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.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): ''para''-Chloroamphetamine"><i>para</i>-Chloroamphetamine</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Para-Chloroamphetamine_Structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Para-Chloroamphetamine_Structure.svg/225px-Para-Chloroamphetamine_Structure.svg.png" decoding="async" width="225" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Para-Chloroamphetamine_Structure.svg/338px-Para-Chloroamphetamine_Structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Para-Chloroamphetamine_Structure.svg/450px-Para-Chloroamphetamine_Structure.svg.png 2x" data-file-width="512" data-file-height="199" /></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">PCA; pCA; <i>p</i>-Chloroamphetamine; 4-Chloroamphetamine; 4-CA; Ro 4-6614/001; NSC-287208; 4-Chloro-α-methylphenethylamine; 1-(4-Chlorophenyl)propan-2-amine</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Serotonin%E2%80%93norepinephrine%E2%80%93dopamine_releasing_agent" title="Serotonin–norepinephrine–dopamine releasing agent">Serotonin–norepinephrine–dopamine releasing agent</a>; <a href="/wiki/Serotonergic_neurotoxin" class="mw-redirect" title="Serotonergic neurotoxin">Serotonergic neurotoxin</a>; <a href="/wiki/Antidepressant" title="Antidepressant">Antidepressant</a>; <a href="/wiki/Stimulant" title="Stimulant">Stimulant</a></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="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_A_drugs" class="mw-redirect" title="Drugs controlled by the UK Misuse of Drugs Act">Class A</a></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pharmacodynamics#Duration_of_action" title="Pharmacodynamics">Duration of action</a></th><td class="infobox-data"><a href="/wiki/Intramuscular_Injection" class="mw-redirect" title="Intramuscular Injection"><abbr title="Intramuscular Injection">IM</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 Intramuscular Injection</span>: 3–7<span class="nowrap"> </span>hours<sup id="cite_ref-Shulgin1978_1-0" class="reference"><a href="#cite_note-Shulgin1978-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">1-(4-Chlorophenyl)propan-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=64-12-0">64-12-0</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/3127">3127</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=4592">4592</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.3015.html">3015</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/897NVD4A52">897NVD4A52</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL358967">ChEMBL358967</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID90897229">DTXSID90897229</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q229944#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>9</sub><span title="Hydrogen">H</span><sub>12</sub><span title="Chlorine">Cl</span><span title="Nitrogen">N</span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002169650000000000♠"></span>169.65</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=Clc1ccc%28cc1%29CC%28N%29C">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Clc1ccc(cc1)CC(N)C</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C9H12ClN/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5,7H,6,11H2,1H3<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:WWPITPSIWMXDPE-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=462272984&page2=Para-Chloroamphetamine">(verify)</a></span></span></td></tr></tbody></table> <p><b><i>para</i>-Chloroamphetamine</b> (<b>PCA</b>), also known as <b>4-chloroamphetamine</b> (<b>4-CA</b>), is 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> (SNDRA) and <a href="/wiki/Serotonergic_neurotoxin" class="mw-redirect" title="Serotonergic neurotoxin">serotonergic neurotoxin</a> of the <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">amphetamine</a> family.<sup id="cite_ref-ShulginManningDaley2011_2-0" class="reference"><a href="#cite_note-ShulginManningDaley2011-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1992_3-0" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1986_4-0" class="reference"><a href="#cite_note-Fuller1986-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-0" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It is used in <a href="/wiki/Scientific_research" class="mw-redirect" title="Scientific research">scientific research</a> in the study of the serotonin system, as a <a href="/wiki/Serotonin_releasing_agent" title="Serotonin releasing agent">serotonin releasing agent</a> (SRA) at lower doses to produce serotonergic effects, and as a serotonergic neurotoxin at higher doses to produce long-lasting depletions of serotonin.<sup id="cite_ref-Fuller1992_3-1" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1986_4-1" class="reference"><a href="#cite_note-Fuller1986-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>PCA has also been clinically studied as an <a href="/wiki/Appetite_suppressant" class="mw-redirect" title="Appetite suppressant">appetite suppressant</a> and <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a>, but findings of neurotoxicity in animals discouraged further evaluation.<sup id="cite_ref-BlanckaertVanquekelbergheCoopman2018_6-0" class="reference"><a href="#cite_note-BlanckaertVanquekelbergheCoopman2018-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Shulgin1978_1-1" class="reference"><a href="#cite_note-Shulgin1978-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It has also been encountered as a <a href="/wiki/Designer_drug" title="Designer drug">designer drug</a>, although it never achieved popularity, again perhaps due to its neurotoxicity.<sup id="cite_ref-LuethiLiechti2020_7-0" class="reference"><a href="#cite_note-LuethiLiechti2020-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BlanckaertVanquekelbergheCoopman2018_6-1" class="reference"><a href="#cite_note-BlanckaertVanquekelbergheCoopman2018-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Effects">Effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=1" title="Edit section: Effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>PCA was studied clinically as an <a href="/wiki/Appetite_suppressant" class="mw-redirect" title="Appetite suppressant">appetite suppressant</a> and antidepressant and its effects in these studies were described.<sup id="cite_ref-BlanckaertVanquekelbergheCoopman2018_6-2" class="reference"><a href="#cite_note-BlanckaertVanquekelbergheCoopman2018-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Shulgin1978_1-2" class="reference"><a href="#cite_note-Shulgin1978-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-vanPraagSchutBosma1971_8-0" class="reference"><a href="#cite_note-vanPraagSchutBosma1971-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-vanPraagKorf1973_9-0" class="reference"><a href="#cite_note-vanPraagKorf1973-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> It has been said to have only slight <a href="/wiki/Psychostimulant" class="mw-redirect" title="Psychostimulant">stimulant</a> effects and to behave more like an <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a> than a stimulant.<sup id="cite_ref-BlanckaertVanquekelbergheCoopman2018_6-3" class="reference"><a href="#cite_note-BlanckaertVanquekelbergheCoopman2018-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> At doses of 80 to 90<span class="nowrap"> </span>mg daily, in 3<span class="nowrap"> </span>doses, it produced no significant acute <a href="/wiki/Psychoactive" class="mw-redirect" title="Psychoactive">psychoactive</a> effects and produced few <a href="/wiki/Adverse_effect" title="Adverse effect">adverse effects</a>.<sup id="cite_ref-BlanckaertVanquekelbergheCoopman2018_6-4" class="reference"><a href="#cite_note-BlanckaertVanquekelbergheCoopman2018-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Shulgin1978_1-3" class="reference"><a href="#cite_note-Shulgin1978-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> However, <a href="/wiki/Sleep_disturbance" class="mw-redirect" title="Sleep disturbance">sleep disturbances</a> and <a href="/wiki/Nausea" title="Nausea">nausea</a> were mentioned.<sup id="cite_ref-BlanckaertVanquekelbergheCoopman2018_6-5" class="reference"><a href="#cite_note-BlanckaertVanquekelbergheCoopman2018-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> No <a href="/wiki/Hallucinogen" title="Hallucinogen">hallucinogenic</a> effects have been reported.<sup id="cite_ref-ShulginManningDaley2011_2-1" class="reference"><a href="#cite_note-ShulginManningDaley2011-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Shulgin1978_1-4" class="reference"><a href="#cite_note-Shulgin1978-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HalberstadtGeyer2018_10-0" class="reference"><a href="#cite_note-HalberstadtGeyer2018-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HalberstadtChathaKlein2020_11-0" class="reference"><a href="#cite_note-HalberstadtChathaKlein2020-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>The profile of PCA is analogous to that of <a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">naphthylaminopropane</a> (NAP; PAL-287), a highly <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> and well-balanced SNDRA with only weak stimulant-like effects.<sup id="cite_ref-RothmanBloughBaumann2008_12-0" class="reference"><a href="#cite_note-RothmanBloughBaumann2008-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> It is thought that concomitant robust serotonin release suppresses the stimulating and <a href="/wiki/Reward_system" title="Reward system">rewarding</a> effects of dopamine release.<sup id="cite_ref-RothmanBloughBaumann2008_12-1" class="reference"><a href="#cite_note-RothmanBloughBaumann2008-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RothmanBaumann2006b_13-0" class="reference"><a href="#cite_note-RothmanBaumann2006b-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=2" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Monoamine_releasing_agent">Monoamine releasing agent</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=3" title="Edit section: Monoamine releasing agent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>PCA acts as a <a href="/wiki/Serotonin%E2%80%93norepinephrine%E2%80%93dopamine_releasing_agent" title="Serotonin–norepinephrine–dopamine releasing agent">serotonin, norepinephrine, and dopamine releasing agent</a> (SNDRA).<sup id="cite_ref-Forsyth2012_14-0" class="reference"><a href="#cite_note-Forsyth2012-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Blough2008_15-0" class="reference"><a href="#cite_note-Blough2008-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Marona-LewickaRheeSprague1995_16-0" class="reference"><a href="#cite_note-Marona-LewickaRheeSprague1995-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Its <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">monoamine release</a> are 28.3<span class="nowrap"> </span>nM for <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, 23.5 to 26.2<span class="nowrap"> </span>nM for <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>, and 42.2 to 68.5<span class="nowrap"> </span>nM for <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, making it a <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> and well-balanced SNDRA.<sup id="cite_ref-Forsyth2012_14-1" class="reference"><a href="#cite_note-Forsyth2012-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Blough2008_15-1" class="reference"><a href="#cite_note-Blough2008-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FitzgeraldGannonWalther2024_17-0" class="reference"><a href="#cite_note-FitzgeraldGannonWalther2024-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nicole2022_18-0" class="reference"><a href="#cite_note-Nicole2022-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Short-term_effects">Short-term effects</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=4" title="Edit section: Short-term effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In animals, doses of PCA of 0.5 to 5<span class="nowrap"> </span>mg/kg acutely produce a variety of behavioral and neurochemical effects thought to be due to serotonin release.<sup id="cite_ref-Fuller1992_3-2" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-0" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SpragueJohnsonSchmidt1996_20-0" class="reference"><a href="#cite_note-SpragueJohnsonSchmidt1996-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Consequent enhancement of serotonergic signaling, serotonergic effects like <a href="/wiki/Myoclonus" title="Myoclonus">myoclonus</a>, the <a href="/wiki/Serotonin_syndrome" title="Serotonin syndrome">serotonin behavioral syndrome</a>, including <a href="/wiki/Muscle_tremor" class="mw-redirect" title="Muscle tremor">tremor</a>, <a href="/wiki/Rigidity_(neurology)" class="mw-redirect" title="Rigidity (neurology)">rigidity</a>, Straub tail, hindlimb abduction, lateral head weaving, and reciprocal forepaw treading, <a href="/wiki/Prepulse_inhibition" title="Prepulse inhibition">inhibition of startle response sensitization</a>, suppression of <a href="/wiki/Sexual_behavior" class="mw-redirect" title="Sexual behavior">sexual behavior</a> in females, and the <a href="/wiki/Head-twitch_response" title="Head-twitch response">head-twitch response</a>.<sup id="cite_ref-Fuller1992_3-3" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-1" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Non-behavioral or physiological effects include activation of the <a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93adrenal_axis" title="Hypothalamic–pituitary–adrenal axis">hypothalamic–pituitary–adrenal axis</a> (HPA axis), increased <a href="/wiki/Prolactin" title="Prolactin">prolactin</a> <a href="/wiki/Secretion" title="Secretion">secretion</a>, and increased <a href="/wiki/Blood_plasma" title="Blood plasma">plasma</a> <a href="/wiki/Renin" title="Renin">renin</a> activity.<sup id="cite_ref-Fuller1992_3-4" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> PCA and other SRAs like <a href="/wiki/MDMA" title="MDMA">MDMA</a> and <a href="/wiki/%CE%91-ethyltryptamine" class="mw-redirect" title="Α-ethyltryptamine">α-ethyltryptamine</a> (αET) produce <a href="/wiki/Locomotor_hyperactivity" class="mw-redirect" title="Locomotor hyperactivity">locomotor hyperactivity</a> in animals and this is thought to be serotonin-dependent.<sup id="cite_ref-Geyer1996_21-0" class="reference"><a href="#cite_note-Geyer1996-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> It is mimicked by <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> <a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT<sub>1B</sub> receptor</a> activation.<sup id="cite_ref-Geyer1996_21-1" class="reference"><a href="#cite_note-Geyer1996-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> However, PCA is also reported to produce <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>-like hyperactivity and <a href="/wiki/Stereotypy" title="Stereotypy">stereotypy</a>, as well as amphetamine-like enhancement of <a href="/wiki/Conditioned_avoidance_responding" class="mw-redirect" title="Conditioned avoidance responding">conditioned avoidance responding</a> that is independent of serotonergic signaling.<sup id="cite_ref-Sanders-BushSteranka1978_19-2" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>PCA does not show effects like those of the <a href="/wiki/Binding_selectivity" title="Binding selectivity">selective</a> <a href="/wiki/Norepinephrine%E2%80%93dopamine_releasing_agent" title="Norepinephrine–dopamine releasing agent">norepinephrine and dopamine releasing agent</a> (NDRA) amphetamine in animals but instead fully substitutes for other <a href="/wiki/Serotonin_releasing_agent" title="Serotonin releasing agent">serotonin releasing agents</a> like <a href="/wiki/MBDB" title="MBDB">(+)-MBDB</a> and <a href="/wiki/MMAI" title="MMAI">MMAI</a> in rodent <a href="/wiki/Drug_discrimination" title="Drug discrimination">drug discrimination</a> tests.<sup id="cite_ref-Marona-LewickaRheeSprague1995_16-1" class="reference"><a href="#cite_note-Marona-LewickaRheeSprague1995-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> The findings with PCA are in contrast to those with <a href="/wiki/Para-fluoroamphetamine" class="mw-redirect" title="Para-fluoroamphetamine"><i>para</i>-fluoroamphetamine</a> (PFA), which acts as a selective NDRA similarly to amphetamine,<sup id="cite_ref-WeeAndersonBaumann2005_22-0" class="reference"><a href="#cite_note-WeeAndersonBaumann2005-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> fully substitutes for amphetamine in animals, and fails to substitute for (+)-MBDB or MMAI.<sup id="cite_ref-Marona-LewickaRheeSprague1995_16-2" class="reference"><a href="#cite_note-Marona-LewickaRheeSprague1995-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> As touched on, PCA can robustly produce the head-twitch response, which is a behavioral proxy of <a href="/wiki/Psychedelic_drug" title="Psychedelic drug">psychedelic</a>-like effects.<sup id="cite_ref-HalberstadtGeyer2018_10-1" class="reference"><a href="#cite_note-HalberstadtGeyer2018-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HalberstadtChathaKlein2020_11-1" class="reference"><a href="#cite_note-HalberstadtChathaKlein2020-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-OrikasaSloley1988_23-0" class="reference"><a href="#cite_note-OrikasaSloley1988-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1992_3-5" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> However, PCA does not seem to produce hallucinogenic effects in humans, and hence its activity in the head-twitch paradigm has been described as a false-positive for psychedelic effects.<sup id="cite_ref-HalberstadtGeyer2018_10-2" class="reference"><a href="#cite_note-HalberstadtGeyer2018-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HalberstadtChathaKlein2020_11-2" class="reference"><a href="#cite_note-HalberstadtChathaKlein2020-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WojtasGołembiowska2023_24-0" class="reference"><a href="#cite_note-WojtasGołembiowska2023-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The head-twitch response with PCA appears to be dependent on induction of serotonin release and not on direct <a href="/wiki/Serotonin_receptor_agonist" title="Serotonin receptor agonist">serotonin receptor agonism</a> by PCA, as it is blocked by <a href="/wiki/Serotonergic_neurotoxin" class="mw-redirect" title="Serotonergic neurotoxin">destruction of presynaptic serotonergic nerve terminals</a> or by <a href="/wiki/Tryptophan_hydroxylase_inhibition" class="mw-redirect" title="Tryptophan hydroxylase inhibition">serotonin synthesis inhibition</a>.<sup id="cite_ref-HalberstadtGeyer2018_10-3" class="reference"><a href="#cite_note-HalberstadtGeyer2018-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-OrikasaSloley1988_23-1" class="reference"><a href="#cite_note-OrikasaSloley1988-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-OgrenRoss1977_25-0" class="reference"><a href="#cite_note-OgrenRoss1977-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Relatedly, PCA is said not to be a serotonin <a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT<sub>2A</sub> receptor</a> <a href="/wiki/Agonist" title="Agonist">agonist</a> (at concentrations up to 10,000<span class="nowrap"> </span>nM).<sup id="cite_ref-VargasDunlapDong2023_26-0" class="reference"><a href="#cite_note-VargasDunlapDong2023-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> However, PCA might nonetheless act as a direct serotonin <a href="/wiki/5-HT2_receptor" title="5-HT2 receptor">5-HT<sub>2</sub> receptor</a> agonist at high doses, as head twitches induced by it are not blocked by serotonin synthesis inhibition at these doses.<sup id="cite_ref-OgrenRoss1977_25-1" class="reference"><a href="#cite_note-OgrenRoss1977-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Although PCA has been reported to produce the head-twitch response, a more modern study reported that it did not do so, at least unless the <a href="/wiki/Serotonin_transporter" title="Serotonin transporter">serotonin transporter</a> (SERT) was artificially expressed in a population of <a href="/wiki/Medial_prefrontal_cortex" class="mw-redirect" title="Medial prefrontal cortex">medial prefrontal cortex</a> (mPFC) serotonergic <a href="/wiki/Neuron" title="Neuron">neurons</a> that normally lack the SERT.<sup id="cite_ref-VargasDunlapDong2023_26-1" class="reference"><a href="#cite_note-VargasDunlapDong2023-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>While <a href="/wiki/Extracellular" class="mw-redirect" title="Extracellular">extracellular</a> serotonin levels and serotonergic signaling are acutely increased by PCA, there is a concomitant depletion of serotonin stores.<sup id="cite_ref-Fuller1992_3-6" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The depletion includes a decrease in total serotonin content, <a href="/wiki/5-hydroxyindoleacetic_acid" class="mw-redirect" title="5-hydroxyindoleacetic acid">5-hydroxyindoleacetic acid</a> (5-HIAA) content, and <a href="/wiki/Tryptophan_hydroxylase" title="Tryptophan hydroxylase">tryptophan hydroxylase</a> activity.<sup id="cite_ref-Fuller1992_3-7" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-3" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The acute depletion of serotonin stores by PCA is likely due to <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibition</a> of tryptophan hydroxylase.