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figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>10,11-Secoergoline </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:10,11-Secoergoline.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/10%2C11-Secoergoline.svg/150px-10%2C11-Secoergoline.svg.png" decoding="async" width="150" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/10%2C11-Secoergoline.svg/225px-10%2C11-Secoergoline.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/81/10%2C11-Secoergoline.svg/300px-10%2C11-Secoergoline.svg.png 2x" data-file-width="395" data-file-height="375" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">3-(piperidin-2-ylmethyl)-1<i>H</i>-indole</div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">3-(2-Piperidylmethyl)indole; α,<i>N</i>-Tetramethylenetryptamine; α,<i>N</i>-Piperidinyltryptamine; α,<i>N</i>-Pip-T</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><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="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=5275-05-8">5275-05-8</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><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=C1CCNC%28C1%29CC2%3DCNC3%3DCC%3DCC%3DC32">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.20064.html">20064</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/21346">21346</a></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><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="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C14H18N2/c1-2-7-14-13(6-1)11(10-16-14)9-12-5-3-4-8-15-12/h1-2,6-7,10,12,15-16H,3-5,8-9H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: NQAIQKCDQAOHIA-UHFFFAOYSA-N</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><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="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C1CCNC(C1)CC2=CNC3=CC=CC=C32</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>14</sub><span title="Hydrogen">H</span><sub>18</sub><span title="Nitrogen">N</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>214.31 g/mol    </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Pharmacology </th></tr> <tr> <td><a href="/wiki/Drug_class" title="Drug class">Drug class</a> </td> <td><a href="/wiki/Simplified/partial_ergoline" class="mw-redirect" title="Simplified/partial ergoline">Simplified/partial ergoline</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>10,11-Secoergoline</b>, also known as <b>3-(2-piperidylmethyl)indole</b> or as <b>α,<i>N</i>-tetramethylenetryptamine</b>, is the <a href="/wiki/Chemical_structure" title="Chemical structure">structure</a> of <a href="/wiki/Ergoline" title="Ergoline">ergoline</a> in which the <a href="/wiki/Covalent_bond" title="Covalent bond">bond</a> between the 10 and 11 positions of the <a href="/wiki/Ring_system_(chemistry)" class="mw-redirect" title="Ring system (chemistry)">ring system</a> has been broken to <a href="/wiki/Conformational_constraint" class="mw-redirect" title="Conformational constraint">unconstrain</a> the <a href="/wiki/Molecule" title="Molecule">molecule</a>.<sup id="cite_ref-Senning2019_1-0" class="reference"><a href="#cite_note-Senning2019-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PubChem_2-0" class="reference"><a href="#cite_note-PubChem-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It is also a <a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">tryptamine</a> with the <a href="/wiki/Amine" title="Amine">amine</a> <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclized</a> into a <a href="/wiki/Piperidine" title="Piperidine">piperidine</a> <a href="/wiki/Ring_(chemistry)" title="Ring (chemistry)">ring</a> connected to the α position.<sup id="cite_ref-Senning2019_1-1" class="reference"><a href="#cite_note-Senning2019-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PubChem_2-1" class="reference"><a href="#cite_note-PubChem-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>A notable <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> of 10,11-secoergoline is <a href="/wiki/CT-5252" title="CT-5252">CT-5252</a> (methyl-12-bromo-8,9-didehydro-2,3β-dihydro-6-methyl-10,11-secoergoline-8-carboxylate), which is an <a href="/wiki/Structural_analog" title="Structural analog">analogue</a> of <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">lysergic acid diethylamide</a> (LSD) with some of the same behavioral effects in animals but with much lower <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a>.<sup id="cite_ref-Nichols1973_3-0" class="reference"><a href="#cite_note-Nichols1973-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SivaSankar1975_4-0" class="reference"><a href="#cite_note-SivaSankar1975-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sivadjian1970_5-0" class="reference"><a href="#cite_note-Sivadjian1970-5"><span class="cite-bracket">[</span>5<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=10,11-Secoergoline&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/Lysergamides#Simplified_or_partial_lysergamides" class="mw-redirect" title="Lysergamides">Lysergamides § Simplified or partial lysergamides</a></li> <li><a href="/wiki/Pyr-T" title="Pyr-T">Pyr-T</a> (<i>N</i>,<i>N</i>-tetramethylenetryptamine)</li> <li><a href="/wiki/SN-22" title="SN-22">SN-22</a> (3-(1-methyl-4-piperidinyl)indole)</li> <li><a href="/wiki/MPMI_(drug)" title="MPMI (drug)">MPMI</a> (3-(<i>N</i>-methylpyrrolidin-2-ylmethyl)-1<i>H</i>-indole)</li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/EMD-386088" title="EMD-386088">EMD-386088</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=10,11-Secoergoline&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-Senning2019-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Senning2019_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Senning2019_1-1"><sup><i><b>b</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="CITEREFAlexander_Senning2019" class="citation book cs1">Alexander Senning (8 October 2019). "4. The IUPAC systematic nomenclature". <i>The Etymology of Chemical Names: Tradition and Convenience vs. Rationality in Chemical Nomenclature</i>. De Gruyter. p. 167–236. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1515%2F9783110612714-004">10.1515/9783110612714-004</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-11-061271-4" title="Special:BookSources/978-3-11-061271-4"><bdi>978-3-11-061271-4</bdi></a>. <q>10,11-Secoergoline (3-{(2S)-[(piperidin-2-yl)methyl]}-1H-indole). The name ergoline is ultimately from ergot (Claviceps purpurea).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=4.+The+IUPAC+systematic+nomenclature&rft.btitle=The+Etymology+of+Chemical+Names%3A+Tradition+and+Convenience+vs.