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class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Names</span> </div> </a> <ul id="toc-Names-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Other_drugs" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Other_drugs"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Other drugs</span> </div> </a> <ul id="toc-Other_drugs-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Notes</span> </div> </a> <ul id="toc-Notes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reference_notes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reference_notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Reference notes</span> </div> </a> <ul id="toc-Reference_notes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">4-Hydroxyamphetamine</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/4-Hidroxianfetamina" title="4-Hidroxianfetamina – Spanish" lang="es" hreflang="es" data-title="4-Hidroxianfetamina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DB%B4-%D9%87%DB%8C%D8%AF%D8%B1%D9%88%DA%A9%D8%B3%DB%8C%E2%80%8C%D8%A2%D9%85%D9%81%D8%AA%D8%A7%D9%85%DB%8C%D9%86" title="۴-هیدروکسی‌آمفتامین – Persian" lang="fa" hreflang="fa" data-title="۴-هیدروکسی‌آمفتامین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%8E%E3%83%AB%E3%83%95%E3%82%A9%E3%83%AC%E3%83%89%E3%83%AA%E3%83%B3" title="ノルフォレドリン – Japanese" lang="ja" hreflang="ja" data-title="ノルフォレドリン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/4-Hidroksiamfetamin" title="4-Hidroksiamfetamin – Serbian" lang="sr" hreflang="sr" data-title="4-Hidroksiamfetamin" 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/Hidroksiamfetamin" title="Hidroksiamfetamin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Hidroksiamfetamin" 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-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine – Vietnamese" lang="vi" hreflang="vi" data-title="4-Hydroxyamphetamine" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q5955531#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div 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item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </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"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Group of stereoisomers</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"Hydroxyamfetamine" redirects here. For other uses, see <a href="/wiki/Hydroxyamphetamine" title="Hydroxyamphetamine">Hydroxyamphetamine</a>.</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title">Hydroxyamphetamine<br /><span style="font-size:85%; font-weight:normal;"><abbr title="International nonproprietary name">INN</abbr>:</span> Hydroxyamfetamine</caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:P-Hydroxyamphetamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/P-Hydroxyamphetamine.svg/225px-P-Hydroxyamphetamine.svg.png" decoding="async" width="225" height="92" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/P-Hydroxyamphetamine.svg/338px-P-Hydroxyamphetamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c7/P-Hydroxyamphetamine.svg/450px-P-Hydroxyamphetamine.svg.png 2x" data-file-width="1144" data-file-height="466" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Paredrine, Paremyd, Pedrolon, Mycadrine, Paredrinex, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">4-Hydroxyamphetamine; 4-HA; Hydroxyamfetamine; Oxamphetamine; Norpholedrine; <i>para</i>-Hydroxyamphetamine; α-Methyltyramine; Methyltyramine, Hydroxyamphetamine (<a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name">USAN</a> <small><abbr title="United States">US</abbr></small>)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Eye_drop" title="Eye drop">Eye drops</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><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>None</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">4-(2-aminopropyl)phenol</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=103-86-6">103-86-6</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/3651">3651</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.3525.html">3525</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/FQR280JW2N">FQR280JW2N</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL1546">ChEMBL1546</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID3023134">DTXSID3023134</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q5955531#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.002.866">100.002.866</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q5955531#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>9</sub><span title="Hydrogen">H</span><sub>13</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002151209000000000♠"></span>151.209</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=NC%28C%29Cc1ccc%28O%29cc1">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">NC(C)Cc1ccc(O)cc1</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3<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></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:GIKNHHRFLCDOEU-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=606168923&page2=4-Hydroxyamphetamine">(verify)</a></span></span></td></tr></tbody></table> <p><b>Hydroxyamphetamine</b>, also known as <b>4-hydroxyamphetamine</b> or <b>norpholedrine</b> and sold under the brand names <b>Paredrine</b> and <b>Paremyd</b> among others, is a <a href="/wiki/Sympathomimetic_drug" title="Sympathomimetic drug">sympathomimetic</a> <a href="/wiki/Medication" title="Medication">medication</a> used in <a href="/wiki/Eye_drop" title="Eye drop">eye drops</a> to <a href="/wiki/Mydriasis" title="Mydriasis">dilate the pupil</a> for <a href="/wiki/Eye_examination" title="Eye examination">eye examinations</a>.<sup id="cite_ref-Elks2014_1-0" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_2-0" class="reference"><a href="#cite_note-MortonHall2012-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2004_3-0" class="reference"><a href="#cite_note-IndexNominum2004-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DrugBank_4-0" class="reference"><a href="#cite_note-DrugBank-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Hydroxyamfetamine acts as a <a href="/wiki/Norepinephrine_releasing_agent" title="Norepinephrine releasing agent">norepinephrine releasing agent</a> and hence is an indirectly acting sympathomimetic.<sup id="cite_ref-Lepore1985_5-0" class="reference"><a href="#cite_note-Lepore1985-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Cho1978_6-0" class="reference"><a href="#cite_note-Cho1978-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It is a <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">substituted phenethylamine</a> and <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">amphetamine</a>.<sup id="cite_ref-DrugBank_4-1" class="reference"><a href="#cite_note-DrugBank-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Hydroxyamphetamine appeared to remain marketed only in the <a href="/wiki/Czech_Republic" title="Czech Republic">Czech Republic</a> as of 2004.<sup id="cite_ref-IndexNominum2004_3-1" class="reference"><a href="#cite_note-IndexNominum2004-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=4-Hydroxyamphetamine&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydroxyamphetamine is used in <a href="/wiki/Eye_drops" class="mw-redirect" title="Eye drops">eye drops</a> to dilate the <a href="/wiki/Pupil" title="Pupil">pupil</a> (a process called <a href="/wiki/Mydriasis" title="Mydriasis">mydriasis</a>) so that the back of the eye can be examined. This is a <a href="/wiki/Diagnostic_test" class="mw-redirect" title="Diagnostic test">diagnostic test</a> for <a href="/wiki/Horner%27s_syndrome" title="Horner's syndrome">Horner's syndrome</a>. Patients with Horner's syndrome exhibit <a href="/wiki/Anisocoria" title="Anisocoria">anisocoria</a> brought about by lesions on the nerves that connect to the <a href="/wiki/Nasociliary_nerve" title="Nasociliary nerve">nasociliary</a> branch of the <a href="/wiki/Ophthalmic_nerve" title="Ophthalmic nerve">ophthalmic nerve</a>.<sup id="cite_ref-Walton2003_7-0" class="reference"><a href="#cite_note-Walton2003-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Application of hydroxyamphetamine to the eye can indicate whether the lesion is <a href="/wiki/Preganglionic_nerve_fibers" title="Preganglionic nerve fibers">preganglionic</a> or <a href="/wiki/Postganglionic_nerve_fibers" title="Postganglionic nerve fibers">postganglionic</a> based on the pupil's response. If the pupil dilates, the lesion is preganglionic. If the pupil does not dilate, the lesion is postganglionic.<sup id="cite_ref-Walton2003_7-1" class="reference"><a href="#cite_note-Walton2003-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Hydroxyamphetamine has some limitations to its use as a diagnostic tool. If it is intended as an immediate follow up to another mydriatic drug (<a href="/wiki/Cocaine" title="Cocaine">cocaine</a> or <a href="/wiki/Apraclonidine" title="Apraclonidine">apraclonidine</a>), then the patient must wait anywhere from a day to a week before hydroxyamphetamine can be administered.<sup id="cite_ref-Davagnanam2013_8-0" class="reference"><a href="#cite_note-Davagnanam2013-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lepore1985_5-1" class="reference"><a href="#cite_note-Lepore1985-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It also has the tendency to falsely localize lesions. False localization can arise in cases of acute onset; in cases where a postganglionic lesion is present, but the nerve still responds to residual norepinephrine; or in cases in which unrelated nerve damage masks the presence of a preganglionic lesion.<sup id="cite_ref-Walton2003_7-2" class="reference"><a href="#cite_note-Walton2003-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Davagnanam2013_8-1" class="reference"><a href="#cite_note-Davagnanam2013-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=4-Hydroxyamphetamine&action=edit&section=2" title="Edit section: Available forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydroxyamphetamine is a component of two controlled (prescription only), name-brand ophthalmic mydriatics: Paredrine and Paremyd. Paredrine consists of a 1% solution of hydroxyamphetamine hydrobromide<sup id="cite_ref-SlamovitsGlaser1999_9-0" class="reference"><a href="#cite_note-SlamovitsGlaser1999-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 543">: 543 </span></sup> while Paremyd consists of a combination of 1% hydroxyamphetamine hydrobromide and 0.25% <a href="/wiki/Tropicamide" title="Tropicamide">tropicamide</a>.<sup id="cite_ref-OrangeBook_10-0" class="reference"><a href="#cite_note-OrangeBook-10"><span class="cite-bracket">[</span>10<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=4-Hydroxyamphetamine&action=edit&section=3" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=4-Hydroxyamphetamine&action=edit&section=4" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Like amphetamine, hydroxyamphetamine is an agonist of human <a href="/wiki/TAAR1" title="TAAR1">TAAR1</a>.<sup id="cite_ref-LewinMillerGilmour2011_11-0" class="reference"><a href="#cite_note-LewinMillerGilmour2011-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Hydroxyamphetamine acts as an <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">indirect sympathomimetic</a> and <a href="/wiki/Norepinephrine_releasing_agent" title="Norepinephrine releasing agent">induces the release of norepinephrine</a> which leads to <a href="/wiki/Mydriasis" title="Mydriasis">mydriasis</a> (pupil dilation).<sup id="cite_ref-Lepore1985_5-2" class="reference"><a href="#cite_note-Lepore1985-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Cho1978_6-1" class="reference"><a href="#cite_note-Cho1978-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>It additionally decreases metabolism of <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> and certain other <a href="/wiki/Monoamine" class="mw-redirect" title="Monoamine">monoamines</a> by inhibiting the activity of <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidases</a> (MAOs), particularly type A (<a href="/wiki/MAO-A" class="mw-redirect" title="MAO-A">MAO-A</a>).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2017)">citation needed</span></a></i>]</sup> The inhibition of MAO-A prevents metabolism of serotonin and <a href="/wiki/Catecholamines" class="mw-redirect" title="Catecholamines">catecholamines</a> in the <a href="/wiki/Chemical_synapse" title="Chemical synapse">presynaptic terminal</a>, and thus increases the amount of neurotransmitters available for release into the <a href="/wiki/Synaptic_cleft" class="mw-redirect" title="Synaptic cleft">synaptic cleft</a>.