#cite_ref-111">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFThomas_J._E.,_Munir_J._A.,_McIntyre_P._Z.,_Ferguson_M._A.2009" class="citation journal cs1">Thomas J. E., Munir J. A., McIntyre P. Z., Ferguson M. A. (2009). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2801940">"STEMI in a 24-year-old man after use of a synephrine-containing dietary supplement: a case report and review of the literature"</a>. <i>Texas Heart Institute Journal</i>. <b>36</b> (6): <span class="nowrap">586–</span>90. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2801940">2801940</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20069086">20069086</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Texas+Heart+Institute+Journal&rft.atitle=STEMI+in+a+24-year-old+man+after+use+of+a+synephrine-containing+dietary+supplement%3A+a+case+report+and+review+of+the+literature&rft.volume=36&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E586-%3C%2Fspan%3E90&rft.date=2009&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2801940%23id-name%3DPMC&rft_id=info%3Apmid%2F20069086&rft.au=Thomas+J.+E.%2C+Munir+J.+A.%2C+McIntyre+P.+Z.%2C+Ferguson+M.+A.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2801940&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-112"><span class="mw-cite-backlink"><b><a href="#cite_ref-112">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFThomas_J._E.,_Munir_J._A.,_McIntyre_P._Z.,_Ferguson_M._A.2010" class="citation journal cs1">Thomas J. E., Munir J. A., McIntyre P. Z., Ferguson M. A. (2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2879205">"Lack of evidence that <i>p</i>-synephrine is responsible for STEMI"</a>. <i>Texas Heart Institute Journal</i>. <b>37</b> (3): <span class="nowrap">383–</span>384. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2879205">2879205</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20548833">20548833</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Texas+Heart+Institute+Journal&rft.atitle=Lack+of+evidence+that+p-synephrine+is+responsible+for+STEMI&rft.volume=37&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E383-%3C%2Fspan%3E384&rft.date=2010&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2879205%23id-name%3DPMC&rft_id=info%3Apmid%2F20548833&rft.au=Thomas+J.+E.%2C+Munir+J.+A.%2C+McIntyre+P.+Z.%2C+Ferguson+M.+A.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2879205&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-113"><span class="mw-cite-backlink"><b><a href="#cite_ref-113">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFStohs_S._J.2010" class="citation journal cs1">Stohs S. J. (2010). "Assessment of the adverse event reports associated with <i>Citrus aurantium</i> (bitter orange) from April 2004 to October 2009". <i>Journal of Functional Foods</i>. <b>2</b> (4): <span class="nowrap">235–</span>239. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.jff.2010.10.003">10.1016/j.jff.2010.10.003</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Functional+Foods&rft.atitle=Assessment+of+the+adverse+event+reports+associated+with+Citrus+aurantium+%28bitter+orange%29+from+April+2004+to+October+2009&rft.volume=2&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E235-%3C%2Fspan%3E239&rft.date=2010&rft_id=info%3Adoi%2F10.1016%2Fj.jff.2010.10.003&rft.au=Stohs+S.+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-114"><span class="mw-cite-backlink"><b><a href="#cite_ref-114">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEvans_P._D.1981" class="citation journal cs1">Evans P. D. (1981). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1245480">"Multiple receptor types for octopamine in the locust"</a>. <i>The Journal of Physiology</i>. <b>318</b>: <span class="nowrap">99–</span>122. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1113%2Fjphysiol.1981.sp013853">10.1113/jphysiol.1981.sp013853</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1245480">1245480</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6275071">6275071</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Physiology&rft.atitle=Multiple+receptor+types+for+octopamine+in+the+locust&rft.volume=318&rft.pages=%3Cspan+class%3D%22nowrap%22%3E99-%3C%2Fspan%3E122&rft.date=1981&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1245480%23id-name%3DPMC&rft_id=info%3Apmid%2F6275071&rft_id=info%3Adoi%2F10.1113%2Fjphysiol.1981.sp013853&rft.au=Evans+P.+D.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1245480&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-115"><span class="mw-cite-backlink"><b><a href="#cite_ref-115">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCarlson_A._D.1968" class="citation journal cs1">Carlson A. D. (1968). "Effect of drugs on luminescence in larval fireflies". <i>The Journal of Experimental Biology</i>. <b>49</b> (1): <span class="nowrap">195–</span>199. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1242%2Fjeb.49.1.195">10.1242/jeb.49.1.195</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/4386272">4386272</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Experimental+Biology&rft.atitle=Effect+of+drugs+on+luminescence+in+larval+fireflies&rft.volume=49&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E195-%3C%2Fspan%3E199&rft.date=1968&rft_id=info%3Adoi%2F10.1242%2Fjeb.49.1.195&rft_id=info%3Apmid%2F4386272&rft.au=Carlson+A.+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-116"><span class="mw-cite-backlink"><b><a href="#cite_ref-116">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBattelle_A.,_Kravitz_E._A.1978" class="citation journal cs1">Battelle A., Kravitz E. A. (1978). "Targets of octopamine action in the lobster: cyclic nucleotide changes and physiological effects in hemolymph, heart and exoskeletal muscle". <i>J. Pharmacol. Exp. Ther</i>. <b>205</b> (2): <span class="nowrap">438–</span>448. <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/347053">347053</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Pharmacol.+Exp.+Ther.&rft.atitle=Targets+of+octopamine+action+in+the+lobster%3A+cyclic+nucleotide+changes+and+physiological+effects+in+hemolymph%2C+heart+and+exoskeletal+muscle&rft.volume=205&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E438-%3C%2Fspan%3E448&rft.date=1978&rft_id=info%3Apmid%2F347053&rft.au=Battelle+A.