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<li id="toc-Pharmacodynamics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Pharmacodynamics</span> </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> <li id="toc-Actions" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Actions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1.1</span> <span>Actions</span> </div> </a> <ul id="toc-Actions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Effects" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1.2</span> <span>Effects</span> </div> </a> <ul id="toc-Effects-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-List_of_DOx_drugs" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#List_of_DOx_drugs"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>List of DOx drugs</span> </div> </a> <ul id="toc-List_of_DOx_drugs-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Related_compounds" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Related_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Related compounds</span> </div> </a> <ul id="toc-Related_compounds-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a 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.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">For other uses, see <a href="/wiki/Dox_(disambiguation)" class="mw-redirect mw-disambig" title="Dox (disambiguation)">Dox</a>.</div> <figure class="mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:2,5-DMA.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/2%2C5-DMA.svg/200px-2%2C5-DMA.svg.png" decoding="async" width="200" height="190" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/2%2C5-DMA.svg/300px-2%2C5-DMA.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/27/2%2C5-DMA.svg/400px-2%2C5-DMA.svg.png 2x" data-file-width="400" data-file-height="380" /></a><figcaption><a href="/wiki/2,5-Dimethoxyamphetamine" title="2,5-Dimethoxyamphetamine">2,5-Dimethoxyamphetamine</a> (2,5-DMA), the base <a href="/wiki/Chemical_structure" title="Chemical structure">chemical structure</a> of the DOx family.</figcaption></figure> <p><b>4-Substituted-2,5-dimethoxyamphetamines</b> (<b>DO<i>x</i></b>) is a <a href="/wiki/Chemical_class" class="mw-redirect" title="Chemical class">chemical class</a> of <a href="/wiki/Substitution_reaction" title="Substitution reaction">substituted</a> <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a> <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivatives</a> featuring <a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">methoxy</a> <a href="/wiki/Functional_group" title="Functional group">groups</a> at the 2- and 5- positions of the <a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a> <a href="/wiki/Simple_aromatic_ring" title="Simple aromatic ring">ring</a>, and a <a href="/wiki/Substituent" title="Substituent">substituent</a> such as <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> or <a href="/wiki/Halogen" title="Halogen">halogen</a> at the 4- position of the phenyl ring.<sup id="cite_ref-Trachsel_1-0" class="reference"><a href="#cite_note-Trachsel-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GlennonDukat2024_2-0" class="reference"><a href="#cite_note-GlennonDukat2024-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> They are 4-substituted derivatives of <a href="/wiki/2,5-dimethoxyamphetamine" class="mw-redirect" title="2,5-dimethoxyamphetamine">2,5-dimethoxyamphetamine</a> (2,5-DMA, DOH) and are <a href="/wiki/Structural_analog" title="Structural analog">structurally related</a> to the <a href="/wiki/Natural_product" title="Natural product">naturally occurring</a> phenethylamine psychedelic <a href="/wiki/Mescaline" title="Mescaline">mescaline</a>. </p><p>The most well-known DOx drugs are <a href="/wiki/2,5-dimethoxy-4-methylamphetamine" class="mw-redirect" title="2,5-dimethoxy-4-methylamphetamine">DOM</a>, <a href="/wiki/2,5-dimethoxy-4-iodoamphetamine" class="mw-redirect" title="2,5-dimethoxy-4-iodoamphetamine">DOI</a>, <a href="/wiki/2,5-dimethoxy-4-bromoamphetamine" class="mw-redirect" title="2,5-dimethoxy-4-bromoamphetamine">DOB</a>, <a href="/wiki/2,5-dimethoxy-4-ethylamphetamine" class="mw-redirect" title="2,5-dimethoxy-4-ethylamphetamine">DOET</a>, and <a href="/wiki/2,5-dimethoxy-4-chloroamphetamine" class="mw-redirect" title="2,5-dimethoxy-4-chloroamphetamine">DOC</a>.<sup id="cite_ref-WillsErickson2012_3-0" class="reference"><a href="#cite_note-WillsErickson2012-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> DOI is widely used in <a href="/wiki/Scientific_research" class="mw-redirect" title="Scientific research">scientific research</a>.<sup id="cite_ref-GlennonDukat2024_2-1" class="reference"><a href="#cite_note-GlennonDukat2024-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CanalMorgan2012_4-0" class="reference"><a href="#cite_note-CanalMorgan2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> DOM has been used as a <a href="/wiki/Recreational_drug" class="mw-redirect" title="Recreational drug">recreational drug</a>, while DOET was an <a href="/wiki/Experimental_drug" title="Experimental drug">experimental</a> <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">pharmaceutical drug</a>.<sup id="cite_ref-Baggott2023_5-0" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Most compounds of this class are <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> and <a href="/wiki/Half-life" title="Half-life">long-lasting</a> <a href="/wiki/Psychedelic_drug" title="Psychedelic drug">psychedelic</a> <a href="/wiki/Drug" title="Drug">drugs</a>, and act as <a href="/wiki/Binding_selectivity" title="Binding selectivity">selective</a> <a href="/wiki/5-HT2A" class="mw-redirect" title="5-HT2A">5-HT<sub>2A</sub></a>, <a href="/wiki/5-HT2B" class="mw-redirect" title="5-HT2B">5-HT<sub>2B</sub></a>, and <a href="/wiki/5-HT2C" class="mw-redirect" title="5-HT2C">5-HT<sub>2C</sub></a> <a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">receptor</a> <a href="/wiki/Agonist" title="Agonist">agonists</a>.<sup id="cite_ref-LuethiRudinHoener2022_6-0" class="reference"><a href="#cite_note-LuethiRudinHoener2022-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ray2010_7-0" class="reference"><a href="#cite_note-Ray2010-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> A few bulkier derivatives such as <a href="/wiki/DOAM" class="mw-redirect" title="DOAM">DOAM</a> have similarly high <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> for 5-HT<sub>2</sub> receptors but have reduced <a href="/wiki/Intrinsic_activity" title="Intrinsic activity">activational efficacy</a> and do not produce psychedelic effects.<sup id="cite_ref-GlennonDukat2024_2-2" class="reference"><a href="#cite_note-GlennonDukat2024-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LuethiRudinHoener2022_6-1" class="reference"><a href="#cite_note-LuethiRudinHoener2022-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>DOI has been found to have extraordinarily potent <a href="/wiki/Anti-inflammatory" title="Anti-inflammatory">anti-inflammatory</a> effects.<sup id="cite_ref-NicholsJohnsonNichols2017_8-0" class="reference"><a href="#cite_note-NicholsJohnsonNichols2017-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FlanaganNichols2018_9-0" class="reference"><a href="#cite_note-FlanaganNichols2018-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-YuBecnelZerfaoui2008_10-0" class="reference"><a href="#cite_note-YuBecnelZerfaoui2008-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> These properties are not shared by all other related drugs and appear to be mediated by <a href="/wiki/Functional_selectivity" title="Functional selectivity">functionally selective</a> serotonin 5-HT<sub>2A</sub> receptor activation.<sup id="cite_ref-FlanaganNichols2018_9-1" class="reference"><a href="#cite_note-FlanaganNichols2018-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FlanaganFosterGalbato2024_11-0" class="reference"><a href="#cite_note-FlanaganFosterGalbato2024-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> The anti-inflammatory effects of DOI and related drugs may have medical applications.<sup id="cite_ref-NicholsJohnsonNichols2017_8-1" class="reference"><a href="#cite_note-NicholsJohnsonNichols2017-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FlanaganNichols2018_9-2" class="reference"><a href="#cite_note-FlanaganNichols2018-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Use">Use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=1" title="Edit section: Use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable"> <caption><span class="nowrap">Doses and durations of DOx drugs<sup id="cite_ref-GlennonDukat2024_2-3" class="reference"><a href="#cite_note-GlennonDukat2024-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JacobShulgin1994_12-0" class="reference"><a href="#cite_note-JacobShulgin1994-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NicholsGlennon1984_13-0" class="reference"><a href="#cite_note-NicholsGlennon1984-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WillsErickson2012_3-1" class="reference"><a href="#cite_note-WillsErickson2012-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BallentineFriedmanBzdok2022_14-0" class="reference"><a href="#cite_note-BallentineFriedmanBzdok2022-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PiHKAL1991_15-0" class="reference"><a href="#cite_note-PiHKAL1991-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ShulginManningDaley2011_16-0" class="reference"><a href="#cite_note-ShulginManningDaley2011-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ValterArrizabalagaLandry1998_17-0" class="reference"><a href="#cite_note-ValterArrizabalagaLandry1998-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup></span> </caption> <tbody><tr> <th>Compound</th> <th>Chemical name</th> <th>Dosage</th> <th>Duration </th></tr> <tr> <td><a href="/wiki/DOAM_(drug)" class="mw-redirect" title="DOAM (drug)">DOAM</a></td> <td>4-Amyl-2,5-dimethoxyamphetamine</td> <td>>10 mg</td> <td>Unknown </td></tr> <tr> <td><a href="/wiki/DOB_(drug)" class="mw-redirect" title="DOB (drug)">DOB</a></td> <td>4-Bromo-2,5-dimethoxyamphetamine</td> <td>1–3 mg</td> <td>18–30 hours </td></tr> <tr> <td><a href="/wiki/DOBU_(drug)" class="mw-redirect" title="DOBU (drug)">DOBU</a></td> <td>4-Butyl-2,5-dimethoxyamphetamine</td> <td>>3 mg</td> <td>Very long </td></tr> <tr> <td><a href="/wiki/DOC_(drug)" class="mw-redirect" title="DOC (drug)">DOC</a></td> <td>4-Chloro-2,5-dimethoxyamphetamine</td> <td>1.5–3 mg</td> <td>12–24 hours </td></tr> <tr> <td><a href="/wiki/DOEF_(drug)" class="mw-redirect" title="DOEF (drug)">DOEF</a></td> <td>4-(2-Fluoroethyl)-2,5-dimethoxyamphetamine</td> <td>2–3.5 mg</td> <td>12–16 hours </td></tr> <tr> <td><a href="/wiki/DOET_(drug)" class="mw-redirect" title="DOET (drug)">DOET</a></td> <td>4-Ethyl-2,5-dimethoxyamphetamine</td> <td>2–6 mg</td> <td>5–20 hours </td></tr> <tr> <td><a href="/wiki/DOF_(drug)" class="mw-redirect" title="DOF (drug)">DOF</a></td> <td>4-Fluoro-2,5-dimethoxyamphetamine</td> <td>>18 mg</td> <td>Unknown </td></tr> <tr> <td><a href="/wiki/DOH_(drug)" class="mw-redirect" title="DOH (drug)">DOH</a> (2,5-DMA)</td> <td>2,5-Dimethoxyamphetamine</td> <td>80–160 mg</td> <td>6–8 hours </td></tr> <tr> <td><a href="/wiki/DOI_(drug)" class="mw-redirect" title="DOI (drug)">DOI</a></td> <td>4-Iodo-2,5-dimethoxyamphetamine</td> <td>1.5–3 mg</td> <td>16–30 hours </td></tr> <tr> <td><a href="/wiki/DOIB_(drug)" class="mw-redirect" title="DOIB (drug)">DOIB</a></td> <td>4-Isobutyl-2,5-dimethoxyamphetamine</td> <td>10–15 mg</td> <td>Unknown </td></tr> <tr> <td><a href="/wiki/DOIP_(drug)" class="mw-redirect" title="DOIP (drug)">DOIP</a></td> <td>4-Isopropyl-2,5-dimethoxyamphetamine</td> <td>20–30 mg</td> <td>Unknown </td></tr> <tr> <td><a href="/wiki/DOM_(drug)" class="mw-redirect" title="DOM (drug)">DOM</a></td> <td>4-Methyl-2,5-dimethoxyamphetamine</td> <td>3–10 mg</td> <td>14–20 hours </td></tr> <tr> <td><a href="/wiki/DON_(drug)" class="mw-redirect" title="DON (drug)">DON</a></td> <td>4-Nitro-2,5-dimethoxyamphetamine</td> <td>3–4.5 mg</td> <td>8–15 hours </td></tr> <tr> <td><a href="/wiki/DOPR_(drug)" class="mw-redirect" title="DOPR (drug)">DOPR</a></td> <td>4-Propyl-2,5-dimethoxyamphetamine</td> <td>2.5–5 mg</td> <td>20–30 hours </td></tr> <tr> <td><a href="/wiki/DOSB_(drug)" class="mw-redirect" title="DOSB (drug)">DOSB</a></td> <td>4-<i>sec</i>-Butyl-2,5-dimethoxyamphetamine</td> <td>25–30 mg</td> <td>Unknown </td></tr> <tr> <td><a href="/wiki/DOTB_(drug)" class="mw-redirect" title="DOTB (drug)">DOTB</a></td> <td>4-<i>tert</i>-Butyl-2,5-dimethoxyamphetamine</td> <td>>25 mg</td> <td>Unknown </td></tr> <tr> <td><a href="/wiki/MEM_(drug)" class="mw-redirect" title="MEM (drug)">MEM</a></td> <td>4-Ethoxy-2,5-dimethoxyamphetamine</td> <td>20–50 mg</td> <td>10–14 hours </td></tr> <tr> <td><a href="/wiki/Aleph_(psychedelic)" title="Aleph (psychedelic)">Aleph</a> (DOT)</td> <td>4-Methylthio-2,5-dimethoxyamphetamine</td> <td>5–10 mg</td> <td>6–8 hours </td></tr> <tr> <td><a href="/wiki/Aleph-2" title="Aleph-2">Aleph-2</a></td> <td>4-Ethylthio-2,5-dimethoxyamphetamine</td> <td>4–8 mg</td> <td>8–16 hours </td></tr> <tr> <td><a href="/wiki/Aleph-4" class="mw-redirect" title="Aleph-4">Aleph-4</a></td> <td>4-Isopropylthio-2,5-dimethoxyamphetamine</td> <td>7–12 mg</td> <td>12–20 hours </td></tr> <tr> <td><a href="/wiki/Aleph-6" class="mw-redirect" title="Aleph-6">Aleph-6</a></td> <td>4-Phenylthio-2,5-dimethoxyamphetamine</td> <td>≥40 mg</td> <td>Very long </td></tr> <tr> <td><a href="/wiki/Aleph-7" class="mw-redirect" title="Aleph-7">Aleph-7</a></td> <td>4-Propylthio-2,5-dimethoxyamphetamine</td> <td>4–7 mg</td> <td>15–30 hours </td></tr> <tr> <td><a href="/wiki/Ganesha_(psychedelic)" title="Ganesha (psychedelic)">G-1</a></td> <td>3,4-Dimethyl-2,5-dimethoxyamphetamine</td> <td>20–32 mg</td> <td>18–24 hours </td></tr> <tr> <td><a href="/wiki/G-3_(drug)" class="mw-redirect" title="G-3 (drug)">G-3</a></td> <td>3,4-(Trimethylene)-2,5-dimethoxyamphetamine</td> <td>12–18 mg</td> <td>8–12 hours </td></tr> <tr> <td><a href="/wiki/G-5_(drug)" class="mw-redirect" title="G-5 (drug)">G-5</a></td> <td>3,4-Norbornyl-2,5-dimethoxyamphetamine</td> <td>14–20 mg</td> <td>16–30 hours </td></tr> <tr> <td><a href="/wiki/2,4,5-Trimethoxyamphetamine" title="2,4,5-Trimethoxyamphetamine">TMA-2</a> (2,4,5-TMA)</td> <td>4-Methoxy-2,5-dimethoxyamphetamine</td> <td>20–40 mg</td> <td>8–12 hours </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=2" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DOx drugs like <a href="/wiki/DOM_(drug)" class="mw-redirect" title="DOM (drug)">DOM</a> have been associated with certain <a href="/wiki/Side_effect" title="Side effect">side effects</a> that have not occurred to the same extent with other psychedelics like <a href="/wiki/LSD" title="LSD">LSD</a>.<sup id="cite_ref-Baggott2023_5-1" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Examples of such side effects include physical symptoms like <a href="/wiki/Sweating" class="mw-redirect" title="Sweating">sweating</a>, <a href="/wiki/Tremor" title="Tremor">tremors</a>, and large increases in <a href="/wiki/Heart_rate" title="Heart rate">heart rate</a>.<sup id="cite_ref-Baggott2023_5-2" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=3" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Psychedelic_drug#Interactions" title="Psychedelic drug">Psychedelic drug § Interactions</a>, and <a href="/wiki/Trip_killer#Serotonergic_psychedelic_antidotes" title="Trip killer">Trip killer § Serotonergic psychedelic antidotes</a></div> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=4" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=5" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Actions">Actions</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=6" title="Edit section: Actions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable floatright"> <caption><span class="nowrap">DOx drugs at the human <a href="/wiki/5-HT2_receptor" title="5-HT2 receptor">5-HT<sub>2</sub> receptors</a></span> </caption> <tbody><tr> <th rowspan="2"><a href="/wiki/Chemical_compound" title="Chemical compound">Compound</a></th> <th colspan="3"><a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">Affinity</a> (K<sub>i</sub>, nM) </th></tr> <tr> <th><a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT<sub>2A</sub></a></th> <th><a href="/wiki/5-HT2B_receptor" title="5-HT2B receptor">5-HT<sub>2B</sub></a></th> <th><a href="/wiki/5-HT2C_receptor" title="5-HT2C receptor">5-HT<sub>2C</sub></a> </th></tr> <tr> <td><a href="/wiki/2,5-Dimethoxyamphetamine" title="2,5-Dimethoxyamphetamine"><abbr title="2,5-Dimethoxyamphetamine">2,5-DMA</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 2,5-Dimethoxyamphetamine</span></td> <td>211–2,502</td> <td>1,039</td> <td>104–>5,070 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine"><abbr title="2,5-Dimethoxy-4-methylamphetamine">DOM</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 2,5-Dimethoxy-4-methylamphetamine</span></td> <td>88–507.4</td> <td>11.7</td> <td>404–3,980 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine"><abbr title="2,5-Dimethoxy-4-ethylamphetamine">DOET</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 2,5-Dimethoxy-4-ethylamphetamine</span></td> <td>12–100</td> <td>28.8</td> <td>107.2–108 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-n-propylamphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-n-propylamphetamine"><abbr title="2,5-Dimethoxy-4-n-propylamphetamine">DOPR</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 2,5-Dimethoxy-4-n-propylamphetamine</span></td> <td>0.9</td> <td>54.4</td> <td>1.1 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-n-butylamphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-n-butylamphetamine"><abbr title="2,5-Dimethoxy-4-n-butylamphetamine">DOBU</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 2,5-Dimethoxy-4-n-butylamphetamine</span></td> <td>5.4</td> <td><abbr title="No data">ND</abbr></td> <td>60 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-t-butylamphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-t-butylamphetamine"><abbr title="2,5-Dimethoxy-4-t-butylamphetamine">DOTB</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 2,5-Dimethoxy-4-t-butylamphetamine</span></td> <td>3.7</td> <td>24.6</td> <td>2.2 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-amylamphetamine" title="2,5-Dimethoxy-4-amylamphetamine"><abbr title="2,5-Dimethoxy-4-amylamphetamine">DOAM</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 2,5-Dimethoxy-4-amylamphetamine</span></td> <td>3.5</td> <td><abbr title="No data">ND</abbr></td> <td>75 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-n-hexylamphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-n-hexylamphetamine"><abbr title="2,5-Dimethoxy-4-n-hexylamphetamine">DOHx</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 2,5-Dimethoxy-4-n-hexylamphetamine</span></td> <td>0.1</td> <td>30.3</td> <td>0.7 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-fluoroamphetamine" title="2,5-Dimethoxy-4-fluoroamphetamine"><abbr title="2,5-Dimethoxy-4-fluoroamphetamine">DOF</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 2,5-Dimethoxy-4-fluoroamphetamine</span></td> <td>41.7</td> <td>227</td> <td>28.7 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine"><abbr title="2,5-Dimethoxy-4-chloroamphetamine">DOC</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 2,5-Dimethoxy-4-chloroamphetamine</span></td> <td>1.4</td> <td>31.8</td> <td>2.0 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine"><abbr title="2,5-Dimethoxy-4-bromoamphetamine">DOB</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 2,5-Dimethoxy-4-bromoamphetamine</span></td> <td>0.6–41</td> <td>26.9</td> <td>1.3–60 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine"><abbr title="2,5-Dimethoxy-4-iodoamphetamine">DOI</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 2,5-Dimethoxy-4-iodoamphetamine</span></td> <td>0.7–165.4</td> <td>20.0–335.9</td> <td>2.4–45.8 </td></tr> <tr> <td><a href="/wiki/2,4,5-Trimethoxyamphetamine" title="2,4,5-Trimethoxyamphetamine"><abbr title="2,4,5-Trimethoxyamphetamine">TMA-2</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 2,4,5-Trimethoxyamphetamine</span></td> <td>57.9–584.2</td> <td>154.4–307</td> <td>87.7–4,062 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-ethoxyamphetamine" title="2,5-Dimethoxy-4-ethoxyamphetamine"><abbr title="2,5-Dimethoxy-4-ethoxyamphetamine">MEM</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 2,5-Dimethoxy-4-ethoxyamphetamine</span></td> <td>73.0–3,948</td> <td>64.5–763</td> <td>124–>10,000 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-ethylthioamphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-ethylthioamphetamine"><abbr title="2,5-Dimethoxy-4-ethylthioamphetamine">Aleph-2</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 2,5-Dimethoxy-4-ethylthioamphetamine</span></td> <td>60.4</td> <td>1.6</td> <td>50.3 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-acetylamphetamine" title="2,5-Dimethoxy-4-acetylamphetamine"><abbr title="2,5-Dimethoxy-4-acetylamphetamine">DOAc</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 2,5-Dimethoxy-4-acetylamphetamine</span></td> <td>80.5</td> <td>313</td> <td>91.3 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-nitroamphetamine" title="2,5-Dimethoxy-4-nitroamphetamine"><abbr title="2,5-Dimethoxy-4-nitroamphetamine">DON</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 2,5-Dimethoxy-4-nitroamphetamine</span></td> <td>5.5</td> <td>166</td> <td>22.4 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-cyanoamphetamine" title="2,5-Dimethoxy-4-cyanoamphetamine"><abbr title="2,5-Dimethoxy-4-cyanoamphetamine">DOCN</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 2,5-Dimethoxy-4-cyanoamphetamine</span></td> <td>45.7</td> <td>774</td> <td>1,011 </td></tr> <tr> <td><a href="/wiki/2,5-Dimethoxy-4-benzylamphetamine" title="2,5-Dimethoxy-4-benzylamphetamine"><abbr title="2,5-Dimethoxy-4-benzylamphetamine">DOBZ</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 2,5-Dimethoxy-4-benzylamphetamine</span></td> <td>0.4</td> <td>35.0</td> <td>1.0 </td></tr> <tr> <td><a href="/w/index.php?title=N,N-Dimethyl-2,5-dimethoxy-4-bromoamphetamine&action=edit&redlink=1" class="new" title="N,N-Dimethyl-2,5-dimethoxy-4-bromoamphetamine (page does not exist)"><abbr title="N,N-Dimethyl-2,5-dimethoxy-4-bromoamphetamine">M-154</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 N,N-Dimethyl-2,5-dimethoxy-4-bromoamphetamine</span></td> <td>94.2</td> <td>341</td> <td>68.1 </td></tr> <tr> <td><a href="/w/index.php?title=N-n-Propyl-2,5-dimethoxy-4-bromoamphetamine&action=edit&redlink=1" class="new" title="N-n-Propyl-2,5-dimethoxy-4-bromoamphetamine (page does not exist)"><abbr title="N-n-Propyl-2,5-dimethoxy-4-bromoamphetamine">D-367</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 N-n-Propyl-2,5-dimethoxy-4-bromoamphetamine</span></td> <td>88.5</td> <td>521</td> <td>514 </td></tr> <tr> <td><a href="/w/index.php?title=N,N,N-Trimethyl-2,5-dimethoxy-4-bromoamphetamine&action=edit&redlink=1" class="new" title="N,N,N-Trimethyl-2,5-dimethoxy-4-bromoamphetamine (page does not exist)"><abbr title="N,N,N-Trimethyl-2,5-dimethoxy-4-bromoamphetamine">QDOB</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 N,N,N-Trimethyl-2,5-dimethoxy-4-bromoamphetamine</span></td> <td>2,155</td> <td>>10,000</td> <td>6,298 </td></tr> <tr class="sortbottom"> <td colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Notes:</b> The smaller the value, the more avidly the drug binds to the site. <b>Refs:</b> <sup id="cite_ref-NelsonLucaitesWainscott1999_18-0" class="reference"><a href="#cite_note-NelsonLucaitesWainscott1999-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HemanthNistalaNguyen2023_19-0" class="reference"><a href="#cite_note-HemanthNistalaNguyen2023-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ray2010_7-1" class="reference"><a href="#cite_note-Ray2010-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LuethiRudinHoener2022_6-2" class="reference"><a href="#cite_note-LuethiRudinHoener2022-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RudinLuethiHoener2022_20-0" class="reference"><a href="#cite_note-RudinLuethiHoener2022-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-vanWijngaardenSoudijn1997_21-0" class="reference"><a href="#cite_note-vanWijngaardenSoudijn1997-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <p>The DOx drugs act as <a href="/wiki/Agonist" title="Agonist">agonists</a> of the <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> <a href="/wiki/5-HT2_receptor" title="5-HT2 receptor">5-HT<sub>2</sub> receptors</a>, including of the serotonin <a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT<sub>2A</sub></a>, <a href="/wiki/5-HT2B_receptor" title="5-HT2B receptor">5-HT<sub>2B</sub></a>, and <a href="/wiki/5-HT2C_receptor" title="5-HT2C receptor">5-HT<sub>2C</sub> receptors</a>.<sup id="cite_ref-LuethiRudinHoener2022_6-3" class="reference"><a href="#cite_note-LuethiRudinHoener2022-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NicholsNichols2021_22-0" class="reference"><a href="#cite_note-NicholsNichols2021-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ray2010_7-2" class="reference"><a href="#cite_note-Ray2010-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GlennonDukat2024_2-4" class="reference"><a href="#cite_note-GlennonDukat2024-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WillsErickson2012_3-2" class="reference"><a href="#cite_note-WillsErickson2012-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PottieCannaertStove2020_23-0" class="reference"><a href="#cite_note-PottieCannaertStove2020-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Their <a href="/wiki/Serotonergic_psychedelic" class="mw-redirect" title="Serotonergic psychedelic">psychedelic</a> effects are thought to be mediated specifically by activation of the serotonin 5-HT<sub>2A</sub> receptor.<sup id="cite_ref-NicholsNichols2021_22-1" class="reference"><a href="#cite_note-NicholsNichols2021-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GlennonDukat2024_2-5" class="reference"><a href="#cite_note-GlennonDukat2024-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>In contrast to other amphetamines, DOx drugs like <a href="/wiki/DOC_(drug)" class="mw-redirect" title="DOC (drug)">DOC</a>, <a href="/wiki/DOET_(drug)" class="mw-redirect" title="DOET (drug)">DOET</a>, and <a href="/wiki/DOM_(drug)" class="mw-redirect" title="DOM (drug)">DOM</a> are inactive as <a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">monoamine releasing agents</a> and <a href="/wiki/Monoamine_reuptake_inhibitor" title="Monoamine reuptake inhibitor">reuptake inhibitors</a>.<sup id="cite_ref-EshlemanForsterWolfrum2014_24-0" class="reference"><a href="#cite_note-EshlemanForsterWolfrum2014-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-EshlemanWolfrumReed2018_25-0" class="reference"><a href="#cite_note-EshlemanWolfrumReed2018-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LuethiRudinHoener2022_6-4" class="reference"><a href="#cite_note-LuethiRudinHoener2022-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Some of the DOx drugs, including <a href="/wiki/DOB_(drug)" class="mw-redirect" title="DOB (drug)">DOB</a>, DOET, <a href="/wiki/DOI_(drug)" class="mw-redirect" title="DOI (drug)">DOI</a>, and DOM, are agonists of the rat, <a href="/wiki/Rhesus_monkey" class="mw-redirect" title="Rhesus monkey">rhesus monkey</a>, and/or human <a href="/wiki/Trace_amine-associated_receptor_1" class="mw-redirect" title="Trace amine-associated receptor 1">trace amine-associated receptor 1</a> (TAAR1) with varying potencies.<sup id="cite_ref-LewinMillerGilmour2011_26-0" class="reference"><a href="#cite_note-LewinMillerGilmour2011-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BunzowSondersArttamangkul2001_27-0" class="reference"><a href="#cite_note-BunzowSondersArttamangkul2001-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Effects">Effects</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=7" title="Edit section: Effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In contrast to <a href="/wiki/Amphetamine-type_stimulant" class="mw-redirect" title="Amphetamine-type stimulant">amphetamines</a> like <a href="/wiki/(%E2%80%93)-cathinone" class="mw-redirect" title="(–)-cathinone">(–)-cathinone</a>, but similarly to <a href="/wiki/Mescaline" title="Mescaline">mescaline</a>, DOM has shown no <a href="/wiki/Stimulant" title="Stimulant">stimulant</a>-like or <a href="/wiki/Positive_reinforcement" class="mw-redirect" title="Positive reinforcement">reinforcing</a> effects in <a href="/wiki/Rhesus_monkey" class="mw-redirect" title="Rhesus monkey">rhesus monkeys</a>.<sup id="cite_ref-FantegrossiMurnaneReissig2008_28-0" class="reference"><a href="#cite_note-FantegrossiMurnaneReissig2008-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CanalMurnane2017_29-0" class="reference"><a href="#cite_note-CanalMurnane2017-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Yanagita1986_30-0" class="reference"><a href="#cite_note-Yanagita1986-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Maguire2024_31-0" class="reference"><a href="#cite_note-Maguire2024-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Conversely however, DOC has shown reinforcing effects, including <a href="/wiki/Conditioned_place_preference" title="Conditioned place preference">conditioned place preference</a> (CPP) and <a href="/wiki/Self-administration" title="Self-administration">self-administration</a>, in rodents similarly to <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>.<sup id="cite_ref-ChaJeonJang2018_32-0" class="reference"><a href="#cite_note-ChaJeonJang2018-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> This is analogous to other findings in which various <a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2C</a> and <a href="/wiki/NBOMe" class="mw-redirect" title="NBOMe">NBOMe</a> <a href="/wiki/Drug" title="Drug">drugs</a> have been found to produce brain <a href="/wiki/Dopaminergic" title="Dopaminergic">dopaminergic</a> elevations and reinforcing effects in rodents.<sup id="cite_ref-Gil-MartinsBarbosaBorges2025_33-0" class="reference"><a href="#cite_note-Gil-MartinsBarbosaBorges2025-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KimMaHur2021_34-0" class="reference"><a href="#cite_note-KimMaHur2021-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CustodioSaysonBotanas2020_35-0" class="reference"><a href="#cite_note-CustodioSaysonBotanas2020-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SeoHurKo2019_36-0" class="reference"><a href="#cite_note-SeoHurKo2019-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JoJooYoun2022_37-0" class="reference"><a href="#cite_note-JoJooYoun2022-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LeeHurHwang2023_38-0" class="reference"><a href="#cite_note-LeeHurHwang2023-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KimKookMa2024_39-0" class="reference"><a href="#cite_note-KimKookMa2024-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=8" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The DOx drugs are <a href="/wiki/Oral_administration" title="Oral administration">orally active</a> and many have doses in the range of 1 to 10<span class="nowrap"> </span>mg and <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">durations</a> in the range of 8 to 30<span class="nowrap"> </span>hours.<sup id="cite_ref-BallentineFriedmanBzdok2022_14-1" class="reference"><a href="#cite_note-BallentineFriedmanBzdok2022-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WillsErickson2012_3-3" class="reference"><a href="#cite_note-WillsErickson2012-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GlennonDukat2024_2-6" class="reference"><a href="#cite_note-GlennonDukat2024-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JacobShulgin1994_12-1" class="reference"><a href="#cite_note-JacobShulgin1994-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Baggott2023_5-3" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Some DOx drugs, such as DOM and DOB, appear to have durations that increase non-linearly with dosage, for instance 8<span class="nowrap"> </span>hours at lower doses and as long as 30<span class="nowrap"> </span>hours or even up to 3 or 4<span class="nowrap"> </span>days at higher doses.<sup id="cite_ref-Baggott2023_5-4" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PiHKAL1991_15-1" class="reference"><a href="#cite_note-PiHKAL1991-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> This suggests that the <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">pathways</a> mediating the <a href="/wiki/Drug_metabolism" title="Drug metabolism">metabolism</a> of these drugs can saturate.<sup id="cite_ref-Baggott2023_5-5" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The DOx drugs are metabolized primarily by <i>O</i>-<a href="/wiki/Demethylation" title="Demethylation">demethylation</a>.<sup id="cite_ref-WillsErickson2012_3-4" class="reference"><a href="#cite_note-WillsErickson2012-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> However, DOM is primarily metabolized by <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> at its <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a>.<sup id="cite_ref-WillsErickson2012_3-5" class="reference"><a href="#cite_note-WillsErickson2012-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=9" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/DOM_(drug)" class="mw-redirect" title="DOM (drug)">DOM</a> was the first psychedelic of the DOx series to be discovered.<sup id="cite_ref-CanalMorgan2012_4-1" class="reference"><a href="#cite_note-CanalMorgan2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It was first <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesized</a> by <a href="/wiki/Alexander_Shulgin" title="Alexander Shulgin">Alexander Shulgin</a> at <a href="/wiki/Dow_Chemical_Company" title="Dow Chemical Company">Dow Chemical Company</a> in 1963, who had had his first <a href="/wiki/Psychedelic_experience" title="Psychedelic experience">psychedelic experience</a>, with <a href="/wiki/Mescaline" title="Mescaline">mescaline</a> (3,4,5-trimethoxyphenethylamine), in 1960.<sup id="cite_ref-CanalMorgan2012_4-2" class="reference"><a href="#cite_note-CanalMorgan2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Baggott2023_5-6" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ShulginManningDaley2011_16-1" class="reference"><a href="#cite_note-ShulginManningDaley2011-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Shulgin personally tried DOM on January 4, 1964 and discovered its psychedelic effects.<sup id="cite_ref-openDemocracy2014_40-0" class="reference"><a href="#cite_note-openDemocracy2014-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CanalMorgan2012_4-3" class="reference"><a href="#cite_note-CanalMorgan2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Baggott2023_5-7" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ShulginManningDaley2011_16-2" class="reference"><a href="#cite_note-ShulginManningDaley2011-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> <a href="/wiki/2,4,5-Trimethoxyamphetamine" title="2,4,5-Trimethoxyamphetamine">2,4,5-Trimethoxyamphetamine</a> (TMA-2; "DOMeO") had been synthesized by Bruckner in 1933, but its psychedelic effects were not described until Shulgin tried the compound and reported its effects in the <a href="/wiki/Scientific_literature" title="Scientific literature">scientific literature</a> in 1964.<sup id="cite_ref-Shulgin1978_41-0" class="reference"><a href="#cite_note-Shulgin1978-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bruckner1933_42-0" class="reference"><a href="#cite_note-Bruckner1933-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Shulgin1964_43-0" class="reference"><a href="#cite_note-Shulgin1964-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Prior to this, <a href="/wiki/3,4,5-trimethoxyamphetamine" class="mw-redirect" title="3,4,5-trimethoxyamphetamine">3,4,5-trimethoxyamphetamine</a> (TMA; α-methylmescaline) had been synthesized by Hey in 1947, being found by him to produce <a href="/wiki/Euphoria" title="Euphoria">euphoria</a>, and was described by Peretz and colleagues in 1955 as clearly producing psychedelic effects.