Dimethyllysergamide (DAM-57)
<h1 id="firstHeading" class="firstHeading" lang="en">Dimethyllysergamide</h1>
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<div id="siteSub">From Wikipedia, the free encyclopedia</div>
<div id="contentSub"> (Redirected from <a href="http://en.wikipedia.org/w/index.php?title=DAM-57&redirect=no" title="DAM-57">DAM-57</a>)</div>
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<caption>Dimethyllysergamide</caption>
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<td colspan="2" ><a href="http://en.wikipedia.org/wiki/File:DAM-57.svg" class="image"><img src="/89452f01-bd90-52de-83f8-67f2cd04d14c.png"/></a></td>
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<th colspan="2" >Systematic (<a href="http://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclature" title="International Union of Pure and Applied Chemistry nomenclature" class="mw-redirect">IUPAC</a>) name</th>
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<td colspan="2" >(6a<i>R</i>,9<i>R</i>)-<i>N</i>,<i>N</i>-dimethyl-7-methyl-4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9-carboxamide</td>
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<th colspan="2" >Clinical data</th>
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<div ><a href="http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></div>
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<li><small><abbr title="United States">US</abbr>:</small> <a href="http://en.wikipedia.org/wiki/Controlled_Substances_Act#Schedule_I_drugs" title="Controlled Substances Act">Schedule I</a> Controlled in the <a href="http://en.wikipedia.org/wiki/United_States" title="United States">United States</a> via the <a href="http://en.wikipedia.org/wiki/Federal_Analog_Act" title="Federal Analog Act">Federal Analog Act</a> but only if it is intended for human consumption.</li>
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<div ><a href="http://en.wikipedia.org/wiki/Route_of_administration" title="Route of administration">Routes of
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<td><a href="http://en.wiktionary.org/wiki/oral" class="extiw" title="wiktionary:oral">Oral</a></td>
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<th colspan="2" >Pharmacokinetic data</th>
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<th scope="row" ><a href="http://en.wikipedia.org/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th>
<td>hepatic</td>
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<th scope="row" ><a href="http://en.wikipedia.org/wiki/Excretion" title="Excretion">Excretion</a></th>
<td>renal</td>
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<th colspan="2" >Identifiers</th>
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<th scope="row" ><a href="http://en.wikipedia.org/wiki/PubChem" title="PubChem">PubChem</a></th>
<td><a rel="nofollow" class="external text" href="http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=199478">CID 199478</a></td>
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<th scope="row" ><a href="http://en.wikipedia.org/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th>
<td><a rel="nofollow" class="external text" href="http://www.chemspider.com/Chemical-Structure.172668.html">172668</a><sup> <img src="/71f89512-036a-55a2-a413-2e433305eec1.png"/></sup></td>
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<th scope="row" ><a href="http://en.wikipedia.org/wiki/Synonym" title="Synonym">Synonyms</a></th>
<td>DAM-57, Lysergic acid dimethylamide</td>
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<th colspan="2" >Chemical data</th>
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<th scope="row" ><a href="http://en.wikipedia.org/wiki/Chemical_formula" title="Chemical formula">Formula</a></th>
<td><a href="http://en.wikipedia.org/wiki/Carbon" title="Carbon">C</a><sub>18</sub><a href="http://en.wikipedia.org/wiki/Hydrogen" title="Hydrogen">H</a><sub>21</sub><a href="http://en.wikipedia.org/wiki/Nitrogen" title="Nitrogen">N</a><sub>3</sub><a href="http://en.wikipedia.org/wiki/Oxygen" title="Oxygen">O</a></td>
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<div ><a href="http://en.wikipedia.org/wiki/Molecular_mass" title="Molecular mass">Molecular mass</a></div>
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<td>295.39 g/mol</td>
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<div class="NavHead" ><a href="http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification" title="Simplified molecular input line entry specification" class="mw-redirect">SMILES</a><a href="http://en.wikipedia.org/wiki/Dimethyllysergamide#" id="NavToggle1" class="NavToggle">[show]</a></div>
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<div class="NavHead" ><a href="http://en.wikipedia.org/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a><a href="http://en.wikipedia.org/wiki/Dimethyllysergamide#" id="NavToggle2" class="NavToggle">[show]</a></div>
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<th colspan="2" > <img src="/f0a3a024-b38b-5904-bab0-a2ca400b984a.png"/> <a href="http://en.wikipedia.org/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">(what is this?)</a> <a class="external text" href="http://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=447574383&page2=Dimethyllysergamide">(verify)</a></th>
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<p><b><i>N,N</i>-Dimethyllysergamide</b> or <b><i>N,N</i>-dimethyl-D-lysergamide</b> (<b>DAM-57</b>) is a <a href="http://en.wikipedia.org/wiki/Derivative" title="Derivative">derivative</a> of <a href="http://en.wikipedia.org/wiki/Ergine" title="Ergine">ergine</a>. There has been a single report of observing N,N-dimethyl-D-lysergamide in the illicit drug market.<sup id="cite_ref-1" class="reference"><a href="http://en.wikipedia.org/wiki/Dimethyllysergamide#cite_note-1">[1]</a></sup> This compound did induce autonomic disturbances at oral levels of some ten times the dosage required for LSD, presumably in the high hundreds of micrograms. There is some disagreement as to whether there were psychic changes observed.<sup id="cite_ref-2" class="reference"><a href="http://en.wikipedia.org/wiki/Dimethyllysergamide#cite_note-2">[2]</a></sup></p>
<h2>References</h2>
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<li id="cite_note-1">A. B. Clark, Microgram., 6, 37 (1973)</li>
<li id="cite_note-2"></li>
Shulgin, Shulgin, TIHKAL, #26 (1997)</ul>
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