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title="Racétam – French" lang="fr" hreflang="fr" data-title="Racétam" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Racetam" title="Racetam – Italian" lang="it" hreflang="it" data-title="Racetam" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A8%D7%A6%D7%98%D7%90%D7%9D" title="רצטאם – Hebrew" lang="he" hreflang="he" data-title="רצטאם" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%A9%E3%82%BB%E3%82%BF%E3%83%A0" title="ラセタム – Japanese" lang="ja" 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searchaux" style="display:none">Class of drugs</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:2-Pyrrolidone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/2-Pyrrolidone.png/105px-2-Pyrrolidone.png" decoding="async" width="105" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/2-Pyrrolidone.png/158px-2-Pyrrolidone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/45/2-Pyrrolidone.png/210px-2-Pyrrolidone.png 2x" data-file-width="388" data-file-height="455" /></a><figcaption><a href="/wiki/2-Pyrrolidone" title="2-Pyrrolidone">2-Pyrrolidone</a></figcaption></figure> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Piracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Piracetam.svg/105px-Piracetam.svg.png" decoding="async" width="105" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Piracetam.svg/158px-Piracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Piracetam.svg/210px-Piracetam.svg.png 2x" data-file-width="274" data-file-height="245" /></a><figcaption><a href="/wiki/Piracetam" title="Piracetam">Piracetam</a></figcaption></figure> <p><b>Racetams</b>, also sometimes known simply as <b>pyrrolidones</b>,<sup id="cite_ref-Shorvon2001_1-0" class="reference"><a href="#cite_note-Shorvon2001-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> are a class of <a href="/wiki/Drug" title="Drug">drugs</a> that share a <a href="/wiki/2-pyrrolidone" class="mw-redirect" title="2-pyrrolidone">pyrrolidone</a> nucleus.<sup id="cite_ref-MalykhSadaie2010_2-0" class="reference"><a href="#cite_note-MalykhSadaie2010-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GualtieriManettiRomanelli2002_3-0" class="reference"><a href="#cite_note-GualtieriManettiRomanelli2002-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GouliaevSenning1994_4-0" class="reference"><a href="#cite_note-GouliaevSenning1994-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Many, but not all, specifically have a 2-<a href="/wiki/Carbonyl_group" title="Carbonyl group">oxo</a>-1-<a href="/wiki/Pyrrolidine" title="Pyrrolidine">pyrrolidine</a> <a href="/wiki/Acetamide" title="Acetamide">acetamide</a> (<a href="/wiki/Piracetam" title="Piracetam">piracetam</a>) nucleus. Some racetams, such as <a href="/wiki/Piracetam" title="Piracetam">piracetam</a>, <a href="/wiki/Aniracetam" title="Aniracetam">aniracetam</a>, <a href="/wiki/Oxiracetam" title="Oxiracetam">oxiracetam</a>, <a href="/wiki/Pramiracetam" title="Pramiracetam">pramiracetam</a>, and <a href="/wiki/Phenylpiracetam" title="Phenylpiracetam">phenylpiracetam</a>, are considered <a href="/wiki/Nootropic" title="Nootropic">nootropics</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Phenylpiracetam is also a <a href="/wiki/Stimulant" title="Stimulant">stimulant</a>.<sup id="cite_ref-MalykhSadaie2010_2-1" class="reference"><a href="#cite_note-MalykhSadaie2010-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Others, such as <a href="/wiki/Levetiracetam" title="Levetiracetam">levetiracetam</a>, <a href="/wiki/Brivaracetam" title="Brivaracetam">brivaracetam</a>, and <a href="/wiki/Seletracetam" title="Seletracetam">seletracetam</a>, are <a href="/wiki/Anticonvulsant" title="Anticonvulsant">anticonvulsants</a>.<sup id="cite_ref-WuCaoTian2024_6-0" class="reference"><a href="#cite_note-WuCaoTian2024-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Mechanism">Mechanism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Racetam&action=edit&section=1" title="Edit section: Mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There is no universally accepted mechanism of action for racetams. Racetams generally show negligible <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> for common <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> <a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">receptors</a>, but modulation of central <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitters</a>, including <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a> and <a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>, has been reported. Although <a href="/wiki/Aniracetam" title="Aniracetam">aniracetam</a> and <a href="/wiki/Nebracetam" title="Nebracetam">nebracetam</a> show some affinity for <a href="/wiki/Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">muscarinic acetylcholine receptors</a>, only <a href="/wiki/Nefiracetam" title="Nefiracetam">nefiracetam</a> demonstrates nanomolar interactions with neurotransmitter receptors. Modification of membrane-located mechanisms of central signal transduction is another hypothesis.<sup id="cite_ref-GualtieriManettiRomanelli2002_3-1" class="reference"><a href="#cite_note-GualtieriManettiRomanelli2002-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Like some <a href="/wiki/Ampakine" title="Ampakine">ampakines</a>, some racetams, such as piracetam and aniracetam, are positive <a href="/wiki/Allosteric_modulator" title="Allosteric modulator">allosteric modulators</a> of the <a href="/wiki/AMPA_receptor" title="AMPA receptor">AMPA receptor</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Racetams are understood to work by allosterically modulating <a href="/wiki/Glutamate_receptor" title="Glutamate receptor">glutamate receptors</a>, specifically AMPA receptors, leading to Ca<sup>2+</sup> influx that is excitatory.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Racetams are posited to enhance memory through interaction with glutamate receptors in the central nervous system. </p><p>Phenylpiracetam, unique among racetams in being a <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">phenethylamine</a> and stimulant, is an atypical <a href="/wiki/Dopamine_reuptake_inhibitor" title="Dopamine reuptake inhibitor">dopamine reuptake inhibitor</a>.<sup id="cite_ref-Molina-CarballoCheca-RosMuñoz-Hoyos2016_9-0" class="reference"><a href="#cite_note-Molina-CarballoCheca-RosMuñoz-Hoyos2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-VeinbergVaversOrlova2015_10-0" class="reference"><a href="#cite_note-VeinbergVaversOrlova2015-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SommerDanyszRuss2014_11-0" class="reference"><a href="#cite_note-SommerDanyszRuss2014-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-StutzGolaniWitkin2019_12-0" class="reference"><a href="#cite_note-StutzGolaniWitkin2019-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Anticonvulsant racetams, including <a href="/wiki/Levetiracetam" title="Levetiracetam">levetiracetam</a>, <a href="/wiki/Brivaracetam" title="Brivaracetam">brivaracetam</a>, and <a href="/wiki/Seletracetam" title="Seletracetam">seletracetam</a>, act as <a href="/wiki/Synaptic_vesicle_glycoprotein_2A" class="mw-redirect" title="Synaptic vesicle glycoprotein 2A">synaptic vesicle glycoprotein 2A</a> (SV2A) <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>.