<sup id="cite_ref-Shulgin1978_41-1" class="reference"><a href="#cite_note-Shulgin1978-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PeretzSmythiesGibson1955_44-0" class="reference"><a href="#cite_note-PeretzSmythiesGibson1955-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ShulginBunnell1961_45-0" class="reference"><a href="#cite_note-ShulginBunnell1961-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hey1947_46-0" class="reference"><a href="#cite_note-Hey1947-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>Following his discovery of DOM, Shulgin developed <a href="/wiki/DOET_(drug)" class="mw-redirect" title="DOET (drug)">DOET</a> and found that at low doses it was a remarkable "<a href="/wiki/Psychic_energizer" class="mw-redirect" title="Psychic energizer">psychic energizer</a>" without producing psychedelic effects at these doses.<sup id="cite_ref-Baggott2023_5-8" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Dow Chemical Company decided to move forward with <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trials</a> of DOET as a potential <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">pharmaceutical drug</a> for such purposes.<sup id="cite_ref-Baggott2023_5-9" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Shulgin and Dow Chemical Company filed a <a href="/wiki/Patent" title="Patent">patent</a> for DOET in 1966, although it was not published until 1970.<sup id="cite_ref-Baggott2023_5-10" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CanalMorgan2012_4-4" class="reference"><a href="#cite_note-CanalMorgan2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-US3547999A_47-0" class="reference"><a href="#cite_note-US3547999A-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> Dow Chemical Company tasked <a href="/wiki/Solomon_H._Snyder" title="Solomon H. Snyder">Solomon H. Snyder</a> at <a href="/wiki/Johns_Hopkins_University" title="Johns Hopkins University">Johns Hopkins University</a> with clinically studying DOET.<sup id="cite_ref-Baggott2023_5-11" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>In April 1967, following the banning of <a href="/wiki/LSD" title="LSD">LSD</a> in <a href="/wiki/California" title="California">California</a> in 1966, DOM emerged as a <a href="/wiki/Street_drug" class="mw-redirect" title="Street drug">street drug</a> and legal LSD alternative with the name "STP" (allegedly short for "Serenity, Tranquility, and Peace") in the <a href="/wiki/Haight-Ashbury" title="Haight-Ashbury">Haight-Ashbury</a> district in <a href="/wiki/San_Francisco" title="San Francisco">San Francisco</a>.<sup id="cite_ref-Baggott2023_5-12" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TroutDaley2024_48-0" class="reference"><a href="#cite_note-TroutDaley2024-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> This occurred due to DOM being publicly distributed for free in the form of high-dose <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a> by LSD distributor <a href="/wiki/Owsley_Stanley" title="Owsley Stanley">Owsley Stanley</a>, who had personally learned of DOM from Shulgin.<sup id="cite_ref-Baggott2023_5-13" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TroutDaley2024_48-1" class="reference"><a href="#cite_note-TroutDaley2024-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> It is unclear why Shulgin provided information about DOM to Stanley, since doing so had the potential to risk Shulgin's professional career and the DOET clinical studies.<sup id="cite_ref-Baggott2023_5-14" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TroutDaley2024_48-2" class="reference"><a href="#cite_note-TroutDaley2024-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> One possibility is that Dow Chemical Company was not further looking into DOM and Shulgin thought that it was a promising drug that would otherwise be forgotten.<sup id="cite_ref-Baggott2023_5-15" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> In any case, street use of DOM was short-lived because the tablets caused a public health crisis due to them often producing very long <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">durations</a> (up to 3–4<span class="nowrap"> </span>days), intense experiences, worrying physical <a href="/wiki/Side_effect" title="Side effect">side effects</a>, and <a href="/wiki/Hospitalization" class="mw-redirect" title="Hospitalization">hospitalizations</a>.<sup id="cite_ref-Baggott2023_5-16" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> DOM was first reported on in the media and scientific literature in 1967 as a result of the crisis.<sup id="cite_ref-Baggott2023_5-17" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SnyderFaillaceHollister1967_49-0" class="reference"><a href="#cite_note-SnyderFaillaceHollister1967-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SnyderFaillaceWeingartner1968_50-0" class="reference"><a href="#cite_note-SnyderFaillaceWeingartner1968-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> DOM became illegal in the <a href="/wiki/United_States" title="United States">United States</a> in 1968.<sup id="cite_ref-Baggott2023_5-18" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Dow Chemical Company terminated its clinical research program on DOET due to the DOM public health crisis.<sup id="cite_ref-Baggott2023_5-19" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> DOET was subsequently first described in the literature by Snyder and colleagues in 1968.<sup id="cite_ref-SnyderFaillaceWeingartner1968_50-1" class="reference"><a href="#cite_note-SnyderFaillaceWeingartner1968-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> Snyder continued to be interested in DOET as a potential medicine, but it was never further developed.<sup id="cite_ref-SnyderFaillaceWeingartner1968_50-2" class="reference"><a href="#cite_note-SnyderFaillaceWeingartner1968-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> Snyder also described <a href="/wiki/2,5-dimethoxyamphetamine" class="mw-redirect" title="2,5-dimethoxyamphetamine">2,5-dimethoxyamphetamine</a> (2,5-DMA), which had been synthesized and tested by Shulgin, in the literature in 1968.<sup id="cite_ref-SnyderRichelson1968_51-0" class="reference"><a href="#cite_note-SnyderRichelson1968-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> DOM and DOET were further described in the scientific literature by Shulgin in 1969.<sup id="cite_ref-Shulgin1969_52-0" class="reference"><a href="#cite_note-Shulgin1969-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CanalMorgan2012_4-5" class="reference"><a href="#cite_note-CanalMorgan2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Baggott2023_5-20" class="reference"><a href="#cite_note-Baggott2023-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> In addition, Shulgin discussed DOM, DOET, TMA-2, and 2,5-DMA in a book chapter on hallucinogens published in 1970.<sup id="cite_ref-Shulgin1970_53-0" class="reference"><a href="#cite_note-Shulgin1970-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p>The earlier DOx drugs like DOM and DOET were subsequently followed by <a href="/wiki/DOB_(drug)" class="mw-redirect" title="DOB (drug)">DOB</a>, which was developed by Shulgin and colleagues like <a href="/wiki/Claudio_Naranjo" title="Claudio Naranjo">Claudio Naranjo</a>, in 1971,<sup id="cite_ref-CanalMorgan2012_4-6" class="reference"><a href="#cite_note-CanalMorgan2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ShulginSargentNaranjo1971_54-0" class="reference"><a href="#cite_note-ShulginSargentNaranjo1971-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> and by <a href="/wiki/DOI_(drug)" class="mw-redirect" title="DOI (drug)">DOI</a>, <a href="/wiki/DOC_(drug)" class="mw-redirect" title="DOC (drug)">DOC</a>, and a few other <a href="/wiki/Structural_analog" title="Structural analog">analogues</a>, which were developed by another research group, in 1973.<sup id="cite_ref-CanalMorgan2012_4-7" class="reference"><a href="#cite_note-CanalMorgan2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CouttsMalicky1973_55-0" class="reference"><a href="#cite_note-CouttsMalicky1973-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> After this, numerous other DOx drugs were synthesized and characterized, both by Shulgin and other scientists.<sup id="cite_ref-Shulgin1978_41-2" class="reference"><a href="#cite_note-Shulgin1978-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NicholsGlennon1984_13-1" class="reference"><a href="#cite_note-NicholsGlennon1984-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PiHKAL1991_15-2" class="reference"><a href="#cite_note-PiHKAL1991-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JacobShulgin1994_12-2" class="reference"><a href="#cite_note-JacobShulgin1994-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ShulginManningDaley2011_16-3" class="reference"><a href="#cite_note-ShulginManningDaley2011-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nichols2018_56-0" class="reference"><a href="#cite_note-Nichols2018-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GlennonDukat2024_2-7" class="reference"><a href="#cite_note-GlennonDukat2024-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Following its discovery, DOI has become widely used in <a href="/wiki/Scientific_research" class="mw-redirect" title="Scientific research">scientific research</a> in the study of the serotonin 5-HT<sub>2</sub> receptors.<sup id="cite_ref-CanalMorgan2012_4-8" class="reference"><a href="#cite_note-CanalMorgan2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GlennonDukat2024_2-8" class="reference"><a href="#cite_note-GlennonDukat2024-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="List_of_DOx_drugs">List of DOx drugs</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=10" title="Edit section: List of DOx drugs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The DO<i>x</i> family includes the following members: </p> <table class="wikitable"> <tbody><tr> <th>Structure </th> <th>Name </th> <th>Abbreviation </th> <th>CAS number </th> <th>Ref </th></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2,5-DMA.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/2%2C5-DMA.svg/115px-2%2C5-DMA.svg.png" decoding="async" width="115" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/2%2C5-DMA.svg/173px-2%2C5-DMA.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/27/2%2C5-DMA.svg/230px-2%2C5-DMA.svg.png 2x" data-file-width="400" data-file-height="380" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxyamphetamine" title="2,5-Dimethoxyamphetamine">2,5-Dimethoxyamphetamine</a> </td> <td>2,5-DMA </td> <td>2801-68-5 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOAM.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/DOAM.svg/115px-DOAM.svg.png" decoding="async" width="115" height="61" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/DOAM.svg/173px-DOAM.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/78/DOAM.svg/230px-DOAM.svg.png 2x" data-file-width="705" data-file-height="375" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-amylamphetamine" title="2,5-Dimethoxy-4-amylamphetamine">2,5-Dimethoxy-4-amylamphetamine</a> </td> <td>DOAM </td> <td>63779-90-8 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOB-racemic-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/DOB-racemic-skeletal.svg/115px-DOB-racemic-skeletal.svg.png" decoding="async" width="115" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/DOB-racemic-skeletal.svg/173px-DOB-racemic-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ec/DOB-racemic-skeletal.svg/230px-DOB-racemic-skeletal.svg.png 2x" data-file-width="480" data-file-height="375" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">2,5-Dimethoxy-4-bromoamphetamine</a> </td> <td>DOB </td> <td>64638-07-9 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOBU.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/DOBU.svg/115px-DOBU.svg.png" decoding="async" width="115" height="67" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/DOBU.svg/173px-DOBU.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b2/DOBU.svg/230px-DOBU.svg.png 2x" data-file-width="645" data-file-height="375" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-butylamphetamine" title="2,5-Dimethoxy-4-butylamphetamine">2,5-Dimethoxy-4-butylamphetamine</a> </td> <td>DOBU </td> <td>63779-89-5 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOC-racemic-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/DOC-racemic-skeletal.svg/115px-DOC-racemic-skeletal.svg.png" decoding="async" width="115" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/DOC-racemic-skeletal.svg/173px-DOC-racemic-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1d/DOC-racemic-skeletal.svg/230px-DOC-racemic-skeletal.svg.png 2x" data-file-width="737" data-file-height="484" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">2,5-Dimethoxy-4-chloroamphetamine</a> </td> <td>DOC </td> <td>123431-31-2 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:MEM.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ad/MEM.svg/115px-MEM.svg.png" decoding="async" width="115" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ad/MEM.svg/173px-MEM.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ad/MEM.svg/230px-MEM.svg.png 2x" data-file-width="580" data-file-height="375" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-ethoxyamphetamine" title="2,5-Dimethoxy-4-ethoxyamphetamine">2,5-Dimethoxy-4-ethoxyamphetamine</a> </td> <td>MEM </td> <td>16128-88-4 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOMOM_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fc/DOMOM_structure.png/115px-DOMOM_structure.png" decoding="async" width="115" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fc/DOMOM_structure.png/173px-DOMOM_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fc/DOMOM_structure.png/230px-DOMOM_structure.png 2x" data-file-width="1280" data-file-height="855" /></a></span> </td> <td>2,5-Dimethoxy-4-(methoxymethyl)amphetamine </td> <td>DOMOM </td> <td>260810-10-4 </td> <td><sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOMOE_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/DOMOE_structure.png/115px-DOMOE_structure.png" decoding="async" width="115" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/DOMOE_structure.png/173px-DOMOE_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/73/DOMOE_structure.png/230px-DOMOE_structure.png 2x" data-file-width="1407" data-file-height="856" /></a></span> </td> <td>2,5-Dimethoxy-4-(ethoxymethyl)amphetamine </td> <td>DOMOE </td> <td>930836-81-0 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2,5-Dimethoxy-4-ethylamphetamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cc/2%2C5-Dimethoxy-4-ethylamphetamine.svg/115px-2%2C5-Dimethoxy-4-ethylamphetamine.svg.png" decoding="async" width="115" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cc/2%2C5-Dimethoxy-4-ethylamphetamine.svg/173px-2%2C5-Dimethoxy-4-ethylamphetamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cc/2%2C5-Dimethoxy-4-ethylamphetamine.svg/230px-2%2C5-Dimethoxy-4-ethylamphetamine.svg.png 2x" data-file-width="620" data-file-height="371" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">2,5-Dimethoxy-4-ethylamphetamine</a> </td> <td>DOET </td> <td>22004-32-6 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2,5-dimethoxy-4-ethylthioamphetamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/2%2C5-dimethoxy-4-ethylthioamphetamine.svg/115px-2%2C5-dimethoxy-4-ethylthioamphetamine.svg.png" decoding="async" width="115" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/2%2C5-dimethoxy-4-ethylthioamphetamine.svg/173px-2%2C5-dimethoxy-4-ethylthioamphetamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/56/2%2C5-dimethoxy-4-ethylthioamphetamine.svg/230px-2%2C5-dimethoxy-4-ethylthioamphetamine.svg.png 2x" data-file-width="620" data-file-height="336" /></a></span> </td> <td><a href="/wiki/Aleph_(psychedelic)#Aleph-2" title="Aleph (psychedelic)">2,5-Dimethoxy-4-ethylthioamphetamine</a> </td> <td>Aleph-2 </td> <td>185562-00-9 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2,5-Dimethoxy-4-fluoroamphetamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/2%2C5-Dimethoxy-4-fluoroamphetamine.svg/115px-2%2C5-Dimethoxy-4-fluoroamphetamine.svg.png" decoding="async" width="115" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/2%2C5-Dimethoxy-4-fluoroamphetamine.svg/173px-2%2C5-Dimethoxy-4-fluoroamphetamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/29/2%2C5-Dimethoxy-4-fluoroamphetamine.svg/230px-2%2C5-Dimethoxy-4-fluoroamphetamine.svg.png 2x" data-file-width="620" data-file-height="460" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-fluoroamphetamine" title="2,5-Dimethoxy-4-fluoroamphetamine">2,5-Dimethoxy-4-fluoroamphetamine</a> </td> <td>DOF </td> <td>125903-69-7 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/2%2C5-Dimethoxy-4-%282-fluoroethyl%29amphetamine.svg/115px-2%2C5-Dimethoxy-4-%282-fluoroethyl%29amphetamine.svg.png" decoding="async" width="115" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/2%2C5-Dimethoxy-4-%282-fluoroethyl%29amphetamine.svg/173px-2%2C5-Dimethoxy-4-%282-fluoroethyl%29amphetamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/29/2%2C5-Dimethoxy-4-%282-fluoroethyl%29amphetamine.svg/230px-2%2C5-Dimethoxy-4-%282-fluoroethyl%29amphetamine.svg.png 2x" data-file-width="620" data-file-height="365" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine" title="2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine">2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine</a> </td> <td>DOEF </td> <td>121649-01-2 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOPF_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/DOPF_structure.png/115px-DOPF_structure.png" decoding="async" width="115" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/DOPF_structure.png/173px-DOPF_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/DOPF_structure.png/230px-DOPF_structure.png 2x" data-file-width="1566" data-file-height="926" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-(3-fluoropropyl)amphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-(3-fluoropropyl)amphetamine">2,5-Dimethoxy-4-(3-fluoropropyl)amphetamine</a> </td> <td>DOPF </td> <td>? </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOI-racemic-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/DOI-racemic-skeletal.svg/115px-DOI-racemic-skeletal.svg.png" decoding="async" width="115" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/DOI-racemic-skeletal.svg/173px-DOI-racemic-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/DOI-racemic-skeletal.svg/230px-DOI-racemic-skeletal.svg.png 2x" data-file-width="726" data-file-height="475" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">2,5-Dimethoxy-4-iodoamphetamine</a> </td> <td>DOI </td> <td>42203-78-1 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Aleph-4.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Aleph-4.svg/115px-Aleph-4.svg.png" decoding="async" width="115" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Aleph-4.svg/173px-Aleph-4.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Aleph-4.svg/230px-Aleph-4.svg.png 2x" data-file-width="620" data-file-height="336" /></a></span> </td> <td><a href="/wiki/Aleph_(psychedelic)#Aleph-4" title="Aleph (psychedelic)">2,5-Dimethoxy-4-isopropylthioamphetamine</a> </td> <td>Aleph-4 </td> <td>123643-26-5 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Trimethoxyamphetamine-2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Trimethoxyamphetamine-2.svg/120px-Trimethoxyamphetamine-2.svg.png" decoding="async" width="115" height="92" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Trimethoxyamphetamine-2.svg/250px-Trimethoxyamphetamine-2.svg.png 1.5x" data-file-width="475" data-file-height="380" /></a></span> </td> <td><a href="/wiki/2,4,5-Trimethoxyamphetamine" title="2,4,5-Trimethoxyamphetamine">2,4,5-Trimethoxyamphetamine</a> </td> <td>TMA-2 (DOMeO) </td> <td>1083-09-6 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2,5-Dimethoxy-4-methylamphetamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/2%2C5-Dimethoxy-4-methylamphetamine.svg/115px-2%2C5-Dimethoxy-4-methylamphetamine.svg.png" decoding="async" width="115" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/2%2C5-Dimethoxy-4-methylamphetamine.svg/173px-2%2C5-Dimethoxy-4-methylamphetamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/66/2%2C5-Dimethoxy-4-methylamphetamine.svg/230px-2%2C5-Dimethoxy-4-methylamphetamine.svg.png 2x" data-file-width="620" data-file-height="415" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">2,5-Dimethoxy-4-methylamphetamine</a> </td> <td>DOM </td> <td>15588-95-1 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2,5-dimethoxy-4-methylthioamphetamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/2%2C5-dimethoxy-4-methylthioamphetamine.svg/120px-2%2C5-dimethoxy-4-methylthioamphetamine.svg.png" decoding="async" width="115" height="73" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/2%2C5-dimethoxy-4-methylthioamphetamine.svg/250px-2%2C5-dimethoxy-4-methylthioamphetamine.svg.png 1.5x" data-file-width="620" data-file-height="393" /></a></span> </td> <td><a href="/wiki/Aleph_(psychedelic)" title="Aleph (psychedelic)">2,5-Dimethoxy-4-methylthioamphetamine</a> </td> <td>Aleph-1 (DOT) </td> <td>61638-07-1 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2,5-Dimethoxy-4-nitroamphetamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/2%2C5-Dimethoxy-4-nitroamphetamine.svg/120px-2%2C5-Dimethoxy-4-nitroamphetamine.svg.png" decoding="async" width="115" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/2%2C5-Dimethoxy-4-nitroamphetamine.svg/250px-2%2C5-Dimethoxy-4-nitroamphetamine.svg.png 1.5x" data-file-width="620" data-file-height="413" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-nitroamphetamine" title="2,5-Dimethoxy-4-nitroamphetamine">2,5-Dimethoxy-4-nitroamphetamine</a> </td> <td>DON </td> <td>67460-68-8 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Aleph-6.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Aleph-6.svg/115px-Aleph-6.svg.png" decoding="async" width="115" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Aleph-6.svg/173px-Aleph-6.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/31/Aleph-6.svg/230px-Aleph-6.svg.png 2x" data-file-width="620" data-file-height="336" /></a></span> </td> <td><a href="/wiki/Aleph_(psychedelic)#Aleph-6" title="Aleph (psychedelic)">2,5-Dimethoxy-4-phenylthioamphetamine</a> </td> <td>Aleph-6 </td> <td>952006-44-9 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOBZ_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/DOBZ_structure.png/115px-DOBZ_structure.png" decoding="async" width="115" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/DOBZ_structure.png/173px-DOBZ_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/eb/DOBZ_structure.png/230px-DOBZ_structure.png 2x" data-file-width="1380" data-file-height="856" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-benzylamphetamine" title="2,5-Dimethoxy-4-benzylamphetamine">2,5-Dimethoxy-4-benzylamphetamine</a> </td> <td>DOBz </td> <td>125903-73-3 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DO3MeOBZ_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/DO3MeOBZ_structure.png/115px-DO3MeOBZ_structure.png" decoding="async" width="115" height="61" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/DO3MeOBZ_structure.png/173px-DO3MeOBZ_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8a/DO3MeOBZ_structure.png/230px-DO3MeOBZ_structure.png 2x" data-file-width="1619" data-file-height="861" /></a></span> </td> <td>2,5-Dimethoxy-4-(3-methoxybenzyl)amphetamine </td> <td>DO3MeOBZ </td> <td>930836-90-1 </td> <td><sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOTHFM_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/DOTHFM_structure.png/120px-DOTHFM_structure.png" decoding="async" width="115" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/DOTHFM_structure.png/250px-DOTHFM_structure.png 1.5x" data-file-width="1379" data-file-height="856" /></a></span> </td> <td>2,5-Dimethoxy-4-[(tetrahydrofuran-2-yl)methyl]amphetamine </td> <td>DOTHFM </td> <td>930776-12-8 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2,5-Dimethoxy-4-propylamphetamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/2%2C5-Dimethoxy-4-propylamphetamine.svg/115px-2%2C5-Dimethoxy-4-propylamphetamine.svg.png" decoding="async" width="115" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/2%2C5-Dimethoxy-4-propylamphetamine.svg/173px-2%2C5-Dimethoxy-4-propylamphetamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dd/2%2C5-Dimethoxy-4-propylamphetamine.svg/230px-2%2C5-Dimethoxy-4-propylamphetamine.svg.png 2x" data-file-width="620" data-file-height="336" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-propylamphetamine" title="2,5-Dimethoxy-4-propylamphetamine">2,5-Dimethoxy-4-propylamphetamine</a> </td> <td>DOPR </td> <td>63779-88-4 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOiPR_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/DOiPR_structure.png/120px-DOiPR_structure.png" decoding="async" width="115" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/DOiPR_structure.png/250px-DOiPR_structure.png 1.5x" data-file-width="306" data-file-height="270" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-isopropylamphetamine" title="2,5-Dimethoxy-4-isopropylamphetamine">2,5-Dimethoxy-4-isopropylamphetamine</a> </td> <td>DOiP </td> <td>42306-96-7 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2,5-dimethoxy-4-propylthioamphetamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/2%2C5-dimethoxy-4-propylthioamphetamine.svg/115px-2%2C5-dimethoxy-4-propylthioamphetamine.svg.png" decoding="async" width="115" height="57" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/2%2C5-dimethoxy-4-propylthioamphetamine.svg/173px-2%2C5-dimethoxy-4-propylthioamphetamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0b/2%2C5-dimethoxy-4-propylthioamphetamine.svg/230px-2%2C5-dimethoxy-4-propylthioamphetamine.svg.png 2x" data-file-width="620" data-file-height="308" /></a></span> </td> <td><a href="/wiki/Aleph_(psychedelic)#Aleph-7" title="Aleph (psychedelic)">2,5-Dimethoxy-4-propylthioamphetamine</a> </td> <td>Aleph-7 </td> <td>207740-16-7 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DODFM_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/DODFM_structure.png/120px-DODFM_structure.png" decoding="async" width="115" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/DODFM_structure.png/250px-DODFM_structure.png 1.5x" data-file-width="1136" data-file-height="852" /></a></span> </td> <td>2,5-Dimethoxy-4-(difluoromethyl)amphetamine </td> <td>DODFM </td> <td>? </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2,5-Dimethoxy-4-trifluoromethylamphetamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/2%2C5-Dimethoxy-4-trifluoromethylamphetamine.svg/120px-2%2C5-Dimethoxy-4-trifluoromethylamphetamine.svg.png" decoding="async" width="115" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/2%2C5-Dimethoxy-4-trifluoromethylamphetamine.svg/250px-2%2C5-Dimethoxy-4-trifluoromethylamphetamine.svg.png 1.5x" data-file-width="620" data-file-height="407" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-trifluoromethylamphetamine" title="2,5-Dimethoxy-4-trifluoromethylamphetamine">2,5-Dimethoxy-4-trifluoromethylamphetamine</a> </td> <td>DOTFM </td> <td>159277-07-3 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOTFE_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/DOTFE_structure.png/120px-DOTFE_structure.png" decoding="async" width="115" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/DOTFE_structure.png/250px-DOTFE_structure.png 1.5x" data-file-width="1289" data-file-height="848" /></a></span> </td> <td>2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)amphetamine </td> <td>DOTFE </td> <td>? </td> <td><sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOCN_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/DOCN_structure.png/115px-DOCN_structure.png" decoding="async" width="115" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/DOCN_structure.png/173px-DOCN_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b6/DOCN_structure.png/230px-DOCN_structure.png 2x" data-file-width="1154" data-file-height="863" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-cyanoamphetamine" title="2,5-Dimethoxy-4-cyanoamphetamine">2,5-Dimethoxy-4-cyanoamphetamine</a> </td> <td>DOCN </td> <td>125903-74-4 </td> <td><sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOYN_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/DOYN_structure.png/120px-DOYN_structure.png" decoding="async" width="115" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/DOYN_structure.png/250px-DOYN_structure.png 1.5x" data-file-width="1123" data-file-height="857" /></a></span> </td> <td>2,5-Dimethoxy-4-ethynylamphetamine </td> <td>DOYN </td> <td>633290-70-7 </td> <td><sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOAC_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/DOAC_structure.png/115px-DOAC_structure.png" decoding="async" width="115" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/DOAC_structure.png/173px-DOAC_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/92/DOAC_structure.png/230px-DOAC_structure.png 2x" data-file-width="894" data-file-height="642" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-acetylamphetamine" title="2,5-Dimethoxy-4-acetylamphetamine">2,5-Dimethoxy-4-acetylamphetamine</a> </td> <td>DOAc </td> <td>? </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOIB_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/DOIB_structure.png/115px-DOIB_structure.png" decoding="async" width="115" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/DOIB_structure.png/173px-DOIB_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b2/DOIB_structure.png/230px-DOIB_structure.png 2x" data-file-width="960" data-file-height="639" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-isobutylamphetamine" title="2,5-Dimethoxy-4-isobutylamphetamine">2,5-Dimethoxy-4-isobutylamphetamine</a> </td> <td>DOIB </td> <td>89556-64-9 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOSB_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/DOSB_structure.png/115px-DOSB_structure.png" decoding="async" width="115" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/DOSB_structure.png/173px-DOSB_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0a/DOSB_structure.png/230px-DOSB_structure.png 2x" data-file-width="989" data-file-height="651" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-sec-butylamphetamine" title="2,5-Dimethoxy-4-sec-butylamphetamine">2,5-Dimethoxy-4-<i>sec</i>-butylamphetamine</a> </td> <td>DOSB </td> <td>89556-71-8 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOTB_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/DOTB_structure.png/115px-DOTB_structure.png" decoding="async" width="115" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/DOTB_structure.png/173px-DOTB_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6b/DOTB_structure.png/230px-DOTB_structure.png 2x" data-file-width="940" data-file-height="640" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-tert-butylamphetamine" title="2,5-Dimethoxy-4-tert-butylamphetamine">2,5-Dimethoxy-4-<i>tert</i>-butylamphetamine</a> </td> <td>DOTB </td> <td>41538-42-5 </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOHX_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/DOHX_structure.png/120px-DOHX_structure.png" decoding="async" width="115" height="59" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/DOHX_structure.png/250px-DOHX_structure.png 1.5x" data-file-width="1257" data-file-height="650" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-4-hexylamphetamine" title="2,5-Dimethoxy-4-hexylamphetamine">2,5-Dimethoxy-4-hexylamphetamine</a> </td> <td>DOHx </td> <td>? </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOCT_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/DOCT_structure.png/115px-DOCT_structure.png" decoding="async" width="115" height="52" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/DOCT_structure.png/173px-DOCT_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/88/DOCT_structure.png/230px-DOCT_structure.png 2x" data-file-width="1418" data-file-height="636" /></a></span> </td> <td>2,5-Dimethoxy-4-octylamphetamine </td> <td>DOCT </td> <td>? </td> <td> </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:4-PhPr-2,5-DMA.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/4-PhPr-2%2C5-DMA.svg/115px-4-PhPr-2%2C5-DMA.svg.png" decoding="async" width="115" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/4-PhPr-2%2C5-DMA.svg/173px-4-PhPr-2%2C5-DMA.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f8/4-PhPr-2%2C5-DMA.svg/230px-4-PhPr-2%2C5-DMA.svg.png 2x" data-file-width="765" data-file-height="375" /></a></span> </td> <td><a href="/wiki/4-(3-Phenylpropyl)-2,5-dimethoxyamphetamine" class="mw-redirect" title="4-(3-Phenylpropyl)-2,5-dimethoxyamphetamine">4-(3-Phenylpropyl)-2,5-dimethoxyamphetamine</a> </td> <td>4-PhPr-2,5-DMA </td> <td>? </td> <td> </td></tr> <tr> <td> </td> <td>4-Methallyloxy-2,5-dimethoxyamphetamine </td> <td>MMALM </td> <td>? </td> <td><sup id="cite_ref-KolaczynskaLuethiTrachsel2019_62-0" class="reference"><a href="#cite_note-KolaczynskaLuethiTrachsel2019-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td> </td> <td>4-Allyloxy-2,5-dimethoxyamphetamine </td> <td>MALM </td> <td>? </td> <td><sup id="cite_ref-KolaczynskaLuethiTrachsel2019_62-1" class="reference"><a href="#cite_note-KolaczynskaLuethiTrachsel2019-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td> </td> <td>4-(2-Fluoroethoxy)-2,5-dimethoxyamphetamine </td> <td>MFEM </td> <td>? </td> <td><sup id="cite_ref-KolaczynskaLuethiTrachsel2019_62-2" class="reference"><a href="#cite_note-KolaczynskaLuethiTrachsel2019-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td> </td> <td>4-(2,2-Difluoroethoxy)-2,5-dimethoxyamphetamine </td> <td>MDFEM </td> <td>? </td> <td><sup id="cite_ref-KolaczynskaLuethiTrachsel2019_62-3" class="reference"><a href="#cite_note-KolaczynskaLuethiTrachsel2019-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td> </td> <td>4-(2,2,2-Trifluoroethoxy)-2,5-dimethoxyamphetamine </td> <td>MTFEM </td> <td>? </td> <td><sup id="cite_ref-KolaczynskaLuethiTrachsel2019_62-4" class="reference"><a href="#cite_note-KolaczynskaLuethiTrachsel2019-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td> </td> <td>4-Isopropoxy-2,5-dimethoxyamphetamine </td> <td>MIPM </td> <td>? </td> <td><sup id="cite_ref-KolaczynskaLuethiTrachsel2019_62-5" class="reference"><a href="#cite_note-KolaczynskaLuethiTrachsel2019-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </td></tr> </tbody></table> <div class="mw-heading mw-heading2"><h2 id="Related_compounds">Related compounds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=11" title="Edit section: Related compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A number of additional compounds are known with alternative substitutions: </p> <table class="wikitable"> <tbody><tr> <th>Structure </th> <th>Name </th> <th>Abbreviation </th> <th>CAS number </th></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Ariadne.