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<ul id="toc-Immune_system-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Weight_regulation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Weight_regulation"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Weight regulation</span> </div> </a> <ul id="toc-Weight_regulation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Biochemistry</span> </div> </a> <button aria-controls="toc-Biochemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Biochemistry subsection</span> </button> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mechanism"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Mechanism</span> </div> </a> <ul id="toc-Mechanism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Regulation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Regulation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Regulation</span> </div> </a> <ul id="toc-Regulation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Metabolism</span> </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Measurement" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Measurement"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Measurement</span> </div> </a> <ul id="toc-Measurement-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Use_as_a_medication_and_supplement" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Use_as_a_medication_and_supplement"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Use as a medication and supplement</span> </div> </a> <ul id="toc-Use_as_a_medication_and_supplement-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>History</span> </div> </a> <button aria-controls="toc-History-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle History subsection</span> </button> <ul id="toc-History-sublist" class="vector-toc-list"> <li id="toc-Discovery" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Discovery"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Discovery</span> </div> </a> <ul id="toc-Discovery-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Etymology" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Etymology"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Etymology</span> </div> </a> <ul id="toc-Etymology-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Occurrence" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Occurrence</span> </div> </a> <button aria-controls="toc-Occurrence-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Occurrence subsection</span> </button> <ul id="toc-Occurrence-sublist" class="vector-toc-list"> <li id="toc-Animals_and_Humans" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Animals_and_Humans"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Animals and Humans</span> </div> </a> <ul id="toc-Animals_and_Humans-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Plants" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Plants"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Plants</span> </div> </a> <ul id="toc-Plants-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fungi" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fungi"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Fungi</span> </div> </a> <ul id="toc-Fungi-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bacteria" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bacteria"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Bacteria</span> </div> </a> <ul id="toc-Bacteria-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Archaea" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Archaea"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.5</span> <span>Archaea</span> </div> </a> <ul id="toc-Archaea-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Food_products" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Food_products"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.6</span> <span>Food products</span> </div> </a> <ul id="toc-Food_products-sublist" class="vector-toc-list"> </ul> </li> </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">7</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">8</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" title="Table of Contents" > <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">Melatonin</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 69 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-69" 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">69 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/%D9%85%D9%8A%D9%84%D8%A7%D8%AA%D9%88%D9%86%D9%8A%D9%86" title="ميلاتونين – Arabic" lang="ar" hreflang="ar" data-title="ميلاتونين" 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/Melatonin" title="Melatonin – Azerbaijani" lang="az" hreflang="az" data-title="Melatonin" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%85%D9%84%D8%A7%D8%AA%D9%88%D9%86%DB%8C%D9%86" title="ملاتونین – South Azerbaijani" lang="azb" hreflang="azb" data-title="ملاتونین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9C%D0%B5%D0%BB%D0%B0%D1%82%D0%B0%D0%BD%D1%96%D0%BD" title="Мелатанін – Belarusian" lang="be" hreflang="be" data-title="Мелатанін" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%9C%D1%8D%D0%BB%D1%8F%D1%82%D0%B0%D0%BD%D1%96%D0%BD" title="Мэлятанін – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Мэлятанін" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9C%D0%B5%D0%BB%D0%B0%D1%82%D0%BE%D0%BD%D0%B8%D0%BD" title="Мелатонин – Bulgarian" lang="bg" hreflang="bg" data-title="Мелатонин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Melatonin" title="Melatonin – Bosnian" lang="bs" hreflang="bs" data-title="Melatonin" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Melatonina" title="Melatonina – Catalan" lang="ca" hreflang="ca" data-title="Melatonina" 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/Melatonin" title="Melatonin – Czech" lang="cs" hreflang="cs" data-title="Melatonin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Melatonin" title="Melatonin – Welsh" lang="cy" hreflang="cy" data-title="Melatonin" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Melatonin" title="Melatonin – Danish" lang="da" hreflang="da" data-title="Melatonin" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Melatonin" title="Melatonin – German" lang="de" hreflang="de" data-title="Melatonin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-dv mw-list-item"><a href="https://dv.wikipedia.org/wiki/%DE%89%DE%A8%DE%8D%DE%A6%DE%93%DE%AF%DE%82%DE%A8%DE%82%DE%B0" title="މިލަޓޯނިން – Divehi" lang="dv" hreflang="dv" data-title="މިލަޓޯނިން" data-language-autonym="ދިވެހިބަސް" data-language-local-name="Divehi" class="interlanguage-link-target"><span>ދިވެހިބަސް</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Melatoniin" title="Melatoniin – Estonian" lang="et" hreflang="et" data-title="Melatoniin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9C%CE%B5%CE%BB%CE%B1%CF%84%CE%BF%CE%BD%CE%AF%CE%BD%CE%B7" title="Μελατονίνη – Greek" lang="el" hreflang="el" data-title="Μελατονίνη" 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/Melatonina" title="Melatonina – Spanish" lang="es" hreflang="es" data-title="Melatonina" 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/Melatonino" title="Melatonino – Esperanto" lang="eo" hreflang="eo" data-title="Melatonino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-ext mw-list-item"><a href="https://ext.wikipedia.org/wiki/Melatonina" title="Melatonina – Extremaduran" lang="ext" hreflang="ext" data-title="Melatonina" data-language-autonym="Estremeñu" data-language-local-name="Extremaduran" class="interlanguage-link-target"><span>Estremeñu</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Melatonina" title="Melatonina – Basque" lang="eu" hreflang="eu" data-title="Melatonina" 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%85%D9%84%D8%A7%D8%AA%D9%88%D9%86%DB%8C%D9%86" title="ملاتونین – Persian" lang="fa" hreflang="fa" data-title="ملاتونین" 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/M%C3%A9latonine" title="Mélatonine – French" lang="fr" hreflang="fr" data-title="Mélatonine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Meileatoinin" title="Meileatoinin – Irish" lang="ga" hreflang="ga" data-title="Meileatoinin" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Melatonina" title="Melatonina – Galician" lang="gl" hreflang="gl" data-title="Melatonina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-gu mw-list-item"><a href="https://gu.wikipedia.org/wiki/%E0%AA%AE%E0%AB%87%E0%AA%B2%E0%AA%BE%E0%AA%9F%E0%AB%8B%E0%AA%A8%E0%AA%BF%E0%AA%A8" title="મેલાટોનિન – Gujarati" lang="gu" hreflang="gu" data-title="મેલાટોનિન" data-language-autonym="ગુજરાતી" data-language-local-name="Gujarati" class="interlanguage-link-target"><span>ગુજરાતી</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%A9%9C%EB%9D%BC%ED%86%A0%EB%8B%8C" title="멜라토닌 – Korean" lang="ko" hreflang="ko" data-title="멜라토닌" 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%84%D5%A5%D5%AC%D5%A1%D5%BF%D5%B8%D5%B6%D5%AB%D5%B6" title="Մելատոնին – Armenian" lang="hy" hreflang="hy" data-title="Մելատոնին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Melatonin" title="Melatonin – Indonesian" lang="id" hreflang="id" data-title="Melatonin" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Melat%C3%B3n%C3%ADn" title="Melatónín – Icelandic" lang="is" hreflang="is" data-title="Melatónín" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Melatonina" title="Melatonina – Italian" lang="it" hreflang="it" data-title="Melatonina" 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%9E%D7%9C%D7%98%D7%95%D7%A0%D7%99%D7%9F" title="מלטונין – Hebrew" lang="he" hreflang="he" data-title="מלטונין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9B%E1%83%94%E1%83%9A%E1%83%90%E1%83%A2%E1%83%9D%E1%83%9C%E1%83%98%E1%83%9C%E1%83%98" title="მელატონინი – Georgian" lang="ka" hreflang="ka" data-title="მელატონინი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Melatonina" title="Melatonina – Latin" lang="la" hreflang="la" data-title="Melatonina" 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/Melaton%C4%ABns" title="Melatonīns – Latvian" lang="lv" hreflang="lv" data-title="Melatonīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Melatoninas" title="Melatoninas – Lithuanian" lang="lt" hreflang="lt" data-title="Melatoninas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Melatonin" title="Melatonin – Hungarian" lang="hu" hreflang="hu" data-title="Melatonin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9C%D0%B5%D0%BB%D0%B0%D1%82%D0%BE%D0%BD%D0%B8%D0%BD" title="Мелатонин – Macedonian" lang="mk" hreflang="mk" data-title="Мелатонин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AE%E0%B5%86%E0%B4%B2%E0%B4%BE%E0%B4%9F%E0%B5%8D%E0%B4%9F%E0%B5%8B%E0%B4%A8%E0%B4%BF%E0%B5%BB" title="മെലാട്ടോനിൻ – Malayalam" lang="ml" hreflang="ml" data-title="മെലാട്ടോനിൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Melatonin" title="Melatonin – Malay" lang="ms" hreflang="ms" data-title="Melatonin" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%9C%D0%B5%D0%BB%D0%B0%D1%82%D0%BE%D0%BD%D0%B8%D0%BD" title="Мелатонин – Mongolian" lang="mn" hreflang="mn" data-title="Мелатонин" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%99%E1%80%9A%E1%80%BA%E1%80%9C%E1%80%90%E1%80%AD%E1%80%AF%E1%80%94%E1%80%84%E1%80%BA" title="မယ်လတိုနင် – Burmese" lang="my" hreflang="my" data-title="မယ်လတိုနင်" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Melatonine" title="Melatonine – Dutch" lang="nl" hreflang="nl" data-title="Melatonine" 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%A1%E3%83%A9%E3%83%88%E3%83%8B%E3%83%B3" title="メラトニン – Japanese" lang="ja" hreflang="ja" data-title="メラトニン" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Melatonin" title="Melatonin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Melatonin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Melatonin" title="Melatonin – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Melatonin" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Melatonina" title="Melatonina – Occitan" lang="oc" hreflang="oc" data-title="Melatonina" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%AE%E0%AD%87%E0%AC%B2%E0%AC%BE%E0%AC%9F%E0%AD%8B%E0%AC%A8%E0%AC%BF%E0%AC%A8" title="ମେଲାଟୋନିନ – Odia" lang="or" hreflang="or" data-title="ମେଲାଟୋନିନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Melatonin" title="Melatonin – Uzbek" lang="uz" hreflang="uz" data-title="Melatonin" 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/Melatonina" title="Melatonina – Polish" lang="pl" hreflang="pl" data-title="Melatonina" 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/Melatonina" title="Melatonina – Portuguese" lang="pt" hreflang="pt" data-title="Melatonina" 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/Melatonin%C4%83" title="Melatonină – Romanian" lang="ro" hreflang="ro" data-title="Melatonină" 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%9C%D0%B5%D0%BB%D0%B0%D1%82%D0%BE%D0%BD%D0%B8%D0%BD" title="Мелатонин – Russian" lang="ru" hreflang="ru" data-title="Мелатонин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Melatonin" title="Melatonin – Simple English" lang="en-simple" hreflang="en-simple" data-title="Melatonin" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Melaton%C3%ADn" title="Melatonín – Slovak" lang="sk" hreflang="sk" data-title="Melatonín" 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/Melatonin" title="Melatonin – Slovenian" lang="sl" hreflang="sl" data-title="Melatonin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D9%85%DB%8E%D9%84%D8%A7%D8%AA%DB%86%D9%86%DB%8C%D9%86" title="مێلاتۆنین – Central Kurdish" lang="ckb" hreflang="ckb" data-title="مێلاتۆنین" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Melatonin" title="Melatonin – Serbian" lang="sr" hreflang="sr" data-title="Melatonin" 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/Melatonin" title="Melatonin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Melatonin" 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/Melatoniini" title="Melatoniini – Finnish" lang="fi" hreflang="fi" data-title="Melatoniini" 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/Melatonin" title="Melatonin – Swedish" lang="sv" hreflang="sv" data-title="Melatonin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AE%E0%AF%86%E0%AE%B2%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AF%8B%E0%AE%A9%E0%AE%BF%E0%AE%A9%E0%AF%8D" title="மெலட்டோனின் – Tamil" lang="ta" hreflang="ta" data-title="மெலட்டோனின்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%AE%E0%B1%86%E0%B0%B2%E0%B0%9F%E0%B1%8B%E0%B0%A8%E0%B0%BF%E0%B0%A8%E0%B1%8D" title="మెలటోనిన్ – Telugu" lang="te" hreflang="te" data-title="మెలటోనిన్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%80%E0%B8%A1%E0%B8%A5%E0%B8%B2%E0%B9%82%E0%B8%97%E0%B8%99%E0%B8%B4%E0%B8%99" title="เมลาโทนิน – Thai" lang="th" hreflang="th" data-title="เมลาโทนิน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%9C%D0%B5%D0%BB%D0%BE%D1%82%D0%BE%D0%BD%D0%B8%D0%BD" title="Мелотонин – Tajik" lang="tg" hreflang="tg" data-title="Мелотонин" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Melatonin" title="Melatonin – Turkish" lang="tr" hreflang="tr" data-title="Melatonin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9C%D0%B5%D0%BB%D0%B0%D1%82%D0%BE%D0%BD%D1%96%D0%BD" title="Мелатонін – Ukrainian" lang="uk" hreflang="uk" data-title="Мелатонін" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D9%85%DB%8C%D9%84%D8%A7_%D9%B9%D9%88%D9%86%D9%86" title="میلا ٹونن – Urdu" lang="ur" hreflang="ur" data-title="میلا ٹونن" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Melatonin" title="Melatonin – Vietnamese" lang="vi" hreflang="vi" data-title="Melatonin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%A4%AA%E9%BB%91%E7%B4%A0" title="褪黑素 – Wu" lang="wuu" hreflang="wuu" data-title="褪黑素" 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<div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Hormone released by the pineal gland</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Melanin" title="Melanin">melanin</a>. For the video game see <a href="/wiki/Melatonin_(video_game)" title="Melatonin (video game)"><i>Melatonin</i> (video game)</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">This article is about melatonin as a hormone. For its role as a supplement