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</div> <div class="pre-content heading-holder"> <div class="page-heading"> <h1 id="firstHeading" class="firstHeading mw-first-heading">Phenethylamine</h1> <div class="tagline"></div> </div> <ul id="p-associated-pages" class="minerva__tab-container"> <li class="minerva__tab selected"> <a class="minerva__tab-text" href="/wiki/Phenethylamine" rel="" data-event-name="tabs.subject">Article</a> </li> <li class="minerva__tab "> <a class="minerva__tab-text" href="/wiki/Talk:Phenethylamine" rel="discussion" data-event-name="tabs.talk">Talk</a> </li> </ul> <nav class="page-actions-menu"> <ul id="p-views" class="page-actions-menu__list"> <li id="language-selector" class="page-actions-menu__list-item"> <a role="button" href="#p-lang" data-mw="interface" data-event-name="menu.languages" title="Language" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet language-selector"> Language </a> </li> <li 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block=document.getElementById("mf-section-"+id);block.className+=" open-block";block.previousSibling.className+=" open-block";}</script><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><section class="mf-section-0" id="mf-section-0"> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about 2-phenylethylamine. For its isomer, see <a href="/wiki/1-phenylethylamine" class="mw-redirect" title="1-phenylethylamine">1-phenylethylamine</a>. For its derivatives, see <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">substituted phenethylamine</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style>Phenethylamine<a href="#cite_note-11">[note 1]</a> (PEA) is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a>, <a href="/wiki/Natural_product" title="Natural product">natural</a> <a href="/wiki/Monoamine" class="mw-redirect" title="Monoamine">monoamine</a> <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a>, and <a href="/wiki/Trace_amine" title="Trace amine">trace amine</a>, which acts as a <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> <a href="/wiki/Stimulant" title="Stimulant">stimulant</a> in humans. In the brain, phenethylamine regulates <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmission</a> by binding to <a href="/wiki/Trace_amine-associated_receptor_1" class="mw-redirect" title="Trace amine-associated receptor 1">trace amine-associated receptor 1</a> (TAAR1) and inhibiting <a href="/wiki/Vesicular_monoamine_transporter_2" title="Vesicular monoamine transporter 2">vesicular monoamine transporter 2</a> (VMAT2) in monoamine <a href="/wiki/Neuron" title="Neuron">neurons</a>.<a href="#cite_note-TAAR1_and_TA_pharmacology_2016_review-1">[1]</a><a href="#cite_note-PEA_VMAT2_MEDRS_review-12">[11]</a><a href="#cite_note-Miller-13">[12]</a> To a lesser extent, it also acts as a <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> in the human <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>.<a href="#cite_note-PEA_2-14">[13]</a> In mammals, phenethylamine <a href="/wiki/Biosynthesis" title="Biosynthesis">is produced</a> from the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/L-phenylalanine" class="mw-redirect" title="L-phenylalanine">L-phenylalanine</a> by the enzyme <a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">aromatic L-amino acid decarboxylase</a> via <a href="/wiki/Enzymatic" class="mw-redirect" title="Enzymatic">enzymatic</a> <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a>.<a href="#cite_note-Berry_2004-15">[14]</a> In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as <a href="/wiki/Chocolate" title="Chocolate">chocolate</a>, especially after <a href="/wiki/Microorganism" title="Microorganism">microbial</a> <a href="/wiki/Fermentation_(food)" class="mw-redirect" title="Fermentation (food)">fermentation</a>. <table class="infobox" style="border-spacing:2px;"><caption class="infobox-title">Phenethylamine</caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Phenethylamine2DCSD.svg" class="mw-file-description"><img alt="Image of the phenethylamine skeleton" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/04/Phenethylamine2DCSD.svg/200px-Phenethylamine2DCSD.svg.png" decoding="async" width="200" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/04/Phenethylamine2DCSD.svg/300px-Phenethylamine2DCSD.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/04/Phenethylamine2DCSD.svg/400px-Phenethylamine2DCSD.svg.png 2x" data-file-width="590" data-file-height="245"></a></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Phenethylamine-3D-balls.png" class="mw-file-description"><img alt="Ball-and-stick model of phenethylamine" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Phenethylamine-3D-balls.png/200px-Phenethylamine-3D-balls.png" decoding="async" width="200" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Phenethylamine-3D-balls.png/300px-Phenethylamine-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Phenethylamine-3D-balls.png/400px-Phenethylamine-3D-balls.png 2x" data-file-width="2000" data-file-height="1287"></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/fɛnˈɛθələmiːn/</a> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Phenylethylamine; PEA; β-Phenylethylamine; β-Phenylethylamine; β-PEA; 2-Phenylethylamine; 2-PEA; Phetamine</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Substance_dependence" title="Substance dependence">Dependence liability</a></th><td class="infobox-data"><a href="/wiki/Psychological_dependence" title="Psychological dependence">Psychological</a>: low–moderate[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] <a href="/wiki/Physical_dependence" title="Physical dependence">Physical</a>: none</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Addiction" title="Addiction">Addiction liability</a></th><td class="infobox-data">None–Low (w/o an <a href="/wiki/Monoamine_oxidase_inhibitor#List_of_MAO_inhibiting_drugs" title="Monoamine oxidase inhibitor">MAO-B inhibitor</a>)<a href="#cite_note-TAAR1_and_TA_pharmacology_2016_review-1">[1]</a> Moderate (with an MAO-B inhibitor)<a href="#cite_note-TAAR1_and_TA_pharmacology_2016_review-1">[1]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a> (taken by mouth)</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/Norepinephrine%E2%80%93dopamine_releasing_agent" title="Norepinephrine–dopamine releasing agent">Norepinephrine–dopamine releasing agent</a>; <a href="/wiki/Trace_amine-associated_receptor_1" class="mw-redirect" title="Trace amine-associated receptor 1">Trace amine-associated receptor 1</a> (TAAR1) <a href="/wiki/Agonist" title="Agonist">agonist</a>; <a href="/wiki/Psychostimulant" class="mw-redirect" title="Psychostimulant">Psychostimulant</a>; <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">Sympathomimetic</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>None</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Physiological" class="mw-redirect" title="Physiological">Physiological</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Source <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a></th><td class="infobox-data"><a href="/wiki/Substantia_nigra_pars_compacta" class="mw-redirect" title="Substantia nigra pars compacta">Substantia nigra pars compacta</a>; <a href="/wiki/Ventral_tegmental_area" title="Ventral tegmental area">Ventral tegmental area</a>; <a href="/wiki/Locus_coeruleus" title="Locus coeruleus">Locus coeruleus</a>; many others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Target tissues</th><td class="infobox-data">System-wide</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptors</a></th><td class="infobox-data">Varies greatly across species; Human receptors: <a href="/wiki/HTAAR1" class="mw-redirect" title="HTAAR1">hTAAR1</a><a href="#cite_note-Human_trace_amines_and_hTAARs_October_2016_review-2">[2]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursor</a></th><td class="infobox-data"><a href="/wiki/L-Phenylalanine" class="mw-redirect" title="L-Phenylalanine">L-Phenylalanine</a><a href="#cite_note-Renaissance-3">[3]</a><a href="#cite_note-Vascular-4">[4]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biosynthesis" title="Biosynthesis">Biosynthesis</a></th><td class="infobox-data"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">Aromatic L-amino acid decarboxylase</a> (AADC)<a href="#cite_note-Renaissance-3">[3]</a><a href="#cite_note-Vascular-4">[4]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data">Primarily: <a href="/wiki/Monoamine_oxidase_B" title="Monoamine oxidase B">MAO-B</a><a href="#cite_note-Renaissance-3">[3]</a><a href="#cite_note-Vascular-4">[4]</a><a href="#cite_note-HMDB_PEA-5">[5]</a> Other enzymes: <a href="/wiki/Monoamine_oxidase_A" title="Monoamine oxidase A">MAO-A</a>,<a href="#cite_note-HMDB_PEA-5">[5]</a><a href="#cite_note-PEA_MAO-A_and_B_Substrate-Suzuki-6">[6]</a> <a href="/wiki/Semicarbazide-sensitive_amine_oxidase" class="mw-redirect" title="Semicarbazide-sensitive amine oxidase">SSAOs</a> (<a href="/wiki/AOC2" title="AOC2">AOC2</a> & <a href="/wiki/AOC3" title="AOC3">AOC3</a>),<a href="#cite_note-HMDB_PEA-5">[5]</a><a href="#cite_note-SSAO-7">[7]</a> <a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a>,<a href="#cite_note-Renaissance-3">[3]</a><a href="#cite_note-Vascular-4">[4]</a><a href="#cite_note-HMDB_PEA-5">[5]</a> <a href="/wiki/Aralkylamine_N-acetyltransferase" title="Aralkylamine N-acetyltransferase">AANAT</a>,<a href="#cite_note-HMDB_PEA-5">[5]</a> <a href="/wiki/Flavin-containing_monooxygenase_3" title="Flavin-containing monooxygenase 3">FMO3</a>,<a href="#cite_note-FMO-8">[8]</a><a href="#cite_note-FMO3_catecholamines-9">[9]</a> and others</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><abbr class="country-name" title="Australia">AU</abbr>: Unscheduled</li> <li><abbr class="country-name" title="Canada">CA</abbr>: Unscheduled</li> <li><abbr class="country-name" title="New Zealand">NZ</abbr>: Unscheduled</li> <li><abbr class="country-name" title="United Kingdom">UK</abbr>: Unscheduled</li> <li><abbr class="country-name" title="United States">US</abbr>: Unscheduled</li> <li><abbr class="country-name" title="United Nations">UN</abbr>: Unscheduled</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data">Primarily: <a