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Ariadne.svg/120px-Ariadne.svg.png" decoding="async" width="115" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Ariadne.svg/250px-Ariadne.svg.png 1.5x" data-file-width="512" data-file-height="415" /></a></span> </td> <td><a href="/wiki/Ariadne_(psychedelic)" class="mw-redirect" title="Ariadne (psychedelic)">Dimoxamine ("Ariadne")</a> </td> <td>4C-D </td> <td>52842-59-8 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:4C-E_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/4C-E_structure.png/115px-4C-E_structure.png" decoding="async" width="115" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/4C-E_structure.png/173px-4C-E_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/4C-E_structure.png/230px-4C-E_structure.png 2x" data-file-width="1149" data-file-height="845" /></a></span> </td> <td>1-(2,5-Dimethoxy-4-ethylphenyl)butan-2-amine<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </td> <td>4C-E </td> <td>? </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:4C-P_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/4C-P_structure.png/115px-4C-P_structure.png" decoding="async" width="115" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/4C-P_structure.png/173px-4C-P_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/4C-P_structure.png/230px-4C-P_structure.png 2x" data-file-width="1261" data-file-height="856" /></a></span> </td> <td>1-(2,5-Dimethoxy-4-(n-propyl)phenyl)butan-2-amine </td> <td>4C-P </td> <td>? </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:4C-B_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/4C-B_structure.png/115px-4C-B_structure.png" decoding="async" width="115" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/4C-B_structure.png/173px-4C-B_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/de/4C-B_structure.png/230px-4C-B_structure.png 2x" data-file-width="1024" data-file-height="830" /></a></span> </td> <td><a href="/wiki/4C-B" title="4C-B">1-(2,5-Dimethoxy-4-bromophenyl)butan-2-amine</a> </td> <td>4C-B </td> <td>69294-23-1 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:4C-C_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/4C-C_structure.png/115px-4C-C_structure.png" decoding="async" width="115" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/4C-C_structure.png/173px-4C-C_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/94/4C-C_structure.png/230px-4C-C_structure.png 2x" data-file-width="1006" data-file-height="821" /></a></span> </td> <td>1-(2,5-Dimethoxy-4-chlorophenyl)butan-2-amine </td> <td>4C-C </td> <td>791010-74-7 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:4C-I_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/4C-I_structure.png/115px-4C-I_structure.png" decoding="async" width="115" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/4C-I_structure.png/173px-4C-I_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ca/4C-I_structure.png/230px-4C-I_structure.png 2x" data-file-width="1010" data-file-height="835" /></a></span> </td> <td>1-(2,5-Dimethoxy-4-iodophenyl)butan-2-amine </td> <td>4C-I </td> <td>758631-75-3 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:4C-N_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/4C-N_structure.png/115px-4C-N_structure.png" decoding="async" width="115" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/4C-N_structure.png/173px-4C-N_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dc/4C-N_structure.png/230px-4C-N_structure.png 2x" data-file-width="1118" data-file-height="839" /></a></span> </td> <td>1-(2,5-Dimethoxy-4-nitrophenyl)butan-2-amine </td> <td>4C-N </td> <td>775234-58-7 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:4C-T-2_skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/4C-T-2_skeletal.svg/115px-4C-T-2_skeletal.svg.png" decoding="async" width="115" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/4C-T-2_skeletal.svg/173px-4C-T-2_skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/4C-T-2_skeletal.svg/230px-4C-T-2_skeletal.svg.png 2x" data-file-width="215" data-file-height="146" /></a></span> </td> <td><a href="/wiki/4C-T-2" title="4C-T-2">1-[2,5-Dimethoxy-4-(ethylthio)phenyl]butan-2-amine</a> </td> <td>4C-T-2 </td> <td>850007-13-5 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Beatrice_(psychedelic).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Beatrice_%28psychedelic%29.png/120px-Beatrice_%28psychedelic%29.png" decoding="async" width="115" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Beatrice_%28psychedelic%29.png/250px-Beatrice_%28psychedelic%29.png 1.5x" data-file-width="608" data-file-height="506" /></a></span> </td> <td><a href="/wiki/Beatrice_(psychedelic)" title="Beatrice (psychedelic)">Dimethoxymethamphetamine ("Beatrice")</a> </td> <td><i>N</i>-Methyl-DOM </td> <td>92206-37-6 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DMMDA.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/DMMDA.svg/115px-DMMDA.svg.png" decoding="async" width="115" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/DMMDA.svg/173px-DMMDA.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/DMMDA.svg/230px-DMMDA.svg.png 2x" data-file-width="510" data-file-height="380" /></a></span> </td> <td><a href="/wiki/2,5-Dimethoxy-3,4-methylenedioxyamphetamine" class="mw-redirect" title="2,5-Dimethoxy-3,4-methylenedioxyamphetamine">2,5-Dimethoxy-3,4-methylenedioxyamphetamine</a> </td> <td>DMMDA </td> <td>15183-13-8 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Ganesha.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Ganesha.svg/115px-Ganesha.svg.png" decoding="async" width="115" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Ganesha.svg/173px-Ganesha.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Ganesha.svg/230px-Ganesha.svg.png 2x" data-file-width="512" data-file-height="413" /></a></span> </td> <td><a href="/wiki/Ganesha_(psychedelic)" title="Ganesha (psychedelic)">2,5-Dimethoxy-3,4-dimethylamphetamine ("Ganesha")</a> </td> <td>3-Methyl-DOM </td> <td>207740-37-2 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:3C-G-3.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/3C-G-3.png/115px-3C-G-3.png" decoding="async" width="115" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/3C-G-3.png/173px-3C-G-3.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ea/3C-G-3.png/230px-3C-G-3.png 2x" data-file-width="813" data-file-height="642" /></a></span> </td> <td><a href="/wiki/G-3_(drug)" class="mw-redirect" title="G-3 (drug)">2,5-Dimethoxy-3,4-trimethylenylamphetamine</a> </td> <td>G-3 </td> <td>? </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:3C-G-4.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3d/3C-G-4.png/115px-3C-G-4.png" decoding="async" width="115" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3d/3C-G-4.png/173px-3C-G-4.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3d/3C-G-4.png/230px-3C-G-4.png 2x" data-file-width="837" data-file-height="642" /></a></span> </td> <td><a href="/wiki/G-4_(drug)" class="mw-redirect" title="G-4 (drug)">2,5-Dimethoxy-3,4-tetramethylenylamphetamine</a> </td> <td>G-4 </td> <td>? </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOG5_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/DOG5_structure.png/115px-DOG5_structure.png" decoding="async" width="115" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/DOG5_structure.png/173px-DOG5_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d7/DOG5_structure.png/230px-DOG5_structure.png 2x" data-file-width="1152" data-file-height="850" /></a></span> </td> <td><a href="/wiki/G-5_(drug)" class="mw-redirect" title="G-5 (drug)">2,5-Dimethoxy-3,4-norbornylamphetamine</a> </td> <td>G-5 </td> <td>? </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:3C-G-N.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/3C-G-N.png/115px-3C-G-N.png" decoding="async" width="115" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/3C-G-N.png/173px-3C-G-N.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/3C-G-N.png/230px-3C-G-N.png 2x" data-file-width="837" data-file-height="642" /></a></span> </td> <td><a href="/wiki/G-N_(drug)" class="mw-redirect" title="G-N (drug)">1,4-Dimethoxynaphthyl-2-isopropylamine</a> </td> <td>G-N </td> <td>? </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOGO_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/DOGO_structure.png/115px-DOGO_structure.png" decoding="async" width="115" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/DOGO_structure.png/173px-DOGO_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/DOGO_structure.png/230px-DOGO_structure.png 2x" data-file-width="1152" data-file-height="847" /></a></span> </td> <td><a href="/wiki/G-O_(drug)" class="mw-redirect" title="G-O (drug)">1-(5,8-Dimethoxy-3,4-dihydro-1H-isochromen-7-yl)propan-2-amine</a><sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </td> <td>G-O </td> <td>774538-38-4 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DODC_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/DODC_structure.png/115px-DODC_structure.png" decoding="async" width="115" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/DODC_structure.png/173px-DODC_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/28/DODC_structure.png/230px-DODC_structure.png 2x" data-file-width="1035" data-file-height="860" /></a></span> </td> <td><a href="/wiki/DODC" title="DODC">2,5-Dimethoxy-3,4-dichloroamphetamine</a> </td> <td>DODC </td> <td>1373918-65-0 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:IDNNA.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/IDNNA.png/120px-IDNNA.png" decoding="async" width="115" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/IDNNA.png/250px-IDNNA.png 1.5x" data-file-width="617" data-file-height="506" /></a></span> </td> <td><a href="/wiki/IDNNA" title="IDNNA">2,5-Dimethoxy-4-iodo-<i>N</i>,<i>N</i>-dimethylamphetamine</a> </td> <td>IDNNA </td> <td>67707-78-2 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Methyl-DOB.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Methyl-DOB.png/120px-Methyl-DOB.png" decoding="async" width="115" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Methyl-DOB.png/250px-Methyl-DOB.png 1.5x" data-file-width="666" data-file-height="506" /></a></span> </td> <td><a href="/wiki/Methyl-DOB" title="Methyl-DOB">Methyl-DOB</a> </td> <td><i>N</i>-Methyl-DOB </td> <td>155638-80-5 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2,3,4,5-Tetramethoxyamphetamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/2%2C3%2C4%2C5-Tetramethoxyamphetamine.svg/120px-2%2C3%2C4%2C5-Tetramethoxyamphetamine.svg.png" decoding="async" width="115" height="82" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/2%2C3%2C4%2C5-Tetramethoxyamphetamine.svg/250px-2%2C3%2C4%2C5-Tetramethoxyamphetamine.svg.png 1.5x" data-file-width="419" data-file-height="299" /></a></span> </td> <td><a href="/wiki/2,3,4,5-Tetramethoxyamphetamine" title="2,3,4,5-Tetramethoxyamphetamine">2,3,4,5-Tetramethoxyamphetamine</a> </td> <td>TeMA </td> <td>23693-26-7 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:DOB-FLY_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/DOB-FLY_structure.png/115px-DOB-FLY_structure.png" decoding="async" width="115" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/DOB-FLY_structure.png/173px-DOB-FLY_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/DOB-FLY_structure.png/230px-DOB-FLY_structure.png 2x" data-file-width="1010" data-file-height="750" /></a></span> </td> <td><a href="/wiki/DOB-FLY" title="DOB-FLY">1-(4-Bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl)propan-2-amine</a> </td> <td>DOB-FLY </td> <td>219986-75-1 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:R-Bromo-DragonFLY.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/R-Bromo-DragonFLY.svg/115px-R-Bromo-DragonFLY.svg.png" decoding="async" width="115" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/R-Bromo-DragonFLY.svg/173px-R-Bromo-DragonFLY.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/31/R-Bromo-DragonFLY.svg/230px-R-Bromo-DragonFLY.svg.png 2x" data-file-width="512" data-file-height="337" /></a></span> </td> <td><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a> </td> <td>DOB-DFLY </td> <td>502759-67-3 </td></tr> <tr> <td><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:WO2021-0137908-1_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/WO2021-0137908-1_structure.png/115px-WO2021-0137908-1_structure.png" decoding="async" width="115" height="103" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/WO2021-0137908-1_structure.png/173px-WO2021-0137908-1_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b1/WO2021-0137908-1_structure.png/230px-WO2021-0137908-1_structure.png 2x" data-file-width="716" data-file-height="640" /></a></span> </td> <td><a href="/wiki/ZC-B" title="ZC-B">3-(4-Bromo-2,5-dimethoxyphenyl)azetidine</a> </td> <td>ZC-B<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </td> <td>2641630-65-9 </td></tr> </tbody></table> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=12" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/2,5-Dimethoxyamphetamine" title="2,5-Dimethoxyamphetamine">2,5-Dimethoxyamphetamine</a></li> <li><a href="/wiki/Substituted_mescaline_analogue" title="Substituted mescaline analogue">Substituted mescaline analogue</a></li> <li><a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2Cs</a>, <a href="/wiki/25-NB" title="25-NB">25-NB</a></li> <li><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Substituted amphetamines</a></li> <li><a href="/wiki/Substituted_benzofuran" title="Substituted benzofuran">Substituted benzofurans</a></li> <li><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Substituted cathinones</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">Substituted methylenedioxyphenethylamines</a></li> <li><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Substituted phenethylamines</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Substituted tryptamines</a></li> <li><i><a href="/wiki/PiHKAL" title="PiHKAL">PiHKAL</a></i></li> <li><i><a href="/wiki/The_Shulgin_Index" title="The Shulgin Index">The Shulgin Index</a></i></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=13" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Trachsel-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Trachsel_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFDaniel_TrachselDavid_LehmannChristoph_Enzensperger2013" class="citation book cs1">Daniel Trachsel; David Lehmann & Christoph Enzensperger (2013). <i>Phenethylamine: Von der Struktur zur Funktion</i>. Nachtschatten Verlag AG. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-03788-700-4" title="Special:BookSources/978-3-03788-700-4"><bdi>978-3-03788-700-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Phenethylamine%3A+Von+der+Struktur+zur+Funktion&rft.pub=Nachtschatten+Verlag+AG&rft.date=2013&rft.isbn=978-3-03788-700-4&rft.au=Daniel+Trachsel&rft.au=David+Lehmann&rft.au=Christoph+Enzensperger&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-GlennonDukat2024-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-GlennonDukat2024_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GlennonDukat2024_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-GlennonDukat2024_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-GlennonDukat2024_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-GlennonDukat2024_2-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-GlennonDukat2024_2-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-GlennonDukat2024_2-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-GlennonDukat2024_2-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-GlennonDukat2024_2-8"><sup><i><b>i</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGlennonDukat2024" class="citation journal cs1">Glennon RA, Dukat M (June 2024). "1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane (DOI): From an Obscure to Pivotal Member of the DOX Family of Serotonergic Psychedelic Agents - A Review". <i>ACS Pharmacol Transl Sci</i>. <b>7</b> (6): <span class="nowrap">1722–</span>1745. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facsptsci.4c00157">10.1021/acsptsci.4c00157</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> 11184610. <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/38898956">38898956</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=ACS+Pharmacol+Transl+Sci&rft.atitle=1-%282%2C5-Dimethoxy-4-iodophenyl%29-2-aminopropane+%28DOI%29%3A+From+an+Obscure+to+Pivotal+Member+of+the+DOX+Family+of+Serotonergic+Psychedelic+Agents+-+A+Review&rft.volume=7&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1722-%3C%2Fspan%3E1745&rft.date=2024-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11184610%23id-name%3DPMC&rft_id=info%3Apmid%2F38898956&rft_id=info%3Adoi%2F10.1021%2Facsptsci.4c00157&rft.aulast=Glennon&rft.aufirst=RA&rft.au=Dukat%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-WillsErickson2012-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-WillsErickson2012_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-WillsErickson2012_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-WillsErickson2012_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-WillsErickson2012_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-WillsErickson2012_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-WillsErickson2012_3-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWillsErickson2012" class="citation book cs1">Wills B, Erickson T (9 March 2012). 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New York: Raven Press. pp. <span class="nowrap">95–</span>142. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-89004-990-7" title="Special:BookSources/978-0-89004-990-7"><bdi>978-0-89004-990-7</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/10324237">10324237</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Medicinal+Chemistry+and+Structure-Activity+Relationships+of+Hallucinogens&rft.btitle=Hallucinogens%3A+Neurochemical%2C+Behavioral%2C+and+Clinical+Perspectives&rft.place=New+York&rft.pages=%3Cspan+class%3D%22nowrap%22%3E95-%3C%2Fspan%3E142&rft.pub=Raven+Press&rft.date=1984&rft_id=info%3Aoclcnum%2F10324237&rft.isbn=978-0-89004-990-7&rft.aulast=Nichols&rft.aufirst=DE&rft.au=Glennon%2C+RA&rft_id=https%3A%2F%2Fbitnest.netfirms.com%2Fexternal%2FBooks%2FHallucinogensNBCP95&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-BallentineFriedmanBzdok2022-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-BallentineFriedmanBzdok2022_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-BallentineFriedmanBzdok2022_14-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBallentineFriedmanBzdok2022" class="citation journal cs1">Ballentine G, Friedman SF, Bzdok D (March 2022). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8926331">"Trips and neurotransmitters: Discovering principled patterns across 6850 hallucinogenic experiences"</a>. <i>Sci Adv</i>. <b>8</b> (11): eabl6989. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2022SciA....8L6989B">2022SciA....8L6989B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fsciadv.abl6989">10.1126/sciadv.abl6989</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8926331">8926331</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/35294242">35294242</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Sci+Adv&rft.atitle=Trips+and+neurotransmitters%3A+Discovering+principled+patterns+across+6850+hallucinogenic+experiences&rft.volume=8&rft.issue=11&rft.pages=eabl6989&rft.date=2022-03&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8926331%23id-name%3DPMC&rft_id=info%3Apmid%2F35294242&rft_id=info%3Adoi%2F10.1126%2Fsciadv.abl6989&rft_id=info%3Abibcode%2F2022SciA....8L6989B&rft.aulast=Ballentine&rft.aufirst=G&rft.au=Friedman%2C+SF&rft.au=Bzdok%2C+D&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8926331&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-PiHKAL1991-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-PiHKAL1991_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PiHKAL1991_15-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PiHKAL1991_15-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShulginShulgin1991" class="citation book cs1">Shulgin, A.T.; Shulgin, A. (1991). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=O8AdHBGybpcC"><i>PiHKAL: A Chemical Love Story</i></a>. Transform Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-9630096-0-9" title="Special:BookSources/978-0-9630096-0-9"><bdi>978-0-9630096-0-9</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">2 November</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=PiHKAL%3A+A+Chemical+Love+Story&rft.pub=Transform+Press&rft.date=1991&rft.isbn=978-0-9630096-0-9&rft.aulast=Shulgin&rft.aufirst=A.T.&rft.au=Shulgin%2C+A.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DO8AdHBGybpcC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-ShulginManningDaley2011-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-ShulginManningDaley2011_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ShulginManningDaley2011_16-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ShulginManningDaley2011_16-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-ShulginManningDaley2011_16-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShulginManningDaley2011" class="citation book cs1">Shulgin, A.; Manning, T.; Daley, P.F. (2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=68-huAAACAAJ"><i>The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds</i></a>. Vol. 1. Berkeley: Transform Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-9630096-3-0" title="Special:BookSources/978-0-9630096-3-0"><bdi>978-0-9630096-3-0</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">2 November</span> 2024</span>. <q>A short history of DOM (STP) notes that the original synthesis took place in 1963, psychological effects were discovered the following year, and that the compound had appeared in the Haight-Ashbury scene of mid-1967 (Shulgin, 1977b). The known congeners of DOM were reviewed for structure-activity relationships (Barfknecht et al., 1978). [...] Shulgin, AT. (1977b) Profiles of psychedelic drugs. 5. STP. J. Psych. Drugs 9(2): 171-172.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Shulgin+Index%2C+Volume+One%3A+Psychedelic+Phenethylamines+and+Related+Compounds&rft.place=Berkeley&rft.pub=Transform+Press&rft.date=2011&rft.isbn=978-0-9630096-3-0&rft.aulast=Shulgin&rft.aufirst=A.&rft.au=Manning%2C+T.&rft.au=Daley%2C+P.F.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D68-huAAACAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-ValterArrizabalagaLandry1998-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-ValterArrizabalagaLandry1998_17-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFValterArrizabalagaLandry1998" class="citation book cs1">Valter, K.; Arrizabalaga, P.; Landry, J.C. (1998). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=K5u1TTW7LJ8C&pg=PP1"><i>Designer Drugs Directory</i></a>. Elsevier Science. p. 1. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-053032-1" title="Special:BookSources/978-0-08-053032-1"><bdi>978-0-08-053032-1</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">9 March</span> 2025</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Designer+Drugs+Directory&rft.pages=1&rft.pub=Elsevier+Science&rft.date=1998&rft.isbn=978-0-08-053032-1&rft.aulast=Valter&rft.aufirst=K.&rft.au=Arrizabalaga%2C+P.&rft.au=Landry%2C+J.C.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DK5u1TTW7LJ8C%26pg%3DPP1&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-NelsonLucaitesWainscott1999-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-NelsonLucaitesWainscott1999_18-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNelsonLucaitesWainscottGlennon1999" class="citation journal cs1">Nelson DL, Lucaites VL, Wainscott DB, Glennon RA (January 1999). "Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors". <i>Naunyn Schmiedebergs Arch Pharmacol</i>. <b>359</b> (1): <span class="nowrap">1–</span>6. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fpl00005315">10.1007/pl00005315</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/9933142">9933142</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Naunyn+Schmiedebergs+Arch+Pharmacol&rft.atitle=Comparisons+of+hallucinogenic+phenylisopropylamine+binding+affinities+at+cloned+human+5-HT2A%2C+-HT%282B%29+and+5-HT2C+receptors&rft.volume=359&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E6&rft.date=1999-01&rft_id=info%3Adoi%2F10.1007%2Fpl00005315&rft_id=info%3Apmid%2F9933142&rft.aulast=Nelson&rft.aufirst=DL&rft.au=Lucaites%2C+VL&rft.au=Wainscott%2C+DB&rft.au=Glennon%2C+RA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-HemanthNistalaNguyen2023-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-HemanthNistalaNguyen2023_19-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHemanthNistalaNguyenEltit2023" class="citation journal cs1">Hemanth P, Nistala P, Nguyen VT, Eltit JM, Glennon RA, Dukat M (2023). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9902381">"Binding and functional structure-activity similarities of 4-substituted 2,5-dimethoxyphenyl isopropylamine analogues at 5-HT2A and 5-HT2B serotonin receptors"</a>. <i>Front Pharmacol</i>. <b>14</b>: 1101290. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3389%2Ffphar.2023.1101290">10.3389/fphar.2023.1101290</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9902381">9902381</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/36762110">36762110</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Front+Pharmacol&rft.atitle=Binding+and+functional+structure-activity+similarities+of+4-substituted+2%2C5-dimethoxyphenyl+isopropylamine+analogues+at+5-HT2A+and+5-HT2B+serotonin+receptors&rft.volume=14&rft.pages=1101290&rft.date=2023&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9902381%23id-name%3DPMC&rft_id=info%3Apmid%2F36762110&rft_id=info%3Adoi%2F10.3389%2Ffphar.2023.1101290&rft.aulast=Hemanth&rft.aufirst=P&rft.au=Nistala%2C+P&rft.au=Nguyen%2C+VT&rft.au=Eltit%2C+JM&rft.au=Glennon%2C+RA&rft.au=Dukat%2C+M&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9902381&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-RudinLuethiHoener2022-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-RudinLuethiHoener2022_20-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRudinLuethiHoenerLiechti2022" class="citation journal cs1">Rudin, Deborah; Luethi, Dino; Hoener, Marius C.; Liechti, Matthias E. (2022). <a rel="nofollow" class="external text" href="https://www.researchgate.net/publication/360363617">"Structure-activity Relation of Halogenated 2,5-Dimethoxyamphetamines Compared to their α‑Desmethyl (2C) Analogues"</a>. <i>The FASEB Journal</i>. <b>36</b> (S1). <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1096%2Ffasebj.2022.36.S1.R2121">10.1096/fasebj.2022.36.S1.R2121</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0892-6638">0892-6638</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+FASEB+Journal&rft.atitle=Structure-activity+Relation+of+Halogenated+2%2C5-Dimethoxyamphetamines+Compared+to+their+%CE%B1%E2%80%91Desmethyl+%282C%29+Analogues&rft.volume=36&rft.issue=S1&rft.date=2022&rft_id=info%3Adoi%2F10.1096%2Ffasebj.2022.36.S1.R2121&rft.issn=0892-6638&rft.aulast=Rudin&rft.aufirst=Deborah&rft.au=Luethi%2C+Dino&rft.au=Hoener%2C+Marius+C.&rft.au=Liechti%2C+Matthias+E.&rft_id=https%3A%2F%2Fwww.researchgate.net%2Fpublication%2F360363617&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-vanWijngaardenSoudijn1997-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-vanWijngaardenSoudijn1997_21-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFvan_WijngaardenSoudijn1997" class="citation book cs1">van Wijngaarden, I.; Soudijn, W. (1997). "5-HT2A, 5-HT2B and 5-HT2C receptor ligands". <i>Pharmacochemistry Library</i>. Vol. 27. Elsevier. pp. <span class="nowrap">161–</span>197. <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%2Fs0165-7208%2897%2980013-x">10.1016/s0165-7208(97)80013-x</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-444-82041-9" title="Special:BookSources/978-0-444-82041-9"><bdi>978-0-444-82041-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=5-HT2A%2C+5-HT2B+and+5-HT2C+receptor+ligands&rft.btitle=Pharmacochemistry+Library&rft.pages=%3Cspan+class%3D%22nowrap%22%3E161-%3C%2Fspan%3E197&rft.pub=Elsevier&rft.date=1997&rft_id=info%3Adoi%2F10.1016%2Fs0165-7208%2897%2980013-x&rft.isbn=978-0-444-82041-9&rft.aulast=van+Wijngaarden&rft.aufirst=I.&rft.au=Soudijn%2C+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-NicholsNichols2021-22"><span class="mw-cite-backlink">^ <a href="#cite_ref-NicholsNichols2021_22-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NicholsNichols2021_22-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNicholsNichols2021" class="citation book cs1">Nichols, D.E.; Nichols, C. D. (2021). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ebb2DwAAQBAJ&pg=PA3">"The Pharmacology of Psychedelics"</a>. In Grob, C.S.; Grigsby, J. (eds.). <i>Handbook of Medical Hallucinogens</i>. Guilford Publications. pp. <span class="nowrap">3–</span>28. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4625-4544-5" title="Special:BookSources/978-1-4625-4544-5"><bdi>978-1-4625-4544-5</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">17 January</span> 2025</span>. <q>Phenylalkylamine hallucinogens such as DOM, DOI, and DOB are highly selective for 5-HT2 receptor subtypes (Pierce & Peroutka, 1989; Titeler, Lyon, & Glennon, 1988), and there is a consensus in the literature that the behavioral effects of psychedelics are primarily mediated by the 5-HT2A receptor (Halberstadt, 2015; Nichols, 2016).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=The+Pharmacology+of+Psychedelics&rft.btitle=Handbook+of+Medical+Hallucinogens&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3-%3C%2Fspan%3E28&rft.pub=Guilford+Publications&rft.date=2021&rft.isbn=978-1-4625-4544-5&rft.aulast=Nichols&rft.aufirst=D.E.&rft.au=Nichols%2C+C.+D.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Debb2DwAAQBAJ%26pg%3DPA3&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-PottieCannaertStove2020-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-PottieCannaertStove2020_23-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPottieCannaertStove2020" class="citation journal cs1">Pottie E, Cannaert A, Stove CP (October 2020). "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor". <i>Arch Toxicol</i>. <b>94</b> (10): <span class="nowrap">3449–</span>3460. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00204-020-02836-w">10.1007/s00204-020-02836-w</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/1854%2FLU-8687071">1854/LU-8687071</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/32627074">32627074</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Arch+Toxicol&rft.atitle=In+vitro+structure-activity+relationship+determination+of+30+psychedelic+new+psychoactive+substances+by+means+of+%CE%B2-arrestin+2+recruitment+to+the+serotonin+2A+receptor&rft.volume=94&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3449-%3C%2Fspan%3E3460&rft.date=2020-10&rft_id=info%3Ahdl%2F1854%2FLU-8687071&rft_id=info%3Apmid%2F32627074&rft_id=info%3Adoi%2F10.1007%2Fs00204-020-02836-w&rft.aulast=Pottie&rft.aufirst=E&rft.au=Cannaert%2C+A&rft.au=Stove%2C+CP&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-EshlemanForsterWolfrum2014-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-EshlemanForsterWolfrum2014_24-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEshlemanForsterWolfrumJohnson2014" class="citation journal cs1">Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB (March 2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3945162">"Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function"</a>. <i>Psychopharmacology (Berl)</i>. <b>231</b> (5): <span class="nowrap">875–</span>888. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00213-013-3303-6">10.1007/s00213-013-3303-6</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3945162">3945162</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24142203">24142203</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Psychopharmacology+%28Berl%29&rft.atitle=Behavioral+and+neurochemical+pharmacology+of+six+psychoactive+substituted+phenethylamines%3A+mouse+locomotion%2C+rat+drug+discrimination+and+in+vitro+receptor+and+transporter+binding+and+function&rft.volume=231&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E875-%3C%2Fspan%3E888&rft.date=2014-03&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3945162%23id-name%3DPMC&rft_id=info%3Apmid%2F24142203&rft_id=info%3Adoi%2F10.1007%2Fs00213-013-3303-6&rft.aulast=Eshleman&rft.aufirst=AJ&rft.au=Forster%2C+MJ&rft.au=Wolfrum%2C+KM&rft.au=Johnson%2C+RA&rft.au=Janowsky%2C+A&rft.au=Gatch%2C+MB&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3945162&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-EshlemanWolfrumReed2018-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-EshlemanWolfrumReed2018_25-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEshlemanWolfrumReedKim2018" class="citation journal cs1">Eshleman AJ, Wolfrum KM, Reed JF, Kim SO, Johnson RA, Janowsky A (December 2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6298744">"Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors"</a>. <i>Biochem Pharmacol</i>. <b>158</b>: <span class="nowrap">27–</span>34. <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.bcp.2018.09.024">10.1016/j.bcp.2018.09.024</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6298744">6298744</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30261175">30261175</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochem+Pharmacol&rft.atitle=Neurochemical+pharmacology+of+psychoactive+substituted+N-benzylphenethylamines%3A+High+potency+agonists+at+5-HT2A+receptors&rft.volume=158&rft.pages=%3Cspan+class%3D%22nowrap%22%3E27-%3C%2Fspan%3E34&rft.date=2018-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6298744%23id-name%3DPMC&rft_id=info%3Apmid%2F30261175&rft_id=info%3Adoi%2F10.1016%2Fj.bcp.2018.09.024&rft.aulast=Eshleman&rft.aufirst=AJ&rft.au=Wolfrum%2C+KM&rft.au=Reed%2C+JF&rft.au=Kim%2C+SO&rft.au=Johnson%2C+RA&rft.au=Janowsky%2C+A&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6298744&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-LewinMillerGilmour2011-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-LewinMillerGilmour2011_26-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLewinMillerGilmour2011" class="citation journal cs1">Lewin AH, Miller GM, Gilmour B (December 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3236098">"Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class"</a>. <i>Bioorg Med Chem</i>. <b>19</b> (23): <span class="nowrap">7044–</span>7048. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.bmc.2011.10.007">10.1016/j.bmc.2011.10.007</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3236098">3236098</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22037049">22037049</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioorg+Med+Chem&rft.atitle=Trace+amine-associated+receptor+1+is+a+stereoselective+binding+site+for+compounds+in+the+amphetamine+class&rft.volume=19&rft.issue=23&rft.pages=%3Cspan+class%3D%22nowrap%22%3E7044-%3C%2Fspan%3E7048&rft.date=2011-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3236098%23id-name%3DPMC&rft_id=info%3Apmid%2F22037049&rft_id=info%3Adoi%2F10.1016%2Fj.bmc.2011.10.007&rft.aulast=Lewin&rft.aufirst=AH&rft.au=Miller%2C+GM&rft.au=Gilmour%2C+B&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3236098&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-BunzowSondersArttamangkul2001-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-BunzowSondersArttamangkul2001_27-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBunzowSondersArttamangkulHarrison2001" class="citation journal cs1">Bunzow JR, Sonders MS, Arttamangkul S, Harrison LM, Zhang G, Quigley DI, Darland T, Suchland KL, Pasumamula S, Kennedy JL, Olson SB, Magenis RE, Amara SG, Grandy DK (December 2001). "Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor". <i>Mol Pharmacol</i>. <b>60</b> (6): <span class="nowrap">1181–</span>1188. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fmol.60.6.1181">10.1124/mol.60.6.1181</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11723224">11723224</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Mol+Pharmacol&rft.atitle=Amphetamine%2C+3%2C4-methylenedioxymethamphetamine%2C+lysergic+acid+diethylamide%2C+and+metabolites+of+the+catecholamine+neurotransmitters+are+agonists+of+a+rat+trace+amine+receptor&rft.volume=60&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1181-%3C%2Fspan%3E1188&rft.date=2001-12&rft_id=info%3Adoi%2F10.1124%2Fmol.60.6.1181&rft_id=info%3Apmid%2F11723224&rft.aulast=Bunzow&rft.aufirst=JR&rft.au=Sonders%2C+MS&rft.au=Arttamangkul%2C+S&rft.au=Harrison%2C+LM&rft.au=Zhang%2C+G&rft.au=Quigley%2C+DI&rft.au=Darland%2C+T&rft.au=Suchland%2C+KL&rft.au=Pasumamula%2C+S&rft.au=Kennedy%2C+JL&rft.au=Olson%2C+SB&rft.au=Magenis%2C+RE&rft.au=Amara%2C+SG&rft.au=Grandy%2C+DK&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-FantegrossiMurnaneReissig2008-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-FantegrossiMurnaneReissig2008_28-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFantegrossiMurnaneReissig2008" class="citation journal cs1">Fantegrossi WE, Murnane KS, Reissig CJ (January 2008). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2247373">"The behavioral pharmacology of hallucinogens"</a>. <i>Biochem Pharmacol</i>. <b>75</b> (1): <span class="nowrap">17–</span>33. <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.bcp.2007.07.018">10.1016/j.bcp.2007.07.018</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2247373">2247373</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17977517">17977517</a>. <q>Despite the reasonably constant recreational use of hallucinogens since at least the early 1970s [44], the reinforcing effects of hallucinogens have not been widely investigated in laboratory animals. Indeed, one of the earliest studies on the reinforcing effects of drugs using the intravenous self-administration procedure in rhesus monkeys found that no animal initiated self-injection of mescaline either spontaneously or after one month of programmed administration [45]. Likewise, the phenethylamine hallucinogen 2,5-dimethoxy-4-methylamphetamine (DOM) was not effective in maintaining self-administration in rhesus monkeys [46]. Nevertheless, the hallucinogen-like phenethylamine 3,4-methylenedioxymethamphetamine (MDMA) has been shown to act as a reinforcer in intravenous self-administration paradigms in baboons [47], rhesus monkeys [48 – 50], rats [51] and mice [52].