<sup id="cite_ref-Fuller1978_5-1" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-4" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> How this occurs is unclear, as PCA does not inhibit tryptophan hydroxylase <i><a href="/wiki/In_vitro" title="In vitro">in vitro</a></i> except at very high concentrations.<sup id="cite_ref-Fuller1978_5-2" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-5" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The initial serotonin depletion by lower doses of PCA are not permanent and can readily reverse after a few hours.<sup id="cite_ref-Fuller1978_5-3" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> As such, low doses of PCA, such as 2<span class="nowrap"> </span>mg/kg, are regarded as non-neurotoxic.<sup id="cite_ref-SpragueJohnsonSchmidt1996_20-1" class="reference"><a href="#cite_note-SpragueJohnsonSchmidt1996-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The dopaminergic and noradrenergic systems are also substantially impacted by acute PCA.<sup id="cite_ref-Sanders-BushSteranka1978_19-6" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> However, dopamine and norepinephrine levels are only slightly changed.<sup id="cite_ref-Sanders-BushSteranka1978_19-7" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> In addition, the effects on the dopaminergic and noradrenergic systems are of relatively short duration and return to normal within 24<span class="nowrap"> </span>hours, analogously to the case of the serotonin system.<sup id="cite_ref-Sanders-BushSteranka1978_19-8" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> In line with the preceding neurochemical findings, <a href="/wiki/Drug_tolerance" title="Drug tolerance">tolerance</a> to various of the behavioral effects of acute PCA has been found to develop.<sup id="cite_ref-Sanders-BushSteranka1978_19-9" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Due to its activity as a serotonin releasing agent, PCA is employed in <a href="/wiki/Scientific_research" class="mw-redirect" title="Scientific research">scientific research</a> to acutely enhance and study serotonin signaling.<sup id="cite_ref-Fuller1986_4-2" class="reference"><a href="#cite_note-Fuller1986-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Geyer1996_21-2" class="reference"><a href="#cite_note-Geyer1996-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Long-term_serotonergic_neurotoxicity">Long-term serotonergic neurotoxicity</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=5" title="Edit section: Long-term serotonergic neurotoxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>At higher doses (e.g., 10<span class="nowrap"> </span>mg/kg) and for longer amounts of exposure, PCA produces extremely long-lasting depletion of serotonin and loss of serotonergic function that is considered to reflect <a href="/wiki/Serotonergic_neurotoxin" class="mw-redirect" title="Serotonergic neurotoxin">serotonergic neurotoxicity</a>.<sup id="cite_ref-Fuller1992_3-8" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-10" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SpragueJohnsonSchmidt1996_20-2" class="reference"><a href="#cite_note-SpragueJohnsonSchmidt1996-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> This includes depletion of serotonin content, 5-HIAA content, serotonin <a href="/wiki/Flux_(metabolism)" title="Flux (metabolism)">turnover</a>, tryptophan hydroxylase, serotonin <a href="/wiki/Reuptake" title="Reuptake">reuptake</a> capacity, and <a href="/wiki/Serotonin_transporter" title="Serotonin transporter">serotonin transporters</a> for weeks or months.<sup id="cite_ref-Fuller1992_3-9" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-4" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-11" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> As an example, brain serotonin continued to be reduced by 41% after 38<span class="nowrap"> </span>days.<sup id="cite_ref-Fuller1992_3-10" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In addition, many serotonin-containing <a href="/wiki/Nerve_fiber" class="mw-redirect" title="Nerve fiber">nerve fibers</a> become undetectable and appear to be lost.<sup id="cite_ref-Fuller1992_3-11" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> There have also been observations of <a href="/wiki/Neurodegeneration" class="mw-redirect" title="Neurodegeneration">nerve degeneration</a> in the days after PCA administration.<sup id="cite_ref-Fuller1992_3-12" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-5" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-12" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Different serotonergic areas and projections are differentially susceptible to the neurotoxicity of PCA, with the <a href="/wiki/Dorsal_raphe_nucleus" title="Dorsal raphe nucleus">dorsal raphe nuclei</a> more susceptible and the <a href="/wiki/Median_raphe_nucleus" title="Median raphe nucleus">median raphe nuclei</a>, <a href="/wiki/Raphe_obscurus" class="mw-redirect" title="Raphe obscurus">raphe obscurus</a>, <a href="/wiki/Raphe_pallidus" class="mw-redirect" title="Raphe pallidus">raphe pallidus</a>, <a href="/wiki/Dentate_gyrus" title="Dentate gyrus">dentate gyrus</a>, <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a>, and <a href="/wiki/Spinal_cord" title="Spinal cord">spinal cord</a> all resistant.<sup id="cite_ref-Fuller1992_3-13" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-13" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> PCA is selective for serotonin, without causing depletion of <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a> or <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>.<sup id="cite_ref-Fuller1992_3-14" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-14" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>There are behavioral consequences of the serotonergic neurotoxicity of PCA.<sup id="cite_ref-Fuller1992_3-15" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-15" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Affected animals are still quite normal in overall appearance.<sup id="cite_ref-Fuller1992_3-16" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> However, <a href="/wiki/Hypoactivity" class="mw-redirect" title="Hypoactivity">hypoactivity</a>, increased <a href="/wiki/Defecation" title="Defecation">defecation</a> in the <a href="/wiki/Open_field_test" class="mw-redirect" title="Open field test">open field test</a>, and failed acquisition of shock avoidance in the Y-maze task are all apparent.<sup id="cite_ref-Fuller1992_3-17" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In addition, <a href="/wiki/Hyperlocomotion" class="mw-redirect" title="Hyperlocomotion">increased locomotion</a> in response to the <a href="/wiki/Dopamine_agonist" title="Dopamine agonist">dopamine agonist</a> <a href="/wiki/Apomorphine" title="Apomorphine">apomorphine</a> has been observed, which is consistent with findings that serotonin may inhibit certain aspects of dopamine signaling.<sup id="cite_ref-Fuller1992_3-18" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Failure of acquisition of a <a href="/wiki/Conditioned_avoidance_response_test" title="Conditioned avoidance response test">two-way conditioned avoidance response</a> has been observed, and this could be completely prevented with the SRI <a href="/wiki/Zimelidine" title="Zimelidine">zimelidine</a> (see more on this below).<sup id="cite_ref-Fuller1992_3-19" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Various other changes and deficits have been seen as well.<sup id="cite_ref-Fuller1992_3-20" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The effects of the <a href="/wiki/Binding_selectivity" title="Binding selectivity">non-selective</a> <a href="/wiki/Serotonin_receptor_agonist" title="Serotonin receptor agonist">serotonin receptor agonist</a> and <a href="/wiki/Serotonergic_psychedelic" class="mw-redirect" title="Serotonergic psychedelic">serotonergic psychedelic</a> <a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a> have been found to be greatly potentiated following PCA, which may reflect <a href="/wiki/Receptor_supersensitivity" class="mw-redirect" title="Receptor supersensitivity">receptor supersensitivity</a> in an attempt at compensation for serotonin depletion.<sup id="cite_ref-Fuller1992_3-21" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Conversely, the behavioral and physiological serotonergic effects of acute low-dose PCA challenge are attenuated after high-dose neurotoxic PCA exposure, which may reflect reduced available serotonin stores for release.<sup id="cite_ref-Fuller1992_3-22" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading5"><h5 id="Mechanisms_of_neurotoxicity">Mechanisms of neurotoxicity</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=6" title="Edit section: Mechanisms of neurotoxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although the ultimate cause is <a href="/wiki/Cytotoxicity" title="Cytotoxicity">cytotoxicity</a> to serotonergic <a href="/wiki/Neuron" title="Neuron">neurons</a>, the mechanisms leading to the serotonergic neurotoxicity of PCA are unknown.<sup id="cite_ref-Fuller1992_3-23" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-6" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-16" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> However, uptake of PCA into <a href="/wiki/Neuron" title="Neuron">neurons</a> by the <a href="/wiki/Serotonin_transporter" title="Serotonin transporter">serotonin transporter</a> (SERT) appears to be required.<sup id="cite_ref-Fuller1992_3-24" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-7" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-17" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Serotonin_reuptake_inhibitor" title="Serotonin reuptake inhibitor">Serotonin reuptake inhibitors</a> (SRIs) like <a href="/wiki/Fluoxetine" title="Fluoxetine">fluoxetine</a> can block both the acute short-term effects and the long-term serotonergic neurotoxicity of PCA.<sup id="cite_ref-Fuller1992_3-25" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-8" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-18" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> In addition, they can be given 4<span class="nowrap"> </span>hours after PCA administration, when acute serotonin depletion has already occurred, and will still completely protect against the long-term neurotoxicity.<sup id="cite_ref-Fuller1992_3-26" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> However, the SRI must be long-lasting; the short-acting SRI <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, given before PCA, prevented acute serotonin depletion, but PCA outlasted clomipramine in the body, and the same degree of long-term neurotoxicity occurred as if clomipramine had not been administered.<sup id="cite_ref-Fuller1992_3-27" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>It has been theorized that a toxic <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> of PCA may be formed and that this metabolite is responsible for its neurotoxicity.<sup id="cite_ref-Fuller1978_5-9" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-19" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> However, no compelling evidence in support of this hypothesis has emerged.<sup id="cite_ref-Fuller1992_3-28" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-10" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sanders-BushSteranka1978_19-20" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Severe depletion of serotonin by the combination of <a href="/wiki/Fenclonine" title="Fenclonine"><i>para</i>-chlorophenylalanine</a> (PCPA) and <a href="/wiki/Reserpine" title="Reserpine">reserpine</a> substantially protects against the serotonergic neurotoxicity of PCA.<sup id="cite_ref-Fuller1992_3-29" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> This might be due to serotonin forming neurotoxic metabolites, for instance <a href="/wiki/5,6-dihydroxytryptamine" class="mw-redirect" title="5,6-dihydroxytryptamine">5,6-dihydroxytryptamine</a> (5,6-DHT), in the context of PCA's actions.<sup id="cite_ref-Fuller1992_3-30" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Similarly to prophylactic serotonin depletion, <a href="/wiki/%CE%91-methyl-p-tyrosine" class="mw-redirect" title="Α-methyl-p-tyrosine">α-methyl-<i>p</i>-tyrosine</a>, which depletes dopamine, protects against the serotonergic neurotoxicity of PCA as well.<sup id="cite_ref-Fuller1992_3-31" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It thus appears that dopamine is involved in the neurotoxicity of PCA, which is notable as PCA is a potent dopamine releasing agent in addition to inducing the release of serotonin.<sup id="cite_ref-Fuller1992_3-32" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>It has been reported that direct <a href="/wiki/Intracerebroventricular_injection" title="Intracerebroventricular injection">intracerebroventricular injection</a> of PCA into the brain, in contrast to <a href="/wiki/Peripheral_administration" class="mw-redirect" title="Peripheral administration">peripheral administration</a>, failed to produce serotonergic neurotoxicity.<sup id="cite_ref-Fuller1992_3-33" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> This was the case even with continuous infusion for two days.<sup id="cite_ref-Fuller1992_3-34" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> This seems like it may lend credence to the toxic metabolite theory of PCA neurotoxicity, as a peripherally formed metabolite of PCA might be required for neurotoxicity to occur.<sup id="cite_ref-Fuller1992_3-35" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> However, no toxic metabolite has still yet been identified and no other support for the hypothesis has surfaced.<sup id="cite_ref-Fuller1992_3-36" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Inhibiting the metabolism of PCA does not reduce tryptophan hydroxylase inactivation, suggesting that a metabolite is not responsible for this effect.<sup id="cite_ref-Sanders-BushSteranka1978_19-21" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>There are species differences in the neurotoxicity of PCA between rats and mice, which may help to shed light on the underlying mechanisms.<sup id="cite_ref-Sanders-BushSteranka1978_19-22" class="reference"><a href="#cite_note-Sanders-BushSteranka1978-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading5"><h5 id="Structure–activity_relationships_of_neurotoxicity"><span id="Structure.E2.80.93activity_relationships_of_neurotoxicity"></span>Structure–activity relationships of neurotoxicity</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=7" title="Edit section: Structure–activity relationships of neurotoxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The drug is the most potent <a href="/wiki/Serotonergic_neurotoxin" class="mw-redirect" title="Serotonergic neurotoxin">serotonergic neurotoxin</a> of a series of amphetamines.<sup id="cite_ref-Fuller1992_3-37" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-11" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> In terms of <a href="/wiki/Structure%E2%80%93activity_relationship" title="Structure–activity relationship">structure–activity relationships</a>, the α-<a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> appears to be essential for the neurotoxicity, and the α-<a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a> analogue is less potent as a neurotoxin.<sup id="cite_ref-Fuller1992_3-38" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-12" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Other <a href="/wiki/Side_chain" title="Side chain">side chain</a> homologues with shorter or longer chains were less potent or inactive.<sup id="cite_ref-Fuller1992_3-39" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-13" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Moving the chloro substituent to other positions on the <a href="/wiki/Phenyl_ring" class="mw-redirect" title="Phenyl ring">phenyl ring</a>, as in <a href="/wiki/2-chloroamphetamine" class="mw-redirect" title="2-chloroamphetamine"><i>ortho</i>-chloroamphetamine</a> (OCA) and <a href="/wiki/3-chloroamphetamine" class="mw-redirect" title="3-chloroamphetamine"><i>meta</i>-chloroamphetamine</a> (MCA), resulted in no significant serotonergic depletion, in contrast to the marked depletion with PCA.<sup id="cite_ref-Fuller1992_3-40" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-14" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> However, this was found to be due to rapid <a href="/wiki/Drug_metabolism" title="Drug metabolism">metabolism</a> in the case of MCA, and inhibiting its metabolism resulted in potent neurotoxicity as with PCA.<sup id="cite_ref-Fuller1978_5-15" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Conversely, OCA still does not produce apparent neurotoxicity.<sup id="cite_ref-Fuller1978_5-16" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine"><i>para</i>-Bromoamphetamine</a> (PBA) and <a href="/wiki/Para-bromomethamphetamine" class="mw-redirect" title="Para-bromomethamphetamine"><i>para</i>-bromomethamphetamine</a> (PBMA) show similar serotonergic neurotoxicity to PCA and PCMA.<sup id="cite_ref-Fuller1978_5-17" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Conversely, <a href="/wiki/Para-fluoroamphetamine" class="mw-redirect" title="Para-fluoroamphetamine"><i>para</i>-fluoroamphetamine</a> decreases serotonin levels but its effects appear to be much less persistent than those of PCA.<sup id="cite_ref-Fuller1978_5-18" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Other 4-substituted amphetamines have reduced neurotoxicity (4-trifluoromethylamphetamine, 4-phenoxyamphetamine) or are inactive (<a href="/wiki/4-methylamphetamine" class="mw-redirect" title="4-methylamphetamine">4-methylamphetamine</a>, <a href="/wiki/Para-methoxyamphetamine" class="mw-redirect" title="Para-methoxyamphetamine"><i>para</i>-methoxyamphetamine</a> (PMA)) in terms of serotonin depletion.<sup id="cite_ref-Fuller1978_5-19" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a> and <a href="/wiki/Norfenfluramine" title="Norfenfluramine">norfenfluramine</a>, which are 3-trifluoromethylamphetamines, produce very long-lasting serotonergic neurotoxicity similarly to PCA but are slightly less active.<sup id="cite_ref-Fuller1978_5-20" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>The closely related <i>N</i>-methylated derivative, <a href="/wiki/Para-Chloromethamphetamine" title="Para-Chloromethamphetamine"><i>para</i>-chloromethamphetamine</a> (PCMA), which is rapidly and extensively <a href="/wiki/Drug_metabolism" title="Drug metabolism">metabolized</a> to <i>para</i>-chloroamphetamine <i><a href="/wiki/In_vivo" title="In vivo">in vivo</a></i>, has neurotoxic properties as well, and is only slightly less <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> than PCA in this regard.<sup id="cite_ref-Fuller1992_3-41" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-21" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Other <i>N</i>-<a href="/wiki/Alkyl_group" title="Alkyl group">alkylated</a> <a href="/wiki/Structural_analog" title="Structural analog">analogues</a> of PCA also metabolize at least in part into PCA and produce <a href="/wiki/Serotonergic_neurotoxin" class="mw-redirect" title="Serotonergic neurotoxin">serotonergic neurotoxicity</a>.<sup id="cite_ref-Fuller1992_3-42" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-22" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> However, they show reduced activity, which may be due to their extent of conversion into PCA being reduced.<sup id="cite_ref-Fuller1978_5-23" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>In contrast to PCA, the <a href="/wiki/Phentermine" title="Phentermine">phentermine</a> (i.e., α-methylated) analogue of PCA, <a href="/wiki/Chlorphentermine" title="Chlorphentermine">chlorphentermine</a>, which acts as a highly selective SRA,<sup id="cite_ref-RothmanBaumann2002_27-0" class="reference"><a href="#cite_note-RothmanBaumann2002-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RothmanBaumann2006a_28-0" class="reference"><a href="#cite_note-RothmanBaumann2006a-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> does not appear to produce serotonergic neurotoxicity.<sup id="cite_ref-LovenbergWalkerBaumgarten1976_29-0" class="reference"><a href="#cite_note-LovenbergWalkerBaumgarten1976-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>Rigid analogues of PCA, like <a href="/wiki/6-chloro-2-aminotetralin" class="mw-redirect" title="6-chloro-2-aminotetralin">6-chloro-2-aminotetralin</a> (6-CAT), have also been assessed.<sup id="cite_ref-Fuller1978_5-24" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> 6-CAT depletes serotonin similarly to PCA, but its effects are smaller and shorter-lasting.<sup id="cite_ref-Fuller1978_5-25" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Another analogue, <a href="/wiki/Org_6582" title="Org 6582">Org 6582</a>, in which a third ring structure has been added, is a <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">selective serotonin reuptake inhibitor</a> (SSRI) and no longer shows the serotonergic neurotoxicity of PCA and 6-CAT.