and medication, see <a href="/wiki/Melatonin_as_a_medication_and_supplement" title="Melatonin as a medication and supplement">Melatonin as a medication and supplement</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> </p> <table class="infobox ib-chembox"> <caption>Melatonin </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center skin-invert" typeof="mw:File"><a href="/wiki/File:Melatonin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Melatonin.svg/220px-Melatonin.svg.png" decoding="async" width="220" height="163" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Melatonin.svg/330px-Melatonin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/74/Melatonin.svg/440px-Melatonin.svg.png 2x" data-file-width="270" data-file-height="200" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Melatonin_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Melatonin_molecule_ball.png/220px-Melatonin_molecule_ball.png" decoding="async" width="220" height="151" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Melatonin_molecule_ball.png/330px-Melatonin_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/24/Melatonin_molecule_ball.png/440px-Melatonin_molecule_ball.png 2x" data-file-width="2000" data-file-height="1375" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide</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;">5-Methoxy-N-acetyltryptamine; N-Acetyl-5-methoxytryptamine; NSC-113928</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=73-31-4">73-31-4</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28%3DO%29NCCC1%3DCNC2%3DC1C%3DC%28C%3DC2%29OC">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=16796">CHEBI:16796</a></span></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/ChEMBL45">ChEMBL45</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.872.html">872</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01065">DB01065</a></span></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/100.000.725">100.000.725</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q180912#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>200-797-7200-797-7</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/C01598">C01598</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Melatonin">Melatonin</a></span> </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/896">896</a></span></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/JL5DK93RCL">JL5DK93RCL</a></span></li></ul></div> </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/DTXSID1022421">DTXSID1022421</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q180912#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;"><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/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: DRLFMBDRBRZALE-UHFFFAOYSA-N</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC(=O)NCCC1=CNC2=C1C=C(C=C2)OC</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>13</sub><span title="Hydrogen">H</span><sub>16</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>232.281 g/mol    </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>117 </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Melatonin</b>, an <a href="/wiki/Indoleamine" class="mw-redirect" title="Indoleamine">indoleamine</a>, is a <a href="/wiki/Natural_compound" class="mw-redirect" title="Natural compound">natural compound</a> produced by various <a href="/wiki/Organisms" class="mw-redirect" title="Organisms">organisms</a>, including <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> and <a href="/wiki/Eukaryotes" class="mw-redirect" title="Eukaryotes">eukaryotes</a>.<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> Its discovery in 1958 by <a href="/wiki/Aaron_B._Lerner" title="Aaron B. Lerner">Aaron B. Lerner</a> and colleagues stemmed from the isolation of a substance from the <a href="/wiki/Pineal_gland" title="Pineal gland">pineal gland</a> of cows that could induce <a href="/wiki/Skin_lightening" class="mw-redirect" title="Skin lightening">skin lightening</a> in <a href="/wiki/Common_frogs" class="mw-redirect" title="Common frogs">common frogs</a>. This compound was later identified as a <a href="/wiki/Hormone" title="Hormone">hormone</a> secreted in the <a href="/wiki/Brain" title="Brain">brain</a> during the night, playing a crucial role in regulating the <a href="/wiki/Sleep-wake_cycle" class="mw-redirect" title="Sleep-wake cycle">sleep-wake cycle</a>, also known as the circadian rhythm, in <a href="/wiki/Vertebrates" class="mw-redirect" title="Vertebrates">vertebrates</a>.<sup id="cite_ref-Auld2017_2-0" class="reference"><a href="#cite_note-Auld2017-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><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> </p><p>In vertebrates, melatonin's functions extend to <a href="/wiki/Entrainment_(chronobiology)" title="Entrainment (chronobiology)">synchronizing</a> sleep-wake cycles, encompassing sleep-wake timing and <a href="/wiki/Blood_pressure_regulation" class="mw-redirect" title="Blood pressure regulation">blood pressure regulation</a>, as well as controlling seasonal rhythmicity (<a href="/wiki/Circannual_cycle" title="Circannual cycle">circannual cycle</a>), which includes reproduction, fattening, molting, and hibernation.<sup id="cite_ref-Altun2007_4-0" class="reference"><a href="#cite_note-Altun2007-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Its effects are mediated through the activation of <a href="/wiki/Melatonin_receptor" title="Melatonin receptor">melatonin receptors</a> and its role as an <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a>.<sup id="cite_ref-Boutin2005_5-0" class="reference"><a href="#cite_note-Boutin2005-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hardeland2005_6-0" class="reference"><a href="#cite_note-Hardeland2005-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Reiter2001_7-0" class="reference"><a href="#cite_note-Reiter2001-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> In plants and bacteria, melatonin primarily serves as a defense mechanism against <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a>, indicating its evolutionary significance.<sup id="cite_ref-Tan_2012_8-0" class="reference"><a href="#cite_note-Tan_2012-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a>, key <a href="/wiki/Organelles" class="mw-redirect" title="Organelles">organelles</a> within cells, are the main producers of antioxidant melatonin,<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> underscoring the molecule's "ancient origins" and its fundamental role in protecting the earliest cells from <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a>.<sup id="cite_ref-:0_10-0" class="reference"><a href="#cite_note-:0-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_11-0" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p> In addition to its <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> functions as a hormone and antioxidant, melatonin is also administered exogenously as a <a href="/wiki/Melatonin_as_a_medication_and_supplement" title="Melatonin as a medication and supplement">dietary supplement and medication</a>. It is utilized in the treatment of <a href="/wiki/Sleep_disorder" title="Sleep disorder">sleep disorders</a>, including <a href="/wiki/Insomnia" title="Insomnia">insomnia</a> and various <a href="/wiki/Circadian_rhythm_sleep_disorders" class="mw-redirect" title="Circadian rhythm sleep disorders">circadian rhythm sleep disorders</a>.<style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style></p><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="Biological_activity">Biological activity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=1" title="Edit section: Biological activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In humans, melatonin primarily acts as a potent <a href="/wiki/Full_agonist" class="mw-redirect" title="Full agonist">full agonist</a> of two types of <a href="/wiki/Melatonin_receptors" class="mw-redirect" title="Melatonin receptors">melatonin receptors</a>: <a href="/wiki/Melatonin_receptor_1" class="mw-redirect" title="Melatonin receptor 1">melatonin receptor 1</a>, with <a href="/wiki/Picomolar" class="mw-redirect" title="Picomolar">picomolar</a> <a href="/wiki/Binding_affinity" class="mw-redirect" title="Binding affinity">binding affinity</a>, and <a href="/wiki/Melatonin_receptor_2" class="mw-redirect" title="Melatonin receptor 2">melatonin receptor 2</a>, with nanomolar binding affinity. Both receptors are part of the <a href="/wiki/G-protein_coupled_receptors" class="mw-redirect" title="G-protein coupled receptors">G-protein coupled receptors</a> (GPCRs) family, specifically the <a href="/wiki/Gi/o" class="mw-redirect" title="Gi/o">G<sub>i/o</sub> alpha subunit</a> GPCRs,<sup id="cite_ref-IUPHAR_–_melatonin_receptors_review_12-0" class="reference"><a href="#cite_note-IUPHAR_–_melatonin_receptors_review-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><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> although melatonin receptor 1 also exhibits coupling with <a href="/wiki/Gq_alpha_subunit" title="Gq alpha subunit">G<sub>q</sub> alpha subunit</a>.<sup id="cite_ref-IUPHAR_–_melatonin_receptors_review_12-1" class="reference"><a href="#cite_note-IUPHAR_–_melatonin_receptors_review-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Furthermore, melatonin functions as a high-capacity <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a>, or free radical scavenger, within <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a>, playing a dual role in combating cellular <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a>. First, it directly neutralizes <a href="/wiki/Free_radicals" class="mw-redirect" title="Free radicals">free radicals</a>, and second, it promotes the <a href="/wiki/Gene_expression" title="Gene expression">gene expression</a> of essential antioxidant enzymes, such as <a href="/wiki/Superoxide_dismutase" title="Superoxide dismutase">superoxide dismutase</a>, <a href="/wiki/Glutathione_peroxidase" title="Glutathione peroxidase">glutathione peroxidase</a>, <a href="/wiki/Glutathione_reductase" title="Glutathione reductase">glutathione reductase</a>, and <a href="/wiki/Catalase" title="Catalase">catalase</a>. This increase in antioxidant enzyme expression is mediated through <a href="/wiki/Signal_transduction_pathways" class="mw-redirect" title="Signal transduction pathways">signal transduction pathways</a> activated by the binding of melatonin to its receptors. Through these mechanisms, melatonin protects the cell against oxidative stress in two ways, and plays other roles in human health than only regulating the sleep-wake cycle.<sup id="cite_ref-pmid28400824_14-0" class="reference"><a href="#cite_note-pmid28400824-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IUPHAR_–_melatonin_receptors_review_12-2" class="reference"><a href="#cite_note-IUPHAR_–_melatonin_receptors_review-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Melatonin_as_a_mitochondrial_antioxidant_–_2017_Review_15-0" class="reference"><a href="#cite_note-Melatonin_as_a_mitochondrial_antioxidant_–_2017_Review-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Melatonin_–_2016_Review_16-0" class="reference"><a href="#cite_note-Melatonin_–_2016_Review-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid26272235_17-0" class="reference"><a href="#cite_note-pmid26272235-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Melatonin_transporters_–_2017_review_18-0" class="reference"><a href="#cite_note-Melatonin_transporters_–_2017_review-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biological_functions">Biological functions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=2" title="Edit section: Biological functions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Circadian_rhythm.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Circadian_rhythm.svg/300px-Circadian_rhythm.svg.png" decoding="async" width="300" height="225" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Circadian_rhythm.svg/450px-Circadian_rhythm.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Circadian_rhythm.svg/600px-Circadian_rhythm.svg.png 2x" data-file-width="512" data-file-height="384" /></a><figcaption>Visible light entering the eye and the cascading positive and negative signalling pathways to neuronal structures in the mamallian brain that may follow: When the eyes are exposed to sunlight, the pineal gland's melatonin production is suppressed, resulting in the secretion of hormones that promote wakefulness. Conversely, in the absence of light, the pineal gland synthesizes melatonin unabated, leading to feelings of drowsiness and facilitating the onset of sleep.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Circadian_rhythm">Circadian rhythm</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=3" title="Edit section: Circadian rhythm"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Circadian_rhythm" title="Circadian rhythm">Circadian rhythm</a></div> <p>In mammals, melatonin is critical for the regulation of sleep–wake cycles, or circadian rhythms.<sup id="cite_ref-EmetM_19-0" class="reference"><a href="#cite_note-EmetM-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The establishment of regular melatonin levels in human infants occurs around the third month after birth, with <a href="/wiki/Peak_concentrations" class="mw-redirect" title="Peak concentrations">peak concentrations</a> observed between midnight and 8:00 am.<sup id="cite_ref-pmid12589109_20-0" class="reference"><a href="#cite_note-pmid12589109-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> It has been documented that melatonin production diminishes as a person ages.<sup id="cite_ref-pmid3783419_21-0" class="reference"><a href="#cite_note-pmid3783419-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Additionally, a shift in the timing of melatonin secretion is observed during adolescence, resulting in delayed sleep and wake times, increasing their risk for <a href="/wiki/Delayed_sleep_phase_disorder" title="Delayed sleep phase disorder">delayed sleep phase disorder</a> during this period.<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> </p><p>The antioxidant properties of melatonin were first recognized in 1993.<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> <a href="/wiki/In_vitro" title="In vitro">In vitro</a> studies reveal that melatonin directly neutralizes various <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a>, including <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> (OH•), <a href="/wiki/Superoxide" title="Superoxide">superoxide</a> (O2−•), and <a href="/wiki/Reactive_nitrogen_species" title="Reactive nitrogen species">reactive nitrogen species</a> such as <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> (NO•).<sup id="cite_ref-pmid7832450_24-0" class="reference"><a href="#cite_note-pmid7832450-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Melatonin_Plants_25-0" class="reference"><a href="#cite_note-Melatonin_Plants-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> In plants, melatonin works <a href="/wiki/Synergistically" class="mw-redirect" title="Synergistically">synergistically</a> with other antioxidants, enhancing the overall effectiveness of each antioxidant.<sup id="cite_ref-Melatonin_Plants_25-1" class="reference"><a href="#cite_note-Melatonin_Plants-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> This compound has been found to be twice as efficacious as <a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a>, a known potent <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> antioxidant, at scavenging peroxyl radicals.<sup id="cite_ref-pmid7934611_26-0" class="reference"><a href="#cite_note-pmid7934611-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> The promotion of antioxidant enzyme expression, such as superoxide dismutase, glutathione peroxidase, glutathione reductase, and catalase, is mediated through melatonin receptor-triggered signal transduction pathways.