+Rationality+in+Chemical+Nomenclature&rft.pages=167-236&rft.pub=De+Gruyter&rft.date=2019-10-08&rft_id=info%3Adoi%2F10.1515%2F9783110612714-004&rft.isbn=978-3-11-061271-4&rft.au=Alexander+Senning&rfr_id=info%3Asid%2Fen.wikipedia.org%3A10%2C11-Secoergoline" class="Z3988"></span></span> </li> <li id="cite_note-PubChem-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-PubChem_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PubChem_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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/21346">"Indole, 3-(2-piperidylmethyl)-"</a>. <i>PubChem</i><span class="reference-accessdate">. Retrieved <span class="nowrap">18 March</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=PubChem&rft.atitle=Indole%2C+3-%282-piperidylmethyl%29-&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F21346&rfr_id=info%3Asid%2Fen.wikipedia.org%3A10%2C11-Secoergoline" class="Z3988"></span></span> </li> <li id="cite_note-Nichols1973-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Nichols1973_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDavid_E._Nichols1973" class="citation thesis cs1"><a href="/wiki/David_E._Nichols" title="David E. Nichols">David E. Nichols</a> (May 1973). <a rel="nofollow" class="external text" href="https://bitnest.netfirms.com/external/Theses/Nichols1973"><i>Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid</i></a> (Thesis). <a href="/wiki/University_of_Iowa" title="University of Iowa">University of Iowa</a>. pp. <span class="nowrap">18–</span>19. <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/1194694085">1194694085</a>. <q>The dihydroindole derivative 11 was prepared by Sivajian and found to be 1/48 as active as LSD in studies with guinea pigs (38). Sivajian (38) also reported biological activities in the guinea pig for arecoline 12, 6-methylarecoline 13, and 5-phenyl-6-methylarecoline 14. These compounds were devoid of LSD-like activity in guinea pigs.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adissertation&rft.title=Potential+Psychotomimetics%3A+Bromomethoxyamphetamines+and+Structural+Congeners+of+Lysergic+Acid&rft.inst=University+of+Iowa&rft.date=1973-05&rft_id=info%3Aoclcnum%2F1194694085&rft.au=David+E.+Nichols&rft_id=https%3A%2F%2Fbitnest.netfirms.com%2Fexternal%2FTheses%2FNichols1973&rfr_id=info%3Asid%2Fen.wikipedia.org%3A10%2C11-Secoergoline" class="Z3988"></span></span> </li> <li id="cite_note-SivaSankar1975-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-SivaSankar1975_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFD._V._Siva_Sankar1975" class="citation book cs1">D. V. Siva Sankar (1975). "Molecular Investigations: Relations Between Molecular Structure and Psychobiological Activity / Molecular Aspects: Structure-Activity Relations". <a rel="nofollow" class="external text" href="https://www.samorini.it/doc1/alt_aut/sz/sankar-lsd-a-total-study.pdf#page=69"><i>LSD - A Total Study</i></a> <span class="cs1-format">(PDF)</span>. Westbury, N.Y.: PJD Publications. pp. 65–106 (70–71). <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-9600290-3-7" title="Special:BookSources/978-0-9600290-3-7"><bdi>978-0-9600290-3-7</bdi></a>. <a href="/wiki/LCCN_(identifier)" class="mw-redirect" title="LCCN (identifier)">LCCN</a> <a rel="nofollow" class="external text" href="https://lccn.loc.gov/72-95447">72-95447</a>. <q>Sivadjian reported in 1970 (15) studies on twelve lysergic acid analogues. These included arecoline-HBr, Methyl-12-bromo-8,9-didehydro-2,3-beta-dihydro-6-methyl-10,11-secoergoline-8-carboxylate, and 1,2,5,6-tetrahydro-5-phenyl-1,6-dimethyldiethylnicotinamide-HCI. Of these compounds only the methyl-12-bromo-8,9-didehydro-2,3-beta-dihydro-6-methyl-10,11-secoergoline-8-carboxylate derivative showed some activity. It disrupted the conditioned avoidance response in guinea pigs into a disorderly reflex movement of varying duration. While acetyl LSD was quite active, the acetyl derivatives obtained by acetylation of the indole nitrogen of the compounds were usually less active.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Molecular+Investigations%3A+Relations+Between+Molecular+Structure+and+Psychobiological+Activity+%2F+Molecular+Aspects%3A+Structure-Activity+Relations&rft.btitle=LSD+-+A+Total+Study&rft.place=Westbury%2C+N.Y.&rft.pages=65-106+%2870-71%29&rft.pub=PJD+Publications&rft.date=1975&rft_id=info%3Alccn%2F72-95447&rft.isbn=978-0-9600290-3-7&rft.au=D.+V.+Siva+Sankar&rft_id=https%3A%2F%2Fwww.samorini.it%2Fdoc1%2Falt_aut%2Fsz%2Fsankar-lsd-a-total-study.pdf%23page%3D69&rfr_id=info%3Asid%2Fen.wikipedia.org%3A10%2C11-Secoergoline" class="Z3988"></span></span> </li> <li id="cite_note-Sivadjian1970-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-Sivadjian1970_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSivadjian1970" class="citation journal cs1 cs1-prop-foreign-lang-source">Sivadjian J (May 1970). <a rel="nofollow" class="external text" href="https://erowid.org/references/texts/show/5057docid4847">"Etude psychopharmacologique de quelques dérivés analogues à l'acide lysergique"</a> [Psychopharmacological study of some derivatives analogous with lysergic acid]. <i>C R Acad Hebd Seances Acad Sci D</i> (in French). <b>270</b> (20): <span class="nowrap">2499–</span>2501. <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/4987582">4987582</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=C+R+Acad+Hebd+Seances+Acad+Sci+D&rft.atitle=Etude+psychopharmacologique+de+quelques+d%C3%A9riv%C3%A9s+analogues+%C3%A0+l%27acide+lysergique&rft.volume=270&rft.issue=20&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2499-%3C%2Fspan%3E2501&rft.date=1970-05&rft_id=info%3Apmid%2F4987582&rft.aulast=Sivadjian&rft.aufirst=J&rft_id=https%3A%2F%2Ferowid.org%2Freferences%2Ftexts%2Fshow%2F5057docid4847&rfr_id=info%3Asid%2Fen.wikipedia.org%3A10%2C11-Secoergoline" class="Z3988"></span></span> </li> </ol></div></div> <p><br /> </p> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline 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href="/wiki/Template:Ergolines" title="Template:Ergolines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Ergolines" title="Template talk:Ergolines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Ergolines" title="Special:EditPage/Template:Ergolines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Ergolines128" style="font-size:114%;margin:0 4em"><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_lysergamide" class="mw-redirect" title="Substituted lysergamide">Lysergamides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Non-hallucinogenic lysergamides:</i> <a href="/wiki/1P-BOL-148" title="1P-BOL-148">1P-BOL-148</a></li> <li><a href="/wiki/2-Bromo-LSD" title="2-Bromo-LSD">2-Bromo-LSD (bromolysergide; BOL-148)</a></li> <li><a href="/w/index.php?title=2-Iodo-LSD&action=edit&redlink=1" class="new" title="2-Iodo-LSD (page does not exist)">2-Iodo-LSD</a></li> <li><a href="/wiki/12-Hydroxy-LSD" title="12-Hydroxy-LSD">12-Hydroxy-LSD</a></li> <li><a href="/wiki/12-Methoxy-LSD" title="12-Methoxy-LSD">12-Methoxy-LSD</a></li> <li><a href="/wiki/Amesergide" title="Amesergide">Amesergide</a></li> <li><a href="/wiki/Cabergoline" title="Cabergoline">Cabergoline</a></li> <li><a href="/wiki/Ergometrinine" title="Ergometrinine">Ergometrinine</a></li> <li><a href="/w/index.php?title=IsoLSD&action=edit&redlink=1" class="new" title="IsoLSD (page does not exist)">isoLSD</a></li> <li><a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a></li> <li><a href="/wiki/Lysergic_acid_cyclobutylamide" title="Lysergic acid cyclobutylamide">Lysergic acid cyclobutylamide (LAcB)</a></li> <li><a href="/wiki/Lysergic_acid_cyclopentylamide" class="mw-redirect" title="Lysergic acid cyclopentylamide">Lysergic acid cyclopentylamide (cepentil; LCyP)</a></li> <li><a href="/w/index.php?title=MBL-61&action=edit&redlink=1" class="new" title="MBL-61 (page does not exist)">MBL-61 (2-bromo-1-methyl-LSD)</a></li></ul> <ul><li><i>Psychedelic