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dir="ltr"><p class="mw-empty-elt"> </p> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): 2C-Bu">2C-Bu</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:2C-Bu.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/2C-Bu.svg/220px-2C-Bu.svg.png" decoding="async" width="220" height="128" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/2C-Bu.svg/330px-2C-Bu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d3/2C-Bu.svg/440px-2C-Bu.svg.png 2x" data-file-width="645" data-file-height="375" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">2,5-Dimethoxy-4-butylphenethylamine; 4-Butyl-2,5-dimethoxyphenethylamine; 2C-BU</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">2-(4-butyl-2,5-dimethoxyphenyl)ethan-1-amine</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/172187929">172187929</a></span></li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>14</sub><span title="Hydrogen">H</span><sub>23</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>2</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002237343000000000♠"></span>237.343</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CCCCC1%3DCC%28%3DC%28C%3DC1OC%29CCN%29OC">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CCCCC1=CC(=C(C=C1OC)CCN)OC</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C14H23NO2/c1-4-5-6-11-9-14(17-3)12(7-8-15)10-13(11)16-2/h9-10H,4-8,15H2,1-3H3</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:WVGDKSDIKCPRKV-UHFFFAOYSA-N</div></li></ul> </div></td></tr></tbody></table> <p><b>2C-Bu</b>, also known as <b>2,5-dimethoxy-4-butylphenethylamine</b>, is a <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> of the <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">phenethylamine</a> and <a href="/wiki/4-substituted_2,5-dimethoxyphenethylamine" class="mw-redirect" title="4-substituted 2,5-dimethoxyphenethylamine">2C</a> families.<sup id="cite_ref-TrachselLehmanEnzensperger2013_1-0" class="reference"><a href="#cite_note-TrachselLehmanEnzensperger2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It has been said by <a href="/wiki/Daniel_Trachsel" title="Daniel Trachsel">Daniel Trachsel</a> to be completely unknown.<sup id="cite_ref-TrachselLehmanEnzensperger2013_1-1" class="reference"><a href="#cite_note-TrachselLehmanEnzensperger2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> 2C-Bu is the 2C <a href="/wiki/Structural_analogue" class="mw-redirect" title="Structural analogue">analogue</a> of the <a href="/wiki/4-substituted_2,5-dimethoxyamphetamine" class="mw-redirect" title="4-substituted 2,5-dimethoxyamphetamine">DOx</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> <a href="/wiki/DOBU" class="mw-redirect" title="DOBU">DOBU</a>, which is <a href="/wiki/Pharmacology" title="Pharmacology">active</a> but does not appear to have <a href="/wiki/Psychedelic_drug" title="Psychedelic drug">psychedelic</a>-type effects in either animals or humans.<sup id="cite_ref-TrachselLehmanEnzensperger2013_1-2" class="reference"><a href="#cite_note-TrachselLehmanEnzensperger2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PiHKAL1991_2-0" class="reference"><a href="#cite_note-PiHKAL1991-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SeggelYousifLyon1990_3-0" class="reference"><a href="#cite_note-SeggelYousifLyon1990-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>2C-Bu has several notable <a href="/wiki/Skeletal_isomer" class="mw-redirect" title="Skeletal isomer">skeletal isomers</a>, including <a href="/wiki/2C-iBu" title="2C-iBu">2C-iBu</a>, <a href="/wiki/2C-tBu" title="2C-tBu">2C-tBu</a>, and <a href="/w/index.php?title=2C-sBu&action=edit&redlink=1" class="new" title="2C-sBu (page does not exist)">2C-sBu</a>.<sup id="cite_ref-TrachselLehmanEnzensperger2013_1-3" class="reference"><a href="#cite_note-TrachselLehmanEnzensperger2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-VartyCanalMueller2024_4-0" class="reference"><a href="#cite_note-VartyCanalMueller2024-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> 2C-iBu and 2C-tBu are both active and produce <a href="/wiki/Hallucinogen" title="Hallucinogen">hallucinogen</a>-type effects in animals and/or humans.<sup id="cite_ref-ShulginManningDaley2011_5-0" class="reference"><a href="#cite_note-ShulginManningDaley2011-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WO2020210823A1_6-0" class="reference"><a href="#cite_note-WO2020210823A1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Raz2020_7-0" class="reference"><a href="#cite_note-Raz2020-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-VartyCanalMueller2024_4-1" class="reference"><a href="#cite_note-VartyCanalMueller2024-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> This is in spite of 2C-tBu being predicted to be inactive<sup id="cite_ref-VartyCanalMueller2024_4-2" class="reference"><a href="#cite_note-VartyCanalMueller2024-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/DOTB" class="mw-redirect" title="DOTB">DOTB</a> (the DOx analogue of 2C-tBu) being inactive as a hallucinogen in animals and humans.