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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">Chemical compound</div> <p class="mw-empty-elt"> </p> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): 5-MAPB">5-MAPB</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="mw-default-size skin-invert-image" typeof="mw:File/Frameless"><a href="/wiki/File:5-MAPB.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/5-MAPB.svg/250px-5-MAPB.svg.png" decoding="async" width="220" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/5-MAPB.svg/330px-5-MAPB.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a7/5-MAPB.svg/500px-5-MAPB.svg.png 2x" data-file-width="510" data-file-height="240" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:5-MAPB_molecule_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of 5-MAPB molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/5-MAPB_molecule_ball.png/220px-5-MAPB_molecule_ball.png" decoding="async" width="220" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/5-MAPB_molecule_ball.png/330px-5-MAPB_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/5-MAPB_molecule_ball.png/440px-5-MAPB_molecule_ball.png 2x" data-file-width="2000" data-file-height="1184" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">5-(<i>N</i>-Methyl-2-aminopropyl)benzofuran</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">Oral, Insufflated, Rectal</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Canada">CA</abbr></small>: <a href="/wiki/Controlled_Drugs_and_Substances_Act#Schedule_I" title="Controlled Drugs and Substances Act">Schedule I</a></li> <li><small><abbr class="country-name" title="Germany">DE</abbr></small>: <a href="/wiki/List_of_German_drug_laws#NpGS" title="List of German drug laws">NpSG</a> (Industrial and scientific use only)</li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> <a href="/wiki/Drugs_controlled_by_the_UK_Misuse_of_Drugs_Act#Class_B_drugs" class="mw-redirect" title="Drugs controlled by the UK Misuse of Drugs Act">Class B</a></li> <li>Illegal in China</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">1-(Benzofuran-5-yl)-<i>N</i>-methylpropan-2-amine</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=1354631-77-8">1354631-77-8</a></span></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/102336592">102336592</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.32078887.html">32078887</a></span></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/XW34GUY2OY">XW34GUY2OY</a></span></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/DTXSID301010102,">DTXSID801017189 DTXSID301010102, DTXSID801017189</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q4639615#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 colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>12</sub><span title="Hydrogen">H</span><sub>15</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data">189.25 g/mol (freebase)<br />225.7 g/mol (<a href="/wiki/Hydrochloride" title="Hydrochloride">HCl salt</a>) 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=CC%28NC%29CC1%3DCC%28C%3DCO2%29%3DC2C%3DC1">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%;">CC(NC)CC1=CC(C=CO2)=C2C=C1</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/C12H15NO/c1-9(13-2)7-10-3-4-12-11(8-10)5-6-14-12/h3-6,8-9,13H,7H2,1-2H3</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:ZOVRTIPCNFERHY-UHFFFAOYSA-N</div></li></ul> </div></td></tr></tbody></table> <p><b>5-MAPB</b>, also known as <b>5-(<i>N</i>-methyl-2-aminopropyl)benzofuran</b>, is an <a href="/wiki/Entactogen" class="mw-redirect" title="Entactogen">entactogen</a> and <a href="/wiki/Designer_drug" title="Designer drug">designer drug</a> of the <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">amphetamine</a> family that is similar to <a href="/wiki/MDMA" title="MDMA">MDMA</a> in its <a href="/wiki/Chemical_structure" title="Chemical structure">structure</a> and effects.<sup id="cite_ref-ACMD_report_1-0" class="reference"><a href="#cite_note-ACMD_report-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>It has been <a href="/wiki/Patent" title="Patent">patented</a> by <a href="/wiki/Tactogen" title="Tactogen">Tactogen</a> as an entactogen for potential use as a medicine.<sup id="cite_ref-WO2021/252538_2-0" class="reference"><a href="#cite_note-WO2021/252538-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <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=5-MAPB&action=edit&section=1" 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=5-MAPB&action=edit&section=2" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>5-MAPB acts as a <a href="/wiki/Serotonin%E2%80%93norepinephrine%E2%80%93dopamine_releasing_agent" title="Serotonin–norepinephrine–dopamine releasing agent">serotonin–norepinephrine–dopamine releasing agent</a> with <a href="/wiki/Half-maximal_effective_concentration" class="mw-redirect" title="Half-maximal effective concentration"><abbr title="half-maximal effective concentration">EC<sub>50</sub></abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip half-maximal effective concentration</span> values for <a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">induction of monoamine release</a> of 64<span class="nowrap"> </span>nM for <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, 24<span class="nowrap"> </span>nM for <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>, and 41<span class="nowrap"> </span>nM for <a href="/wiki/Dopamine" title="Dopamine">dopamine</a> using rat brain <a href="/wiki/Synaptosome" title="Synaptosome">synaptosomes</a>.<sup id="cite_ref-RoqueBravoSilvaCarmo2022_3-0" class="reference"><a href="#cite_note-RoqueBravoSilvaCarmo2022-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Oeri2021_4-0" class="reference"><a href="#cite_note-Oeri2021-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BrandtWaltersPartilla2020_5-0" class="reference"><a href="#cite_note-BrandtWaltersPartilla2020-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SahaiDavidsonKhelashvili2017_6-0" class="reference"><a href="#cite_note-SahaiDavidsonKhelashvili2017-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It is also a <a href="/wiki/Partial_agonist" title="Partial agonist">partial agonist</a> of the serotonin <a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT<sub>2A</sub></a>, <a href="/wiki/5-HT2B_receptor" title="5-HT2B receptor">5-HT<sub>2B</sub></a>, and <a href="/wiki/5-HT2C_receptor" title="5-HT2C receptor">5-HT<sub>2C</sub> receptors</a>.<sup id="cite_ref-RoqueBravoSilvaCarmo2022_3-1" class="reference"><a href="#cite_note-RoqueBravoSilvaCarmo2022-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Oeri2021_4-1" class="reference"><a href="#cite_note-Oeri2021-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ShimshoniWinklerGolan2017_7-0" class="reference"><a href="#cite_note-ShimshoniWinklerGolan2017-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption>Monoamine release of 5-MAPB and its enantiomers<sup id="cite_ref-WO2021/252538_2-1" class="reference"><a href="#cite_note-WO2021/252538-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th>Compound</th> <th><a href="/wiki/Serotonin_transporter" title="Serotonin transporter"><abbr title="Serotonin transporter">SERT</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 transporter</span></th> <th><a href="/wiki/Norepinephrine_transporter" title="Norepinephrine transporter"><abbr title="Norepinephrine transporter">NET</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 transporter</span></th> <th><a href="/wiki/Dopamine_transporter" title="Dopamine transporter"><abbr title="Dopamine transporter">DAT</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 transporter</span></th> <th>DAT/SERT ratio </th></tr> <tr> <td>(<i>S</i>)-5-MAPB</td> <td>67</td> <td><abbr title="No data">ND</abbr></td> <td>258</td> <td>0.26 </td></tr> <tr> <td>75% (<i>S</i>)-5-MAPB</td> <td>80</td> <td><abbr title="No data">ND</abbr></td> <td>632</td> <td>0.13 </td></tr> <tr> <td>(<i>RS</i>)-5-MAPB</td> <td>90</td> <td><abbr title="No data">ND</abbr></td> <td>459</td> <td>0.20 </td></tr> <tr> <td>75% (<i>R</i>)-5-MAPB</td> <td>122</td> <td><abbr title="No data">ND</abbr></td> <td>794</td> <td>0.15 </td></tr> <tr> <td>(<i>R</i>)-5-MAPB</td> <td>184</td> <td><abbr title="No data">ND</abbr></td> <td>1951</td> <td>0.09 </td></tr> <tr class="sortbottom"> <td colspan="5" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Note:</b> This assay used <a href="/wiki/Chinese_hamster_ovary_cell" title="Chinese hamster ovary cell">Chinese hamster ovary</a> (CHO) <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a> expressing human <a href="/wiki/Monoamine_transporter" title="Monoamine transporter">monoamine transporters</a> rather than the more typical rat brain synaptosomes assay.<sup id="cite_ref-WO2021/252538_2-2" class="reference"><a href="#cite_note-WO2021/252538-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <p>5-MAPB has been described by Matthew Baggott as the MDMA analogue so far known that has the closest effects and so-called "magic" to MDMA itself.<sup id="cite_ref-Baggott2023_8-0" class="reference"><a href="#cite_note-Baggott2023-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Baggott2024_9-0" class="reference"><a href="#cite_note-Baggott2024-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Other analogues that lack the full quality of MDMA include <a href="/wiki/MBDB" title="MBDB">MBDB</a>, <a href="/wiki/Methylone" title="Methylone">methylone</a>, <a href="/wiki/6-APDB" title="6-APDB">6-APDB</a>, <a href="/wiki/5-APDB" title="5-APDB">5-APDB</a>, <a href="/wiki/6-APB" title="6-APB">6-APB</a>, <a href="/wiki/5-APB" title="5-APB">5-APB</a>, <a href="/wiki/MDAT" title="MDAT">MDAT</a>, and <a href="/wiki/MDAI" title="MDAI">MDAI</a>, among others.<sup id="cite_ref-Baggott2023_8-1" class="reference"><a href="#cite_note-Baggott2023-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Baggott2024_9-1" class="reference"><a href="#cite_note-Baggott2024-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>5-MAPB has been marketed as a less- or non-<a href="/wiki/Neurotoxicity" title="Neurotoxicity">neurotoxic</a> alternative to MDMA.