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</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:204px;max-width:204px"><div class="trow"><div class="theader">Catecholamines</div></div><div class="trow"><div class="tsingle" style="width:202px;max-width:202px"><div class="thumbimage"><span typeof="mw:File"></span></div><div class="thumbcaption"><a href="Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a> (adrenaline)</div></div></div><div class="trow"><div class="tsingle" style="width:202px;max-width:202px"><div class="thumbimage"><span typeof="mw:File"></span></div><div class="thumbcaption"><a href="Norepinephrine" title="Norepinephrine">Norepinephrine</a> (noradrenaline)</div></div></div><div class="trow"><div class="tsingle" style="width:202px;max-width:202px"><div class="thumbimage"><span typeof="mw:File"></span></div><div class="thumbcaption"><a href="Dopamine" title="Dopamine">Dopamine</a></div></div></div></div></div></div>

<p>A <b>catecholamine</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa">/<span style="border-bottom:1px dotted"><span title="/ˌ/: secondary stress follows">ˌ</span><span title="'k' in 'kind'">k</span><span title="/æ/: 'a' in 'bad'">æ</span><span title="'t' in 'tie'">t</span><span title="/ə/: 'a' in 'about'">ə</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'k' in 'kind'">k</span><span title="/oʊ/: 'o' in 'code'">oʊ</span><span title="'l' in 'lie'">l</span><span title="/ə/: 'a' in 'about'">ə</span><span title="'m' in 'my'">m</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</span></span>; abbreviated <b>CA</b>), most typically a <b>3,4-dihydroxyphenethylamine</b>, is a <a href="Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitter</a>, an <a href="Organic_compound" title="Organic compound">organic compound</a> that has a <a href="Catechol" title="Catechol">catechol</a> (<a href="Benzene" title="Benzene">benzene</a> with two <a href="Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> side groups next to each other) and a <a href="Side_chain" title="Side chain">side-chain</a> <a href="Amine" title="Amine">amine</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>

</p><p><a href="Catechol" title="Catechol">Catechol</a> can be either a free molecule or a <a href="Substituent" title="Substituent">substituent</a> of a larger molecule, where it represents a 1,2-dihydroxybenzene group.

</p><p>Catecholamines are derived from the <a href="Amino_acid" title="Amino acid">amino acid</a> <a href="Tyrosine" title="Tyrosine">tyrosine</a>, which is derived from dietary sources as well as synthesis from <a href="Phenylalanine" title="Phenylalanine">phenylalanine</a>.<sup id="cite_ref-Purves_2-0" class="reference"><a href="#cite_note-Purves-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Catecholamines are water-soluble and are 50% bound to plasma proteins in circulation.

</p><p>Included among catecholamines are <a href="Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a> (adrenaline), <a href="Norepinephrine" title="Norepinephrine">norepinephrine</a> (noradrenaline), and <a href="Dopamine" title="Dopamine">dopamine</a>. Release of the <a href="Hormone" title="Hormone">hormones</a> epinephrine and norepinephrine from the <a href="Adrenal_medulla" title="Adrenal medulla">adrenal medulla</a> of the <a href="Adrenal_gland" title="Adrenal gland">adrenal glands</a> is part of the <a href="Fight-or-flight_response" title="Fight-or-flight response">fight-or-flight response</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>

</p><p>Tyrosine is created from phenylalanine by <a href="Hydroxylation" title="Hydroxylation">hydroxylation</a> by the enzyme <a href="Phenylalanine_hydroxylase" title="Phenylalanine hydroxylase">phenylalanine hydroxylase</a>. Tyrosine is also ingested directly from dietary protein. Catecholamine-secreting cells use several reactions to convert tyrosine serially to <a href="L-DOPA" title="L-DOPA"><small>L</small>-DOPA</a> and then to dopamine. Depending on the cell type, dopamine may be further converted to norepinephrine or even further converted to epinephrine.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>

</p><p>Various <a href="Stimulant" title="Stimulant">stimulant</a> drugs (such as a number of <a href="Substituted_amphetamine" title="Substituted amphetamine">substituted amphetamines</a>) are catecholamine analogues.

</p>

<div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2></div>

<p>Catecholamines have the distinct structure of a <a href="Benzene_ring" class="mw-redirect" title="Benzene ring">benzene ring</a> with two <a href="Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> groups, an intermediate <a href="Ethyl_group" title="Ethyl group">ethyl</a> chain, and a terminal <a href="Amine" title="Amine">amine</a> group. Phenylethanolamines such as norepinephrine have a hydroxyl group on the ethyl chain.

</p>

<div class="mw-heading mw-heading2"><h2 id="Production_and_degradation">Production and degradation</h2></div>

<div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: light-dark(#F0F8FF,var(--background-color-neutral)); color:var(--color-base,light-dark(#202122,#eaecf0)); margin-bottom:3px;">Biosynthetic pathways for and <a href="Trace_amine" title="Trace amine">trace amines</a> in the <a href="Human_brain" title="Human brain">human brain</a><sup id="cite_ref-Trace_amine_template_1_5-0" class="reference"><a href="#cite_note-Trace_amine_template_1-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Trace_amine_template_2_6-0" class="reference"><a href="#cite_note-Trace_amine_template_2-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CYP2D6_tyramine-dopamine_metabolism_7-0" class="reference"><a href="#cite_note-CYP2D6_tyramine-dopamine_metabolism-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></div>

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<div style="background-color:transparent; color:var(--color-base,#202122)"><div id="annotation_40x60" style="position:absolute; left:40px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="Phenylalanine" title="Phenylalanine"><small>L</small>-Phenylalanine</a></span></div>

<div id="annotation_50x185" style="position:absolute; left:50px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="Tyrosine" title="Tyrosine"><small>L</small>-Tyrosine</a></span></div>

<div id="annotation_50x445" style="position:absolute; left:50px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><mark style="color:black;background:yellow"><a href="Adrenaline" title="Adrenaline">Epinephrine</a></mark></span></div>

<div id="annotation_245x60" style="position:absolute; left:245px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="Phenethylamine" title="Phenethylamine">Phenethylamine</a></span></div>

<div id="annotation_245x185" style="position:absolute; left:245px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></span></div>

<div id="annotation_245x315" style="position:absolute; left:245px; top:315px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><mark style="color:black;background:yellow"><a href="Dopamine" title="Dopamine">Dopamine</a></mark></span></div>

<div id="annotation_245x445" style="position:absolute; left:245px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><mark style="color:black;background:yellow"><a href="Norepinephrine" title="Norepinephrine">Norepinephrine</a></mark></span></div>

<div id="annotation_415x60" style="position:absolute; left:415px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></span></div>

<div id="annotation_440x138" style="position:absolute; left:440px; top:138px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="N-Methyltyramine" title="N-Methyltyramine"><i>N</i>-Methyltyramine</a></span></div>

<div id="annotation_440x228" style="position:absolute; left:440px; top:228px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></span></div>

<div id="annotation_455x350" style="position:absolute; left:455px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="Synephrine" title="Synephrine">Synephrine</a></span></div>

<div id="annotation_445x445" style="position:absolute; left:445px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></span></div>

<div id="annotation_164x295" style="position:absolute; left:164px; top:295px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;">primary<br>pathway</span></div>

<div id="annotation_225x215" style="position:absolute; left:225px; top:215px; line-height:110%;"><span style="background-color:transparent; color:inherit;">brain<br><a href="CYP2D6" title="CYP2D6">CYP2D6</a></span></div>

<div id="annotation_291x217" style="position:absolute; left:291px; top:217px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;">minor<br>pathway</span></div>