</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochem+Pharmacol&rft.atitle=The+behavioral+pharmacology+of+hallucinogens&rft.volume=75&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E17-%3C%2Fspan%3E33&rft.date=2008-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2247373%23id-name%3DPMC&rft_id=info%3Apmid%2F17977517&rft_id=info%3Adoi%2F10.1016%2Fj.bcp.2007.07.018&rft.aulast=Fantegrossi&rft.aufirst=WE&rft.au=Murnane%2C+KS&rft.au=Reissig%2C+CJ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2247373&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-CanalMurnane2017-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-CanalMurnane2017_29-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCanalMurnane2017" class="citation journal cs1">Canal CE, Murnane KS (January 2017). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5445387">"The serotonin 5-HT2C receptor and the non-addictive nature of classic hallucinogens"</a>. <i>J Psychopharmacol</i>. <b>31</b> (1): <span class="nowrap">127–</span>143. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F0269881116677104">10.1177/0269881116677104</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5445387">5445387</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27903793">27903793</a>. <q>One of the earliest studies on the reinforcing effects of drugs using the intravenous self-administration procedure in rhesus monkeys found that no animal initiated self-injection of mescaline either spontaneously or after one month of programmed administration, [...] (Deneau et al., 1969). The lack of mescaline self-administration stood in contrast to positive findings of self-administration of morphine, codeine, cocaine, amphetamine, pentobarbital, ethanol, and caffeine. A subsequent study with rhesus monkeys using 2,5-dimethoxy-4-methylamphetamine (DOM; Yanagita, 1986) provided similar results as the mescaline study. These findings have withstood the test of time, as the primary literature is virtually devoid of any accounts of self-administration of [classical hallucinogens (CH)], suggesting that there are very limited conditions under which laboratory animals voluntarily consume CH.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Psychopharmacol&rft.atitle=The+serotonin+5-HT2C+receptor+and+the+non-addictive+nature+of+classic+hallucinogens&rft.volume=31&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E127-%3C%2Fspan%3E143&rft.date=2017-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5445387%23id-name%3DPMC&rft_id=info%3Apmid%2F27903793&rft_id=info%3Adoi%2F10.1177%2F0269881116677104&rft.aulast=Canal&rft.aufirst=CE&rft.au=Murnane%2C+KS&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5445387&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-Yanagita1986-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-Yanagita1986_30-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFYanagita1986" class="citation journal cs1">Yanagita T (June 1986). 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Retrieved <span class="nowrap">26 January</span> 2025</span>. <q>[Shulgin's] attention was drawn to the 4-position after he conceived of and synthesized the compound DOM, which he bioassayed on January 4, 1964 and discovered to be surprisingly potent: it was psychoactive at the 1 mg dose.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=openDemocracy&rft.atitle=Alexander+Theodore+Shulgin+%281925-2014%29&rft.date=2014-06-09&rft_id=https%3A%2F%2Fwww.opendemocracy.net%2Fen%2Falexander-theodore-shulgin-19252014%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-Shulgin1978-41"><span class="mw-cite-backlink">^ <a href="#cite_ref-Shulgin1978_41-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Shulgin1978_41-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Shulgin1978_41-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShulgin1978" class="citation book cs1">Shulgin AT (1978). <a rel="nofollow" class="external text" href="https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_6">"Psychotomimetic Drugs: Structure-Activity Relationships"</a>. In Iversen LL, Iversen SD, Snyder SH (eds.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=h0_uBwAAQBAJ&pg=PA261"><i>Stimulants</i></a>. Boston, MA: Springer US. pp. <span class="nowrap">243–</span>333. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-1-4757-0510-2_6">10.1007/978-1-4757-0510-2_6</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-0512-6" title="Special:BookSources/978-1-4757-0512-6"><bdi>978-1-4757-0512-6</bdi></a>. <q>3,4,5-Trimethoxyphenylisopropylamine (33, TMA, trimethoxyamphetamine) is the first psychotomimetic drug that evolved from the systematic application of the principles discovered in studying the relationships between chemical structure and biological activity. Armed with the known structure of mescaline, the proclivity of most phenethylamines to be of only fleeting activity centrally (due to facile deamination), and the effectiveness of a methyl group alpha- to the nitrogen as a stabilizing factor in central activity, Her (1947) synthesized TMA. His favorable impressions on the euphoric properties of the compound encouraged the Canadian group of Peretz and co-workers (1955) to explore its psychopharmacological nature and to evaluate its potential as a psychotomimetic. [...] 3.1.6. 2,4,5-Trimethoxyphenylisopropylamine This geometric isomer of TMA was first synthesized by Bruckner (1933) and its psychotomimetic properties were first observed some 30 years later (Shulgin, 1964a), 2,4,5-Trimethoxyphenylisopropylamine (34, TMA-2, 2,4,5-trimethoxyamphetamine) was the second of the six possible positional isomers found to be psychotomimetic, and was thus called TMA-2.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Psychotomimetic+Drugs%3A+Structure-Activity+Relationships&rft.btitle=Stimulants&rft.place=Boston%2C+MA&rft.pages=%3Cspan+class%3D%22nowrap%22%3E243-%3C%2Fspan%3E333&rft.pub=Springer+US&rft.date=1978&rft_id=info%3Adoi%2F10.1007%2F978-1-4757-0510-2_6&rft.isbn=978-1-4757-0512-6&rft.aulast=Shulgin&rft.aufirst=Alexander+T.&rft_id=https%3A%2F%2Fbitnest.netfirms.com%2Fexternal%2F10.1007%2F978-1-4757-0510-2_6&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-Bruckner1933-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-Bruckner1933_42-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBruckner1933" class="citation journal cs1">Bruckner, Viktor (24 October 1933). "Über das Pseudonitrosit des Asarons". <i>Journal für Praktische Chemie</i>. <b>138</b> (<span class="nowrap">9–</span>10): <span class="nowrap">268–</span>274. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fprac.19331380907">10.1002/prac.19331380907</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0021-8383">0021-8383</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+f%C3%BCr+Praktische+Chemie&rft.atitle=%C3%9Cber+das+Pseudonitrosit+des+Asarons&rft.volume=138&rft.issue=%3Cspan+class%3D%22nowrap%22%3E9%E2%80%93%3C%2Fspan%3E10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E268-%3C%2Fspan%3E274&rft.date=1933-10-24&rft_id=info%3Adoi%2F10.1002%2Fprac.19331380907&rft.issn=0021-8383&rft.aulast=Bruckner&rft.aufirst=Viktor&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-Shulgin1964-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-Shulgin1964_43-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShulgin1964" class="citation journal cs1">Shulgin AT (July 1964). 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"A new hallucinogen: 3,4,5-trimethoxyphenyl-beta-aminopropane with notes on the stroboscopic phenomenon". <i>J Ment Sci</i>. <b>101</b> (423): <span class="nowrap">317–</span>329. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1192%2Fbjp.101.423.317">10.1192/bjp.101.423.317</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/13243046">13243046</a>. <q>3,4,5-Trimethoxyphenyl-β-aminopropane (Trimethoxyamphetamine, TMA) was first synthesized by Hey in 1947 (Hey, 1947) who was impressed with its euphoric properties (private communication). [...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Ment+Sci&rft.atitle=A+new+hallucinogen%3A+3%2C4%2C5-trimethoxyphenyl-beta-aminopropane+with+notes+on+the+stroboscopic+phenomenon&rft.volume=101&rft.issue=423&rft.pages=%3Cspan+class%3D%22nowrap%22%3E317-%3C%2Fspan%3E329&rft.date=1955-04&rft_id=info%3Adoi%2F10.1192%2Fbjp.101.423.317&rft_id=info%3Apmid%2F13243046&rft.aulast=Peretz&rft.aufirst=DI&rft.au=Smythies%2C+JR&rft.au=Gibson%2C+WC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-ShulginBunnell1961-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-ShulginBunnell1961_45-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShulginBunnellSargent1961" class="citation journal cs1">Shulgin, Alexander T.; Bunnell, Sterling; Sargent, Thornton (1961). 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Archived from <a rel="nofollow" class="external text" href="https://www.thevespiary.org/rhodium/Rhodium/chemistry/tma.hey.html">the original</a> on 19 July 2019.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Q+J+Pharm+Pharmacol&rft.atitle=The+synthesis+of+a+new+homologue+of+mescaline&rft.volume=20&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E129-%3C%2Fspan%3E134&rft.date=1947&rft_id=info%3Apmid%2F20260568&rft.aulast=Hey&rft.aufirst=P&rft_id=https%3A%2F%2Fwww.thevespiary.org%2Frhodium%2FRhodium%2Fchemistry%2Ftma.hey.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-US3547999A-47"><span class="mw-cite-backlink"><b><a href="#cite_ref-US3547999A_47-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://patents.google.com/patent/US3547999A/en">"phenethylamines and their pharmacologically-acceptable salts"</a>. <i>Google Patents</i>. 1970<span class="reference-accessdate">. Retrieved <span class="nowrap">26 January</span> 2025</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Google+Patents&rft.atitle=phenethylamines+and+their+pharmacologically-acceptable+salts&rft.date=1970&rft_id=https%3A%2F%2Fpatents.google.com%2Fpatent%2FUS3547999A%2Fen&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-TroutDaley2024-48"><span class="mw-cite-backlink">^ <a href="#cite_ref-TroutDaley2024_48-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-TroutDaley2024_48-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-TroutDaley2024_48-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTroutDaley2024" class="citation journal cs1">Trout K, Daley PF (December 2024). <a rel="nofollow" class="external text" href="https://shulginresearch.net/wp-content/uploads/2024/03/The-origin-of-25-dimethoxy-4-methylamphetamine-DOM-STP.-Trout.-Drug-Test.-Anal.-DOI-10.1002-dta.3667-2024.pdf">"The origin of 2,5-dimethoxy-4-methylamphetamine (DOM, STP)"</a> <span class="cs1-format">(PDF)</span>. <i>Drug Test Anal</i>. <b>16</b> (12): <span class="nowrap">1496–</span>1508. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fdta.3667">10.1002/dta.3667</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/38419183">38419183</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drug+Test+Anal&rft.atitle=The+origin+of+2%2C5-dimethoxy-4-methylamphetamine+%28DOM%2C+STP%29&rft.volume=16&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1496-%3C%2Fspan%3E1508&rft.date=2024-12&rft_id=info%3Adoi%2F10.1002%2Fdta.3667&rft_id=info%3Apmid%2F38419183&rft.aulast=Trout&rft.aufirst=K&rft.au=Daley%2C+PF&rft_id=https%3A%2F%2Fshulginresearch.net%2Fwp-content%2Fuploads%2F2024%2F03%2FThe-origin-of-25-dimethoxy-4-methylamphetamine-DOM-STP.-Trout.-Drug-Test.-Anal.-DOI-10.1002-dta.3667-2024.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-SnyderFaillaceHollister1967-49"><span class="mw-cite-backlink"><b><a href="#cite_ref-SnyderFaillaceHollister1967_49-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSnyderFaillaceHollister1967" class="citation journal cs1">Snyder SH, Faillace L, Hollister L (November 1967). "2,5-dimethoxy-4-methyl-amphetamine (STP): a new hallucinogenic drug". <i>Science</i>. <b>158</b> (3801): <span class="nowrap">669–</span>670. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1967Sci...158..669S">1967Sci...158..669S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.158.3801.669">10.1126/science.158.3801.669</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/4860952">4860952</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=2%2C5-dimethoxy-4-methyl-amphetamine+%28STP%29%3A+a+new+hallucinogenic+drug&rft.volume=158&rft.issue=3801&rft.pages=%3Cspan+class%3D%22nowrap%22%3E669-%3C%2Fspan%3E670&rft.date=1967-11&rft_id=info%3Apmid%2F4860952&rft_id=info%3Adoi%2F10.1126%2Fscience.158.3801.669&rft_id=info%3Abibcode%2F1967Sci...158..669S&rft.aulast=Snyder&rft.aufirst=SH&rft.au=Faillace%2C+L&rft.au=Hollister%2C+L&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-SnyderFaillaceWeingartner1968-50"><span class="mw-cite-backlink">^ <a href="#cite_ref-SnyderFaillaceWeingartner1968_50-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-SnyderFaillaceWeingartner1968_50-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-SnyderFaillaceWeingartner1968_50-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSnyderFaillaceWeingartner1968" class="citation journal cs1">Snyder SH, Faillace LA, Weingartner H (September 1968). "DOM (STP), a new hallucinogenic drug, and DOET: effects in normal subjects". <i>Am J Psychiatry</i>. <b>125</b> (3): <span class="nowrap">113–</span>120. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1176%2Fajp.125.3.357">10.1176/ajp.125.3.357</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/4385937">4385937</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Am+J+Psychiatry&rft.atitle=DOM+%28STP%29%2C+a+new+hallucinogenic+drug%2C+and+DOET%3A+effects+in+normal+subjects&rft.volume=125&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E113-%3C%2Fspan%3E120&rft.date=1968-09&rft_id=info%3Adoi%2F10.1176%2Fajp.125.3.357&rft_id=info%3Apmid%2F4385937&rft.aulast=Snyder&rft.aufirst=SH&rft.au=Faillace%2C+LA&rft.au=Weingartner%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-SnyderRichelson1968-51"><span class="mw-cite-backlink"><b><a href="#cite_ref-SnyderRichelson1968_51-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSnyderRichelson1968" class="citation journal cs1">Snyder SH, Richelson E (May 1968). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC539103">"Psychedelic drugs: steric factors that predict psychotropic activity"</a>. <i>Proc Natl Acad Sci U S A</i>. <b>60</b> (1): <span class="nowrap">206–</span>213. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1968PNAS...60..206S">1968PNAS...60..206S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.60.1.206">10.1073/pnas.60.1.206</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC539103">539103</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/5241523">5241523</a>. <q>Shulgin (personal communication) has synthesized 2,5-dimethoxyamphetamine (2,5-DMA) (Fig. 4) and observed its potency in man as between 8 and 10 MU. This compound corresponds to TMA-2 with the absence of the methoxy at C-4. 2,5-DMA is considerably more potent than TMA, TMA-3, or TMA-4, all of which have three methoxy groupings. [...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proc+Natl+Acad+Sci+U+S+A&rft.atitle=Psychedelic+drugs%3A+steric+factors+that+predict+psychotropic+activity&rft.volume=60&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E206-%3C%2Fspan%3E213&rft.date=1968-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC539103%23id-name%3DPMC&rft_id=info%3Apmid%2F5241523&rft_id=info%3Adoi%2F10.1073%2Fpnas.60.1.206&rft_id=info%3Abibcode%2F1968PNAS...60..206S&rft.aulast=Snyder&rft.aufirst=SH&rft.au=Richelson%2C+E&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC539103&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-Shulgin1969-52"><span class="mw-cite-backlink"><b><a href="#cite_ref-Shulgin1969_52-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShulgin1969" class="citation journal cs1">Shulgin, Alexander T. (1969). "Psychotomimetic Agents Related to the Catecholamines". <i>Journal of Psychedelic Drugs</i>. <b>2</b> (2): <span class="nowrap">14–</span>19. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F02791072.1969.10524409">10.1080/02791072.1969.10524409</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-393X">0022-393X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Psychedelic+Drugs&rft.atitle=Psychotomimetic+Agents+Related+to+the+Catecholamines&rft.volume=2&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E14-%3C%2Fspan%3E19&rft.date=1969&rft_id=info%3Adoi%2F10.1080%2F02791072.1969.10524409&rft.issn=0022-393X&rft.aulast=Shulgin&rft.aufirst=Alexander+T.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-Shulgin1970-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-Shulgin1970_53-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAlexander_Shulgin1970" class="citation book cs1"><a href="/wiki/Alexander_Shulgin" title="Alexander Shulgin">Alexander Shulgin</a> (1970). "Chemistry and Structure-Activity Relationships of the Psychotomimetics". In D. H. Efron (ed.). <a rel="nofollow" class="external text" href="https://www.erowid.org/library/books_online/psychotomimetic_drugs.pdf#page=23"><i>Psychotomimetic Drugs</i></a> <span class="cs1-format">(PDF)</span>. New York: Raven Press. pp. <span class="nowrap">21–</span>41.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chemistry+and+Structure-Activity+Relationships+of+the+Psychotomimetics&rft.btitle=Psychotomimetic+Drugs&rft.place=New+York&rft.pages=%3Cspan+class%3D%22nowrap%22%3E21-%3C%2Fspan%3E41&rft.pub=Raven+Press&rft.date=1970&rft.au=Alexander+Shulgin&rft_id=https%3A%2F%2Fwww.erowid.org%2Flibrary%2Fbooks_online%2Fpsychotomimetic_drugs.pdf%23page%3D23&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-ShulginSargentNaranjo1971-54"><span class="mw-cite-backlink"><b><a href="#cite_ref-ShulginSargentNaranjo1971_54-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShulginSargentNaranjo1971" class="citation journal cs1">Shulgin AT, Sargent T, Naranjo C (1971). "4-Bromo-2,5-dimethoxyphenylisopropylamine, a new centrally active amphetamine analog". <i>Pharmacology</i>. <b>5</b> (2): <span class="nowrap">103–</span>107. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000136181">10.1159/000136181</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/5570923">5570923</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacology&rft.atitle=4-Bromo-2%2C5-dimethoxyphenylisopropylamine%2C+a+new+centrally+active+amphetamine+analog&rft.volume=5&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E103-%3C%2Fspan%3E107&rft.date=1971&rft_id=info%3Adoi%2F10.1159%2F000136181&rft_id=info%3Apmid%2F5570923&rft.aulast=Shulgin&rft.aufirst=AT&rft.au=Sargent%2C+T&rft.au=Naranjo%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-CouttsMalicky1973-55"><span class="mw-cite-backlink"><b><a href="#cite_ref-CouttsMalicky1973_55-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCouttsMalicky1973" class="citation journal cs1">Coutts, Ronald T.; Malicky, Jerry L. (1 May 1973). <a rel="nofollow" class="external text" href="https://doi.org/10.1139%2Fv73-210">"The Synthesis of Some Analogs of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM)"</a>. <i>Canadian Journal of Chemistry</i>. <b>51</b> (9): <span class="nowrap">1402–</span>1409. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1139%2Fv73-210">10.1139/v73-210</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0008-4042">0008-4042</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Canadian+Journal+of+Chemistry&rft.atitle=The+Synthesis+of+Some+Analogs+of+the+Hallucinogen+1-%282%2C5-Dimethoxy-4-methylphenyl%29-2-aminopropane+%28DOM%29&rft.volume=51&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1402-%3C%2Fspan%3E1409&rft.date=1973-05-01&rft_id=info%3Adoi%2F10.1139%2Fv73-210&rft.issn=0008-4042&rft.aulast=Coutts&rft.aufirst=Ronald+T.&rft.au=Malicky%2C+Jerry+L.&rft_id=https%3A%2F%2Fdoi.org%2F10.1139%252Fv73-210&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-Nichols2018-56"><span class="mw-cite-backlink"><b><a href="#cite_ref-Nichols2018_56-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNichols2018" class="citation book cs1">Nichols DE (2018). <i>Chemistry and Structure-Activity Relationships of Psychedelics</i>. 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"Synthesis of Novel (Phenylalkyl) amines for the Investigation of Structure–Activity Relationships, Part 3: 4-Ethynyl-2,5-dimethoxyphenethylamine (= 4-Ethynyl-2, 5-dimethoxybenzeneethanamine; 2C-YN)". <i>Helvetica Chimica Acta</i>. <b>86</b> (8): <span class="nowrap">2754–</span>9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fhlca.200390224">10.1002/hlca.200390224</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Helvetica+Chimica+Acta&rft.atitle=Synthesis+of+Novel+%28Phenylalkyl%29+amines+for+the+Investigation+of+Structure%E2%80%93Activity+Relationships%2C+Part+3%3A+4-Ethynyl-2%2C5-dimethoxyphenethylamine+%28%3D+4-Ethynyl-2%2C+5-dimethoxybenzeneethanamine%3B+2C-YN%29.&rft.volume=86&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2754-%3C%2Fspan%3E9&rft.date=2003-08&rft_id=info%3Adoi%2F10.1002%2Fhlca.200390224&rft.aulast=Trachsel&rft.aufirst=D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-KolaczynskaLuethiTrachsel2019-62"><span class="mw-cite-backlink">^ <a href="#cite_ref-KolaczynskaLuethiTrachsel2019_62-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-KolaczynskaLuethiTrachsel2019_62-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-KolaczynskaLuethiTrachsel2019_62-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-KolaczynskaLuethiTrachsel2019_62-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-KolaczynskaLuethiTrachsel2019_62-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-KolaczynskaLuethiTrachsel2019_62-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKolaczynskaLuethiTrachselHoener2019" class="citation journal cs1">Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2019). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6893898">"Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines"</a>. <i>Front Pharmacol</i>. <b>10</b>: 1423. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3389%2Ffphar.2019.01423">10.3389/fphar.2019.01423</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6893898">6893898</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/31849671">31849671</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Front+Pharmacol&rft.atitle=Receptor+Interaction+Profiles+of+4-Alkoxy-Substituted+2%2C5-Dimethoxyphenethylamines+and+Related+Amphetamines&rft.volume=10&rft.pages=1423&rft.date=2019&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6893898%23id-name%3DPMC&rft_id=info%3Apmid%2F31849671&rft_id=info%3Adoi%2F10.3389%2Ffphar.2019.01423&rft.aulast=Kolaczynska&rft.aufirst=KE&rft.au=Luethi%2C+D&rft.au=Trachsel%2C+D&rft.au=Hoener%2C+MC&rft.au=Liechti%2C+ME&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6893898&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADOx" class="Z3988"></span></span> </li> <li id="cite_note-63"><span class="mw-cite-backlink"><b><a href="#cite_ref-63">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://patents.google.com/patent/US4034113A">Shulgin AT. Treatment of senile geriatric patients to restore performance. Patent US 4034113</a></span> </li> <li id="cite_note-64"><span class="mw-cite-backlink"><b><a href="#cite_ref-64">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://patents.google.com/patent/US7396856">Hellberg MR, Namil A. Benzopyran analogs and their use for the treatment of glaucoma. Patent US 7396856</a></span> </li> <li id="cite_note-65"><span class="mw-cite-backlink"><b><a href="#cite_ref-65">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://patentimages.storage.googleapis.com/a2/12/19/8424e3822cbe82/US20210137908A1.pdf">Kristensen J, et al. 5-HT2A Agonists for Use in Treatment of Depression. Patent US 2021/0137908</a></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DOx&action=edit&section=14" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://isomerdesign.com/PiHKAL/">PiHKAL ("Phenethylamines I Have Known And Loved")</a> by <a href="/wiki/Alexander_Shulgin" title="Alexander Shulgin">Alexander "Sasha" Shulgin</a> (1991)</li> <li><a rel="nofollow" class="external text" href="http://www.erowid.org/archive/rhodium/chemistry/shulgin.pea.sar.hop.html">Psychotomimetic Drugs: Structure-Activity Relationships</a> by <a href="/wiki/Alexander_Shulgin" title="Alexander Shulgin">Alexander "Sasha" Shulgin</a> (1978)</li></ul> <div class="navbox-styles"><style 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exist)">1cP-MiPLA</a></li> <li><a href="/wiki/1V-LSD" title="1V-LSD">1V-LSD</a></li> <li><a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">2-Butyllysergamide</a></li> <li><a href="/wiki/Lysergic_acid_3-pentyl_amide" title="Lysergic acid 3-pentyl amide">3-Pentyllysergamide</a></li> <li><a href="/wiki/AL-LAD" title="AL-LAD">AL-LAD</a></li> <li><a href="/wiki/ALD-52" title="ALD-52">ALD-52</a></li> <li><a href="/wiki/BU-LAD" title="BU-LAD">BU-LAD</a></li> <li><a href="/wiki/Diallyllysergamide" title="Diallyllysergamide">Diallyllysergamide</a></li> <li><a href="/wiki/Dimethyllysergamide" title="Dimethyllysergamide">Dimethyllysergamide</a></li> <li><a href="/wiki/ECPLA" title="ECPLA">ECPLA</a></li> <li><a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">Ergometrine</a></li> <li><a href="/wiki/ETH-LAD" title="ETH-LAD">ETH-LAD</a></li> <li><a href="/wiki/IP-LAD" class="mw-redirect" title="IP-LAD">IP-LAD</a></li> <li><a href="/wiki/LAE-32" title="LAE-32">LAE-32</a></li> <li><a href="/wiki/LAMPA" title="LAMPA">LAMPA</a></li> <li><a href="/wiki/LPD-824" title="LPD-824">LPD-824</a></li> <li><a href="/wiki/Ergine" title="Ergine">LSA</a></li> <li><a href="/wiki/LSD" title="LSD">LSD</a></li> <li><a href="/wiki/LSD-Pip" title="LSD-Pip">LSD-Pip</a></li> <li><a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">LSH</a></li> <li><a href="/wiki/LSM-775" title="LSM-775">LSM-775</a></li> <li><a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">LSZ</a></li> <li><a href="/wiki/Methylergometrine" title="Methylergometrine">Methylergometrine</a></li> <li><a href="/wiki/Methylisopropyllysergamide" title="Methylisopropyllysergamide">MIPLA</a></li> <li><a href="/wiki/Methysergide" title="Methysergide">Methysergide</a></li> <li><a href="/wiki/N1-Methyl-lysergic_acid_diethylamide" class="mw-redirect" title="N1-Methyl-lysergic acid diethylamide">MLD-41</a></li> <li><a href="/wiki/PARGY-LAD" title="PARGY-LAD">PARGY-LAD</a></li> <li><a href="/wiki/PRO-LAD" title="PRO-LAD">PRO-LAD</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethyl‐<br />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 id="2C-x217" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2C-<i>x</i></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B" title="2C-B">2C-B</a></li> <li><a href="/w/index.php?title=2C-B-AN&action=edit&redlink=1" class="new" title="2C-B-AN (page does not exist)">2C-B-AN</a></li> <li><a href="/w/index.php?title=2C-Bn&action=edit&redlink=1" class="new" title="2C-Bn (page does not exist)">2C-Bn</a></li> <li><a href="/wiki/2C-Bu" title="2C-Bu">2C-Bu</a></li> <li><a href="/wiki/2C-C" title="2C-C">2C-C</a></li> <li><a href="/w/index.php?title=2C-CN&action=edit&redlink=1" class="new" title="2C-CN (page does not exist)">2C-CN</a></li> <li><a href="/wiki/2C-CP" title="2C-CP">2C-CP</a></li> <li><a href="/wiki/2C-D" title="2C-D">2C-D</a></li> <li><a href="/wiki/2C-E" title="2C-E">2C-E</a></li> <li><a href="/wiki/2C-EF" title="2C-EF">2C-EF</a></li> <li><a href="/wiki/2C-F" title="2C-F">2C-F</a></li> <li><a href="/wiki/2C-G" title="2C-G">2C-G</a></li> <li><a href="/wiki/2C-G-1" class="mw-redirect" title="2C-G-1">2C-G-1</a></li> <li><a href="/wiki/2C-G-2" class="mw-redirect" title="2C-G-2">2C-G-2</a></li> <li><a href="/wiki/2C-G-3" class="mw-redirect" title="2C-G-3">2C-G-3</a></li> <li><a href="/wiki/2C-G-4" class="mw-redirect" title="2C-G-4">2C-G-4</a></li> <li><a href="/wiki/2C-G-5" class="mw-redirect" title="2C-G-5">2C-G-5</a></li> <li><a href="/wiki/2C-G-6" class="mw-redirect" title="2C-G-6">2C-G-6</a></li> <li><a href="/wiki/2C-G-N" class="mw-redirect" title="2C-G-N">2C-G-N</a></li> <li><a href="/wiki/2C-H" title="2C-H">2C-H</a></li> <li><a href="/wiki/2C-I" title="2C-I">2C-I</a></li> <li><a href="/wiki/2C-iBu" title="2C-iBu">2C-iBu</a></li> <li><a href="/wiki/2C-iP" title="2C-iP">2C-iP</a></li> <li><a href="/wiki/2C-N" title="2C-N">2C-N</a></li> <li><a href="/w/index.php?title=2C-NH2&action=edit&redlink=1" class="new" title="2C-NH2 (page does not exist)">2C-NH2</a></li> <li><a href="/wiki/2C-O" class="mw-redirect" title="2C-O">2C-O</a></li> <li><a href="/wiki/2C-O-4" title="2C-O-4">2C-O-4</a></li> <li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li> <li><a href="/wiki/2C-Ph" title="2C-Ph">2C-Ph</a></li> <li><a href="/wiki/2C-SE" class="mw-redirect" title="2C-SE">2C-SE</a></li> <li><a href="/wiki/2C-T" title="2C-T">2C-T</a></li> <li><a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a></li> <li><a href="/wiki/2C-T-3" title="2C-T-3">2C-T-3</a></li> <li><a href="/wiki/2C-T-4" title="2C-T-4">2C-T-4</a></li> <li><a href="/w/index.php?title=2C-T-5&action=edit&redlink=1" class="new" title="2C-T-5 (page does not exist)">2C-T-5</a></li> <li><a href="/w/index.php?title=2C-T-6&action=edit&redlink=1" class="new" title="2C-T-6 (page does not exist)">2C-T-6</a></li> <li><a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a></li> <li><a href="/wiki/2C-T-8" title="2C-T-8">2C-T-8</a></li> <li><a href="/wiki/2C-T-9" class="mw-redirect" title="2C-T-9">2C-T-9</a></li> <li><a href="/w/index.php?title=2C-T-10&action=edit&redlink=1" class="new" title="2C-T-10 (page does not exist)">2C-T-10</a></li> <li><a href="/w/index.php?title=2C-T-11&action=edit&redlink=1" class="new" title="2C-T-11 (page does not exist)">2C-T-11</a></li> <li><a href="/w/index.php?title=2C-T-12&action=edit&redlink=1" class="new" title="2C-T-12 (page does not exist)">2C-T-12</a></li> <li><a href="/wiki/2C-T-13" title="2C-T-13">2C-T-13</a></li> <li><a href="/w/index.php?title=2C-T-14&action=edit&redlink=1" class="new" title="2C-T-14 (page does not exist)">2C-T-14</a></li> <li><a href="/wiki/2C-T-15" title="2C-T-15">2C-T-15</a></li> <li><a href="/wiki/2C-T-16" title="2C-T-16">2C-T-16</a></li> <li><a href="/wiki/2C-T-17" title="2C-T-17">2C-T-17</a></li> <li><a href="/w/index.php?title=2C-T-18&action=edit&redlink=1" class="new" title="2C-T-18 (page does not exist)">2C-T-18</a></li> <li><a href="/wiki/2C-T-19" title="2C-T-19">2C-T-19</a></li> <li><a href="/w/index.php?title=2C-T-20&action=edit&redlink=1" class="new" title="2C-T-20 (page does not exist)">2C-T-20</a></li> <li><a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a></li> <li><a href="/w/index.php?title=2C-T-22&action=edit&redlink=1" class="new" title="2C-T-22 (page does not exist)">2C-T-22</a></li> <li><a href="/w/index.php?title=2C-T-22.5&action=edit&redlink=1" class="new" title="2C-T-22.5 (page does not exist)">2C-T-22.5</a></li> <li><a href="/w/index.php?title=2C-T-23&action=edit&redlink=1" class="new" title="2C-T-23 (page does not exist)">2C-T-23</a></li> <li><a href="/w/index.php?title=2C-T-24&action=edit&redlink=1" class="new" title="2C-T-24 (page does not exist)">2C-T-24</a></li> <li><a href="/w/index.php?title=2C-T-25&action=edit&redlink=1" class="new" title="2C-T-25 (page does not exist)">2C-T-25</a></li> <li><a href="/wiki/2C-T-27" title="2C-T-27">2C-T-27</a></li> <li><a href="/wiki/2C-T-28" title="2C-T-28">2C-T-28</a></li> <li><a href="/w/index.php?title=2C-T-30&action=edit&redlink=1" class="new" title="2C-T-30 (page does not exist)">2C-T-30</a></li> <li><a href="/w/index.php?title=2C-T-31&action=edit&redlink=1" class="new" title="2C-T-31 (page does not exist)">2C-T-31</a></li> <li><a href="/w/index.php?title=2C-T-32&action=edit&redlink=1" class="new" title="2C-T-32 (page does not exist)">2C-T-32</a></li> <li><a href="/wiki/2C-T-33" title="2C-T-33">2C-T-33</a></li> <li><a href="/wiki/2C-tBu" title="2C-tBu">2C-tBu</a></li> <li><a href="/wiki/2C-TFE" title="2C-TFE">2C-TFE</a></li> <li><a href="/wiki/2C-TFM" title="2C-TFM">2C-TFM</a></li> <li><a href="/wiki/2C-YN" title="2C-YN">2C-YN</a></li> <li><a href="/wiki/2C-V" title="2C-V">2C-V</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/25-NB" title="25-NB">25<i>x</i>-NB<i>x</i></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%">25<i>x</i>-<abbr title="NB: N-benzyl">NB</abbr></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/25B-NB" class="mw-redirect" title="25B-NB">25B-NB</a></li> <li><a href="/w/index.php?title=25C-NB&action=edit&redlink=1" class="new" title="25C-NB (page does not exist)">25C-NB</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-<abbr title="NB: N-benzyl; 3OMe: 3-methoxy">NB3OMe</abbr></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="/w/index.php?title=25B-NB3OMe&action=edit&redlink=1" class="new" title="25B-NB3OMe (page does not exist)">25B-NB3OMe</a></li> <li><a href="/wiki/25C-NB3OMe" title="25C-NB3OMe">25C-NB3OMe</a></li> <li><a href="/w/index.php?title=25D-NB3OMe&action=edit&redlink=1" class="new" title="25D-NB3OMe (page does not exist)">25D-NB3OMe</a></li> <li><a href="/w/index.php?title=25E-NB3OMe&action=edit&redlink=1" class="new" title="25E-NB3OMe (page does not exist)">25E-NB3OMe</a></li> <li><a href="/w/index.php?title=25H-NB3OMe&action=edit&redlink=1" class="new" title="25H-NB3OMe (page does not exist)">25H-NB3OMe</a></li> <li><a href="/wiki/25I-NB3OMe" title="25I-NB3OMe">25I-NB3OMe</a></li> <li><a href="/w/index.php?title=25N-NB3OMe&action=edit&redlink=1" class="new" title="25N-NB3OMe (page does not exist)">25N-NB3OMe</a></li> <li><a href="/w/index.php?title=25P-NB3OMe&action=edit&redlink=1" class="new" title="25P-NB3OMe (page does not exist)">25P-NB3OMe</a></li> <li><a href="/w/index.php?title=25T2-NB3OMe&action=edit&redlink=1" class="new" title="25T2-NB3OMe (page does not exist)">25T2-NB3OMe</a></li> <li><a href="/w/index.php?title=25T4-NB3OMe&action=edit&redlink=1" class="new" title="25T4-NB3OMe (page does not exist)">25T4-NB3OMe</a></li> <li><a href="/w/index.php?title=25T7-NB3OMe&action=edit&redlink=1" class="new" title="25T7-NB3OMe (page does not exist)">25T7-NB3OMe</a></li> <li><a href="/w/index.php?title=25TFM-NB3OMe&action=edit&redlink=1" class="new" title="25TFM-NB3OMe (page does not exist)">25TFM-NB3OMe</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-<abbr title="NB: N-benzyl; 4OMe: 4-methoxy">NB4OMe</abbr></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="/w/index.php?title=25B-NB4OMe&action=edit&redlink=1" class="new" title="25B-NB4OMe (page does not exist)">25B-NB4OMe</a></li> <li><a href="/wiki/25C-NB4OMe" title="25C-NB4OMe">25C-NB4OMe</a></li> <li><a href="/w/index.php?title=25D-NB4OMe&action=edit&redlink=1" class="new" title="25D-NB4OMe (page does not exist)">25D-NB4OMe</a></li> <li><a href="/w/index.php?title=25E-NB4OMe&action=edit&redlink=1" class="new" title="25E-NB4OMe (page does not exist)">25E-NB4OMe</a></li> <li><a href="/w/index.php?title=25H-NB4OMe&action=edit&redlink=1" class="new" title="25H-NB4OMe (page does not exist)">25H-NB4OMe</a></li> <li><a href="/wiki/25I-NB4OMe" title="25I-NB4OMe">25I-NB4OMe</a></li> <li><a href="/w/index.php?title=25N-NB4OMe&action=edit&redlink=1" class="new" title="25N-NB4OMe (page does not exist)">25N-NB4OMe</a></li> <li><a href="/w/index.php?title=25P-NB4OMe&action=edit&redlink=1" class="new" title="25P-NB4OMe (page does not exist)">25P-NB4OMe</a></li> <li><a href="/w/index.php?title=25T2-NB4OMe&action=edit&redlink=1" class="new" title="25T2-NB4OMe (page does not exist)">25T2-NB4OMe</a></li> <li><a href="/w/index.php?title=25T4-NB4OMe&action=edit&redlink=1" class="new" title="25T4-NB4OMe (page does not exist)">25T4-NB4OMe</a></li> <li><a href="/w/index.php?title=25T7-NB4OMe&action=edit&redlink=1" class="new" title="25T7-NB4OMe (page does not exist)">25T7-NB4OMe</a></li> <li><a href="/w/index.php?title=25TFM-NB4OMe&action=edit&redlink=1" class="new" title="25TFM-NB4OMe (page does not exist)">25TFM-NB4OMe</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-<abbr title="NB: N-benzyl; F: fluoro">NBF</abbr></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/25B-NBF" title="25B-NBF">25B-NBF</a></li> <li><a href="/wiki/25C-NBF" title="25C-NBF">25C-NBF</a></li> <li><a href="/w/index.php?title=25D-NBF&action=edit&redlink=1" class="new" title="25D-NBF (page does not exist)">25D-NBF</a></li> <li><a