lysergamides:</i> <a href="/wiki/1B-LSD" title="1B-LSD">1B-LSD</a></li> <li><a href="/wiki/1cP-AL-LAD" title="1cP-AL-LAD">1cP-AL-LAD</a></li> <li><a href="/wiki/1cP-LSD" title="1cP-LSD">1cP-LSD</a></li> <li><a href="/wiki/1D-LSD" title="1D-LSD">1D-LSD</a></li> <li><a href="/wiki/1DD-LSD" title="1DD-LSD">1DD-LSD</a></li> <li><a href="/wiki/1H-LSD" title="1H-LSD">1H-LSD</a></li> <li><a href="/wiki/1P-AL-LAD" title="1P-AL-LAD">1P-AL-LAD</a></li> <li><a href="/wiki/1P-ETH-LAD" title="1P-ETH-LAD">1P-ETH-LAD</a></li> <li><a href="/wiki/1P-LSD" title="1P-LSD">1P-LSD</a></li> <li><a href="/w/index.php?title=1P-MIPLA&action=edit&redlink=1" class="new" title="1P-MIPLA (page does not exist)">1P-MIPLA</a></li> <li><a href="/wiki/1S-LSD" title="1S-LSD">1S-LSD</a></li> <li><a href="/wiki/1T-AL-LAD" title="1T-AL-LAD">1T-AL-LAD</a></li> <li><a href="/wiki/1T-LSD" title="1T-LSD">1T-LSD</a></li> <li><a href="/wiki/1V-LSD" title="1V-LSD">1V-LSD</a></li> <li><a href="/wiki/AL-LAD" title="AL-LAD">AL-LAD</a></li> <li><a href="/w/index.php?title=ALA-10&action=edit&redlink=1" class="new" title="ALA-10 (page does not exist)">ALA-10 (1-acety-LAE)</a></li> <li><a href="/wiki/ALD-52" title="ALD-52">ALD-52 (1-acetyl-LSD)</a></li> <li><a href="/wiki/BU-LAD" title="BU-LAD">BU-LAD</a></li> <li><a href="/wiki/CYP-LAD" title="CYP-LAD">CYP-LAD</a></li> <li><a href="/wiki/Diallyllysergamide" title="Diallyllysergamide">Diallyllysergamide (DAL)</a></li> <li><a href="/wiki/Dimethyllysergamide" title="Dimethyllysergamide">Dimethyllysergamide (DAM-57)</a></li> <li><a href="/wiki/Lysergic_acid_dipropylamide" title="Lysergic acid dipropylamide">Dipropyllysergamide (DPL)</a></li> <li><a href="/wiki/Ergine" title="Ergine">Ergine (lysergic acid amide; LSA; LA-111; lysergamide)</a></li> <li><a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">Ergometrine (ergonovine, ergobasine)</a></li> <li><a href="/wiki/ETH-LAD" title="ETH-LAD">ETH-LAD</a></li> <li><a href="/wiki/Ethylcyclopropyllysergamide" class="mw-redirect" title="Ethylcyclopropyllysergamide">Ethylcyclopropyllysergamide (ECPLA)</a></li> <li><a href="/wiki/Ethylisopropyllysergamide" title="Ethylisopropyllysergamide">Ethylisopropyllysergamide (EIPLA)</a></li> <li><a href="/wiki/Ethyltrifluoroethyllysergamide" class="mw-redirect" title="Ethyltrifluoroethyllysergamide">Ethyltrifluoroethyllysergamide (ETFELA)</a></li> <li><a href="/wiki/IP-LAD" class="mw-redirect" title="IP-LAD">IP-LAD</a></li> <li><a href="/wiki/Methylpropyllysergamide" class="mw-redirect" title="Methylpropyllysergamide">Methylpropyllysergamide (LAMPA)</a></li> <li><a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">Lysergic acid diethylamide (LSD; lysergide)</a></li> <li><a href="/wiki/Lysergic_acid_ethylamide" class="mw-redirect" title="Lysergic acid ethylamide">Lysergic acid ethylamide (LAE-32, LAE)</a></li> <li><a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">Lysergic acid hydroxyethylamide (LSH)</a></li> <li><a href="/wiki/Lysergic_acid_morpholide" class="mw-redirect" title="Lysergic acid morpholide">Lysergic acid morpholide (LSM-775)</a></li> <li><a href="/wiki/Lysergic_acid_pyrrolidine" class="mw-redirect" title="Lysergic acid pyrrolidine">Lysergic acid pyrrolidine (LPD-824)</a></li> <li><a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">Lysergic acid 2-butylamide (LSB)</a></li> <li><a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ)</a></li> <li><a href="/wiki/Lysergic_acid_3-pentyl_amide" title="Lysergic acid 3-pentyl amide">Lysergic acid 3-pentylamide (LSP)</a></li> <li><a href="/wiki/Methylergometrine" title="Methylergometrine">Methylergometrine (methylergonovine, methylergobasine; Methergine)</a></li> <li><a href="/wiki/Methylisopropyllysergamide" title="Methylisopropyllysergamide">Methylisopropyllysergamide (MIPLA)</a></li> <li><a href="/wiki/Methysergide" title="Methysergide">Methysergide (1-methylmethylergonovine; UML-491)</a></li> <li><a href="/w/index.php?title=MLA-74&action=edit&redlink=1" class="new" title="MLA-74 (page does not exist)">MLA-74 (1-methyl-LAE)</a></li> <li><a href="/wiki/MLD-41" title="MLD-41">MLD-41 (1-methyl-LSD)</a></li> <li><a href="/w/index.php?title=1-Methyllysergic_acid_pyrrolidide&action=edit&redlink=1" class="new" title="1-Methyllysergic acid pyrrolidide (page does not exist)">MPD-75 (1-methyllysergic acid pyrrolidide)</a></li> <li><a href="/w/index.php?title=OML-632&action=edit&redlink=1" class="new" title="OML-632 (page does not exist)">OML-632 (1-hydroxymethyl-LSD)</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> <ul><li><i>Unsorted lysergamides:</i> <a href="/w/index.php?title=13-Fluoro-LSD&action=edit&redlink=1" class="new" title="13-Fluoro-LSD (page does not exist)">13-Fluoro-LSD</a></li> <li><a href="/w/index.php?title=13-Hydroxy-LSD&action=edit&redlink=1" class="new" title="13-Hydroxy-LSD (page does not exist)">13-Hydroxy-LSD</a></li> <li><a href="/w/index.php?title=14-Hydroxy-LSD&action=edit&redlink=1" class="new" title="14-Hydroxy-LSD (page does not exist)">14-Hydroxy-LSD</a></li> <li><a href="/w/index.php?title=Dihydroergometrine&action=edit&redlink=1" class="new" title="Dihydroergometrine (page does not exist)">Dihydroergometrine (dihydroergonovine, dihydroergobasine)</a></li> <li><a href="/wiki/Ethylpropyllysergamide" title="Ethylpropyllysergamide">Ethylpropyllysergamide (EPLA; LEP-57)</a></li> <li><a href="/wiki/FLUORETH-LAD" title="FLUORETH-LAD">FLUORETH-LAD</a></li> <li><a href="/w/index.php?title=Lysergic_acid_ethyl-2-hydroxyethylamide&action=edit&redlink=1" class="new" title="Lysergic acid ethyl-2-hydroxyethylamide (page does not exist)">Lysergic acid ethyl-2-hydroxyethylamide (LEO)</a></li> <li><a href="/w/index.php?title=Lysergic_acid_azepane&action=edit&redlink=1" class="new" title="Lysergic acid azepane (page does not exist)">Lysergic acid azepane (LSD-Azepane)</a></li> <li><a href="/w/index.php?title=Lysergic_acid_isopropylamide&action=edit&redlink=1" class="new" title="Lysergic acid isopropylamide (page does not exist)">Lysergic acid isopropylamide (LAiP)</a></li> <li><a href="/wiki/Lysergic_acid_piperidine" class="mw-redirect" title="Lysergic acid piperidine">Lysergic acid piperidine (LSD-Pip)</a></li> <li><a href="/w/index.php?title=Lysergic_acid_tert-butylamide&action=edit&redlink=1" class="new" title="Lysergic acid tert-butylamide (page does not exist)">Lysergic acid <i>tert</i>-butylamide (LAtB)</a></li> <li><a href="/wiki/Propisergide" title="Propisergide">Propisergide (1-methylergonovine)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Ergopeptine" class="mw-redirect" title="Ergopeptine">Ergopeptines</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/Bromocriptine" title="Bromocriptine">Bromocriptine</a></li> <li><a href="/wiki/Dihydroergocornine" title="Dihydroergocornine">Dihydroergocornine</a></li> <li><a href="/wiki/Dihydroergocristine" title="Dihydroergocristine">Dihydroergocristine</a></li> <li><a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">Dihydroergocryptine</a></li> <li><a href="/w/index.php?title=Dihydroergosine&action=edit&redlink=1" class="new" title="Dihydroergosine (page does not exist)">Dihydroergosine</a></li> <li><a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">Dihydroergotamine</a></li> <li><a href="/wiki/Epicriptine" title="Epicriptine">Epicriptine</a></li> <li><a