%2C+Kravitz+E.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-117"><span class="mw-cite-backlink"><b><a href="#cite_ref-117">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBarrett_M.,_Orchard_I.1990" class="citation journal cs1">Barrett M., Orchard I. (1990). "Serotonin-induced elevation of cAMP levels in the epidermis of the blood-sucking bug, <i>Rhodnius prolixus</i>". <i>Journal of Insect Physiology</i>. <b>36</b> (9): <span class="nowrap">625–</span>633. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1990JInsP..36..625B">1990JInsP..36..625B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0022-1910%2890%2990066-o">10.1016/0022-1910(90)90066-o</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Insect+Physiology&rft.atitle=Serotonin-induced+elevation+of+cAMP+levels+in+the+epidermis+of+the+blood-sucking+bug%2C+Rhodnius+prolixus&rft.volume=36&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E625-%3C%2Fspan%3E633&rft.date=1990&rft_id=info%3Adoi%2F10.1016%2F0022-1910%2890%2990066-o&rft_id=info%3Abibcode%2F1990JInsP..36..625B&rft.au=Barrett+M.%2C+Orchard+I.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-118"><span class="mw-cite-backlink"><b><a href="#cite_ref-118">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRachinsky_A1994" class="citation journal cs1">Rachinsky A (1994). "Octopamine and serotonin influence on <i>corpora allata</i> activity in honey bee (<i>Apis mellifera</i>) larvae". <i>Journal of Insect Physiology</i>. <b>40</b> (7): <span class="nowrap">549–</span>554. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1994JInsP..40..549R">1994JInsP..40..549R</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0022-1910%2894%2990141-4">10.1016/0022-1910(94)90141-4</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Insect+Physiology&rft.atitle=Octopamine+and+serotonin+influence+on+corpora+allata+activity+in+honey+bee+%28Apis+mellifera%29+larvae&rft.volume=40&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E549-%3C%2Fspan%3E554&rft.date=1994&rft_id=info%3Adoi%2F10.1016%2F0022-1910%2894%2990141-4&rft_id=info%3Abibcode%2F1994JInsP..40..549R&rft.au=Rachinsky+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> <li id="cite_note-119"><span class="mw-cite-backlink"><b><a href="#cite_ref-119">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWoodring_J.,_Hoffmann_K._H.1994" class="citation journal cs1">Woodring J., Hoffmann K. H. (1994). "The effects of octopamine, dopamine and serotonin on juvenile hormone synthesis, In vitro, in the cricket, <i>Gryllus bimaculatus</i>". <i>Journal of Insect Physiology</i>. <b>40</b> (9): <span class="nowrap">797–</span>802. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1994JInsP..40..797W">1994JInsP..40..797W</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0022-1910%2894%2990009-4">10.1016/0022-1910(94)90009-4</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Insect+Physiology&rft.atitle=The+effects+of+octopamine%2C+dopamine+and+serotonin+on+juvenile+hormone+synthesis%2C+In+vitro%2C+in+the+cricket%2C+Gryllus+bimaculatus&rft.volume=40&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E797-%3C%2Fspan%3E802&rft.date=1994&rft_id=info%3Adoi%2F10.1016%2F0022-1910%2894%2990009-4&rft_id=info%3Abibcode%2F1994JInsP..40..797W&rft.au=Woodring+J.%2C+Hoffmann+K.+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASynephrine" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline 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style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Major excitatory /<br />inhibitory systems</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%;font-weight:normal;">Glutamate system</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/Agmatine" title="Agmatine">Agmatine</a></li> <li><a href="/wiki/Aspartic_acid" title="Aspartic acid">Aspartic acid (aspartate)</a></li> <li><a href="/wiki/Glutamate_(neurotransmitter)" title="Glutamate (neurotransmitter)">Glutamic acid (glutamate)</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">Glutathione</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/S-Nitrosoglutathione" title="S-Nitrosoglutathione">GSNO</a></li> <li><a href="/wiki/Glutathione_disulfide" title="Glutathione disulfide">GSSG</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/N-Acetylaspartic_acid" title="N-Acetylaspartic acid">NAA</a></li> <li><a href="/wiki/N-Acetylaspartylglutamic_acid" title="N-Acetylaspartylglutamic acid">NAAG</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">GABA system</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/GABA" title="GABA">GABA</a></li> <li><a href="/wiki/%CE%93-Amino-%CE%B2-hydroxybutyric_acid" title="Γ-Amino-β-hydroxybutyric acid">GABOB</a></li> <li><a href="/wiki/%CE%93-Hydroxybutyric_acid" title="Γ-Hydroxybutyric acid">GHB</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">Glycine system</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/Alanine" title="Alanine">α-Alanine</a></li> <li><a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Hypotaurine" title="Hypotaurine">Hypotaurine</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;"><a href="/wiki/GHB_receptor" title="GHB receptor">GHB system</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/%CE%93-Hydroxybutyric_acid" title="Γ-Hydroxybutyric acid">GHB</a></li> <li><a href="/wiki/T-HCA" title="T-HCA">T-HCA (GHC)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Biogenic_amine" title="Biogenic amine">Biogenic amines</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:4em;font-weight:normal; text-align: center;">Monoamines</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-OHM</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Adrenaline" title="Adrenaline">Epinephrine (adrenaline)</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">NAS (normelatonin)</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Trace amines</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine">N-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methyltryptamine" title="N-Methyltryptamine">N-Methyltryptamine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine"><i>m</i>-Octopamine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a class="mw-selflink selflink">Synephrine</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Neuropeptide" title="Neuropeptide">Neuropeptides</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Neuropeptides" title="Template:Neuropeptides">here</a> instead.