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Morphine - Wikipedia

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<li id="toc-Pain" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pain"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Pain</span> </div> </a> <ul id="toc-Pain-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Shortness_of_breath" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Shortness_of_breath"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Shortness of breath</span> </div> </a> <ul id="toc-Shortness_of_breath-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Opioid_use_disorder" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Opioid_use_disorder"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Opioid use disorder</span> </div> </a> <ul id="toc-Opioid_use_disorder-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Contraindications" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Contraindications"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Contraindications</span> </div> </a> <ul id="toc-Contraindications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Adverse_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Adverse_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Adverse effects</span> </div> </a> <button aria-controls="toc-Adverse_effects-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 Adverse effects subsection</span> </button> <ul id="toc-Adverse_effects-sublist" class="vector-toc-list"> <li id="toc-Constipation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Constipation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Constipation</span> </div> </a> <ul id="toc-Constipation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hormone_imbalance" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hormone_imbalance"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Hormone imbalance</span> </div> </a> <ul id="toc-Hormone_imbalance-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Effects_on_human_performance" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Effects_on_human_performance"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Effects on human performance</span> </div> </a> <ul id="toc-Effects_on_human_performance-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reinforcement_disorders" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reinforcement_disorders"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Reinforcement disorders</span> </div> </a> <ul id="toc-Reinforcement_disorders-sublist" class="vector-toc-list"> <li id="toc-Addiction" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Addiction"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4.1</span> <span>Addiction</span> </div> </a> <ul id="toc-Addiction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tolerance" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Tolerance"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4.2</span> <span>Tolerance</span> </div> </a> <ul id="toc-Tolerance-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dependence_and_withdrawal" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Dependence_and_withdrawal"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4.3</span> <span>Dependence and withdrawal</span> </div> </a> <ul id="toc-Dependence_and_withdrawal-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Toxicity</span> </div> </a> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Pharmacology</span> </div> </a> <button aria-controls="toc-Pharmacology-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 Pharmacology subsection</span> </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Pharmacodynamics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Pharmacodynamics</span> </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> <li id="toc-Analgesia_creation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Analgesia_creation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.1</span> <span>Analgesia creation</span> </div> </a> <ul id="toc-Analgesia_creation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Gene_expression" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Gene_expression"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.2</span> <span>Gene expression</span> </div> </a> <ul id="toc-Gene_expression-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Effects_on_the_immune_system" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Effects_on_the_immune_system"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.3</span> <span>Effects on the immune system</span> </div> </a> <ul id="toc-Effects_on_the_immune_system-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> <li id="toc-Absorption_and_metabolism" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Absorption_and_metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.1</span> <span>Absorption and metabolism</span> </div> </a> <ul id="toc-Absorption_and_metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Extended-release" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Extended-release"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.2</span> <span>Extended-release</span> </div> </a> <ul id="toc-Extended-release-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Detection_in_body_fluids" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Detection_in_body_fluids"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.3</span> <span>Detection in body fluids</span> </div> </a> <ul id="toc-Detection_in_body_fluids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chirality_and_biological_activity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chirality_and_biological_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Chirality and biological activity</span> </div> </a> <ul id="toc-Chirality_and_biological_activity-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Natural_occurrence" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Natural_occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Natural occurrence</span> </div> </a> <button aria-controls="toc-Natural_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 Natural occurrence subsection</span> </button> <ul id="toc-Natural_occurrence-sublist" class="vector-toc-list"> <li id="toc-Human_biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Human_biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Human biosynthesis</span> </div> </a> <ul id="toc-Human_biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis_in_the_opium_poppy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis_in_the_opium_poppy"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Biosynthesis in the opium poppy</span> </div> </a> <ul id="toc-Biosynthesis_in_the_opium_poppy-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Chemistry</span> </div> </a> <button aria-controls="toc-Chemistry-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 Chemistry subsection</span> </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Structure_description" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Structure_description"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Structure description</span> </div> </a> <ul id="toc-Structure_description-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uses_and_derivatives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Uses_and_derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Uses and derivatives</span> </div> </a> <ul id="toc-Uses_and_derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemical_salts_of_Morphine" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chemical_salts_of_Morphine"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Chemical salts of Morphine</span> </div> </a> <ul id="toc-Chemical_salts_of_Morphine-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Production" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Production"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Production</span> </div> </a> <button aria-controls="toc-Production-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 Production subsection</span> </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-Chemical_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chemical_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Chemical synthesis</span> </div> </a> <ul id="toc-Chemical_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-GMO_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#GMO_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2</span> <span>GMO synthesis</span> </div> </a> <ul id="toc-GMO_synthesis-sublist" class="vector-toc-list"> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2.1</span> <span>Research</span> </div> </a> <ul id="toc-Research-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Precursor_to_other_opioids" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Precursor_to_other_opioids"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Precursor to other opioids</span> </div> </a> <button aria-controls="toc-Precursor_to_other_opioids-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 Precursor to other opioids subsection</span> </button> <ul id="toc-Precursor_to_other_opioids-sublist" class="vector-toc-list"> <li id="toc-Pharmaceutical" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmaceutical"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1</span> <span>Pharmaceutical</span> </div> </a> <ul id="toc-Pharmaceutical-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Illicit" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Illicit"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.2</span> <span>Illicit</span> </div> </a> <ul id="toc-Illicit-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Society and culture</span> </div> </a> <button aria-controls="toc-Society_and_culture-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 Society and culture subsection</span> </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Legal_status" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Legal_status"> <div class="vector-toc-text"> <span class="vector-toc-numb">11.1</span> <span>Legal status</span> </div> </a> <ul id="toc-Legal_status-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Non-medical_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Non-medical_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">11.2</span> <span>Non-medical use</span> </div> </a> <ul id="toc-Non-medical_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Names"> <div class="vector-toc-text"> <span class="vector-toc-numb">11.3</span> <span>Names</span> </div> </a> <ul id="toc-Names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Access_in_developing_countries" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Access_in_developing_countries"> <div class="vector-toc-text"> <span class="vector-toc-numb">11.4</span> <span>Access in developing countries</span> </div> </a> <ul id="toc-Access_in_developing_countries-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</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"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">13</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">Morphine</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 85 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-85" 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">85 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Morfien" title="Morfien – Afrikaans" lang="af" hreflang="af" data-title="Morfien" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-als mw-list-item"><a href="https://als.wikipedia.org/wiki/Morphin" title="Morphin – Alemannic" lang="gsw" hreflang="gsw" data-title="Morphin" data-language-autonym="Alemannisch" data-language-local-name="Alemannic" class="interlanguage-link-target"><span>Alemannisch</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D9%88%D8%B1%D9%81%D9%8A%D9%86" title="مورفين – Arabic" lang="ar" hreflang="ar" data-title="مورفين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Morfina" title="Morfina – Asturian" lang="ast" hreflang="ast" data-title="Morfina" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Morfin" title="Morfin – Azerbaijani" lang="az" hreflang="az" data-title="Morfin" 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%D8%B1%D9%81%DB%8C%D9%86" title="مرفین – South Azerbaijani" lang="azb" hreflang="azb" data-title="مرفین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AE%E0%A6%B0%E0%A6%AB%E0%A6%BF%E0%A6%A8" title="মরফিন – Bangla" lang="bn" hreflang="bn" data-title="মরফিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/M%C3%B4%CD%98-hui" title="Mô͘-hui – Minnan" lang="nan" hreflang="nan" data-title="Mô͘-hui" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9C%D0%B0%D1%80%D1%84%D1%96%D0%BD" title="Марфін – Belarusian" lang="be" hreflang="be" data-title="Марфін" 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%D0%B0%D1%80%D1%84%D1%96%D0%BD" title="Марфін – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Марфін" 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%BE%D1%80%D1%84%D0%B8%D0%BD" title="Морфин – Bulgarian" lang="bg" hreflang="bg" data-title="Морфин" 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/Morfin" title="Morfin – Bosnian" lang="bs" hreflang="bs" data-title="Morfin" 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/Morfina" title="Morfina – Catalan" lang="ca" hreflang="ca" data-title="Morfina" 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/Morfin" title="Morfin – Czech" lang="cs" hreflang="cs" data-title="Morfin" 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/Morffin" title="Morffin – Welsh" lang="cy" hreflang="cy" data-title="Morffin" 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/Morfin" title="Morfin – Danish" lang="da" hreflang="da" data-title="Morfin" 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/Morphin" title="Morphin – German" lang="de" hreflang="de" data-title="Morphin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Morfiin" title="Morfiin – Estonian" lang="et" hreflang="et" data-title="Morfiin" 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%BF%CF%81%CF%86%CE%AF%CE%BD%CE%B7" title="Μορφίνη – Greek" lang="el" hreflang="el" data-title="Μορφίνη" 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/Morfina" title="Morfina – Spanish" lang="es" hreflang="es" data-title="Morfina" 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/Morfino" title="Morfino – Esperanto" lang="eo" hreflang="eo" data-title="Morfino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Morfina" title="Morfina – Basque" lang="eu" hreflang="eu" data-title="Morfina" 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%88%D8%B1%D9%81%DB%8C%D9%86" title="مورفین – Persian" lang="fa" hreflang="fa" data-title="مورفین" 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/Morphine" title="Morphine – French" lang="fr" hreflang="fr" data-title="Morphine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-fy mw-list-item"><a href="https://fy.wikipedia.org/wiki/Morfine" title="Morfine – Western Frisian" lang="fy" hreflang="fy" data-title="Morfine" data-language-autonym="Frysk" data-language-local-name="Western Frisian" class="interlanguage-link-target"><span>Frysk</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Moirf%C3%ADn" title="Moirfín – Irish" lang="ga" hreflang="ga" data-title="Moirfín" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gd mw-list-item"><a href="https://gd.wikipedia.org/wiki/Moirfin" title="Moirfin – Scottish Gaelic" lang="gd" hreflang="gd" data-title="Moirfin" data-language-autonym="Gàidhlig" data-language-local-name="Scottish Gaelic" class="interlanguage-link-target"><span>Gàidhlig</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Morfina" title="Morfina – Galician" lang="gl" hreflang="gl" data-title="Morfina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%AA%A8%EB%A5%B4%ED%95%80" title="모르핀 – Korean" lang="ko" hreflang="ko" data-title="모르핀" 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%B8%D6%80%D6%86%D5%AB%D5%B6" title="Մորֆին – Armenian" lang="hy" hreflang="hy" data-title="Մորֆին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AE%E0%A5%89%E0%A4%B0%E0%A4%AB%E0%A5%80%E0%A4%A8" title="मॉरफीन – Hindi" lang="hi" hreflang="hi" data-title="मॉरफीन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Morfin" title="Morfin – Croatian" lang="hr" hreflang="hr" data-title="Morfin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Morfino" title="Morfino – Ido" lang="io" hreflang="io" data-title="Morfino" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-ilo mw-list-item"><a href="https://ilo.wikipedia.org/wiki/Morfina" title="Morfina – Iloko" lang="ilo" hreflang="ilo" data-title="Morfina" data-language-autonym="Ilokano" data-language-local-name="Iloko" class="interlanguage-link-target"><span>Ilokano</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Morfin" title="Morfin – Indonesian" lang="id" hreflang="id" data-title="Morfin" 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-zu mw-list-item"><a href="https://zu.wikipedia.org/wiki/I-Morphine" title="I-Morphine – Zulu" lang="zu" hreflang="zu" data-title="I-Morphine" data-language-autonym="IsiZulu" data-language-local-name="Zulu" class="interlanguage-link-target"><span>IsiZulu</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Morf%C3%ADn" title="Morfín – Icelandic" lang="is" hreflang="is" data-title="Morfín" 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/Morfina" title="Morfina – Italian" lang="it" hreflang="it" data-title="Morfina" 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%95%D7%A8%D7%A4%D7%99%D7%9F" title="מורפין – Hebrew" lang="he" hreflang="he" data-title="מורפין" 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%9D%E1%83%A0%E1%83%A4%E1%83%98%E1%83%9C%E1%83%98" title="მორფინი – Georgian" lang="ka" hreflang="ka" data-title="მორფინი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-ks mw-list-item"><a href="https://ks.wikipedia.org/wiki/%D9%85%D9%88%D8%B1%D9%81%DB%8C%D9%86" title="مورفین – Kashmiri" lang="ks" hreflang="ks" data-title="مورفین" data-language-autonym="कॉशुर / کٲشُر" data-language-local-name="Kashmiri" class="interlanguage-link-target"><span>कॉशुर / کٲشُر</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9C%D0%BE%D1%80%D1%84%D0%B8%D0%BD" title="Морфин – Kazakh" lang="kk" hreflang="kk" data-title="Морфин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Morphina" title="Morphina – Latin" lang="la" hreflang="la" data-title="Morphina" 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/Morf%C4%ABns" title="Morfīns – Latvian" lang="lv" hreflang="lv" data-title="Morfīns" 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/Morfinas" title="Morfinas – Lithuanian" lang="lt" hreflang="lt" data-title="Morfinas" 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/Morfin" title="Morfin – Hungarian" lang="hu" hreflang="hu" data-title="Morfin" 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%BE%D1%80%D1%84%D0%B8%D0%BD" title="Морфин – Macedonian" lang="mk" hreflang="mk" data-title="Морфин" 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%8B%E0%B5%BC%E0%B4%AB%E0%B4%BF%E0%B5%BB" title="മോർഫിൻ – Malayalam" lang="ml" hreflang="ml" data-title="മോർഫിൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-xmf mw-list-item"><a href="https://xmf.wikipedia.org/wiki/%E1%83%9B%E1%83%9D%E1%83%A0%E1%83%A4%E1%83%98%E1%83%9C%E1%83%98" title="მორფინი – Mingrelian" lang="xmf" hreflang="xmf" data-title="მორფინი" data-language-autonym="მარგალური" data-language-local-name="Mingrelian" class="interlanguage-link-target"><span>მარგალური</span></a></li><li class="interlanguage-link interwiki-arz mw-list-item"><a href="https://arz.wikipedia.org/wiki/%D9%85%D9%88%D8%B1%D9%81%D9%8A%D9%86" title="مورفين – Egyptian Arabic" lang="arz" hreflang="arz" data-title="مورفين" data-language-autonym="مصرى" data-language-local-name="Egyptian Arabic" class="interlanguage-link-target"><span>مصرى</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Morfina" title="Morfina – Malay" lang="ms" hreflang="ms" data-title="Morfina" 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-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Morfine" title="Morfine – Dutch" lang="nl" hreflang="nl" data-title="Morfine" 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%A2%E3%83%AB%E3%83%92%E3%83%8D" title="モルヒネ – Japanese" lang="ja" hreflang="ja" data-title="モルヒネ" 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/Morfin" title="Morfin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Morfin" 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/Morfin" title="Morfin – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Morfin" 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/Morfina" title="Morfina – Occitan" lang="oc" hreflang="oc" data-title="Morfina" 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%AC%B0%E0%AD%8D%E0%AC%AB%E0%AC%BF%E0%AC%A8" title="ମର୍ଫିନ – Odia" lang="or" hreflang="or" data-title="ମର୍ଫିନ" 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/Morfin" title="Morfin – Uzbek" lang="uz" hreflang="uz" data-title="Morfin" 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-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%AE%E0%A8%BE%E0%A8%B0%E0%A8%AB%E0%A8%BC%E0%A9%80%E0%A8%A8" title="ਮਾਰਫ਼ੀਨ – Punjabi" lang="pa" hreflang="pa" data-title="ਮਾਰਫ਼ੀਨ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D9%85%D9%88%D8%B1%D9%81%D9%8A%D9%86" title="مورفين – Pashto" lang="ps" hreflang="ps" data-title="مورفين" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Morfina" title="Morfina – Polish" lang="pl" hreflang="pl" data-title="Morfina" 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/Morfina" title="Morfina – Portuguese" lang="pt" hreflang="pt" data-title="Morfina" 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/Morfin%C4%83" title="Morfină – Romanian" lang="ro" hreflang="ro" data-title="Morfină" 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%BE%D1%80%D1%84%D0%B8%D0%BD" title="Морфин – Russian" lang="ru" hreflang="ru" data-title="Морфин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Morfina" title="Morfina – Albanian" lang="sq" hreflang="sq" data-title="Morfina" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Morphine" title="Morphine – Simple English" lang="en-simple" hreflang="en-simple" data-title="Morphine" 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/Morf%C3%ADn" title="Morfín – Slovak" lang="sk" hreflang="sk" data-title="Morfín" 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/Morfin" title="Morfin – Slovenian" lang="sl" hreflang="sl" data-title="Morfin" 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%86%D8%B1%D9%81%DB%8C%D9%86" title="مۆرفین – Central Kurdish" lang="ckb" hreflang="ckb" data-title="مۆرفین" 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/%D0%9C%D0%BE%D1%80%D1%84%D0%B8%D0%BD" title="Морфин – Serbian" lang="sr" hreflang="sr" data-title="Морфин" 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/Morfin" title="Morfin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Morfin" 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/Morfiini" title="Morfiini – Finnish" lang="fi" hreflang="fi" data-title="Morfiini" 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/Morfin" title="Morfin – Swedish" lang="sv" hreflang="sv" data-title="Morfin" 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%AE%BE%E0%AE%B0%E0%AF%8D%E0%AE%83%E0%AE%AA%E0%AF%80%E0%AE%A9%E0%AF%8D" title="மார்ஃபீன் – Tamil" lang="ta" hreflang="ta" data-title="மார்ஃபீன்" 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%B0%BE%E0%B0%B0%E0%B1%8D%E0%B0%AB%E0%B0%BF%E0%B0%A8%E0%B1%8D" title="మార్ఫిన్ – Telugu" lang="te" hreflang="te" data-title="మార్ఫిన్" 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%B8%A1%E0%B8%AD%E0%B8%A3%E0%B9%8C%E0%B8%9F%E0%B8%B5%E0%B8%99" title="มอร์ฟีน – Thai" lang="th" hreflang="th" data-title="มอร์ฟีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Morfin" title="Morfin – Turkish" lang="tr" hreflang="tr" data-title="Morfin" 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%BE%D1%80%D1%84%D1%96%D0%BD" title="Морфін – Ukrainian" lang="uk" hreflang="uk" data-title="Морфін" 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%D9%88%D8%B1%D9%81%DB%8C%D9%86" title="مورفین – Urdu" lang="ur" hreflang="ur" data-title="مورفین" 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/Morphin" title="Morphin – Vietnamese" lang="vi" hreflang="vi" data-title="Morphin" 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-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E5%97%8E%E5%95%A1" title="嗎啡 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="嗎啡" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Morfina" title="Morfina – Waray" lang="war" hreflang="war" data-title="Morfina" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E5%90%97%E5%95%A1" title="吗啡 – Wu" lang="wuu" hreflang="wuu" data-title="吗啡" data-language-autonym="吴语" 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aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <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">Pain medication of the opiate family</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pain medication of the opiate family</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">This article is about the chemical compound. For other uses, see <a href="/wiki/Morphine_(disambiguation)" class="mw-disambig" title="Morphine (disambiguation)">morphine (disambiguation)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">"Morphia" redirects here. For other uses, see <a href="/wiki/Morphia_(disambiguation)" class="mw-disambig" title="Morphia (disambiguation)">Morphia (disambiguation)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Morpheein" title="Morpheein">morpheein</a> or <a href="/wiki/Morpheme" title="Morpheme">morpheme</a>.</div> <p class="mw-empty-elt"> </p> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Morphine">Morphine</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Morphine2DCSDS.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Morphine2DCSDS.svg/180px-Morphine2DCSDS.svg.png" decoding="async" width="180" height="175" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Morphine2DCSDS.svg/270px-Morphine2DCSDS.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Morphine2DCSDS.svg/360px-Morphine2DCSDS.svg.png 2x" data-file-width="819" data-file-height="794" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:Morphine_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Morphine_molecule_ball.png/180px-Morphine_molecule_ball.png" decoding="async" width="180" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Morphine_molecule_ball.png/270px-Morphine_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Morphine_molecule_ball.png/360px-Morphine_molecule_ball.png 2x" data-file-width="2000" data-file-height="1537" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data"><span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="&#39;m&#39; in &#39;my&#39;">m</span><span title="/ɔː/: &#39;au&#39; in &#39;fraud&#39;">ɔː</span><span title="&#39;r&#39; in &#39;rye&#39;">r</span><span title="&#39;f&#39; in &#39;find&#39;">f</span><span title="/iː/: &#39;ee&#39; in &#39;fleece&#39;">iː</span><span title="&#39;n&#39; in &#39;nigh&#39;">n</span></span>/</a></span></span>&#x20;</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Statex, MS Contin, Oramorph, others<sup id="cite_ref-drugs.com-page_1-0" class="reference"><a href="#cite_note-drugs.com-page-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/morphine.html">Monograph</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><span title="medlineplus.gov"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a682133.html">a682133</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</a></th><td class="infobox-data"><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><small><abbr class="country-name" title="United States">US</abbr></small>&#160;<a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>:&#160;<span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&amp;query=Morphine">Morphine</a></span></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small>&#x20;C<sup id="cite_ref-Drugs.com_pregnancy_2-0" class="reference"><a href="#cite_note-Drugs.com_pregnancy-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Substance_dependence" title="Substance dependence">Dependence<br />liability</a></th><td class="infobox-data">High</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Addiction" title="Addiction">Addiction<br />liability</a></th><td class="infobox-data">High<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Inhalation" title="Inhalation">Inhalation</a>, <a href="/wiki/Insufflation_(medicine)" title="Insufflation (medicine)">insufflation</a>, <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>, <a href="/wiki/Rectal_administration" title="Rectal administration">rectal</a>, <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">subcutaneous</a>, <a href="/wiki/Intramuscular" class="mw-redirect" title="Intramuscular">intramuscular</a>, <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">intravenous</a>, <a href="/wiki/Epidural" class="mw-redirect" title="Epidural">epidural</a>, <a href="/wiki/Intrathecal" class="mw-redirect" title="Intrathecal">intrathecal</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Opiate" title="Opiate">Opiate</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/ATC_code_N02" title="ATC code N02">N02AA01</a>&#x20;(<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N02AA01">WHO</a></span>)&#x20;</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small>&#x20;<a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_8" title="Standard for the Uniform Scheduling of Medicines and Poisons">S8</a> (Controlled drug)</li> <li><small><abbr class="country-name" title="Brazil">BR</abbr>:</small>&#x20;<a href="/wiki/Brazilian_Controlled_Drugs_and_Substances_Act#Class_A1" title="Brazilian Controlled Drugs and Substances Act">Class A1</a> (Narcotic drugs)</li> <li><small><abbr class="country-name" title="Canada">CA</abbr></small>:&#x20;<a href="/wiki/Controlled_Drugs_and_Substances_Act#Schedule_I" title="Controlled Drugs and Substances Act">Schedule I</a><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup></li> <li><small><abbr class="country-name" title="Germany">DE</abbr></small>:&#x20;<a href="/wiki/Drugs_controlled_by_the_German_Narcotic_Drugs_Act#Anlage_III" title="Drugs controlled by the German Narcotic Drugs Act">Anlage III</a> (Special prescription form required)</li> <li><small><abbr class="country-name" title="New Zealand">NZ</abbr></small>:&#x20;<a href="/wiki/Misuse_of_Drugs_Act_1975#Class_B" title="Misuse of Drugs Act 1975">Class B</a></li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small>&#x20;<a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)&#x20;/<span class="nowrap">&#160;</span>Class A<sup id="cite_ref-Black&#39;s_5-0" class="reference"><a href="#cite_note-Black&#39;s-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup></li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small>&#x20;<a href="/wiki/Controlled_Substances_Act#Schedule_II_drugs" title="Controlled Substances Act">Schedule II</a>&#x20;/<span class="nowrap">&#160;</span>Schedule III<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup></li> <li><small><abbr class="country-name" title="United Nations">UN</abbr>:</small>&#x20;<a href="/wiki/Single_Convention_on_Narcotic_Drugs#List_of_controlled_narcotic_drugs" title="Single Convention on Narcotic Drugs">Narcotic Schedules&#160;I and&#160;III</a></li> <li><small><abbr class="country-name" title="European Union">EU</abbr>:</small>&#x20;Rx-only<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">20–40% (by mouth), 36–71% (rectal),<sup id="cite_ref-pmid3387374_9-0" class="reference"><a href="#cite_note-pmid3387374-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> 100% (IV/IM)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">30–40%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a>: <a href="/wiki/UGT2B7" title="UGT2B7">UGT2B7</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data">• <a href="/wiki/Morphine-3-glucuronide" title="Morphine-3-glucuronide">Morphine-3-glucuronide</a> (90%)<br />• <a href="/wiki/Morphine-6-glucuronide" title="Morphine-6-glucuronide">Morphine-6-glucuronide</a> (10%)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Onset_of_action" title="Onset of action">Onset of action</a></th><td class="infobox-data">5&#160;minutes (IV), 15&#160;minutes (IM),<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup> 20&#160;minutes (PO)<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">2–3&#160;hours</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pharmacodynamics#Duration_of_action" title="Pharmacodynamics">Duration of action</a></th><td class="infobox-data">3–7&#160;hours<sup id="cite_ref-AHFS2015_12-0" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Rockwood2009_13-0" class="reference"><a href="#cite_note-Rockwood2009-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Kidney" title="Kidney">Kidney</a> 90%, <a href="/wiki/Bile_duct" title="Bile duct">bile duct</a> 10%</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</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; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(4<i>R</i>,4a<i>R</i>,7<i>S</i>,7a<i>R</i>,12b<i>S</i>)-3-Methyl-2,3,4,4a,7,7a-hexahydro-1<i>H</i>-4,12-methano[1]benzofuro[3,2-<i>e</i>]isoquinoline-7,9-diol</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=57-27-2">57-27-2</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup> <br />64-31-3 (neutral sulfate),<br />52-26-6 (hydrochloride)</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><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/5288826">5288826</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=1627">1627</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><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/DB00295">DB00295</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><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.4450907.html">4450907</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><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/76I7G6D29C">76I7G6D29C</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><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/D08233">D08233</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><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=CHEBI:17303">CHEBI:17303</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><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/ChEMBL70">ChEMBL70</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB ligand</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>MOI (<span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=MOI">PDBe</a></span>, <span title="www.rcsb.org"><a rel="nofollow" class="external text" href="https://www.rcsb.org/ligand/MOI">RCSB&#160;PDB</a></span>)</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><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></th><td class="infobox-data"><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/DTXSID9023336">DTXSID9023336</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q81225#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><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.291">100.000.291</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q81225#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><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>17</sub><span title="Hydrogen">H</span><sub>19</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>3</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002285343000000000♠"></span>285.343</span>&#160;g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><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=CN1CC%5BC%40%5D23C4%3DC5C%3DCC%28O%29%3DC4O%5BC%40H%5D2%5BC%40%40H%5D%28O%29C%3DC%5BC%40H%5D3%5BC%40H%5D1C5">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></th><td class="infobox-data">HCl &amp; sulf.: 60</td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><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="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><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="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1<sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:BQJCRHHNABKAKU-KBQPJGBKSA-N<sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">&#160;&#160;<span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&amp;rev1=477170110&amp;page2=Morphine">(verify)</a></span></span></td></tr></tbody></table> <p><b>Morphine</b>, formerly also called <b>morphia</b>,<sup id="cite_ref-Morphia_14-0" class="reference"><a href="#cite_note-Morphia-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> is an <a href="/wiki/Opiate" title="Opiate">opiate</a> that is found naturally in <a href="/wiki/Opium" title="Opium">opium</a>, a dark brown resin produced by drying the latex of opium poppies (<i><a href="/wiki/Papaver_somniferum" title="Papaver somniferum">Papaver somniferum</a></i>). It is mainly used as an <a href="/wiki/Analgesic" title="Analgesic">analgesic</a> (pain medication). There are numerous methods used to administer morphine: orally; <a href="/wiki/Sublingual_administration" title="Sublingual administration">administered under the tongue</a>; via inhalation; <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection">injection into a vein</a>, <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">injection into a muscle</a>, <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">injection under the skin</a>, or injection into the <a href="/wiki/Spinal_cord" title="Spinal cord">spinal cord</a> area; <a href="/wiki/Transdermal" title="Transdermal">transdermal</a>; or via <a href="/wiki/Rectal_administration" title="Rectal administration">administered into the rectal canal</a> <a href="/wiki/Suppository" title="Suppository">suppository</a>.<sup id="cite_ref-AHFS2015_12-1" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-St2012_15-0" class="reference"><a href="#cite_note-St2012-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> It acts directly on the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> (CNS) to induce <a href="/wiki/Analgesia" class="mw-redirect" title="Analgesia">analgesia</a> and alter perception and emotional response to pain. Physical and psychological dependence and tolerance may develop with repeated administration.<sup id="cite_ref-AHFS2015_12-2" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> It can be taken for both <a href="/wiki/Acute_pain" class="mw-redirect" title="Acute pain">acute pain</a> and <a href="/wiki/Chronic_pain" title="Chronic pain">chronic pain</a> and is frequently used for pain from <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a>, <a href="/wiki/Kidney_stone" class="mw-redirect" title="Kidney stone">kidney stones</a>, and during <a href="/wiki/Childbirth" title="Childbirth">labor</a>.<sup id="cite_ref-AHFS2015_12-3" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> Its maximum effect is reached after about 20&#160;minutes when administered intravenously and 60&#160;minutes when administered by mouth, while the duration of its effect is 3–7&#160;hours.<sup id="cite_ref-AHFS2015_12-4" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Rockwood2009_13-1" class="reference"><a href="#cite_note-Rockwood2009-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Extended-release_morphine" title="Extended-release morphine">Long-acting formulations of morphine</a> are sold under the brand names <b>MS Contin</b> and <b>Kadian</b>, among others. Generic long-acting formulations are also available.<sup id="cite_ref-AHFS2015_12-5" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> </p><p>Common side effects of morphine include <a href="/wiki/Drowsiness" class="mw-redirect" title="Drowsiness">drowsiness</a>, <a href="/wiki/Euphoria" title="Euphoria">euphoria</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, <a href="/wiki/Sweating" class="mw-redirect" title="Sweating">sweating</a>, and <a href="/wiki/Constipation" title="Constipation">constipation</a>.<sup id="cite_ref-AHFS2015_12-6" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> Potentially serious <a href="/wiki/Side_effects" class="mw-redirect" title="Side effects">side effects</a> of morphine include <a href="/wiki/Hypoventilation" title="Hypoventilation">decreased respiratory effort</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, and <a href="/wiki/Low_blood_pressure" class="mw-redirect" title="Low blood pressure">low blood pressure</a>.<sup id="cite_ref-AHFS2015_12-7" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> Morphine is highly <a href="/wiki/Addiction" title="Addiction">addictive</a> and prone to <a href="/wiki/Substance_abuse" title="Substance abuse">abuse</a>.<sup id="cite_ref-AHFS2015_12-8" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> If one's dose is reduced after long-term use, <a href="/wiki/Opioid_withdrawal" title="Opioid withdrawal">opioid withdrawal</a> symptoms may occur.<sup id="cite_ref-AHFS2015_12-9" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> Caution is advised for the use of morphine during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> or <a href="/wiki/Breastfeeding" title="Breastfeeding">breastfeeding</a>, as it may affect the health of the baby.<sup id="cite_ref-AHFS2015_12-10" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Drugs.com_pregnancy_2-1" class="reference"><a href="#cite_note-Drugs.com_pregnancy-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> </p><p>Morphine was first isolated in 1804 by German pharmacist <a href="/wiki/Friedrich_Sert%C3%BCrner" title="Friedrich Sertürner">Friedrich Sertürner</a>.<sup id="cite_ref-pmid18443637_16-0" class="reference"><a href="#cite_note-pmid18443637-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Court2009_17-0" class="reference"><a href="#cite_note-Court2009-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> This is believed to be the first isolation of a medicinal alkaloid from a plant.<sup id="cite_ref-Luch2009_18-0" class="reference"><a href="#cite_note-Luch2009-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Merck_Group" title="Merck Group">Merck</a> began marketing it commercially in 1827.<sup id="cite_ref-Court2009_17-1" class="reference"><a href="#cite_note-Court2009-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> Morphine was more widely used after the invention of the <a href="/wiki/Hypodermic_syringe" class="mw-redirect" title="Hypodermic syringe">hypodermic syringe</a> in 1853–1855.