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<div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><span typeof="mw:File"><span title="The image above contains clickable links"></span></span></div>In humans, catecholamines (shown in yellow) are derived from the <a href="Amino_acid" title="Amino acid">amino acid</a> <small>L</small>-phenylalanine.<br><small>L</small>-Phenylalanine is converted into <small>L</small>-tyrosine by an <a href="Aromatic_amino_acid_hydroxylase" class="mw-redirect" title="Aromatic amino acid hydroxylase">aromatic amino acid hydroxylase (AAAH)</a> enzyme (<a href="Phenylalanine_4-hydroxylase" class="mw-redirect" title="Phenylalanine 4-hydroxylase">phenylalanine 4-hydroxylase</a>), with molecular <a href="Oxygen" title="Oxygen">oxygen</a> (O<sub>2</sub>) and <a href="Tetrahydrobiopterin" title="Tetrahydrobiopterin">tetrahydrobiopterin</a> as <a href="Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactors</a>. <small>L</small>-Tyrosine is converted into <small>L</small>-DOPA by another AAAH enzyme (<a href="Tyrosine_3-hydroxylase" class="mw-redirect" title="Tyrosine 3-hydroxylase">tyrosine 3-hydroxylase</a>) with <a href="Tetrahydrobiopterin" title="Tetrahydrobiopterin">tetrahydrobiopterin</a>, O<sub>2</sub>, and <a href="Ferrous" title="Ferrous">ferrous</a> <a href="Iron" title="Iron">iron</a> (Fe<sup>2+</sup>) as cofactors. <small>L</small>-DOPA is converted into dopamine by the enzyme <a href="Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">aromatic <small>L</small>-amino acid decarboxylase (AADC)</a>, with <a href="Pyridoxal_phosphate" title="Pyridoxal phosphate">pyridoxal phosphate</a> as the cofactor. Dopamine itself is also used as precursor in the synthesis of the neurotransmitters <a href="Norepinephrine" title="Norepinephrine">norepinephrine</a> and <a href="Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a>. Dopamine is converted into norepinephrine by the enzyme <a href="Dopamine_beta_hydroxylase" class="mw-redirect" title="Dopamine beta hydroxylase">dopamine β-hydroxylase (DBH)</a>, with O<sub>2</sub> and <a href="Ascorbic_acid" class="mw-redirect" title="Ascorbic acid"><small>L</small>-ascorbic acid</a> as cofactors. Norepinephrine is converted into epinephrine by the enzyme <a href="Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">phenylethanolamine <i>N</i>-methyltransferase</a> (PNMT) with <a href="S-Adenosyl_methionine" title="S-Adenosyl methionine"><i>S</i>-adenosyl-<small>L</small>-methionine</a> as the cofactor.</div>

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<div class="mw-heading mw-heading3"><h3 id="Location">Location</h3></div>

<p>Catecholamines are produced mainly by the <a href="Chromaffin_cells" class="mw-redirect" title="Chromaffin cells">chromaffin cells</a> of the <a href="Adrenal_medulla" title="Adrenal medulla">adrenal medulla</a> and the <a href="Postganglionic_fiber" class="mw-redirect" title="Postganglionic fiber">postganglionic fibers</a> of the <a href="Sympathetic_nervous_system" title="Sympathetic nervous system">sympathetic nervous system</a>. <a href="Dopamine" title="Dopamine">Dopamine</a>, which acts as a <a href="Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> in the <a href="Central_nervous_system" title="Central nervous system">central nervous system</a>, is largely produced in neuronal cell bodies in two areas of the brainstem: the <a href="Ventral_tegmental_area" title="Ventral tegmental area">ventral tegmental area</a> and the <a href="Substantia_nigra" title="Substantia nigra">substantia nigra</a>, the latter of which contains <a href="Neuromelanin" title="Neuromelanin">neuromelanin</a>-pigmented neurons. The similarly neuromelanin-pigmented cell bodies of the <a href="Locus_coeruleus" title="Locus coeruleus">locus coeruleus</a> produce <a href="Norepinephrine" title="Norepinephrine">norepinephrine</a>. <a href="Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a> is produced in small groups of neurons in the human brain which express its synthesizing enzyme, <a href="Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">phenylethanolamine <i>N</i>-methyltransferase</a>;<sup id="cite_ref-Human_PNMT_neurons_8-0" class="reference"><a href="#cite_note-Human_PNMT_neurons-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> these neurons project from a nucleus that is adjacent (ventrolateral) to the <a href="Area_postrema" title="Area postrema">area postrema</a> and from a nucleus in the dorsal region of the <a href="Solitary_tract" title="Solitary tract">solitary tract</a>.<sup id="cite_ref-Human_PNMT_neurons_8-1" class="reference"><a href="#cite_note-Human_PNMT_neurons-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3></div>

<p>Dopamine is the first catecholamine synthesized from DOPA. In turn, norepinephrine and epinephrine are derived from further metabolic modification of dopamine. The enzyme dopamine hydroxylase requires copper as a <a href="Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactor</a> (not shown in the diagram) and DOPA decarboxylase requires <a href="Pyridoxal_phosphate" title="Pyridoxal phosphate">PLP</a> (not shown in the diagram). The rate limiting step in catecholamine biosynthesis through the predominant metabolic pathway is the hydroxylation of <small>L</small>-tyrosine to <small>L</small>-DOPA.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup>

</p><p>Catecholamine synthesis is inhibited by alpha-methyl-<i>p</i>-tyrosine (<a href="AMPT" class="mw-redirect" title="AMPT">AMPT</a>), which inhibits <a href="Tyrosine_hydroxylase" title="Tyrosine hydroxylase">tyrosine hydroxylase</a>.

</p><p>The amino acids <a href="Phenylalanine" title="Phenylalanine">phenylalanine</a> and <a href="Tyrosine" title="Tyrosine">tyrosine</a> are precursors for catecholamines. Both amino acids are found in high concentrations in <a href="Blood_plasma" title="Blood plasma">blood plasma</a> and the brain. In mammals, tyrosine can be formed from dietary phenylalanine by the enzyme <a href="Phenylalanine_hydroxylase" title="Phenylalanine hydroxylase">phenylalanine hydroxylase</a>, found in large amounts in the liver. Insufficient amounts of phenylalanine hydroxylase result in <a href="Phenylketonuria" title="Phenylketonuria">phenylketonuria</a>, a metabolic disorder that leads to intellectual deficits unless treated by dietary manipulation. Catecholamine synthesis is usually considered to begin with tyrosine. The enzyme <a href="Tyrosine_hydroxylase" title="Tyrosine hydroxylase">tyrosine hydroxylase</a> (TH) converts the amino acid <small>L</small>-tyrosine into 3,4-dihydroxyphenylalanine (<small>L</small>-DOPA). The hydroxylation of <small>L</small>-tyrosine by TH results in the formation of the DA precursor <small>L</small>-DOPA, which is metabolized by <a href="Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">aromatic <small>L</small>-amino acid decarboxylase</a> (AADC; see Cooper et al., 2002) to the transmitter dopamine. This step occurs so rapidly that it is difficult to measure <small>L</small>-DOPA in the brain without first inhibiting AADC. In <a href="Neuron" title="Neuron">neurons</a> that use DA as the transmitter, the decarboxylation of <small>L</small>-DOPA to dopamine is the final step in formation of the transmitter; however, in those neurons using <a href="Norepinephrine" title="Norepinephrine">norepinephrine</a> (noradrenaline) or <a href="Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a> (adrenaline) as transmitters, the enzyme <a href="Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">dopamine β-hydroxylase</a> (DBH), which converts dopamine to yield norepinephrine, is also present. In still other neurons in which epinephrine is the transmitter, a third enzyme <a href="Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">phenylethanolamine <i>N</i>-methyltransferase (PNMT)</a> converts norepinephrine into epinephrine. Thus, a cell that uses epinephrine as its transmitter contains four enzymes (TH, AADC, DBH, and PNMT), whereas norepinephrine neurons contain only three enzymes (lacking PNMT) and dopamine cells only two (TH and AADC).

</p>

<div class="mw-heading mw-heading3"><h3 id="Degradation">Degradation</h3></div>

<p>Catecholamines have a half-life of a few minutes when circulating in the blood. They can be degraded either by methylation by <a href="Catechol-O-methyl_transferase" class="mw-redirect" title="Catechol-O-methyl transferase">catechol-<i>O</i>-methyltransferases (COMT)</a> or by deamination by <a href="Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidases (MAO)</a>.

</p><p><a href="MAOI" class="mw-redirect" title="MAOI">MAOIs</a> bind to MAO, thereby preventing it from breaking down catecholamines and other monoamines.