</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Lipid" title="Lipid">Lipid</a>-derived</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 id="Endocannabinoids33" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Endocannabinoids</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/2-Arachidonoylglycerol" title="2-Arachidonoylglycerol">2-AG</a></li> <li><a href="/wiki/2-Arachidonyl_glyceryl_ether" title="2-Arachidonyl glyceryl ether">2-AGE (noladin ether)</a></li> <li><a href="/w/index.php?title=2-Arachidonoyl_lysophosphatidylinositol&action=edit&redlink=1" class="new" title="2-Arachidonoyl lysophosphatidylinositol (page does not exist)">2-ALPI</a></li> <li><a href="/wiki/2-Oleoylglycerol" title="2-Oleoylglycerol">2-OG</a></li> <li><a href="/wiki/Arachidonoyl_serotonin" title="Arachidonoyl serotonin">AA-5-HT</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide (AEA)</a></li> <li><a href="/wiki/Docosatetraenoylethanolamide" title="Docosatetraenoylethanolamide">DEA</a></li> <li><a href="/wiki/Lysophosphatidylinositol" title="Lysophosphatidylinositol">LPI</a></li> <li><a href="/wiki/N-Arachidonoyl_dopamine" title="N-Arachidonoyl dopamine">NADA</a></li> <li><a href="/wiki/N-Arachidonylglycine" title="N-Arachidonylglycine">NAGly</a></li> <li><a href="/wiki/Oleoylethanolamide" title="Oleoylethanolamide">OEA</a></li> <li><a href="/wiki/Oleamide" title="Oleamide">Oleamide</a></li> <li><a href="/wiki/Palmitoylethanolamide" title="Palmitoylethanolamide">PEA</a></li> <li><a href="/wiki/RVD-Hp%CE%B1" title="RVD-Hpα">RVD-Hpα</a></li> <li><a href="/wiki/Stearoylethanolamide" title="Stearoylethanolamide">SEA</a></li> <li><a href="/wiki/Virodhamine" title="Virodhamine">Virodhamine (O-AEA)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Neurosteroid" title="Neurosteroid">Neurosteroids</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">Nucleobase</a>-derived</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 id="Nucleosides11" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Nucleosides</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 id="Adenosine_system20" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a> system</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/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Vitamin" title="Vitamin">Vitamin</a>-derived</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"></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">Miscellaneous</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 id="Cholinergic_system18" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Cholinergic system</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/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Gasotransmitters16" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Gasotransmitters</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/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide (CO)</a></li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide (H<sub>2</sub>S)</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide (NO)</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Candidates10" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Candidates</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/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia (NH<sub>3</sub>)</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide (COS)</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide (N<sub>2</sub>O)</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide (SO<sub>2</sub>)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /></div><div role="navigation" class="navbox" aria-labelledby="Cardiac_stimulants_excluding_cardiac_glycosides_(C01C)544" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cardiac_stimulants_excluding_cardiac_glycosides" title="Template:Cardiac stimulants excluding cardiac glycosides"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cardiac_stimulants_excluding_cardiac_glycosides" title="Template talk:Cardiac stimulants excluding cardiac glycosides"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cardiac_stimulants_excluding_cardiac_glycosides" title="Special:EditPage/Template:Cardiac stimulants excluding cardiac glycosides"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cardiac_stimulants_excluding_cardiac_glycosides_(C01C)544" style="font-size:114%;margin:0 4em"><a href="/wiki/Cardiac_stimulant" title="Cardiac stimulant">Cardiac stimulants</a> excluding cardiac glycosides (<a href="/wiki/ATC_code_C01#C01C" title="ATC code C01">C01C</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Adrenergic</a> and<br /><a href="/wiki/Dopaminergic" title="Dopaminergic">dopaminergic</a> agents</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adrenergic_agonist" title="Adrenergic agonist">Adrenergic agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">α</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Midodrine" title="Midodrine">Midodrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a></li> <li><a class="mw-selflink selflink">Oxedrine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">β</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Prenalterol" title="Prenalterol">Prenalterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">mixed</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amezinium_metilsulfate" title="Amezinium metilsulfate">Amezinium metilsulfate</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a> #</li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Norepinephrine_(medication)" title="Norepinephrine (medication)">Norepinephrine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dopamine_agonist" title="Dopamine agonist">Dopamine agonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fenoldopam" title="Fenoldopam">Fenoldopam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Both</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Docarpamine" title="Docarpamine">Docarpamine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a> #</li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine">Octopamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Unknown/ungrouped</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a href="/wiki/Dimetofrine" title="Dimetofrine">Dimetofrine</a></li> <li><a href="/wiki/Gepefrine" title="Gepefrine">Gepefrine</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">Phosphodiesterase inhibitors</a> (<a href="/wiki/PDE3_inhibitor" title="PDE3 inhibitor">PDE3I</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amrinone" title="Amrinone">Amrinone</a></li> <li><a href="/wiki/Bucladesine" title="Bucladesine">Bucladesine</a></li> <li><a href="/wiki/Enoximone" title="Enoximone">Enoximone</a></li> <li><a href="/wiki/Milrinone" title="Milrinone">Milrinone</a></li> <li><a href="/wiki/Vesnarinone" title="Vesnarinone">Vesnarinone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other cardiac stimulants</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Angiotensinamide" title="Angiotensinamide">Angiotensinamide</a></li> <li><a href="/wiki/Levosimendan" title="Levosimendan">Levosimendan</a></li> <li><a href="/wiki/Omecamtiv_mecarbil" title="Omecamtiv mecarbil">Omecamtiv mecarbil</a></li> <li><a href="/wiki/Pimobendan" title="Pimobendan">Pimobendan</a></li> <li><a href="/wiki/Xamoterol" title="Xamoterol">Xamoterol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Adrenergic_receptor_modulators685" 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_modulators685" 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">α<sub>1</sub></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, <i>N</i>-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 href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a class="mw-selflink selflink">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">α<sub>2</sub></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, <i>N</i>-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/Butopamine" title="Butopamine">Butopamine</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, <i>N</i>-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><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></li> <li><i><a href="/wiki/Template:Dopamine_receptor_modulators" title="Template:Dopamine receptor modulators">Dopaminergics</a></i></li> <li><i><a href="/wiki/Template:Serotonin_receptor_modulators" title="Template:Serotonin receptor modulators">Serotonergics</a></i></li> <li><i><a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a></i></li> <li><i><a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">Monoamine releasing agents</a></i></li> <li><i><a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></i></li> <li><i><a href="/wiki/Template:Monoamine_neurotoxins" class="mw-redirect" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></i></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="Trace_amine-associated_receptor_modulators1416" 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:TAAR_modulators" title="Template:TAAR modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:TAAR_modulators" title="Template talk:TAAR modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:TAAR_modulators" title="Special:EditPage/Template:TAAR modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Trace_amine-associated_receptor_modulators1416" style="font-size:114%;margin:0 4em"><a href="/wiki/Trace_amine-associated_receptor" title="Trace amine-associated receptor">Trace amine-associated receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Trace_amine-associated_receptor_1" class="mw-redirect" title="Trace amine-associated receptor 1"><abbr title="Trace amine-associated receptor 1">TAAR1</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 Trace amine-associated receptor 1</span></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%;text-align: center;"><a href="/wiki/Agonist" title="Agonist">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%;text-align: center;"><a href="/wiki/Trace_amine" title="Trace amine">Endogenous</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/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">Monoamine neurotransmitters</a> <ul><li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a></li></ul></li> <li><a href="/wiki/Trace_amine" title="Trace amine">Trace amines</a> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li> <li><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methyltyramine" title="N-Methyltyramine"><i>N</i>-Methyltyramine</a></li> <li><a href="/wiki/Meta-Octopamine" class="mw-redirect" title="Meta-Octopamine"><i>m</i>-Octopamine</a></li> <li><a href="/wiki/Para-Octopamine" class="mw-redirect" title="Para-Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">β-Phenethylamine</a></li> <li><a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a class="mw-selflink selflink">Synephrine</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Para-Tyramine" class="mw-redirect" title="Para-Tyramine"><i>p</i>-Tyramine</a></li></ul></li> <li>Others <ul><li><a href="/wiki/Cyclohexylamine" title="Cyclohexylamine">Cyclohexylamine</a></li> <li><a href="/w/index.php?title=Isoamylamine&action=edit&redlink=1" class="new" title="Isoamylamine (page does not exist)">Isoamylamine</a></li> <li><a href="/wiki/Trimethylamine" title="Trimethylamine">Trimethylamine</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Exogenous" class="mw-redirect" title="Exogenous">Exogenous</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/2C-B" title="2C-B">2C-B</a></li> <li><a href="/wiki/2C-B-Fly" class="mw-redirect" title="2C-B-Fly">2C-B-Fly</a></li> <li><a href="/wiki/2C-E" title="2C-E">2C-E</a></li> <li><a href="/wiki/2C-H" title="2C-H">2C-H</a></li> <li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li> <li><a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a></li> <li><a href="/wiki/A-77636" title="A-77636">A-77636</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-Aminoindane</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/w/index.php?title=AP163&action=edit&redlink=1" class="new" title="AP163 (page does not exist)">AP163</a></li> <li><a href="/wiki/Apomorphine" title="Apomorphine">Apomorphine</a></li> <li><a href="/wiki/Asenapine" title="Asenapine">Asenapine</a></li> <li><a href="/wiki/Bromocriptine" title="Bromocriptine">Bromocriptine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Clonidine" title="Clonidine">Clonidine</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">Dihydroergotamine</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">Dimethyltryptamine</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-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/N,N-Dimethylphenethylamine" title="N,N-Dimethylphenethylamine"><i>N</i>,<i>N</i>-Dimethylphenethylamine</a></li> <li><a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">Ergometrine</a></li> <li><a href="/wiki/Fenoldopam" title="Fenoldopam">Fenoldopam</a></li> <li><a href="/wiki/Fenoterol" title="Fenoterol">Fenoterol</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-Fluoroamphetamine</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/Halostachine" title="Halostachine">Halostachine</a></li> <li><a href="/wiki/Higenamine" title="Higenamine">Higenamine</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine (norpholedrine)</a></li> <li><a href="/wiki/Idazoxan" title="Idazoxan">Idazoxan</a></li> <li><a href="/wiki/5-Iodo-2-aminoindane" class="mw-redirect" title="5-Iodo-2-aminoindane">5-Iodo-2-aminoindane</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isopropyloctopamine" class="mw-redirect" title="Isopropyloctopamine">Isopropyloctopamine</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/LK00764" title="LK00764">LK00764</a></li> <li><a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">LSD</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyaminoindane" class="mw-redirect" title="Methylenedioxyaminoindane">MDAI</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metergoline" title="Metergoline">Metergoline</a></li> <li><a href="/wiki/N-Methyl-2-AI" class="mw-redirect" title="N-Methyl-2-AI"><i>N</i>-Methyl-2-AI</a></li> <li><a href="/wiki/2-Methylphenethylamine" title="2-Methylphenethylamine">2-Methylphenethylamine</a></li> <li><a href="/wiki/3-Methylphenethylamine" title="3-Methylphenethylamine">3-Methylphenethylamine</a></li> <li><a href="/wiki/4-Methylphenethylamine" title="4-Methylphenethylamine">4-Methylphenethylamine</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/3-Methoxyamphetamine" title="3-Methoxyamphetamine">MMA</a></li> <li><a href="/wiki/MPTP" title="MPTP">MPTP</a></li> <li><a href="/wiki/Naphazoline" title="Naphazoline">Naphazoline</a></li> <li><a href="/wiki/Nomifensine" title="Nomifensine">Nomifensine</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/Phentolamine" title="Phentolamine">Phentolamine</a></li> <li><a href="/wiki/O-Phenyl-3-iodotyramine" title="O-Phenyl-3-iodotyramine"><i>o</i>-PIT</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">Psilocin</a></li> <li><a href="/wiki/Ralmitaront" title="Ralmitaront">Ralmitaront (RG-7906, RO6889450)</a></li> <li><a href="/wiki/RG-7351" title="RG-7351">RG-7351</a></li> <li><a href="/wiki/RG-7410" title="RG-7410">RG-7410</a></li> <li><a href="/wiki/RO5073012" title="RO5073012">RO5073012</a></li> <li><a href="/wiki/RO5166017" title="RO5166017">RO5166017</a></li> <li><a href="/wiki/RO5203648" title="RO5203648">RO5203648</a></li> <li><a href="/wiki/RO5256390" title="RO5256390">RO5256390</a></li> <li><a href="/wiki/RO5263397" title="RO5263397">RO5263397</a></li> <li><a href="/w/index.php?title=S18616&action=edit&redlink=1" class="new" title="S18616 (page does not exist)">S18616</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline (<small>L</small>-deprenyl)</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Tolazoline" title="Tolazoline">Tolazoline</a></li> <li><a href="/wiki/Ulotaront" title="Ulotaront">Ulotaront (SEP-363856)</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/Receptor_antagonist" title="Receptor antagonist">Antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Compound_22_(TAAR1_antagonist)" title="Compound 22 (TAAR1 antagonist)">Compound 22</a></li> <li><a href="/wiki/EPPTB" title="EPPTB">EPPTB (RO-5212773)</a></li> <li><a href="/wiki/RTI-7470-44" title="RTI-7470-44">RTI-7470-44</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Inverse_agonist" title="Inverse agonist">Inverse 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/EPPTB" title="EPPTB">EPPTB (RO-5212773)</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/Trace_amine-associated_receptor_5" class="mw-redirect" title="Trace amine-associated receptor 5"><abbr title="Trace amine-associated receptor 5">TAAR5</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 Trace amine-associated receptor 5</span></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 id="Agonists32" scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Agonist" title="Agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N,N-Dimethylethylamine" title="N,N-Dimethylethylamine"><i>N</i>,<i>N</i>-Dimethylethylamine</a></li> <li><a href="/wiki/Trimethylamine" title="Trimethylamine">Trimethylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Inverse_agonist" title="Inverse agonist">Inverse 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/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><small><i><b>Notes:</b></i> (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the <a href="/wiki/Trace_amine#List_of_trace_amines" title="Trace amine">List of trace amines</a>, <a href="/wiki/Trace_amine-associated_receptor" title="Trace amine-associated receptor">TAAR</a>, and <a href="/wiki/TAAR1" title="TAAR1">TAAR1</a> pages. <i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></small></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Phenethylamines353" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Phenethylamines" title="Template:Phenethylamines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenethylamines" title="Template