<sup id="cite_ref-Fuller1978_5-26" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading5"><h5 id="Use_as_a_neurotoxin_in_scientific_research">Use as a neurotoxin in scientific research</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=8" title="Edit section: Use as a neurotoxin in scientific research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>PCA is useful and widely employed as a serotonergic neurotoxin in <a href="/wiki/Scientific_research" class="mw-redirect" title="Scientific research">scientific research</a>.<sup id="cite_ref-Fuller1992_3-43" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1986_4-3" class="reference"><a href="#cite_note-Fuller1986-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> A variety of scientific findings have been made and published through employment of PCA.<sup id="cite_ref-Fuller1992_3-44" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The drug is advantageous over other serotonergic neurotoxins like <a href="/wiki/5,6-dihydroxytryptamine" class="mw-redirect" title="5,6-dihydroxytryptamine">5,6-dihydroxytryptamine</a> (5,6-DHT) and <a href="/wiki/5,7-dihydroxytryptamine" class="mw-redirect" title="5,7-dihydroxytryptamine">5,7-dihydroxytryptamine</a> (5,7-DHT) in that it is active by <a href="/wiki/Systemic_administration" title="Systemic administration">systemic administration</a>.<sup id="cite_ref-Fuller1992_3-45" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Conversely, 5,6-DHT and 5,7-DHT do not cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> and must be administered directly into the brain.<sup id="cite_ref-Fuller1992_3-46" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> PCA also produces a different anatomical pattern of serotonergic neurotoxicity than 5,6-DHT and 5,7-DHT, which can be useful as well if there is a need to study different serotonergic areas or pathways.<sup id="cite_ref-Fuller1992_3-47" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_actions">Other actions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=9" title="Edit section: Other actions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>PCA has been found to act as a relatively <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> <a href="/wiki/Monoamine_oxidase_A" title="Monoamine oxidase A">monoamine oxidase A</a> (MAO-A) <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">inhibitor</a>, with an <a href="/wiki/Half-maximal_inhibitory_concentration" class="mw-redirect" title="Half-maximal inhibitory concentration"><abbr title="half-maximal inhibitory concentration">IC<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 inhibitory concentration</span> of 1,900 to 4,000<span class="nowrap"> </span>nM.<sup id="cite_ref-Reyes-ParadaIturriaga-VasquezCassels2019_30-0" class="reference"><a href="#cite_note-Reyes-ParadaIturriaga-VasquezCassels2019-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p><p>PCA has been reported to act as an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the rat <a href="/wiki/Trace_amine-associated_receptor" title="Trace amine-associated receptor">trace amine-associated receptor</a> (TAAR1).<sup id="cite_ref-LiuWuLi2020_31-0" class="reference"><a href="#cite_note-LiuWuLi2020-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BunzowSondersArttamangkul2001_32-0" class="reference"><a href="#cite_note-BunzowSondersArttamangkul2001-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Conversely, it is not a significant agonist of the human TAAR1.<sup id="cite_ref-DiCaraMaggioAloisi2011_33-0" class="reference"><a href="#cite_note-DiCaraMaggioAloisi2011-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> The drug also appears to be inactive as an agonist of the mouse TAAR1.<sup id="cite_ref-DiCaraMaggioAloisi2011_33-1" class="reference"><a href="#cite_note-DiCaraMaggioAloisi2011-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> TAAR1 agonism has been implicated in modulating the effects of <a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">monoamine releasing agents</a> (MRAs).<sup id="cite_ref-JingLi2015_34-0" class="reference"><a href="#cite_note-JingLi2015-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> In contrast to PCA, the MRA MDMA is a potent agonist of the mouse TAAR1.<sup id="cite_ref-DiCaraMaggioAloisi2011_33-2" class="reference"><a href="#cite_note-DiCaraMaggioAloisi2011-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GainetdinovHoenerBerry2018_35-0" class="reference"><a href="#cite_note-GainetdinovHoenerBerry2018-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> MDMA-induced <i><a href="/wiki/In_vivo" title="In vivo">in-vivo</a></i> brain <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> and <a href="/wiki/Dopamine" title="Dopamine">dopamine</a> release and <a href="/wiki/Hyperlocomotion" class="mw-redirect" title="Hyperlocomotion">hyperlocomotion</a> are augmented in TAAR1 <a href="/wiki/Knockout_mice" class="mw-redirect" title="Knockout mice">knockout mice</a> relative to normal mice, whereas the <i>in-vivo</i> brain serotonin and dopamine release of PCA are not different between normal mice and TAAR1 knockout mice.<sup id="cite_ref-DiCaraMaggioAloisi2011_33-3" class="reference"><a href="#cite_note-DiCaraMaggioAloisi2011-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ZhangMantasAlvarsson2018_36-0" class="reference"><a href="#cite_note-ZhangMantasAlvarsson2018-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> In the same study, the TAAR1 agonist <a href="/wiki/O-phenyl-3-iodotyramine" class="mw-redirect" title="O-phenyl-3-iodotyramine"><i>o</i>-phenyl-3-iodotyramine</a> (<i>o</i>-PIT) blunted the dopamine and serotonin release of PCA in mouse <a href="/wiki/Synaptosome" title="Synaptosome">synaptosomes</a> <i><a href="/wiki/In_vitro" title="In vitro">in vitro</a></i>, an effect that was absent in synaptosomes from TAAR1 knockout mice.<sup id="cite_ref-DiCaraMaggioAloisi2011_33-4" class="reference"><a href="#cite_note-DiCaraMaggioAloisi2011-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ZhangMantasAlvarsson2018_36-1" class="reference"><a href="#cite_note-ZhangMantasAlvarsson2018-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> These findings led to conclusions that TAAR1 agonism by MDMA but not PCA auto-inhibits and constrains its own effects in rodents.<sup id="cite_ref-ZhangMantasAlvarsson2018_36-2" class="reference"><a href="#cite_note-ZhangMantasAlvarsson2018-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DiCaraMaggioAloisi2011_33-5" class="reference"><a href="#cite_note-DiCaraMaggioAloisi2011-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Unlike in rodents however, MDMA is not a significant TAAR1 agonist in humans.<sup id="cite_ref-GainetdinovHoenerBerry2018_35-1" class="reference"><a href="#cite_note-GainetdinovHoenerBerry2018-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SimmlerBuchyChaboz2016_37-0" class="reference"><a href="#cite_note-SimmlerBuchyChaboz2016-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LewinMillerGilmour2011_38-0" class="reference"><a href="#cite_note-LewinMillerGilmour2011-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DunlapAndrewsOlson2018_39-0" class="reference"><a href="#cite_note-DunlapAndrewsOlson2018-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=10" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>PCA, also known as 4-chloroamphetamine, is a <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">phenethylamine</a> and <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">amphetamine</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a>.<sup id="cite_ref-Shulgin1978_1-5" class="reference"><a href="#cite_note-Shulgin1978-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-27" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Structural_analog" title="Structural analog">Analogues</a> of PCA include <a href="/wiki/Para-chloromethamphetamine" class="mw-redirect" title="Para-chloromethamphetamine"><i>para</i>-chloromethamphetamine</a> (PCMA/4-CMA), <a href="/wiki/Para-bromoamphetamine" class="mw-redirect" title="Para-bromoamphetamine"><i>para</i>-bromoamphetamine</a> (PBA/4-BA), <a href="/wiki/Para-fluoroamphetamine" class="mw-redirect" title="Para-fluoroamphetamine"><i>para</i>-fluoroamphetamine</a> (PFA/4-FA), <a href="/wiki/Para-iodoamphetamine" class="mw-redirect" title="Para-iodoamphetamine"><i>para</i>-iodoamphetamine</a> (PIA/4-IA), <a href="/wiki/4-methylamphetamine" class="mw-redirect" title="4-methylamphetamine">4-methylamphetamine</a> (4-MA), <a href="/wiki/Meta-chloroamphetamine" class="mw-redirect" title="Meta-chloroamphetamine"><i>meta</i>-chloroamphetamine</a> (MCA/4-CA), <a href="/wiki/2-chloroamphetamine" class="mw-redirect" title="2-chloroamphetamine"><i>ortho</i>-chloroamphetamine</a> (OCA/2-CA), <a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">3,4-dichloroamphetamine</a> (3,4-DCA), <a href="/wiki/2,4-dichloroamphetamine" class="mw-redirect" title="2,4-dichloroamphetamine">2,4-dichloroamphetamine</a> (2,4-DCA), <a href="/wiki/Chlorphentermine" title="Chlorphentermine">chlorphentermine</a>, <a href="/wiki/4-Chloromethcathinone" title="4-Chloromethcathinone">4-chloromethcathinone</a> (4-CMC; clephedrone), <a href="/wiki/4-chlorophenylisobutylamine" class="mw-redirect" title="4-chlorophenylisobutylamine">4-chlorophenylisobutylamine</a> (4-CAB; AEPCA), <a href="/wiki/6-chloro-2-aminotetralin" class="mw-redirect" title="6-chloro-2-aminotetralin">6-chloro-2-aminotetralin</a> (6-CAT), <a href="/wiki/5-iodo-2-aminoindane" class="mw-redirect" title="5-iodo-2-aminoindane">5-iodo-2-aminoindane</a> (5-IAI), and <a href="/wiki/Org_6582" title="Org 6582">Org 6582</a>, among others.<sup id="cite_ref-ShulginManningDaley2011_2-2" class="reference"><a href="#cite_note-ShulginManningDaley2011-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1992_3-48" class="reference"><a href="#cite_note-Fuller1992-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuller1978_5-28" class="reference"><a href="#cite_note-Fuller1978-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Shulgin1978_1-6" class="reference"><a href="#cite_note-Shulgin1978-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=11" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>PCA was first <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesized</a> by 1936<sup id="cite_ref-Shulgin1978_1-7" class="reference"><a href="#cite_note-Shulgin1978-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> and was first developed for potential medical use in the 1960s.<sup id="cite_ref-Shulgin1978_1-8" class="reference"><a href="#cite_note-Shulgin1978-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HollandBuckWeissman1963_40-0" class="reference"><a href="#cite_note-HollandBuckWeissman1963-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FullerHinesMills1965_41-0" class="reference"><a href="#cite_note-FullerHinesMills1965-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-vanPraagSchutBosma1971_8-1" class="reference"><a href="#cite_note-vanPraagSchutBosma1971-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-vanPraagKorf1973_9-1" class="reference"><a href="#cite_note-vanPraagKorf1973-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=12" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Legal_status">Legal status</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=13" title="Edit section: Legal status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="China">China</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=14" title="Edit section: China"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As of October 2015, 4-CA is a <a href="/wiki/Controlled_substance" title="Controlled substance">controlled substance</a> in <a href="/wiki/China" title="China">China</a>.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="United_States">United States</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=15" title="Edit section: United States"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>PCA is not a <a href="/wiki/Controlled_substance" title="Controlled substance">scheduled compound</a> in the <a href="/wiki/United_States" title="United States">United States</a>.<sup id="cite_ref-ShulginManningDaley2011_2-3" class="reference"><a href="#cite_note-ShulginManningDaley2011-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Para-Chloroamphetamine&action=edit&section=16" 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 reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-Shulgin1978-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Shulgin1978_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Shulgin1978_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Shulgin1978_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Shulgin1978_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Shulgin1978_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Shulgin1978_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Shulgin1978_1-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Shulgin1978_1-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Shulgin1978_1-8"><sup><i><b>i</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFShulgin1978" class="citation book cs1">Shulgin AT (1978). <a rel="nofollow" class="external text" href="https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_6">"Psychotomimetic Drugs: Structure-Activity Relationships"</a>. In Iversen LL, Iversen SD, Snyder SH (eds.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=h0_uBwAAQBAJ&pg=PA261"><i>Stimulants</i></a>. Boston, MA: Springer US. pp. <span class="nowrap">243–</span>333. <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%2F978-1-4757-0510-2_6">10.1007/978-1-4757-0510-2_6</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-0512-6" title="Special:BookSources/978-1-4757-0512-6"><bdi>978-1-4757-0512-6</bdi></a>. <q>Considerable clinical application of 4-CA has been made, and it has been found effective as an antidepressant when used chronically at levels of 75 mg/day (van Praag et al., 1971; van Praag and Korf, 1976). There are very few side effects noted and the drug is tolerated very well. However, indications of raphe-nucleus degeneration (Yunger et al., 1974) and related neurotoxicity (Harvey and McMaster, 1976) in experimental animals have discouraged further clinical study. [...] There were no reports from the clinical studies of 4-CA that suggested any psychotomimetic action.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Psychotomimetic+Drugs%3A+Structure-Activity+Relationships&rft.btitle=Stimulants&rft.place=Boston%2C+MA&rft.pages=%3Cspan+class%3D%22nowrap%22%3E243-%3C%2Fspan%3E333&rft.pub=Springer+US&rft.date=1978&rft_id=info%3Adoi%2F10.1007%2F978-1-4757-0510-2_6&rft.isbn=978-1-4757-0512-6&rft.aulast=Shulgin&rft.aufirst=Alexander+T.&rft_id=https%3A%2F%2Fbitnest.netfirms.com%2Fexternal%2F10.1007%2F978-1-4757-0510-2_6&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-ShulginManningDaley2011-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-ShulginManningDaley2011_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ShulginManningDaley2011_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ShulginManningDaley2011_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-ShulginManningDaley2011_2-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShulginManningDaley2011" class="citation book cs1">Shulgin A, Manning T, Daley PF (2011). <i><a href="/wiki/The_Shulgin_Index" title="The Shulgin Index">The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds</a></i>. Vol. 1. Berkeley: Transform Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-9630096-3-0" title="Special:BookSources/978-0-9630096-3-0"><bdi>978-0-9630096-3-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Shulgin+Index%2C+Volume+One%3A+Psychedelic+Phenethylamines+and+Related+Compounds&rft.place=Berkeley&rft.pub=Transform+Press&rft.date=2011&rft.isbn=978-0-9630096-3-0&rft.aulast=Shulgin&rft.aufirst=A&rft.au=Manning%2C+T&rft.au=Daley%2C+PF&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Fuller1992-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Fuller1992_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-13"><sup><i><b>n</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-14"><sup><i><b>o</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-15"><sup><i><b>p</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-16"><sup><i><b>q</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-17"><sup><i><b>r</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-18"><sup><i><b>s</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-19"><sup><i><b>t</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-20"><sup><i><b>u</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-21"><sup><i><b>v</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-22"><sup><i><b>w</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-23"><sup><i><b>x</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-24"><sup><i><b>y</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-25"><sup><i><b>z</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-26"><sup><i><b>aa</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-27"><sup><i><b>ab</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-28"><sup><i><b>ac</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-29"><sup><i><b>ad</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-30"><sup><i><b>ae</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-31"><sup><i><b>af</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-32"><sup><i><b>ag</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-33"><sup><i><b>ah</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-34"><sup><i><b>ai</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-35"><sup><i><b>aj</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-36"><sup><i><b>ak</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-37"><sup><i><b>al</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-38"><sup><i><b>am</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-39"><sup><i><b>an</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-40"><sup><i><b>ao</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-41"><sup><i><b>ap</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-42"><sup><i><b>aq</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-43"><sup><i><b>ar</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-44"><sup><i><b>as</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-45"><sup><i><b>at</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-46"><sup><i><b>au</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-47"><sup><i><b>av</b></i></sup></a> <a href="#cite_ref-Fuller1992_3-48"><sup><i><b>aw</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFuller1992" class="citation journal cs1">Fuller RW (May 1992). "Effects of p-chloroamphetamine on brain serotonin neurons". <i>Neurochem Res</i>. <b>17</b> (5): <span class="nowrap">449–</span>456. <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%2FBF00969891">10.1007/BF00969891</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/1528354">1528354</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neurochem+Res&rft.atitle=Effects+of+p-chloroamphetamine+on+brain+serotonin+neurons&rft.volume=17&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E449-%3C%2Fspan%3E456&rft.date=1992-05&rft_id=info%3Adoi%2F10.1007%2FBF00969891&rft_id=info%3Apmid%2F1528354&rft.aulast=Fuller&rft.aufirst=RW&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Fuller1986-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Fuller1986_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Fuller1986_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Fuller1986_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Fuller1986_4-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFuller1986" class="citation journal cs1">Fuller RW (1986). "Biochemical pharmacology of the serotonin system". <i>Adv Neurol</i>. <b>43</b>: <span class="nowrap">469–</span>480. <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/2936068">2936068</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Adv+Neurol&rft.atitle=Biochemical+pharmacology+of+the+serotonin+system&rft.volume=43&rft.pages=%3Cspan+class%3D%22nowrap%22%3E469-%3C%2Fspan%3E480&rft.date=1986&rft_id=info%3Apmid%2F2936068&rft.aulast=Fuller&rft.aufirst=RW&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Fuller1978-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-Fuller1978_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-13"><sup><i><b>n</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-14"><sup><i><b>o</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-15"><sup><i><b>p</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-16"><sup><i><b>q</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-17"><sup><i><b>r</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-18"><sup><i><b>s</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-19"><sup><i><b>t</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-20"><sup><i><b>u</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-21"><sup><i><b>v</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-22"><sup><i><b>w</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-23"><sup><i><b>x</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-24"><sup><i><b>y</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-25"><sup><i><b>z</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-26"><sup><i><b>aa</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-27"><sup><i><b>ab</b></i></sup></a> <a href="#cite_ref-Fuller1978_5-28"><sup><i><b>ac</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFuller1978" class="citation journal cs1">Fuller RW (June 1978). "Structure-activity relationships among the halogenated amphetamines". <i>Ann N Y Acad Sci</i>. <b>305</b> (1): <span class="nowrap">147–</span>159. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1978NYASA.305..147F">1978NYASA.305..147F</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1749-6632.1978.tb31518.x">10.1111/j.1749-6632.1978.tb31518.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/152079">152079</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Ann+N+Y+Acad+Sci&rft.atitle=Structure-activity+relationships+among+the+halogenated+amphetamines&rft.volume=305&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E147-%3C%2Fspan%3E159&rft.date=1978-06&rft_id=info%3Apmid%2F152079&rft_id=info%3Adoi%2F10.1111%2Fj.1749-6632.1978.tb31518.x&rft_id=info%3Abibcode%2F1978NYASA.305..147F&rft.aulast=Fuller&rft.aufirst=RW&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-BlanckaertVanquekelbergheCoopman2018-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-BlanckaertVanquekelbergheCoopman2018_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-BlanckaertVanquekelbergheCoopman2018_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-BlanckaertVanquekelbergheCoopman2018_6-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-BlanckaertVanquekelbergheCoopman2018_6-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-BlanckaertVanquekelbergheCoopman2018_6-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-BlanckaertVanquekelbergheCoopman2018_6-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlanckaertVanquekelbergheCoopmanRisseeuw2018" class="citation journal cs1">Blanckaert P, Vanquekelberghe S, Coopman V, Risseeuw MD, Van Calenbergh S, Cordonnier J (July 2018). "Identification and characterization of 4-chloromethamphetamine (4-CMA) in seized ecstacy - a risk to public health". <i>Forensic Sci Int</i>. <b>288</b>: <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%2Fj.forsciint.2018.04.023">10.1016/j.forsciint.2018.04.023</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/1854%2FLU-8569680">1854/LU-8569680</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/29753935">29753935</a>. <q>Psychoactive effects of 4-CMA and 4-CA were evaluated in humans while researching both compounds as antidepressants. In the dosages used (80-90 mg daily, in 3 doses), no significant acute psychoactive effects were noticed; adverse effects were also low, although an effect on sleep and nausea was mentioned [7].</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Forensic+Sci+Int&rft.atitle=Identification+and+characterization+of+4-chloromethamphetamine+%284-CMA%29+in+seized+ecstacy+-+a+risk+to+public+health&rft.volume=288&rft.pages=%3Cspan+class%3D%22nowrap%22%3E173-%3C%2Fspan%3E180&rft.date=2018-07&rft_id=info%3Ahdl%2F1854%2FLU-8569680&rft_id=info%3Apmid%2F29753935&rft_id=info%3Adoi%2F10.1016%2Fj.forsciint.2018.04.023&rft.aulast=Blanckaert&rft.aufirst=P&rft.au=Vanquekelberghe%2C+S&rft.au=Coopman%2C+V&rft.au=Risseeuw%2C+MD&rft.au=Van+Calenbergh%2C+S&rft.au=Cordonnier%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-LuethiLiechti2020-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-LuethiLiechti2020_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLuethiLiechti2020" class="citation journal cs1">Luethi D, Liechti ME (April 2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7225206">"Designer drugs: mechanism of action and adverse effects"</a>. <i>Arch Toxicol</i>. <b>94</b> (4): <span class="nowrap">1085–</span>1133. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2020ArTox..94.1085L">2020ArTox..94.1085L</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00204-020-02693-7">10.1007/s00204-020-02693-7</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/PMC7225206">7225206</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/32249347">32249347</a>. <q>Compared with amphetamine, an increase in serotonergic toxicity has been reported for the para-chlorinated derivative 4-chloroamphetamine, likely explained by highly potent serotonergic activity coupled with considerably potent dopaminergic activity (Colado et al. 1993; Fuller 1992; Johnson et al. 1990; Luethi et al. 2019b; Miller et al. 1986). However, unlike other halogenated stimulants, such as 4-fluoroamphetamine, 4-chloroamphetamine never achieved popularity as a designer drug, possibly because of its well-documented neurotoxicity.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Arch+Toxicol&rft.atitle=Designer+drugs%3A+mechanism+of+action+and+adverse+effects&rft.volume=94&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1085-%3C%2Fspan%3E1133&rft.date=2020-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7225206%23id-name%3DPMC&rft_id=info%3Apmid%2F32249347&rft_id=info%3Adoi%2F10.1007%2Fs00204-020-02693-7&rft_id=info%3Abibcode%2F2020ArTox..94.1085L&rft.aulast=Luethi&rft.aufirst=D&rft.au=Liechti%2C+ME&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7225206&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-vanPraagSchutBosma1971-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-vanPraagSchutBosma1971_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-vanPraagSchutBosma1971_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="CITEREFvan_PraagSchutBosmavan_den_Bergh1971" class="citation journal cs1">van Praag HM, Schut T, Bosma E, van den Bergh R (1971). "A comparative study of the therapeutic effects of sone 4-chlorinated amphetamine derivatives in depressive patients". <i>Psychopharmacologia</i>. <b>20</b> (1): <span class="nowrap">66–</span>76. <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%2FBF00404060">10.1007/BF00404060</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/5565748">5565748</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Psychopharmacologia&rft.atitle=A+comparative+study+of+the+therapeutic+effects+of+sone+4-chlorinated+amphetamine+derivatives+in+depressive+patients&rft.volume=20&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E66-%3C%2Fspan%3E76&rft.date=1971&rft_id=info%3Adoi%2F10.1007%2FBF00404060&rft_id=info%3Apmid%2F5565748&rft.aulast=van+Praag&rft.aufirst=HM&rft.au=Schut%2C+T&rft.au=Bosma%2C+E&rft.au=van+den+Bergh%2C+R&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-vanPraagKorf1973-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-vanPraagKorf1973_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-vanPraagKorf1973_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 id="CITEREFvan_PraagKorf1973" class="citation journal cs1">van Praag HM, Korf J (January 1973). "4-Chloramphetamines. Chance and trend in the development of new antidepressants". <i>J Clin Pharmacol New Drugs</i>. <b>13</b> (1): <span class="nowrap">3–</span>14. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fj.1552-4604.1973.tb00063.x">10.1002/j.1552-4604.1973.tb00063.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4566121">4566121</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Clin+Pharmacol+New+Drugs&rft.atitle=4-Chloramphetamines.+Chance+and+trend+in+the+development+of+new+antidepressants&rft.volume=13&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3-%3C%2Fspan%3E14&rft.date=1973-01&rft_id=info%3Adoi%2F10.1002%2Fj.1552-4604.1973.tb00063.x&rft_id=info%3Apmid%2F4566121&rft.aulast=van+Praag&rft.aufirst=HM&rft.au=Korf%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-HalberstadtGeyer2018-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-HalberstadtGeyer2018_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-HalberstadtGeyer2018_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-HalberstadtGeyer2018_10-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-HalberstadtGeyer2018_10-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHalberstadtGeyer2018" class="citation book cs1">Halberstadt AL, Geyer MA (2018). "Effect of Hallucinogens on Unconditioned Behavior". In Halberstadt AL, Vollenweider FX, Nichols DE (eds.). <i>Behavioral Neurobiology of Psychedelic Drugs</i>. Current Topics in Behavioral Neurosciences. Vol. 36. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. <span class="nowrap">159–</span>199. <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/10.1007%2F7854_2016_466">10.1007/7854_2016_466</a></span>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-662-55878-2" title="Special:BookSources/978-3-662-55878-2"><bdi>978-3-662-55878-2</bdi></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/PMC5787039">5787039</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/28224459">28224459</a>. <q>Amphetamine and methamphetamine, which act primarily by increasing carrier-mediated release of dopamine and norepinephrine, do not provoke head twitches (Corne and Pickering 1967; Silva and Calil 1975; Yamamoto and Ueki 1975; Jacobs et al. 1976; Bedard and Pycock 1977; Halberstadt and Geyer 2013). By contrast, the 5-HT releasing drugs fenfluramine and p-chloroamphetamine (PCA) do produce a robust HTR (Singleton and Marsden 1981; Darmani 1998a). Fenfluramine and PCA are thought to act indirectly, by increasing carrier-mediated release of 5-HT, because the response can be blocked by inhibition of the 5-HT transporter (Balsara et al. 1986; Darmani 1998a) or by depletion of 5-HT (Singleton and Marsden 1981; Balsara et al. 1986). [...] Because indirect 5-HT agonists such as fenfluramine, PCA, and 5-HTP are not hallucinogenic (Van Praag et al. 1971; Brauer et al. 1996; Turner et al. 2006), their effects on HTR can potentially be classified as false-positive responses.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Effect+of+Hallucinogens+on+Unconditioned+Behavior&rft.btitle=Behavioral+Neurobiology+of+Psychedelic+Drugs&rft.place=Berlin%2C+Heidelberg&rft.series=Current+Topics+in+Behavioral+Neurosciences&rft.pages=%3Cspan+class%3D%22nowrap%22%3E159-%3C%2Fspan%3E199&rft.pub=Springer+Berlin+Heidelberg&rft.date=2018&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5787039%23id-name%3DPMC&rft_id=info%3Apmid%2F28224459&rft_id=info%3Adoi%2F10.1007%2F7854_2016_466&rft.isbn=978-3-662-55878-2&rft.aulast=Halberstadt&rft.aufirst=AL&rft.au=Geyer%2C+MA&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-HalberstadtChathaKlein2020-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-HalberstadtChathaKlein2020_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-HalberstadtChathaKlein2020_11-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-HalberstadtChathaKlein2020_11-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHalberstadtChathaKleinWallach2020" class="citation journal cs1">Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9191653">"Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species"</a>. <i>Neuropharmacology</i>. <b>167</b>: 107933. <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.neuropharm.2019.107933">10.1016/j.neuropharm.2019.107933</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/PMC9191653">9191653</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/31917152">31917152</a>. <q>Indirect 5-HT2A agonists such as fenfluramine, p-chloroamphetamine (PCA), and 5-hydroxytryptophan (5-HTP) induce head twitches in rodents (Corne et al. 1963; Singleton and Marsden 1981; Darmani 1998) but do not act as hallucinogens in humans (van Praag et al. 1971; Brauer et al. 1996; Turner et al. 2006), However, overdoses of compounds that increase serotonin (5-HT) release can result in 5-HT syndrome, which sometimes includes hallucinations (Birmes et al. 2003; Evans and Sebastian 2007).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neuropharmacology&rft.atitle=Correlation+between+the+potency+of+hallucinogens+in+the+mouse+head-twitch+response+assay+and+their+behavioral+and+subjective+effects+in+other+species&rft.volume=167&rft.pages=107933&rft.date=2020-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9191653%23id-name%3DPMC&rft_id=info%3Apmid%2F31917152&rft_id=info%3Adoi%2F10.1016%2Fj.neuropharm.2019.107933&rft.aulast=Halberstadt&rft.aufirst=AL&rft.au=Chatha%2C+M&rft.au=Klein%2C+AK&rft.au=Wallach%2C+J&rft.au=Brandt%2C+SD&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9191653&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-RothmanBloughBaumann2008-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-RothmanBloughBaumann2008_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-RothmanBloughBaumann2008_12-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRothmanBloughBaumann2008" class="citation journal cs1">Rothman RB, Blough BE, Baumann MH (December 2008). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2683464">"Dual dopamine/serotonin releasers: potential treatment agents for stimulant addiction"</a>. <i>Exp Clin Psychopharmacol</i>. <b>16</b> (6): <span class="nowrap">458–</span>474. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1037%2Fa0014103">10.1037/a0014103</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/PMC2683464">2683464</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/19086767">19086767</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Exp+Clin+Psychopharmacol&rft.atitle=Dual+dopamine%2Fserotonin+releasers%3A+potential+treatment+agents+for+stimulant+addiction&rft.volume=16&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E458-%3C%2Fspan%3E474&rft.date=2008-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2683464%23id-name%3DPMC&rft_id=info%3Apmid%2F19086767&rft_id=info%3Adoi%2F10.1037%2Fa0014103&rft.aulast=Rothman&rft.aufirst=RB&rft.au=Blough%2C+BE&rft.au=Baumann%2C+MH&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2683464&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-RothmanBaumann2006b-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-RothmanBaumann2006b_13-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRothmanBaumann2006" class="citation journal cs1">Rothman RB, Baumann MH (August 2006). "Balance between dopamine and serotonin release modulates behavioral effects of amphetamine-type drugs". <i>Ann N Y Acad Sci</i>. <b>1074</b> (1): <span class="nowrap">245–</span>260. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2006NYASA1074..245R">2006NYASA1074..245R</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1196%2Fannals.1369.064">10.1196/annals.1369.064</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/17105921">17105921</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Ann+N+Y+Acad+Sci&rft.atitle=Balance+between+dopamine+and+serotonin+release+modulates+behavioral+effects+of+amphetamine-type+drugs&rft.volume=1074&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E245-%3C%2Fspan%3E260&rft.date=2006-08&rft_id=info%3Apmid%2F17105921&rft_id=info%3Adoi%2F10.1196%2Fannals.1369.064&rft_id=info%3Abibcode%2F2006NYASA1074..245R&rft.aulast=Rothman&rft.aufirst=RB&rft.au=Baumann%2C+MH&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Forsyth2012-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-Forsyth2012_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Forsyth2012_14-1"><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="CITEREFForsyth2012" class="citation journal cs1">Forsyth AN (22 May 2012). <a rel="nofollow" class="external text" href="https://scholarworks.uno.edu/td/1436/">"Synthesis and Biological Evaluation of Rigid Analogues of Methamphetamines"</a>. <i>ScholarWorks@UNO</i><span class="reference-accessdate">. Retrieved <span class="nowrap">4 November</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=ScholarWorks%40UNO&rft.atitle=Synthesis+and+Biological+Evaluation+of+Rigid+Analogues+of+Methamphetamines&rft.date=2012-05-22&rft.aulast=Forsyth&rft.aufirst=AN&rft_id=https%3A%2F%2Fscholarworks.uno.edu%2Ftd%2F1436%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Blough2008-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-Blough2008_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Blough2008_15-1"><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="CITEREFBlough2008" class="citation book cs1">Blough B (July 2008). <a rel="nofollow" class="external text" href="https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf">"Dopamine-releasing agents"</a> <span class="cs1-format">(PDF)</span>. In Trudell ML, Izenwasser S (eds.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=QCagLAAACAAJ"><i>Dopamine Transporters: Chemistry, Biology and Pharmacology</i></a>. Hoboken [NJ]: Wiley. pp. <span class="nowrap">305–</span>320. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-11790-3" title="Special:BookSources/978-0-470-11790-3"><bdi>978-0-470-11790-3</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/181862653">181862653</a>. <a href="/wiki/OL_(identifier)" class="mw-redirect" title="OL (identifier)">OL</a> <a rel="nofollow" class="external text" href="https://openlibrary.org/works/OL18589888W">18589888W</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Dopamine-releasing+agents&rft.btitle=Dopamine+Transporters%3A+Chemistry%2C+Biology+and+Pharmacology&rft.place=Hoboken+%5BNJ%5D&rft.pages=%3Cspan+class%3D%22nowrap%22%3E305-%3C%2Fspan%3E320&rft.pub=Wiley&rft.date=2008-07&rft_id=info%3Aoclcnum%2F181862653&rft_id=https%3A%2F%2Fopenlibrary.org%2Fworks%2FOL18589888W%23id-name%3DOL&rft.isbn=978-0-470-11790-3&rft.aulast=Blough&rft.aufirst=B&rft_id=https%3A%2F%2Fbitnest.netfirms.com%2Fexternal%2FBooks%2FDopamine-releasing-agents_c11.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Marona-LewickaRheeSprague1995-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-Marona-LewickaRheeSprague1995_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Marona-LewickaRheeSprague1995_16-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Marona-LewickaRheeSprague1995_16-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMarona-LewickaRheeSpragueNichols1995" class="citation journal cs1">Marona-Lewicka D, Rhee GS, Sprague JE, Nichols DE (December 1995). "Psychostimulant-like effects of p-fluoroamphetamine in the rat". <i>European Journal of Pharmacology</i>. <b>287</b> (2): <span class="nowrap">105–</span>113. <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%2895%2900478-5">10.1016/0014-2999(95)00478-5</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/8749023">8749023</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=Psychostimulant-like+effects+of+p-fluoroamphetamine+in+the+rat&rft.volume=287&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E105-%3C%2Fspan%3E113&rft.date=1995-12&rft_id=info%3Adoi%2F10.1016%2F0014-2999%2895%2900478-5&rft_id=info%3Apmid%2F8749023&rft.aulast=Marona-Lewicka&rft.aufirst=D&rft.au=Rhee%2C+GS&rft.au=Sprague%2C+JE&rft.au=Nichols%2C+DE&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-FitzgeraldGannonWalther2024-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-FitzgeraldGannonWalther2024_17-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFitzgeraldGannonWaltherLandavazo2024" class="citation journal cs1">Fitzgerald LR, Gannon BM, Walther D, Landavazo A, Hiranita T, Blough BE, et al. (March 2024). "Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones". <i>Neuropharmacology</i>. <b>245</b>: 109827. <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.neuropharm.2023.109827">10.1016/j.neuropharm.2023.109827</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> 10842458. <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/38154512">38154512</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neuropharmacology&rft.atitle=Structure-activity+relationships+for+locomotor+stimulant+effects+and+monoamine+transporter+interactions+of+substituted+amphetamines+and+cathinones&rft.volume=245&rft.pages=109827&rft.date=2024-03&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10842458%23id-name%3DPMC&rft_id=info%3Apmid%2F38154512&rft_id=info%3Adoi%2F10.1016%2Fj.neuropharm.2023.109827&rft.aulast=Fitzgerald&rft.aufirst=LR&rft.au=Gannon%2C+BM&rft.au=Walther%2C+D&rft.au=Landavazo%2C+A&rft.au=Hiranita%2C+T&rft.au=Blough%2C+BE&rft.au=Baumann%2C+MH&rft.au=Fantegrossi%2C+WE&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Nicole2022-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-Nicole2022_18-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNicole2022" class="citation web cs1">Nicole L (2022). <a rel="nofollow" class="external text" href="https://www.proquest.com/openview/a207e98868b4a9c5ac9296fb24abbcd8/">"In vivo Structure-Activity Relationships of Substituted Amphetamines and Substituted Cathinones"</a>. <i>ProQuest</i><span class="reference-accessdate">. Retrieved <span class="nowrap">5 December</span> 2024</span>. <q>FIGURE 2-6: Release: Effects of the specified test drug on monoamine release by DAT (red circles), NET (blue squares), and SERT (black traingles) in rat brain tissue. [...] EC50 values determined for the drug indicated within the panel. [...