<sup id="cite_ref-JohnsonBurroughsBaggott2022_10-0" class="reference"><a href="#cite_note-JohnsonBurroughsBaggott2022-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> However, 5-MAPB has been found to be a <a href="/wiki/Dose_dependence" class="mw-redirect" title="Dose dependence">dose-dependent</a> <a href="/wiki/Serotonergic_neurotoxin" class="mw-redirect" title="Serotonergic neurotoxin">serotonergic neurotoxin</a> in rodents similarly to MDMA, and might also be a <a href="/wiki/Dopaminergic_neurotoxin" class="mw-redirect" title="Dopaminergic neurotoxin">dopaminergic neurotoxin</a>.<sup id="cite_ref-JohnsonBurroughsBaggott2022_10-1" class="reference"><a href="#cite_note-JohnsonBurroughsBaggott2022-10"><span class="cite-bracket">[</span>10<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=5-MAPB&action=edit&section=3" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Little formal knowledge exists on 5-MAPB. It does not form the <a href="/wiki/%CE%91-methyldopamine" class="mw-redirect" title="Α-methyldopamine">α-methyldopamine</a> metabolite that contributes to the <a href="/wiki/Neurotoxin" title="Neurotoxin">neurotoxicity</a> of <a href="/wiki/3,4-Methylenedioxymethamphetamine" class="mw-redirect" title="3,4-Methylenedioxymethamphetamine">MDMA</a> or <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> A study in rats indicated that the major metabolites of 5-MAPB are <a href="/wiki/5-APB" title="5-APB">5-APB</a> and 3-carboxymethyl-4-hydroxymethamphetamine.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Legal_Status">Legal Status</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-MAPB&action=edit&section=4" title="Edit section: Legal Status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Canada">Canada</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-MAPB&action=edit&section=5" title="Edit section: Canada"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>5-MAPB is not listed itself in the CDSA but since it is structurally related to <a href="/wiki/MDMA" title="MDMA">MDMA</a> it may be considered illegal in Canada, although this has not been tested in court.<sup id="cite_ref-Schedule_1_of_the_CDSA_16-0" class="reference"><a href="#cite_note-Schedule_1_of_the_CDSA-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="China">China</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-MAPB&action=edit&section=6" title="Edit section: China"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As of October 2015 5-MAPB is a controlled substance in China.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Luxembourg">Luxembourg</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-MAPB&action=edit&section=7" title="Edit section: Luxembourg"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As of July 2021, 5-MAPB is not cited in the list of prohibited substances.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Therefore, it is still a legal substance. </p> <div class="mw-heading mw-heading3"><h3 id="United_Kingdom">United Kingdom</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-MAPB&action=edit&section=8" title="Edit section: United Kingdom"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>5-MAPB was originally banned in the UK in June 2013 under a <a href="/wiki/Temporary_class_drug" title="Temporary class drug">Temporary class drug</a> order.<sup id="cite_ref-HO_press_release_19-0" class="reference"><a href="#cite_note-HO_press_release-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> On March 5, 2014, the UK Home Office announced that 5-MAPB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-MAPB&action=edit&section=9" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Borax_combo" title="Borax combo">Borax combo</a></li> <li><a href="/wiki/6-APB" title="6-APB">6-APB</a></li> <li><a href="/wiki/5-APB" title="5-APB">5-APB</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-MAPB&action=edit&section=10" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-ACMD_report-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-ACMD_report_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds">"Temporary class drug order report on 5-6APB and NBOMe compounds"</a>. UK Home Office. 4 June 2013<span class="reference-accessdate">. Retrieved <span class="nowrap">2013-07-10</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Temporary+class+drug+order+report+on+5-6APB+and+NBOMe+compounds&rft.pub=UK+Home+Office&rft.date=2013-06-04&rft_id=https%3A%2F%2Fwww.gov.uk%2Fgovernment%2Fpublications%2Ftemporary-class-drug-order-report-on-benzofury-and-nbome-compounds&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-WO2021/252538-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-WO2021/252538_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-WO2021/252538_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-WO2021/252538_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1041539562">.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}</style><span class="citation patent" id="CITEREFBaggott_M2021"><a rel="nofollow" class="external text" href="https://patents.google.com/patent/WO2021252538A2/en?oq=WO2021252538">WO 2021/252538</a>, Baggott M, "Advantageous benzofuran compositions for mental disorders or enhancement", published 16 December 2021,  assigned to Tactogen Inc.</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Apatent&rft.number=2021/252538&rft.cc=WO&rft.title=Advantageous+benzofuran+compositions+for+mental+disorders+or+enhancement&rft.inventor=Baggott+M&rft.assignee=Tactogen+Inc.&rft.pubdate=16 December 2021"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-RoqueBravoSilvaCarmo2022-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-RoqueBravoSilvaCarmo2022_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-RoqueBravoSilvaCarmo2022_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRoque_BravoSilvaCarmoCarvalho2022" class="citation book cs1">Roque Bravo R, Silva JP, Carmo H, Carvalho F, Dias da Silva D (2022). "The Toll of Benzofurans in the Context of Drug Abuse". <i>Handbook of Substance Misuse and Addictions</i>. Cham: Springer International Publishing. p. 1–24. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-030-67928-6_168-1">10.1007/978-3-030-67928-6_168-1</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-030-67928-6" title="Special:BookSources/978-3-030-67928-6"><bdi>978-3-030-67928-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=The+Toll+of+Benzofurans+in+the+Context+of+Drug+Abuse&rft.btitle=Handbook+of+Substance+Misuse+and+Addictions&rft.place=Cham&rft.pages=1-24&rft.pub=Springer+International+Publishing&rft.date=2022&rft_id=info%3Adoi%2F10.1007%2F978-3-030-67928-6_168-1&rft.isbn=978-3-030-67928-6&rft.aulast=Roque+Bravo&rft.aufirst=R&rft.au=Silva%2C+JP&rft.au=Carmo%2C+H&rft.au=Carvalho%2C+F&rft.au=Dias+da+Silva%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-Oeri2021-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Oeri2021_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Oeri2021_4-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOeri2021" class="citation journal cs1">Oeri HE (May 2021). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8155739">"Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy"</a>. <i>Journal of Psychopharmacology</i>. <b>35</b> (5): <span class="nowrap">512–</span>536. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F0269881120920420">10.1177/0269881120920420</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/PMC8155739">8155739</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/32909493">32909493</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+Psychopharmacology&rft.atitle=Beyond+ecstasy%3A+Alternative+entactogens+to+3%2C4-methylenedioxymethamphetamine+with+potential+applications+in+psychotherapy&rft.volume=35&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E512-%3C%2Fspan%3E536&rft.date=2021-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8155739%23id-name%3DPMC&rft_id=info%3Apmid%2F32909493&rft_id=info%3Adoi%2F10.1177%2F0269881120920420&rft.aulast=Oeri&rft.aufirst=HE&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8155739&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-BrandtWaltersPartilla2020-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-BrandtWaltersPartilla2020_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBrandtWaltersPartillaBlough2020" class="citation journal cs1">Brandt SD, Walters HM, Partilla JS, Blough BE, Kavanagh PV, Baumann MH (December 2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7686291">"The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats"</a>. <i>Psychopharmacology (Berl)</i>. <b>237</b> (12): <span class="nowrap">3703–</span>3714. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00213-020-05648-z">10.1007/s00213-020-05648-z</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/PMC7686291">7686291</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/32875347">32875347</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Psychopharmacology+%28Berl%29&rft.atitle=The+psychoactive+aminoalkylbenzofuran+derivatives%2C+5-APB+and+6-APB%2C+mimic+the+effects+of+3%2C4-methylenedioxyamphetamine+%28MDA%29+on+monoamine+transmission+in+male+rats&rft.volume=237&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3703-%3C%2Fspan%3E3714&rft.date=2020-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7686291%23id-name%3DPMC&rft_id=info%3Apmid%2F32875347&rft_id=info%3Adoi%2F10.1007%2Fs00213-020-05648-z&rft.aulast=Brandt&rft.aufirst=SD&rft.au=Walters%2C+HM&rft.au=Partilla%2C+JS&rft.au=Blough%2C+BE&rft.au=Kavanagh%2C+PV&rft.au=Baumann%2C+MH&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7686291&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-SahaiDavidsonKhelashvili2017-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-SahaiDavidsonKhelashvili2017_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSahaiDavidsonKhelashviliBarrese2017" class="citation journal cs1">Sahai MA, Davidson C, Khelashvili G, Barrese V, Dutta N, Weinstein H, et al. (April 2017). <a rel="nofollow" class="external text" href="http://openaccess.sgul.ac.uk/108925/1/Combined_in_vitro_and_in_silico_approaches.pdf">"Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances - The case of the benzofuran 5-MAPB"</a> <span class="cs1-format">(PDF)</span>. <i>Progress in Neuro-Psychopharmacology & Biological Psychiatry</i>. <b>75</b>: <span class="nowrap">1–</span>9. <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.pnpbp.2016.11.004">10.1016/j.pnpbp.2016.11.004</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/27890676">27890676</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:30943496">30943496</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Progress+in+Neuro-Psychopharmacology+%26+Biological+Psychiatry&rft.atitle=Combined+in+vitro+and+in+silico+approaches+to+the+assessment+of+stimulant+properties+of+novel+psychoactive+substances+-+The+case+of+the+benzofuran+5-MAPB&rft.volume=75&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E9&rft.date=2017-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A30943496%23id-name%3DS2CID&rft_id=info%3Apmid%2F27890676&rft_id=info%3Adoi%2F10.1016%2Fj.pnpbp.2016.11.004&rft.aulast=Sahai&rft.aufirst=MA&rft.au=Davidson%2C+C&rft.au=Khelashvili%2C+G&rft.au=Barrese%2C+V&rft.au=Dutta%2C+N&rft.au=Weinstein%2C+H&rft.au=Opacka-Juffry%2C+J&rft_id=http%3A%2F%2Fopenaccess.sgul.ac.uk%2F108925%2F1%2FCombined_in_vitro_and_in_silico_approaches.