talk:Phenethylamines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenethylamines" title="Special:EditPage/Template:Phenethylamines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Phenethylamines353" style="font-size:114%;margin:0 4em"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Psychedelics:</i> <a href="/wiki/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a></li> <li><a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a></li> <li><a href="/wiki/25D-NBOMe" title="25D-NBOMe">25D-NBOMe</a></li> <li><a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a></li> <li><a href="/wiki/25N-NBOMe" title="25N-NBOMe">25N-NBOMe</a></li> <li><a href="/wiki/2C-B" title="2C-B">2C-B</a></li> <li><a href="/w/index.php?title=2C-B-AN&action=edit&redlink=1" class="new" title="2C-B-AN (page does not exist)">2C-B-AN</a></li> <li><a href="/w/index.php?title=2C-Bn&action=edit&redlink=1" class="new" title="2C-Bn (page does not exist)">2C-Bn</a></li> <li><a href="/wiki/2C-Bu" title="2C-Bu">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-iBu" title="2C-iBu">2C-iBu</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="/wiki/2C-Ph" title="2C-Ph">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="/wiki/2C-T-27" title="2C-T-27">2C-T-27</a></li> <li><a href="/wiki/2C-T-28" title="2C-T-28">2C-T-28</a></li> <li><a href="/w/index.php?title=2C-T-30&action=edit&redlink=1" class="new" title="2C-T-30 (page does not exist)">2C-T-30</a></li> <li><a href="/w/index.php?title=2C-T-31&action=edit&redlink=1" class="new" title="2C-T-31 (page does not exist)">2C-T-31</a></li> <li><a href="/w/index.php?title=2C-T-32&action=edit&redlink=1" class="new" title="2C-T-32 (page does not exist)">2C-T-32</a></li> <li><a href="/wiki/2C-T-33" title="2C-T-33">2C-T-33</a></li> <li><a href="/wiki/2C-tBu" title="2C-tBu">2C-tBu</a></li> <li><a href="/wiki/2C-TFE" title="2C-TFE">2C-TFE</a></li> <li><a href="/wiki/2C-TFM" title="2C-TFM">2C-TFM</a></li> <li><a href="/wiki/2C-YN" title="2C-YN">2C-YN</a></li> <li><a href="/wiki/2C-V" title="2C-V">2C-V</a></li> <li><a href="/wiki/Allylescaline" title="Allylescaline">Allylescaline</a></li> <li><a href="/wiki/DESOXY" title="DESOXY">DESOXY</a></li> <li><a href="/wiki/Escaline" title="Escaline">Escaline</a></li> <li><a href="/wiki/Isoproscaline" title="Isoproscaline">Isoproscaline</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Macromerine" title="Macromerine">Macromerine</a></li> <li><a href="/wiki/3-Methoxy-4-ethoxyphenethylamine" title="3-Methoxy-4-ethoxyphenethylamine">MEPEA</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metaescaline" title="Metaescaline">Metaescaline</a></li> <li><a href="/wiki/Methallylescaline" title="Methallylescaline">Methallylescaline</a></li> <li><a href="/wiki/Proscaline" title="Proscaline">Proscaline</a></li> <li><a href="/wiki/Psi-2C-T-4" class="mw-redirect" title="Psi-2C-T-4">Psi-2C-T-4</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li></ul> <ul><li><i>Stimulants:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">α-Methylphenethylamine</a> (amphetamine)</li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/M-Methylphenethylamine" class="mw-redirect" title="M-Methylphenethylamine"><i>m</i>-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li> <li><a href="/wiki/O-Methylphenethylamine" class="mw-redirect" title="O-Methylphenethylamine"><i>o</i>-Methylphenethylamine</a></li> <li><a href="/wiki/P-Methylphenethylamine" class="mw-redirect" title="P-Methylphenethylamine"><i>p</i>-Methylphenethylamine</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li></ul> <ul><li><i>Entactogens:</i> <a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a><br /><i>Others:</i> <a href="/wiki/Biscaline" title="Biscaline">Biscaline</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Buscaline" title="Buscaline">Buscaline</a></li> <li><a href="/wiki/3,4-Dimethoxyphenethylamine" title="3,4-Dimethoxyphenethylamine">DMPEA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Psychedelics:</i> <a href="/wiki/3C-AL" title="3C-AL">3C-AL</a></li> <li><a href="/wiki/3C-BZ" title="3C-BZ">3C-BZ</a></li> <li><a href="/wiki/3C-E" title="3C-E">3C-E</a></li> <li><a href="/wiki/3C-MAL" title="3C-MAL">3C-MAL</a></li> <li><a href="/wiki/3C-P" title="3C-P">3C-P</a></li> <li><a href="/wiki/Aleph_(psychedelic)" title="Aleph (psychedelic)">Aleph</a></li> <li><a href="/wiki/Beatrice_(psychedelic)" title="Beatrice (psychedelic)">Beatrice</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/4-Methyl-2,5-methoxyphenylcyclopropylamine" class="mw-redirect" title="4-Methyl-2,5-methoxyphenylcyclopropylamine">DMCPA</a></li> <li><a href="/wiki/DMMDA" title="DMMDA">DMMDA</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-fluoroethylamphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-fluoroethylamphetamine">DOEF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-nitroamphetamine" title="2,5-Dimethoxy-4-nitroamphetamine">DON</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-propylamphetamine" title="2,5-Dimethoxy-4-propylamphetamine">DOPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-trifluoromethylamphetamine" title="2,5-Dimethoxy-4-trifluoromethylamphetamine">DOTFM</a></li> <li><a href="/wiki/Ganesha_(psychedelic)" title="Ganesha (psychedelic)">Ganesha</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDA-2" title="MMDA-2">MMDA-2</a></li> <li><a href="/wiki/Psi-DOM" class="mw-redirect" title="Psi-DOM">Psi-DOM</a></li> <li><a href="/wiki/Trimethoxyamphetamine" class="mw-redirect" title="Trimethoxyamphetamine">TMA</a></li> <li><a href="/wiki/Tetramethoxyamphetamine" class="mw-redirect" title="Tetramethoxyamphetamine">TeMA</a></li> <li><a href="/wiki/ZDCM-04" title="ZDCM-04">ZDCM-04</a><br /><i>Stimulants:</i> <a href="/wiki/2-Fluoroamphetamine" title="2-Fluoroamphetamine">2-FA</a></li> <li><a href="/wiki/2-Fluoromethamphetamine" title="2-Fluoromethamphetamine">2-FMA</a></li> <li><a href="/wiki/3-Fluoroamphetamine" title="3-Fluoroamphetamine">3-FA</a></li> <li><a href="/wiki/3-Fluoromethamphetamine" title="3-Fluoromethamphetamine">3-FMA</a></li> <li><a href="/wiki/Acridorex" title="Acridorex">Acridorex</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a>, <a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/Benfluorex" title="Benfluorex">Benfluorex</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Fencamfamin" title="Fencamfamin">Fencamfamin</a></li> <li><a