<sup id="cite_ref-Court2009_17-2" class="reference"><a href="#cite_note-Court2009-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Clay2013_19-0" class="reference"><a href="#cite_note-Clay2013-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup> Sertürner originally named the substance <i>morphium</i>, after the Greek god of dreams, <a href="/wiki/Morpheus_(mythology)" class="mw-redirect" title="Morpheus (mythology)">Morpheus</a>, as it has a tendency to cause sleep.<sup id="cite_ref-Clay2013_19-1" class="reference"><a href="#cite_note-Clay2013-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup> </p><p>The primary source of morphine is isolation from <a href="/wiki/Poppy_straw" title="Poppy straw">poppy straw</a> of the <a href="/wiki/Papaver_somniferum" title="Papaver somniferum">opium poppy</a>.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup> In 2013, approximately 523 tons of morphine were produced.<sup id="cite_ref-UN2015_22-0" class="reference"><a href="#cite_note-UN2015-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup> Approximately 45 tons were used directly for pain, an increase of 400% over the last twenty years.<sup id="cite_ref-UN2015_22-1" class="reference"><a href="#cite_note-UN2015-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup> Most use for this purpose was in the <a href="/wiki/Developed_world" class="mw-redirect" title="Developed world">developed world</a>.<sup id="cite_ref-UN2015_22-2" class="reference"><a href="#cite_note-UN2015-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup> About 70% of morphine is used to make other <a href="/wiki/Opioids" class="mw-redirect" title="Opioids">opioids</a> such as <a href="/wiki/Hydromorphone" title="Hydromorphone">hydromorphone</a>, <a href="/wiki/Oxymorphone" title="Oxymorphone">oxymorphone</a>, and <a href="/wiki/Heroin" title="Heroin">heroin</a>.<sup id="cite_ref-UN2015_22-3" class="reference"><a href="#cite_note-UN2015-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Trig2006_23-0" class="reference"><a href="#cite_note-Trig2006-23"><span class="cite-bracket">&#91;</span>23<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Kar2006_24-0" class="reference"><a href="#cite_note-Kar2006-24"><span class="cite-bracket">&#91;</span>24<span class="cite-bracket">&#93;</span></a></sup> It is a <a href="/wiki/List_of_Schedule_II_drugs_(US)" class="mw-redirect" title="List of Schedule II drugs (US)">Schedule II drug</a> in the United States,<sup id="cite_ref-Trig2006_23-1" class="reference"><a href="#cite_note-Trig2006-23"><span class="cite-bracket">&#91;</span>23<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Class_A_drug" class="mw-redirect" title="Class A drug">Class A</a> in the United Kingdom,<sup id="cite_ref-Black&#39;s_5-1" class="reference"><a href="#cite_note-Black&#39;s-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> and <a href="/wiki/Controlled_Drugs_and_Substances_Act" title="Controlled Drugs and Substances Act">Schedule I</a> in Canada.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">&#91;</span>25<span class="cite-bracket">&#93;</span></a></sup> It is on the <a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">World Health Organization's List of Essential Medicines</a>.<sup id="cite_ref-WHO22nd_26-0" class="reference"><a href="#cite_note-WHO22nd-26"><span class="cite-bracket">&#91;</span>26<span class="cite-bracket">&#93;</span></a></sup> In 2022, it was the 139th most commonly prescribed medication in the United States, with more than 4<span class="nowrap">&#160;</span>million prescriptions.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">&#91;</span>27<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">&#91;</span>28<span class="cite-bracket">&#93;</span></a></sup> It is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a>.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">&#91;</span>29<span class="cite-bracket">&#93;</span></a></sup> </p> <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><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pain">Pain</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=2" title="Edit section: Pain"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Morphine is used primarily to treat both acute and <a href="/wiki/Chronic_pain" title="Chronic pain">chronic</a> severe <a href="/wiki/Pain" title="Pain">pain</a>. Its duration of analgesia is about three to seven hours.<sup id="cite_ref-AHFS2015_12-11" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Rockwood2009_13-2" class="reference"><a href="#cite_note-Rockwood2009-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup> Side effects of nausea and constipation are rarely severe enough to warrant stopping treatment. </p><p>It is used for pain due to <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a> and for labor pains.<sup id="cite_ref-AHFS2015_12-12" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> However, concerns exist that morphine may increase mortality in the event of <a href="/wiki/Non_ST_elevation_myocardial_infarction" class="mw-redirect" title="Non ST elevation myocardial infarction">non ST elevation myocardial infarction</a>.<sup id="cite_ref-pmid15976786_30-0" class="reference"><a href="#cite_note-pmid15976786-30"><span class="cite-bracket">&#91;</span>30<span class="cite-bracket">&#93;</span></a></sup> </p><p>Morphine has also traditionally been used in the treatment of <a href="/wiki/Acute_pulmonary_edema" class="mw-redirect" title="Acute pulmonary edema">acute pulmonary edema</a>.<sup id="cite_ref-AHFS2015_12-13" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> However, a 2006 review found little evidence to support this practice.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">&#91;</span>31<span class="cite-bracket">&#93;</span></a></sup> </p><p>A 2016 Cochrane review concluded that morphine is effective in relieving <a href="/wiki/Cancer_pain" title="Cancer pain">cancer pain</a>.<sup id="cite_ref-Wiffen_2016_32-0" class="reference"><a href="#cite_note-Wiffen_2016-32"><span class="cite-bracket">&#91;</span>32<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Shortness_of_breath">Shortness of breath</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=3" title="Edit section: Shortness of breath"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Morphine is beneficial in reducing the symptom of <a href="/wiki/Shortness_of_breath" title="Shortness of breath">shortness of breath</a> due to both <a href="/wiki/Cancer" title="Cancer">cancer</a> and non-cancer causes.<sup id="cite_ref-Pal2010_33-0" class="reference"><a href="#cite_note-Pal2010-33"><span class="cite-bracket">&#91;</span>33<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">&#91;</span>34<span class="cite-bracket">&#93;</span></a></sup> In the setting of breathlessness at rest or on minimal exertion from conditions such as advanced cancer or end-stage cardiorespiratory diseases, regular, low-dose sustained-release morphine significantly reduces breathlessness safely, with its benefits maintained over time.<sup id="cite_ref-pmid22336677_35-0" class="reference"><a href="#cite_note-pmid22336677-35"><span class="cite-bracket">&#91;</span>35<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid20202949_36-0" class="reference"><a href="#cite_note-pmid20202949-36"><span class="cite-bracket">&#91;</span>36<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Opioid_use_disorder">Opioid use disorder</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=4" title="Edit section: Opioid use disorder"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Morphine is also available as a slow-release formulation for <a href="/wiki/Opiate_substitution_therapy" class="mw-redirect" title="Opiate substitution therapy">opiate substitution therapy</a> (OST) in Austria, Germany, Bulgaria, Slovenia, and Canada for persons with <a href="/wiki/Opioid_addiction" class="mw-redirect" title="Opioid addiction">opioid addiction</a> who cannot tolerate either <a href="/wiki/Methadone" title="Methadone">methadone</a> or <a href="/wiki/Buprenorphine" title="Buprenorphine">buprenorphine</a>.<sup id="cite_ref-NEPOD_Report_37-0" class="reference"><a href="#cite_note-NEPOD_Report-37"><span class="cite-bracket">&#91;</span>37<span class="cite-bracket">&#93;</span></a></sup> </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:GT-Capros-Morphinsulfat-2018.jpg" class="mw-file-description" title="Two capsules (5&#160;mg &amp; 10&#160;mg) of morphine sulfate extended-release"><img alt="Two capsules (5&#160;mg &amp; 10&#160;mg) of morphine sulfate extended-release" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/GT-Capros-Morphinsulfat-2018.jpg/120px-GT-Capros-Morphinsulfat-2018.jpg" decoding="async" width="120" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/GT-Capros-Morphinsulfat-2018.jpg/180px-GT-Capros-Morphinsulfat-2018.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a8/GT-Capros-Morphinsulfat-2018.jpg/240px-GT-Capros-Morphinsulfat-2018.jpg 2x" data-file-width="2343" data-file-height="1823" /></a></span></div> <div class="gallerytext">Two capsules (5&#160;mg &amp; 10&#160;mg) of morphine sulfate extended-release</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Morphine_1mL_Vial.jpg" class="mw-file-description" title="1 milliliter ampoule containing 10&#160;mg of morphine"><img alt="1 milliliter ampoule containing 10&#160;mg of morphine" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Morphine_1mL_Vial.jpg/80px-Morphine_1mL_Vial.jpg" decoding="async" width="80" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Morphine_1mL_Vial.jpg/121px-Morphine_1mL_Vial.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/32/Morphine_1mL_Vial.jpg/161px-Morphine_1mL_Vial.jpg 2x" data-file-width="976" data-file-height="1454" /></a></span></div> <div class="gallerytext">1 milliliter ampoule containing 10&#160;mg of morphine</div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=5" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Relative <a href="/wiki/Contraindication" title="Contraindication">contraindications</a> to morphine include: </p> <ul><li><a href="/wiki/Hypoventilation" title="Hypoventilation">respiratory depression</a> when appropriate equipment is not available.<sup id="cite_ref-AHFS2015_12-14" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup></li> <li>Although it has previously been thought that morphine was contraindicated in <a href="/wiki/Acute_pancreatitis" title="Acute pancreatitis">acute pancreatitis</a>, a review of the literature shows no evidence for this.<sup id="cite_ref-pmid11316181_38-0" class="reference"><a href="#cite_note-pmid11316181-38"><span class="cite-bracket">&#91;</span>38<span class="cite-bracket">&#93;</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects">Adverse effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=6" title="Edit section: Adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1224211176">.mw-parser-output .quotebox{background-color:#F9F9F9;border:1px solid #aaa;box-sizing:border-box;padding:10px;font-size:88%;max-width:100%}.mw-parser-output .quotebox.floatleft{margin:.5em 1.4em .8em 0}.mw-parser-output .quotebox.floatright{margin:.5em 0 .8em 1.4em}.mw-parser-output .quotebox.centered{overflow:hidden;position:relative;margin:.5em auto .8em auto}.mw-parser-output .quotebox.floatleft span,.mw-parser-output .quotebox.floatright span{font-style:inherit}.mw-parser-output .quotebox>blockquote{margin:0;padding:0;border-left:0;font-family:inherit;font-size:inherit}.mw-parser-output .quotebox-title{text-align:center;font-size:110%;font-weight:bold}.mw-parser-output .quotebox-quote>:first-child{margin-top:0}.mw-parser-output .quotebox-quote:last-child>:last-child{margin-bottom:0}.mw-parser-output .quotebox-quote.quoted:before{font-family:"Times New Roman",serif;font-weight:bold;font-size:large;color:gray;content:" “ ";vertical-align:-45%;line-height:0}.mw-parser-output .quotebox-quote.quoted:after{font-family:"Times New Roman",serif;font-weight:bold;font-size:large;color:gray;content:" ” ";line-height:0}.mw-parser-output .quotebox .left-aligned{text-align:left}.mw-parser-output .quotebox .right-aligned{text-align:right}.mw-parser-output .quotebox .center-aligned{text-align:center}.mw-parser-output .quotebox .quote-title,.mw-parser-output .quotebox .quotebox-quote{display:block}.mw-parser-output .quotebox cite{display:block;font-style:normal}@media screen and (max-width:640px){.mw-parser-output .quotebox{width:100%!important;margin:0 0 .8em!important;float:none!important}}</style><div class="quotebox pullquote floatright" style=";"> <div class="quotebox-title" style="">Adverse effects of opioids</div> <blockquote class="quotebox-quote left-aligned" style=""> <dl><dt>Common and short term</dt></dl> <ul><li><a href="/wiki/Itch" title="Itch">Itchiness</a><sup id="cite_ref-Furlan_39-0" class="reference"><a href="#cite_note-Furlan-39"><span class="cite-bracket">&#91;</span>39<span class="cite-bracket">&#93;</span></a></sup></li> <li><a href="/wiki/Nausea" title="Nausea">Nausea</a><sup id="cite_ref-Furlan_39-1" class="reference"><a href="#cite_note-Furlan-39"><span class="cite-bracket">&#91;</span>39<span class="cite-bracket">&#93;</span></a></sup></li> <li><a href="/wiki/Vomiting" title="Vomiting">Vomiting</a><sup id="cite_ref-Furlan_39-2" class="reference"><a href="#cite_note-Furlan-39"><span class="cite-bracket">&#91;</span>39<span class="cite-bracket">&#93;</span></a></sup></li> <li><a href="/wiki/Constipation" title="Constipation">Constipation</a><sup id="cite_ref-Furlan_39-3" class="reference"><a href="#cite_note-Furlan-39"><span class="cite-bracket">&#91;</span>39<span class="cite-bracket">&#93;</span></a></sup></li> <li><a href="/wiki/Somnolence" title="Somnolence">Drowsiness</a><sup id="cite_ref-Furlan_39-4" class="reference"><a href="#cite_note-Furlan-39"><span class="cite-bracket">&#91;</span>39<span class="cite-bracket">&#93;</span></a></sup></li> <li><a href="/wiki/Xerostomia" title="Xerostomia">Dry mouth</a><sup id="cite_ref-Furlan_39-5" class="reference"><a href="#cite_note-Furlan-39"><span class="cite-bracket">&#91;</span>39<span class="cite-bracket">&#93;</span></a></sup></li> <li><a href="/wiki/Respiratory_depression" class="mw-redirect" title="Respiratory depression">Respiratory depression</a><sup id="cite_ref-AHFS2015_12-15" class="reference"><a href="#cite_note-AHFS2015-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup></li></ul> <dl><dt>Other</dt></dl> <ul><li><a href="/wiki/Opioid_dependence" class="mw-redirect" title="Opioid dependence">Opioid dependence</a></li> <li><a href="/wiki/Dizziness" title="Dizziness">Dizziness</a></li> <li>Decreased sex drive</li> <li><a href="/wiki/Anorexia_(symptom)" title="Anorexia (symptom)">Loss of appetite</a></li> <li>Impaired sexual function</li> <li>Decreased testosterone levels</li> <li><a href="/wiki/Depression_(mood)" title="Depression (mood)">Depression</a></li> <li><a href="/wiki/Immunodeficiency" title="Immunodeficiency">Immunodeficiency</a></li> <li><a href="/wiki/Opioid-induced_hyperalgesia" title="Opioid-induced hyperalgesia">Opioid-induced abnormal pain sensitivity</a></li> <li><a href="/wiki/Irregular_menstruation" title="Irregular menstruation">Irregular menstruation</a></li> <li>Increased risk of <a href="/wiki/Falling_(accident)" title="Falling (accident)">falls</a></li> <li>Slowed breathing</li> <li><a href="/wiki/Hallucinations" class="mw-redirect" title="Hallucinations">Hallucinations</a></li></ul> </blockquote> </div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:MorphineRx.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/MorphineRx.JPG/220px-MorphineRx.JPG" decoding="async" width="220" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/MorphineRx.JPG/330px-MorphineRx.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/MorphineRx.JPG/440px-MorphineRx.JPG 2x" data-file-width="3910" data-file-height="1885" /></a><figcaption>A localized reaction to intravenous morphine caused by histamine release in the veins</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Constipation">Constipation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=7" title="Edit section: Constipation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Like <a href="/wiki/Loperamide" title="Loperamide">loperamide</a> and other opioids, morphine acts on the <a href="/wiki/Myenteric_plexus" title="Myenteric plexus">myenteric plexus</a> in the intestinal tract, reducing gut motility, and causing constipation. The gastrointestinal effects of morphine are mediated primarily by <a href="/wiki/Mu_Opioid_receptor" class="mw-redirect" title="Mu Opioid receptor">μ-opioid receptors</a> in the bowel. By inhibiting gastric emptying and reducing propulsive <a href="/wiki/Peristalsis" title="Peristalsis">peristalsis</a> of the intestine, morphine decreases the rate of intestinal transit. Reduction in gut secretion and increased intestinal fluid absorption also contribute to the constipating effect. Opioids also may act on the gut indirectly through tonic gut spasms after inhibition of <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> generation.<sup id="cite_ref-pmid15082884_40-0" class="reference"><a href="#cite_note-pmid15082884-40"><span class="cite-bracket">&#91;</span>40<span class="cite-bracket">&#93;</span></a></sup> This effect was shown in animals when a nitric oxide precursor, <a href="/wiki/L-arginine" class="mw-redirect" title="L-arginine">L-arginine</a>, reversed morphine-induced changes in gut motility.<sup id="cite_ref-Calignano,_Moncada_and_Di_Rosa_41-0" class="reference"><a href="#cite_note-Calignano,_Moncada_and_Di_Rosa-41"><span class="cite-bracket">&#91;</span>41<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Hormone_imbalance">Hormone imbalance</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=8" title="Edit section: Hormone imbalance"><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">See also: <a href="/wiki/Opioid#Hormone_imbalance" title="Opioid">Opioid §&#160;Hormone imbalance</a></div> <p>Clinical studies consistently conclude that morphine, like other opioids, often causes <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a> and <a href="/wiki/Hormone_imbalance" class="mw-redirect" title="Hormone imbalance">hormone imbalances</a> in chronic users of both sexes. This side effect is <a href="/wiki/Dose%E2%80%93response_relationship" title="Dose–response relationship">dose-dependent</a> and occurs in both therapeutic and recreational users. Morphine can interfere with menstruation by suppressing levels of <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a>. Many studies suggest the majority (perhaps as many as 90%) of chronic opioid users have opioid-induced hypogonadism. This effect may cause the increased likelihood of <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a> and <a href="/wiki/Bone_fracture" title="Bone fracture">bone fracture</a> observed in chronic morphine users. Studies suggest the effect is temporary. As of 2013<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Morphine&amp;action=edit">&#91;update&#93;</a></sup>, the effect of low-dose or acute use of morphine on the endocrine system is unclear.<sup id="cite_ref-pmid23414717_42-0" class="reference"><a href="#cite_note-pmid23414717-42"><span class="cite-bracket">&#91;</span>42<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid19193821_43-0" class="reference"><a href="#cite_note-pmid19193821-43"><span class="cite-bracket">&#91;</span>43<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Effects_on_human_performance">Effects on human performance</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=9" title="Edit section: Effects on human performance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most reviews conclude that opioids produce minimal impairment of human performance on tests of sensory, motor, or attentional abilities. However, recent studies have been able to show some impairments caused by morphine, which is not surprising, given that morphine is a <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> <a href="/wiki/Depressant" title="Depressant">depressant</a>. Morphine has resulted in impaired functioning on critical flicker frequency (a measure of overall CNS arousal) and impaired performance on the <a href="/wiki/Maddox_wing" title="Maddox wing">Maddox wing</a> test (a measure of the deviation of the visual axes of the eyes). Few studies have investigated the effects of morphine on motor abilities; a high dose of morphine can impair finger tapping and the ability to maintain a low constant level of <a href="/wiki/Isometric_exercise" title="Isometric exercise">isometric force</a> (i.e. fine motor control is impaired),<sup id="cite_ref-pmid1755931_44-0" class="reference"><a href="#cite_note-pmid1755931-44"><span class="cite-bracket">&#91;</span>44<span class="cite-bracket">&#93;</span></a></sup> though no studies have shown a correlation between morphine and gross motor abilities. </p><p>In terms of <a href="/wiki/Cognitive" class="mw-redirect" title="Cognitive">cognitive</a> abilities, one study has shown that morphine may negatively impact <a href="/wiki/Anterograde_amnesia" title="Anterograde amnesia">anterograde</a> and <a href="/wiki/Retrograde_amnesia" title="Retrograde amnesia">retrograde memory</a>,<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">&#91;</span>45<span class="cite-bracket">&#93;</span></a></sup> but these effects are minimal and transient. Overall, it seems that acute doses of opioids in non-tolerant subjects produce minor effects in some sensory and motor abilities, and perhaps also in <a href="/wiki/Attention" title="Attention">attention</a> and cognition. The effects of morphine will likely be more pronounced in opioid-naive subjects than in chronic opioid users. </p><p>In chronic opioid users, such as those on Chronic Opioid Analgesic Therapy (COAT) for managing severe, <a href="/wiki/Chronic_pain" title="Chronic pain">chronic pain</a>, behavioural testing has shown normal functioning on perception, cognition, coordination, and behaviour in most cases. One 2000 study<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">&#91;</span>46<span class="cite-bracket">&#93;</span></a></sup> analysed COAT patients to determine whether they were able to safely operate a motor vehicle. The findings from this study suggest that stable opioid use does not significantly impair abilities inherent in driving (this includes physical, cognitive, and perceptual skills). COAT patients showed rapid completion of tasks that require the speed of responding for successful performance (e.g., <a href="/wiki/Rey_Complex_Figure" class="mw-redirect" title="Rey Complex Figure">Rey Complex Figure</a> Test) but made more errors than controls. COAT patients showed no deficits in visual-spatial perception and organization (as shown in the <a href="/wiki/Wechsler_Adult_Intelligence_Scale" title="Wechsler Adult Intelligence Scale">WAIS-R</a> Block Design Test) but did show impaired immediate and short-term visual memory (as shown on the Rey Complex Figure Test&#160;– Recall). These patients showed no impairments in higher-order cognitive abilities (i.e., planning). COAT patients appeared to have difficulty following instructions and showed a propensity toward impulsive behaviour, yet this did not reach statistical significance. It is important to note that this study reveals that COAT patients have no domain-specific deficits, which supports the notion that chronic opioid use has minor effects on <a href="/wiki/Psychomotor_learning" title="Psychomotor learning">psychomotor</a>, <a href="/wiki/Cognitive" class="mw-redirect" title="Cognitive">cognitive</a>, or <a href="/wiki/Neuropsychological" class="mw-redirect" title="Neuropsychological">neuropsychological</a> functioning. </p> <div class="mw-heading mw-heading3"><h3 id="Reinforcement_disorders">Reinforcement disorders</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=10" title="Edit section: Reinforcement disorders"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Addiction">Addiction</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=11" title="Edit section: Addiction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Santiago_Rusinol_Before_the_Morphine.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Santiago_Rusinol_Before_the_Morphine.jpg/220px-Santiago_Rusinol_Before_the_Morphine.jpg" decoding="async" width="220" height="176" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Santiago_Rusinol_Before_the_Morphine.jpg/330px-Santiago_Rusinol_Before_the_Morphine.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Santiago_Rusinol_Before_the_Morphine.jpg/440px-Santiago_Rusinol_Before_the_Morphine.jpg 2x" data-file-width="800" data-file-height="639" /></a><figcaption><i>Before the Morphine</i> by <a href="/wiki/Santiago_Rusi%C3%B1ol" title="Santiago Rusiñol">Santiago Rusiñol</a></figcaption></figure> <p>Morphine is a highly <a href="/wiki/Addictive" class="mw-redirect" title="Addictive">addictive</a> substance. Numerous studies, including one by <i>The Lancet</i>, ranked morphine/heroin as the #1 most addictive substance, followed by <a href="/wiki/Cocaine" title="Cocaine">cocaine</a> at #2, <a href="/wiki/Nicotine" title="Nicotine">nicotine</a> #3, <a href="/wiki/Barbiturates" class="mw-redirect" title="Barbiturates">barbiturates</a> at #4, and <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> at #5. In controlled studies comparing the physiological and subjective effects of <a href="/wiki/Heroin" title="Heroin">heroin</a> and morphine in individuals formerly addicted to opiates, subjects showed no preference for one drug over the other. Equipotent, injected doses had comparable action courses, with heroin crossing the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> slightly quicker. No difference in subjects' self-rated feelings of <a href="/wiki/Euphoria" title="Euphoria">euphoria</a>, ambition, nervousness, relaxation, or drowsiness.<sup id="cite_ref-martin_and_fraser_47-0" class="reference"><a href="#cite_note-martin_and_fraser-47"><span class="cite-bracket">&#91;</span>47<span class="cite-bracket">&#93;</span></a></sup> Short-term addiction studies by the same researchers demonstrated that tolerance developed at a similar rate to both heroin and morphine. When compared to the opioids <a href="/wiki/Hydromorphone" title="Hydromorphone">hydromorphone</a>, <a href="/wiki/Fentanyl" title="Fentanyl">fentanyl</a>, <a href="/wiki/Oxycodone" title="Oxycodone">oxycodone</a>, and <a href="/wiki/Pethidine" title="Pethidine">pethidine</a>, former addicts showed a strong preference for heroin and morphine, suggesting that heroin and morphine are particularly susceptible to abuse and addiction. Morphine and heroin also produced higher rates of euphoria and other positive subjective effects when compared to these other opioids.<sup id="cite_ref-martin_and_fraser_47-1" class="reference"><a href="#cite_note-martin_and_fraser-47"><span class="cite-bracket">&#91;</span>47<span class="cite-bracket">&#93;</span></a></sup> The choice of heroin and morphine over other opioids by former drug addicts may also be because heroin is an ester of morphine and morphine <a href="/wiki/Prodrug" title="Prodrug">prodrug</a>, essentially meaning they are identical drugs <i>in vivo</i>. Heroin is converted to morphine before binding to the <a href="/wiki/Opioid_receptor" title="Opioid receptor">opioid receptors</a> in the brain and spinal cord, where morphine causes subjective effects, which is what the addicted individuals are seeking.<sup id="cite_ref-NIDA-2013_48-0" class="reference"><a href="#cite_note-NIDA-2013-48"><span class="cite-bracket">&#91;</span>48<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Tolerance">Tolerance</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=12" title="Edit section: Tolerance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several hypotheses are given about how tolerance develops, including opioid receptor <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylation</a> (which would change the receptor conformation), functional decoupling of receptors from <a href="/wiki/G-proteins" class="mw-redirect" title="G-proteins">G-proteins</a> (leading to receptor desensitization),<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">&#91;</span>49<span class="cite-bracket">&#93;</span></a></sup> μ-opioid receptor internalization or receptor down-regulation (reducing the number of available receptors for morphine to act on), and upregulation of the <a href="/wiki/Cyclic_adenosine_monophosphate" title="Cyclic adenosine monophosphate">cAMP</a> pathway (a counterregulatory mechanism to opioid effects) (For a review of these processes, see Koch and Hollt<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">&#91;</span>50<span class="cite-bracket">&#93;</span></a></sup>). </p> <div class="mw-heading mw-heading4"><h4 id="Dependence_and_withdrawal">Dependence and withdrawal</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=13" title="Edit section: Dependence and withdrawal"><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">See also: <a href="/wiki/Opioid_use_disorder" title="Opioid use disorder">Opioid use disorder</a> and <a href="/wiki/Opioid_withdrawal" title="Opioid withdrawal">Opioid withdrawal</a></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output 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.mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-More_citations_needed plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Morphine" title="Special:EditPage/Morphine">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a>&#32;in this section. Unsourced material may be challenged and removed.<br /><small><span class="plainlinks"><i>Find sources:</i>&#160;<a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&amp;q=%22Morphine%22">"Morphine"</a>&#160;–&#160;<a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&amp;q=%22Morphine%22+-wikipedia&amp;tbs=ar:1">news</a>&#160;<b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&amp;q=%22Morphine%22&amp;tbs=bkt:s&amp;tbm=bks">newspapers</a>&#160;<b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&amp;q=%22Morphine%22+-wikipedia">books</a>&#160;<b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Morphine%22">scholar</a>&#160;<b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Morphine%22&amp;acc=on&amp;wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">November 2019</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <p>Cessation of dosing with morphine creates the prototypical opioid withdrawal syndrome, which, unlike that of <a href="/wiki/Barbiturates" class="mw-redirect" title="Barbiturates">barbiturates</a>, <a href="/wiki/Benzodiazepines" class="mw-redirect" title="Benzodiazepines">benzodiazepines</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">alcohol</a>, or <a href="/wiki/Sedative" title="Sedative">sedative</a>-hypnotics, is not fatal by itself in otherwise healthy people. </p><p>Acute morphine withdrawal, along with that of any other opioid, proceeds through a number of stages. Other opioids differ in the intensity and length of each, and weak opioids and mixed agonist-antagonists may have acute withdrawal syndromes that do not reach the highest level. As commonly cited<sup class="noprint Inline-Template" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Manual_of_Style/Words_to_watch#Unsupported_attributions" title="Wikipedia:Manual of Style/Words to watch"><span title="The material near this tag may use weasel words or too-vague attribution. (November 2010)">by whom?</span></a></i>&#93;</sup>, they are: </p> <ul><li><b>Stage I</b>, 6&#160;h to 14&#160;h after last dose: Drug craving, anxiety, irritability, perspiration, and mild to moderate <a href="/wiki/Dysphoria" title="Dysphoria">dysphoria</a></li> <li><b>Stage II</b>, 14&#160;h to 18&#160;h after last dose: <a href="/wiki/Yawn" title="Yawn">Yawning</a>, heavy <a href="/wiki/Perspiration" title="Perspiration">perspiration</a>, mild <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>, <a href="/wiki/Lacrimation" class="mw-redirect" title="Lacrimation">lacrimation</a>, <a href="/wiki/Crying" title="Crying">crying</a>, headaches, runny nose, dysphoria, also intensification of the above symptoms, "yen sleep" (a waking trance-like state)</li> <li><b>Stage III</b>, 16&#160;h to 24&#160;h after last dose: Increase in all of the above, <a href="/wiki/Mydriasis" title="Mydriasis">dilated pupils</a>, <a href="/wiki/Goose_bumps" title="Goose bumps">piloerection</a> (goose bumps),<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">&#91;</span>51<span class="cite-bracket">&#93;</span></a></sup> muscle twitches, <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>, cold flashes, aching bones and muscles, <a href="/wiki/Anorexia_(symptom)" title="Anorexia (symptom)">loss of appetite</a>, and the beginning of intestinal cramping</li> <li><b>Stage IV</b>, 24&#160;h to 36&#160;h after last dose: Increase in all of the above including severe cramping, <a href="/wiki/Restless_leg_syndrome" class="mw-redirect" title="Restless leg syndrome">restless legs syndrome</a> (RLS), loose stool, <a href="/wiki/Insomnia" title="Insomnia">insomnia</a>, elevation of blood pressure, <a href="/wiki/Fever" title="Fever">fever</a>, increase in frequency of breathing and tidal volume, <a href="/wiki/Tachycardia" title="Tachycardia">tachycardia</a> (elevated pulse), <a href="/wiki/Psychomotor_agitation" title="Psychomotor agitation">restlessness</a>, nausea</li> <li><b>Stage V</b>, 36&#160;h to 72&#160;h after last dose: Increase in all of the above, fetal position, vomiting, free and frequent liquid diarrhea, weight loss of 2&#160;kg to 5&#160;kg per 24&#160;h, increased <a href="/wiki/White_blood_cell" title="White blood cell">white cell count</a>, and other blood changes</li> <li><b>Stage VI</b>, after completion of above: Recovery of appetite and normal bowel function, beginning of transition to <a href="/wiki/Post-acute-withdrawal_syndrome" title="Post-acute-withdrawal syndrome">post-acute withdrawal symptoms</a> that are mainly psychological, but may also include increased sensitivity to pain, <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, <a href="/wiki/Colitis" title="Colitis">colitis</a> or other gastrointestinal afflictions related to motility, and problems with weight control in either direction</li></ul> <p>In advanced stages of withdrawal, ultrasonographic evidence of pancreatitis has been demonstrated in some patients and is presumably attributed to spasm of the pancreatic <a href="/wiki/Sphincter_of_Oddi" title="Sphincter of Oddi">sphincter of Oddi</a>.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">&#91;</span>52<span class="cite-bracket">&#93;</span></a></sup> </p><p>The withdrawal symptoms associated with morphine addiction are usually experienced shortly before the time of the next scheduled dose, sometimes within as early as a few hours (usually 6&#160;h to 12&#160;h) after the last administration. Early symptoms include watery eyes, insomnia, diarrhea, runny nose, yawning, <a href="/wiki/Dysphoria" title="Dysphoria">dysphoria</a>, sweating, and, in some cases, a strong drug craving. Severe headache, restlessness, <a href="/wiki/Irritability" title="Irritability">irritability</a>, loss of appetite, body aches, severe abdominal pain, nausea and vomiting, tremors, and even stronger and more intense drug craving appear as the syndrome progresses. Severe depression and vomiting are very common. During the acute withdrawal period, systolic and diastolic blood pressures increase, usually beyond premorphine levels, and heart rate increases,<sup id="cite_ref-Chan,_Irvine,_and_White_53-0" class="reference"><a href="#cite_note-Chan,_Irvine,_and_White-53"><span class="cite-bracket">&#91;</span>53<span class="cite-bracket">&#93;</span></a></sup> which have potential to cause a heart attack, blood clot, or stroke. </p><p>Chills or cold flashes with goose bumps alternating with flushing (hot flashes), kicking movements of the legs,<sup id="cite_ref-NIDA-2013_48-1" class="reference"><a href="#cite_note-NIDA-2013-48"><span class="cite-bracket">&#91;</span>48<span class="cite-bracket">&#93;</span></a></sup> and excessive sweating are also characteristic symptoms.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">&#91;</span>54<span class="cite-bracket">&#93;</span></a></sup> Severe pains in the bones and muscles of the back and extremities occur, as do muscle spasms. At any point during this process, a suitable narcotic can be administered that will dramatically reverse the withdrawal symptoms. Major withdrawal symptoms peak between 48&#160;h and 96&#160;h after the last dose and subside after about 8 to 12 days. Sudden discontinuation of morphine by heavily <a href="/wiki/Drug_dependence" class="mw-redirect" title="Drug dependence">dependent</a> users who are in poor health is very rarely fatal. Morphine withdrawal is considered less dangerous than alcohol, barbiturate, or benzodiazepine withdrawal.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">&#91;</span>55<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">&#91;</span>56<span class="cite-bracket">&#93;</span></a></sup> </p><p>The psychological dependence associated with morphine <a href="/wiki/Substance_use_disorder" title="Substance use disorder">addiction</a> is complex and protracted. Long after the physical need for morphine has passed, addicts will usually continue to think and talk about the use of morphine (or other drugs) and feel strange or overwhelmed coping with daily activities without being under the influence of morphine. Psychological withdrawal from morphine is usually a very long and painful process. Addicts often experience severe depression, anxiety, insomnia, mood swings, forgetfulness, low <a href="/wiki/Self-esteem" title="Self-esteem">self-esteem</a>, <a href="/wiki/Confusion" title="Confusion">confusion</a>, <a href="/wiki/Paranoia" title="Paranoia">paranoia</a>, and other psychological problems. Without intervention, the syndrome will run its course, and most of the overt physical symptoms will disappear within 7 to 10 days including psychological dependence. A high probability of relapse exists after morphine withdrawal when neither the physical environment nor the behavioral motivators that contributed to the abuse have been altered. Testimony of morphine's addictive and reinforcing nature is its relapse rate. Users of morphine have one of the highest relapse rates among all drug users, ranging up to 98% in the estimation of some medical experts.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">&#91;</span>57<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=14" title="Edit section: Toxicity"><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">See also: <a href="/wiki/Opioid_overdose" title="Opioid overdose">Opioid overdose</a></div> <table border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; float: right; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"> <tbody><tr> <th style="background: #F8EABA; text-align: center;" colspan="2">Properties of Morphine </th></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a><sup id="cite_ref-CRC_85_58-0" class="reference"><a href="#cite_note-CRC_85-58"><span class="cite-bracket">&#91;</span>58<span class="cite-bracket">&#93;</span></a></sup> </td> <td>285.338 g/mol </td></tr> <tr> <td><a href="/wiki/Acidity" class="mw-redirect" title="Acidity">Acidity</a> (p<i>K</i><sub>a</sub>)<sup id="cite_ref-CRC_85_58-1" class="reference"><a href="#cite_note-CRC_85-58"><span class="cite-bracket">&#91;</span>58<span class="cite-bracket">&#93;</span></a></sup> </td> <td> <table> <tbody><tr> <td>Step 1: 8.21</td> <td>at 25&#160;°C </td></tr> <tr> <td>Step 2: 9.85</td> <td>at 20&#160;°C </td></tr></tbody></table> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a><sup id="cite_ref-CRC_85_58-2" class="reference"><a href="#cite_note-CRC_85-58"><span class="cite-bracket">&#91;</span>58<span class="cite-bracket">&#93;</span></a></sup> </td> <td>0.15 g/L at 20&#160;°C </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a><sup id="cite_ref-CRC_85_58-3" class="reference"><a href="#cite_note-CRC_85-58"><span class="cite-bracket">&#91;</span>58<span class="cite-bracket">&#93;</span></a></sup> </td> <td>255&#160;°C </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a><sup id="cite_ref-CRC_85_58-4" class="reference"><a href="#cite_note-CRC_85-58"><span class="cite-bracket">&#91;</span>58<span class="cite-bracket">&#93;</span></a></sup> </td> <td>190&#160;°C sublimes </td></tr> </tbody></table> <p>A large <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a> can cause <a href="/wiki/Asphyxia" title="Asphyxia">asphyxia</a> and death by respiratory depression if the person does not receive medical attention immediately.<sup id="cite_ref-Duldner_59-0" class="reference"><a href="#cite_note-Duldner-59"><span class="cite-bracket">&#91;</span>59<span class="cite-bracket">&#93;</span></a></sup> Overdose treatment includes the administration of <a href="/wiki/Naloxone" title="Naloxone">naloxone</a>. The latter completely reverses morphine's effects but may result in the immediate onset of withdrawal in opiate-addicted subjects. Multiple doses may be needed as the duration of action of morphine is longer than that of naloxone.