href="/wiki/Monoamine_oxidase_B" title="Monoamine oxidase B">MAO-B</a><a href="#cite_note-Renaissance-3">[3]</a><a href="#cite_note-Vascular-4">[4]</a><a href="#cite_note-HMDB_PEA-5">[5]</a> Other enzymes: <a href="/wiki/Monoamine_oxidase_A" title="Monoamine oxidase A">MAO-A</a>,<a href="#cite_note-HMDB_PEA-5">[5]</a><a href="#cite_note-PEA_MAO-A_and_B_Substrate-Suzuki-6">[6]</a> <a href="/wiki/Semicarbazide-sensitive_amine_oxidase" class="mw-redirect" title="Semicarbazide-sensitive amine oxidase">SSAOs</a> (<a href="/wiki/AOC2" title="AOC2">AOC2</a> & <a href="/wiki/AOC3" title="AOC3">AOC3</a>),<a href="#cite_note-HMDB_PEA-5">[5]</a><a href="#cite_note-SSAO-7">[7]</a> <a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a>,<a href="#cite_note-Renaissance-3">[3]</a><a href="#cite_note-Vascular-4">[4]</a><a href="#cite_note-HMDB_PEA-5">[5]</a> <a href="/wiki/Aralkylamine_N-acetyltransferase" title="Aralkylamine N-acetyltransferase">AANAT</a>,<a href="#cite_note-HMDB_PEA-5">[5]</a> <a href="/wiki/Flavin-containing_monooxygenase_3" title="Flavin-containing monooxygenase 3">FMO3</a>,<a href="#cite_note-FMO-8">[8]</a><a href="#cite_note-FMO3_catecholamines-9">[9]</a> and others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination half-life</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>Exogenous: 5–10 minutes<a href="#cite_note-PubChem-10">[10]</a></li><li>Endogenous: ~30 seconds<a href="#cite_note-Renaissance-3">[3]</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Renal" class="mw-redirect" title="Renal">Renal</a> (kidneys)</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">2-Phenylethan-1-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><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=64-04-0">64-04-0</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/1001">1001</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=2144">2144</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB04325">DB04325</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.13856352.html">13856352</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/327C7L2BXQ">327C7L2BXQ</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C05332">C05332</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18397">CHEBI:18397</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL610">ChEMBL610</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/NIAID_ChemDB" title="NIAID ChemDB">NIAID ChemDB</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemdb.niaid.nih.gov/CompoundDetails.aspx?AIDSNO=018561">018561</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID5058773">DTXSID5058773</a> <a href="https://www.wikidata.org/wiki/Q407411#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20"></a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.523">100.000.523</a> <a href="https://www.wikidata.org/wiki/Q407411#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20"></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data">C8H11N</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">121.183 g·mol−1</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=NCCc1ccccc1">Interactive image</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Density" title="Density">Density</a></th><td class="infobox-data">0.9640 g/cm3 <a href="#cite_note-PubChem-10">[10]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">−60 °C (−76 °F) <a href="#cite_note-PubChem-10">[10]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a></th><td class="infobox-data">195 °C (383 °F) <a href="#cite_note-PubChem-10">[10]</a></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%;">NCCc1ccccc1</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/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2 <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:BHHGXPLMPWCGHP-UHFFFAOYSA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style> <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=612854585&page2=Phenethylamine">(verify)</a></td></tr></tbody></table> Phenethylamine is sold as a <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a> for purported <a href="/wiki/Mood_(psychology)" title="Mood (psychology)">mood</a> and <a href="/wiki/Weight_loss" title="Weight loss">weight loss</a>-related <a href="/wiki/Therapeutic_benefit" class="mw-redirect" title="Therapeutic benefit">therapeutic benefits</a>; however, in <a href="/wiki/Oral_administration" title="Oral administration">orally</a> ingested phenethylamine, a significant amount is metabolized in the <a href="/wiki/Small_intestine" title="Small intestine">small intestine</a> by <a href="/wiki/Monoamine_oxidase_B" title="Monoamine oxidase B">monoamine oxidase B</a> (MAO-B) and then <a href="/wiki/Aldehyde_dehydrogenase" title="Aldehyde dehydrogenase">aldehyde dehydrogenase</a> (ALDH), which converts it to <a href="/wiki/Phenylacetic_acid" title="Phenylacetic acid">phenylacetic acid</a>.<a href="#cite_note-HMDB_PEA-5">[5]</a> This means that for significant <a href="/wiki/Concentration" title="Concentration">concentrations</a> to reach the <a href="/wiki/Brain" title="Brain">brain</a>, the dosage must be higher than for other methods of administration.<a href="#cite_note-HMDB_PEA-5">[5]</a><a href="#cite_note-PEA_MAO-A_and_B_Substrate-Suzuki-6">[6]</a><a href="#cite_note-PEA_MAO-B_Substrate-Yang-16">[15]</a> Some authors postulated its role in people's falling-in-love without substantiating it with any direct evidence.<a href="#cite_note-17">[16]</a><a href="#cite_note-18">[17]</a> Phenethylamines, or more properly, <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">substituted phenethylamines</a>, are the group of phenethylamine <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivatives</a> that contain phenethylamine as a "backbone"; in other words, this <a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical class</a> includes <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivative</a> compounds that are formed by replacing one or more hydrogen atoms in the phenethylamine core structure with <a href="/wiki/Substituent" title="Substituent">substituents</a>. The class of <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">substituted phenethylamines</a> includes all <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">substituted amphetamines</a>, and <a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">substituted methylenedioxyphenethylamines</a> (MDxx), and contains many drugs which act as <a href="/wiki/Empathogen-entactogen" class="mw-redirect" title="Empathogen-entactogen">empathogens</a>, <a href="/wiki/Stimulant" title="Stimulant">stimulants</a>, <a href="/wiki/Psychedelic_drug" title="Psychedelic drug">psychedelics</a>, <a href="/wiki/Anorectic" title="Anorectic">anorectics</a>, <a href="/wiki/Bronchodilator" title="Bronchodilator">bronchodilators</a>, <a href="/wiki/Decongestant" title="Decongestant">decongestants</a>, and/or <a href="/wiki/Antidepressant" title="Antidepressant">antidepressants</a>, among others. <div id="toc" class="toc" role="navigation" aria-labelledby="mw-toc-heading"><input type="checkbox" role="button" id="toctogglecheckbox" class="toctogglecheckbox" style="display:none"><div class="toctitle" lang="en" dir="ltr"><h2 id="mw-toc-heading">Contents</h2><label class="toctogglelabel" for="toctogglecheckbox"></label></div> <ul> <li class="toclevel-1 tocsection-1"><a href="#Natural_occurrence">1 Natural occurrence</a></li> <li class="toclevel-1 tocsection-2"><a href="#Chemistry">2 Chemistry</a> <ul> <li class="toclevel-2 tocsection-3"><a href="#Substituted_derivatives">2.1 Substituted derivatives</a></li> <li class="toclevel-2 tocsection-4"><a href="#Synthesis">2.2 Synthesis</a></li> <li class="toclevel-2 tocsection-5"><a href="#Detection_in_body_fluids">2.3 Detection in body fluids</a></li> </ul> </li> <li class="toclevel-1 tocsection-6"><a href="#Biological_activity">3 Biological activity</a> <ul> <li class="toclevel-2 tocsection-7"><a href="#Monoamine_releasing_agent">3.1 Monoamine releasing agent</a></li> <li class="toclevel-2 tocsection-8"><a href="#TAAR1_agonist">3.2 TAAR1 agonist</a></li> <li class="toclevel-2 tocsection-9"><a href="#Monoaminergic_activity_enhancer">3.3 Monoaminergic activity enhancer</a></li> <li class="toclevel-2 tocsection-10"><a href="#Other_activities">3.4 Other activities</a></li> <li class="toclevel-2 tocsection-11"><a href="#Effects_in_animals_and_humans">3.5 Effects in animals and humans</a></li> </ul> </li> <li class="toclevel-1 tocsection-12"><a href="#Pharmacokinetics">4 Pharmacokinetics</a></li> <li class="toclevel-1 tocsection-13"><a href="#Notes">5 Notes</a></li> <li class="toclevel-1 tocsection-14"><a href="#References">6 References</a></li> <li class="toclevel-1 tocsection-15"><a href="#External_links">7 External links</a></li> </ul> </div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(1)"><h2 id="Natural_occurrence">Natural occurrence</h2> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=1" title="Edit section: Natural occurrence" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-1 collapsible-block" id="mf-section-1"> Phenethylamine is produced by a wide range of species throughout the plant and animal kingdoms, including humans;<a href="#cite_note-Berry_2004-15">[14]</a><a href="#cite_note-19">[18]</a> it is also produced by certain <a href="/wiki/Fungi" class="mw-redirect" title="Fungi">fungi</a> and <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> (genera: <a href="/wiki/Lactobacillus" title="Lactobacillus">Lactobacillus</a>, <a href="/wiki/Clostridium" title="Clostridium">Clostridium</a>, <a href="/wiki/Pseudomonas" title="Pseudomonas">Pseudomonas</a> and the family <a href="/wiki/Enterobacteriaceae" title="Enterobacteriaceae">Enterobacteriaceae</a>) and acts as a potent <a href="/wiki/Antimicrobial" title="Antimicrobial">antimicrobial</a> against certain pathogenic strains of <a href="/wiki/Escherichia_coli" title="Escherichia coli">Escherichia coli</a> (e.g., the <a href="/wiki/Escherichia_coli_O157:H7" title="Escherichia coli O157:H7">O157:H7 strain</a>) at sufficient concentrations.