href="/wiki/Fencamine" title="Fencamine">Fencamine</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a> (<a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a>)</li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flucetorex" title="Flucetorex">Flucetorex</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Formetorex" title="Formetorex">Formetorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Gepefrine" title="Gepefrine">Gepefrine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Isopropylamphetamine" title="Isopropylamphetamine">Isopropylamphetamine</a></li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> (Dextromethamphetamine, <a href="/wiki/Levomethamphetamine" title="Levomethamphetamine">Levomethamphetamine</a>)</li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/L-Norpseudoephedrine" title="L-Norpseudoephedrine"><span style="font-size: 85%;">L</span>-Norpseudoephedrine</a></li> <li><a href="/wiki/N,alpha-Diethylphenylethylamine" class="mw-redirect" title="N,alpha-Diethylphenylethylamine">N,alpha-Diethylphenylethylamine</a></li> <li><a href="/wiki/Oxifentorex" title="Oxifentorex">Oxifentorex</a></li> <li><a href="/wiki/Oxilofrine" title="Oxilofrine">Oxilofrine</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">PBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">PCA</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">PFA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">PFMA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">PIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxy-N-ethylamphetamine" title="Para-Methoxy-N-ethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxy-N-methylamphetamine" class="mw-redirect" title="Para-Methoxy-N-methylamphetamine">PMMA</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a 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><br /><i>Entactogens:</i> <a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APB" title="5-APB">5-APB</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-EAPB" title="5-EAPB">5-EAPB</a></li> <li><a href="/wiki/5-IT" class="mw-redirect" title="5-IT">5-IT</a></li> <li><a href="/wiki/5-MAPB" title="5-MAPB">5-MAPB</a></li> <li><a href="/wiki/5-MAPDB" title="5-MAPDB">5-MAPDB</a></li> <li><a href="/wiki/6-APB" title="6-APB">6-APB</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Chloro-MDMA" title="6-Chloro-MDMA">6-Chloro-MDMA</a></li> <li><a href="/wiki/6-EAPB" title="6-EAPB">6-EAPB</a></li> <li><a href="/wiki/6-IT" class="mw-redirect" title="6-IT">6-IT</a></li> <li><a href="/wiki/6-MAPB" title="6-MAPB">6-MAPB</a></li> <li><a href="/wiki/6-MAPDB" title="6-MAPDB">6-MAPDB</a></li> <li><a href="/wiki/Ethylidenedioxyamphetamine" class="mw-redirect" title="Ethylidenedioxyamphetamine">EDA</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/2,3-Methylenedioxyamphetamine" title="2,3-Methylenedioxyamphetamine">2,3-MDA</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">3,4-MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxylmethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxylmethamphetamine">MDHMA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a><br /><i>Others:</i> <a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">3,4-DCA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/DiFMDA" class="mw-redirect" title="DiFMDA">DiFMDA</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl"><span style="font-size: 85%;">D</span>-Deprenyl</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phentermine" title="Phentermine">Phentermines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a><br /><i>Entactogens:</i> <a href="/wiki/Methylenedioxyphentermine" class="mw-redirect" title="Methylenedioxyphentermine">MDPH</a></li> <li><a href="/wiki/Methylenedioxymethylphentermine" class="mw-redirect" title="Methylenedioxymethylphentermine">MDMPH</a><br /><i>Others:</i> <a href="/wiki/Cericlamine" title="Cericlamine">Cericlamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Cathinones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/3-Fluoromethcathinone" title="3-Fluoromethcathinone">3-FMC</a></li> <li><a href="/wiki/4-Methylcathinone" title="4-Methylcathinone">4-MC</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">4-BMC</a></li> <li><a href="/wiki/4-Chloromethcathinone" title="4-Chloromethcathinone">4-CMC</a></li> <li><a href="/wiki/4-Ethylmethcathinone" title="4-Ethylmethcathinone">4-EMC</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">4-FMC</a></li> <li><a href="/wiki/4-Methylethcathinone" title="4-Methylethcathinone">4-MEC</a></li> <li><a href="/wiki/4-Methylbuphedrone" title="4-Methylbuphedrone">4-MeMABP</a></li> <li><a href="/wiki/4-Methylpentedrone" title="4-Methylpentedrone">4-MPD</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Benzedrone" title="Benzedrone">Benzedrone</a></li> <li><a href="/wiki/Brephedrone" class="mw-redirect" title="Brephedrone">Brephedrone</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Dimethylcathinone" title="Dimethylcathinone">Dimethylcathinone</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/N-Ethylbuphedrone" title="N-Ethylbuphedrone">NEB</a></li> <li><a href="/wiki/N-Ethylhexedrone" title="N-Ethylhexedrone">N-Ethylhexedrone</a></li> <li><a href="/wiki/N-Ethylpentedrone" title="N-Ethylpentedrone">N-Ethylpentedrone</a></li> <li><a href="/wiki/Pentedrone" title="Pentedrone">Pentedrone</a></li> <li><a href="/wiki/Pentylone" title="Pentylone">Pentylone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a><br /><i>Entactogens:</i> <a href="/wiki/3,4-Dimethylmethcathinone" title="3,4-Dimethylmethcathinone">3,4-DMMC</a></li> <li><a href="/wiki/3-Methylmethcathinone" title="3-Methylmethcathinone">3-MMC</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Methylenedioxycathinone" title="Methylenedioxycathinone">Methylenedioxycathinone</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Propylone" title="Propylone">Propylone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Entactogens:</i> <a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Methylphenylisobutylamine" title="4-Methylphenylisobutylamine">4-MAB</a></li> <li><a