<sup id="cite_ref-NakagawasaiAraiSatoh2004_12-0" class="reference"><a href="#cite_note-NakagawasaiAraiSatoh2004-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=4-Hydroxyamphetamine&action=edit&section=5" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydroxyamphetamine is a major <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> of <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a> and a minor metabolite of <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>. In humans, amphetamine is metabolized to hydroxyamphetamine by <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a>, which is a member of the <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> superfamily and is found in the <a href="/wiki/Liver" title="Liver">liver</a>.<sup id="cite_ref-MarkowitzPatrick2001_13-0" class="reference"><a href="#cite_note-MarkowitzPatrick2001-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HaefelyBartholiniPletscher1976_14-0" class="reference"><a href="#cite_note-HaefelyBartholiniPletscher1976-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> 4-Hydroxyamphetamine is then metabolized by <a href="/wiki/Dopamine_%CE%B2-hydroxylase" class="mw-redirect" title="Dopamine β-hydroxylase">dopamine β-hydroxylase</a> into <a href="/wiki/4-hydroxynorephedrine" class="mw-redirect" title="4-hydroxynorephedrine">4-hydroxynorephedrine</a> or <a href="/wiki/Elimination_(pharmacology)" title="Elimination (pharmacology)">eliminated</a> in the <a href="/wiki/Urine" title="Urine">urine</a>.<sup id="cite_ref-Cho1978_6-2" class="reference"><a href="#cite_note-Cho1978-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="skin-invert-image"> <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:687px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: aliceblue;margin-bottom:3px;">Metabolic pathways of amphetamine in humans<sup id="cite_ref-amphetamine_metabolism_23-0" class="reference"><a href="#cite_note-amphetamine_metabolism-23"><span class="cite-bracket">[</span>sources 1<span class="cite-bracket">]</span></a></sup></div> <div style="position:relative; width:685px; height:375px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:-10px; top:3px; width:700px; position:absolute"> <span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/File:Amph_pathway.svg" title="commons:File:Amph pathway.svg"><img alt="Graphic of several routes of amphetamine metabolism" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Amph_pathway.svg/700px-Amph_pathway.svg.png" decoding="async" width="700" height="386" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Amph_pathway.svg/1050px-Amph_pathway.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/74/Amph_pathway.svg/1400px-Amph_pathway.svg.png 2x" data-file-width="725" data-file-height="400" /></a></span> </div> <div style="text-align:center; font-size:16px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_2x350" style="position:absolute; left:2px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/4-Hydroxyphenylacetone" title="4-Hydroxyphenylacetone">4-Hydroxyphenylacetone</a></span></div> <div id="annotation_210x350" style="position:absolute; left:210px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylacetone" title="Phenylacetone">Phenylacetone</a></span></div> <div id="annotation_380x350" style="position:absolute; left:380px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Benzoic_acid" title="Benzoic acid">Benzoic acid</a></span></div> <div id="annotation_560x350" style="position:absolute; left:560px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Hippuric_acid" title="Hippuric acid">Hippuric acid</a></span></div> <div id="annotation_45x220" style="position:absolute; left:45px; top:220px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> </span></div> <div id="annotation_300x220" style="position:absolute; left:300px; top:220px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Norephedrine</a></span></div> <div id="annotation_255x90" style="position:absolute; left:255px; top:90px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a class="mw-selflink selflink">4-Hydroxyamphetamine</a></span></div> <div id="annotation_490x90" style="position:absolute; left:490px; top:90px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/P-Hydroxynorephedrine" title="P-Hydroxynorephedrine">4-Hydroxynorephedrine</a></span></div> <div id="annotation_145x115" style="position:absolute; left:145px; top:115px; font-size:10px; font-size:10; line-height:12px;"><span style="background-color:transparent; color:inherit;">Para-<br />Hydroxylation</span></div> <div id="annotation_384x115" style="position:absolute; left:384px; top:115px; font-size:10px; font-size:10; line-height:12px;"><span style="background-color:transparent; color:inherit;">Para-<br />Hydroxylation</span></div> <div id="annotation_150x294" style="position:absolute; left:150px; top:294px; font-size:10px; font-size:10; line-height:12px;"><span style="background-color:transparent; color:inherit;">Para-<br />Hydroxylation</span></div> <div id="annotation_151x138" style="position:absolute; left:151px; top:138px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a></span></div> <div id="annotation_390x138" style="position:absolute; left:390px; top:138px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a></span></div> <div id="annotation_150x330" style="position:absolute; left:150px; top:330px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;">unidentified</span></div> <div id="annotation_190x165" style="position:absolute; left:190px; top:165px; font-size:10px; font-size:10; line-height:12px;"><span style="background-color:transparent; color:inherit;">Beta-<br />Hydroxylation</span></div> <div id="annotation_415x25" style="position:absolute; left:415px; top:25px; font-size:10px; font-size:10; line-height:12px;"><span style="background-color:transparent; color:inherit;">Beta-<br />Hydroxylation</span></div> <div id="annotation_206x195" style="position:absolute; left:206px; top:195px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">DBH</a></span></div> <div id="annotation_428x55" style="position:absolute; left:428px; top:55px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">DBH</a><br /><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>note 1<span class="cite-bracket">]</span></a></sup></span></div> <div id="annotation_210x220" style="position:absolute; left:210px; top:220px; font-size:10px; font-size:10; line-height:12px;"><span style="background-color:transparent; color:inherit;">Oxidative<br />Deamination</span></div> <div id="annotation_220x242" style="position:absolute; left:220px; top:242px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Flavin-containing_monooxygenase_3" title="Flavin-containing monooxygenase 3">FMO3</a></span></div> <div id="annotation_330x307" style="position:absolute; left:330px; top:307px; font-size:10px; font-size:10; line-height:12px;"><span style="background-color:transparent; color:inherit;">Oxidation</span></div> <div id="annotation_323x330" style="position:absolute; left:323px; top:330px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;">unidentified</span></div> <div id="annotation_478x293" style="position:absolute; left:478px; top:293px; font-size:10px; font-size:10; line-height:12px;"><span style="background-color:transparent; color:inherit;">Glycine<br />Conjugation</span></div> <div id="annotation_480x330" style="position:absolute; left:480px; top:330px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Butyrate%E2%80%94CoA_ligase" title="Butyrate—CoA ligase">XM-ligase</a><br /><a href="/wiki/Glycine_N-acyltransferase" title="Glycine N-acyltransferase">GLYAT</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/18px-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/27px-Interactive_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/36px-Interactive_icon.svg.png 2x" data-file-width="133" data-file-height="200" /></span></span></div>In humans, 4-hydroxyamphetamine is formed from <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a> metabolism of amphetamine; 4-hydroxyamphetamine may subsequently be metabolized by <a href="/wiki/Dopamine_%CE%B2-hydroxylase" class="mw-redirect" title="Dopamine β-hydroxylase">dopamine β-hydroxylase</a> into <a href="/wiki/4-hydroxynorephedrine" class="mw-redirect" title="4-hydroxynorephedrine">4-hydroxynorephedrine</a>.</div> </div> </div> </td></tr></tbody></table> </div> <p><br /> </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=4-Hydroxyamphetamine&action=edit&section=6" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydroxyamphetamine, also known as 4-hydroxy-α-methylphenethylamine, 4-hydroxyamphetamine, or α-methyltyramine, is a <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">substituted phenethylamine</a> and <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">amphetamine</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a>. It is the 4-<a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxylated</a> <a href="/wiki/Structural_analog" title="Structural analog">analogue</a> of <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>, the <i>N</i>-<a href="/wiki/Demethylation" title="Demethylation">demethylated</a> analogue of <a href="/wiki/Pholedrine" title="Pholedrine">pholedrine</a> (4-hydroxy-<i>N</i>-methylamphetamine), and the α-methylated analogue of <a href="/wiki/Tyramine" title="Tyramine">tyramine</a> (4-hydroxyphenethylamine). Other analogues include <a href="/wiki/%CE%91-methyldopamine" class="mw-redirect" title="Α-methyldopamine">α-methyldopamine</a>, <a href="/wiki/Corbadrine" title="Corbadrine">corbadrine</a> (levonordefrin; α-methylnorepinephrine), and <a href="/wiki/Dioxifedrine" title="Dioxifedrine">dioxifedrine</a> (α-methylepinephrine). </p><p>It has a predicted <a href="/wiki/Partition_coefficient" title="Partition coefficient">log P</a> of 0.58 to 1.4.<sup id="cite_ref-PubChem_28-0" class="reference"><a href="#cite_note-PubChem-28"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DrugBank_4-2" class="reference"><a href="#cite_note-DrugBank-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ChemSpider_29-0" class="reference"><a href="#cite_note-ChemSpider-29"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>Hydroxyamphetamine is used <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">pharmaceutically</a> as the <a href="/wiki/Hydrobromide" title="Hydrobromide">hydrobromide</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a>.<sup id="cite_ref-Elks2014_1-1" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=4-Hydroxyamphetamine&action=edit&section=7" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydroxyamphetamine was first <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesized</a> by 1910.<sup id="cite_ref-Elks2014_1-2" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>In the 1990s, the trade name rights, patents, and <a href="/wiki/New_drug_application" class="mw-redirect" title="New drug application">new drug applications</a> (NDAs) for Paredrine and Paremyd were exchanged among a few different manufacturers after a shortage of the raw material required for their production, which caused both drugs to be indefinitely removed from the market.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Around 1997, <a href="/wiki/Akorn" title="Akorn">Akorn, Inc.</a>, obtained the rights to both Paredrine and Paremyd,<sup id="cite_ref-Akorn_31-0" class="reference"><a href="#cite_note-Akorn-31"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> and in 2002, the company reintroduced Paremyd to the market as a fast acting ophthalmic mydriatic agent.<sup id="cite_ref-OrangeBook_10-1" class="reference"><a href="#cite_note-OrangeBook-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Akorn-2_32-0" class="reference"><a href="#cite_note-Akorn-2-32"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lurcott2002_33-0" class="reference"><a href="#cite_note-Lurcott2002-33"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>In 2004, hydroxyamphetamine appeared to remain marketed only in the <a href="/wiki/Czech_Republic" title="Czech Republic">Czech Republic</a>.<sup id="cite_ref-IndexNominum2004_3-2" class="reference"><a href="#cite_note-IndexNominum2004-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=4-Hydroxyamphetamine&action=edit&section=8" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Names">Names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=4-Hydroxyamphetamine&action=edit&section=9" title="Edit section: Names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>Hydroxyamphetamine</i> is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of the drug and its <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name</span> and <a href="/wiki/D%C3%A9nomination_Commune_Fran%C3%A7aise" title="Dénomination Commune Française"><abbr title="Dénomination Commune Française">DCF</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dénomination Commune Française</span>, while <i>hydroxyamfetamine</i> is its <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip International Nonproprietary Name</span>.