href="/wiki/Ergocornine" title="Ergocornine">Ergocornine</a></li> <li><a href="/wiki/Ergocristine" title="Ergocristine">Ergocristine</a></li> <li><a href="/wiki/Ergocryptine" title="Ergocryptine">Ergocryptine</a></li> <li><a href="/wiki/Ergoloid" title="Ergoloid">Ergoloid (dihydroergotoxine; Hydergine)</a></li> <li><a href="/w/index.php?title=Ergonine&action=edit&redlink=1" class="new" title="Ergonine (page does not exist)">Ergonine</a></li> <li><a href="/wiki/Ergosine" title="Ergosine">Ergosine</a></li> <li><a href="/wiki/Ergostine" title="Ergostine">Ergostine</a></li> <li><a href="/wiki/Ergotamine" title="Ergotamine">Ergotamine</a></li> <li><a href="/wiki/Ergotoxine" class="mw-redirect" title="Ergotoxine">Ergotoxine</a></li> <li><a href="/wiki/Ergovaline" title="Ergovaline">Ergovaline</a></li> <li><a href="/w/index.php?title=Fludihydroergotamine&action=edit&redlink=1" class="new" title="Fludihydroergotamine (page does not exist)">Fludihydroergotamine</a></li> <li><a href="/w/index.php?title=Mergocriptine&action=edit&redlink=1" class="new" title="Mergocriptine (page does not exist)">Mergocriptine</a></li> <li><a href="/w/index.php?title=Metergotamine&action=edit&redlink=1" class="new" title="Metergotamine (page does not exist)">Metergotamine</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/Clavine" class="mw-redirect" title="Clavine">Clavines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=6,8-Dimethylergoline&action=edit&redlink=1" class="new" title="6,8-Dimethylergoline (page does not exist)">6,8-Dimethylergoline (clavine)</a></li> <li><a href="/wiki/9-Deacetoxyfumigaclavine_C" title="9-Deacetoxyfumigaclavine C">9-Deacetoxyfumigaclavine C</a></li> <li><a href="/wiki/Agroclavine" title="Agroclavine">Agroclavine</a></li> <li><a href="/wiki/Chanoclavine" title="Chanoclavine">Chanoclavine</a></li> <li><a href="/wiki/Chanoclavine_II" title="Chanoclavine II">Chanoclavine II</a></li> <li><a href="/wiki/Costaclavin" title="Costaclavin">Costaclavin</a></li> <li><a href="/wiki/Cycloclavine" title="Cycloclavine">Cycloclavine</a></li> <li><a href="/wiki/Elymoclavine" title="Elymoclavine">Elymoclavine</a></li> <li><a href="/wiki/Epoxyagroclavine" title="Epoxyagroclavine">Epoxyagroclavine</a></li> <li><a href="/wiki/Festuclavine" title="Festuclavine">Festuclavine</a></li> <li><a href="/wiki/Fumigaclavine_A" title="Fumigaclavine A">Fumigaclavine A</a></li> <li><a href="/wiki/Fumigaclavine_B" title="Fumigaclavine B">Fumigaclavine B</a></li> <li><a href="/wiki/Fumigaclavine_C" title="Fumigaclavine C">Fumigaclavine C</a></li> <li><a href="/wiki/Paliclavine" title="Paliclavine">Paliclavine</a></li> <li><a href="/wiki/Penniclavine" title="Penniclavine">Penniclavine</a></li> <li><a href="/wiki/Setoclavine" title="Setoclavine">Setoclavine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other<br /> ergolines</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/13-Fluorolysergol" title="13-Fluorolysergol">13-Fluorolysergol</a></li> <li><a href="/wiki/Acetergamine" title="Acetergamine">Acetergamine</a></li> <li><a href="/w/index.php?title=Brazergoline&action=edit&redlink=1" class="new" title="Brazergoline (page does not exist)">Brazergoline</a></li> <li><a href="/wiki/Bromerguride" title="Bromerguride">Bromerguride (2-bromolisuride)</a></li> <li><a href="/w/index.php?title=Cianergoline&action=edit&redlink=1" class="new" title="Cianergoline (page does not exist)">Cianergoline</a></li> <li><a href="/wiki/CY-208,243" title="CY-208,243">CY-208,243</a></li> <li><a href="/w/index.php?title=Delergotrile&action=edit&redlink=1" class="new" title="Delergotrile (page does not exist)">Delergotrile</a></li> <li><a href="/wiki/Descarboxylysergic_acid" title="Descarboxylysergic acid">Descarboxylysergic acid</a></li> <li><a href="/w/index.php?title=Dihydrolysergic_acid&action=edit&redlink=1" class="new" title="Dihydrolysergic acid (page does not exist)">Dihydrolysergic acid</a></li> <li><a href="/w/index.php?title=Disulergine&action=edit&redlink=1" class="new" title="Disulergine (page does not exist)">Disulergine</a></li> <li><a href="/w/index.php?title=Dosergoside&action=edit&redlink=1" class="new" title="Dosergoside (page does not exist)">Dosergoside</a></li> <li><a href="/w/index.php?title=Ergolene&action=edit&redlink=1" class="new" title="Ergolene (page does not exist)">Ergolene</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergoline</a></li> <li><a href="/w/index.php?title=Etisulergine&action=edit&redlink=1" class="new" title="Etisulergine (page does not exist)">Etisulergine</a></li> <li><a href="/wiki/Lergotrile" title="Lergotrile">Lergotrile</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/Lysergic_acid" title="Lysergic acid">Lysergic acid</a></li> <li><a href="/wiki/Lysergic_acid_methyl_ester" title="Lysergic acid methyl ester">Lysergic acid methyl ester</a></li> <li><a href="/wiki/Lysergine" title="Lysergine">Lysergine</a></li> <li><a href="/wiki/Lysergol" title="Lysergol">Lysergol</a></li> <li><a href="/wiki/Mesulergine" title="Mesulergine">Mesulergine</a></li> <li><a href="/wiki/Metergoline" title="Metergoline">Metergoline</a></li> <li><a href="/wiki/Nicergoline" title="Nicergoline">Nicergoline</a></li> <li><a href="/wiki/Pergolide" title="Pergolide">Pergolide</a></li> <li><a href="/w/index.php?title=Proterguride&action=edit&redlink=1" class="new" title="Proterguride (page does not exist)">Proterguride</a></li> <li><a href="/w/index.php?title=Romergoline&action=edit&redlink=1" class="new" title="Romergoline (page does not exist)">Romergoline</a></li> <li><a href="/wiki/Sergolexole" title="Sergolexole">Sergolexole</a></li> <li><a href="/wiki/Terguride" title="Terguride">Terguride</a></li> <li><a href="/w/index.php?title=Tiomergine&action=edit&redlink=1" class="new" title="Tiomergine (page does not exist)">Tiomergine</a></li> <li><a href="/wiki/Voxergolide" title="Voxergolide">Voxergolide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related<br /> compounds</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/A-86929" title="A-86929">A-86929</a></li> <li><a href="/wiki/Adrogolide" class="mw-redirect" title="Adrogolide">Adrogolide</a></li> <li><a href="/wiki/Naxagolide" title="Naxagolide">Naxagolide</a></li> <li><a href="/wiki/Quinagolide" title="Quinagolide">Quinagolide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Simplified_ergoline" class="mw-redirect" title="Simplified ergoline">Simplified or<br /> partial ergolines</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/Bay_R_1531" title="Bay R 1531">Bay R 1531 (LY-197206)</a></li> <li><a href="/wiki/CT-5252" title="CT-5252">CT-5252</a></li> <li><a href="/w/index.php?title=N-DEAOP-NMPEA&action=edit&redlink=1" class="new" title="N-DEAOP-NMPEA (page does not exist)"><i>N</i>-DEAOP-NMPEA</a></li> <li><a href="/wiki/N-DEAOP-NMT" title="N-DEAOP-NMT"><i>N</i>-DEAOP-NMT</a></li> <li><a href="/wiki/DEIMDHPCA" title="DEIMDHPCA">DEIMDHPCA</a></li> <li><a href="/wiki/LY-178210" title="LY-178210">LY-178210</a></li> <li><a href="/wiki/LY-293284" title="LY-293284">LY-293284</a></li> <li><a href="/wiki/5-MeO-N-DEAOP-NET" class="mw-redirect" title="5-MeO-N-DEAOP-NET">5-MeO-<i>N</i>-DEAOP-NET</a></li> <li><a href="/wiki/5-MeO-N-DEAOP-NMT" class="mw-redirect" title="5-MeO-N-DEAOP-NMT">5-MeO-<i>N</i>-DEAOP-NMT</a></li> <li><a href="/wiki/NDTDI" title="NDTDI">NDTDI</a></li> <li><a href="/w/index.php?title=RU-27251&action=edit&redlink=1" class="new" title="RU-27251 (page does not exist)">RU-27251</a></li> <li><a href="/wiki/RU-27849" title="RU-27849">RU-27849</a></li> <li><a href="/w/index.php?title=RU-28251&action=edit&redlink=1" class="new" title="RU-28251 (page does not exist)">RU-28251</a></li> <li><a class="mw-selflink selflink">10,11-Secoergoline (α,<i>N</i>-Pip-T)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Natural<br /> sources</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><a href="/wiki/Achnatherum_robustum" title="Achnatherum robustum">Achnatherum robustum</a></i> (Sleepy Grass)</li> <li><a href="/wiki/Claviceps" class="mw-redirect" title="Claviceps"><i>Claviceps</i> spp.