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href="#Natural_occurrence_of_piperidine_and_derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Natural occurrence of piperidine and derivatives</span> </div> </a> <ul id="toc-Natural_occurrence_of_piperidine_and_derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Conformation" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Conformation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Conformation</span> </div> </a> <ul id="toc-Conformation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Reactions</span> </div> </a> <ul id="toc-Reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-NMR_chemical_control" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#NMR_chemical_control"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>NMR chemical control</span> </div> </a> <ul id="toc-NMR_chemical_control-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Uses</span> </div> </a> <ul id="toc-Uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-List_of_piperidine_medications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#List_of_piperidine_medications"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>List of piperidine medications</span> </div> </a> <ul id="toc-List_of_piperidine_medications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Piperidine</span></h1> <div id="p-lang-btn" 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Available in 36 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-36" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">36 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A8%D9%8A%D8%A8%D8%B1%D9%8A%D8%AF%D9%8A%D9%86" title="بيبريدين – Arabic" lang="ar" hreflang="ar" data-title="بيبريدين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Piperidin" title="Piperidin – Azerbaijani" lang="az" hreflang="az" data-title="Piperidin" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Piperidina" title="Piperidina – Catalan" lang="ca" hreflang="ca" data-title="Piperidina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Piperidin" title="Piperidin – Czech" lang="cs" hreflang="cs" data-title="Piperidin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Piperidin" title="Piperidin – German" lang="de" hreflang="de" data-title="Piperidin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A0%CE%B9%CF%80%CE%B5%CF%81%CE%B9%CE%B4%CE%AF%CE%BD%CE%B7" title="Πιπεριδίνη – Greek" lang="el" hreflang="el" data-title="Πιπεριδίνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Piperidina" title="Piperidina – Spanish" lang="es" hreflang="es" data-title="Piperidina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Piperidino" title="Piperidino – Esperanto" lang="eo" hreflang="eo" data-title="Piperidino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Piperidina" title="Piperidina – Basque" lang="eu" hreflang="eu" data-title="Piperidina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%BE%DB%8C%D9%BE%D8%B1%DB%8C%D8%AF%DB%8C%D9%86" title="پیپریدین – Persian" lang="fa" hreflang="fa" data-title="پیپریدین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Pip%C3%A9ridine" title="Pipéridine – French" lang="fr" hreflang="fr" data-title="Pipéridine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%94%BC%ED%8E%98%EB%A6%AC%EB%94%98" title="피페리딘 – Korean" lang="ko" hreflang="ko" data-title="피페리딘" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8A%D5%AB%D5%BA%D5%A5%D6%80%D5%AB%D5%A4%D5%AB%D5%B6" title="Պիպերիդին – Armenian" lang="hy" hreflang="hy" data-title="Պիպերիդին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Piperidin" title="Piperidin – Croatian" lang="hr" hreflang="hr" data-title="Piperidin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Piperidina" title="Piperidina – Italian" lang="it" hreflang="it" data-title="Piperidina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9F%D0%B8%D0%BF%D0%B5%D1%80%D0%B8%D0%B4%D0%B8%D0%BD" title="Пиперидин – Kazakh" lang="kk" hreflang="kk" data-title="Пиперидин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9F%D0%B8%D0%BF%D0%B5%D1%80%D0%B8%D0%B4%D0%B8%D0%BD" title="Пиперидин – Kyrgyz" lang="ky" hreflang="ky" data-title="Пиперидин" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Piperidinum" title="Piperidinum – Latin" lang="la" hreflang="la" data-title="Piperidinum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Piperid%C4%ABns" title="Piperidīns – Latvian" lang="lv" hreflang="lv" data-title="Piperidīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Piperidin" title="Piperidin – Hungarian" lang="hu" hreflang="hu" data-title="Piperidin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Piperidine" title="Piperidine – Dutch" lang="nl" hreflang="nl" data-title="Piperidine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%94%E3%83%9A%E3%83%AA%E3%82%B8%E3%83%B3" title="ピペリジン – Japanese" lang="ja" hreflang="ja" data-title="ピペリジン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Piperidin" title="Piperidin – Uzbek" lang="uz" hreflang="uz" data-title="Piperidin" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Piperydyna" title="Piperydyna – Polish" lang="pl" hreflang="pl" data-title="Piperydyna" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Piperidina" title="Piperidina – Portuguese" lang="pt" hreflang="pt" data-title="Piperidina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Piperidin%C4%83" title="Piperidină – Romanian" lang="ro" hreflang="ro" data-title="Piperidină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9F%D0%B8%D0%BF%D0%B5%D1%80%D0%B8%D0%B4%D0%B8%D0%BD" title="Пиперидин – Russian" lang="ru" hreflang="ru" data-title="Пиперидин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Piperid%C3%ADn" title="Piperidín – Slovak" lang="sk" hreflang="sk" data-title="Piperidín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Piperidin" title="Piperidin – Slovenian" lang="sl" hreflang="sl" data-title="Piperidin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Piperidin" title="Piperidin – Serbian" lang="sr" hreflang="sr" data-title="Piperidin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Piperidin" title="Piperidin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Piperidin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Piperidiini" title="Piperidiini – Finnish" lang="fi" hreflang="fi" data-title="Piperidiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Piperidin" title="Piperidin – Swedish" lang="sv" hreflang="sv" data-title="Piperidin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9F%D1%96%D0%BF%D0%B5%D1%80%D0%B8%D0%B4%D0%B8%D0%BD" title="Піперидин – Ukrainian" lang="uk" hreflang="uk" data-title="Піперидин" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link 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td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Piperidine<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Piperidin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/Piperidin.svg/80px-Piperidin.svg.png" decoding="async" width="80" height="126" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/Piperidin.svg/120px-Piperidin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/54/Piperidin.svg/160px-Piperidin.svg.png 2x" data-file-width="70" data-file-height="110" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Piperidine-equatorial-3D-balls-B.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Piperidine-equatorial-3D-balls-B.png/140px-Piperidine-equatorial-3D-balls-B.png" decoding="async" width="140" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Piperidine-equatorial-3D-balls-B.png/210px-Piperidine-equatorial-3D-balls-B.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Piperidine-equatorial-3D-balls-B.png/280px-Piperidine-equatorial-3D-balls-B.png 2x" data-file-width="1100" data-file-height="857" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Piperidine-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Piperidine-3D-vdW.png/150px-Piperidine-3D-vdW.png" decoding="async" width="150" height="137" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Piperidine-3D-vdW.png/225px-Piperidine-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/33/Piperidine-3D-vdW.png/300px-Piperidine-3D-vdW.png 2x" data-file-width="1100" data-file-height="1003" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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;">Piperidine</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Piperidine<sup id="cite_ref-iupac2013_2-0" class="reference"><a href="#cite_note-iupac2013-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></div></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;">Hexahydropyridine<br />Azacyclohexane<br />Pentamethyleneamine<br />Azinane</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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=110-89-4">110-89-4</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></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=C1CCNCC1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=18049">CHEBI:18049</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL15487">ChEMBL15487</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></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.7791.html">7791</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.003.467">100.003.467</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q410234#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>203-813-0</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=5477">5477</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C01746">C01746</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/8082">8082</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>TM3500000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/67I85E138Y">67I85E138Y</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>2401 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID6021165">DTXSID6021165</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q410234#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></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; background:transparent;"><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/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: NQRYJNQNLNOLGT-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><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=1/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2</div></div></li><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=1/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: NQRYJNQNLNOLGT-UHFFFAOYAY</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; background:transparent;"><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%;">C1CCNCC1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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>5</sub><span title="Hydrogen">H</span><sub>11</sub><span title="Nitrogen">N</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001851500000000000♠"></span>85.150</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Semen-like,<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> fishy-ammoniacal, pungent </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.862 g/mL </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−7 °C (19 °F; 266 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>106 °C (223 °F; 379 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Miscible </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>11.22 (protonated)<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>-64.2·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>1.573 <a href="/wiki/Poise_(unit)" title="Poise (unit)">cP</a> at 25 °C </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/50px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/75px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/100px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H225: Highly flammable liquid and vapour">H225</abbr>, <abbr class="abbr" title="H311: Toxic in contact with skin">H311</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr>, <abbr class="abbr" title="H331: Toxic if inhaled">H331</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P233: Keep container tightly closed.">P233</abbr>, <abbr class="abbr" title="P240: Ground and bond container and receiving equipment.">P240</abbr>, <abbr class="abbr" title="P241: Use explosion-proof electrical/ventilating/light/.../equipment.">P241</abbr>, <abbr class="abbr" title="P242: Use only non-sparking tools.">P242</abbr>, <abbr class="abbr" title="P243: Take precautionary measures to prevent static discharges.">P243</abbr>, <abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.">P301+P330+P331</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr>, <abbr class="abbr" title="P311: Call a POISON CENTER or doctor/physician.">P311</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P322: Specific measures (see ... on this label).">P322</abbr>, <abbr class="abbr" title="P361: Remove/Take off immediately all contaminated clothing.">P361</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</abbr>, <abbr class="abbr" title="P370+P378: In case of fire: Use ... to extinguish.">P370+P378</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P403+P235: Store in a well ventilated place. Keep cool.">P403+P235</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_e7ff6424fc1bdd38" /></span><map name="ImageMap_e7ff6424fc1bdd38"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" class="notheme mw-no-invert">3</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=411027&brand=ALDRICH&PageToGoToURL=https%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fsearch%3Fterm%3Dpiperidine%26interface%3DAll%26N%3D0%26mode%3Dmatch%2520partialmax%26lang%3Den%26region%3DUS%26focus%3Dproduct">MSDS1</a> </td></tr> <tr> <td><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Brazil">BR</abbr>:</small> <a