href="/w/index.php?title=25E-NBF&action=edit&redlink=1" class="new" title="25E-NBF (page does not exist)">25E-NBF</a></li> <li><a href="/w/index.php?title=25H-NBF&action=edit&redlink=1" class="new" title="25H-NBF (page does not exist)">25H-NBF</a></li> <li><a href="/wiki/25I-NBF" title="25I-NBF">25I-NBF</a></li> <li><a href="/w/index.php?title=25P-NBF&action=edit&redlink=1" class="new" title="25P-NBF (page does not exist)">25P-NBF</a></li> <li><a href="/w/index.php?title=25T2-NBF&action=edit&redlink=1" class="new" title="25T2-NBF (page does not exist)">25T2-NBF</a></li> <li><a href="/w/index.php?title=25T7-NBF&action=edit&redlink=1" class="new" title="25T7-NBF (page does not exist)">25T7-NBF</a></li> <li><a href="/w/index.php?title=25TFM-NBF&action=edit&redlink=1" class="new" title="25TFM-NBF (page does not exist)">25TFM-NBF</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-<abbr title="NB: N-benzyl; MD: methylenedioxy">NBMD</abbr></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="/w/index.php?title=25B-NBMD&action=edit&redlink=1" class="new" title="25B-NBMD (page does not exist)">25B-NBMD</a></li> <li><a href="/w/index.php?title=25C-NBMD&action=edit&redlink=1" class="new" title="25C-NBMD (page does not exist)">25C-NBMD</a></li> <li><a href="/w/index.php?title=25D-NBMD&action=edit&redlink=1" class="new" title="25D-NBMD (page does not exist)">25D-NBMD</a></li> <li><a href="/w/index.php?title=25E-NBMD&action=edit&redlink=1" class="new" title="25E-NBMD (page does not exist)">25E-NBMD</a></li> <li><a href="/w/index.php?title=25F-NBMD&action=edit&redlink=1" class="new" title="25F-NBMD (page does not exist)">25F-NBMD</a></li> <li><a href="/w/index.php?title=25H-NBMD&action=edit&redlink=1" class="new" title="25H-NBMD (page does not exist)">25H-NBMD</a></li> <li><a href="/wiki/25I-NBMD" title="25I-NBMD">25I-NBMD</a></li> <li><a href="/w/index.php?title=25P-NBMD&action=edit&redlink=1" class="new" title="25P-NBMD (page does not exist)">25P-NBMD</a></li> <li><a href="/w/index.php?title=25T2-NBMD&action=edit&redlink=1" class="new" title="25T2-NBMD (page does not exist)">25T2-NBMD</a></li> <li><a href="/w/index.php?title=25T7-NBMD&action=edit&redlink=1" class="new" title="25T7-NBMD (page does not exist)">25T7-NBMD</a></li> <li><a href="/w/index.php?title=25TFM-NBMD&action=edit&redlink=1" class="new" title="25TFM-NBMD (page does not exist)">25TFM-NBMD</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-<abbr title="NB: N-benzyl; OH: hydroxy">NBOH</abbr></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/25B-NBOH" title="25B-NBOH">25B-NBOH</a></li> <li><a href="/wiki/25C-NBOH" title="25C-NBOH">25C-NBOH</a></li> <li><a href="/wiki/25CN-NBOH" title="25CN-NBOH">25CN-NBOH</a></li> <li><a href="/w/index.php?title=25D-NBOH&action=edit&redlink=1" class="new" title="25D-NBOH (page does not exist)">25D-NBOH</a></li> <li><a href="/wiki/25E-NBOH" title="25E-NBOH">25E-NBOH</a></li> <li><a href="/w/index.php?title=25F-NBOH&action=edit&redlink=1" class="new" title="25F-NBOH (page does not exist)">25F-NBOH</a></li> <li><a href="/w/index.php?title=25H-NBOH&action=edit&redlink=1" class="new" title="25H-NBOH (page does not exist)">25H-NBOH</a></li> <li><a href="/wiki/25I-NBOH" title="25I-NBOH">25I-NBOH</a></li> <li><a href="/w/index.php?title=25P-NBOH&action=edit&redlink=1" class="new" title="25P-NBOH (page does not exist)">25P-NBOH</a></li> <li><a href="/w/index.php?title=25T2-NBOH&action=edit&redlink=1" class="new" title="25T2-NBOH (page does not exist)">25T2-NBOH</a></li> <li><a href="/w/index.php?title=25T7-NBOH&action=edit&redlink=1" class="new" title="25T7-NBOH (page does not exist)">25T7-NBOH</a></li> <li><a href="/w/index.php?title=25TFM-NBOH&action=edit&redlink=1" class="new" title="25TFM-NBOH (page does not exist)">25TFM-NBOH</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-<abbr title="NB: N-benzyl; OMe: methoxy">NBOMe</abbr></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a></li> <li><a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a></li> <li><a href="/wiki/25CN-NBOMe" title="25CN-NBOMe">25CN-NBOMe</a></li> <li><a href="/wiki/25D-NBOMe" title="25D-NBOMe">25D-NBOMe</a></li> <li><a href="/wiki/25E-NBOMe" title="25E-NBOMe">25E-NBOMe</a></li> <li><a href="/w/index.php?title=25F-NBOMe&action=edit&redlink=1" class="new" title="25F-NBOMe (page does not exist)">25F-NBOMe</a></li> <li><a href="/wiki/25G-NBOMe" title="25G-NBOMe">25G-NBOMe</a></li> <li><a href="/wiki/25H-NBOMe" title="25H-NBOMe">25H-NBOMe</a></li> <li><a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a></li> <li><a href="/wiki/25iP-NBOMe" title="25iP-NBOMe">25iP-NBOMe</a></li> <li><a href="/wiki/25N-NBOMe" title="25N-NBOMe">25N-NBOMe</a></li> <li><a href="/wiki/25P-NBOMe" title="25P-NBOMe">25P-NBOMe</a></li> <li><a href="/w/index.php?title=25T-NBOMe&action=edit&redlink=1" class="new" title="25T-NBOMe (page does not exist)">25T-NBOMe</a></li> <li><a href="/w/index.php?title=25T2-NBOMe&action=edit&redlink=1" class="new" title="25T2-NBOMe (page does not exist)">25T2-NBOMe</a></li> <li><a href="/w/index.php?title=25T4-NBOMe&action=edit&redlink=1" class="new" title="25T4-NBOMe (page does not exist)">25T4-NBOMe</a></li> <li><a href="/wiki/25T7-NBOMe" title="25T7-NBOMe">25T7-NBOMe</a></li> <li><a href="/wiki/25TFM-NBOMe" title="25TFM-NBOMe">25TFM-NBOMe</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Atypical structures</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="/w/index.php?title=25B-N1POMe&action=edit&redlink=1" class="new" title="25B-N1POMe (page does not exist)">25B-N1POMe</a></li> <li><a href="/w/index.php?title=25B-NAcPip&action=edit&redlink=1" class="new" title="25B-NAcPip (page does not exist)">25B-NAcPip</a></li> <li><a href="/w/index.php?title=25B-NB23DM&action=edit&redlink=1" class="new" title="25B-NB23DM (page does not exist)">25B-NB23DM</a></li> <li><a href="/w/index.php?title=25B-NB25DM&action=edit&redlink=1" class="new" title="25B-NB25DM (page does not exist)">25B-NB25DM</a></li> <li><a href="/w/index.php?title=25C-NBCl&action=edit&redlink=1" class="new" title="25C-NBCl (page does not exist)">25C-NBCl</a></li> <li><a href="/w/index.php?title=25C-NBOEt&action=edit&redlink=1" class="new" title="25C-NBOEt (page does not exist)">25C-NBOEt</a></li> <li><a href="/w/index.php?title=25C-NBOiPr&action=edit&redlink=1" class="new" title="25C-NBOiPr (page does not exist)">25C-NBOiPr</a></li> <li><a href="/w/index.php?title=25I-N2Nap1OH&action=edit&redlink=1" class="new" title="25I-N2Nap1OH (page does not exist)">25I-N2Nap1OH</a></li> <li><a href="/w/index.php?title=25I-N3MT2M&action=edit&redlink=1" class="new" title="25I-N3MT2M (page does not exist)">25I-N3MT2M</a></li> <li><a href="/w/index.php?title=25I-N4MT3M&action=edit&redlink=1" class="new" title="25I-N4MT3M (page does not exist)">25I-N4MT3M</a></li> <li><a href="/wiki/25I-NB34MD" title="25I-NB34MD">25I-NB34MD</a></li> <li><a href="/w/index.php?title=25I-NBAm&action=edit&redlink=1" class="new" title="25I-NBAm (page does not exist)">25I-NBAm</a></li> <li><a href="/w/index.php?title=25I-NBBr&action=edit&redlink=1" class="new" title="25I-NBBr (page does not exist)">25I-NBBr</a></li> <li><a href="/w/index.php?title=25I-NBMeOH&action=edit&redlink=1" class="new" title="25I-NBMeOH (page does not exist)">25I-NBMeOH</a></li> <li><a href="/w/index.php?title=25I-NBTFM&action=edit&redlink=1" class="new" title="25I-NBTFM (page does not exist)">25I-NBTFM</a></li> <li><a href="/wiki/2CBCB-NBOMe" title="2CBCB-NBOMe">2CBCB-NBOMe</a></li> <li><a href="/wiki/2CBFly-NBOMe" title="2CBFly-NBOMe">2CBFly-NBOMe</a></li> <li><a href="/wiki/4-EA-NBOMe" title="4-EA-NBOMe">4-EA-NBOMe</a></li> <li><a href="/w/index.php?title=5-APB-NBOMe&action=edit&redlink=1" class="new" title="5-APB-NBOMe (page does not exist)">5-APB-NBOMe</a></li> <li><a href="/w/index.php?title=5MT-NBOMe&action=edit&redlink=1" class="new" title="5MT-NBOMe (page does not exist)">5MT-NBOMe</a></li> <li><a href="/w/index.php?title=C30-NBOMe&action=edit&redlink=1" class="new" title="C30-NBOMe (page does not exist)">C30-NBOMe</a></li> <li><a href="/w/index.php?title=DOB-NBOMe&action=edit&redlink=1" class="new" title="DOB-NBOMe (page does not exist)">DOB-NBOMe</a></li> <li><a href="/w/index.php?title=DOI-NBOMe&action=edit&redlink=1" class="new" title="DOI-NBOMe (page does not exist)">DOI-NBOMe</a></li> <li><a href="/w/index.php?title=FECIMBI-36&action=edit&redlink=1" class="new" title="FECIMBI-36 (page does not exist)">FECIMBI-36</a></li> <li><a href="/w/index.php?title=MDPEA-NBOMe&action=edit&redlink=1" class="new" title="MDPEA-NBOMe (page does not exist)">MDPEA-NBOMe</a></li> <li><a href="/wiki/N-Ethyl-2C-B" title="N-Ethyl-2C-B">N-Ethyl-2C-B</a></li> <li><a href="/w/index.php?title=NBOMe-escaline&action=edit&redlink=1" class="new" title="NBOMe-escaline (page does not exist)">NBOMe-escaline</a></li> <li><a href="/wiki/NBOMe-mescaline" title="NBOMe-mescaline">NBOMe-mescaline</a></li> <li><a href="/wiki/ZDCM-04" title="ZDCM-04">ZDCM-04</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-NM<i>x</i></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="/w/index.php?title=25B-NMe7BF&action=edit&redlink=1" class="new" title="25B-NMe7BF (page does not exist)">25B-NMe7BF</a></li> <li><a href="/w/index.php?title=25B-NMe7BT&action=edit&redlink=1" class="new" title="25B-NMe7BT (page does not exist)">25B-NMe7BT</a></li> <li><a href="/w/index.php?title=25B-NMe7Bim&action=edit&redlink=1" class="new" title="25B-NMe7Bim (page does not exist)">25B-NMe7Bim</a></li> <li><a href="/w/index.php?title=25B-NMe7Box&action=edit&redlink=1" class="new" title="25B-NMe7Box (page does not exist)">25B-NMe7Box</a></li> <li><a href="/w/index.php?title=25B-NMe7DHBF&action=edit&redlink=1" class="new" title="25B-NMe7DHBF (page does not exist)">25B-NMe7DHBF</a></li> <li><a href="/w/index.php?title=25B-NMe7Ind&action=edit&redlink=1" class="new" title="25B-NMe7Ind (page does not exist)">25B-NMe7Ind</a></li> <li><a href="/w/index.php?title=25B-NMe7Indz&action=edit&redlink=1" class="new" title="25B-NMe7Indz (page does not exist)">25B-NMe7Indz</a></li> <li><a href="/w/index.php?title=25B-NMePyr&action=edit&redlink=1" class="new" title="25B-NMePyr (page does not exist)">25B-NMePyr</a></li> <li><a href="/w/index.php?title=25I-NMe7DHBF&action=edit&redlink=1" class="new" title="25I-NMe7DHBF (page does not exist)">25I-NMe7DHBF</a></li> <li><a href="/w/index.php?title=25I-NMeFur&action=edit&redlink=1" class="new" title="25I-NMeFur (page does not exist)">25I-NMeFur</a></li> <li><a href="/w/index.php?title=25I-NMeTHF&action=edit&redlink=1" class="new" title="25I-NMeTHF (page does not exist)">25I-NMeTHF</a></li> <li><a href="/w/index.php?title=25I-NMeTh&action=edit&redlink=1" class="new" title="25I-NMeTh (page does not exist)">25I-NMeTh</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/N-(2C)-fentanyl" class="mw-redirect" title="N-(2C)-fentanyl">N-(2C)-fentanyl</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="/w/index.php?title=N-(2C-B)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-B) fentanyl (page does not exist)">N-(2C-B) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-C)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-C) fentanyl (page does not exist)">N-(2C-C) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-D)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-D) fentanyl (page does not exist)">N-(2C-D) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-E)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-E) fentanyl (page does not exist)">N-(2C-E) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-G)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-G) fentanyl (page does not exist)">N-(2C-G) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-H)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-H) fentanyl (page does not exist)">N-(2C-H) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-I)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-I) fentanyl (page does not exist)">N-(2C-I) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-IP)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-IP) fentanyl (page does not exist)">N-(2C-IP) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-N)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-N) fentanyl (page does not exist)">N-(2C-N) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-P)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-P) fentanyl (page does not exist)">N-(2C-P) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-T)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-T) fentanyl (page does not exist)">N-(2C-T) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-T-2)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-T-2) fentanyl (page does not exist)">N-(2C-T-2) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-T-4)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-T-4) fentanyl (page does not exist)">N-(2C-T-4) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-T-7)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-T-7) fentanyl (page does not exist)">N-(2C-T-7) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-TFM)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-TFM) fentanyl (page does not exist)">N-(2C-TFM) fentanyl</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">3C-<i>x</i></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3C-AL" title="3C-AL">3C-AL</a></li> <li><a href="/wiki/3C-BZ" title="3C-BZ">3C-BZ</a></li> <li><a href="/wiki/3C-DFE" title="3C-DFE">3C-DFE</a></li> <li><a href="/wiki/3C-E" title="3C-E">3C-E</a></li> <li><a href="/wiki/3C-MAL" title="3C-MAL">3C-MAL</a></li> <li><a href="/wiki/3C-P" title="3C-P">3C-P</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">4C-<i>x</i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4C-B" title="4C-B">4C-B</a></li> <li><a href="/w/index.php?title=4C-C&action=edit&redlink=1" class="new" title="4C-C (page does not exist)">4C-C</a></li> <li><a href="/wiki/4C-D" class="mw-redirect" title="4C-D">4C-D</a></li> <li><a href="/w/index.php?title=4C-E&action=edit&redlink=1" class="new" title="4C-E (page does not exist)">4C-E</a></li> <li><a href="/w/index.php?title=4C-I&action=edit&redlink=1" class="new" title="4C-I (page does not exist)">4C-I</a></li> <li><a href="/w/index.php?title=4C-N&action=edit&redlink=1" class="new" title="4C-N (page does not exist)">4C-N</a></li> <li><a href="/w/index.php?title=4C-P&action=edit&redlink=1" class="new" title="4C-P (page does not exist)">4C-P</a></li> <li><a href="/wiki/4C-T-2" title="4C-T-2">4C-T-2</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">DO<i>x</i></a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aleph_(psychedelic)" title="Aleph (psychedelic)">DOT</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine" title="2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine">DOEF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-fluoroamphetamine" title="2,5-Dimethoxy-4-fluoroamphetamine">DOF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-isopropylamphetamine" title="2,5-Dimethoxy-4-isopropylamphetamine">DOiPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-nitroamphetamine" title="2,5-Dimethoxy-4-nitroamphetamine">DON</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-propylamphetamine" title="2,5-Dimethoxy-4-propylamphetamine">DOPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-trifluoromethylamphetamine" title="2,5-Dimethoxy-4-trifluoromethylamphetamine">DOTFM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethoxyamphetamine" title="2,5-Dimethoxy-4-ethoxyamphetamine">MEM</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">HOT-<i>x</i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/HOT-2" title="HOT-2">HOT-2</a></li> <li><a href="/wiki/HOT-7" title="HOT-7">HOT-7</a></li> <li><a href="/wiki/HOT-17" title="HOT-17">HOT-17</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MD<em>xx</em></a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/DMMDA" title="DMMDA">DMMDA</a></li> <li><a href="/wiki/2,3-Dimethoxy-4,5-methylenedioxyamphetamine" class="mw-redirect" title="2,3-Dimethoxy-4,5-methylenedioxyamphetamine">DMMDA-2</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA</a></li> <li><a href="/wiki/MDAI" title="MDAI">MDAI</a></li> <li><a href="/wiki/MDBZ" class="mw-redirect" title="MDBZ">MDBZ</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDA-2" title="MMDA-2">MMDA-2</a></li> <li><a href="/wiki/MMDA-3a" title="MMDA-3a">MMDA-3a</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_mescaline_analogue" title="Substituted mescaline analogue">Mescaline (subst.)</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Bromomescaline" title="2-Bromomescaline">2-Bromomescaline</a></li> <li><a href="/wiki/Thioescaline" title="Thioescaline">3-TE</a></li> <li><a href="/wiki/Thioescaline" title="Thioescaline">4-TE</a></li> <li><a href="/wiki/Thiomescaline" title="Thiomescaline">3-TM</a></li> <li><a href="/wiki/Thiomescaline" title="Thiomescaline">4-TM</a></li> <li><a href="/wiki/Allylescaline" title="Allylescaline">Allylescaline</a></li> <li><a href="/wiki/Asymbescaline" title="Asymbescaline">Asymbescaline</a></li> <li><a href="/wiki/Buscaline" title="Buscaline">Buscaline</a></li> <li><a href="/wiki/Cyclopropylmescaline" title="Cyclopropylmescaline">Cyclopropylmescaline</a></li> <li><a href="/w/index.php?title=Difluoromescaline&action=edit&redlink=1" class="new" title="Difluoromescaline (page does not exist)">Difluoromescaline</a></li> <li><a href="/w/index.php?title=Difluoroescaline&action=edit&redlink=1" class="new" title="Difluoroescaline (page does not exist)">Difluoroescaline</a></li> <li><a href="/wiki/Escaline" title="Escaline">Escaline</a></li> <li><a href="/w/index.php?title=Fluoroproscaline&action=edit&redlink=1" class="new" title="Fluoroproscaline (page does not exist)">Fluoroproscaline</a></li> <li><a href="/w/index.php?title=Isobuscaline&action=edit&redlink=1" class="new" title="Isobuscaline (page does not exist)">Isobuscaline</a></li> <li><a href="/wiki/Isoproscaline" title="Isoproscaline">Isoproscaline</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metaescaline" title="Metaescaline">Metaescaline</a></li> <li><a href="/wiki/Methallylescaline" title="Methallylescaline">Methallylescaline</a></li> <li><a href="/wiki/Proscaline" title="Proscaline">Proscaline</a></li> <li><a href="/wiki/Thioproscaline" title="Thioproscaline">Thioproscaline</a></li> <li><a href="/w/index.php?title=Trifluoroescaline&action=edit&redlink=1" class="new" title="Trifluoroescaline (page does not exist)">Trifluoroescaline</a></li> <li><a href="/wiki/Trifluoromescaline" title="Trifluoromescaline">Trifluoromescaline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trimethoxyamphetamine" class="mw-redirect" title="Trimethoxyamphetamine">TMAs</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/TMA-1_(psychedelic)" class="mw-redirect" title="TMA-1 (psychedelic)">TMA</a></li> <li><a href="/wiki/TMA-2_(psychedelic)" class="mw-redirect" title="TMA-2 (psychedelic)">TMA-2</a></li> <li><a href="/wiki/TMA-3_(psychedelic)" class="mw-redirect" title="TMA-3 (psychedelic)">TMA-3</a></li> <li><a href="/wiki/TMA-4_(psychedelic)" class="mw-redirect" title="TMA-4 (psychedelic)">TMA-4</a></li> <li><a href="/wiki/TMA-5_(psychedelic)" class="mw-redirect" title="TMA-5 (psychedelic)">TMA-5</a></li> <li><a href="/wiki/TMA-6_(psychedelic)" class="mw-redirect" title="TMA-6 (psychedelic)">TMA-6</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B-BUTTERFLY" title="2C-B-BUTTERFLY">2C-B-BUTTERFLY</a></li> <li><a href="/w/index.php?title=2C-B-DragonFLY&action=edit&redlink=1" class="new" title="2C-B-DragonFLY (page does not exist)">2C-B-DragonFLY</a></li> <li><a href="/w/index.php?title=2C-B-DragonFLY-NBOH&action=edit&redlink=1" class="new" title="2C-B-DragonFLY-NBOH (page does not exist)">2C-B-DragonFLY-NBOH</a></li> <li><a href="/w/index.php?title=2C-B-FLY-NB2EtO5Cl&action=edit&redlink=1" class="new" title="2C-B-FLY-NB2EtO5Cl (page does not exist)">2C-B-FLY-NB2EtO5Cl</a></li> <li><a href="/w/index.php?title=2CB-5-hemifly&action=edit&redlink=1" class="new" title="2CB-5-hemifly (page does not exist)">2CB-5-hemifly</a></li> <li><a href="/wiki/2CB-Ind" title="2CB-Ind">2CB-Ind</a></li> <li><a href="/wiki/2CD-5EtO" title="2CD-5EtO">2CD-5EtO</a></li> <li><a href="/wiki/TOET_(psychedelic)#2-TOET" title="TOET (psychedelic)">2-TOET</a></li> <li><a href="/wiki/TOET_(psychedelic)#5-TOET" title="TOET (psychedelic)">5-TOET</a></li> <li><a href="/wiki/TOM_(psychedelic)" title="TOM (psychedelic)">2-TOM</a></li> <li><a href="/wiki/TOM_(psychedelic)" title="TOM (psychedelic)">5-TOM</a></li> <li><a href="/wiki/BOB_(psychedelic)" title="BOB (psychedelic)">BOB</a></li> <li><a href="/wiki/BOD_(psychedelic)" title="BOD (psychedelic)">BOD</a></li> <li><a href="/wiki/%CE%92k-2C-B" title="Βk-2C-B">βk-2C-B</a></li> <li><a href="/w/index.php?title=%CE%92k-2C-I&action=edit&redlink=1" class="new" title="Βk-2C-I (page does not exist)">βk-2C-I</a></li> <li><a href="/wiki/DESOXY" title="DESOXY">DESOXY</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylphenylcyclopropylamine" title="2,5-Dimethoxy-4-methylphenylcyclopropylamine">DMCPA</a></li> <li><a href="/wiki/DMBMPP" title="DMBMPP">DMBMPP</a></li> <li><a href="/wiki/DOB-FLY" title="DOB-FLY">DOB-FLY</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Ganesha_(psychedelic)" title="Ganesha (psychedelic)">Ganesha</a></li> <li><a href="/wiki/Macromerine" title="Macromerine">Macromerine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li> <li><a href="/wiki/TOMSO" title="TOMSO">TOMSO</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_piperazine" title="Substituted piperazine">Piperazines</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B-PP" title="2C-B-PP">2C-B-PP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-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="/wiki/Substituted_alpha-alkyltryptamine" class="mw-redirect" title="Substituted alpha-alkyltryptamine"><i>alpha</i>-alkyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AL-37350A" title="AL-37350A">4,5-DHP-α-MT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-α-ET</a></li> <li><a href="/wiki/5-MeO-aMT" class="mw-redirect" title="5-MeO-aMT">5-MeO-α-MT</a></li> <li><a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">α-ET</a></li> <li><a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">α-MT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N,N-Diallyltryptamine">DALT</abbr></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="/w/index.php?title=4-HO-DALT&action=edit&redlink=1" class="new" title="4-HO-DALT (page does not exist)">(Daltocin) 4-HO-DALT</a></li> <li><a href="/wiki/4-AcO-DALT" title="4-AcO-DALT">(Daltacetin) 4-AcO-DALT</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/DALT" title="DALT">DALT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N,N-Diethyltryptamine">DET</abbr></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Acetoxy-DET" class="mw-redirect" title="4-Acetoxy-DET">(Ethacetin) 4-AcO-DET</a></li> <li><a href="/wiki/4-HO-DET" title="4-HO-DET">(Ethocin) 4-HO-DET</a></li> <li><a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a></li> <li><a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">(T-9) DET</a></li> <li><a href="/wiki/Ethocybin" title="Ethocybin">(Ethocybin) 4-PO-DET</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N,N-Diisopropyltryptamine">DiPT</abbr></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Acetoxy-DiPT" title="4-Acetoxy-DiPT">(Ipracetin) 4-AcO-DiPT</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">(Iprocin) 4-HO-DiPT</a></li> <li><a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a></li> <li><a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N,N-Dimethyltryptamine">DMT</abbr></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole" class="mw-redirect" title="1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole">4,5-DHP-DMT</a></li> <li><a href="/wiki/2,N,N-TMT" title="2,N,N-TMT">2,N,N-TMT</a></li> <li><a href="/wiki/O-Acetylpsilocin" class="mw-redirect" title="O-Acetylpsilocin">4-AcO-DMT</a></li> <li><a href="/wiki/4-Hydroxy-5-methoxydimethyltryptamine" class="mw-redirect" title="4-Hydroxy-5-methoxydimethyltryptamine">4-HO-5-MeO-DMT</a></li> <li><a href="/w/index.php?title=4,N,N-TMT&action=edit&redlink=1" class="new" title="4,N,N-TMT (page does not exist)">4,N,N-TMT</a></li> <li><a href="/wiki/4-Propionyloxy-DMT" class="mw-redirect" title="4-Propionyloxy-DMT">4-Propionyloxy-DMT</a></li> <li><a href="/w/index.php?title=5,6-diBr-DMT&action=edit&redlink=1" class="new" title="5,6-diBr-DMT (page does not exist)">5,6-diBr-DMT</a></li> <li><a href="/wiki/5-AcO-DMT" class="mw-redirect" title="5-AcO-DMT">5-AcO-DMT</a></li> <li><a href="/wiki/5-Bromo-DMT" title="5-Bromo-DMT">5-Bromo-DMT</a></li> <li><a href="/w/index.php?title=(Indapex)_5-MeO-2-TMT&action=edit&redlink=1" class="new" title="(Indapex) 5-MeO-2-TMT (page does not exist)">5-MeO-2,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/w/index.php?title=5-MeO-4,N,N-TMT&action=edit&redlink=1" class="new" title="5-MeO-4,N,N-TMT (page does not exist)">5-MeO-4,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/5-MeO-%CE%B1,N,N-TMT" class="mw-redirect" title="5-MeO-α,N,N-TMT">5-MeO-α,N,N-TMT</a></li> <li><a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a></li> <li><a href="/wiki/5,N,N-TMT" title="5,N,N-TMT">5-<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/7,N,N-TMT" title="7,N,N-TMT">7,N,N-TMT</a></li> <li><a href="/wiki/Alpha-N,N-Trimethyltryptamine" class="mw-redirect" title="Alpha-N,N-Trimethyltryptamine">α,N,N-TMT</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">(Bufotenin) 5-HO-DMT</a></li> <li><a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Norbaeocystin" title="Norbaeocystin">Norbaeocystin</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">(Psilocin) 4-HO-DMT</a></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">(Psilocybin) 4-PO-DMT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N,N-Dipropyltryptamine">DPT</abbr></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="/w/index.php?title=4-Acetoxy-DPT&action=edit&redlink=1" class="new" title="4-Acetoxy-DPT (page does not exist)">(Depracetin) 4-AcO-DPT</a></li> <li><a href="/wiki/4-HO-DPT" title="4-HO-DPT">(Deprocin) 4-HO-DPT</a></li> <li><a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a></li> <li><a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">(The Light) DPT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Ibogaine-related</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/18-Methylaminocoronaridine" title="18-Methylaminocoronaridine">18-MAC</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Ibogamine" title="Ibogamine">Ibogamine</a></li> <li><a href="/wiki/2-Methoxyethyl-18-methoxycoronaridinate" title="2-Methoxyethyl-18-methoxycoronaridinate">ME-18-MC</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Tabernanthine" title="Tabernanthine">Tabernanthine</a></li> <li><a href="/wiki/Voacangine" title="Voacangine">Voacangine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N-Methyl-N-ethyltryptamine">MET</abbr></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-HO-MET" title="4-HO-MET">(Metocin) 4-HO-MET</a></li> <li><a href="/wiki/4-AcO-MET" title="4-AcO-MET">(Metocetin) 4-AcO-MET</a></li> <li><a href="/wiki/5-MeO-MET" title="5-MeO-MET">5-MeO-MET</a></li> <li><a href="/wiki/N-Methyl-N-ethyltryptamine" title="N-Methyl-N-ethyltryptamine">MET</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N-Methyl-N-isopropyltryptamine">MiPT</abbr></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Acetoxy-MiPT" class="mw-redirect" title="4-Acetoxy-MiPT">(Mipracetin) 4-AcO-MiPT</a></li> <li><a href="/wiki/4-HO-MiPT" title="4-HO-MiPT">(Miprocin) 4-HO-MiPT</a></li> <li><a href="/wiki/5,N-Dimethyl-N-isopropyltryptamine" class="mw-redirect" title="5,N-Dimethyl-N-isopropyltryptamine">5-Me-MiPT</a></li> <li><a href="/wiki/5-MeO-MiPT" title="5-MeO-MiPT">(Moxy) 5-MeO-MiPT</a></li> <li><a href="/wiki/Methylisopropyltryptamine" class="mw-redirect" title="Methylisopropyltryptamine">MiPT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">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><a href="/wiki/4-HO-DBT" title="4-HO-DBT">4-HO-DBT</a></li> <li><a href="/wiki/4-HO-EPT" title="4-HO-EPT">4-HO-EPT</a></li> <li><a href="/wiki/4-HO-McPT" title="4-HO-McPT">4-HO-McPT</a></li> <li><a href="/wiki/4-HO-MPMI" title="4-HO-MPMI">(Lucigenol) 4-HO-MPMI</a></li> <li><a href="/wiki/4-HO-MPT" title="4-HO-MPT">(Meprocin) 4-HO-MPT</a></li> <li><a href="/wiki/5-MeO-EiPT" title="5-MeO-EiPT">5-MeO-EiPT</a></li> <li><a href="/wiki/5-MeO-MALT" title="5-MeO-MALT">5-MeO-MALT</a></li> <li><a href="/wiki/5-MeO-MPMI" title="5-MeO-MPMI">5-MeO-MPMI</a></li> <li><a href="/wiki/Aeruginascin" title="Aeruginascin">Aeruginascin</a></li> <li><a href="/wiki/Baeocystin" title="Baeocystin">Baeocystin</a></li> <li><a href="/wiki/Dibutyltryptamine" title="Dibutyltryptamine">DBT</a></li> <li><a href="/w/index.php?title=Dicyclopropyltryptamine&action=edit&redlink=1" class="new" title="Dicyclopropyltryptamine (page does not exist)">DCPT</a></li> <li><a href="/wiki/Ethylisopropyltryptamine" title="Ethylisopropyltryptamine">EiPT</a></li> <li><a href="/wiki/Ethylpropyltryptamine" title="Ethylpropyltryptamine">EPT</a></li> <li><a href="/wiki/Methylpropyltryptamine" title="Methylpropyltryptamine">MPT</a></li> <li><a href="/wiki/Propylisopropyltryptamine" title="Propylisopropyltryptamine">PiPT</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AL-38022A" title="AL-38022A">AL-38022A</a></li> <li><a href="/wiki/ALPHA_(psychedelic)" title="ALPHA (psychedelic)">ALPHA</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/M-ALPHA" class="mw-redirect" title="M-ALPHA">M-ALPHA</a></li> <li><a href="/wiki/RH-34" title="RH-34">RH-34</a><br /><small>Also <a href="/wiki/Empathogen-entactogen" class="mw-redirect" title="Empathogen-entactogen">empathogens</a> in general (e. g.: <a href="/wiki/5-APB" title="5-APB">5-APB</a>, <a href="/wiki/5-MAPB" title="5-MAPB">5-MAPB</a>, <a href="/wiki/6-APB" title="6-APB">6-APB</a> and other <a href="/wiki/Substituted_benzofuran" title="Substituted benzofuran">substituted benzofurans</a>).</small></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dissociative" title="Dissociative">Dissociatives</a><br /><small>(<a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDAR</a><br /><a href="/wiki/NMDA_receptor_antagonist" title="NMDA receptor antagonist">antagonists</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclo‐<br />hexylamines</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%">Ketamine-related</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Fluorodeschloroketamine" title="2-Fluorodeschloroketamine">2-Fluorodeschloroketamine</a></li> <li><a href="/wiki/Arketamine" title="Arketamine">Arketamine</a> ((R)-ketamine)</li> <li><a href="/wiki/Deschloroketamine" title="Deschloroketamine">Deschloroketamine</a></li> <li><a href="/wiki/Ethketamine" class="mw-redirect" title="Ethketamine">Ethketamine</a> (N-Ethylnorketamine)</li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a> ((S)-ketamine)</li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Methoxetamine" title="Methoxetamine">Methoxetamine</a></li> <li><a href="/wiki/Methoxmetamine" title="Methoxmetamine">Methoxmetamine</a></li> <li><a href="/wiki/Methoxyketamine" title="Methoxyketamine">Methoxyketamine</a></li> <li><a href="/wiki/MXiPr" class="mw-redirect" title="MXiPr">MXiPr</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Tiletamine" title="Tiletamine">Tiletamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">PCP-related</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2%27-Oxo-PCE" class="mw-redirect" title="2'-Oxo-PCE">2'-Oxo-PCE</a></li> <li><a href="/w/index.php?title=3-HO-PCE&action=edit&redlink=1" class="new" title="3-HO-PCE (page does not exist)">3-HO-PCE</a></li> <li><a href="/wiki/3-HO-PCP" title="3-HO-PCP">3-HO-PCP</a></li> <li><a href="/wiki/3-MeO-PCE" title="3-MeO-PCE">3-MeO-PCE</a></li> <li><a href="/wiki/3-MeO-PCMo" title="3-MeO-PCMo">3-MeO-PCMo</a></li> <li><a href="/wiki/3-MeO-PCP" title="3-MeO-PCP">3-MeO-PCP</a></li> <li><a href="/w/index.php?title=3-MeO-PCPr&action=edit&redlink=1" class="new" title="3-MeO-PCPr (page does not exist)">3-MeO-PCPr</a></li> <li><a href="/w/index.php?title=3-MeO-PCPy&action=edit&redlink=1" class="new" title="3-MeO-PCPy (page does not exist)">3-MeO-PCPy</a></li> <li><a href="/wiki/4-MeO-PCP" title="4-MeO-PCP">4-MeO-PCP</a></li> <li><a href="/wiki/BDPC" title="BDPC">BDPC</a></li> <li><a href="/wiki/Dieticyclidine" title="Dieticyclidine">Dieticyclidine</a> (PCDE)</li> <li><a href="/wiki/Eticyclidine" title="Eticyclidine">Eticyclidine</a> (PCE)</li> <li><a href="/wiki/PCPr" title="PCPr">PCPr</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a> (PCP)</li> <li><a href="/wiki/Rolicyclidine" title="Rolicyclidine">Rolicyclidine</a> (PCPy)</li> <li><a href="/wiki/Tenocyclidine" title="Tenocyclidine">Tenocyclidine</a> (TCP)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">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><a href="/wiki/BTCP" class="mw-redirect" title="BTCP">BTCP</a></li> <li><a href="/wiki/Gacyclidine" title="Gacyclidine">Gacyclidine</a></li> <li><a href="/wiki/PRE-084" title="PRE-084">PRE-084</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adamantane" title="Adamantane">Adamantanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Rimantadine" title="Rimantadine">Rimantadine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Diarylethylamines</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diphenidine" title="Diphenidine">Diphenidine</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><a href="/wiki/Fluorolintane" title="Fluorolintane">Fluorolintane</a></li> <li><a href="/wiki/Methoxphenidine" title="Methoxphenidine">Methoxphenidine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Morphinan" title="Morphinan">Morphinans</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dextrallorphan" title="Dextrallorphan">Dextrallorphan</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/wiki/Racemethorphan" class="mw-redirect" title="Racemethorphan">Racemethorphan</a></li> <li><a href="/wiki/Racemorphan" title="Racemorphan">Racemorphan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">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><a href="/wiki/2-EMSB" class="mw-redirect" title="2-EMSB">2-EMSB</a></li> <li><a href="/wiki/2-MDP" title="2-MDP">2-MDP</a></li> <li><a href="/wiki/8A-PDHQ" title="8A-PDHQ">8A-PDHQ</a></li> <li><a href="/wiki/Aptiganel" title="Aptiganel">Aptiganel</a></li> <li><a href="/wiki/Budipine" title="Budipine">Budipine</a></li> <li><a href="/wiki/Delucemine" title="Delucemine">Delucemine</a></li> <li><a href="/wiki/Dexoxadrol" title="Dexoxadrol">Dexoxadrol</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Etoxadrol" title="Etoxadrol">Etoxadrol</a></li> <li><a href="/wiki/Herkinorin" title="Herkinorin">Herkinorin</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Midafotel" title="Midafotel">Midafotel</a></li> <li><a href="/wiki/NEFA_(drug)" title="NEFA (drug)">NEFA</a></li> <li><a href="/wiki/Neramexane" title="Neramexane">Neramexane</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Perzinfotel" title="Perzinfotel">Perzinfotel</a></li> <li><a href="/wiki/RB-64" title="RB-64">RB-64</a></li> <li><a href="/wiki/Remacemide" title="Remacemide">Remacemide</a></li> <li><a href="/wiki/Selfotel" title="Selfotel">Selfotel</a></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deliriant" title="Deliriant">Deliriants</a><br /><small>(<a href="/wiki/Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">mAChR</a><br /><a href="/wiki/Anticholinergic" title="Anticholinergic">antagonists</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Atropine" title="Atropine">Atropine</a></li> <li><a href="/wiki/Benactyzine" title="Benactyzine">Benactyzine</a></li> <li><a href="/wiki/Benzatropine" title="Benzatropine">Benzatropine</a></li> <li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Biperiden" title="Biperiden">Biperiden</a></li> <li><a href="/w/index.php?title=BRN-1484501&action=edit&redlink=1" class="new" title="BRN-1484501 (page does not exist)">BRN-1484501</a></li> <li><a href="/wiki/Brompheniramine" title="Brompheniramine">Brompheniramine</a></li> <li><a href="/wiki/3-Quinuclidinyl_benzilate" title="3-Quinuclidinyl benzilate">BZ</a></li> <li><a href="/wiki/CAR-226,086" title="CAR-226,086">CAR-226,086</a></li> <li><a href="/wiki/CAR-301,060" title="CAR-301,060">CAR-301,060</a></li> <li><a href="/wiki/CAR-302,196" title="CAR-302,196">CAR-302,196</a></li> <li><a href="/wiki/CAR-302,282" title="CAR-302,282">CAR-302,282</a></li> <li><a href="/w/index.php?title=CAR-302,368&action=edit&redlink=1" class="new" title="CAR-302,368 (page does not exist)">CAR-302,368</a></li> <li><a href="/w/index.php?title=CAR-302,537&action=edit&redlink=1" class="new" title="CAR-302,537 (page does not exist)">CAR-302,537</a></li> <li><a href="/wiki/CAR-302,668" title="CAR-302,668">CAR-302,668</a></li> <li><a href="/wiki/Chloropyramine" title="Chloropyramine">Chloropyramine</a></li> <li><a href="/wiki/Chlorphenamine" title="Chlorphenamine">Chlorphenamine</a></li> <li><a href="/wiki/Clemastine" title="Clemastine">Clemastine</a></li> <li><a href="/wiki/CS-27349" title="CS-27349">CS-27349</a></li> <li><a href="/wiki/Cyclizine" title="Cyclizine">Cyclizine</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Dicycloverine" title="Dicycloverine">Dicycloverine</a></li> <li><a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">Dimenhydrinate</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li> <li><a href="/wiki/Ditran" title="Ditran">Ditran</a></li> <li><a href="/wiki/Doxylamine" title="Doxylamine">Doxylamine</a></li> <li><a href="/wiki/EA-3167" title="EA-3167">EA-3167</a></li> <li><a href="/wiki/EA-3443" title="EA-3443">EA-3443</a></li> <li><a href="/wiki/EA-3580" title="EA-3580">EA-3580</a></li> <li><a href="/wiki/EA-3834" title="EA-3834">EA-3834</a></li> <li><a href="/wiki/Flavoxate" title="Flavoxate">Flavoxate</a></li> <li><a href="/wiki/Hyoscyamine" title="Hyoscyamine">Hyoscyamine</a></li> <li><a href="/wiki/N-Ethyl-3-piperidyl_benzilate" title="N-Ethyl-3-piperidyl benzilate">JB-318</a></li> <li><a href="/wiki/N-Methyl-3-piperidyl_benzilate" title="N-Methyl-3-piperidyl benzilate">JB-336</a></li> <li><a href="/wiki/Meclozine" class="mw-redirect" title="Meclozine">Meclozine</a></li> <li><a href="/wiki/Mepyramine" title="Mepyramine">Mepyramine</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li> <li><a href="/wiki/Oxybutynin" title="Oxybutynin">Oxybutynin</a></li> <li><a href="/wiki/Pheniramine" title="Pheniramine">Pheniramine</a></li> <li><a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">Phenyltoloxamine</a></li> <li><a href="/wiki/Procyclidine" title="Procyclidine">Procyclidine</a></li> <li><a href="/wiki/Promethazine" title="Promethazine">Promethazine</a></li> <li><a href="/wiki/Scopolamine" title="Scopolamine">Scopolamine</a></li> <li><a href="/wiki/Tolterodine" title="Tolterodine">Tolterodine</a></li> <li><a href="/wiki/Trihexyphenidyl" title="Trihexyphenidyl">Trihexyphenidyl</a></li> <li><a href="/wiki/Tripelennamine" title="Tripelennamine">Tripelennamine</a></li> <li><a href="/wiki/Triprolidine" title="Triprolidine">Triprolidine</a></li> <li><a href="/wiki/WIN-2299" title="WIN-2299">WIN-2299</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</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="/wiki/Cannabinoid" title="Cannabinoid">Cannabinoids</a><br /><small>(<a href="/wiki/Cannabinoid_receptor_type_1" class="mw-redirect" title="Cannabinoid receptor type 1">CB<sub>1</sub></a> agonists)</small></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="/wiki/Phytocannabinoids" class="mw-redirect" title="Phytocannabinoids">Natural</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">THC (Dronabinol)</a></li> <li><a href="/wiki/THCV" class="mw-redirect" title="THCV">THCV</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Synthetic_cannabinoids" title="Synthetic cannabinoids">Synthetic</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="/wiki/List_of_AM_cannabinoids" title="List of AM cannabinoids">AM-<i>x</i></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AM-087" title="AM-087">AM-087</a></li> <li><a href="/wiki/AM251" class="mw-redirect" title="AM251">AM-251</a></li> <li><a href="/w/index.php?title=AM-279_(disambiguation)&action=edit&redlink=1" class="new" title="AM-279 (disambiguation) (page does not exist)">AM-279</a></li> <li><a href="/w/index.php?title=AM-281_(disambiguation)&action=edit&redlink=1" class="new" title="AM-281 (disambiguation) (page does not exist)">AM-281</a></li> <li><a href="/w/index.php?title=AM-356_(disambiguation)&action=edit&redlink=1" class="new" title="AM-356 (disambiguation) (page does not exist)">AM-356</a></li> <li><a href="/w/index.php?title=AM-374_(disambiguation)&action=edit&redlink=1" class="new" title="AM-374 (disambiguation) (page does not exist)">AM-374</a></li> <li><a href="/w/index.php?title=AM-381_(disambiguation)&action=edit&redlink=1" class="new" title="AM-381 (disambiguation) (page does not exist)">AM-381</a></li> <li><a href="/wiki/AM-404" class="mw-redirect" title="AM-404">AM-404</a></li> <li><a href="/wiki/AM-411" title="AM-411">AM-411</a></li> <li><a href="/wiki/AM-630" title="AM-630">AM-630</a></li> <li><a href="/w/index.php?title=AM-661&action=edit&redlink=1" class="new" title="AM-661 (page does not exist)">AM-661</a></li> <li><a href="/wiki/AM-678" class="mw-redirect" title="AM-678">AM-678</a></li> <li><a href="/wiki/AM-679_(cannabinoid)" title="AM-679 (cannabinoid)">AM-679</a></li> <li><a href="/wiki/AM-694" title="AM-694">AM-694</a></li> <li><a href="/w/index.php?title=AM-735&action=edit&redlink=1" class="new" title="AM-735 (page does not exist)">AM-735</a></li> <li><a href="/wiki/AM-855" title="AM-855">AM-855</a></li> <li><a href="/w/index.php?title=AM-881&action=edit&redlink=1" class="new" title="AM-881 (page does not exist)">AM-881</a></li> <li><a href="/wiki/AM-883" class="mw-redirect" title="AM-883">AM-883</a></li> <li><a href="/wiki/AM-905" title="AM-905">AM-905</a></li> <li><a href="/wiki/AM-906" title="AM-906">AM-906</a></li> <li><a href="/wiki/AM-919" title="AM-919">AM-919</a></li> <li><a href="/wiki/AM-926" class="mw-redirect" title="AM-926">AM-926</a></li> <li><a href="/wiki/AM-938" title="AM-938">AM-938</a></li> <li><a href="/w/index.php?title=AM-1116&action=edit&redlink=1" class="new" title="AM-1116 (page does not exist)">AM-1116</a></li> <li><a href="/w/index.php?title=AM-1172&action=edit&redlink=1" class="new" title="AM-1172 (page does not exist)">AM-1172</a></li> <li><a href="/wiki/AM-1220" title="AM-1220">AM-1220</a></li> <li><a href="/wiki/AM-1221" title="AM-1221">AM-1221</a></li> <li><a href="/wiki/AM-1235" title="AM-1235">AM-1235</a></li> <li><a href="/wiki/AM-1241" title="AM-1241">AM-1241</a></li> <li><a href="/wiki/AM-1248" title="AM-1248">AM-1248</a></li> <li><a href="/w/index.php?title=AM-1710&action=edit&redlink=1" class="new" title="AM-1710 (page does not exist)">AM-1710</a></li> <li><a href="/wiki/AM-1714" title="AM-1714">AM-1714</a></li> <li><a href="/w/index.php?title=AM-1902&action=edit&redlink=1" class="new" title="AM-1902 (page does not exist)">AM-1902</a></li> <li><a href="/wiki/AM-2201" title="AM-2201">AM-2201</a></li> <li><a href="/w/index.php?title=AM-2212&action=edit&redlink=1" class="new" title="AM-2212 (page does not exist)">AM-2212</a></li> <li><a href="/w/index.php?title=AM-2213&action=edit&redlink=1" class="new" title="AM-2213 (page does not exist)">AM-2213</a></li> <li><a href="/wiki/AM-2232" title="AM-2232">AM-2232</a></li> <li><a href="/wiki/AM-2233" title="AM-2233">AM-2233</a></li> <li><a href="/wiki/AM-2389" title="AM-2389">AM-2389</a></li> <li><a href="/w/index.php?title=AM-3102&action=edit&redlink=1" class="new" title="AM-3102 (page does not exist)">AM-3102</a></li> <li><a href="/wiki/AM-4030" title="AM-4030">AM-4030</a></li> <li><a href="/w/index.php?title=AM-4054&action=edit&redlink=1" class="new" title="AM-4054 (page does not exist)">AM-4054</a></li> <li><a href="/wiki/AM-4056" class="mw-redirect" title="AM-4056">AM-4056</a></li> <li><a href="/wiki/AM-4113" class="mw-redirect" title="AM-4113">AM-4113</a></li> <li><a href="/wiki/AM-6545" title="AM-6545">AM-6545</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_CP_cannabinoids" title="List of CP cannabinoids">CP <i>x</i></a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CP_47,497" title="CP 47,497">CP 47,497</a></li> <li><a href="/wiki/CP_55,244" title="CP 55,244">CP 55,244</a></li> <li><a href="/wiki/CP_55,940" title="CP 55,940">CP 55,940</a></li> <li><a href="/w/index.php?title=(%C2%B1)-CP_55,940&action=edit&redlink=1" class="new" title="(±)-CP 55,940 (page does not exist)">(±)-CP 55,940</a></li> <li><a href="/w/index.php?title=(%2B)-CP_55,940&action=edit&redlink=1" class="new" title="(+)-CP 55,940 (page does not exist)">(+)-CP 55,940</a></li> <li><a href="/w/index.php?title=(-)-CP_55,940&action=edit&redlink=1" class="new" title="(-)-CP 55,940 (page does not exist)">(-)-CP 55,940</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_HU_cannabinoids" title="List of HU cannabinoids">HU-<i>x</i></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/HU-210" title="HU-210">HU-210</a></li> <li><a href="/wiki/HU-211" class="mw-redirect" title="HU-211">HU-211</a></li> <li><a href="/wiki/HU-239" class="mw-redirect" title="HU-239">HU-239</a></li> <li><a href="/wiki/HU-243" title="HU-243">HU-243</a></li> <li><a href="/wiki/HU-308" class="mw-redirect" title="HU-308">HU-308</a></li> <li><a href="/wiki/HU-320" title="HU-320">HU-320</a></li> <li><a href="/wiki/HU-331" title="HU-331">HU-331</a></li> <li><a href="/wiki/HU-336" title="HU-336">HU-336</a></li> <li><a href="/wiki/HU-345" title="HU-345">HU-345</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_JWH_cannabinoids" title="List of JWH cannabinoids">JWH-<i>x</i></a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/JWH-007" title="JWH-007">JWH-007</a></li> <li><a href="/wiki/JWH-015" title="JWH-015">JWH-015</a></li> <li><a href="/wiki/JWH-018" title="JWH-018">JWH-018</a></li> <li><a href="/wiki/JWH-019" title="JWH-019">JWH-019</a></li> <li><a href="/wiki/JWH-030" title="JWH-030">JWH-030</a></li> <li><a href="/wiki/JWH-047" title="JWH-047">JWH-047</a></li> <li><a href="/wiki/JWH-048" title="JWH-048">JWH-048</a></li> <li><a href="/wiki/JWH-051" title="JWH-051">JWH-051</a></li> <li><a href="/wiki/JWH-057" title="JWH-057">JWH-057</a></li> <li><a href="/wiki/JWH-073" title="JWH-073">JWH-073</a></li> <li><a href="/wiki/JWH-081" title="JWH-081">JWH-081</a></li> <li><a href="/wiki/JWH-098" title="JWH-098">JWH-098</a></li> <li><a href="/wiki/JWH-116" title="JWH-116">JWH-116</a></li> <li><a href="/wiki/JWH-120" title="JWH-120">JWH-120</a></li> <li><a href="/wiki/JWH-122" title="JWH-122">JWH-122</a></li> <li><a href="/wiki/JWH-133" title="JWH-133">JWH-133</a></li> <li><a href="/w/index.php?title=JWH-139&action=edit&redlink=1" class="new" title="JWH-139 (page does not exist)">JWH-139</a></li> <li><a href="/wiki/JWH-147" title="JWH-147">JWH-147</a></li> <li><a href="/wiki/JWH-148" title="JWH-148">JWH-148</a></li> <li><a href="/wiki/JWH-149" title="JWH-149">JWH-149</a></li> <li><a href="/wiki/JWH-149" title="JWH-149">JWH-149</a></li> <li><a href="/wiki/JWH-161" title="JWH-161">JWH-161</a></li> <li><a href="/wiki/JWH-164" title="JWH-164">JWH-164</a></li> <li><a href="/w/index.php?title=JWH-166&action=edit&redlink=1" class="new" title="JWH-166 (page does not exist)">JWH-166</a></li> <li><a href="/wiki/JWH-167" title="JWH-167">JWH-167</a></li> <li><a href="/wiki/JWH-171" class="mw-redirect" title="JWH-171">JWH-171</a></li> <li><a href="/wiki/JWH-175" title="JWH-175">JWH-175</a></li> <li><a href="/wiki/JWH-176" title="JWH-176">JWH-176</a></li> <li><a href="/w/index.php?title=JWH-181&action=edit&redlink=1" class="new" title="JWH-181 (page does not exist)">JWH-181</a></li> <li><a href="/wiki/JWH-182" class="mw-redirect" title="JWH-182">JWH-182</a></li> <li><a href="/wiki/JWH-184" title="JWH-184">JWH-184</a></li> <li><a href="/wiki/JWH-185" title="JWH-185">JWH-185</a></li> <li><a href="/w/index.php?title=JWH-192&action=edit&redlink=1" class="new" title="JWH-192 (page does not exist)">JWH-192</a></li> <li><a href="/wiki/JWH-193" title="JWH-193">JWH-193</a></li> <li><a href="/w/index.php?title=JWH-194&action=edit&redlink=1" class="new" title="JWH-194 (page does not exist)">JWH-194</a></li> <li><a href="/w/index.php?title=JWH-195&action=edit&redlink=1" class="new" title="JWH-195 (page does not exist)">JWH-195</a></li> <li><a href="/wiki/JWH-196" title="JWH-196">JWH-196</a></li> <li><a href="/w/index.php?title=JWH-197&action=edit&redlink=1" class="new" title="JWH-197 (page does not exist)">JWH-197</a></li> <li><a href="/wiki/JWH-198" title="JWH-198">JWH-198</a></li> <li><a href="/w/index.php?title=JWH-199&action=edit&redlink=1" class="new" title="JWH-199 (page does not exist)">JWH-199</a></li> <li><a href="/wiki/JWH-200" title="JWH-200">JWH-200</a></li> <li><a href="/wiki/JWH-203" title="JWH-203">JWH-203</a></li> <li><a href="/w/index.php?title=JWH-205&action=edit&redlink=1" class="new" title="JWH-205 (page does not exist)">JWH-205</a></li> <li><a href="/wiki/JWH-210" title="JWH-210">JWH-210</a></li> <li><a href="/wiki/JWH-210" title="JWH-210">JWH-210</a></li> <li><a href="/w/index.php?title=JWH-213&action=edit&redlink=1" class="new" title="JWH-213 (page does not exist)">JWH-213</a></li> <li><a href="/w/index.php?title=JWH-220&action=edit&redlink=1" class="new" title="JWH-220 (page does not exist)">JWH-220</a></li> <li><a href="/w/index.php?title=JWH-229&action=edit&redlink=1" class="new" title="JWH-229 (page does not exist)">JWH-229</a></li> <li><a href="/w/index.php?title=JWH-234&action=edit&redlink=1" class="new" title="JWH-234 (page does not exist)">JWH-234</a></li> <li><a href="/wiki/JWH-249" title="JWH-249">JWH-249</a></li> <li><a href="/wiki/JWH-250" title="JWH-250">JWH-250</a></li> <li><a href="/wiki/JWH-251" title="JWH-251">JWH-251</a></li> <li><a href="/w/index.php?title=JWH-253&action=edit&redlink=1" class="new" title="JWH-253 (page does not exist)">JWH-253</a></li> <li><a href="/w/index.php?title=JWH-258&action=edit&redlink=1" class="new" title="JWH-258 (page does not exist)">JWH-258</a></li> <li><a href="/w/index.php?title=JWH-300&action=edit&redlink=1" class="new" title="JWH-300 (page does not exist)">JWH-300</a></li> <li><a href="/wiki/JWH-302" title="JWH-302">JWH-302</a></li> <li><a href="/wiki/JWH-307" title="JWH-307">JWH-307</a></li> <li><a href="/w/index.php?title=JWH-336&action=edit&redlink=1" class="new" title="JWH-336 (page does not exist)">JWH-336</a></li> <li><a href="/w/index.php?title=JWH-350&action=edit&redlink=1" class="new" title="JWH-350 (page does not exist)">JWH-350</a></li> <li><a href="/wiki/JWH-359" title="JWH-359">JWH-359</a></li> <li><a href="/w/index.php?title=JWH-387&action=edit&redlink=1" class="new" title="JWH-387 (page does not exist)">JWH-387</a></li> <li><a href="/wiki/JWH-398" title="JWH-398">JWH-398</a></li> <li><a href="/wiki/JWH-424" title="JWH-424">JWH-424</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_miscellaneous_designer_cannabinoids" title="List of miscellaneous designer cannabinoids">Misc. designer cannabinoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-HTMPIPO" title="4-HTMPIPO">4-HTMPIPO</a></li> <li><a href="/wiki/5F-AB-FUPPYCA" title="5F-AB-FUPPYCA">5F-AB-FUPPYCA</a></li> <li><a href="/wiki/5F-AB-PINACA" title="5F-AB-PINACA">5F-AB-PINACA</a></li> <li><a href="/wiki/5F-ADB" title="5F-ADB">5F-ADB</a></li> <li><a href="/wiki/5F-ADB-PINACA" title="5F-ADB-PINACA">5F-ADB-PINACA</a></li> <li><a href="/wiki/5F-ADBICA" title="5F-ADBICA">5F-ADBICA</a></li> <li><a href="/wiki/5F-AMB" title="5F-AMB">5F-AMB</a></li> <li><a href="/wiki/5F-APINACA" title="5F-APINACA">5F-APINACA</a></li> <li><a href="/wiki/5F-CUMYL-PINACA" title="5F-CUMYL-PINACA">5F-CUMYL-PINACA</a></li> <li><a href="/wiki/5F-NNE1" title="5F-NNE1">5F-NNE1</a></li> <li><a href="/wiki/5F-PB-22" title="5F-PB-22">5F-PB-22</a></li> <li><a href="/wiki/5F-SDB-006" title="5F-SDB-006">5F-SDB-006</a></li> <li><a href="/wiki/A-796,260" title="A-796,260">A-796,260</a></li> <li><a href="/wiki/A-836,339" title="A-836,339">A-836,339</a></li> <li><a href="/wiki/AB-001" title="AB-001">AB-001</a></li> <li><a href="/wiki/AB-005" title="AB-005">AB-005</a></li> <li><a href="/wiki/AB-CHFUPYCA" title="AB-CHFUPYCA">AB-CHFUPYCA</a></li> <li><a href="/wiki/AB-CHMINACA" title="AB-CHMINACA">AB-CHMINACA</a></li> <li><a href="/wiki/AB-FUBINACA" title="AB-FUBINACA">AB-FUBINACA</a></li> <li><a href="/wiki/AB-PINACA" title="AB-PINACA">AB-PINACA</a></li> <li><a href="/wiki/ADAMANTYL-THPINACA" class="mw-redirect" title="ADAMANTYL-THPINACA">ADAMANTYL-THPINACA</a></li> <li><a href="/wiki/ADB-CHMINACA" title="ADB-CHMINACA">ADB-CHMINACA</a></li> <li><a href="/wiki/ADB-FUBINACA" title="ADB-FUBINACA">ADB-FUBINACA</a></li> <li><a href="/wiki/ADB-PINACA" title="ADB-PINACA">ADB-PINACA</a></li> <li><a href="/wiki/ADBICA" title="ADBICA">ADBICA</a></li> <li><a href="/wiki/ADSB-FUB-187" title="ADSB-FUB-187">ADSB-FUB-187</a></li> <li><a href="/wiki/AMB-FUBINACA" title="AMB-FUBINACA">AMB-FUBINACA</a></li> <li><a href="/wiki/APICA_(synthetic_cannabinoid_drug)" title="APICA (synthetic cannabinoid drug)">APICA</a></li> <li><a href="/wiki/APINACA" title="APINACA">APINACA</a></li> <li><a href="/wiki/APP-FUBINACA" title="APP-FUBINACA">APP-FUBINACA</a></li> <li><a href="/wiki/CB-13" title="CB-13">CB-13</a></li> <li><a href="/wiki/CUMYL-PICA" title="CUMYL-PICA">CUMYL-PICA</a></li> <li><a href="/wiki/CUMYL-PINACA" title="CUMYL-PINACA">CUMYL-PINACA</a></li> <li><a href="/wiki/CUMYL-THPINACA" title="CUMYL-THPINACA">CUMYL-THPINACA</a></li> <li><a href="/wiki/Dimethylheptylpyran" title="Dimethylheptylpyran">DMHP</a></li> <li><a href="/wiki/EAM-2201" title="EAM-2201">EAM-2201</a></li> <li><a href="/wiki/FAB-144" title="FAB-144">FAB-144</a></li> <li><a href="/wiki/FDU-PB-22" title="FDU-PB-22">FDU-PB-22</a></li> <li><a href="/wiki/FUB-144" title="FUB-144">FUB-144</a></li> <li><a href="/wiki/FUB-APINACA" title="FUB-APINACA">FUB-APINACA</a></li> <li><a href="/wiki/FUB-JWH-018" title="FUB-JWH-018">FUB-JWH-018</a></li> <li><a href="/wiki/FUB-PB-22" title="FUB-PB-22">FUB-PB-22</a></li> <li><a href="/wiki/FUBIMINA" title="FUBIMINA">FUBIMINA</a></li> <li><a href="/wiki/JTE_7-31" title="JTE 7-31">JTE 7-31</a></li> <li><a href="/wiki/JTE-907" title="JTE-907">JTE-907</a></li> <li><a href="/wiki/Levonantradol" title="Levonantradol">Levonantradol</a></li> <li><a href="/wiki/MDMB-CHMICA" title="MDMB-CHMICA">MDMB-CHMICA</a></li> <li><a href="/wiki/MDMB-CHMINACA" title="MDMB-CHMINACA">MDMB-CHMINACA</a></li> <li><a href="/wiki/MDMB-FUBINACA" title="MDMB-FUBINACA">MDMB-FUBINACA</a></li> <li><a href="/wiki/MEPIRAPIM" class="mw-redirect" title="MEPIRAPIM">MEPIRAPIM</a></li> <li><a href="/wiki/MAM-2201" title="MAM-2201">MAM-2201</a></li> <li><a href="/wiki/MDA-19" title="MDA-19">MDA-19</a></li> <li><a href="/wiki/MN-18" title="MN-18">MN-18</a></li> <li><a href="/wiki/MN-25" title="MN-25">MN-25</a></li> <li><a href="/wiki/NESS-0327" title="NESS-0327">NESS-0327</a></li> <li><a href="/wiki/NESS-040C5" title="NESS-040C5">NESS-040C5</a></li> <li><a href="/wiki/Nabilone" title="Nabilone">Nabilone</a></li> <li><a href="/wiki/Nabitan" title="Nabitan">Nabitan</a></li> <li><a href="/wiki/NM-2201" title="NM-2201">NM-2201</a></li> <li><a href="/wiki/NNE1" title="NNE1">NNE1</a></li> <li><a href="/wiki/Org_28611" title="Org 28611">Org 28611</a></li> <li><a href="/wiki/Parahexyl" title="Parahexyl">Parahexyl</a></li> <li><a href="/wiki/PTI-1" title="PTI-1">PTI-1</a></li> <li><a href="/wiki/PTI-2" title="PTI-2">PTI-2</a></li> <li><a href="/wiki/PX-1" title="PX-1">PX-1</a></li> <li><a href="/wiki/PX-2" title="PX-2">PX-2</a></li> <li><a href="/wiki/PX-3" title="PX-3">PX-3</a></li> <li><a href="/wiki/QUCHIC" title="QUCHIC">QUCHIC</a></li> <li><a href="/wiki/QUPIC" class="mw-redirect" title="QUPIC">QUPIC</a></li> <li><a href="/wiki/RCS-4" title="RCS-4">RCS-4</a></li> <li><a href="/wiki/RCS-8" title="RCS-8">RCS-8</a></li> <li><a href="/wiki/SDB-005" title="SDB-005">SDB-005</a></li> <li><a href="/wiki/SDB-006" title="SDB-006">SDB-006</a></li> <li><a href="/wiki/STS-135_(drug)" title="STS-135 (drug)">STS-135</a></li> <li><a href="/wiki/THC-O-acetate" title="THC-O-acetate">THC-O-acetate</a></li> <li><a href="/wiki/THC-O-phosphate" title="THC-O-phosphate">THC-O-phosphate</a></li> <li><a href="/wiki/THJ-018" title="THJ-018">THJ-018</a></li> <li><a href="/wiki/THJ-2201" title="THJ-2201">THJ-2201</a></li> <li><a href="/wiki/UR-144" title="UR-144">UR-144</a></li> <li><a href="/wiki/WIN_55,212-2" title="WIN 55,212-2">WIN 55,212-2</a></li> <li><a href="/wiki/XLR-11" title="XLR-11">XLR-11</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dopamine_receptor_D2" title="Dopamine receptor D2">D<sub>2</sub></a> <a href="/wiki/Dopamine_agonist" title="Dopamine agonist">agonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apomorphine" title="Apomorphine">Apomorphine</a></li> <li><a href="/wiki/Aporphine" title="Aporphine">Aporphine</a></li> <li><a href="/wiki/Bromocriptine" title="Bromocriptine">Bromocriptine</a></li> <li><a href="/wiki/Cabergoline" title="Cabergoline">Cabergoline</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/LSD" title="LSD">LSD</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Nuciferine" title="Nuciferine">Nuciferine</a></li> <li><a href="/wiki/Pergolide" title="Pergolide">Pergolide</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Piribedil" title="Piribedil">Piribedil</a></li> <li><a href="/wiki/Pramipexole" title="Pramipexole">Pramipexole</a></li> <li><a href="/wiki/Ropinirole" title="Ropinirole">Ropinirole</a></li> <li><a href="/wiki/Rotigotine" title="Rotigotine">Rotigotine</a></li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a><br /><small>Also indirect D<sub>2</sub> agonists, such as <a href="/wiki/Dopamine_reuptake_inhibitor" title="Dopamine reuptake inhibitor">dopamine reuptake inhibitors</a> (<a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/wiki/Methylphenidate" title="Methylphenidate">methylphenidate</a>), <a href="/wiki/Releasing_agent" class="mw-redirect" title="Releasing agent">releasing agents</a> (<a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>, <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>), and <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursors</a> (<a href="/wiki/L-DOPA" title="L-DOPA">levodopa</a>).</small></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GABAA_receptor" title="GABAA receptor">GABA<sub>A</sub></a><br />enhancers</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CI-966" title="CI-966">CI-966</a></li> <li><a href="/wiki/Eszopiclone" title="Eszopiclone">Eszopiclone</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/Muscimol" title="Muscimol">Muscimol</a> (<i><a href="/wiki/Amanita_muscaria" title="Amanita muscaria">Amanita muscaria</a></i>)</li> <li><a href="/wiki/Zaleplon" title="Zaleplon">Zaleplon</a></li> <li><a href="/wiki/Zolpidem" title="Zolpidem">Zolpidem</a></li> <li><a href="/wiki/Zopiclone" title="Zopiclone">Zopiclone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inhalant" title="Inhalant">Inhalants</a><br /><small>(Mixed <a href="/wiki/Mechanism_of_action" title="Mechanism of action">MOA</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aliphatic_hydrocarbons" class="mw-redirect" title="Aliphatic hydrocarbons">Aliphatic hydrocarbons</a> <ul><li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Gasoline" title="Gasoline">Gasoline</a></li> <li><a href="/wiki/Kerosene" title="Kerosene">Kerosene</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li></ul></li> <li><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic hydrocarbons</a> <ul><li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ethers</a> <ul><li><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li></ul></li> <li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkanes</a> <ul><li><a href="/wiki/Chlorofluorocarbon" title="Chlorofluorocarbon">Chlorofluorocarbons</a></li> <li><a href="/wiki/Chloroform" title="Chloroform">Chloroform</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%CE%9A-opioid_receptor" title="Κ-opioid receptor">κOR</a> <a href="/wiki/Opioid" title="Opioid">agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Salvinorin_B_ethoxymethyl_ether" class="mw-redirect" title="Salvinorin B ethoxymethyl ether">2-EMSB</a></li> <li><a href="/wiki/Alazocine" title="Alazocine">Alazocine</a></li> <li><a href="/wiki/Bremazocine" title="Bremazocine">Bremazocine</a></li> <li><a href="/wiki/Butorphan" class="mw-redirect" title="Butorphan">Butorphan</a></li> <li><a href="/wiki/Butorphanol" title="Butorphanol">Butorphanol</a></li> <li><a href="/wiki/Cyclazocine" title="Cyclazocine">Cyclazocine</a></li> <li><a href="/wiki/Cyclorphan" title="Cyclorphan">Cyclorphan</a></li> <li><a href="/wiki/Cyprenorphine" title="Cyprenorphine">Cyprenorphine</a></li> <li><a href="/wiki/Diprenorphine" title="Diprenorphine">Diprenorphine</a></li> <li><a href="/wiki/Enadoline" title="Enadoline">Enadoline</a></li> <li><a href="/wiki/Herkinorin" title="Herkinorin">Herkinorin</a></li> <li><a href="/wiki/Heroin" title="Heroin">Heroin</a></li> <li><a href="/wiki/HZ-2" title="HZ-2">HZ-2</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Ketazocine" title="Ketazocine">Ketazocine</a></li> <li><a href="/wiki/Levallorphan" title="Levallorphan">Levallorphan</a></li> <li><a href="/wiki/Levomethorphan" title="Levomethorphan">Levomethorphan</a></li> <li><a href="/wiki/Levorphanol" title="Levorphanol">Levorphanol</a></li> <li><a href="/wiki/LPK-26" title="LPK-26">LPK-26</a></li> <li><a href="/wiki/Metazocine" title="Metazocine">Metazocine</a></li> <li><a href="/wiki/Morphine" title="Morphine">Morphine</a></li> <li><a href="/wiki/Nalbuphine" title="Nalbuphine">Nalbuphine</a></li> <li><a href="/wiki/Nalmefene" title="Nalmefene">Nalmefene</a></li> <li><a href="/wiki/Nalorphine" title="Nalorphine">Nalorphine</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Oxilorphan" title="Oxilorphan">Oxilorphan</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Phenazocine" title="Phenazocine">Phenazocine</a></li> <li><a href="/wiki/Proxorphan" title="Proxorphan">Proxorphan</a></li> <li><a href="/wiki/Racemethorphan" class="mw-redirect" title="Racemethorphan">Racemethorphan</a></li> <li><a href="/wiki/Racemorphan" title="Racemorphan">Racemorphan</a></li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a></li> <li><a href="/wiki/Spiradoline" title="Spiradoline">Spiradoline</a></li> <li><a href="/wiki/Tifluadom" title="Tifluadom">Tifluadom</a></li> <li><a href="/wiki/U-50488" title="U-50488">U-50488</a></li> <li><a href="/wiki/U-69,593" title="U-69,593">U-69,593</a></li> <li><a href="/wiki/Xorphanol" title="Xorphanol">Xorphanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oneirogen" title="Oneirogen">Oneirogens</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Calea_ternifolia" title="Calea ternifolia">Calea zacatechichi</a></li> <li><a href="/wiki/Silene_undulata" title="Silene undulata">Silene capensis</a></li> <li><a href="/wiki/Galantamine" title="Galantamine">Galantamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/wiki/Isoaminile" title="Isoaminile">Isoaminile</a></li> <li><a href="/wiki/Noscapine" title="Noscapine">Noscapine</a></li> <li><a href="/wiki/Prenoxdiazine" title="Prenoxdiazine">Prenoxdiazine</a></li> <li><a href="/wiki/Pukateine" title="Pukateine">Pukateine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Serotonin_receptor_modulators871" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Serotonin_receptor_modulators" title="Template:Serotonin receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Serotonin_receptor_modulators" title="Template talk:Serotonin receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Serotonin_receptor_modulators" title="Special:EditPage/Template:Serotonin receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Serotonin_receptor_modulators871" style="font-size:114%;margin:0 4em"><a href="/wiki/5-HT_receptor" title="5-HT receptor">Serotonin receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1_receptor" title="5-HT1 receptor">5-HT<sub>1</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1A_receptor" title="5-HT1A receptor">5-HT<sub>1A</sub></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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/8-OH-DPAT" title="8-OH-DPAT">8-OH-DPAT</a></li> <li><a href="/wiki/Adatanserin" title="Adatanserin">Adatanserin</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/Antidepressant" title="Antidepressant">Antidepressants</a> (e.g., <a href="/wiki/Etoperidone" title="Etoperidone">etoperidone</a>, <a href="/wiki/Hydroxynefazodone" title="Hydroxynefazodone">hydroxynefazodone</a>, <a href="/wiki/Nefazodone" title="Nefazodone">nefazodone</a>, <a href="/wiki/Trazodone" title="Trazodone">trazodone</a>, <a href="/wiki/Triazoledione" title="Triazoledione">triazoledione</a>, <a href="/wiki/Vilazodone" title="Vilazodone">vilazodone</a>, <a href="/wiki/Vortioxetine" title="Vortioxetine">vortioxetine</a>)</li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Cariprazine" title="Cariprazine">cariprazine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Lurasidone" title="Lurasidone">lurasidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>)</li> <li><a href="/wiki/Azapirone" title="Azapirone">Azapirones</a> (e.g., <a href="/wiki/Buspirone" title="Buspirone">buspirone</a>, <a href="/wiki/Eptapirone" title="Eptapirone">eptapirone</a>, <a href="/wiki/Gepirone" title="Gepirone">gepirone</a>, <a href="/wiki/Perospirone" title="Perospirone">perospirone</a>, <a href="/wiki/Tandospirone" title="Tandospirone">tandospirone</a>)</li> <li><a href="/wiki/Bay_R_1531" title="Bay R 1531">Bay R 1531</a></li> <li><a href="/wiki/Befiradol" title="Befiradol">Befiradol</a></li> <li><a href="/wiki/BMY-14802" title="BMY-14802">BMY-14802</a></li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Ebalzotan" title="Ebalzotan">Ebalzotan</a></li> <li><a href="/wiki/Eltoprazine" title="Eltoprazine">Eltoprazine</a></li> <li><a href="/wiki/Enciprazine" title="Enciprazine">Enciprazine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/F-11,461" title="F-11,461">F-11,461</a></li> <li><a href="/w/index.php?title=F-12826&action=edit&redlink=1" class="new" title="F-12826 (page does not exist)">F-12826</a></li> <li><a href="/w/index.php?title=F-13714&action=edit&redlink=1" class="new" title="F-13714 (page does not exist)">F-13714</a></li> <li><a href="/w/index.php?title=F-14679&action=edit&redlink=1" class="new" title="F-14679 (page does not exist)">F-14679</a></li> <li><a href="/wiki/F-15063" title="F-15063">F-15063</a></li> <li><a href="/wiki/F-15,599" title="F-15,599">F-15,599</a></li> <li><a href="/wiki/Flesinoxan" title="Flesinoxan">Flesinoxan</a></li> <li><a href="/wiki/Flibanserin" title="Flibanserin">Flibanserin</a></li> <li><a href="/wiki/Flumexadol" title="Flumexadol">Flumexadol</a></li> <li><a href="/wiki/Hypidone" title="Hypidone">Hypidone</a></li> <li><a href="/wiki/Lesopitron" title="Lesopitron">Lesopitron</a></li> <li><a href="/wiki/LY-293284" title="LY-293284">LY-293284</a></li> <li><a href="/w/index.php?title=LY-301317&action=edit&redlink=1" class="new" title="LY-301317 (page does not exist)">LY-301317</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Osemozotan" title="Osemozotan">MKC-242</a></li> <li><a href="/wiki/Naluzotan" title="Naluzotan">Naluzotan</a></li> <li><a href="/wiki/NBUMP" title="NBUMP">NBUMP</a></li> <li><a href="/wiki/Osemozotan" title="Osemozotan">Osemozotan</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/Pardoprunox" title="Pardoprunox">Pardoprunox</a></li> <li><a href="/wiki/Piclozotan" title="Piclozotan">Piclozotan</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Repinotan" title="Repinotan">Repinotan</a></li> <li><a href="/wiki/Roxindole" title="Roxindole">Roxindole</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/S-14,506" title="S-14,506">S-14,506</a></li> <li><a href="/wiki/S-14671" title="S-14671">S-14671</a></li> <li><a href="/wiki/S-15535" title="S-15535">S-15535</a></li> <li><a href="/wiki/Sarizotan" title="Sarizotan">Sarizotan</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/w/index.php?title=SSR-181507&action=edit&redlink=1" class="new" title="SSR-181507 (page does not exist)">SSR-181507</a></li> <li><a href="/wiki/Sunepitron" title="Sunepitron">Sunepitron</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Indorenate" title="Indorenate">indorenate</a>, <a href="/wiki/N-Methylserotonin" title="N-Methylserotonin">N-Me-5-HT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>)</li> <li><a href="/wiki/TGBA01AD" title="TGBA01AD">TGBA01AD</a></li> <li><a href="/wiki/U-92,016-A" title="U-92,016-A">U-92,016-A</a></li> <li><a href="/wiki/Urapidil" title="Urapidil">Urapidil</a></li> <li><a href="/wiki/Vilazodone" title="Vilazodone">Vilazodone</a></li> <li><a href="/wiki/Xaliproden" title="Xaliproden">Xaliproden</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>)</li> <li><a href="/w/index.php?title=AV965&action=edit&redlink=1" class="new" title="AV965 (page does not exist)">AV965</a></li> <li><a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> (e.g., <a href="/wiki/Alprenolol" title="Alprenolol">alprenolol</a>, <a href="/wiki/Carteolol" title="Carteolol">carteolol</a>, <a href="/wiki/Cyanopindolol" title="Cyanopindolol">cyanopindolol</a>, <a href="/wiki/Iodocyanopindolol" title="Iodocyanopindolol">iodocyanopindolol</a>, <a href="/wiki/Isamoltane" title="Isamoltane">isamoltane</a>, <a href="/wiki/Oxprenolol" title="Oxprenolol">oxprenolol</a>, <a href="/wiki/Penbutolol" title="Penbutolol">penbutolol</a>, <a href="/wiki/Pindobind" title="Pindobind">pindobind</a>, <a href="/wiki/Pindolol" title="Pindolol">pindolol</a>, <a href="/wiki/Propranolol" title="Propranolol">propranolol</a>, <a href="/wiki/Tertatolol" title="Tertatolol">tertatolol</a>)</li> <li><a href="/wiki/BMY-7,378" class="mw-redirect" title="BMY-7,378">BMY-7,378</a></li> <li><a href="/wiki/CSP-2503" title="CSP-2503">CSP-2503</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>)</li> <li><a href="/w/index.php?title=FCE-24379&action=edit&redlink=1" class="new" title="FCE-24379 (page does not exist)">FCE-24379</a></li> <li><a href="/wiki/Flopropione" title="Flopropione">Flopropione</a></li> <li><a href="/w/index.php?title=GR-46611&action=edit&redlink=1" class="new" title="GR-46611 (page does not exist)">GR-46611</a></li> <li><a href="/wiki/Isamoltane" title="Isamoltane">Isamoltane</a></li> <li><a href="/wiki/Lecozotan" title="Lecozotan">Lecozotan</a></li> <li><a href="/wiki/Mefway_(18F)" title="Mefway (18F)">Mefway</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/MIN-117" title="MIN-117">MIN-117 (WF-516)</a></li> <li><a href="/wiki/MPPF" title="MPPF">MPPF</a></li> <li><a href="/wiki/NAN-190" title="NAN-190">NAN-190</a></li> <li><a href="/wiki/Robalzotan" title="Robalzotan">Robalzotan</a></li> <li><a href="/wiki/S-15535" title="S-15535">S-15535</a></li> <li><a href="/wiki/SB-649,915" title="SB-649,915">SB-649,915</a></li> <li><a href="/w/index.php?title=SDZ_216-525&action=edit&redlink=1" class="new" title="SDZ 216-525 (page does not exist)">SDZ 216-525</a></li> <li><a href="/wiki/Spiperone" title="Spiperone">Spiperone</a></li> <li><a href="/wiki/Spiramide" title="Spiramide">Spiramide</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/wiki/UH-301" title="UH-301">UH-301</a></li> <li><a href="/wiki/WAY-100135" title="WAY-100135">WAY-100135</a></li> <li><a href="/wiki/WAY-100635" title="WAY-100635">WAY-100635</a></li> <li><a href="/wiki/Xylamidine" title="Xylamidine">Xylamidine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">ergometrine (ergonovine)</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT<sub>1B</sub></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><i>Agonists:</i> <a href="/wiki/Anpirtoline" title="Anpirtoline">Anpirtoline</a></li> <li><a href="/wiki/CGS-12066A" title="CGS-12066A">CGS-12066A</a></li> <li><a href="/wiki/CP-93129" title="CP-93129">CP-93129</a></li> <li><a href="/wiki/CP-94253" title="CP-94253">CP-94253</a></li> <li><a href="/wiki/CP-122,288" title="CP-122,288">CP-122,288</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/wiki/Eltoprazine" title="Eltoprazine">Eltoprazine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/Donitriptan" title="Donitriptan">donitriptan</a>, <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>, <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>, <a href="/wiki/Zolmitriptan" title="Zolmitriptan">zolmitriptan</a>)</li> <li><a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>)</li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/AR-A000002" title="AR-A000002">AR-A000002</a></li> <li><a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> (e.g., <a href="/wiki/Alprenolol" title="Alprenolol">alprenolol</a>, <a href="/wiki/Carteolol" title="Carteolol">carteolol</a>, <a href="/wiki/Isamoltane" title="Isamoltane">isamoltane</a>, <a href="/wiki/Oxprenolol" title="Oxprenolol">oxprenolol</a>, <a href="/wiki/Penbutolol" title="Penbutolol">penbutolol</a>, <a href="/wiki/Propranolol" title="Propranolol">propranolol</a>, <a href="/wiki/Tertatolol" title="Tertatolol">tertatolol</a>)</li> <li><a