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">&#91;</span>60<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=15" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=16" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable floatright" style="text-align: center;"> <caption>Morphine at opioid receptors </caption> <tbody><tr> <th rowspan="2">Compound</th> <th colspan="3"><a href="/wiki/Binding_affinity" class="mw-redirect" title="Binding affinity">Affinities</a> (<a href="/wiki/Inhibitor_constant" class="mw-redirect" title="Inhibitor constant"><abbr title="Inhibitor constant">K<sub>i</sub></abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Inhibitor constant</span>)</th> <th>Ratio</th> <th rowspan="2">Ref </th></tr> <tr> <th><a href="/wiki/%CE%9C-Opioid_receptor" class="mw-redirect" title="Μ-Opioid receptor"><abbr title="μ-Opioid receptor">MOR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip μ-Opioid receptor</span></th> <th><a href="/wiki/%CE%94-Opioid_receptor" class="mw-redirect" title="Δ-Opioid receptor"><abbr title="δ-Opioid receptor">DOR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip δ-Opioid receptor</span></th> <th><a href="/wiki/%CE%9A-Opioid_receptor" class="mw-redirect" title="Κ-Opioid receptor"><abbr title="κ-Opioid receptor">KOR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip κ-Opioid receptor</span></th> <th>MOR:DOR:KOR </th></tr> <tr> <td>Morphine</td> <td>1.8 nM</td> <td>90 nM</td> <td>317 nM</td> <td>1:50:176</td> <td><sup id="cite_ref-CorbettPaterson1993_61-0" class="reference"><a href="#cite_note-CorbettPaterson1993-61"><span class="cite-bracket">&#91;</span>61<span class="cite-bracket">&#93;</span></a></sup> </td></tr> <tr> <td>(−)-Morphine</td> <td>1.24 nM</td> <td>145 nM</td> <td>23.4 nM</td> <td>1:117:19</td> <td><sup id="cite_ref-pmid7562497_62-0" class="reference"><a href="#cite_note-pmid7562497-62"><span class="cite-bracket">&#91;</span>62<span class="cite-bracket">&#93;</span></a></sup> </td></tr> <tr> <td>(+)-Morphine</td> <td>&gt;10 μM</td> <td>&gt;100 μM</td> <td>&gt;300 μM</td> <td><abbr title="No data">ND</abbr></td> <td><sup id="cite_ref-pmid7562497_62-1" class="reference"><a href="#cite_note-pmid7562497-62"><span class="cite-bracket">&#91;</span>62<span class="cite-bracket">&#93;</span></a></sup> </td></tr></tbody></table> <table class="wikitable floatright"> <caption><br />Equianalgesic doses<sup id="cite_ref-King2010_63-0" class="reference"><a href="#cite_note-King2010-63"><span class="cite-bracket">&#91;</span>63<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-ChestnutWong2014_64-0" class="reference"><a href="#cite_note-ChestnutWong2014-64"><span class="cite-bracket">&#91;</span>64<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Tiziani2013_65-0" class="reference"><a href="#cite_note-Tiziani2013-65"><span class="cite-bracket">&#91;</span>65<span class="cite-bracket">&#93;</span></a></sup> </caption> <tbody><tr> <th>Compound</th> <th><a href="/wiki/Route_of_administration" title="Route of administration">Route</a></th> <th><a href="/wiki/Dose_(biochemistry)" title="Dose (biochemistry)">Dose</a> </th></tr> <tr> <td><a href="/wiki/Codeine" title="Codeine">Codeine</a></td> <td><abbr title="Oral administration">PO</abbr></td> <td>200&#160;mg </td></tr> <tr> <td><a href="/wiki/Hydrocodone" title="Hydrocodone">Hydrocodone</a></td> <td><abbr title="Oral administration">PO</abbr></td> <td>30&#160;mg </td></tr> <tr> <td><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone</a></td> <td><abbr title="Oral administration">PO</abbr></td> <td>7.5&#160;mg </td></tr> <tr> <td><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone</a></td> <td><abbr title="Intravenous administration">IV</abbr></td> <td>2&#160;mg </td></tr> <tr> <td>Morphine</td> <td><abbr title="Oral administration">PO</abbr></td> <td>30&#160;mg </td></tr> <tr> <td>Morphine</td> <td><abbr title="Intravenous administration">IV</abbr></td> <td>10&#160;mg </td></tr> <tr> <td><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a></td> <td><abbr title="Oral administration">PO</abbr></td> <td>20&#160;mg </td></tr> <tr> <td><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a></td> <td><abbr title="Intravenous administration">IV</abbr></td> <td>20&#160;mg </td></tr> <tr> <td><a href="/wiki/Oxymorphone" title="Oxymorphone">Oxymorphone</a></td> <td><abbr title="Oral administration">PO</abbr></td> <td>10&#160;mg </td></tr> <tr> <td><a href="/wiki/Oxymorphone" title="Oxymorphone">Oxymorphone</a></td> <td><abbr title="Intravenous administration">IV</abbr></td> <td>1&#160;mg </td></tr></tbody></table> <p>Due to its long history and established use as a pain medication, this compound has become the benchmark to which all other opioids are compared.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">&#91;</span>66<span class="cite-bracket">&#93;</span></a></sup> It interacts predominantly with the μ–δ-opioid (Mu-Delta) <a href="/wiki/GPCR_oligomer" title="GPCR oligomer">receptor heteromer</a>.<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">&#91;</span>67<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">&#91;</span>68<span class="cite-bracket">&#93;</span></a></sup> The μ-binding sites are discretely distributed in the <a href="/wiki/Human_brain" title="Human brain">human brain</a>, with high densities in the posterior <a href="/wiki/Amygdala" title="Amygdala">amygdala</a>, <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a>, <a href="/wiki/Thalamus" title="Thalamus">thalamus</a>, <a href="/wiki/Nucleus_caudatus" class="mw-redirect" title="Nucleus caudatus">nucleus caudatus</a>, <a href="/wiki/Putamen" title="Putamen">putamen</a>, and certain cortical areas. They are also found on the <a href="/wiki/Chemical_synapse" title="Chemical synapse">terminal axons</a> of primary afferents within laminae <a href="/wiki/Posteromarginal_nucleus" class="mw-redirect" title="Posteromarginal nucleus">I</a> and II (<a href="/wiki/Substantia_gelatinosa_of_Rolando" title="Substantia gelatinosa of Rolando">substantia gelatinosa</a>) of the spinal cord and in the spinal nucleus of the <a href="/wiki/Trigeminal_nerve" title="Trigeminal nerve">trigeminal nerve</a>.<sup id="cite_ref-rxlist.com_69-0" class="reference"><a href="#cite_note-rxlist.com-69"><span class="cite-bracket">&#91;</span>69<span class="cite-bracket">&#93;</span></a></sup> </p><p>Morphine is a <a href="/wiki/Phenanthrene" title="Phenanthrene">phenanthrene</a> <a href="/wiki/Opioid_receptor" title="Opioid receptor">opioid receptor</a> <a href="/wiki/Receptor_agonist" class="mw-redirect" title="Receptor agonist">agonist</a>&#160;– its main effect is binding to and activating the <a href="/wiki/%CE%9C-opioid_receptor" title="Μ-opioid receptor">μ-opioid receptor</a> (MOR) in the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>. Its <a href="/wiki/Intrinsic_activity" title="Intrinsic activity">intrinsic activity</a> at the MOR is heavily dependent on the <a href="/wiki/Assay" title="Assay">assay</a> and tissue being tested; in some situations it is a <a href="/wiki/Full_agonist" class="mw-redirect" title="Full agonist">full agonist</a> while in others it can be a <a href="/wiki/Partial_agonist" title="Partial agonist">partial agonist</a> or even <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a>.<sup id="cite_ref-pmid23646826_70-0" class="reference"><a href="#cite_note-pmid23646826-70"><span class="cite-bracket">&#91;</span>70<span class="cite-bracket">&#93;</span></a></sup> In clinical settings, morphine exerts its principal pharmacological effect on the central nervous system and <a href="/wiki/Human_gastrointestinal_tract" class="mw-redirect" title="Human gastrointestinal tract">gastrointestinal tract</a>. Its primary actions of therapeutic value are analgesia and sedation. Activation of the MOR is associated with analgesia, sedation, <a href="/wiki/Euphoria_(emotion)" class="mw-redirect" title="Euphoria (emotion)">euphoria</a>, physical <a href="/wiki/Chemical_dependency" class="mw-redirect" title="Chemical dependency">dependence</a>, and <a href="/wiki/Respiratory_depression" class="mw-redirect" title="Respiratory depression">respiratory depression</a>. Morphine is also a <a href="/wiki/%CE%9A-opioid_receptor" title="Κ-opioid receptor">κ-opioid receptor</a> (KOR) and <a href="/wiki/%CE%94-opioid_receptor" title="Δ-opioid receptor">δ-opioid receptor</a> (DOR) agonist. Activation of the KOR is associated with spinal analgesia, <a href="/wiki/Miosis" title="Miosis">miosis</a> (pinpoint pupils), and <a href="/wiki/Psychotomimetic" class="mw-redirect" title="Psychotomimetic">psychotomimetic</a> effects. The DOR is thought to play a role in analgesia.<sup id="cite_ref-rxlist.com_69-1" class="reference"><a href="#cite_note-rxlist.com-69"><span class="cite-bracket">&#91;</span>69<span class="cite-bracket">&#93;</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability"><span title="The material near this tag failed verification of its source citation(s). (August 2023)">failed verification</span></a></i>&#93;</sup> Although morphine does not bind to the <a href="/wiki/Sigma_receptor" title="Sigma receptor">σ receptor</a>, it has been shown that σ receptor agonists, such as <a href="/wiki/Pentazocine" title="Pentazocine">(+)-pentazocine</a>, inhibit morphine analgesia, and σ receptor antagonists enhance morphine analgesia,<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">&#91;</span>71<span class="cite-bracket">&#93;</span></a></sup> suggesting downstream involvement of the σ receptor in the actions of morphine. </p><p>The effects of morphine can be countered with <a href="/wiki/Opioid_receptor_antagonist" class="mw-redirect" title="Opioid receptor antagonist">opioid receptor antagonists</a> such as <a href="/wiki/Naloxone" title="Naloxone">naloxone</a> and <a href="/wiki/Naltrexone" title="Naltrexone">naltrexone</a>; the development of tolerance to morphine may be inhibited by <a href="/wiki/NMDA_receptor_antagonist" title="NMDA receptor antagonist">NMDA receptor antagonists</a> such as <a href="/wiki/Ketamine" title="Ketamine">ketamine</a>, <a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a>, and <a href="/wiki/Memantine" title="Memantine">memantine</a>.<sup id="cite_ref-pmid8747752_72-0" class="reference"><a href="#cite_note-pmid8747752-72"><span class="cite-bracket">&#91;</span>72<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-73" class="reference"><a href="#cite_note-73"><span class="cite-bracket">&#91;</span>73<span class="cite-bracket">&#93;</span></a></sup> The rotation of morphine with chemically dissimilar opioids in the long-term treatment of pain will slow down the growth of tolerance in the longer run, particularly agents known to have significantly incomplete cross-tolerance with morphine such as <a href="/wiki/Levorphanol" title="Levorphanol">levorphanol</a>, <a href="/wiki/Ketobemidone" title="Ketobemidone">ketobemidone</a>, <a href="/wiki/Piritramide" title="Piritramide">piritramide</a>, and <a href="/wiki/Methadone" title="Methadone">methadone</a> and its derivatives; all of these drugs also have NMDA antagonist properties. It is believed that the strong opioid with the most incomplete cross-tolerance with morphine is either methadone<sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span class="cite-bracket">&#91;</span>74<span class="cite-bracket">&#93;</span></a></sup> or <a href="/wiki/Dextromoramide" title="Dextromoramide">dextromoramide</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (October 2021)">citation needed</span></a></i>&#93;</sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Morphine_Ampoule_For_Veterinary_Use.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Morphine_Ampoule_For_Veterinary_Use.jpg/220px-Morphine_Ampoule_For_Veterinary_Use.jpg" decoding="async" width="220" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Morphine_Ampoule_For_Veterinary_Use.jpg/330px-Morphine_Ampoule_For_Veterinary_Use.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Morphine_Ampoule_For_Veterinary_Use.jpg/440px-Morphine_Ampoule_For_Veterinary_Use.jpg 2x" data-file-width="4284" data-file-height="2718" /></a><figcaption>Morphine <a href="/wiki/Hydrochloride" title="Hydrochloride">hydrochloride</a> ampoule for <a href="/wiki/Veterinary_medicine" title="Veterinary medicine">veterinary use</a></figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Analgesia_creation">Analgesia creation</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=17" title="Edit section: Analgesia creation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Morphine creates analgesia through the activation of a specific group of neurons in the <a href="/wiki/Rostral_ventromedial_medulla" title="Rostral ventromedial medulla">rostral ventromedial medulla</a>, called the "morphine ensemble."<sup id="cite_ref-j866_75-0" class="reference"><a href="#cite_note-j866-75"><span class="cite-bracket">&#91;</span>75<span class="cite-bracket">&#93;</span></a></sup> This ensemble includes glutamatergic neurons that project to the spinal cord, known as RVM<sup>BDNF</sup> neurons. These neurons connect to inhibitory neurons in the spinal cord, called SC<sup>Gal</sup> neurons, which release the neurotransmitter GABA and the neuropeptide <a href="/wiki/Galanin" title="Galanin">galanin</a>. The inhibition of SC<sup>Gal</sup> neurons is crucial for morphine's pain-relieving effects. Additionally, the neurotrophic factor <a href="/wiki/Brain-derived_neurotrophic_factor" title="Brain-derived neurotrophic factor">BDNF</a>, produced within the RVM<sup>BDNF</sup> neurons, is required for morphine's action. Increasing BDNF levels enhances morphine's analgesic effects, even at lower doses.<sup id="cite_ref-v878_76-0" class="reference"><a href="#cite_note-v878-76"><span class="cite-bracket">&#91;</span>76<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-j866_75-1" class="reference"><a href="#cite_note-j866-75"><span class="cite-bracket">&#91;</span>75<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Gene_expression">Gene expression</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=18" title="Edit section: Gene expression"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Studies have shown that morphine can alter the expression of several <a href="/wiki/Genes" class="mw-redirect" title="Genes">genes</a>. A single injection of morphine has been shown to alter the expression of two major groups of genes, for proteins involved in <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondrial</a> respiration and for <a href="/wiki/Cytoskeleton" title="Cytoskeleton">cytoskeleton</a>-related proteins.<sup id="cite_ref-77" class="reference"><a href="#cite_note-77"><span class="cite-bracket">&#91;</span>77<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Effects_on_the_immune_system">Effects on the immune system</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=19" title="Edit section: Effects on the immune system"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Morphine has long been known to act on receptors expressed in cells of the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> resulting in pain relief and <a href="/wiki/Analgesia" class="mw-redirect" title="Analgesia">analgesia</a>. In the 1970s and '80s, evidence suggesting that people addicted to opioids show an increased risk of infection (such as increased <a href="/wiki/Pneumonia" title="Pneumonia">pneumonia</a>, <a href="/wiki/Tuberculosis" title="Tuberculosis">tuberculosis</a>, and <a href="/wiki/HIV/AIDS" title="HIV/AIDS">HIV/AIDS</a>) led scientists to believe that morphine may also affect the <a href="/wiki/Immune_system" title="Immune system">immune system</a>. This possibility increased interest in the effect of chronic morphine use on the immune system.<sup id="cite_ref-78" class="reference"><a href="#cite_note-78"><span class="cite-bracket">&#91;</span>78<span class="cite-bracket">&#93;</span></a></sup> </p><p>The first step in determining that morphine may affect the immune system was to establish that the opiate receptors known to be expressed on cells of the central nervous system are also expressed on cells of the immune system. One study successfully showed that <a href="/wiki/Dendritic_cells" class="mw-redirect" title="Dendritic cells">dendritic cells</a>, part of the innate immune system, display opiate receptors. Dendritic cells are responsible for producing <a href="/wiki/Cytokine" title="Cytokine">cytokines</a>, which are the tools for communication in the immune system. This same study showed that dendritic cells chronically treated with morphine during their differentiation produce more <a href="/wiki/Interleukin-12" class="mw-redirect" title="Interleukin-12">interleukin-12</a> (IL-12), a cytokine responsible for promoting the proliferation, growth, and differentiation of T-cells (another cell of the adaptive immune system) and less <a href="/wiki/Interleukin-10" class="mw-redirect" title="Interleukin-10">interleukin-10</a> (IL-10), a cytokine responsible for promoting a B-cell immune response (B cells produce antibodies to fight off infection).<sup id="cite_ref-messmer_2006_79-0" class="reference"><a href="#cite_note-messmer_2006-79"><span class="cite-bracket">&#91;</span>79<span class="cite-bracket">&#93;</span></a></sup> </p><p>This regulation of cytokines appears to occur via the <a href="/wiki/P38_MAPK_pathway" class="mw-redirect" title="P38 MAPK pathway">p38 MAPKs (mitogen-activated protein kinase)-dependent pathway</a>. Usually, the p38 within the dendritic cell expresses <a href="/wiki/TLR_4" class="mw-redirect" title="TLR 4">TLR 4</a> (toll-like receptor 4), which is activated through the ligand LPS (<a href="/wiki/Lipopolysaccharide" title="Lipopolysaccharide">lipopolysaccharide</a>). This causes the p38 MAPK to be <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylated</a>. This phosphorylation activates the <a href="/wiki/P38_mitogen-activated_protein_kinases" title="P38 mitogen-activated protein kinases">p38 MAPK</a> to begin producing IL-10 and IL-12. When the dendritic cells are chronically exposed to morphine during their differentiation process and then treated with LPS, the production of cytokines is different. Once treated with morphine, the p38 MAPK does not produce IL-10, instead favoring the production of IL-12. The exact mechanism through which the production of one cytokine is increased in favor over another is not known. Most likely, the morphine causes increased phosphorylation of the p38 MAPK. Transcriptional level interactions between IL-10 and IL-12 may further increase the production of IL-12 once IL-10 is not being produced. This increased production of IL-12 causes increased T-cell immune response. </p><p>Further studies on the effects of morphine on the immune system have shown that morphine influences the production of <a href="/wiki/Neutrophils" class="mw-redirect" title="Neutrophils">neutrophils</a> and other <a href="/wiki/Cytokines" class="mw-redirect" title="Cytokines">cytokines</a>. Since cytokines are produced as part of the immediate immunological response (<a href="/wiki/Inflammation" title="Inflammation">inflammation</a>), it has been suggested that they may also influence pain. In this way, cytokines may be a logical target for analgesic development. Recently, one study has used an animal model (hind-paw incision) to observe the effects of morphine administration on the acute immunological response. Following the hind-paw incision, pain thresholds and cytokine production were measured. Normally, cytokine production in and around the wounded area increases to fight <a href="/wiki/Infection" title="Infection">infection</a> and control healing (and, possibly, to control pain), but pre-incisional morphine administration (0.1&#160;mg/kg to 10.0&#160;mg/kg) reduced the number of cytokines found around the wound in a dose-dependent manner. The authors suggest that morphine administration in the acute post-injury period may reduce resistance to infection and may impair the healing of the wound.<sup id="cite_ref-pmid17908329_80-0" class="reference"><a href="#cite_note-pmid17908329-80"><span class="cite-bracket">&#91;</span>80<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=20" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Absorption_and_metabolism">Absorption and metabolism</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=21" title="Edit section: Absorption and metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Morphine can be taken <a href="/wiki/Oral_administration" title="Oral administration">orally</a>, <a href="/wiki/Sublingual_administration" title="Sublingual administration">sublingually</a>, <a href="/wiki/Buccal_space" title="Buccal space">bucally</a>, <a href="/wiki/Rectal_administration" title="Rectal administration">rectally</a>, <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">subcutaneously</a>, <a href="/wiki/Insufflation_(medicine)" title="Insufflation (medicine)">intranasally</a>, <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">intravenously</a>, <a href="/wiki/Intrathecal" class="mw-redirect" title="Intrathecal">intrathecally</a> or <a href="/wiki/Epidural" class="mw-redirect" title="Epidural">epidurally</a> and inhaled via a nebulizer. As a recreational drug, it is becoming more common to inhale ("<a href="/wiki/Chasing_the_Dragon" class="mw-redirect" title="Chasing the Dragon">Chasing the Dragon</a>"), but, for medical purposes, intravenous (IV) injection is the most common method of administration. Morphine is subject to extensive <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first-pass metabolism</a> (a large proportion is broken down in the liver), so, if taken orally, only 40% to 50% of the dose reaches the central nervous system. Resultant plasma levels after subcutaneous (SC), intramuscular (IM), and IV injection are all comparable. After IM or SC injections, morphine plasma levels peak in approximately 20&#160;min, and, after oral administration, levels peak in approximately 30&#160;min.<sup id="cite_ref-81" class="reference"><a href="#cite_note-81"><span class="cite-bracket">&#91;</span>81<span class="cite-bracket">&#93;</span></a></sup> Morphine is <a href="/wiki/Metabolised" class="mw-redirect" title="Metabolised">metabolised</a> primarily in the <a href="/wiki/Liver" title="Liver">liver</a> and approximately 87% of a dose of morphine is excreted in the <a href="/wiki/Urine" title="Urine">urine</a> within 72&#160;h of administration. Morphine is metabolized primarily into <a href="/wiki/Morphine-3-glucuronide" title="Morphine-3-glucuronide">morphine-3-glucuronide</a> (M3G) and <a href="/wiki/Morphine-6-glucuronide" title="Morphine-6-glucuronide">morphine-6-glucuronide</a> (M6G)<sup id="cite_ref-Kilpatrick_2005_82-0" class="reference"><a href="#cite_note-Kilpatrick_2005-82"><span class="cite-bracket">&#91;</span>82<span class="cite-bracket">&#93;</span></a></sup> via <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> by phase II metabolism enzyme <a href="/wiki/UGT2B7" title="UGT2B7">UDP-glucuronosyl transferase-2B7</a> (UGT2B7). About 60% of morphine is converted to M3G, and 6% to 10% is converted to M6G.<sup id="cite_ref-van_Dorp_83-0" class="reference"><a href="#cite_note-van_Dorp-83"><span class="cite-bracket">&#91;</span>83<span class="cite-bracket">&#93;</span></a></sup> Not only does the metabolism occur in the liver but it may also take place in the brain and the kidneys. M3G does not undergo opioid receptor binding and has no analgesic effect. M6G binds to μ-receptors and is half as potent an analgesic as morphine in humans.<sup id="cite_ref-van_Dorp_83-1" class="reference"><a href="#cite_note-van_Dorp-83"><span class="cite-bracket">&#91;</span>83<span class="cite-bracket">&#93;</span></a></sup> Morphine may also be metabolized into small amounts of <a href="/wiki/Normorphine" title="Normorphine">normorphine</a>, <a href="/wiki/Codeine" title="Codeine">codeine</a>, and <a href="/wiki/Hydromorphone" title="Hydromorphone">hydromorphone</a>. Metabolism rate is determined by gender, age, diet, genetic makeup, disease state (if any), and use of other medications. The elimination <a href="/wiki/Half-life" title="Half-life">half-life</a> of morphine is approximately 120&#160;min, though there may be slight differences between men and women. Morphine can be stored in fat, and, thus, can be detectable even after death. Morphine can cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a>, but, because of poor lipid solubility, protein binding, rapid conjugation with glucuronic acid, and ionization, it does not cross easily. <a href="/wiki/Heroin" title="Heroin">Heroin</a>, which is derived from morphine, crosses the blood-brain barrier more easily, making it more potent.<sup id="cite_ref-Jenkins_AJ_2008_84-0" class="reference"><a href="#cite_note-Jenkins_AJ_2008-84"><span class="cite-bracket">&#91;</span>84<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Extended-release">Extended-release</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=22" title="Edit section: Extended-release"><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/Extended-release_morphine" title="Extended-release morphine">Extended-release morphine</a></div> <p>There are <a href="/wiki/Time_release_technology" class="mw-redirect" title="Time release technology">extended-release</a> formulations of orally administered morphine whose effect lasts longer, which can be given once per day. Brand names for this formulation of morphine include Avinza,<sup id="cite_ref-maryland_85-0" class="reference"><a href="#cite_note-maryland-85"><span class="cite-bracket">&#91;</span>85<span class="cite-bracket">&#93;</span></a></sup> Kadian,<sup id="cite_ref-maryland_85-1" class="reference"><a href="#cite_note-maryland-85"><span class="cite-bracket">&#91;</span>85<span class="cite-bracket">&#93;</span></a></sup> MS Contin,<sup id="cite_ref-maryland_85-2" class="reference"><a href="#cite_note-maryland-85"><span class="cite-bracket">&#91;</span>85<span class="cite-bracket">&#93;</span></a></sup> Dolcontin, and DepoDur.<sup id="cite_ref-PedersenFredheim2015_86-0" class="reference"><a href="#cite_note-PedersenFredheim2015-86"><span class="cite-bracket">&#91;</span>86<span class="cite-bracket">&#93;</span></a></sup> For constant pain, the relieving effect of extended-release morphine given once (for Kadian)<sup id="cite_ref-medscape_87-0" class="reference"><a href="#cite_note-medscape-87"><span class="cite-bracket">&#91;</span>87<span class="cite-bracket">&#93;</span></a></sup> or twice (for MS Contin)<sup id="cite_ref-medscape_87-1" class="reference"><a href="#cite_note-medscape-87"><span class="cite-bracket">&#91;</span>87<span class="cite-bracket">&#93;</span></a></sup> every 24 hours is roughly the same as multiple administrations of <i>immediate release</i> (or "regular") morphine.<sup id="cite_ref-northwestern_88-0" class="reference"><a href="#cite_note-northwestern-88"><span class="cite-bracket">&#91;</span>88<span class="cite-bracket">&#93;</span></a></sup> Extended-release morphine can be administered together with "rescue doses" of immediate-release morphine as needed in case of breakthrough pain, each generally consisting of 5% to 15% of the 24-hour extended-release dosage.<sup id="cite_ref-northwestern_88-1" class="reference"><a href="#cite_note-northwestern-88"><span class="cite-bracket">&#91;</span>88<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Detection_in_body_fluids">Detection in body fluids</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=23" title="Edit section: Detection in body fluids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Morphine and its major metabolites, morphine-3-glucuronide, and morphine-6-glucuronide, can be detected in blood, plasma, hair, and urine using an <a href="/wiki/Immunoassay" title="Immunoassay">immunoassay</a>. <a href="/wiki/Chromatography" title="Chromatography">Chromatography</a> can be used to test for each of these substances individually. Some testing procedures <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyze</a> metabolic products into morphine before the immunoassay, which must be considered when comparing morphine levels in separately published results. Morphine can also be isolated from whole blood samples by <a href="/wiki/Solid_phase_extraction" class="mw-redirect" title="Solid phase extraction">solid phase extraction</a> (SPE) and detected using <a href="/wiki/Liquid_chromatography-mass_spectrometry" class="mw-redirect" title="Liquid chromatography-mass spectrometry">liquid chromatography-mass spectrometry</a> (LC-MS). </p><p>Ingestion of codeine or food containing poppy seeds can cause false positives.<sup id="cite_ref-89" class="reference"><a href="#cite_note-89"><span class="cite-bracket">&#91;</span>89<span class="cite-bracket">&#93;</span></a></sup> </p><p>A 1999 review estimated that relatively low doses of heroin (which metabolizes immediately into morphine) are detectable by standard urine tests for 1–1.5 days after use.<sup id="cite_ref-pmid11484423_90-0" class="reference"><a href="#cite_note-pmid11484423-90"><span class="cite-bracket">&#91;</span>90<span class="cite-bracket">&#93;</span></a></sup> A 2009 review determined that, when the <a href="/wiki/Analyte" title="Analyte">analyte</a> is morphine and the <a href="/wiki/Limit_of_detection" class="mw-redirect" title="Limit of detection">limit of detection</a> is 1<span class="nowrap">&#160;</span>ng/ml, a 20<span class="nowrap">&#160;</span>mg intravenous (IV) dose of morphine is detectable for 12–24 hours. A limit of detection of 0.6<span class="nowrap">&#160;</span>ng/ml had similar results.<sup id="cite_ref-pmid15228165_91-0" class="reference"><a href="#cite_note-pmid15228165-91"><span class="cite-bracket">&#91;</span>91<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Chirality_and_biological_activity">Chirality and biological activity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=24" title="Edit section: Chirality and biological activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Morphine is a pentacyclic 3°amine (alkaloid) with <b>5 stereogenic centers</b> and exists in <b>32 stereoisomeric forms</b>. But the desired analgesic activity resides exclusively in the natural product, the (-)-enantiomer with the configuration (<b>5R,6S,9R,13S,14R).</b><sup id="cite_ref-92" class="reference"><a href="#cite_note-92"><span class="cite-bracket">&#91;</span>92<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-93" class="reference"><a href="#cite_note-93"><span class="cite-bracket">&#91;</span>93<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=25" title="Edit section: Natural occurrence"><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">See also: <a href="/wiki/Opium" title="Opium">Opium</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Slaapbol_R0017600.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Slaapbol_R0017600.JPG/220px-Slaapbol_R0017600.JPG" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Slaapbol_R0017600.JPG/330px-Slaapbol_R0017600.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Slaapbol_R0017600.JPG/440px-Slaapbol_R0017600.JPG 2x" data-file-width="2048" data-file-height="1536" /></a><figcaption>Latex bleeding from a freshly-scored seed pod</figcaption></figure> <p>Morphine is the most abundant opiate found in <a href="/wiki/Opium" title="Opium">opium</a>, the dried <a href="/wiki/Latex" title="Latex">latex</a> extracted by shallowly scoring the unripe seedpods of the <i><a href="/wiki/Papaver_somniferum" title="Papaver somniferum">Papaver somniferum</a></i> poppy. Morphine is generally 8–14% of the dry weight of opium.<sup id="cite_ref-Kapoor_94-0" class="reference"><a href="#cite_note-Kapoor-94"><span class="cite-bracket">&#91;</span>94<span class="cite-bracket">&#93;</span></a></sup> Przemko and Norman cultivars of the opium poppy, are used to produce two other alkaloids, <a href="/wiki/Thebaine" title="Thebaine">thebaine</a> and <a href="/wiki/Oripavine" title="Oripavine">oripavine</a>, which are used in the manufacture of semi-synthetic and synthetic opioids like <a href="/wiki/Oxycodone" title="Oxycodone">oxycodone</a> and <a href="/wiki/Etorphine" title="Etorphine">etorphine</a>. <i><a href="/wiki/Papaver_bracteatum" title="Papaver bracteatum">P. bracteatum</a></i> does not contain morphine or <a href="/wiki/Codeine" title="Codeine">codeine</a>, or other narcotic <a href="/wiki/Phenanthrene" title="Phenanthrene">phenanthrene</a>-type, alkaloids. This species is rather a source of <a href="/wiki/Thebaine" title="Thebaine">thebaine</a>.<sup id="cite_ref-pmid925935_95-0" class="reference"><a href="#cite_note-pmid925935-95"><span class="cite-bracket">&#91;</span>95<span class="cite-bracket">&#93;</span></a></sup> Occurrence of morphine in other <a href="/wiki/Papaverales" class="mw-redirect" title="Papaverales">Papaverales</a> and <a href="/wiki/Papaveraceae" title="Papaveraceae">Papaveraceae</a>, as well as in some species of <a href="/wiki/Hops" title="Hops">hops</a> and <a href="/wiki/Mulberry" class="mw-redirect" title="Mulberry">mulberry</a> trees has not been confirmed. Morphine is produced most predominantly early in the life cycle of the plant. Past the optimum point for extraction, various processes in the plant produce codeine, <a href="/wiki/Thebaine" title="Thebaine">thebaine</a>, and in some cases negligible amounts of <a href="/wiki/Hydromorphone" title="Hydromorphone">hydromorphone</a>, <a href="/wiki/Dihydromorphine" title="Dihydromorphine">dihydromorphine</a>, <a href="/wiki/Dihydrocodeine" title="Dihydrocodeine">dihydrocodeine</a>, tetrahydro-thebaine, and <a href="/wiki/Hydrocodone" title="Hydrocodone">hydrocodone</a> (these compounds are rather synthesized from thebaine and oripavine). </p><p>In the brains of mammals, morphine is detectable in trace steady-state concentrations.<sup id="cite_ref-St2012_15-1" class="reference"><a href="#cite_note-St2012-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> The human body also produces <a href="/wiki/Endorphins" title="Endorphins">endorphins</a>, which are chemically related <a href="/wiki/Endogenous_opioid" class="mw-redirect" title="Endogenous opioid">endogenous opioid</a> <a href="/wiki/Peptide" title="Peptide">peptides</a> that function as <a href="/wiki/Neuropeptide" title="Neuropeptide">neuropeptides</a> and have similar effects to morphine.<sup id="cite_ref-96" class="reference"><a href="#cite_note-96"><span class="cite-bracket">&#91;</span>96<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Human_biosynthesis">Human biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=26" title="Edit section: Human biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-Expand_section plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Wiki_letter_w_cropped.svg" class="mw-file-description"><img alt="[icon]" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/44px-Wiki_letter_w_cropped.svg.png" decoding="async" width="44" height="31" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/66px-Wiki_letter_w_cropped.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/88px-Wiki_letter_w_cropped.svg.png 2x" data-file-width="44" data-file-height="31" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs expansion</b>&#32;with: a more standard presentation, without a scheme-in-text, and with a description of key enzymes, points of pathway regulation, etc. You can help by <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Morphine&amp;action=edit&amp;section=">adding to it</a>. <span class="date-container"><i>(<span class="date">October 2016</span>)</i></span></div></td></tr></tbody></table> <p>Morphine is an <a href="/wiki/Endogenous_opioid" class="mw-redirect" title="Endogenous opioid">endogenous opioid</a> in humans. Various human cells are capable of synthesizing and releasing it, including <a href="/wiki/White_blood_cell" title="White blood cell">white blood cells</a>.<sup id="cite_ref-St2012_15-2" class="reference"><a href="#cite_note-St2012-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-IUPHAR_-_μ-opioid_receptor_97-0" class="reference"><a href="#cite_note-IUPHAR_-_μ-opioid_receptor-97"><span class="cite-bracket">&#91;</span>97<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Poeaknapo_2004_98-0" class="reference"><a href="#cite_note-Poeaknapo_2004-98"><span class="cite-bracket">&#91;</span>98<span class="cite-bracket">&#93;</span></a></sup> The primary biosynthetic pathway for morphine in humans consists of <sup id="cite_ref-St2012_15-3" class="reference"><a href="#cite_note-St2012-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> </p> <figure class="mw-halign-center skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Morphine_biosynthesis_in_humans.png" class="mw-file-description"><img alt="Morphine biosynthesis in humans" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Morphine_biosynthesis_in_humans.png/770px-Morphine_biosynthesis_in_humans.png" decoding="async" width="770" height="516" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Morphine_biosynthesis_in_humans.png/1155px-Morphine_biosynthesis_in_humans.png 1.5x, //upload.wikimedia.org/wikipedia/commons/7/7d/Morphine_biosynthesis_in_humans.png 2x" data-file-width="1410" data-file-height="944" /></a><figcaption>Morphine biosynthesis in humans</figcaption></figure> <dl><dd><a href="/wiki/L-tyrosine" class="mw-redirect" title="L-tyrosine">L-tyrosine</a> → <a href="/wiki/Tyramine" title="Tyramine"><i>para</i>-tyramine</a> or <a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA</a> → <a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></dd> <dd>L-tyrosine → L-DOPA → <a href="/wiki/3,4-dihydroxyphenylacetaldehyde" class="mw-redirect" title="3,4-dihydroxyphenylacetaldehyde">3,4-dihydroxyphenylacetaldehyde</a> (DOPAL)</dd> <dd>Dopamine + DOPAL → <a href="/wiki/Tetrahydropapaveroline" title="Tetrahydropapaveroline">(<i>S</i>)-norlaudanosoline</a> →→→ (<i>S</i>)-<a href="/wiki/Reticuline" title="Reticuline">reticuline</a> → <a href="/w/index.php?title=1,2-dehydroreticulinium&amp;action=edit&amp;redlink=1" class="new" title="1,2-dehydroreticulinium (page does not exist)">1,2-dehydroreticulinium</a> → (<i>R</i>)-reticuline → <a href="/wiki/Salutaridine" title="Salutaridine">salutaridine</a> → <a href="/wiki/Salutaridinol" title="Salutaridinol">salutaridinol</a> → <a href="/wiki/Thebaine" title="Thebaine">thebaine</a> → <a href="/w/index.php?title=Neopinone&amp;action=edit&amp;redlink=1" class="new" title="Neopinone (page does not exist)">neopinone</a> → <a href="/wiki/Codeinone" title="Codeinone">codeinone</a> → <a href="/wiki/Codeine" title="Codeine">codeine</a> → morphine</dd></dl> <p>The intermediate (<i>S</i>)-norlaudanosoline (also known as tetrahydropapaveroline) is synthesized through the addition of DOPAL and dopamine.<sup id="cite_ref-St2012_15-4" class="reference"><a href="#cite_note-St2012-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a>, a <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> isoenzyme is involved in two steps along the biosynthetic pathway, catalyzing both the biosynthesis of dopamine from tyramine and of morphine from codeine.<sup id="cite_ref-St2012_15-5" class="reference"><a href="#cite_note-St2012-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-CYP2D6_tyramine-dopamine_metabolism_99-0" class="reference"><a href="#cite_note-CYP2D6_tyramine-dopamine_metabolism-99"><span class="cite-bracket">&#91;</span>99<span class="cite-bracket">&#93;</span></a></sup> </p><p>Urinary concentrations of endogenous codeine and morphine have been found to significantly increase in individuals taking <a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA</a> for the treatment of <a href="/wiki/Parkinson%27s_disease" title="Parkinson&#39;s disease">Parkinson's disease</a>.<sup id="cite_ref-St2012_15-6" class="reference"><a href="#cite_note-St2012-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis_in_the_opium_poppy">Biosynthesis in the opium poppy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=27" title="Edit section: Biosynthesis in the opium poppy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-center skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Morphine_biosynthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Morphine_biosynthesis.png/750px-Morphine_biosynthesis.png" decoding="async" width="750" height="546" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/9/94/Morphine_biosynthesis.png 1.5x" data-file-width="1021" data-file-height="743" /></a><figcaption>Morphine biosynthesis in the opium poppy</figcaption></figure> <p>Biosynthesis of morphine in the <a href="/wiki/Papaver_somniferum" title="Papaver somniferum">opium poppy</a> begins with two tyrosine derivatives, <a href="/wiki/Dopamine" title="Dopamine">dopamine</a> and <a href="/wiki/4-hydroxyphenylacetaldehyde" class="mw-redirect" title="4-hydroxyphenylacetaldehyde">4-hydroxyphenylacetaldehyde</a>. Condensation of these precursors yields the primary intermediate <a href="/wiki/Higenamine" title="Higenamine">higenamine</a> (norcoclaurine).<sup id="cite_ref-100" class="reference"><a href="#cite_note-100"><span class="cite-bracket">&#91;</span>100<span class="cite-bracket">&#93;</span></a></sup> Subsequent action of four enzymes yields the tetrahydroisoquinoline <a href="/wiki/Reticuline" title="Reticuline">reticuline</a>, which is converted into <a href="/wiki/Salutaridine" title="Salutaridine">salutaridine</a>, <a href="/wiki/Thebaine" title="Thebaine">thebaine</a>, and <a href="/wiki/Oripavine" title="Oripavine">oripavine</a>. The enzymes involved in this process are the <a href="/wiki/Salutaridine_synthase" title="Salutaridine synthase">salutaridine synthase</a>, <a href="/wiki/Salutaridine_reductase_(NADPH)" title="Salutaridine reductase (NADPH)">salutaridine:NADPH 7-oxidoreductase</a> and the <a href="/wiki/Codeinone_reductase_(NADPH)" title="Codeinone reductase (NADPH)">codeinone reductase</a>.<sup id="cite_ref-101" class="reference"><a href="#cite_note-101"><span class="cite-bracket">&#91;</span>101<span class="cite-bracket">&#93;</span></a></sup> Researchers are attempting to reproduce the biosynthetic pathway that produces morphine in <a href="/wiki/Genetically_engineered" class="mw-redirect" title="Genetically engineered">genetically engineered</a> <a href="/wiki/Yeast" title="Yeast">yeast</a>.<sup id="cite_ref-102" class="reference"><a href="#cite_note-102"><span class="cite-bracket">&#91;</span>102<span class="cite-bracket">&#93;</span></a></sup> In June 2015 the <i>S</i>-reticuline could be produced from sugar and <i>R</i>-reticuline could be converted to morphine, but the intermediate reaction could not be performed.<sup id="cite_ref-103" class="reference"><a href="#cite_note-103"><span class="cite-bracket">&#91;</span>103<span class="cite-bracket">&#93;</span></a></sup> In August 2015 the first complete synthesis of thebaine and hydrocodone in yeast was reported, but the process would need to be 100,000 times more productive to be suitable for commercial use.<sup id="cite_ref-104" class="reference"><a href="#cite_note-104"><span class="cite-bracket">&#91;</span>104<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-105" class="reference"><a href="#cite_note-105"><span class="cite-bracket">&#91;</span>105<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=28" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><style data-mw-deduplicate="TemplateStyles:r1248332772">.mw-parser-output .multiple-issues-text{width:95%;margin:0.2em 0}.mw-parser-output .multiple-issues-text>.mw-collapsible-content{margin-top:0.3em}.mw-parser-output .compact-ambox .ambox{border:none;border-collapse:collapse;background-color:transparent;margin:0 0 0 1.6em!important;padding:0!important;width:auto;display:block}body.mediawiki .mw-parser-output .compact-ambox .ambox.mbox-small-left{font-size:100%;width:auto;margin:0}.mw-parser-output .compact-ambox .ambox .mbox-text{padding:0!important;margin:0!important}.mw-parser-output .compact-ambox .ambox .mbox-text-span{display:list-item;line-height:1.5em;list-style-type:disc}body.skin-minerva .mw-parser-output .multiple-issues-text>.mw-collapsible-toggle,.mw-parser-output .compact-ambox .ambox .mbox-image,.mw-parser-output .compact-ambox .ambox .mbox-imageright,.mw-parser-output .compact-ambox .ambox .mbox-empty-cell,.mw-parser-output .compact-ambox .hide-when-compact{display:none}</style><table class="box-Multiple_issues plainlinks metadata ambox ambox-content ambox-multiple_issues compact-ambox" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/40px-Ambox_important.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/60px-Ambox_important.