<sup id="cite_ref-WuCaoTian2024_6-1" class="reference"><a href="#cite_note-WuCaoTian2024-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> A newer <a href="/wiki/Structural_analog" title="Structural analog">analogue</a> of these agents, <a href="/w/index.php?title=Padsevonil&action=edit&redlink=1" class="new" title="Padsevonil (page does not exist)">padsevonil</a>, is no longer a racetam itself but is much more <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> in comparison and interacts with not only SV2A but also <a href="/wiki/Synaptic_vesicle_glycoprotein_2B" class="mw-redirect" title="Synaptic vesicle glycoprotein 2B">synaptic vesicle glycoprotein 2B</a> (SV2B) and <a href="/w/index.php?title=Synaptic_vesicle_glycoprotein_2C&action=edit&redlink=1" class="new" title="Synaptic vesicle glycoprotein 2C (page does not exist)">synaptic vesicle glycoprotein 2C</a> (SV2C).<sup id="cite_ref-WuCaoTian2024_6-2" class="reference"><a href="#cite_note-WuCaoTian2024-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Methylphenylpiracetam" title="Methylphenylpiracetam">Methylphenylpiracetam</a>, a derivative of phenylpiracetam, is a <a href="/wiki/Positive_allosteric_modulator" class="mw-redirect" title="Positive allosteric modulator">positive allosteric modulator</a> of the <a href="/wiki/Sigma_receptor" title="Sigma receptor">sigma</a> <a href="/wiki/Sigma-1_receptor" title="Sigma-1 receptor">σ<sub>1</sub> receptor</a>.<sup id="cite_ref-VeinbergVaversOrlova2015_10-1" class="reference"><a href="#cite_note-VeinbergVaversOrlova2015-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-VaversZvejnieceMaurice2019_13-0" class="reference"><a href="#cite_note-VaversZvejnieceMaurice2019-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ZvejnieceVaversSvalbe2014_14-0" class="reference"><a href="#cite_note-ZvejnieceVaversSvalbe2014-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4-S1-P51_15-0" class="reference"><a href="#cite_note-4-S1-P51-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> It is currently the only racetam known to possess this action.<sup id="cite_ref-VeinbergVaversOrlova2015_10-2" class="reference"><a href="#cite_note-VeinbergVaversOrlova2015-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cofactors">Cofactors</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Racetam&action=edit&section=2" title="Edit section: Cofactors"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In studies with aged rats, marked improvement has been observed in cognitive tasks in experimental groups given piracetam. Performance was further increased when piracetam was combined with <a href="/wiki/Choline" title="Choline">choline</a>. Evidence in studies with rats has indicated that the potency of piracetam is increased when administered with <a href="/wiki/Choline" title="Choline">choline</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="List_of_racetams">List of racetams</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Racetam&action=edit&section=3" title="Edit section: List of racetams"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable"> <tbody><tr> <th>Structure</th> <th>Name </th></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Piracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Piracetam.svg/125px-Piracetam.svg.png" decoding="async" width="125" height="112" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Piracetam.svg/188px-Piracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Piracetam.svg/250px-Piracetam.svg.png 2x" data-file-width="274" data-file-height="245" /></a></span></td> <td><a href="/wiki/Piracetam" title="Piracetam">Piracetam</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Oxiracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Oxiracetam.svg/125px-Oxiracetam.svg.png" decoding="async" width="125" height="139" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Oxiracetam.svg/188px-Oxiracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Oxiracetam.svg/250px-Oxiracetam.svg.png 2x" data-file-width="274" data-file-height="305" /></a></span></td> <td><a href="/wiki/Oxiracetam" title="Oxiracetam">Oxiracetam</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Fonturacetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Fonturacetam.svg/125px-Fonturacetam.svg.png" decoding="async" width="125" height="178" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Fonturacetam.svg/188px-Fonturacetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/Fonturacetam.svg/250px-Fonturacetam.svg.png 2x" data-file-width="512" data-file-height="729" /></a></span></td> <td><a href="/wiki/Phenylpiracetam" title="Phenylpiracetam">Phenylpiracetam</a> / Fonturacetam </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Fonturacetam_hydrazide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Fonturacetam_hydrazide.svg/125px-Fonturacetam_hydrazide.svg.png" decoding="async" width="125" height="152" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Fonturacetam_hydrazide.svg/188px-Fonturacetam_hydrazide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/67/Fonturacetam_hydrazide.svg/250px-Fonturacetam_hydrazide.svg.png 2x" data-file-width="512" data-file-height="624" /></a></span></td> <td><a href="/wiki/Phenylpiracetam_Hydrazide" class="mw-redirect" title="Phenylpiracetam Hydrazide">Phenylpiracetam Hydrazide</a> / Fonturacetam Hydrazide </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Aniracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Aniracetam.svg/125px-Aniracetam.svg.png" decoding="async" width="125" height="97" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Aniracetam.svg/188px-Aniracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Aniracetam.svg/250px-Aniracetam.svg.png 2x" data-file-width="512" data-file-height="398" /></a></span></td> <td><a href="/wiki/Aniracetam" title="Aniracetam">Aniracetam</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Pramiracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Pramiracetam.svg/125px-Pramiracetam.svg.png" decoding="async" width="125" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Pramiracetam.svg/188px-Pramiracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Pramiracetam.svg/250px-Pramiracetam.svg.png 2x" data-file-width="458" data-file-height="261" /></a></span></td> <td><a href="/wiki/Pramiracetam" title="Pramiracetam">Pramiracetam</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Seletracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Seletracetam.svg/125px-Seletracetam.svg.png" decoding="async" width="125" height="164" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Seletracetam.svg/188px-Seletracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/13/Seletracetam.svg/250px-Seletracetam.svg.png 2x" data-file-width="512" data-file-height="671" /></a></span></td> <td><a