<sup id="cite_ref-IUPHAR_–_melatonin_receptors_review_12-3" class="reference"><a href="#cite_note-IUPHAR_–_melatonin_receptors_review-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid28400824_14-1" class="reference"><a href="#cite_note-pmid28400824-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Melatonin's concentration in the <a href="/wiki/Mitochondrial_matrix" title="Mitochondrial matrix">mitochondrial matrix</a> is significantly higher than that found in the <a href="/wiki/Blood_plasma" title="Blood plasma">blood plasma</a>,<sup id="cite_ref-Melatonin_as_a_mitochondrial_antioxidant_–_2017_Review_15-1" class="reference"><a href="#cite_note-Melatonin_as_a_mitochondrial_antioxidant_–_2017_Review-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Melatonin_–_2016_Review_16-1" class="reference"><a href="#cite_note-Melatonin_–_2016_Review-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid26272235_17-1" class="reference"><a href="#cite_note-pmid26272235-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> emphasizing its role not only in direct free radical scavenging but also in modulating the expression of antioxidant enzymes and maintaining mitochondrial integrity. This multifaceted role shows the physiological significance of melatonin as a mitochondrial antioxidant, a notion supported by numerous scholars.<sup id="cite_ref-pmid28400824_14-2" class="reference"><a href="#cite_note-pmid28400824-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Melatonin_as_a_mitochondrial_antioxidant_–_2017_Review_15-2" class="reference"><a href="#cite_note-Melatonin_as_a_mitochondrial_antioxidant_–_2017_Review-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Melatonin_–_2016_Review_16-2" class="reference"><a href="#cite_note-Melatonin_–_2016_Review-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid26272235_17-2" class="reference"><a href="#cite_note-pmid26272235-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Melatonin_transporters_–_2017_review_18-1" class="reference"><a href="#cite_note-Melatonin_transporters_–_2017_review-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>Furthermore, the interaction of melatonin with reactive oxygen and nitrogen species results in the formation of metabolites capable of reducing free radicals.<sup id="cite_ref-IUPHAR_–_melatonin_receptors_review_12-4" class="reference"><a href="#cite_note-IUPHAR_–_melatonin_receptors_review-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Melatonin_transporters_–_2017_review_18-2" class="reference"><a href="#cite_note-Melatonin_transporters_–_2017_review-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> These metabolites, including <a href="/wiki/Cyclic_3-hydroxymelatonin" title="Cyclic 3-hydroxymelatonin">cyclic 3-hydroxymelatonin</a>, <a href="/wiki/N1-acetyl-N2-formyl-5-methoxykynuramine" class="mw-redirect" title="N1-acetyl-N2-formyl-5-methoxykynuramine">N1-acetyl-N2-formyl-5-methoxykynuramine</a> (AFMK), and <a href="/wiki/N1-Acetyl-5-methoxykynuramine" title="N1-Acetyl-5-methoxykynuramine">N1-acetyl-5-methoxykynuramine</a> (AMK), contribute to the broader antioxidative effects of melatonin through further <a href="/wiki/Redox_reactions" class="mw-redirect" title="Redox reactions">redox reactions</a> with free radicals.<sup id="cite_ref-IUPHAR_–_melatonin_receptors_review_12-5" class="reference"><a href="#cite_note-IUPHAR_–_melatonin_receptors_review-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Melatonin_transporters_–_2017_review_18-3" class="reference"><a href="#cite_note-Melatonin_transporters_–_2017_review-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Immune_system">Immune system</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=4" title="Edit section: Immune system"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Melatonin's interaction with the <a href="/wiki/Immune_system" title="Immune system">immune system</a> is recognized, yet the specifics of these interactions remain inadequately defined.<sup id="cite_ref-Carrillo-Vico2005_27-0" class="reference"><a href="#cite_note-Carrillo-Vico2005-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Arushanian2002_28-0" class="reference"><a href="#cite_note-Arushanian2002-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Chronological_items" title="Wikipedia:Manual of Style/Dates and numbers"><span title="The date of the event predicted near this tag has passed. (March 2024)">needs update</span></a></i>]</sup> An anti-inflammatory effect appears to be the most significant.<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 2023)">citation needed</span></a></i>]</sup> The efficacy of melatonin in disease treatment has been the subject of limited trials, with most available data deriving from small-scale, preliminary studies. It is posited that any beneficial immunological impact is attributable to melatonin's action on high-affinity receptors (MT1 and MT2), which are present on immunocompetent cells. Preclinical investigations suggest that melatonin may augment <a href="/wiki/Cytokine" title="Cytokine">cytokine</a> production and promote the expansion of <a href="/wiki/T_cell" title="T cell">T cells</a>,<sup id="cite_ref-pmid16729718_29-0" class="reference"><a href="#cite_note-pmid16729718-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> thereby potentially mitigating <a href="/wiki/Acquired_immunodeficiences" class="mw-redirect" title="Acquired immunodeficiences">acquired immunodeficiencies</a>.<sup id="cite_ref-Pp_30-0" class="reference"><a href="#cite_note-Pp-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Weight_regulation">Weight regulation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=5" title="Edit section: Weight regulation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Melatonin's potential to regulate weight gain is posited to involve its inhibitory effect on <a href="/wiki/Leptin" title="Leptin">leptin</a>, a hormone that serves as a long-term indicator of the body's energy status.<sup id="cite_ref-:2_31-0" class="reference"><a href="#cite_note-:2-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Leptin is important for regulating <a href="/wiki/Energy_balance_(biology)" class="mw-redirect" title="Energy balance (biology)">energy balance</a> and body weight by signaling satiety and reducing food intake. Melatonin, by modulating leptin's actions outside of waking hours, may contribute to the restoration of leptin sensitivity during daytime, thereby counteracting <a href="/wiki/Leptin_resistance" class="mw-redirect" title="Leptin resistance">leptin resistance</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=6" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=7" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Melatonin_biosynth.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Melatonin_biosynth.jpg/220px-Melatonin_biosynth.jpg" decoding="async" width="220" height="118" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Melatonin_biosynth.jpg/330px-Melatonin_biosynth.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/Melatonin_biosynth.jpg/440px-Melatonin_biosynth.jpg 2x" data-file-width="609" data-file-height="327" /></a><figcaption>Melatonin biosynthesis</figcaption></figure> <p>The <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> of melatonin in animals involves a sequence of <a href="/wiki/Enzymatic_Reactions" class="mw-redirect" title="Enzymatic Reactions">enzymatic reactions</a> starting with <a href="/wiki/L-tryptophan" class="mw-redirect" title="L-tryptophan"><small>L</small>-tryptophan</a>, which can be synthesized through the <a href="/wiki/Shikimate_pathway" title="Shikimate pathway">shikimate pathway</a> from <a href="/wiki/Chorismate" class="mw-redirect" title="Chorismate">chorismate</a>, found in plants, or obtained from <a href="/wiki/Protein_catabolism" title="Protein catabolism">protein catabolism</a>. The initial step in the melatonin biosynthesis pathway is the <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> of <small>L</small>-tryptophan's <a href="/wiki/Indole_ring" class="mw-redirect" title="Indole ring">indole ring</a> by the enzyme <a href="/wiki/Tryptophan_hydroxylase" title="Tryptophan hydroxylase">tryptophan hydroxylase</a>, resulting in the formation of <a href="/wiki/5-hydroxytryptophan" class="mw-redirect" title="5-hydroxytryptophan">5-hydroxytryptophan</a> (5-HTP). Subsequently, 5-HTP undergoes <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a>, facilitated by <a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">pyridoxal phosphate</a> and the enzyme <a href="/wiki/5-hydroxytryptophan_decarboxylase" class="mw-redirect" title="5-hydroxytryptophan decarboxylase">5-hydroxytryptophan decarboxylase</a>, yielding <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>Serotonin, an essential <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a>, is further converted into <a href="/wiki/N-acetylserotonin" class="mw-redirect" title="N-acetylserotonin"><i>N</i>-acetylserotonin</a> by the action of <a href="/wiki/Serotonin_N-acetyltransferase" class="mw-redirect" title="Serotonin N-acetyltransferase">serotonin <i>N</i>-acetyltransferase</a>, utilizing <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a>.<sup id="cite_ref-TordjmanS_34-0" class="reference"><a href="#cite_note-TordjmanS-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> The final step in the pathway involves the <a href="/wiki/Methylation" title="Methylation">methylation</a> of <a href="/wiki/N-acetylserotonin" class="mw-redirect" title="N-acetylserotonin"><i>N</i>-acetylserotonin</a>'s <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> by <a href="/wiki/Hydroxyindole_O-methyltransferase" class="mw-redirect" title="Hydroxyindole O-methyltransferase">hydroxyindole <i>O</i>-methyltransferase</a>, with <a href="/wiki/S-adenosyl_methionine" class="mw-redirect" title="S-adenosyl methionine"><i>S</i>-adenosyl methionine</a> as the <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> donor, to produce melatonin.<sup id="cite_ref-TordjmanS_34-1" class="reference"><a href="#cite_note-TordjmanS-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p><p>In <a href="/wiki/Bacteria" title="Bacteria">bacteria</a>, <a href="/wiki/Protists" class="mw-redirect" title="Protists">protists</a>, <a href="/wiki/Fungi" class="mw-redirect" title="Fungi">fungi</a>, and plants, the synthesis of melatonin also involves tryptophan as an intermediate but originates indirectly from the shikimate pathway. The pathway commences with <small><a href="/wiki/D-erythrose_4-phosphate" class="mw-redirect" title="D-erythrose 4-phosphate">D</a></small><a href="/wiki/D-erythrose_4-phosphate" class="mw-redirect" title="D-erythrose 4-phosphate">-erythrose 4-phosphate</a> and <a href="/wiki/Phosphoenolpyruvate" class="mw-redirect" title="Phosphoenolpyruvate">phosphoenolpyruvate</a>, and in <a href="/wiki/Photosynthetic" class="mw-redirect" title="Photosynthetic">photosynthetic</a> cells, additionally involves <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>. While the subsequent biosynthetic reactions share similarities with those in animals, there are slight variations in the enzymes involved in the final stages.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-hardeland2015_36-0" class="reference"><a href="#cite_note-hardeland2015-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>The hypothesis that melatonin synthesis occurs within mitochondria and <a href="/wiki/Chloroplasts" class="mw-redirect" title="Chloroplasts">chloroplasts</a> suggests an evolutionary and functional significance of melatonin in cellular <a href="/wiki/Energy_metabolism" class="mw-redirect" title="Energy metabolism">energy metabolism</a> and defense mechanisms against oxidative stress, reflecting the molecule's ancient origins and its multifaceted roles across different <a href="/wiki/Domains_of_life" class="mw-redirect" title="Domains of life">domains of life</a>.<sup id="cite_ref-Mitochondrial_biosynthesis_37-0" class="reference"><a href="#cite_note-Mitochondrial_biosynthesis-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Mechanism">Mechanism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=8" title="Edit section: Mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Melatonin_mechanism.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Melatonin_mechanism.jpg/220px-Melatonin_mechanism.jpg" decoding="async" width="220" height="428" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Melatonin_mechanism.jpg/330px-Melatonin_mechanism.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Melatonin_mechanism.jpg/440px-Melatonin_mechanism.jpg 2x" data-file-width="519" data-file-height="1009" /></a><figcaption>Mechanism of melatonin biosynthesis</figcaption></figure> <p>The mechanism of melatonin biosynthesis initiates with the hydroxylation of <small>L</small>-tryptophan, a process that requires the <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactor</a> <a href="/wiki/Tetrahydrobiopterin" title="Tetrahydrobiopterin">tetrahydrobiopterin</a> (THB) to react with oxygen and the active site iron of tryptophan hydroxylase. Although the complete mechanism is not entirely understood, two main mechanisms have been proposed: </p><p>The first mechanism involves a slow transfer of one <a href="/wiki/Electron" title="Electron">electron</a> from THB to molecular oxygen (O<sub>2</sub>), potentially producing a superoxide (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">O<span class="template-chem2-su"><span>−</span><span>2</span></span></span>). This superoxide could then recombine with the THB <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical</a> to form 4a-peroxypterin. 4a-peroxypterin may either react with the active site iron (II) to create an iron-peroxypterin intermediate or directly transfer an oxygen atom to the iron, facilitating the hydroxylation of <small>L</small>-tryptophan. </p><p>Alternatively, the second mechanism proposes that oxygen interacts with the active site iron (II) first, forming iron (III) superoxide. This molecule could then react with THB to form an iron-peroxypterin intermediate. </p><p>Following the formation of iron (IV) oxide from the iron-peroxypterin intermediate, this oxide selectively <a href="/wiki/Nucleophile" title="Nucleophile">attacks</a> a <a href="/wiki/Double_bond" title="Double bond">double bond</a> to yield a <a href="/wiki/Carbocation" title="Carbocation">carbocation</a> at the C5 position of the indole ring. A subsequent <a href="/wiki/1,2-shift" class="mw-redirect" title="1,2-shift">1,2-shift</a> of the hydrogen and the loss of one of the two hydrogen atoms on C5 would restore <a href="/wiki/Aromaticity" title="Aromaticity">aromaticity</a>, producing 5-hydroxy-<small>L</small>-tryptophan.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p><p>The decarboxylation of 5-hydroxy-<small>L</small>-tryptophan to produce 5-hydroxytryptamine is then facilitated by a decarboxylase enzyme with <a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">pyridoxal phosphate</a> (PLP) as a cofactor.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> PLP forms an <a href="/wiki/Imine" title="Imine">imine</a> with the amino acid derivative, facilitating the breaking of the <a href="/wiki/Carbon%E2%80%93carbon_bond" title="Carbon–carbon bond">carbon–carbon bond</a> and release of carbon dioxide. The <a href="/wiki/Protonation" title="Protonation">protonation</a> of the amine derived from tryptophan restores the aromaticity of the <a href="/wiki/Pyridine_ring" class="mw-redirect" title="Pyridine ring">pyridine ring</a>, leading to the production of 5-hydroxytryptamine and PLP.<sup id="cite_ref-ReferenceA_40-0" class="reference"><a href="#cite_note-ReferenceA-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>Serotonin <i>N</i>-acetyltransferase, with <a href="/wiki/Histidine" title="Histidine">histidine</a> residue His122, is hypothesized to <a href="/wiki/Deprotonate" class="mw-redirect" title="Deprotonate">deprotonate</a> the primary amine of 5-hydroxytryptamine. This deprotonation allows the <a href="/wiki/Lone_pair" title="Lone pair">lone pair</a> on the amine to attack acetyl-CoA, forming a <a href="/wiki/Tetrahedral_intermediate" class="mw-redirect" title="Tetrahedral intermediate">tetrahedral intermediate</a>. The <a href="/wiki/Thiol" title="Thiol">thiol</a> from <a href="/wiki/Coenzyme_A" title="Coenzyme A">coenzyme A</a> then acts as a <a href="/wiki/Leaving_group" title="Leaving group">leaving group</a> when attacked by a general base, producing <i>N</i>-acetylserotonin.