href="/wiki/Brazilian_Controlled_Drugs_and_Substances_Act#Class_D1" title="Brazilian Controlled Drugs and Substances Act">Class D1</a> (Drug precursors)<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></li></ul></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Pyridine" title="Pyridine">Pyridine</a><br /><a href="/wiki/Pyrrolidine" title="Pyrrolidine">Pyrrolidine</a><br /><a href="/wiki/Piperazine" title="Piperazine">Piperazine</a><br /><a href="/w/index.php?title=Phosphorinane&action=edit&redlink=1" class="new" title="Phosphorinane (page does not exist)">Phosphorinane</a><br /><a href="/w/index.php?title=Arsinane&action=edit&redlink=1" class="new" title="Arsinane (page does not exist)">Arsinane</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; 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 style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464207528&page2=Piperidine">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></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>Piperidine</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the molecular formula (CH<sub>2</sub>)<sub>5</sub>NH. This <a href="/wiki/Heterocyclic_compound" title="Heterocyclic compound">heterocyclic</a> <a href="/wiki/Amine" title="Amine">amine</a> consists of a six-membered ring containing five <a href="/wiki/Methylene_bridge" title="Methylene bridge">methylene bridges</a> (–CH<sub>2</sub>–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, typical of <a href="/wiki/Amine" title="Amine">amines</a>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The name comes from the genus name <i><a href="/wiki/Piper_(genus)" class="mw-redirect" title="Piper (genus)">Piper</a></i>, which is the Latin word for <a href="/wiki/Black_pepper" title="Black pepper">pepper</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> Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and <a href="/wiki/Alkaloid" title="Alkaloid">alkaloids</a>, such as natural-occurring <a href="/wiki/Solenopsin" title="Solenopsin">solenopsins</a>.<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Piperidine&action=edit&section=1" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Piperidine was first reported in 1850 by the Scottish chemist <a href="/wiki/Thomas_Anderson_(chemist)" title="Thomas Anderson (chemist)">Thomas Anderson</a> and again, independently, in 1852 by the French chemist <a href="/wiki/Auguste_Andr%C3%A9_Thomas_Cahours" title="Auguste André Thomas Cahours">Auguste Cahours</a>, who named it.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Both of them obtained piperidine by reacting <a href="/wiki/Piperine" title="Piperine">piperine</a> with <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a>. </p><p>Industrially, piperidine is produced by the <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> of <a href="/wiki/Pyridine" title="Pyridine">pyridine</a>, usually over a <a href="/wiki/Molybdenum_disulfide" title="Molybdenum disulfide">molybdenum disulfide</a> catalyst:<sup id="cite_ref-Ullmann_12-0" class="reference"><a href="#cite_note-Ullmann-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>C<sub>5</sub>H<sub>5</sub>N + 3 H<sub>2</sub> → C<sub>5</sub>H<sub>10</sub>NH</dd></dl> <p>Pyridine can also be reduced to piperidine via a modified <a href="/wiki/Birch_reduction" title="Birch reduction">Birch reduction</a> using <a href="/wiki/Sodium" title="Sodium">sodium</a> in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence_of_piperidine_and_derivatives">Natural occurrence of piperidine and derivatives</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Piperidine&action=edit&section=2" title="Edit section: Natural occurrence of piperidine and derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Piperidine itself has been obtained from <a href="/wiki/Black_pepper" title="Black pepper">black pepper</a>,<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> from <i><a href="/w/index.php?title=Psilocaulon_absimile&action=edit&redlink=1" class="new" title="Psilocaulon absimile (page does not exist)">Psilocaulon absimile</a></i> (<a href="/wiki/Aizoaceae" title="Aizoaceae">Aizoaceae</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> and in <i><a href="/w/index.php?title=Petrosimonia_monandra&action=edit&redlink=1" class="new" title="Petrosimonia monandra (page does not exist)">Petrosimonia monandra</a></i>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>The piperidine structural motif is present in numerous natural <a href="/wiki/Alkaloid" title="Alkaloid">alkaloids</a>. These include <a href="/wiki/Piperine" title="Piperine">piperine</a>, which