href="/wiki/Seletracetam" title="Seletracetam">Seletracetam</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Levetiracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Levetiracetam.svg/125px-Levetiracetam.svg.png" decoding="async" width="125" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Levetiracetam.svg/188px-Levetiracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Levetiracetam.svg/250px-Levetiracetam.svg.png 2x" data-file-width="512" data-file-height="478" /></a></span></td> <td><a href="/wiki/Levetiracetam" title="Levetiracetam">Levetiracetam</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Coluracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Coluracetam.svg/125px-Coluracetam.svg.png" decoding="async" width="125" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Coluracetam.svg/188px-Coluracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Coluracetam.svg/250px-Coluracetam.svg.png 2x" data-file-width="625" data-file-height="524" /></a></span></td> <td><a href="/wiki/Coluracetam" title="Coluracetam">Coluracetam</a> / BCI-540 </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Fasoracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Fasoracetam.svg/125px-Fasoracetam.svg.png" decoding="async" width="125" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Fasoracetam.svg/188px-Fasoracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Fasoracetam.svg/250px-Fasoracetam.svg.png 2x" data-file-width="500" data-file-height="280" /></a></span></td> <td><a href="/wiki/Fasoracetam" title="Fasoracetam">Fasoracetam</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Brivaracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Brivaracetam.svg/125px-Brivaracetam.svg.png" decoding="async" width="125" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Brivaracetam.svg/188px-Brivaracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Brivaracetam.svg/250px-Brivaracetam.svg.png 2x" data-file-width="512" data-file-height="649" /></a></span></td> <td><a href="/wiki/Brivaracetam" title="Brivaracetam">Brivaracetam</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Dimiracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Dimiracetam.svg/125px-Dimiracetam.svg.png" decoding="async" width="125" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Dimiracetam.svg/188px-Dimiracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Dimiracetam.svg/250px-Dimiracetam.svg.png 2x" data-file-width="330" data-file-height="275" /></a></span></td> <td><a href="/wiki/Dimiracetam" title="Dimiracetam">Dimiracetam</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:E1R.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/E1R.svg/125px-E1R.svg.png" decoding="async" width="125" height="178" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/E1R.svg/188px-E1R.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0c/E1R.svg/250px-E1R.svg.png 2x" data-file-width="512" data-file-height="728" /></a></span></td> <td><a href="/wiki/Methylphenylpiracetam" title="Methylphenylpiracetam">Methylphenylpiracetam</a> / E1R </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Nebracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Nebracetam.svg/125px-Nebracetam.svg.png" decoding="async" width="125" height="152" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Nebracetam.svg/188px-Nebracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Nebracetam.svg/250px-Nebracetam.svg.png 2x" data-file-width="92" data-file-height="112" /></a></span></td> <td><a href="/wiki/Nebracetam" title="Nebracetam">Nebracetam</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Nefiracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Nefiracetam.svg/125px-Nefiracetam.svg.png" decoding="async" width="125" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Nefiracetam.svg/188px-Nefiracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Nefiracetam.svg/250px-Nefiracetam.svg.png 2x" data-file-width="361" data-file-height="261" /></a></span></td> <td><a href="/wiki/Nefiracetam" title="Nefiracetam">Nefiracetam</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Noopept.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Noopept.svg/125px-Noopept.svg.png" decoding="async" width="125" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Noopept.svg/188px-Noopept.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/80/Noopept.svg/250px-Noopept.svg.png 2x" data-file-width="609" data-file-height="508" /></a></span></td> <td><a href="/wiki/Omberacetam" class="mw-redirect" title="Omberacetam">Omberacetam</a> / Noopept </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Rolziracetam_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Rolziracetam_structure.svg/125px-Rolziracetam_structure.svg.png" decoding="async" width="125" height="114" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Rolziracetam_structure.svg/188px-Rolziracetam_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Rolziracetam_structure.svg/250px-Rolziracetam_structure.svg.png 2x" data-file-width="381" data-file-height="348" /></a></span></td> <td><a href="/wiki/Rolziracetam" title="Rolziracetam">Rolziracetam</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Cebaracetam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Cebaracetam.svg/125px-Cebaracetam.svg.png" decoding="async" width="125" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Cebaracetam.svg/188px-Cebaracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/38/Cebaracetam.svg/250px-Cebaracetam.svg.png 2x" data-file-width="730" data-file-height="369" /></a></span></td> <td><a href="/wiki/Cebaracetam" title="Cebaracetam">Cebaracetam</a> </td></tr> </tbody></table> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Racetam&action=edit&section=4" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Racetams are <a href="/wiki/2-pyrrolidone" class="mw-redirect" title="2-pyrrolidone">2-pyrrolidone</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivatives</a> and may sometimes be referred to simply as pyrrolidones (2-oxopyrrolidines).<sup id="cite_ref-Shorvon2001_1-1" class="reference"><a href="#cite_note-Shorvon2001-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Many, but not all, specifically have a 2-<a href="/wiki/Carbonyl_group" title="Carbonyl group">oxo</a>-1-<a href="/wiki/Pyrrolidine" title="Pyrrolidine">pyrrolidine</a> <a href="/wiki/Acetamide" title="Acetamide">acetamide</a> nucleus, which is the <a href="/wiki/Chemical_structure" title="Chemical structure">chemical structure</a> of <a href="/wiki/Piracetam" title="Piracetam">piracetam</a>. </p><p>Racetams are <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclic</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivatives</a> of the <a href="/wiki/Inhibitory_postsynaptic_potential" title="Inhibitory postsynaptic potential">inhibitory</a> <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> <a href="/wiki/%CE%93-aminobutyric_acid" class="mw-redirect" title="Γ-aminobutyric acid">γ-aminobutyric acid</a> (GABA).