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>The final step in the biosynthesis of melatonin involves the methylation of <i>N</i>-acetylserotonin at the hydroxyl position by SAM, resulting in the production of <a href="/wiki/S-adenosyl_homocysteine" class="mw-redirect" title="S-adenosyl homocysteine"><i>S</i>-adenosyl homocysteine</a> (SAH) and melatonin.<sup id="cite_ref-ReferenceA_40-1" class="reference"><a href="#cite_note-ReferenceA-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Regulation">Regulation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=9" title="Edit section: Regulation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In vertebrates, the secretion of melatonin is regulated through the activation of the <a href="/wiki/Beta-1_adrenergic_receptor" title="Beta-1 adrenergic receptor">beta-1 adrenergic receptor</a> by the hormone <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>.<sup id="cite_ref-Nesbitt2014_43-0" class="reference"><a href="#cite_note-Nesbitt2014-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Norepinephrine increases the concentration of intracellular <a href="/wiki/Cyclic_amp" class="mw-redirect" title="Cyclic amp">cAMP</a> via <a href="/wiki/Beta-adrenergic_receptors" class="mw-redirect" title="Beta-adrenergic receptors">beta-adrenergic receptors</a>, which in turn activates the <a href="/wiki/CAMP-dependent_protein_kinase_A" class="mw-redirect" title="CAMP-dependent protein kinase A">cAMP-dependent protein kinase A</a> (PKA). PKA then <a href="/wiki/Phosphorylates" class="mw-redirect" title="Phosphorylates">phosphorylates</a> <a href="/wiki/Aralkylamine_N-acetyltransferase" title="Aralkylamine N-acetyltransferase">arylalkylamine <i>N</i>-acetyltransferase</a> (AANAT), the penultimate enzyme in the melatonin synthesis pathway. When exposed to daylight, noradrenergic stimulation ceases, leading to the immediate degradation of the protein by <a href="/wiki/Proteasomal_degradation" class="mw-redirect" title="Proteasomal degradation">proteasomal</a> <a href="/wiki/Proteolysis" title="Proteolysis">proteolysis</a>.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> The production of melatonin recommences in the evening, a phase known as the <a href="/wiki/Dim-light_melatonin_onset" class="mw-redirect" title="Dim-light melatonin onset">dim-light melatonin onset</a>. </p><p>Blue light, especially within the <span class="nowrap">460–480 <a href="/wiki/Nanometre" title="Nanometre">nm</a></span> range, inhibits the biosynthesis of melatonin,<sup id="cite_ref-Brainard_2001_45-0" class="reference"><a href="#cite_note-Brainard_2001-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> with the degree of suppression being directly proportional to the intensity and duration of light exposure. Historically, humans in temperate climates experienced limited exposure to blue daylight during winter months, primarily receiving light from sources that emitted predominantly yellow light, such as fires.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Incandescent_light_bulbs" class="mw-redirect" title="Incandescent light bulbs">incandescent light bulbs</a> used extensively throughout the 20th century emitted relatively low levels of blue light.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> It has been found that light containing only wavelengths greater than 530 nm does not suppress melatonin under bright-light conditions.<sup id="cite_ref-Kayumov_2005_48-0" class="reference"><a href="#cite_note-Kayumov_2005-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> The use of glasses that block blue light in the hours preceding bedtime can mitigate melatonin suppression.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> Additionally, wearing blue-blocking goggles during the last hours before bedtime is recommended for individuals needing to adjust to an earlier bedtime since melatonin facilitates the onset of sleep.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism">Metabolism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=10" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Melatonin is <a href="/wiki/Metabolized" class="mw-redirect" title="Metabolized">metabolized</a> with an <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> ranging from 20 to 50 minutes.<sup id="cite_ref-drugbank_51-0" class="reference"><a href="#cite_note-drugbank-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Auld2017_2-1" class="reference"><a href="#cite_note-Auld2017-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid18368944_52-0" class="reference"><a href="#cite_note-pmid18368944-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> The primary metabolic pathway transforms melatonin into <a href="/wiki/6-hydroxymelatonin" class="mw-redirect" title="6-hydroxymelatonin">6-hydroxymelatonin</a>, which is then conjugated with sulfate and excreted in urine as a waste product.<sup id="cite_ref-metabolism_53-0" class="reference"><a href="#cite_note-metabolism-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> It is primarily metabolized by the liver enzyme <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a> and to a lesser extent by <a href="/wiki/CYP1A1" title="CYP1A1">CYP1A1</a>, <a href="/wiki/CYP2C19" title="CYP2C19">CYP2C19</a>, and <a href="/wiki/CYP1B1" title="CYP1B1">CYP1B1</a>.<sup id="cite_ref-metabolism_53-1" class="reference"><a href="#cite_note-metabolism-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Measurement">Measurement</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=11" title="Edit section: Measurement"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>For both research and clinical purposes, melatonin levels in humans can be determined through saliva or blood plasma analysis.<sup id="cite_ref-pmid30919486_54-0" class="reference"><a href="#cite_note-pmid30919486-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Use_as_a_medication_and_supplement">Use as a medication and supplement</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=12" title="Edit section: Use as a medication and supplement"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Melatonin_as_a_medication_and_supplement" title="Melatonin as a medication and supplement">Melatonin as a medication and supplement</a></div> <p>Melatonin is used both as a <a href="/wiki/Prescription_medication" class="mw-redirect" title="Prescription medication">prescription medication</a> and an <a href="/wiki/Over-the-counter" class="mw-redirect" title="Over-the-counter">over-the-counter</a> <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a> for the management of <a href="/wiki/Sleep_disorder" title="Sleep disorder">sleep disorders</a>, including <a href="/wiki/Insomnia" title="Insomnia">insomnia</a> and various <a href="/wiki/Circadian_rhythm_sleep_disorders" class="mw-redirect" title="Circadian rhythm sleep disorders">circadian rhythm sleep disorders</a> such as <a href="/wiki/Delayed_sleep_phase_disorder" title="Delayed sleep phase disorder">delayed sleep phase disorder</a>, <a href="/wiki/Jet_lag_disorder" class="mw-redirect" title="Jet lag disorder">jet lag disorder</a>, and <a href="/wiki/Shift_work_sleep_disorder" title="Shift work sleep disorder">shift work sleep disorder</a>.<sup id="cite_ref-pmid30148726_55-0" class="reference"><a href="#cite_note-pmid30148726-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> In addition to melatonin, a range of synthetic <a href="/wiki/Melatonin_receptor_agonists" class="mw-redirect" title="Melatonin receptor agonists">melatonin receptor agonists</a>, namely <a href="/wiki/Ramelteon" title="Ramelteon">ramelteon</a>, <a href="/wiki/Tasimelteon" title="Tasimelteon">tasimelteon</a>, and <a href="/wiki/Agomelatine" title="Agomelatine">agomelatine</a>, are used in medicine.<sup id="cite_ref-pmid27500861_56-0" class="reference"><a href="#cite_note-pmid27500861-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid29487083_57-0" class="reference"><a href="#cite_note-pmid29487083-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p><p>A study published by the <a href="/wiki/Journal_of_the_American_Medical_Association" class="mw-redirect" title="Journal of the American Medical Association">Journal of the American Medical Association</a> (JAMA) in April 2023 found that only 12% of the 30 melatonin gummy product preparations analyzed had melatonin quantities within ±10% of the amounts specified on their labels. Some gummy supplements were found to contain up to 347% of the declared melatonin content. In Europe, melatonin is classified as an <a href="/wiki/Active_pharmaceutical_ingredient" class="mw-redirect" title="Active pharmaceutical ingredient">active pharmaceutical ingredient</a>, highlighting the regulatory oversight of its use and distribution. Conversely, as of 2022<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Melatonin&action=edit">[update]</a></sup>, the United States was considering the inclusion of melatonin in <a href="/wiki/Pharmacy_compounding" class="mw-redirect" title="Pharmacy compounding">pharmacy compounding</a> practices. A preceding study from 2022 concluded that consuming unregulated melatonin products can expose individuals, including children, to melatonin quantities ranging from 40 to 130 times higher than the recommended levels when products are used 'as directed'.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p><p>Anecdotal reports and formal research studies over the past few decades have established a link between melatonin supplementation and more vivid <a href="/wiki/Dream" title="Dream">dreams</a>.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=13" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/History_of_the_pineal_gland" title="History of the pineal gland">History of the pineal gland</a></div> <div class="mw-heading mw-heading3"><h3 id="Discovery">Discovery</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=14" title="Edit section: Discovery"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Melatonin's discovery is linked to the study of skin color changes in some amphibians and reptiles, a phenomenon initially observed through the administration of pineal gland extracts.<sup id="cite_ref-Filadelfi1996_60-0" class="reference"><a href="#cite_note-Filadelfi1996-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sugden2004_61-0" class="reference"><a href="#cite_note-Sugden2004-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> In 1917, Carey Pratt McCord and Floyd P. Allen found that feeding extracts from the pineal glands of cows caused the skin of tadpoles to lighten by contracting the dark <a href="/wiki/Epidermal" class="mw-redirect" title="Epidermal">epidermal</a> <a href="/wiki/Melanophores" class="mw-redirect" title="Melanophores">melanophores</a>.<sup id="cite_ref-Coates_62-0" class="reference"><a href="#cite_note-Coates-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-McCord_63-0" class="reference"><a href="#cite_note-McCord-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p><p>The hormone melatonin was isolated in 1958 by <a href="/wiki/Aaron_B._Lerner" title="Aaron B. Lerner">Aaron B. Lerner</a>, a <a href="/wiki/Dermatology" title="Dermatology">dermatology</a> professor, and his team at <a href="/wiki/Yale_University" title="Yale University">Yale University</a>. Motivated by the possibility that a substance from the pineal gland could be beneficial in treating <a href="/wiki/Skin_diseases" class="mw-redirect" title="Skin diseases">skin diseases</a>, they extracted and identified melatonin from bovine pineal gland extracts.<sup id="cite_ref-pmid14415935_64-0" class="reference"><a href="#cite_note-pmid14415935-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> Subsequent research in the mid-1970s by Lynch and others demonstrated that melatonin production follows a circadian rhythm in human pineal glands.<sup id="cite_ref-pmid1167425_65-0" class="reference"><a href="#cite_note-pmid1167425-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </p><p>The first patent for the therapeutic use of melatonin as a low-dose sleep aid was awarded to <a href="/wiki/Richard_Wurtman" title="Richard Wurtman">Richard Wurtman</a> at the <a href="/wiki/Massachusetts_Institute_of_Technology" title="Massachusetts Institute of Technology">Massachusetts Institute of Technology</a> in 1995.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Etymology">Etymology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=15" title="Edit section: Etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The etymology of <i>melatonin</i> stems from its skin-lightening properties. As detailed in their publication in the <i><a href="/wiki/Journal_of_the_American_Chemical_Society" title="Journal of the American Chemical Society">Journal of the American Chemical Society</a></i>,<sup id="cite_ref-:3_67-0" class="reference"><a href="#cite_note-:3-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> Lerner and his colleagues proposed the name melatonin, derived from the Greek words <i>melas</i>, meaning 'black' or 'dark', and <i>tonos</i>, meaning 'labour',<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> 'colour'<sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> or 'suppress'.<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> This naming convention follows that of <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, another agent affecting skin color, discovered in 1948 as a modulator of <a href="/wiki/Vascular_tone" class="mw-redirect" title="Vascular tone">vascular tone</a>, which influenced its name based on its serum <a href="/wiki/Vasoconstrictor" class="mw-redirect" title="Vasoconstrictor">vasoconstrictor</a> effect.<sup id="cite_ref-pmid18100415_71-0" class="reference"><a href="#cite_note-pmid18100415-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> Melatonin was thus aptly named to reflect its role in preventing the darkening of the skin, highlighting the intersection of biochemistry and linguistics in scientific discovery.<sup id="cite_ref-:3_67-1" class="reference"><a href="#cite_note-:3-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=16" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Animals_and_Humans">Animals and Humans</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=17" title="Edit section: Animals and Humans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In vertebrates, melatonin is produced in darkness, thus usually at night, by the <a href="/wiki/Pineal_gland" title="Pineal gland">pineal gland</a>, a small <a href="/wiki/Endocrine_gland" title="Endocrine gland">endocrine gland</a><sup id="cite_ref-Reiter_72-0" class="reference"><a href="#cite_note-Reiter-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> located in the center of the brain but outside the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a>. Light/dark information reaches the <a href="/wiki/Suprachiasmatic_nucleus" title="Suprachiasmatic nucleus">suprachiasmatic nuclei</a> from retinal <a href="/wiki/Photosensitive_ganglion_cell" class="mw-redirect" title="Photosensitive ganglion cell">photosensitive ganglion cells</a> of the eyes<sup id="cite_ref-Richardson2005_73-0" class="reference"><a href="#cite_note-Richardson2005-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Perreau-Lenz2004_74-0" class="reference"><a href="#cite_note-Perreau-Lenz2004-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> rather than the melatonin signal (as was once postulated). Known as "the hormone of darkness", the onset of melatonin at dusk promotes activity in <a href="/wiki/Nocturnal" class="mw-redirect" title="Nocturnal">nocturnal</a> (night-active) animals and sleep in <a href="/wiki/Diurnality" title="Diurnality">diurnal</a> ones including humans.<sup id="cite_ref-75" class="reference"><a href="#cite_note-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> </p><p>In humans, ~30 μg of melatonin is produced daily and 80% of the total amount is produced in the night (W). The plasma maximum concentration of melatonin at night are 80–120 pg/mL and the concentrations during the day are between 10–20 pg/mL.<sup id="cite_ref-76" class="reference"><a href="#cite_note-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-77" class="reference"><a href="#cite_note-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> </p><p>Many animals and humans use the variation in duration of melatonin production each day as a seasonal clock.