<sup id="cite_ref-Elks2014_1-3" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_2-1" class="reference"><a href="#cite_note-MortonHall2012-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2004_3-3" class="reference"><a href="#cite_note-IndexNominum2004-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In the case of the <a href="/wiki/Hydrobromide" title="Hydrobromide">hydrobromide</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a>, its generic name is <i>hydroxyamphetamine hydrobromide</i> and this is its <a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name"><abbr title="United States Adopted Name">USAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Adopted Name</span>.<sup id="cite_ref-Elks2014_1-4" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_2-2" class="reference"><a href="#cite_note-MortonHall2012-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2004_3-4" class="reference"><a href="#cite_note-IndexNominum2004-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is also known by synonyms including <i>methyltyramine</i>, <i>norpholedrine</i>, and <i>oxamphetamine</i>.<sup id="cite_ref-Elks2014_1-5" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_2-3" class="reference"><a href="#cite_note-MortonHall2012-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2004_3-5" class="reference"><a href="#cite_note-IndexNominum2004-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PubChem_28-1" class="reference"><a href="#cite_note-PubChem-28"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> The drug is sold under brand names including <i>Paredrine</i>, <i>Paredrinex</i>, <i>Paremyd</i>, <i>Pedrolon</i>, and <i>Mycadrine</i>.<sup id="cite_ref-Elks2014_1-6" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2004_3-6" class="reference"><a href="#cite_note-IndexNominum2004-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Other_drugs">Other drugs</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=4-Hydroxyamphetamine&action=edit&section=10" title="Edit section: Other drugs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>4-Hydroxyamphetamine is also a <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> of <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a> and certain other amphetamines.<sup id="cite_ref-MortonHall2012_2-4" class="reference"><a href="#cite_note-MortonHall2012-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=4-Hydroxyamphetamine&action=edit&section=11" title="Edit section: Notes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><span class="nowrap">4-Hydroxyamphetamine</span> has been shown to be metabolized into <span class="nowrap">4-hydroxynorephedrine</span> by dopamine beta-hydroxylase (DBH) <i><a href="/wiki/In_vitro" title="In vitro">in vitro</a></i> and it is presumed to be metabolized similarly <i><a href="/wiki/In_vivo" title="In vivo">in vivo</a></i>.<sup id="cite_ref-Substituted_amphetamines,_FMO,_and_DBH_16-1" class="reference"><a href="#cite_note-Substituted_amphetamines,_FMO,_and_DBH-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid13977820_21-1" class="reference"><a href="#cite_note-pmid13977820-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Evidence from studies that measured the effect of serum DBH concentrations on <span class="nowrap">4-hydroxyamphetamine</span> metabolism in humans suggests that a different enzyme may mediate the conversion of <span class="nowrap">4-hydroxyamphetamine</span> to <span class="nowrap">4-hydroxynorephedrine</span>;<sup id="cite_ref-pmid13977820_21-2" class="reference"><a href="#cite_note-pmid13977820-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DBH_4-HA_primary_24-0" class="reference"><a href="#cite_note-DBH_4-HA_primary-24"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> however, other evidence from animal studies suggests that this reaction is catalyzed by DBH in <a href="/wiki/Synaptic_vesicle" title="Synaptic vesicle">synaptic vesicles</a> within noradrenergic neurons in the brain.<sup id="cite_ref-pmid4457764_25-0" class="reference"><a href="#cite_note-pmid4457764-25"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid2600821_26-0" class="reference"><a href="#cite_note-pmid2600821-26"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Reference_notes">Reference notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=4-Hydroxyamphetamine&action=edit&section=12" title="Edit section: Reference notes"><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"><ol class="references"> <li id="cite_note-amphetamine_metabolism-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-amphetamine_metabolism_23-0">^</a></b></span> <span class="reference-text"><sup id="cite_ref-FDA_Pharmacokinetics_15-0" class="reference"><a href="#cite_note-FDA_Pharmacokinetics-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Substituted_amphetamines,_FMO,_and_DBH_16-0" class="reference"><a href="#cite_note-Substituted_amphetamines,_FMO,_and_DBH-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DBH_amph_primary_17-0" class="reference"><a href="#cite_note-DBH_amph_primary-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FMO_18-0" class="reference"><a href="#cite_note-FMO-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FMO3-Primary_19-0" class="reference"><a href="#cite_note-FMO3-Primary-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Metabolites_20-0" class="reference"><a href="#cite_note-Metabolites-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid13977820_21-0" class="reference"><a href="#cite_note-pmid13977820-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Glycine_conjugation_review_22-0" class="reference"><a href="#cite_note-Glycine_conjugation_review-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup></span> </li> </ol></div></div> <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=4-Hydroxyamphetamine&action=edit&section=13" 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-Elks2014-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Elks2014_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Elks2014_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Elks2014_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Elks2014_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Elks2014_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Elks2014_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Elks2014_1-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFElks2014" class="citation book cs1">Elks J (2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA74"><i>The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies</i></a>. Springer US. p. 74. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-2085-3" title="Special:BookSources/978-1-4757-2085-3"><bdi>978-1-4757-2085-3</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">August 30,</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Dictionary+of+Drugs%3A+Chemical+Data%3A+Chemical+Data%2C+Structures+and+Bibliographies&rft.pages=74&rft.pub=Springer+US&rft.date=2014&rft.isbn=978-1-4757-2085-3&rft.aulast=Elks&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0vXTBwAAQBAJ%26pg%3DPA74&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-MortonHall2012-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-MortonHall2012_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MortonHall2012_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-MortonHall2012_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-MortonHall2012_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-MortonHall2012_2-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMortonHall2012" class="citation book cs1">Morton IK, Hall JM (2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA90"><i>Concise Dictionary of Pharmacological Agents: Properties and Synonyms</i></a>. Springer Netherlands. p. 90. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-011-4439-1" title="Special:BookSources/978-94-011-4439-1"><bdi>978-94-011-4439-1</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">August 30,</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Concise+Dictionary+of+Pharmacological+Agents%3A+Properties+and+Synonyms&rft.pages=90&rft.pub=Springer+Netherlands&rft.date=2012&rft.isbn=978-94-011-4439-1&rft.aulast=Morton&rft.aufirst=IK&rft.au=Hall%2C+JM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DtsjrCAAAQBAJ%26pg%3DPA90&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-IndexNominum2004-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-IndexNominum2004_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IndexNominum2004_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-IndexNominum2004_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-IndexNominum2004_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-IndexNominum2004_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-IndexNominum2004_3-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-IndexNominum2004_3-6"><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="CITEREFSchweizerischer_Apotheker-Verein2004" class="citation book cs1">Schweizerischer Apotheker-Verein (2004). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=EgeuA47Ocm4C&pg=PA609"><i>Index Nominum: International Drug Directory</i></a>. Index Nominum: International Drug Directory. Medpharm Scientific Publishers. p. 609. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-88763-101-7" title="Special:BookSources/978-3-88763-101-7"><bdi>978-3-88763-101-7</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">August 30,</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Index+Nominum%3A+International+Drug+Directory&rft.series=Index+Nominum%3A+International+Drug+Directory&rft.pages=609&rft.pub=Medpharm+Scientific+Publishers&rft.date=2004&rft.isbn=978-3-88763-101-7&rft.au=Schweizerischer+Apotheker-Verein&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DEgeuA47Ocm4C%26pg%3DPA609&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-DrugBank-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-DrugBank_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-DrugBank_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-DrugBank_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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://go.drugbank.com/drugs/DB09352">"Hydroxyamphetamine: Uses, Interactions, Mechanism of Action"</a>. <i>DrugBank Online</i>. 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In Lemke TL, Williams DA, Roche VF, Zito W (eds.). <i>Foye's principles of medicinal chemistry</i> (7th ed.). Philadelphia, US: Wolters Kluwer Health/Lippincott Williams & Wilkins. pp. 646–648. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781609133450" title="Special:BookSources/9781609133450"><bdi>9781609133450</bdi></a>. <q>The simplest unsubstituted phenylisopropylamine, 1-phenyl-2-aminopropane, or amphetamine, serves as a common structural template for hallucinogens and psychostimulants. Amphetamine produces central stimulant, anorectic, and sympathomimetic actions, and it is the prototype member of this class (39). ... The phase 1 metabolism of amphetamine analogs is catalyzed by two systems: cytochrome P450 and flavin monooxygenase. ... Amphetamine can also undergo aromatic hydroxylation to <i>p</i>-hydroxyamphetamine. ... Subsequent oxidation at the benzylic position by DA β-hydroxylase affords <i>p</i>-hydroxynorephedrine. Alternatively, direct oxidation of amphetamine by DA β-hydroxylase can afford norephedrine.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Phenylisopropylamine+stimulants%3A+amphetamine-related+agents&rft.btitle=Foye%27s+principles+of+medicinal+chemistry&rft.place=Philadelphia%2C+US&rft.pages=646-648&rft.edition=7th&rft.pub=Wolters+Kluwer+Health%2FLippincott+Williams+%26+Wilkins&rft.date=2013&rft.isbn=9781609133450&rft.au=Glennon+RA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DSd6ot9ul-bUC%26pg%3DPA646&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-DBH_amph_primary-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-DBH_amph_primary_17-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTaylor_KB1974" class="citation journal cs1">Taylor KB (January 1974). <a rel="nofollow" class="external text" href="http://www.jbc.org/content/249/2/454.full.pdf">"Dopamine-beta-hydroxylase. Stereochemical course of the reaction"</a> <span class="cs1-format">(PDF)</span>. <i>Journal of Biological Chemistry</i>. <b>249</b> (2): 454–458. <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%2819%2943051-2">10.1016/S0021-9258(19)43051-2</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/4809526">4809526</a><span class="reference-accessdate">. Retrieved <span class="nowrap">November 6,</span> 2014</span>. <q>Dopamine-β-hydroxylase catalyzed the removal of the pro-<i>R</i> hydrogen atom and the production of 1-norephedrine, (2<i>S</i>,1<i>R</i>)-2-amino-1-hydroxyl-1-phenylpropane, from <i>d</i>-amphetamine.