<a href="#cite_note-pmid23896151-20">[19]</a> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(2)"><h2 id="Chemistry">Chemistry</h2> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=2" title="Edit section: Chemistry" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-2 collapsible-block" id="mf-section-2"> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:224px;max-width:224px"><div class="trow"><div class="tsingle" style="width:222px;max-width:222px"><div class="thumbimage"><a href="/wiki/File:PEA_powder.jpg" class="mw-file-description"><noscript><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/PEA_powder.jpg/220px-PEA_powder.jpg" decoding="async" width="220" height="128" class="mw-file-element" data-file-width="4075" data-file-height="2378"></noscript><span class="lazy-image-placeholder" style="width: 220px;height: 128px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/PEA_powder.jpg/220px-PEA_powder.jpg" data-alt="" data-width="220" data-height="128" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/PEA_powder.jpg/330px-PEA_powder.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/PEA_powder.jpg/440px-PEA_powder.jpg 2x" data-class="mw-file-element"> </a></div></div></div><div class="trow"><div class="tsingle" style="width:222px;max-width:222px"><div class="thumbimage"><a href="/wiki/File:PEA_crystals.jpg" class="mw-file-description"><noscript><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/PEA_crystals.jpg/220px-PEA_crystals.jpg" decoding="async" width="220" height="131" class="mw-file-element" data-file-width="5026" data-file-height="2982"></noscript><span class="lazy-image-placeholder" style="width: 220px;height: 131px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/PEA_crystals.jpg/220px-PEA_crystals.jpg" data-alt="" data-width="220" data-height="131" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/PEA_crystals.jpg/330px-PEA_crystals.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9d/PEA_crystals.jpg/440px-PEA_crystals.jpg 2x" data-class="mw-file-element"> </a></div><div class="thumbcaption">PEA powder and crystals</div></div></div></div></div> Phenethylamine is a primary amine, the amino-group being attached to a <a href="/wiki/Benzene_ring" class="mw-redirect" title="Benzene ring">benzene ring</a> through a two-carbon, or <a href="/wiki/Ethyl_group" title="Ethyl group">ethyl group</a>.<a href="#cite_note-PubChem-10">[10]</a> It is a colourless liquid at room temperature that has a fishy odor, and is soluble in water, <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> and <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>.<a href="#cite_note-PubChem-10">[10]</a> Its density is 0.964 g/ml and its boiling point is 195 °C.<a href="#cite_note-PubChem-10">[10]</a> Upon exposure to air, it combines with <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> to form a solid <a href="/wiki/Carbonate" title="Carbonate">carbonate</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a>.<a href="#cite_note-Merck-21">[20]</a> Phenethylamine is strongly <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">basic</a>, pKb = 4.17 (or pKa = 9.83), as measured using the HCl salt, and forms a stable crystalline <a href="/wiki/Hydrochloride" title="Hydrochloride">hydrochloride</a> salt with a melting point of 217 °C.<a href="#cite_note-PubChem-10">[10]</a><a href="#cite_note-22">[21]</a> Its experimental <a href="/wiki/Partition_coefficient" title="Partition coefficient">log P</a> is 1.41.<a href="#cite_note-PubChem-10">[10]</a> <div class="mw-heading mw-heading3"><h3 id="Substituted_derivatives">Substituted derivatives</h3> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=3" title="Edit section: Substituted derivatives" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Substituted phenethylamine</a></div> Substituted phenethylamines are a <a href="/wiki/Chemical_class" class="mw-redirect" title="Chemical class">chemical class</a> of <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> based upon the phenethylamine structure;<a href="#cite_note-23">[note 2]</a> the class is composed of all the <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivative</a> compounds of phenethylamine which can be formed by replacing, or <a href="/wiki/Substitution_reaction" title="Substitution reaction">substituting</a>, one or more <a href="/wiki/Hydrogen_atom" title="Hydrogen atom">hydrogen atoms</a> in the phenethylamine core structure with <a href="/wiki/Substituent" title="Substituent">substituents</a>. Many substituted phenethylamines are psychoactive drugs, which belong to a variety of different drug classes, including <a href="/wiki/Central_nervous_system_stimulant" class="mw-redirect" title="Central nervous system stimulant">central nervous system stimulants</a> (e.g., <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>), <a href="/wiki/Hallucinogen" title="Hallucinogen">hallucinogens</a> (e.g., <a href="/wiki/2,5-dimethoxy-4-methylamphetamine" class="mw-redirect" title="2,5-dimethoxy-4-methylamphetamine">2,5-dimethoxy-4-methylamphetamine</a>), <a href="/wiki/Entactogen" class="mw-redirect" title="Entactogen">entactogens</a> (e.g., <a href="/wiki/3,4-methylenedioxyamphetamine" class="mw-redirect" title="3,4-methylenedioxyamphetamine">3,4-methylenedioxyamphetamine</a>), <a href="/wiki/Appetite_suppressant" class="mw-redirect" title="Appetite suppressant">appetite suppressants</a> (e.g. <a href="/wiki/Phentermine" title="Phentermine">phentermine</a>), <a href="/wiki/Nasal_decongestant" class="mw-redirect" title="Nasal decongestant">nasal decongestants</a> and <a href="/wiki/Bronchodilator" title="Bronchodilator">bronchodilators</a> (e.g., <a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">pseudoephedrine</a>), <a href="/wiki/Antidepressant" title="Antidepressant">antidepressants</a> (e.g. <a href="/wiki/Bupropion" title="Bupropion">bupropion</a>), <a href="/wiki/Management_of_Parkinson%27s_disease#Medication" title="Management of Parkinson's disease">antiparkinson agents</a> (e.g., <a href="/wiki/Selegiline" title="Selegiline">selegiline</a>), and <a href="/wiki/Vasopressor" class="mw-redirect" title="Vasopressor">vasopressors</a> (e.g., <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>), among others. Many of these psychoactive compounds exert their pharmacological effects primarily by modulating <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitter</a> systems; however, there is no mechanism of action or biological target that is common to all members of this subclass. Numerous <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> compounds – including <a href="/wiki/Hormone" title="Hormone">hormones</a>, monoamine neurotransmitters, and many <a href="/wiki/Trace_amine" title="Trace amine">trace amines</a> (e.g., <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>, <a href="/wiki/Adrenaline" title="Adrenaline">adrenaline</a>, <a href="/wiki/Tyramine" title="Tyramine">tyramine</a>, and others) – are substituted phenethylamines. Dopamine is simply phenethylamine with a hydroxyl group attached to the 3 and 4 position of the benzene ring. Several notable recreational drugs, such as <a href="/wiki/MDMA" title="MDMA">MDMA</a> (ecstasy), <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>, and <a href="/wiki/Cathinone" title="Cathinone">cathinones</a>, are also members of the class. All of the <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">substituted amphetamines</a> are phenethylamines, as well. Pharmaceutical drugs that are substituted phenethylamines include <a href="/wiki/Phenelzine" title="Phenelzine">phenelzine</a>, <a href="/wiki/Phenformin" title="Phenformin">phenformin</a>, and <a href="/wiki/Fanetizole" title="Fanetizole">fanetizole</a>, among many others. The N-<a href="/wiki/Methyl_group" title="Methyl group">methylated</a> derivative of phenethylamine is <a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine">N-methylphenethylamine</a>. <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=4" title="Edit section: Synthesis" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> One method for preparing β-phenethylamine, set forth in J. C. Robinson and H. R. Snyder's Organic Syntheses (published 1955), involves the reduction of <a href="/wiki/Benzyl_cyanide" title="Benzyl cyanide">benzyl cyanide</a> with <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> in liquid <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>, in the presence of a <a href="/wiki/Raney-Nickel" class="mw-redirect" title="Raney-Nickel">Raney-Nickel</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>, at a temperature of 130 °C and a pressure of 13.8 MPa. Alternative syntheses are outlined in the footnotes to this preparation.<a href="#cite_note-24">[22]</a> A much more convenient method for the synthesis of β-phenethylamine is the reduction of <a href="/wiki/Beta-Nitrostyrene" class="mw-redirect" title="Beta-Nitrostyrene">ω-nitrostyrene</a> by <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a> in ether, whose successful execution was first reported by R. F. Nystrom and W. G. Brown in 1948.<a href="#cite_note-25">[23]</a> Phenethylamine can also be produced via the cathodic reduction of <a href="/wiki/Benzyl_cyanide" title="Benzyl cyanide">benzyl cyanide</a> in a divided cell.