<sup id="cite_ref-Lincoln2003_78-0" class="reference"><a href="#cite_note-Lincoln2003-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> In animals including humans,<sup id="cite_ref-Arendt2005_79-0" class="reference"><a href="#cite_note-Arendt2005-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> the profile of melatonin synthesis and secretion is affected by the variable duration of night in summer as compared to winter. The change in duration of secretion thus serves as a biological signal for the organization of daylength-dependent (<a href="/wiki/Photoperiodism" title="Photoperiodism">photoperiodic</a>) seasonal functions such as reproduction, behavior, coat growth, and camouflage <a href="/wiki/Animal_colouration" class="mw-redirect" title="Animal colouration">coloring</a> in seasonal animals.<sup id="cite_ref-Arendt2005_79-1" class="reference"><a href="#cite_note-Arendt2005-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> In seasonal breeders that do not have long gestation periods and that mate during longer daylight hours, the melatonin signal controls the seasonal variation in their sexual physiology, and similar physiological effects can be induced by exogenous melatonin in animals including <a href="/wiki/Mynah_birds" class="mw-redirect" title="Mynah birds">mynah birds</a><sup id="cite_ref-Chaturvedi_80-0" class="reference"><a href="#cite_note-Chaturvedi-80"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup> and hamsters.<sup id="cite_ref-Chen1981_81-0" class="reference"><a href="#cite_note-Chen1981-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup> Melatonin can suppress <a href="/wiki/Libido" title="Libido">libido</a> by inhibiting secretion of <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> and <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a> from the <a href="/wiki/Anterior_pituitary" title="Anterior pituitary">anterior pituitary</a> gland, especially in mammals that have a <a href="/wiki/Reproduction" title="Reproduction">breeding</a> season when daylight hours are long. The reproduction of <a href="/wiki/Polyestrous" class="mw-redirect" title="Polyestrous">long-day breeders</a> is <a href="/wiki/Estrous_cycle#Anestrus" title="Estrous cycle">repressed by melatonin</a> and the reproduction of <a href="/wiki/Polyestrous" class="mw-redirect" title="Polyestrous">short-day breeders</a> is stimulated by melatonin. In sheep, melatonin administration has also shown antioxidant and immune-modulatory regime in prenatally stressed offspring helping them survive the crucial first days of their lives.<sup id="cite_ref-82" class="reference"><a href="#cite_note-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup> </p><p>During the night, melatonin regulates <a href="/wiki/Leptin" title="Leptin">leptin</a>, lowering its levels. </p><p><a href="/wiki/Cetacean" class="mw-redirect" title="Cetacean">Cetaceans</a> have lost all the genes for melatonin synthesis as well as those for melatonin receptors.<sup id="cite_ref-Huelsmann2019_83-0" class="reference"><a href="#cite_note-Huelsmann2019-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> This is thought to be related to their <a href="/wiki/Unihemispheric_sleep" class="mw-redirect" title="Unihemispheric sleep">unihemispheric sleep</a> pattern (one <a href="/wiki/Brain_hemisphere" class="mw-redirect" title="Brain hemisphere">brain hemisphere</a> at a time). Similar trends have been found in <a href="/wiki/Sirenia" title="Sirenia">sirenians</a>.<sup id="cite_ref-Huelsmann2019_83-1" class="reference"><a href="#cite_note-Huelsmann2019-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Plants">Plants</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=18" title="Edit section: Plants"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Until its identification in plants in 1987, melatonin was for decades thought to be primarily an animal neurohormone. When melatonin was identified in coffee extracts in the 1970s, it was believed to be a byproduct of the extraction process. Subsequently, however, melatonin has been found in all plants that have been investigated. It is present in all the different parts of plants, including leaves, stems, roots, fruits, and seeds, in varying proportions.<sup id="cite_ref-Tan_2012_8-1" class="reference"><a href="#cite_note-Tan_2012-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-84" class="reference"><a href="#cite_note-84"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> Melatonin concentrations differ not only among plant species, but also between varieties of the same species depending on the agronomic growing conditions, varying from picograms to several micrograms per gram.<sup id="cite_ref-hardeland2015_36-1" class="reference"><a href="#cite_note-hardeland2015-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bonnefont-Rousselot_2010_55–67_85-0" class="reference"><a href="#cite_note-Bonnefont-Rousselot_2010_55–67-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> Notably high melatonin concentrations have been measured in popular beverages such as coffee, <a href="/wiki/Tea" title="Tea">tea</a>, <a href="/wiki/Wine" title="Wine">wine</a>, and <a href="/wiki/Beer" title="Beer">beer</a>, and crops including <a href="/wiki/Maize" title="Maize">corn</a>, <a href="/wiki/Rice" title="Rice">rice</a>, <a href="/wiki/Wheat" title="Wheat">wheat</a>, <a href="/wiki/Barley" title="Barley">barley</a>, and <a href="/wiki/Oat" title="Oat">oats</a>.<sup id="cite_ref-Tan_2012_8-2" class="reference"><a href="#cite_note-Tan_2012-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> In some common foods and beverages, including coffee<sup id="cite_ref-Tan_2012_8-3" class="reference"><a href="#cite_note-Tan_2012-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Walnut" title="Walnut">walnuts</a>,<sup id="cite_ref-86" class="reference"><a href="#cite_note-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup> the concentration of melatonin has been estimated or measured to be sufficiently high to raise the blood level of melatonin above daytime baseline values. </p><p>Although a role for melatonin as a plant hormone has not been clearly established, its involvement in processes such as growth and photosynthesis is well established. Only limited evidence of endogenous circadian rhythms in melatonin levels has been demonstrated in some plant species and no membrane-bound receptors analogous to those known in animals have been described. Rather, melatonin performs important roles in plants as a growth regulator, as well as environmental stress protector. It is synthesized in plants when they are exposed to both biological stresses, for example, fungal infection, and nonbiological stresses such as extremes of temperature, toxins, increased <a href="/wiki/Soil_salinity" title="Soil salinity">soil salinity</a>, drought, etc.<sup id="cite_ref-hardeland2015_36-2" class="reference"><a href="#cite_note-hardeland2015-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-reiter2015_87-0" class="reference"><a href="#cite_note-reiter2015-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-88" class="reference"><a href="#cite_note-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Herbicide" title="Herbicide">Herbicide</a>-induced <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a> has been experimentally mitigated <i>in vivo</i> in a high-melatonin <a href="/wiki/Genetically_modified_rice" title="Genetically modified rice">transgenic rice</a>.<sup id="cite_ref-Park-et-al-2012_89-0" class="reference"><a href="#cite_note-Park-et-al-2012-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Arnao-Hernandez-Ruiz-2014_90-0" class="reference"><a href="#cite_note-Arnao-Hernandez-Ruiz-2014-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FH_91-0" class="reference"><a href="#cite_note-FH-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> Studies conducted on lettuce grown in saline soil conditions have shown that the application of melatonin significantly mitigates the harmful effects of salinity. Foliar application increases the number of leaves, their surface area, increases fresh weight and the content of chlorophyll a and chlorophyll b, and the content of carotenoids compared to plants not treated with melatonin.<sup id="cite_ref-FH_91-1" class="reference"><a href="#cite_note-FH-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> </p><p>Fungal disease resistance is another role. Added melatonin increases <a href="/wiki/Plant_disease_resistance" title="Plant disease resistance">resistance</a> in <i><a href="/wiki/Malus_prunifolia" title="Malus prunifolia">Malus prunifolia</a></i> against <i><a href="/wiki/Diplocarpon_mali" class="mw-redirect" title="Diplocarpon mali">Diplocarpon mali</a></i>.<sup id="cite_ref-Arnao-Hernandez-Ruiz-2014_90-1" class="reference"><a href="#cite_note-Arnao-Hernandez-Ruiz-2014-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Arnao-Hernandez-Ruiz-2015_92-0" class="reference"><a href="#cite_note-Arnao-Hernandez-Ruiz-2015-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup> Also acts as a <a href="/wiki/Growth_inhibition" title="Growth inhibition">growth inhibitor</a> on <a href="/wiki/Fungal_plant_pathogen" class="mw-redirect" title="Fungal plant pathogen">fungal pathogens</a> including <i><a href="/wiki/Alternaria" title="Alternaria">Alternaria</a></i>, <i><a href="/wiki/Botrytis_(fungus)" title="Botrytis (fungus)">Botrytis</a></i>, and <i><a href="/wiki/Fusarium" title="Fusarium">Fusarium</a></i> spp. Decreases the speed of infection. As a <a href="/wiki/Seed_treatment" title="Seed treatment">seed treatment</a>, protects <i><a href="/wiki/Lupinus_albus" title="Lupinus albus">Lupinus albus</a></i> from fungi. Dramatically slows <a href="/wiki/Pseudomonas_syringae#Pseudomonas_syringae_pv._tomato_strain_DC3000_and_Arabidopsis_thaliana" title="Pseudomonas syringae"><i>Pseudomonas syringae tomato</i> DC3000 infecting <i>Arabidopsis thaliana</i></a> and <a href="/wiki/Pseudomonas_syringae#Pseudomonas_syringae_as_a_model_system" title="Pseudomonas syringae">infecting <i>Nicotiana benthamiana</i></a>.<sup id="cite_ref-Arnao-Hernandez-Ruiz-2015_92-1" class="reference"><a href="#cite_note-Arnao-Hernandez-Ruiz-2015-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Fungi">Fungi</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=19" title="Edit section: Fungi"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Melatonin has been observed to reduce stress tolerance in <i><a href="/wiki/Phytophthora_infestans" title="Phytophthora infestans">Phytophthora infestans</a></i> in plant-pathogen systems.<sup id="cite_ref-Socaciu-et-al-2020_93-0" class="reference"><a href="#cite_note-Socaciu-et-al-2020-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup> Danish pharmaceutical company <a href="/wiki/Novo_Nordisk" title="Novo Nordisk">Novo Nordisk</a> have used genetically modified yeast (<i><a href="/wiki/Saccharomyces_cerevisiae" title="Saccharomyces cerevisiae">Saccharomyces cerevisiae</a></i>) to produce melatonin.<sup id="cite_ref-94" class="reference"><a href="#cite_note-94"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Bacteria">Bacteria</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=20" title="Edit section: Bacteria"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Melatonin is produced by α-proteobacteria and photosynthetic cyanobacteria. There is no report of its occurrence in archaea which indicates that melatonin originated in bacteria<sup id="cite_ref-:1_11-1" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> most likely to prevent the first cells from the damaging effects of oxygen in the primitive Earth's atmosphere.<sup id="cite_ref-:0_10-1" class="reference"><a href="#cite_note-:0-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Novo Nordisk have used genetically modified <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">Escherichia coli</a></i> to produce melatonin.<sup id="cite_ref-95" class="reference"><a href="#cite_note-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-96" class="reference"><a href="#cite_note-96"><span class="cite-bracket">[</span>96<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Archaea">Archaea</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=21" title="Edit section: Archaea"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2022, the discovery of serotonin N-acetyltransferase (SNAT)<b>—</b>the penultimate, rate-limiting enzyme in the melatonin biosynthetic pathway<b>—</b>in the archaeon <i><a href="/wiki/Thermoplasma_volcanium" title="Thermoplasma volcanium">Thermoplasma volcanium</a></i> <sup id="cite_ref-97" class="reference"><a href="#cite_note-97"><span class="cite-bracket">[</span>97<span class="cite-bracket">]</span></a></sup> firmly places melatonin biosynthesis in all three major domains of life, dating back to ~4 Gya.<sup id="cite_ref-98" class="reference"><a href="#cite_note-98"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Food_products">Food products</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Melatonin&action=edit&section=22" title="Edit section: Food products"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Naturally-occurring melatonin has been reported in foods including <a href="/wiki/Prunus_cerasus" title="Prunus cerasus">tart cherries</a> to about 0.17–13.46 ng/g,<sup id="cite_ref-pmid11600041_99-0" class="reference"><a href="#cite_note-pmid11600041-99"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Banana" title="Banana">bananas</a>, <a href="/wiki/Plum" title="Plum">plums</a>, <a href="/wiki/Grape" title="Grape">grapes</a>, rice, <a href="/wiki/Cereal" title="Cereal">cereals</a>, <a href="/wiki/Herb" title="Herb">herbs</a>,<sup id="cite_ref-100" class="reference"><a href="#cite_note-100"><span class="cite-bracket">[</span>100<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Olive_oil" title="Olive oil">olive oil</a>, wine,<sup id="cite_ref-pmid21342247_101-0" class="reference"><a href="#cite_note-pmid21342247-101"><span class="cite-bracket">[</span>101<span class="cite-bracket">]</span></a></sup> and beer.<sup id="cite_ref-102" class="reference"><a href="#cite_note-102"><span class="cite-bracket">[</span>102<span class="cite-bracket">]</span></a></sup> The consumption of <a href="/wiki/Milk" title="Milk">milk</a> and sour cherries may improve sleep quality.<sup id="cite_ref-103" class="reference"><a href="#cite_note-103"><span class="cite-bracket">[</span>103<span class="cite-bracket">]</span></a></sup> When birds ingest melatonin-rich plant feed, such as rice, the melatonin binds to melatonin receptors in their brains.<sup id="cite_ref-Hattori1995_104-0" class="reference"><a href="#cite_note-Hattori1995-104"><span class="cite-bracket">[</span>104<span class="cite-bracket">]</span></a></sup> When humans consume foods rich in melatonin, such as banana, <a href="/wiki/Pineapple" title="Pineapple">pineapple</a>, and <a href="/wiki/Orange_(fruit)" title="Orange (fruit)">orange</a>, the blood levels of melatonin increase significantly.<sup id="cite_ref-pmid23137025_105-0" class="reference"><a href="#cite_note-pmid23137025-105"><span class="cite-bracket">[</span>105<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=Melatonin&action=edit&section=23" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><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 id="CITEREFAmaralCipolla-Neto2018" class="citation journal cs1">Amaral FG, Cipolla-Neto J (2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10118741">"A brief review about melatonin, a pineal hormone"</a>. <i>Archives of Endocrinology and Metabolism</i>. <b>62</b> (4): <span class="nowrap">472–</span>479. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.20945%2F2359-3997000000066">10.20945/2359-3997000000066</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/PMC10118741">10118741</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/30304113">30304113</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:52954755">52954755</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archives+of+Endocrinology+and+Metabolism&rft.atitle=A+brief+review+about+melatonin%2C+a+pineal+hormone&rft.volume=62&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E472-%3C%2Fspan%3E479&rft.date=2018&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10118741%23id-name%3DPMC&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A52954755%23id-name%3DS2CID&rft_id=info%3Apmid%2F30304113&rft_id=info%3Adoi%2F10.20945%2F2359-3997000000066&rft.aulast=Amaral&rft.aufirst=Fernanda+Gaspar+do&rft.au=Cipolla-Neto%2C+Jos%C3%A9&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10118741&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMelatonin" class="Z3988"></span></span> </li> <li id="cite_note-Auld2017-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Auld2017_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Auld2017_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAuldMaschauerMorrisonSkene2017" class="citation journal cs1">Auld F, Maschauer EL, Morrison I, Skene DJ, Riha RL (August 2017). <a rel="nofollow" class="external text" href="http://epubs.surrey.ac.uk/813219/1/Riha%20accepted%20MS%202016.pdf">"Evidence for the efficacy of melatonin in the treatment of primary adult sleep disorders"</a> <span class="cs1-format">(PDF)</span>. <i>Sleep Medicine Reviews</i>. <b>34</b>: <span class="nowrap">10–</span>22. <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.smrv.2016.06.005">10.1016/j.smrv.2016.06.005</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/20.500.11820%2F0e890bda-4b1d-4786-a907-a03b1580fd07">20.500.11820/0e890bda-4b1d-4786-a907-a03b1580fd07</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/28648359">28648359</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Sleep+Medicine+Reviews&rft.atitle=Evidence+for+the+efficacy+of+melatonin+in+the+treatment+of+primary+adult+sleep+disorders&rft.volume=34&rft.pages=%3Cspan+class%3D%22nowrap%22%3E10-%3C%2Fspan%3E22&rft.date=2017-08&rft_id=info%3Ahdl%2F20.500.11820%2F0e890bda-4b1d-4786-a907-a03b1580fd07&rft_id=info%3Apmid%2F28648359&rft_id=info%3Adoi%2F10.1016%2Fj.smrv.2016.06.005&rft.aulast=Auld&rft.aufirst=F&rft.au=Maschauer%2C+EL&rft.au=Morrison%2C+I&rft.au=Skene%2C+DJ&rft.au=Riha%2C+RL&rft_id=http%3A%2F%2Fepubs.surrey.ac.uk%2F813219%2F1%2FRiha%2520accepted%2520MS%25202016.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMelatonin" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFaraone2014" class="citation book cs1">Faraone SV (2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=lNSlBAAAQBAJ&pg=PA888"><i>ADHD: Non-Pharmacologic Interventions, An Issue of Child and Adolescent Psychiatric Clinics of North America, E-Book</i></a>. Elsevier Health Sciences. p. 888. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-32602-5" title="Special:BookSources/978-0-323-32602-5"><bdi>978-0-323-32602-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=ADHD%3A+Non-Pharmacologic+Interventions%2C+An+Issue+of+Child+and+Adolescent+Psychiatric+Clinics+of+North+America%2C+E-Book&rft.pages=888&rft.pub=Elsevier+Health+Sciences&rft.date=2014&rft.isbn=978-0-323-32602-5&rft.aulast=Faraone&rft.aufirst=SV&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DlNSlBAAAQBAJ%26pg%3DPA888&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMelatonin" class="Z3988"></span></span> </li> <li id="cite_note-Altun2007-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-Altun2007_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAltunUgur-Altun2007" class="citation journal cs1">Altun A, Ugur-Altun B (May 2007). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1742-1241.2006.01191.x">"Melatonin: therapeutic and clinical utilization"</a>. <i>International Journal of Clinical Practice</i>. <b>61</b> (5): <span class="nowrap">835–</span>45. <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/10.1111%2Fj.1742-1241.2006.01191.x">10.1111/j.1742-1241.2006.01191.x</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/17298593">17298593</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:18050554">18050554</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=International+Journal+of+Clinical+Practice&rft.atitle=Melatonin%3A+therapeutic+and+clinical+utilization&rft.volume=61&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E835-%3C%2Fspan%3E45&rft.date=2007-05&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A18050554%23id-name%3DS2CID&rft_id=info%3Apmid%2F17298593&rft_id=info%3Adoi%2F10.1111%2Fj.1742-1241.2006.01191.x&rft.aulast=Altun&rft.aufirst=A&rft.au=Ugur-Altun%2C+B&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fj.1742-1241.2006.01191.x&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMelatonin" class="Z3988"></span></span> </li> <li id="cite_note-Boutin2005-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-Boutin2005_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBoutinAudinotFerryDelagrange2005" class="citation journal cs1">Boutin JA, Audinot V, Ferry G, Delagrange P (August 2005). 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"Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance". <i>Endocrine</i>. <b>27</b> (2): <span class="nowrap">119–</span>30. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1385%2FENDO%3A27%3A2%3A119">10.1385/ENDO:27:2:119</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/16217125">16217125</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:46984486">46984486</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocrine&rft.atitle=Antioxidative+protection+by+melatonin%3A+multiplicity+of+mechanisms+from+radical+detoxification+to+radical+avoidance&rft.volume=27&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E119-%3C%2Fspan%3E30&rft.date=2005-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A46984486%23id-name%3DS2CID&rft_id=info%3Apmid%2F16217125&rft_id=info%3Adoi%2F10.1385%2FENDO%3A27%3A2%3A119&rft.aulast=Hardeland&rft.aufirst=R&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMelatonin" class="Z3988"></span></span> </li> <li id="cite_note-Reiter2001-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-Reiter2001_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFReiterAcuña-CastroviejoTanBurkhardt2001" class="citation journal cs1">Reiter RJ, Acuña-Castroviejo D, Tan DX, Burkhardt S (June 2001). 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class="Z3988"></span></span> </li> <li id="cite_note-IUPHAR_–_melatonin_receptors_review-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-IUPHAR_–_melatonin_receptors_review_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IUPHAR_–_melatonin_receptors_review_12-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-IUPHAR_–_melatonin_receptors_review_12-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-IUPHAR_–_melatonin_receptors_review_12-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-IUPHAR_–_melatonin_receptors_review_12-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-IUPHAR_–_melatonin_receptors_review_12-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJockersDelagrangeDubocovichMarkus2016" class="citation journal cs1">Jockers R, Delagrange P, Dubocovich ML, Markus RP, Renault N, Tosini G, et al. 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The measurement of the subcellular distribution of melatonin has shown that the concentration of this indole in the mitochondria greatly exceeds that in the blood.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cellular+and+Molecular+Life+Sciences&rft.atitle=Melatonin+as+a+mitochondria-targeted+antioxidant%3A+one+of+evolution%27s+best+ideas&rft.volume=74&rft.issue=21&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3863-%3C%2Fspan%3E3881&rft.date=2017-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11107735%23id-name%3DPMC&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A23820389%23id-name%3DS2CID&rft_id=info%3Apmid%2F28864909&rft_id=info%3Adoi%2F10.1007%2Fs00018-017-2609-7&rft.aulast=Reiter&rft.aufirst=RJ&rft.au=Rosales-Corral%2C+S&rft.au=Tan%2C+DX&rft.au=Jou%2C+MJ&rft.au=Galano%2C+A&rft.au=Xu%2C+B&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11107735&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMelatonin" class="Z3988"></span></span> </li> <li id="cite_note-Melatonin_–_2016_Review-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-Melatonin_–_2016_Review_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Melatonin_–_2016_Review_16-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Melatonin_–_2016_Review_16-2"><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="CITEREFReiterMayoTanSainz2016" class="citation journal cs1">Reiter RJ, Mayo JC, Tan DX, Sainz RM, Alatorre-Jimenez M, Qin L (October 2016). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fjpi.12360">"Melatonin as an antioxidant: under promises but over delivers"</a>. <i>Journal of Pineal Research</i>. <b>61</b> (3): <span class="nowrap">253–</span>78. <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/10.1111%2Fjpi.12360">10.1111/jpi.12360</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/27500468">27500468</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:35435683">35435683</a>. <q>There is credible evidence to suggest that melatonin should be classified as a mitochondria-targeted antioxidant.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Pineal+Research&rft.atitle=Melatonin+as+an+antioxidant%3A+under+promises+but+over+delivers&rft.volume=61&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E253-%3C%2Fspan%3E78&rft.date=2016-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A35435683%23id-name%3DS2CID&rft_id=info%3Apmid%2F27500468&rft_id=info%3Adoi%2F10.1111%2Fjpi.12360&rft.aulast=Reiter&rft.aufirst=RJ&rft.au=Mayo%2C+JC&rft.au=Tan%2C+DX&rft.au=Sainz%2C+RM&rft.au=Alatorre-Jimenez%2C+M&rft.au=Qin%2C+L&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fjpi.12360&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMelatonin" class="Z3988"></span></span> </li> <li id="cite_note-pmid26272235-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid26272235_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid26272235_17-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid26272235_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 id="CITEREFManchesterCoto-MontesBogaAndersen2015" class="citation journal cs1">Manchester LC, Coto-Montes A, Boga JA, Andersen LP, Zhou Z, Galano A, et al. (November 2015). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fjpi.12267">"Melatonin: an ancient molecule that makes oxygen metabolically tolerable"</a>. <i>Journal of Pineal Research</i>. <b>59</b> (4): <span class="nowrap">403–</span>19. <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/10.1111%2Fjpi.12267">10.1111/jpi.12267</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/26272235">26272235</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:24373303">24373303</a>. <q>While originally thought to be produced exclusively in and secreted from the vertebrate pineal gland [53], it is now known that the indole is present in many, perhaps all, vertebrate organs [54] and in organs of all plants that have been investigated [48, 55, 56]. That melatonin is not relegated solely to the pineal gland is also emphasized by the reports that it is present in invertebrates [57–59], which lack a pineal gland and some of which consist of only a single cell.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Pineal+Research&rft.atitle=Melatonin%3A+an+ancient+molecule+that+makes+oxygen+metabolically+tolerable&rft.volume=59&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E403-%3C%2Fspan%3E19&rft.date=2015-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24373303%23id-name%3DS2CID&rft_id=info%3Apmid%2F26272235&rft_id=info%3Adoi%2F10.1111%2Fjpi.12267&rft.aulast=Manchester&rft.aufirst=LC&rft.au=Coto-Montes%2C+A&rft.au=Boga%2C+JA&rft.au=Andersen%2C+LP&rft.au=Zhou%2C+Z&rft.au=Galano%2C+A&rft.au=Vriend%2C+J&rft.au=Tan%2C+DX&rft.au=Reiter%2C+RJ&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fjpi.12267&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMelatonin" class="Z3988"></span></span> </li> <li id="cite_note-Melatonin_transporters_–_2017_review-18"><span class="mw-cite-backlink">^ <a href="#cite_ref-Melatonin_transporters_–_2017_review_18-0"><sup><i><b>a</b></i></sup></a> <a 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href="https://doi.org/10.1007%2Fs00018-017-2616-8">10.1007/s00018-017-2616-8</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/PMC11107582">11107582</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/28828619">28828619</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:10920415">10920415</a>.</cite><span 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class="navbox-group" style="width:1%"><a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93gonadal_axis" title="Hypothalamic–pituitary–gonadal axis">Gonadal axis</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Testicle" title="Testicle">Testis</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li> <li><a href="/wiki/Anti-M%C3%BCllerian_hormone" title="Anti-Müllerian hormone">AMH</a></li> <li><a href="/wiki/Activin_and_inhibin" title="Activin and inhibin">Inhibin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ovary" title="Ovary">Ovary</a></th><td 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title="Pineal gland">Pineal gland</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Melatonin</a></li> <li><a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">N,N-Dimethyltryptamine</a></li> <li><a href="/wiki/5-Methoxy-N,N-dimethyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-dimethyltryptamine">5-Methoxy-N,N-dimethyltryptamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thymus" title="Thymus">Thymus</a></th><td class="navbox-list-with-group navbox-list navbox-even" 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style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gastrin" title="Gastrin">Gastrin</a></li> <li><a href="/wiki/Ghrelin" title="Ghrelin">Ghrelin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Duodenum" title="Duodenum">Duodenum</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cholecystokinin" title="Cholecystokinin">CCK</a></li> <li><a href="/wiki/Gastric_inhibitory_polypeptide" title="Gastric inhibitory polypeptide">GIP</a></li> <li><a href="/wiki/Secretin" title="Secretin">Secretin</a></li> <li><a href="/wiki/Motilin" title="Motilin">Motilin</a></li> <li><a href="/wiki/Vasoactive_intestinal_peptide" title="Vasoactive intestinal peptide">VIP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ileum" title="Ileum">Ileum</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Enteroglucagon" title="Enteroglucagon">Enteroglucagon</a></li> <li><a href="/wiki/Peptide_YY" title="Peptide YY">Peptide YY</a></li> <li><a href="/wiki/Glucagon-like_peptide-1" title="Glucagon-like peptide-1">GLP-1</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Liver" title="Liver">Liver</a>/other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Insulin-like_growth_factor" title="Insulin-like growth factor">Insulin-like growth factor</a> <ul><li><a href="/wiki/Insulin-like_growth_factor_1" title="Insulin-like growth factor 1">IGF-1</a></li> <li><a href="/wiki/Insulin-like_growth_factor_2" title="Insulin-like growth factor 2">IGF-2</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adipose_tissue" title="Adipose tissue">Adipose tissue</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Leptin" title="Leptin">Leptin</a></li> <li><a href="/wiki/Adiponectin" title="Adiponectin">Adiponectin</a></li> <li><a href="/wiki/Resistin" title="Resistin">Resistin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Human_skeleton" title="Human skeleton">Skeleton</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Osteocalcin" title="Osteocalcin">Osteocalcin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Kidney" title="Kidney">Kidney</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Renin" title="Renin">Renin</a></li> <li><a href="/wiki/Erythropoietin" title="Erythropoietin">EPO</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol</a></li> <li><a href="/wiki/Prostaglandin" title="Prostaglandin">Prostaglandin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Heart" title="Heart">Heart</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Natriuretic_peptide" title="Natriuretic peptide">Natriuretic peptide</a> <ul><li><a href="/wiki/Atrial_natriuretic_peptide" title="Atrial natriuretic peptide">ANP</a></li> <li><a href="/wiki/Brain_natriuretic_peptide_32" title="Brain