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Biological+Chemistry&rft.atitle=Dopamine-beta-hydroxylase.+Stereochemical+course+of+the+reaction&rft.volume=249&rft.issue=2&rft.pages=454-458&rft.date=1974-01&rft_id=info%3Adoi%2F10.1016%2FS0021-9258%2819%2943051-2&rft_id=info%3Apmid%2F4809526&rft.au=Taylor+KB&rft_id=http%3A%2F%2Fwww.jbc.org%2Fcontent%2F249%2F2%2F454.full.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-FMO-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-FMO_18-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKruegerWilliams2005" class="citation journal cs1">Krueger SK, Williams DE (June 2005). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1828602">"Mammalian flavin-containing monooxygenases: structure/function, genetic polymorphisms and role in drug metabolism"</a>. <i>Pharmacology & Therapeutics</i>. <b>106</b> (3): 357–387. <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.2005.01.001">10.1016/j.pharmthera.2005.01.001</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/PMC1828602">1828602</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/15922018">15922018</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=Mammalian+flavin-containing+monooxygenases%3A+structure%2Ffunction%2C+genetic+polymorphisms+and+role+in+drug+metabolism&rft.volume=106&rft.issue=3&rft.pages=357-387&rft.date=2005-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1828602%23id-name%3DPMC&rft_id=info%3Apmid%2F15922018&rft_id=info%3Adoi%2F10.1016%2Fj.pharmthera.2005.01.001&rft.aulast=Krueger&rft.aufirst=SK&rft.au=Williams%2C+DE&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1828602&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span><br /><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1828602/table/T5/">Table 5: N-containing drugs and xenobiotics oxygenated by FMO</a></span> </li> <li id="cite_note-FMO3-Primary-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-FMO3-Primary_19-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCashmanXiongXuJanowsky1999" class="citation journal cs1">Cashman JR, Xiong YN, Xu L, Janowsky A (March 1999). "N-oxygenation of amphetamine and methamphetamine by the human flavin-containing monooxygenase (form 3): role in bioactivation and detoxication". <i>Journal of Pharmacology and Experimental Therapeutics</i>. <b>288</b> (3): 1251–1260. <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/10027866">10027866</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=N-oxygenation+of+amphetamine+and+methamphetamine+by+the+human+flavin-containing+monooxygenase+%28form+3%29%3A+role+in+bioactivation+and+detoxication&rft.volume=288&rft.issue=3&rft.pages=1251-1260&rft.date=1999-03&rft_id=info%3Apmid%2F10027866&rft.aulast=Cashman&rft.aufirst=JR&rft.au=Xiong%2C+YN&rft.au=Xu%2C+L&rft.au=Janowsky%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Metabolites-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-Metabolites_20-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSantagatiFerraraMarrazzoRonsisvalle2002" class="citation journal cs1">Santagati NA, Ferrara G, Marrazzo A, Ronsisvalle G (September 2002). "Simultaneous determination of amphetamine and one of its metabolites by HPLC with electrochemical detection". <i>Journal of Pharmaceutical and Biomedical Analysis</i>. <b>30</b> (2): 247–255. <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%2900330-8">10.1016/S0731-7085(02)00330-8</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/12191709">12191709</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=Simultaneous+determination+of+amphetamine+and+one+of+its+metabolites+by+HPLC+with+electrochemical+detection&rft.volume=30&rft.issue=2&rft.pages=247-255&rft.date=2002-09&rft_id=info%3Adoi%2F10.1016%2FS0731-7085%2802%2900330-8&rft_id=info%3Apmid%2F12191709&rft.aulast=Santagati&rft.aufirst=NA&rft.au=Ferrara%2C+G&rft.au=Marrazzo%2C+A&rft.au=Ronsisvalle%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-pmid13977820-21"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid13977820_21-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid13977820_21-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid13977820_21-2"><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="CITEREFSjoerdsmavon_Studnitz1963" class="citation journal cs1">Sjoerdsma A, von Studnitz W (April 1963). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1703637">"Dopamine-beta-oxidase activity in man, using hydroxyamphetamine as substrate"</a>. <i>British Journal of Pharmacology and Chemotherapy</i>. <b>20</b> (2): 278–284. <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.1476-5381.1963.tb01467.x">10.1111/j.1476-5381.1963.tb01467.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/PMC1703637">1703637</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/13977820">13977820</a>. <q>Hydroxyamphetamine was administered orally to five human subjects ... Since conversion of hydroxyamphetamine to hydroxynorephedrine occurs in vitro by the action of dopamine-β-oxidase, a simple method is suggested for measuring the activity of this enzyme and the effect of its inhibitors in man. ... The lack of effect of administration of neomycin to one patient indicates that the hydroxylation occurs in body tissues. ... a major portion of the β-hydroxylation of hydroxyamphetamine occurs in non-adrenal tissue. Unfortunately, at the present time one cannot be completely certain that the hydroxylation of hydroxyamphetamine in vivo is accomplished by the same enzyme which converts dopamine to noradrenaline.</q></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=Dopamine-beta-oxidase+activity+in+man%2C+using+hydroxyamphetamine+as+substrate&rft.volume=20&rft.issue=2&rft.pages=278-284&rft.date=1963-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1703637%23id-name%3DPMC&rft_id=info%3Apmid%2F13977820&rft_id=info%3Adoi%2F10.1111%2Fj.1476-5381.1963.tb01467.x&rft.aulast=Sjoerdsma&rft.aufirst=A&rft.au=von+Studnitz%2C+W&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1703637&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Glycine_conjugation_review-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-Glycine_conjugation_review_22-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBadenhorstvan_der_SluisErasmusvan_Dijk2013" class="citation journal cs1">Badenhorst CP, van der Sluis R, Erasmus E, van Dijk AA (September 2013). "Glycine conjugation: importance in metabolism, the role of glycine N-acyltransferase, and factors that influence interindividual variation". <i>Expert Opinion on Drug Metabolism & Toxicology</i>. <b>9</b> (9): 1139–1153. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1517%2F17425255.2013.796929">10.1517/17425255.2013.796929</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/23650932">23650932</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:23738007">23738007</a>. <q>Figure 1. Glycine conjugation of benzoic acid. The glycine conjugation pathway consists of two steps. First benzoate is ligated to CoASH to form the high-energy benzoyl-CoA thioester. This reaction is catalyzed by the HXM-A and HXM-B medium-chain acid:CoA ligases and requires energy in the form of ATP. ... The benzoyl-CoA is then conjugated to glycine by GLYAT to form hippuric acid, releasing CoASH. In addition to the factors listed in the boxes, the levels of ATP, CoASH, and glycine may influence the overall rate of the glycine conjugation pathway.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Opinion+on+Drug+Metabolism+%26+Toxicology&rft.atitle=Glycine+conjugation%3A+importance+in+metabolism%2C+the+role+of+glycine+N-acyltransferase%2C+and+factors+that+influence+interindividual+variation&rft.volume=9&rft.issue=9&rft.pages=1139-1153&rft.date=2013-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A23738007%23id-name%3DS2CID&rft_id=info%3Apmid%2F23650932&rft_id=info%3Adoi%2F10.1517%2F17425255.2013.796929&rft.aulast=Badenhorst&rft.aufirst=CP&rft.au=van+der+Sluis%2C+R&rft.au=Erasmus%2C+E&rft.au=van+Dijk%2C+AA&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-DBH_4-HA_primary-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-DBH_4-HA_primary_24-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHorwitzAlexanderLovenbergKeiser1973" class="citation journal cs1">Horwitz D, Alexander RW, Lovenberg W, Keiser HR (May 1973). "Human serum dopamine-β-hydroxylase. Relationship to hypertension and sympathetic activity". <i>Circulation Research</i>. <b>32</b> (5): 594–599. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1161%2F01.RES.32.5.594">10.1161/01.RES.32.5.594</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/4713201">4713201</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:28641000">28641000</a>. <q>The biologic significance of the different levels of serum DβH activity was studied in two ways. First, in vivo ability to β-hydroxylate the synthetic substrate hydroxyamphetamine was compared in two subjects with low serum DβH activity and two subjects with average activity. ... In one study, hydroxyamphetamine (Paredrine), a synthetic substrate for DβH, was administered to subjects with either low or average levels of serum DβH activity. The percent of the drug hydroxylated to hydroxynorephedrine was comparable in all subjects (6.5-9.62) (Table 3).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Circulation+Research&rft.atitle=Human+serum+dopamine-%CE%B2-hydroxylase.+Relationship+to+hypertension+and+sympathetic+activity&rft.volume=32&rft.issue=5&rft.pages=594-599&rft.date=1973-05&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A28641000%23id-name%3DS2CID&rft_id=info%3Apmid%2F4713201&rft_id=info%3Adoi%2F10.1161%2F01.RES.32.5.594&rft.aulast=Horwitz&rft.aufirst=D&rft.au=Alexander%2C+RW&rft.au=Lovenberg%2C+W&rft.au=Keiser%2C+HR&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-pmid4457764-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid4457764_25-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFreemanSulser1974" class="citation journal cs1">Freeman JJ, Sulser F (December 1974). "Formation of p-hydroxynorephedrine in brain following intraventricular administration of p-hydroxyamphetamine". <i>Neuropharmacology</i>. <b>13</b> (12): 1187–1190. <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%2F0028-3908%2874%2990069-0">10.1016/0028-3908(74)90069-0</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/4457764">4457764</a>. <q>In species where aromatic hydroxylation of amphetamine is the major metabolic pathway, <i>p</i>-hydroxyamphetamine (POH) and <i>p</i>-hydroxynorephedrine (PHN) may contribute to the pharmacological profile of the parent drug. ... The location of the <i>p</i>-hydroxylation and β-hydroxylation reactions is important in species where aromatic hydroxylation of amphetamine is the predominant pathway of metabolism. Following systemic administration of amphetamine to rats, POH has been found in urine and in plasma.<br />The observed lack of a significant accumulation of PHN in brain following the intraventricular administration of (+)-amphetamine and the formation of appreciable amounts of PHN from (+)-POH in brain tissue in vivo supports the view that the aromatic hydroxylation of amphetamine following its systemic administration occurs predominantly in the periphery, and that POH is then transported through the blood-brain barrier, taken up by noradrenergic neurones in brain where (+)-POH is converted in the storage vesicles by dopamine β-hydroxylase to PHN.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neuropharmacology&rft.atitle=Formation+of+p-hydroxynorephedrine+in+brain+following+intraventricular+administration+of+p-hydroxyamphetamine&rft.volume=13&rft.issue=12&rft.pages=1187-1190&rft.date=1974-12&rft_id=info%3Adoi%2F10.1016%2F0028-3908%2874%2990069-0&rft_id=info%3Apmid%2F4457764&rft.aulast=Freeman&rft.aufirst=JJ&rft.au=Sulser%2C+F&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-pmid2600821-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid2600821_26-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMatsudaHansonGibb1989" class="citation journal cs1">Matsuda LA, Hanson GR, Gibb JW (December 1989). "Neurochemical effects of amphetamine metabolites on central dopaminergic and serotonergic systems". <i>Journal of Pharmacology and Experimental Therapeutics</i>. <b>251</b> (3): 901–908. <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/2600821">2600821</a>. <q>The metabolism of <i>p</i>-OHA to <i>p</i>-OHNor is well documented and dopamine-β hydroxylase present in noradrenergic neurons could easily convert <i>p</i>-OHA to <i>p</i>-OHNor after intraventricular administration.