</p>

<p><a href="Catabolism" title="Catabolism">Catabolism</a> of catecholamines is mediated by two main enzymes: catechol-<i>O</i>-methyltransferase (COMT) which is present in the synaptic cleft and cytosol of the cell and monoamine oxidase (MAO) which is located in the mitochondrial membrane. Both enzymes require cofactors: COMT uses <a href="Magnesium_in_biology" title="Magnesium in biology">Mg<sup>2+</sup></a> as a cofactor while MAO uses <a href="Flavin_adenine_dinucleotide" title="Flavin adenine dinucleotide">FAD</a>. The first step of the catabolic process is mediated by either MAO or COMT which depends on the tissue and location of catecholamines (for example degradation of catecholamines in the synaptic cleft is mediated by COMT because MAO is a mitochondrial enzyme). The next catabolic steps in the pathway involve <a href="Alcohol_dehydrogenase" title="Alcohol dehydrogenase">alcohol dehydrogenase</a>, <a href="Aldehyde_dehydrogenase" title="Aldehyde dehydrogenase">aldehyde dehydrogenase</a> and <a href="Aldehyde_reductase" class="mw-redirect" title="Aldehyde reductase">aldehyde reductase</a>. The end product of epinephrine and norepinephrine is <a href="Vanillylmandelic_acid" title="Vanillylmandelic acid">vanillylmandelic acid (VMA)</a> which is excreted in the <a href="Urine" title="Urine">urine</a>. Dopamine catabolism leads to the production of <a href="Homovanillic_acid" title="Homovanillic acid">homovanillic acid (HVA)</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading2"><h2 id="Function">Function</h2></div>

<div class="mw-heading mw-heading3"><h3 id="Modality">Modality</h3></div>

<p>Two catecholamines, <a href="Norepinephrine" title="Norepinephrine">norepinephrine</a> and <a href="Dopamine" title="Dopamine">dopamine</a>, act as <a href="Neuromodulators" class="mw-redirect" title="Neuromodulators">neuromodulators</a> in the <a href="Central_nervous_system" title="Central nervous system">central nervous system</a> and as hormones in the blood circulation. The catecholamine <a href="Norepinephrine" title="Norepinephrine">norepinephrine</a> is a neuromodulator of the peripheral sympathetic nervous system but is also present in the blood (mostly through "spillover" from the <a href="Synapse" title="Synapse">synapses</a> of the sympathetic system).

</p><p>High catecholamine levels in blood are associated with <a href="Stress_(medicine)" class="mw-redirect" title="Stress (medicine)">stress</a>, which can be induced from psychological reactions or environmental stressors such as <a href="Noise_health_effects" class="mw-redirect" title="Noise health effects">elevated sound levels</a>, <a href="Light_pollution" title="Light pollution">intense light</a>, or <a href="Hypoglycemia" title="Hypoglycemia">low blood sugar levels</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup>

</p><p>Extremely high levels of catecholamines (also known as catecholamine toxicity) can occur in <a href="Central_nervous_system" title="Central nervous system">central nervous system</a> trauma due to stimulation or damage of <a href="Nucleus_(neuroanatomy)" title="Nucleus (neuroanatomy)">nuclei</a> in the <a href="Brainstem" title="Brainstem">brainstem</a>, in particular, those nuclei affecting the <a href="Sympathetic_nervous_system" title="Sympathetic nervous system">sympathetic nervous system</a>. In <a href="Emergency_medicine" title="Emergency medicine">emergency medicine</a>, this occurrence is widely known as a "catecholamine dump".

</p><p>Extremely high levels of catecholamine can also be caused by <a href="Neuroendocrine_tumor" title="Neuroendocrine tumor">neuroendocrine tumors</a> in the <a href="Adrenal_medulla" title="Adrenal medulla">adrenal medulla</a>, a treatable condition known as <a href="Pheochromocytoma" title="Pheochromocytoma">pheochromocytoma</a>.

</p><p>High levels of catecholamines can also be caused by <a href="Monoamine_oxidase_A" title="Monoamine oxidase A">monoamine oxidase A (MAO-A)</a> deficiency, known as <a href="Brunner_syndrome" title="Brunner syndrome">Brunner syndrome</a>. As MAO-A is one of the enzymes responsible for degradation of these neurotransmitters, its deficiency increases the <a href="Bioavailability" title="Bioavailability">bioavailability</a> of these neurotransmitters considerably. It occurs in the absence of <a href="Pheochromocytoma" title="Pheochromocytoma">pheochromocytoma</a>, <a href="Neuroendocrine_tumor" title="Neuroendocrine tumor">neuroendocrine tumors</a>, and <a href="Carcinoid_syndrome" title="Carcinoid syndrome">carcinoid syndrome</a>, but it looks similar to carcinoid syndrome with symptoms such as facial flushing and aggression.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup>

</p><p>Acute <a href="Porphyria" title="Porphyria">porphyria</a> can cause elevated catecholamines.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading2"><h2 id="Aging">Aging</h2></div>

<p>Degeneration of the <a href="Locus_coeruleus" title="Locus coeruleus">locus coeruleus</a> and reduced production of norepinephrine during aging are under preliminary research as possible factors in the pathogenesis of <a href="Alzheimer's_disease" title="Alzheimer's disease">Alzheimer's disease</a>.<sup id="cite_ref-heneka_15-0" class="reference"><a href="#cite_note-heneka-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading2"><h2 id="Physiological_effects">Physiological effects</h2></div>

<p>Catecholamines cause general physiological changes that prepare the body for physical activity (the <a href="Fight-or-flight_response" title="Fight-or-flight response">fight-or-flight response</a>). Some typical effects are increases in <a href="Heart_rate" title="Heart rate">heart rate</a>, <a href="Blood_pressure" title="Blood pressure">blood pressure</a>, <a href="Blood_glucose" class="mw-redirect" title="Blood glucose">blood glucose</a> levels, and a general reaction of the <a href="Sympathetic_nervous_system" title="Sympathetic nervous system">sympathetic nervous system</a>. Some drugs, like <a href="Tolcapone" title="Tolcapone">tolcapone</a> (a central <a href="COMT" class="mw-redirect" title="COMT">COMT</a>-inhibitor), raise the levels of all the catecholamines. Increased catecholamines may also cause an increased respiratory rate (<a href="Tachypnea" title="Tachypnea">tachypnoea</a>) in patients.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup>

</p><p>Catecholamine is secreted into urine after being broken down, and its secretion level can be measured for the diagnosis of illnesses associated with catecholamine levels in the body.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> <a href="Clinical_urine_tests" class="mw-redirect" title="Clinical urine tests">Urine testing</a> for catecholamine is used to detect <a href="Pheochromocytoma" title="Pheochromocytoma">pheochromocytoma</a>.

</p>

<div class="mw-heading mw-heading3"><h3 id="Function_in_plants">Function in plants</h3></div>

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</style><blockquote class="templatequote"><p>They have been found in 44 plant families, but no essential metabolic function has been established for them. They are precursors of benzo[<i>c</i>]phenanthridine <a href="Alkaloid" title="Alkaloid">alkaloids</a>, which are the active principal ingredients of many <a href="Medicinal_plant" class="mw-redirect" title="Medicinal plant">medicinal plant</a> extracts. CAs have been implicated to have a possible protective role against insect predators, injuries, and nitrogen detoxification. They have been shown to promote plant tissue growth, somatic <a href="Embryogenesis" class="mw-redirect" title="Embryogenesis">embryogenesis</a> from in vitro cultures, and flowering. CAs inhibit <a href="Indole-3-acetic_acid" title="Indole-3-acetic acid">indole-3-acetic acid</a> oxidation and enhance <a href="Ethylene" title="Ethylene">ethylene</a> biosynthesis. They have also been shown to enhance synergistically various effects of <a href="Gibberellin" title="Gibberellin">gibberellins</a>.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup></p></blockquote>

<div class="mw-heading mw-heading2"><h2 id="Testing_for_catecholamines">Testing for catecholamines</h2></div>

<p>Catecholamines are secreted by cells in tissues of different systems of the human body, mostly by the nervous and the endocrine systems. The adrenal glands secrete certain catecholamines into the blood when the person is physically or mentally stressed and this is usually a healthy physiological response. However, acute or chronic excess of circulating catecholamines can potentially increase blood pressure and heart rate to very high levels and eventually provoke dangerous effects. Tests for fractionated plasma free <a href="Metanephrines" title="Metanephrines">metanephrines</a> or the urine metanephrines are used to confirm or exclude certain diseases when the doctor identifies signs of <a href="Hypertension" title="Hypertension">hypertension</a> and <a href="Tachycardia" title="Tachycardia">tachycardia</a> that don't adequately respond to treatment.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Each of the tests measure the amount of adrenaline and noradrenaline metabolites, respectively called <a href="Metanephrine" title="Metanephrine">metanephrine</a> and <a href="Normetanephrine" title="Normetanephrine">normetanephrine</a>.

</p><p>Blood tests are also done to analyze the amount of catecholamines present in the body.