href="/wiki/Elzasonan" title="Elzasonan">Elzasonan</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>)</li> <li><a href="/wiki/GR-127935" title="GR-127935">GR-127935</a></li> <li><a href="/wiki/Isamoltane" title="Isamoltane">Isamoltane</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/SB-216641" title="SB-216641">SB-216641</a></li> <li><a href="/wiki/SB-224289" title="SB-224289">SB-224289</a></li> <li><a href="/wiki/SB-236057" title="SB-236057">SB-236057</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1D_receptor" title="5-HT1D receptor">5-HT<sub>1D</sub></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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/CP-122,288" title="CP-122,288">CP-122,288</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/w/index.php?title=CP-286601&action=edit&redlink=1" class="new" title="CP-286601 (page does not exist)">CP-286601</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/w/index.php?title=GR-46611&action=edit&redlink=1" class="new" title="GR-46611 (page does not exist)">GR-46611</a></li> <li><a href="/wiki/L-694247" title="L-694247">L-694247</a></li> <li><a href="/w/index.php?title=L-772405&action=edit&redlink=1" class="new" title="L-772405 (page does not exist)">L-772405</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/w/index.php?title=PNU-109291&action=edit&redlink=1" class="new" title="PNU-109291 (page does not exist)">PNU-109291</a></li> <li><a href="/wiki/PNU-142633" title="PNU-142633">PNU-142633</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/TGBA01AD" title="TGBA01AD">TGBA01AD</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Almotriptan" title="Almotriptan">almotriptan</a>, <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/Donitriptan" title="Donitriptan">donitriptan</a>, <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>, <a href="/wiki/Frovatriptan" title="Frovatriptan">frovatriptan</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>, <a href="/wiki/Rizatriptan" title="Rizatriptan">rizatriptan</a>, <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>, <a href="/wiki/Zolmitriptan" title="Zolmitriptan">zolmitriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Ethyl-DMT" title="5-Ethyl-DMT">5-Et-DMT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/5-(Nonyloxy)tryptamine" title="5-(Nonyloxy)tryptamine">5-(nonyloxy)tryptamine</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Alniditan" title="Alniditan">Alniditan</a></li> <li><a href="/wiki/BRL-15,572" title="BRL-15,572">BRL-15,572</a></li> <li><a href="/wiki/Elzasonan" title="Elzasonan">Elzasonan</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>)</li> <li><a href="/wiki/GR-127935" title="GR-127935">GR-127935</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/LY-310762" title="LY-310762">LY-310762</a></li> <li><a href="/wiki/LY-367642" title="LY-367642">LY-367642</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/LY-456219" title="LY-456219">LY-456219</a></li> <li><a href="/wiki/LY-456220" title="LY-456220">LY-456220</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li> <li><a href="/wiki/Ziprasidone" title="Ziprasidone">Ziprasidone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Lysergol" title="Lysergol">lysergol</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1E_receptor" title="5-HT1E receptor">5-HT<sub>1E</sub></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><i>Agonists:</i> <a href="/wiki/BRL-54443" title="BRL-54443">BRL-54443</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Lysergol" title="Lysergol">lysergol</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1F_receptor" title="5-HT1F receptor">5-HT<sub>1F</sub></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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/BRL-54443" title="BRL-54443">BRL-54443</a></li> <li><a href="/wiki/CP-122,288" title="CP-122,288">CP-122,288</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Lysergol" title="Lysergol">lysergol</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a> <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Lasmiditan" title="Lasmiditan">Lasmiditan</a></li> <li><a href="/wiki/LY-334370" title="LY-334370">LY-334370</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>, <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT2_receptor" title="5-HT2 receptor">5-HT<sub>2</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT<sub>2A</sub></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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> 25H/NB series (e.g., <a href="/wiki/25I-NBF" title="25I-NBF">25I-NBF</a>, <a href="/wiki/25I-NBMD" title="25I-NBMD">25I-NBMD</a>, <a href="/wiki/25I-NBOH" title="25I-NBOH">25I-NBOH</a>, <a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a>, <a href="/wiki/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a>, <a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a>, <a href="/wiki/25TFM-NBOMe" title="25TFM-NBOMe">25TFM-NBOMe</a>, <a href="/wiki/2CBCB-NBOMe" title="2CBCB-NBOMe">2CBCB-NBOMe</a>, <a href="/wiki/25CN-NBOH" title="25CN-NBOH">25CN-NBOH</a>, <a href="/wiki/2CBFly-NBOMe" title="2CBFly-NBOMe">2CBFly-NBOMe</a>)</li> <li><a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2Cs</a> (e.g., <a href="/wiki/2C-B" title="2C-B">2C-B</a>, <a href="/wiki/2C-E" title="2C-E">2C-E</a>, <a href="/wiki/2C-I" title="2C-I">2C-I</a>, <a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a>, <a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a>, <a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a>)</li> <li><a href="/wiki/2C-B-FLY" title="2C-B-FLY">2C-B-FLY</a></li> <li><a href="/wiki/2CB-Ind" title="2CB-Ind">2CB-Ind</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamines</a> (<a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a>, <a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a>, <a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a>, <a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>)</li> <li><a href="/wiki/Substituted_alpha-alkyltryptamine" class="mw-redirect" title="Substituted alpha-alkyltryptamine">α-Alkyltryptamines</a> (e.g., <a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Cl-αMT</a>, <a href="/wiki/5-Fluoro-AMT" title="5-Fluoro-AMT">5-Fl-αMT</a>, <a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a>, <a href="/wiki/5-MeO-aMT" class="mw-redirect" title="5-MeO-aMT">5-MeO-αMT</a>, <a href="/wiki/Alpha-Methylserotonin" class="mw-redirect" title="Alpha-Methylserotonin">α-Me-5-HT</a>, <a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a>, <a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a>)</li> <li><a href="/wiki/AL-34662" title="AL-34662">AL-34662</a></li> <li><a href="/wiki/AL-37350A" title="AL-37350A">AL-37350A</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/DMBMPP" title="DMBMPP">DMBMPP</a></li> <li><a class="mw-selflink selflink">DOx</a> (e.g., <a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a>, <a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a>, <a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a>, <a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a>)</li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/1P-LSD" title="1P-LSD">1P-LSD</a>, <a href="/wiki/ALD-52" title="ALD-52">ALD-52</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Ergine" title="Ergine">ergine (LSA)</a>, <a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">LA-SS-Az</a>, <a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">LSB</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/LSD-Pip" title="LSD-Pip">LSD-Pip</a>, <a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">LSH</a>, <a href="/wiki/Lysergic_acid_3-pentyl_amide" title="Lysergic acid 3-pentyl amide">LSP</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Flumexadol" title="Flumexadol">Flumexadol</a></li> <li><a href="/wiki/IHCH-7113" title="IHCH-7113">IHCH-7113</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MDxx</a> (e.g., <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a>, <a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a>, <a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</a>, <a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a>)</li> <li><a href="/wiki/O-4310" title="O-4310">O-4310</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/PHA-57378" title="PHA-57378">PHA-57378</a></li> <li><a href="/wiki/PNU-22394" title="PNU-22394">PNU-22394</a></li> <li><a href="/wiki/PNU-181731" title="PNU-181731">PNU-181731</a></li> <li><a href="/wiki/RH-34" title="RH-34">RH-34</a></li> <li><a href="/wiki/SCHEMBL5334361" title="SCHEMBL5334361">SCHEMBL5334361</a></li> <li><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a> (e.g., <a href="/wiki/Lophophine" title="Lophophine">lophophine</a>, <a href="/wiki/Mescaline" title="Mescaline">mescaline</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a>, <a href="/wiki/Quipazine" title="Quipazine">quipazine</a>, <a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a>)</li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li> <li><a href="/wiki/TFMFly" title="TFMFly">TFMFly</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a>, <a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/5-I-R91150" title="5-I-R91150">5-I-R91150</a></li> <li><a href="/wiki/5-MeO-NBpBrT" title="5-MeO-NBpBrT">5-MeO-NBpBrT</a></li> <li><a href="/wiki/AC-90179" title="AC-90179">AC-90179</a></li> <li><a href="/wiki/Adatanserin" title="Adatanserin">Adatanserin</a></li> <li><a href="/wiki/Altanserin" title="Altanserin">Altanserin</a></li> <li><a href="/wiki/Antihistamine" title="Antihistamine">Antihistamines</a> (e.g., <a href="/wiki/Cyproheptadine" title="Cyproheptadine">cyproheptadine</a>, <a href="/wiki/Hydroxyzine" title="Hydroxyzine">hydroxyzine</a>, <a href="/wiki/Ketotifen" title="Ketotifen">ketotifen</a>, <a href="/wiki/Perlapine" title="Perlapine">perlapine</a>)</li> <li><a href="/wiki/9-Aminomethyl-9,10-dihydroanthracene" title="9-Aminomethyl-9,10-dihydroanthracene">AMDA</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Amperozide" title="Amperozide">amperozide</a>, <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Blonanserin" title="Blonanserin">blonanserin</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Carpipramine" title="Carpipramine">carpipramine</a>, <a href="/wiki/Clocapramine" title="Clocapramine">clocapramine</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Gevotroline" title="Gevotroline">gevotroline</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Lurasidone" title="Lurasidone">lurasidone</a>, <a href="/wiki/Melperone" title="Melperone">melperone</a>, <a href="/wiki/Mosapramine" title="Mosapramine">mosapramine</a>, <a href="/wiki/Ocaperidone" title="Ocaperidone">ocaperidone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Paliperidone" title="Paliperidone">paliperidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>, <a href="/wiki/Zicronapine" title="Zicronapine">zicronapine</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Chlorprothixene" title="Chlorprothixene">Chlorprothixene</a></li> <li><a href="/wiki/Cinanserin" title="Cinanserin">Cinanserin</a></li> <li><a href="/wiki/CSP-2503" title="CSP-2503">CSP-2503</a></li> <li><a href="/wiki/Deramciclane" title="Deramciclane">Deramciclane</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Eplivanserin" title="Eplivanserin">Eplivanserin</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Sergolexole" title="Sergolexole">sergolexole</a>)</li> <li><a href="/wiki/Fananserin" title="Fananserin">Fananserin</a></li> <li><a href="/wiki/Flibanserin" title="Flibanserin">Flibanserin</a></li> <li><a href="/wiki/Glemanserin" title="Glemanserin">Glemanserin</a></li> <li><a href="/w/index.php?title=Irindalone&action=edit&redlink=1" class="new" title="Irindalone (page does not exist)">Irindalone</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/KML-010" title="KML-010">KML-010</a></li> <li><a href="/w/index.php?title=Landipirdine&action=edit&redlink=1" class="new" title="Landipirdine (page does not exist)">Landipirdine</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/MIN-117" title="MIN-117">MIN-117 (WF-516)</a></li> <li><a href="/wiki/Naftidrofuryl" title="Naftidrofuryl">Naftidrofuryl</a></li> <li><a href="/wiki/Nantenine" title="Nantenine">Nantenine</a></li> <li><a href="/wiki/Nelotanserin" title="Nelotanserin">Nelotanserin</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/wiki/Pelanserin" title="Pelanserin">Pelanserin</a></li> <li><a href="/wiki/Phenoxybenzamine" title="Phenoxybenzamine">Phenoxybenzamine</a></li> <li><a href="/wiki/Pimavanserin" title="Pimavanserin">Pimavanserin</a></li> <li><a href="/wiki/Pirenperone" title="Pirenperone">Pirenperone</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Pruvanserin" title="Pruvanserin">Pruvanserin</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/Roluperidone" title="Roluperidone">Roluperidone</a></li> <li><a href="/wiki/S-14671" title="S-14671">S-14671</a></li> <li><a href="/wiki/Sarpogrelate" title="Sarpogrelate">Sarpogrelate</a></li> <li><a href="/wiki/Serotonin_antagonist_and_reuptake_inhibitor" title="Serotonin antagonist and reuptake inhibitor">Serotonin antagonists and reuptake inhibitors</a> (e.g., <a href="/wiki/Etoperidone" title="Etoperidone">etoperidone</a>, <a href="/wiki/Hydroxynefazodone" title="Hydroxynefazodone">hydroxynefazodone</a>, <a href="/wiki/Lubazodone" title="Lubazodone">lubazodone</a>, <a href="/wiki/Mepiprazole" title="Mepiprazole">mepiprazole</a>, <a href="/wiki/Nefazodone" title="Nefazodone">nefazodone</a>, <a href="/wiki/Triazoledione" title="Triazoledione">triazoledione</a>, <a href="/wiki/Trazodone" title="Trazodone">trazodone</a>)</li> <li><a href="/w/index.php?title=SR-46349B&action=edit&redlink=1" class="new" title="SR-46349B (page does not exist)">SR-46349B</a></li> <li><a href="/wiki/TGBA01AD" title="TGBA01AD">TGBA01AD</a></li> <li><a href="/wiki/Teniloxazine" title="Teniloxazine">Teniloxazine</a></li> <li><a href="/w/index.php?title=Temanogrel&action=edit&redlink=1" class="new" title="Temanogrel (page does not exist)">Temanogrel</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Aptazapine" title="Aptazapine">aptazapine</a>, <a href="/wiki/Esmirtazapine" title="Esmirtazapine">esmirtazapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Perphenazine" title="Perphenazine">perphenazine</a>, <a href="/wiki/Pimozide" title="Pimozide">pimozide</a>, <a href="/wiki/Pipamperone" title="Pipamperone">pipamperone</a>, <a href="/wiki/Prochlorperazine" title="Prochlorperazine">prochlorperazine</a>, <a href="/wiki/Setoperone" title="Setoperone">setoperone</a>, <a href="/wiki/Spiperone" title="Spiperone">spiperone</a>, <a href="/wiki/Spiramide" title="Spiramide">spiramide</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>, <a href="/wiki/Tiotixene" title="Tiotixene">thiothixene</a>, <a href="/wiki/Trifluoperazine" title="Trifluoperazine">trifluoperazine</a>)</li> <li><a href="/wiki/Volinanserin" title="Volinanserin">Volinanserin</a></li> <li><a href="/wiki/Xylamidine" title="Xylamidine">Xylamidine</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Nicergoline" title="Nicergoline">nicergoline</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT2B_receptor" title="5-HT2B receptor">5-HT<sub>2B</sub></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><i>Agonists:</i> <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-Methylaminorex</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</a> (e.g., <a href="/wiki/Chlorphentermine" title="Chlorphentermine">chlorphentermine</a>, <a href="/wiki/Cloforex" title="Cloforex">cloforex</a>, <a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">dexfenfluramine</a>, <a href="/wiki/Fenfluramine" title="Fenfluramine">fenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">levofenfluramine</a>, <a href="/wiki/Norfenfluramine" title="Norfenfluramine">norfenfluramine</a>)</li> <li><a href="/wiki/BW-723C86" title="BW-723C86">BW-723C86</a></li> <li><a class="mw-selflink selflink">DOx</a> (e.g., <a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a>, <a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a>, <a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a>, <a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a>)</li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">dihydroergocryptine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MDxx</a> (e.g., <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a>, <a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a>, <a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</a>, <a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a>)</li> <li><a href="/wiki/Substituted_piperazine" title="Substituted piperazine">Piperazines</a> (e.g., <a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a>)</li> <li><a href="/wiki/PNU-22394" title="PNU-22394">PNU-22394</a></li> <li><a href="/wiki/Ro60-0175" title="Ro60-0175">Ro60-0175</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Alpha-Methylserotonin" class="mw-redirect" title="Alpha-Methylserotonin">α-Me-5-HT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a>, <a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Agomelatine" title="Agomelatine">Agomelatine</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Amisulpride" title="Amisulpride">amisulpride</a>, <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Cariprazine" title="Cariprazine">cariprazine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/w/index.php?title=N-desalkylquetiapine&action=edit&redlink=1" class="new" title="N-desalkylquetiapine (page does not exist)">N-desalkylquetiapine (norquetiapine)</a>, <a href="/wiki/Desmethylclozapine" title="Desmethylclozapine">N-desmethylclozapine (norclozapine)</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Pipamperone" title="Pipamperone">pipamperone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>)</li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/EGIS-7625" title="EGIS-7625">EGIS-7625</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-272,015" title="LY-272,015">LY-272015</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>)</li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Metadoxine" title="Metadoxine">Metadoxine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Pirenperone" title="Pirenperone">Pirenperone</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/PRX-08066" title="PRX-08066">PRX-08066</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/RS-127445" title="RS-127445">RS-127445</a></li> <li><a href="/wiki/Sarpogrelate" title="Sarpogrelate">Sarpogrelate</a></li> <li><a href="/wiki/SB-200646" title="SB-200646">SB-200646</a></li> <li><a href="/wiki/SB-204741" title="SB-204741">SB-204741</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/wiki/SB-215505" title="SB-215505">SB-215505</a></li> <li><a href="/wiki/SB-221284" title="SB-221284">SB-221284</a></li> <li><a href="/wiki/SB-228357" title="SB-228357">SB-228357</a></li> <li><a href="/wiki/SDZ_SER-082" title="SDZ SER-082">SDZ SER-082</a></li> <li><a href="/wiki/Tegaserod" title="Tegaserod">Tegaserod</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Trazodone" title="Trazodone">Trazodone</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>)</li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">ergometrine (ergonovine)</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT2C_receptor" title="5-HT2C receptor">5-HT<sub>2C</sub></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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2Cs</a> (e.g., <a href="/wiki/2C-B" title="2C-B">2C-B</a>, <a href="/wiki/2C-E" title="2C-E">2C-E</a>, <a href="/wiki/2C-I" title="2C-I">2C-I</a>, <a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a>, <a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a>, <a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a>)</li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamines</a> (<a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a>, <a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a>, <a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a>, <a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>)</li> <li><a href="/wiki/Substituted_alpha-alkyltryptamine" class="mw-redirect" title="Substituted alpha-alkyltryptamine">α-Alkyltryptamines</a> (e.g., <a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Cl-αMT</a>, <a href="/wiki/5-Fluoro-AMT" title="5-Fluoro-AMT">5-Fl-αMT</a>, <a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a>, <a href="/wiki/5-MeO-aMT" class="mw-redirect" title="5-MeO-aMT">5-MeO-αMT</a>, <a href="/wiki/Alpha-Methylserotonin" class="mw-redirect" title="Alpha-Methylserotonin">α-Me-5-HT</a>, <a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a>, <a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a>)</li> <li><a href="/wiki/A-372159" title="A-372159">A-372159</a></li> <li><a href="/wiki/AL-38022A" title="AL-38022A">AL-38022A</a></li> <li><a href="/wiki/Alstonine" title="Alstonine">Alstonine</a></li> <li><a href="/wiki/CP-809101" title="CP-809101">CP-809101</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a class="mw-selflink selflink">DOx</a> (e.g., <a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a>, <a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a>, <a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a>, <a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a>)</li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/ALD-52" title="ALD-52">ALD-52</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergine" title="Ergine">ergine (LSA)</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">LA-SS-Az</a>, <a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">LSB</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/LSD-Pip" title="LSD-Pip">LSD-Pip</a>, <a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">LSH</a>, <a href="/wiki/Lysergic_acid_3-pentyl_amide" title="Lysergic acid 3-pentyl amide">LSP</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Flumexadol" title="Flumexadol">Flumexadol</a></li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MDxx</a> (e.g., <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a>, <a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a>, <a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</a>, <a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a>)</li> <li><a href="/wiki/MK-212" title="MK-212">MK-212</a></li> <li><a href="/wiki/ORG-12962" title="ORG-12962">ORG-12962</a></li> <li><a href="/wiki/ORG-37684" title="ORG-37684">ORG-37684</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/PHA-57378" title="PHA-57378">PHA-57378</a></li> <li><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a> (e.g., <a href="/wiki/Lophophine" title="Lophophine">lophophine</a>, <a href="/wiki/Mescaline" title="Mescaline">mescaline</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a>, <a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a>, <a href="/wiki/Quipazine" title="Quipazine">quipazine</a>, <a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a>)</li> <li><a href="/wiki/PNU-22394" title="PNU-22394">PNU-22394</a></li> <li><a href="/wiki/PNU-181731" title="PNU-181731">PNU-181731</a></li> <li><a href="/wiki/Ro60-0175" title="Ro60-0175">Ro60-0175</a></li> <li><a href="/wiki/Ro60-0213" title="Ro60-0213">Ro60-0213</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a>, <a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li> <li><a href="/wiki/Vabicaserin" title="Vabicaserin">Vabicaserin</a></li> <li><a href="/wiki/WAY-629" title="WAY-629">WAY-629</a></li> <li><a href="/wiki/WAY-161503" title="WAY-161503">WAY-161503</a></li> <li><a href="/wiki/YM-348" title="YM-348">YM-348</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Adatanserin" title="Adatanserin">Adatanserin</a></li> <li><a href="/wiki/Agomelatine" title="Agomelatine">Agomelatine</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Melperone" title="Melperone">melperone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Paliperidone" title="Paliperidone">paliperidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Captodiame" title="Captodiame">Captodiame</a></li> <li><a href="/wiki/6-Chloro-5-ethoxy-N-(pyridin-2-yl)indoline-1-carboxamide" title="6-Chloro-5-ethoxy-N-(pyridin-2-yl)indoline-1-carboxamide">CEPC</a></li> <li><a href="/wiki/Cinanserin" title="Cinanserin">Cinanserin</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Deramciclane" title="Deramciclane">Deramciclane</a></li> <li><a href="/wiki/Desmetramadol" title="Desmetramadol">Desmetramadol</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Eltoprazine" title="Eltoprazine">Eltoprazine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Sergolexole" title="Sergolexole">sergolexole</a>)</li> <li><a href="/wiki/Etoperidone" title="Etoperidone">Etoperidone</a></li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/w/index.php?title=FR-260010&action=edit&redlink=1" class="new" title="FR-260010 (page does not exist)">FR-260010</a></li> <li><a href="/w/index.php?title=Irindalone&action=edit&redlink=1" class="new" title="Irindalone (page does not exist)">Irindalone</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/Ketotifen" title="Ketotifen">Ketotifen</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine (dimebolin)</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Pirenperone" title="Pirenperone">Pirenperone</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/RS-102221" title="RS-102221">RS-102221</a></li> <li><a href="/wiki/S-14671" title="S-14671">S-14671</a></li> <li><a href="/wiki/SB-200646" title="SB-200646">SB-200646</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/wiki/SB-221284" title="SB-221284">SB-221284</a></li> <li><a href="/wiki/SB-228357" title="SB-228357">SB-228357</a></li> <li><a href="/wiki/SB-242084" title="SB-242084">SB-242084</a></li> <li><a href="/wiki/SB-243213" title="SB-243213">SB-243213</a></li> <li><a href="/wiki/SDZ_SER-082" title="SDZ SER-082">SDZ SER-082</a></li> <li><a href="/wiki/Tedatioxetine" title="Tedatioxetine">Tedatioxetine</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Aptazapine" title="Aptazapine">aptazapine</a>, <a href="/wiki/Esmirtazapine" title="Esmirtazapine">esmirtazapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Trazodone" title="Trazodone">Trazodone</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Pimozide" title="Pimozide">pimozide</a>, <a href="/wiki/Pipamperone" title="Pipamperone">pipamperone</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Xylamidine" title="Xylamidine">Xylamidine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT3_receptor" title="5-HT3 receptor">5-HT<sub>3</sub></a><sub>–<a href="/wiki/5-HT7_receptor" title="5-HT7 receptor">7</a></sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT3_receptor" title="5-HT3 receptor">5-HT<sub>3</sub></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><i>Agonists:</i> <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> (e.g., <a href="/wiki/N-Butanol" class="mw-redirect" title="N-Butanol">butanol</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">ethanol (alcohol)</a>, <a href="/wiki/2,2,2-Trichloroethanol" title="2,2,2-Trichloroethanol">trichloroethanol</a>)</li> <li><a href="/wiki/Chlorophenylbiguanide" title="Chlorophenylbiguanide">m-CPBG</a></li> <li><a href="/wiki/Phenylbiguanide" title="Phenylbiguanide">Phenylbiguanide</a></li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a>, <a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a>, <a href="/wiki/Quipazine" title="Quipazine">quipazine</a>)</li> <li><a href="/wiki/RS-56812" title="RS-56812">RS-56812</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/SR-57227" title="SR-57227">SR-57227</a></li> <li><a href="/w/index.php?title=SR-57227A&action=edit&redlink=1" class="new" title="SR-57227A (page does not exist)">SR-57227A</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Me-5-HT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/Bufotenidine" title="Bufotenidine">bufotenidine (5-HTQ)</a>)</li> <li><a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">Volatiles/gases</a> (e.g., <a href="/wiki/Halothane" title="Halothane">halothane</a>, <a href="/wiki/Isoflurane" title="Isoflurane">isoflurane</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/1,1,1-Trichloroethane" title="1,1,1-Trichloroethane">trichloroethane</a>)</li> <li><a href="/wiki/YM-31636" title="YM-31636">YM-31636</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Alosetron" title="Alosetron">Alosetron</a></li> <li><a href="/wiki/Anpirtoline" title="Anpirtoline">Anpirtoline</a></li> <li><a href="/wiki/Arazasetron" class="mw-redirect" title="Arazasetron">Arazasetron</a></li> <li><a href="/wiki/AS-8112" title="AS-8112">AS-8112</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>)</li> <li><a href="/wiki/Azasetron" title="Azasetron">Azasetron</a></li> <li><a href="/wiki/Batanopride" title="Batanopride">Batanopride</a></li> <li><a href="/wiki/Bemesetron" title="Bemesetron">Bemesetron (MDL-72222)</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Cilansetron" title="Cilansetron">Cilansetron</a></li> <li><a href="/wiki/CSP-2503" title="CSP-2503">CSP-2503</a></li> <li><a href="/wiki/Dazopride" title="Dazopride">Dazopride</a></li> <li><a href="/wiki/Dolasetron" title="Dolasetron">Dolasetron</a></li> <li><a href="/wiki/Galanolactone" title="Galanolactone">Galanolactone</a></li> <li><a href="/wiki/Granisetron" title="Granisetron">Granisetron</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Lerisetron" title="Lerisetron">Lerisetron</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Ondansetron" title="Ondansetron">Ondansetron</a></li> <li><a href="/wiki/Palonosetron" title="Palonosetron">Palonosetron</a></li> <li><a href="/wiki/Ramosetron" title="Ramosetron">Ramosetron</a></li> <li><a href="/wiki/Renzapride" title="Renzapride">Renzapride</a></li> <li><a href="/wiki/Ricasetron" title="Ricasetron">Ricasetron</a></li> <li><a href="/wiki/Tedatioxetine" title="Tedatioxetine">Tedatioxetine</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Thujone" title="Thujone">Thujone</a></li> <li><a href="/wiki/Tropanserin" title="Tropanserin">Tropanserin</a></li> <li><a href="/wiki/Tropisetron" title="Tropisetron">Tropisetron</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>)</li> <li><a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">Volatiles/gases</a> (e.g., <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">nitrous oxide</a>, <a href="/wiki/Sevoflurane" title="Sevoflurane">sevoflurane</a>, <a href="/wiki/Xenon" title="Xenon">xenon</a>)</li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li> <li><a href="/wiki/Zacopride" title="Zacopride">Zacopride</a></li> <li><a href="/wiki/Zatosetron" title="Zatosetron">Zatosetron</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a></li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT4_receptor" title="5-HT4 receptor">5-HT<sub>4</sub></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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a></li> <li><a href="/wiki/BIMU8" title="BIMU8">BIMU8</a></li> <li><a href="/wiki/Capeserod" title="Capeserod">Capeserod</a></li> <li><a href="/wiki/Cinitapride" title="Cinitapride">Cinitapride</a></li> <li><a href="/wiki/Cisapride" title="Cisapride">Cisapride</a></li> <li><a href="/wiki/CJ-033466" title="CJ-033466">CJ-033466</a></li> <li><a href="/wiki/Dazopride" title="Dazopride">Dazopride</a></li> <li><a href="/wiki/Metoclopramide" title="Metoclopramide">Metoclopramide</a></li> <li><a href="/w/index.php?title=Minesapride&action=edit&redlink=1" class="new" title="Minesapride (page does not exist)">Minesapride</a></li> <li><a href="/wiki/Mosapride" title="Mosapride">Mosapride</a></li> <li><a href="/wiki/Prucalopride" title="Prucalopride">Prucalopride</a></li> <li><a href="/wiki/PRX-03140" title="PRX-03140">PRX-03140</a></li> <li><a href="/wiki/Renzapride" title="Renzapride">Renzapride</a></li> <li><a href="/wiki/RS-67,333" title="RS-67,333">RS-67,333</a></li> <li><a href="/w/index.php?title=RS-67,506&action=edit&redlink=1" class="new" title="RS-67,506 (page does not exist)">RS-67,506</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Tegaserod" title="Tegaserod">Tegaserod</a></li> <li><a href="/w/index.php?title=Usmarapride&action=edit&redlink=1" class="new" title="Usmarapride (page does not exist)">Usmarapride</a></li> <li><a href="/wiki/Velusetrag" title="Velusetrag">Velusetrag</a></li> <li><a href="/wiki/Zacopride" title="Zacopride">Zacopride</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/GR-113808" title="GR-113808">GR-113808</a></li> <li><a href="/w/index.php?title=GR-125487&action=edit&redlink=1" class="new" title="GR-125487 (page does not exist)">GR-125487</a></li> <li><a href="/wiki/Lysine" title="Lysine">L-Lysine</a></li> <li><a href="/wiki/Piboserod" title="Piboserod">Piboserod</a></li> <li><a href="/w/index.php?title=RS-39604&action=edit&redlink=1" class="new" title="RS-39604 (page does not exist)">RS-39604</a></li> <li><a href="/w/index.php?title=RS-67532&action=edit&redlink=1" class="new" title="RS-67532 (page does not exist)">RS-67532</a></li> <li><a href="/w/index.php?title=SB-203186&action=edit&redlink=1" class="new" title="SB-203186 (page does not exist)">SB-203186</a></li> <li><a href="/wiki/SB-204070" title="SB-204070">SB-204070</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT5A_receptor" title="5-HT5A receptor">5-HT<sub>5A</sub></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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/2-Bromo-LSD" title="2-Bromo-LSD">2-Br-LSD (BOL-148)</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/LSD" title="LSD">LSD</a>)</li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>)</li> <li><a href="/wiki/Valerenic_acid" title="Valerenic acid">Valerenic acid</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Asenapine" title="Asenapine">Asenapine</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine (dimebolin)</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/SB-699551" title="SB-699551">SB-699551</a></li></ul> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT6_receptor" title="5-HT6 receptor">5-HT<sub>6</sub></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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">dihydroergocryptine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Hypidone" title="Hypidone">Hypidone</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Me-5-HT</a>, <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin</a>, <a href="/wiki/E-6801" title="E-6801">E-6801</a>, <a href="/wiki/E-6837" title="E-6837">E-6837</a>, <a href="/wiki/EMD-386088" title="EMD-386088">EMD-386088</a>, <a href="/wiki/EMDT" title="EMDT">EMDT</a>, <a href="/w/index.php?title=LY-586713&action=edit&redlink=1" class="new" title="LY-586713 (page does not exist)">LY-586713</a>, <a href="/w/index.php?title=N-Methyl-5-HT&action=edit&redlink=1" class="new" title="N-Methyl-5-HT (page does not exist)">N-Me-5-HT</a>, <a href="/wiki/ST-1936" title="ST-1936">ST-1936</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li> <li><a href="/wiki/WAY-181187" title="WAY-181187">WAY-181187</a></li> <li><a href="/wiki/WAY-208466" title="WAY-208466">WAY-208466</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=ABT-354&action=edit&redlink=1" class="new" title="ABT-354 (page does not exist)">ABT-354</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Tiospirone" title="Tiospirone">tiospirone</a>)</li> <li><a href="/wiki/AVN-101" class="mw-redirect" title="AVN-101">AVN-101</a></li> <li><a href="/wiki/AVN-211" title="AVN-211">AVN-211</a></li> <li><a href="/wiki/AVN-322" title="AVN-322">AVN-322</a></li> <li><a href="/wiki/AVN-397" title="AVN-397">AVN-397</a></li> <li><a href="/w/index.php?title=BGC20-760&action=edit&redlink=1" class="new" title="BGC20-760 (page does not exist)">BGC20-760</a></li> <li><a href="/w/index.php?title=BVT-5182&action=edit&redlink=1" class="new" title="BVT-5182 (page does not exist)">BVT-5182</a></li> <li><a href="/w/index.php?title=BVT-74316&action=edit&redlink=1" class="new" title="BVT-74316 (page does not exist)">BVT-74316</a></li> <li><a href="/wiki/Cerlapirdine" title="Cerlapirdine">Cerlapirdine</a></li> <li><a href="/wiki/EGIS-12,233" title="EGIS-12,233">EGIS-12,233</a></li> <li><a href="/w/index.php?title=GW-742457&action=edit&redlink=1" class="new" title="GW-742457 (page does not exist)">GW-742457</a></li> <li><a href="/wiki/Idalopirdine" title="Idalopirdine">Idalopirdine</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/w/index.php?title=Landipirdine&action=edit&redlink=1" class="new" title="Landipirdine (page does not exist)">Landipirdine</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine (dimebolin)</a></li> <li><a