href="/wiki/Ariadne_(psychedelic)" class="mw-redirect" title="Ariadne (psychedelic)">Ariadne</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/MBDB" title="MBDB">MBDB</a><br /><i>Stimulants:</i> <a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">Phenylalkylpyrrolidines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/Alpha-Pyrrolidinobutiophenone" class="mw-redirect" title="Alpha-Pyrrolidinobutiophenone">α-PBP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinohexiophenone" class="mw-redirect" title="Alpha-Pyrrolidinohexiophenone">α-PHP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopropiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopropiophenone">α-PPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiophenone">α-PVP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinobutiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinobutiophenone">MDPBP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinopropiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinopropiophenone">MDPPP</a></li> <li><a href="/wiki/3,4-Methylenedioxypyrovalerone" class="mw-redirect" title="3,4-Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">4-MePBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">4-MePHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">4-MePPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopropiophenone" title="4'-Methoxy-α-pyrrolidinopropiophenone">MOPPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopentiophenone" title="4'-Methoxy-α-pyrrolidinopentiophenone">MOPVP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">MPBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">MPHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">MPPP</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">PEP</a></li> <li><a href="/wiki/Prolintane" title="Prolintane">Prolintane</a></li> <li><a href="/wiki/Pyrovalerone" title="Pyrovalerone">Pyrovalerone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Catecholamine" title="Catecholamine">Catecholamines</a><br /><span style="font-size: 85%;">(and close relatives)</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/6-Hydroxydopamine" class="mw-redirect" title="6-Hydroxydopamine">6-OHDA</a></li> <li><a href="/wiki/Alpha-Methyldopamine" class="mw-redirect" title="Alpha-Methyldopamine">a-Me-DA</a></li> <li><a href="/wiki/Alpha-Methyltyramine" class="mw-redirect" title="Alpha-Methyltyramine">a-Me-TRA</a></li> <li><a href="/wiki/Adrenochrome" title="Adrenochrome">Adrenochrome</a></li> <li><a href="/wiki/Ciladopa" title="Ciladopa">Ciladopa</a></li> <li><a href="/wiki/D-DOPA" title="D-DOPA"><span style="font-size: 85%;">D</span>-DOPA</a> (Dextrodopa)</li> <li><a href="/wiki/Dimetofrine" title="Dimetofrine">Dimetofrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Epinephrine_(neurotransmitter)" class="mw-redirect" title="Epinephrine (neurotransmitter)">Epinephrine</a></li> <li><a href="/wiki/Epinine" class="mw-redirect" title="Epinine">Epinine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Fenclonine" title="Fenclonine">Fenclonine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA"><span style="font-size: 85%;">L</span>-DOPA</a> (Levodopa)</li> <li><a href="/wiki/L-DOPS" class="mw-redirect" title="L-DOPS"><span style="font-size: 85%;">L</span>-DOPS</a> (Droxidopa)</li> <li><a href="/wiki/L-Phenylalanine" class="mw-redirect" title="L-Phenylalanine"><span style="font-size: 85%;">L</span>-Phenylalanine</a></li> <li><a href="/wiki/L-Tyrosine" class="mw-redirect" title="L-Tyrosine"><span style="font-size: 85%;">L</span>-Tyrosine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Metaterol" title="Metaterol">Metaterol</a></li> <li><a href="/wiki/Metirosine" class="mw-redirect" title="Metirosine">Metirosine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/N,N-Dimethyldopamine" title="N,N-Dimethyldopamine">N,N-Dimethyldopamine</a></li> <li><a href="/wiki/Nordefrin" class="mw-redirect" title="Nordefrin">Nordefrin</a> (<a href="/wiki/Levonordefrin" class="mw-redirect" title="Levonordefrin">Levonordefrin</a>)</li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a> (<i>m</i>-Octopamine)</li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a class="mw-selflink selflink">Synephrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AL-LAD" title="AL-LAD">AL-LAD</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Desvenlafaxine" title="Desvenlafaxine">Desvenlafaxine</a></li> <li><a href="/wiki/Diphenidine" title="Diphenidine">Diphenidine</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/ETH-LAD" title="ETH-LAD">ETH-LAD</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fluorolintane" title="Fluorolintane">Fluorolintane</a></li> <li><a href="/wiki/Hexapradol" title="Hexapradol">Hexapradol</a></li> <li><a href="/wiki/IP-LAD" class="mw-redirect" title="IP-LAD">IP-LAD</a></li> <li><a href="/wiki/Lysergic_acid_amide" class="mw-redirect" title="Lysergic acid amide">Lysergic acid amide</a></li> <li><a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">Lysergic acid 2-butyl amide</a></li> <li><a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">Lysergic acid 2,4-dimethylazetidide</a></li> <li><a href="/wiki/LSD" title="LSD">Lysergic acid diethylamide</a></li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Methoxphenidine" title="Methoxphenidine">Methoxphenidine</a></li> <li><a href="/wiki/MT-45" title="MT-45">MT-45</a></li> <li><a href="/wiki/PARGY-LAD" title="PARGY-LAD">PARGY-LAD</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a href="/wiki/PRO-LAD" title="PRO-LAD">PRO-LAD</a></li> <li><a href="/wiki/Pronethalol" title="Pronethalol">Pronethalol</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a> (<a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a>)</li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Thiamphenicol" title="Thiamphenicol">Thiamphenicol</a></li> <li><a href="/wiki/UWA-101" title="UWA-101">UWA-101</a></li> <li><a href="/wiki/Venlafaxine" title="Venlafaxine">Venlafaxine</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img 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