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-ShimshoniWinklerGolan2017-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-ShimshoniWinklerGolan2017_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShimshoniWinklerGolanNutt2017" class="citation journal cs1">Shimshoni JA, Winkler I, Golan E, Nutt D (January 2017). "Neurochemical binding profiles of novel indole and benzofuran MDMA analogues". <i>Naunyn Schmiedebergs Arch Pharmacol</i>. <b>390</b> (1): <span class="nowrap">15–</span>24. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00210-016-1297-4">10.1007/s00210-016-1297-4</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/10044%2F1%2F43622">10044/1/43622</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/27650729">27650729</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Naunyn+Schmiedebergs+Arch+Pharmacol&rft.atitle=Neurochemical+binding+profiles+of+novel+indole+and+benzofuran+MDMA+analogues&rft.volume=390&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E15-%3C%2Fspan%3E24&rft.date=2017-01&rft_id=info%3Ahdl%2F10044%2F1%2F43622&rft_id=info%3Apmid%2F27650729&rft_id=info%3Adoi%2F10.1007%2Fs00210-016-1297-4&rft.aulast=Shimshoni&rft.aufirst=JA&rft.au=Winkler%2C+I&rft.au=Golan%2C+E&rft.au=Nutt%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-Baggott2023-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-Baggott2023_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Baggott2023_8-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBaggott2023" class="citation conference cs1">Baggott M (23 June 2023). <a rel="nofollow" class="external text" href="https://2023.psychedelicscience.org/sessions/beyond-ecstasy-progress-in-developing-and-understanding-a-novel-class-of-therapeutic-medicine/"><i>Beyond Ecstasy: Progress in Developing and Understanding a Novel Class of Therapeutic Medicine</i></a>. PS2023 [Psychedelic Science 2023, June 19-23, 2023, Denver, Colorado]. Denver, CO: Multidisciplinary Association for Psychedelic Studies.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=conference&rft.btitle=Beyond+Ecstasy%3A+Progress+in+Developing+and+Understanding+a+Novel+Class+of+Therapeutic+Medicine&rft.place=Denver%2C+CO&rft.pub=Multidisciplinary+Association+for+Psychedelic+Studies&rft.date=2023-06-23&rft.aulast=Baggott&rft.aufirst=M&rft_id=https%3A%2F%2F2023.psychedelicscience.org%2Fsessions%2Fbeyond-ecstasy-progress-in-developing-and-understanding-a-novel-class-of-therapeutic-medicine%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-Baggott2024-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-Baggott2024_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Baggott2024_9-1"><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://www.youtube.com/watch?v=OnhJvKxwfZI&t=1048">"Better Than Ecstasy: Progress in Developing a Novel Class of Therapeutic with Matthew Baggott, PhD"</a>. <i>YouTube</i>. 6 March 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">20 November</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=YouTube&rft.atitle=Better+Than+Ecstasy%3A+Progress+in+Developing+a+Novel+Class+of+Therapeutic+with+Matthew+Baggott%2C+PhD.&rft.date=2024-03-06&rft_id=https%3A%2F%2Fwww.youtube.com%2Fwatch%3Fv%3DOnhJvKxwfZI%26t%3D1048&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-JohnsonBurroughsBaggott2022-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-JohnsonBurroughsBaggott2022_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-JohnsonBurroughsBaggott2022_10-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJohnsonBurroughsBaggottDavidson2022" class="citation conference cs1">Johnson CB, Burroughs RL, Baggott MJ, Davidson CJ, Perrine SA, Baker LE (2022). <a rel="nofollow" class="external text" href="https://www.abstractsonline.com/pp8/#!/10619/presentation/67382"><i>314.03 / RR6 - Locomotor stimulant effects and persistent serotonin depletions following [1-Benzofuran-5-yl)-N-methylpropan-2-amine (5-MAPB) treatment in Sprague-Dawley rats</i></a>. Society for Neuroscience Conference, Nov. 14, 2022, San Diego, CA. <q>5-MAPB has been marketed as a less neurotoxic analogue of MDMA, but no studies have addressed whether 5-MAPB can cause the long lasting serotonergic changes seen with high or repeated MDMA dosing. [...] Neurochemical analyses indicated a statistically significant reduction in 5‑HT and 5-HIAA in all brain regions assessed 24 hours and two weeks after 6 mg/kg 5‑MAPB, with no statistically significant differences in monoamine levels between 1.2 mg/kg and saline-treated rats. There were also non-significant trends for reductions in striatal dopamine at both time intervals after 6 mg/kg 5-MAPB. These results show that 5-MAPB can dose-dependently produce persistent changes in 5-HT and 5-HIAA that appear analogous to those produced by MDMA.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=conference&rft.btitle=314.03+%2F+RR6+-+Locomotor+stimulant+effects+and+persistent+serotonin+depletions+following+%5B1-Benzofuran-5-yl%29-N-methylpropan-2-amine+%285-MAPB%29+treatment+in+Sprague-Dawley+rats&rft.date=2022&rft.aulast=Johnson&rft.aufirst=CB&rft.au=Burroughs%2C+RL&rft.au=Baggott%2C+MJ&rft.au=Davidson%2C+CJ&rft.au=Perrine%2C+SA&rft.au=Baker%2C+LE&rft_id=https%3A%2F%2Fwww.abstractsonline.com%2Fpp8%2F%23%21%2F10619%2Fpresentation%2F67382&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShimshoniWinklerGolanNutt2017" class="citation journal cs1">Shimshoni JA, Winkler I, Golan E, Nutt D (January 2017). "Neurochemical binding profiles of novel indole and benzofuran MDMA analogues". <i>Naunyn-Schmiedeberg's Archives of Pharmacology</i>. <b>390</b> (1): <span class="nowrap">15–</span>24. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00210-016-1297-4">10.1007/s00210-016-1297-4</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/10044%2F1%2F43622">10044/1/43622</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/27650729">27650729</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Naunyn-Schmiedeberg%27s+Archives+of+Pharmacology&rft.atitle=Neurochemical+binding+profiles+of+novel+indole+and+benzofuran+MDMA+analogues&rft.volume=390&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E15-%3C%2Fspan%3E24&rft.date=2017-01&rft_id=info%3Ahdl%2F10044%2F1%2F43622&rft_id=info%3Apmid%2F27650729&rft_id=info%3Adoi%2F10.1007%2Fs00210-016-1297-4&rft.aulast=Shimshoni&rft.aufirst=JA&rft.au=Winkler%2C+I&rft.au=Golan%2C+E&rft.au=Nutt%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMcCannRicaurte1991" class="citation journal cs1">McCann UD, Ricaurte GA (April 1991). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0006-8993%2891%2991297-E">"Major metabolites of (+/-)3,4-methylenedioxyamphetamine (MDA) do not mediate its toxic effects on brain serotonin neurons"</a>. <i>Brain Research</i>. <b>545</b> (<span class="nowrap">1–</span>2): <span class="nowrap">279–</span>282. <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%2F0006-8993%2891%2991297-E">10.1016/0006-8993(91)91297-E</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/1860050">1860050</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:2574803">2574803</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Brain+Research&rft.atitle=Major+metabolites+of+%28%2B%2F-%293%2C4-methylenedioxyamphetamine+%28MDA%29+do+not+mediate+its+toxic+effects+on+brain+serotonin+neurons&rft.volume=545&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E279-%3C%2Fspan%3E282&rft.date=1991-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A2574803%23id-name%3DS2CID&rft_id=info%3Apmid%2F1860050&rft_id=info%3Adoi%2F10.1016%2F0006-8993%2891%2991297-E&rft.aulast=McCann&rft.aufirst=UD&rft.au=Ricaurte%2C+GA&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252F0006-8993%252891%252991297-E&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMillerLauMonks1997" class="citation journal cs1">Miller RT, Lau SS, Monks TJ (April 1997). "2,5-Bis-(glutathion-S-yl)-alpha-methyldopamine, a putative metabolite of (+/-)-3,4-methylenedioxyamphetamine, decreases brain serotonin concentrations". <i>European Journal of Pharmacology</i>. <b>323</b> (<span class="nowrap">2–</span>3): <span class="nowrap">173–</span>180. <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%2FS0014-2999%2897%2900044-7">10.1016/S0014-2999(97)00044-7</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/9128836">9128836</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Pharmacology&rft.atitle=2%2C5-Bis-%28glutathion-S-yl%29-alpha-methyldopamine%2C+a+putative+metabolite+of+%28%2B%2F-%29-3%2C4-methylenedioxyamphetamine%2C+decreases+brain+serotonin+concentrations&rft.volume=323&rft.issue=%3Cspan+class%3D%22nowrap%22%3E2%E2%80%93%3C%2Fspan%3E3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E173-%3C%2Fspan%3E180&rft.date=1997-04&rft_id=info%3Adoi%2F10.1016%2FS0014-2999%2897%2900044-7&rft_id=info%3Apmid%2F9128836&rft.aulast=Miller&rft.aufirst=RT&rft.au=Lau%2C+SS&rft.au=Monks%2C+TJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFConwayLouisJarrott1978" class="citation journal cs1">Conway EL, Louis WJ, Jarrott B (December 1978). "Acute and chronic administration of alpha-methyldopa: regional levels of endogenous and alpha-methylated catecholamines in rat brain". <i>European Journal of Pharmacology</i>. <b>52</b> (<span class="nowrap">3–</span>4): <span class="nowrap">271–</span>280. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0014-2999%2878%2990279-0">10.1016/0014-2999(78)90279-0</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/729639">729639</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Pharmacology&rft.atitle=Acute+and+chronic+administration+of+alpha-methyldopa%3A+regional+levels+of+endogenous+and+alpha-methylated+catecholamines+in+rat+brain&rft.volume=52&rft.issue=%3Cspan+class%3D%22nowrap%22%3E3%E2%80%93%3C%2Fspan%3E4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E271-%3C%2Fspan%3E280&rft.date=1978-12&rft_id=info%3Adoi%2F10.1016%2F0014-2999%2878%2990279-0&rft_id=info%3Apmid%2F729639&rft.aulast=Conway&rft.aufirst=EL&rft.au=Louis%2C+WJ&rft.au=Jarrott%2C+B&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWelterKavanaghMeyerMaurer2015" class="citation journal cs1">Welter J, Kavanagh P, Meyer MR, Maurer HH (February 2015). "Benzofuran analogues of amphetamine and methamphetamine: studies on the metabolism and toxicological analysis of 5-APB and 5-MAPB in urine and plasma using GC-MS and LC-(HR)-MS(n) techniques". <i>Analytical and Bioanalytical Chemistry</i>. <b>407</b> (5): <span class="nowrap">1371–</span>1388. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00216-014-8360-0">10.1007/s00216-014-8360-0</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/25471293">25471293</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:20653012">20653012</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Analytical+and+Bioanalytical+Chemistry&rft.atitle=Benzofuran+analogues+of+amphetamine+and+methamphetamine%3A+studies+on+the+metabolism+and+toxicological+analysis+of+5-APB+and+5-MAPB+in+urine+and+plasma+using+GC-MS+and+LC-%28HR%29-MS%28n%29+techniques&rft.volume=407&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1371-%3C%2Fspan%3E1388&rft.date=2015-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A20653012%23id-name%3DS2CID&rft_id=info%3Apmid%2F25471293&rft_id=info%3Adoi%2F10.1007%2Fs00216-014-8360-0&rft.aulast=Welter&rft.aufirst=J&rft.au=Kavanagh%2C+P&rft.au=Meyer%2C+MR&rft.au=Maurer%2C+HH&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-Schedule_1_of_the_CDSA-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-Schedule_1_of_the_CDSA_16-0">^</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/20131122143804/http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-24.html#h-28">"Schedule I"</a>. Government Of Canada. 2014-12-12. Archived from <a rel="nofollow" class="external text" href="https://laws-lois.justice.gc.ca/eng/acts/c-38.8/page-24.html#h-28">the original</a> on 2013-11-22<span class="reference-accessdate">. Retrieved <span class="nowrap">2014-12-13</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Schedule+I&rft.pub=Government+Of+Canada&rft.date=2014-12-12&rft_id=http%3A%2F%2Flaws-lois.justice.gc.ca%2Feng%2Facts%2Fc-38.8%2Fpage-24.html%23h-28&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1 cs1-prop-foreign-lang-source"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html">"关于印发《非药用类麻醉药品和精神药品列管办法》的通知"</a> [Notice on the issuance of the "Regulations on the Listing of Non-Medicinal Narcotic Drugs and Psychotropic Drugs"] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from <a rel="nofollow" class="external text" href="http://www.sfda.gov.cn/WS01/CL0056/130753.html">the original</a> on 1 October 2015<span class="reference-accessdate">. Retrieved <span class="nowrap">1 October</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%E5%85%B3%E4%BA%8E%E5%8D%B0%E5%8F%91%E3%80%8A%E9%9D%9E%E8%8D%AF%E7%94%A8%E7%B1%BB%E9%BA%BB%E9%86%89%E8%8D%AF%E5%93%81%E5%92%8C%E7%B2%BE%E7%A5%9E%E8%8D%AF%E5%93%81%E5%88%97%E7%AE%A1%E5%8A%9E%E6%B3%95%E3%80%8B%E7%9A%84%E9%80%9A%E7%9F%A5&rft.pub=China+Food+and+Drug+Administration&rft.date=2015-09-27&rft_id=http%3A%2F%2Fwww.sfda.gov.cn%2FWS01%2FCL0056%2F130753.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1 cs1-prop-foreign-lang-source"><a rel="nofollow" class="external text" href="http://legilux.public.lu/eli/etat/leg/loi/1973/02/19/n1/jo">"Loi du 19 février 1973 concernant la vente de substances médicamenteuses et la lutte contre la toxicomanie"</a> [Law of February 19, 1973 concerning the sale of medicinal substances and the fight against drug addiction.]. <i>Journal officiel du Grand-Duché de Luxembourg</i> (in French).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Journal+officiel+du+Grand-Duch%C3%A9+de+Luxembourg&rft.atitle=Loi+du+19+f%C3%A9vrier+1973+concernant+la+vente+de+substances+m%C3%A9dicamenteuses+et+la+lutte+contre+la+toxicomanie.&rft_id=http%3A%2F%2Flegilux.public.lu%2Feli%2Fetat%2Fleg%2Floi%2F1973%2F02%2F19%2Fn1%2Fjo&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-HO_press_release-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-HO_press_release_19-0">^</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.gov.uk/government/news/nbome-and-benzofury-to-be-banned">"<span class="cs1-kern-left"></span>'NBOMe' and 'Benzofury' banned"</a>. UK Home Office. 2013-06-04<span class="reference-accessdate">. Retrieved <span class="nowrap">10 April</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=%27NBOMe%27+and+%27Benzofury%27+banned&rft.pub=UK+Home+Office&rft.date=2013-06-04&rft_id=https%3A%2F%2Fwww.gov.uk%2Fgovernment%2Fnews%2Fnbome-and-benzofury-to-be-banned&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFUK_Home_Office2014" class="citation web cs1">UK Home Office (2014-03-05). <a rel="nofollow" class="external text" href="http://www.legislation.gov.uk/ukdsi/2014/9780111110904">"The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014"</a>. UK Government<span class="reference-accessdate">. Retrieved <span class="nowrap">2014-03-11</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=The+Misuse+of+Drugs+Act+1971+%28Ketamine+etc.%29+%28Amendment%29+Order+2014&rft.pub=UK+Government&rft.date=2014-03-05&rft.au=UK+Home+Office&rft_id=http%3A%2F%2Fwww.legislation.gov.uk%2Fukdsi%2F2014%2F9780111110904&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-MAPB" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output 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.navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Entactogens" title="Template:Entactogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Entactogens" title="Template talk:Entactogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Entactogens" title="Special:EditPage/Template:Entactogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Empathogens/entactogens340" style="font-size:114%;margin:0 4em"><a href="/wiki/Empathogen-entactogen" class="mw-redirect" title="Empathogen-entactogen">Empathogens/entactogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenylalkyl-<br />amines</a><br />(other than<br />cathinones)</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>Unfused benzene ring:</i> <a href="/wiki/3-Chloromethamphetamine" title="3-Chloromethamphetamine">3-CMA</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-methylamphetamine" class="mw-redirect" title="4-methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/4,4%27-Dimethylaminorex" title="4,4'-Dimethylaminorex">4,4'-DMAR</a></li> <li><a href="/wiki/Ariadne_(psychedelic)" class="mw-redirect" title="Ariadne (psychedelic)">Ariadne</a></li> <li><a href="/wiki/Metaescaline" title="Metaescaline">Metaescaline</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxy-N-ethylamphetamine" title="Para-Methoxy-N-ethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxy-N-methylamphetamine" class="mw-redirect" title="Para-Methoxy-N-methylamphetamine">PMMA</a></li> <li><a href="/wiki/3-Methoxy-N-methylamphetamine" class="mw-redirect" title="3-Methoxy-N-methylamphetamine">mMMA</a><br /><i>Benzodioxine:</i> <a href="/wiki/EDMA" title="EDMA">EDMA</a><br /><i>Benzodioxoles:</i> Phenethylamine: { <a href="/wiki/Lophophine" title="Lophophine">Lophophine</a> }</li> <li>Amphetamines: { <a href="/wiki/2-Methyl-MDA" title="2-Methyl-MDA">2-Methyl-MDA</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/5-Methyl-MDA" title="5-Methyl-MDA">5-Methyl-MDA</a></li> <li><a href="/wiki/6-Methyl-MDA" title="6-Methyl-MDA">6-Methyl-MDA</a></li> <li><a href="/wiki/DFMDA" title="DFMDA">DFMDA</a></li> <li><a href="/wiki/DMMDA" title="DMMDA">DMMDA</a></li> <li><a href="/wiki/DMMDA-2" title="DMMDA-2">DMMDA-2</a></li> <li><a href="/wiki/3,4-Ethylidenedioxyamphetamine" title="3,4-Ethylidenedioxyamphetamine">EIDA</a></li> <li><a href="/wiki/Lys-MDA" title="Lys-MDA">Lys-MDA</a></li> <li><a href="/wiki/3,4-Methylenedioxy-N-ethylamphetamine" title="3,4-Methylenedioxy-N-ethylamphetamine">MDEA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a> <ul><li><a href="/wiki/(R)-MDMA" title="(R)-MDMA">(<i>R</i>)-MDMA</a></li></ul></li> <li><a href="/wiki/3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine" title="3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine">MDMOH</a></li> <li><a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</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/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/N-t-BOC-MDMA" title="N-t-BOC-MDMA">N-t-BOC-MDMA</a> }</li> <li>1-Phenylbutan-2-amines: { <a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/MBDB" title="MBDB">MBDB</a> }</li> <li>Phentermines: { <a href="/wiki/3,4-Methylenedioxy-N-methylphentermine" title="3,4-Methylenedioxy-N-methylphentermine">MDMP</a></li> <li><a href="/wiki/3,4-Methylenedioxyphentermine" title="3,4-Methylenedioxyphentermine">MDPH</a> }<br /><i>Benzofurans, dihydrobenzofurans and benzothiophenes:</i> <a href="/wiki/2-MAPB" title="2-MAPB">2-MAPB</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 class="mw-selflink selflink">5-MAPB</a></li> <li><a href="/wiki/5-MAPDB" title="5-MAPDB">5-MAPDB</a></li> <li><a href="/wiki/5-MAPBT" title="5-MAPBT">5-MAPBT</a></li> <li><a href="/wiki/5-MBPB" title="5-MBPB">5-MBPB (5-MABB)</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-EAPB" title="6-EAPB">6-EAPB</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/6-MBPB" title="6-MBPB">6-MBPB (6-MABB)</a></li> <li><a href="/wiki/IBF5MAP" title="IBF5MAP">IBF5MAP</a><br /><i>Indanes:</i> <a href="/wiki/5-APDI" title="5-APDI">5-APDI</a></li> <li><a href="/wiki/5-MAPDI" title="5-MAPDI">5-MAPDI</a><br /><i>Indoles:</i> <a href="/wiki/5-IT" class="mw-redirect" title="5-IT">5-IT</a></li> <li><a href="/wiki/6-(2-Aminopropyl)indole" title="6-(2-Aminopropyl)indole">6-API</a><br /><i>Naphthalenes:</i> <a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a><br /><i>Tetralin:</i> <a href="/wiki/6-APT" title="6-APT">6-APT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cyclic_compound" title="Cyclic compound">Cyclized</a> <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">phenyl-<br />alkylamines</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>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/BFAI" title="BFAI">BFAI</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/MEAI" title="MEAI">MEAI</a></li> <li><a href="/wiki/NM-2-AI" title="NM-2-AI">NM-2-AI</a></li> <li><a href="/wiki/Trifluoromethylaminoindane" title="Trifluoromethylaminoindane">TAI</a><br /><i>Aminotetralins:</i> <a href="/wiki/6-CAT" title="6-CAT">6-CAT</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><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Cathinones</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Chloromethcathinone" title="3-Chloromethcathinone">3-CMC</a></li> <li><a href="/wiki/3-Methylmethcathinone" title="3-Methylmethcathinone">3-MMC</a></li> <li><a href="/wiki/4-Ethylmethcathinone" title="4-Ethylmethcathinone">4-EMC</a></li> <li><a href="/wiki/BK-5-MAPB" title="BK-5-MAPB">BK-5-MAPB</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/Dimethylone" title="Dimethylone">Dimethylone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</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/TH-PVP" title="TH-PVP">TH-PVP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Methyl-%CE%B1-ethyltryptamine" title="4-Methyl-α-ethyltryptamine">4-Methyl-αET</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></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">Chemical classes</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/Substituted_amphetamine" title="Substituted amphetamine">Substituted amphetamine</a></li> <li><a href="/wiki/Substituted_benzofuran" title="Substituted benzofuran">Sub. benzofuran</a></li> <li><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Sub. cathinone</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">Sub. MDPEA</a></li> <li><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Sub. PEA</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Sub. tryptamine</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_agents1712" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoamine_releasing_agents" title="Template talk:Monoamine releasing agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoamine_releasing_agents" title="Special:EditPage/Template:Monoamine releasing agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoamine_releasing_agents1712" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">Monoamine releasing agents</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Dopamine_releasing_agents" class="mw-redirect" title="Dopamine releasing agents"><abbr title="Dopamine releasing agents">DRAs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dopamine releasing agents</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Morpholines:</i> <a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Oxazolines:</i> <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-MAR</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Cyclazodone" title="Cyclazodone">Cyclazodone</a></li> <li><a href="/wiki/Fenozolone" title="Fenozolone">Fenozolone</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li> <li><a href="/wiki/Pemoline" title="Pemoline">Pemoline</a></li> <li><a href="/wiki/Thozalinone" title="Thozalinone">Thozalinone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Phenethylamines:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">2-OH-PEA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Me-PEA</a></li> <li><a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" class="mw-redirect" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Iofetamine_(123I)" title="Iofetamine (123I)">Iofetamine (123I)</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" 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" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> <ul><li><a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a></li></ul></li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Me-PEA</a></li> <li><a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" class="mw-redirect" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/5-APDI" title="5-APDI">5-APDI</a> (IAP)</li> <li><a href="/wiki/Iofetamine_(123I)" title="Iofetamine (123I)">Iofetamine (123I)</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-methylbutanamine" class="mw-redirect" title="1,3-Benzodioxolyl-N-methylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" 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 href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-HA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-Methyl-MDA" title="5-Methyl-MDA">5-Methyl-MDA</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Methyl-MDA" title="6-Methyl-MDA">6-Methyl-MDA</a></li> <li><a href="/wiki/3-Methoxy-4-methyl-%CE%B1-ethylphenethylamine" class="mw-redirect" title="3-Methoxy-4-methyl-α-ethylphenethylamine">AEMMA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">Brephedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">DCA</a></li> <li><a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a></li> <li><a href="/wiki/DFMDA" title="DFMDA">DFMDA</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" class="mw-redirect" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/EDMA" title="EDMA">EDMA</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Flucetorex" title="Flucetorex">Flucetorex</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylbenzodioxolylbutanamine" class="mw-redirect" title="Methylbenzodioxolylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxymethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxymethamphetamine">MDHMA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/3-Methoxy-4-methylmethamphetamine" class="mw-redirect" title="3-Methoxy-4-methylmethamphetamine">MMMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">NAP</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/4-Trifluoromethylamphetamine" class="mw-redirect" title="4-Trifluoromethylamphetamine">4-TFMA</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">pBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">pCA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">pIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxyethylamphetamine" class="mw-redirect" title="Para-Methoxyethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxymethamphetamine" title="Para-Methoxymethamphetamine">PMMA</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Piperazines:</i> <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/w/index.php?title=3-Methoxyphenylpiperazine&action=edit&redlink=1" class="new" title="3-Methoxyphenylpiperazine (page does not exist)">3-MeOPP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/3,4-Dichlorophenylpiperazine" class="mw-redirect" title="3,4-Dichlorophenylpiperazine">DCPP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Mepiprazole" title="Mepiprazole">Mepiprazole</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Para-Chlorophenylpiperazine" title="Para-Chlorophenylpiperazine">pCPP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li> <li><a href="/wiki/1-(4-Trifluoromethyl-phenyl)-piperazine" class="mw-redirect" title="1-(4-Trifluoromethyl-phenyl)-piperazine">pTFMPP</a></li> <li><a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Tryptamines:</i> <a href="/wiki/4-Methyl-AET" class="mw-redirect" title="4-Methyl-AET">4-Methyl-αET</a></li> <li><a href="/wiki/4-Methyl-AMT" class="mw-redirect" title="4-Methyl-AMT">4-Methyl-αMT</a></li> <li><a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a></li> <li><a href="/wiki/5-MeO-AMT" title="5-MeO-AMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a></li> <li><a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a></li> <li><a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Others:</i> <a href="/wiki/Indeloxazine" title="Indeloxazine">Indeloxazine</a></li> <li><a href="/wiki/Viqualine" title="Viqualine">Viqualine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>DAT modulators:</i> <i>Agonist-like:</i> <a href="/wiki/SoRI-9804" title="SoRI-9804">SoRI-9804</a></li> <li><a href="/w/index.php?title=SoRI-20040&action=edit&redlink=1" class="new" title="SoRI-20040 (page does not exist)">SoRI-20040</a>; <i>Antagonist-like:</i> <a href="/wiki/SoRI-20041" title="SoRI-20041">SoRI-20041</a></li></ul> <ul><li><i>Adrenergic release blockers:</i> <a href="/wiki/Bethanidine" title="Bethanidine">Bethanidine</a></li> <li><a href="/wiki/Bretylium" title="Bretylium">Bretylium</a></li> <li><a href="/wiki/Guanadrel" title="Guanadrel">Guanadrel</a></li> <li><a href="/wiki/Guanazodine" title="Guanazodine">Guanazodine</a></li> <li><a href="/wiki/Guanethidine" title="Guanethidine">Guanethidine</a></li> <li><a href="/wiki/Guanoxan" title="Guanoxan">Guanoxan</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><small><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> • <a href="/wiki/Template:Adrenergics" class="mw-redirect" title="Template:Adrenergics">Adrenergics</a> • <a href="/wiki/Template:Dopaminergics" class="mw-redirect" title="Template:Dopaminergics">Dopaminergics</a> • <a href="/wiki/Template:Serotonergics" class="mw-redirect" title="Template:Serotonergics">Serotonergics</a> • <a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a> • <a href="/wiki/Template:Monoamine_neurotoxins" class="mw-redirect" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></i></small></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Monoaminergic_neurotoxins598" 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:Monoaminergic_neurotoxins" title="Template:Monoaminergic neurotoxins"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoaminergic_neurotoxins" title="Template talk:Monoaminergic neurotoxins"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoaminergic_neurotoxins" title="Special:EditPage/Template:Monoaminergic neurotoxins"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoaminergic_neurotoxins598" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoaminergic_neurotoxin" class="mw-redirect" title="Monoaminergic neurotoxin">Monoaminergic neurotoxins</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Dopaminergic" title="Dopaminergic">Dopaminergic</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/2%E2%80%B2-CH3-MPTP" title="2′-CH3-MPTP">2′-CH<sub>3</sub>-MPTP (2′-methyl-MPTP)</a></li> <li><a href="/wiki/2,4,5-Trihydroxyamphetamine" title="2,4,5-Trihydroxyamphetamine">2,4,5-THA</a></li> <li><a