</p><p>Catecholamine tests are done to identify rare tumors at the adrenal gland or in the nervous system. Catecholamine tests provide information relative to tumors such as: pheochromocytoma, paraganglioma, and neuroblastoma.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup>

</p>

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<ul><li><a href="Catechol-O-methyltransferase" title="Catechol-O-methyltransferase">Catechol-<i>O</i>-methyltransferase</a></li>

<li><a href="Catecholaminergic_polymorphic_ventricular_tachycardia" title="Catecholaminergic polymorphic ventricular tachycardia">Catecholaminergic polymorphic ventricular tachycardia</a></li>

<li><a href="History_of_catecholamine_research" title="History of catecholamine research">History of catecholamine research</a></li>

<li><a href="Hormone" title="Hormone">Hormone</a></li>

<li><a href="Julius_Axelrod" title="Julius Axelrod">Julius Axelrod</a></li>

<li><a href="Peptide_hormone" title="Peptide hormone">Peptide hormone</a></li>

<li><a href="Phenethylamine" title="Phenethylamine">Phenethylamine</a></li>

<li><a href="Steroid_hormone" title="Steroid hormone">Steroid hormone</a></li>

<li><a href="Sympathomimetic_drug" title="Sympathomimetic drug">Sympathomimetic drug</a></li>

<li><a href="Vanillylmandelic_acid" title="Vanillylmandelic acid">Vanillylmandelic acid</a></li></ul>

</div>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

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<li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><cite id="CITEREFManorTyanoMelEisenberg2002" class="citation journal cs1">Manor, I.; Tyano, S.; Mel, E.; Eisenberg, J.; Bachner-Melman, R.; Kotler, M.; Ebstein, R. P. (2002). <a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fsj.mp.4001037">"Family-Based and Association Studies of Monoamine Oxidase A and Attention Deficit Hyperactivity Disorder (ADHD): Preferential Transmission of the Long Promoter-Region Repeat and its Association with Impaired Performance on a Continuous Performance Test (TOVA)"</a>. <i>Molecular Psychiatry</i>. <b>7</b> (6): <span class="nowrap">626–</span>632. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fsj.mp.4001037">10.1038/sj.mp.4001037</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12140786">12140786</a>.</cite></span>

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<li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><cite id="CITEREFBrunner,_H._G.1996" class="citation book cs1">Brunner, H. G. (1996). "MAOA Deficiency and Abnormal Behaviour: Perspectives on an Association". <i>Genetics of Criminal and Antisocial Behaviour</i>. Ciba Foundation Symposium. Vol. 194. Wiley. pp. <span class="nowrap">155–</span>167. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470514825.ch9">10.1002/9780470514825.ch9</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0-470-51482-5</bdi>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8862875">8862875</a>.</cite></span>

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<li id="cite_note-heneka-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-heneka_15-0">^</a></b></span> <span class="reference-text"><cite id="CITEREFHenekaCarsonEl_Khoury2015" class="citation journal cs1">Heneka MT, Carson MJ, El Khoury J, et al. (April 2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5909703">"Neuroinflammation in Alzheimer's disease"</a>. <i>The Lancet. Neurology</i>. <b>14</b> (4): <span class="nowrap">388–</span>405. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS1474-4422%2815%2970016-5">10.1016/S1474-4422(15)70016-5</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5909703">5909703</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25792098">25792098</a>.</cite></span>

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<li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><cite id="CITEREFEstes2016" class="citation book cs1">Estes, Mary (2016). <i>Health assessment and physical examination</i> (2nd ed.). <a href="Melbourne" title="Melbourne">Melbourne</a>: <a href="Cengage" class="mw-redirect" title="Cengage">Cengage</a>. p. 143. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0-17-035484-4</bdi>.</cite></span>

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<li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.webmd.com/heart-disease/catecholamines-14697#1">"Catecholamines in Urine"</a>. <i>webmd.com</i><span class="reference-accessdate">. Retrieved <span class="nowrap">4 May</span> 2017</span>.</cite></span>

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<li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://labtestsonline.org/tests/urine-metanephrines">"Urine Metanephrines | Lab Tests Online"</a>. <i>labtestsonline.org</i>. 6 December 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">2019-12-24</span></span>.</cite></span>

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</ol></div></div>

<div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2></div>

<ul><li><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?name=Catecholamines">Catecholamines</a> at the U.S. National Library of Medicine <a href="Medical_Subject_Headings" title="Medical Subject Headings">Medical Subject Headings</a> (MeSH)</li></ul>

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</style><div id="Neurotransmitters114" style="font-size:114%;margin:0 4em"><a href="Neurotransmitter" title="Neurotransmitter">Neurotransmitters</a></div></th></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="Amino_acid" title="Amino acid">Amino acid</a>-derived</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Major excitatory /<br>inhibitory systems</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">Glutamate system</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Agmatine" title="Agmatine">Agmatine</a></li>

<li><a href="Aspartic_acid" title="Aspartic acid">Aspartic acid (aspartate)</a></li>

<li><a href="Glutamate_(neurotransmitter)" title="Glutamate (neurotransmitter)">Glutamic acid (glutamate)</a></li>

<li><a href="Glutathione" title="Glutathione">Glutathione</a></li>

<li><a href="Glycine" title="Glycine">Glycine</a></li>

<li><a href="Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li>

<li><a href="Proline" title="Proline">Proline</a></li>

<li><a href="Serine" title="Serine">Serine</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">GABA system</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<li><a href="%CE%93-Amino-%CE%B2-hydroxybutyric_acid" title="Γ-Amino-β-hydroxybutyric acid">GABOB</a></li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">Glycine system</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Alanine" title="Alanine">α-Alanine</a></li>

<li><a href="%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li>

<li><a href="Glycine" title="Glycine">Glycine</a></li>

<li><a href="Hypotaurine" title="Hypotaurine">Hypotaurine</a></li>

<li><a href="Proline" title="Proline">Proline</a></li>

<li><a href="Sarcosine" title="Sarcosine">Sarcosine</a></li>

<li><a href="Serine" title="Serine">Serine</a></li>

<li><a href="Taurine" title="Taurine">Taurine</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;"><a href="GHB_receptor" title="GHB receptor">GHB system</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="Biogenic_amine" title="Biogenic amine">Biogenic amines</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Monoamines</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em">

<li><a href="Dopamine" title="Dopamine">Dopamine</a></li>

<li><a href="Adrenaline" title="Adrenaline">Epinephrine (adrenaline)</a></li>

<li><a href="N-Acetylserotonin" title="N-Acetylserotonin">NAS (normelatonin)</a></li>

<li><a href="Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li>

<li><a href="Serotonin" title="Serotonin">Serotonin (5-HT)</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Trace amines</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em">

<ul><li><a href="3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li>

<li><a href="N-Methylphenethylamine" title="N-Methylphenethylamine">N-Methylphenethylamine</a></li>

<li><a href="N-Methyltryptamine" title="N-Methyltryptamine">N-Methyltryptamine</a></li>

<li><a href="Norfenefrine" title="Norfenefrine"><i>m</i>-Octopamine</a></li>

<li><a href="Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></li>

<li><a href="Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li>

<li><a href="Phenethylamine" title="Phenethylamine">Phenethylamine</a></li>

<li><a href="Synephrine" title="Synephrine">Synephrine</a></li>

<li><a href="Tryptamine" title="Tryptamine">Tryptamine</a></li>

<li><a href="Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li>

<li><a href="Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Histamine" title="Histamine">Histamine</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="Neuropeptide" title="Neuropeptide">Neuropeptides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li>See here instead.</li></ul>

</div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="Lipid" title="Lipid">Lipid</a>-derived</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Endocannabinoids33" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Endocannabinoids</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<li><a href="2-Arachidonyl_glyceryl_ether" title="2-Arachidonyl glyceryl ether">2-AGE (noladin ether)</a></li>

<li><a href="Anandamide" title="Anandamide">Anandamide (AEA)</a></li>

<li><a href="N-Arachidonylglycine" title="N-Arachidonylglycine">NAGly</a></li>

<li><a href="Oleamide" title="Oleamide">Oleamide</a></li>

<li><a href="Virodhamine" title="Virodhamine">Virodhamine (O-AEA)</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="Neurosteroid" title="Neurosteroid">Neurosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li>See here instead.</li></ul>

</div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="Nucleobase" class="mw-redirect" title="Nucleobase">Nucleobase</a>-derived</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Nucleosides11" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Nucleosides</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Adenosine_system20" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="Adenosine" title="Adenosine">Adenosine</a> system</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

</div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="Vitamin" title="Vitamin">Vitamin</a>-derived</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">Miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Cholinergic_system18" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Cholinergic system</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Acetylcholine" title="Acetylcholine">Acetylcholine</a></li></ul>

</div></td></tr></tbody></table><div>

</div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Gasotransmitters16" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Gasotransmitters</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Carbon_monoxide" title="Carbon monoxide">Carbon monoxide (CO)</a></li>

<li><a href="Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide (H<sub>2</sub>S)</a></li>

<li><a href="Nitric_oxide" title="Nitric oxide">Nitric oxide (NO)</a></li></ul>

</div></td></tr></tbody></table><div>

</div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Candidates10" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Candidates</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li>

<li><a href="Ammonia" title="Ammonia">Ammonia (NH<sub>3</sub>)</a></li>

<li><a href="Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide (COS)</a></li>