</a> (Ergot)<br />Morning glory: <i><a href="/wiki/Argyreia_nervosa" title="Argyreia nervosa">Argyreia nervosa</a></i> (Hawaiian Baby Woodrose), <i><a href="/wiki/Ipomoea" title="Ipomoea"><i>Ipomoea</i> spp.</a></i> (Morning Glory, Tlitliltzin, Badoh Negro), <i><a href="/wiki/Turbina_corymbosa" class="mw-redirect" title="Turbina corymbosa">Rivea corymbosa</a></i> (Coaxihuitl, Ololiúqui)</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="Tryptamines232" 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:Tryptamines" title="Template:Tryptamines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tryptamines" title="Template talk:Tryptamines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tryptamines" title="Special:EditPage/Template:Tryptamines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Tryptamines232" style="font-size:114%;margin:0 4em"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Methyltryptamine" title="1-Methyltryptamine">1-Methyl-T</a></li> <li><a href="/wiki/1-Methylpsilocin" title="1-Methylpsilocin">1-Methylpsilocin</a></li> <li><a href="/wiki/1-Pr-5-MeO-AMT" class="mw-redirect" title="1-Pr-5-MeO-AMT">1-Pr-5-MeO-AMT</a></li> <li><a href="/wiki/2-HO-NMT" title="2-HO-NMT">2-HO-NMT</a></li> <li><a href="/wiki/2-Me-DET" title="2-Me-DET">2-Me-DET</a></li> <li><a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Methyl-5-HT</a></li> <li><a href="/wiki/2,N,N-TMT" title="2,N,N-TMT">2,<i>N</i>,<i>N</i>-TMT</a></li> <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/4,5-Dihydroxytryptamine" title="4,5-Dihydroxytryptamine">4,5-DHT</a></li> <li><a href="/wiki/4-AcO-DALT" title="4-AcO-DALT">4-AcO-DALT</a></li> <li><a href="/wiki/4-Acetoxy-DET" class="mw-redirect" title="4-Acetoxy-DET">4-AcO-DET</a></li> <li><a href="/wiki/4-Acetoxy-DiPT" title="4-Acetoxy-DiPT">4-AcO-DiPT</a></li> <li><a href="/wiki/4-AcO-DPT" title="4-AcO-DPT">4-AcO-DPT</a></li> <li><a href="/w/index.php?title=4-AcO-EPT&action=edit&redlink=1" class="new" title="4-AcO-EPT (page does not exist)">4-AcO-EPT</a></li> <li><a href="/w/index.php?title=4-AcO-MALT&action=edit&redlink=1" class="new" title="4-AcO-MALT (page does not exist)">4-AcO-MALT</a></li> <li><a href="/wiki/4-Acetoxy-MET" class="mw-redirect" title="4-Acetoxy-MET">4-AcO-MET</a></li> <li><a href="/wiki/4-Acetoxy-MiPT" class="mw-redirect" title="4-Acetoxy-MiPT">4-AcO-MiPT</a></li> <li><a href="/w/index.php?title=4-AcO-NMT&action=edit&redlink=1" class="new" title="4-AcO-NMT (page does not exist)">4-AcO-NMT</a></li> <li><a href="/w/index.php?title=4-AcO-TMT&action=edit&redlink=1" class="new" title="4-AcO-TMT (page does not exist)">4-AcO-TMT</a></li> <li><a href="/wiki/4-Fluoro-5-MeO-pyr-T" class="mw-redirect" title="4-Fluoro-5-MeO-pyr-T">4-F-5-MeO-pyr-T</a></li> <li><a href="/wiki/4-Fluoro-5-methoxy-DMT" title="4-Fluoro-5-methoxy-DMT">4-F-5-MeO-DMT</a></li> <li><a href="/wiki/4-Fluoro-DMT" title="4-Fluoro-DMT">4-Fluoro-DMT</a></li> <li><a href="/w/index.php?title=4-Fluorotryptamine&action=edit&redlink=1" class="new" title="4-Fluorotryptamine (page does not exist)">4-Fluoro-T</a></li> <li><a href="/wiki/4-Hydroxy-5-methoxytryptamine" title="4-Hydroxy-5-methoxytryptamine">4-HO-5-MeO-T</a></li> <li><a href="/w/index.php?title=4-HO-DALT&action=edit&redlink=1" class="new" title="4-HO-DALT (page does not exist)">4-HO-DALT</a></li> <li><a href="/wiki/4-HO-DBT" title="4-HO-DBT">4-HO-DBT</a></li> <li><a href="/wiki/4-HO-DET" title="4-HO-DET">4-HO-DET</a></li> <li><a href="/wiki/4-HO-DPT" title="4-HO-DPT">4-HO-DPT</a></li> <li><a href="/wiki/4-HO-DSBT" title="4-HO-DSBT">4-HO-DSBT</a></li> <li><a href="/wiki/4-HO-EPT" title="4-HO-EPT">4-HO-EPT</a></li> <li><a href="/wiki/4-HO-MALT" title="4-HO-MALT">4-HO-MALT</a></li> <li><a href="/wiki/4-HO-MET" title="4-HO-MET">4-HO-MET</a></li> <li><a href="/wiki/4-HO-McPT" title="4-HO-McPT">4-HO-McPT</a></li> <li><a href="/wiki/4-HO-McPeT" title="4-HO-McPeT">4-HO-McPeT</a></li> <li><a href="/wiki/4-HO-MiPT" title="4-HO-MiPT">4-HO-MiPT</a></li> <li><a href="/wiki/4-HO-MPT" title="4-HO-MPT">4-HO-MPT</a></li> <li><a href="/w/index.php?title=4-HO-MsBT&action=edit&redlink=1" class="new" title="4-HO-MsBT (page does not exist)">4-HO-MsBT</a></li> <li><a href="/wiki/4-HO-NALT" title="4-HO-NALT">4-HO-NALT</a></li> <li><a href="/w/index.php?title=4-HO-NiPT&action=edit&redlink=1" class="new" title="4-HO-NiPT (page does not exist)">4-HO-NiPT</a></li> <li><a href="/wiki/4-HO-NMT" class="mw-redirect" title="4-HO-NMT">4-HO-NMT</a></li> <li><a href="/wiki/4-HO-PiPT" title="4-HO-PiPT">4-HO-PiPT</a></li> <li><a href="/wiki/4-HO-pyr-T" title="4-HO-pyr-T">4-HO-pyr-T</a></li> <li><a href="/wiki/4-HO-TMT" title="4-HO-TMT">4-HO-TMT</a></li> <li><a href="/wiki/4-Hydroxytryptamine" title="4-Hydroxytryptamine">4-HT</a></li> <li><a href="/w/index.php?title=4-MeO-DiPT&action=edit&redlink=1" class="new" title="4-MeO-DiPT (page does not exist)">4-MeO-DiPT</a></li> <li><a href="/wiki/4-MeO-DMT" title="4-MeO-DMT">4-MeO-DMT</a></li> <li><a href="/wiki/4-MeO-MiPT" title="4-MeO-MiPT">4-MeO-MiPT</a></li> <li><a href="/w/index.php?title=4-MeO-T&action=edit&redlink=1" class="new" title="4-MeO-T (page does not exist)">4-MeO-T</a></li> <li><a href="/wiki/4-PrO-DMT" title="4-PrO-DMT">4-PrO-DMT</a></li> <li><a href="/wiki/4,5-MDO-DMT" title="4,5-MDO-DMT">4,5-MDO-DMT</a></li> <li><a href="/wiki/4,5-MDO-DiPT" title="4,5-MDO-DiPT">4,5-MDO-DiPT</a></li> <li><a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</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=5-Bromotryptamine&action=edit&redlink=1" class="new" title="5-Bromotryptamine (page does not exist)">5-Bromo-T</a></li> <li><a href="/wiki/5-Chloro-DMT" title="5-Chloro-DMT">5-Chloro-DMT</a></li> <li><a href="/w/index.php?title=5-Chlorotryptamine&action=edit&redlink=1" class="new" title="5-Chlorotryptamine (page does not exist)">5-Chloro-T</a></li> <li><a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a></li> <li><a href="/wiki/5-Ethoxy-DMT" title="5-Ethoxy-DMT">5-Ethoxy-DMT</a></li> <li><a href="/wiki/5-Ethyl-DMT" title="5-Ethyl-DMT">5-Ethyl-DMT</a></li> <li><a href="/wiki/5-Fluoro-DET" title="5-Fluoro-DET">5-Fluoro-DET</a></li> <li><a href="/wiki/5-Fluoro-DMT" title="5-Fluoro-DMT">5-Fluoro-DMT</a></li> <li><a href="/wiki/5-Fluoro-EPT" title="5-Fluoro-EPT">5-Fluoro-EPT</a></li> <li><a href="/wiki/5-Fluorotryptamine" title="5-Fluorotryptamine">5-Fluoro-T</a></li> <li><a href="/wiki/5-HO-DiPT" title="5-HO-DiPT">5-HO-DiPT</a></li> <li><a href="/w/index.php?title=5-HO-NiPT&action=edit&redlink=1" class="new" title="5-HO-NiPT (page does not exist)">5-HO-NiPT</a></li> <li><a href="/wiki/5-Hydroxytryptophan" title="5-Hydroxytryptophan">5-HTP (oxitriptan)</a></li> <li><a href="/wiki/5-MeO-2-TMT" title="5-MeO-2-TMT">5-MeO-2-TMT</a></li> <li><a href="/w/index.php?title=5-MeO-34MPEMT&action=edit&redlink=1" class="new" title="5-MeO-34MPEMT (page does not exist)">5-MeO-34MPEMT</a></li> <li><a href="/wiki/5-Methoxy-7,N,N-trimethyltryptamine" title="5-Methoxy-7,N,N-trimethyltryptamine">5-MeO-7,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/5-MeO-DBT" title="5-MeO-DBT">5-MeO-DBT</a></li> <li><a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</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/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a></li> <li><a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a></li> <li><a href="/wiki/5-MeO-EiPT" title="5-MeO-EiPT">5-MeO-EiPT</a></li> <li><a href="/wiki/5-MeO-EPT" title="5-MeO-EPT">5-MeO-EPT</a></li> <li><a href="/wiki/5-MeO-MALT" title="5-MeO-MALT">5-MeO-MALT</a></li> <li><a href="/wiki/5-MeO-MET" title="5-MeO-MET">5-MeO-MET</a></li> <li><a href="/wiki/5-MeO-MiPT" title="5-MeO-MiPT">5-MeO-MiPT</a></li> <li><a href="/wiki/5-MeO-NET" title="5-MeO-NET">5-MeO-NET</a></li> <li><a href="/wiki/5-MeO-NiPT" title="5-MeO-NiPT">5-MeO-NiPT</a></li> <li><a href="/wiki/5-MeO-NMT" title="5-MeO-NMT">5-MeO-NMT</a></li> <li><a href="/wiki/5-MeO-pyr-T" title="5-MeO-pyr-T">5-MeO-pyr-T</a></li> <li><a href="/wiki/5-MeO-NBpBrT" title="5-MeO-NBpBrT">5-MeO-NBpBrT</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MeO-T (5-MT; mexamine)</a></li> <li><a href="/wiki/5-MeO-T-NBOMe" title="5-MeO-T-NBOMe">5-MeO-T-NBOMe</a></li> <li><a href="/wiki/5-MeS-DMT" title="5-MeS-DMT">5-MeS-DMT</a></li> <li><a href="/wiki/5,N,N-TMT" title="5,N,N-TMT">5-Methyl-DMT</a></li> <li><a href="/wiki/5-Methyltryptamine" title="5-Methyltryptamine">5-Methyl-T</a></li> <li><a href="/w/index.php?title=5-MT-NB3OMe&action=edit&redlink=1" class="new" title="5-MT-NB3OMe (page does not exist)">5-MT-NB3OMe</a></li> <li><a href="/wiki/5-(Nonyloxy)tryptamine" title="5-(Nonyloxy)tryptamine">5-NOT</a></li> <li><a href="/wiki/5,6-MeO-MiPT" title="5,6-MeO-MiPT">5,6-MeO-MiPT</a></li> <li><a href="/wiki/5,6-MDO-DiPT" title="5,6-MDO-DiPT">5,6-MDO-DiPT</a></li> <li><a href="/wiki/5,6-MDO-DMT" title="5,6-MDO-DMT">5,6-MDO-DMT</a></li> <li><a href="/wiki/5,6-MDO-MiPT" title="5,6-MDO-MiPT">5,6-MDO-MiPT</a></li> <li><a href="/wiki/5,6-Dihydroxytryptamine" title="5,6-Dihydroxytryptamine">5,6-DHT</a></li> <li><a href="/wiki/5,7-Dihydroxytryptamine" title="5,7-Dihydroxytryptamine">5,7-DHT</a></li> <li><a href="/wiki/6-Fluoro-DET" title="6-Fluoro-DET">6-Fluoro-DET</a></li> <li><a href="/wiki/6-Fluoro-DMT" title="6-Fluoro-DMT">6-Fluoro-DMT</a></li> <li><a href="/wiki/6-Fluorotryptamine" title="6-Fluorotryptamine">6-Fluoro-T</a></li> <li><a href="/wiki/6-MeO-DMT" title="6-MeO-DMT">6-MeO-DMT</a></li> <li><a href="/w/index.php?title=6-Methoxytryptamine&action=edit&redlink=1" class="new" title="6-Methoxytryptamine (page does not exist)">6-MeO-T</a></li> <li><a href="/w/index.php?title=6-Methyltryptamine&action=edit&redlink=1" class="new" title="6-Methyltryptamine (page does not exist)">6-Methyl-T</a></li> <li><a href="/wiki/6,7-Dihydroxytryptamine" title="6,7-Dihydroxytryptamine">6,7-DHT</a></li> <li><a href="/wiki/7-Chlorotryptamine" title="7-Chlorotryptamine">7-Chloro-T</a></li> <li><a href="/w/index.php?title=7-Methoxytryptamine&action=edit&redlink=1" class="new" title="7-Methoxytryptamine (page does not exist)">7-MeO-T</a></li> <li><a href="/wiki/7,N,N-TMT" title="7,N,N-TMT">7-Methyl-DMT</a></li> <li><a href="/w/index.php?title=7-Methyltryptamine&action=edit&redlink=1" class="new" title="7-Methyltryptamine (page does not exist)">7-Methyl-T</a></li> <li><a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine (5-AT)</a></li> <li><a href="/wiki/Aeruginascin" title="Aeruginascin">Aeruginascin (4-PO-TMT)</a></li> <li><a href="/wiki/AGH-107" title="AGH-107">AGH-107</a></li> <li><a href="/wiki/AGH-192" title="AGH-192">AGH-192</a></li> <li><a href="/wiki/AH-494" title="AH-494">AH-494</a></li> <li><a href="/w/index.php?title=ALiPT&action=edit&redlink=1" class="new" title="ALiPT (page does not exist)">ALiPT</a></li> <li><a href="/wiki/Alpertine" title="Alpertine">Alpertine</a></li> <li><a href="/wiki/Baeocystin" title="Baeocystin">Baeocystin (4-PO-NMT)</a></li> <li><a href="/wiki/Benzotript" title="Benzotript">Benzotript (4-chlorobenzoyl-<small>L</small>-tryptophan)</a></li> <li><a href="/wiki/Bretisilocin" title="Bretisilocin">Bretisilocin (5-fluoro-MET)</a></li> <li><a href="/wiki/Bufotenidine" title="Bufotenidine">Bufotenidine (5-HTQ)</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin (5-HO-DMT)</a></li> <li><a href="/wiki/Convolutindole_A" title="Convolutindole A">Convolutindole A</a></li> <li><a href="/wiki/CP-132,484" title="CP-132,484">CP-132,484</a></li> <li><a href="/wiki/DALT" title="DALT">DALT</a></li> <li><a href="/wiki/Dibutyltryptamine" title="Dibutyltryptamine">DBT</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a></li> <li><a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a></li> <li><a href="/wiki/E-6801" title="E-6801">E-6801</a></li> <li><a href="/wiki/E-6837" title="E-6837">E-6837</a></li> <li><a href="/wiki/Ethylisopropyltryptamine" title="Ethylisopropyltryptamine">EiPT</a></li> <li><a href="/wiki/EMDT" title="EMDT">EMDT</a></li> <li><a href="/wiki/Ethylpropyltryptamine" title="Ethylpropyltryptamine">EPT</a></li> <li><a href="/wiki/Ethocybin" title="Ethocybin">Ethocybin (4-PO-DET)</a></li> <li><a href="/wiki/FGIN-127" title="FGIN-127">FGIN-127</a></li> <li><a href="/wiki/FGIN-143" title="FGIN-143">FGIN-143</a></li> <li><a href="/wiki/FT-104" class="mw-redirect" title="FT-104">FT-104</a></li> <li><a href="/wiki/HIOC" title="HIOC">HIOC</a></li> <li><a href="/wiki/Idalopirdine" title="Idalopirdine">Idalopirdine</a></li> <li><a href="/w/index.php?title=Indolylethylfentanyl&action=edit&redlink=1" class="new" title="Indolylethylfentanyl (page does not exist)">Indolylethylfentanyl</a></li> <li><a href="/wiki/Indorenate" title="Indorenate">Indorenate</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">Iprocin (4-HO-DiPT)</a></li> <li><a href="/wiki/Isamide" title="Isamide">Isamide</a></li> <li><a href="/wiki/Lespedamine" title="Lespedamine">Lespedamine</a></li> <li><a href="/wiki/Methylbutyltryptamine" title="Methylbutyltryptamine">MBT</a></li> <li><a href="/wiki/N-Methyl-N-ethyltryptamine" title="N-Methyl-N-ethyltryptamine">MET</a></li> <li><a href="/wiki/Milipertine" title="Milipertine">Milipertine</a></li> <li><a href="/wiki/4-HO-MiPT" title="4-HO-MiPT">Miprocin (4-HO-MiPT)</a></li> <li><a href="/wiki/Methylisopropyltryptamine" class="mw-redirect" title="Methylisopropyltryptamine">MiPT</a></li> <li><a href="/wiki/4-Acetoxy-MiPT" class="mw-redirect" title="4-Acetoxy-MiPT">MPT</a></li> <li><a href="/wiki/MS-245" title="MS-245">MS-245</a></li> <li><a href="/wiki/Methylbutyltryptamine#MSBT" title="Methylbutyltryptamine">MSBT</a></li> <li><a href="/wiki/N-Feruloylserotonin" title="N-Feruloylserotonin"><i>N</i>-Feruloylserotonin (moschamine)</a></li> <li><a href="/wiki/NBoc-DMT" title="NBoc-DMT">NBoc-DMT</a></li> <li><a href="/wiki/N-Ethyltryptamine" title="N-Ethyltryptamine">NET/NETP</a></li> <li><a href="/wiki/N-Isopropyltryptamine" title="N-Isopropyltryptamine">NiPT</a></li> <li><a href="/wiki/N-Methyltryptamine" title="N-Methyltryptamine">NMT</a></li> <li><a