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ProQuest&rft.atitle=In+vivo+Structure-Activity+Relationships+of+Substituted+Amphetamines+and+Substituted+Cathinones&rft.date=2022&rft.aulast=Nicole&rft.aufirst=L&rft_id=https%3A%2F%2Fwww.proquest.com%2Fopenview%2Fa207e98868b4a9c5ac9296fb24abbcd8%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Sanders-BushSteranka1978-19"><span class="mw-cite-backlink">^ <a href="#cite_ref-Sanders-BushSteranka1978_19-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-13"><sup><i><b>n</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-14"><sup><i><b>o</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-15"><sup><i><b>p</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-16"><sup><i><b>q</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-17"><sup><i><b>r</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-18"><sup><i><b>s</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-19"><sup><i><b>t</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-20"><sup><i><b>u</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-21"><sup><i><b>v</b></i></sup></a> <a href="#cite_ref-Sanders-BushSteranka1978_19-22"><sup><i><b>w</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSanders-BushSteranka1978" class="citation journal cs1">Sanders-Bush E, Steranka LR (June 1978). "Immediate and long-term effects of p-chloroamphetamine on brain amines". <i>Ann N Y Acad Sci</i>. <b>305</b> (1): <span class="nowrap">208–</span>221. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1978NYASA.305..208S">1978NYASA.305..208S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1749-6632.1978.tb31525.x">10.1111/j.1749-6632.1978.tb31525.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/360935">360935</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Ann+N+Y+Acad+Sci&rft.atitle=Immediate+and+long-term+effects+of+p-chloroamphetamine+on+brain+amines&rft.volume=305&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E208-%3C%2Fspan%3E221&rft.date=1978-06&rft_id=info%3Apmid%2F360935&rft_id=info%3Adoi%2F10.1111%2Fj.1749-6632.1978.tb31525.x&rft_id=info%3Abibcode%2F1978NYASA.305..208S&rft.aulast=Sanders-Bush&rft.aufirst=E&rft.au=Steranka%2C+LR&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-SpragueJohnsonSchmidt1996-20"><span class="mw-cite-backlink">^ <a href="#cite_ref-SpragueJohnsonSchmidt1996_20-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-SpragueJohnsonSchmidt1996_20-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-SpragueJohnsonSchmidt1996_20-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSpragueJohnsonSchmidtNichols1996" class="citation journal cs1">Sprague JE, Johnson MP, Schmidt CJ, Nichols DE (October 1996). "Studies on the mechanism of p-chloroamphetamine neurotoxicity". <i>Biochem Pharmacol</i>. <b>52</b> (8): <span class="nowrap">1271–</span>1277. <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%2F0006-2952%2896%2900482-0">10.1016/0006-2952(96)00482-0</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/8937435">8937435</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochem+Pharmacol&rft.atitle=Studies+on+the+mechanism+of+p-chloroamphetamine+neurotoxicity&rft.volume=52&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1271-%3C%2Fspan%3E1277&rft.date=1996-10&rft_id=info%3Adoi%2F10.1016%2F0006-2952%2896%2900482-0&rft_id=info%3Apmid%2F8937435&rft.aulast=Sprague&rft.aufirst=JE&rft.au=Johnson%2C+MP&rft.au=Schmidt%2C+CJ&rft.au=Nichols%2C+DE&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Geyer1996-21"><span class="mw-cite-backlink">^ <a href="#cite_ref-Geyer1996_21-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Geyer1996_21-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Geyer1996_21-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGeyer1996" class="citation journal cs1">Geyer MA (1996). "Serotonergic functions in arousal and motor activity". <i>Behav Brain Res</i>. <b>73</b> (<span class="nowrap">1–</span>2): <span class="nowrap">31–</span>35. <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%2F0166-4328%2896%2900065-4">10.1016/0166-4328(96)00065-4</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/8788473">8788473</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Behav+Brain+Res&rft.atitle=Serotonergic+functions+in+arousal+and+motor+activity&rft.volume=73&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E31-%3C%2Fspan%3E35&rft.date=1996&rft_id=info%3Adoi%2F10.1016%2F0166-4328%2896%2900065-4&rft_id=info%3Apmid%2F8788473&rft.aulast=Geyer&rft.aufirst=MA&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-WeeAndersonBaumann2005-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-WeeAndersonBaumann2005_22-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWeeAndersonBaumannRothman2005" class="citation journal cs1">Wee S, Anderson KG, Baumann MH, Rothman RB, Blough BE, Woolverton WL (May 2005). "Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs". <i>The Journal of Pharmacology and Experimental Therapeutics</i>. <b>313</b> (2): <span class="nowrap">848–</span>854. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fjpet.104.080101">10.1124/jpet.104.080101</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/15677348">15677348</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:12135483">12135483</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Pharmacology+and+Experimental+Therapeutics&rft.atitle=Relationship+between+the+serotonergic+activity+and+reinforcing+effects+of+a+series+of+amphetamine+analogs&rft.volume=313&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E848-%3C%2Fspan%3E854&rft.date=2005-05&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A12135483%23id-name%3DS2CID&rft_id=info%3Apmid%2F15677348&rft_id=info%3Adoi%2F10.1124%2Fjpet.104.080101&rft.aulast=Wee&rft.aufirst=S&rft.au=Anderson%2C+KG&rft.au=Baumann%2C+MH&rft.au=Rothman%2C+RB&rft.au=Blough%2C+BE&rft.au=Woolverton%2C+WL&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-OrikasaSloley1988-23"><span class="mw-cite-backlink">^ <a href="#cite_ref-OrikasaSloley1988_23-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-OrikasaSloley1988_23-1"><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="CITEREFOrikasaSloley1988" class="citation journal cs1">Orikasa S, Sloley BD (1988). "Effects of 5,7-dihydroxytryptamine and 6-hydroxydopamine on head-twitch response induced by serotonin, p-chloroamphetamine, and tryptamine in mice". <i>Psychopharmacology (Berl)</i>. <b>95</b> (1): <span class="nowrap">124–</span>131. <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%2FBF00212780">10.1007/BF00212780</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/3133691">3133691</a>. <q>Head-twitch response (HTR) in mice was induced by intracerebroventricular injection of tryptamine (TRA) as well as serotonin (5-HT) and p-chloroamphetamine (PCA). Pretreatment with 5,7-dihydroxytryptamine enhanced both the 5-HT-induced and the TRA-induced HTR. The PCA-induced HTR, however, was attenuated by the drug. On the other hand, pretreatment with 6-hydroxydopamine did not alter the 5-HT response but enhanced both the PCA- and the TRA-induced response. These results suggest that 5-HT may directly stimulate the post-synaptic receptors, while the PCA response may be based on the release of endogenous 5-HT.</q></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=Effects+of+5%2C7-dihydroxytryptamine+and+6-hydroxydopamine+on+head-twitch+response+induced+by+serotonin%2C+p-chloroamphetamine%2C+and+tryptamine+in+mice&rft.volume=95&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E124-%3C%2Fspan%3E131&rft.date=1988&rft_id=info%3Adoi%2F10.1007%2FBF00212780&rft_id=info%3Apmid%2F3133691&rft.aulast=Orikasa&rft.aufirst=S&rft.au=Sloley%2C+BD&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-WojtasGołembiowska2023-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-WojtasGołembiowska2023_24-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWojtasGołembiowska2023" class="citation journal cs1">Wojtas A, Gołembiowska K (December 2023). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10778977">"Molecular and Medical Aspects of Psychedelics"</a>. <i>Int J Mol Sci</i>. <b>25</b> (1): 241. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fijms25010241">10.3390/ijms25010241</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10778977">10778977</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/38203411">38203411</a>. <q>While some false positives have been identified, such as fenfluramine, p-chloroamphetamine, and 5-hydroxytryptophan, the test predominantly exhibits specificity for 5-HT2A receptor agonists [15].</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Int+J+Mol+Sci&rft.atitle=Molecular+and+Medical+Aspects+of+Psychedelics&rft.volume=25&rft.issue=1&rft.pages=241&rft.date=2023-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10778977%23id-name%3DPMC&rft_id=info%3Apmid%2F38203411&rft_id=info%3Adoi%2F10.3390%2Fijms25010241&rft.aulast=Wojtas&rft.aufirst=A&rft.au=Go%C5%82embiowska%2C+K&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10778977&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-OgrenRoss1977-25"><span class="mw-cite-backlink">^ <a href="#cite_ref-OgrenRoss1977_25-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-OgrenRoss1977_25-1"><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="CITEREFOgrenRoss1977" class="citation journal cs1">Ogren SO, Ross SB (October 1977). "Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones". <i>Acta Pharmacol Toxicol (Copenh)</i>. <b>41</b> (4): <span class="nowrap">353–</span>368. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1600-0773.1977.tb02674.x">10.1111/j.1600-0773.1977.tb02674.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/303437">303437</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Pharmacol+Toxicol+%28Copenh%29&rft.atitle=Substituted+amphetamine+derivatives.+II.+Behavioural+effects+in+mice+related+to+monoaminergic+neurones&rft.volume=41&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E353-%3C%2Fspan%3E368&rft.date=1977-10&rft_id=info%3Adoi%2F10.1111%2Fj.1600-0773.1977.tb02674.x&rft_id=info%3Apmid%2F303437&rft.aulast=Ogren&rft.aufirst=SO&rft.au=Ross%2C+SB&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-VargasDunlapDong2023-26"><span class="mw-cite-backlink">^ <a href="#cite_ref-VargasDunlapDong2023_26-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-VargasDunlapDong2023_26-1"><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="CITEREFVargasDunlapDongCarter2023" class="citation journal cs1">Vargas MV, Dunlap LE, Dong C, Carter SJ, Tombari RJ, Jami SA, et al. (February 2023). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10108900">"Psychedelics promote neuroplasticity through the activation of intracellular 5-HT2A receptors"</a>. <i>Science</i>. <b>379</b> (6633): <span class="nowrap">700–</span>706. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2023Sci...379..700V">2023Sci...379..700V</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.adf0435">10.1126/science.adf0435</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/PMC10108900">10108900</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/36795823">36795823</a>. <q>[...] both groups were administered (±)-para-chloroamphetamine (PCA, 5 mg/kg, IP)—a selective serotonin-releasing agent (43). [...] Importantly, PCA is not a 5-HT2AR agonist (fig. S10A), [...] and does not induce a HTR in wild type mice (fig. S10C). [...] In addition to promoting psychedelic-induced structural neuroplasticity, the intracellular population of 5-HT2ARs might also contribute to the hallucinogenic effects of psychedelics. When we administered a serotonin-releasing agent to wild type mice, we did not observe a HTR. However, the same drug was able to induce a HTR in mice expressing SERT on cortical neurons of the mPFC—a brain region known to be essential for the HTR (49).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Psychedelics+promote+neuroplasticity+through+the+activation+of+intracellular+5-HT2A+receptors&rft.volume=379&rft.issue=6633&rft.pages=%3Cspan+class%3D%22nowrap%22%3E700-%3C%2Fspan%3E706&rft.date=2023-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10108900%23id-name%3DPMC&rft_id=info%3Apmid%2F36795823&rft_id=info%3Adoi%2F10.1126%2Fscience.adf0435&rft_id=info%3Abibcode%2F2023Sci...379..700V&rft.aulast=Vargas&rft.aufirst=MV&rft.au=Dunlap%2C+LE&rft.au=Dong%2C+C&rft.au=Carter%2C+SJ&rft.au=Tombari%2C+RJ&rft.au=Jami%2C+SA&rft.au=Cameron%2C+LP&rft.au=Patel%2C+SD&rft.au=Hennessey%2C+JJ&rft.au=Saeger%2C+HN&rft.au=McCorvy%2C+JD&rft.au=Gray%2C+JA&rft.au=Tian%2C+L&rft.au=Olson%2C+DE&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10108900&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-RothmanBaumann2002-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-RothmanBaumann2002_27-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRothmanBaumann2002" class="citation journal cs1">Rothman RB, Baumann MH (July 2002). "Therapeutic and adverse actions of serotonin transporter substrates". <i>Pharmacology & Therapeutics</i>. <b>95</b> (1): <span class="nowrap">73–</span>88. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0163-7258%2802%2900234-6">10.1016/s0163-7258(02)00234-6</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/12163129">12163129</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacology+%26+Therapeutics&rft.atitle=Therapeutic+and+adverse+actions+of+serotonin+transporter+substrates&rft.volume=95&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E73-%3C%2Fspan%3E88&rft.date=2002-07&rft_id=info%3Adoi%2F10.1016%2Fs0163-7258%2802%2900234-6&rft_id=info%3Apmid%2F12163129&rft.aulast=Rothman&rft.aufirst=RB&rft.au=Baumann%2C+MH&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-RothmanBaumann2006a-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-RothmanBaumann2006a_28-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRothmanBaumann2006" class="citation journal cs1">Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". <i>Current Topics in Medicinal Chemistry</i>. <b>6</b> (17): <span class="nowrap">1845–</span>1859. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2174%2F156802606778249766">10.2174/156802606778249766</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/17017961">17017961</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Topics+in+Medicinal+Chemistry&rft.atitle=Therapeutic+potential+of+monoamine+transporter+substrates&rft.volume=6&rft.issue=17&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1845-%3C%2Fspan%3E1859&rft.date=2006&rft_id=info%3Adoi%2F10.2174%2F156802606778249766&rft_id=info%3Apmid%2F17017961&rft.aulast=Rothman&rft.aufirst=RB&rft.au=Baumann%2C+MH&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-LovenbergWalkerBaumgarten1976-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-LovenbergWalkerBaumgarten1976_29-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLovenbergWalkerBaumgarten1976" class="citation book cs1">Lovenberg W, Walker MN, Baumgarten HG (1976). "Chlorinated amphetamines: drugs or toxins". <i>Clinical Pharmacology of Serotonin</i>. Monographs in Neural Sciences. Vol. 3. pp. <span class="nowrap">109–</span>114. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000399342">10.1159/000399342</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-8055-2328-8" title="Special:BookSources/978-3-8055-2328-8"><bdi>978-3-8055-2328-8</bdi></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/790166">790166</a>. <q>A methylated analogue of p-chloroamphetamine is chlorphentermine (fig. 1). This compound is marketed as an appetite suppressant Pre-Sate® and it seemed of interest to reevaluate the effects of this compound on the serotonergic system. One day following the administration of 20 mg/kg to rats there appeared to be little loss of tryptophan hydroxylase in any of the brain regions; e.g., mesencephalic tegmentum 124 %, mesencephalic tectum 95.7 % and striatum 103.5 %, of control values. While this preliminary experiment would suggest that chlorphentermine is not neurotoxic, it would seem in view of the similarity of its structure to p-chloroamphetamine that considerably more detailed experiments should be done to evaluate the long-term effects of this drug and its potential neurotoxicity.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chlorinated+amphetamines%3A+drugs+or+toxins&rft.btitle=Clinical+Pharmacology+of+Serotonin&rft.series=Monographs+in+Neural+Sciences&rft.pages=%3Cspan+class%3D%22nowrap%22%3E109-%3C%2Fspan%3E114&rft.date=1976&rft_id=info%3Apmid%2F790166&rft_id=info%3Adoi%2F10.1159%2F000399342&rft.isbn=978-3-8055-2328-8&rft.aulast=Lovenberg&rft.aufirst=W&rft.au=Walker%2C+MN&rft.au=Baumgarten%2C+HG&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-Reyes-ParadaIturriaga-VasquezCassels2019-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-Reyes-ParadaIturriaga-VasquezCassels2019_30-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFReyes-ParadaIturriaga-VasquezCassels2019" class="citation journal cs1">Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6989591">"Amphetamine Derivatives as Monoamine Oxidase Inhibitors"</a>. <i>Front Pharmacol</i>. <b>10</b>: 1590. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3389%2Ffphar.2019.01590">10.3389/fphar.2019.01590</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6989591">6989591</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/32038257">32038257</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Front+Pharmacol&rft.atitle=Amphetamine+Derivatives+as+Monoamine+Oxidase+Inhibitors&rft.volume=10&rft.pages=1590&rft.date=2019&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6989591%23id-name%3DPMC&rft_id=info%3Apmid%2F32038257&rft_id=info%3Adoi%2F10.3389%2Ffphar.2019.01590&rft.aulast=Reyes-Parada&rft.aufirst=M&rft.au=Iturriaga-Vasquez%2C+P&rft.au=Cassels%2C+BK&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6989591&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-LiuWuLi2020-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-LiuWuLi2020_31-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLiuWuLi2020" class="citation journal cs1">Liu J, Wu R, Li JX (March 2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7845786">"TAAR1 and Psychostimulant Addiction"</a>. <i>Cell Mol Neurobiol</i>. <b>40</b> (2): <span class="nowrap">229–</span>238. <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%2Fs10571-020-00792-8">10.1007/s10571-020-00792-8</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/PMC7845786">7845786</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/31974906">31974906</a>. <q>Amphetamine-like compounds, including amphetamine (AMPH), methamphetamine (METH), MDMA, 4-OH-amphetamine, 4-Cl-amphetamine could induce cAMP accumulation in the HEK-293 cells expressing [rat] TAAR1, indicating that amphetamines are potent agonists of TAAR1 (Bunzow et al. 2001; Miller et al. 2005).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cell+Mol+Neurobiol&rft.atitle=TAAR1+and+Psychostimulant+Addiction&rft.volume=40&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E229-%3C%2Fspan%3E238&rft.date=2020-03&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7845786%23id-name%3DPMC&rft_id=info%3Apmid%2F31974906&rft_id=info%3Adoi%2F10.1007%2Fs10571-020-00792-8&rft.aulast=Liu&rft.aufirst=J&rft.au=Wu%2C+R&rft.au=Li%2C+JX&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7845786&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-BunzowSondersArttamangkul2001-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-BunzowSondersArttamangkul2001_32-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBunzowSondersArttamangkulHarrison2001" class="citation journal cs1">Bunzow JR, Sonders MS, Arttamangkul S, Harrison LM, Zhang G, Quigley DI, et al. (December 2001). "Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor". <i>Mol Pharmacol</i>. <b>60</b> (6): <span class="nowrap">1181–</span>1188. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fmol.60.6.1181">10.1124/mol.60.6.1181</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/11723224">11723224</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Mol+Pharmacol&rft.atitle=Amphetamine%2C+3%2C4-methylenedioxymethamphetamine%2C+lysergic+acid+diethylamide%2C+and+metabolites+of+the+catecholamine+neurotransmitters+are+agonists+of+a+rat+trace+amine+receptor&rft.volume=60&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1181-%3C%2Fspan%3E1188&rft.date=2001-12&rft_id=info%3Adoi%2F10.1124%2Fmol.60.6.1181&rft_id=info%3Apmid%2F11723224&rft.aulast=Bunzow&rft.aufirst=JR&rft.au=Sonders%2C+MS&rft.au=Arttamangkul%2C+S&rft.au=Harrison%2C+LM&rft.au=Zhang%2C+G&rft.au=Quigley%2C+DI&rft.au=Darland%2C+T&rft.au=Suchland%2C+KL&rft.au=Pasumamula%2C+S&rft.au=Kennedy%2C+JL&rft.au=Olson%2C+SB&rft.au=Magenis%2C+RE&rft.au=Amara%2C+SG&rft.au=Grandy%2C+DK&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-DiCaraMaggioAloisi2011-33"><span class="mw-cite-backlink">^ <a href="#cite_ref-DiCaraMaggioAloisi2011_33-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-DiCaraMaggioAloisi2011_33-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-DiCaraMaggioAloisi2011_33-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-DiCaraMaggioAloisi2011_33-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-DiCaraMaggioAloisi2011_33-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-DiCaraMaggioAloisi2011_33-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDi_CaraMaggioAloisiRivet2011" class="citation journal cs1">Di Cara B, Maggio R, Aloisi G, Rivet JM, Lundius EG, Yoshitake T, et al. (November 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6623861">"Genetic deletion of trace amine 1 receptors reveals their role in auto-inhibiting the actions of ecstasy (MDMA)"</a>. <i>J Neurosci</i>. <b>31</b> (47): <span class="nowrap">16928–</span>16940. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1523%2FJNEUROSCI.2502-11.2011">10.1523/JNEUROSCI.2502-11.2011</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/PMC6623861">6623861</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/22114263">22114263</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Neurosci&rft.atitle=Genetic+deletion+of+trace+amine+1+receptors+reveals+their+role+in+auto-inhibiting+the+actions+of+ecstasy+%28MDMA%29&rft.volume=31&rft.issue=47&rft.pages=%3Cspan+class%3D%22nowrap%22%3E16928-%3C%2Fspan%3E16940&rft.date=2011-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6623861%23id-name%3DPMC&rft_id=info%3Apmid%2F22114263&rft_id=info%3Adoi%2F10.1523%2FJNEUROSCI.2502-11.2011&rft.aulast=Di+Cara&rft.aufirst=B&rft.au=Maggio%2C+R&rft.au=Aloisi%2C+G&rft.au=Rivet%2C+JM&rft.au=Lundius%2C+EG&rft.au=Yoshitake%2C+T&rft.au=Svenningsson%2C+P&rft.au=Brocco%2C+M&rft.au=Gobert%2C+A&rft.au=De+Groote%2C+L&rft.au=Cistarelli%2C+L&rft.au=Veiga%2C+S&rft.au=De+Montrion%2C+C&rft.au=Rodriguez%2C+M&rft.au=Galizzi%2C+JP&rft.au=Lockhart%2C+BP&rft.au=Cog%C3%A9%2C+F&rft.au=Boutin%2C+JA&rft.au=Vayer%2C+P&rft.au=Verdouw%2C+PM&rft.au=Groenink%2C+L&rft.au=Millan%2C+MJ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6623861&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-JingLi2015-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-JingLi2015_34-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJingLi2015" class="citation journal cs1">Jing L, Li JX (August 2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4532615">"Trace amine-associated receptor 1: A promising target for the treatment of psychostimulant addiction"</a>. <i>Eur J Pharmacol</i>. <b>761</b>: <span class="nowrap">345–</span>352. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ejphar.2015.06.019">10.1016/j.ejphar.2015.06.019</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/PMC4532615">4532615</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/26092759">26092759</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Eur+J+Pharmacol&rft.atitle=Trace+amine-associated+receptor+1%3A+A+promising+target+for+the+treatment+of+psychostimulant+addiction&rft.volume=761&rft.pages=%3Cspan+class%3D%22nowrap%22%3E345-%3C%2Fspan%3E352&rft.date=2015-08&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4532615%23id-name%3DPMC&rft_id=info%3Apmid%2F26092759&rft_id=info%3Adoi%2F10.1016%2Fj.ejphar.2015.06.019&rft.aulast=Jing&rft.aufirst=L&rft.au=Li%2C+JX&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4532615&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-GainetdinovHoenerBerry2018-35"><span class="mw-cite-backlink">^ <a href="#cite_ref-GainetdinovHoenerBerry2018_35-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GainetdinovHoenerBerry2018_35-1"><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="CITEREFGainetdinovHoenerBerry2018" class="citation journal cs1">Gainetdinov RR, Hoener MC, Berry MD (July 2018). <a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fpr.117.015305">"Trace Amines and Their Receptors"</a>. <i>Pharmacol Rev</i>. <b>70</b> (3): <span class="nowrap">549–</span>620. <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/10.1124%2Fpr.117.015305">10.1124/pr.117.015305</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/29941461">29941461</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacol+Rev&rft.atitle=Trace+Amines+and+Their+Receptors&rft.volume=70&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E549-%3C%2Fspan%3E620&rft.date=2018-07&rft_id=info%3Adoi%2F10.1124%2Fpr.117.015305&rft_id=info%3Apmid%2F29941461&rft.aulast=Gainetdinov&rft.aufirst=RR&rft.au=Hoener%2C+MC&rft.au=Berry%2C+MD&rft_id=https%3A%2F%2Fdoi.org%2F10.1124%252Fpr.117.015305&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-ZhangMantasAlvarsson2018-36"><span class="mw-cite-backlink">^ <a href="#cite_ref-ZhangMantasAlvarsson2018_36-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ZhangMantasAlvarsson2018_36-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ZhangMantasAlvarsson2018_36-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZhangMantasAlvarssonYoshitake2018" class="citation journal cs1">Zhang X, Mantas I, Alvarsson A, Yoshitake T, Shariatgorji M, Pereira M, et al. (2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5837966">"Striatal Tyrosine Hydroxylase Is Stimulated via TAAR1 by 3-Iodothyronamine, But Not by Tyramine or β-Phenylethylamine"</a>. <i>Front Pharmacol</i>. <b>9</b>: 166. <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/10.3389%2Ffphar.2018.00166">10.3389/fphar.2018.00166</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5837966">5837966</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/29545750">29545750</a>. <q>Di Cara et al. (2011) showed that TAAR1 decreases the amplitude of Methylenedioxymethamphetamine (MDMA) induced dopamine release both in ventral and dorsal striatum. In the same study it was observed that the TAAR1 agonist, o-phenyl-3-iodotyramine (o-PIT) blunted the para-chloroamphetamine (PCA) induced dopamine release in both structures (Di Cara et al., 2011).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Front+Pharmacol&rft.atitle=Striatal+Tyrosine+Hydroxylase+Is+Stimulated+via+TAAR1+by+3-Iodothyronamine%2C+But+Not+by+Tyramine+or+%CE%B2-Phenylethylamine&rft.volume=9&rft.pages=166&rft.date=2018&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5837966%23id-name%3DPMC&rft_id=info%3Apmid%2F29545750&rft_id=info%3Adoi%2F10.3389%2Ffphar.2018.00166&rft.aulast=Zhang&rft.aufirst=X&rft.au=Mantas%2C+I&rft.au=Alvarsson%2C+A&rft.au=Yoshitake%2C+T&rft.au=Shariatgorji%2C+M&rft.au=Pereira%2C+M&rft.au=Nilsson%2C+A&rft.au=Kehr%2C+J&rft.au=Andr%C3%A9n%2C+PE&rft.au=Millan%2C+MJ&rft.au=Chergui%2C+K&rft.au=Svenningsson%2C+P&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5837966&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-SimmlerBuchyChaboz2016-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-SimmlerBuchyChaboz2016_37-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSimmlerBuchyChabozHoener2016" class="citation journal cs1">Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". <i>J Pharmacol Exp Ther</i>. <b>357</b> (1): <span class="nowrap">134–</span>144. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fjpet.115.229765">10.1124/jpet.115.229765</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/26791601">26791601</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Pharmacol+Exp+Ther&rft.atitle=In+Vitro+Characterization+of+Psychoactive+Substances+at+Rat%2C+Mouse%2C+and+Human+Trace+Amine-Associated+Receptor+1&rft.volume=357&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E134-%3C%2Fspan%3E144&rft.date=2016-04&rft_id=info%3Adoi%2F10.1124%2Fjpet.115.229765&rft_id=info%3Apmid%2F26791601&rft.aulast=Simmler&rft.aufirst=LD&rft.au=Buchy%2C+D&rft.au=Chaboz%2C+S&rft.au=Hoener%2C+MC&rft.au=Liechti%2C+ME&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-LewinMillerGilmour2011-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-LewinMillerGilmour2011_38-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLewinMillerGilmour2011" class="citation journal cs1">Lewin AH, Miller GM, Gilmour B (December 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3236098">"Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class"</a>. <i>Bioorganic & Medicinal Chemistry</i>. <b>19</b> (23): <span class="nowrap">7044–</span>7048. <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.bmc.2011.10.007">10.1016/j.bmc.2011.10.007</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/PMC3236098">3236098</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/22037049">22037049</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioorganic+%26+Medicinal+Chemistry&rft.atitle=Trace+amine-associated+receptor+1+is+a+stereoselective+binding+site+for+compounds+in+the+amphetamine+class&rft.volume=19&rft.issue=23&rft.pages=%3Cspan+class%3D%22nowrap%22%3E7044-%3C%2Fspan%3E7048&rft.date=2011-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3236098%23id-name%3DPMC&rft_id=info%3Apmid%2F22037049&rft_id=info%3Adoi%2F10.1016%2Fj.bmc.2011.10.007&rft.aulast=Lewin&rft.aufirst=AH&rft.au=Miller%2C+GM&rft.au=Gilmour%2C+B&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3236098&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-DunlapAndrewsOlson2018-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-DunlapAndrewsOlson2018_39-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDunlapAndrewsOlson2018" class="citation journal cs1">Dunlap LE, Andrews AM, Olson DE (October 2018). <a rel="nofollow" class="external text" href="https://shaunlacob.com/wp-content/uploads/2020/12/DC-MDMA.pdf">"Dark Classics in Chemical Neuroscience: 3,4-Methylenedioxymethamphetamine"</a> <span class="cs1-format">(PDF)</span>. <i>ACS Chem Neurosci</i>. <b>9</b> (10): <span class="nowrap">2408–</span>2427. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facschemneuro.8b00155">10.1021/acschemneuro.8b00155</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/PMC6197894">6197894</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/30001118">30001118</a>. <q>[...] it is unclear if TAAR1 plays any role in the effects of MDMA in humans, as MDMA does not activate human TAAR1 in cellular assays like it does mouse and rat TAAR1.84</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=ACS+Chem+Neurosci&rft.atitle=Dark+Classics+in+Chemical+Neuroscience%3A+3%2C4-Methylenedioxymethamphetamine&rft.volume=9&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2408-%3C%2Fspan%3E2427&rft.date=2018-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6197894%23id-name%3DPMC&rft_id=info%3Apmid%2F30001118&rft_id=info%3Adoi%2F10.1021%2Facschemneuro.8b00155&rft.aulast=Dunlap&rft.aufirst=LE&rft.au=Andrews%2C+AM&rft.au=Olson%2C+DE&rft_id=https%3A%2F%2Fshaunlacob.com%2Fwp-content%2Fuploads%2F2020%2F12%2FDC-MDMA.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-HollandBuckWeissman1963-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-HollandBuckWeissman1963_40-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHollandBuckWeissman1963" class="citation journal cs1">Holland GF, Buck CJ, Weissman A (September 1963). "Anorexigenic Agents: Aromatic Substituted 1-Phenyl-2-propylamines". <i>J Med Chem</i>. <b>6</b> (5): <span class="nowrap">519–</span>524. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjm00341a011">10.1021/jm00341a011</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/14173573">14173573</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Med+Chem&rft.atitle=Anorexigenic+Agents%3A+Aromatic+Substituted+1-Phenyl-2-propylamines&rft.volume=6&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E519-%3C%2Fspan%3E524&rft.date=1963-09&rft_id=info%3Adoi%2F10.1021%2Fjm00341a011&rft_id=info%3Apmid%2F14173573&rft.aulast=Holland&rft.aufirst=GF&rft.au=Buck%2C+CJ&rft.au=Weissman%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-FullerHinesMills1965-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-FullerHinesMills1965_41-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFullerHinesMills1965" class="citation journal cs1">Fuller RW, Hines CW, Mills J (April 1965). "Lowering of Brain Serotonin Level By Chloroamphetamines". <i>Biochem Pharmacol</i>. <b>14</b> (4): <span class="nowrap">483–</span>488. <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%2F0006-2952%2865%2990221-2">10.1016/0006-2952(65)90221-2</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/14322972">14322972</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochem+Pharmacol&rft.atitle=Lowering+of+Brain+Serotonin+Level+By+Chloroamphetamines&rft.volume=14&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E483-%3C%2Fspan%3E488&rft.date=1965-04&rft_id=info%3Adoi%2F10.1016%2F0006-2952%2865%2990221-2&rft_id=info%3Apmid%2F14322972&rft.aulast=Fuller&rft.aufirst=RW&rft.au=Hines%2C+CW&rft.au=Mills%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> <li id="cite_note-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-42">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite 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> (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%3APara-Chloroamphetamine" class="Z3988"></span></span> </li> </ol></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 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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 href="/wiki/5-MAPB" title="5-MAPB">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 class="mw-selflink selflink">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="Monoamine_releasing_agents1712" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoamine_releasing_agents" title="Template talk:Monoamine releasing agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoamine_releasing_agents" title="Special:EditPage/Template:Monoamine releasing agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoamine_releasing_agents1712" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">Monoamine releasing agents</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Dopamine_releasing_agents" class="mw-redirect" title="Dopamine releasing agents"><abbr title="Dopamine releasing agents">DRAs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dopamine releasing agents</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Morpholines:</i> <a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Oxazolines:</i> <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-MAR</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Cyclazodone" title="Cyclazodone">Cyclazodone</a></li> <li><a href="/wiki/Fenozolone" title="Fenozolone">Fenozolone</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li> <li><a href="/wiki/Pemoline" title="Pemoline">Pemoline</a></li> <li><a href="/wiki/Thozalinone" title="Thozalinone">Thozalinone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Phenethylamines:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">2-OH-PEA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Me-PEA</a></li> <li><a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" class="mw-redirect" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Iofetamine_(123I)" title="Iofetamine (123I)">Iofetamine (123I)</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></li></ul></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-methylbutanamine" class="mw-redirect" title="1,3-Benzodioxolyl-N-methylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine"><i>p</i>BA</a></li> <li><a class="mw-selflink selflink"><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" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></li></ul></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine"><i>p</i>BA</a></li> <li><a class="mw-selflink selflink"><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 class="mw-selflink selflink">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="Monoamine_metabolism_modulators806" 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_metabolism_modulators" title="Template:Monoamine metabolism modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoamine_metabolism_modulators" title="Template talk:Monoamine metabolism modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoamine_metabolism_modulators" title="Special:EditPage/Template:Monoamine metabolism modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoamine_metabolism_modulators806" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">Monoamine</a> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> <a href="/wiki/Enzyme_modulator" title="Enzyme modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Non-specific</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase"><abbr title="Aromatic L-amino acid decarboxylase">AAAD</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 Aromatic L-amino acid decarboxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/L-DOPA" title="L-DOPA"><small>L</small>-DOPA (levodopa)</a>→<a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/5-HTP" class="mw-redirect" title="5-HTP">5-HTP</a>→<a href="/wiki/Serotonin" title="Serotonin">Serotonin</a></li> <li><a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><small>L</small>-Histidine</a>→<a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a>→<a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/L-Tyrosine" class="mw-redirect" title="L-Tyrosine"><small>L</small>-Tyrosine</a>→<a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a>→<a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/Benserazide" title="Benserazide">Benserazide</a></li> <li><a href="/wiki/Carbidopa" title="Carbidopa">Carbidopa</a></li> <li><a href="/wiki/Alpha-Difluoromethyl-DOPA" class="mw-redirect" title="Alpha-Difluoromethyl-DOPA">DFMD</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase"><abbr title="Monoamine oxidase">MAO</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 Monoamine oxidase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products (with <a href="/wiki/Aldehyde_dehydrogenase" title="Aldehyde dehydrogenase"><abbr title="Aldehyde dehydrogenase">ALDH</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 Aldehyde dehydrogenase</span>/<a href="/wiki/Aldehyde_reductase" class="mw-redirect" title="Aldehyde reductase"><abbr title="Aldehyde reductase">ALR</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 ALR</span>):</b> <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a>→<a href="/wiki/3,4-Dihydroxymandelic_acid" title="3,4-Dihydroxymandelic acid">DHMA</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a>→<a href="/wiki/3-Methoxy-4-hydroxyphenylglycol" title="3-Methoxy-4-hydroxyphenylglycol">MHPG</a>/<a href="/wiki/Vanillylmandelic_acid" title="Vanillylmandelic acid">VMA</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a>→<a href="/wiki/3,4-Dihydroxymandelic_acid" title="3,4-Dihydroxymandelic acid">DHMA</a></li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a>→<a href="/wiki/3-Methoxy-4-hydroxyphenylglycol" title="3-Methoxy-4-hydroxyphenylglycol">MHPG</a>/<a href="/wiki/Vanillylmandelic_acid" title="Vanillylmandelic acid">VMA</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a>→<a href="/wiki/3,4-Dihydroxyphenylacetic_acid" title="3,4-Dihydroxyphenylacetic acid">DOPAC</a></li> <li><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a>→<a href="/wiki/Homovanillic_acid" title="Homovanillic acid">HVA</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a>→<a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li></ul> <ul><li><b>Inhibitors:</b> <i>Non-selective:</i> <a href="/wiki/Benmoxin" title="Benmoxin">Benmoxin</a></li> <li><a href="/wiki/Caroxazone" title="Caroxazone">Caroxazone</a></li> <li><a href="/wiki/Echinopsidine" title="Echinopsidine">Echinopsidine</a></li> <li><a href="/wiki/Furazolidone" title="Furazolidone">Furazolidone</a></li> <li><a href="/wiki/Guineesine" title="Guineesine">Guineesine</a></li> <li><a href="/wiki/Hydralazine" title="Hydralazine">Hydralazine</a></li> <li><a href="/wiki/Indantadol" title="Indantadol">Indantadol</a></li> <li><a href="/wiki/Iproclozide" title="Iproclozide">Iproclozide</a></li> <li><a href="/wiki/Iproniazid" title="Iproniazid">Iproniazid</a></li> <li><a href="/wiki/Isocarboxazid" title="Isocarboxazid">Isocarboxazid</a></li> <li><a href="/wiki/Isoniazid" title="Isoniazid">Isoniazid</a></li> <li><a href="/wiki/Linezolid" title="Linezolid">Linezolid</a></li> <li><a href="/wiki/Mebanazine" title="Mebanazine">Mebanazine</a></li> <li><a href="/wiki/Metfendrazine" title="Metfendrazine">Metfendrazine</a></li> <li><a href="/wiki/Nialamide" title="Nialamide">Nialamide</a></li> <li><a href="/wiki/Octamoxin" title="Octamoxin">Octamoxin</a></li> <li><a href="/wiki/Paraxazone" title="Paraxazone">Paraxazone</a></li> <li><a href="/wiki/Phenelzine" title="Phenelzine">Phenelzine</a></li> <li><a href="/wiki/Pheniprazine" title="Pheniprazine">Pheniprazine</a></li> <li><a href="/wiki/Phenoxypropazine" title="Phenoxypropazine">Phenoxypropazine</a></li> <li><a href="/wiki/Pivhydrazine" title="Pivhydrazine">Pivhydrazine</a></li> <li><a href="/wiki/Procarbazine" title="Procarbazine">Procarbazine</a></li> <li><a href="/wiki/Safrazine" title="Safrazine">Safrazine</a></li> <li><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</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><b>Inhibitors:</b> <i>MAO-A-selective:</i> <a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/Bazinaprine" title="Bazinaprine">Bazinaprine</a></li> <li><a href="/wiki/Befloxatone" title="Befloxatone">Befloxatone</a></li> <li><a href="/wiki/Brofaromine" title="Brofaromine">Brofaromine</a></li> <li><a href="/wiki/Cimoxatone" title="Cimoxatone">Cimoxatone</a></li> <li><a href="/wiki/Clorgiline" title="Clorgiline">Clorgiline</a></li> <li><a href="/wiki/CX157" title="CX157">CX157 (Tyrima)</a></li> <li><a href="/wiki/Eprobemide" title="Eprobemide">Eprobemide</a></li> <li><a href="/wiki/Esuprone" title="Esuprone">Esuprone</a></li> <li><a href="/wiki/Harmala_alkaloid" title="Harmala alkaloid">Harmala alkaloids</a> (e.g., <a href="/wiki/Harmine" title="Harmine">harmine</a>, <a href="/wiki/Harmaline" title="Harmaline">harmaline</a>, <a href="/wiki/Harmane" title="Harmane">harman</a>, <a href="/wiki/Norharman" class="mw-redirect" title="Norharman">norharman</a>, <a href="/wiki/Tetrahydroharmine" title="Tetrahydroharmine">tetrahydroharmine</a>)</li> <li><a href="/wiki/Methylene_blue" title="Methylene blue">Methylene blue</a></li> <li><a href="/wiki/Metralindole" title="Metralindole">Metralindole</a></li> <li><a