<li><a href="Nitrous_oxide" title="Nitrous oxide">Nitrous oxide (N<sub>2</sub>O)</a></li>

<li><a href="Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide (SO<sub>2</sub>)</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr></tbody></table></div>

<div class="navbox-styles"></div><div role="navigation" class="navbox" aria-labelledby="Neurotransmitter_metabolic_intermediates170" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="Neurotransmitter_metabolic_intermediates170" style="font-size:114%;margin:0 4em"><a href="Neurotransmitter" title="Neurotransmitter">Neurotransmitter</a> <a href="Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Anabolism" title="Anabolism">Anabolism</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Phenylalanine" title="Phenylalanine">Phenylalanine</a> → <a href="Tyrosine" title="Tyrosine">Tyrosine</a> → <a href="L-DOPA" title="L-DOPA">DOPA (levodopa)</a> → <a href="Dopamine" title="Dopamine">Dopamine</a> → <a href="Norepinephrine" title="Norepinephrine">Norepinephrine</a> → <a href="Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Catabolism" title="Catabolism">Catabolism</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Dopamine" title="Dopamine">Dopamine</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="3%2C4-Dihydroxyphenylacetaldehyde" title="3,4-Dihydroxyphenylacetaldehyde">3,4-Dihydroxyphenylacetaldehyde (DOPAL)</a></li>

<li><a href="3%2C4-Dihydroxyphenylacetic_acid" title="3,4-Dihydroxyphenylacetic acid">3,4-Dihydroxyphenylacetic acid (DOPAC)</a></li>

<li><a href="Homovanillyl_alcohol" title="Homovanillyl alcohol">Homovanillyl alcohol</a></li>

<li><a href="Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol (3,4-dihydroxyphenylethanol; DOPET)</a></li>

<li><a href="3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine (3-MT)</a></li>

<li><a href="Homovanillic_acid" title="Homovanillic acid">Homovanillic acid (HVA)</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Norepinephrine" title="Norepinephrine">Norepinephrine</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="3%2C4-Dihydroxyphenylglycolaldehyde" title="3,4-Dihydroxyphenylglycolaldehyde">3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL)</a></li>

<li><a href="3%2C4-Dihydroxymandelic_acid" title="3,4-Dihydroxymandelic acid">3,4-Dihydroxymandelic acid (DHMA)</a></li>

<li><a href="Normetanephrine" title="Normetanephrine">Normetanephrine</a></li>

<li>3-Methoxy-4-hydroxymandelaldehyde (MHMAL)</li>

<li><a href="Vanillylmandelic_acid" title="Vanillylmandelic acid">Vanillylmandelic acid (VMA)</a></li>

<li><a href="Dihydroxyphenylethylene_glycol" title="Dihydroxyphenylethylene glycol">3,4-Dihydroxyphenylethylene glycol (DOPEG, DHPG)</a></li>

<li><a href="3-Methoxy-4-hydroxyphenylglycol" title="3-Methoxy-4-hydroxyphenylglycol">3-Methoxy-4-hydroxyphenylglycol (MHPG, MOPEG)</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="3%2C4-Dihydroxyphenylglycolaldehyde" title="3,4-Dihydroxyphenylglycolaldehyde">3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL)</a></li>

<li><a href="Metanephrine" title="Metanephrine">Metanephrine</a></li>

<li>3-Methoxy-4-hydroxymandelaldehyde (MHMAL)</li></ul>

</div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Tryptophan" title="Tryptophan">Tryptophan</a>→<a href="Serotonin" title="Serotonin">Serotonin</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Anabolism" title="Anabolism">Anabolism</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Tryptophan" title="Tryptophan">Tryptophan</a></li>

<li><a href="5-Hydroxytryptophan" title="5-Hydroxytryptophan">5-Hydroxytryptophan (5-HTP)</a></li></ul>

<ul><li><a href="5-Hydroxyindoleacetaldehyde" title="5-Hydroxyindoleacetaldehyde">5-Hydroxyindoleacetaldehyde (5-HIAL)</a></li>

<li><a href="5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-Hydroxyindoleacetic acid (5-HIAA)</a></li>

<li>5-Hydroxytryptophol (5-HTOL)</li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Serotonin" title="Serotonin">Serotonin</a>→<a href="Melatonin" title="Melatonin">Melatonin</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="N-Acetylserotonin" title="N-Acetylserotonin"><i>N</i>-Acetylserotonin (NAS; normelatonin)</a></li>

<li><a href="5-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamine (5-MT)</a></li>

<li>5-Methoxyindoleacetaldehyde (5-MIAL)</li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Trace_amine" title="Trace amine">Trace amines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li>3-Methoxy-4-hydroxyphenylacetaldehyde (HMPAL)</li>

<li><a href="4-Hydroxyphenylacetaldehyde" title="4-Hydroxyphenylacetaldehyde">4-Hydroxyphenylacetaldehyde (HPAL)</a></li>

<li><a href="Indole-3-acetaldehyde" title="Indole-3-acetaldehyde">Indoleacetaldehyde (IAL)</a></li>

<li>Phenacetaldehyde (PAL)</li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="%CE%93-Aminobutyric_acid" class="mw-redirect" title="Γ-Aminobutyric acid">GABA</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></li>

<li><a href="Putrescine" title="Putrescine">Putrescine</a></li>

<li><a href="4-Aminobutanal" title="4-Aminobutanal">γ-Aminobutyraldehyde (GABAL)</a></li>

<li><a href="N-Acetylputrescine" title="N-Acetylputrescine"><i>N</i>-Acetylputrescine</a></li>

<li><a href="4-Acetamidobutanal" title="4-Acetamidobutanal"><i>N</i>-Acetyl-γ-aminobutyraldehyde (<i>N</i>-acetyl-GABAL)</a></li>

<li><a href="N-Acetyl-%CE%B3-aminobutyric_acid" title="N-Acetyl-γ-aminobutyric acid"><i>N</i>-Acetyl-γ-aminobutyric acid (<i>N</i>-acetyl-GABA)</a></li></ul>

</div></td></tr></tbody></table></div>

<div class="navbox-styles"></div><div role="navigation" class="navbox" aria-labelledby="Trace_amine-associated_receptor_modulators1406" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="Trace_amine-associated_receptor_modulators1406" style="font-size:114%;margin:0 4em"><a href="Trace_amine-associated_receptor" title="Trace amine-associated receptor">Trace amine-associated receptor</a> <a href="Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="Trace_amine-associated_receptor_1" class="mw-redirect" title="Trace amine-associated receptor 1"><abbr title="Trace amine-associated receptor 1">TAAR1</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Trace amine-associated receptor 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="Agonist" title="Agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="Trace_amine" title="Trace amine">Endogenous</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Monoamine_neurotransmitter" title="Monoamine neurotransmitter">Monoamine neurotransmitters</a>

<ul><li><a href="Dopamine" title="Dopamine">Dopamine</a></li>

<li><a href="Histamine" title="Histamine">Histamine</a></li>

<li><a href="Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a></li>

<li><a href="Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li>

<li><a href="Serotonin" title="Serotonin">Serotonin</a></li></ul></li>

<li><a href="Trace_amine" title="Trace amine">Trace amines</a>

<ul><li><a href="3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li>

<li><a href="3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></li>

<li><a href="N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li>

<li><a href="N-Methyltyramine" title="N-Methyltyramine"><i>N</i>-Methyltyramine</a></li>

<li><a href="Meta-Octopamine" class="mw-redirect" title="Meta-Octopamine"><i>m</i>-Octopamine</a></li>

<li><a href="Para-Octopamine" class="mw-redirect" title="Para-Octopamine"><i>p</i>-Octopamine</a></li>

<li><a href="Phenethylamine" title="Phenethylamine">β-Phenethylamine</a></li>

<li><a href="Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li>

<li><a href="Synephrine" title="Synephrine">Synephrine</a></li>

<li><a href="Tryptamine" title="Tryptamine">Tryptamine</a></li>

<li><a href="Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li>

<li><a href="Para-Tyramine" class="mw-redirect" title="Para-Tyramine"><i>p</i>-Tyramine</a></li></ul></li>

<li>Others

<ul><li><a href="Cyclohexylamine" title="Cyclohexylamine">Cyclohexylamine</a></li>

<li>Isoamylamine</li>

<li><a href="Trimethylamine" title="Trimethylamine">Trimethylamine</a></li></ul></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="Exogenous" class="mw-redirect" title="Exogenous">Exogenous</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<li><a href="2-Aminoindane" title="2-Aminoindane">2-Aminoindane</a></li>