href="/wiki/Masupirdine" title="Masupirdine">Masupirdine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/MS-245" title="MS-245">MS-245</a></li> <li><a href="/wiki/PRX-07034" title="PRX-07034">PRX-07034</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/Ro_04-6790" title="Ro 04-6790">Ro 04-6790</a></li> <li><a href="/w/index.php?title=Ro_63-0563&action=edit&redlink=1" class="new" title="Ro 63-0563 (page does not exist)">Ro 63-0563</a></li> <li><a href="/wiki/SB-258585" title="SB-258585">SB-258585</a></li> <li><a href="/wiki/SB-271046" title="SB-271046">SB-271046</a></li> <li><a href="/wiki/SB-357134" title="SB-357134">SB-357134</a></li> <li><a href="/wiki/SB-399885" title="SB-399885">SB-399885</a></li> <li><a href="/wiki/Intepirdine" title="Intepirdine">SB-742457</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>)</li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Doxepin" title="Doxepin">doxepin</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/2-Bromo-LSD" title="2-Bromo-LSD">2-Br-LSD (BOL-148)</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Lergotrile" title="Lergotrile">lergotrile</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT7_receptor" title="5-HT7 receptor">5-HT<sub>7</sub></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><i>Agonists:</i> <a href="/wiki/8-OH-DPAT" title="8-OH-DPAT">8-OH-DPAT</a></li> <li><a href="/wiki/AS-19_(drug)" title="AS-19 (drug)">AS-19</a></li> <li><a href="/wiki/Bifeprunox" title="Bifeprunox">Bifeprunox</a></li> <li><a href="/wiki/E-55888" title="E-55888">E-55888</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/LSD" title="LSD">LSD</a>)</li> <li><a href="/wiki/LP-12" title="LP-12">LP-12</a></li> <li><a href="/wiki/LP-44" title="LP-44">LP-44</a></li> <li><a href="/wiki/LP-211" title="LP-211">LP-211</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/Sarizotan" title="Sarizotan">Sarizotan</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Frovatriptan" title="Frovatriptan">frovatriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/N-Methylserotonin" title="N-Methylserotonin">N-Me-5-HT</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Amisulpride" title="Amisulpride">amisulpride</a>, <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>, <a href="/wiki/Tiospirone" title="Tiospirone">tiospirone</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Butaclamol" title="Butaclamol">Butaclamol</a></li> <li><a href="/wiki/DR-4485" title="DR-4485">DR-4485</a></li> <li><a href="/wiki/EGIS-12,233" title="EGIS-12,233">EGIS-12,233</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/2-Bromo-LSD" title="2-Bromo-LSD">2-Br-LSD (BOL-148)</a>, <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Sergolexole" title="Sergolexole">sergolexole</a>)</li> <li><a href="/wiki/JNJ-18038683" title="JNJ-18038683">JNJ-18038683</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/SB-258719" title="SB-258719">SB-258719</a></li> <li><a href="/w/index.php?title=SB-258741&action=edit&redlink=1" class="new" title="SB-258741 (page does not exist)">SB-258741</a></li> <li><a href="/wiki/SB-269970" title="SB-269970">SB-269970</a></li> <li><a href="/w/index.php?title=SB-656104&action=edit&redlink=1" class="new" title="SB-656104 (page does not exist)">SB-656104</a></li> <li><a href="/w/index.php?title=SB-656104A&action=edit&redlink=1" class="new" title="SB-656104A (page does not exist)">SB-656104A</a></li> <li><a href="/w/index.php?title=SB-691673&action=edit&redlink=1" class="new" title="SB-691673 (page does not exist)">SB-691673</a></li> <li><a href="/w/index.php?title=SLV-313&action=edit&redlink=1" class="new" title="SLV-313 (page does not exist)">SLV-313</a></li> <li><a href="/w/index.php?title=SLV-314&action=edit&redlink=1" class="new" title="SLV-314 (page does not exist)">SLV-314</a></li> <li><a href="/wiki/Spiperone" title="Spiperone">Spiperone</a></li> <li><a href="/w/index.php?title=SSR-181507&action=edit&redlink=1" class="new" title="SSR-181507 (page does not exist)">SSR-181507</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Acetophenazine" title="Acetophenazine">acetophenazine</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Chlorprothixene" title="Chlorprothixene">chlorprothixene</a>, <a href="/wiki/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Pimozide" title="Pimozide">pimozide</a>)</li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><small><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></small></li> <li><small><i><a href="/wiki/Template:Adrenergic_receptor_modulators" title="Template:Adrenergic receptor modulators">Adrenergics</a></i></small></li> <li><small><i><a href="/wiki/Template:Dopamine_receptor_modulators" title="Template:Dopamine receptor modulators">Dopaminergics</a></i></small></li> <li><small><i><a href="/wiki/Template:Melatonin_receptor_modulators" title="Template:Melatonin receptor modulators">Melatonergics</a></i></small></li> <li><small><i><a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> and <a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">releasing agents</a></i></small></li> <li><small><i><a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></i></small></li> <li><small><i><a href="/wiki/Template:Monoamine_neurotoxins" class="mw-redirect" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></i></small></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Trace_amine-associated_receptor_modulators1416" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:TAAR_modulators" title="Template:TAAR modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:TAAR_modulators" title="Template talk:TAAR modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:TAAR_modulators" title="Special:EditPage/Template:TAAR modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Trace_amine-associated_receptor_modulators1416" style="font-size:114%;margin:0 4em"><a href="/wiki/Trace_amine-associated_receptor" title="Trace amine-associated receptor">Trace amine-associated receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Trace_amine-associated_receptor_1" class="mw-redirect" title="Trace amine-associated receptor 1"><abbr title="Trace amine-associated receptor 1">TAAR1</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Trace amine-associated receptor 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Agonist" title="Agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Trace_amine" title="Trace amine">Endogenous</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">Monoamine neurotransmitters</a> <ul><li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a></li></ul></li> <li><a href="/wiki/Trace_amine" title="Trace amine">Trace amines</a> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li> <li><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methyltyramine" title="N-Methyltyramine"><i>N</i>-Methyltyramine</a></li> <li><a href="/wiki/Meta-Octopamine" class="mw-redirect" title="Meta-Octopamine"><i>m</i>-Octopamine</a></li> <li><a href="/wiki/Para-Octopamine" class="mw-redirect" title="Para-Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">β-Phenethylamine</a></li> <li><a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Para-Tyramine" class="mw-redirect" title="Para-Tyramine"><i>p</i>-Tyramine</a></li></ul></li> <li>Others <ul><li><a href="/wiki/Cyclohexylamine" title="Cyclohexylamine">Cyclohexylamine</a></li> <li><a href="/w/index.php?title=Isoamylamine&action=edit&redlink=1" class="new" title="Isoamylamine (page does not exist)">Isoamylamine</a></li> <li><a href="/wiki/Trimethylamine" title="Trimethylamine">Trimethylamine</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Exogenous" class="mw-redirect" title="Exogenous">Exogenous</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B" title="2C-B">2C-B</a></li> <li><a href="/wiki/2C-B-Fly" class="mw-redirect" title="2C-B-Fly">2C-B-Fly</a></li> <li><a href="/wiki/2C-E" title="2C-E">2C-E</a></li> <li><a href="/wiki/2C-H" title="2C-H">2C-H</a></li> <li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li> <li><a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a></li> <li><a href="/wiki/A-77636" title="A-77636">A-77636</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-Aminoindane</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/w/index.php?title=AP163&action=edit&redlink=1" class="new" title="AP163 (page does not exist)">AP163</a></li> <li><a href="/wiki/Apomorphine" title="Apomorphine">Apomorphine</a></li> <li><a href="/wiki/Asenapine" title="Asenapine">Asenapine</a></li> <li><a href="/wiki/Bromocriptine" title="Bromocriptine">Bromocriptine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Clonidine" title="Clonidine">Clonidine</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">Dihydroergotamine</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">Dimethyltryptamine</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/N,N-Dimethylphenethylamine" title="N,N-Dimethylphenethylamine"><i>N</i>,<i>N</i>-Dimethylphenethylamine</a></li> <li><a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">Ergometrine</a></li> <li><a href="/wiki/Fenoldopam" title="Fenoldopam">Fenoldopam</a></li> <li><a href="/wiki/Fenoterol" title="Fenoterol">Fenoterol</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-Fluoroamphetamine</a></li> <li><a href="/wiki/Guanabenz" title="Guanabenz">Guanabenz</a></li> <li><a href="/wiki/Guanfacine" title="Guanfacine">Guanfacine</a></li> <li><a href="/wiki/Halostachine" title="Halostachine">Halostachine</a></li> <li><a href="/wiki/Higenamine" title="Higenamine">Higenamine</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine (norpholedrine)</a></li> <li><a href="/wiki/Idazoxan" title="Idazoxan">Idazoxan</a></li> <li><a href="/wiki/5-Iodo-2-aminoindane" class="mw-redirect" title="5-Iodo-2-aminoindane">5-Iodo-2-aminoindane</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isopropyloctopamine" class="mw-redirect" title="Isopropyloctopamine">Isopropyloctopamine</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/LK00764" title="LK00764">LK00764</a></li> <li><a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">LSD</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyaminoindane" class="mw-redirect" title="Methylenedioxyaminoindane">MDAI</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metergoline" title="Metergoline">Metergoline</a></li> <li><a href="/wiki/N-Methyl-2-AI" class="mw-redirect" title="N-Methyl-2-AI"><i>N</i>-Methyl-2-AI</a></li> <li><a href="/wiki/2-Methylphenethylamine" title="2-Methylphenethylamine">2-Methylphenethylamine</a></li> <li><a href="/wiki/3-Methylphenethylamine" title="3-Methylphenethylamine">3-Methylphenethylamine</a></li> <li><a href="/wiki/4-Methylphenethylamine" title="4-Methylphenethylamine">4-Methylphenethylamine</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/3-Methoxyamphetamine" title="3-Methoxyamphetamine">MMA</a></li> <li><a href="/wiki/MPTP" title="MPTP">MPTP</a></li> <li><a href="/wiki/Naphazoline" title="Naphazoline">Naphazoline</a></li> <li><a href="/wiki/Nomifensine" title="Nomifensine">Nomifensine</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/Phentolamine" title="Phentolamine">Phentolamine</a></li> <li><a href="/wiki/O-Phenyl-3-iodotyramine" title="O-Phenyl-3-iodotyramine"><i>o</i>-PIT</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">Psilocin</a></li> <li><a href="/wiki/Ralmitaront" title="Ralmitaront">Ralmitaront (RG-7906, RO6889450)</a></li> <li><a href="/wiki/RG-7351" title="RG-7351">RG-7351</a></li> <li><a href="/wiki/RG-7410" title="RG-7410">RG-7410</a></li> <li><a href="/wiki/RO5073012" title="RO5073012">RO5073012</a></li> <li><a href="/wiki/RO5166017" title="RO5166017">RO5166017</a></li> <li><a href="/wiki/RO5203648" title="RO5203648">RO5203648</a></li> <li><a href="/wiki/RO5256390" title="RO5256390">RO5256390</a></li> <li><a href="/wiki/RO5263397" title="RO5263397">RO5263397</a></li> <li><a href="/w/index.php?title=S18616&action=edit&redlink=1" class="new" title="S18616 (page does not exist)">S18616</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline (<small>L</small>-deprenyl)</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Tolazoline" title="Tolazoline">Tolazoline</a></li> <li><a href="/wiki/Ulotaront" title="Ulotaront">Ulotaront (SEP-363856)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Compound_22_(TAAR1_antagonist)" title="Compound 22 (TAAR1 antagonist)">Compound 22</a></li> <li><a href="/wiki/EPPTB" title="EPPTB">EPPTB (RO-5212773)</a></li> <li><a href="/wiki/RTI-7470-44" title="RTI-7470-44">RTI-7470-44</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Inverse_agonist" title="Inverse agonist">Inverse agonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/EPPTB" title="EPPTB">EPPTB (RO-5212773)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Trace_amine-associated_receptor_5" class="mw-redirect" title="Trace amine-associated receptor 5"><abbr title="Trace amine-associated receptor 5">TAAR5</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Trace amine-associated receptor 5</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Agonists32" scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Agonist" title="Agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N,N-Dimethylethylamine" title="N,N-Dimethylethylamine"><i>N</i>,<i>N</i>-Dimethylethylamine</a></li> <li><a href="/wiki/Trimethylamine" title="Trimethylamine">Trimethylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Inverse_agonist" title="Inverse agonist">Inverse agonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><small><i><b>Notes:</b></i> (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the <a href="/wiki/Trace_amine#List_of_trace_amines" title="Trace amine">List of trace amines</a>, <a href="/wiki/Trace_amine-associated_receptor" title="Trace amine-associated receptor">TAAR</a>, and <a href="/wiki/TAAR1" title="TAAR1">TAAR1</a> pages. <i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></small></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Phenethylamines352" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Phenethylamines" title="Template:Phenethylamines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenethylamines" title="Template talk:Phenethylamines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenethylamines" title="Special:EditPage/Template:Phenethylamines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Phenethylamines352" style="font-size:114%;margin:0 4em"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Psychedelics:</i> <a href="/wiki/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a></li> <li><a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a></li> <li><a href="/wiki/25D-NBOMe" title="25D-NBOMe">25D-NBOMe</a></li> <li><a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a></li> <li><a href="/wiki/25N-NBOMe" title="25N-NBOMe">25N-NBOMe</a></li> <li><a href="/wiki/2C-B" title="2C-B">2C-B</a></li> <li><a href="/w/index.php?title=2C-B-AN&action=edit&redlink=1" class="new" title="2C-B-AN (page does not exist)">2C-B-AN</a></li> <li><a href="/w/index.php?title=2C-Bn&action=edit&redlink=1" class="new" title="2C-Bn (page does not exist)">2C-Bn</a></li> <li><a href="/wiki/2C-Bu" title="2C-Bu">2C-Bu</a></li> <li><a href="/wiki/2C-C" title="2C-C">2C-C</a></li> <li><a href="/w/index.php?title=2C-CN&action=edit&redlink=1" class="new" title="2C-CN (page does not exist)">2C-CN</a></li> <li><a href="/wiki/2C-CP" title="2C-CP">2C-CP</a></li> <li><a href="/wiki/2C-D" title="2C-D">2C-D</a></li> <li><a href="/wiki/2C-E" title="2C-E">2C-E</a></li> <li><a href="/wiki/2C-EF" title="2C-EF">2C-EF</a></li> <li><a href="/wiki/2C-F" title="2C-F">2C-F</a></li> <li><a href="/wiki/2C-G" title="2C-G">2C-G</a></li> <li><a href="/wiki/2C-G-1" class="mw-redirect" title="2C-G-1">2C-G-1</a></li> <li><a href="/wiki/2C-G-2" class="mw-redirect" title="2C-G-2">2C-G-2</a></li> <li><a href="/wiki/2C-G-3" class="mw-redirect" title="2C-G-3">2C-G-3</a></li> <li><a href="/wiki/2C-G-4" class="mw-redirect" title="2C-G-4">2C-G-4</a></li> <li><a href="/wiki/2C-G-5" class="mw-redirect" title="2C-G-5">2C-G-5</a></li> <li><a href="/wiki/2C-G-6" class="mw-redirect" title="2C-G-6">2C-G-6</a></li> <li><a href="/wiki/2C-G-N" class="mw-redirect" title="2C-G-N">2C-G-N</a></li> <li><a href="/wiki/2C-H" title="2C-H">2C-H</a></li> <li><a href="/wiki/2C-I" title="2C-I">2C-I</a></li> <li><a href="/wiki/2C-iBu" title="2C-iBu">2C-iBu</a></li> <li><a href="/wiki/2C-iP" title="2C-iP">2C-iP</a></li> <li><a href="/wiki/2C-N" title="2C-N">2C-N</a></li> <li><a href="/w/index.php?title=2C-NH2&action=edit&redlink=1" class="new" title="2C-NH2 (page does not exist)">2C-NH2</a></li> <li><a href="/wiki/2C-O" class="mw-redirect" title="2C-O">2C-O</a></li> <li><a href="/wiki/2C-O-4" title="2C-O-4">2C-O-4</a></li> <li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li> <li><a href="/wiki/2C-Ph" title="2C-Ph">2C-Ph</a></li> <li><a href="/wiki/2C-SE" class="mw-redirect" title="2C-SE">2C-SE</a></li> <li><a href="/wiki/2C-T" title="2C-T">2C-T</a></li> <li><a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a></li> <li><a href="/wiki/2C-T-3" title="2C-T-3">2C-T-3</a></li> <li><a href="/wiki/2C-T-4" title="2C-T-4">2C-T-4</a></li> <li><a href="/w/index.php?title=2C-T-5&action=edit&redlink=1" class="new" title="2C-T-5 (page does not exist)">2C-T-5</a></li> <li><a href="/w/index.php?title=2C-T-6&action=edit&redlink=1" class="new" title="2C-T-6 (page does not exist)">2C-T-6</a></li> <li><a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a></li> <li><a href="/wiki/2C-T-8" title="2C-T-8">2C-T-8</a></li> <li><a href="/wiki/2C-T-9" class="mw-redirect" title="2C-T-9">2C-T-9</a></li> <li><a href="/w/index.php?title=2C-T-10&action=edit&redlink=1" class="new" title="2C-T-10 (page does not exist)">2C-T-10</a></li> <li><a href="/w/index.php?title=2C-T-11&action=edit&redlink=1" class="new" title="2C-T-11 (page does not exist)">2C-T-11</a></li> <li><a href="/w/index.php?title=2C-T-12&action=edit&redlink=1" class="new" title="2C-T-12 (page does not exist)">2C-T-12</a></li> <li><a href="/wiki/2C-T-13" title="2C-T-13">2C-T-13</a></li> <li><a href="/w/index.php?title=2C-T-14&action=edit&redlink=1" class="new" title="2C-T-14 (page does not exist)">2C-T-14</a></li> <li><a href="/wiki/2C-T-15" title="2C-T-15">2C-T-15</a></li> <li><a href="/wiki/2C-T-16" title="2C-T-16">2C-T-16</a></li> <li><a href="/wiki/2C-T-17" title="2C-T-17">2C-T-17</a></li> <li><a href="/w/index.php?title=2C-T-18&action=edit&redlink=1" class="new" title="2C-T-18 (page does not exist)">2C-T-18</a></li> <li><a href="/wiki/2C-T-19" title="2C-T-19">2C-T-19</a></li> <li><a href="/w/index.php?title=2C-T-20&action=edit&redlink=1" class="new" title="2C-T-20 (page does not exist)">2C-T-20</a></li> <li><a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a></li> <li><a href="/w/index.php?title=2C-T-22&action=edit&redlink=1" class="new" title="2C-T-22 (page does not exist)">2C-T-22</a></li> <li><a href="/w/index.php?title=2C-T-22.5&action=edit&redlink=1" class="new" title="2C-T-22.5 (page does not exist)">2C-T-22.5</a></li> <li><a href="/w/index.php?title=2C-T-23&action=edit&redlink=1" class="new" title="2C-T-23 (page does not exist)">2C-T-23</a></li> <li><a href="/w/index.php?title=2C-T-24&action=edit&redlink=1" class="new" title="2C-T-24 (page does not exist)">2C-T-24</a></li> <li><a href="/w/index.php?title=2C-T-25&action=edit&redlink=1" class="new" title="2C-T-25 (page does not exist)">2C-T-25</a></li> <li><a href="/wiki/2C-T-27" title="2C-T-27">2C-T-27</a></li> <li><a href="/wiki/2C-T-28" title="2C-T-28">2C-T-28</a></li> <li><a href="/w/index.php?title=2C-T-30&action=edit&redlink=1" class="new" title="2C-T-30 (page does not exist)">2C-T-30</a></li> <li><a href="/w/index.php?title=2C-T-31&action=edit&redlink=1" class="new" title="2C-T-31 (page does not exist)">2C-T-31</a></li> <li><a href="/w/index.php?title=2C-T-32&action=edit&redlink=1" class="new" title="2C-T-32 (page does not exist)">2C-T-32</a></li> <li><a href="/wiki/2C-T-33" title="2C-T-33">2C-T-33</a></li> <li><a href="/wiki/2C-tBu" title="2C-tBu">2C-tBu</a></li> <li><a href="/wiki/2C-TFE" title="2C-TFE">2C-TFE</a></li> <li><a href="/wiki/2C-TFM" title="2C-TFM">2C-TFM</a></li> <li><a href="/wiki/2C-YN" title="2C-YN">2C-YN</a></li> <li><a href="/wiki/2C-V" title="2C-V">2C-V</a></li> <li><a href="/wiki/Allylescaline" title="Allylescaline">Allylescaline</a></li> <li><a href="/wiki/DESOXY" title="DESOXY">DESOXY</a></li> <li><a href="/wiki/Escaline" title="Escaline">Escaline</a></li> <li><a href="/wiki/Isoproscaline" title="Isoproscaline">Isoproscaline</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Macromerine" title="Macromerine">Macromerine</a></li> <li><a href="/wiki/3-Methoxy-4-ethoxyphenethylamine" title="3-Methoxy-4-ethoxyphenethylamine">MEPEA</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metaescaline" title="Metaescaline">Metaescaline</a></li> <li><a href="/wiki/Methallylescaline" title="Methallylescaline">Methallylescaline</a></li> <li><a href="/wiki/Proscaline" title="Proscaline">Proscaline</a></li> <li><a href="/wiki/Psi-2C-T-4" class="mw-redirect" title="Psi-2C-T-4">Psi-2C-T-4</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li></ul> <ul><li><i>Stimulants:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">α-Methylphenethylamine</a> (amphetamine)</li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/M-Methylphenethylamine" class="mw-redirect" title="M-Methylphenethylamine"><i>m</i>-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li> <li><a href="/wiki/O-Methylphenethylamine" class="mw-redirect" title="O-Methylphenethylamine"><i>o</i>-Methylphenethylamine</a></li> <li><a href="/wiki/P-Methylphenethylamine" class="mw-redirect" title="P-Methylphenethylamine"><i>p</i>-Methylphenethylamine</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li></ul> <ul><li><i>Entactogens:</i> <a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a><br /><i>Others:</i> <a href="/wiki/Biscaline" title="Biscaline">Biscaline</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Buscaline" title="Buscaline">Buscaline</a></li> <li><a href="/wiki/3,4-Dimethoxyphenethylamine" title="3,4-Dimethoxyphenethylamine">DMPEA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Psychedelics:</i> <a href="/wiki/3C-AL" title="3C-AL">3C-AL</a></li> <li><a href="/wiki/3C-BZ" title="3C-BZ">3C-BZ</a></li> <li><a href="/wiki/3C-E" title="3C-E">3C-E</a></li> <li><a href="/wiki/3C-MAL" title="3C-MAL">3C-MAL</a></li> <li><a href="/wiki/3C-P" title="3C-P">3C-P</a></li> <li><a href="/wiki/Aleph_(psychedelic)" title="Aleph (psychedelic)">Aleph</a></li> <li><a href="/wiki/Beatrice_(psychedelic)" title="Beatrice (psychedelic)">Beatrice</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/4-Methyl-2,5-methoxyphenylcyclopropylamine" class="mw-redirect" title="4-Methyl-2,5-methoxyphenylcyclopropylamine">DMCPA</a></li> <li><a href="/wiki/DMMDA" title="DMMDA">DMMDA</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-fluoroethylamphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-fluoroethylamphetamine">DOEF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-nitroamphetamine" title="2,5-Dimethoxy-4-nitroamphetamine">DON</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-propylamphetamine" title="2,5-Dimethoxy-4-propylamphetamine">DOPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-trifluoromethylamphetamine" title="2,5-Dimethoxy-4-trifluoromethylamphetamine">DOTFM</a></li> <li><a href="/wiki/Ganesha_(psychedelic)" title="Ganesha (psychedelic)">Ganesha</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDA-2" title="MMDA-2">MMDA-2</a></li> <li><a href="/wiki/Psi-DOM" class="mw-redirect" title="Psi-DOM">Psi-DOM</a></li> <li><a href="/wiki/Trimethoxyamphetamine" class="mw-redirect" title="Trimethoxyamphetamine">TMA</a></li> <li><a href="/wiki/Tetramethoxyamphetamine" class="mw-redirect" title="Tetramethoxyamphetamine">TeMA</a></li> <li><a href="/wiki/ZDCM-04" title="ZDCM-04">ZDCM-04</a><br /><i>Stimulants:</i> <a href="/wiki/2-Fluoroamphetamine" title="2-Fluoroamphetamine">2-FA</a></li> <li><a href="/wiki/2-Fluoromethamphetamine" title="2-Fluoromethamphetamine">2-FMA</a></li> <li><a href="/wiki/3-Fluoroamphetamine" title="3-Fluoroamphetamine">3-FA</a></li> <li><a href="/wiki/3-Fluoromethamphetamine" title="3-Fluoromethamphetamine">3-FMA</a></li> <li><a href="/wiki/Acridorex" title="Acridorex">Acridorex</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a>, <a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/Benfluorex" title="Benfluorex">Benfluorex</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Fencamfamin" title="Fencamfamin">Fencamfamin</a></li> <li><a href="/wiki/Fencamine" title="Fencamine">Fencamine</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a> (<a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a>)</li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flucetorex" title="Flucetorex">Flucetorex</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Formetorex" title="Formetorex">Formetorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Gepefrine" title="Gepefrine">Gepefrine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Isopropylamphetamine" title="Isopropylamphetamine">Isopropylamphetamine</a></li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> (Dextromethamphetamine, <a href="/wiki/Levomethamphetamine" title="Levomethamphetamine">Levomethamphetamine</a>)</li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/L-Norpseudoephedrine" title="L-Norpseudoephedrine"><span style="font-size:85%;">L</span>-Norpseudoephedrine</a></li> <li><a href="/wiki/N,alpha-Diethylphenylethylamine" class="mw-redirect" title="N,alpha-Diethylphenylethylamine">N,alpha-Diethylphenylethylamine</a></li> <li><a href="/wiki/Oxifentorex" title="Oxifentorex">Oxifentorex</a></li> <li><a href="/wiki/Oxilofrine" title="Oxilofrine">Oxilofrine</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">PBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">PCA</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">PFA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">PFMA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">PIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxy-N-ethylamphetamine" title="Para-Methoxy-N-ethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxy-N-methylamphetamine" class="mw-redirect" title="Para-Methoxy-N-methylamphetamine">PMMA</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Sibutramine" title="Sibutramine">Sibutramine</a></li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a><br /><i>Entactogens:</i> <a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APB" title="5-APB">5-APB</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-EAPB" title="5-EAPB">5-EAPB</a></li> <li><a href="/wiki/5-IT" class="mw-redirect" title="5-IT">5-IT</a></li> <li><a href="/wiki/5-MAPB" title="5-MAPB">5-MAPB</a></li> <li><a href="/wiki/5-MAPDB" title="5-MAPDB">5-MAPDB</a></li> <li><a href="/wiki/6-APB" title="6-APB">6-APB</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Chloro-MDMA" title="6-Chloro-MDMA">6-Chloro-MDMA</a></li> <li><a href="/wiki/6-EAPB" title="6-EAPB">6-EAPB</a></li> <li><a href="/wiki/6-IT" class="mw-redirect" title="6-IT">6-IT</a></li> <li><a href="/wiki/6-MAPB" title="6-MAPB">6-MAPB</a></li> <li><a href="/wiki/6-MAPDB" title="6-MAPDB">6-MAPDB</a></li> <li><a href="/wiki/Ethylidenedioxyamphetamine" class="mw-redirect" title="Ethylidenedioxyamphetamine">EDA</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/2,3-Methylenedioxyamphetamine" title="2,3-Methylenedioxyamphetamine">2,3-MDA</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">3,4-MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxylmethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxylmethamphetamine">MDHMA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a><br /><i>Others:</i> <a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">3,4-DCA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/DiFMDA" class="mw-redirect" title="DiFMDA">DiFMDA</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl"><span style="font-size:85%;">D</span>-Deprenyl</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phentermine" title="Phentermine">Phentermines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a><br /><i>Entactogens:</i> <a href="/wiki/Methylenedioxyphentermine" class="mw-redirect" title="Methylenedioxyphentermine">MDPH</a></li> <li><a href="/wiki/Methylenedioxymethylphentermine" class="mw-redirect" title="Methylenedioxymethylphentermine">MDMPH</a><br /><i>Others:</i> <a href="/wiki/Cericlamine" title="Cericlamine">Cericlamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Cathinones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/3-Fluoromethcathinone" title="3-Fluoromethcathinone">3-FMC</a></li> <li><a href="/wiki/4-Methylcathinone" title="4-Methylcathinone">4-MC</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">4-BMC</a></li> <li><a href="/wiki/4-Chloromethcathinone" title="4-Chloromethcathinone">4-CMC</a></li> <li><a href="/wiki/4-Ethylmethcathinone" title="4-Ethylmethcathinone">4-EMC</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">4-FMC</a></li> <li><a href="/wiki/4-Methylethcathinone" title="4-Methylethcathinone">4-MEC</a></li> <li><a href="/wiki/4-Methylbuphedrone" title="4-Methylbuphedrone">4-MeMABP</a></li> <li><a href="/wiki/4-Methylpentedrone" title="4-Methylpentedrone">4-MPD</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Benzedrone" title="Benzedrone">Benzedrone</a></li> <li><a href="/wiki/Brephedrone" class="mw-redirect" title="Brephedrone">Brephedrone</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Dimethylcathinone" title="Dimethylcathinone">Dimethylcathinone</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/N-Ethylbuphedrone" title="N-Ethylbuphedrone">NEB</a></li> <li><a href="/wiki/N-Ethylhexedrone" title="N-Ethylhexedrone">N-Ethylhexedrone</a></li> <li><a href="/wiki/N-Ethylpentedrone" title="N-Ethylpentedrone">N-Ethylpentedrone</a></li> <li><a href="/wiki/Pentedrone" title="Pentedrone">Pentedrone</a></li> <li><a href="/wiki/Pentylone" title="Pentylone">Pentylone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a><br /><i>Entactogens:</i> <a href="/wiki/3,4-Dimethylmethcathinone" title="3,4-Dimethylmethcathinone">3,4-DMMC</a></li> <li><a href="/wiki/3-Methylmethcathinone" title="3-Methylmethcathinone">3-MMC</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Methylenedioxycathinone" title="Methylenedioxycathinone">Methylenedioxycathinone</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Propylone" title="Propylone">Propylone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Entactogens:</i> <a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Methylphenylisobutylamine" title="4-Methylphenylisobutylamine">4-MAB</a></li> <li><a href="/wiki/Ariadne_(psychedelic)" class="mw-redirect" title="Ariadne (psychedelic)">Ariadne</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/MBDB" title="MBDB">MBDB</a><br /><i>Stimulants:</i> <a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">Phenylalkylpyrrolidines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/Alpha-Pyrrolidinobutiophenone" class="mw-redirect" title="Alpha-Pyrrolidinobutiophenone">α-PBP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinohexiophenone" class="mw-redirect" title="Alpha-Pyrrolidinohexiophenone">α-PHP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopropiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopropiophenone">α-PPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiophenone">α-PVP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinobutiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinobutiophenone">MDPBP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinopropiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinopropiophenone">MDPPP</a></li> <li><a href="/wiki/3,4-Methylenedioxypyrovalerone" class="mw-redirect" title="3,4-Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">4-MePBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">4-MePHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">4-MePPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopropiophenone" title="4'-Methoxy-α-pyrrolidinopropiophenone">MOPPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopentiophenone" title="4'-Methoxy-α-pyrrolidinopentiophenone">MOPVP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">MPBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">MPHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">MPPP</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">PEP</a></li> <li><a href="/wiki/Prolintane" title="Prolintane">Prolintane</a></li> <li><a href="/wiki/Pyrovalerone" title="Pyrovalerone">Pyrovalerone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Catecholamine" title="Catecholamine">Catecholamines</a><br /><span style="font-size:85%;">(and close relatives)</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/6-Hydroxydopamine" class="mw-redirect" title="6-Hydroxydopamine">6-OHDA</a></li> <li><a href="/wiki/Alpha-Methyldopamine" class="mw-redirect" title="Alpha-Methyldopamine">a-Me-DA</a></li> <li><a href="/wiki/Alpha-Methyltyramine" class="mw-redirect" title="Alpha-Methyltyramine">a-Me-TRA</a></li> <li><a href="/wiki/Adrenochrome" title="Adrenochrome">Adrenochrome</a></li> <li><a href="/wiki/Ciladopa" title="Ciladopa">Ciladopa</a></li> <li><a href="/wiki/D-DOPA" title="D-DOPA"><span style="font-size:85%;">D</span>-DOPA</a> (Dextrodopa)</li> <li><a href="/wiki/Dimetofrine" title="Dimetofrine">Dimetofrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Epinephrine_(neurotransmitter)" class="mw-redirect" title="Epinephrine (neurotransmitter)">Epinephrine</a></li> <li><a href="/wiki/Epinine" class="mw-redirect" title="Epinine">Epinine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Fenclonine" title="Fenclonine">Fenclonine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA"><span style="font-size:85%;">L</span>-DOPA</a> (Levodopa)</li> <li><a href="/wiki/L-DOPS" class="mw-redirect" title="L-DOPS"><span style="font-size:85%;">L</span>-DOPS</a> (Droxidopa)</li> <li><a href="/wiki/L-Phenylalanine" class="mw-redirect" title="L-Phenylalanine"><span style="font-size:85%;">L</span>-Phenylalanine</a></li> <li><a href="/wiki/L-Tyrosine" class="mw-redirect" title="L-Tyrosine"><span style="font-size:85%;">L</span>-Tyrosine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Metaterol" title="Metaterol">Metaterol</a></li> <li><a href="/wiki/Metirosine" class="mw-redirect" title="Metirosine">Metirosine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/N,N-Dimethyldopamine" title="N,N-Dimethyldopamine">N,N-Dimethyldopamine</a></li> <li><a href="/wiki/Nordefrin" class="mw-redirect" title="Nordefrin">Nordefrin</a> (<a href="/wiki/Levonordefrin" class="mw-redirect" title="Levonordefrin">Levonordefrin</a>)</li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a> (<i>m</i>-Octopamine)</li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AL-LAD" title="AL-LAD">AL-LAD</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Desvenlafaxine" title="Desvenlafaxine">Desvenlafaxine</a></li> <li><a href="/wiki/Diphenidine" title="Diphenidine">Diphenidine</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/ETH-LAD" title="ETH-LAD">ETH-LAD</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fluorolintane" title="Fluorolintane">Fluorolintane</a></li> <li><a href="/wiki/Hexapradol" title="Hexapradol">Hexapradol</a></li> <li><a href="/wiki/IP-LAD" class="mw-redirect" title="IP-LAD">IP-LAD</a></li> <li><a href="/wiki/Lysergic_acid_amide" class="mw-redirect" title="Lysergic acid amide">Lysergic acid amide</a></li> <li><a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">Lysergic acid 2-butyl amide</a></li> <li><a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">Lysergic acid 2,4-dimethylazetidide</a></li> <li><a href="/wiki/LSD" title="LSD">Lysergic acid diethylamide</a></li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Methoxphenidine" title="Methoxphenidine">Methoxphenidine</a></li> <li><a href="/wiki/MT-45" title="MT-45">MT-45</a></li> <li><a href="/wiki/PARGY-LAD" title="PARGY-LAD">PARGY-LAD</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a href="/wiki/PRO-LAD" title="PRO-LAD">PRO-LAD</a></li> <li><a href="/wiki/Pronethalol" title="Pronethalol">Pronethalol</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a> (<a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a>)</li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Thiamphenicol" title="Thiamphenicol">Thiamphenicol</a></li> <li><a href="/wiki/UWA-101" title="UWA-101">UWA-101</a></li> <li><a href="/wiki/Venlafaxine" title="Venlafaxine">Venlafaxine</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img 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