href="/wiki/Minaprine" title="Minaprine">Minaprine</a></li> <li><a href="/wiki/Moclobemide" title="Moclobemide">Moclobemide</a></li> <li><a href="/wiki/Pirlindole" title="Pirlindole">Pirlindole</a></li> <li><a href="/wiki/Sercloremine" title="Sercloremine">Sercloremine</a></li> <li><a href="/wiki/Tetrindole" title="Tetrindole">Tetrindole</a></li> <li><a href="/wiki/Toloxatone" title="Toloxatone">Toloxatone</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><b>Inhibitors:</b> <i>MAO-B selective:</i> <a href="/w/index.php?title=Adarigiline&action=edit&redlink=1" class="new" title="Adarigiline (page does not exist)">Adarigiline</a></li> <li><a href="/wiki/Almoxatone" title="Almoxatone">Almoxatone</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl"><small>D</small>-Deprenyl</a></li> <li><a href="/wiki/Desmethylselegiline" title="Desmethylselegiline">Desmethylselegiline</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Lazabemide" title="Lazabemide">Lazabemide</a></li> <li><a href="/wiki/Milacemide" title="Milacemide">Milacemide</a></li> <li><a href="/wiki/Mofegiline" title="Mofegiline">Mofegiline</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/Pargyline" title="Pargyline">Pargyline</a><sup>‡</sup></li> <li><a href="/wiki/Rasagiline" title="Rasagiline">Rasagiline</a></li> <li><a href="/wiki/Safinamide" title="Safinamide">Safinamide</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline (<small>L</small>-Deprenyl)</a></li> <li><a href="/w/index.php?title=Sembragiline&action=edit&redlink=1" class="new" title="Sembragiline (page does not exist)">Sembragiline</a></li> <li><a href="/w/index.php?title=Tisolagiline&action=edit&redlink=1" class="new" title="Tisolagiline (page does not exist)">Tisolagiline</a></li> <li><a href="/wiki/Vafidemstat" title="Vafidemstat">Vafidemstat</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a><br /><small>(<a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a>,<br /><a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Phenylalanine_hydroxylase" title="Phenylalanine hydroxylase"><abbr title="Phenylalanine hydroxylase">PAH</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 Phenylalanine hydroxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a>→<a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/3,4-Dihydroxystyrene" title="3,4-Dihydroxystyrene">3,4-Dihydroxystyrene</a></li> <li><a href="/wiki/%CE%91-Methylphenylalanine" title="Α-Methylphenylalanine">α-Methylphenylalanine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Tyrosine_hydroxylase" title="Tyrosine hydroxylase"><abbr title="Tyrosine hydroxylase">TH</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 Tyrosine hydroxylase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a>→<a href="/wiki/L-DOPA" title="L-DOPA"><small>L</small>-DOPA (levodopa)</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Iodotyrosine" title="3-Iodotyrosine">3-Iodotyrosine</a></li> <li><a href="/wiki/%CE%91-Methyl-5-hydroxytryptophan" title="Α-Methyl-5-hydroxytryptophan">α-Methyl-5-hydroxytryptophan (α-Me-5-HTP)</a></li> <li><a href="/wiki/%CE%91-Methylphenylalanine" title="Α-Methylphenylalanine">α-Methylphenylalanine</a></li> <li><a href="/wiki/Aquayamycin" title="Aquayamycin">Aquayamycin</a></li> <li><a href="/wiki/Bulbocapnine" title="Bulbocapnine">Bulbocapnine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa (α-methyl-<small>L</small>-DOPA)</a></li> <li><a href="/wiki/Metirosine" class="mw-redirect" title="Metirosine">Metirosine (α-methyl-<i>p</i>-tyrosine)</a></li> <li><a href="/wiki/Oudenone" title="Oudenone">Oudenone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase"><abbr title="Dopamine beta-hydroxylase">DBH</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 beta-hydroxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Dopamine" title="Dopamine">Dopamine</a>→<a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (Noradrenaline)</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/Bupicomide" title="Bupicomide">Bupicomide</a></li> <li><a href="/wiki/Disulfiram" title="Disulfiram">Disulfiram</a></li> <li><a href="/wiki/Dopastin" title="Dopastin">Dopastin</a></li> <li><a href="/wiki/Etamicastat" title="Etamicastat">Etamicastat</a></li> <li><a href="/wiki/Fusaric_acid" title="Fusaric acid">Fusaric acid</a></li> <li><a href="/wiki/Nepicastat" title="Nepicastat">Nepicastat</a></li> <li><a href="/wiki/Phenopicolinic_acid" title="Phenopicolinic acid">Phenopicolinic acid</a></li> <li><a href="/wiki/Tropolone" title="Tropolone">Tropolone</a></li> <li><a href="/wiki/Zamicastat" title="Zamicastat">Zamicastat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase"><abbr title="Phenylethanolamine N-methyltransferase">PNMT</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 Phenylethanolamine N-methyltransferase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a>→<a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/w/index.php?title=CGS-19281A&action=edit&redlink=1" class="new" title="CGS-19281A (page does not exist)">CGS-19281A</a></li> <li><a href="/w/index.php?title=SKF-64139&action=edit&redlink=1" class="new" title="SKF-64139 (page does not exist)">SKF-64139</a></li> <li><a href="/w/index.php?title=SKF-7698&action=edit&redlink=1" class="new" title="SKF-7698 (page does not exist)">SKF-7698</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Catechol-O-methyl_transferase" class="mw-redirect" title="Catechol-O-methyl transferase"><abbr title="Catechol-O-methyl transferase">COMT</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 Catechol-O-methyl transferase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Dopamine" title="Dopamine">Dopamine</a>→<a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></li> <li><a href="/wiki/DOPAC" class="mw-redirect" title="DOPAC">DOPAC</a>→<a href="/wiki/Homovanillic_acid" title="Homovanillic acid">Homovanillic acid</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a>→<a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a>→<a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Dihydroxyphenylethylene_glycol" title="Dihydroxyphenylethylene glycol">DOPEG</a>→<a href="/wiki/Methoxyhydroxyphenylglycol" class="mw-redirect" title="Methoxyhydroxyphenylglycol">MOPEG</a></li> <li><a href="/wiki/3,4-Dihydroxymandelic_acid" title="3,4-Dihydroxymandelic acid">DOMA</a>→<a href="/wiki/Vanillylmandelic_acid" title="Vanillylmandelic acid">VMA</a></li> <li><a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a>→<a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a>→<a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a>→<a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a>→<a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/Entacapone" title="Entacapone">Entacapone</a></li> <li><a href="/wiki/Nebicapone" title="Nebicapone">Nebicapone</a></li> <li><a href="/wiki/Neluxicapone" title="Neluxicapone">Neluxicapone</a></li> <li><a href="/wiki/Nitecapone" title="Nitecapone">Nitecapone</a></li> <li><a href="/wiki/Opicapone" title="Opicapone">Opicapone</a></li> <li><a href="/wiki/Quinalizarin" title="Quinalizarin">Quinalizarin</a></li> <li><a href="/wiki/Tolcapone" title="Tolcapone">Tolcapone</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/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a><br /><small>(<a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, <a href="/wiki/Melatonin" title="Melatonin">melatonin</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Tryptophan_hydroxylase" title="Tryptophan hydroxylase"><abbr title="Tryptophan hydroxylase">TPH</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 Tryptophan hydroxylase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a>→<a href="/wiki/5-HTP" class="mw-redirect" title="5-HTP">5-HTP</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/AGN-2979" title="AGN-2979">AGN-2979</a></li> <li><a href="/wiki/Fenclonine" title="Fenclonine">Fenclonine (PCPA)</a></li> <li><a href="/wiki/Telotristat_ethyl" title="Telotristat ethyl">Telotristat ethyl</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Serotonin_N-acetyl_transferase" class="mw-redirect" title="Serotonin N-acetyl transferase"><abbr title="Serotonin N-acetyl transferase">AANAT</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 N-acetyl transferase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Serotonin" title="Serotonin">Serotonin</a>→<a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">N-Acetylserotonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Acetylserotonin_O-methyltransferase" title="Acetylserotonin O-methyltransferase"><abbr title="Acetylserotonin O-methyltransferase">ASMT</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 Acetylserotonin O-methyltransferase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">N-Acetylserotonin</a>→<a href="/wiki/Melatonin" title="Melatonin">Melatonin</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/Histamine" title="Histamine">Histamine</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Histidine_decarboxylase" title="Histidine decarboxylase"><abbr title="Histidine decarboxylase">HDC</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 Histidine decarboxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><small>L</small>-Histidine</a>→<a href="/wiki/Histamine" title="Histamine">Histamine</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/(%2B)-Catechin" class="mw-redirect" title="(+)-Catechin">Catechin</a></li> <li><a href="/wiki/Alpha-Fluoromethylhistidine" class="mw-redirect" title="Alpha-Fluoromethylhistidine">Alpha-Fluoromethylhistidine</a></li> <li><a href="/wiki/Histidine_methyl_ester" title="Histidine methyl ester">Histidine methyl ester</a></li> <li><a href="/wiki/Meciadanol" title="Meciadanol">Meciadanol</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/wiki/Tritoqualine" title="Tritoqualine">Tritoqualine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Histamine_N-methyltransferase" title="Histamine N-methyltransferase"><abbr title="Histamine N-methyltransferase">HNMT</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 Histamine N-methyltransferase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Histamine" title="Histamine">Histamine</a>→<a href="/w/index.php?title=N-Methylhistamine&action=edit&redlink=1" class="new" title="N-Methylhistamine (page does not exist)">N-Methylhistamine</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/Amodiaquine" title="Amodiaquine">Amodiaquine</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li> <li><a href="/wiki/Harmaline" title="Harmaline">Harmaline</a></li> <li><a href="/w/index.php?title=Metoprine&action=edit&redlink=1" class="new" title="Metoprine (page does not exist)">Metoprine</a></li> <li><a href="/wiki/Quinacrine" class="mw-redirect" title="Quinacrine">Quinacrine</a></li> <li><a href="/wiki/SKF-91488" title="SKF-91488">SKF-91488</a></li> <li><a href="/wiki/Tacrine" title="Tacrine">Tacrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Diamine_oxidase" title="Diamine oxidase"><abbr title="Diamine oxidase">DAO</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 Diamine oxidase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Histamine" title="Histamine">Histamine</a>→<a href="/w/index.php?title=Imidazole_acetic_acid&action=edit&redlink=1" class="new" title="Imidazole acetic acid (page does not exist)">Imidazole acetic acid</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/Pimagedine" title="Pimagedine">Pimagedine (aminoguanidine)</a></li></ul> </div></td></tr></tbody></table><div></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_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="Trace_amine-associated_receptor_modulators1416" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:TAAR_modulators" title="Template:TAAR modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:TAAR_modulators" title="Template talk:TAAR modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:TAAR_modulators" title="Special:EditPage/Template:TAAR modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Trace_amine-associated_receptor_modulators1416" style="font-size:114%;margin:0 4em"><a href="/wiki/Trace_amine-associated_receptor" title="Trace amine-associated receptor">Trace amine-associated receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Trace_amine-associated_receptor_1" class="mw-redirect" title="Trace amine-associated receptor 1"><abbr title="Trace amine-associated receptor 1">TAAR1</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Trace amine-associated receptor 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Agonist" title="Agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Trace_amine" title="Trace amine">Endogenous</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">Monoamine neurotransmitters</a> <ul><li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a></li></ul></li> <li><a href="/wiki/Trace_amine" title="Trace amine">Trace amines</a> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li> <li><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methyltyramine" title="N-Methyltyramine"><i>N</i>-Methyltyramine</a></li> <li><a href="/wiki/Meta-Octopamine" class="mw-redirect" title="Meta-Octopamine"><i>m</i>-Octopamine</a></li> <li><a href="/wiki/Para-Octopamine" class="mw-redirect" title="Para-Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">β-Phenethylamine</a></li> <li><a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Para-Tyramine" class="mw-redirect" title="Para-Tyramine"><i>p</i>-Tyramine</a></li></ul></li> <li>Others <ul><li><a href="/wiki/Cyclohexylamine" title="Cyclohexylamine">Cyclohexylamine</a></li> <li><a href="/w/index.php?title=Isoamylamine&action=edit&redlink=1" class="new" title="Isoamylamine (page does not exist)">Isoamylamine</a></li> <li><a href="/wiki/Trimethylamine" title="Trimethylamine">Trimethylamine</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Exogenous" class="mw-redirect" title="Exogenous">Exogenous</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B" title="2C-B">2C-B</a></li> <li><a href="/wiki/2C-B-Fly" class="mw-redirect" title="2C-B-Fly">2C-B-Fly</a></li> <li><a href="/wiki/2C-E" title="2C-E">2C-E</a></li> <li><a href="/wiki/2C-H" title="2C-H">2C-H</a></li> <li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li> <li><a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a></li> <li><a href="/wiki/A-77636" title="A-77636">A-77636</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-Aminoindane</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/w/index.php?title=AP163&action=edit&redlink=1" class="new" title="AP163 (page does not exist)">AP163</a></li> <li><a href="/wiki/Apomorphine" title="Apomorphine">Apomorphine</a></li> <li><a href="/wiki/Asenapine" title="Asenapine">Asenapine</a></li> <li><a href="/wiki/Bromocriptine" title="Bromocriptine">Bromocriptine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Clonidine" title="Clonidine">Clonidine</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">Dihydroergotamine</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">Dimethyltryptamine</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/N,N-Dimethylphenethylamine" title="N,N-Dimethylphenethylamine"><i>N</i>,<i>N</i>-Dimethylphenethylamine</a></li> <li><a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">Ergometrine</a></li> <li><a href="/wiki/Fenoldopam" title="Fenoldopam">Fenoldopam</a></li> <li><a href="/wiki/Fenoterol" title="Fenoterol">Fenoterol</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-Fluoroamphetamine</a></li> <li><a href="/wiki/Guanabenz" title="Guanabenz">Guanabenz</a></li> <li><a href="/wiki/Guanfacine" title="Guanfacine">Guanfacine</a></li> <li><a href="/wiki/Halostachine" title="Halostachine">Halostachine</a></li> <li><a href="/wiki/Higenamine" title="Higenamine">Higenamine</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine (norpholedrine)</a></li> <li><a href="/wiki/Idazoxan" title="Idazoxan">Idazoxan</a></li> <li><a href="/wiki/5-Iodo-2-aminoindane" class="mw-redirect" title="5-Iodo-2-aminoindane">5-Iodo-2-aminoindane</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isopropyloctopamine" class="mw-redirect" title="Isopropyloctopamine">Isopropyloctopamine</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/LK00764" title="LK00764">LK00764</a></li> <li><a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">LSD</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyaminoindane" class="mw-redirect" title="Methylenedioxyaminoindane">MDAI</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metergoline" title="Metergoline">Metergoline</a></li> <li><a href="/wiki/N-Methyl-2-AI" class="mw-redirect" title="N-Methyl-2-AI"><i>N</i>-Methyl-2-AI</a></li> <li><a href="/wiki/2-Methylphenethylamine" title="2-Methylphenethylamine">2-Methylphenethylamine</a></li> <li><a href="/wiki/3-Methylphenethylamine" title="3-Methylphenethylamine">3-Methylphenethylamine</a></li> <li><a href="/wiki/4-Methylphenethylamine" title="4-Methylphenethylamine">4-Methylphenethylamine</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/3-Methoxyamphetamine" title="3-Methoxyamphetamine">MMA</a></li> <li><a href="/wiki/MPTP" title="MPTP">MPTP</a></li> <li><a href="/wiki/Naphazoline" title="Naphazoline">Naphazoline</a></li> <li><a href="/wiki/Nomifensine" title="Nomifensine">Nomifensine</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/Phentolamine" title="Phentolamine">Phentolamine</a></li> <li><a href="/wiki/O-Phenyl-3-iodotyramine" title="O-Phenyl-3-iodotyramine"><i>o</i>-PIT</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">Psilocin</a></li> <li><a href="/wiki/Ralmitaront" title="Ralmitaront">Ralmitaront (RG-7906, RO6889450)</a></li> <li><a href="/wiki/RG-7351" title="RG-7351">RG-7351</a></li> <li><a href="/wiki/RG-7410" title="RG-7410">RG-7410</a></li> <li><a href="/wiki/RO5073012" title="RO5073012">RO5073012</a></li> <li><a href="/wiki/RO5166017" title="RO5166017">RO5166017</a></li> <li><a href="/wiki/RO5203648" title="RO5203648">RO5203648</a></li> <li><a href="/wiki/RO5256390" title="RO5256390">RO5256390</a></li> <li><a href="/wiki/RO5263397" title="RO5263397">RO5263397</a></li> <li><a href="/w/index.php?title=S18616&action=edit&redlink=1" class="new" title="S18616 (page does not exist)">S18616</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline (<small>L</small>-deprenyl)</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Tolazoline" title="Tolazoline">Tolazoline</a></li> <li><a href="/wiki/Ulotaront" title="Ulotaront">Ulotaront (SEP-363856)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Compound_22_(TAAR1_antagonist)" title="Compound 22 (TAAR1 antagonist)">Compound 22</a></li> <li><a href="/wiki/EPPTB" title="EPPTB">EPPTB (RO-5212773)</a></li> <li><a href="/wiki/RTI-7470-44" title="RTI-7470-44">RTI-7470-44</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Inverse_agonist" title="Inverse agonist">Inverse agonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/EPPTB" title="EPPTB">EPPTB (RO-5212773)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Trace_amine-associated_receptor_5" class="mw-redirect" title="Trace amine-associated receptor 5"><abbr title="Trace amine-associated receptor 5">TAAR5</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Trace amine-associated receptor 5</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Agonists32" scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Agonist" title="Agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N,N-Dimethylethylamine" title="N,N-Dimethylethylamine"><i>N</i>,<i>N</i>-Dimethylethylamine</a></li> <li><a href="/wiki/Trimethylamine" title="Trimethylamine">Trimethylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Inverse_agonist" title="Inverse agonist">Inverse agonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><small><i><b>Notes:</b></i> (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the <a href="/wiki/Trace_amine#List_of_trace_amines" title="Trace amine">List of trace amines</a>, <a href="/wiki/Trace_amine-associated_receptor" title="Trace amine-associated receptor">TAAR</a>, and <a href="/wiki/TAAR1" title="TAAR1">TAAR1</a> pages. <i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></small></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Phenethylamines352" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Phenethylamines" title="Template:Phenethylamines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenethylamines" title="Template talk:Phenethylamines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenethylamines" title="Special:EditPage/Template:Phenethylamines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Phenethylamines352" style="font-size:114%;margin:0 4em"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Psychedelics:</i> <a href="/wiki/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a></li> <li><a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a></li> <li><a href="/wiki/25D-NBOMe" title="25D-NBOMe">25D-NBOMe</a></li> <li><a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a></li> <li><a href="/wiki/25N-NBOMe" title="25N-NBOMe">25N-NBOMe</a></li> <li><a href="/wiki/2C-B" title="2C-B">2C-B</a></li> <li><a href="/w/index.php?title=2C-B-AN&action=edit&redlink=1" class="new" title="2C-B-AN (page does not exist)">2C-B-AN</a></li> <li><a href="/w/index.php?title=2C-Bn&action=edit&redlink=1" class="new" title="2C-Bn (page does not exist)">2C-Bn</a></li> <li><a href="/w/index.php?title=2C-Bu&action=edit&redlink=1" class="new" title="2C-Bu (page does not exist)">2C-Bu</a></li> <li><a href="/wiki/2C-C" title="2C-C">2C-C</a></li> <li><a href="/w/index.php?title=2C-CN&action=edit&redlink=1" class="new" title="2C-CN (page does not exist)">2C-CN</a></li> <li><a href="/wiki/2C-CP" title="2C-CP">2C-CP</a></li> <li><a href="/wiki/2C-D" title="2C-D">2C-D</a></li> <li><a href="/wiki/2C-E" title="2C-E">2C-E</a></li> <li><a href="/wiki/2C-EF" title="2C-EF">2C-EF</a></li> <li><a href="/wiki/2C-F" title="2C-F">2C-F</a></li> <li><a href="/wiki/2C-G" title="2C-G">2C-G</a></li> <li><a href="/wiki/2C-G-1" class="mw-redirect" title="2C-G-1">2C-G-1</a></li> <li><a href="/wiki/2C-G-2" class="mw-redirect" title="2C-G-2">2C-G-2</a></li> <li><a href="/wiki/2C-G-3" class="mw-redirect" title="2C-G-3">2C-G-3</a></li> <li><a href="/wiki/2C-G-4" class="mw-redirect" title="2C-G-4">2C-G-4</a></li> <li><a href="/wiki/2C-G-5" class="mw-redirect" title="2C-G-5">2C-G-5</a></li> <li><a href="/wiki/2C-G-6" class="mw-redirect" title="2C-G-6">2C-G-6</a></li> <li><a href="/wiki/2C-G-N" class="mw-redirect" title="2C-G-N">2C-G-N</a></li> <li><a href="/wiki/2C-H" title="2C-H">2C-H</a></li> <li><a href="/wiki/2C-I" title="2C-I">2C-I</a></li> <li><a href="/wiki/2C-iP" title="2C-iP">2C-iP</a></li> <li><a href="/wiki/2C-N" title="2C-N">2C-N</a></li> <li><a href="/w/index.php?title=2C-NH2&action=edit&redlink=1" class="new" title="2C-NH2 (page does not exist)">2C-NH2</a></li> <li><a href="/wiki/2C-O" class="mw-redirect" title="2C-O">2C-O</a></li> <li><a href="/wiki/2C-O-4" title="2C-O-4">2C-O-4</a></li> <li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li> <li><a href="/w/index.php?title=2C-Ph&action=edit&redlink=1" class="new" title="2C-Ph (page does not exist)">2C-Ph</a></li> <li><a href="/wiki/2C-SE" class="mw-redirect" title="2C-SE">2C-SE</a></li> <li><a href="/wiki/2C-T" title="2C-T">2C-T</a></li> <li><a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a></li> <li><a href="/wiki/2C-T-3" title="2C-T-3">2C-T-3</a></li> <li><a href="/wiki/2C-T-4" title="2C-T-4">2C-T-4</a></li> <li><a href="/w/index.php?title=2C-T-5&action=edit&redlink=1" class="new" title="2C-T-5 (page does not exist)">2C-T-5</a></li> <li><a href="/w/index.php?title=2C-T-6&action=edit&redlink=1" class="new" title="2C-T-6 (page does not exist)">2C-T-6</a></li> <li><a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a></li> <li><a href="/wiki/2C-T-8" title="2C-T-8">2C-T-8</a></li> <li><a href="/wiki/2C-T-9" class="mw-redirect" title="2C-T-9">2C-T-9</a></li> <li><a href="/w/index.php?title=2C-T-10&action=edit&redlink=1" class="new" title="2C-T-10 (page does not exist)">2C-T-10</a></li> <li><a href="/w/index.php?title=2C-T-11&action=edit&redlink=1" class="new" title="2C-T-11 (page does not exist)">2C-T-11</a></li> <li><a href="/w/index.php?title=2C-T-12&action=edit&redlink=1" class="new" title="2C-T-12 (page does not exist)">2C-T-12</a></li> <li><a href="/wiki/2C-T-13" title="2C-T-13">2C-T-13</a></li> <li><a href="/w/index.php?title=2C-T-14&action=edit&redlink=1" class="new" title="2C-T-14 (page does not exist)">2C-T-14</a></li> <li><a href="/wiki/2C-T-15" title="2C-T-15">2C-T-15</a></li> <li><a href="/wiki/2C-T-16" title="2C-T-16">2C-T-16</a></li> <li><a href="/wiki/2C-T-17" title="2C-T-17">2C-T-17</a></li> <li><a href="/w/index.php?title=2C-T-18&action=edit&redlink=1" class="new" title="2C-T-18 (page does not exist)">2C-T-18</a></li> <li><a href="/wiki/2C-T-19" title="2C-T-19">2C-T-19</a></li> <li><a href="/w/index.php?title=2C-T-20&action=edit&redlink=1" class="new" title="2C-T-20 (page does not exist)">2C-T-20</a></li> <li><a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a></li> <li><a href="/w/index.php?title=2C-T-22&action=edit&redlink=1" class="new" title="2C-T-22 (page does not exist)">2C-T-22</a></li> <li><a href="/w/index.php?title=2C-T-22.5&action=edit&redlink=1" class="new" title="2C-T-22.5 (page does not exist)">2C-T-22.5</a></li> <li><a href="/w/index.php?title=2C-T-23&action=edit&redlink=1" class="new" title="2C-T-23 (page does not exist)">2C-T-23</a></li> <li><a href="/w/index.php?title=2C-T-24&action=edit&redlink=1" class="new" title="2C-T-24 (page does not exist)">2C-T-24</a></li> <li><a href="/w/index.php?title=2C-T-25&action=edit&redlink=1" class="new" title="2C-T-25 (page does not exist)">2C-T-25</a></li> <li><a href="/w/index.php?title=2C-T-27&action=edit&redlink=1" class="new" title="2C-T-27 (page does not exist)">2C-T-27</a></li> <li><a href="/wiki/2C-T-28" title="2C-T-28">2C-T-28</a></li> <li><a href="/w/index.php?title=2C-T-30&action=edit&redlink=1" class="new" title="2C-T-30 (page does not exist)">2C-T-30</a></li> <li><a href="/w/index.php?title=2C-T-31&action=edit&redlink=1" class="new" title="2C-T-31 (page does not exist)">2C-T-31</a></li> <li><a href="/w/index.php?title=2C-T-32&action=edit&redlink=1" class="new" title="2C-T-32 (page does not exist)">2C-T-32</a></li> <li><a href="/wiki/2C-T-33" title="2C-T-33">2C-T-33</a></li> <li><a href="/wiki/2C-TFE" title="2C-TFE">2C-TFE</a></li> <li><a href="/wiki/2C-TFM" title="2C-TFM">2C-TFM</a></li> <li><a href="/wiki/2C-YN" title="2C-YN">2C-YN</a></li> <li><a href="/wiki/2C-V" title="2C-V">2C-V</a></li> <li><a href="/wiki/Allylescaline" title="Allylescaline">Allylescaline</a></li> <li><a href="/wiki/DESOXY" title="DESOXY">DESOXY</a></li> <li><a href="/wiki/Escaline" title="Escaline">Escaline</a></li> <li><a href="/wiki/Isoproscaline" title="Isoproscaline">Isoproscaline</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Macromerine" title="Macromerine">Macromerine</a></li> <li><a href="/wiki/3-Methoxy-4-ethoxyphenethylamine" title="3-Methoxy-4-ethoxyphenethylamine">MEPEA</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metaescaline" title="Metaescaline">Metaescaline</a></li> <li><a href="/wiki/Methallylescaline" title="Methallylescaline">Methallylescaline</a></li> <li><a href="/wiki/Proscaline" title="Proscaline">Proscaline</a></li> <li><a href="/wiki/Psi-2C-T-4" class="mw-redirect" title="Psi-2C-T-4">Psi-2C-T-4</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li></ul> <ul><li><i>Stimulants:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">α-Methylphenethylamine</a> (amphetamine)</li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/M-Methylphenethylamine" class="mw-redirect" title="M-Methylphenethylamine"><i>m</i>-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li> <li><a href="/wiki/O-Methylphenethylamine" class="mw-redirect" title="O-Methylphenethylamine"><i>o</i>-Methylphenethylamine</a></li> <li><a href="/wiki/P-Methylphenethylamine" class="mw-redirect" title="P-Methylphenethylamine"><i>p</i>-Methylphenethylamine</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li></ul> <ul><li><i>Entactogens:</i> <a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a><br /><i>Others:</i> <a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/3,4-Dimethoxyphenethylamine" title="3,4-Dimethoxyphenethylamine">DMPEA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Psychedelics:</i> <a href="/wiki/3C-AL" title="3C-AL">3C-AL</a></li> <li><a href="/wiki/3C-BZ" title="3C-BZ">3C-BZ</a></li> <li><a href="/wiki/3C-E" title="3C-E">3C-E</a></li> <li><a href="/wiki/3C-MAL" title="3C-MAL">3C-MAL</a></li> <li><a href="/wiki/3C-P" title="3C-P">3C-P</a></li> <li><a href="/wiki/Aleph_(psychedelic)" title="Aleph (psychedelic)">Aleph</a></li> <li><a href="/wiki/Beatrice_(psychedelic)" title="Beatrice (psychedelic)">Beatrice</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/4-Methyl-2,5-methoxyphenylcyclopropylamine" class="mw-redirect" title="4-Methyl-2,5-methoxyphenylcyclopropylamine">DMCPA</a></li> <li><a href="/wiki/DMMDA" title="DMMDA">DMMDA</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-fluoroethylamphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-fluoroethylamphetamine">DOEF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-nitroamphetamine" title="2,5-Dimethoxy-4-nitroamphetamine">DON</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-propylamphetamine" title="2,5-Dimethoxy-4-propylamphetamine">DOPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-trifluoromethylamphetamine" title="2,5-Dimethoxy-4-trifluoromethylamphetamine">DOTFM</a></li> <li><a href="/wiki/Ganesha_(psychedelic)" title="Ganesha (psychedelic)">Ganesha</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDA-2" title="MMDA-2">MMDA-2</a></li> <li><a href="/wiki/Psi-DOM" class="mw-redirect" title="Psi-DOM">Psi-DOM</a></li> <li><a href="/wiki/Trimethoxyamphetamine" class="mw-redirect" title="Trimethoxyamphetamine">TMA</a></li> <li><a href="/wiki/Tetramethoxyamphetamine" class="mw-redirect" title="Tetramethoxyamphetamine">TeMA</a></li> <li><a href="/wiki/ZDCM-04" title="ZDCM-04">ZDCM-04</a><br /><i>Stimulants:</i> <a href="/wiki/2-Fluoroamphetamine" title="2-Fluoroamphetamine">2-FA</a></li> <li><a href="/wiki/2-Fluoromethamphetamine" title="2-Fluoromethamphetamine">2-FMA</a></li> <li><a href="/wiki/3-Fluoroamphetamine" title="3-Fluoroamphetamine">3-FA</a></li> <li><a href="/wiki/3-Fluoromethamphetamine" title="3-Fluoromethamphetamine">3-FMA</a></li> <li><a href="/wiki/Acridorex" title="Acridorex">Acridorex</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a>, <a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/Benfluorex" title="Benfluorex">Benfluorex</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Fencamfamin" title="Fencamfamin">Fencamfamin</a></li> <li><a href="/wiki/Fencamine" title="Fencamine">Fencamine</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a> (<a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a>)</li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flucetorex" title="Flucetorex">Flucetorex</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Formetorex" title="Formetorex">Formetorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Gepefrine" title="Gepefrine">Gepefrine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Isopropylamphetamine" title="Isopropylamphetamine">Isopropylamphetamine</a></li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> (Dextromethamphetamine, <a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a>)</li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/L-Norpseudoephedrine" title="L-Norpseudoephedrine"><span style="font-size:85%;">L</span>-Norpseudoephedrine</a></li> <li><a href="/wiki/N,alpha-Diethylphenylethylamine" class="mw-redirect" title="N,alpha-Diethylphenylethylamine">N,alpha-Diethylphenylethylamine</a></li> <li><a href="/wiki/Oxifentorex" title="Oxifentorex">Oxifentorex</a></li> <li><a href="/wiki/Oxilofrine" title="Oxilofrine">Oxilofrine</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">PBA</a></li> <li><a class="mw-selflink selflink">PCA</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">PFA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">PFMA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">PIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxy-N-ethylamphetamine" title="Para-Methoxy-N-ethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxy-N-methylamphetamine" class="mw-redirect" title="Para-Methoxy-N-methylamphetamine">PMMA</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Sibutramine" title="Sibutramine">Sibutramine</a></li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a><br /><i>Entactogens:</i> <a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APB" title="5-APB">5-APB</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-EAPB" title="5-EAPB">5-EAPB</a></li> <li><a href="/wiki/5-IT" class="mw-redirect" title="5-IT">5-IT</a></li> <li><a href="/wiki/5-MAPB" title="5-MAPB">5-MAPB</a></li> <li><a href="/wiki/5-MAPDB" title="5-MAPDB">5-MAPDB</a></li> <li><a href="/wiki/6-APB" title="6-APB">6-APB</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Chloro-MDMA" title="6-Chloro-MDMA">6-Chloro-MDMA</a></li> <li><a href="/wiki/6-EAPB" title="6-EAPB">6-EAPB</a></li> <li><a href="/wiki/6-IT" class="mw-redirect" title="6-IT">6-IT</a></li> <li><a href="/wiki/6-MAPB" title="6-MAPB">6-MAPB</a></li> <li><a href="/wiki/6-MAPDB" title="6-MAPDB">6-MAPDB</a></li> <li><a href="/wiki/Ethylidenedioxyamphetamine" class="mw-redirect" title="Ethylidenedioxyamphetamine">EDA</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/2,3-Methylenedioxyamphetamine" title="2,3-Methylenedioxyamphetamine">2,3-MDA</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">3,4-MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxylmethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxylmethamphetamine">MDHMA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a><br /><i>Others:</i> <a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">3,4-DCA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/DiFMDA" class="mw-redirect" title="DiFMDA">DiFMDA</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl"><span style="font-size:85%;">D</span>-Deprenyl</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phentermine" title="Phentermine">Phentermines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a><br /><i>Entactogens:</i> <a href="/wiki/Methylenedioxyphentermine" class="mw-redirect" title="Methylenedioxyphentermine">MDPH</a></li> <li><a href="/wiki/Methylenedioxymethylphentermine" class="mw-redirect" title="Methylenedioxymethylphentermine">MDMPH</a><br /><i>Others:</i> <a href="/wiki/Cericlamine" title="Cericlamine">Cericlamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Cathinones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/3-Fluoromethcathinone" title="3-Fluoromethcathinone">3-FMC</a></li> <li><a href="/wiki/4-Methylcathinone" title="4-Methylcathinone">4-MC</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">4-BMC</a></li> <li><a href="/wiki/4-Chloromethcathinone" title="4-Chloromethcathinone">4-CMC</a></li> <li><a href="/wiki/4-Ethylmethcathinone" title="4-Ethylmethcathinone">4-EMC</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">4-FMC</a></li> <li><a href="/wiki/4-Methylethcathinone" title="4-Methylethcathinone">4-MEC</a></li> <li><a href="/wiki/4-Methylbuphedrone" title="4-Methylbuphedrone">4-MeMABP</a></li> <li><a href="/wiki/4-Methylpentedrone" title="4-Methylpentedrone">4-MPD</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Benzedrone" title="Benzedrone">Benzedrone</a></li> <li><a href="/wiki/Brephedrone" class="mw-redirect" title="Brephedrone">Brephedrone</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Dimethylcathinone" class="mw-redirect" title="Dimethylcathinone">Dimethylcathinone</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/N-Ethylbuphedrone" title="N-Ethylbuphedrone">NEB</a></li> <li><a href="/wiki/N-Ethylhexedrone" title="N-Ethylhexedrone">N-Ethylhexedrone</a></li> <li><a href="/wiki/N-Ethylpentedrone" title="N-Ethylpentedrone">N-Ethylpentedrone</a></li> <li><a href="/wiki/Pentedrone" title="Pentedrone">Pentedrone</a></li> <li><a href="/wiki/Pentylone" title="Pentylone">Pentylone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a><br /><i>Entactogens:</i> <a href="/wiki/3,4-Dimethylmethcathinone" title="3,4-Dimethylmethcathinone">3,4-DMMC</a></li> <li><a href="/wiki/3-Methylmethcathinone" title="3-Methylmethcathinone">3-MMC</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Methylenedioxycathinone" title="Methylenedioxycathinone">Methylenedioxycathinone</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Entactogens:</i> <a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Methylphenylisobutylamine" title="4-Methylphenylisobutylamine">4-MAB</a></li> <li><a href="/wiki/Ariadne_(psychedelic)" class="mw-redirect" title="Ariadne (psychedelic)">Ariadne</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/MBDB" title="MBDB">MBDB</a><br /><i>Stimulants:</i> <a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">Phenylalkylpyrrolidines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/Alpha-Pyrrolidinobutiophenone" class="mw-redirect" title="Alpha-Pyrrolidinobutiophenone">α-PBP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinohexiophenone" class="mw-redirect" title="Alpha-Pyrrolidinohexiophenone">α-PHP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopropiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopropiophenone">α-PPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiophenone">α-PVP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinobutiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinobutiophenone">MDPBP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinopropiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinopropiophenone">MDPPP</a></li> <li><a href="/wiki/3,4-Methylenedioxypyrovalerone" class="mw-redirect" title="3,4-Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">4-MePBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">4-MePHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">4-MePPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopropiophenone" title="4'-Methoxy-α-pyrrolidinopropiophenone">MOPPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopentiophenone" title="4'-Methoxy-α-pyrrolidinopentiophenone">MOPVP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">MPBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">MPHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">MPPP</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">PEP</a></li> <li><a href="/wiki/Prolintane" title="Prolintane">Prolintane</a></li> <li><a href="/wiki/Pyrovalerone" title="Pyrovalerone">Pyrovalerone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Catecholamine" title="Catecholamine">Catecholamines</a><br /><span style="font-size:85%;">(and close relatives)</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/6-Hydroxydopamine" class="mw-redirect" title="6-Hydroxydopamine">6-OHDA</a></li> <li><a href="/wiki/Alpha-Methyldopamine" class="mw-redirect" title="Alpha-Methyldopamine">a-Me-DA</a></li> <li><a href="/wiki/Alpha-Methyltyramine" class="mw-redirect" title="Alpha-Methyltyramine">a-Me-TRA</a></li> <li><a href="/wiki/Adrenochrome" title="Adrenochrome">Adrenochrome</a></li> <li><a href="/wiki/Ciladopa" title="Ciladopa">Ciladopa</a></li> <li><a href="/wiki/D-DOPA" title="D-DOPA"><span style="font-size:85%;">D</span>-DOPA</a> (Dextrodopa)</li> <li><a href="/wiki/Dimetofrine" title="Dimetofrine">Dimetofrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Epinephrine_(neurotransmitter)" class="mw-redirect" title="Epinephrine (neurotransmitter)">Epinephrine</a></li> <li><a href="/wiki/Epinine" class="mw-redirect" title="Epinine">Epinine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Fenclonine" title="Fenclonine">Fenclonine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA"><span style="font-size:85%;">L</span>-DOPA</a> (Levodopa)</li> <li><a href="/wiki/L-DOPS" class="mw-redirect" title="L-DOPS"><span style="font-size:85%;">L</span>-DOPS</a> (Droxidopa)</li> <li><a href="/wiki/L-Phenylalanine" class="mw-redirect" title="L-Phenylalanine"><span style="font-size:85%;">L</span>-Phenylalanine</a></li> <li><a href="/wiki/L-Tyrosine" class="mw-redirect" title="L-Tyrosine"><span style="font-size:85%;">L</span>-Tyrosine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Metaterol" title="Metaterol">Metaterol</a></li> <li><a href="/wiki/Metirosine" class="mw-redirect" title="Metirosine">Metirosine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/N,N-Dimethyldopamine" title="N,N-Dimethyldopamine">N,N-Dimethyldopamine</a></li> <li><a href="/wiki/Nordefrin" class="mw-redirect" title="Nordefrin">Nordefrin</a> (<a href="/wiki/Levonordefrin" class="mw-redirect" title="Levonordefrin">Levonordefrin</a>)</li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a> (<i>m</i>-Octopamine)</li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AL-LAD" title="AL-LAD">AL-LAD</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Desvenlafaxine" title="Desvenlafaxine">Desvenlafaxine</a></li> <li><a href="/wiki/Diphenidine" title="Diphenidine">Diphenidine</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/ETH-LAD" title="ETH-LAD">ETH-LAD</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fluorolintane" title="Fluorolintane">Fluorolintane</a></li> <li><a href="/wiki/Hexapradol" title="Hexapradol">Hexapradol</a></li> <li><a href="/wiki/IP-LAD" class="mw-redirect" title="IP-LAD">IP-LAD</a></li> <li><a href="/wiki/Lysergic_acid_amide" class="mw-redirect" title="Lysergic acid amide">Lysergic acid amide</a></li> <li><a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">Lysergic acid 2-butyl amide</a></li> <li><a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">Lysergic acid 2,4-dimethylazetidide</a></li> <li><a href="/wiki/LSD" title="LSD">Lysergic acid diethylamide</a></li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Methoxphenidine" title="Methoxphenidine">Methoxphenidine</a></li> <li><a href="/wiki/MT-45" title="MT-45">MT-45</a></li> <li><a href="/wiki/PARGY-LAD" title="PARGY-LAD">PARGY-LAD</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a href="/wiki/PRO-LAD" title="PRO-LAD">PRO-LAD</a></li> <li><a href="/wiki/Pronethalol" title="Pronethalol">Pronethalol</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a> (<a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a>)</li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Thiamphenicol" title="Thiamphenicol">Thiamphenicol</a></li> <li><a href="/wiki/UWA-101" title="UWA-101">UWA-101</a></li> <li><a href="/wiki/Venlafaxine" title="Venlafaxine">Venlafaxine</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img 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