<sup id="cite_ref-PiHKAL1991_2-1" class="reference"><a href="#cite_note-PiHKAL1991-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Oberlender1989_8-0" class="reference"><a href="#cite_note-Oberlender1989-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> 2C-iBu may have reduced hallucinogenic <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a> than other 2C drugs and is being developed as a potential <a href="/wiki/Anti-inflammatory" title="Anti-inflammatory">anti-inflammatory</a> medication.<sup id="cite_ref-WO2020210823A1_6-1" class="reference"><a href="#cite_note-WO2020210823A1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Raz2020_7-1" class="reference"><a href="#cite_note-Raz2020-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=2C-Bu&action=edit&section=1" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=2C-Bu&action=edit&section=2" 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"><ol class="references"> <li id="cite_note-TrachselLehmanEnzensperger2013-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-TrachselLehmanEnzensperger2013_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-TrachselLehmanEnzensperger2013_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-TrachselLehmanEnzensperger2013_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-TrachselLehmanEnzensperger2013_1-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFTrachselLehmannEnzensperger2013" class="citation book cs1 cs1-prop-foreign-lang-source">Trachsel D, Lehmann D, Enzensperger C (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=-Us1kgEACAAJ"><i>Phenethylamine: von der Struktur zur Funktion</i></a> [<i>Phenethylamines: From Structure to Function</i>]. Nachtschatten-Science (in German). Solothurn: Nachtschatten-Verlag. pp. <span class="nowrap">763–</span>764, <span class="nowrap">766–</span>767, 771, 901. <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>. <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/858805226">858805226</a><span class="reference-accessdate">. Retrieved <span class="nowrap">29 January</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=Phenethylamine%3A+von+der+Struktur+zur+Funktion&rft.place=Solothurn&rft.series=Nachtschatten-Science&rft.pages=%3Cspan+class%3D%22nowrap%22%3E763-%3C%2Fspan%3E764%2C+%3Cspan+class%3D%22nowrap%22%3E766-%3C%2Fspan%3E767%2C+771%2C+901&rft.pub=Nachtschatten-Verlag&rft.date=2013&rft_id=info%3Aoclcnum%2F858805226&rft.isbn=978-3-03788-700-4&rft.aulast=Trachsel&rft.aufirst=D&rft.au=Lehmann%2C+D&rft.au=Enzensperger%2C+C&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D-Us1kgEACAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3A2C-Bu" class="Z3988"></span></span> </li> <li id="cite_note-PiHKAL1991-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-PiHKAL1991_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PiHKAL1991_2-1"><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="CITEREFShulginShulgin1991" class="citation book cs1"><a href="/wiki/Alexander_T._Shulgin" class="mw-redirect" title="Alexander T. Shulgin">Shulgin AT</a>, <a href="/wiki/Ann_Shulgin" title="Ann Shulgin">Shulgin A</a> (1991). <a rel="nofollow" class="external text" href="https://erowid.org/library/books_online/pihkal/pihkal063.shtml">"#63 DOBU 2,5-DIMETHOXY-4-(n)-BUTYLAMPHETAMINE"</a>. <a rel="nofollow" class="external text" href="https://books.google.com/books?id=O8AdHBGybpcC"><i>PiHKAL: A Chemical Love Story</i></a> (1st ed.). Berkeley, CA: 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>. <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/25627628">25627628</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=%2363+DOBU+2%2C5-DIMETHOXY-4-%28n%29-BUTYLAMPHETAMINE&rft.btitle=PiHKAL%3A+A+Chemical+Love+Story&rft.place=Berkeley%2C+CA&rft.edition=1st&rft.pub=Transform+Press&rft.date=1991&rft_id=info%3Aoclcnum%2F25627628&rft.isbn=978-0-9630096-0-9&rft.aulast=Shulgin&rft.aufirst=AT&rft.au=Shulgin%2C+A&rft_id=https%3A%2F%2Ferowid.org%2Flibrary%2Fbooks_online%2Fpihkal%2Fpihkal063.shtml&rfr_id=info%3Asid%2Fen.wikipedia.org%3A2C-Bu" class="Z3988"></span></span> </li> <li id="cite_note-SeggelYousifLyon1990-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-SeggelYousifLyon1990_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSeggelYousifLyonTiteler1990" class="citation journal cs1">Seggel MR, Yousif MY, Lyon RA, Titeler M, <a href="/wiki/Bryan_Roth" title="Bryan Roth">Roth BL</a>, Suba EA, et al. (March 1990). "A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors". <i>Journal of Medicinal Chemistry</i>. <b>33</b> (3): <span