gives <a href="/wiki/Black_pepper" title="Black pepper">black pepper</a> its spicy taste. This gave the compound its name. Other examples are the <a href="/wiki/Fire_ant" title="Fire ant">fire ant</a> toxin <a href="/wiki/Solenopsin" title="Solenopsin">solenopsin</a>,<sup id="cite_ref-bowen_18-0" class="reference"><a href="#cite_note-bowen-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> the <a href="/wiki/Nicotine" title="Nicotine">nicotine</a> analog <a href="/wiki/Anabasine" title="Anabasine">anabasine</a> of tree tobacco (<i><a href="/wiki/Nicotiana_glauca" title="Nicotiana glauca">Nicotiana glauca</a></i>), <a href="/wiki/Lobeline" title="Lobeline">lobeline</a> of <a href="/wiki/Lobelia_inflata" title="Lobelia inflata">Indian tobacco</a>, and the toxic alkaloid <a href="/wiki/Coniine" title="Coniine">coniine</a> from <a href="/wiki/Poison_hemlock" class="mw-redirect" title="Poison hemlock">poison hemlock</a>, which was used to put <a href="/wiki/Socrates" title="Socrates">Socrates</a> to death.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Conformation">Conformation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Piperidine&action=edit&section=3" title="Edit section: Conformation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Piperidine prefers a <a href="/wiki/Chair_conformation" class="mw-redirect" title="Chair conformation">chair conformation</a>, similar to <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a>. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an <a href="/wiki/Axial_position#Chair_conformation" class="mw-redirect" title="Axial position">axial position</a>, and the other in an equatorial position. After much controversy during the 1950s–1970s, the equatorial conformation was found to be more stable by 0.72 kcal/mol in the gas phase.<sup id="cite_ref-conf1_20-0" class="reference"><a href="#cite_note-conf1-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> In <a href="/wiki/Nonpolar_solvent" class="mw-redirect" title="Nonpolar solvent">nonpolar solvents</a>, a range between 0.2 and 0.6 kcal/mol has been estimated, but in polar solvents the axial conformer may be more stable.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> The two conformers interconvert rapidly through <a href="/wiki/Nitrogen_inversion" class="mw-redirect" title="Nitrogen inversion">nitrogen inversion</a>; the free energy <a href="/wiki/Activation_barrier" class="mw-redirect" title="Activation barrier">activation barrier</a> for this process, estimated at 6.1 kcal/mol, is substantially lower than the 10.4 kcal/mol for <a href="/wiki/Ring_inversion" class="mw-redirect" title="Ring inversion">ring inversion</a>.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> In the case of <i>N</i>-methylpiperidine, the equatorial conformation is preferred by 3.16 kcal/mol,<sup id="cite_ref-conf1_20-1" class="reference"><a href="#cite_note-conf1-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> which is much larger than the preference in <a href="/wiki/Methylcyclohexane" title="Methylcyclohexane">methylcyclohexane</a>, 1.74 kcal/mol. </p> <table class="wikitable" style="margin:1em auto; text-align:center;"> <tbody><tr> <td><span typeof="mw:File"><a href="/wiki/File:Piperidine-axial-3D-balls-A.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Piperidine-axial-3D-balls-A.png/200px-Piperidine-axial-3D-balls-A.png" decoding="async" width="200" height="187" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Piperidine-axial-3D-balls-A.png/300px-Piperidine-axial-3D-balls-A.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Piperidine-axial-3D-balls-A.png/400px-Piperidine-axial-3D-balls-A.png 2x" data-file-width="1100" data-file-height="1031" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Piperidine-equatorial-3D-balls-A.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Piperidine-equatorial-3D-balls-A.png/200px-Piperidine-equatorial-3D-balls-A.png" decoding="async" width="200" height="168" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Piperidine-equatorial-3D-balls-A.png/300px-Piperidine-equatorial-3D-balls-A.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/Piperidine-equatorial-3D-balls-A.png/400px-Piperidine-equatorial-3D-balls-A.png 2x" data-file-width="1100" data-file-height="926" /></a></span> </td></tr> <tr> <td>axial conformation</td> <td>equatorial conformation </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Piperidine&action=edit&section=4" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Piperidine is widely used to convert <a href="/wiki/Ketone" title="Ketone">ketones</a> to <a href="/wiki/Enamine" title="Enamine">enamines</a>.