href="/wiki/2,4,5-Trihydroxymethamphetamine" title="2,4,5-Trihydroxymethamphetamine">2,4,5-THMA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/w/index.php?title=5-S-Cysteinyldopamine&action=edit&redlink=1" class="new" title="5-S-Cysteinyldopamine (page does not exist)">5-<i>S</i>-Cysteinyldopamine</a></li> <li><a href="/wiki/5,6-Dihydroxytryptamine" title="5,6-Dihydroxytryptamine">5,6-DHT</a></li> <li><a href="/wiki/6-Hydroxydopa" title="6-Hydroxydopa">6-Hydroxydopa</a></li> <li><a href="/w/index.php?title=6-Hydroxydopamine_quinone&action=edit&redlink=1" class="new" title="6-Hydroxydopamine quinone (page does not exist)">6-OHDA quinone</a></li> <li><a href="/wiki/6,7-Dihydroxytryptamine" title="6,7-Dihydroxytryptamine">6,7-DHT</a></li> <li><a href="/wiki/Aldehyde_dehydrogenase_inhibitor" class="mw-redirect" title="Aldehyde dehydrogenase inhibitor">ALDH inhibitors</a> (e.g., <a href="/wiki/Disulfiram" title="Disulfiram">disulfiram</a>, <a href="/wiki/Methylmercury" title="Methylmercury">methylmercury</a>)</li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/Benomyl" title="Benomyl">Benomyl</a></li> <li><a href="/wiki/Daidzin" title="Daidzin">Daidzin</a></li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/w/index.php?title=DOPA_quinone&action=edit&redlink=1" class="new" title="DOPA quinone (page does not exist)">DOPA quinone</a></li> <li><a href="/wiki/3,4-Dihydroxyphenylacetaldehyde" title="3,4-Dihydroxyphenylacetaldehyde">DOPAL</a></li> <li><a href="/w/index.php?title=DOPAL_quinone&action=edit&redlink=1" class="new" title="DOPAL quinone (page does not exist)">DOPAL quinone</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/w/index.php?title=Dopamine_quinone&action=edit&redlink=1" class="new" title="Dopamine quinone (page does not exist)">Dopamine quinone</a></li> <li><a href="/wiki/Fenpropathrin" title="Fenpropathrin">Fenpropathrin</a></li> <li><a href="/wiki/Haloperidol" title="Haloperidol">Haloperidol</a></li> <li><a href="/wiki/HPP%2B" title="HPP+">HPP<sup>+</sup></a></li> <li><a href="/wiki/HPTP" title="HPTP">HPTP</a></li> <li><a href="/wiki/Mancozeb" title="Mancozeb">Mancozeb</a></li> <li><a href="/wiki/Maneb" title="Maneb">Maneb</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/MPP%2B" title="MPP+">MPP<sup>+</sup> (cyperquat)</a></li> <li><a href="/wiki/MPTP" title="MPTP">MPTP</a></li> <li><a href="/w/index.php?title=N-Methylnorsalsolinol&action=edit&redlink=1" class="new" title="N-Methylnorsalsolinol (page does not exist)"><i>N</i>-Methylnorsalsolinol</a></li> <li><a href="/wiki/Norsalsolinol" title="Norsalsolinol">Norsalsolinol</a></li> <li><a href="/wiki/Oxidopamine" title="Oxidopamine">Oxidopamine (6-OHDA)</a></li> <li><a href="/wiki/Paraquat" title="Paraquat">Paraquat</a></li> <li><a href="/wiki/Rotenone" title="Rotenone">Rotenone</a></li> <li><a href="/wiki/Salsolinol" title="Salsolinol">Salsolinol</a></li> <li><a href="/wiki/Zinc_bis(dimethyldithiocarbamate)" title="Zinc bis(dimethyldithiocarbamate)">Ziram</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Noradrenergic" class="mw-redirect" title="Noradrenergic">Noradrenergic</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2%E2%80%B2-NH2-MPTP" title="2′-NH2-MPTP">2′-NH<sub>2</sub>-MPTP (2′-amino-MPTP)</a></li> <li><a href="/wiki/2,4,5-Trihydroxyamphetamine" title="2,4,5-Trihydroxyamphetamine">2,4,5-THA</a></li> <li><a href="/wiki/4,5-Dihydroxytryptamine" title="4,5-Dihydroxytryptamine">4,5-DHT</a></li> <li><a href="/wiki/5,6-Dihydroxytryptamine" title="5,6-Dihydroxytryptamine">5,6-DHT</a></li> <li><a href="/wiki/5,7-Dihydroxytryptamine" title="5,7-Dihydroxytryptamine">5,7-DHT</a></li> <li><a href="/wiki/6-Hydroxydopa" title="6-Hydroxydopa">6-Hydroxydopa</a></li> <li><a href="/wiki/3,4-Dihydroxyphenylglycolaldehyde" title="3,4-Dihydroxyphenylglycolaldehyde">DOPEGAL</a></li> <li><a href="/wiki/DSP-4" title="DSP-4">DSP-4</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Oxidopamine" title="Oxidopamine">Oxidopamine (6-OHDA)</a></li> <li><a href="/wiki/Xylamine" title="Xylamine">Xylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Serotonin" title="Serotonin">Serotonergic</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/2%E2%80%B2-NH2-MPTP" title="2′-NH2-MPTP">2′-NH<sub>2</sub>-MPTP (2′-amino-MPTP)</a></li> <li><a href="/wiki/2,4-Dichloroamphetamine" title="2,4-Dichloroamphetamine">2,4-DCA</a></li> <li><a href="/wiki/2,4,5-Trihydroxyamphetamine" title="2,4,5-Trihydroxyamphetamine">2,4,5-THA</a></li> <li><a href="/wiki/2,4,5-Trihydroxymethamphetamine" title="2,4,5-Trihydroxymethamphetamine">2,4,5-THMA</a></li> <li><a href="/wiki/3-Chloroamphetamine" title="3-Chloroamphetamine">3-CA</a></li> <li><a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">3,4-DCA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB (α-ethyl-PCA)</a></li> <li><a href="/wiki/Para-Chloromethamphetamine" title="Para-Chloromethamphetamine">4-CMA</a></li> <li><a href="/wiki/4-Hydroxy-5-methoxytryptamine" title="4-Hydroxy-5-methoxytryptamine">4-HO-5-MeO-T</a></li> <li><a href="/wiki/4,5-Dihydroxytryptamine" title="4,5-Dihydroxytryptamine">4,5-DHT</a></li> <li><a href="/wiki/5-Iodo-2-aminoindane" class="mw-redirect" title="5-Iodo-2-aminoindane">5-IAI</a></li> <li><a class="mw-selflink selflink">5-MAPB</a></li> <li><a href="/wiki/5,6-Dihydroxytryptamine" title="5,6-Dihydroxytryptamine">5,6-DHT</a></li> <li><a href="/wiki/5,7-Dihydroxytryptamine" title="5,7-Dihydroxytryptamine">5,7-DHT</a></li> <li><a href="/wiki/6,7-Dihydroxytryptamine" title="6,7-Dihydroxytryptamine">6,7-DHT</a></li> <li><a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Haloperidol" title="Haloperidol">Haloperidol</a></li> <li><a href="/wiki/3,4-Dihydroxyamphetamine" class="mw-redirect" title="3,4-Dihydroxyamphetamine">HHA (α-methyldopamine)</a></li> <li><a href="/wiki/3,4-Dihydroxymethamphetamine" title="3,4-Dihydroxymethamphetamine">HHMA (α-methylepinine, α,<i>N</i>-dimethyldopamine)</a></li> <li><a href="/wiki/HPP%2B" title="HPP+">HPP<sup>+</sup></a></li> <li><a href="/wiki/HPTP" title="HPTP">HPTP</a></li> <li><a href="/wiki/MBDB" title="MBDB">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/3,4-Methylenedioxymethamphetamine" class="mw-redirect" title="3,4-Methylenedioxymethamphetamine">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">PBA</a></li> <li><a href="/wiki/Para-Bromomethamphetamine" title="Para-Bromomethamphetamine">PBMA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">PCA</a></li> <li><a href="/wiki/Para-Chloromethamphetamine" title="Para-Chloromethamphetamine">PCMA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">PIA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Unsorted</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5-Hydroxyindoleacetaldehyde" title="5-Hydroxyindoleacetaldehyde">5-HIAL</a></li> <li><a href="/w/index.php?title=RHPP%2B&action=edit&redlink=1" class="new" title="RHPP+ (page does not exist)">RHPP<sup>+</sup></a></li> <li><a href="/w/index.php?title=RHPTP&action=edit&redlink=1" class="new" title="RHPTP (page does not exist)">RHPTP</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: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:Melatonergics" class="mw-redirect" title="Template:Melatonergics">Melatonergics</a> • <a href="/wiki/Template:Serotonergics" class="mw-redirect" title="Template:Serotonergics">Serotonergics</a> • <a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> • <a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">Monoamine releasing agents</a> • <a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></i></small></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Phenethylamines353" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Phenethylamines" title="Template:Phenethylamines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenethylamines" title="Template talk:Phenethylamines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenethylamines" title="Special:EditPage/Template:Phenethylamines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Phenethylamines353" style="font-size:114%;margin:0 4em"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Psychedelics:</i> <a href="/wiki/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a></li> <li><a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a></li> <li><a href="/wiki/25D-NBOMe" title="25D-NBOMe">25D-NBOMe</a></li> <li><a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a></li> <li><a href="/wiki/25N-NBOMe" title="25N-NBOMe">25N-NBOMe</a></li> <li><a href="/wiki/2C-B" title="2C-B">2C-B</a></li> <li><a href="/w/index.php?title=2C-B-AN&action=edit&redlink=1" class="new" title="2C-B-AN (page does not exist)">2C-B-AN</a></li> <li><a href="/w/index.php?title=2C-Bn&action=edit&redlink=1" class="new" title="2C-Bn (page does not exist)">2C-Bn</a></li> <li><a href="/wiki/2C-Bu" title="2C-Bu">2C-Bu</a></li> <li><a href="/wiki/2C-C" title="2C-C">2C-C</a></li> <li><a href="/w/index.php?title=2C-CN&action=edit&redlink=1" class="new" title="2C-CN (page does not exist)">2C-CN</a></li> <li><a href="/wiki/2C-CP" title="2C-CP">2C-CP</a></li> <li><a href="/wiki/2C-D" title="2C-D">2C-D</a></li> <li><a href="/wiki/2C-E" title="2C-E">2C-E</a></li> <li><a href="/wiki/2C-EF" title="2C-EF">2C-EF</a></li> <li><a href="/wiki/2C-F" title="2C-F">2C-F</a></li> <li><a href="/wiki/2C-G" title="2C-G">2C-G</a></li> <li><a href="/wiki/2C-G-1" class="mw-redirect" title="2C-G-1">2C-G-1</a></li> <li><a href="/wiki/2C-G-2" class="mw-redirect" title="2C-G-2">2C-G-2</a></li> <li><a href="/wiki/2C-G-3" class="mw-redirect" title="2C-G-3">2C-G-3</a></li> <li><a href="/wiki/2C-G-4" class="mw-redirect" title="2C-G-4">2C-G-4</a></li> <li><a href="/wiki/2C-G-5" class="mw-redirect" title="2C-G-5">2C-G-5</a></li> <li><a href="/wiki/2C-G-6" class="mw-redirect" title="2C-G-6">2C-G-6</a></li> <li><a href="/wiki/2C-G-N" class="mw-redirect" title="2C-G-N">2C-G-N</a></li> <li><a href="/wiki/2C-H" title="2C-H">2C-H</a></li> <li><a href="/wiki/2C-I" title="2C-I">2C-I</a></li> <li><a href="/wiki/2C-iBu" title="2C-iBu">2C-iBu</a></li> <li><a href="/wiki/2C-iP" title="2C-iP">2C-iP</a></li> <li><a href="/wiki/2C-N" title="2C-N">2C-N</a></li> <li><a href="/w/index.php?title=2C-NH2&action=edit&redlink=1" class="new" title="2C-NH2 (page does not exist)">2C-NH2</a></li> <li><a href="/wiki/2C-O" class="mw-redirect" title="2C-O">2C-O</a></li> <li><a href="/wiki/2C-O-4" title="2C-O-4">2C-O-4</a></li> <li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li> <li><a