href="/wiki/Norbaeocystin" title="Norbaeocystin">Norbaeocystin (4-PO-T)</a></li> <li><a href="/wiki/N-t-Butyltryptamine" title="N-t-Butyltryptamine">NTBT</a></li> <li><a href="/wiki/O-4310" title="O-4310">O-4310</a></li> <li><a href="/wiki/O-Pivalylbufotenine" title="O-Pivalylbufotenine"><i>O</i>-Pivalylbufotenine</a></li> <li><a href="/wiki/Oxypertine" title="Oxypertine">Oxypertine</a></li> <li><a href="/wiki/Propylisopropyltryptamine" title="Propylisopropyltryptamine">PiPT</a></li> <li><a href="/wiki/Psilacetin" class="mw-redirect" title="Psilacetin">Psilacetin (<i>O</i>-acetylpsilocin; 4-AcO-DMT)</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> <li><a href="/wiki/Psilomethoxin" title="Psilomethoxin">Psilomethoxin (4-HO-5-MeO-DMT)</a></li> <li><a href="/wiki/Pyr-T" title="Pyr-T">Pyr-T</a></li> <li><a href="/wiki/RS134-49" title="RS134-49">RS134-49</a></li> <li><a class="mw-selflink selflink">10,11-Secoergoline (α,<i>N</i>-Pip-T)</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Solypertine" title="Solypertine">Solypertine</a></li> <li><a href="/wiki/ST-1936" title="ST-1936">ST-1936</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine (T)</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/Yuremamine" title="Yuremamine">Yuremamine</a></li> <li><a href="/w/index.php?title=Z2876442907&action=edit&redlink=1" class="new" title="Z2876442907 (page does not exist)">Z2876442907</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine"><i>N</i>-Acetyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Iodomelatonin" title="2-Iodomelatonin">2-Iodomelatonin</a></li> <li><a href="/w/index.php?title=2-Phenylmelatonin&action=edit&redlink=1" class="new" title="2-Phenylmelatonin (page does not exist)">2-Phenylmelatonin</a></li> <li><a href="/w/index.php?title=5-Methoxyluzindole&action=edit&redlink=1" class="new" title="5-Methoxyluzindole (page does not exist)">5-Methoxyluzindole</a></li> <li><a href="/w/index.php?title=6-Chloromelatonin&action=edit&redlink=1" class="new" title="6-Chloromelatonin (page does not exist)">6-Chloromelatonin</a></li> <li><a href="/w/index.php?title=6-Fluoromelatonin&action=edit&redlink=1" class="new" title="6-Fluoromelatonin (page does not exist)">6-Fluoromelatonin</a></li> <li><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-Hydroxymelatonin</a></li> <li><a href="/w/index.php?title=6-Methoxymelatonin&action=edit&redlink=1" class="new" title="6-Methoxymelatonin (page does not exist)">6-Methoxymelatonin</a></li> <li><a href="/w/index.php?title=6,7-Dichloro-2-methylmelatonin&action=edit&redlink=1" class="new" title="6,7-Dichloro-2-methylmelatonin (page does not exist)">6,7-Dichloro-2-methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/Luzindole" title="Luzindole">Luzindole</a></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">Normelatonin (<i>N</i>-acetylserotonin; NAS)</a></li> <li><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine"><i>N</i>-Acetyltryptamine</a></li> <li><a href="/w/index.php?title=N-Butanoylmelatonin&action=edit&redlink=1" class="new" title="N-Butanoylmelatonin (page does not exist)"><i>N</i>-Butanoylmelatonin</a></li> <li><a href="/w/index.php?title=N-Propionylmelatonin&action=edit&redlink=1" class="new" title="N-Propionylmelatonin (page does not exist)"><i>N</i>-Propionylmelatonin</a></li> <li><a href="/wiki/Piromelatine" title="Piromelatine">Piromelatine</a></li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/%CE%91-Alkyltryptamine" class="mw-redirect" title="Α-Alkyltryptamine">α-Alkyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,%CE%B1-Dimethyltryptamine" title="2,α-Dimethyltryptamine">2,α-DMT</a></li> <li><a href="/wiki/4-HO-%CE%B1MT" title="4-HO-αMT">4-HO-αMT</a></li> <li><a href="/wiki/4-HO-MPMI" title="4-HO-MPMI">4-HO-MPMI (lucigenol)</a></li> <li><a href="/wiki/4-Methyl-%CE%B1-ethyltryptamine" title="4-Methyl-α-ethyltryptamine">4-Me-αET</a></li> <li><a href="/wiki/4-Me-%CE%B1MT" class="mw-redirect" title="4-Me-αMT">4-Me-αMT</a></li> <li><a href="/wiki/5-Allyloxy-AMT" title="5-Allyloxy-AMT">5-Allyloxy-AMT</a></li> <li><a href="/wiki/5-Chloro-%CE%B1ET" title="5-Chloro-αET">5-Chloro-αET</a></li> <li><a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Chloro-αMT</a></li> <li><a href="/wiki/5-Ethoxy-AMT" class="mw-redirect" title="5-Ethoxy-AMT">5-Ethoxy-αMT</a></li> <li><a href="/wiki/5-Fluoro-AET" title="5-Fluoro-AET">5-Fluoro-αET</a></li> <li><a href="/wiki/5-Fluoro-AMT" title="5-Fluoro-AMT">5-Fluoro-αMT</a></li> <li><a href="/w/index.php?title=5-Isopropoxy-AMT&action=edit&redlink=1" class="new" title="5-Isopropoxy-AMT (page does not exist)">5-iPrO-αMT</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,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET </a></li> <li><a href="/wiki/5-MeO-aMT" class="mw-redirect" title="5-MeO-aMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-MeO-MPMI" title="5-MeO-MPMI">5-MeO-MPMI</a></li> <li><a href="/w/index.php?title=5-Methyl-AET&action=edit&redlink=1" class="new" title="5-Methyl-AET (page does not exist)">5-Methyl-αET</a></li> <li><a href="/wiki/6-Fluoro-AMT" title="6-Fluoro-AMT">6-Fluoro-αMT</a></li> <li><a href="/wiki/7-Chloro-AMT" title="7-Chloro-AMT">7-Chloro-αMT</a></li> <li><a href="/wiki/7-Methyl-%CE%B1-ethyltryptamine" title="7-Methyl-α-ethyltryptamine">7-Methyl-αET</a></li> <li><a href="/wiki/%CE%91-Methyl-5-hydroxytryptophan" title="Α-Methyl-5-hydroxytryptophan">α-Methyl-5-HTP</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylserotonin" title="Α-Methylserotonin">α-Methylserotonin (5-HO-αMT)</a></li> <li><a href="/wiki/%CE%91-Methyltryptophan" title="Α-Methyltryptophan">α-Methyltryptophan (αMTP)</a></li> <li><a href="/wiki/Alpha,N-DMT" class="mw-redirect" title="Alpha,N-DMT">α,<i>N</i>-DMT (<i>N</i>-methyl-αMT)</a></li> <li><a href="/wiki/%CE%91,N,N-Trimethyltryptamine" title="Α,N,N-Trimethyltryptamine">α,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/Alpha,N,O-TMS" class="mw-redirect" title="Alpha,N,O-TMS">α,<i>N</i>,<i>O</i>-TMS</a></li> <li><a href="/wiki/%CE%91-Ethyltryptamine" title="Α-Ethyltryptamine">αET (etryptamine)</a></li> <li><a href="/wiki/%CE%91-Methyltryptamine" title="Α-Methyltryptamine">αMT</a></li> <li><a href="/wiki/AL-37350A" title="AL-37350A">AL-37350A (4,5-DHP-αMT)</a></li> <li><a href="/wiki/BK-5Br-NM-AMT" title="BK-5Br-NM-AMT">BK-5Br-NM-AMT</a></li> <li><a href="/wiki/BK-5Cl-NM-AMT" title="BK-5Cl-NM-AMT">BK-5Cl-NM-AMT</a></li> <li><a href="/wiki/BK-5F-NM-AMT" title="BK-5F-NM-AMT">BK-5F-NM-AMT</a></li> <li><a href="/wiki/BK-NM-AMT" title="BK-NM-AMT">BK-NM-AMT</a></li> <li><a href="/wiki/BW-723C86" title="BW-723C86">BW-723C86</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/wiki/Indolylpropylaminopentane" title="Indolylpropylaminopentane">IPAP (α,<i>N</i>-DPT)</a></li> <li><a href="/wiki/MPMI_(drug)" title="MPMI (drug)">MPMI</a></li> <li><a href="/wiki/Soclenicant" title="Soclenicant">Soclenicant (BNC-210)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Triptan" title="Triptan">Triptans</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Almotriptan" title="Almotriptan">Almotriptan</a></li> <li><a href="/wiki/Donitriptan" title="Donitriptan">Donitriptan</a></li> <li><a href="/wiki/Eletriptan" title="Eletriptan">Eletriptan</a></li> <li><a href="/wiki/Frovatriptan" title="Frovatriptan">Frovatriptan</a></li> <li><a