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/80px-Ambox_important.svg.png 2x" data-file-width="40" data-file-height="40" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span"><div class="multiple-issues-text mw-collapsible"><b>This section has multiple issues.</b> Please help <b><a href="/wiki/Special:EditPage/Morphine" title="Special:EditPage/Morphine">improve it</a></b> or discuss these issues on the <b><a href="/wiki/Talk:Morphine" title="Talk:Morphine">talk page</a></b>. <small><i>(<a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove these messages</a>)</i></small> <div class="mw-collapsible-content"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-Unreferenced_section plainlinks metadata ambox ambox-content ambox-Unreferenced" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>does not <a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources">cite</a> any <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">sources</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Morphine" title="Special:EditPage/Morphine">improve this section</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a>. Unsourced material may be challenged and <a href="/wiki/Wikipedia:Verifiability#Burden_of_evidence" title="Wikipedia:Verifiability">removed</a>.</span> <span class="date-container"><i>(<span class="date">February 2020</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-Original_research plainlinks metadata ambox ambox-content ambox-Original_research" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/40px-Ambox_important.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/60px-Ambox_important.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/80px-Ambox_important.svg.png 2x" data-file-width="40" data-file-height="40" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>possibly contains <a href="/wiki/Wikipedia:No_original_research" title="Wikipedia:No original research">original research</a></b>.<span class="hide-when-compact"> Please <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Morphine&amp;action=edit">improve it</a> by <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verifying</a> the claims made and adding <a href="/wiki/Wikipedia:Citing_sources#Inline_citations" title="Wikipedia:Citing sources">inline citations</a>. Statements consisting only of original research should be removed.</span> <span class="date-container"><i>(<span class="date">February 2020</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> </div> </div><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <p>Elements of the morphine structure have been used to create completely synthetic drugs such as the <a href="/wiki/Morphinan" title="Morphinan">morphinan</a> family (<a href="/wiki/Levorphanol" title="Levorphanol">levorphanol</a>, <a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a> and others) and other groups that have many members with morphine-like qualities.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> The modification of morphine and the aforementioned synthetics has also given rise to non-narcotic drugs with other uses such as emetics, stimulants, antitussives, anticholinergics, muscle relaxants, local anaesthetics, general anaesthetics, and others.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> Morphine-derived <a href="/wiki/Agonist%E2%80%93antagonist" class="mw-redirect" title="Agonist–antagonist">agonist–antagonist</a> drugs have also been developed.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Structure_description">Structure description</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=29" title="Edit section: Structure description"><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:Benzylisoquinoline_structure_in_Morphine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Benzylisoquinoline_structure_in_Morphine.svg/220px-Benzylisoquinoline_structure_in_Morphine.svg.png" decoding="async" width="220" height="187" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Benzylisoquinoline_structure_in_Morphine.svg/330px-Benzylisoquinoline_structure_in_Morphine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/31/Benzylisoquinoline_structure_in_Morphine.svg/440px-Benzylisoquinoline_structure_in_Morphine.svg.png 2x" data-file-width="254" data-file-height="216" /></a><figcaption>Chemical structure of morphine. The <a href="/wiki/Benzylisoquinoline" title="Benzylisoquinoline">benzylisoquinoline</a> backbone is shown in green.</figcaption></figure> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Morphine_numbered.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Morphine_numbered.svg/220px-Morphine_numbered.svg.png" decoding="async" width="220" height="201" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Morphine_numbered.svg/330px-Morphine_numbered.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Morphine_numbered.svg/440px-Morphine_numbered.svg.png 2x" data-file-width="164" data-file-height="150" /></a><figcaption>Morphine structure showing its standard ring lettering and carbon numbering system<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup></figcaption></figure> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Morphine_chemical_structure_in_3D.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Morphine_chemical_structure_in_3D.png/220px-Morphine_chemical_structure_in_3D.png" decoding="async" width="220" height="164" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Morphine_chemical_structure_in_3D.png/330px-Morphine_chemical_structure_in_3D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/09/Morphine_chemical_structure_in_3D.png/440px-Morphine_chemical_structure_in_3D.png 2x" data-file-width="742" data-file-height="553" /></a><figcaption>Same structure, but in a three-dimensional perspective</figcaption></figure><p> Morphine is a <a href="/wiki/Benzylisoquinoline" title="Benzylisoquinoline">benzylisoquinoline</a> alkaloid with two additional ring closures.<sup id="cite_ref-106" class="reference"><a href="#cite_note-106"><span class="cite-bracket">&#91;</span>106<span class="cite-bracket">&#93;</span></a></sup> As Jack DeRuiter of the Department of Drug Discovery and Development (formerly, Pharmacal Sciences), Harrison School of Pharmacy, Auburn University stated in his Fall 2000 course notes for that earlier department's "Principles of Drug Action 2" course, "Examination of the morphine molecule reveals the following structural features important to its pharmacological profile...<style data-mw-deduplicate="TemplateStyles:r1244412712">.mw-parser-output .templatequote{overflow:hidden;margin:1em 0;padding:0 32px}.mw-parser-output .templatequotecite{line-height:1.5em;text-align:left;margin-top:0}@media(min-width:500px){.mw-parser-output .templatequotecite{padding-left:1.6em}}</style></p><blockquote class="templatequote"> <ol><li>A rigid <a href="/wiki/Pentacyclic" class="mw-redirect" title="Pentacyclic">pentacyclic</a> structure consisting of a <a href="/wiki/Benzene" title="Benzene">benzene</a> ring (A), two partially unsaturated <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> rings (B and C), a <a href="/wiki/Piperidine" title="Piperidine">piperidine</a> ring (D) and a <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a> ring (E). Rings A, B, and C are the <a href="/wiki/Phenanthrene" title="Phenanthrene">phenanthrene</a> ring system. This ring system has little conformational flexibility...</li> <li>Two hydroxyl functional groups: a C3-<a href="/wiki/Phenol" title="Phenol">phenolic</a> [hydroxyl group] (p<i>K</i><sub>a</sub> 9.9) and a C6-<a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allylic</a> [hydroxyl group],</li> <li>An <a href="/wiki/Ether" title="Ether">ether</a> linkage between E4 and E5,</li> <li><a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">Unsaturation</a> between C7 and C8,</li> <li>A basic, [tertiary]-amine function at position 17, [and]</li> <li>[Five] centers of chirality (C5, C6, C9, C13, and C14) with morphine exhibiting a high degree of stereoselectivity of analgesic action."<sup id="cite_ref-urlwww.auburn.edu_107-0" class="reference"><a href="#cite_note-urlwww.auburn.edu-107"><span class="cite-bracket">&#91;</span>107<span class="cite-bracket">&#93;</span></a></sup><sup class="noprint Inline-Template noprint noexcerpt Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:NOTRS" class="mw-redirect" title="Wikipedia:NOTRS"><span title="This claim needs references to better sources. (February 2020)">better&#160;source&#160;needed</span></a></i>&#93;</sup><sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Chronological_items" title="Wikipedia:Manual of Style/Dates and numbers"><span title="The text near this tag is dated. (February 2020)">needs update</span></a></i>&#93;</sup></li></ol></blockquote> <p>Morphine and most of its derivatives do not exhibit optical isomerism, although some more distant relatives like the morphinan series (levorphanol, dextrorphan, and the racemic parent chemical racemorphan) do,<sup id="cite_ref-108" class="reference"><a href="#cite_note-108"><span class="cite-bracket">&#91;</span>108<span class="cite-bracket">&#93;</span></a></sup> and as noted above stereoselectivity in vivo is an important issue.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Uses_and_derivatives">Uses and derivatives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=30" title="Edit section: Uses and derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most of the licit morphine produced is used to make <a href="/wiki/Codeine" title="Codeine">codeine</a> by methylation.<sup id="cite_ref-109" class="reference"><a href="#cite_note-109"><span class="cite-bracket">&#91;</span>109<span class="cite-bracket">&#93;</span></a></sup> It is also a precursor for many drugs including <a href="/wiki/Heroin" title="Heroin">heroin</a> (3,6-diacetylmorphine), <a href="/wiki/Hydromorphone" title="Hydromorphone">hydromorphone</a> (dihydromorphinone), and <a href="/wiki/Oxymorphone" title="Oxymorphone">oxymorphone</a> (14-hydroxydihydromorphinone).<sup id="cite_ref-110" class="reference"><a href="#cite_note-110"><span class="cite-bracket">&#91;</span>110<span class="cite-bracket">&#93;</span></a></sup> Most semi-synthetic opioids, both of the morphine and <a href="/wiki/Codeine" title="Codeine">codeine</a> subgroups, are created by modifying one or more of the following:<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> </p> <ul><li>Halogenating or making other modifications at positions 1 or 2 on the morphine carbon skeleton.</li> <li>The methyl group that makes morphine into codeine can be removed or added back, or replaced with another functional group like ethyl and others to make codeine analogues of morphine-derived drugs and vice versa. Codeine analogues of morphine-based drugs often serve as prodrugs of the stronger drug, as in codeine and morphine, hydrocodone and hydromorphone, oxycodone and oxymorphone, nicocodeine and nicomorphine, dihydrocodeine and dihydromorphine, etc.</li> <li>Saturating, opening, or other changes to the bond between positions 7 and 8, as well as adding, removing, or modifying functional groups to these positions; saturating, reducing, eliminating, or otherwise modifying the 7–8 bond and attaching a functional group at 14 yields <a href="/wiki/Hydromorphinol" title="Hydromorphinol">hydromorphinol</a>; the oxidation of the hydroxyl group to a carbonyl and changing the 7–8 bond to single from double changes codeine into oxycodone.</li> <li>Attachment, removal, or modification of functional groups to positions 3 or 6 (dihydrocodeine and related, hydrocodone, nicomorphine); in the case of moving the methyl functional group from position 3 to 6, codeine becomes <a href="/wiki/Heterocodeine" title="Heterocodeine">heterocodeine</a>, which is 72 times stronger, and therefore six times stronger than morphine</li> <li>Attachment of functional groups or other modification at position 14 (oxymorphone, oxycodone, naloxone)</li> <li>Modifications at positions 2, 4, 5, or 17, usually along with other changes to the molecule elsewhere on the morphine skeleton. Often this is done with drugs produced by catalytic reduction, hydrogenation, oxidation, or the like, producing strong derivatives of morphine and codeine.</li></ul> <p>Many morphine derivatives can also be manufactured using <a href="/wiki/Thebaine" title="Thebaine">thebaine</a> or codeine as a starting material.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> Replacement of the <i>N</i>-methyl group of morphine with an <i>N</i>-phenylethyl group results in a product that is 18 times more powerful than morphine in its opiate agonist potency.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> Combining this modification with the replacement of the 6-<a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> with a 6-<a href="/wiki/Methylene_group" title="Methylene group">methylene group</a> produces a compound some 1,443 times more potent than morphine, stronger than the <a href="/wiki/Bentley_compounds" title="Bentley compounds">Bentley compounds</a> such as <a href="/wiki/Etorphine" title="Etorphine">etorphine</a> (M99, the Immobilon tranquilliser dart) by some measures.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> Closely related to morphine are the opioids morphine-<i>N</i>-oxide (genomorphine), which is a pharmaceutical that is no longer in common use;<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> and pseudomorphine, an alkaloid that exists in opium, form as degradation products of morphine.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> </p><p>As a result of the extensive study and use of this molecule, more than 250 morphine derivatives (also counting codeine and related drugs) have been developed since the last quarter of the 19th century.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> These drugs range from 25% the analgesic strength of codeine (or slightly more than 2% of the strength of morphine) to several thousand times the strength of morphine, to powerful opioid antagonists, including <a href="/wiki/Naloxone" title="Naloxone">naloxone</a> (Narcan), <a href="/wiki/Naltrexone" title="Naltrexone">naltrexone</a> (Trexan), <a href="/wiki/Diprenorphine" title="Diprenorphine">diprenorphine</a> (M5050, the reversing agent for the Immobilon dart) and <a href="/wiki/Nalorphine" title="Nalorphine">nalorphine</a> (Nalline).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> Some opioid agonist-antagonists, partial agonists, and inverse agonists are also derived from morphine.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> The receptor-activation profile of the semi-synthetic morphine derivatives varies widely and some, like <a href="/wiki/Apomorphine" title="Apomorphine">apomorphine</a> are devoid of narcotic effects.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Chemical_salts_of_Morphine">Chemical salts of Morphine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=31" title="Edit section: Chemical salts of Morphine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-More_citations_needed_section plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Relevant discussion may be found on the <a href="/wiki/Talk:Morphine#Need_for_expert_attention" title="Talk:Morphine">talk page</a>. Please help <a href="/wiki/Special:EditPage/Morphine" title="Special:EditPage/Morphine">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a>&#32;in this section. Unsourced material may be challenged and removed.</span> <span class="date-container"><i>(<span class="date">March 2021</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <p>Both morphine and its hydrated form are sparingly soluble in water.<sup id="cite_ref-111" class="reference"><a href="#cite_note-111"><span class="cite-bracket">&#91;</span>111<span class="cite-bracket">&#93;</span></a></sup> For this reason, pharmaceutical companies produce sulfate and <a href="/wiki/Hydrochloride" title="Hydrochloride">hydrochloride salts</a> of the drug, both of which are over 300 times more water-soluble than their parent molecule.<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (February 2020)">clarification needed</span></a></i>&#93;</sup><sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> Whereas the pH of a saturated morphine hydrate solution is 8.5, the salts are acidic.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> Since they derive from a strong acid but weak base, they are both at about pH = 5;<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (February 2020)">clarification needed</span></a></i>&#93;</sup><sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> as a consequence, the morphine salts are mixed with small amounts of <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">NaOH</a> to make them suitable for injection.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> </p><p>Many salts of morphine are used, with the most common in current clinical use being the hydrochloride, sulfate, tartrate, and citrate;<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> less commonly methobromide, hydrobromide, hydroiodide, lactate, chloride, and bitartrate and the others listed below.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> Morphine diacetate (heroin) is not a salt, but rather a further derivative,<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> see above.<sup id="cite_ref-112" class="reference"><a href="#cite_note-112"><span class="cite-bracket">&#91;</span>112<span class="cite-bracket">&#93;</span></a></sup> </p><p>Morphine meconate is a major form of the alkaloid in the poppy, as is morphine pectinate, nitrate, sulfate, and some others.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> Like codeine, dihydrocodeine and other (especially older) opiates, morphine has been used as the salicylate salt by some suppliers and can be easily compounded, imparting the therapeutic advantage of both the opioid and the <a href="/wiki/NSAID" class="mw-redirect" title="NSAID">NSAID</a>;<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> multiple <a href="/wiki/Barbiturate" title="Barbiturate">barbiturate</a> salts of morphine were also used in the past, as was/is morphine valerate, the salt of the acid being the active principle of <a href="/wiki/Valerian_(herb)" title="Valerian (herb)">valerian</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> <a href="/wiki/Calcium_morphenate" title="Calcium morphenate">Calcium morphenate</a> is the intermediate in various latex and poppy-straw methods of morphine production, more rarely sodium morphenate takes its place.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> Morphine ascorbate and other salts such as the tannate, citrate, and acetate, phosphate, valerate and others may be present in poppy tea depending on the method of preparation.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup><sup id="cite_ref-113" class="reference"><a href="#cite_note-113"><span class="cite-bracket">&#91;</span>113<span class="cite-bracket">&#93;</span></a></sup> </p><p>The salts listed by the <a href="/wiki/United_States_Drug_Enforcement_Administration" class="mw-redirect" title="United States Drug Enforcement Administration">United States Drug Enforcement Administration</a> for reporting purposes, in addition to a few others, are as follows:<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> </p> <table class="talk collapsed collapsible"> <tbody><tr> <th>Select salts of morphine with their <a href="/wiki/Controlled_Substances_Act" title="Controlled Substances Act">Controlled Substances Act</a> (CSA) schedule, <a href="/wiki/Administrative_Controlled_Substances_Code_Number" title="Administrative Controlled Substances Code Number">Administrative Controlled Substances Code Number</a> (ACSCN), and free base conversion ratio.<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (February 2020)">clarification needed</span></a></i>&#93;</sup><sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> </th></tr> <tr style="text-align: left;"> <td> <table class="wikitable"> <tbody><tr> <th>Salt or drug</th> <th><a href="/wiki/Controlled_Substances_Act" title="Controlled Substances Act">CSA</a> schedule</th> <th><a href="/wiki/Administrative_Controlled_Substances_Code_Number" title="Administrative Controlled Substances Code Number">ACSCN</a></th> <th>Free base conversion ratio </th></tr> <tr> <td>Morphine (base) </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>1 </td></tr> <tr> <td>Morphine citrate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.81 </td></tr> <tr> <td>Morphine bitartrate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.66 </td></tr> <tr> <td>Morphine stearate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.51 </td></tr> <tr> <td>Morphine phthalate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.89 </td></tr> <tr> <td>Morphine hydrobromide </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.78 </td></tr> <tr> <td>Morphine hydrobromide (2 H<sub>2</sub>O) </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.71 </td></tr> <tr> <td>Morphine hydrochloride </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.89 </td></tr> <tr> <td>Morphine hydrochloride (3 H<sub>2</sub>O) </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.76 </td></tr> <tr> <td>Morphine acetate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.71 </td></tr> <tr> <td>Morphine hydriodide (2 H<sub>2</sub>O) </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.64 </td></tr> <tr> <td>Morphine lactate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.76 </td></tr> <tr> <td>Morphine monohydrate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.94 </td></tr> <tr> <td>Morphine meconate (5 H<sub>2</sub>O) </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.66 </td></tr> <tr> <td>Morphine mucate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.57 </td></tr> <tr> <td>Morphine nitrate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.82 </td></tr> <tr> <td>Morphine phosphate (<style data-mw-deduplicate="TemplateStyles:r1154941027">.mw-parser-output .frac{white-space:nowrap}.mw-parser-output .frac .num,.mw-parser-output .frac .den{font-size:80%;line-height:0;vertical-align:super}.mw-parser-output .frac .den{vertical-align:sub}.mw-parser-output .sr-only{border:0;clip:rect(0,0,0,0);clip-path:polygon(0px 0px,0px 0px,0px 0px);height:1px;margin:-1px;overflow:hidden;padding:0;position:absolute;width:1px}</style><span class="frac"><span class="num">1</span>&#8260;<span class="den">2</span></span> H<sub>2</sub>O) </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.73 </td></tr> <tr> <td>Morphine phosphate (7 H<sub>2</sub>O) </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.73 </td></tr> <tr> <td>Morphine salicylate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td> </td></tr> <tr> <td>Morphine pectinate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.778 </td></tr> <tr> <td>Morphine phenylpropionate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.65 </td></tr> <tr> <td>Morphine methyliodide </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.67 </td></tr> <tr> <td>Morphine isobutyrate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.76 </td></tr> <tr> <td>Morphine hypophosphite </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.81 </td></tr> <tr> <td>Morphine sulfate (5 H<sub>2</sub>O) </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.75 </td></tr> <tr> <td>Morphine tannate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td> </td></tr> <tr> <td>Morphine tartrate (3 H<sub>2</sub>O) </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.74 </td></tr> <tr> <td>Morphine valerate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.74 </td></tr> <tr> <td>Morphine diethylbarbiturate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.619 </td></tr> <tr> <td>Morphine cyclopentylallylbarbiturate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9300 </td> <td>0.561 </td></tr> <tr> <td>Morphine diacetate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_I_controlled_substances" title="Controlled Substances Act">I</a> </td> <td>9200 </td> <td>0.74 </td></tr> <tr> <td>Morphine methylbromide </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_I_controlled_substances" title="Controlled Substances Act">I</a> </td> <td>9305 </td> <td>0.75 </td></tr> <tr> <td>Morphine methylsulfonate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_I_controlled_substances" title="Controlled Substances Act">I</a> </td> <td>9306 </td> <td>0.75 </td></tr> <tr> <td>Morphine-N-oxide </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_I_controlled_substances" title="Controlled Substances Act">I</a> </td> <td>9307 </td> <td>1 </td></tr> <tr> <td>Morphine-N-oxide quinate </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_I_controlled_substances" title="Controlled Substances Act">I</a> </td> <td>9307 </td> <td>0.60 </td></tr> <tr> <td>Morphine dinicotinate HCl (Nicomorphine) </td> <td><a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">II</a> </td> <td>9312 </td> <td>0.931 </td></tr></tbody></table> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=32" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Alkaloids.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Alkaloids.png/290px-Alkaloids.png" decoding="async" width="290" height="186" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Alkaloids.png/435px-Alkaloids.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/Alkaloids.png/580px-Alkaloids.png 2x" data-file-width="649" data-file-height="416" /></a><figcaption>First generation production of alkaloids from licit latex-derived opium</figcaption></figure> <p>In the <a href="/wiki/Opium_poppy" class="mw-redirect" title="Opium poppy">opium poppy</a>, the alkaloids are bound to <a href="/wiki/Meconic_acid" title="Meconic acid">meconic acid</a>. The method is to extract from the crushed plant with diluted sulfuric acid, which is a stronger acid than meconic acid, but not so strong to react with alkaloid molecules. The <a href="/wiki/Extraction_(chemistry)" title="Extraction (chemistry)">extraction</a> is performed in many steps (one amount of crushed plant is extracted at least six to ten times, so practically every <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> goes into the solution). From the solution obtained at the last extraction step, the alkaloids are precipitated by either ammonium hydroxide or sodium carbonate. The last step is purifying and separating morphine from other opium alkaloids. The somewhat similar Gregory process was developed in the United Kingdom during the Second World War, which begins with stewing the entire plant, in most cases save the roots and leaves, in plain or mildly acidified water, then proceeding through steps of concentration, extraction, and purification of alkaloids.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2014)">citation needed</span></a></i>&#93;</sup> Other methods of processing "poppy straw" (i.e., dried pods and stalks) use steam, one or more of several types of alcohol, or other organic solvents. </p><p>The poppy straw methods predominate in Continental Europe and the British Commonwealth, with the latex method in most common use in India. The latex method can involve either vertical or horizontal slicing of the unripe pods with a two-to five-bladed knife with a guard developed specifically for this purpose to the depth of a fraction of a millimetre and scoring of the pods can be done up to five times. An alternative latex method sometimes used in China in the past is to cut off the poppy heads, run a large needle through them, and collect the dried latex 24 to 48 hours later.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2014)">citation needed</span></a></i>&#93;</sup> </p><p>In India, opium harvested by licensed poppy farmers is dehydrated to uniform levels of hydration at government processing centers and then sold to pharmaceutical companies that extract morphine from the opium. However, in Turkey and Tasmania, morphine is obtained by harvesting and processing the fully mature dry seed pods with attached stalks, called <i>poppy straw</i>. In Turkey, a water extraction process is used, while in Tasmania, a solvent extraction process is used.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (April 2014)">citation needed</span></a></i>&#93;</sup> </p><p>Opium poppy contains at least 50 different alkaloids, but most of them are of very low concentration. Morphine is the principal alkaloid in raw opium and constitutes roughly 8–19% of <a href="/wiki/Opium" title="Opium">opium</a> by dry weight (depending on growing conditions).<sup id="cite_ref-Jenkins_AJ_2008_84-1" class="reference"><a href="#cite_note-Jenkins_AJ_2008-84"><span class="cite-bracket">&#91;</span>84<span class="cite-bracket">&#93;</span></a></sup> Some purpose-developed strains of poppy now produce opium that is up to 26% morphine by weight.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2014)">citation needed</span></a></i>&#93;</sup> A rough rule of thumb to determine the morphine content of pulverised dried poppy straw is to divide the percentage expected for the strain or crop via the latex method by eight or an empirically determined factor, which is often in the range of 5 to 15.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2014)">citation needed</span></a></i>&#93;</sup> The Norman strain of <i>P. somniferum</i>, also developed in <a href="/wiki/Tasmania" title="Tasmania">Tasmania</a>, produces down to 0.04% morphine but with much higher amounts of <a href="/wiki/Thebaine" title="Thebaine">thebaine</a> and <a href="/wiki/Oripavine" title="Oripavine">oripavine</a>, which can be used to synthesise semi-synthetic opioids as well as other drugs like stimulants, emetics, opioid antagonists, anticholinergics, and smooth-muscle agents.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2014)">citation needed</span></a></i>&#93;</sup> </p><p>In the 1950s and 1960s, <a href="/wiki/Hungary" title="Hungary">Hungary</a> supplied nearly 60% of Europe's total medication-purpose morphine production. To this day, poppy farming is legal in Hungary, but poppy farms are limited by law to 2 acres (8,100&#160;m<sup>2</sup>). It is also legal to sell dried poppies in flower shops for use in floral arrangements. </p><p>It was announced in 1973 that a team at the National Institutes of Health in the United States had developed a method for total synthesis of morphine, <a href="/wiki/Codeine" title="Codeine">codeine</a>, and thebaine using coal tar as a starting material. A shortage in codeine-hydrocodone class cough suppressants (all of which can be made from morphine in one or more steps, as well as from codeine or thebaine) was the initial reason for the research. </p><p>Most morphine produced for pharmaceutical use around the world is converted into codeine as the concentration of the latter in both raw opium and poppy straw is much lower than that of morphine; in most countries, the usage of codeine (both as end-product and precursor) is at least equal or greater than that of morphine on a weight basis. </p> <div class="mw-heading mw-heading3"><h3 id="Chemical_synthesis">Chemical synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=33" title="Edit section: Chemical synthesis"><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/Morphine_total_synthesis" class="mw-redirect" title="Morphine total synthesis">Morphine total synthesis</a></div> <p>The first <a href="/wiki/Morphine_total_synthesis" class="mw-redirect" title="Morphine total synthesis">morphine total synthesis</a>, devised by <a href="/wiki/Marshall_D._Gates,_Jr." class="mw-redirect" title="Marshall D. Gates, Jr.">Marshall D. Gates, Jr.</a> in 1952, remains a widely used example of <a href="/wiki/Total_synthesis" title="Total synthesis">total synthesis</a>.<sup id="cite_ref-114" class="reference"><a href="#cite_note-114"><span class="cite-bracket">&#91;</span>114<span class="cite-bracket">&#93;</span></a></sup> Several other syntheses were reported, notably by the research groups of Rice,<sup id="cite_ref-115" class="reference"><a href="#cite_note-115"><span class="cite-bracket">&#91;</span>115<span class="cite-bracket">&#93;</span></a></sup> Evans,<sup id="cite_ref-116" class="reference"><a href="#cite_note-116"><span class="cite-bracket">&#91;</span>116<span class="cite-bracket">&#93;</span></a></sup> Fuchs,<sup id="cite_ref-117" class="reference"><a href="#cite_note-117"><span class="cite-bracket">&#91;</span>117<span class="cite-bracket">&#93;</span></a></sup> Parker,<sup id="cite_ref-118" class="reference"><a href="#cite_note-118"><span class="cite-bracket">&#91;</span>118<span class="cite-bracket">&#93;</span></a></sup> Overman,<sup id="cite_ref-119" class="reference"><a href="#cite_note-119"><span class="cite-bracket">&#91;</span>119<span class="cite-bracket">&#93;</span></a></sup> Mulzer-Trauner,<sup id="cite_ref-120" class="reference"><a href="#cite_note-120"><span class="cite-bracket">&#91;</span>120<span class="cite-bracket">&#93;</span></a></sup> White,<sup id="cite_ref-121" class="reference"><a href="#cite_note-121"><span class="cite-bracket">&#91;</span>121<span class="cite-bracket">&#93;</span></a></sup> Taber,<sup id="cite_ref-122" class="reference"><a href="#cite_note-122"><span class="cite-bracket">&#91;</span>122<span class="cite-bracket">&#93;</span></a></sup> Trost,<sup id="cite_ref-123" class="reference"><a href="#cite_note-123"><span class="cite-bracket">&#91;</span>123<span class="cite-bracket">&#93;</span></a></sup> Fukuyama,<sup id="cite_ref-124" class="reference"><a href="#cite_note-124"><span class="cite-bracket">&#91;</span>124<span class="cite-bracket">&#93;</span></a></sup> Guillou,<sup id="cite_ref-125" class="reference"><a href="#cite_note-125"><span class="cite-bracket">&#91;</span>125<span class="cite-bracket">&#93;</span></a></sup> and Stork.<sup id="cite_ref-126" class="reference"><a href="#cite_note-126"><span class="cite-bracket">&#91;</span>126<span class="cite-bracket">&#93;</span></a></sup> Because of the stereochemical complexity and consequent synthetic challenge presented by this <a href="/wiki/Polycyclic_compound" title="Polycyclic compound">polycyclic</a> structure, Michael Freemantle has expressed the view that it is "highly unlikely" that a chemical synthesis will ever be cost-effective such that it could compete with the cost of producing morphine from the opium poppy.<sup id="cite_ref-127" class="reference"><a href="#cite_note-127"><span class="cite-bracket">&#91;</span>127<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="GMO_synthesis">GMO synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=34" title="Edit section: GMO synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Research">Research</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=35" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Thebaine has been produced by <a href="/wiki/GMO" class="mw-redirect" title="GMO">GMO</a> <i><a href="/wiki/E._coli" class="mw-redirect" title="E. coli">E. coli</a></i>.<sup id="cite_ref-128" class="reference"><a href="#cite_note-128"><span class="cite-bracket">&#91;</span>128<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Precursor_to_other_opioids">Precursor to other opioids</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=36" title="Edit section: Precursor to other opioids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pharmaceutical">Pharmaceutical</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=37" title="Edit section: Pharmaceutical"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-Expand_section plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Wiki_letter_w_cropped.svg" class="mw-file-description"><img alt="[icon]" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/44px-Wiki_letter_w_cropped.svg.png" decoding="async" width="44" height="31" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/66px-Wiki_letter_w_cropped.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/88px-Wiki_letter_w_cropped.svg.png 2x" data-file-width="44" data-file-height="31" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs expansion</b>&#32;with: sourced content that briefly summarises how morphine is used, industrially and globally, to produce other compounds with utility in medicine or research. You can help by <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Morphine&amp;action=edit&amp;section=">adding to it</a>. <span class="date-container"><i>(<span class="date">February 2020</span>)</i></span></div></td></tr></tbody></table> <p>Morphine is a precursor in the manufacture of several opioids such as <a href="/wiki/Dihydromorphine" title="Dihydromorphine">dihydromorphine</a>, <a href="/wiki/Hydromorphone" title="Hydromorphone">hydromorphone</a>, <a href="/wiki/Hydrocodone" title="Hydrocodone">hydrocodone</a>, and <a href="/wiki/Oxycodone" title="Oxycodone">oxycodone</a> as well as <a href="/wiki/Codeine" title="Codeine">codeine</a>, which itself has a large family of semi-synthetic derivatives.<sup id="cite_ref-129" class="reference"><a href="#cite_note-129"><span class="cite-bracket">&#91;</span>129<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Illicit">Illicit</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=38" title="Edit section: Illicit"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Illicit morphine is produced, though rarely, from codeine found in over-the-counter cough and pain medicines.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> Another illicit source is morphine extracted from extended-release morphine products.<sup id="cite_ref-130" class="reference"><a href="#cite_note-130"><span class="cite-bracket">&#91;</span>130<span class="cite-bracket">&#93;</span></a></sup> Chemical reactions can then be used to convert morphine, dihydromorphine, and hydrocodone into <a href="/wiki/Heroin" title="Heroin">heroin</a> or other opioids [e.g., <a href="/wiki/Diacetyldihydromorphine" title="Diacetyldihydromorphine">diacetyldihydromorphine</a> (Paralaudin), and <a href="/wiki/Thebacon" title="Thebacon">thebacon</a>].<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> Other clandestine conversions—of morphine, into ketones of the hydromorphone class, or other derivatives like <a href="/wiki/Dihydromorphine" title="Dihydromorphine">dihydromorphine</a> (Paramorfan), <a href="/wiki/Desomorphine" title="Desomorphine">desomorphine</a> (Permonid), <a href="/wiki/Metopon" title="Metopon">metopon</a>, etc., and of codeine into <a href="/wiki/Hydrocodone" title="Hydrocodone">hydrocodone</a> (Dicodid), <a href="/wiki/Dihydrocodeine" title="Dihydrocodeine">dihydrocodeine</a> (Paracodin), etc. —require greater expertise, and types and quantities of chemicals and equipment that are more difficult to source, and so are more rarely used, illicitly (but cases have been recorded).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</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=Morphine&amp;action=edit&amp;section=39" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Friedrich_Wilhelm_Adam_Sertuerner.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/59/Friedrich_Wilhelm_Adam_Sertuerner.jpg/220px-Friedrich_Wilhelm_Adam_Sertuerner.jpg" decoding="async" width="220" height="182" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/59/Friedrich_Wilhelm_Adam_Sertuerner.jpg/330px-Friedrich_Wilhelm_Adam_Sertuerner.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/59/Friedrich_Wilhelm_Adam_Sertuerner.jpg/440px-Friedrich_Wilhelm_Adam_Sertuerner.jpg 2x" data-file-width="1640" data-file-height="1353" /></a><figcaption><a href="/wiki/Friedrich_Sert%C3%BCrner" title="Friedrich Sertürner">Friedrich Sertürner</a></figcaption></figure> <p>The earliest known reference to morphine can be traced back to Theophrastus in the 3rd century BC, however, possible references to morphine may go as far back as 2100 BC as Sumerian clay tablets which records lists of medical prescriptions including opium-based cures.<sup id="cite_ref-131" class="reference"><a href="#cite_note-131"><span class="cite-bracket">&#91;</span>131<span class="cite-bracket">&#93;</span></a></sup> </p><p>An opium-based elixir has been ascribed to <a href="/wiki/Alchemy" title="Alchemy">alchemists</a> of <a href="/wiki/Byzantine_Empire" title="Byzantine Empire">Byzantine</a> times, but the specific formula was lost during the Ottoman conquest of <a href="/wiki/Constantinople" title="Constantinople">Constantinople</a> (<a href="/wiki/Istanbul" title="Istanbul">Istanbul</a>).<sup id="cite_ref-132" class="reference"><a href="#cite_note-132"><span class="cite-bracket">&#91;</span>132<span class="cite-bracket">&#93;</span></a></sup> Around 1522, <a href="/wiki/Paracelsus" title="Paracelsus">Paracelsus</a> made reference to an opium-based elixir that he called <i>laudanum</i> from the Latin word <i>laudāre</i>, meaning "to praise". He described it as a potent painkiller but recommended that it be used sparingly. The recipe given differs substantially from that of modern-day laudanum.<sup id="cite_ref-Sigerist_133-0" class="reference"><a href="#cite_note-Sigerist-133"><span class="cite-bracket">&#91;</span>133<span class="cite-bracket">&#93;</span></a></sup> </p><p>Morphine was discovered as the first active alkaloid extracted from the <a href="/wiki/Opium_poppy" class="mw-redirect" title="Opium poppy">opium poppy</a> plant in December 1804 in <a href="/wiki/Paderborn,_Germany" class="mw-redirect" title="Paderborn, Germany">Paderborn</a> by German pharmacist <a href="/wiki/Friedrich_Sert%C3%BCrner" title="Friedrich Sertürner">Friedrich Sertürner</a>.<sup id="cite_ref-pmid18443637_16-1" class="reference"><a href="#cite_note-pmid18443637-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Luch2009_18-1" class="reference"><a href="#cite_note-Luch2009-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-134" class="reference"><a href="#cite_note-134"><span class="cite-bracket">&#91;</span>134<span class="cite-bracket">&#93;</span></a></sup> In 1817, Sertürner reported experiments in which he administered morphine to himself, three young boys, three dogs, and a mouse; all four people almost died.<sup id="cite_ref-Dahan2010_135-0" class="reference"><a href="#cite_note-Dahan2010-135"><span class="cite-bracket">&#91;</span>135<span class="cite-bracket">&#93;</span></a></sup> Sertürner originally named the substance <i>morphium</i> after the Greek god of dreams, <a href="/wiki/Morpheus_(mythology)" class="mw-redirect" title="Morpheus (mythology)">Morpheus</a>, as it has a tendency to cause sleep.<sup id="cite_ref-Clay2013_19-2" class="reference"><a href="#cite_note-Clay2013-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-136" class="reference"><a href="#cite_note-136"><span class="cite-bracket">&#91;</span>136<span class="cite-bracket">&#93;</span></a></sup> Sertürner's morphium was six times stronger than opium. He hypothesized that, because lower doses of the drug were needed, it would be less addictive. However, Sertürner became addicted to the drug, warning that "I consider it my duty to attract attention to the terrible effects of this new substance I called morphium in order that calamity may be averted."