natriuretic peptide 32">BNP</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Antioxidants62" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Antioxidants" title="Template:Antioxidants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Antioxidants" title="Template talk:Antioxidants"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Antioxidants" title="Special:EditPage/Template:Antioxidants"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antioxidants62" style="font-size:114%;margin:0 4em"><a href="/wiki/Antioxidant" title="Antioxidant">Antioxidants</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Food antioxidants</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-Hydroxymelatonin</a></li> <li><a href="/wiki/Acetylcarnitine" title="Acetylcarnitine">Acetyl-<small>L</small>-carnitine</a> (ALCAR)</li> <li><a href="/wiki/Lipoic_acid" title="Lipoic acid">Alpha-lipoic acid</a> (ALA)</li> <li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid</a> (vitamin C)</li> <li><a href="/wiki/Carotenoid" title="Carotenoid">Carotenoids</a> (<a href="/wiki/Vitamin_A" title="Vitamin A">vitamin A</a>)</li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></li> <li><a href="/wiki/Edaravone" title="Edaravone">Edaravone</a></li> <li><a href="/wiki/Antioxidant_effect_of_polyphenols_and_natural_phenols" title="Antioxidant effect of polyphenols and natural phenols">Polyphenols</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">Glutathione</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Carnitine" title="Carnitine"><small>L</small>-carnitine</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a class="mw-selflink selflink">Melatonin</a></li> <li><a href="/wiki/Mofegiline" title="Mofegiline">Mofegiline</a></li> <li><a href="/wiki/Acetylcysteine" title="Acetylcysteine"><i>N</i>-Acetylcysteine</a> (NAC)</li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin"><i>N</i>-Acetylserotonin</a> (NAS)</li> <li><a href="/wiki/Oleocanthal" title="Oleocanthal">Oleocanthal</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Rasagiline" title="Rasagiline">Rasagiline</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a></li> <li><a href="/wiki/Selenium" title="Selenium">Selenium</a></li> <li><a href="/wiki/Tocopherol" title="Tocopherol">Tocopherols</a> (<a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a>)</li> <li><a href="/wiki/Tocotrienol" title="Tocotrienol">Tocotrienols</a> (<a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a>)</li> <li><a href="/wiki/Tyrosol" title="Tyrosol">Tyrosol</a></li> <li><a href="/wiki/Coenzyme_Q10" title="Coenzyme Q10">Ubiquinone</a> (coenzyme Q)</li> <li><a href="/wiki/Uric_acid" title="Uric acid">Uric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fuel antioxidants</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Butylated_hydroxyanisole" title="Butylated hydroxyanisole">Butylated hydroxyanisole</a></li> <li><a href="/wiki/Butylated_hydroxytoluene" title="Butylated hydroxytoluene">Butylated hydroxytoluene</a></li> <li><a href="/wiki/2,6-Di-tert-butylphenol" title="2,6-Di-tert-butylphenol">2,6-Di-<i>tert</i>-butylphenol</a></li> <li><a href="/wiki/1,2-Diaminopropane" title="1,2-Diaminopropane">1,2-Diaminopropane</a></li> <li><a href="/wiki/2,4-Dimethyl-6-tert-butylphenol" title="2,4-Dimethyl-6-tert-butylphenol">2,4-Dimethyl-6-<i>tert</i>-butylphenol</a></li> <li><a href="/wiki/Ethylenediamine" title="Ethylenediamine">Ethylenediamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Measurements</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Folin%E2%80%93Ciocalteu_reagent" title="Folin–Ciocalteu reagent">Folin method</a></li> <li><a href="/wiki/Oxygen_radical_absorbance_capacity" title="Oxygen radical absorbance capacity">ORAC</a></li> <li><a href="/wiki/Trolox_equivalent_antioxidant_capacity" title="Trolox equivalent antioxidant capacity">TEAC</a></li> <li><a href="/wiki/Ferric_reducing_ability_of_plasma" title="Ferric reducing ability of plasma">FRAP</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Tryptamines232" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Tryptamines" title="Template:Tryptamines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tryptamines" title="Template talk:Tryptamines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tryptamines" title="Special:EditPage/Template:Tryptamines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Tryptamines232" style="font-size:114%;margin:0 4em"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=1-Methyltryptamine&action=edit&redlink=1" class="new" title="1-Methyltryptamine (page does not exist)">1-Methyl-T</a></li> <li><a href="/wiki/1-Methylpsilocin" title="1-Methylpsilocin">1-Methylpsilocin</a></li> <li><a href="/wiki/2-HO-NMT" title="2-HO-NMT">2-HO-NMT</a></li> <li><a href="/wiki/2-Me-DET" title="2-Me-DET">2-Me-DET</a></li> <li><a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Methyl-5-HT</a></li> <li><a href="/wiki/2,N,N-TMT" title="2,N,N-TMT">2,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole" class="mw-redirect" title="1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole">4,5-DHP-DMT</a></li> <li><a href="/wiki/4,5-Dihydroxytryptamine" title="4,5-Dihydroxytryptamine">4,5-DHT</a></li> <li><a href="/wiki/4-AcO-DALT" title="4-AcO-DALT">4-AcO-DALT</a></li> <li><a href="/wiki/4-Acetoxy-DET" class="mw-redirect" title="4-Acetoxy-DET">4-AcO-DET</a></li> <li><a href="/wiki/4-Acetoxy-DiPT" title="4-Acetoxy-DiPT">4-AcO-DiPT</a></li> <li><a href="/wiki/4-AcO-DPT" title="4-AcO-DPT">4-AcO-DPT</a></li> <li><a href="/w/index.php?title=4-AcO-EPT&action=edit&redlink=1" class="new" title="4-AcO-EPT (page does not exist)">4-AcO-EPT</a></li> <li><a href="/w/index.php?title=4-AcO-MALT&action=edit&redlink=1" class="new" title="4-AcO-MALT (page does not exist)">4-AcO-MALT</a></li> <li><a href="/wiki/4-Acetoxy-MET" class="mw-redirect" title="4-Acetoxy-MET">4-AcO-MET</a></li> <li><a href="/wiki/4-Acetoxy-MiPT" class="mw-redirect" title="4-Acetoxy-MiPT">4-AcO-MiPT</a></li> <li><a href="/w/index.php?title=4-AcO-NMT&action=edit&redlink=1" class="new" title="4-AcO-NMT (page does not exist)">4-AcO-NMT</a></li> <li><a href="/w/index.php?title=4-AcO-TMT&action=edit&redlink=1" class="new" title="4-AcO-TMT (page does not exist)">4-AcO-TMT</a></li> <li><a href="/wiki/4-Fluoro-5-methoxy-DMT" title="4-Fluoro-5-methoxy-DMT">4-F-5-MeO-DMT</a></li> <li><a href="/w/index.php?title=4-Fluorotryptamine&action=edit&redlink=1" class="new" title="4-Fluorotryptamine (page does not exist)">4-Fluoro-T</a></li> <li><a href="/wiki/4-Hydroxy-5-methoxytryptamine" title="4-Hydroxy-5-methoxytryptamine">4-HO-5-MeO-T</a></li> <li><a href="/w/index.php?title=4-HO-DALT&action=edit&redlink=1" class="new" title="4-HO-DALT (page does not exist)">4-HO-DALT</a></li> <li><a href="/wiki/4-HO-DBT" title="4-HO-DBT">4-HO-DBT</a></li> <li><a href="/wiki/4-HO-DET" title="4-HO-DET">4-HO-DET</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">4-HO-DiPT</a></li> <li><a href="/wiki/4-HO-DPT" title="4-HO-DPT">4-HO-DPT</a></li> <li><a href="/wiki/4-HO-DSBT" title="4-HO-DSBT">4-HO-DSBT</a></li> <li><a href="/wiki/4-HO-EPT" title="4-HO-EPT">4-HO-EPT</a></li> <li><a href="/wiki/4-HO-MALT" title="4-HO-MALT">4-HO-MALT</a></li> <li><a href="/wiki/4-HO-MET" title="4-HO-MET">4-HO-MET</a></li> <li><a href="/wiki/4-HO-McPT" title="4-HO-McPT">4-HO-McPT</a></li> <li><a href="/wiki/4-HO-McPeT" title="4-HO-McPeT">4-HO-McPeT</a></li> <li><a href="/wiki/4-HO-MiPT" title="4-HO-MiPT">4-HO-MiPT</a></li> <li><a href="/wiki/4-HO-MPT" title="4-HO-MPT">4-HO-MPT</a></li> <li><a href="/w/index.php?title=4-HO-MsBT&action=edit&redlink=1" class="new" title="4-HO-MsBT (page does not exist)">4-HO-MsBT</a></li> <li><a href="/wiki/4-HO-NALT" title="4-HO-NALT">4-HO-NALT</a></li> <li><a href="/wiki/4-HO-NMT" class="mw-redirect" title="4-HO-NMT">4-HO-NMT</a></li> <li><a href="/wiki/4-HO-PiPT" title="4-HO-PiPT">4-HO-PiPT</a></li> <li><a href="/wiki/4-HO-pyr-T" title="4-HO-pyr-T">4-HO-pyr-T</a></li> <li><a href="/wiki/4-HO-TMT" title="4-HO-TMT">4-HO-TMT</a></li> <li><a href="/wiki/4-Hydroxytryptamine" title="4-Hydroxytryptamine">4-HT</a></li> <li><a href="/w/index.php?title=4-MeO-DiPT&action=edit&redlink=1" class="new" title="4-MeO-DiPT (page does not exist)">4-MeO-DiPT</a></li> <li><a href="/wiki/4-MeO-DMT" title="4-MeO-DMT">4-MeO-DMT</a></li> <li><a href="/wiki/4-MeO-MiPT" title="4-MeO-MiPT">4-MeO-MiPT</a></li> <li><a href="/w/index.php?title=4-MeO-T&action=edit&redlink=1" class="new" title="4-MeO-T (page does not exist)">4-MeO-T</a></li> <li><a href="/wiki/4-PrO-DMT" title="4-PrO-DMT">4-PrO-DMT</a></li> <li><a href="/wiki/4,5-MDO-DMT" title="4,5-MDO-DMT">4,5-MDO-DMT</a></li> <li><a href="/wiki/4,5-MDO-DiPT" title="4,5-MDO-DiPT">4,5-MDO-DiPT</a></li> <li><a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a></li> <li><a href="/wiki/5-Bromo-DMT" title="5-Bromo-DMT">5-Bromo-DMT</a></li> <li><a href="/w/index.php?title=5-Bromotryptamine&action=edit&redlink=1" class="new" title="5-Bromotryptamine (page does not exist)">5-Bromo-T</a></li> <li><a href="/wiki/5-Chloro-DMT" title="5-Chloro-DMT">5-Chloro-DMT</a></li> <li><a href="/w/index.php?title=5-Chlorotryptamine&action=edit&redlink=1" class="new" title="5-Chlorotryptamine (page does not exist)">5-Chloro-T</a></li> <li><a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a></li> <li><a href="/wiki/5-Ethoxy-DMT" title="5-Ethoxy-DMT">5-Ethoxy-DMT</a></li> <li><a href="/wiki/5-Ethyl-DMT" title="5-Ethyl-DMT">5-Ethyl-DMT</a></li> <li><a href="/wiki/5-Fluoro-DET" title="5-Fluoro-DET">5-Fluoro-DET</a></li> <li><a href="/wiki/5-Fluoro-DMT" title="5-Fluoro-DMT">5-Fluoro-DMT</a></li> <li><a href="/wiki/5-Fluoro-EPT" title="5-Fluoro-EPT">5-Fluoro-EPT</a></li> <li><a href="/wiki/5-Fluoro-MET" title="5-Fluoro-MET">5-Fluoro-MET</a></li> <li><a href="/w/index.php?title=5-Fluorotryptamine&action=edit&redlink=1" class="new" title="5-Fluorotryptamine (page does not exist)">5-Fluoro-T</a></li> <li><a href="/wiki/5-HO-DiPT" title="5-HO-DiPT">5-HO-DiPT</a></li> <li><a href="/wiki/5-Hydroxytryptophan" title="5-Hydroxytryptophan">5-HTP (oxitriptan)</a></li> <li><a href="/wiki/5-MeO-2-TMT" title="5-MeO-2-TMT">5-MeO-2-TMT</a></li> <li><a href="/w/index.php?title=5-MeO-34MPEMT&action=edit&redlink=1" class="new" title="5-MeO-34MPEMT (page does not exist)">5-MeO-34MPEMT</a></li> <li><a href="/wiki/5-Methoxy-7,N,N-trimethyltryptamine" title="5-Methoxy-7,N,N-trimethyltryptamine">5-MeO-7,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/5-MeO-DBT" title="5-MeO-DBT">5-MeO-DBT</a></li> <li><a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a></li> <li><a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a></li> <li><a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a></li> <li><a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a></li> <li><a href="/wiki/5-MeO-EiPT" title="5-MeO-EiPT">5-MeO-EiPT</a></li> <li><a href="/wiki/5-MeO-EPT" title="5-MeO-EPT">5-MeO-EPT</a></li> <li><a href="/wiki/5-MeO-MALT" title="5-MeO-MALT">5-MeO-MALT</a></li> <li><a href="/wiki/5-MeO-MET" title="5-MeO-MET">5-MeO-MET</a></li> <li><a href="/wiki/5-MeO-MiPT" title="5-MeO-MiPT">5-MeO-MiPT</a></li> <li><a href="/w/index.php?title=5-MeO-NET&action=edit&redlink=1" class="new" title="5-MeO-NET (page does not exist)">5-MeO-NET</a></li> <li><a href="/w/index.php?title=5-MeO-NiPT&action=edit&redlink=1" class="new" title="5-MeO-NiPT (page does not exist)">5-MeO-NiPT</a></li> <li><a href="/wiki/5-MeO-NMT" title="5-MeO-NMT">5-MeO-NMT</a></li> <li><a href="/wiki/5-MeO-pyr-T" title="5-MeO-pyr-T">5-MeO-pyr-T</a></li> <li><a href="/wiki/5-MeO-NBpBrT" title="5-MeO-NBpBrT">5-MeO-NBpBrT</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MeO-T (5-MT; mexamine)</a></li> <li><a href="/wiki/5-MeO-T-NBOMe" title="5-MeO-T-NBOMe">5-MeO-T-NBOMe</a></li> <li><a href="/wiki/5-MeS-DMT" title="5-MeS-DMT">5-MeS-DMT</a></li> <li><a href="/wiki/5,N,N-TMT" title="5,N,N-TMT">5-Methyl-DMT</a></li> <li><a href="/wiki/5-Methyltryptamine" title="5-Methyltryptamine">5-Methyl-T</a></li> <li><a href="/w/index.php?title=5-MT-NB3OMe&action=edit&redlink=1" class="new" title="5-MT-NB3OMe (page does not exist)">5-MT-NB3OMe</a></li> <li><a href="/wiki/5-(Nonyloxy)tryptamine" title="5-(Nonyloxy)tryptamine">5-NOT</a></li> <li><a href="/wiki/5,6-MeO-MiPT" title="5,6-MeO-MiPT">5,6-MeO-MiPT</a></li> <li><a href="/wiki/5,6-MDO-DiPT" title="5,6-MDO-DiPT">5,6-MDO-DiPT</a></li> <li><a href="/wiki/5,6-MDO-DMT" title="5,6-MDO-DMT">5,6-MDO-DMT</a></li> <li><a href="/wiki/5,6-MDO-MiPT" title="5,6-MDO-MiPT">5,6-MDO-MiPT</a></li> <li><a href="/wiki/5,6-Dihydroxytryptamine" title="5,6-Dihydroxytryptamine">5,6-DHT</a></li> <li><a href="/wiki/5,7-Dihydroxytryptamine" title="5,7-Dihydroxytryptamine">5,7-DHT</a></li> <li><a href="/wiki/6-Fluoro-DMT" title="6-Fluoro-DMT">6-Fluoro-DMT</a></li> <li><a href="/w/index.php?title=6-Fluorotryptamine&action=edit&redlink=1" class="new" title="6-Fluorotryptamine (page does not exist)">6-Fluoro-T</a></li> <li><a href="/wiki/6-MeO-DMT" title="6-MeO-DMT">6-MeO-DMT</a></li> <li><a href="/w/index.php?title=6-Methoxytryptamine&action=edit&redlink=1" class="new" title="6-Methoxytryptamine (page does not exist)">6-MeO-T</a></li> <li><a href="/w/index.php?title=6-Methyltryptamine&action=edit&redlink=1" class="new" title="6-Methyltryptamine (page does not exist)">6-Methyl-T</a></li> <li><a href="/wiki/6,7-Dihydroxytryptamine" title="6,7-Dihydroxytryptamine">6,7-DHT</a></li> <li><a href="/w/index.php?title=7-Chlorotryptamine&action=edit&redlink=1" class="new" title="7-Chlorotryptamine (page does not exist)">7-Chloro-T</a></li> <li><a href="/w/index.php?title=7-Methoxytryptamine&action=edit&redlink=1" class="new" title="7-Methoxytryptamine (page does not exist)">7-MeO-T</a></li> <li><a href="/wiki/7,N,N-TMT" title="7,N,N-TMT">7-Methyl-DMT</a></li> <li><a href="/w/index.php?title=7-Methyltryptamine&action=edit&redlink=1" class="new" title="7-Methyltryptamine (page does not exist)">7-Methyl-T</a></li> <li><a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine (5-AT)</a></li> <li><a href="/wiki/Aeruginascin" title="Aeruginascin">Aeruginascin (4-PO-TMT)</a></li> <li><a href="/wiki/AGH-107" title="AGH-107">AGH-107</a></li> <li><a href="/wiki/AGH-192" title="AGH-192">AGH-192</a></li> <li><a href="/wiki/AH-494" title="AH-494">AH-494</a></li> <li><a href="/w/index.php?title=ALiPT&action=edit&redlink=1" class="new" title="ALiPT (page does not exist)">ALiPT</a></li> <li><a href="/wiki/Alpertine" title="Alpertine">Alpertine</a></li> <li><a href="/wiki/Baeocystin" title="Baeocystin">Baeocystin (4-PO-NMT)</a></li> <li><a href="/wiki/Benzotript" title="Benzotript">Benzotript (4-chlorobenzoyl-<small>L</small>-tryptophan)</a></li> <li><a href="/wiki/Bufotenidine" title="Bufotenidine">Bufotenidine (5-HTQ)</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin (5-HO-DMT)</a></li> <li><a href="/wiki/Convolutindole_A" title="Convolutindole A">Convolutindole A</a></li> <li><a href="/wiki/CP-132,484" title="CP-132,484">CP-132,484</a></li> <li><a href="/wiki/DALT" title="DALT">DALT</a></li> <li><a href="/wiki/Dibutyltryptamine" title="Dibutyltryptamine">DBT</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a></li> <li><a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a></li> <li><a href="/wiki/E-6801" title="E-6801">E-6801</a></li> <li><a href="/wiki/E-6837" title="E-6837">E-6837</a></li> <li><a href="/wiki/Ethylisopropyltryptamine" title="Ethylisopropyltryptamine">EiPT</a></li> <li><a href="/wiki/EMDT" title="EMDT">EMDT</a></li> <li><a href="/wiki/Ethylpropyltryptamine" title="Ethylpropyltryptamine">EPT</a></li> <li><a href="/wiki/Ethocybin" title="Ethocybin">Ethocybin (4-PO-DET)</a></li> <li><a href="/wiki/FGIN-127" title="FGIN-127">FGIN-127</a></li> <li><a href="/wiki/FGIN-143" title="FGIN-143">FGIN-143</a></li> <li><a href="/wiki/FT-104" title="FT-104">FT-104</a></li> <li><a href="/wiki/HIOC" title="HIOC">HIOC</a></li> <li><a href="/wiki/Idalopirdine" title="Idalopirdine">Idalopirdine</a></li> <li><a href="/w/index.php?title=Indolylethylfentanyl&action=edit&redlink=1" class="new" title="Indolylethylfentanyl (page does not exist)">Indolylethylfentanyl</a></li> <li><a href="/wiki/Indorenate" title="Indorenate">Indorenate</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">Iprocin (4-HO-DiPT)</a></li> <li><a href="/wiki/Isamide" title="Isamide">Isamide</a></li> <li><a