<sup id="cite_ref-MalykhSadaie2010_2-2" class="reference"><a href="#cite_note-MalykhSadaie2010-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> They are also <a href="/wiki/Structural_analog" title="Structural analog">structurally related</a> to the <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> cyclic <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Pyroglutamic_acid" title="Pyroglutamic acid">pyroglutamic acid</a> (pyroglutamate), a cyclic analogue of the endogenous <a href="/wiki/Excitatory_postsynaptic_potential" title="Excitatory postsynaptic potential">excitatory</a> neurotransmitter <a href="/wiki/Glutamic_acid" title="Glutamic acid">glutamic acid</a> (glutamate).<sup id="cite_ref-GualtieriManettiRomanelli2002_3-2" class="reference"><a href="#cite_note-GualtieriManettiRomanelli2002-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GouliaevSenning1994_4-1" class="reference"><a href="#cite_note-GouliaevSenning1994-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <style data-mw-deduplicate="TemplateStyles:r1248256098">@media all and (max-width:720px){.mw-parser-output .mod-gallery{width:100%!important}}.mw-parser-output .mod-gallery{display:table}.mw-parser-output .mod-gallery-default{background:transparent;margin-top:4px}.mw-parser-output .mod-gallery-center{margin-left:auto;margin-right:auto}.mw-parser-output .mod-gallery-left{float:left}.mw-parser-output .mod-gallery-right{float:right}.mw-parser-output .mod-gallery-none{float:none}.mw-parser-output .mod-gallery-collapsible{width:100%}.mw-parser-output .mod-gallery .title,.mw-parser-output .mod-gallery .main,.mw-parser-output .mod-gallery .footer{display:table-row}.mw-parser-output .mod-gallery .title>div{display:table-cell;padding:0 4px 4px;text-align:center;font-weight:bold}.mw-parser-output .mod-gallery .main>div{display:table-cell}.mw-parser-output .mod-gallery .gallery{line-height:1.35em}.mw-parser-output .mod-gallery .footer>div{display:table-cell;padding:4px;text-align:right;font-size:85%;line-height:1em}.mw-parser-output .mod-gallery .title>div *,.mw-parser-output .mod-gallery .footer>div *{overflow:visible}.mw-parser-output .mod-gallery .gallerybox img{background:none!important}.mw-parser-output .mod-gallery .bordered-images .thumb img{border:solid var(--background-color-neutral,#eaecf0)1px}.mw-parser-output .mod-gallery .whitebg .thumb{background:var(--background-color-base,#fff)!important}</style><div class="mod-gallery mod-gallery-default"><div class="main"><div><ul class="gallery mw-gallery-traditional nochecker bordered-images whitebg"> <li class="gallerybox" style="width: 180px"> <div class="thumb" style="width: 175px; height: 210px;"><span typeof="mw:File"><a href="/wiki/File:Gamma-Aminobutters%C3%A4ure_-_gamma-aminobutyric_acid.svg" class="mw-file-description" title="γ-Aminobutyric acid (GABA)"><img alt="γ-Aminobutyric acid (GABA)" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Gamma-Aminobutters%C3%A4ure_-_gamma-aminobutyric_acid.svg/145px-Gamma-Aminobutters%C3%A4ure_-_gamma-aminobutyric_acid.svg.png" decoding="async" width="145" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Gamma-Aminobutters%C3%A4ure_-_gamma-aminobutyric_acid.svg/218px-Gamma-Aminobutters%C3%A4ure_-_gamma-aminobutyric_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Gamma-Aminobutters%C3%A4ure_-_gamma-aminobutyric_acid.svg/290px-Gamma-Aminobutters%C3%A4ure_-_gamma-aminobutyric_acid.svg.png 2x" data-file-width="232" data-file-height="77" /></a></span></div> <div class="gallerytext"><a href="/wiki/%CE%93-Aminobutyric_acid" class="mw-redirect" title="Γ-Aminobutyric acid">γ-Aminobutyric acid</a> (GABA)</div> </li> <li class="gallerybox" style="width: 180px"> <div class="thumb" style="width: 175px; height: 210px;"><span typeof="mw:File"><a href="/wiki/File:Structural_formula_of_2-pyrrolidone.svg" class="mw-file-description" title="2-Pyrrolidone"><img alt="2-Pyrrolidone" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Structural_formula_of_2-pyrrolidone.svg/145px-Structural_formula_of_2-pyrrolidone.svg.png" decoding="async" width="145" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Structural_formula_of_2-pyrrolidone.svg/218px-Structural_formula_of_2-pyrrolidone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Structural_formula_of_2-pyrrolidone.svg/290px-Structural_formula_of_2-pyrrolidone.svg.png 2x" data-file-width="158" data-file-height="133" /></a></span></div> <div class="gallerytext"><a href="/wiki/2-Pyrrolidone" title="2-Pyrrolidone">2-Pyrrolidone</a></div> </li> <li class="gallerybox" style="width: 180px"> <div class="thumb" style="width: 175px; height: 210px;"><span typeof="mw:File"><a href="/wiki/File:L-Glutamins%C3%A4ure_-_L-Glutamic_acid.svg" class="mw-file-description" title="Glutamic acid (glutamate)"><img alt="Glutamic acid (glutamate)" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/L-Glutamins%C3%A4ure_-_L-Glutamic_acid.svg/145px-L-Glutamins%C3%A4ure_-_L-Glutamic_acid.svg.png" decoding="async" width="145" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/L-Glutamins%C3%A4ure_-_L-Glutamic_acid.svg/218px-L-Glutamins%C3%A4ure_-_L-Glutamic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/L-Glutamins%C3%A4ure_-_L-Glutamic_acid.svg/290px-L-Glutamins%C3%A4ure_-_L-Glutamic_acid.svg.png 2x" data-file-width="256" data-file-height="121" /></a></span></div> <div class="gallerytext"><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid</a> (glutamate)</div> </li> <li class="gallerybox" style="width: 180px"> <div class="thumb" style="width: 175px; height: 210px;"><span typeof="mw:File"><a href="/wiki/File:(S)-Pyroglutamic_acid_Structural_Formulae.png" class="mw-file-description" title="Pyroglutamic acid"><img alt="Pyroglutamic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/%28S%29-Pyroglutamic_acid_Structural_Formulae.png/145px-%28S%29-Pyroglutamic_acid_Structural_Formulae.png" decoding="async" width="145" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/%28S%29-Pyroglutamic_acid_Structural_Formulae.png/218px-%28S%29-Pyroglutamic_acid_Structural_Formulae.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c8/%28S%29-Pyroglutamic_acid_Structural_Formulae.png/290px-%28S%29-Pyroglutamic_acid_Structural_Formulae.png 2x" data-file-width="1812" data-file-height="789" /></a></span></div> <div class="gallerytext"><a href="/wiki/Pyroglutamic_acid" title="Pyroglutamic acid">Pyroglutamic acid</a></div> </li> <li class="gallerybox" style="width: 180px"> <div class="thumb" style="width: 175px; height: 210px;"><span typeof="mw:File"><a href="/wiki/File:Piracetam.svg" class="mw-file-description" title="Piracetam"><img alt="Piracetam" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Piracetam.svg/145px-Piracetam.svg.png" decoding="async" width="145" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Piracetam.svg/218px-Piracetam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Piracetam.svg/290px-Piracetam.svg.png 2x" data-file-width="274" data-file-height="245" /></a></span></div> <div class="gallerytext"><a href="/wiki/Piracetam" title="Piracetam">Piracetam</a></div> </li> </ul></div></div></div> <p>Some agents included in the racetam family are not technically racetams themselves in terms of chemical structure and instead are closely related compounds.