</q></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=Neurochemical+effects+of+amphetamine+metabolites+on+central+dopaminergic+and+serotonergic+systems&rft.volume=251&rft.issue=3&rft.pages=901-908&rft.date=1989-12&rft_id=info%3Apmid%2F2600821&rft.aulast=Matsuda&rft.aufirst=LA&rft.au=Hanson%2C+GR&rft.au=Gibb%2C+JW&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-PubChem-28"><span class="mw-cite-backlink">^ <a href="#cite_ref-PubChem_28-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PubChem_28-1"><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="https://pubchem.ncbi.nlm.nih.gov/compound/3651">"4-(2-Aminopropyl)phenol"</a>. <i>PubChem</i><span class="reference-accessdate">. Retrieved <span class="nowrap">August 30,</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PubChem&rft.atitle=4-%282-Aminopropyl%29phenol&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F3651&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-ChemSpider-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-ChemSpider_29-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.3525.html">"C9H13NO"</a>. <i>Hydroxyamphetamine</i>. August 30, 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">August 30,</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Hydroxyamphetamine&rft.atitle=C9H13NO&rft.date=2024-08-30&rft_id=https%3A%2F%2Fwww.chemspider.com%2FChemical-Structure.3525.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20180916144249/https://www.thefreelibrary.com/Akorn+Acquires+Paredrine+-+Specialty+Ophthalmic+Diagnostic+Product...-a054197191">"Akorn Acquires Paredrine - Specialty Ophthalmic Diagnostic Product From Pharmics, Inc"</a>. <i>Akorn press release</i>. March 24, 1999. Archived from <a rel="nofollow" class="external text" href="http://www.thefreelibrary.com/Akorn+Acquires+Paredrine+-+Specialty+Ophthalmic+Diagnostic+Product...-a054197191">the original</a> on September 16, 2018<span class="reference-accessdate">. Retrieved <span class="nowrap">December 9,</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Akorn+press+release&rft.atitle=Akorn+Acquires+Paredrine+-+Specialty+Ophthalmic+Diagnostic+Product+From+Pharmics%2C+Inc.&rft.date=1999-03-24&rft_id=http%3A%2F%2Fwww.thefreelibrary.com%2FAkorn%2BAcquires%2BParedrine%2B-%2BSpecialty%2BOphthalmic%2BDiagnostic%2BProduct...-a054197191&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Akorn-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-Akorn_31-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://investors.akorn.com/phoenix.zhtml?c=78132&p=irol-newsArticle&ID=247062">"Akorn press release"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Akorn+press+release&rft_id=http%3A%2F%2Finvestors.akorn.com%2Fphoenix.zhtml%3Fc%3D78132%26p%3Dirol-newsArticle%26ID%3D247062&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span><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 July 2023">permanent dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup></span> </li> <li id="cite_note-Akorn-2-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-Akorn-2_32-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20190626065749/http://www.akorn.com/about_timeline.php">"Akorn timeline"</a>. Archived from <a rel="nofollow" class="external text" href="http://www.akorn.com/about_timeline.php">the original</a> on June 26, 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">December 9,</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Akorn+timeline&rft_id=http%3A%2F%2Fwww.akorn.com%2Fabout_timeline.php&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Lurcott2002-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-Lurcott2002_33-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLurcott2002" class="citation web cs1">Lurcott R (December 1, 2002). <a rel="nofollow" class="external text" href="http://www.ophthalmologymanagement.com/articleviewer.aspx?articleID=85623">"Unique Mydriatic Returns: The combination formula fosters patient flow efficiencies"</a>. <i>Ophthalmology Management</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Ophthalmology+Management&rft.atitle=Unique+Mydriatic+Returns%3A+The+combination+formula+fosters+patient+flow+efficiencies&rft.date=2002-12-01&rft.aulast=Lurcott&rft.aufirst=R&rft_id=http%3A%2F%2Fwww.ophthalmologymanagement.com%2Farticleviewer.aspx%3FarticleID%3D85623&rfr_id=info%3Asid%2Fen.wikipedia.org%3A4-Hydroxyamphetamine" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=4-Hydroxyamphetamine&action=edit&section=14" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?name=p-Hydroxyamphetamine">p-Hydroxyamphetamine</a> at the U.S. National 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.navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Amphetamine" style="padding:3px"><table class="nowraplinks mw-collapsible expanded 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"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night 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center">Main articles <br />and <br />pharmaceuticals</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:10.5em"><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Adzenys ER</i></li> <li><i><span class="nowrap">Adzenys XR-ODT</span></i></li> <li><i>Dyanavel XR</i></li> <li><i>Evekeo</i></li> <li><i>Evekeo ODT</i></li> <li>Mixed amphetamine salts <ul><li><i><a href="/wiki/Adderall" title="Adderall">Adderall</a></i></li> <li><i>Adderall XR</i></li> <li><i>Mydayis</i></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10.5em"><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em">N/A</div></td></tr><tr><th scope="row" class="navbox-group" style="width:10.5em"><a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Dexedrine</i></li> <li><i>ProCentra</i></li> <li><i>Zenzedi</i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10.5em"><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Vyvanse</i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center">Neuropharmacology</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:10.5em"><a href="/wiki/Biological_target" title="Biological target">Biomolecular targets</a></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/TAAR1" title="TAAR1">TAAR1</a> (<a href="/wiki/Agonist#Types_of_agonists" title="Agonist">full agonist</a>)</li> <li><a href="/wiki/Cocaine_and_amphetamine_regulated_transcript" title="Cocaine and amphetamine regulated transcript">CART</a> (<a href="/wiki/Messenger_RNA" title="Messenger RNA"><abbr title="messenger RNA">mRNA</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 messenger RNA</span> inducer)</li> <li><a href="/wiki/5-HT1A_receptor" title="5-HT1A receptor">5-HT1A receptor</a> (low affinity <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligand</a>)</li> <li><a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">MAO</a> (weak <a href="/wiki/Competitive_inhibition" title="Competitive inhibition">competitive inhibitor</a>)</li> <li><a href="/wiki/Carbonic_anhydrase" title="Carbonic anhydrase">Carbonic anhydrases</a> <a href="/wiki/Carbonic_anhydrase_4" title="Carbonic anhydrase 4">hCA4</a>, <a href="/wiki/Carbonic_anhydrase_5A" class="mw-redirect" title="Carbonic anhydrase 5A">hCA5A</a>, <a href="/wiki/Carbonic_anhydrase_5B" class="mw-redirect" title="Carbonic anhydrase 5B">hCA5B</a>, <a href="/wiki/Carbonic_anhydrase_7" title="Carbonic anhydrase 7">hCA7</a>, <a href="/wiki/Carbonic_anhydrase_12" title="Carbonic anhydrase 12">hCA12</a>, <a href="/wiki/Carbonic_anhydrase_13" title="Carbonic anhydrase 13">hCA13</a>, and <a href="/wiki/Carbonic_anhydrase_14" title="Carbonic anhydrase 14">hCA14</a> (<a href="/wiki/Enzyme_activator" title="Enzyme activator">enzyme activator</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10.5em">Inhibited <a href="/wiki/Membrane_transport_protein" title="Membrane transport protein">transporters</a></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/Dopamine_transporter" title="Dopamine transporter">DAT</a></li> <li><a href="/wiki/Norepinephrine_transporter" title="Norepinephrine transporter">NET</a></li> <li><a href="/wiki/Serotonin_transporter" title="Serotonin transporter">SERT</a></li> <li><a href="/wiki/Vesicular_monoamine_transporter_1" title="Vesicular monoamine transporter 1">VMAT1</a></li> <li><a href="/wiki/Vesicular_monoamine_transporter_2" title="Vesicular monoamine transporter 2">VMAT2</a></li> <li><a href="/wiki/Glutamate_transporter#EAATs" title="Glutamate transporter">EAAT3</a></li> <li><a href="/wiki/SLC22A3" title="SLC22A3">SLC22A3</a></li> <li><a href="/wiki/SLC22A5" title="SLC22A5">SLC22A5</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">Active metabolites</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 class="mw-selflink selflink">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/P-Hydroxynorephedrine" title="P-Hydroxynorephedrine">4-Hydroxynorephedrine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Norephedrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center">Related articles</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/Attention_deficit_hyperactivity_disorder" title="Attention deficit hyperactivity disorder">ADHD</a></li> <li><a href="/wiki/Attention_deficit_hyperactivity_disorder_management" class="mw-redirect" title="Attention deficit hyperactivity disorder management">ADHD management</a></li> <li><a href="/wiki/Stimulant_psychosis#Substituted_amphetamines" title="Stimulant psychosis">Amphetamine psychosis</a></li> <li><a href="/wiki/Benzedrine_in_popular_culture" class="mw-redirect" title="Benzedrine in popular culture">Benzedrine in popular culture</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Doping_in_sport" title="Doping in sport">Doping in sport</a></li> <li><a href="/wiki/Executive_functions" title="Executive functions">Executive functions</a></li> <li><a href="/wiki/Formetorex" title="Formetorex">Formetorex</a></li> <li><a href="/wiki/FOSB#ΔFosB" title="FOSB">ΔFosB</a></li> <li><a href="/wiki/History_and_culture_of_substituted_amphetamines" title="History and culture of substituted amphetamines">History and culture of substituted amphetamines</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li> <li><a href="/wiki/Motivational_salience" title="Motivational salience">Motivational salience</a> <ul><li><a href="/wiki/Motivational_salience#Incentive_salience" title="Motivational salience">Incentive salience</a></li></ul></li> <li><a href="/wiki/Narcolepsy" title="Narcolepsy">Narcolepsy</a></li> <li><a href="/wiki/Neurobiological_effects_of_physical_exercise#Attention_deficit_hyperactivity_disorder" title="Neurobiological effects of physical exercise">Neurobiological effects of physical exercise § Attention deficit hyperactivity disorder</a></li> <li><a href="/wiki/Nootropic" title="Nootropic">Nootropic</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Obesity" title="Obesity">Obesity</a></li> <li><a href="/wiki/Performance-enhancing_substance" title="Performance-enhancing substance">Performance-enhancing substance</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/Phenylacetone" title="Phenylacetone">Phenylacetone</a></li> <li><a href="/wiki/Recreational_drug_use" title="Recreational drug use">Recreational drug use</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a></li> <li><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Substituted amphetamine</a></li> <li><a href="/wiki/Trace_amine" title="Trace amine">Trace amine</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow hlist" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Amphetamine" title="Category:Amphetamine">Category</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Ophthalmologicals:_mydriasis_and_cycloplegia_(S01F)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Mydriatics_and_cycloplegics" title="Template:Mydriatics and cycloplegics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Mydriatics_and_cycloplegics" title="Template talk:Mydriatics and cycloplegics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Mydriatics_and_cycloplegics" title="Special:EditPage/Template:Mydriatics and cycloplegics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Ophthalmologicals:_mydriasis_and_cycloplegia_(S01F)" style="font-size:114%;margin:0 4em"><a href="/wiki/Ophthalmology" title="Ophthalmology">Ophthalmologicals</a>: <a href="/wiki/Mydriasis" title="Mydriasis">mydriasis</a> and <a href="/wiki/Cycloplegia" title="Cycloplegia">cycloplegia</a> (<a href="/wiki/ATC_code_S01#S01F" title="ATC code S01">S01F</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anticholinergic" title="Anticholinergic">Anticholinergics</a>/<a href="/wiki/Muscarinic_antagonist" title="Muscarinic antagonist">antimuscarinics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Atropine" title="Atropine">Atropine</a></li> <li><a href="/wiki/Hyoscine_hydrobromide" class="mw-redirect" title="Hyoscine hydrobromide">Scopolamine</a></li> <li><a