<a href="#cite_note-Shamelessly_stolen_from_the_Electrosynthesis_article-26">[24]</a> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Benzyl_cyanide_electrolytic_reduction.png" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/Benzyl_cyanide_electrolytic_reduction.png/450px-Benzyl_cyanide_electrolytic_reduction.png" decoding="async" width="450" height="68" class="mw-file-element" data-file-width="3070" data-file-height="466"></noscript><span class="lazy-image-placeholder" style="width: 450px;height: 68px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/Benzyl_cyanide_electrolytic_reduction.png/450px-Benzyl_cyanide_electrolytic_reduction.png" data-width="450" data-height="68" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/Benzyl_cyanide_electrolytic_reduction.png/675px-Benzyl_cyanide_electrolytic_reduction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/43/Benzyl_cyanide_electrolytic_reduction.png/900px-Benzyl_cyanide_electrolytic_reduction.png 2x" data-class="mw-file-element"> </a><figcaption><a href="/wiki/Electrosynthesis" title="Electrosynthesis">Electrosynthesis</a> of phenethylamine from <a href="/wiki/Benzyl_cyanide" title="Benzyl cyanide">benzyl cyanide</a><a href="#cite_note-Shamelessly_stolen_from_the_Electrosynthesis_article-26">[24]</a></figcaption></figure> Assembling phenethylamine structures for synthesis of compounds such as epinephrine, amphetamines, tyrosine, and dopamine by adding the beta-aminoethyl side chain to the <a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a> ring is possible. This can be done via <a href="/wiki/Friedel-Crafts_acylation" class="mw-redirect" title="Friedel-Crafts acylation">Friedel-Crafts acylation</a> with N-protected <a href="/wiki/Acyl_chloride" title="Acyl chloride">acyl chlorides</a> when the arene is activated, or by <a href="/wiki/Heck_reaction" title="Heck reaction">Heck reaction</a> of the phenyl with N-vinyl<a href="/wiki/Oxazolone" title="Oxazolone">oxazolone</a>, followed by <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a>, or by cross-coupling with beta-amino <a href="/wiki/Organozinc" class="mw-redirect" title="Organozinc">organozinc</a> reagents, or reacting a brominated arene with beta-aminoethyl <a href="/wiki/Organolithium" class="mw-redirect" title="Organolithium">organolithium</a> reagents, or by <a href="/wiki/Suzuki_cross-coupling" class="mw-redirect" title="Suzuki cross-coupling">Suzuki cross-coupling</a>.<a href="#cite_note-27">[25]</a> <div class="mw-heading mw-heading3"><h3 id="Detection_in_body_fluids">Detection in body fluids</h3> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=5" title="Edit section: Detection in body fluids" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Expand_section plainlinks metadata ambox mbox-small-left ambox-content" role="presentation"><tbody><tr><td class="mbox-text"><div class="mbox-text-span">This section needs expansion with: <a href="#cite_note-HMDB_PEA-5">[5]</a>. You can help by <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Phenethylamine&action=edit&section=">adding to it</a>. (September 2016)</div></td></tr></tbody></table> Reviews that cover <a href="/wiki/Attention_deficit_hyperactivity_disorder" title="Attention deficit hyperactivity disorder">attention deficit hyperactivity disorder</a> (ADHD) and phenethylamine indicate that several studies have found abnormally low urinary phenethylamine concentrations in ADHD individuals when compared with controls.<a href="#cite_note-Zinc_and_PEA-28">[26]</a> In treatment-responsive individuals, amphetamine and <a href="/wiki/Methylphenidate" title="Methylphenidate">methylphenidate</a> greatly increase urinary phenethylamine concentration.<a href="#cite_note-Zinc_and_PEA-28">[26]</a> An ADHD <a href="/wiki/Biomarker_(medicine)" title="Biomarker (medicine)">biomarker</a> review also indicated that urinary phenethylamine levels could be a diagnostic biomarker for ADHD.<a href="#cite_note-Zinc_and_PEA-28">[26]</a> Thirty minutes of moderate- to high-intensity physical exercise has been shown to induce an increase in urinary <a href="/wiki/Phenylacetic_acid" title="Phenylacetic acid">phenylacetic acid</a>, the primary metabolite of phenethylamine.<a href="#cite_note-Renaissance-3">[3]</a><a href="#cite_note-PEA_exercise_primary-29">[27]</a><a href="#cite_note-Neuropsychiatric-30">[28]</a> Two reviews noted a study where the mean 24 hour urinary phenylacetic acid concentration following just 30 minutes of intense exercise rose 77% above its base level;<a href="#cite_note-Renaissance-3">[3]</a><a href="#cite_note-PEA_exercise_primary-29">[27]</a><a href="#cite_note-Neuropsychiatric-30">[28]</a> the reviews suggest that phenethylamine synthesis sharply increases during physical exercise during which it is rapidly metabolized due to its short half-life of roughly 30 seconds.<a href="#cite_note-Renaissance-3">[3]</a><a href="#cite_note-PEA_exercise_primary-29">[27]</a><a href="#cite_note-Neuropsychiatric-30">[28]</a><a href="#cite_note-Vascular-4">[4]</a> In a resting state, phenethylamine is synthesized in <a href="/wiki/Catecholamine" title="Catecholamine">catecholamine</a> neurons from L-<a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a> by <a href="/wiki/Aromatic_amino_acid_decarboxylase" class="mw-redirect" title="Aromatic amino acid decarboxylase">aromatic amino acid decarboxylase</a> at approximately the same rate as dopamine is produced.<a href="#cite_note-Vascular-4">[4]</a> Monoamine oxidase deaminates primary and secondary amines that are free in the neuronal cytoplasm but not those bound in storage vesicles of the sympathetic neurone. Similarly, β-PEA would not be completely deaminated in the gut as it is a selective substrate for MAO-B, which is not primarily found in the gut. Brain levels of endogenous trace amines are several hundred-fold below those for the classical neurotransmitters noradrenaline, dopamine, and <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, but their rates of synthesis are equivalent to those of noradrenaline and dopamine and they have a very rapid turnover rate.<a href="#cite_note-Berry_2004-15">[14]</a> Endogenous extracellular tissue levels of trace amines measured in the brain are in the low nanomolar range. These low concentrations arise because of their very short half-life. Because of the pharmacological relationship between phenethylamine and amphetamine, the original paper and both reviews suggest that phenethylamine plays a prominent role in mediating the mood-enhancing <a href="/wiki/Euphoria" title="Euphoria">euphoric</a> effects of a <a href="/wiki/Runner%27s_high" title="Runner's high">runner's high</a>, as both phenethylamine and amphetamine are potent <a href="/wiki/Euphoriant" class="mw-redirect" title="Euphoriant">euphoriants</a>.<a href="#cite_note-Renaissance-3">[3]</a><a href="#cite_note-PEA_exercise_primary-29">[27]</a><a href="#cite_note-Neuropsychiatric-30">[28]</a> <a href="/wiki/Skydiving" class="mw-redirect" title="Skydiving">Skydiving</a> has also been shown to induce a marked increase in urinary phenethylamine concentrations.<a href="#cite_note-PubChem-10">[10]</a><a href="#cite_note-Skydiving-31">[29]</a> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(3)"><h2 id="Biological_activity">Biological activity</h2> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=6" title="Edit section: Biological activity" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-3 collapsible-block" id="mf-section-3"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Neurobiological_effects_of_physical_exercise#%CE%B2-Phenylethylamine" title="Neurobiological effects of physical exercise">Neurobiological effects of physical exercise § β-Phenylethylamine</a></div> <table class="wikitable floatright" style="font-size:small;"> <caption><a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">Monoamine release</a> of phenethylamine and related agents (<a href="/wiki/Half_maximal_effective_concentration" class="mw-redirect" title="Half maximal effective concentration"><abbr title="Half maximal effective concentration">EC50</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, nM) </caption> <tbody><tr> <th>Compound</th> <th data-sort-type="number"><a href="/wiki/Norepinephrine" title="Norepinephrine"><abbr title="Norepinephrine">NE</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</th> <th data-sort-type="number"><a href="/wiki/Dopamine" title="Dopamine"><abbr title="Dopamine">DA</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</th> <th data-sort-type="number"><a href="/wiki/Serotonin" title="Serotonin"><abbr title="Serotonin">5-HT</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</th> <th>Ref </th></tr> <tr> <td><a class="mw-selflink selflink">Phenethylamine</a></td> <td>10.9</td> <td>39.5</td> <td>>10000</td> <td><a href="#cite_note-ReithBLoughHong2015-32">[30]</a><a href="#cite_note-Forsyth2012-33">[31]</a><a href="#cite_note-Blough2008-34">[32]</a> </td></tr> <tr> <td><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></td> <td>40.6</td> <td>119</td> <td>2775</td> <td><a href="#cite_note-RothmanBaumannDersch2001-35">[33]</a><a href="#cite_note-Blough2008-34">[32]</a> </td></tr> <tr> <td><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></td> <td>716</td> <td>164</td> <td>32.6</td> <td><a href="#cite_note-BloughLandavazoDecker2014-36">[34]</a><a href="#cite_note-BloughLandavazoPartilla2014-37">[35]</a> </td></tr> <tr> <td><a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></td> <td>6.6–7.2</td> <td>5.8–24.8</td> <td>698–1765</td> <td><a href="#cite_note-RothmanBaumannDersch2001-35">[33]</a><a href="#cite_note-BaumannPartillaLehner2013-38">[36]</a> </td></tr> <tr> <td><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a></td> <td>9.5</td> <td>27.7</td> <td><abbr title="No data">ND</abbr></td> <td><a href="#cite_note-Forsyth2012-33">[31]</a><a href="#cite_note-Blough2008-34">[32]</a> </td></tr> <tr> <td><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></td> <td>12.3–13.8</td> <td>8.5–24.5</td> <td>736–1291.7</td> <td><a href="#cite_note-RothmanBaumannDersch2001-35">[33]</a><a href="#cite_note-BaumannAyestasPartilla2012-39">[37]</a> </td></tr> <tr> <td><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></td> <td>28.5</td> <td>416</td> <td>4640</td> <td><a href="#cite_note-RothmanBaumannDersch2001-35">[33]</a> </td></tr> <tr> <td colspan="7" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. See also <a href="/wiki/Monoamine_releasing_agent#Activity_profiles" title="Monoamine releasing agent">Monoamine releasing agent § Activity profiles</a> for a larger table with more compounds. Refs: <a href="#cite_note-RothmanBaumann2003-40">[38]</a><a href="#cite_note-RothmanBaumann2006-41">[39]</a> </td></tr></tbody></table> <div class="skin-invert-image"> <table role="presentation" cellpadding="0" style="border-spacing:0; clear:right; float:right;"> <tbody><tr> <td><div class="thumb tright"> <div class="thumbinner" style="width:542px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: #F0F8FF;margin-bottom:3px;">Phenethylamine pharmacodynamics in a TAAR1–dopamine neuron <style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist 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<div style="left:0px; top:0px; width:540px; position:absolute"> <a href="https://commons.wikimedia.org/wiki/File:TAAR1_Dopamine.svg" title="commons:File:TAAR1 Dopamine.svg"><noscript><img alt="A pharmacodynamic model of amphetamine and