href="/wiki/Lespedamine" title="Lespedamine">Lespedamine</a></li> <li><a href="/wiki/Methylbutyltryptamine" title="Methylbutyltryptamine">MBT</a></li> <li><a href="/wiki/N-Methyl-N-ethyltryptamine" title="N-Methyl-N-ethyltryptamine">MET</a></li> <li><a href="/wiki/Milipertine" title="Milipertine">Milipertine</a></li> <li><a href="/wiki/4-HO-MiPT" title="4-HO-MiPT">Miprocin (4-HO-MiPT)</a></li> <li><a href="/wiki/Methylisopropyltryptamine" class="mw-redirect" title="Methylisopropyltryptamine">MiPT</a></li> <li><a href="/wiki/4-Acetoxy-MiPT" class="mw-redirect" title="4-Acetoxy-MiPT">MPT</a></li> <li><a href="/wiki/MS-245" title="MS-245">MS-245</a></li> <li><a href="/wiki/Methylbutyltryptamine#MSBT" title="Methylbutyltryptamine">MSBT</a></li> <li><a href="/wiki/N-Feruloylserotonin" title="N-Feruloylserotonin"><i>N</i>-Feruloylserotonin (moschamine)</a></li> <li><a href="/wiki/NBoc-DMT" title="NBoc-DMT">NBoc-DMT</a></li> <li><a href="/wiki/N-Ethyltryptamine" title="N-Ethyltryptamine">NET/NETP</a></li> <li><a href="/w/index.php?title=N-Isopropyltryptamine&action=edit&redlink=1" class="new" title="N-Isopropyltryptamine (page does not exist)">NiPT</a></li> <li><a href="/wiki/N-Methyltryptamine" title="N-Methyltryptamine">NMT</a></li> <li><a href="/wiki/Norbaeocystin" title="Norbaeocystin">Norbaeocystin (4-PO-T)</a></li> <li><a href="/wiki/N-t-Butyltryptamine" title="N-t-Butyltryptamine">NTBT</a></li> <li><a href="/wiki/O-4310" title="O-4310">O-4310</a></li> <li><a href="/wiki/O-Pivalylbufotenine" title="O-Pivalylbufotenine"><i>O</i>-Pivalylbufotenine</a></li> <li><a href="/wiki/Oxypertine" title="Oxypertine">Oxypertine</a></li> <li><a href="/wiki/Propylisopropyltryptamine" title="Propylisopropyltryptamine">PiPT</a></li> <li><a href="/wiki/Psilacetin" class="mw-redirect" title="Psilacetin">Psilacetin (<i>O</i>-acetylpsilocin; 4-AcO-DMT)</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">Psilocin (4-HO-DMT)</a></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">Psilocybin (4-PO-DMT)</a></li> <li><a href="/wiki/Psilomethoxin" title="Psilomethoxin">Psilomethoxin (4-HO-5-MeO-DMT)</a></li> <li><a href="/wiki/Pyr-T" title="Pyr-T">Pyr-T</a></li> <li><a href="/wiki/RS134-49" title="RS134-49">RS134-49</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Solypertine" title="Solypertine">Solypertine</a></li> <li><a href="/wiki/ST-1936" title="ST-1936">ST-1936</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine (T)</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/Yuremamine" title="Yuremamine">Yuremamine</a></li> <li><a href="/w/index.php?title=Z2876442907&action=edit&redlink=1" class="new" title="Z2876442907 (page does not exist)">Z2876442907</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine"><i>N</i>-Acetyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Iodomelatonin" title="2-Iodomelatonin">2-Iodomelatonin</a></li> <li><a href="/w/index.php?title=2-Phenylmelatonin&action=edit&redlink=1" class="new" title="2-Phenylmelatonin (page does not exist)">2-Phenylmelatonin</a></li> <li><a href="/w/index.php?title=5-Methoxyluzindole&action=edit&redlink=1" class="new" title="5-Methoxyluzindole (page does not exist)">5-Methoxyluzindole</a></li> <li><a href="/w/index.php?title=6-Chloromelatonin&action=edit&redlink=1" class="new" title="6-Chloromelatonin (page does not exist)">6-Chloromelatonin</a></li> <li><a href="/w/index.php?title=6-Fluoromelatonin&action=edit&redlink=1" class="new" title="6-Fluoromelatonin (page does not exist)">6-Fluoromelatonin</a></li> <li><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-Hydroxymelatonin</a></li> <li><a href="/w/index.php?title=6-Methoxymelatonin&action=edit&redlink=1" class="new" title="6-Methoxymelatonin (page does not exist)">6-Methoxymelatonin</a></li> <li><a href="/w/index.php?title=6,7-Dichloro-2-methylmelatonin&action=edit&redlink=1" class="new" title="6,7-Dichloro-2-methylmelatonin (page does not exist)">6,7-Dichloro-2-methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/Luzindole" title="Luzindole">Luzindole</a></li> <li><a class="mw-selflink selflink">Melatonin</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">Normelatonin (<i>N</i>-acetylserotonin; NAS)</a></li> <li><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine"><i>N</i>-Acetyltryptamine</a></li> <li><a href="/w/index.php?title=N-Butanoylmelatonin&action=edit&redlink=1" class="new" title="N-Butanoylmelatonin (page does not exist)"><i>N</i>-Butanoylmelatonin</a></li> <li><a href="/w/index.php?title=N-Propionylmelatonin&action=edit&redlink=1" class="new" title="N-Propionylmelatonin (page does not exist)"><i>N</i>-Propionylmelatonin</a></li> <li><a href="/wiki/Piromelatine" title="Piromelatine">Piromelatine</a></li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/%CE%91-Alkyltryptamine" class="mw-redirect" title="Α-Alkyltryptamine">α-Alkyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,%CE%B1-Dimethyltryptamine" title="2,α-Dimethyltryptamine">2,α-DMT</a></li> <li><a href="/wiki/4-HO-%CE%B1MT" title="4-HO-αMT">4-HO-αMT</a></li> <li><a href="/wiki/4-HO-MPMI" title="4-HO-MPMI">4-HO-MPMI (lucigenol)</a></li> <li><a href="/wiki/4-Methyl-%CE%B1-ethyltryptamine" title="4-Methyl-α-ethyltryptamine">4-Me-αET</a></li> <li><a href="/wiki/4-Me-%CE%B1MT" class="mw-redirect" title="4-Me-αMT">4-Me-αMT</a></li> <li><a href="/wiki/5-Chloro-%CE%B1ET" title="5-Chloro-αET">5-Chloro-αET</a></li> <li><a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Chloro-αMT</a></li> <li><a href="/wiki/5-Ethoxy-AMT" class="mw-redirect" title="5-Ethoxy-AMT">5-Ethoxy-αMT</a></li> <li><a href="/wiki/5-Fluoro-AET" title="5-Fluoro-AET">5-Fluoro-αET</a></li> <li><a href="/wiki/5-Fluoro-AMT" title="5-Fluoro-AMT">5-Fluoro-αMT</a></li> <li><a href="/w/index.php?title=5-Isopropoxy-AMT&action=edit&redlink=1" class="new" title="5-Isopropoxy-AMT (page does not exist)">5-iPrO-αMT</a></li> <li><a href="/wiki/5-MeO-%CE%B1,N,N-TMT" class="mw-redirect" title="5-MeO-α,N,N-TMT">5-MeO-α,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET </a></li> <li><a href="/wiki/5-MeO-aMT" class="mw-redirect" title="5-MeO-aMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-MeO-MPMI" title="5-MeO-MPMI">5-MeO-MPMI</a></li> <li><a href="/w/index.php?title=5-Methyl-AET&action=edit&redlink=1" class="new" title="5-Methyl-AET (page does not exist)">5-Methyl-αET</a></li> <li><a href="/wiki/6-Fluoro-AMT" title="6-Fluoro-AMT">6-Fluoro-αMT</a></li> <li><a href="/wiki/7-Chloro-AMT" title="7-Chloro-AMT">7-Chloro-αMT</a></li> <li><a href="/wiki/7-Methyl-%CE%B1-ethyltryptamine" title="7-Methyl-α-ethyltryptamine">7-Methyl-αET</a></li> <li><a href="/wiki/%CE%91-Methyl-5-hydroxytryptophan" title="Α-Methyl-5-hydroxytryptophan">α-Methyl-5-HTP</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylserotonin" title="Α-Methylserotonin">α-Methylserotonin (5-HO-αMT)</a></li> <li><a href="/wiki/%CE%91-Methyltryptophan" title="Α-Methyltryptophan">α-Methyltryptophan (αMTP)</a></li> <li><a href="/wiki/Alpha,N-DMT" class="mw-redirect" title="Alpha,N-DMT">α,<i>N</i>-DMT (<i>N</i>-methyl-αMT)</a></li> <li><a href="/wiki/%CE%91,N,N-Trimethyltryptamine" title="Α,N,N-Trimethyltryptamine">α,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/Alpha,N,O-TMS" class="mw-redirect" title="Alpha,N,O-TMS">α,<i>N</i>,<i>O</i>-TMS</a></li> <li><a href="/wiki/%CE%91-Ethyltryptamine" title="Α-Ethyltryptamine">αET (etryptamine)</a></li> <li><a href="/wiki/%CE%91-Methyltryptamine" title="Α-Methyltryptamine">αMT</a></li> <li><a href="/wiki/AL-37350A" title="AL-37350A">AL-37350A (4,5-DHP-αMT)</a></li> <li><a href="/w/index.php?title=BK-5Br-NM-AMT&action=edit&redlink=1" class="new" title="BK-5Br-NM-AMT (page does not exist)">BK-5Br-NM-AMT</a></li> <li><a href="/w/index.php?title=BK-5Cl-NM-AMT&action=edit&redlink=1" class="new" title="BK-5Cl-NM-AMT (page does not exist)">BK-5Cl-NM-AMT</a></li> <li><a href="/w/index.php?title=BK-5F-NM-AMT&action=edit&redlink=1" class="new" title="BK-5F-NM-AMT (page does not exist)">BK-5F-NM-AMT</a></li> <li><a href="/wiki/BK-NM-AMT" title="BK-NM-AMT">BK-NM-AMT</a></li> <li><a href="/wiki/BNC-210" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/BW-723C86" title="BW-723C86">BW-723C86</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/wiki/Indolylpropylaminopentane" title="Indolylpropylaminopentane">IPAP (α,<i>N</i>-DPT)</a></li> <li><a href="/wiki/MPMI_(drug)" title="MPMI (drug)">MPMI</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Triptan" title="Triptan">Triptans</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Almotriptan" title="Almotriptan">Almotriptan</a></li> <li><a href="/wiki/Donitriptan" title="Donitriptan">Donitriptan</a></li> <li><a href="/wiki/Eletriptan" title="Eletriptan">Eletriptan</a></li> <li><a href="/wiki/Frovatriptan" title="Frovatriptan">Frovatriptan</a></li> <li><a href="/wiki/L-694247" title="L-694247">L-694247</a></li> <li><a href="/wiki/Rizatriptan" title="Rizatriptan">Rizatriptan</a></li> <li><a href="/wiki/Sumatriptan" title="Sumatriptan">Sumatriptan</a></li> <li><a href="/wiki/Zolmitriptan" title="Zolmitriptan">Zolmitriptan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Cyclic_compound" title="Cyclic compound">Cyclized tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bay_R_1531" title="Bay R 1531">Bay R 1531</a></li> <li><a href="/wiki/Ciclindole" title="Ciclindole">Ciclindole</a></li> <li><a href="/wiki/Cyclic_3-hydroxymelatonin" title="Cyclic 3-hydroxymelatonin">Cyclic 3-OHM</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> and <a href="/wiki/Lysergamide" class="mw-redirect" title="Lysergamide">lysergamides</a> (e.g., <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">LSD</a>)</li> <li><a href="/wiki/Flucindole" title="Flucindole">Flucindole</a></li> <li><a href="/wiki/Harmala_alkaloid" title="Harmala alkaloid"><i>Harmala</i> alkaloids</a> and <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carbolines</a> (e.g., <a href="/wiki/6-MeO-THH" title="6-MeO-THH">6-MeO-THH</a>, <a href="/wiki/9-Methyl-%CE%B2-carboline" title="9-Methyl-β-carboline">9-Me-BC</a>, <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carboline (norharman)</a>, <a href="/wiki/Harmaline" title="Harmaline">harmaline</a>, <a href="/wiki/Harmalol" title="Harmalol">harmalol</a>, <a href="/wiki/Harmane" title="Harmane">harmane</a>, <a href="/wiki/Harmine" title="Harmine">harmine</a>, <a href="/wiki/Pinoline" title="Pinoline">pinoline</a>, <a href="/wiki/Tetrahydroharmine" title="Tetrahydroharmine">tetrahydroharmine</a>, <a href="/wiki/Tryptoline" title="Tryptoline">tryptoline</a>)</li> <li><a href="/wiki/Iboga-type_alkaloid" title="Iboga-type alkaloid"><i>Iboga</i> alkaloids</a> and related (e.g., <a href="/wiki/DM-506" title="DM-506">DM-506 (ibogaminalog)</a>, <a href="/wiki/Ibogaine" title="Ibogaine">ibogaine</a>, <a href="/wiki/Ibogamine" title="Ibogamine">ibogamine</a>, <a href="/wiki/Noribogaine" title="Noribogaine">noribogaine</a>, <a href="/wiki/Tabernanthalog" title="Tabernanthalog">tabernanthalog</a>, <a href="/wiki/Tabernanthine" title="Tabernanthine">tabernanthine</a>)</li> <li><a href="/wiki/LY-266,097" title="LY-266,097">LY-266,097</a></li> <li><a href="/wiki/Metralindole" title="Metralindole">Metralindole</a></li> <li><a href="/wiki/NDTDI" title="NDTDI">NDTDI</a></li> <li><a href="/wiki/PHA-57378" title="PHA-57378">PHA-57378</a></li> <li><a href="/wiki/PNU-22394" title="PNU-22394">PNU-22394</a></li> <li><a href="/wiki/PNU-181731" title="PNU-181731">PNU-181731</a></li> <li><a href="/wiki/RU-28306" title="RU-28306">RU-28306</a></li> <li><a href="/wiki/Yohimban" title="Yohimban">Yohimbans</a> (e.g., <a href="/wiki/Yohimbine" title="Yohimbine">yohimbine</a>, <a href="/wiki/Rauwolscine" title="Rauwolscine">rauwolscine</a>, <a href="/wiki/Spegatrine" title="Spegatrine">spegatrine</a>, <a href="/wiki/Corynanthine" title="Corynanthine">corynanthine</a>, <a href="/wiki/Ajmalicine" title="Ajmalicine">ajmalicine</a>, <a href="/wiki/Reserpine" title="Reserpine">reserpine</a>, <a href="/wiki/Deserpidine" title="Deserpidine">deserpidine</a>, <a href="/wiki/Rescinnamine" title="Rescinnamine">rescinnamine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Isotryptamine" title="Isotryptamine">Isotryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5-MeO-isoDMT" title="5-MeO-isoDMT">5-MeO-isoDMT</a></li> <li><a href="/wiki/6-MeO-isoDMT" title="6-MeO-isoDMT">6-MeO-isoDMT</a></li> <li><a href="/wiki/AAZ-A-154" class="mw-redirect" title="AAZ-A-154">AAZ-A-154 (DLX-001)</a></li> <li><a href="/wiki/IsoAMT" class="mw-redirect" title="IsoAMT">isoAMT</a></li> <li><a href="/wiki/IsoDMT" title="IsoDMT">isoDMT</a></li> <li><a href="/wiki/Isotryptamine" title="Isotryptamine">Isotryptamine (isoT)</a></li> <li><a href="/wiki/PNU-181731" title="PNU-181731">PNU-181731</a></li> <li><a href="/wiki/Ro60-0175" title="Ro60-0175">Ro60-0175</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Related compounds</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=2-Azapsilocin&action=edit&redlink=1" class="new" title="2-Azapsilocin (page does not exist)">2-Azapsilocin</a></li> <li><a href="/w/index.php?title=4-Aza-5-MeO-DPT&action=edit&redlink=1" class="new" title="4-Aza-5-MeO-DPT (page does not exist)">4-Aza-5-MeO-DPT</a></li> <li><a href="/w/index.php?title=5-Aza-4-MeO-DiPT&action=edit&redlink=1" class="new" title="5-Aza-4-MeO-DiPT (page does not exist)">5-Aza-4-MeO-DiPT</a></li> <li><a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li> <li><a href="/wiki/5-Hydroxyindoleacetaldehyde" title="5-Hydroxyindoleacetaldehyde">5-HIAL</a></li> <li><a href="/w/index.php?title=5-Hydroxyindole_thiazoladine_carboxylic_acid&action=edit&redlink=1" class="new" title="5-Hydroxyindole thiazoladine carboxylic acid (page does not exist)">5-HITCA</a></li> <li><a href="/w/index.php?title=5-Methoxyindoleacetaldehyde&action=edit&redlink=1" class="new" title="5-Methoxyindoleacetaldehyde (page does not exist)">5-MIAL</a></li> <li><a href="/w/index.php?title=7-Aza-5-MeO-DiPT&action=edit&redlink=1" class="new" title="7-Aza-5-MeO-DiPT (page does not exist)">7-Aza-5-MeO-DiPT</a></li> <li><a href="/wiki/AAZ-A-154" class="mw-redirect" title="AAZ-A-154">AAZ-A-154</a></li> <li><a href="/wiki/AL-34662" title="AL-34662">AL-34662</a></li> <li><a href="/wiki/AL-38022A" title="AL-38022A">AL-38022A</a></li> <li><a href="/wiki/Substituted_benzofuran" title="Substituted benzofuran">Benzofurans</a> (e.g., <a href="/wiki/3-(2-aminopropyl)benzofuran" class="mw-redirect" title="3-(2-aminopropyl)benzofuran">3-APB</a>, <a href="/wiki/5-MeO-DiBF" title="5-MeO-DiBF">5-MeO-DiBF</a>, <a href="/wiki/Benzofuranylpropylaminopentane" title="Benzofuranylpropylaminopentane">BPAP</a>, <a href="/wiki/Dimemebfe" title="Dimemebfe">dimemebfe</a>, <a href="/wiki/Mebfap" title="Mebfap">mebfap</a>)</li> <li><a href="/wiki/BRL-54443" title="BRL-54443">BRL-54443</a></li> <li><a href="/wiki/CP-94253" title="CP-94253">CP-94253</a></li> <li><a href="/wiki/EMD-386088" title="EMD-386088">EMD-386088</a></li> <li><a href="/w/index.php?title=I-32_(drug)&action=edit&redlink=1" class="new" title="I-32 (drug) (page does not exist)">I-32</a></li> <li><a href="/wiki/Indoleacetaldehyde" class="mw-redirect" title="Indoleacetaldehyde">IAL</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine</a></li> <li><a href="/wiki/LY-367,265" title="LY-367,265">LY-367265</a></li> <li>Non-tryptamine <a href="/wiki/Triptan" title="Triptan">triptans</a> (e.g., <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/LY-334370" title="LY-334370">LY-334370</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>)</li> <li><a href="/wiki/Pirlindole" title="Pirlindole">Pirlindole</a></li> <li><a href="/wiki/(R)-69" title="(R)-69">(<i>R</i>)-69 (3IQ)</a></li> <li><a href="/wiki/Ro60-0213" title="Ro60-0213">Ro60-0213</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/Sertindole" title="Sertindole">Sertindole</a></li> <li><a href="/wiki/SN-22" title="SN-22">SN-22</a></li> <li><a href="/wiki/Tepirindole" title="Tepirindole">Tepirindole</a></li> <li><a href="/wiki/Tetrindole" title="Tetrindole">Tetrindole</a></li> <li><a href="/wiki/VER-3323" title="VER-3323">VER-3323</a></li> <li><a href="/wiki/VU6067416" title="VU6067416">VU6067416</a></li> <li><a href="/wiki/YM-348" title="YM-348">YM-348</a></li></ul> </div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output 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