href="/wiki/Methylscopolamine_bromide" title="Methylscopolamine bromide">Methylscopolamine</a></li> <li><a href="/wiki/Cyclopentolate" title="Cyclopentolate">Cyclopentolate</a></li> <li><a href="/wiki/Homatropine" title="Homatropine">Homatropine</a></li> <li><a href="/wiki/Tropicamide" title="Tropicamide">Tropicamide</a> (<a href="/wiki/Tropicamide/phenylephrine" title="Tropicamide/phenylephrine">+phenylephrine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sympathomimetic_drug" title="Sympathomimetic drug">Sympathomimetics</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a class="mw-selflink selflink">Hydroxyamphetamine (norpholedrine)</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a> (<a href="/wiki/Phenylephrine/ketorolac" title="Phenylephrine/ketorolac">+ketorolac</a>)</li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Monoamine_releasing_agents" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoamine_releasing_agents" title="Template talk:Monoamine releasing agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoamine_releasing_agents" title="Special:EditPage/Template:Monoamine releasing agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoamine_releasing_agents" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">Monoamine releasing agents</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Dopamine_releasing_agents" class="mw-redirect" title="Dopamine releasing agents"><abbr title="Dopamine releasing agents">DRAs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dopamine releasing agents</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Morpholines:</i> <a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Oxazolines:</i> <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-MAR</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Cyclazodone" title="Cyclazodone">Cyclazodone</a></li> <li><a href="/wiki/Fenozolone" title="Fenozolone">Fenozolone</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li> <li><a href="/wiki/Pemoline" title="Pemoline">Pemoline</a></li> <li><a href="/wiki/Thozalinone" title="Thozalinone">Thozalinone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Phenethylamines:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">2-OH-PEA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" class="mw-redirect" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Me-PEA</a></li> <li><a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a class="mw-selflink selflink">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Iofetamine_(123I)" title="Iofetamine (123I)">Iofetamine (123I)</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></li></ul></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-methylbutanamine" class="mw-redirect" title="1,3-Benzodioxolyl-N-methylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine"><i>p</i>BA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine"><i>p</i>CA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine"><i>p</i>IA</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Piperazines:</i> <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Others:</i> <a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-ADN</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-AI</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-AT</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-BP</a></li> <li><a href="/wiki/5-APDI" title="5-APDI">5-APDI</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/Amineptine" title="Amineptine">Amineptine</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <li><a href="/wiki/Cyclopentamine" title="Cyclopentamine">Cyclopentamine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexanamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</a></li> <li><a href="/wiki/Phenylbiguanide" title="Phenylbiguanide">Phenylbiguanide</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Norepinephrine_releasing_agents" class="mw-redirect" title="Norepinephrine releasing agents"><abbr title="Norepinephrine releasing agents">NRAs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Norepinephrine releasing agents</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Morpholines:</i> <a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Oxazolines:</i> <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-MAR</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Cyclazodone" title="Cyclazodone">Cyclazodone</a></li> <li><a href="/wiki/Fenozolone" title="Fenozolone">Fenozolone</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li> <li><a href="/wiki/Pemoline" title="Pemoline">Pemoline</a></li> <li><a href="/wiki/Thozalinone" title="Thozalinone">Thozalinone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Phenethylamines:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">2-OH-PEA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" class="mw-redirect" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> <ul><li><a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a></li></ul></li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Me-PEA</a></li> <li><a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a class="mw-selflink selflink">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/5-APDI" title="5-APDI">5-APDI</a> (IAP)</li> <li><a href="/wiki/Iofetamine_(123I)" title="Iofetamine (123I)">Iofetamine (123I)</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-methylbutanamine" class="mw-redirect" title="1,3-Benzodioxolyl-N-methylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></li></ul></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine"><i>p</i>BA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine"><i>p</i>CA</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine"><i>p</i>IA</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl"><span style="font-size:85%;">D</span>-Deprenyl</a>)</li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Piperazines:</i> <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Others:</i> <a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-ADN</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-AI</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-AT</a></li> <li><a href="/wiki/2-Benzylpiperidine" title="2-Benzylpiperidine">2-BP</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-BP</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <li><a href="/wiki/Cyclopentamine" title="Cyclopentamine">Cyclopentamine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexanamine</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li> <li><a href="/wiki/Tuaminoheptane" title="Tuaminoheptane">Tuaminoheptane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Serotonin_releasing_agents" class="mw-redirect" title="Serotonin releasing agents"><abbr title="Serotonin releasing agents">SRAs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Serotonin releasing agents</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Aminoindanes:</i> <a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/1-Aminomethyl-5-methoxyindane" title="1-Aminomethyl-5-methoxyindane">AMMI</a></li> <li><a href="/wiki/Ethyltrifluoromethylaminoindane" title="Ethyltrifluoromethylaminoindane">ETAI</a></li> <li><a href="/wiki/MDAI" title="MDAI">MDAI</a></li> <li><a href="/wiki/MDMAI" title="MDMAI">MDMAI</a></li> <li><a href="/wiki/MMAI" title="MMAI">MMAI</a></li> <li><a href="/wiki/Trifluoromethylaminoindane" title="Trifluoromethylaminoindane">TAI</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Aminotetralins:</i> <a href="/wiki/6-CAT" title="6-CAT">6-CAT</a></li> <li><a href="/wiki/8-OH-DPAT" title="8-OH-DPAT">8-OH-DPAT</a></li> <li><a href="/wiki/MDAT" title="MDAT">MDAT</a></li> <li><a href="/wiki/MDMAT" title="MDMAT">MDMAT</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Oxazolines:</i> <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-Methylaminorex</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Phenethylamines:</i> <a href="/wiki/2-Methyl-MDA" title="2-Methyl-MDA">2-Methyl-MDA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a class="mw-selflink selflink">4-HA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-Methyl-MDA" title="5-Methyl-MDA">5-Methyl-MDA</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Methyl-MDA" title="6-Methyl-MDA">6-Methyl-MDA</a></li> <li><a href="/wiki/3-Methoxy-4-methyl-%CE%B1-ethylphenethylamine" class="mw-redirect" title="3-Methoxy-4-methyl-α-ethylphenethylamine">AEMMA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">Brephedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">DCA</a></li> <li><a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a></li> <li><a href="/wiki/DFMDA" title="DFMDA">DFMDA</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/EDMA" title="EDMA">EDMA</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Flucetorex" title="Flucetorex">Flucetorex</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylbenzodioxolylbutanamine" class="mw-redirect" title="Methylbenzodioxolylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxymethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxymethamphetamine">MDHMA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/3-Methoxy-4-methylmethamphetamine" class="mw-redirect" title="3-Methoxy-4-methylmethamphetamine">MMMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">NAP</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/4-Trifluoromethylamphetamine" class="mw-redirect" title="4-Trifluoromethylamphetamine">4-TFMA</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">pBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">pCA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">pIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxyethylamphetamine" class="mw-redirect" title="Para-Methoxyethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxymethamphetamine" class="mw-redirect" title="Para-Methoxymethamphetamine">PMMA</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Piperazines:</i> <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/w/index.php?title=3-Methoxyphenylpiperazine&action=edit&redlink=1" class="new" title="3-Methoxyphenylpiperazine (page does not exist)">3-MeOPP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/3,4-Dichlorophenylpiperazine" class="mw-redirect" title="3,4-Dichlorophenylpiperazine">DCPP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Mepiprazole" title="Mepiprazole">Mepiprazole</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Para-Chlorophenylpiperazine" title="Para-Chlorophenylpiperazine">pCPP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li> <li><a href="/wiki/1-(4-Trifluoromethyl-phenyl)-piperazine" class="mw-redirect" title="1-(4-Trifluoromethyl-phenyl)-piperazine">pTFMPP</a></li> <li><a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Tryptamines:</i> <a href="/wiki/4-Methyl-AET" class="mw-redirect" title="4-Methyl-AET">4-Methyl-αET</a></li> <li><a href="/wiki/4-Methyl-AMT" class="mw-redirect" title="4-Methyl-AMT">4-Methyl-αMT</a></li> <li><a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a></li> <li><a href="/wiki/5-MeO-AMT" class="mw-redirect" title="5-MeO-AMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a></li> <li><a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a></li> <li><a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Others:</i> <a href="/wiki/Indeloxazine" title="Indeloxazine">Indeloxazine</a></li> <li><a href="/wiki/Viqualine" title="Viqualine">Viqualine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>DAT modulators:</i> <i>Agonist-like:</i> <a href="/wiki/SoRI-9804" title="SoRI-9804">SoRI-9804</a></li> <li><a href="/w/index.php?title=SoRI-20040&action=edit&redlink=1" class="new" title="SoRI-20040 (page does not exist)">SoRI-20040</a>; <i>Antagonist-like:</i> <a href="/wiki/SoRI-20041" title="SoRI-20041">SoRI-20041</a></li></ul> <ul><li><i>Adrenergic release blockers:</i> <a href="/wiki/Bethanidine" title="Bethanidine">Bethanidine</a></li> <li><a href="/wiki/Bretylium" title="Bretylium">Bretylium</a></li> <li><a href="/wiki/Guanadrel" title="Guanadrel">Guanadrel</a></li> <li><a href="/wiki/Guanazodine" title="Guanazodine">Guanazodine</a></li> <li><a href="/wiki/Guanethidine" title="Guanethidine">Guanethidine</a></li> <li><a href="/wiki/Guanoxan" title="Guanoxan">Guanoxan</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><small><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> • <a href="/wiki/Template:Adrenergics" class="mw-redirect" title="Template:Adrenergics">Adrenergics</a> • <a href="/wiki/Template:Dopaminergics" class="mw-redirect" title="Template:Dopaminergics">Dopaminergics</a> • <a href="/wiki/Template:Serotonergics" class="mw-redirect" title="Template:Serotonergics">Serotonergics</a> • <a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a> • <a href="/wiki/Template:Monoamine_neurotoxins" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></i></small></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Human_trace_amine-associated_receptor_ligands" style="padding:3px"><table