class="nowrap">1032–</span>1036. <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%2Fjm00165a023">10.1021/jm00165a023</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/2308135">2308135</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+Medicinal+Chemistry&rft.atitle=A+structure-affinity+study+of+the+binding+of+4-substituted+analogues+of+1-%282%2C5-dimethoxyphenyl%29-2-aminopropane+at+5-HT2+serotonin+receptors&rft.volume=33&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1032-%3C%2Fspan%3E1036&rft.date=1990-03&rft_id=info%3Adoi%2F10.1021%2Fjm00165a023&rft_id=info%3Apmid%2F2308135&rft.aulast=Seggel&rft.aufirst=MR&rft.au=Yousif%2C+MY&rft.au=Lyon%2C+RA&rft.au=Titeler%2C+M&rft.au=Roth%2C+BL&rft.au=Suba%2C+EA&rft.au=Glennon%2C+RA&rfr_id=info%3Asid%2Fen.wikipedia.org%3A2C-Bu" class="Z3988"></span></span> </li> <li id="cite_note-VartyCanalMueller2024-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-VartyCanalMueller2024_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-VartyCanalMueller2024_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-VartyCanalMueller2024_4-2"><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="CITEREFVartyCanalMuellerHartsel2024" class="citation journal cs1">Varty GB, Canal CE, Mueller TA, Hartsel JA, Tyagi R, Avery K, et al. (April 2024). "Synthesis and Structure-Activity Relationships of 2,5-Dimethoxy-4-Substituted Phenethylamines and the Discovery of CYB210010: A Potent, Orally Bioavailable and Long-Acting Serotonin 5-HT2 Receptor Agonist". <i>J Med Chem</i>. <b>67</b> (8): <span class="nowrap">6144–</span>6188. <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%2Facs.jmedchem.3c01961">10.1021/acs.jmedchem.3c01961</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/38593423">38593423</a>. <q>The 4-tert-butyl group was considered as a spot for potential hydroxylation by cytochrome P450s to discover analogs with short-lasting effects. However, 2C-t-Bu was a potent agonist at the 5-HT2A receptor (Ki = 9.9 nM, EC50 = 4.2 nM) and elicited a robust HTR (Supporting Information, Table S1), providing in vivo evidence that the tert-butyl group is not rapidly metabolized to an inactive compound in mice, despite predictions.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Med+Chem&rft.atitle=Synthesis+and+Structure-Activity+Relationships+of+2%2C5-Dimethoxy-4-Substituted+Phenethylamines+and+the+Discovery+of+CYB210010%3A+A+Potent%2C+Orally+Bioavailable+and+Long-Acting+Serotonin+5-HT2+Receptor+Agonist&rft.volume=67&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E6144-%3C%2Fspan%3E6188&rft.date=2024-04&rft_id=info%3Adoi%2F10.1021%2Facs.jmedchem.3c01961&rft_id=info%3Apmid%2F38593423&rft.aulast=Varty&rft.aufirst=GB&rft.au=Canal%2C+CE&rft.au=Mueller%2C+TA&rft.au=Hartsel%2C+JA&rft.au=Tyagi%2C+R&rft.au=Avery%2C+K&rft.au=Morgan%2C+ME&rft.au=Reichelt%2C+AC&rft.au=Pathare%2C+P&rft.au=Stang%2C+E&rft.au=Palfreyman%2C+MG&rft.au=Nivorozhkin%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3A2C-Bu" class="Z3988"></span></span> </li> <li id="cite_note-ShulginManningDaley2011-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-ShulginManningDaley2011_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShulginManningDaley2011" class="citation book cs1">Shulgin A, Manning T, Daley PF (2011). <a rel="nofollow" class="external text" href="https://archive.org/details/shulgin-index-vol-1/page/118/mode/1up">"#60. DOM"</a>. <i><a href="/wiki/The_Shulgin_Index,_Volume_One:_Psychedelic_Phenethylamines_and_Related_Compounds" class="mw-redirect" title="The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds">The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds</a></i>. Vol. 1. Berkeley, CA: Transform Press. pp. <span class="nowrap">118–</span>129. <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>. <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/709667010">709667010</a>. <q>2c-IB: [...] (15) Synthesis (from 2,5-dimethoxyisobutylbenzene) (Mueller, 2006); although this compound was reported here, a structure-search in Chemical Abstracts does not produce a CAS registry number (16) Threshold activity in humans at 5 mg orally; long duration (about 20 hours; Mueller, 2006). [...] Mueller, M. (2006) Personal communication with A.T. Shulgin.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=%2360.+DOM&rft.btitle=The+Shulgin+Index%2C+Volume+One%3A+Psychedelic+Phenethylamines+and+Related+Compounds&rft.place=Berkeley%2C+CA&rft.pages=%3Cspan+class%3D%22nowrap%22%3E118-%3C%2Fspan%3E129&rft.pub=Transform+Press&rft.date=2011&rft_id=info%3Aoclcnum%2F709667010&rft.isbn=978-0-9630096-3-0&rft.aulast=Shulgin&rft.aufirst=A&rft.au=Manning%2C+T&rft.au=Daley%2C+PF&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fshulgin-index-vol-1%2Fpage%2F118%2Fmode%2F1up&rfr_id=info%3Asid%2Fen.wikipedia.org%3A2C-Bu" class="Z3988"></span></span> </li> <li id="cite_note-WO2020210823A1-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-WO2020210823A1_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-WO2020210823A1_6-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1041539562">.