<sup id="cite_ref-137" class="reference"><a href="#cite_note-137"><span class="cite-bracket">&#91;</span>137<span class="cite-bracket">&#93;</span></a></sup> </p><p>The drug was first marketed to the general public by Sertürner and Company in 1817 as a <a href="/wiki/Analgesic" title="Analgesic">pain medication</a>, and also as a treatment for opium and alcohol addiction. It was first used as a poison in 1822 when <a href="/wiki/Edme_Castaing" title="Edme Castaing">Edme Castaing</a> of France was convicted of murdering a patient.<sup id="cite_ref-138" class="reference"><a href="#cite_note-138"><span class="cite-bracket">&#91;</span>138<span class="cite-bracket">&#93;</span></a></sup> Commercial production began in Darmstadt, Germany, in 1827 by the pharmacy that became the pharmaceutical company Merck, with morphine sales being a large part of their early growth.<sup id="cite_ref-139" class="reference"><a href="#cite_note-139"><span class="cite-bracket">&#91;</span>139<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-140" class="reference"><a href="#cite_note-140"><span class="cite-bracket">&#91;</span>140<span class="cite-bracket">&#93;</span></a></sup> In the 1850s, <a href="/wiki/Alexander_Wood_(physician)" title="Alexander Wood (physician)">Alexander Wood</a> reported that he had injected morphine into his wife Rebecca as an experiment; the myth goes that this killed her because of respiratory depression,<sup id="cite_ref-Dahan2010_135-1" class="reference"><a href="#cite_note-Dahan2010-135"><span class="cite-bracket">&#91;</span>135<span class="cite-bracket">&#93;</span></a></sup> but she outlived her husband by ten years.<sup id="cite_ref-141" class="reference"><a href="#cite_note-141"><span class="cite-bracket">&#91;</span>141<span class="cite-bracket">&#93;</span></a></sup> </p><p>Later it was found that morphine was more addictive than either alcohol or opium, and its extensive use during the <a href="/wiki/American_Civil_War" title="American Civil War">American Civil War</a> allegedly resulted in over 400,000<sup id="cite_ref-142" class="reference"><a href="#cite_note-142"><span class="cite-bracket">&#91;</span>142<span class="cite-bracket">&#93;</span></a></sup> people with the "soldier's disease" of morphine addiction.<sup id="cite_ref-143" class="reference"><a href="#cite_note-143"><span class="cite-bracket">&#91;</span>143<span class="cite-bracket">&#93;</span></a></sup> This idea has been a subject of controversy, as there have been suggestions that such a disease was in fact a fabrication; the first documented use of the phrase "soldier's disease" was in 1915.<sup id="cite_ref-144" class="reference"><a href="#cite_note-144"><span class="cite-bracket">&#91;</span>144<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-145" class="reference"><a href="#cite_note-145"><span class="cite-bracket">&#91;</span>145<span class="cite-bracket">&#93;</span></a></sup> </p><p>Diacetylmorphine (better known as <a href="/wiki/Heroin" title="Heroin">heroin</a>) was synthesized from morphine in 1874 and brought to market by <a href="/wiki/Bayer" title="Bayer">Bayer</a> in 1898. Heroin is approximately 1.5 to 2 times more potent than morphine weight for weight. Due to the <a href="/wiki/Lipophilicity" title="Lipophilicity">lipid solubility</a> of diacetylmorphine, it can cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> faster than morphine, subsequently increasing the reinforcing component of addiction.<sup id="cite_ref-pmid11961074_146-0" class="reference"><a href="#cite_note-pmid11961074-146"><span class="cite-bracket">&#91;</span>146<span class="cite-bracket">&#93;</span></a></sup> Using a variety of subjective and objective measures, one study estimated the relative potency of heroin to morphine administered intravenously to post-addicts to be 1.80–2.66&#160;mg of morphine sulfate to 1&#160;mg of diamorphine hydrochloride (heroin).<sup id="cite_ref-martin_and_fraser_47-2" class="reference"><a href="#cite_note-martin_and_fraser-47"><span class="cite-bracket">&#91;</span>47<span class="cite-bracket">&#93;</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:MorphineAdvertisement1900_-_no_watermark.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/1/1c/MorphineAdvertisement1900_-_no_watermark.JPG/220px-MorphineAdvertisement1900_-_no_watermark.JPG" decoding="async" width="220" height="46" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/1/1c/MorphineAdvertisement1900_-_no_watermark.JPG/330px-MorphineAdvertisement1900_-_no_watermark.JPG 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/1/1c/MorphineAdvertisement1900_-_no_watermark.JPG/440px-MorphineAdvertisement1900_-_no_watermark.JPG 2x" data-file-width="1247" data-file-height="259" /></a><figcaption>Advertisement for curing morphine addiction, c. 1900<sup id="cite_ref-147" class="reference"><a href="#cite_note-147"><span class="cite-bracket">&#91;</span>147<span class="cite-bracket">&#93;</span></a></sup></figcaption></figure> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Morphine_Monojet.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/52/Morphine_Monojet.jpg/220px-Morphine_Monojet.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/52/Morphine_Monojet.jpg/330px-Morphine_Monojet.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/52/Morphine_Monojet.jpg/440px-Morphine_Monojet.jpg 2x" data-file-width="3264" data-file-height="2448" /></a><figcaption>An ampoule of morphine with integral needle for immediate use. Also known as a "<a href="/wiki/Syrette" title="Syrette">syrette</a>". From WWII. On display at the <a href="/wiki/Army_Medical_Services_Museum" class="mw-redirect" title="Army Medical Services Museum">Army Medical Services Museum</a>.</figcaption></figure> <p>Morphine became a controlled substance in the US under the <a href="/wiki/Harrison_Narcotics_Tax_Act" title="Harrison Narcotics Tax Act">Harrison Narcotics Tax Act</a> of 1914, and possession without a prescription in the US is a criminal offense. Morphine was the most commonly abused narcotic analgesic in the world until heroin was synthesized and came into use. In general, until the synthesis of <a href="/wiki/Dihydromorphine" title="Dihydromorphine">dihydromorphine</a> (<abbr title="circa">c.</abbr><span style="white-space:nowrap;">&#8201;1900</span>), the dihydromorphinone class of opioids (1920s), and <a href="/wiki/Oxycodone" title="Oxycodone">oxycodone</a> (1916) and similar drugs, there were no other drugs in the same efficacy range as opium, morphine, and heroin, with synthetics still several years away (<a href="/wiki/Pethidine" title="Pethidine">pethidine</a> was invented in Germany in 1937) and opioid agonists among the semi-synthetics were analogues and derivatives of codeine such as <a href="/wiki/Dihydrocodeine" title="Dihydrocodeine">dihydrocodeine</a> (Paracodin), <a href="/wiki/Ethylmorphine" title="Ethylmorphine">ethylmorphine</a> (Dionine), and <a href="/wiki/Benzylmorphine" title="Benzylmorphine">benzylmorphine</a> (Peronine). Even today, morphine is the most sought-after prescription narcotic by heroin addicts when heroin is scarce, all other things being equal; local conditions and user preference may cause <a href="/wiki/Hydromorphone" title="Hydromorphone">hydromorphone</a>, <a href="/wiki/Oxymorphone" title="Oxymorphone">oxymorphone</a>, high-dose oxycodone, or <a href="/wiki/Methadone" title="Methadone">methadone</a> as well as <a href="/wiki/Dextromoramide" title="Dextromoramide">dextromoramide</a> in specific instances such as 1970s Australia, to top that particular list. The stop-gap drugs used by the largest absolute number of heroin addicts is probably codeine, with significant use also of <a href="/wiki/Dihydrocodeine" title="Dihydrocodeine">dihydrocodeine</a>, poppy straw derivatives like poppy pod and poppy seed tea, <a href="/wiki/Propoxyphene" class="mw-redirect" title="Propoxyphene">propoxyphene</a>, and <a href="/wiki/Tramadol" title="Tramadol">tramadol</a>. </p><p>The structural formula of morphine was determined by 1925 by <a href="/wiki/Robert_Robinson_(organic_chemist)" class="mw-redirect" title="Robert Robinson (organic chemist)">Robert Robinson</a>.<sup id="cite_ref-148" class="reference"><a href="#cite_note-148"><span class="cite-bracket">&#91;</span>148<span class="cite-bracket">&#93;</span></a></sup> At least three methods of total synthesis of morphine from starting materials such as coal tar and petroleum distillates have been patented, the first of which was announced in 1952, by <a href="/wiki/Marshall_D._Gates,_Jr." class="mw-redirect" title="Marshall D. Gates, Jr.">Marshall D. Gates, Jr.</a> at the <a href="/wiki/University_of_Rochester" title="University of Rochester">University of Rochester</a>.<sup id="cite_ref-149" class="reference"><a href="#cite_note-149"><span class="cite-bracket">&#91;</span>149<span class="cite-bracket">&#93;</span></a></sup> Still, the vast majority of morphine is derived from the opium poppy by either the traditional method of gathering latex from the scored, unripe pods of the poppy, or processes using poppy straw, the dried pods and stems of the plant, the most widespread of which was invented in Hungary in 1925 and announced in 1930 by Hungarian pharmacologist <a href="/w/index.php?title=J%C3%A1nos_Kabay&amp;action=edit&amp;redlink=1" class="new" title="János Kabay (page does not exist)">János Kabay</a>.<sup id="cite_ref-150" class="reference"><a href="#cite_note-150"><span class="cite-bracket">&#91;</span>150<span class="cite-bracket">&#93;</span></a></sup> </p><p>In 2003, there was a discovery of endogenous morphine occurring naturally in the human body. Thirty years of speculation were made on this subject because there was a receptor that, it appeared, reacted only to morphine: the <a href="/wiki/%CE%9C-opioid_receptor" title="Μ-opioid receptor">μ<sub>3</sub>-opioid receptor</a> in human tissue.<sup id="cite_ref-151" class="reference"><a href="#cite_note-151"><span class="cite-bracket">&#91;</span>151<span class="cite-bracket">&#93;</span></a></sup> Human cells that form in reaction to cancerous <a href="/wiki/Neuroblastoma" title="Neuroblastoma">neuroblastoma</a> cells have been found to contain trace amounts of endogenous morphine.<sup id="cite_ref-Poeaknapo_2004_98-1" class="reference"><a href="#cite_note-Poeaknapo_2004-98"><span class="cite-bracket">&#91;</span>98<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=40" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Legal_status">Legal status</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=41" title="Edit section: Legal status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>In Australia, morphine is classified as a <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Drugs_and_Poisons#Schedule_8_Controlled_Drug_(Possession_without_authority_illegal)" class="mw-redirect" title="Standard for the Uniform Scheduling of Drugs and Poisons">Schedule 8</a> drug under the variously titled State and Territory Poisons Acts.</li> <li>In Canada, morphine is classified as a <a href="/wiki/Controlled_Drugs_and_Substances_Act#Schedule_I" title="Controlled Drugs and Substances Act">Schedule I</a> drug under the <a href="/wiki/Controlled_Drugs_and_Substances_Act" title="Controlled Drugs and Substances Act">Controlled Drugs and Substances Act</a>.</li> <li>In France, morphine is in the strictest schedule of controlled substances, based upon the December 1970 French controlled substances law.</li> <li>In Germany, morphine is a <i>verkehrsfähiges und verschreibungsfähiges Betäubungsmittel</i> listed under <i>Anlage III</i> (the equivalent of CSA Schedule II) of the <a href="/wiki/Bet%C3%A4ubungsmittelgesetz" class="mw-redirect" title="Betäubungsmittelgesetz">Betäubungsmittelgesetz</a>.<sup id="cite_ref-152" class="reference"><a href="#cite_note-152"><span class="cite-bracket">&#91;</span>152<span class="cite-bracket">&#93;</span></a></sup></li> <li>In Switzerland, morphine is scheduled similarly to Germany's legal classification of the drug.</li> <li>In Japan, morphine is classified as a narcotic under the <a href="https://ja.wikipedia.org/wiki/%E9%BA%BB%E8%96%AC%E5%8F%8A%E3%81%B3%E5%90%91%E7%B2%BE%E7%A5%9E%E8%96%AC%E5%8F%96%E7%B7%A0%E6%B3%95" class="extiw" title="ja:麻薬及び向精神薬取締法">Narcotics and Psychotropics Control Act</a> (<span title="Japanese-language text"><span lang="ja">麻薬及び向精神薬取締法</span></span>, <i>mayaku oyobi kōseishinyaku torishimarihō</i>).</li> <li>In the Netherlands, morphine is classified as a List 1 drug under the <a href="/wiki/Opium_Law" title="Opium Law">Opium Law</a>.</li> <li>In New Zealand, morphine is classified as a Class B drug under the <a href="/wiki/Misuse_of_Drugs_Act_1975" title="Misuse of Drugs Act 1975">Misuse of Drugs Act 1975</a>.<sup id="cite_ref-153" class="reference"><a href="#cite_note-153"><span class="cite-bracket">&#91;</span>153<span class="cite-bracket">&#93;</span></a></sup></li> <li>In the United Kingdom, morphine is listed as a Class A drug under the <a href="/wiki/Misuse_of_Drugs_Act_1971" title="Misuse of Drugs Act 1971">Misuse of Drugs Act 1971</a> and a Schedule 2 Controlled Drug under the <a href="/wiki/Misuse_of_Drugs_Regulations_2001" class="mw-redirect" title="Misuse of Drugs Regulations 2001">Misuse of Drugs Regulations 2001</a>.</li> <li>In the United States, morphine is classified as a <a href="/wiki/Controlled_Substances_Act#Schedule_II_controlled_substances" title="Controlled Substances Act">Schedule II</a> controlled substance under the <a href="/wiki/Controlled_Substances_Act" title="Controlled Substances Act">Controlled Substances Act</a> under main <a href="/wiki/Administrative_Controlled_Substances_Code_Number" title="Administrative Controlled Substances Code Number">Administrative Controlled Substances Code Number</a>&#160;9300. Morphine pharmaceuticals are subject to annual manufacturing quotas; in 2017 these quotas were 35.0 <a href="/wiki/Tonnes" class="mw-redirect" title="Tonnes">tonnes</a> of production for sale, and 27.3 tonnes of production as an intermediate, or chemical precursor, for conversion into other drugs.<sup id="cite_ref-154" class="reference"><a href="#cite_note-154"><span class="cite-bracket">&#91;</span>154<span class="cite-bracket">&#93;</span></a></sup> Morphine produced for use in extremely dilute formulations is excluded from the manufacturing quota.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2018)">citation needed</span></a></i>&#93;</sup></li> <li><a href="/wiki/United_Nations" title="United Nations">Internationally</a> (UN), morphine is a Schedule I drug under the <a href="/wiki/Single_Convention_on_Narcotic_Drugs" title="Single Convention on Narcotic Drugs">Single Convention on Narcotic Drugs</a>.<sup id="cite_ref-155" class="reference"><a href="#cite_note-155"><span class="cite-bracket">&#91;</span>155<span class="cite-bracket">&#93;</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Non-medical_use">Non-medical use</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=42" title="Edit section: Non-medical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Morphine_DOJ.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/7/7f/Morphine_DOJ.jpg" decoding="async" width="196" height="510" class="mw-file-element" data-file-width="196" data-file-height="510" /></a><figcaption>Example of different morphine tablets</figcaption></figure> <p>The euphoria, comprehensive alleviation of distress and therefore all aspects of suffering, promotion of sociability and empathy, "body high", and <a href="/wiki/Anxiolysis" class="mw-redirect" title="Anxiolysis">anxiolysis</a> provided by narcotic drugs including opioids can cause the use of high doses in the absence of pain for a protracted period, which can impart a craving for the drug in the user.<sup id="cite_ref-156" class="reference"><a href="#cite_note-156"><span class="cite-bracket">&#91;</span>156<span class="cite-bracket">&#93;</span></a></sup> As the prototype of the entire opioid class of drugs, morphine has properties that may lead to its misuse. Morphine addiction is the model upon which the current perception of addiction is based.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (October 2015)">medical citation needed</span></a></i>&#93;</sup> </p><p>Animal and human studies and clinical experience back up the contention that morphine is one of the most euphoric drugs known, and via all but the IV route heroin and morphine cannot be distinguished according to studies because heroin is a prodrug for the delivery of systemic morphine. Chemical changes to the morphine molecule yield other euphorigenics such as <a href="/wiki/Dihydromorphine" title="Dihydromorphine">dihydromorphine</a>, <a href="/wiki/Hydromorphone" title="Hydromorphone">hydromorphone</a> (Dilaudid, Hydal), and <a href="/wiki/Oxymorphone" title="Oxymorphone">oxymorphone</a> (Numorphan, Opana), as well as the latter three's methylated equivalents <a href="/wiki/Dihydrocodeine" title="Dihydrocodeine">dihydrocodeine</a>, <a href="/wiki/Hydrocodone" title="Hydrocodone">hydrocodone</a>, and oxycodone, respectively; in addition to heroin, there are <a href="/wiki/Dipropanoylmorphine" title="Dipropanoylmorphine">dipropanoylmorphine</a>, <a href="/wiki/Diacetyldihydromorphine" title="Diacetyldihydromorphine">diacetyldihydromorphine</a>, and other members of the 3,6 morphine diester category like <a href="/wiki/Nicomorphine" title="Nicomorphine">nicomorphine</a> and other similar semi-synthetic opiates like <a href="/wiki/Desomorphine" title="Desomorphine">desomorphine</a>, <a href="/wiki/Hydromorphinol" title="Hydromorphinol">hydromorphinol</a>, etc. used clinically in many countries of the world but also produced illicitly in rare instances.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (October 2015)">medical citation needed</span></a></i>&#93;</sup> </p><p>In general, non-medical use of morphine entails taking more than prescribed or outside of medical supervision, injecting oral formulations, mixing it with unapproved potentiators such as alcohol, cocaine, and the like, or defeating the extended-release mechanism by chewing the tablets or turning into a powder for snorting or preparing injectables. The latter method can be as time-consuming and involved as traditional methods of smoking opium. This and the fact that the liver destroys a large percentage of the drug on the first pass impacts the demand side of the equation for clandestine re-sellers, as many customers are not needle users and may have been disappointed with ingesting the drug orally. As morphine is generally as hard or harder to divert than <a href="/wiki/Oxycodone" title="Oxycodone">oxycodone</a> in a lot of cases, morphine in any form is uncommon on the street, although ampoules and phials of morphine injection, pure pharmaceutical morphine powder, and soluble multi-purpose tablets are very popular where available.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (October 2015)">medical citation needed</span></a></i>&#93;</sup> </p><p>Morphine is also available in a paste that is used in the production of heroin, which can be smoked by itself or turned into a soluble salt and injected; the same goes for the penultimate products of the Kompot (Polish Heroin) and black tar processes. Poppy straw as well as opium can yield morphine of purity levels ranging from poppy tea to near-pharmaceutical-grade morphine by itself or with all of the more than 50 other alkaloids. It also is the active narcotic ingredient in opium and all of its forms, derivatives, and analogues as well as forming from the breakdown of heroin and otherwise present in many batches of illicit heroin as the result of incomplete acetylation.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (October 2015)">medical citation needed</span></a></i>&#93;</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Names">Names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=43" title="Edit section: Names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Morphine is <a href="/wiki/Marketing" title="Marketing">marketed</a> under many different brand names in various parts of the world.<sup id="cite_ref-drugs.com-page_1-1" class="reference"><a href="#cite_note-drugs.com-page-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> It was formerly called Morphia in British English.<sup id="cite_ref-Morphia_14-1" class="reference"><a href="#cite_note-Morphia-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> </p><p>Informal names for morphine include: Cube Juice, Dope, Dreamer, Emsel, First Line, God's Drug, Hard Stuff, Hocus, Hows, Lydia, Lydic, M, Miss Emma, Mister Blue, Monkey, Morf, Morph, Morphide, Morphie, Morpho, Mother, MS, Ms. Emma, Mud, New Jack Swing (if mixed with <a href="/wiki/Heroin" title="Heroin">heroin</a>), Sister, Tab, Unkie, Unkie White, and Stuff.<sup id="cite_ref-157" class="reference"><a href="#cite_note-157"><span class="cite-bracket">&#91;</span>157<span class="cite-bracket">&#93;</span></a></sup> </p><p>MS Contin tablets are known as misties, and the 100&#160;mg extended-release tablets as greys and blockbusters. The "<a href="/wiki/Speedball_(drug)" title="Speedball (drug)">speedball</a>" can use morphine as the opioid component, which is combined with cocaine, <a href="/wiki/Amphetamines" class="mw-redirect" title="Amphetamines">amphetamines</a>, <a href="/wiki/Methylphenidate" title="Methylphenidate">methylphenidate</a>, or similar drugs. "Blue Velvet" is a combination of morphine with the antihistamine <a href="/wiki/Tripelennamine" title="Tripelennamine">tripelennamine</a> (Pyrabenzamine, PBZ, Pelamine) taken by injection. </p> <div class="mw-heading mw-heading3"><h3 id="Access_in_developing_countries">Access in developing countries</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=44" title="Edit section: Access in developing countries"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although morphine is cheap, people in poorer countries often do not have access to it. According to a 2005 estimate by the <a href="/wiki/International_Narcotics_Control_Board" title="International Narcotics Control Board">International Narcotics Control Board</a>, six countries (Australia, Canada, France, Germany, the United Kingdom, and the United States) consume 79% of the world's morphine. The less affluent countries, accounting for 80% of the world's population, consumed only about 6% of the global morphine supply.<sup id="cite_ref-158" class="reference"><a href="#cite_note-158"><span class="cite-bracket">&#91;</span>158<span class="cite-bracket">&#93;</span></a></sup> Some countries<sup class="noprint Inline-Template" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Avoid_weasel_words" class="mw-redirect" title="Wikipedia:Avoid weasel words"><span title="The material near this tag possibly uses too vague attribution or weasel words. (June 2017)">which?</span></a></i>&#93;</sup> import virtually no morphine, and in others<sup class="noprint Inline-Template" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Avoid_weasel_words" class="mw-redirect" title="Wikipedia:Avoid weasel words"><span title="The material near this tag possibly uses too vague attribution or weasel words. (June 2017)">which?</span></a></i>&#93;</sup> the drug is rarely available even for relieving severe pain while dying.<sup id="cite_ref-159" class="reference"><a href="#cite_note-159"><span class="cite-bracket">&#91;</span>159<span class="cite-bracket">&#93;</span></a></sup> </p><p>Experts in pain management attribute the under-distribution of morphine to an unwarranted fear of the drug's potential for addiction and abuse. While morphine is clearly addictive, Western doctors believe it is worthwhile to use the drug and then wean the patient off when the treatment is over.<sup id="cite_ref-160" class="reference"><a href="#cite_note-160"><span class="cite-bracket">&#91;</span>160<span class="cite-bracket">&#93;</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=Morphine&amp;action=edit&amp;section=45" 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-drugs.com-page-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-drugs.com-page_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-drugs.com-page_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20150614052020/http://www.drugs.com/international/morphine.html">"International listings for Morphine"</a>. <i>Drugs.com</i>. Archived from <a rel="nofollow" class="external text" href="https://www.drugs.com/international/morphine.html">the original</a> on 14 June 2015<span class="reference-accessdate">. Retrieved <span class="nowrap">2 June</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Drugs.com&amp;rft.atitle=International+listings+for+Morphine&amp;rft_id=https%3A%2F%2Fwww.drugs.com%2Finternational%2Fmorphine.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-Drugs.com_pregnancy-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Drugs.com_pregnancy_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Drugs.com_pregnancy_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/pregnancy/morphine.html">"Morphine Use During Pregnancy"</a>. <i>Drugs.com</i>. 14 October 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">21 August</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Drugs.com&amp;rft.atitle=Morphine+Use+During+Pregnancy&amp;rft.date=2019-10-14&amp;rft_id=https%3A%2F%2Fwww.drugs.com%2Fpregnancy%2Fmorphine.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" 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="CITEREFBonewit-WestHuntApplegate2012" class="citation book cs1">Bonewit-West K, Hunt SA, Applegate E (2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=YalYPI1KqTQC&amp;pg=PA571"><i>Today's Medical Assistant: Clinical and Administrative Procedures</i></a>. Elsevier Health Sciences. p.&#160;571. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-1-4557-0150-6" title="Special:BookSources/978-1-4557-0150-6"><bdi>978-1-4557-0150-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Today%27s+Medical+Assistant%3A+Clinical+and+Administrative+Procedures&amp;rft.pages=571&amp;rft.pub=Elsevier+Health+Sciences&amp;rft.date=2012&amp;rft.isbn=978-1-4557-0150-6&amp;rft.aulast=Bonewit-West&amp;rft.aufirst=K&amp;rft.au=Hunt%2C+SA&amp;rft.au=Applegate%2C+E&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DYalYPI1KqTQC%26pg%3DPA571&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://health-products.canada.ca/dpd-bdpp/info?lang=eng&amp;code=3042">"Morphine Product information"</a>. <i><a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a></i>. 9 August 2005<span class="reference-accessdate">. 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Vol.&#160;87 (40th&#160;ed.). p.&#160;162. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1911Natur..87R.313.">1911Natur..87R.313.</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2F087313b0">10.1038/087313b0</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-7136-5442-4" title="Special:BookSources/978-0-7136-5442-4"><bdi>978-0-7136-5442-4</bdi></a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:3979058">3979058</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908135509/https://books.google.com/books?id=bUnCAwAAQBAJ&amp;pg=PA162">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Black%27s+Medical+Dictionary&amp;rft.series=Nature&amp;rft.pages=162&amp;rft.edition=40th&amp;rft.date=2002&amp;rft_id=info%3Adoi%2F10.1038%2F087313b0&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A3979058%23id-name%3DS2CID&amp;rft_id=info%3Abibcode%2F1911Natur..87R.313.&amp;rft.isbn=978-0-7136-5442-4&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DbUnCAwAAQBAJ%26pg%3DPA162&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.medicines.org.uk/emc/product/1020/smpc">"Sevredol Summary of Product Characteristics (SmPC)"</a>. <i>(emc)</i>. 13 February 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">20 February</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=%28emc%29&amp;rft.atitle=Sevredol+Summary+of+Product+Characteristics+%28SmPC%29&amp;rft.date=2024-02-13&amp;rft_id=https%3A%2F%2Fwww.medicines.org.uk%2Femc%2Fproduct%2F1020%2Fsmpc&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf">"Orange Book - List of Controlled Substances and Regulated Chemicals"</a> <span class="cs1-format">(PDF)</span>. <i>DEA</i>. 31 December 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">10 January</span> 2025</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=DEA&amp;rft.atitle=Orange+Book+-+List+of+Controlled+Substances+and+Regulated+Chemicals&amp;rft.date=2024-12-31&amp;rft_id=https%3A%2F%2Fwww.deadiversion.usdoj.gov%2Fschedules%2Forangebook%2Forangebook.pdf&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.ema.europa.eu/en/medicines/human/referrals/modified-released-oral-opioids">"Modified-released oral opioids"</a>. <i>European Medicines Agency</i>. 18 November 2010<span class="reference-accessdate">. Retrieved <span class="nowrap">20 February</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=European+Medicines+Agency&amp;rft.atitle=Modified-released+oral+opioids&amp;rft.date=2010-11-18&amp;rft_id=https%3A%2F%2Fwww.ema.europa.eu%2Fen%2Fmedicines%2Fhuman%2Freferrals%2Fmodified-released-oral-opioids&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-pmid3387374-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid3387374_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJonssonChristensenJordeningFrølund1988" class="citation journal cs1">Jonsson T, Christensen CB, Jordening H, Frølund C (April 1988). "The bioavailability of rectally administered morphine". <i>Pharmacology &amp; Toxicology</i>. <b>62</b> (4): <span class="nowrap">203–</span>5. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1600-0773.1988.tb01872.x">10.1111/j.1600-0773.1988.tb01872.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/3387374">3387374</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Pharmacology+%26+Toxicology&amp;rft.atitle=The+bioavailability+of+rectally+administered+morphine&amp;rft.volume=62&amp;rft.issue=4&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E203-%3C%2Fspan%3E5&amp;rft.date=1988-04&amp;rft_id=info%3Adoi%2F10.1111%2Fj.1600-0773.1988.tb01872.x&amp;rft_id=info%3Apmid%2F3387374&amp;rft.aulast=Jonsson&amp;rft.aufirst=T&amp;rft.au=Christensen%2C+CB&amp;rft.au=Jordening%2C+H&amp;rft.au=Fr%C3%B8lund%2C+C&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWhimster1997" class="citation book cs1">Whimster F (1997). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=m0bNaDhkaukC&amp;pg=PA191"><i>Cambridge textbook of accident and emergency medicine</i></a>. Cambridge: Cambridge University Press. p.&#160;191. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-521-43379-2" title="Special:BookSources/978-0-521-43379-2"><bdi>978-0-521-43379-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908135509/https://books.google.com/books?id=m0bNaDhkaukC&amp;pg=PA191">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Cambridge+textbook+of+accident+and+emergency+medicine&amp;rft.place=Cambridge&amp;rft.pages=191&amp;rft.pub=Cambridge+University+Press&amp;rft.date=1997&amp;rft.isbn=978-0-521-43379-2&amp;rft.aulast=Whimster&amp;rft.aufirst=F&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dm0bNaDhkaukC%26pg%3DPA191&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLiben2012" class="citation book cs1">Liben S (2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=k3XNeNseoHIC&amp;pg=PA240"><i>Oxford textbook of palliative care for children</i></a> (2&#160;ed.). Oxford: Oxford University Press. p.&#160;240. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-19-959510-5" title="Special:BookSources/978-0-19-959510-5"><bdi>978-0-19-959510-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908135509/https://books.google.com/books?id=k3XNeNseoHIC&amp;pg=PA240">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Oxford+textbook+of+palliative+care+for+children&amp;rft.place=Oxford&amp;rft.pages=240&amp;rft.edition=2&amp;rft.pub=Oxford+University+Press&amp;rft.date=2012&amp;rft.isbn=978-0-19-959510-5&amp;rft.aulast=Liben&amp;rft.aufirst=S&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dk3XNeNseoHIC%26pg%3DPA240&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-AHFS2015-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-AHFS2015_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-13"><sup><i><b>n</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-14"><sup><i><b>o</b></i></sup></a> <a href="#cite_ref-AHFS2015_12-15"><sup><i><b>p</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/morphine-sulfate.html">"Morphine sulfate"</a>. The American Society of Health-System Pharmacists. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150502143444/http://www.drugs.com/monograph/morphine-sulfate.html">Archived</a> from the original on 2 May 2015<span class="reference-accessdate">. Retrieved <span class="nowrap">1 June</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=Morphine+sulfate&amp;rft.pub=The+American+Society+of+Health-System+Pharmacists&amp;rft_id=https%3A%2F%2Fwww.drugs.com%2Fmonograph%2Fmorphine-sulfate.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-Rockwood2009-13"><span class="mw-cite-backlink">^ <a href="#cite_ref-Rockwood2009_13-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Rockwood2009_13-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Rockwood2009_13-2"><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="CITEREFRockwood2009" class="citation book cs1">Rockwood CA (2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=QVIdXV_F8M4C&amp;pg=PA54"><i>Rockwood and Wilkins' fractures in children</i></a> (7th&#160;ed.). Philadelphia, Pa.: Lippincott Williams &amp; Wilkins. p.&#160;54. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-1-58255-784-7" title="Special:BookSources/978-1-58255-784-7"><bdi>978-1-58255-784-7</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908135509/https://books.google.com/books?id=QVIdXV_F8M4C&amp;pg=PA54">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Rockwood+and+Wilkins%27+fractures+in+children&amp;rft.place=Philadelphia%2C+Pa.&amp;rft.pages=54&amp;rft.edition=7th&amp;rft.pub=Lippincott+Williams+%26+Wilkins&amp;rft.date=2009&amp;rft.isbn=978-1-58255-784-7&amp;rft.aulast=Rockwood&amp;rft.aufirst=CA&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DQVIdXV_F8M4C%26pg%3DPA54&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-Morphia-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-Morphia_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Morphia_14-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20200804021300/https://www.lexico.com/en/definition/morphia">"Morphia"</a>. <i>Lexico Dictionaries | English</i>. 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Retrieved <span class="nowrap">14 September</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Lexico+Dictionaries+%7C+English&amp;rft.atitle=Morphia&amp;rft_id=https%3A%2F%2Fwww.lexonico.com%2Fen%2Fdefinition%2Fmorphia&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-St2012-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-St2012_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-St2012_15-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-St2012_15-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-St2012_15-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-St2012_15-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-St2012_15-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-St2012_15-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStefanoPtáčekKuželováKream2012" class="citation journal cs1">Stefano GB, Ptáček R, Kuželová H, Kream RM (2012). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160824130751/http://fb.cuni.cz/file/5635/FB2012A0008.pdf">"Endogenous morphine: up-to-date review 2011"</a> <span class="cs1-format">(PDF)</span>. <i>Folia Biologica</i>. <b>58</b> (2): <span class="nowrap">49–</span>56. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.14712%2Ffb2012058020049">10.14712/fb2012058020049</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22578954">22578954</a>. Archived from <a rel="nofollow" class="external text" href="http://fb.cuni.cz/file/5635/FB2012A0008.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 24 August 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">10 October</span> 2016</span>. <q>Positive evolutionary pressure has apparently preserved the ability to synthesize chemically authentic morphine, albeit in homeopathic concentrations, throughout animal phyla.</q></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Folia+Biologica&amp;rft.atitle=Endogenous+morphine%3A+up-to-date+review+2011&amp;rft.volume=58&amp;rft.issue=2&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E49-%3C%2Fspan%3E56&amp;rft.date=2012&amp;rft_id=info%3Adoi%2F10.14712%2Ffb2012058020049&amp;rft_id=info%3Apmid%2F22578954&amp;rft.aulast=Stefano&amp;rft.aufirst=GB&amp;rft.au=Pt%C3%A1%C4%8Dek%2C+R&amp;rft.au=Ku%C5%BEelov%C3%A1%2C+H&amp;rft.au=Kream%2C+RM&amp;rft_id=http%3A%2F%2Ffb.cuni.cz%2Ffile%2F5635%2FFB2012A0008.pdf&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-pmid18443637-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid18443637_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid18443637_16-1"><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="CITEREFTrescotDattaLeeHansen2008" class="citation journal cs1">Trescot AM, Datta S, Lee M, Hansen, H (March 2008). "Opioid Pharmacology". <i>Pain Physician Journal</i>. <b>11</b> (2): S133-53. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.36076%2Fppj.2008%2F11%2FS133">10.36076/ppj.2008/11/S133</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18443637">18443637</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Pain+Physician+Journal&amp;rft.atitle=Opioid+Pharmacology&amp;rft.volume=11&amp;rft.issue=2&amp;rft.pages=S133-53&amp;rft.date=2008-03&amp;rft_id=info%3Adoi%2F10.36076%2Fppj.2008%2F11%2FS133&amp;rft_id=info%3Apmid%2F18443637&amp;rft.aulast=Trescot&amp;rft.aufirst=AM&amp;rft.au=Datta%2C+S&amp;rft.au=Lee%2C+M&amp;rft.au=Hansen&amp;rft.au=H&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-Court2009-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-Court2009_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Court2009_17-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Court2009_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="CITEREFCourtwright2009" class="citation book cs1">Courtwright DT (2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=GHqV3elHYvMC&amp;pg=PA36"><i>Forces of habit drugs and the making of the modern world</i></a> (1&#160;ed.). Cambridge, Mass.: Harvard University Press. pp.&#160;<span class="nowrap">36–</span>37. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-674-02990-3" title="Special:BookSources/978-0-674-02990-3"><bdi>978-0-674-02990-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908135509/https://books.google.com/books?id=GHqV3elHYvMC&amp;pg=PA36">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Forces+of+habit+drugs+and+the+making+of+the+modern+world&amp;rft.place=Cambridge%2C+Mass.&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E36-%3C%2Fspan%3E37&amp;rft.edition=1&amp;rft.pub=Harvard+University+Press&amp;rft.date=2009&amp;rft.isbn=978-0-674-02990-3&amp;rft.aulast=Courtwright&amp;rft.aufirst=DT&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DGHqV3elHYvMC%26pg%3DPA36&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-Luch2009-18"><span class="mw-cite-backlink">^ <a href="#cite_ref-Luch2009_18-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Luch2009_18-1"><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="CITEREFLuch2009" class="citation book cs1">Luch A, ed. (2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=MtOiLVWBn8cC&amp;pg=PA20"><i>Molecular, clinical and environmental toxicology</i></a>. Springer. p.&#160;20. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-3-7643-8335-0" title="Special:BookSources/978-3-7643-8335-0"><bdi>978-3-7643-8335-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Molecular%2C+clinical+and+environmental+toxicology&amp;rft.pages=20&amp;rft.pub=Springer&amp;rft.date=2009&amp;rft.isbn=978-3-7643-8335-0&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DMtOiLVWBn8cC%26pg%3DPA20&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-Clay2013-19"><span class="mw-cite-backlink">^ <a href="#cite_ref-Clay2013_19-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Clay2013_19-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Clay2013_19-2"><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="CITEREFMosher2013" class="citation book cs1">Mosher CJ (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=2UQXBAAAQBAJ&amp;pg=PA123"><i>Drugs and Drug Policy: The Control of Consciousness Alteration</i></a>. SAGE Publications. p.&#160;123. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-1-4833-2188-2" title="Special:BookSources/978-1-4833-2188-2"><bdi>978-1-4833-2188-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908135509/https://books.google.com/books?id=2UQXBAAAQBAJ&amp;pg=PA123">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Drugs+and+Drug+Policy%3A+The+Control+of+Consciousness+Alteration&amp;rft.pages=123&amp;rft.pub=SAGE+Publications&amp;rft.date=2013&amp;rft.isbn=978-1-4833-2188-2&amp;rft.aulast=Mosher&amp;rft.aufirst=CJ&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D2UQXBAAAQBAJ%26pg%3DPA123&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFisher2009" class="citation book cs1">Fisher GL (2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=DFR2AwAAQBAJ&amp;pg=PT598"><i>Encyclopedia of substance abuse prevention, treatment, &amp; recovery</i></a>. Los Angeles: SAGE. p.&#160;564. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-1-4522-6601-5" title="Special:BookSources/978-1-4522-6601-5"><bdi>978-1-4522-6601-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908135509/https://books.google.com/books?id=DFR2AwAAQBAJ&amp;pg=PT598">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Encyclopedia+of+substance+abuse+prevention%2C+treatment%2C+%26+recovery&amp;rft.place=Los+Angeles&amp;rft.pages=564&amp;rft.pub=SAGE&amp;rft.date=2009&amp;rft.isbn=978-1-4522-6601-5&amp;rft.aulast=Fisher&amp;rft.aufirst=GL&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DDFR2AwAAQBAJ%26pg%3DPT598&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=0_9QHvacPzYC&amp;pg=PA77"><i>Narcotic Drugs Estimated World Requirements for 2008, Statistics for 2006</i></a>. New York: United Nations Pubns. 2008. p.&#160;77. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-92-1-048119-9" title="Special:BookSources/978-92-1-048119-9"><bdi>978-92-1-048119-9</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908135509/https://books.google.com/books?id=0_9QHvacPzYC&amp;pg=PA77">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Narcotic+Drugs+Estimated+World+Requirements+for+2008%2C+Statistics+for+2006&amp;rft.place=New+York&amp;rft.pages=77&amp;rft.pub=United+Nations+Pubns&amp;rft.date=2008&amp;rft.isbn=978-92-1-048119-9&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0_9QHvacPzYC%26pg%3DPA77&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-UN2015-22"><span class="mw-cite-backlink">^ <a href="#cite_ref-UN2015_22-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-UN2015_22-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-UN2015_22-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-UN2015_22-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://www.incb.org/documents/Narcotic-Drugs/Technical-Publications/2014/Narcotic_Drugs_Report_2014.pdf"><i>Narcotic Drugs 2014</i></a> <span class="cs1-format">(PDF)</span>. INTERNATIONAL NARCOTICS CONTROL BOARD. 2015. pp.&#160;21, 30. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-92-1-048157-1" title="Special:BookSources/978-92-1-048157-1"><bdi>978-92-1-048157-1</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150602192211/https://www.incb.org/documents/Narcotic-Drugs/Technical-Publications/2014/Narcotic_Drugs_Report_2014.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 2 June 2015.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Narcotic+Drugs+2014&amp;rft.pages=21%2C+30&amp;rft.pub=INTERNATIONAL+NARCOTICS+CONTROL+BOARD&amp;rft.date=2015&amp;rft.isbn=978-92-1-048157-1&amp;rft_id=https%3A%2F%2Fwww.incb.org%2Fdocuments%2FNarcotic-Drugs%2FTechnical-Publications%2F2014%2FNarcotic_Drugs_Report_2014.pdf&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-Trig2006-23"><span class="mw-cite-backlink">^ <a href="#cite_ref-Trig2006_23-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Trig2006_23-1"><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="CITEREFTriggle2006" class="citation book cs1">Triggle DJ (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=sud4ORAMNkYC&amp;pg=PA20"><i>Morphine</i></a>. New York: Chelsea House Publishers. pp.&#160;<span class="nowrap">20–</span>21. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-1-4381-0211-5" title="Special:BookSources/978-1-4381-0211-5"><bdi>978-1-4381-0211-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Morphine&amp;rft.place=New+York&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E20-%3C%2Fspan%3E21&amp;rft.pub=Chelsea+House+Publishers&amp;rft.date=2006&amp;rft.isbn=978-1-4381-0211-5&amp;rft.aulast=Triggle&amp;rft.aufirst=DJ&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dsud4ORAMNkYC%26pg%3DPA20&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-Kar2006-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-Kar2006_24-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKarch2006" class="citation book cs1">Karch SB (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=F0mUte90ATUC&amp;pg=PA7"><i>Drug abuse handbook</i></a> (2nd&#160;ed.). 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New York: Springer. p.&#160;116. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-387-98543-5" title="Special:BookSources/978-0-387-98543-5"><bdi>978-0-387-98543-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Functional+Neuroscience&amp;rft.place=New+York&amp;rft.pages=116&amp;rft.pub=Springer&amp;rft.date=2000&amp;rft.isbn=978-0-387-98543-5&amp;rft.aulast=Stewart&amp;rft.aufirst=O&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DnNH3p29wjK4C%26q%3Dendorphins%2Bneurotransmitter%26pg%3DPA116&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-IUPHAR_-_μ-opioid_receptor-97"><span class="mw-cite-backlink"><b><a href="#cite_ref-IUPHAR_-_μ-opioid_receptor_97-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/ObjectDisplayForward?objectId=319">"μ receptor"</a>. <i>IUPHAR/BPS Guide to PHARMACOLOGY</i>. 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Retrieved <span class="nowrap">28 December</span> 2017</span>. <q>Morphine occurs endogenously</q></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=IUPHAR%2FBPS+Guide+to+PHARMACOLOGY&amp;rft.atitle=%CE%BC+receptor&amp;rft.date=2017-03-15&amp;rft_id=http%3A%2F%2Fwww.guidetopharmacology.org%2FGRAC%2FObjectDisplayForward%3FobjectId%3D319&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-Poeaknapo_2004-98"><span class="mw-cite-backlink">^ <a href="#cite_ref-Poeaknapo_2004_98-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Poeaknapo_2004_98-1"><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="CITEREFPoeaknapoSchmidtBrandschDräger2004" class="citation journal cs1">Poeaknapo C, Schmidt J, Brandsch M, Dräger B, Zenk MH (September 2004). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC521124">"Endogenous formation of morphine in human cells"</a>. <i>Proceedings of the National Academy of Sciences of the United States of America</i>. <b>101</b> (39): <span class="nowrap">14091–</span>6. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2004PNAS..10114091P">2004PNAS..10114091P</a>. <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/10.1073%2Fpnas.0405430101">10.1073/pnas.0405430101</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a>&#160;<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC521124">521124</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15383669">15383669</a>. <q>Without doubt, human cells can produce the alkaloid morphine.</q></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences+of+the+United+States+of+America&amp;rft.atitle=Endogenous+formation+of+morphine+in+human+cells&amp;rft.volume=101&amp;rft.issue=39&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E14091-%3C%2Fspan%3E6&amp;rft.date=2004-09&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC521124%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F15383669&amp;rft_id=info%3Adoi%2F10.1073%2Fpnas.0405430101&amp;rft_id=info%3Abibcode%2F2004PNAS..10114091P&amp;rft.aulast=Poeaknapo&amp;rft.aufirst=C&amp;rft.au=Schmidt%2C+J&amp;rft.au=Brandsch%2C+M&amp;rft.au=Dr%C3%A4ger%2C+B&amp;rft.au=Zenk%2C+MH&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC521124&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-CYP2D6_tyramine-dopamine_metabolism-99"><span class="mw-cite-backlink"><b><a href="#cite_ref-CYP2D6_tyramine-dopamine_metabolism_99-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWangLiDongYue2014" class="citation journal cs1">Wang X, Li J, Dong G, Yue J (February 2014). 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title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=European+Journal+of+Pharmacology&amp;rft.atitle=The+endogenous+substrates+of+brain+CYP2D&amp;rft.volume=724&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E211-%3C%2Fspan%3E8&amp;rft.date=2014-02&amp;rft_id=info%3Adoi%2F10.1016%2Fj.ejphar.2013.12.025&amp;rft_id=info%3Apmid%2F24374199&amp;rft.aulast=Wang&amp;rft.aufirst=X&amp;rft.au=Li%2C+J&amp;rft.au=Dong%2C+G&amp;rft.au=Yue%2C+J&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-100"><span class="mw-cite-backlink"><b><a href="#cite_ref-100">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOnoyovweHagelChenKhan2013" class="citation journal cs1">Onoyovwe A, Hagel JM, Chen X, Khan MF, Schriemer DC, Facchini PJ (2013). <a rel="nofollow" class="external text" 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title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Current+Organic+Chemistry&amp;rft.atitle=Morphine+Synthesis+and+Biosynthesis-An+Update&amp;rft.volume=4&amp;rft.issue=3&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E343-%3C%2Fspan%3E362&amp;rft.date=2000-03&amp;rft_id=https%3A%2F%2Fciteseerx.ist.psu.edu%2Fviewdoc%2Fsummary%3Fdoi%3D10.1.1.515.9096%23id-name%3DCiteSeerX&amp;rft_id=info%3Adoi%2F10.2174%2F1385272003376292&amp;rft.aulast=Novak&amp;rft.aufirst=B&amp;rft.au=Hudlicky%2C+T&amp;rft.au=Reed%2C+J&amp;rft.au=Mulzer%2C+J&amp;rft.au=Trauner%2C+D&amp;rft_id=http%3A%2F%2Fbrocku.ca%2Fmathematics-science%2Fdepartments-and-centres%2Fchemistry%2Ffaculty%2FHudlicky%2FCurrOrgChem-2000-4-343.pdf&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-102"><span class="mw-cite-backlink"><b><a href="#cite_ref-102">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLe_Page2015" class="citation magazine cs1">Le Page M (18 May 2015). <a rel="nofollow" class="external text" href="https://www.newscientist.com/article/dn27546-home-brew-heroin-soon-anyone-will-be-able-to-make-illegal-drugs/">"Home-brew heroin: soon anyone will be able to make illegal drugs"</a>. <i>New Scientist</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160413033207/https://www.newscientist.com/article/dn27546-home-brew-heroin-soon-anyone-will-be-able-to-make-illegal-drugs/">Archived</a> from the original on 13 April 2016.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=New+Scientist&amp;rft.atitle=Home-brew+heroin%3A+soon+anyone+will+be+able+to+make+illegal+drugs&amp;rft.date=2015-05-18&amp;rft.aulast=Le+Page&amp;rft.aufirst=M&amp;rft_id=https%3A%2F%2Fwww.newscientist.com%2Farticle%2Fdn27546-home-brew-heroin-soon-anyone-will-be-able-to-make-illegal-drugs%2F&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-103"><span class="mw-cite-backlink"><b><a href="#cite_ref-103">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFService2015" class="citation web cs1">Service RF (25 June 2015). <a rel="nofollow" class="external text" href="https://www.science.org/content/article/final-step-sugar-morphine-conversion-deciphered">"Final step in sugar-to-morphine conversion deciphered"</a>. Science. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150821122148/http://news.sciencemag.org/biology/2015/06/final-step-sugar-morphine-conversion-deciphered">Archived</a> from the original on 21 August 2015.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=Final+step+in+sugar-to-morphine+conversion+deciphered&amp;rft.pub=Science&amp;rft.date=2015-06-25&amp;rft.aulast=Service&amp;rft.aufirst=RF&amp;rft_id=https%3A%2F%2Fwww.science.org%2Fcontent%2Farticle%2Ffinal-step-sugar-morphine-conversion-deciphered&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-104"><span class="mw-cite-backlink"><b><a href="#cite_ref-104">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGalanieThodeyTrenchardFilsinger_Interrante2015" class="citation journal cs1">Galanie S, Thodey K, Trenchard IJ, Filsinger Interrante M, Smolke CD (September 2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4924617">"Complete biosynthesis of opioids in yeast"</a>. <i>Science</i>. <b>349</b> (6252): <span class="nowrap">1095–</span>100. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2015Sci...349.1095G">2015Sci...349.1095G</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.aac9373">10.1126/science.aac9373</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a>&#160;<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4924617">4924617</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/26272907">26272907</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Science&amp;rft.atitle=Complete+biosynthesis+of+opioids+in+yeast&amp;rft.volume=349&amp;rft.issue=6252&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E1095-%3C%2Fspan%3E100&amp;rft.date=2015-09&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4924617%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F26272907&amp;rft_id=info%3Adoi%2F10.1126%2Fscience.aac9373&amp;rft_id=info%3Abibcode%2F2015Sci...349.1095G&amp;rft.aulast=Galanie&amp;rft.aufirst=S&amp;rft.au=Thodey%2C+K&amp;rft.au=Trenchard%2C+IJ&amp;rft.au=Filsinger+Interrante%2C+M&amp;rft.au=Smolke%2C+CD&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4924617&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-105"><span class="mw-cite-backlink"><b><a href="#cite_ref-105">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://mobile.the-scientist.com/article/43739/yeast-based-opioid-production-completed">"Yeast-Based Opioid Production Completed"</a>. 13 August 2015. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150907025856/http://mobile.the-scientist.com/article/43739/yeast-based-opioid-production-completed">Archived</a> from the original on 7 September 2015<span class="reference-accessdate">. Retrieved <span class="nowrap">15 August</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=Yeast-Based+Opioid+Production+Completed&amp;rft.date=2015-08-13&amp;rft_id=http%3A%2F%2Fmobile.the-scientist.com%2Farticle%2F43739%2Fyeast-based-opioid-production-completed&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-106"><span class="mw-cite-backlink"><b><a href="#cite_ref-106">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOlawaleOkoliFontenotHollerman2016" class="citation book cs1">Olawale DO, Okoli OO, Fontenot RS, Hollerman WA (2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=5G6zDAAAQBAJ"><i>Triboluminescence: Theory, Synthesis, and Application</i></a> (illustrated&#160;ed.). Springer. p.&#160;193. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-3-319-38842-7" title="Special:BookSources/978-3-319-38842-7"><bdi>978-3-319-38842-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Triboluminescence%3A+Theory%2C+Synthesis%2C+and+Application&amp;rft.pages=193&amp;rft.edition=illustrated&amp;rft.pub=Springer&amp;rft.date=2016&amp;rft.isbn=978-3-319-38842-7&amp;rft.aulast=Olawale&amp;rft.aufirst=DO&amp;rft.au=Okoli%2C+OO&amp;rft.au=Fontenot%2C+RS&amp;rft.au=Hollerman%2C+WA&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5G6zDAAAQBAJ&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span> <a rel="nofollow" class="external text" href="https://books.google.com/books?id=5G6zDAAAQBAJ&amp;pg=PA193">Extract of page 193</a></span> </li> <li id="cite_note-urlwww.auburn.edu-107"><span class="mw-cite-backlink"><b><a href="#cite_ref-urlwww.auburn.edu_107-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDeRuiter2000" class="citation web cs1">DeRuiter J (Fall 2000). <a rel="nofollow" class="external text" href="http://www.auburn.edu/~deruija/opioids_morphine.pdf">"Narcotic analgesics: morphine and "peripherally modified" morphine analogs"</a> <span class="cs1-format">(PDF)</span>. <i>Principles of Drug Action 2</i>. Auburn University. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20120111171903/http://www.auburn.edu/~deruija/opioids_morphine.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 11 January 2012.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Principles+of+Drug+Action+2&amp;rft.atitle=Narcotic+analgesics%3A+morphine+and+%22peripherally+modified%22+morphine+analogs&amp;rft.ssn=fall&amp;rft.date=2000&amp;rft.aulast=DeRuiter&amp;rft.aufirst=J&amp;rft_id=http%3A%2F%2Fwww.auburn.edu%2F~deruija%2Fopioids_morphine.pdf&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-108"><span class="mw-cite-backlink"><b><a href="#cite_ref-108">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWayAdler1962" class="citation journal cs1">Way EL, Adler TK (1962). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2555766">"The biological disposition of morphine and its surrogates"</a>. <i>Bulletin of the World Health Organization</i>. <b>27</b> (3): <span class="nowrap">359–</span>394. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a>&#160;<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2555766">2555766</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/13999272">13999272</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Bulletin+of+the+World+Health+Organization&amp;rft.atitle=The+biological+disposition+of+morphine+and+its+surrogates&amp;rft.volume=27&amp;rft.issue=3&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E359-%3C%2Fspan%3E394&amp;rft.date=1962&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2555766%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F13999272&amp;rft.aulast=Way&amp;rft.aufirst=EL&amp;rft.au=Adler%2C+TK&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2555766&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-109"><span class="mw-cite-backlink"><b><a href="#cite_ref-109">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1958-01-01_3_page006.html">"UNODC - Bulletin on Narcotics - 1958 Issue 3 - 005"</a>. <i>United Nations&#160;: Office on Drugs and Crime</i><span class="reference-accessdate">. Retrieved <span class="nowrap">11 February</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=United+Nations+%3A+Office+on+Drugs+and+Crime&amp;rft.atitle=UNODC+-+Bulletin+on+Narcotics+-+1958+Issue+3+-+005&amp;rft_id=https%3A%2F%2Fwww.unodc.org%2Funodc%2Fen%2Fdata-and-analysis%2Fbulletin%2Fbulletin_1958-01-01_3_page006.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-110"><span class="mw-cite-backlink"><b><a href="#cite_ref-110">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><a rel="nofollow" class="external text" href="http://www.ncbi.nlm.nih.gov/books/NBK547864/">"Opioids"</a>, <i>LiverTox: Clinical and Research Information on Drug-Induced Liver Injury</i>, Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases, 2012, <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/31643200">31643200</a><span class="reference-accessdate">, retrieved <span class="nowrap">14 November</span> 2023</span></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=LiverTox%3A+Clinical+and+Research+Information+on+Drug-Induced+Liver+Injury&amp;rft.atitle=Opioids&amp;rft.date=2012&amp;rft_id=info%3Apmid%2F31643200&amp;rft_id=http%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fbooks%2FNBK547864%2F&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-111"><span class="mw-cite-backlink"><b><a href="#cite_ref-111">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLoftsson2013" class="citation book cs1">Loftsson T (2013). <a rel="nofollow" class="external text" href="http://worldcat.org/oclc/1136560730"><i>Drug Stability for Pharmaceutical Scientists</i></a>. Elsevier Science &amp; Technology. p.&#160;82. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a>&#160;<a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/1136560730">1136560730</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Drug+Stability+for+Pharmaceutical+Scientists&amp;rft.pages=82&amp;rft.pub=Elsevier+Science+%26+Technology&amp;rft.date=2013&amp;rft_id=info%3Aoclcnum%2F1136560730&amp;rft.aulast=Loftsson&amp;rft.aufirst=T&amp;rft_id=http%3A%2F%2Fworldcat.org%2Foclc%2F1136560730&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-112"><span class="mw-cite-backlink"><b><a href="#cite_ref-112">^</a></b></span> <span class="reference-text">Heroin (morphine diacetate) is a Schedule I controlled substance, so it is not used clinically in the United States;<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> it is a sanctioned medication in the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a> and in <a href="/wiki/Canada" title="Canada">Canada</a> and some countries in Continental Europe, its use being particularly common (nearly to the degree of the hydrochloride salt)<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (February 2020)">clarification needed</span></a></i>&#93;</sup> in the United Kingdom.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup></span> </li> <li id="cite_note-113"><span class="mw-cite-backlink"><b><a href="#cite_ref-113">^</a></b></span> <span class="reference-text">Morphine valerate was one ingredient of a medication available for both oral and parenteral administration popular many years ago in Europe and elsewhere called Trivalin—not to be confused with the current, unrelated herbal preparation of the same name—which also included the valerates of <a href="/wiki/Caffeine" title="Caffeine">caffeine</a> and <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup> A version containing codeine valerate as a fourth ingredient is distributed under the name Tetravalin.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2020)">citation needed</span></a></i>&#93;</sup></span> </li> <li id="cite_note-114"><span class="mw-cite-backlink"><b><a href="#cite_ref-114">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGatesTschudi1956" class="citation journal cs1">Gates M, Tschudi G (April 1956). 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Archived from <a rel="nofollow" class="external text" href="https://books.google.com/books?id=8A09AAAAcAAJ&amp;pg=PA229">the original</a> on 17 August 2016.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+der+Pharmacie+f%C3%BCr+Aerzte%2C+Apotheker+und+Chemisten&amp;rft.atitle=Friedrich+Sert%C3%BCrner+%28Untitled+letter+to+the+editor%29&amp;rft.volume=13&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E229-%3C%2Fspan%3E243%2C+see+especially+%22III.+S%C3%A4ure+im+Opium%22+%28acid+in+opium%29%2C+pp.+234-235%2C+and+%22I.+Nachtrag+zur+Charakteristik+der+S%C3%A4ure+im+Opium%22+%28Addendum+on+the+characteristics+of+the+acid+in+opium%29%2C+pp.+236-241&amp;rft.date=1805&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D8A09AAAAcAAJ%26pg%3DPA229&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-Dahan2010-135"><span class="mw-cite-backlink">^ <a href="#cite_ref-Dahan2010_135-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Dahan2010_135-1"><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="CITEREFDahanAartsSmith2010" class="citation journal cs1">Dahan A, Aarts L, Smith TW (January 2010). <a rel="nofollow" class="external text" href="https://doi.org/10.1097%2FALN.0b013e3181c38c25">"Incidence, Reversal, and Prevention of Opioid-induced Respiratory Depression"</a>. <i>Anesthesiology</i>. <b>112</b> (1): <span class="nowrap">226–</span>38. <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/10.1097%2FALN.0b013e3181c38c25">10.1097/ALN.0b013e3181c38c25</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20010421">20010421</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Anesthesiology&amp;rft.atitle=Incidence%2C+Reversal%2C+and+Prevention+of+Opioid-induced+Respiratory+Depression&amp;rft.volume=112&amp;rft.issue=1&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E226-%3C%2Fspan%3E38&amp;rft.date=2010-01&amp;rft_id=info%3Adoi%2F10.1097%2FALN.0b013e3181c38c25&amp;rft_id=info%3Apmid%2F20010421&amp;rft.aulast=Dahan&amp;rft.aufirst=A&amp;rft.au=Aarts%2C+L&amp;rft.au=Smith%2C+TW&amp;rft_id=https%3A%2F%2Fdoi.org%2F10.1097%252FALN.0b013e3181c38c25&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-136"><span class="mw-cite-backlink"><b><a href="#cite_ref-136">^</a></b></span> <span class="reference-text">Sertürner coined the term <i>morphium</i> in: Sertuerner (1817) <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=uc1.b4433519;view=1up;seq=74">"Ueber das Morphium, eine neue salzfähige Grundlage, und die Mekonsäure, als Hauptbestandtheile des Opiums"</a> (On morphine, a new salifiable [i.e., precipitable], fundamental substance, and meconic acid, as principal components of opium), <i>Annalen der Physik</i>, <b>55</b>&#160;: 56–89. It was <a href="/wiki/Joseph_Louis_Gay-Lussac" title="Joseph Louis Gay-Lussac">Gay-Lussac</a>, a French chemist and editor of <i>Annales de Chimie et de Physique</i>, who coined the word <i>morphine</i> in a French translation of Sertuener's original German article: Sertuener (1817) <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=nyp.33433062742444;view=1up;seq=29">"Analyse de l'opium: De la morphine et de l'acide méconique, considérés comme parties essentielles de l'opium"</a> (Analysis of opium: On morphine and on meconic acid, considered as essential constituents of opium), <i>Annales de Chimie et de Physique</i>, 2nd series, <b>5</b>&#160;: 21–42. From p. 22: <i>" ... car il a pris pour cette substance, que j'appelle </i>morphine<i> (</i>morphium<i>), ce qui n'en était qu'une combinaison avec </i>l'acide de l'opium<i>."</i> ( ... for he [i.e., French chemist and pharmacist Charles Derosne (1780–1846)] took as that substance [i.e., the active ingredient in opium], which I call "morphine" (or <i>morphium</i>), what was only a compound of it with <i>acid of opium</i>.)</span> </li> <li id="cite_note-137"><span class="mw-cite-backlink"><b><a href="#cite_ref-137">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOffit2017" class="citation journal cs1">Offit P (March–April 2017). "God's Own Medicine". <i><a href="/wiki/Skeptical_Inquirer" title="Skeptical Inquirer">Skeptical Inquirer</a></i>. <b>41</b> (2): 44.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Skeptical+Inquirer&amp;rft.atitle=God%27s+Own+Medicine&amp;rft.volume=41&amp;rft.issue=2&amp;rft.pages=44&amp;rft.date=2017-03%2F2017-04&amp;rft.aulast=Offit&amp;rft.aufirst=P&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-138"><span class="mw-cite-backlink"><b><a href="#cite_ref-138">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://archive.org/details/annualregister03dodsgoog"><i>Annual Register</i></a>. J. Dodsley. 1824. p.&#160;<a rel="nofollow" class="external text" href="https://archive.org/details/annualregister03dodsgoog/page/n2">1</a><span class="reference-accessdate">. Retrieved <span class="nowrap">1 September</span> 2015</span>. <q>Edme.</q></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Annual+Register&amp;rft.pages=1&amp;rft.pub=J.+Dodsley&amp;rft.date=1824&amp;rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fannualregister03dodsgoog&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-139"><span class="mw-cite-backlink"><b><a href="#cite_ref-139">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKirsch2016" class="citation book cs1">Kirsch DR (2016). <a rel="nofollow" class="external text" href="https://www.worldcat.org/oclc/966360188"><i>Drug Hunters</i></a>. Arcade Publishing. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-1-62872-719-7" title="Special:BookSources/978-1-62872-719-7"><bdi>978-1-62872-719-7</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a>&#160;<a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/966360188">966360188</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Drug+Hunters.&amp;rft.pub=Arcade+Publishing&amp;rft.date=2016&amp;rft_id=info%3Aoclcnum%2F966360188&amp;rft.isbn=978-1-62872-719-7&amp;rft.aulast=Kirsch&amp;rft.aufirst=DR&amp;rft_id=https%3A%2F%2Fwww.worldcat.org%2Foclc%2F966360188&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> <li id="cite_note-140"><span class="mw-cite-backlink"><b><a href="#cite_ref-140">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGootenberg1999" class="citation book cs1">Gootenberg P (1999). <a rel="nofollow" class="external text" href="https://www.worldcat.org/oclc/1162209949"><i>Cocaine global histories</i></a>. 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Retrieved <span class="nowrap">11 September</span> 2007</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=The+New+York+Times&amp;rft.atitle=Drugs+Banned%2C+Many+of+World%27s+Poor+Suffer+in+Pain&amp;rft.date=2007-09-10&amp;rft.aulast=McNeil+Jr&amp;rft.aufirst=DG&amp;rft_id=https%3A%2F%2Fwww.nytimes.com%2F2007%2F09%2F10%2Fhealth%2F10pain.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AMorphine" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Morphine&amp;action=edit&amp;section=46" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 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a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Components_of_opium" title="Template:Components of opium"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Components_of_opium" title="Template talk:Components of opium"><abbr title="Discuss this template">t</abbr></a></li><li 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(page does not exist)">Codamine</a></li> <li><a href="/wiki/Coptisine" title="Coptisine">Coptisine</a></li> <li><a href="/w/index.php?title=Coreximine&amp;action=edit&amp;redlink=1" class="new" title="Coreximine (page does not exist)">Coreximine</a></li> <li><a href="/w/index.php?title=Cycloartenone&amp;action=edit&amp;redlink=1" class="new" title="Cycloartenone (page does not exist)">Cycloartenone</a></li> <li><a href="/w/index.php?title=Cyclolaudenol&amp;action=edit&amp;redlink=1" class="new" title="Cyclolaudenol (page does not exist)">Cyclolaudenol</a></li> <li><a href="/w/index.php?title=Dehydroreticuline&amp;action=edit&amp;redlink=1" class="new" title="Dehydroreticuline (page does not exist)">Dehydroreticuline</a></li> <li><a href="/wiki/Dihydrosanguinarine" title="Dihydrosanguinarine">Dihydrosanguinarine</a></li> <li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/wiki/Isoboldine" class="mw-redirect" title="Isoboldine">Isoboldine</a></li> <li><a href="/w/index.php?title=Isocorypalmine&amp;action=edit&amp;redlink=1" class="new" title="Isocorypalmine (page does not exist)">Isocorypalmine</a></li> <li><a href="/w/index.php?title=Laudanidine&amp;action=edit&amp;redlink=1" class="new" title="Laudanidine (page does not exist)">Laudanidine</a></li> <li><a href="/wiki/Magnoflorine" title="Magnoflorine">Magnoflorine</a></li> <li><a href="/wiki/Narceine" title="Narceine">Narceine</a></li> <li><a href="/w/index.php?title=Narceinone&amp;action=edit&amp;redlink=1" class="new" title="Narceinone (page does not exist)">Narceinone</a></li> <li><a href="/wiki/Norlaudanosoline" class="mw-redirect" title="Norlaudanosoline">Norlaudanosoline</a></li> <li><a href="/w/index.php?title=Norsanguinarine&amp;action=edit&amp;redlink=1" class="new" title="Norsanguinarine (page does not exist)">Norsanguinarine</a></li> <li><a href="/wiki/Oripavine" title="Oripavine">Oripavine</a></li> <li><a href="/w/index.php?title=Oxysanguinarine&amp;action=edit&amp;redlink=1" class="new" title="Oxysanguinarine (page does not exist)">Oxysanguinarine</a></li> <li><a href="/w/index.php?title=Palaudine&amp;action=edit&amp;redlink=1" class="new" title="Palaudine (page does not exist)">Palaudine</a></li> <li><a href="/w/index.php?title=Papaverrubine_B&amp;action=edit&amp;redlink=1" class="new" title="Papaverrubine B (page does not exist)">Papaverrubine B (O-methyl-porphyroxine)</a></li> <li><a href="/w/index.php?title=Papaverrubine_C&amp;action=edit&amp;redlink=1" class="new" title="Papaverrubine C (page does not exist)">Papaverrubine C (epiporphyroxine)</a></li> <li><a href="/wiki/Reticuline" title="Reticuline">Reticuline</a></li> <li><a href="/wiki/Salutaridine" title="Salutaridine">Salutaridine (sinoacutine)</a></li> <li><a href="/wiki/Sanguinarine" title="Sanguinarine">Sanguinarine</a></li> <li><a href="/wiki/Scoulerine" title="Scoulerine">Scoulerine</a></li> <li><a href="/w/index.php?title=Somniferine&amp;action=edit&amp;redlink=1" class="new" title="Somniferine (page does not exist)">Somniferine</a></li> <li><a href="/wiki/Stepholidine" title="Stepholidine">Stepholidine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;"><a class="mw-selflink selflink">Morphine</a> group<br />(<a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrenes</a>. Includes <a href="/wiki/Template:Opioids" class="mw-redirect" title="Template:Opioids">opioids</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/Codeine" title="Codeine">Codeine</a></li> <li><a class="mw-selflink selflink">Morphine</a></li> <li><a href="/wiki/Narcotoline" title="Narcotoline">Narcotoline</a></li> <li><a href="/w/index.php?title=Neopine&amp;action=edit&amp;redlink=1" class="new" title="Neopine (page does not exist)">Neopine</a></li> <li><a href="/w/index.php?title=Perparin&amp;action=edit&amp;redlink=1" class="new" title="Perparin (page does not exist)">Perparin</a></li> <li><a href="/w/index.php?title=Porphyroxine&amp;action=edit&amp;redlink=1" class="new" title="Porphyroxine (page does not exist)">Papaverrubine D (porphyroxine)</a></li> <li><a href="/w/index.php?title=Pseudocodeine&amp;action=edit&amp;redlink=1" class="new" title="Pseudocodeine (page does not exist)">Pseudocodeine</a></li> <li><a href="/wiki/Pseudomorphine" title="Pseudomorphine">Pseudomorphine</a></li> <li><a href="/wiki/Thebaine" title="Thebaine">Thebaine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;"><a href="/wiki/Isoquinoline" title="Isoquinoline">Isoquinolines</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=Cotarnine&amp;action=edit&amp;redlink=1" class="new" title="Cotarnine (page does not exist)">Cotarnine</a></li> <li><a href="/w/index.php?title=Eupaverine&amp;action=edit&amp;redlink=1" class="new" title="Eupaverine (page does not exist)">Eupaverine</a></li> <li><a href="/w/index.php?title=Hydrocotarnine&amp;action=edit&amp;redlink=1" class="new" title="Hydrocotarnine (page does not exist)">Hydrocotarnine</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/wiki/Laudanine" class="mw-redirect" title="Laudanine">Laudanine</a></li> <li><a href="/wiki/Noscapine" title="Noscapine">Noscapine (narcotine)</a></li> <li><a href="/wiki/Papaverine" title="Papaverine">Papaverine</a></li> <li><a href="/w/index.php?title=Papaveraldine&amp;action=edit&amp;redlink=1" class="new" title="Papaveraldine (page does not exist)">Papaveraldine</a></li> <li><a href="/w/index.php?title=Xanthaline&amp;action=edit&amp;redlink=1" class="new" title="Xanthaline (page does not exist)">Xanthaline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;"><a href="/wiki/Protopine" title="Protopine">Protopine</a> group</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/Allocryptopine" title="Allocryptopine">α-Allocryptopine</a></li> <li><a href="/w/index.php?title=Corycavamine&amp;action=edit&amp;redlink=1" class="new" title="Corycavamine (page does not exist)">Corycavamine</a></li> <li><a href="/w/index.php?title=Corycavine&amp;action=edit&amp;redlink=1" class="new" title="Corycavine (page does not exist)">Corycavine</a></li> <li><a href="/wiki/Cryptopine" title="Cryptopine">Cryptopine</a></li> <li><a href="/wiki/Protopine" title="Protopine">Protopine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;"><a href="/w/index.php?title=Tetrahydroprotoberberine&amp;action=edit&amp;redlink=1" class="new" title="Tetrahydroprotoberberine (page does not exist)">Tetrahydroprotoberberine</a> group</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/Corydaline" title="Corydaline">Corydaline</a></li> <li><a href="/w/index.php?title=Corybulbine&amp;action=edit&amp;redlink=1" class="new" title="Corybulbine (page does not exist)">Corybulbine</a></li> <li><a href="/w/index.php?title=Isocorybulbine&amp;action=edit&amp;redlink=1" class="new" title="Isocorybulbine (page does not exist)">Isocorybulbine</a></li> <li><a href="/w/index.php?title=Capaurine&amp;action=edit&amp;redlink=1" class="new" title="Capaurine (page does not exist)">Capaurine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;"><a href="/wiki/Aporphine" title="Aporphine">Aporphine</a> group</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/Dicentrine" title="Dicentrine">Dicentrine</a></li> <li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/w/index.php?title=Corytuberine&amp;action=edit&amp;redlink=1" class="new" title="Corytuberine (page does not exist)">Corytuberine</a></li> <li><a href="/w/index.php?title=Cularine&amp;action=edit&amp;redlink=1" class="new" title="Cularine (page does not exist)">Cularine</a></li> <li><a href="/w/index.php?title=Corydine&amp;action=edit&amp;redlink=1" class="new" title="Corydine (page does not exist)">Corydine</a></li> <li><a href="/w/index.php?title=Isocorydine&amp;action=edit&amp;redlink=1" class="new" title="Isocorydine (page does not exist)">Isocorydine</a></li> <li><a href="/wiki/Bulbocapnine" title="Bulbocapnine">Bulbocapnine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;"><a href="/w/index.php?title=Phtalide-isoquinoline&amp;action=edit&amp;redlink=1" class="new" title="Phtalide-isoquinoline (page does not exist)">Phtalide-isoquinolines</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=Adulmine&amp;action=edit&amp;redlink=1" class="new" title="Adulmine (page does not exist)">Adulmine</a></li> <li><a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/w/index.php?title=Bicucine&amp;action=edit&amp;redlink=1" class="new" title="Bicucine (page does not exist)">Bicucine</a></li> <li><a href="/w/index.php?title=Corlumine&amp;action=edit&amp;redlink=1" class="new" title="Corlumine (page does not exist)">Corlumine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;"><a href="/w/index.php?title=%CE%91-Naphthaphenanthridine&amp;action=edit&amp;redlink=1" class="new" title="Α-Naphthaphenanthridine (page does not exist)">α-Naphthaphenanthridines</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/Chelidonine" title="Chelidonine">Chelidonine</a></li> <li><a href="/w/index.php?title=%CE%92-Homochelidonoine&amp;action=edit&amp;redlink=1" class="new" title="Β-Homochelidonoine (page does not exist)">β-Homochelidonoine</a></li> <li><a href="/wiki/Chelerythrine" title="Chelerythrine">Chelerythrine</a></li> <li><a href="/wiki/Sanguinarine" title="Sanguinarine">Sanguinarine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;">Other components</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/Meconic_acid" title="Meconic acid">Meconic acid</a></li> <li><a href="/wiki/Cycloartenol" title="Cycloartenol">Cycloartenol</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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Analgesics_(N02A,_N02B)251" 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:Analgesics" title="Template:Analgesics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Analgesics" title="Template talk:Analgesics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Analgesics" title="Special:EditPage/Template:Analgesics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Analgesics_(N02A,_N02B)251" style="font-size:114%;margin:0 4em"><a href="/wiki/Analgesic" title="Analgesic">Analgesics</a> (<a href="/wiki/ATC_code_N02#N02A" title="ATC code N02">N02A</a>, <a href="/wiki/ATC_code_N02#N02B" title="ATC code N02">N02B</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opioid" title="Opioid">Opioids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opiate" title="Opiate">Opiates</a>/<a href="/wiki/Opium" title="Opium">opium</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/Codeine" title="Codeine">Codeine</a><sup>#</sup> <ul><li><a href="/wiki/Codeine/aspirin" class="mw-redirect" title="Codeine/aspirin">+aspirin</a></li> <li><a href="/wiki/Codeine/paracetamol" title="Codeine/paracetamol">+paracetamol</a></li></ul></li> <li><a class="mw-selflink selflink">Morphine</a><sup>#</sup> (<a href="/wiki/Morphine/naltrexone" title="Morphine/naltrexone">+naltrexone</a>)</li> <li><a href="/wiki/Opium" title="Opium">Opium</a></li> <li><a href="/wiki/Laudanum" title="Laudanum">Laudanum</a></li> <li><a href="/wiki/Paregoric" title="Paregoric">Paregoric</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Semisynthetic</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/Acetyldihydrocodeine" title="Acetyldihydrocodeine">Acetyldihydrocodeine</a></li> <li><a href="/wiki/Benzylmorphine" title="Benzylmorphine">Benzylmorphine</a></li> <li><a href="/wiki/Buprenorphine" title="Buprenorphine">Buprenorphine</a><span class="nowrap">&#160;</span>(<a href="/wiki/Buprenorphine/naloxone" title="Buprenorphine/naloxone">+naloxone</a>)</li> <li><a href="/wiki/Butorphanol" title="Butorphanol">Butorphanol</a></li> <li><a href="/wiki/Desomorphine" title="Desomorphine">Desomorphine</a></li> <li><a href="/wiki/Heroin" title="Heroin">Diamorphine (heroin)</a></li> <li><a href="/wiki/Dihydrocodeine" title="Dihydrocodeine">Dihydrocodeine</a><span class="nowrap">&#160;</span>(<a href="/wiki/Co-dydramol" title="Co-dydramol">+paracetamol</a>)</li> <li><a href="/wiki/Dihydromorphine" title="Dihydromorphine">Dihydromorphine</a></li> <li><a href="/wiki/Etorphine" title="Etorphine">Etorphine</a></li> <li><a href="/wiki/Ethylmorphine" title="Ethylmorphine">Ethylmorphine</a></li> <li><a href="/wiki/Hydrocodone" title="Hydrocodone">Hydrocodone</a><span class="nowrap">&#160;</span>(<a href="/wiki/Hydrocodone/paracetamol" title="Hydrocodone/paracetamol">+paracetamol</a>, <a href="/wiki/Hydrocodone/ibuprofen" title="Hydrocodone/ibuprofen">+ibuprofen</a>, <a href="/wiki/Hydrocodone/aspirin" title="Hydrocodone/aspirin">+aspirin</a>)</li> <li><a href="/wiki/Hydromorphinol" title="Hydromorphinol">Hydromorphinol</a></li> <li><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone</a></li> <li><a href="/wiki/Levorphanol" title="Levorphanol">Levorphanol</a></li> <li><a href="/wiki/Metopon" title="Metopon">Metopon</a></li> <li><a href="/wiki/Nalbuphine" title="Nalbuphine">Nalbuphine</a></li> <li><a href="/wiki/Nicocodeine" title="Nicocodeine">Nicocodeine</a></li> <li><a href="/wiki/Nicodicodine" title="Nicodicodine">Nicodicodine</a></li> <li><a href="/wiki/Nicomorphine" title="Nicomorphine">Nicomorphine</a></li> <li><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a><span class="nowrap">&#160;</span>(<a href="/wiki/Oxycodone/paracetamol" title="Oxycodone/paracetamol">+paracetamol</a>, <a href="/wiki/Oxycodone/aspirin" title="Oxycodone/aspirin">+aspirin</a>, <a href="/wiki/Oxycodone/ibuprofen" title="Oxycodone/ibuprofen">+ibuprofen</a>, <a href="/wiki/Oxycodone/naloxone" title="Oxycodone/naloxone">+naloxone</a>, <a href="/w/index.php?title=Oxycodone/naltrexone&amp;action=edit&amp;redlink=1" class="new" title="Oxycodone/naltrexone (page does not exist)">+naltrexone</a>)</li> <li><a href="/wiki/Oxymorphone" title="Oxymorphone">Oxymorphone</a></li> <li><a href="/wiki/Papaveretum" title="Papaveretum">Papaveretum</a></li> <li><a href="/wiki/Thebacon" title="Thebacon">Thebacon</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Synthetic</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/Alfentanil" title="Alfentanil">Alfentanil</a></li> <li><a href="/wiki/Prodine" title="Prodine">Alphaprodine</a></li> <li><a href="/wiki/Anileridine" title="Anileridine">Anileridine</a></li> <li><a href="/wiki/Bezitramide" title="Bezitramide">Bezitramide</a></li> <li><a href="/wiki/Carfentanil" title="Carfentanil">Carfentanil</a></li> <li><a href="/wiki/Dextromoramide" title="Dextromoramide">Dextromoramide</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a></li> <li><a href="/wiki/Dezocine" title="Dezocine">Dezocine</a></li> <li><a href="/wiki/Dimenoxadol" title="Dimenoxadol">Dimenoxadol</a></li> <li><a href="/wiki/Dipipanone" title="Dipipanone">Dipipanone</a></li> <li><a href="/wiki/Ethoheptazine" title="Ethoheptazine">Ethoheptazine</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a><sup>#</sup> (<a href="/wiki/Fentanyl/fluanisone" title="Fentanyl/fluanisone">+fluanisone</a>)</li> <li><a href="/wiki/Ketobemidone" title="Ketobemidone">Ketobemidone</a></li> <li><a href="/wiki/Lofentanil" title="Lofentanil">Lofentanil</a></li> <li><a href="/wiki/Meptazinol" title="Meptazinol">Meptazinol</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a><sup>#</sup></li> <li><a href="/wiki/NFEPP" title="NFEPP">NFEPP</a></li> <li><a href="/wiki/Norpipanone" title="Norpipanone">Norpipanone</a></li> <li><a href="/wiki/Oliceridine" title="Oliceridine">Oliceridine</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine (meperidine)</a></li> <li><a