class="nowraplinks hlist 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:TAAR_ligands" title="Template:TAAR ligands"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:TAAR_ligands" title="Template talk:TAAR ligands"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:TAAR_ligands" title="Special:EditPage/Template:TAAR ligands"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Human_trace_amine-associated_receptor_ligands" style="font-size:114%;margin:0 4em"><a href="/wiki/Human_trace_amine-associated_receptor" class="mw-redirect" title="Human trace amine-associated receptor">Human trace amine-associated receptor</a> <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center"><a href="/wiki/TAAR1" title="TAAR1">TAAR1</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:6em;text-align: center"><a href="/wiki/Agonist" title="Agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:5em;text-align: center"><a href="/wiki/Trace_amine" title="Trace amine">Endogenous</a><sup>†</sup></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0;background:white"><div style="padding:0 0.25em"> <ul><li>Classical <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">Phenethylamine</a></li> <li><a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">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></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;text-align: center">Synthetic and natural<sup>‡</sup></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0;background:white"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</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/N,N-Dimethylphenethylamine" title="N,N-Dimethylphenethylamine"><i>N</i>,<i>N</i>-Dimethylphenethylamine</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 class="mw-selflink selflink">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Isopropyloctopamine" class="mw-redirect" title="Isopropyloctopamine">Isopropyloctopamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</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-Methoxymethamphetamine" title="3-Methoxymethamphetamine">3-MMA</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</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/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li> <li><a href="/wiki/Ralmitaront" title="Ralmitaront">Ralmitaront (RG-7906, RO-6889450)</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/RO5166017" title="RO5166017">RO-5166017</a></li> <li><a href="/wiki/RO5256390" title="RO5256390">RO-5256390</a></li> <li><a href="/wiki/RO5263397" title="RO5263397">RO-5263397</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</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:6em;text-align: center"><a href="/wiki/Neutral_antagonist" class="mw-redirect" title="Neutral antagonist">Neutral antagonists</a></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/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:6em;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="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/TAAR2" title="TAAR2">TAAR2</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:6em;text-align: center">Agonists<sup>‡</sup></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center">Neutral antagonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li> </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/TAAR5" title="TAAR5">TAAR5</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:6em;text-align: center">Agonists<sup>‡</sup></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/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:6em;text-align: center">Neutral antagonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li> </li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center">Inverse agonists<sup>‡</sup></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/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><div style="float: left;"><small><sup>†</sup> References for all endogenous human TAAR1 ligands are provided at <a href="/wiki/Trace_amine#list" title="Trace amine">List of trace amines</a></small></div> <p><br /> </p> <div style="float: left;"><small><sup>‡</sup> References for synthetic TAAR1 agonists can be found at <a href="/wiki/TAAR1" title="TAAR1">TAAR1</a> or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see <a href="/wiki/Trace_amine-associated_receptor#Receptor_function_and_ligands" title="Trace amine-associated receptor">TAAR</a> for references.</small></div> <p><br /> </p> <small><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="Phenethylamines" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Phenethylamines" title="Template:Phenethylamines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenethylamines" title="Template talk:Phenethylamines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenethylamines" title="Special:EditPage/Template:Phenethylamines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Phenethylamines" style="font-size:114%;margin:0 4em"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><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></ul> <ul><li><a href="/wiki/2C-B" title="2C-B">2C-B</a></li> <li><a href="/w/index.php?title=2C-B-AN&action=edit&redlink=1" class="new" title="2C-B-AN (page does not exist)">2C-B-AN</a></li> <li><a href="/w/index.php?title=2C-Bn&action=edit&redlink=1" class="new" title="2C-Bn (page does not exist)">2C-Bn</a></li> <li><a href="/w/index.php?title=2C-Bu&action=edit&redlink=1" class="new" title="2C-Bu (page does not exist)">2C-Bu</a></li> <li><a href="/wiki/2C-C" title="2C-C">2C-C</a></li> <li><a href="/w/index.php?title=2C-CN&action=edit&redlink=1" class="new" title="2C-CN (page does not exist)">2C-CN</a></li> <li><a href="/wiki/2C-CP" title="2C-CP">2C-CP</a></li> <li><a href="/wiki/2C-D" title="2C-D">2C-D</a></li> <li><a href="/wiki/2C-E" title="2C-E">2C-E</a></li> <li><a href="/wiki/2C-EF" title="2C-EF">2C-EF</a></li> <li><a href="/wiki/2C-F" title="2C-F">2C-F</a></li> <li><a href="/wiki/2C-G" title="2C-G">2C-G</a></li> <li><a href="/wiki/2C-G-1" class="mw-redirect" title="2C-G-1">2C-G-1</a></li> <li><a href="/wiki/2C-G-2" class="mw-redirect" title="2C-G-2">2C-G-2</a></li> <li><a href="/wiki/2C-G-3" class="mw-redirect" title="2C-G-3">2C-G-3</a></li> <li><a href="/wiki/2C-G-4" class="mw-redirect" title="2C-G-4">2C-G-4</a></li> <li><a href="/wiki/2C-G-5" class="mw-redirect" title="2C-G-5">2C-G-5</a></li> <li><a href="/wiki/2C-G-6" class="mw-redirect" title="2C-G-6">2C-G-6</a></li> <li><a href="/wiki/2C-G-N" class="mw-redirect" title="2C-G-N">2C-G-N</a></li> <li><a href="/wiki/2C-H" title="2C-H">2C-H</a></li> <li><a href="/wiki/2C-I" title="2C-I">2C-I</a></li> <li><a href="/wiki/2C-iP" title="2C-iP">2C-iP</a></li> <li><a href="/wiki/2C-N" title="2C-N">2C-N</a></li> <li><a href="/w/index.php?title=2C-NH2&action=edit&redlink=1" class="new" title="2C-NH2 (page does not exist)">2C-NH2</a></li> <li><a href="/wiki/2C-O" class="mw-redirect" title="2C-O">2C-O</a></li> <li><a href="/wiki/2C-O-4" title="2C-O-4">2C-O-4</a></li> <li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li> <li><a href="/w/index.php?title=2C-Ph&action=edit&redlink=1" class="new" title="2C-Ph (page does not exist)">2C-Ph</a></li> <li><a href="/wiki/2C-SE" class="mw-redirect" title="2C-SE">2C-SE</a></li> <li><a href="/wiki/2C-T" title="2C-T">2C-T</a></li> <li><a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a></li> <li><a href="/wiki/2C-T-3" title="2C-T-3">2C-T-3</a></li> <li><a href="/wiki/2C-T-4" title="2C-T-4">2C-T-4</a></li> <li><a href="/w/index.php?title=2C-T-5&action=edit&redlink=1" class="new" title="2C-T-5 (page does not exist)">2C-T-5</a></li> <li><a href="/w/index.php?title=2C-T-6&action=edit&redlink=1" class="new" title="2C-T-6 (page does not exist)">2C-T-6</a></li> <li><a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a></li> <li><a href="/wiki/2C-T-8" title="2C-T-8">2C-T-8</a></li> <li><a href="/wiki/2C-T-9" class="mw-redirect" title="2C-T-9">2C-T-9</a></li> <li><a href="/w/index.php?title=2C-T-10&action=edit&redlink=1" class="new" title="2C-T-10 (page does not exist)">2C-T-10</a></li> <li><a href="/w/index.php?title=2C-T-11&action=edit&redlink=1" class="new" title="2C-T-11 (page does not exist)">2C-T-11</a></li> <li><a href="/w/index.php?title=2C-T-12&action=edit&redlink=1" class="new" title="2C-T-12 (page does not exist)">2C-T-12</a></li> <li><a href="/wiki/2C-T-13" title="2C-T-13">2C-T-13</a></li> <li><a href="/w/index.php?title=2C-T-14&action=edit&redlink=1" class="new" title="2C-T-14 (page does not exist)">2C-T-14</a></li> <li><a href="/wiki/2C-T-15" title="2C-T-15">2C-T-15</a></li> <li><a href="/wiki/2C-T-16" title="2C-T-16">2C-T-16</a></li> <li><a href="/wiki/2C-T-17" title="2C-T-17">2C-T-17</a></li> <li><a href="/w/index.php?title=2C-T-18&action=edit&redlink=1" class="new" title="2C-T-18 (page does not exist)">2C-T-18</a></li> <li><a href="/wiki/2C-T-19" title="2C-T-19">2C-T-19</a></li> <li><a href="/w/index.php?title=2C-T-20&action=edit&redlink=1" class="new" title="2C-T-20 (page does not exist)">2C-T-20</a></li> <li><a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a></li> <li><a href="/w/index.php?title=2C-T-22&action=edit&redlink=1" class="new" title="2C-T-22 (page does not exist)">2C-T-22</a></li> <li><a href="/w/index.php?title=2C-T-22.5&action=edit&redlink=1" class="new" title="2C-T-22.5 (page does not exist)">2C-T-22.5</a></li> <li><a href="/w/index.php?title=2C-T-23&action=edit&redlink=1" class="new" title="2C-T-23 (page does not exist)">2C-T-23</a></li> <li><a href="/w/index.php?title=2C-T-24&action=edit&redlink=1" class="new" title="2C-T-24 (page does not exist)">2C-T-24</a></li> <li><a href="/w/index.php?title=2C-T-25&action=edit&redlink=1" class="new" title="2C-T-25 (page does not exist)">2C-T-25</a></li> <li><a href="/w/index.php?title=2C-T-27&action=edit&redlink=1" class="new" title="2C-T-27 (page does not exist)">2C-T-27</a></li> <li><a href="/wiki/2C-T-28" title="2C-T-28">2C-T-28</a></li> <li><a href="/w/index.php?title=2C-T-30&action=edit&redlink=1" class="new" title="2C-T-30 (page does not exist)">2C-T-30</a></li> <li><a href="/w/index.php?title=2C-T-31&action=edit&redlink=1" class="new" title="2C-T-31 (page does not exist)">2C-T-31</a></li> <li><a href="/w/index.php?title=2C-T-32&action=edit&redlink=1" class="new" title="2C-T-32 (page does not exist)">2C-T-32</a></li> <li><a href="/w/index.php?title=2C-T-33&action=edit&redlink=1" class="new" title="2C-T-33 (page does not exist)">2C-T-33</a></li> <li><a href="/wiki/2C-TFE" title="2C-TFE">2C-TFE</a></li> <li><a href="/wiki/2C-TFM" title="2C-TFM">2C-TFM</a></li> <li><a href="/wiki/2C-YN" title="2C-YN">2C-YN</a></li> <li><a href="/wiki/2C-V" title="2C-V">2C-V</a></li></ul> <ul><li><a href="/wiki/Allylescaline" title="Allylescaline">Allylescaline</a></li> <li><a href="/wiki/DESOXY" title="DESOXY">DESOXY</a></li> <li><a href="/wiki/Escaline" title="Escaline">Escaline</a></li> <li><a href="/wiki/Isoproscaline" title="Isoproscaline">Isoproscaline</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Macromerine" title="Macromerine">Macromerine</a></li> <li><a href="/wiki/3-Methoxy-4-ethoxyphenethylamine" title="3-Methoxy-4-ethoxyphenethylamine">MEPEA</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metaescaline" title="Metaescaline">Metaescaline</a></li> <li><a href="/wiki/Methallylescaline" title="Methallylescaline">Methallylescaline</a></li> <li><a href="/wiki/Proscaline" title="Proscaline">Proscaline</a></li> <li><a href="/wiki/Psi-2C-T-4" class="mw-redirect" title="Psi-2C-T-4">Psi-2C-T-4</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li></ul> <p><br /><i>Stimulants:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a> </p> <ul><li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">α-Methylphenethylamine</a> (amphetamine)</li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/M-Methylphenethylamine" class="mw-redirect" title="M-Methylphenethylamine"><i>m</i>-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li> <li><a href="/wiki/O-Methylphenethylamine" class="mw-redirect" title="O-Methylphenethylamine"><i>o</i>-Methylphenethylamine</a></li> <li><a href="/wiki/P-Methylphenethylamine" class="mw-redirect" title="P-Methylphenethylamine"><i>p</i>-Methylphenethylamine</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li></ul> <ul><li><i>Entactogens:</i> <a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a><br /><i>Others:</i> <a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/3,4-Dimethoxyphenethylamine" title="3,4-Dimethoxyphenethylamine">DMPEA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Psychedelics:</i> <a href="/wiki/3C-AL" title="3C-AL">3C-AL</a></li> <li><a href="/wiki/3C-BZ" title="3C-BZ">3C-BZ</a></li> <li><a