<li><a href="Amphetamine" title="Amphetamine">Amphetamine</a></li>

<li><a href="Apomorphine" title="Apomorphine">Apomorphine</a></li>

<li><a href="Asenapine" title="Asenapine">Asenapine</a></li>

<li><a href="Bromocriptine" title="Bromocriptine">Bromocriptine</a></li>

<li><a href="Cathinone" title="Cathinone">Cathinone</a></li>

<li><a href="Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li>

<li><a href="Clonidine" title="Clonidine">Clonidine</a></li>

<li><a href="Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li>

<li><a href="Dihydroergotamine" title="Dihydroergotamine">Dihydroergotamine</a></li>

<li><a href="Dimethyltryptamine" title="Dimethyltryptamine">Dimethyltryptamine</a></li>

<li><a href="N%2CN-Dimethylphenethylamine" title="N,N-Dimethylphenethylamine"><i>N</i>,<i>N</i>-Dimethylphenethylamine</a></li>

<li><a href="Ergometrine" class="mw-redirect" title="Ergometrine">Ergometrine</a></li>

<li><a href="Fenoldopam" title="Fenoldopam">Fenoldopam</a></li>

<li><a href="Fenoterol" title="Fenoterol">Fenoterol</a></li>

<li><a href="4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-Fluoroamphetamine</a></li>

<li><a href="Guanabenz" title="Guanabenz">Guanabenz</a></li>

<li><a href="Guanfacine" title="Guanfacine">Guanfacine</a></li>

<li><a href="Halostachine" title="Halostachine">Halostachine</a></li>

<li><a href="Higenamine" title="Higenamine">Higenamine</a></li>

<li><a href="Hordenine" title="Hordenine">Hordenine</a></li>

<li><a href="4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine (norpholedrine)</a></li>

<li><a href="Idazoxan" title="Idazoxan">Idazoxan</a></li>

<li><a href="5-Iodo-2-aminoindane" class="mw-redirect" title="5-Iodo-2-aminoindane">5-Iodo-2-aminoindane</a></li>

<li><a href="Isoprenaline" title="Isoprenaline">Isoprenaline</a></li>

<li><a href="Isopropyloctopamine" class="mw-redirect" title="Isopropyloctopamine">Isopropyloctopamine</a></li>

<li><a href="Lisuride" title="Lisuride">Lisuride</a></li>

<li><a href="3%2C4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li>

<li><a href="MDMA" title="MDMA">MDMA (midomafetamine)</a></li>

<li><a href="Mescaline" title="Mescaline">Mescaline</a></li>

<li><a href="Metergoline" title="Metergoline">Metergoline</a></li>

<li><a href="N-Methyl-2-AI" class="mw-redirect" title="N-Methyl-2-AI"><i>N</i>-Methyl-2-AI</a></li>

<li><a href="2-Methylphenethylamine" title="2-Methylphenethylamine">2-Methylphenethylamine</a></li>

<li><a href="3-Methylphenethylamine" title="3-Methylphenethylamine">3-Methylphenethylamine</a></li>

<li><a href="4-Methylphenethylamine" title="4-Methylphenethylamine">4-Methylphenethylamine</a></li>

<li><a href="%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li>

<li><a href="Methamphetamine" title="Methamphetamine">Methamphetamine</a></li>

<li><a href="Naphazoline" title="Naphazoline">Naphazoline</a></li>

<li><a href="Nomifensine" title="Nomifensine">Nomifensine</a></li>

<li><a href="Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li>

<li><a href="Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li>

<li><a href="Phentermine" title="Phentermine">Phentermine</a></li>

<li><a href="Phentolamine" title="Phentolamine">Phentolamine</a></li>

<li><a href="Psilocin" title="Psilocin">Psilocin</a></li>

<li><a href="Ralmitaront" title="Ralmitaront">Ralmitaront (RG-7906, RO6889450)</a></li>

<li><a href="Selegiline" title="Selegiline">Selegiline (<small>L</small>-deprenyl)</a></li>

<li><a href="Solriamfetol" title="Solriamfetol">Solriamfetol</a></li>

<li><a href="Tolazoline" title="Tolazoline">Tolazoline</a></li>

<li><a href="Ulotaront" title="Ulotaront">Ulotaront (SEP-363856)</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="Receptor_antagonist" title="Receptor antagonist">Antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Compound_22_(TAAR1_antagonist)" title="Compound 22 (TAAR1 antagonist)">Compound 22</a></li>

<li><a href="EPPTB" title="EPPTB">EPPTB (RO-5212773)</a></li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="Inverse_agonist" title="Inverse agonist">Inverse agonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="EPPTB" title="EPPTB">EPPTB (RO-5212773)</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="Trace_amine-associated_receptor_5" class="mw-redirect" title="Trace amine-associated receptor 5"><abbr title="Trace amine-associated receptor 5">TAAR5</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Trace amine-associated receptor 5</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Agonists32" scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="Agonist" title="Agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="N%2CN-Dimethylethylamine" title="N,N-Dimethylethylamine"><i>N</i>,<i>N</i>-Dimethylethylamine</a></li>

<li><a href="Trimethylamine" title="Trimethylamine">Trimethylamine</a></li></ul>

<ul><li><a href="3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>Notes:</b></i> (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the <a href="Trace_amine#List_of_trace_amines" title="Trace amine">List of trace amines</a>, <a href="Trace_amine-associated_receptor" title="Trace amine-associated receptor">TAAR</a>, and <a href="TAAR1" title="TAAR1">TAAR1</a> pages.<br><i><b>See also:</b> Receptor/signaling modulators</i></div></td></tr></tbody></table></div>

<div class="navbox-styles"></div><div role="navigation" class="navbox" aria-labelledby="Chemical_classes_of_psychoactive_drugs153" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="Chemical_classes_of_psychoactive_drugs153" style="font-size:114%;margin:0 4em"><a href="Chemical_class" class="mw-redirect" title="Chemical class">Chemical classes</a> of <a href="Psychoactive_drug" title="Psychoactive drug">psychoactive drugs</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="Stimulant" title="Stimulant">Stimulants</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><i>Amphetamine-type/dopamine releasing agents:</i> <a href="Psychotropic_alkylamine" class="mw-redirect" title="Psychotropic alkylamine">Alkylamines</a>

<ul><li><a href="Cycloalkylaminopropane" title="Cycloalkylaminopropane">Cycloalkylaminopropanes</a></li></ul></li>

<li><a href="Substituted_piperazine" title="Substituted piperazine">Arylpiperazines</a>

<ul><li><a href="Substituted_benzylpiperazine" class="mw-redirect" title="Substituted benzylpiperazine">Benzylpiperazines</a></li>

<li><a href="Substituted_phenylpiperazine" class="mw-redirect" title="Substituted phenylpiperazine">Phenylpiperazines</a></li></ul></li>

<li><a href="Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a>

<ul><li><a href="List_of_aminorex_analogues" title="List of aminorex analogues">Aminorexes/phenyloxazolamines</a></li>

<li><a href="Substituted_amphetamine" title="Substituted amphetamine">Amphetamines/α-methylphenethylamines</a>

<ul><li><a href="Substituted_cathinone" title="Substituted cathinone">Cathinones/β-ketoamphetamines</a></li>

<li><a href="Substituted_%CE%B2-hydroxyamphetamine" title="Substituted β-hydroxyamphetamine">β-Hydroxyamphetamines/cathinols</a></li>

<li><a href="Substituted_naphthylethylamine" title="Substituted naphthylethylamine">Naphthylaminopropanes</a></li>

<li><a href="Substituted_phentermine" class="mw-redirect" title="Substituted phentermine">Phentermines</a></li>

<li><a href="Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamines/α-ethylphenethylamines</a></li>

<li><a href="%CE%91-Propylphenethylamine" title="Α-Propylphenethylamine">α-Propylphenethylamines</a></li></ul></li>

<li><a href="Substituted_phenylmorpholine" title="Substituted phenylmorpholine">Phenylmorpholines/phenmetrazines</a></li></ul></li>

<li><a href="Thiopropamine" title="Thiopropamine">Thiopropamines/thienylaminopropanes</a></li></ul>

<ul><li><i>Cocaine-type/typical dopamine reuptake inhibitors:</i> <a href="Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a>

<ul><li><a href="List_of_methylphenidate_analogues" title="List of methylphenidate analogues">Phenidates</a>/<a href="2-benzylpiperidine" class="mw-redirect" title="2-benzylpiperidine">benzylpiperidines</a></li>

<li><a href="Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">Phenylethylpyrrolidines</a>

<ul><li><a href="Pyrrolidinophenone" title="Pyrrolidinophenone">Pyrrolidinophenones</a></li></ul></li></ul></li>