href="/wiki/2C-Ph" title="2C-Ph">2C-Ph</a></li> <li><a href="/wiki/2C-SE" class="mw-redirect" title="2C-SE">2C-SE</a></li> <li><a href="/wiki/2C-T" title="2C-T">2C-T</a></li> <li><a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a></li> <li><a href="/wiki/2C-T-3" title="2C-T-3">2C-T-3</a></li> <li><a href="/wiki/2C-T-4" title="2C-T-4">2C-T-4</a></li> <li><a href="/w/index.php?title=2C-T-5&action=edit&redlink=1" class="new" title="2C-T-5 (page does not exist)">2C-T-5</a></li> <li><a href="/w/index.php?title=2C-T-6&action=edit&redlink=1" class="new" title="2C-T-6 (page does not exist)">2C-T-6</a></li> <li><a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a></li> <li><a href="/wiki/2C-T-8" title="2C-T-8">2C-T-8</a></li> <li><a href="/wiki/2C-T-9" class="mw-redirect" title="2C-T-9">2C-T-9</a></li> <li><a href="/w/index.php?title=2C-T-10&action=edit&redlink=1" class="new" title="2C-T-10 (page does not exist)">2C-T-10</a></li> <li><a href="/w/index.php?title=2C-T-11&action=edit&redlink=1" class="new" title="2C-T-11 (page does not exist)">2C-T-11</a></li> <li><a href="/w/index.php?title=2C-T-12&action=edit&redlink=1" class="new" title="2C-T-12 (page does not exist)">2C-T-12</a></li> <li><a href="/wiki/2C-T-13" title="2C-T-13">2C-T-13</a></li> <li><a href="/w/index.php?title=2C-T-14&action=edit&redlink=1" class="new" title="2C-T-14 (page does not exist)">2C-T-14</a></li> <li><a href="/wiki/2C-T-15" title="2C-T-15">2C-T-15</a></li> <li><a href="/wiki/2C-T-16" title="2C-T-16">2C-T-16</a></li> <li><a href="/wiki/2C-T-17" title="2C-T-17">2C-T-17</a></li> <li><a href="/w/index.php?title=2C-T-18&action=edit&redlink=1" class="new" title="2C-T-18 (page does not exist)">2C-T-18</a></li> <li><a href="/wiki/2C-T-19" title="2C-T-19">2C-T-19</a></li> <li><a href="/w/index.php?title=2C-T-20&action=edit&redlink=1" class="new" title="2C-T-20 (page does not exist)">2C-T-20</a></li> <li><a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a></li> <li><a href="/w/index.php?title=2C-T-22&action=edit&redlink=1" class="new" title="2C-T-22 (page does not exist)">2C-T-22</a></li> <li><a href="/w/index.php?title=2C-T-22.5&action=edit&redlink=1" class="new" title="2C-T-22.5 (page does not exist)">2C-T-22.5</a></li> <li><a href="/w/index.php?title=2C-T-23&action=edit&redlink=1" class="new" title="2C-T-23 (page does not exist)">2C-T-23</a></li> <li><a href="/w/index.php?title=2C-T-24&action=edit&redlink=1" class="new" title="2C-T-24 (page does not exist)">2C-T-24</a></li> <li><a href="/w/index.php?title=2C-T-25&action=edit&redlink=1" class="new" title="2C-T-25 (page does not exist)">2C-T-25</a></li> <li><a href="/wiki/2C-T-27" title="2C-T-27">2C-T-27</a></li> <li><a href="/wiki/2C-T-28" title="2C-T-28">2C-T-28</a></li> <li><a href="/w/index.php?title=2C-T-30&action=edit&redlink=1" class="new" title="2C-T-30 (page does not exist)">2C-T-30</a></li> <li><a href="/w/index.php?title=2C-T-31&action=edit&redlink=1" class="new" title="2C-T-31 (page does not exist)">2C-T-31</a></li> <li><a href="/w/index.php?title=2C-T-32&action=edit&redlink=1" class="new" title="2C-T-32 (page does not exist)">2C-T-32</a></li> <li><a href="/wiki/2C-T-33" title="2C-T-33">2C-T-33</a></li> <li><a href="/wiki/2C-tBu" title="2C-tBu">2C-tBu</a></li> <li><a href="/wiki/2C-TFE" title="2C-TFE">2C-TFE</a></li> <li><a href="/wiki/2C-TFM" title="2C-TFM">2C-TFM</a></li> <li><a href="/wiki/2C-YN" title="2C-YN">2C-YN</a></li> <li><a href="/wiki/2C-V" title="2C-V">2C-V</a></li> <li><a href="/wiki/Allylescaline" title="Allylescaline">Allylescaline</a></li> <li><a href="/wiki/DESOXY" title="DESOXY">DESOXY</a></li> <li><a href="/wiki/Escaline" title="Escaline">Escaline</a></li> <li><a href="/wiki/Isoproscaline" title="Isoproscaline">Isoproscaline</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Macromerine" title="Macromerine">Macromerine</a></li> <li><a href="/wiki/3-Methoxy-4-ethoxyphenethylamine" title="3-Methoxy-4-ethoxyphenethylamine">MEPEA</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metaescaline" title="Metaescaline">Metaescaline</a></li> <li><a href="/wiki/Methallylescaline" title="Methallylescaline">Methallylescaline</a></li> <li><a href="/wiki/Proscaline" title="Proscaline">Proscaline</a></li> <li><a href="/wiki/Psi-2C-T-4" class="mw-redirect" title="Psi-2C-T-4">Psi-2C-T-4</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li></ul> <ul><li><i>Stimulants:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">α-Methylphenethylamine</a> (amphetamine)</li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/M-Methylphenethylamine" class="mw-redirect" title="M-Methylphenethylamine"><i>m</i>-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li> <li><a href="/wiki/O-Methylphenethylamine" class="mw-redirect" title="O-Methylphenethylamine"><i>o</i>-Methylphenethylamine</a></li> <li><a href="/wiki/P-Methylphenethylamine" class="mw-redirect" title="P-Methylphenethylamine"><i>p</i>-Methylphenethylamine</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li></ul> <ul><li><i>Entactogens:</i> <a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a><br /><i>Others:</i> <a href="/wiki/Biscaline" title="Biscaline">Biscaline</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Buscaline" title="Buscaline">Buscaline</a></li> <li><a href="/wiki/3,4-Dimethoxyphenethylamine" title="3,4-Dimethoxyphenethylamine">DMPEA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Psychedelics:</i> <a href="/wiki/3C-AL" title="3C-AL">3C-AL</a></li> <li><a href="/wiki/3C-BZ" title="3C-BZ">3C-BZ</a></li> <li><a href="/wiki/3C-E" title="3C-E">3C-E</a></li> <li><a href="/wiki/3C-MAL" title="3C-MAL">3C-MAL</a></li> <li><a href="/wiki/3C-P" title="3C-P">3C-P</a></li> <li><a href="/wiki/Aleph_(psychedelic)" title="Aleph (psychedelic)">Aleph</a></li> <li><a href="/wiki/Beatrice_(psychedelic)" title="Beatrice (psychedelic)">Beatrice</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/4-Methyl-2,5-methoxyphenylcyclopropylamine" class="mw-redirect" title="4-Methyl-2,5-methoxyphenylcyclopropylamine">DMCPA</a></li> <li><a href="/wiki/DMMDA" title="DMMDA">DMMDA</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-fluoroethylamphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-fluoroethylamphetamine">DOEF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-nitroamphetamine" title="2,5-Dimethoxy-4-nitroamphetamine">DON</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-propylamphetamine" title="2,5-Dimethoxy-4-propylamphetamine">DOPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-trifluoromethylamphetamine" title="2,5-Dimethoxy-4-trifluoromethylamphetamine">DOTFM</a></li> <li><a href="/wiki/Ganesha_(psychedelic)" title="Ganesha (psychedelic)">Ganesha</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDA-2" title="MMDA-2">MMDA-2</a></li> <li><a href="/wiki/Psi-DOM" class="mw-redirect" title="Psi-DOM">Psi-DOM</a></li> <li><a href="/wiki/Trimethoxyamphetamine" class="mw-redirect" title="Trimethoxyamphetamine">TMA</a></li> <li><a href="/wiki/Tetramethoxyamphetamine" class="mw-redirect" title="Tetramethoxyamphetamine">TeMA</a></li> <li><a href="/wiki/ZDCM-04" title="ZDCM-04">ZDCM-04</a><br /><i>Stimulants:</i> <a href="/wiki/2-Fluoroamphetamine" title="2-Fluoroamphetamine">2-FA</a></li> <li><a href="/wiki/2-Fluoromethamphetamine" title="2-Fluoromethamphetamine">2-FMA</a></li> <li><a href="/wiki/3-Fluoroamphetamine" title="3-Fluoroamphetamine">3-FA</a></li> <li><a href="/wiki/3-Fluoromethamphetamine" title="3-Fluoromethamphetamine">3-FMA</a></li> <li><a href="/wiki/Acridorex" title="Acridorex">Acridorex</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a>, <a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/Benfluorex" title="Benfluorex">Benfluorex</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Fencamfamin" title="Fencamfamin">Fencamfamin</a></li> <li><a href="/wiki/Fencamine" title="Fencamine">Fencamine</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a> (<a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a>)</li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flucetorex" title="Flucetorex">Flucetorex</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Formetorex" title="Formetorex">Formetorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Gepefrine" title="Gepefrine">Gepefrine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Isopropylamphetamine" title="Isopropylamphetamine">Isopropylamphetamine</a></li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> (Dextromethamphetamine, <a href="/wiki/Levomethamphetamine" title="Levomethamphetamine">Levomethamphetamine</a>)</li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/L-Norpseudoephedrine" title="L-Norpseudoephedrine"><span style="font-size: 85%;">L</span>-Norpseudoephedrine</a></li> <li><a href="/wiki/N,alpha-Diethylphenylethylamine" class="mw-redirect" title="N,alpha-Diethylphenylethylamine">N,alpha-Diethylphenylethylamine</a></li> <li><a href="/wiki/Oxifentorex" title="Oxifentorex">Oxifentorex</a></li> <li><a href="/wiki/Oxilofrine" title="Oxilofrine">Oxilofrine</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">PBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">PCA</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">PFA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">PFMA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">PIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxy-N-ethylamphetamine" title="Para-Methoxy-N-ethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxy-N-methylamphetamine" class="mw-redirect" title="Para-Methoxy-N-methylamphetamine">PMMA</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Sibutramine" title="Sibutramine">Sibutramine</a></li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a><br /><i>Entactogens:</i> <a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APB" title="5-APB">5-APB</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-EAPB" title="5-EAPB">5-EAPB</a></li> <li><a href="/wiki/5-IT" class="mw-redirect" title="5-IT">5-IT</a></li> <li><a class="mw-selflink selflink">5-MAPB</a></li> <li><a href="/wiki/5-MAPDB" title="5-MAPDB">5-MAPDB</a></li> <li><a href="/wiki/6-APB" title="6-APB">6-APB</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Chloro-MDMA" title="6-Chloro-MDMA">6-Chloro-MDMA</a></li> <li><a href="/wiki/6-EAPB" title="6-EAPB">6-EAPB</a></li> <li><a href="/wiki/6-IT" class="mw-redirect" title="6-IT">6-IT</a></li> <li><a