<sup id="cite_ref-Medsafe2015_17-0" class="reference"><a href="#cite_note-Medsafe2015-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> They may be referred to as "racetam-like".<sup id="cite_ref-Medsafe2015_17-1" class="reference"><a href="#cite_note-Medsafe2015-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MalykhSadaie2010_2-3" class="reference"><a href="#cite_note-MalykhSadaie2010-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> These agents include <a href="/wiki/Aloracetam" title="Aloracetam">aloracetam</a>, <a href="/w/index.php?title=Molracetam&action=edit&redlink=1" class="new" title="Molracetam (page does not exist)">molracetam</a>, <a href="/wiki/Omberacetam" class="mw-redirect" title="Omberacetam">omberacetam</a> (noopept), <a href="/w/index.php?title=Padsevonil&action=edit&redlink=1" class="new" title="Padsevonil (page does not exist)">padsevonil</a>, and <a href="/w/index.php?title=Tenilsetam&action=edit&redlink=1" class="new" title="Tenilsetam (page does not exist)">tenilsetam</a>.<sup id="cite_ref-Medsafe2015_17-2" class="reference"><a href="#cite_note-Medsafe2015-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WuCaoTian2024_6-3" class="reference"><a href="#cite_note-WuCaoTian2024-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WHO-INN-Stembook2018_18-0" class="reference"><a href="#cite_note-WHO-INN-Stembook2018-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Racetam&action=edit&section=5" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Legality">Legality</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Racetam&action=edit&section=6" title="Edit section: Legality"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Australia">Australia</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Racetam&action=edit&section=7" title="Edit section: Australia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>All racetams are schedule 4 substances in Australia under the <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons" title="Standard for the Uniform Scheduling of Medicines and Poisons">Poisons Standard (February 2020)</a>.<sup id="cite_ref-Poisons_Stanrard_19-0" class="reference"><a href="#cite_note-Poisons_Stanrard-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> A schedule 4 substance is classified as "Prescription Only Medicine, or Prescription Animal Remedy – Substances, the use or supply of which should be by or on the order of persons permitted by State or Territory legislation to prescribe and should be available from a pharmacist on prescription."<sup id="cite_ref-Poisons_Stanrard_19-1" class="reference"><a href="#cite_note-Poisons_Stanrard-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <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=Racetam&action=edit&section=8" 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 reflist-columns references-column-width" style="column-width: 32em;"> <ol class="references"> <li id="cite_note-Shorvon2001-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Shorvon2001_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Shorvon2001_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="CITEREFShorvon2001" class="citation journal cs1">Shorvon S (December 2001). 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</li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCohenZakharevichGerona2019" class="citation journal cs1">Cohen, Pieter A.; Zakharevich, Igor; Gerona, Roy (25 November 2019). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6902196">"Presence of Piracetam in Cognitive Enhancement Dietary Supplements"</a>. <i>JAMA Internal Medicine</i>. <b>180</b> (3): 458–459. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1001%2Fjamainternmed.2019.5507">10.1001/jamainternmed.2019.5507</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6902196">6902196</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/31764936">31764936</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=JAMA+Internal+Medicine&rft.atitle=Presence+of+Piracetam+in+Cognitive+Enhancement+Dietary+Supplements&rft.volume=180&rft.issue=3&rft.pages=458-459&rft.date=2019-11-25&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6902196%23id-name%3DPMC&rft_id=info%3Apmid%2F31764936&rft_id=info%3Adoi%2F10.1001%2Fjamainternmed.2019.5507&rft.aulast=Cohen&rft.aufirst=Pieter+A.&rft.au=Zakharevich%2C+Igor&rft.au=Gerona%2C+Roy&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6902196&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARacetam" class="Z3988"></span></span> </li> <li id="cite_note-WuCaoTian2024-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-WuCaoTian2024_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-WuCaoTian2024_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-WuCaoTian2024_6-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-WuCaoTian2024_6-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWuCaoTianGao2024" class="citation journal cs1">Wu PP, Cao BR, Tian FY, Gao ZB (May 2024). <a rel="nofollow" class="external text" href="https://www.researchgate.net/profile/Zhao-Bing-Gao/publication/375065148_Development_of_SV2A_Ligands_for_Epilepsy_Treatment_A_Review_of_Levetiracetam_Brivaracetam_and_Padsevonil/links/65419dd00426ef6369edf136/Development-of-SV2A-Ligands-for-Epilepsy-Treatment-A-Review-of-Levetiracetam-Brivaracetam-and-Padsevonil.pdf">"Development of SV2A Ligands for Epilepsy Treatment: A Review of 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neurosci+Bull&rft.atitle=Development+of+SV2A+Ligands+for+Epilepsy+Treatment%3A+A+Review+of+Levetiracetam%2C+Brivaracetam%2C+and+Padsevonil&rft.volume=40&rft.issue=5&rft.pages=594-608&rft.date=2024-05&rft_id=info%3Adoi%2F10.1007%2Fs12264-023-01138-2&rft_id=info%3Apmid%2F37897555&rft.aulast=Wu&rft.aufirst=PP&rft.au=Cao%2C+BR&rft.au=Tian%2C+FY&rft.au=Gao%2C+ZB&rft_id=https%3A%2F%2Fwww.researchgate.net%2Fprofile%2FZhao-Bing-Gao%2Fpublication%2F375065148_Development_of_SV2A_Ligands_for_Epilepsy_Treatment_A_Review_of_Levetiracetam_Brivaracetam_and_Padsevonil%2Flinks%2F65419dd00426ef6369edf136%2FDevelopment-of-SV2A-Ligands-for-Epilepsy-Treatment-A-Review-of-Levetiracetam-Brivaracetam-and-Padsevonil.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARacetam" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAhmedOswald2010" class="citation journal cs1">Ahmed AH, Oswald RE (March 2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2872987">"Piracetam defines a new binding site for allosteric modulators of alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) receptors"</a>. <i>Journal of Medicinal Chemistry</i>. <b>53</b> (5): 2197–203. <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%2Fjm901905j">10.1021/jm901905j</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2872987">2872987</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20163115">20163115</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=Piracetam+defines+a+new+binding+site+for+allosteric+modulators+of+alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionic+acid+%28AMPA%29+receptors&rft.volume=53&rft.issue=5&rft.pages=2197-203&rft.date=2010-03&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2872987%23id-name%3DPMC&rft_id=info%3Apmid%2F20163115&rft_id=info%3Adoi%2F10.1021%2Fjm901905j&rft.aulast=Ahmed&rft.aufirst=AH&rft.au=Oswald%2C+RE&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2872987&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARacetam" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCopaniGenazzaniAleppoCasabona1992" class="citation journal cs1">Copani A, Genazzani AA, Aleppo G, Casabona G, Canonico PL, Scapagnini U, Nicoletti F (April 1992). "Nootropic drugs positively modulate alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid-sensitive glutamate receptors in neuronal cultures". <i>Journal of Neurochemistry</i>. <b>58</b> (4): 1199–204. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1471-4159.1992.tb11329.x">10.1111/j.1471-4159.1992.tb11329.x</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/1372342">1372342</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+Neurochemistry&rft.atitle=Nootropic+drugs+positively+modulate+alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic+acid-sensitive+glutamate+receptors+in+neuronal+cultures&rft.volume=58&rft.issue=4&rft.pages=1199-204&rft.date=1992-04&rft_id=info%3Adoi%2F10.1111%2Fj.1471-4159.1992.tb11329.x&rft_id=info%3Apmid%2F1372342&rft.aulast=Copani&rft.aufirst=A&rft.au=Genazzani%2C+AA&rft.au=Aleppo%2C+G&rft.au=Casabona%2C+G&rft.au=Canonico%2C+PL&rft.au=Scapagnini%2C+U&rft.au=Nicoletti%2C+F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARacetam" class="Z3988"></span></span> </li> <li id="cite_note-Molina-CarballoCheca-RosMuñoz-Hoyos2016-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-Molina-CarballoCheca-RosMuñoz-Hoyos2016_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMolina-CarballoCheca-RosMuñoz-Hoyos2016" class="citation journal cs1">Molina-Carballo A, Checa-Ros A, Muñoz-Hoyos A (July 2016). "Treatments and compositions for attention deficit hyperactivity disorder: a patent review". <i>Expert Opin Ther Pat</i>. <b>26</b> (7): 799–814. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F13543776.2016.1182989">10.1080/13543776.2016.1182989</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/27138211">27138211</a>. <q>The racetams have different activities [e.g., phenylpiracetam is a stimulant developed and marketed in Russia, piracetam is a nootropic, and levetiracetam is widely used as an anticonvulsant (Figure 17)].</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Opin+Ther+Pat&rft.atitle=Treatments+and+compositions+for+attention+deficit+hyperactivity+disorder%3A+a+patent+review&rft.volume=26&rft.issue=7&rft.pages=799-814&rft.date=2016-07&rft_id=info%3Adoi%2F10.1080%2F13543776.2016.1182989&rft_id=info%3Apmid%2F27138211&rft.aulast=Molina-Carballo&rft.aufirst=A&rft.au=Checa-Ros%2C+A&rft.au=Mu%C3%B1oz-Hoyos%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARacetam" class="Z3988"></span></span> </li> <li id="cite_note-VeinbergVaversOrlova2015-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-VeinbergVaversOrlova2015_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-VeinbergVaversOrlova2015_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-VeinbergVaversOrlova2015_10-2"><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="CITEREFVeinbergVaversOrlovaKuznecovs2015" class="citation journal cs1">Veinberg G, Vavers E, Orlova N, Kuznecovs J, Domracheva I, Vorona M, Zvejniece L, Dambrova M (2015). "Stereochemistry of phenylpiracetam and its methyl derivative: improvement of the pharmacological profile". <i>Chemistry of Heterocyclic Compounds</i>. <b>51</b> (7): 601–606. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs10593-015-1747-9">10.1007/s10593-015-1747-9</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0009-3122">0009-3122</a>. <q>Phenylpiracetam was originally designed as a nootropic drug for the sustenance and improvement of the physical condition and cognition abilities of Soviet space crews.2 Later, especially during the last decade, phenylpiracetam was introduced into general clinical practice in Russia and in some Eastern European countries. The possible target receptors and mechanisms for the acute activity of this drug remained unclear, until very recently it was found that (R)-phenylpiracetam (5) (MRZ-9547) is a selective dopamine transporter inhibitor that moderately stimulates striatal dopamine release.19</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemistry+of+Heterocyclic+Compounds&rft.atitle=Stereochemistry+of+phenylpiracetam+and+its+methyl+derivative%3A+improvement+of+the+pharmacological+profile&rft.volume=51&rft.issue=7&rft.pages=601-606&rft.date=2015&rft_id=info%3Adoi%2F10.1007%2Fs10593-015-1747-9&rft.issn=0009-3122&rft.aulast=Veinberg&rft.aufirst=G&rft.au=Vavers%2C+E&rft.au=Orlova%2C+N&rft.au=Kuznecovs%2C+J&rft.au=Domracheva%2C+I&rft.au=Vorona%2C+M&rft.au=Zvejniece%2C+L&rft.au=Dambrova%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARacetam" class="Z3988"></span></span> </li> <li id="cite_note-SommerDanyszRuss2014-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-SommerDanyszRuss2014_11-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSommerDanyszRussValastro2014" class="citation journal cs1">Sommer S, Danysz W, Russ H, Valastro B, Flik G, Hauber W (December 2014). "The dopamine reuptake inhibitor MRZ-9547 increases progressive ratio responding in rats". <i>The International Journal of Neuropsychopharmacology</i>. <b>17</b> (12): 2045–2056. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1017%2FS1461145714000996">10.1017/S1461145714000996</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/24964269">24964269</a>. <q>Here, we tested the effects of MRZ-9547 [...], and its l-enantiomer MRZ-9546 on effort-related decision making in rats. The racemic form of these compounds referred to as phenotropil has been shown to stimulate motor activity in rats (Zvejniece et al., 2011) and enhance physical capacity and cognition in humans (Malykh and Sadaie, 2010). [...] MRZ-9547 turned out to be a DAT inhibitor as shown by displacement of binding of [125I] RTI-55 (IC50 = 4.82 ± 0.05 μM, n=3) to human recombinant DAT expressed in CHO-K1 cells and inhibition of DA uptake (IC50 = 14.5 ± 1.6 μM, n=2) in functional assays in the same cells. It inhibited norepinephrine transporter (NET) with an IC50 of 182 μM (one experiment in duplicate). The potencies for the l-enantiomer MRZ-9546 were as follows: DAT binding (Ki = 34.8 ± 14.8 μM, n=3), DAT function (IC50 = 65.5 ± 8.3 μM, n=2) and NET function (IC50 = 667 μM, one experiment performed in duplicate).