href="/wiki/3C-E" title="3C-E">3C-E</a></li> <li><a href="/wiki/3C-MAL" title="3C-MAL">3C-MAL</a></li> <li><a href="/wiki/3C-P" title="3C-P">3C-P</a></li> <li><a href="/wiki/Aleph_(psychedelic)" title="Aleph (psychedelic)">Aleph</a></li> <li><a href="/wiki/Beatrice_(psychedelic)" title="Beatrice (psychedelic)">Beatrice</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/4-Methyl-2,5-methoxyphenylcyclopropylamine" class="mw-redirect" title="4-Methyl-2,5-methoxyphenylcyclopropylamine">DMCPA</a></li> <li><a href="/wiki/DMMDA" title="DMMDA">DMMDA</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-fluoroethylamphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-fluoroethylamphetamine">DOEF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-nitroamphetamine" title="2,5-Dimethoxy-4-nitroamphetamine">DON</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-propylamphetamine" title="2,5-Dimethoxy-4-propylamphetamine">DOPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-trifluoromethylamphetamine" title="2,5-Dimethoxy-4-trifluoromethylamphetamine">DOTFM</a></li> <li><a href="/wiki/Ganesha_(psychedelic)" title="Ganesha (psychedelic)">Ganesha</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDA-2" title="MMDA-2">MMDA-2</a></li> <li><a href="/wiki/Psi-DOM" class="mw-redirect" title="Psi-DOM">Psi-DOM</a></li> <li><a href="/wiki/Trimethoxyamphetamine" 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 class="mw-selflink selflink">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Isopropylamphetamine" title="Isopropylamphetamine">Isopropylamphetamine</a></li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> (Dextromethamphetamine, <a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a>)</li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/L-Norpseudoephedrine" title="L-Norpseudoephedrine"><span style="font-size:85%;">L</span>-Norpseudoephedrine</a></li> <li><a href="/wiki/N,alpha-Diethylphenylethylamine" class="mw-redirect" title="N,alpha-Diethylphenylethylamine">N,alpha-Diethylphenylethylamine</a></li> <li><a href="/wiki/Oxifentorex" title="Oxifentorex">Oxifentorex</a></li> <li><a href="/wiki/Oxilofrine" title="Oxilofrine">Oxilofrine</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">PBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">PCA</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">PFA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">PFMA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">PIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxy-N-ethylamphetamine" title="Para-Methoxy-N-ethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxy-N-methylamphetamine" 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" class="mw-redirect" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APB" title="5-APB">5-APB</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-EAPB" title="5-EAPB">5-EAPB</a></li> <li><a href="/wiki/5-IT" title="5-IT">5-IT</a></li> <li><a href="/wiki/5-MAPB" title="5-MAPB">5-MAPB</a></li> <li><a href="/wiki/5-MAPDB" title="5-MAPDB">5-MAPDB</a></li> <li><a href="/wiki/6-APB" title="6-APB">6-APB</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Chloro-MDMA" title="6-Chloro-MDMA">6-Chloro-MDMA</a></li> <li><a href="/wiki/6-EAPB" title="6-EAPB">6-EAPB</a></li> <li><a href="/wiki/6-IT" class="mw-redirect" title="6-IT">6-IT</a></li> <li><a href="/wiki/6-MAPB" title="6-MAPB">6-MAPB</a></li> <li><a href="/wiki/6-MAPDB" title="6-MAPDB">6-MAPDB</a></li> <li><a href="/wiki/Ethylidenedioxyamphetamine" class="mw-redirect" title="Ethylidenedioxyamphetamine">EDA</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/2,3-Methylenedioxyamphetamine" title="2,3-Methylenedioxyamphetamine">2,3-MDA</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">3,4-MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxylmethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxylmethamphetamine">MDHMA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a><br /><i>Others:</i> <a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">3,4-DCA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/DiFMDA" class="mw-redirect" title="DiFMDA">DiFMDA</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl"><span style="font-size:85%;">D</span>-Deprenyl</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phentermine" title="Phentermine">Phentermines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a><br /><i>Entactogens:</i> <a href="/wiki/Methylenedioxyphentermine" class="mw-redirect" title="Methylenedioxyphentermine">MDPH</a></li> <li><a href="/wiki/Methylenedioxymethylphentermine" class="mw-redirect" title="Methylenedioxymethylphentermine">MDMPH</a><br /><i>Others:</i> <a href="/wiki/Cericlamine" title="Cericlamine">Cericlamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Cathinones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/3-Fluoromethcathinone" title="3-Fluoromethcathinone">3-FMC</a></li> <li><a href="/wiki/4-Methylcathinone" title="4-Methylcathinone">4-MC</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">4-BMC</a></li> <li><a href="/wiki/4-Chloromethcathinone" title="4-Chloromethcathinone">4-CMC</a></li> <li><a href="/wiki/4-Ethylmethcathinone" title="4-Ethylmethcathinone">4-EMC</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">4-FMC</a></li> <li><a href="/wiki/4-Methylethcathinone" title="4-Methylethcathinone">4-MEC</a></li> <li><a href="/wiki/4-Methylbuphedrone" title="4-Methylbuphedrone">4-MeMABP</a></li> <li><a href="/wiki/4-Methylpentedrone" title="4-Methylpentedrone">4-MPD</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Benzedrone" title="Benzedrone">Benzedrone</a></li> <li><a href="/wiki/Brephedrone" class="mw-redirect" title="Brephedrone">Brephedrone</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Dimethylcathinone" class="mw-redirect" title="Dimethylcathinone">Dimethylcathinone</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/N-Ethylbuphedrone" title="N-Ethylbuphedrone">NEB</a></li> <li><a href="/wiki/N-Ethylhexedrone" title="N-Ethylhexedrone">N-Ethylhexedrone</a></li> <li><a href="/wiki/N-Ethylpentedrone" title="N-Ethylpentedrone">N-Ethylpentedrone</a></li> <li><a href="/wiki/Pentedrone" title="Pentedrone">Pentedrone</a></li> <li><a href="/wiki/Pentylone" title="Pentylone">Pentylone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a><br /><i>Entactogens:</i> <a href="/wiki/3,4-Dimethylmethcathinone" title="3,4-Dimethylmethcathinone">3,4-DMMC</a></li> <li><a href="/wiki/3-Methylmethcathinone" title="3-Methylmethcathinone">3-MMC</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Methylenedioxycathinone" title="Methylenedioxycathinone">Methylenedioxycathinone</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Entactogens:</i> <a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Methylphenylisobutylamine" title="4-Methylphenylisobutylamine">4-MAB</a></li> <li><a href="/wiki/Ariadne_(psychedelic)" class="mw-redirect" title="Ariadne (psychedelic)">Ariadne</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/MBDB" title="MBDB">MBDB</a><br /><i>Stimulants:</i> <a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">Phenylalkylpyrrolidines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/Alpha-Pyrrolidinobutiophenone" class="mw-redirect" title="Alpha-Pyrrolidinobutiophenone">α-PBP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinohexiophenone" class="mw-redirect" title="Alpha-Pyrrolidinohexiophenone">α-PHP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopropiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopropiophenone">α-PPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiophenone">α-PVP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinobutiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinobutiophenone">MDPBP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinopropiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinopropiophenone">MDPPP</a></li> <li><a href="/wiki/3,4-Methylenedioxypyrovalerone" class="mw-redirect" title="3,4-Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">4-MePBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">4-MePHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">4-MePPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopropiophenone" title="4'-Methoxy-α-pyrrolidinopropiophenone">MOPPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopentiophenone" title="4'-Methoxy-α-pyrrolidinopentiophenone">MOPVP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">MPBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">MPHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">MPPP</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">PEP</a></li> <li><a href="/wiki/Prolintane" title="Prolintane">Prolintane</a></li> <li><a href="/wiki/Pyrovalerone" title="Pyrovalerone">Pyrovalerone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Catecholamine" title="Catecholamine">Catecholamines</a><br /><span style="font-size:85%;">(and close relatives)</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/6-Hydroxydopamine" class="mw-redirect" title="6-Hydroxydopamine">6-OHDA</a></li> <li><a href="/wiki/Alpha-Methyldopamine" class="mw-redirect" title="Alpha-Methyldopamine">a-Me-DA</a></li> <li><a href="/wiki/Alpha-Methyltyramine" class="mw-redirect" title="Alpha-Methyltyramine">a-Me-TRA</a></li> <li><a href="/wiki/Adrenochrome" title="Adrenochrome">Adrenochrome</a></li> <li><a href="/wiki/Ciladopa" title="Ciladopa">Ciladopa</a></li> <li><a href="/wiki/D-DOPA" title="D-DOPA"><span style="font-size:85%;">D</span>-DOPA</a> (Dextrodopa)</li> <li><a href="/wiki/Dimetofrine" title="Dimetofrine">Dimetofrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Epinephrine_(neurotransmitter)" class="mw-redirect" title="Epinephrine (neurotransmitter)">Epinephrine</a></li> <li><a href="/wiki/Epinine" class="mw-redirect" title="Epinine">Epinine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Fenclonine" title="Fenclonine">Fenclonine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA"><span style="font-size:85%;">L</span>-DOPA</a> (Levodopa)</li> <li><a href="/wiki/L-DOPS" class="mw-redirect" title="L-DOPS"><span style="font-size:85%;">L</span>-DOPS</a> (Droxidopa)</li> <li><a href="/wiki/L-Phenylalanine" class="mw-redirect" title="L-Phenylalanine"><span style="font-size:85%;">L</span>-Phenylalanine</a></li> <li><a href="/wiki/L-Tyrosine" class="mw-redirect" title="L-Tyrosine"><span style="font-size:85%;">L</span>-Tyrosine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Metaterol" title="Metaterol">Metaterol</a></li> <li><a href="/wiki/Metirosine" class="mw-redirect" title="Metirosine">Metirosine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/N,N-Dimethyldopamine" title="N,N-Dimethyldopamine">N,N-Dimethyldopamine</a></li> <li><a href="/wiki/Nordefrin" class="mw-redirect" title="Nordefrin">Nordefrin</a> (<a href="/wiki/Levonordefrin" class="mw-redirect" title="Levonordefrin">Levonordefrin</a>)</li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a> (<i>m</i>-Octopamine)</li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AL-LAD" title="AL-LAD">AL-LAD</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Desvenlafaxine" title="Desvenlafaxine">Desvenlafaxine</a></li> <li><a href="/wiki/Diphenidine" title="Diphenidine">Diphenidine</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/ETH-LAD" title="ETH-LAD">ETH-LAD</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fluorolintane" title="Fluorolintane">Fluorolintane</a></li> <li><a href="/wiki/Hexapradol" title="Hexapradol">Hexapradol</a></li> <li><a href="/wiki/IP-LAD" class="mw-redirect" title="IP-LAD">IP-LAD</a></li> <li><a href="/wiki/Lysergic_acid_amide" class="mw-redirect" title="Lysergic acid amide">Lysergic acid amide</a></li> <li><a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">Lysergic acid 2-butyl amide</a></li> <li><a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">Lysergic acid 2,4-dimethylazetidide</a></li> <li><a href="/wiki/LSD" title="LSD">Lysergic acid diethylamide</a></li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Methoxphenidine" title="Methoxphenidine">Methoxphenidine</a></li> <li><a href="/wiki/MT-45" title="MT-45">MT-45</a></li> <li><a href="/wiki/PARGY-LAD" title="PARGY-LAD">PARGY-LAD</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a href="/wiki/PRO-LAD" title="PRO-LAD">PRO-LAD</a></li> <li><a href="/wiki/Pronethalol" title="Pronethalol">Pronethalol</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a> (<a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a>)</li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Thiamphenicol" title="Thiamphenicol">Thiamphenicol</a></li> <li><a href="/wiki/UWA-101" title="UWA-101">UWA-101</a></li> <li><a href="/wiki/Venlafaxine" title="Venlafaxine">Venlafaxine</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img 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