<li><a href="List_of_phenyltropanes" title="List of phenyltropanes">Phenyltropanes</a>/<a href="List_of_cocaine_analogues" title="List of cocaine analogues">cocaine analogues</a></li></ul>

<ul><li><i>Modafinil-type/atypical dopamine reuptake inhibitors:</i> <a href="List_of_modafinil_analogues_and_derivatives" title="List of modafinil analogues and derivatives">Modafinil analogues</a></li>

<li><a href="Phenylpiracetam" title="Phenylpiracetam">Phenylpiracetams</a></li></ul>

<ul><li><i>Caffeine-type/adenosine receptor antagonists:</i> <a href="Xanthine" title="Xanthine">Xanthines</a>/<a href="Methylxanthine" class="mw-redirect" title="Methylxanthine">methylxanthines</a></li></ul>

<ul><li><i>Nicotine-type/nicotinic acetylcholine receptor agonists:</i> <a href="Nicotine_analogue" class="mw-redirect" title="Nicotine analogue">Nicotine analogues</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="Central_depressant" class="mw-redirect" title="Central depressant">Depressants</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><i>GABA<sub>A</sub> receptor positive allosteric modulators:</i> <a href="Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a>/<a href="Alcohol_(drug)#Analogues" title="Alcohol (drug)">ethanol analogues</a></li>

<li><a href="Barbiturate" title="Barbiturate">Barbiturates</a></li>

<li><a href="Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a>

<ul><li><a href="Pyrrolobenzodiazepine" title="Pyrrolobenzodiazepine">Pyrrolobenzodiazepines</a></li>

<li><a href="Thienobenzodiazepine" title="Thienobenzodiazepine">Thienobenzodiazepines</a></li>

<li><a href="Thienodiazepine" title="Thienodiazepine">Thienodiazepines</a></li>

<li><a href="Thienotriazolodiazepine" title="Thienotriazolodiazepine">Thienotriazolodiazepines</a></li>

<li><a href="Triazolobenzodiazepine" title="Triazolobenzodiazepine">Triazolobenzodiazepines</a></li></ul></li>

<li><a href="Carbamate" title="Carbamate">Carbamates</a></li>

<li><a href="Ether" title="Ether">Ethers</a></li>

<li><a href="Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a></li>

<li><a href="Nonbenzodiazepine" title="Nonbenzodiazepine">Nonbenzodiazepines</a>

<ul><li><a href="Substituted_%CE%B2-carboline" title="Substituted β-carboline">β-Carbolines</a></li>

<li><a href="Cyclopyrrolones" title="Cyclopyrrolones">Cyclopyrrolones</a></li>

<li><a href="Imidazopyridine" title="Imidazopyridine">Imidazopyridines</a></li>

<li><a href="Pyrazolopyrimidine" title="Pyrazolopyrimidine">Pyrazolopyrimidines</a></li></ul></li>

<li><a href="Phenol" title="Phenol">Phenols</a></li>

<li><a href="Piperidinedione" class="mw-redirect" title="Piperidinedione">Piperidinediones</a></li>

<li><a href="Quinazolinone" title="Quinazolinone">Quinazolinones</a></li></ul>

<ul><li><i>GABA<sub>A</sub> receptor agonists:</i> <a href="Isoxazole" title="Isoxazole">Isoxazoles</a></li></ul>

<ul><li><i>GHB receptor agonists:</i> <a href="Substituted_1%2C4-butanediol" class="mw-redirect" title="Substituted 1,4-butanediol">1,4-Butanediols</a></li></ul>

<ul><li><i>α<sub>2</sub>δ subunit-containing voltage-gated calcium channel blockers:</i> <a href="Gabapentinoid" title="Gabapentinoid">Gabapentinoids</a></li></ul>

<ul><li><i>Opioids/μ-opioid receptor agonists:</i> <a href="List_of_benzimidazole_opioids" title="List of benzimidazole opioids">Benzimidazoles</a>

<ul><li><a href="Nitazenes" title="Nitazenes">Nitazenes</a></li></ul></li>

<li><a href="List_of_fentanyl_analogues" title="List of fentanyl analogues">Fentanyl analogues</a>/<a href="Phenylpiperidines" title="Phenylpiperidines">phenylpiperidines</a></li>

<li><a href="Mitragyna_alkaloid" class="mw-redirect" title="Mitragyna alkaloid"><i>Mitragyna</i> alkaloids</a></li>

<li><a href="Morphinan" title="Morphinan">Morphinans</a>/<a href="Phenanthrene" title="Phenanthrene">phenanthrenes</a>

<ul><li><a href="Opiate" title="Opiate">Opiates</a>/<a href="Opium_alkaloid" class="mw-redirect" title="Opium alkaloid">opium alkaloids</a></li></ul></li>

<li><a href="Utopioid_(drug_class)" title="Utopioid (drug class)">Utopioids</a></li></ul>

<ul><li><i>Antihistamines/H<sub>1</sub> receptor antagonists:</i> <a href="Benzimidazole" title="Benzimidazole">Benzimidazoles</a></li>

<li><a href="Substituted_diarylmethane" class="mw-redirect" title="Substituted diarylmethane">Diarylmethanes</a></li>

<li><a href="Ethylenediamine" title="Ethylenediamine">Ethylenediamines</a></li>

<li><a href="Tricyclic_compound" class="mw-redirect" title="Tricyclic compound">Tricyclics</a>

<ul><li><a href="Dibenzocycloheptene" title="Dibenzocycloheptene">Dibenzocycloheptenes</a></li></ul></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="Hallucinogen" title="Hallucinogen">Hallucinogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><i>Serotonergic psychedelics/serotonin 5-HT<sub>2A</sub> receptor agonists:</i> <a href="Substituted_arylpiperazine" class="mw-redirect" title="Substituted arylpiperazine">Arylpiperazines</a>

<ul><li><a href="Substituted_phenylpiperazine" class="mw-redirect" title="Substituted phenylpiperazine">Phenylpiperazines</a></li>

<li><a href="Substituted_quinolinylpiperazine" class="mw-redirect" title="Substituted quinolinylpiperazine">Quinolinylpiperazines</a></li></ul></li>

<li><a href="Cyclized_tryptamine" class="mw-redirect" title="Cyclized tryptamine">Cyclized tryptamines</a>

<ul><li><a href="Azepinoindole" title="Azepinoindole">Azepinoindoles</a>

<ul><li><a href="Ibogalog" title="Ibogalog">Ibogalogs</a></li>

<li><a href="Iboga-type_alkaloid" title="Iboga-type alkaloid"><i>Iboga</i> alkaloids</a></li></ul></li>

<li><a href="Substituted_%CE%B2-carboline" title="Substituted β-carboline">β-Carbolines</a>

<ul><li><a href="Harmala_alkaloid" title="Harmala alkaloid">Harmala alkaloids</a></li></ul></li>

<li><a href="Substituted_ergoline" class="mw-redirect" title="Substituted ergoline">Ergolines</a>

<ul><li><a href="Substituted_lysergamide" class="mw-redirect" title="Substituted lysergamide">Lysergamides</a></li></ul></li>

<li><a href="Simplified/partial_lysergamide" class="mw-redirect" title="Simplified/partial lysergamide">Simplified/partial lysergamides</a></li></ul></li>

<li><a href="Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a> (<a href="Substituted_methoxyphenethylamine" title="Substituted methoxyphenethylamine">methoxyphenethylamines</a>)

<ul><li><a href="25-NB" title="25-NB">25-NB/NBOMes</a></li>

<li><a href="TWEETIO" title="TWEETIO">TWEETIOs</a></li></ul></li>

<li><a href="Substituted_amphetamine" title="Substituted amphetamine">Amphetamines/α-methylphenethylamines</a>

<li><a href="Dimethoxyamphetamine" title="Dimethoxyamphetamine">Dimethoxyamphetamines/DMAs</a></li>

<ul><li><a href="Aleph_(psychedelic)" title="Aleph (psychedelic)">Alephs</a></li></ul></li>

<li><a href="Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">Methylenedioxyamphetamines/MDxx</a></li>

<li><a href="Trimethoxyamphetamine" class="mw-redirect" title="Trimethoxyamphetamine">Trimethoxyamphetamines/TMAs</a></li></ul></li>

<li><a href="FLY_(psychedelics)" title="FLY (psychedelics)">FLYs</a>/<a href="Substituted_benzofuran" title="Substituted benzofuran">benzofurans</a></li>

<li><a href="Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamines/α-ethylphenethylamines</a>

<li><a href="Scaline" class="mw-redirect" title="Scaline">Scalines</a></li></ul></li>