TAAR1" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/10/TAAR1_Dopamine.svg/540px-TAAR1_Dopamine.svg.png" decoding="async" width="540" height="685" class="mw-file-element" data-file-width="725" data-file-height="920"></noscript><span class="lazy-image-placeholder" style="width: 540px;height: 685px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/1/10/TAAR1_Dopamine.svg/540px-TAAR1_Dopamine.svg.png" data-alt="A pharmacodynamic model of amphetamine and TAAR1" data-width="540" data-height="685" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/10/TAAR1_Dopamine.svg/810px-TAAR1_Dopamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/10/TAAR1_Dopamine.svg/1080px-TAAR1_Dopamine.svg.png 2x" data-class="mw-file-element"> </a> </div> <div style="text-align:center; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_190x45" style="position:absolute; left:190px; top:45px; line-height:110%;">via <a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><noscript><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" data-file-width="133" data-file-height="200"></noscript><span class="lazy-image-placeholder" style="width: 18px;height: 27px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" data-alt="The image above contains clickable links" data-width="18" data-height="27" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/27px-Interactive_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/36px-Interactive_icon.svg.png 2x" data-class="mw-file-element"> </div>Both amphetamine and phenethylamine induce neurotransmitter release from <a href="/wiki/VMAT2" class="mw-redirect" title="VMAT2">VMAT2</a><a href="#cite_note-PEA_VMAT2_MEDRS_review-12">[11]</a><a href="#cite_note-pmid8643547-42">[40]</a><a href="#cite_note-Offermanns-43">[41]</a> and bind to <a href="/wiki/TAAR1" title="TAAR1">TAAR1</a>.<a href="#cite_note-Miller-13">[12]</a><a href="#cite_note-Cites_Miller_2011_review-44">[42]</a> When either binds to TAAR1, it reduces neuron firing rate and triggers <a href="/wiki/Protein_kinase_A" title="Protein kinase A">protein kinase A</a> (PKA) and <a href="/wiki/Protein_kinase_C" title="Protein kinase C">protein kinase C</a> (PKC) signaling, resulting in DAT phosphorylation.<a href="#cite_note-Miller-13">[12]</a><a href="#cite_note-Cites_Miller_2011_review-44">[42]</a> Phosphorylated DAT then either operates in reverse or <a href="/wiki/Endocytosis" title="Endocytosis">withdraws into the axon terminal</a> and ceases transport.<a href="#cite_note-Miller-13">[12]</a><a href="#cite_note-Cites_Miller_2011_review-44">[42]</a></div> </div> </div> </td></tr></tbody></table> </div> <div class="mw-heading mw-heading3"><h3 id="Monoamine_releasing_agent">Monoamine releasing agent</h3> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=7" title="Edit section: Monoamine releasing agent" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Phenethylamine, being similar to <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a> in its action at their common <a href="/wiki/Biomolecular_target" class="mw-redirect" title="Biomolecular target">biomolecular targets</a>, is a <a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">releasing agent</a> of <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a> and <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>.<a href="#cite_note-PEA_VMAT2_MEDRS_review-12">[11]</a><a href="#cite_note-Miller-13">[12]</a><a href="#cite_note-Cites_Miller_2011_review-44">[42]</a> It is roughly <a href="/wiki/Equipotent" class="mw-redirect" title="Equipotent">equipotent</a> to amphetamine in this regard <a href="/wiki/In_vitro" title="In vitro">in vitro</a>.<a href="#cite_note-Blough2008-34">[32]</a> Phenethylamine is inactive as a <a href="/wiki/Psychostimulant" class="mw-redirect" title="Psychostimulant">psychostimulant</a> under normal circumstances due to rapid <a href="/wiki/Drug_metabolism" title="Drug metabolism">metabolism</a> by <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidase</a> (MAO), but can become active in the presence of a <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">monoamine oxidase inhibitor</a> (MAOI).<a href="#cite_note-Blough2008-34">[32]</a> <div class="mw-heading mw-heading3"><h3 id="TAAR1_agonist">TAAR1 agonist</h3> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=8" title="Edit section: TAAR1 agonist" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Phenethylamine has been shown to bind to <a href="/wiki/Human_trace_amine-associated_receptor_1" class="mw-redirect" title="Human trace amine-associated receptor 1">human trace amine-associated receptor 1</a> (hTAAR1) as an <a href="/wiki/Receptor_agonist" class="mw-redirect" title="Receptor agonist">agonist</a>.<a href="#cite_note-Human_trace_amines_and_hTAARs_October_2016_review-2">[2]</a> β-PEA is also an odorant binding TAAR4 in mice thought to mediate predator avoidance.<a href="#cite_note-Liberles_2015-45">[43]</a> <div class="mw-heading mw-heading3"><h3 id="Monoaminergic_activity_enhancer">Monoaminergic activity enhancer</h3> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=9" title="Edit section: Monoaminergic activity enhancer" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Phenethylamine is a <a href="/wiki/Monoaminergic_activity_enhancer" title="Monoaminergic activity enhancer">monoaminergic activity enhancer</a> (MAE) of <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>, and <a href="/wiki/Dopamine" title="Dopamine">dopamine</a> in addition to its catecholamine-releasing activity.<a href="#cite_note-ShimazuMiklya2004-46">[44]</a><a href="#cite_note-Knoll2003-47">[45]</a><a href="#cite_note-KnollMiklyaKnoll1996-48">[46]</a> That is, it enhances the <a href="/wiki/Action_potential" title="Action potential">action potential</a>-mediated release of these <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitters</a>.<a href="#cite_note-ShimazuMiklya2004-46">[44]</a><a href="#cite_note-Knoll2003-47">[45]</a><a href="#cite_note-KnollMiklyaKnoll1996-48">[46]</a> The compound is active as a MAE at much lower concentrations than the concentrations at which it induces the release of catecholamines.<a href="#cite_note-ShimazuMiklya2004-46">[44]</a><a href="#cite_note-Knoll2003-47">[45]</a><a href="#cite_note-KnollMiklyaKnoll1996-48">[46]</a> The MAE actions of phenethylamine and other MAEs may be mediated by TAAR1 agonism.<a href="#cite_note-HarsingKnollMiklya2022-49">[47]</a><a href="#cite_note-HarsingTimarMiklya2023-50">[48]</a> <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">Synthetic</a> and more <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> MAEs like <a href="/wiki/Phenylpropylaminopentane" title="Phenylpropylaminopentane">phenylpropylaminopentane</a> (PPAP) and <a href="/wiki/Selegiline" title="Selegiline">selegiline</a> (L-deprenyl) have been <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derived</a> from phenethylamine.<a href="#cite_note-ShimazuMiklya2004-46">[44]</a><a href="#cite_note-Knoll2003-47">[45]</a> <div class="mw-heading mw-heading3"><h3 id="Other_activities">Other activities</h3> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=10" title="Edit section: Other activities" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Unlike its derivatives <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a> (adrenaline) and <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a> (adrenaline), phenethylamine is inactive as an agonist of the <a href="/wiki/Alpha-adrenergic_receptor" class="mw-redirect" title="Alpha-adrenergic receptor">α-</a> and <a href="/wiki/%CE%92-adrenergic_receptor" class="mw-redirect" title="Β-adrenergic receptor">β-adrenergic receptors</a>.<a href="#cite_note-PinckaersBlankesteijnMircheva2024-51">[49]</a> <div class="mw-heading mw-heading3"><h3 id="Effects_in_animals_and_humans">Effects in animals and humans</h3> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=11" title="Edit section: Effects in animals and humans" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> According to <a href="/wiki/Alexander_Shulgin" title="Alexander Shulgin">Alexander Shulgin</a> in <a href="/wiki/PiHKAL" title="PiHKAL">PiHKAL</a>, phenethylamine is completely inactive in humans at doses of up to 1,600 mg <a href="/wiki/Oral_administration" title="Oral administration">orally</a> and 50 mg <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenously</a>.<a href="#cite_note-PiHKAL-52">[50]</a> This can be attributed to its extremely rapid <a href="/wiki/Catabolism" title="Catabolism">metabolic breakdown</a> rather than <a href="/wiki/Pharmacodynamic" class="mw-redirect" title="Pharmacodynamic">pharmacodynamic</a> inactivity.<a href="#cite_note-PiHKAL-52">[50]</a> Although <a href="/wiki/Exogenous" class="mw-redirect" title="Exogenous">exogenous</a> phenethylamine on its own is inactive, its metabolism can be strongly inhibited and it can thereby become active, showing <a href="/wiki/Psychostimulant" class="mw-redirect" title="Psychostimulant">psychostimulant</a> effects, when <a href="/wiki/Combination_drug" title="Combination drug">combined</a> with a <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">monoamine oxidase inhibitor</a> (MAOI), specifically <a href="/wiki/Monoamine_oxidase_B" title="Monoamine oxidase B">monoamine oxidase B</a> (MAO-B) <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a> like <a href="/wiki/Selegiline" title="Selegiline">selegiline</a>.<a href="#cite_note-YasarGoldbergGoldberg1996-53">[51]</a><a href="#cite_note-HeinonenLammintausta1991-54">[52]</a> Oral <a href="/wiki/Phenylalanine" title="Phenylalanine">L-phenylalanine</a> (a <a href="/wiki/Precursor_(biochemistry)" class="mw-redirect" title="Precursor (biochemistry)">precursor</a> of phenethylamine) and/or phenethylamine itself in combination with selegiline has been studied in the treatment of <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a> and has been reported to be effective.<a href="#cite_note-ShimazuMiklya2004-46">[44]</a><a href="#cite_note-JanssenLeysenMegens1999-55">[53]</a><a href="#cite_note-BirkmayerRiedererLinauer1984-56">[54]</a><a href="#cite_note-Sabelli1991-57">[55]</a><a href="#cite_note-SabelliFinkFawcett1996-58">[56]</a> <a href="/wiki/Misuse_potential" class="mw-redirect" title="Misuse potential">Misuse</a> of phenethylamine in combination with selegiline has also been reported.