href="/wiki/L-694247" title="L-694247">L-694247</a></li> <li><a href="/wiki/Rizatriptan" title="Rizatriptan">Rizatriptan</a></li> <li><a href="/wiki/Sumatriptan" title="Sumatriptan">Sumatriptan</a></li> <li><a href="/wiki/Zolmitriptan" title="Zolmitriptan">Zolmitriptan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Cyclic_compound" title="Cyclic compound">Cyclized tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bay_R_1531" title="Bay R 1531">Bay R 1531</a></li> <li><a href="/wiki/Ciclindole" title="Ciclindole">Ciclindole</a></li> <li><a href="/wiki/Cyclic_3-hydroxymelatonin" title="Cyclic 3-hydroxymelatonin">Cyclic 3-OHM</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> and <a href="/wiki/Lysergamide" class="mw-redirect" title="Lysergamide">lysergamides</a> (e.g., <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">LSD</a>)</li> <li><a href="/wiki/Flucindole" title="Flucindole">Flucindole</a></li> <li><a href="/wiki/Harmala_alkaloid" title="Harmala alkaloid"><i>Harmala</i> alkaloids</a> and <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carbolines</a> (e.g., <a href="/wiki/6-MeO-THH" title="6-MeO-THH">6-MeO-THH</a>, <a href="/wiki/9-Methyl-%CE%B2-carboline" title="9-Methyl-β-carboline">9-Me-BC</a>, <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carboline (norharman)</a>, <a href="/wiki/Harmaline" title="Harmaline">harmaline</a>, <a href="/wiki/Harmalol" title="Harmalol">harmalol</a>, <a href="/wiki/Harmane" title="Harmane">harmane</a>, <a href="/wiki/Harmine" title="Harmine">harmine</a>, <a href="/wiki/Pinoline" title="Pinoline">pinoline</a>, <a href="/wiki/Tetrahydroharmine" title="Tetrahydroharmine">tetrahydroharmine</a>, <a href="/wiki/Tryptoline" title="Tryptoline">tryptoline</a>)</li> <li><a href="/wiki/Iboga-type_alkaloid" title="Iboga-type alkaloid"><i>Iboga</i> alkaloids</a> and related (e.g., <a href="/wiki/DM-506" class="mw-redirect" title="DM-506">DM-506 (ibogaminalog)</a>, <a href="/wiki/Ibogaine" title="Ibogaine">ibogaine</a>, <a href="/wiki/Ibogamine" title="Ibogamine">ibogamine</a>, <a href="/wiki/Noribogaine" title="Noribogaine">noribogaine</a>, <a href="/wiki/Tabernanthalog" title="Tabernanthalog">tabernanthalog</a>, <a href="/wiki/Tabernanthine" title="Tabernanthine">tabernanthine</a>)</li> <li><a href="/wiki/LY-266,097" title="LY-266,097">LY-266,097</a></li> <li><a href="/wiki/Metralindole" title="Metralindole">Metralindole</a></li> <li><a href="/wiki/NDTDI" title="NDTDI">NDTDI</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/RU-28306" title="RU-28306">RU-28306</a></li> <li><a href="/wiki/Yohimban" title="Yohimban">Yohimbans</a> (e.g., <a href="/wiki/Yohimbine" title="Yohimbine">yohimbine</a>, <a href="/wiki/Rauwolscine" title="Rauwolscine">rauwolscine</a>, <a href="/wiki/Spegatrine" title="Spegatrine">spegatrine</a>, <a href="/wiki/Corynanthine" title="Corynanthine">corynanthine</a>, <a href="/wiki/Ajmalicine" title="Ajmalicine">ajmalicine</a>, <a href="/wiki/Reserpine" title="Reserpine">reserpine</a>, <a href="/wiki/Deserpidine" title="Deserpidine">deserpidine</a>, <a href="/wiki/Rescinnamine" title="Rescinnamine">rescinnamine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Isotryptamine" title="Isotryptamine">Isotryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5-MeO-isoDMT" title="5-MeO-isoDMT">5-MeO-isoDMT</a></li> <li><a href="/wiki/6-MeO-isoDMT" title="6-MeO-isoDMT">6-MeO-isoDMT</a></li> <li><a href="/wiki/IsoAMT" class="mw-redirect" title="IsoAMT">isoAMT</a></li> <li><a href="/wiki/IsoDMT" title="IsoDMT">isoDMT</a></li> <li><a href="/wiki/Isotryptamine" title="Isotryptamine">Isotryptamine (isoT)</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/Zalsupindole" title="Zalsupindole">Zalsupindole (DLX-001, AAZ-A-154)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Related compounds</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="/w/index.php?title=2-Azapsilocin&action=edit&redlink=1" class="new" title="2-Azapsilocin (page does not exist)">2-Azapsilocin</a></li> <li><a href="/w/index.php?title=4-Aza-5-MeO-DPT&action=edit&redlink=1" class="new" title="4-Aza-5-MeO-DPT (page does not exist)">4-Aza-5-MeO-DPT</a></li> <li><a href="/w/index.php?title=5-Aza-4-MeO-DiPT&action=edit&redlink=1" class="new" title="5-Aza-4-MeO-DiPT (page does not exist)">5-Aza-4-MeO-DiPT</a></li> <li><a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li> <li><a href="/wiki/5-Hydroxyindoleacetaldehyde" title="5-Hydroxyindoleacetaldehyde">5-HIAL</a></li> <li><a href="/w/index.php?title=5-Hydroxyindole_thiazoladine_carboxylic_acid&action=edit&redlink=1" class="new" title="5-Hydroxyindole thiazoladine carboxylic acid (page does not exist)">5-HITCA</a></li> <li><a href="/w/index.php?title=5-Methoxyindoleacetaldehyde&action=edit&redlink=1" class="new" title="5-Methoxyindoleacetaldehyde (page does not exist)">5-MIAL</a></li> <li><a href="/w/index.php?title=7-Aza-5-MeO-DiPT&action=edit&redlink=1" class="new" title="7-Aza-5-MeO-DiPT (page does not exist)">7-Aza-5-MeO-DiPT</a></li> <li><a href="/wiki/AL-34662" title="AL-34662">AL-34662</a></li> <li><a href="/wiki/AL-38022A" title="AL-38022A">AL-38022A</a></li> <li><a href="/wiki/Substituted_benzofuran" title="Substituted benzofuran">Benzofurans</a> (e.g., <a href="/wiki/3-(2-aminopropyl)benzofuran" class="mw-redirect" title="3-(2-aminopropyl)benzofuran">3-APB</a>, <a href="/wiki/5-MeO-DiBF" title="5-MeO-DiBF">5-MeO-DiBF</a>, <a href="/wiki/Benzofuranylpropylaminopentane" title="Benzofuranylpropylaminopentane">BPAP</a>, <a href="/wiki/Dimemebfe" title="Dimemebfe">dimemebfe</a>, <a href="/wiki/Mebfap" title="Mebfap">mebfap</a>)</li> <li><a href="/wiki/BRL-54443" title="BRL-54443">BRL-54443</a></li> <li><a href="/wiki/CP-94253" title="CP-94253">CP-94253</a></li> <li><a href="/wiki/EMD-386088" title="EMD-386088">EMD-386088</a></li> <li><a href="/w/index.php?title=I-32_(drug)&action=edit&redlink=1" class="new" title="I-32 (drug) (page does not exist)">I-32</a></li> <li><a href="/wiki/Indoleacetaldehyde" class="mw-redirect" title="Indoleacetaldehyde">IAL</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine</a></li> <li><a href="/wiki/LY-367,265" title="LY-367,265">LY-367265</a></li> <li><a href="/wiki/Masupirdine" title="Masupirdine">Masupirdine</a></li> <li>Non-tryptamine <a href="/wiki/Triptan" title="Triptan">triptans</a> (e.g., <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/LY-334370" title="LY-334370">LY-334370</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>)</li> <li><a href="/wiki/Pirlindole" title="Pirlindole">Pirlindole</a></li> <li><a href="/wiki/(R)-69" title="(R)-69">(<i>R</i>)-69 (3IQ)</a></li> <li><a href="/wiki/Ro60-0213" title="Ro60-0213">Ro60-0213</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/Sertindole" title="Sertindole">Sertindole</a></li> <li><a href="/wiki/SN-22" title="SN-22">SN-22</a></li> <li><a href="/wiki/Tepirindole" title="Tepirindole">Tepirindole</a></li> <li><a href="/wiki/Tetrindole" title="Tetrindole">Tetrindole</a></li> <li><a href="/wiki/VER-3323" title="VER-3323">VER-3323</a></li> <li><a href="/wiki/VU6067416" title="VU6067416">VU6067416</a></li> <li><a href="/wiki/YM-348" title="YM-348">YM-348</a></li></ul> </div></td></tr></tbody></table></div> <p><br /> </p> <style data-mw-deduplicate="TemplateStyles:r1271159938">.mw-parser-output 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