<li><a href="Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a>

<ul><li><a href="Substituted_%CE%B1-alkyltryptamine" class="mw-redirect" title="Substituted α-alkyltryptamine">α-Alkyltryptamines</a>

<ul><li><a href="Substituted_%CE%B2-ketotryptamine" class="mw-redirect" title="Substituted β-ketotryptamine">α-Alkyl-β-ketotryptamines</a></li></ul></li>

<li><a href="Substituted_4-hydroxytryptamine" class="mw-redirect" title="Substituted 4-hydroxytryptamine">4-Hydroxytryptamines</a></li>

<li><a href="Substituted_5-hydroxytryptamine" class="mw-redirect" title="Substituted 5-hydroxytryptamine">5-Hydroxytryptamines</a>

<ul><li><a href="Substituted_5-methoxytryptamine" class="mw-redirect" title="Substituted 5-methoxytryptamine">5-Methoxytryptamines</a></li></ul></li></ul></li>

<li><a href="List_of_miscellaneous_5-HT2A_receptor_agonists" title="List of miscellaneous 5-HT2A receptor agonists">Miscellaneous</a></li></ul>

<ul><li><i>Dissociatives/NMDA receptor antagonists:</i> <a href="Adamantane" title="Adamantane">Adamantanes</a></li>

<li><a href="Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclohexylamines</a></li>

<li><a href="Diarylethylamine" class="mw-redirect" title="Diarylethylamine">Diarylethylamines</a></li>

<li><a href="Morphinan" title="Morphinan">Morphinans</a></li></ul>

<ul><li><i>κ-Opioid receptor agonists:</i> <a href="Benzomorphan" title="Benzomorphan">Benzomorphans</a></li>

<li><a href="Salvinorin" title="Salvinorin">Salvinorins</a></li></ul>

<ul><li><i>GABA<sub>A</sub> receptor agonists:</i> <a href="Isoxazole" title="Isoxazole">Isoxazoles</a></li></ul>

<ul><li><i>Deliriants/anticholinergics/muscarinic acetylcholine receptor antagonists:</i> <a href="Substituted_diarylmethane" class="mw-redirect" title="Substituted diarylmethane">Diarylmethanes</a></li>

<li><a href="Tropanes" class="mw-redirect" title="Tropanes">Tropanes</a></li></ul>

<ul><li><i>Others:</i> <a href="Cyclized_tryptamine" class="mw-redirect" title="Cyclized tryptamine">Cyclized tryptamines</a>

<ul><li><a href="Azepinoindole" title="Azepinoindole">Azepinoindoles</a>

<ul><li><a href="Iboga-type_alkaloid" title="Iboga-type alkaloid"><i>Iboga</i> alkaloids</a></li></ul></li></ul></li>

<li><a href="Cannabinoid" title="Cannabinoid">(Phyto)cannabinoids</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="Entactogen" title="Entactogen">Entactogens</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><i>Serotonin releasing agents:</i> <a href="Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a>

<ul><li><a href="Aminoindane" title="Aminoindane">Aminoindanes</a></li>

<li><a href="Aminotetralin" title="Aminotetralin">Aminotetralins</a></li>

<li><a href="Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</a>

<ul><li><a href="Substituted_benzofuran" title="Substituted benzofuran">Benzofuranylaminopropanes</a></li>

<li><a href="Substituted_benzothiophene" title="Substituted benzothiophene">Benzothiophenylaminopropanes</a></li>

<li><a href="Ethylenedioxyamphetamine" class="mw-redirect" title="Ethylenedioxyamphetamine">Ethylenedioxyamphetamines</a></li>

<li><a href="Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">Indanylaminopropanes</a></li>

<li><a href="Indolylaminopropane" class="mw-redirect" title="Indolylaminopropane">Indolylaminopropanes</a></li>

<li><a href="Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">Methylenedioxyamphetamine/MDxx</a></li>

<li><a href="Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">Tetralinylaminopropanes</a></li></ul></li></ul></li>

<li><a href="Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a>

<ul><li><a href="Substituted_%CE%B1-alkyltryptamine" class="mw-redirect" title="Substituted α-alkyltryptamine">α-Alkyltryptamines</a></li></ul></li>

<li><a href="Substituted_methylenedioxyphenethylamine#Related_compounds" title="Substituted methylenedioxyphenethylamine">Miscellaneous</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="Psychiatric_drug" class="mw-redirect" title="Psychiatric drug">Psychiatric drugs</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><i>Anxiolytics:</i> <a href="Azapirone" title="Azapirone">Azapirones</a></li>

<li><a href="Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a>

<ul><li><a href="Pyrrolobenzodiazepine" title="Pyrrolobenzodiazepine">Pyrrolobenzodiazepines</a></li>

<li><a href="Thienobenzodiazepine" title="Thienobenzodiazepine">Thienobenzodiazepines</a></li>

<li><a href="Thienodiazepine" title="Thienodiazepine">Thienodiazepines</a></li>

<li><a href="Thienotriazolodiazepine" title="Thienotriazolodiazepine">Thienotriazolodiazepines</a></li>

<li><a href="Triazolobenzodiazepine" title="Triazolobenzodiazepine">Triazolobenzodiazepines</a></li></ul></li></ul>

<ul><li><i>Antidepressants:</i> <a href="Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a>

<ul><li><a href="Dibenzazepine" title="Dibenzazepine">Dibenzazepines</a></li>

<li><a href="Dibenzocycloheptene" title="Dibenzocycloheptene">Dibenzocycloheptenes</a></li>

<li><a href="Dibenzothiepin" title="Dibenzothiepin">Dibenzothiepins</a></li>

<li><a href="Dibenzoxazepine" class="mw-redirect" title="Dibenzoxazepine">Dibenzoxazepines</a></li>

<li><a href="Dibenzoxepin" title="Dibenzoxepin">Dibenzoxepins</a></li></ul></li>

<li><a href="Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a></li></ul>

<ul><li><i>Antipsychotics/dopamine D<sub>2</sub> receptor antagonists or partial agonists:</i> <a href="Benzamide" title="Benzamide">Benzamides</a></li>

<li><a href="Benzimidazole" title="Benzimidazole">Benzimidazoles</a></li>

<li><a href="Benzothiazole" title="Benzothiazole">Benzisothiazoles</a></li>

<li><a href="Benzisoxazole" title="Benzisoxazole">Benzisoxazoles</a></li>

<li><a href="Butyrophenone" title="Butyrophenone">Butyrophenones</a></li>

<li><a href="Diphenylbutylpiperidine" title="Diphenylbutylpiperidine">Diphenylbutylpiperidines</a></li>

<li><a href="Phenylpiperazine" title="Phenylpiperazine">Phenylpiperazines</a></li>

<li><a href="Tricyclic_compound" class="mw-redirect" title="Tricyclic compound">Tricyclics</a>

<ul><li><a href="Dibenzazepine" title="Dibenzazepine">Dibenzazepines</a></li>

<li><a href="Dibenzodiazepine" title="Dibenzodiazepine">Dibenzodiazepines</a></li>

<li><a href="Dibenzothiazepine" title="Dibenzothiazepine">Dibenzothiazepines</a></li>

<li><a href="Dibenzothiepin" title="Dibenzothiepin">Dibenzothiepins</a></li>

<li><a href="Dibenzoxazepine" class="mw-redirect" title="Dibenzoxazepine">Dibenzoxazepines</a></li>

<li><a href="Phenothiazine" title="Phenothiazine">Phenothiazines</a></li>

<li><a href="Thienobenzodiazepine" title="Thienobenzodiazepine">Thienobenzodiazepines</a></li></ul></li></ul>

<ul><li><i>Mood stabilizers/anticonvulsants:</i> <a href="Gabapentinoid" title="Gabapentinoid">Gabapentinoids</a></li>

<li><a href="Tricyclic_compound" class="mw-redirect" title="Tricyclic compound">Tricyclics</a>

<ul><li><a href="Dibenzazepine" title="Dibenzazepine">Dibenzazepines</a></li></ul></li>

<li><a href="Valproate" title="Valproate">Valproates</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><i>Nootropics:</i> <a href="Racetam" title="Racetam">Racetams</a>

<ul><li><a href="Phenylpiracetam" title="Phenylpiracetam">Phenylpiracetams</a></li></ul></li></ul>

<ul><li><i>Miscellaneous:</i> <a href="Adamantane" title="Adamantane">Adamantanes</a></li>

<li><a href="Substituted_tetrahydroisoquinoline" title="Substituted tetrahydroisoquinoline">Tetrahydroisoquinolines</a></li>

<li><a href="Yohimban" title="Yohimban">Yohimbans</a></li></ul>

</div></td></tr></tbody></table></div>

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