<a href="#cite_note-McKeanLeungDare2015-59">[57]</a><a href="#cite_note-MonteithGlennBauer2016-60">[58]</a> The <a href="/wiki/Median_lethal_dose" title="Median lethal dose"><abbr title="median lethal dose">LD50</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 median lethal dose values of phenethylamine include 175 mg/kg i.p. in mice, 320 mg/kg s.c. in mice, 100 mg/kg i.v. in mice, 100 mg/kg parenterally in mice, 39 mg/kg intracervically in mice, and 200 mg/kg i.p. in guinea pigs.<a href="#cite_note-PubChem-10">[10]</a> Its <a href="/wiki/Lethal_dose#Lowest_lethal_dose" title="Lethal dose"><abbr title="Lowest lethal dose">LDLo</abbr></a> values include 800 mg/kg p.o. in rats, 100 mg/kg i.p. in rats, 450 μg/kg s.c. in rats, and 300 mg/kg via an unspecified route in mice.<a href="#cite_note-PubChem-10">[10]</a> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(4)"><h2 id="Pharmacokinetics">Pharmacokinetics</h2> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=12" title="Edit section: Pharmacokinetics" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-4 collapsible-block" id="mf-section-4"> <div class="skin-invert-image"> <table role="presentation" cellpadding="0" style="border-spacing:0; clear:right; float:right;"> <tbody><tr> <td><div class="thumb tright"> <div class="thumbinner" style="width:592px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: #F0F8FF;margin-bottom:3px;">Biosynthetic pathways for <a href="/wiki/Catecholamine" title="Catecholamine">catecholamines</a> and <a href="/wiki/Trace_amine" title="Trace amine">trace amines</a> in the <a href="/wiki/Human_brain" title="Human brain">human brain</a><a href="#cite_note-Trace_amine_template_1-61">[59]</a><a href="#cite_note-Trace_amine_template_2-62">[60]</a><a href="#cite_note-CYP2D6_tyramine-dopamine_metabolism-63">[61]</a></div> <div style="position:relative; width:590px; height:465px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:5px; top:0px; width:580px; position:absolute"> <a href="https://commons.wikimedia.org/wiki/File:Catecholamine_and_trace_amine_biosynthesis.svg" title="commons:File:Catecholamine and trace amine biosynthesis.svg"><noscript><img alt="Graphic of catecholamine and trace amine biosynthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/580px-Catecholamine_and_trace_amine_biosynthesis.svg.png" decoding="async" width="580" height="458" class="mw-file-element" data-file-width="512" data-file-height="404"></noscript><span class="lazy-image-placeholder" style="width: 580px;height: 458px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/580px-Catecholamine_and_trace_amine_biosynthesis.svg.png" data-alt="Graphic of catecholamine and trace amine biosynthesis" data-width="580" data-height="458" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/870px-Catecholamine_and_trace_amine_biosynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/1160px-Catecholamine_and_trace_amine_biosynthesis.svg.png 2x" data-class="mw-file-element"> </a> </div> <div style="text-align:center; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_40x60" style="position:absolute; left:40px; top:60px; line-height:110%;"><a href="/wiki/Phenylalanine" title="Phenylalanine">L-Phenylalanine</a></div> <div id="annotation_50x185" style="position:absolute; left:50px; top:185px; line-height:110%;"><a href="/wiki/Tyrosine" title="Tyrosine">L-Tyrosine</a></div> <div id="annotation_60x315" style="position:absolute; left:60px; top:315px; line-height:110%;"><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA</a></div> <div id="annotation_50x445" style="position:absolute; left:50px; top:445px; line-height:110%;"><a href="/wiki/Adrenaline" title="Adrenaline">Epinephrine</a></div> <div id="annotation_245x60" style="position:absolute; left:245px; top:60px; line-height:110%;">Phenethylamine</div> <div id="annotation_245x185" style="position:absolute; left:245px; top:185px; line-height:110%;"><a href="/wiki/Tyramine" title="Tyramine">p-Tyramine</a></div> <div id="annotation_245x315" style="position:absolute; left:245px; top:315px; line-height:110%;"><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></div> <div id="annotation_245x445" style="position:absolute; left:245px; top:445px; line-height:110%;"><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></div> <div id="annotation_415x60" style="position:absolute; left:415px; top:60px; line-height:110%;"><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine">N-Methylphenethylamine</a></div> <div id="annotation_440x138" style="position:absolute; left:440px; top:138px; line-height:110%;"><a href="/wiki/N-Methyltyramine" title="N-Methyltyramine">N-Methyltyramine</a></div> <div id="annotation_440x228" style="position:absolute; left:440px; top:228px; line-height:110%;"><a href="/wiki/Octopamine" title="Octopamine">p-Octopamine</a></div> <div id="annotation_455x350" style="position:absolute; left:455px; top:350px; line-height:110%;"><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></div> <div id="annotation_445x445" style="position:absolute; left:445px; top:445px; line-height:110%;"><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></div> <div id="annotation_167x16" style="position:absolute; left:167px; top:16px; line-height:110%;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></div> <div id="annotation_167x145" style="position:absolute; left:167px; top:145px; line-height:110%;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></div> <div id="annotation_167x275" style="position:absolute; left:167px; top:275px; line-height:110%;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></div> <div id="annotation_164x295" style="position:absolute; left:164px; top:295px; font-size:12px; font-size:12; line-height:14px;">primary pathway</div> <div id="annotation_370x17" style="position:absolute; left:370px; top:17px; line-height:110%;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></div> <div id="annotation_360x120" style="position:absolute; left:360px; top:120px; line-height:110%;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></div> <div id="annotation_445x255" style="position:absolute; left:445px; top:255px; line-height:110%;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></div> <div id="annotation_176x407" style="position:absolute; left:176px; top:407px; line-height:110%;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></div> <div id="annotation_40x90" style="position:absolute; left:40px; top:90px; line-height:110%;"><a href="/wiki/Biopterin-dependent_aromatic_amino_acid_hydroxylase" title="Biopterin-dependent aromatic amino acid hydroxylase">AAAH</a></div> <div id="annotation_40x220" style="position:absolute; left:40px; top:220px; line-height:110%;"><a href="/wiki/Biopterin-dependent_aromatic_amino_acid_hydroxylase" title="Biopterin-dependent aromatic amino acid hydroxylase">AAAH</a></div> <div id="annotation_225x215" style="position:absolute; left:225px; top:215px; line-height:110%;">brain <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a></div> <div id="annotation_291x217" style="position:absolute; left:291px; top:217px; font-size:12px; font-size:12; line-height:14px; text-align:left;">minor pathway</div> <div id="annotation_325x350" style="position:absolute; left:325px; top:350px; line-height:110%;"><a href="/wiki/Catechol-O-methyltransferase" title="Catechol-O-methyltransferase">COMT</a></div> <div id="annotation_250x350" style="position:absolute; left:250px; top:350px; line-height:110%;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">DBH</a></div> <div id="annotation_360x185" style="position:absolute; left:360px; top:185px; line-height:110%;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">DBH</a></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><noscript><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" data-file-width="133" data-file-height="200"></noscript><span class="lazy-image-placeholder" style="width: 18px;height: 27px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" data-alt="The image above contains clickable links" data-width="18" data-height="27" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/27px-Interactive_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/36px-Interactive_icon.svg.png 2x" data-class="mw-file-element"> </div>In humans, <a href="/wiki/Catecholamine" title="Catecholamine">catecholamines</a> and phenethylaminergic <a href="/wiki/Trace_amine" title="Trace amine">trace amines</a> are derived from the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Phenylalanine" title="Phenylalanine">L-phenylalanine</a>.</div> </div> </div> </td></tr></tbody></table> </div> By <a href="/wiki/Oral_route" class="mw-redirect" title="Oral route">oral route</a>, phenethylamine's <a href="/wiki/Half-life" title="Half-life">half-life</a> is 5–10 minutes;<a href="#cite_note-PubChem-10">[10]</a> endogenously produced PEA in catecholamine neurons has a half-life of roughly 30 seconds.<a href="#cite_note-Renaissance-3">[3]</a> In humans, PEA is metabolized by <a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">phenylethanolamine N-methyltransferase</a> (PNMT),<a href="#cite_note-Renaissance-3">[3]</a><a href="#cite_note-Vascular-4">[4]</a><a href="#cite_note-HMDB_PEA-5">[5]</a><a href="#cite_note-pmid7432557-64">[62]</a> <a href="/wiki/MAO-A" class="mw-redirect" title="MAO-A">monoamine oxidase A</a> (MAO-A),<a href="#cite_note-HMDB_PEA-5">[5]</a><a href="#cite_note-PEA_MAO-A_and_B_Substrate-Suzuki-6">[6]</a> <a href="/wiki/MAO-B" class="mw-redirect" title="MAO-B">monoamine oxidase B</a> (MAO-B),<a href="#cite_note-Renaissance-3">[3]</a><a href="#cite_note-Vascular-4">[4]</a><a href="#cite_note-HMDB_PEA-5">[5]</a><a href="#cite_note-PEA_MAO-B_Substrate-Yang-16">[15]</a> the <a href="/wiki/Semicarbazide-sensitive_amine_oxidase" class="mw-redirect" title="Semicarbazide-sensitive amine oxidase">semicarbazide-sensitive amine oxidases</a> (SSAOs) <a href="/wiki/AOC2" title="AOC2">AOC2</a> and <a href="/wiki/AOC3" title="AOC3">AOC3</a>,<a href="#cite_note-HMDB_PEA-5">[5]</a><a href="#cite_note-SSAO-7">[7]</a> <a href="/wiki/Flavin-containing_monooxygenase_3" title="Flavin-containing monooxygenase 3">flavin-containing monooxygenase 3</a> (FMO3),<a href="#cite_note-FMO-8">[8]</a><a href="#cite_note-FMO3_catecholamines-9">[9]</a> and <a href="/wiki/Aralkylamine_N-acetyltransferase" title="Aralkylamine N-acetyltransferase">aralkylamine N-acetyltransferase</a> (AANAT).