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+International+Journal+of+Neuropsychopharmacology&rft.atitle=The+dopamine+reuptake+inhibitor+MRZ-9547+increases+progressive+ratio+responding+in+rats&rft.volume=17&rft.issue=12&rft.pages=2045-2056&rft.date=2014-12&rft_id=info%3Adoi%2F10.1017%2FS1461145714000996&rft_id=info%3Apmid%2F24964269&rft.aulast=Sommer&rft.aufirst=S&rft.au=Danysz%2C+W&rft.au=Russ%2C+H&rft.au=Valastro%2C+B&rft.au=Flik%2C+G&rft.au=Hauber%2C+W&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARacetam" class="Z3988"></span></span> </li> <li id="cite_note-StutzGolaniWitkin2019-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-StutzGolaniWitkin2019_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStutzGolaniWitkin2019" class="citation journal cs1">Stutz PV, Golani LK, Witkin JM (February 2019). "Animal models of fatigue in major depressive disorder". <i>Physiology & Behavior</i>. <b>199</b>: 300–305. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.physbeh.2018.11.042">10.1016/j.physbeh.2018.11.042</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/30513290">30513290</a>. <q>In a study performed by Sommer et al. (2014), healthy rats treated with the selective dopamine transport (DAT) inhibitor MRZ-9547 (Fig. 1) chose high effort, high reward more often than their untreated matched controls. Unlike similar studies, however, depressive symptoms were not induced before treatment; rather, baseline healthy controls were compared to healthy rats treated with MRZ-9547. [...] In one study, the selective DAT inhibitor MRZ-9547 increased the number of lever presses more than untreated controls (Sommer et al., 2014). The investigators concluded that such effort-based "decision making in rodents could provide an animal model for motivational dysfunctions related to effort expenditure such as fatigue, e.g. in Parkinson's disease or major depression." Based upon the findings with MRZ-9547, they suggested that this drug mechanism might be a valuable therapeutic entity for fatigue in neurological and neuropsychiatric disorders. [...] A high effort bias been reported with bupropion (Randall et al., 2015), lisdexamfetamine (Yohn etal., 2016e), and the DA uptake blockers MRZ-9547 (Sommer et al., 2014), PRX-14040 (Fig. 1) (Yohn et al., 2016d) and GBR12909 (Fig. 1) (Yohn et al., 2016c).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Physiology+%26+Behavior&rft.atitle=Animal+models+of+fatigue+in+major+depressive+disorder&rft.volume=199&rft.pages=300-305&rft.date=2019-02&rft_id=info%3Adoi%2F10.1016%2Fj.physbeh.2018.11.042&rft_id=info%3Apmid%2F30513290&rft.aulast=Stutz&rft.aufirst=PV&rft.au=Golani%2C+LK&rft.au=Witkin%2C+JM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARacetam" class="Z3988"></span></span> </li> <li id="cite_note-VaversZvejnieceMaurice2019-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-VaversZvejnieceMaurice2019_13-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVaversZvejnieceMauriceDambrova2019" class="citation journal cs1">Vavers E, Zvejniece L, Maurice T, Dambrova M (2019). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6433746">"Allosteric Modulators of Sigma-1 Receptor: A Review"</a>. <i>Front Pharmacol</i>. <b>10</b>: 223. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3389%2Ffphar.2019.00223">10.3389/fphar.2019.00223</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6433746">6433746</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30941035">30941035</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Front+Pharmacol&rft.atitle=Allosteric+Modulators+of+Sigma-1+Receptor%3A+A+Review&rft.volume=10&rft.pages=223&rft.date=2019&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6433746%23id-name%3DPMC&rft_id=info%3Apmid%2F30941035&rft_id=info%3Adoi%2F10.3389%2Ffphar.2019.00223&rft.aulast=Vavers&rft.aufirst=E&rft.au=Zvejniece%2C+L&rft.au=Maurice%2C+T&rft.au=Dambrova%2C+M&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6433746&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARacetam" class="Z3988"></span></span> </li> <li id="cite_note-ZvejnieceVaversSvalbe2014-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-ZvejnieceVaversSvalbe2014_14-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZvejnieceVaversSvalbeVilskersts2014" class="citation journal cs1">Zvejniece L, Vavers E, Svalbe B, Vilskersts R, Domracheva I, Vorona M, Veinberg G, Misane I, Stonans I, Kalvinsh I, Dambrova M (February 2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3969087">"The cognition-enhancing activity of E1R, a novel positive allosteric modulator of sigma-1 receptors"</a>. <i>Br J Pharmacol</i>. <b>171</b> (3): 761–771. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fbph.12506">10.1111/bph.12506</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3969087">3969087</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24490863">24490863</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Br+J+Pharmacol&rft.atitle=The+cognition-enhancing+activity+of+E1R%2C+a+novel+positive+allosteric+modulator+of+sigma-1+receptors&rft.volume=171&rft.issue=3&rft.pages=761-771&rft.date=2014-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3969087%23id-name%3DPMC&rft_id=info%3Apmid%2F24490863&rft_id=info%3Adoi%2F10.1111%2Fbph.12506&rft.aulast=Zvejniece&rft.aufirst=L&rft.au=Vavers%2C+E&rft.au=Svalbe%2C+B&rft.au=Vilskersts%2C+R&rft.au=Domracheva%2C+I&rft.au=Vorona%2C+M&rft.au=Veinberg%2C+G&rft.au=Misane%2C+I&rft.au=Stonans%2C+I&rft.au=Kalvinsh%2C+I&rft.au=Dambrova%2C+M&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3969087&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARacetam" class="Z3988"></span></span> </li> <li id="cite_note-4-S1-P51-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-4-S1-P51_15-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVaversZvejnieceVeinbergSvalbe2015" class="citation journal cs1">Vavers E, Zvejniece L, Veinberg G, Svalbe B, Domracheva I, Vilskersts R, Dambrova M (2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4797911">"Novel positive allosteric modulators of sigma-1 receptor"</a>. <i>SpringerPlus</i>. <b>4</b> (Suppl 1): P51. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1186%2F2193-1801-4-S1-P51">10.1186/2193-1801-4-S1-P51</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4797911">4797911</a></span>. <q>The <i>R</i>-configuration enantiomers of methylphenylpiracetam are more active positive allosteric modulators of Sigma-1 receptor than <i>S</i>-configuration enantiomers.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=SpringerPlus&rft.atitle=Novel+positive+allosteric+modulators+of+sigma-1+receptor&rft.volume=4&rft.issue=Suppl+1&rft.pages=P51&rft.date=2015&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4797911%23id-name%3DPMC&rft_id=info%3Adoi%2F10.1186%2F2193-1801-4-S1-P51&rft.aulast=Vavers&rft.aufirst=E&rft.au=Zvejniece%2C+L&rft.au=Veinberg%2C+G&rft.au=Svalbe%2C+B&rft.au=Domracheva%2C+I&rft.au=Vilskersts%2C+R&rft.au=Dambrova%2C+M&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4797911&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARacetam" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBartusDeanShermanFriedman1981" class="citation journal cs1">Bartus RT, Dean RL, Sherman KA, Friedman E, Beer B (1981). "Profound effects of combining choline and piracetam on memory enhancement and cholinergic function in aged rats". <i>Neurobiology of Aging</i>. <b>2</b> (2): 105–11. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0197-4580%2881%2990007-5">10.1016/0197-4580(81)90007-5</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/7301036">7301036</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neurobiology+of+Aging&rft.atitle=Profound+effects+of+combining+choline+and+piracetam+on+memory+enhancement+and+cholinergic+function+in+aged+rats&rft.volume=2&rft.issue=2&rft.pages=105-11&rft.date=1981&rft_id=info%3Adoi%2F10.1016%2F0197-4580%2881%2990007-5&rft_id=info%3Apmid%2F7301036&rft.aulast=Bartus&rft.aufirst=RT&rft.au=Dean%2C+RL&rft.au=Sherman%2C+KA&rft.au=Friedman%2C+E&rft.au=Beer%2C+B&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARacetam" class="Z3988"></span></span> </li> <li id="cite_note-Medsafe2015-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-Medsafe2015_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Medsafe2015_17-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Medsafe2015_17-2"><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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://medsafe.govt.nz/profs/class/Agendas/agen53Racetams.pdf">"Classification Status of Racetams"</a> <span class="cs1-format">(PDF)</span>. Medsafe. 2015<span class="reference-accessdate">. Retrieved <span class="nowrap">1 October</span> 2024</span>. <q>Many of the products are based on a group of compounds known collectively as racetams or 'racetam-like' substances. [...] In addition, three substances that do not strictly meet the racetam definition (due to lack of a 2-pyrrolidone ring) are typically described as being part of the racetam family. These are aloracetam, molracetam and noopept.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Classification+Status+of+Racetams&rft.pub=Medsafe&rft.date=2015&rft_id=https%3A%2F%2Fmedsafe.govt.nz%2Fprofs%2Fclass%2FAgendas%2Fagen53Racetams.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARacetam" class="Z3988"></span></span> </li> <li id="cite_note-WHO-INN-Stembook2018-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-WHO-INN-Stembook2018_18-0">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external free" href="https://cdn.who.int/media/docs/default-source/international-nonproprietary-names-(inn)/stembook-2018.pdf">https://cdn.who.int/media/docs/default-source/international-nonproprietary-names-(inn)/stembook-2018.pdf</a></span> </li> <li id="cite_note-Poisons_Stanrard-19"><span class="mw-cite-backlink">^ <a href="#cite_ref-Poisons_Stanrard_19-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Poisons_Stanrard_19-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://www.legislation.gov.au/Details/F2020C00148">Poisons Standard February 2020</a>. comlaw.gov.au</span> </li> </ol></div> <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 dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul 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.navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Racetams" style="padding:3px"><table 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template">e</abbr></a></li></ul></div><div id="Racetams" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Racetams</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Racetams</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>Nootropics:</i> <a href="/wiki/Aniracetam" title="Aniracetam">Aniracetam</a></li> <li><a href="/wiki/Coluracetam" title="Coluracetam">Coluracetam</a></li> <li><a href="/wiki/Dimiracetam" title="Dimiracetam">Dimiracetam</a></li> <li><a href="/wiki/Doliracetam" title="Doliracetam">Doliracetam</a></li> <li><a href="/wiki/Dupracetam" title="Dupracetam">Dupracetam</a></li> <li><a href="/wiki/Fasoracetam" title="Fasoracetam">Fasoracetam</a></li> <li><a href="/wiki/Imuracetam" title="Imuracetam">Imuracetam</a></li> <li><a href="/wiki/Nebracetam" title="Nebracetam">Nebracetam</a></li> <li><a href="/wiki/Nefiracetam" title="Nefiracetam">Nefiracetam</a></li> <li><a href="/w/index.php?title=Nicoracetam&action=edit&redlink=1" class="new" title="Nicoracetam (page does not exist)">Nicoracetam</a></li> <li><a href="/wiki/Oxiracetam" title="Oxiracetam">Oxiracetam</a></li> <li><a href="/w/index.php?title=Piperacetam&action=edit&redlink=1" class="new" title="Piperacetam (page does not exist)">Piperacetam</a></li> <li><a href="/wiki/Piracetam" title="Piracetam">Piracetam</a></li> <li><a href="/wiki/Pramiracetam" title="Pramiracetam">Pramiracetam</a></li> <li><a href="/wiki/Rolipram" title="Rolipram">Rolipram</a></li> <li><a href="/wiki/Rolziracetam" title="Rolziracetam">Rolziracetam</a></li></ul> <ul><li><i>Anticonvulsants:</i> <a href="/wiki/Brivaracetam" title="Brivaracetam">Brivaracetam</a></li> <li><a href="/wiki/Etiracetam" title="Etiracetam">Etiracetam</a> <ul><li><a href="/wiki/Levetiracetam" title="Levetiracetam">Levetiracetam</a></li></ul></li> <li><a href="/wiki/Seletracetam" title="Seletracetam">Seletracetam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylpiracetam" title="Phenylpiracetam">Phenylpiracetams</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>Nootropics and/or stimulants:</i> <a href="/wiki/Cebaracetam" title="Cebaracetam">Cebaracetam</a></li> <li><a href="/wiki/Methylphenylpiracetam" title="Methylphenylpiracetam">Methylphenylpiracetam</a> <ul><li><a href="/wiki/E1R" class="mw-redirect" title="E1R">E1R ((4<i>R</i>,5<i>S</i>)-methylphenylpiracetam)</a></li></ul></li> <li><a href="/wiki/Phenylpiracetam" title="Phenylpiracetam">Phenylpiracetam (phenotropil; fonturacetam)</a> <ul><li><a href="/wiki/MRZ-9547" title="MRZ-9547">MRZ-9547 ((<i>R</i>)-phenylpiracetam)</a></li> <li><a href="/w/index.php?title=(S)-Phenylpiracetam&action=edit&redlink=1" class="new" title="(S)-Phenylpiracetam (page does not exist)">(<i>S</i>)-Phenylpiracetam</a></li></ul></li> <li><a href="/wiki/RGPU-95" title="RGPU-95">RGPU-95 (chlorophenylpiracetam)</a></li></ul> <ul><li><i>Anticonvulsants:</i> <a href="/wiki/Phenylpiracetam_hydrazide" title="Phenylpiracetam hydrazide">Phenylpiracetam hydrazide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Racetam-like</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>Nootropics:</i> <a href="/wiki/Aloracetam" title="Aloracetam">Aloracetam</a></li> <li><a href="/w/index.php?title=Molracetam&action=edit&redlink=1" class="new" title="Molracetam (page does not exist)">Molracetam</a></li> <li><a href="/wiki/Omberacetam" class="mw-redirect" title="Omberacetam">Omberacetam (Noopept)</a></li> <li><a href="/w/index.php?title=Tenilsetam&action=edit&redlink=1" class="new" title="Tenilsetam (page does not exist)">Tenilsetam</a></li> <li><a href="/wiki/Traneurocin" title="Traneurocin">Traneurocin (cycloprolylglycine; NA-831)</a></li></ul> <ul><li><i>Anticonvulsants:</i> <a href="/w/index.php?title=Padsevonil&action=edit&redlink=1" class="new" title="Padsevonil (page does not exist)">Padsevonil</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" 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=Racetam&oldid=1248860118">https://en.wikipedia.org/w/index.php?title=Racetam&oldid=1248860118</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" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Racetams" 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