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}</style><span class="citation patent" id="CITEREFNichols_CD,_Billac_G,_Nichols_DE"><a rel="nofollow" class="external text" href="https://patents.google.com/patent/WO2020210823A1/en">WO published 2020210823</a>, <a href="/wiki/Charles_D._Nichols" title="Charles D. Nichols">Nichols CD</a>, Billac G, <a href="/wiki/David_E._Nichols" title="David E. Nichols">Nichols DE</a>, "Compounds and methods for treating inflammatory disorders", published 15 October 2020</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Apatent&rft.number=2020210823&rft.cc=WO&rft.title=Compounds+and+methods+for+treating+inflammatory+disorders&rft.inventor=%5B%5BCharles+D.+Nichols%7CNichols+CD%5D%5D%2C+Billac+G%2C+%5B%5BDavid+E.+Nichols%7CNichols+DE%5D%5D&rft.appldate=13 April 2020&rft.pubdate=15 October 2020&rft.prioritydate=13 April 2020"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-Raz2020-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-Raz2020_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Raz2020_7-1"><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="CITEREFRaz2020" class="citation conference cs1">Raz S (February 2020). <a rel="nofollow" class="external text" href="https://www.youtube.com/watch?v=VwblUOQQwMI"><i>Eleusis Drug Development Overview</i></a>. LSX World Congress 2020.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=conference&rft.btitle=Eleusis+Drug+Development+Overview&rft.date=2020-02&rft.aulast=Raz&rft.aufirst=S&rft_id=https%3A%2F%2Fwww.youtube.com%2Fwatch%3Fv%3DVwblUOQQwMI&rfr_id=info%3Asid%2Fen.wikipedia.org%3A2C-Bu" class="Z3988"></span></span> </li> <li id="cite_note-Oberlender1989-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-Oberlender1989_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOberlender1989" class="citation web cs1">Oberlender RA (May 1989). <a rel="nofollow" class="external text" href="https://bitnest.netfirms.com/external/Theses/Oberlender1989">"Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens"</a>. <i>Purdue e-Pubs</i>. Purdue University<span class="reference-accessdate">. Retrieved <span class="nowrap">17 February</span> 2025</span>. <q>Table 7. Hallucinogenic potency of 4-alkyl-2,5-dimethoxyamphetamines.a [...] DOTB: [...] Hallucinogenic Potencyb: -c. [...] c this compound has not been established as hallucinogenic. [...] Within this homologous series, optimum activity is straight chain alkyl group, two and three carbons in length 1975). The potency increases by an order of magnitude as associated with a (Shulgin and Dyer, the 4-hydrogen of 2,5-DMA is replaced by a short alkyl chain, then decreases if the chain length exceeds four carbons. In addition, the lack of hallucinogenic activity for the tertiary butyl derivative, DOTB, suggested that branching of the 4-alkyl substituent was not tolerated. [...] In a study employing 5-MeO-DMT as the training drug in rats, DOTB and DOAM were distinguishable from this hallucinogen, while 2,5-DMA and DOM were not (Glennon et al., 1981). This was consistent with the studies described above. Surprisingly, however, stimulus generalization was not observed for DOET, DOPR, and DOBU (Glennon et al., 1981a). [...] Aldous et al. (1974) noted steric restrictions on the 4-substituent in the rabbit hyperthermia model since the 4-isopropyl derivative was more potent than the 4-tert-butyl analogue, DOTB. Additional studies with DOTB, which contains a more highly hindered benzylic carbon, indicate that hallucinogen-like activity may actually be abolished in man (Shulgin and Dyer, 1975) and drastically attenuated in animals (Glennon et al., 1982).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Purdue+e-Pubs&rft.atitle=Stereoselective+aspects+of+hallucinogenic+drug+action+and+drug+discrimination+studies+of+entactogens&rft.date=1989-05&rft.aulast=Oberlender&rft.aufirst=RA&rft_id=https%3A%2F%2Fbitnest.netfirms.com%2Fexternal%2FTheses%2FOberlender1989&rfr_id=info%3Asid%2Fen.wikipedia.org%3A2C-Bu" class="Z3988"></span></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=2C-Bu&action=edit&section=3" title="Edit section: External links"><span>edit</span></a><span 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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 src="https://auth.wikimedia.org/loginwiki/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=2C-Bu&oldid=1283153017">https://en.wikipedia.org/w/index.php?title=2C-Bu&oldid=1283153017</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" 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