<a href="#cite_note-HMDB_PEA-5">[5]</a><a href="#cite_note-65">[63]</a> <a href="/wiki/N-methylphenethylamine" class="mw-redirect" title="N-methylphenethylamine">N-Methylphenethylamine</a>, an <a href="/wiki/Isomer" title="Isomer">isomer</a> of <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>, is produced in humans via the metabolism of phenethylamine by PNMT.<a href="#cite_note-Renaissance-3">[3]</a><a href="#cite_note-Vascular-4">[4]</a><a href="#cite_note-pmid7432557-64">[62]</a> <a href="/wiki/%CE%92-Phenylacetic_acid" class="mw-redirect" title="Β-Phenylacetic acid">β-Phenylacetic acid</a> is the primary urinary metabolite of phenethylamine and is produced via <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidase</a> metabolism and subsequent <a href="/wiki/Aldehyde_dehydrogenase" title="Aldehyde dehydrogenase">aldehyde dehydrogenase</a> metabolism.<a href="#cite_note-HMDB_PEA-5">[5]</a> <a href="/wiki/Phenylacetaldehyde" title="Phenylacetaldehyde">Phenylacetaldehyde</a> is the intermediate product which is produced by monoamine oxidase and then further metabolized into β-phenylacetic acid by aldehyde dehydrogenase.<a href="#cite_note-HMDB_PEA-5">[5]</a><a href="#cite_note-66">[64]</a> When the initial phenylethylamine concentration in the brain is low, brain levels can be increased 1000-fold when taking a <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">monoamine oxidase inhibitor</a> (MAOI), particularly a <a href="/wiki/Monoamine_oxidase_inhibitor#List_of_MAO_inhibiting_drugs" title="Monoamine oxidase inhibitor">MAO-B inhibitor</a>, and by 3–4 times when the initial concentration is high.<a href="#cite_note-Sabelli78-67">[65]</a> <div style="clear:both;" class=""></div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(5)"><h2 id="Notes">Notes</h2> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=13" title="Edit section: Notes" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-5 collapsible-block" id="mf-section-5"> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-11"><a href="#cite_ref-11">^</a> Synonyms and alternate spellings include: phenylethylamine, β-phenylethylamine (β-PEA), 2-phenylethylamine, 1-amino-2-phenylethane, and 2-phenylethan-1-amine. </li> <li id="cite_note-23"><a href="#cite_ref-23">^</a> In other words, all of the compounds that belong to this class are <a href="/wiki/Structural_analog#Chemistry" title="Structural analog">structural analogs</a> of phenethylamine. </li> </ol></div></div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(6)"><h2 id="References">References</h2> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=14" title="Edit section: References" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-6 collapsible-block" id="mf-section-6"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-TAAR1_and_TA_pharmacology_2016_review-1">^ <a href="#cite_ref-TAAR1_and_TA_pharmacology_2016_review_1-0">a</a> <a href="#cite_ref-TAAR1_and_TA_pharmacology_2016_review_1-1">b</a> <a href="#cite_ref-TAAR1_and_TA_pharmacology_2016_review_1-2">c</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFPeiAsif-MalikCanales2016" class="citation journal cs1">Pei Y, Asif-Malik A, Canales JJ (April 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4820462">"Trace Amines and the Trace Amine-Associated Receptor 1: Pharmacology, Neurochemistry, and Clinical Implications"</a>. Frontiers in Neuroscience. 10: 148. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3389%2Ffnins.2016.00148">10.3389/fnins.2016.00148</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4820462">4820462</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/27092049">27092049</a>. <q>Furthermore, evidence has accrued on the ability of TAs to modulate brain reward (i.e., the subjective experience of pleasure) and reinforcement (i.e., the strengthening of a conditioned response by a given stimulus; Greenshaw, 2021), suggesting the involvement of the TAs in the neurological adaptations underlying drug addiction, a chronic relapsing syndrome characterized by compulsive drug taking, inability to control drug intake and dysphoria when access to the drug is prevented (Koob, 2009). Consistent with its hypothesized role as "endogenous amphetamine," β-PEA was shown to possess reinforcing properties, a defining feature that underlies the abuse liability of amphetamine and other psychomotor stimulants. β-PEA was also as effective as amphetamine in its ability to produce conditioned place preference (i.e., the process by which an organism learns an association between drug effects and a particular place or context) in rats (Gilbert and Cooper, 1983) and was readily self-administered by dogs that had a stable history (i.e., consisting of early acquisition and later maintenance) of amphetamine or cocaine self-administration (Risner and Jones, 1977; Shannon and Thompson, 1984). In another study, high concentrations of β-PEA dose-dependently maintained responding in monkeys that were previously trained to self-administer cocaine, and pretreatment with a MAO-B inhibitor, which delayed β-PEA deactivation, further increased response rates (Bergman et al., 2001).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Frontiers+in+Neuroscience&rft.atitle=Trace+Amines+and+the+Trace+Amine-Associated+Receptor+1%3A+Pharmacology%2C+Neurochemistry%2C+and+Clinical+Implications&rft.volume=10&rft.pages=148&rft.date=2016-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4820462%23id-name%3DPMC&rft_id=info%3Apmid%2F27092049&rft_id=info%3Adoi%2F10.3389%2Ffnins.2016.00148&rft.aulast=Pei&rft.aufirst=Y&rft.au=Asif-Malik%2C+A&rft.au=Canales%2C+JJ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4820462&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenethylamine" class="Z3988"> </li> <li id="cite_note-Human_trace_amines_and_hTAARs_October_2016_review-2">^ <a href="#cite_ref-Human_trace_amines_and_hTAARs_October_2016_review_2-0">a</a> <a href="#cite_ref-Human_trace_amines_and_hTAARs_October_2016_review_2-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKhanNawaz2016" class="citation journal cs1">Khan MZ, Nawaz W (October 2016). 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Biomedicine & Pharmacotherapy. 83: 439–449. <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.biopha.2016.07.002">10.1016/j.biopha.2016.07.002</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/27424325">27424325</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biomedicine+%26+Pharmacotherapy&rft.atitle=The+emerging+roles+of+human+trace+amines+and+human+trace+amine-associated+receptors+%28hTAARs%29+in+central+nervous+system&rft.volume=83&rft.pages=439-449&rft.date=2016-10&rft_id=info%3Adoi%2F10.1016%2Fj.biopha.2016.07.002&rft_id=info%3Apmid%2F27424325&rft.aulast=Khan&rft.aufirst=MZ&rft.au=Nawaz%2C+W&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenethylamine" class="Z3988"> </li> <li id="cite_note-Renaissance-3">^ <a href="#cite_ref-Renaissance_3-0">a</a> <a href="#cite_ref-Renaissance_3-1">b</a> <a href="#cite_ref-Renaissance_3-2">c</a> <a href="#cite_ref-Renaissance_3-3">d</a> <a href="#cite_ref-Renaissance_3-4">e</a> <a href="#cite_ref-Renaissance_3-5">f</a> <a href="#cite_ref-Renaissance_3-6">g</a> <a href="#cite_ref-Renaissance_3-7">h</a> <a href="#cite_ref-Renaissance_3-8">i</a> <a href="#cite_ref-Renaissance_3-9">j</a> <a href="#cite_ref-Renaissance_3-10">k</a> <a href="#cite_ref-Renaissance_3-11">l</a> <a href="#cite_ref-Renaissance_3-12">m</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLindemannHoener2005" class="citation journal cs1">Lindemann L, Hoener MC (May 2005). 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In addition to the various beneficial effects for brain function mainly attributed to an upregulation of peptide growth factors [52,53], exercise induces a rapidly enhanced excretion of the main β-PEA metabolite β-phenylacetic acid (b-PAA) by on average 77%, compared with resting control subjects [54], which mirrors increased β-PEA synthesis in view of its limited endogenous pool half-life of ~30 s [18,55].</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Trends+in+Pharmacological+Sciences&rft.atitle=A+renaissance+in+trace+amines+inspired+by+a+novel+GPCR+family&rft.volume=26&rft.issue=5&rft.pages=274-281&rft.date=2005-05&rft_id=info%3Adoi%2F10.1016%2Fj.tips.2005.03.007&rft_id=info%3Apmid%2F15860375&rft.aulast=Lindemann&rft.aufirst=L&rft.au=Hoener%2C+MC&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenethylamine" class="Z3988"> </li> <li id="cite_note-Vascular-4">^ <a href="#cite_ref-Vascular_4-0">a</a> <a href="#cite_ref-Vascular_4-1">b</a> <a href="#cite_ref-Vascular_4-2">c</a> <a href="#cite_ref-Vascular_4-3">d</a> <a href="#cite_ref-Vascular_4-4">e</a> <a href="#cite_ref-Vascular_4-5">f</a> <a href="#cite_ref-Vascular_4-6">g</a> <a href="#cite_ref-Vascular_4-7">h</a> <a href="#cite_ref-Vascular_4-8">i</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBroadley2010" class="citation journal cs1">Broadley KJ (March 2010). 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"Biomarkers and attention-deficit/hyperactivity disorder: a systematic review and meta-analyses". Journal of the American Academy of Child and Adolescent Psychiatry. 