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Enamines derived from piperidine are substrates in the <a href="/wiki/Stork_enamine_alkylation" title="Stork enamine alkylation">Stork enamine alkylation</a> reaction.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Upon treatment with <a href="/wiki/Calcium_hypochlorite" title="Calcium hypochlorite">calcium hypochlorite</a>, piperidine converts to <a href="/wiki/N-Chloropiperidine" title="N-Chloropiperidine">N-chloropiperidine</a>, a <a href="/wiki/Chloramine" class="mw-redirect" title="Chloramine">chloramine</a> with the formula C<sub>5</sub>H<sub>10</sub>NCl. The resulting chloramine undergoes <a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">dehydrohalogenation</a> to afford the cyclic imine.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="NMR_chemical_control">NMR chemical control</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Piperidine&action=edit&section=5" title="Edit section: NMR chemical control"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Carbon-13_NMR" class="mw-redirect" title="Carbon-13 NMR"><sup>13</sup>C NMR</a>: (<a href="/wiki/Deuterated_chloroform" title="Deuterated chloroform">CDCl<sub>3</sub></a>, ppm) 47, 27.2, 25.2<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2016)">citation needed</span></a></i>]</sup></li> <li><a href="/wiki/Proton_NMR" class="mw-redirect" title="Proton NMR"><sup>1</sup>H NMR</a>: (CDCl<sub>3</sub>, ppm) 2.79, 2.19, 1.51<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2016)">citation needed</span></a></i>]</sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Piperidine&action=edit&section=6" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Piperidine is used as a <a href="/wiki/Solvent" title="Solvent">solvent</a> and as a <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a>. The same is true for certain derivatives: <a href="/wiki/N-formylpiperidine" class="mw-redirect" title="N-formylpiperidine"><i>N</i>-formylpiperidine</a> is a <a href="/wiki/Polar_aprotic_solvent" title="Polar aprotic solvent">polar aprotic solvent</a> with better hydrocarbon solubility than other amide solvents, and <a href="/wiki/2,2,6,6-tetramethylpiperidine" class="mw-redirect" title="2,2,6,6-tetramethylpiperidine">2,2,6,6-tetramethylpiperidine</a> is a highly <a href="/wiki/Steric_effects" title="Steric effects">sterically hindered</a> base, useful because of its low <a href="/wiki/Nucleophilicity" class="mw-redirect" title="Nucleophilicity">nucleophilicity</a> and high solubility in <a href="/wiki/Organic_solvent" class="mw-redirect" title="Organic solvent">organic solvents</a>. </p><p>A significant industrial application of piperidine is for the production of dipiperidinyl dithiuram tetrasulfide, which is used as an accelerator of the <a href="/wiki/Sulfur_vulcanization" title="Sulfur vulcanization">sulfur vulcanization</a> of rubber.<sup id="cite_ref-Ullmann_12-1" class="reference"><a href="#cite_note-Ullmann-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="List_of_piperidine_medications">List of piperidine medications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Piperidine&action=edit&section=7" title="Edit section: List of piperidine medications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Minoxidil_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Minoxidil_structure.svg/160px-Minoxidil_structure.svg.png" decoding="async" width="160" height="192" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Minoxidil_structure.svg/240px-Minoxidil_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/94/Minoxidil_structure.svg/320px-Minoxidil_structure.svg.png 2x" data-file-width="512" data-file-height="613" /></a><figcaption><a href="/wiki/Minoxidil" title="Minoxidil">Minoxidil</a> is a piperidine derivative widely used to prevent hair loss.</figcaption></figure> <p>Piperidine and its derivatives are ubiquitous building blocks in pharmaceuticals<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> and fine chemicals. The piperidine structure is found in, for example: </p> <ul><li><a href="/wiki/Icaridin" title="Icaridin">Icaridin</a> (Insect repellent)</li> <li>SSRIs (<a href="/wiki/Selective_serotonin_reuptake_inhibitors" class="mw-redirect" title="Selective serotonin reuptake inhibitors">selective serotonin reuptake inhibitors</a>) <ul><li><a href="/wiki/Paroxetine" title="Paroxetine">Paroxetine</a></li></ul></li> <li><a href="/wiki/Stimulants" class="mw-redirect" title="Stimulants">Stimulants</a> and <a href="/wiki/Nootropic" title="Nootropic">nootropics</a>: <ul><li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li> <li><a href="/wiki/Ethylphenidate" title="Ethylphenidate">Ethylphenidate</a></li> <li><a href="/wiki/Pipradrol" title="Pipradrol">Pipradrol</a></li> <li><a href="/wiki/Desoxypipradrol" title="Desoxypipradrol">Desoxypipradrol</a></li></ul></li> <li>Histamine 1 (H<sub>1</sub>) receptor antagonists/inverse agonists: <ul><li><a href="/wiki/Loratadine" title="Loratadine">Loratadine</a></li></ul></li> <li><a href="/wiki/Histamine_H3_receptor" title="Histamine H3 receptor">Histamine 3 (H<sub>3</sub>) receptor</a> antagonists/<a href="/wiki/Inverse_agonist" title="Inverse agonist">inverse agonists</a>: <ul><li><a href="/wiki/Pitolisant" title="Pitolisant">Pitolisant</a></li></ul></li> <li>SERM (<a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators">selective estrogen receptor modulators</a>) <ul><li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li></ul></li> <li><a href="/wiki/Vasodilator" class="mw-redirect" title="Vasodilator">Vasodilators</a> <ul><li><a href="/wiki/Minoxidil" title="Minoxidil">Minoxidil</a></li></ul></li> <li><a href="/wiki/Antipsychotic" title="Antipsychotic">Antipsychotic</a> medications: <ul><li><a href="/wiki/Droperidol" title="Droperidol">Droperidol</a></li> <li><a href="/wiki/Haloperidol" title="Haloperidol">Haloperidol</a></li> <li><a href="/wiki/Melperone" title="Melperone">Melperone</a></li> <li><a href="/wiki/Mesoridazine" title="Mesoridazine">Mesoridazine</a></li> <li><a href="/wiki/Risperidone" title="Risperidone">Risperidone</a></li> <li><a href="/wiki/Thioridazine" title="Thioridazine">Thioridazine</a></li></ul></li> <li><a href="/wiki/Opioid" title="Opioid">Opioids</a>: <ul><li><a href="/wiki/Dipipanone" title="Dipipanone">Dipipanone</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a> and analogs</li> <li><a href="/wiki/Loperamide" title="Loperamide">Loperamide</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine</a> (meperidine)</li> <li><a href="/wiki/Prodine" title="Prodine">Prodine</a></li></ul></li> <li><a href="/wiki/Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclohexylamines</a>: <ul><li><a href="/wiki/Phencyclidine" title="Phencyclidine">PCP</a> and analogs</li></ul></li> <li><a href="/wiki/Anticholinergic" title="Anticholinergic">anticholinergic</a> <a href="/wiki/Chemical_weapons" class="mw-redirect" title="Chemical weapons">chemical weapons</a> <ul><li><a href="/wiki/Ditran" title="Ditran">Ditran</a></li> <li><a href="/wiki/N-methyl-3-piperidyl_benzilate" class="mw-redirect" title="N-methyl-3-piperidyl benzilate"><i>N</i>-Methyl-3-piperidyl benzilate</a> (JB-336, BZ)</li></ul></li></ul> <p>Piperidine is also commonly used in chemical degradation reactions, such as the sequencing of <a href="/wiki/DNA" title="DNA">DNA</a> in the cleavage of particular modified <a href="/wiki/Nucleotides" class="mw-redirect" title="Nucleotides">nucleotides</a>. Piperidine is also commonly used as a base for the <a href="/wiki/Protecting_group" title="Protecting group">deprotection</a> of <a href="/wiki/Fmoc" class="mw-redirect" title="Fmoc">Fmoc</a>-<a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> used in solid-phase <a href="/wiki/Peptide_synthesis" title="Peptide synthesis">peptide synthesis</a>. </p><p>Piperidine is listed as a Table II precursor under the <a href="/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances" title="United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances">United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances</a> due to its use (peaking in the 1970s) in the clandestine manufacture of <a href="/wiki/Phencyclidine" title="Phencyclidine">phencyclidine</a>.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<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=Piperidine&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: 30em;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc03/icsc0317.htm">"International Chemical Safety Card 0317"</a>. 28 January 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=International+Chemical+Safety+Card+0317&rft.date=2024-01-28&rft_id=http%3A%2F%2Fwww.ilo.org%2Fpublic%2Fenglish%2Fprotection%2Fsafework%2Fcis%2Fproducts%2Ficsc%2Fdtasht%2F_icsc03%2Ficsc0317.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3APiperidine" class="Z3988"></span></span> </li> <li id="cite_note-iupac2013-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-iupac2013_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1">"Front Matter". <i>Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. 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