href="/wiki/6-MAPB" title="6-MAPB">6-MAPB</a></li> <li><a href="/wiki/6-MAPDB" title="6-MAPDB">6-MAPDB</a></li> <li><a href="/wiki/Ethylidenedioxyamphetamine" class="mw-redirect" title="Ethylidenedioxyamphetamine">EDA</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/2,3-Methylenedioxyamphetamine" title="2,3-Methylenedioxyamphetamine">2,3-MDA</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">3,4-MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxylmethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxylmethamphetamine">MDHMA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a><br /><i>Others:</i> <a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">3,4-DCA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/DiFMDA" class="mw-redirect" title="DiFMDA">DiFMDA</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl"><span style="font-size: 85%;">D</span>-Deprenyl</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phentermine" title="Phentermine">Phentermines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a><br /><i>Entactogens:</i> <a href="/wiki/Methylenedioxyphentermine" class="mw-redirect" title="Methylenedioxyphentermine">MDPH</a></li> <li><a href="/wiki/Methylenedioxymethylphentermine" class="mw-redirect" title="Methylenedioxymethylphentermine">MDMPH</a><br /><i>Others:</i> <a href="/wiki/Cericlamine" title="Cericlamine">Cericlamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Cathinones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/3-Fluoromethcathinone" title="3-Fluoromethcathinone">3-FMC</a></li> <li><a href="/wiki/4-Methylcathinone" title="4-Methylcathinone">4-MC</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">4-BMC</a></li> <li><a href="/wiki/4-Chloromethcathinone" title="4-Chloromethcathinone">4-CMC</a></li> <li><a href="/wiki/4-Ethylmethcathinone" title="4-Ethylmethcathinone">4-EMC</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">4-FMC</a></li> <li><a href="/wiki/4-Methylethcathinone" title="4-Methylethcathinone">4-MEC</a></li> <li><a href="/wiki/4-Methylbuphedrone" title="4-Methylbuphedrone">4-MeMABP</a></li> <li><a href="/wiki/4-Methylpentedrone" title="4-Methylpentedrone">4-MPD</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Benzedrone" title="Benzedrone">Benzedrone</a></li> <li><a href="/wiki/Brephedrone" class="mw-redirect" title="Brephedrone">Brephedrone</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Dimethylcathinone" title="Dimethylcathinone">Dimethylcathinone</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/N-Ethylbuphedrone" title="N-Ethylbuphedrone">NEB</a></li> <li><a href="/wiki/N-Ethylhexedrone" title="N-Ethylhexedrone">N-Ethylhexedrone</a></li> <li><a href="/wiki/N-Ethylpentedrone" title="N-Ethylpentedrone">N-Ethylpentedrone</a></li> <li><a href="/wiki/Pentedrone" title="Pentedrone">Pentedrone</a></li> <li><a href="/wiki/Pentylone" title="Pentylone">Pentylone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a><br /><i>Entactogens:</i> <a href="/wiki/3,4-Dimethylmethcathinone" title="3,4-Dimethylmethcathinone">3,4-DMMC</a></li> <li><a href="/wiki/3-Methylmethcathinone" title="3-Methylmethcathinone">3-MMC</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Methylenedioxycathinone" title="Methylenedioxycathinone">Methylenedioxycathinone</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Propylone" title="Propylone">Propylone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Entactogens:</i> <a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Methylphenylisobutylamine" title="4-Methylphenylisobutylamine">4-MAB</a></li> <li><a href="/wiki/Ariadne_(psychedelic)" class="mw-redirect" title="Ariadne (psychedelic)">Ariadne</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/MBDB" title="MBDB">MBDB</a><br /><i>Stimulants:</i> <a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">Phenylalkylpyrrolidines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/Alpha-Pyrrolidinobutiophenone" class="mw-redirect" title="Alpha-Pyrrolidinobutiophenone">α-PBP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinohexiophenone" class="mw-redirect" title="Alpha-Pyrrolidinohexiophenone">α-PHP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopropiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopropiophenone">α-PPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiophenone">α-PVP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinobutiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinobutiophenone">MDPBP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinopropiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinopropiophenone">MDPPP</a></li> <li><a href="/wiki/3,4-Methylenedioxypyrovalerone" class="mw-redirect" title="3,4-Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">4-MePBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">4-MePHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">4-MePPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopropiophenone" title="4'-Methoxy-α-pyrrolidinopropiophenone">MOPPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopentiophenone" title="4'-Methoxy-α-pyrrolidinopentiophenone">MOPVP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">MPBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">MPHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">MPPP</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">PEP</a></li> <li><a href="/wiki/Prolintane" title="Prolintane">Prolintane</a></li> <li><a href="/wiki/Pyrovalerone" title="Pyrovalerone">Pyrovalerone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Catecholamine" title="Catecholamine">Catecholamines</a><br /><span style="font-size: 85%;">(and close relatives)</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/6-Hydroxydopamine" class="mw-redirect" title="6-Hydroxydopamine">6-OHDA</a></li> <li><a href="/wiki/Alpha-Methyldopamine" class="mw-redirect" title="Alpha-Methyldopamine">a-Me-DA</a></li> <li><a href="/wiki/Alpha-Methyltyramine" class="mw-redirect" title="Alpha-Methyltyramine">a-Me-TRA</a></li> <li><a href="/wiki/Adrenochrome" title="Adrenochrome">Adrenochrome</a></li> <li><a href="/wiki/Ciladopa" title="Ciladopa">Ciladopa</a></li> <li><a href="/wiki/D-DOPA" title="D-DOPA"><span style="font-size: 85%;">D</span>-DOPA</a> (Dextrodopa)</li> <li><a href="/wiki/Dimetofrine" title="Dimetofrine">Dimetofrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Epinephrine_(neurotransmitter)" class="mw-redirect" title="Epinephrine (neurotransmitter)">Epinephrine</a></li> <li><a href="/wiki/Epinine" class="mw-redirect" title="Epinine">Epinine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Fenclonine" title="Fenclonine">Fenclonine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA"><span style="font-size: 85%;">L</span>-DOPA</a> (Levodopa)</li> <li><a href="/wiki/L-DOPS" class="mw-redirect" title="L-DOPS"><span style="font-size: 85%;">L</span>-DOPS</a> (Droxidopa)</li> <li><a href="/wiki/L-Phenylalanine" class="mw-redirect" title="L-Phenylalanine"><span style="font-size: 85%;">L</span>-Phenylalanine</a></li> <li><a href="/wiki/L-Tyrosine" class="mw-redirect" title="L-Tyrosine"><span style="font-size: 85%;">L</span>-Tyrosine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Metaterol" title="Metaterol">Metaterol</a></li> <li><a href="/wiki/Metirosine" class="mw-redirect" title="Metirosine">Metirosine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/N,N-Dimethyldopamine" title="N,N-Dimethyldopamine">N,N-Dimethyldopamine</a></li> <li><a href="/wiki/Nordefrin" class="mw-redirect" title="Nordefrin">Nordefrin</a> (<a href="/wiki/Levonordefrin" class="mw-redirect" title="Levonordefrin">Levonordefrin</a>)</li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a> (<i>m</i>-Octopamine)</li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a 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> 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class="vector-sticky-header-end" aria-hidden="true"> <div class="vector-sticky-header-icons"> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-talk-sticky-header" tabindex="-1" data-event-name="talk-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbles mw-ui-icon-wikimedia-speechBubbles"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-subject-sticky-header" tabindex="-1" data-event-name="subject-sticky-header"><span class="vector-icon mw-ui-icon-article mw-ui-icon-wikimedia-article"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-history-sticky-header" tabindex="-1" data-event-name="history-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-history mw-ui-icon-wikimedia-wikimedia-history"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only mw-watchlink" id="ca-watchstar-sticky-header" tabindex="-1" data-event-name="watch-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-star mw-ui-icon-wikimedia-wikimedia-star"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-edit-sticky-header" tabindex="-1" data-event-name="wikitext-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-wikiText mw-ui-icon-wikimedia-wikimedia-wikiText"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-ve-edit-sticky-header" tabindex="-1" data-event-name="ve-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-edit mw-ui-icon-wikimedia-wikimedia-edit"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-viewsource-sticky-header" tabindex="-1" data-event-name="ve-edit-protected-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-editLock mw-ui-icon-wikimedia-wikimedia-editLock"></span> <span></span> </a> </div> <div class="vector-sticky-header-buttons"> <button class="cdx-button cdx-button--weight-quiet mw-interlanguage-selector" id="p-lang-btn-sticky-header" tabindex="-1" data-event-name="ui.dropdown-p-lang-btn-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-language mw-ui-icon-wikimedia-wikimedia-language"></span> <span>3 languages</span> </button> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive" id="ca-addsection-sticky-header" tabindex="-1" data-event-name="addsection-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbleAdd-progressive mw-ui-icon-wikimedia-speechBubbleAdd-progressive"></span> <span>Add topic</span> </a> </div> <div class="vector-sticky-header-icon-end"> <div class="vector-user-links"> </div> </div> </div> </div> </div> <div class="mw-portlet mw-portlet-dock-bottom emptyPortlet" id="p-dock-bottom"> <ul> </ul> </div> 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