51 (10): 1003–1019.e20. <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.jaac.2012.08.015">10.1016/j.jaac.2012.08.015</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/23021477">23021477</a>. <q>Although we did not find a sufficient number of studies suitable for a meta-analysis of PEA and ADHD, three studies20,57,58 confirmed that urinary levels of PEA were significantly lower in patients with ADHD compared with controls. ... Administration of D-amphetamine and methylphenidate resulted in a markedly increased urinary excretion of PEA,20,60 suggesting that ADHD treatments normalize PEA levels. ... Similarly, urinary biogenic trace amine PEA levels could be a biomarker for the diagnosis of ADHD,20,57,58 for treatment efficacy,20,60 and associated with symptoms of inattentivenesss.59 ... With regard to zinc supplementation, a placebo controlled trial reported that doses up to 30 mg/day of zinc were safe for at least 8 weeks, but the clinical effect was equivocal except for the finding of a 37% reduction in amphetamine optimal dose with 30 mg per day of zinc.110</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Academy+of+Child+and+Adolescent+Psychiatry&rft.atitle=Biomarkers+and+attention-deficit%2Fhyperactivity+disorder%3A+a+systematic+review+and+meta-analyses&rft.volume=51&rft.issue=10&rft.pages=1003-1019.e20&rft.date=2012-10&rft_id=info%3Adoi%2F10.1016%2Fj.jaac.2012.08.015&rft_id=info%3Apmid%2F23021477&rft.aulast=Scassellati&rft.aufirst=C&rft.au=Bonvicini%2C+C&rft.au=Faraone%2C+SV&rft.au=Gennarelli%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenethylamine" class="Z3988"> </li> <li id="cite_note-PEA_exercise_primary-29">^ <a href="#cite_ref-PEA_exercise_primary_29-0">a</a> <a href="#cite_ref-PEA_exercise_primary_29-1">b</a> <a href="#cite_ref-PEA_exercise_primary_29-2">c</a> <a href="#cite_ref-PEA_exercise_primary_29-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSzaboBillettTurner2001" class="citation journal cs1">Szabo A, Billett E, Turner J (October 2001). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1724404">"Phenylethylamine, a possible link to the antidepressant effects of exercise?"</a>. 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As phenylacetic acid reflects phenylethylamine levels3, and the latter has antidepressant effects, the antidepressant effects of exercise appear to be linked to increased phenylethylamine concentrations. Furthermore, considering the structural and pharmacological analogy between amphetamines and phenylethylamine, it is conceivable that phenylethylamine plays a role in the commonly reported "runners high" thought to be linked to cerebral β-endorphin activity. The substantial increase in phenylacetic acid excretion in this study implies that phenylethylamine levels are affected by exercise. ... A 30 minute bout of moderate to high intensity aerobic exercise increases phenylacetic acid levels in healthy regularly exercising men. 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</section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(7)"><h2 id="External_links">External links</h2> <a role="button" href="/w/index.php?title=Phenethylamine&action=edit&section=15" title="Edit section: External links" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-7 collapsible-block" id="mf-section-7"> <ul><li><a rel="nofollow" class="external text" href="http://gmd.mpimp-golm.mpg.de/Spectrums/af2a22f3-4aa9-4e5c-9e61-bf278b87a7c4.aspx">Phenethylamine MS Spectrum</a></li> <li><a rel="nofollow" class="external text" href="https://isomerdesign.com/pihkal/explore/142">PEA (phenethylamine) - isomer design</a> (<a rel="nofollow" class="external text" href="https://isomerdesign.com/pihkal/read/pk/142">PiHKAL entry</a>)</li></ul> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" 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href="/w/index.php?title=Phenethylamine&action=history"> <div class="post-content last-modified-bar__content"> Last edited on 19 November 2024, at 03:19 </div> </a> <div class="post-content footer-content"> <div id='mw-data-after-content'> <div class="read-more-container"></div> </div> <div id="p-lang"> <h4>Languages</h4> <section> <ul id="p-variants" class="minerva-languages"></ul> <ul class="minerva-languages"><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%8A%D9%86%D9%8A%D8%AB%D9%8A%D9%84%D8%A7%D9%85%D9%8A%D9%86" title="فينيثيلامين – Arabic" lang="ar" hreflang="ar" data-title="فينيثيلامين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B8%D0%BB%D0%B5%D1%82%D0%B8%D0%BB%D0%B0%D0%BC%D0%B8%D0%BD" title="Фенилетиламин – Bulgarian" lang="bg" hreflang="bg" data-title="Фенилетиламин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target">Български</a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Fenetilamin" title="Fenetilamin – Bosnian" lang="bs" hreflang="bs" data-title="Fenetilamin" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target">Bosanski</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Fenetilamina" title="Fenetilamina – Catalan" lang="ca" hreflang="ca" data-title="Fenetilamina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Fenylethylamin" title="Fenylethylamin – Czech" lang="cs" hreflang="cs" data-title="Fenylethylamin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Phenethylamin" title="Phenethylamin – Danish" lang="da" hreflang="da" data-title="Phenethylamin" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Phenethylamin" title="Phenethylamin – German" lang="de" hreflang="de" data-title="Phenethylamin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/2-%CF%86%CE%B1%CE%B9%CE%BD%CF%85%CE%BB%CE%B1%CE%B9%CE%B8%CE%B1%CE%BD%CE%B1%CE%BC%CE%AF%CE%BD%CE%B7" title="2-φαινυλαιθαναμίνη – Greek" lang="el" hreflang="el" data-title="2-φαινυλαιθαναμίνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Feniletilamina" title="Feniletilamina – Spanish" lang="es" hreflang="es" data-title="Feniletilamina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Fenetilamino" title="Fenetilamino – Esperanto" lang="eo" hreflang="eo" data-title="Fenetilamino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target">Esperanto</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%D9%86%D8%AA%DB%8C%D9%84%E2%80%8C%D8%A2%D9%85%DB%8C%D9%86" title="فنتیل‌آمین – Persian" lang="fa" hreflang="fa" data-title="فنتیل‌آمین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/2-Ph%C3%A9nyl%C3%A9thylamine" title="2-Phényléthylamine – French" lang="fr" hreflang="fr" data-title="2-Phényléthylamine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8E%9C%EC%97%90%ED%8B%B8%EC%95%84%EB%AF%BC" title="펜에틸아민 – Korean" lang="ko" hreflang="ko" data-title="펜에틸아민" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Feniletilamin" title="Feniletilamin – Croatian" lang="hr" hreflang="hr" data-title="Feniletilamin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/2-feniletilammina" title="2-feniletilammina – Italian" lang="it" hreflang="it" data-title="2-feniletilammina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A4%D7%A0%D7%AA%D7%99%D7%9C%D7%90%D7%9E%D7%99%D7%9F" title="פנתילאמין – Hebrew" lang="he" hreflang="he" data-title="פנתילאמין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Fenetilam%C4%ABns" title="Fenetilamīns – Latvian" lang="lv" hreflang="lv" data-title="Fenetilamīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target">Latviešu</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Fenetil-amin" title="Fenetil-amin – Hungarian" lang="hu" hreflang="hu" data-title="Fenetil-amin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Fenylethylamine" title="Fenylethylamine – Dutch" lang="nl" hreflang="nl" data-title="Fenylethylamine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%82%A7%E3%83%8D%E3%83%81%E3%83%AB%E3%82%A2%E3%83%9F%E3%83%B3" title="フェネチルアミン – Japanese" lang="ja" hreflang="ja" data-title="フェネチルアミン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Fenetylamin" title="Fenetylamin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Fenetylamin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Fenetylamin" title="Fenetylamin – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Fenetylamin" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target">Norsk nynorsk</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/2-Fenyloetyloamina" title="2-Fenyloetyloamina – Polish" lang="pl" hreflang="pl" data-title="2-Fenyloetyloamina" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Feniletilamina" title="Feniletilamina – Portuguese" lang="pt" hreflang="pt" data-title="Feniletilamina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Fenetilamin%C4%83" title="Fenetilamină – Romanian" lang="ro" hreflang="ro" data-title="Fenetilamină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B8%D0%BB%D1%8D%D1%82%D0%B8%D0%BB%D0%B0%D0%BC%D0%B8%D0%BD" title="Фенилэтиламин – Russian" lang="ru" hreflang="ru" data-title="Фенилэтиламин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Fenyletylam%C3%ADn" title="Fenyletylamín – Slovak" lang="sk" hreflang="sk" data-title="Fenyletylamín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target">Slovenčina</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Fenetilamin" title="Fenetilamin – Serbian" lang="sr" hreflang="sr" data-title="Fenetilamin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Fenetilamin" title="Fenetilamin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Fenetilamin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Fenyylietyyliamiini" title="Fenyylietyyliamiini – Finnish" lang="fi" hreflang="fi" data-title="Fenyylietyyliamiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Fenetylamin" title="Fenetylamin – Swedish" lang="sv" hreflang="sv" data-title="Fenetylamin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Feniletilamin" title="Feniletilamin – Turkish" lang="tr" hreflang="tr" data-title="Feniletilamin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D1%96%D0%BB%D0%B5%D1%82%D0%B8%D0%BB%D0%B0%D0%BC%D1%96%D0%BD" title="Фенілетиламін – Ukrainian" lang="uk" hreflang="uk" data-title="Фенілетиламін" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Phenethylamin" title="Phenethylamin – Vietnamese" lang="vi" hreflang="vi" data-title="Phenethylamin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%8B%AF%E4%B9%99%E8%83%BA" title="苯乙胺 – Chinese" lang="zh" hreflang="zh" data-title="苯乙胺" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target">中文</a></li></ul> </section> </div> <div class="minerva-footer-logo"><img src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" alt="Wikipedia" width="120" height="18" style="width: 7.5em; height: 1.125em;"/> </div> <ul id="footer-info" class="footer-info hlist hlist-separated"> <li id="footer-info-lastmod"> This page was last edited on 19 November 2024, at 03:19 (UTC).</li> <li id="footer-info-copyright">Content is available under <a class="external" rel="nofollow" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">CC BY-SA 4.0</a> unless otherwise noted.</li> </ul> <ul id="footer-places" class="footer-places hlist hlist-separated"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a href="/wiki/Wikipedia:About">About 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