href="/wiki/Phenadoxone" title="Phenadoxone">Phenadoxone</a></li> <li><a href="/wiki/Phenazocine" title="Phenazocine">Phenazocine</a></li> <li><a href="/wiki/Phenoperidine" title="Phenoperidine">Phenoperidine</a></li> <li><a href="/wiki/Piminodine" title="Piminodine">Piminodine</a></li> <li><a href="/wiki/Piritramide" title="Piritramide">Piritramide</a></li> <li><a href="/wiki/Proheptazine" title="Proheptazine">Proheptazine</a></li> <li><a href="/wiki/Propiram" title="Propiram">Propiram</a></li> <li><a href="/wiki/Remifentanil" title="Remifentanil">Remifentanil</a></li> <li><a href="/wiki/Sufentanil" title="Sufentanil">Sufentanil</a></li> <li><a href="/wiki/Tapentadol" title="Tapentadol">Tapentadol</a></li> <li><a href="/wiki/Tilidine" title="Tilidine">Tilidine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a><span class="nowrap">&#160;</span>(<a href="/wiki/Celecoxib/tramadol" title="Celecoxib/tramadol">+celecoxib</a>, <a href="/wiki/Tramadol/paracetamol" title="Tramadol/paracetamol">+paracetamol</a>)</li> <li><a href="/wiki/Viminol" title="Viminol">Viminol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol</a>-type</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/Acetanilide" title="Acetanilide">Acetanilide</a><sup>‡</sup></li> <li><a href="/wiki/Bucetin" title="Bucetin">Bucetin</a><sup>‡</sup></li> <li><a href="/w/index.php?title=Butacetin&amp;action=edit&amp;redlink=1" class="new" title="Butacetin (page does not exist)">Butacetin</a><sup>‡</sup></li> <li><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol (acetaminophen)</a><sup>#</sup> <ul><li><a href="/wiki/Aspirin/paracetamol/caffeine" title="Aspirin/paracetamol/caffeine">+aspirin/caffeine</a></li> <li><a href="/wiki/Codeine/paracetamol" title="Codeine/paracetamol">+codeine</a></li> <li><a href="/wiki/Hydrocodone/paracetamol" title="Hydrocodone/paracetamol">+hydrocodone</a></li> <li><a href="/wiki/Ibuprofen/paracetamol" title="Ibuprofen/paracetamol">+ibuprofen</a></li> <li><a href="/wiki/Paracetamol/metoclopramide" title="Paracetamol/metoclopramide">+metoclopramide</a></li> <li><a href="/wiki/Oxycodone/paracetamol" title="Oxycodone/paracetamol">+oxycodone</a></li> <li><a href="/wiki/Propyphenazone/paracetamol/caffeine" title="Propyphenazone/paracetamol/caffeine">+propyphenazone/caffeine</a></li> <li><a href="/wiki/Tramadol/paracetamol" title="Tramadol/paracetamol">+tramadol</a></li></ul></li> <li><a href="/w/index.php?title=Parapropamol&amp;action=edit&amp;redlink=1" class="new" title="Parapropamol (page does not exist)">Parapropamol</a><sup>‡</sup></li> <li><a href="/wiki/Phenacetin" title="Phenacetin">Phenacetin</a><sup>‡</sup></li> <li><a href="/wiki/Propacetamol" title="Propacetamol">Propacetamol</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nonsteroidal_anti-inflammatory_drug" title="Nonsteroidal anti-inflammatory drug">NSAIDs</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Propionates</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/Benoxaprofen" title="Benoxaprofen">Benoxaprofen</a> <sup>‡</sup></li> <li><a href="/wiki/Fenoprofen" title="Fenoprofen">Fenoprofen</a></li> <li><a href="/wiki/Flurbiprofen" title="Flurbiprofen">Flurbiprofen</a></li> <li><a href="/wiki/Ibuprofen" title="Ibuprofen">Ibuprofen</a><sup>#</sup><span class="nowrap">&#160;</span>(<a href="/wiki/Dexibuprofen" title="Dexibuprofen">Dexibuprofen</a>)<span class="nowrap">&#160;</span>(<a href="/wiki/Ibuprofen/paracetamol" title="Ibuprofen/paracetamol">+paracetamol</a>)</li> <li><a href="/wiki/Ketoprofen" title="Ketoprofen">Ketoprofen</a><span class="nowrap">&#160;</span>(<a href="/wiki/Dexketoprofen" title="Dexketoprofen">Dexketoprofen</a>)</li> <li><a href="/wiki/Loxoprofen" title="Loxoprofen">Loxoprofen</a></li> <li><a href="/wiki/Naproxen" title="Naproxen">Naproxen</a></li> <li><a href="/wiki/Oxaprozin" title="Oxaprozin">Oxaprozin</a></li> <li><a href="/wiki/Suprofen" title="Suprofen">Suprofen</a></li> <li><a href="/wiki/Tiaprofenic_acid" title="Tiaprofenic acid">Tiaprofenic acid</a></li> <li><a href="/wiki/Zaltoprofen" title="Zaltoprofen">Zaltoprofen</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Oxicams</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/Isoxicam" title="Isoxicam">Isoxicam</a></li> <li><a href="/wiki/Lornoxicam" title="Lornoxicam">Lornoxicam</a></li> <li><a href="/wiki/Meloxicam" title="Meloxicam">Meloxicam</a></li> <li><a href="/wiki/Piroxicam" title="Piroxicam">Piroxicam</a></li> <li><a href="/wiki/Tenoxicam" title="Tenoxicam">Tenoxicam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Acetates</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/Acemetacin" title="Acemetacin">Acemetacin</a></li> <li><a href="/wiki/Bromfenac" title="Bromfenac">Bromfenac</a></li> <li><a href="/wiki/Diclofenac" title="Diclofenac">Diclofenac</a></li> <li><a href="/wiki/Etodolac" title="Etodolac">Etodolac</a></li> <li><a href="/wiki/Indometacin" title="Indometacin">Indometacin</a><span class="nowrap">&#160;</span>(<a href="/wiki/Indometacin_farnesil" title="Indometacin farnesil">Indometacin farnesil</a>)</li> <li><a href="/wiki/Ketorolac" title="Ketorolac">Ketorolac</a></li> <li><a href="/wiki/Sulindac" title="Sulindac">Sulindac</a></li> <li><a href="/wiki/Tolmetin" title="Tolmetin">Tolmetin</a></li> <li><a href="/wiki/Zomepirac" title="Zomepirac">Zomepirac</a> <sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/COX-2_inhibitor" class="mw-redirect" title="COX-2 inhibitor">COX-2 inhibitors</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/Celecoxib" title="Celecoxib">Celecoxib</a><span class="nowrap">&#160;</span>(<a href="/wiki/Celecoxib/tramadol" title="Celecoxib/tramadol">+tramadol</a>)</li> <li><a href="/wiki/Etoricoxib" title="Etoricoxib">Etoricoxib</a></li> <li><a href="/wiki/Lumiracoxib" title="Lumiracoxib">Lumiracoxib</a> <sup>‡</sup></li> <li><a href="/wiki/Parecoxib" title="Parecoxib">Parecoxib</a></li> <li><a href="/wiki/Rofecoxib" title="Rofecoxib">Rofecoxib</a> <sup>‡</sup></li> <li><a href="/wiki/Valdecoxib" title="Valdecoxib">Valdecoxib</a> <sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Fenamic_acid" title="Fenamic acid">Fenamates</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/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><a href="/wiki/Mefenamic_acid" title="Mefenamic acid">Mefenamic acid</a></li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Salicylic_acid" title="Salicylic acid">Salicylates</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/Aspirin" title="Aspirin">Aspirin (acetylsalicylic acid)</a><sup>#</sup> (<a href="/wiki/Aspirin/paracetamol/caffeine" title="Aspirin/paracetamol/caffeine">+paracetamol/caffeine</a>)</li> <li><a href="/wiki/Aloxiprin" title="Aloxiprin">Aloxiprin</a></li> <li><a href="/wiki/Benorilate" title="Benorilate">Benorylate</a></li> <li><a href="/wiki/Carbasalate_calcium" title="Carbasalate calcium">Carbasalate calcium</a></li> <li><a href="/wiki/Choline_salicylate" class="mw-redirect" title="Choline salicylate">Choline salicylate</a></li> <li><a href="/wiki/Diflunisal" title="Diflunisal">Diflunisal</a></li> <li><a href="/wiki/Dipyrocetyl" title="Dipyrocetyl">Dipyrocetyl</a></li> <li><a href="/wiki/Ethenzamide" title="Ethenzamide">Ethenzamide</a></li> <li><a href="/wiki/Guacetisal" title="Guacetisal">Guacetisal</a></li> <li><a href="/wiki/Imidazole_salicylate" title="Imidazole salicylate">Imidazole salicylate</a></li> <li><a href="/wiki/Magnesium_salicylate" title="Magnesium salicylate">Magnesium salicylate</a></li> <li><a href="/wiki/Morpholine_salicylate" title="Morpholine salicylate">Morpholine salicylate</a></li> <li><a href="/wiki/Potassium_salicylate" title="Potassium salicylate">Potassium salicylate</a></li> <li><a href="/wiki/Salicin" title="Salicin">Salicin</a></li> <li><a href="/wiki/Salicylamide" title="Salicylamide">Salicylamide</a></li> <li><a href="/wiki/Salsalate" title="Salsalate">Salsalate</a></li> <li><a href="/wiki/Sodium_salicylate" title="Sodium salicylate">Sodium salicylate</a></li> <li><a href="/wiki/Wintergreen" title="Wintergreen">Wintergreen</a><span class="nowrap">&#160;</span>(<a href="/wiki/Methyl_salicylate" title="Methyl salicylate">methyl salicylate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrazolone" title="Pyrazolone">Pyrazolones</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/Aminophenazone" title="Aminophenazone">Aminophenazone</a><sup>‡</sup></li> <li><a href="/wiki/Ampyrone" title="Ampyrone">Ampyrone</a></li> <li><a href="/wiki/Metamizole" title="Metamizole">Metamizole (dipyrone)</a></li> <li><a href="/wiki/Nifenazone" title="Nifenazone">Nifenazone</a></li> <li><a href="/wiki/Phenazone" title="Phenazone">Phenazone</a></li> <li><a href="/wiki/Propyphenazone" title="Propyphenazone">Propyphenazone</a><span class="nowrap">&#160;</span>(<a href="/wiki/Propyphenazone/paracetamol/caffeine" title="Propyphenazone/paracetamol/caffeine">+paracetamol/caffeine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</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/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Floctafenine" title="Floctafenine">Floctafenine</a></li> <li><a href="/wiki/Glafenine" title="Glafenine">Glafenine</a></li> <li><a href="/wiki/Nabumetone" title="Nabumetone">Nabumetone</a></li> <li><a href="/wiki/Nimesulide" title="Nimesulide">Nimesulide</a></li> <li><a href="/wiki/Proquazone" title="Proquazone">Proquazone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cannabinoid" title="Cannabinoid">Cannabinoids</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/Cannabidiol" title="Cannabidiol">Cannabidiol</a></li> <li><a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">Cannabis</a></li> <li><a href="/wiki/Nabilone" title="Nabilone">Nabilone</a></li> <li><a href="/wiki/Nabiximols" title="Nabiximols">Nabiximols</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol (dronabinol)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Channel_modulator" title="Channel modulator">Ion channel<br />modulators</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">Calcium blockers</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/Alcohol_(drug)" title="Alcohol (drug)">Alcohol (ethanol)</a></li> <li><a href="/wiki/Gabapentin" title="Gabapentin">Gabapentin</a></li> <li><a href="/wiki/Gabapentin_enacarbil" title="Gabapentin enacarbil">Gabapentin enacarbil</a></li> <li><a href="/wiki/Leconotide" title="Leconotide">Leconotide</a></li> <li><a href="/wiki/Mirogabalin" title="Mirogabalin">Mirogabalin</a></li> <li><a href="/wiki/Pregabalin" title="Pregabalin">Pregabalin</a></li> <li><a href="/wiki/Ziconotide" title="Ziconotide">Ziconotide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sodium_channel_blocker" title="Sodium channel blocker">Sodium blockers</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/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Lacosamide" title="Lacosamide">Lacosamide</a></li> <li><a href="/wiki/Local_anesthetic" title="Local anesthetic">Local anesthetics</a> (e.g., <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/wiki/Lidocaine" title="Lidocaine">lidocaine</a>)</li> <li><a href="/wiki/Mexiletine" title="Mexiletine">Mexiletine</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a><sup>#</sup>)</li></ul> <ul><li><i>Na<sub>v</sub>1.7/1.8-selective:</i> <a href="/wiki/DSP-2230" title="DSP-2230">DSP-2230</a><sup>§</sup></li> <li><a href="/wiki/Funapide" title="Funapide">Funapide</a><sup>§</sup></li> <li><a href="/wiki/PF-05089771" title="PF-05089771">PF-05089771</a><sup>§</sup></li> <li><a href="/wiki/Suzetrigine" title="Suzetrigine">Suzetrigine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Potassium openers</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/Flupirtine" title="Flupirtine">Flupirtine</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Muscle_relaxant" title="Muscle relaxant">Myorelaxants</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/Carisoprodol" title="Carisoprodol">Carisoprodol</a></li> <li><a href="/wiki/Chlorzoxazone" title="Chlorzoxazone">Chlorzoxazone</a></li> <li><a href="/wiki/Cyclobenzaprine" title="Cyclobenzaprine">Cyclobenzaprine</a></li> <li><a href="/wiki/Mephenoxalone" title="Mephenoxalone">Mephenoxalone</a></li> <li><a href="/wiki/Methocarbamol" title="Methocarbamol">Methocarbamol</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</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/Analgecine" title="Analgecine">Analgecine</a></li> <li><a href="/wiki/Analgesic_adjuvant" title="Analgesic adjuvant">Analgesic adjuvant</a></li> <li><a href="/wiki/Bedinvetmab" title="Bedinvetmab">Bedinvetmab</a></li> <li><a href="/wiki/Camphor" title="Camphor">Camphor</a></li> <li><a href="/wiki/Capsaicin" title="Capsaicin">Capsaicin</a></li> <li><a href="/wiki/Clonidine" title="Clonidine">Clonidine</a></li> <li><a href="/wiki/Frunevetmab" title="Frunevetmab">Frunevetmab</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Phenazopyridine" title="Phenazopyridine">Phenazopyridine</a></li> <li><a href="/wiki/Proglumide" title="Proglumide">Proglumide</a></li> <li><a href="/wiki/Rimazolium" title="Rimazolium">Rimazolium</a></li> <li><a href="/wiki/Tanezumab" title="Tanezumab">Tanezumab</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="General_anesthetics_(N01A)155" 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:General_anesthetics" title="Template:General anesthetics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:General_anesthetics" title="Template talk:General anesthetics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:General_anesthetics" title="Special:EditPage/Template:General anesthetics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="General_anesthetics_(N01A)155" style="font-size:114%;margin:0 4em"><a href="/wiki/General_anaesthetic" title="General anaesthetic">General anesthetics</a> (<a href="/wiki/ATC_code_N01#N01A" title="ATC code N01">N01A</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inhalational_anesthetic" title="Inhalational anesthetic">Inhalational</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/Chloroform" title="Chloroform">Chloroform</a><sup>‡</sup></li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a><sup>‡</sup></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a><sup>‡</sup></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a><sup>‡</sup></li> <li><a href="/wiki/Fluroxene" title="Fluroxene">Fluroxene</a><sup>‡</sup></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a><sup>#</sup></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a><sup>#</sup></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Methoxypropane" title="Methoxypropane">Methoxypropane</a><sup>‡</sup></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a><sup>#</sup></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Trichloroethylene" title="Trichloroethylene">Trichloroethylene</a><sup>‡</sup></li> <li><a href="/wiki/Divinyl_ether" title="Divinyl ether">Vinyl ether</a><sup>‡</sup></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/General_anaesthetic#Injection" title="General anaesthetic">Injection</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenols" title="Phenols">Phenols</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/Ciprofol" title="Ciprofol">Ciprofol</a><sup>†</sup></li> <li><a href="/wiki/Fospropofol" title="Fospropofol">Fospropofol</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</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/Amobarbital" title="Amobarbital">Amobarbital</a></li> <li><a href="/wiki/Hexobarbital" title="Hexobarbital">Hexobarbital</a></li> <li><a href="/wiki/Methohexital" title="Methohexital">Methohexital</a></li> <li><a href="/wiki/Narcobarbital" title="Narcobarbital">Narcobarbital</a></li> <li><a href="/wiki/Thiamylal" title="Thiamylal">Thiamylal</a></li> <li><a href="/wiki/Sodium_thiopental" title="Sodium thiopental">Thiopental</a><sup>#</sup></li> <li><a href="/wiki/Thiotetrabarbital" title="Thiotetrabarbital">Thiotetrabarbital</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</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/Midazolam" title="Midazolam">Midazolam</a><sup>#</sup></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a><sup>#</sup></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a><sup>#</sup></li> <li><a href="/wiki/Remimazolam" title="Remimazolam">Remimazolam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opioid" title="Opioid">Opioids</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">Morphine</a><sup>#</sup></li> <li><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a></li> <li><a href="/wiki/Anileridine" title="Anileridine">Anileridine</a><sup>‡</sup></li> <li><a href="/wiki/Embutramide" title="Embutramide">Embutramide</a><sup>‡</sup></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a><sup>#</sup></li> <li><a href="/wiki/Alfentanil" title="Alfentanil">Alfentanil</a></li> <li><a href="/wiki/Phenoperidine" title="Phenoperidine">Phenoperidine</a></li> <li><a href="/wiki/Remifentanil" title="Remifentanil">Remifentanil</a>÷</li> <li><a href="/wiki/Sufentanil" title="Sufentanil">Sufentanil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclohexylamines</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/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a><sup>#</sup></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a><sup>‡</sup></li> <li><a href="/wiki/Tiletamine" title="Tiletamine">Tiletamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neurosteroid" title="Neurosteroid">Neuroactive steroids</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/Alfadolone" title="Alfadolone">Alfadolone</a></li> <li><a href="/wiki/Alfaxalone" title="Alfaxalone">Alfaxalone</a></li> <li><a href="/wiki/Hydroxydione" title="Hydroxydione">Hydroxydione</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</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/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Propanidid" title="Propanidid">Propanidid</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </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="Drugs_which_induce_euphoria105" style="padding:3px"><table class="nowraplinks hlist 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:Euphoriants" title="Template:Euphoriants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Euphoriants" title="Template talk:Euphoriants"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Euphoriants" title="Special:EditPage/Template:Euphoriants"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Drugs_which_induce_euphoria105" style="font-size:114%;margin:0 4em">Drugs which induce <a href="/wiki/Euphoriant" class="mw-redirect" title="Euphoriant">euphoria</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/%CE%9C-Opioid_receptor" class="mw-redirect" title="Μ-Opioid receptor">μ-Opioid receptor</a> <a href="/wiki/Agonist" title="Agonist">agonists</a> (<a href="/wiki/Opioid" title="Opioid">opioids</a>) (e.g., <a class="mw-selflink selflink">morphine</a>, <a href="/wiki/Heroin" title="Heroin">heroin</a>, <a href="/wiki/Hydrocodone" title="Hydrocodone">hydrocodone</a>, <a href="/wiki/Oxycodone" title="Oxycodone">oxycodone</a>, <a href="/wiki/Opium" title="Opium">opium</a>, <a href="/wiki/Kratom" class="mw-redirect" title="Kratom">kratom</a>)</li> <li><a href="/wiki/Voltage-dependent_calcium_channel#.CE.B12.CE.B4_Subunit" class="mw-redirect" title="Voltage-dependent calcium channel">α<sub>2</sub>δ subunit</a>-containing <a href="/wiki/Voltage-dependent_calcium_channel" class="mw-redirect" title="Voltage-dependent calcium channel">voltage-dependent calcium channels</a> <a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">blockers</a> (<a href="/wiki/Gabapentinoid" title="Gabapentinoid">gabapentinoids</a>) (e.g., <a href="/wiki/Gabapentin" title="Gabapentin">gabapentin</a>, <a href="/wiki/Pregabalin" title="Pregabalin">pregabalin</a>, <a href="/wiki/Phenibut" title="Phenibut">phenibut</a>)</li> <li><a href="/wiki/AMPA_receptor" title="AMPA receptor">AMPA receptor</a> <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonists</a> (e.g., <a href="/wiki/Perampanel" title="Perampanel">perampanel</a>)</li> <li><a href="/wiki/CB1_receptor" class="mw-redirect" title="CB1 receptor">CB<sub>1</sub> receptor</a> <a href="/wiki/Agonist" title="Agonist">agonists</a> (<a href="/wiki/Cannabinoid" title="Cannabinoid">cannabinoids</a>) (e.g., <a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">THC</a>, <a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">cannabis</a>)</li> <li><a href="/wiki/Dopamine_agonist" title="Dopamine agonist">Dopamine receptor agonists</a> (e.g., <a href="/wiki/Levodopa" title="Levodopa">levodopa</a>)</li> <li><a href="/wiki/Dopamine_releasing_agent" title="Dopamine releasing agent">Dopamine releasing agents</a> (e.g., <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>, <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>, <a href="/wiki/MDMA" title="MDMA">MDMA</a>, <a href="/wiki/Mephedrone" title="Mephedrone">mephedrone</a>)</li> <li><a href="/wiki/Dopamine_reuptake_inhibitor" title="Dopamine reuptake inhibitor">Dopamine reuptake inhibitors</a> (e.g., <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/wiki/Methylphenidate" title="Methylphenidate">methylphenidate</a>)</li> <li><a href="/wiki/GABAA_receptor" title="GABAA receptor">GABA<sub>A</sub> receptor</a> <a href="/wiki/Positive_allosteric_modulator" class="mw-redirect" title="Positive allosteric modulator">positive allosteric modulators</a> (e.g., <a href="/wiki/Barbiturate" title="Barbiturate">barbiturates</a>, <a href="/wiki/Benzodiazepine" title="Benzodiazepine">benzodiazepines</a>, <a href="/wiki/Carbamate" title="Carbamate">carbamates</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">ethanol (alcohol)</a> (<a href="/wiki/Alcoholic_drink" class="mw-redirect" title="Alcoholic drink">alcoholic drink</a>), <a href="/wiki/Inhalant" title="Inhalant">inhalants</a>, <a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">nonbenzodiazepines</a>, <a href="/wiki/Quinazolinone" title="Quinazolinone">quinazolinones</a>)</li> <li><a href="/wiki/Gamma-Hydroxybutyric_acid" class="mw-redirect" title="Gamma-Hydroxybutyric acid">GHB</a> (<a href="/wiki/Sodium_oxybate" title="Sodium oxybate">sodium oxybate</a>) and <a href="/wiki/Structural_analog" title="Structural analog">analogues</a></li> <li><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Glucocorticoids (corticosteroids)</a> (e.g., <a href="/wiki/Dexamethasone" title="Dexamethasone">dexamethasone</a>, <a href="/wiki/Prednisone" title="Prednisone">prednisone</a>)</li> <li><a href="/wiki/Nicotinic_agonist" title="Nicotinic agonist">nACh receptor agonists</a> (e.g., <a href="/wiki/Nicotine" title="Nicotine">nicotine</a>, <a href="/wiki/Tobacco" title="Tobacco">tobacco</a>, <a href="/wiki/Arecoline" title="Arecoline">arecoline</a>, <a href="/wiki/Areca_nut" title="Areca nut">areca nut</a>)</li> <li><a href="/wiki/Nitric_oxide_donor" class="mw-redirect" title="Nitric oxide donor">Nitric oxide prodrugs</a> (e.g., <a href="/wiki/Alkyl_nitrite" title="Alkyl nitrite">alkyl nitrites</a> (<a href="/wiki/Poppers" title="Poppers">poppers</a>))</li> <li><a href="/wiki/NMDA_receptor_antagonist" title="NMDA receptor antagonist">NMDA receptor antagonists</a> (e.g., <a href="/wiki/Dextromethorphan" title="Dextromethorphan">DXM</a>, <a href="/wiki/Ketamine" title="Ketamine">ketamine</a>, <a href="/wiki/Methoxetamine" title="Methoxetamine">methoxetamine</a>, <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">nitrous oxide</a>, <a href="/wiki/Phencyclidine" title="Phencyclidine">phencyclidine</a>, <a href="/wiki/Inhalant" title="Inhalant">inhalants</a>)</li> <li><a href="/wiki/Orexin_antagonist" title="Orexin antagonist">Orexin receptor antagonists</a> (e.g., <a href="/wiki/Suvorexant" title="Suvorexant">suvorexant</a>)</li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Drug_use" title="Template:Drug use">Recreational drug use</a></i></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="Opioid_receptor_modulators225" 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:Opioid_receptor_modulators" title="Template:Opioid receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Opioid_receptor_modulators" title="Template talk:Opioid receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Opioid_receptor_modulators" title="Special:EditPage/Template:Opioid receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Opioid_receptor_modulators225" style="font-size:114%;margin:0 4em"><a href="/wiki/Opioid_receptor" title="Opioid receptor">Opioid receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/%CE%9C-opioid_receptor" title="Μ-opioid receptor">μ-opioid</a><br />(MOR)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Agonists(abridged;full_list)67" scope="row" class="navbox-group" style="width:1%">Agonists<br />(abridged;<br /><a href="/wiki/List_of_opioids" title="List of opioids">full list</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/3-HO-PCP" title="3-HO-PCP">3-HO-PCP</a></li> <li><a href="/w/index.php?title=7-Acetoxymitragynine&amp;action=edit&amp;redlink=1" class="new" title="7-Acetoxymitragynine (page does not exist)">7-Acetoxymitragynine</a></li> <li><a href="/wiki/7-Hydroxymitragynine" title="7-Hydroxymitragynine">7-Hydroxymitragynine</a></li> <li><a href="/w/index.php?title=%CE%A8-Akuammigine&amp;action=edit&amp;redlink=1" class="new" title="Ψ-Akuammigine (page does not exist)">ψ-Akuammigine</a></li> <li><a href="/wiki/Chlornaltrexamine" class="mw-redirect" title="Chlornaltrexamine">α-Chlornaltrexamine</a></li> <li><a href="/w/index.php?title=Alpha-Narcotine&amp;action=edit&amp;redlink=1" class="new" title="Alpha-Narcotine (page does not exist)">α-Narcotine</a></li> <li><a href="/wiki/Acetyldihydrocodeine" title="Acetyldihydrocodeine">Acetyldihydrocodeine</a></li> <li><a href="/wiki/Acetylfentanyl" title="Acetylfentanyl">Acetylfentanyl</a></li> <li><a href="/wiki/Acrylfentanyl" title="Acrylfentanyl">Acrylfentanyl</a></li> <li><a href="/wiki/Adrenorphin" title="Adrenorphin">Adrenorphin (metorphamide)</a></li> <li><a href="/wiki/AH-7921" title="AH-7921">AH-7921</a></li> <li><a href="/wiki/Akuammicine" title="Akuammicine">Akuammicine</a></li> <li><a href="/w/index.php?title=Akuammidine&amp;action=edit&amp;redlink=1" class="new" title="Akuammidine (page does not exist)">Akuammidine</a></li> <li><a href="/wiki/Alfentanil" title="Alfentanil">Alfentanil</a></li> <li><a href="/wiki/Anileridine" title="Anileridine">Anileridine</a></li> <li><a href="/wiki/Apparicine" title="Apparicine">Apparicine</a></li> <li><a href="/wiki/Beta-Endorphin" class="mw-redirect" title="Beta-Endorphin">β-Endorphin</a></li> <li><a href="/w/index.php?title=Bovine_adrenal_medullary_peptide-12P&amp;action=edit&amp;redlink=1" class="new" title="Bovine adrenal medullary peptide-12P (page does not exist)">BAM-12P</a></li> <li><a href="/w/index.php?title=Bovine_adrenal_medullary_peptide-18P&amp;action=edit&amp;redlink=1" class="new" title="Bovine adrenal medullary peptide-18P (page does not exist)">BAM-18P</a></li> <li><a href="/w/index.php?title=Bovine_adrenal_medullary_peptide-22P&amp;action=edit&amp;redlink=1" class="new" title="Bovine adrenal medullary peptide-22P (page does not exist)">BAM-22P</a></li> <li><a href="/wiki/Benzhydrocodone" title="Benzhydrocodone">Benzhydrocodone</a></li> <li><a href="/wiki/Benzylmorphine" title="Benzylmorphine">Benzylmorphine</a></li> <li><a href="/wiki/Bezitramide" title="Bezitramide">Bezitramide</a></li> <li><a href="/wiki/Biphalin" title="Biphalin">Biphalin</a></li> <li><a href="/w/index.php?title=BU08070&amp;action=edit&amp;redlink=1" class="new" title="BU08070 (page does not exist)">BU08070</a></li> <li><a href="/wiki/Buprenorphine" title="Buprenorphine">Buprenorphine</a></li> <li><a href="/wiki/Butorphan" class="mw-redirect" title="Butorphan">Butorphan</a></li> <li><a href="/wiki/Butorphanol" title="Butorphanol">Butorphanol</a></li> <li><a href="/wiki/Butyrfentanyl" title="Butyrfentanyl">Butyrfentanyl</a></li> <li><a href="/wiki/BW373U86" title="BW373U86">BW373U86</a></li> <li><a href="/wiki/Carfentanil" title="Carfentanil">Carfentanil</a></li> <li><a href="/wiki/Casokefamide" title="Casokefamide">Casokefamide</a></li> <li><a href="/wiki/Cebranopadol" title="Cebranopadol">Cebranopadol</a></li> <li><a href="/wiki/Chloroxymorphamine" title="Chloroxymorphamine">Chloroxymorphamine</a></li> <li><a href="/wiki/Codeine" title="Codeine">Codeine</a></li> <li><a href="/wiki/DADLE" title="DADLE">DADLE</a></li> <li><a href="/wiki/DAMGO" title="DAMGO">DAMGO (DAGO)</a></li> <li><a href="/wiki/Dermorphin" title="Dermorphin">Dermorphin</a></li> <li><a href="/wiki/Desmetramadol" title="Desmetramadol">Desmetramadol</a> (desmethyltramadol)</li> <li><a href="/wiki/Desomorphine" title="Desomorphine">Desomorphine</a></li> <li><a href="/wiki/Dextromoramide" title="Dextromoramide">Dextromoramide</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a> (propoxyphene)</li> <li><a href="/wiki/Dezocine" title="Dezocine">Dezocine</a></li> <li><a href="/wiki/Dimenoxadol" title="Dimenoxadol">Dimenoxadol</a></li> <li><a href="/wiki/Dimethylaminopivalophenone" title="Dimethylaminopivalophenone">Dimethylaminopivalophenone</a></li> <li><a href="/wiki/Eluxadoline" title="Eluxadoline">Eluxadoline</a></li> <li><a href="/wiki/Heroin" title="Heroin">Diamorphine</a> (heroin)</li> <li><a href="/wiki/Dihydrocodeine" title="Dihydrocodeine">Dihydrocodeine</a></li> <li><a href="/wiki/Dihydroetorphine" title="Dihydroetorphine">Dihydroetorphine</a></li> <li><a href="/wiki/Dihydromorphine" title="Dihydromorphine">Dihydromorphine</a></li> <li><a href="/wiki/Dinalbuphine_sebacate" title="Dinalbuphine sebacate">Dinalbuphine sebacate</a></li> <li><a href="/wiki/Diphenoxylate" title="Diphenoxylate">Diphenoxylate</a></li> <li><a href="/wiki/Dipipanone" title="Dipipanone">Dipipanone</a></li> <li><a href="/wiki/Dynorphin_A" title="Dynorphin A">Dynorphin A</a></li> <li><a href="/wiki/Embutramide" title="Embutramide">Embutramide</a></li> <li><a href="/wiki/Endomorphin-1" title="Endomorphin-1">Endomorphin-1</a></li> <li><a href="/wiki/Endomorphin-2" title="Endomorphin-2">Endomorphin-2</a></li> <li><a href="/wiki/Eseroline" title="Eseroline">Eseroline</a></li> <li><a href="/wiki/Ethylmorphine" title="Ethylmorphine">Ethylmorphine</a></li> <li><a href="/wiki/Etorphine" title="Etorphine">Etorphine</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a></li> <li><a href="/wiki/Fluorophen" title="Fluorophen">Fluorophen</a></li> <li><a href="/wiki/Frakefamide" title="Frakefamide">Frakefamide</a></li> <li><a href="/wiki/Furanylfentanyl" title="Furanylfentanyl">Furanylfentanyl</a></li> <li><a href="/wiki/Hemorphin-4" title="Hemorphin-4">Hemorphin-4</a></li> <li><a href="/wiki/Herkinorin" title="Herkinorin">Herkinorin</a></li> <li><a href="/wiki/Hodgkinsine" title="Hodgkinsine">Hodgkinsine</a></li> <li><a href="/wiki/Hydrocodone" title="Hydrocodone">Hydrocodone</a></li> <li><a href="/wiki/Hydromorphinol" title="Hydromorphinol">Hydromorphinol</a></li> <li><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone</a></li> <li><a href="/wiki/IBNtxA" title="IBNtxA">IBNtxA</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Ketobemidone" title="Ketobemidone">Ketobemidone</a></li> <li><a href="/wiki/Mitragyna_speciosa" title="Mitragyna speciosa">Kratom</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Leu-enkephalin" title="Leu-enkephalin">Leu-enkephalin</a></li> <li><a href="/wiki/Levacetylmethadol" title="Levacetylmethadol">Levacetylmethadol</a></li> <li><a href="/wiki/Levomethorphan" title="Levomethorphan">Levomethorphan</a></li> <li><a href="/wiki/Levorphanol" title="Levorphanol">Levorphanol</a></li> <li><a href="/w/index.php?title=Lexanopadol&amp;action=edit&amp;redlink=1" class="new" title="Lexanopadol (page does not exist)">Lexanopadol</a></li> <li><a href="/wiki/Loperamide" title="Loperamide">Loperamide</a></li> <li><a href="/wiki/Loxicodegol" class="mw-redirect" title="Loxicodegol">Loxicodegol</a></li> <li><a href="/wiki/LS-115509" title="LS-115509">LS-115509</a></li> <li><a href="/wiki/Matrine" title="Matrine">Matrine</a></li> <li><a href="/wiki/Meptazinol" title="Meptazinol">Meptazinol</a></li> <li><a href="/wiki/Met-enkephalin" title="Met-enkephalin">Met-enkephalin</a> (metenkefalin)</li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Metkefamide" title="Metkefamide">Metkefamide</a></li> <li><a href="/wiki/Metopon" title="Metopon">Metopon</a></li> <li><a href="/wiki/Mitragynine" title="Mitragynine">Mitragynine</a></li> <li><a href="/wiki/Mitragynine_pseudoindoxyl" title="Mitragynine pseudoindoxyl">Mitragynine pseudoindoxyl</a></li> <li><a href="/wiki/Morphiceptin" title="Morphiceptin">Morphiceptin</a></li> <li><a class="mw-selflink selflink">Morphine</a></li> <li><a href="/wiki/Nalbuphine" title="Nalbuphine">Nalbuphine</a></li> <li><a href="/w/index.php?title=Naloxone_benzoylhydrazone&amp;action=edit&amp;redlink=1" class="new" title="Naloxone benzoylhydrazone (page does not exist)">Naloxone benzoylhydrazone</a> (NalBzOH)</li> <li><a href="/wiki/Nalmexone" title="Nalmexone">Nalmexone</a></li> <li><a href="/wiki/Naltalimide" title="Naltalimide">Naltalimide</a></li> <li><a href="/w/index.php?title=Neopine&amp;action=edit&amp;redlink=1" class="new" title="Neopine (page does not exist)">Neopine</a></li> <li><a href="/wiki/NFEPP" title="NFEPP">NFEPP</a></li> <li><a href="/wiki/Nicocodeine" title="Nicocodeine">Nicocodeine</a></li> <li><a href="/wiki/Nicodicodine" title="Nicodicodine">Nicodicodine</a></li> <li><a href="/wiki/Nicomorphine" title="Nicomorphine">Nicomorphine</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Nufenoxole" title="Nufenoxole">Nufenoxole</a></li> <li><a href="/wiki/Octreotide" title="Octreotide">Octreotide</a></li> <li><a href="/wiki/Oliceridine" title="Oliceridine">Oliceridine</a></li> <li><a href="/wiki/Oxycodegol" title="Oxycodegol">Oxycodegol</a></li> <li><a href="/wiki/Oxymorphone-3-methoxynaltrexonazine" title="Oxymorphone-3-methoxynaltrexonazine">Oxymorphone-3-methoxynaltrexonazine</a> (OM-3-MNZ)</li> <li><a href="/wiki/Oripavine" title="Oripavine">Oripavine</a></li> <li><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a></li> <li><a href="/wiki/Oxymorphazone" title="Oxymorphazone">Oxymorphazone</a></li> <li><a href="/w/index.php?title=Oxymorphonazine&amp;action=edit&amp;redlink=1" class="new" title="Oxymorphonazine (page does not exist)">Oxymorphonazine</a></li> <li><a href="/wiki/Oxymorphone" title="Oxymorphone">Oxymorphone</a></li> <li><a href="/w/index.php?title=Oxymorphone_phenylhydrazone&amp;action=edit&amp;redlink=1" class="new" title="Oxymorphone phenylhydrazone (page does not exist)">Oxymorphone phenylhydrazone</a></li> <li><a href="/w/index.php?title=Oxymorphone_p-nitrophenylhydrazone&amp;action=edit&amp;redlink=1" class="new" title="Oxymorphone p-nitrophenylhydrazone (page does not exist)">OxyPNPH</a></li> <li><i><a href="/wiki/Papaver_somniferum" title="Papaver somniferum">Papaver somniferum</a></i> (<a href="/wiki/Opium" title="Opium">opium</a>)</li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Pericine" title="Pericine">Pericine</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine (meperidine)</a></li> <li><a href="/wiki/Phenazocine" title="Phenazocine">Phenazocine</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Piminodine" title="Piminodine">Piminodine</a></li> <li><a href="/wiki/Piritramide" title="Piritramide">Piritramide</a></li> <li><a href="/w/index.php?title=PL-017&amp;action=edit&amp;redlink=1" class="new" title="PL-017 (page does not exist)">PL-017</a></li> <li><a href="/wiki/Prodine" title="Prodine">Prodine</a></li> <li><a href="/wiki/Propiram" title="Propiram">Propiram</a></li> <li><a href="/wiki/PZM21" title="PZM21">PZM21</a></li> <li><a href="/wiki/Methorphan" title="Methorphan">Racemethorphan</a></li> <li><a href="/wiki/Racemorphan" title="Racemorphan">Racemorphan</a></li> <li><a href="/wiki/Remifentanil" title="Remifentanil">Remifentanil</a></li> <li><a href="/wiki/Salsolinol" title="Salsolinol">Salsolinol</a></li> <li><a href="/wiki/SC-17599" title="SC-17599">SC-17599</a></li> <li><a href="/wiki/Sinomenine" title="Sinomenine">Sinomenine</a></li> <li><a href="/wiki/Sufentanil" title="Sufentanil">Sufentanil</a></li> <li><a href="/wiki/Tapentadol" title="Tapentadol">Tapentadol</a></li> <li><a href="/wiki/Tetrahydropapaveroline" title="Tetrahydropapaveroline">Tetrahydropapaveroline</a></li> <li><a href="/wiki/TH-030418" title="TH-030418">TH-030418</a></li> <li><a href="/wiki/Thebaine" title="Thebaine">Thebaine</a></li> <li><a href="/wiki/Thienorphine" title="Thienorphine">Thienorphine</a></li> <li><a href="/wiki/Tianeptine" title="Tianeptine">Tianeptine</a></li> <li><a href="/wiki/Tilidine" title="Tilidine">Tilidine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Trimebutine" title="Trimebutine">Trimebutine</a></li> <li><a href="/wiki/TRIMU_5" title="TRIMU 5">TRIMU 5</a></li> <li><a href="/wiki/TRV734" title="TRV734">TRV734</a></li> <li><a href="/w/index.php?title=Tubotaiwine&amp;action=edit&amp;redlink=1" class="new" title="Tubotaiwine (page does not exist)">Tubotaiwine</a></li> <li><a href="/wiki/U-47700" title="U-47700">U-47700</a></li> <li><a href="/wiki/Valorphin" title="Valorphin">Valorphin</a></li> <li><a href="/wiki/Viminol" title="Viminol">Viminol</a></li> <li><a href="/wiki/Xorphanol" title="Xorphanol">Xorphanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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/Picenadol" title="Picenadol">(3S,4S)-Picenadol</a></li> <li><a href="/wiki/Viminol" title="Viminol">2-(S)-N,N-(R)-Viminol</a></li> <li><a href="/w/index.php?title=3CS-nalmefene&amp;action=edit&amp;redlink=1" class="new" title="3CS-nalmefene (page does not exist)">3CS-nalmefene</a></li> <li><a href="/wiki/4-Caffeoyl-1,5-quinide" title="4-Caffeoyl-1,5-quinide">4-Caffeoyl-1,5-quinide</a></li> <li><a href="/wiki/4%E2%80%B2-Hydroxyflavanone" class="mw-redirect" title="4′-Hydroxyflavanone">4′-Hydroxyflavanone</a></li> <li><a href="/wiki/4%27,7-Dihydroxyflavone" title="4&#39;,7-Dihydroxyflavone">4',7-Dihydroxyflavone</a></li> <li><a href="/wiki/6%CE%B2-Naltrexol" title="6β-Naltrexol">6β-Naltrexol</a></li> <li><a href="/wiki/6%CE%B2-Naltrexol-d4" title="6β-Naltrexol-d4">6β-Naltrexol-d4</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/Alpha-Gliadin" class="mw-redirect" title="Alpha-Gliadin">α-Gliadin</a></li> <li><a href="/wiki/Chlornaltrexamine" class="mw-redirect" title="Chlornaltrexamine">β-Chlornaltrexamine</a></li> <li><a href="/wiki/Beta-Funaltrexamine" class="mw-redirect" title="Beta-Funaltrexamine">β-Funaltrexamine</a></li> <li><a href="/wiki/Akuammine" title="Akuammine">Akuammine</a></li> <li><a href="/wiki/Alvimopan" title="Alvimopan">Alvimopan</a></li> <li><a href="/wiki/AM-251_(drug)" title="AM-251 (drug)">AM-251</a></li> <li><a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/AT-076" title="AT-076">AT-076</a></li> <li><a href="/wiki/Axelopran" title="Axelopran">Axelopran</a></li> <li><a href="/wiki/Bevenopran" title="Bevenopran">Bevenopran</a></li> <li><a href="/wiki/Catechin" title="Catechin">Catechin</a></li> <li><a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">Catechin gallate</a></li> <li><a href="/wiki/Clocinnamox" title="Clocinnamox">Clocinnamox</a></li> <li>CTAP</li> <li><a href="/w/index.php?title=CTOP&amp;action=edit&amp;redlink=1" class="new" title="CTOP (page does not exist)">CTOP</a></li> <li><a href="/w/index.php?title=Cyclofoxy&amp;action=edit&amp;redlink=1" class="new" title="Cyclofoxy (page does not exist)">Cyclofoxy</a></li> <li><a href="/wiki/Cyprodime" title="Cyprodime">Cyprodime</a></li> <li><a href="/wiki/Diacetylnalorphine" title="Diacetylnalorphine">Diacetylnalorphine</a></li> <li><a href="/wiki/Diprenorphine" title="Diprenorphine">Diprenorphine</a></li> <li><a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a></li> <li><a href="/wiki/Gallocatechol" title="Gallocatechol">EGC</a></li> <li><a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">Epicatechin</a></li> <li><a href="/wiki/Eptazocine" title="Eptazocine">Eptazocine</a></li> <li><a href="/wiki/Gemazocine" title="Gemazocine">Gemazocine</a></li> <li><a href="/w/index.php?title=Ginsenoside_R&amp;action=edit&amp;redlink=1" class="new" title="Ginsenoside R (page does not exist)">Ginsenoside R</a></li> <li><a href="/wiki/Hyperoside" title="Hyperoside">Hyperoside</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/JDTic" title="JDTic">JDTic</a></li> <li><a href="/wiki/Levallorphan" title="Levallorphan">Levallorphan</a></li> <li><a href="/wiki/Lobeline" title="Lobeline">Lobeline</a></li> <li><a href="/wiki/LY-255582" title="LY-255582">LY-255582</a></li> <li><a href="/wiki/LY-2196044" class="mw-redirect" title="LY-2196044">LY-2196044</a></li> <li><a href="/wiki/Methocinnamox" title="Methocinnamox">Methocinnamox</a></li> <li><a href="/wiki/Methylnaltrexone" title="Methylnaltrexone">Methylnaltrexone</a></li> <li><a href="/w/index.php?title=Methylsamidorphan_chloride&amp;action=edit&amp;redlink=1" class="new" title="Methylsamidorphan chloride (page does not exist)">Methylsamidorphan chloride</a></li> <li><a href="/wiki/Naldemedine" title="Naldemedine">Naldemedine</a></li> <li><a href="/wiki/Nalmefene" title="Nalmefene">Nalmefene</a></li> <li><a href="/wiki/Nalodeine" title="Nalodeine">Nalodeine (N-allylnorcodeine)</a></li> <li><a href="/wiki/Nalorphine" title="Nalorphine">Nalorphine</a></li> <li><a href="/wiki/Nalorphine_dinicotinate" title="Nalorphine dinicotinate">Nalorphine dinicotinate</a></li> <li><a href="/wiki/Naloxazone" title="Naloxazone">Naloxazone</a></li> <li><a href="/wiki/Naloxegol" title="Naloxegol">Naloxegol</a></li> <li><a href="/wiki/Naloxol" title="Naloxol">Naloxol</a></li> <li><a href="/wiki/Naloxonazine" title="Naloxonazine">Naloxonazine</a></li> <li><a href="/wiki/Naloxone" title="Naloxone">Naloxone</a></li> <li><a href="/w/index.php?title=Naltrexazone&amp;action=edit&amp;redlink=1" class="new" title="Naltrexazone (page does not exist)">Naltrexazone</a></li> <li><a href="/w/index.php?title=Naltrexonazine&amp;action=edit&amp;redlink=1" class="new" title="Naltrexonazine (page does not exist)">Naltrexonazine</a></li> <li><a href="/wiki/Naltrexone" title="Naltrexone">Naltrexone</a></li> <li><a href="/wiki/Naltrindole" title="Naltrindole">Naltrindole</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Oxilorphan" title="Oxilorphan">Oxilorphan</a></li> <li><a href="/wiki/Pawhuskin_A" title="Pawhuskin A">Pawhuskin A</a></li> <li><a href="/wiki/Rimonabant" title="Rimonabant">Rimonabant</a></li> <li><a href="/wiki/Quadazocine" title="Quadazocine">Quadazocine</a></li> <li><a href="/wiki/Samidorphan" title="Samidorphan">Samidorphan</a></li> <li><a href="/wiki/Taxifolin" title="Taxifolin">Taxifolin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/%CE%94-opioid_receptor" title="Δ-opioid receptor">δ-opioid</a><br />(DOR)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Agonists</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="/w/index.php?title=3CS-nalmefene&amp;action=edit&amp;redlink=1" class="new" title="3CS-nalmefene (page does not exist)">3CS-nalmefene</a></li> <li><a href="/wiki/6%27-Guanidinonaltrindole" title="6&#39;-Guanidinonaltrindole">6'-GNTI</a></li> <li><a href="/wiki/7-Spiroindanyloxymorphone" title="7-Spiroindanyloxymorphone">7-SIOM</a></li> <li><a href="/wiki/ADL-5747" title="ADL-5747">ADL-5747 (PF-04856881)</a></li> <li><a href="/wiki/ADL-5859" title="ADL-5859">ADL-5859</a></li> <li><a href="/wiki/Alazocine" title="Alazocine">Alazocine (SKF-10047)</a></li> <li><a href="/wiki/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/ARM390" title="ARM390">AR-M100390 (ARM390)</a></li> <li><a href="/wiki/AZD2327" class="mw-redirect" title="AZD2327">AZD2327</a></li> <li><a href="/wiki/Beta-Endorphin" class="mw-redirect" title="Beta-Endorphin">β-Endorphin</a></li> <li><a href="/w/index.php?title=Bovine_adrenal_medullary_peptide-18P&amp;action=edit&amp;redlink=1" class="new" title="Bovine adrenal medullary peptide-18P (page does not exist)">BAM-18P</a></li> <li><a href="/wiki/Biphalin" title="Biphalin">Biphalin</a></li> <li><a href="/wiki/BU-48" title="BU-48">BU-48</a></li> <li><a href="/wiki/Butorphan" class="mw-redirect" title="Butorphan">Butorphan</a></li> <li><a href="/wiki/Butorphanol" title="Butorphanol">Butorphanol</a></li> <li><a href="/wiki/BW373U86" title="BW373U86">BW373U86</a></li> <li><a href="/wiki/Casokefamide" title="Casokefamide">Casokefamide</a></li> <li><a href="/wiki/Cebranopadol" title="Cebranopadol">Cebranopadol</a></li> <li><a href="/wiki/Codeine" title="Codeine">Codeine</a></li> <li><a href="/wiki/Cyclazocine" title="Cyclazocine">Cyclazocine</a></li> <li><a href="/wiki/DADLE" title="DADLE">DADLE</a></li> <li><a href="/wiki/Deltorphin" title="Deltorphin">Deltorphin A</a></li> <li><a href="/wiki/Deltorphin_I" title="Deltorphin I">Deltorphin I</a></li> <li><a href="/w/index.php?title=Deltorphin_II&amp;action=edit&amp;redlink=1" class="new" title="Deltorphin II (page does not exist)">Deltorphin II</a></li> <li><a href="/wiki/Desmethylclozapine" title="Desmethylclozapine">Desmethylclozapine</a></li> <li><a href="/wiki/Desmetramadol" title="Desmetramadol">Desmetramadol (desmethyltramadol)</a></li> <li><a href="/wiki/Dezocine" title="Dezocine">Dezocine</a></li> <li><a href="/wiki/Heroin" title="Heroin">Diamorphine (heroin)</a></li> <li><a href="/wiki/Dihydroetorphine" title="Dihydroetorphine">Dihydroetorphine</a></li> <li><a href="/wiki/Dihydromorphine" title="Dihydromorphine">Dihydromorphine</a></li> <li><a href="/wiki/DPDPE" title="DPDPE">DPDPE</a></li> <li><a href="/wiki/DPI-221" title="DPI-221">DPI-221</a></li> <li><a href="/wiki/DPI-3290" title="DPI-3290">DPI-3290</a></li> <li><a href="/w/index.php?title=(D-Ser2,_Leu5,_Thr6)-Enkephalin&amp;action=edit&amp;redlink=1" class="new" title="(D-Ser2, Leu5, Thr6)-Enkephalin (page does not exist)">DSLET</a></li> <li><a href="/wiki/Ethylketazocine" title="Ethylketazocine">Ethylketazocine</a></li> <li><a href="/wiki/Etorphine" title="Etorphine">Etorphine</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a></li> <li><a href="/w/index.php?title=Fentanyl_isothiocyanate&amp;action=edit&amp;redlink=1" class="new" title="Fentanyl isothiocyanate (page does not exist)">FIT</a></li> <li><a href="/wiki/Fluorophen" title="Fluorophen">Fluorophen</a></li> <li><a href="/wiki/Hemorphin-4" title="Hemorphin-4">Hemorphin-4</a></li> <li><a href="/wiki/Hydrocodone" title="Hydrocodone">Hydrocodone</a></li> <li><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Isomethadone" title="Isomethadone">Isomethadone</a></li> <li><a href="/wiki/JNJ-20788560" title="JNJ-20788560">JNJ-20788560</a></li> <li><a href="/wiki/KNT-127" title="KNT-127">KNT-127</a></li> <li><a href="/wiki/Mitragyna_speciosa" title="Mitragyna speciosa">Kratom</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/wiki/Leu-enkephalin" title="Leu-enkephalin">Leu-enkephalin</a></li> <li><a href="/wiki/Levomethorphan" title="Levomethorphan">Levomethorphan</a></li> <li><a href="/wiki/Levorphanol" title="Levorphanol">Levorphanol</a></li> <li><a href="/w/index.php?title=Lexanopadol&amp;action=edit&amp;redlink=1" class="new" title="Lexanopadol (page does not exist)">Lexanopadol</a></li> <li><a href="/wiki/Lofentanil" title="Lofentanil">Lofentanil</a></li> <li><a href="/wiki/Met-enkephalin" title="Met-enkephalin">Met-enkephalin (metenkefalin)</a></li> <li><a href="/wiki/Metazocine" title="Metazocine">Metazocine</a></li> <li><a href="/wiki/Metkefamide" title="Metkefamide">Metkefamide</a></li> <li><a href="/wiki/Mitragynine" title="Mitragynine">Mitragynine</a></li> <li><a href="/wiki/Mitragynine_pseudoindoxyl" title="Mitragynine pseudoindoxyl">Mitragynine pseudoindoxyl</a></li> <li><a class="mw-selflink selflink">Morphine</a></li> <li><a href="/wiki/N-Phenethyl-14-ethoxymetopon" title="N-Phenethyl-14-ethoxymetopon">N-Phenethyl-14-ethoxymetopon</a></li> <li><a href="/wiki/Norbuprenorphine" title="Norbuprenorphine">Norbuprenorphine</a></li> <li><a href="/w/index.php?title=Naloxone_benzoylhydrazone&amp;action=edit&amp;redlink=1" class="new" title="Naloxone benzoylhydrazone (page does not exist)">NalBzOH</a></li> <li><a href="/wiki/Oripavine" title="Oripavine">Oripavine</a></li> <li><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a></li> <li><a href="/wiki/Oxymorphone" title="Oxymorphone">Oxymorphone</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine (meperidine)</a></li> <li><a href="/wiki/Proglumide" title="Proglumide">Proglumide</a></li> <li><a href="/wiki/Methorphan" title="Methorphan">Racemethorphan</a></li> <li><a href="/wiki/Racemorphan" title="Racemorphan">Racemorphan</a></li> <li><a href="/wiki/RWJ-394674" title="RWJ-394674">RWJ-394674</a></li> <li><a href="/wiki/Samidorphan" title="Samidorphan">Samidorphan</a></li> <li><a href="/w/index.php?title=SB-235863&amp;action=edit&amp;redlink=1" class="new" title="SB-235863 (page does not exist)">SB-235863</a></li> <li><a href="/wiki/SNC-80" title="SNC-80">SNC-80</a></li> <li><a href="/w/index.php?title=SNC-162&amp;action=edit&amp;redlink=1" class="new" title="SNC-162 (page does not exist)">SNC-162</a></li> <li><a href="/wiki/TAN-67" title="TAN-67">TAN-67 (SB-205,607)</a></li> <li><a href="/wiki/TH-030418" title="TH-030418">TH-030418</a></li> <li><a href="/wiki/Thebaine" title="Thebaine">Thebaine</a></li> <li><a href="/wiki/C-8813" title="C-8813">Thiobromadol (C-8813)</a></li> <li><a href="/wiki/Tonazocine" title="Tonazocine">Tonazocine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/w/index.php?title=TRV250&amp;action=edit&amp;redlink=1" class="new" title="TRV250 (page does not exist)">TRV250</a></li> <li><a href="/wiki/Xorphanol" title="Xorphanol">Xorphanol</a></li> <li><a href="/wiki/Zenazocine" title="Zenazocine">Zenazocine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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/4%27,7-Dihydroxyflavone" title="4&#39;,7-Dihydroxyflavone">4',7-Dihydroxyflavone</a></li> <li><a href="/w/index.php?title=Naltrindole-5%27-isothiocyanate&amp;action=edit&amp;redlink=1" class="new" title="Naltrindole-5&#39;-isothiocyanate (page does not exist)">5'-NTII</a></li> <li><a href="/wiki/6%CE%B2-Naltrexol" title="6β-Naltrexol">6β-Naltrexol</a></li> <li><a href="/wiki/6%CE%B2-Naltrexol-d4" title="6β-Naltrexol-d4">6β-Naltrexol-d4</a></li> <li><a href="/w/index.php?title=Alpha-Santolol&amp;action=edit&amp;redlink=1" class="new" title="Alpha-Santolol (page does not exist)">α-Santolol</a></li> <li><a href="/wiki/Chlornaltrexamine" class="mw-redirect" title="Chlornaltrexamine">β-Chlornaltrexamine</a></li> <li><a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/AT-076" title="AT-076">AT-076</a></li> <li><a href="/wiki/Axelopran" title="Axelopran">Axelopran</a></li> <li><a href="/wiki/Bevenopran" title="Bevenopran">Bevenopran</a></li> <li><a href="/w/index.php?title=7-Benzylidenenaltrexone&amp;action=edit&amp;redlink=1" class="new" title="7-Benzylidenenaltrexone (page does not exist)">BNTX</a></li> <li><a href="/wiki/Catechin" title="Catechin">Catechin</a></li> <li><a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">Catechin gallate</a></li> <li><a href="/wiki/Clocinnamox" title="Clocinnamox">Clocinnamox</a></li> <li><a href="/wiki/Diacetylnalorphine" title="Diacetylnalorphine">Diacetylnalorphine</a></li> <li><a href="/wiki/Diprenorphine" title="Diprenorphine">Diprenorphine</a></li> <li><a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a></li> <li><a href="/wiki/Gallocatechol" title="Gallocatechol">EGC</a></li> <li><a href="/wiki/Eluxadoline" title="Eluxadoline">Eluxadoline</a></li> <li><a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">Epicatechin</a></li> <li><a href="/w/index.php?title=ICI-154129&amp;action=edit&amp;redlink=1" class="new" title="ICI-154129 (page does not exist)">ICI-154129</a></li> <li><a href="/w/index.php?title=ICI-174864&amp;action=edit&amp;redlink=1" class="new" title="ICI-174864 (page does not exist)">ICI-174864</a></li> <li><a href="/wiki/LY-255582" title="LY-255582">LY-255582</a></li> <li><a href="/wiki/LY-2196044" class="mw-redirect" title="LY-2196044">LY-2196044</a></li> <li><a href="/wiki/Methylnaltrexone" title="Methylnaltrexone">Methylnaltrexone</a></li> <li><a href="/w/index.php?title=Methylnaltrindole&amp;action=edit&amp;redlink=1" class="new" title="Methylnaltrindole (page does not exist)">Methylnaltrindole</a></li> <li><a href="/w/index.php?title=N-Benzylnaltrindole&amp;action=edit&amp;redlink=1" class="new" title="N-Benzylnaltrindole (page does not exist)">N-Benzylnaltrindole</a></li> <li><a href="/wiki/Nalmefene" title="Nalmefene">Nalmefene</a></li> <li><a href="/wiki/Nalorphine" title="Nalorphine">Nalorphine</a></li> <li><a href="/wiki/Naltrexone" title="Naltrexone">Naltrexone</a></li> <li><a href="/wiki/Naltriben" title="Naltriben">Naltriben</a></li> <li><a href="/wiki/Naltrindole" title="Naltrindole">Naltrindole</a></li> <li><a href="/wiki/Naloxone" title="Naloxone">Naloxone</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Pawhuskin_A" title="Pawhuskin A">Pawhuskin A</a></li> <li><a href="/wiki/Quadazocine" title="Quadazocine">Quadazocine</a></li> <li><a href="/w/index.php?title=SDM25N&amp;action=edit&amp;redlink=1" class="new" title="SDM25N (page does not exist)">SDM25N</a></li> <li><a href="/wiki/SoRI-9409" title="SoRI-9409">SoRI-9409</a></li> <li><a href="/wiki/Taxifolin" title="Taxifolin">Taxifolin</a></li> <li><a href="/wiki/Thienorphine" title="Thienorphine">Thienorphine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/%CE%9A-opioid_receptor" title="Κ-opioid receptor">κ-opioid</a><br />(KOR)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Agonists</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="/w/index.php?title=3CS-nalmefene&amp;action=edit&amp;redlink=1" class="new" title="3CS-nalmefene (page does not exist)">3CS-nalmefene</a></li> <li><a href="/wiki/6%27-Guanidinonaltrindole" title="6&#39;-Guanidinonaltrindole">6'-GNTI</a></li> <li><a href="/wiki/8-Carboxamidocyclazocine" title="8-Carboxamidocyclazocine">8-CAC</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/14-Methoxymetopon" title="14-Methoxymetopon">14-Methoxymetopon</a></li> <li><a href="/wiki/Chlornaltrexamine" class="mw-redirect" title="Chlornaltrexamine">β-Chlornaltrexamine</a></li> <li><a href="/wiki/Beta-Funaltrexamine" class="mw-redirect" title="Beta-Funaltrexamine">β-Funaltrexamine</a></li> <li><a href="/wiki/Adrenorphin" title="Adrenorphin">Adrenorphin (metorphamide)</a></li> <li><a href="/wiki/Akuammicine" title="Akuammicine">Akuammicine</a></li> <li><a href="/wiki/Alazocine" title="Alazocine">Alazocine (SKF-10047)</a></li> <li><a href="/wiki/Allomatrine" class="mw-redirect" title="Allomatrine">Allomatrine</a></li> <li><a href="/w/index.php?title=Apadoline&amp;action=edit&amp;redlink=1" class="new" title="Apadoline (page does not exist)">Apadoline</a></li> <li><a href="/wiki/Asimadoline" title="Asimadoline">Asimadoline</a></li> <li><a href="/w/index.php?title=Bovine_adrenal_medullary_peptide-12P&amp;action=edit&amp;redlink=1" class="new" title="Bovine adrenal medullary peptide-12P (page does not exist)">BAM-12P</a></li> <li><a href="/w/index.php?title=Bovine_adrenal_medullary_peptide-18P&amp;action=edit&amp;redlink=1" class="new" title="Bovine adrenal medullary peptide-18P (page does not exist)">BAM-18P</a></li> <li><a href="/w/index.php?title=Bovine_adrenal_medullary_peptide-22P&amp;action=edit&amp;redlink=1" class="new" title="Bovine adrenal medullary peptide-22P (page does not exist)">BAM-22P</a></li> <li><a href="/wiki/Big_dynorphin" title="Big dynorphin">Big dynorphin</a></li> <li><a href="/wiki/Bremazocine" title="Bremazocine">Bremazocine</a></li> <li><a href="/wiki/BRL-52537" title="BRL-52537">BRL-52537</a></li> <li><a href="/wiki/Butorphan" class="mw-redirect" title="Butorphan">Butorphan</a></li> <li><a href="/wiki/Butorphanol" title="Butorphanol">Butorphanol</a></li> <li><a href="/wiki/BW373U86" title="BW373U86">BW373U86</a></li> <li><a href="/wiki/Cebranopadol" title="Cebranopadol">Cebranopadol</a></li> <li><a href="/wiki/Ciprefadol" title="Ciprefadol">Ciprefadol</a></li> <li><a href="/wiki/CR665" title="CR665">CR665</a></li> <li><a href="/wiki/Cyclazocine" title="Cyclazocine">Cyclazocine</a></li> <li><a href="/wiki/Cyclorphan" title="Cyclorphan">Cyclorphan</a></li> <li><a href="/wiki/Cyprenorphine" title="Cyprenorphine">Cyprenorphine</a></li> <li><a href="/wiki/Desmetramadol" title="Desmetramadol">Desmetramadol (desmethyltramadol)</a></li> <li><a href="/wiki/Heroin" title="Heroin">Diamorphine (heroin)</a></li> <li><a href="/wiki/Diacetylnalorphine" title="Diacetylnalorphine">Diacetylnalorphine</a></li> <li><a href="/wiki/Difelikefalin" title="Difelikefalin">Difelikefalin</a></li> <li><a href="/wiki/Dihydroetorphine" title="Dihydroetorphine">Dihydroetorphine</a></li> <li><a href="/wiki/Dihydromorphine" title="Dihydromorphine">Dihydromorphine</a></li> <li><a href="/wiki/Dinalbuphine_sebacate" title="Dinalbuphine sebacate">Dinalbuphine sebacate</a></li> <li><a href="/wiki/Diprenorphine" title="Diprenorphine">Diprenorphine</a></li> <li><a href="/wiki/Dynorphin_A" title="Dynorphin A">Dynorphin A</a></li> <li><a href="/wiki/Dynorphin_B" title="Dynorphin B">Dynorphin B (rimorphin)</a></li> <li><a href="/wiki/Eluxadoline" title="Eluxadoline">Eluxadoline</a></li> <li><a href="/wiki/Enadoline" title="Enadoline">Enadoline</a></li> <li><a href="/wiki/Eptazocine" title="Eptazocine">Eptazocine</a></li> <li><a href="/w/index.php?title=Erinacine_E&amp;action=edit&amp;redlink=1" class="new" title="Erinacine E (page does not exist)">Erinacine E</a></li> <li><a href="/wiki/Ethylketazocine" title="Ethylketazocine">Ethylketazocine</a></li> <li><a href="/wiki/Etorphine" title="Etorphine">Etorphine</a></li> <li><a href="/wiki/Fedotozine" title="Fedotozine">Fedotozine</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a></li> <li><a href="/wiki/Gemazocine" title="Gemazocine">Gemazocine</a></li> <li><a href="/wiki/GR-89696" title="GR-89696">GR-89696</a></li> <li><a href="/w/index.php?title=GR-103545&amp;action=edit&amp;redlink=1" class="new" title="GR-103545 (page does not exist)">GR-103545</a></li> <li><a href="/wiki/Hemorphin-4" title="Hemorphin-4">Hemorphin-4</a></li> <li><a href="/wiki/Herkinorin" title="Herkinorin">Herkinorin</a></li> <li><a href="/wiki/HS665" title="HS665">HS665</a></li> <li><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone</a></li> <li><a href="/wiki/HZ-2" title="HZ-2">HZ-2</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/ICI-199,441" title="ICI-199,441">ICI-199,441</a></li> <li><a href="/wiki/ICI-204,448" title="ICI-204,448">ICI-204,448</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Ketazocine" title="Ketazocine">Ketazocine</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/wiki/Leumorphin" title="Leumorphin">Leumorphin (dynorphin B-29)</a></li> <li><a href="/wiki/Levallorphan" title="Levallorphan">Levallorphan</a></li> <li><a href="/wiki/Levomethorphan" title="Levomethorphan">Levomethorphan</a></li> <li><a href="/wiki/Levorphanol" title="Levorphanol">Levorphanol</a></li> <li><a href="/w/index.php?title=Lexanopadol&amp;action=edit&amp;redlink=1" class="new" title="Lexanopadol (page does not exist)">Lexanopadol</a></li> <li><a href="/wiki/Lofentanil" title="Lofentanil">Lofentanil</a></li> <li><a href="/wiki/LPK-26" title="LPK-26">LPK-26</a></li> <li><a href="/wiki/Lufuradom" title="Lufuradom">Lufuradom</a></li> <li><a href="/wiki/Matrine" title="Matrine">Matrine</a></li> <li><a href="/w/index.php?title=MB-1C-OH&amp;action=edit&amp;redlink=1" class="new" title="MB-1C-OH (page does not exist)">MB-1C-OH</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/Metazocine" title="Metazocine">Metazocine</a></li> <li><a href="/wiki/Metkefamide" title="Metkefamide">Metkefamide</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li> <li><a href="/wiki/Mirtazapine" title="Mirtazapine">Mirtazapine</a></li> <li><a class="mw-selflink selflink">Morphine</a></li> <li><a href="/wiki/Moxazocine" title="Moxazocine">Moxazocine</a></li> <li><a href="/w/index.php?title=MR-2034&amp;action=edit&amp;redlink=1" class="new" title="MR-2034 (page does not exist)">MR-2034</a></li> <li><a href="/w/index.php?title=N-MPPP&amp;action=edit&amp;redlink=1" class="new" title="N-MPPP (page does not exist)">N-MPPP</a></li> <li><a href="/wiki/Nalbuphine" title="Nalbuphine">Nalbuphine</a></li> <li><a href="/w/index.php?title=Naloxone_benzoylhydrazone&amp;action=edit&amp;redlink=1" class="new" title="Naloxone benzoylhydrazone (page does not exist)">NalBzOH</a></li> <li><a href="/wiki/Nalfurafine" title="Nalfurafine">Nalfurafine</a></li> <li><a href="/wiki/Nalmefene" title="Nalmefene">Nalmefene</a></li> <li><a href="/wiki/Nalodeine" title="Nalodeine">Nalodeine (N-allylnorcodeine)</a></li> <li><a href="/wiki/Nalorphine" title="Nalorphine">Nalorphine</a></li> <li><a href="/wiki/Naltriben" title="Naltriben">Naltriben</a></li> <li><a href="/wiki/Niravoline" title="Niravoline">Niravoline</a></li> <li><a href="/wiki/Norbuprenorphine" title="Norbuprenorphine">Norbuprenorphine</a></li> <li><a href="/wiki/Norbuprenorphine-3-glucuronide" title="Norbuprenorphine-3-glucuronide">Norbuprenorphine-3-glucuronide</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Oripavine" title="Oripavine">Oripavine</a></li> <li><a href="/wiki/Oxilorphan" title="Oxilorphan">Oxilorphan</a></li> <li><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine (meperidine)</a></li> <li><a href="/wiki/Phenazocine" title="Phenazocine">Phenazocine</a></li> <li><a href="/wiki/Proxorphan" title="Proxorphan">Proxorphan</a></li> <li><a href="/wiki/Methorphan" title="Methorphan">Racemethorphan</a></li> <li><a href="/wiki/Racemorphan" title="Racemorphan">Racemorphan</a></li> <li><a href="/wiki/RB-64" title="RB-64">RB-64</a></li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a> (<a href="/wiki/Salvia_divinorum" title="Salvia divinorum">salvia</a>)</li> <li><a href="/wiki/Salvinorin_B_ethoxymethyl_ether" class="mw-redirect" title="Salvinorin B ethoxymethyl ether">Salvinorin B ethoxymethyl ether</a></li> <li><a href="/wiki/Salvinorin_B_methoxymethyl_ether" title="Salvinorin B methoxymethyl ether">Salvinorin B methoxymethyl ether</a></li> <li><a href="/wiki/Samidorphan" title="Samidorphan">Samidorphan</a></li> <li><a href="/wiki/Spiradoline" title="Spiradoline">Spiradoline</a> (U-62066)</li> <li><a href="/wiki/TH-030418" title="TH-030418">TH-030418</a></li> <li><a href="/wiki/Thienorphine" title="Thienorphine">Thienorphine</a></li> <li><a href="/wiki/Tifluadom" title="Tifluadom">Tifluadom</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Desipramine" title="Desipramine">desipramine</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>)</li> <li><a href="/wiki/U-50488" title="U-50488">U-50488</a></li> <li><a href="/w/index.php?title=U-54494A&amp;action=edit&amp;redlink=1" class="new" title="U-54494A (page does not exist)">U-54494A</a></li> <li><a href="/wiki/U-69593" class="mw-redirect" title="U-69593">U-69593</a></li> <li><a href="/wiki/Xorphanol" title="Xorphanol">Xorphanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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/4%E2%80%B2-Hydroxyflavanone" class="mw-redirect" title="4′-Hydroxyflavanone">4′-Hydroxyflavanone</a></li> <li><a href="/wiki/4%27,7-Dihydroxyflavone" title="4&#39;,7-Dihydroxyflavone">4',7-Dihydroxyflavone</a></li> <li><a href="/wiki/5%27-Guanidinonaltrindole" title="5&#39;-Guanidinonaltrindole">5'-GNTI</a></li> <li><a href="/wiki/6%27-Guanidinonaltrindole" title="6&#39;-Guanidinonaltrindole">6'-GNTI</a></li> <li><a href="/wiki/6%CE%B2-Naltrexol" title="6β-Naltrexol">6β-Naltrexol</a></li> <li><a href="/wiki/6%CE%B2-Naltrexol-d4" title="6β-Naltrexol-d4">6β-Naltrexol-d4</a></li> <li><a href="/wiki/Chlornaltrexamine" class="mw-redirect" title="Chlornaltrexamine">β-Chlornaltrexamine</a></li> <li><a href="/wiki/Buprenorphine/samidorphan" title="Buprenorphine/samidorphan">Buprenorphine/samidorphan</a></li> <li><a href="/wiki/Amentoflavone" title="Amentoflavone">Amentoflavone</a></li> <li><a href="/w/index.php?title=5%27-Acetamidinoethylnaltrindole&amp;action=edit&amp;redlink=1" class="new" title="5&#39;-Acetamidinoethylnaltrindole (page does not exist)">ANTI</a></li> <li><a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/w/index.php?title=Arodyne&amp;action=edit&amp;redlink=1" class="new" title="Arodyne (page does not exist)">Arodyne</a></li> <li><a href="/wiki/AT-076" title="AT-076">AT-076</a></li> <li><a href="/wiki/Aticaprant" title="Aticaprant">Aticaprant</a></li> <li><a href="/wiki/Axelopran" title="Axelopran">Axelopran</a></li> <li><a href="/w/index.php?title=AZ-MTAB&amp;action=edit&amp;redlink=1" class="new" title="AZ-MTAB (page does not exist)">AZ-MTAB</a></li> <li><a href="/wiki/Binaltorphimine" title="Binaltorphimine">Binaltorphimine</a></li> <li><a href="/wiki/BU09059" title="BU09059">BU09059</a></li> <li><a href="/wiki/Buprenorphine" title="Buprenorphine">Buprenorphine</a></li> <li><a href="/wiki/Catechin" title="Catechin">Catechin</a></li> <li><a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">Catechin gallate</a></li> <li><a href="/wiki/CERC-501" class="mw-redirect" title="CERC-501">CERC-501 (LY-2456302)</a></li> <li><a href="/wiki/Clocinnamox" title="Clocinnamox">Clocinnamox</a></li> <li><a href="/wiki/Icalcaprant" title="Icalcaprant">CVL-354</a></li> <li><a href="/w/index.php?title=Cyclofoxy&amp;action=edit&amp;redlink=1" class="new" title="Cyclofoxy (page does not exist)">Cyclofoxy</a></li> <li><a href="/wiki/Dezocine" title="Dezocine">Dezocine</a></li> <li><a href="/w/index.php?title=DIPPA&amp;action=edit&amp;redlink=1" class="new" title="DIPPA (page does not exist)">DIPPA</a></li> <li><a href="/wiki/Gallocatechol" title="Gallocatechol">EGC</a></li> <li><a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a></li> <li><a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">Epicatechin</a></li> <li><a href="/wiki/Hyperoside" title="Hyperoside">Hyperoside</a></li> <li><a href="/wiki/JDTic" title="JDTic">JDTic</a></li> <li><a href="/wiki/LY-255582" title="LY-255582">LY-255582</a></li> <li><a href="/wiki/LY-2196044" class="mw-redirect" title="LY-2196044">LY-2196044</a></li> <li><a href="/w/index.php?title=LY-2444296&amp;action=edit&amp;redlink=1" class="new" title="LY-2444296 (page does not exist)">LY-2444296</a></li> <li><a href="/wiki/LY-2459989" title="LY-2459989">LY-2459989</a></li> <li><a href="/w/index.php?title=LY-2795050&amp;action=edit&amp;redlink=1" class="new" title="LY-2795050 (page does not exist)">LY-2795050</a></li> <li><a href="/w/index.php?title=MeJDTic&amp;action=edit&amp;redlink=1" class="new" title="MeJDTic (page does not exist)">MeJDTic</a></li> <li><a href="/wiki/Methylnaltrexone" title="Methylnaltrexone">Methylnaltrexone</a></li> <li><a href="/w/index.php?title=ML190&amp;action=edit&amp;redlink=1" class="new" title="ML190 (page does not exist)">ML190</a></li> <li><a href="/w/index.php?title=ML350&amp;action=edit&amp;redlink=1" class="new" title="ML350 (page does not exist)">ML350</a></li> <li><a href="/w/index.php?title=MR-2266&amp;action=edit&amp;redlink=1" class="new" title="MR-2266 (page does not exist)">MR-2266</a></li> <li><a href="/w/index.php?title=N-Fluoropropyl-JDTic&amp;action=edit&amp;redlink=1" class="new" title="N-Fluoropropyl-JDTic (page does not exist)">N-Fluoropropyl-JDTic</a></li> <li><a href="/wiki/Naloxone" title="Naloxone">Naloxone</a></li> <li><a href="/wiki/Naltrexone" title="Naltrexone">Naltrexone</a></li> <li><a href="/wiki/Naltrindole" title="Naltrindole">Naltrindole</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/wiki/Navacaprant" title="Navacaprant">Navacaprant</a></li> <li><a href="/wiki/Norbinaltorphimine" title="Norbinaltorphimine">Norbinaltorphimine</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Pawhuskin_A" title="Pawhuskin A">Pawhuskin A</a></li> <li><a href="/wiki/PF-4455242" class="mw-redirect" title="PF-4455242">PF-4455242</a></li> <li><a href="/wiki/RB-64" title="RB-64">RB-64</a></li> <li><a href="/wiki/Quadazocine" title="Quadazocine">Quadazocine</a></li> <li><a href="/wiki/Taxifolin" title="Taxifolin">Taxifolin</a></li> <li><a href="/w/index.php?title=UPHIT&amp;action=edit&amp;redlink=1" class="new" title="UPHIT (page does not exist)">UPHIT</a></li> <li><a href="/wiki/Zyklophin" title="Zyklophin">Zyklophin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Nociceptin_receptor" title="Nociceptin receptor">Nociceptin</a><br />(NOP)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Agonists</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="/w/index.php?title=(Arg14,Lys15)Nociceptin&amp;action=edit&amp;redlink=1" class="new" title="(Arg14,Lys15)Nociceptin (page does not exist)">(Arg14,Lys15)Nociceptin</a></li> <li><a href="/w/index.php?title=((pF)Phe4)Nociceptin(1-13)NH2&amp;action=edit&amp;redlink=1" class="new" title="((pF)Phe4)Nociceptin(1-13)NH2 (page does not exist)">((pF)Phe<sup>4</sup>)Nociceptin(1-13)NH<sub>2</sub></a></li> <li><a href="/w/index.php?title=(Phe1%CE%A8(CH2-NH)Gly2)Nociceptin(1-13)NH2&amp;action=edit&amp;redlink=1" class="new" title="(Phe1Ψ(CH2-NH)Gly2)Nociceptin(1-13)NH2 (page does not exist)">(Phe<sup>1</sup>Ψ(CH<sub>2</sub>-NH)Gly<sup>2</sup>)Nociceptin(1-13)NH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Ac-RYYRWK-NH2&amp;action=edit&amp;redlink=1" class="new" title="Ac-RYYRWK-NH2 (page does not exist)">Ac-RYYRWK-NH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Ac-RYYRIK-NH2&amp;action=edit&amp;redlink=1" class="new" title="Ac-RYYRIK-NH2 (page does not exist)">Ac-RYYRIK-NH<sub>2</sub></a></li> <li><a href="/w/index.php?title=BU08070&amp;action=edit&amp;redlink=1" class="new" title="BU08070 (page does not exist)">BU08070</a></li> <li><a href="/wiki/Buprenorphine" title="Buprenorphine">Buprenorphine</a></li> <li><a href="/wiki/Cebranopadol" title="Cebranopadol">Cebranopadol</a></li> <li><a href="/wiki/Dihydroetorphine" title="Dihydroetorphine">Dihydroetorphine</a></li> <li><a href="/wiki/Etorphine" title="Etorphine">Etorphine</a></li> <li><a href="/w/index.php?title=JNJ-19385899&amp;action=edit&amp;redlink=1" class="new" title="JNJ-19385899 (page does not exist)">JNJ-19385899</a></li> <li><a href="/wiki/Levomethorphan" title="Levomethorphan">Levomethorphan</a></li> <li><a href="/wiki/Levorphanol" title="Levorphanol">Levorphanol</a></li> <li><a href="/w/index.php?title=Lexanopadol&amp;action=edit&amp;redlink=1" class="new" title="Lexanopadol (page does not exist)">Lexanopadol</a></li> <li><a href="/wiki/MCOPPB" title="MCOPPB">MCOPPB</a></li> <li><a href="/wiki/MT-7716" title="MT-7716">MT-7716</a></li> <li><a href="/wiki/NNC_63-0532" title="NNC 63-0532">NNC 63-0532</a></li> <li><a href="/wiki/Nociceptin" title="Nociceptin">Nociceptin (orphanin FQ)</a></li> <li><a href="/w/index.php?title=Nociceptin_(1-11)&amp;action=edit&amp;redlink=1" class="new" title="Nociceptin (1-11) (page does not exist)">Nociceptin (1-11)</a></li> <li><a href="/w/index.php?title=Nociceptin_(1-13)NH2&amp;action=edit&amp;redlink=1" class="new" title="Nociceptin (1-13)NH2 (page does not exist)">Nociceptin (1-13)NH<sub>2</sub></a></li> <li><a href="/wiki/Norbuprenorphine" title="Norbuprenorphine">Norbuprenorphine</a></li> <li><a href="/wiki/Methorphan" title="Methorphan">Racemethorphan</a></li> <li><a href="/wiki/Racemorphan" title="Racemorphan">Racemorphan</a></li> <li><a href="/wiki/Ro64-6198" title="Ro64-6198">Ro64-6198</a></li> <li><a href="/wiki/Ro65-6570" title="Ro65-6570">Ro65-6570</a></li> <li><a href="/wiki/SCH-221510" title="SCH-221510">SCH-221510</a></li> <li><a href="/w/index.php?title=SCH-486757&amp;action=edit&amp;redlink=1" class="new" title="SCH-486757 (page does not exist)">SCH-486757</a></li> <li><a href="/w/index.php?title=SR-8993&amp;action=edit&amp;redlink=1" class="new" title="SR-8993 (page does not exist)">SR-8993</a></li> <li><a href="/wiki/SR-16435" title="SR-16435">SR-16435</a></li> <li><a href="/wiki/Sunobinop" title="Sunobinop">Sunobinop (S-117957)</a></li> <li><a href="/wiki/TH-030418" title="TH-030418">TH-030418</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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="/w/index.php?title=(Nphe1)Nociceptin(1-13)NH2&amp;action=edit&amp;redlink=1" class="new" title="(Nphe1)Nociceptin(1-13)NH2 (page does not exist)">(Nphe<sup>1</sup>)Nociceptin(1-13)NH<sub>2</sub></a></li> <li><a href="/wiki/AT-076" title="AT-076">AT-076</a></li> <li><a href="/w/index.php?title=BAN-ORL-24&amp;action=edit&amp;redlink=1" class="new" title="BAN-ORL-24 (page does not exist)">BAN-ORL-24</a></li> <li><a href="/wiki/BTRX-246040" title="BTRX-246040">BTRX-246040 (LY-2940094)</a></li> <li><a href="/wiki/J-113397" class="mw-redirect" title="J-113397">J-113397</a></li> <li><a href="/wiki/JTC-801" title="JTC-801">JTC-801</a></li> <li><a href="/w/index.php?title=Naloxone_benzoylhydrazone&amp;action=edit&amp;redlink=1" class="new" title="Naloxone benzoylhydrazone (page does not exist)">NalBzOH</a></li> <li><a href="/w/index.php?title=Nociceptin_(1-7)&amp;action=edit&amp;redlink=1" class="new" title="Nociceptin (1-7) (page does not exist)">Nociceptin (1-7)</a></li> <li><a href="/w/index.php?title=Nocistatin&amp;action=edit&amp;redlink=1" class="new" title="Nocistatin (page does not exist)">Nocistatin</a></li> <li><a href="/wiki/SB-612111" class="mw-redirect" title="SB-612111">SB-612111</a></li> <li><a href="/w/index.php?title=SR-16430&amp;action=edit&amp;redlink=1" class="new" title="SR-16430 (page does not exist)">SR-16430</a></li> <li><a href="/wiki/Thienorphine" title="Thienorphine">Thienorphine</a></li> <li><a href="/w/index.php?title=Trap-101&amp;action=edit&amp;redlink=1" class="new" title="Trap-101 (page does not exist)">Trap-101</a></li> <li><a href="/w/index.php?title=UFP-101&amp;action=edit&amp;redlink=1" class="new" title="UFP-101 (page does not exist)">UFP-101</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Enkephalinase_inhibitor" title="Enkephalinase inhibitor">Enkephalinase inhibitors</a>:</i> <a href="/wiki/Amastatin" title="Amastatin">Amastatin</a></li> <li><a href="/w/index.php?title=BL-2401&amp;action=edit&amp;redlink=1" class="new" title="BL-2401 (page does not exist)">BL-2401</a></li> <li><a href="/wiki/Candoxatril" title="Candoxatril">Candoxatril</a></li> <li><a href="/wiki/Phenylalanine#D-,_L-_and_DL-phenylalanine" title="Phenylalanine"><span style="font-size:85%;">D</span>-Phenylalanine</a></li> <li><a href="/w/index.php?title=Dexecadotril&amp;action=edit&amp;redlink=1" class="new" title="Dexecadotril (page does not exist)">Dexecadotril (retorphan)</a></li> <li><a href="/wiki/Ecadotril" title="Ecadotril">Ecadotril (sinorphan)</a></li> <li><a href="/wiki/Kelatorphan" title="Kelatorphan">Kelatorphan</a></li> <li><a href="/wiki/Racecadotril" title="Racecadotril">Racecadotril (acetorphan)</a></li> <li><a href="/wiki/RB-101" title="RB-101">RB-101</a></li> <li><a href="/wiki/RB-120" title="RB-120">RB-120</a></li> <li><a href="/wiki/RB-3007" title="RB-3007">RB-3007</a></li> <li><a href="/w/index.php?title=Opiorphan&amp;action=edit&amp;redlink=1" class="new" title="Opiorphan (page does not exist)">Opiorphan</a></li> <li><a href="/wiki/Selank" title="Selank">Selank</a></li> <li><a href="/wiki/Semax" title="Semax">Semax</a></li> <li><a href="/wiki/Spinorphin" title="Spinorphin">Spinorphin</a></li> <li><a href="/wiki/Thiorphan" title="Thiorphan">Thiorphan</a></li> <li><a href="/wiki/Tynorphin" title="Tynorphin">Tynorphin</a></li> <li><a href="/wiki/Ubenimex" title="Ubenimex">Ubenimex (bestatin)</a></li></ul> <ul><li><i>Propeptides:</i> <a href="/wiki/Lipotropin" title="Lipotropin">β-Lipotropin (proendorphin)</a></li> <li><a href="/wiki/Prodynorphin" title="Prodynorphin">Prodynorphin</a></li> <li><a href="/wiki/Proenkephalin" title="Proenkephalin">Proenkephalin</a></li> <li><a href="/w/index.php?title=Pronociceptin&amp;action=edit&amp;redlink=1" class="new" title="Pronociceptin (page does not exist)">Pronociceptin</a></li> <li><a href="/wiki/Proopiomelanocortin" title="Proopiomelanocortin">Proopiomelanocortin (POMC)</a></li></ul> <ul><li><i>Others:</i> <a href="/wiki/Kyotorphin" title="Kyotorphin">Kyotorphin</a> (met-enkephalin releaser/degradation stabilizer)</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="Glycine_receptor_modulators592" style="padding:3px"><table class="nowraplinks hlist 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:Glycine_receptor_modulators" title="Template:Glycine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glycine_receptor_modulators" title="Template talk:Glycine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glycine_receptor_modulators" title="Special:EditPage/Template:Glycine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glycine_receptor_modulators592" style="font-size:114%;margin:0 4em"><a href="/wiki/Glycine_receptor" title="Glycine receptor">Glycine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></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:4em;;text-align:center;"><a href="/wiki/Glycine_receptor" title="Glycine receptor"><abbr title="Glycine receptor">GlyR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Beta-Aminobutyric_acid" class="mw-redirect" title="Beta-Aminobutyric acid">β-ABA (BABA)</a></li> <li><a href="/wiki/%CE%92-Aminoisobutyric_acid" class="mw-redirect" title="Β-Aminoisobutyric acid">β-AIBA</a></li> <li><a href="/wiki/Caesium" title="Caesium">Caesium</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>D</small>-Alanine</a></li> <li><a href="/wiki/Serine" title="Serine"><small>D</small>-Serine</a></li> <li><a href="/wiki/Gamma-Aminobutyric_acid" class="mw-redirect" title="Gamma-Aminobutyric acid">GABA</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Hypotaurine" title="Hypotaurine">Hypotaurine</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>L</small>-Alanine</a></li> <li><a href="/wiki/Proline" title="Proline"><small>L</small>-Proline</a></li> <li><a href="/wiki/Serine" title="Serine"><small>L</small>-Serine</a></li> <li><a href="/wiki/Threonine" title="Threonine"><small>L</small>-Threonine</a></li> <li><a href="/w/index.php?title=MDL-27531&amp;action=edit&amp;redlink=1" class="new" title="MDL-27531 (page does not exist)">MDL-27531</a></li> <li><a href="/wiki/Milacemide" title="Milacemide">Milacemide</a></li> <li><a href="/wiki/Picolinic_acid" title="Picolinic acid">Picolinic acid</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Quisqualamine" title="Quisqualamine">Quisqualamine</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li></ul> <ul><li><b>Positive modulators:</b> <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> (e.g., <a href="/w/index.php?title=Brometone&amp;action=edit&amp;redlink=1" class="new" title="Brometone (page does not exist)">brometone</a>, <a href="/wiki/Chlorobutanol" title="Chlorobutanol">chlorobutanol (chloretone)</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">ethanol (alcohol)</a>, <a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-butanol (2M2P)</a>, <a href="/wiki/Tribromoethanol" title="Tribromoethanol">tribromoethanol</a>, <a href="/wiki/Trichloroethanol" class="mw-redirect" title="Trichloroethanol">trichloroethanol</a>, <a href="/wiki/Trifluoroethanol" class="mw-redirect" title="Trifluoroethanol">trifluoroethanol</a>)</li> <li><a href="/wiki/Alkylbenzene_sulfonate" title="Alkylbenzene sulfonate">Alkylbenzene sulfonate</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/Chlormethiazole" class="mw-redirect" title="Chlormethiazole">Chlormethiazole</a></li> <li><a href="/w/index.php?title=D12-116&amp;action=edit&amp;redlink=1" class="new" title="D12-116 (page does not exist)">D12-116</a></li> <li><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a> (e.g., <a href="/wiki/Nicardipine" title="Nicardipine">nicardipine</a>)</li> <li><a href="/wiki/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">Ginseng</a> constituents (e.g., <a href="/wiki/Ginsenoside" title="Ginsenoside">ginsenosides</a> (e.g., <a href="/w/index.php?title=Ginsenoside-Rf&amp;action=edit&amp;redlink=1" class="new" title="Ginsenoside-Rf (page does not exist)">ginsenoside-Rf</a>))</li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid (glutamate)</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/Alfaxolone" class="mw-redirect" title="Alfaxolone">alfaxolone</a>, <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone (eltanolone)</a>, <a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">pregnenolone acetate</a>, <a href="/wiki/Minaxolone" title="Minaxolone">minaxolone</a>, <a href="/wiki/ORG-20599" title="ORG-20599">ORG-20599</a>)</li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Penicillin_G" class="mw-redirect" title="Penicillin G">Penicillin G</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a></li> <li><a href="/wiki/Triclofos" title="Triclofos">Triclofos</a></li> <li><a href="/w/index.php?title=Tropeine&amp;action=edit&amp;redlink=1" class="new" title="Tropeine (page does not exist)">Tropeines</a> (e.g., <a href="/wiki/Atropine" title="Atropine">atropine</a>, <a href="/wiki/Bemesetron" title="Bemesetron">bemesetron</a>, <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/w/index.php?title=LY-278584&amp;action=edit&amp;redlink=1" class="new" title="LY-278584 (page does not exist)">LY-278584</a>, <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, <a href="/wiki/Zatosetron" title="Zatosetron">zatosetron</a>)</li> <li><a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">Volatiles</a>/<a href="/wiki/Gas" title="Gas">gases</a> (e.g., <a href="/wiki/Chloral_hydrate" title="Chloral hydrate">chloral hydrate</a>, <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, <a href="/wiki/Desflurane" title="Desflurane">desflurane</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether (ether)</a>, <a href="/wiki/Enflurane" title="Enflurane">enflurane</a>, <a href="/wiki/Halothane" title="Halothane">halothane</a>, <a href="/wiki/Isoflurane" title="Isoflurane">isoflurane</a>, <a href="/wiki/Methoxyflurane" title="Methoxyflurane">methoxyflurane</a>, <a href="/wiki/Sevoflurane" title="Sevoflurane">sevoflurane</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/1,1,1-trichloroethane" class="mw-redirect" title="1,1,1-trichloroethane">trichloroethane (methyl chloroform)</a>, <a href="/wiki/Trichloroethylene" title="Trichloroethylene">trichloroethylene</a>)</li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=2-Aminostrychnine&amp;action=edit&amp;redlink=1" class="new" title="2-Aminostrychnine (page does not exist)">2-Aminostrychnine</a></li> <li><a href="/w/index.php?title=2-Nitrostrychnine&amp;action=edit&amp;redlink=1" class="new" title="2-Nitrostrychnine (page does not exist)">2-Nitrostrychnine</a></li> <li><a href="/w/index.php?title=4-Phenyl-4-formyl-N-methylpiperidine&amp;action=edit&amp;redlink=1" class="new" title="4-Phenyl-4-formyl-N-methylpiperidine (page does not exist)">4-Phenyl-4-formyl-N-methylpiperidine</a></li> <li><a href="/w/index.php?title=%CE%91-Ethyl-%CE%B1-methyl-%CE%B3-thiobutyrolactone&amp;action=edit&amp;redlink=1" class="new" title="Α-Ethyl-α-methyl-γ-thiobutyrolactone (page does not exist)">αEMBTL</a></li> <li><a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/wiki/Brucine" title="Brucine">Brucine</a></li> <li><a href="/wiki/Cacotheline" title="Cacotheline">Cacotheline</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Colchicine" title="Colchicine">Colchicine</a></li> <li><a href="/wiki/Colubrine" class="mw-redirect" title="Colubrine">Colubrine</a></li> <li><a href="/w/index.php?title=Cyanotriphenylborate&amp;action=edit&amp;redlink=1" class="new" title="Cyanotriphenylborate (page does not exist)">Cyanotriphenylborate</a></li> <li><a href="/wiki/Dendrobine" title="Dendrobine">Dendrobine</a></li> <li><a href="/w/index.php?title=Diaboline&amp;action=edit&amp;redlink=1" class="new" title="Diaboline (page does not exist)">Diaboline</a></li> <li><a href="/wiki/Endocannabinoid" class="mw-redirect" title="Endocannabinoid">Endocannabinoids</a> (e.g., <a href="/wiki/2-arachidonylglycerol" class="mw-redirect" title="2-arachidonylglycerol">2-AG</a>, <a href="/wiki/Anandamide" title="Anandamide">anandamide (AEA)</a>)</li> <li><a href="/wiki/Gaboxadol" title="Gaboxadol">Gaboxadol (THIP)</a></li> <li><a href="/wiki/Gelsemine" title="Gelsemine">Gelsemine</a></li> <li><a href="/w/index.php?title=Iso-THAZ&amp;action=edit&amp;redlink=1" class="new" title="Iso-THAZ (page does not exist)">iso-THAZ</a></li> <li><a href="/wiki/Isobutyric_acid" title="Isobutyric acid">Isobutyric acid</a></li> <li><a href="/wiki/Isonipecotic_acid" title="Isonipecotic acid">Isonipecotic acid</a></li> <li><a href="/w/index.php?title=Isostrychnine&amp;action=edit&amp;redlink=1" class="new" title="Isostrychnine (page does not exist)">Isostrychnine</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/w/index.php?title=N-Methylbicuculline&amp;action=edit&amp;redlink=1" class="new" title="N-Methylbicuculline (page does not exist)">N-Methylbicuculline</a></li> <li><a href="/w/index.php?title=N-Methylstrychnine&amp;action=edit&amp;redlink=1" class="new" title="N-Methylstrychnine (page does not exist)">N-Methylstrychnine</a></li> <li><a href="/w/index.php?title=N,N-Dimethylmuscimol&amp;action=edit&amp;redlink=1" class="new" title="N,N-Dimethylmuscimol (page does not exist)">N,N-Dimethylmuscimol</a></li> <li><a href="/wiki/Nipecotic_acid" title="Nipecotic acid">Nipecotic acid</a></li> <li><a href="/wiki/Pitrazepin" title="Pitrazepin">Pitrazepin</a></li> <li><a href="/w/index.php?title=Pseudostrychnine&amp;action=edit&amp;redlink=1" class="new" title="Pseudostrychnine (page does not exist)">Pseudostrychnine</a></li> <li><a href="/wiki/Quinoline" title="Quinoline">Quinolines</a> (e.g., <a href="/w/index.php?title=4-hydroxyquinoline&amp;action=edit&amp;redlink=1" class="new" title="4-hydroxyquinoline (page does not exist)">4-hydroxyquinoline</a>, <a href="/w/index.php?title=4-hydroxyquinoline-3-carboxylic_acid&amp;action=edit&amp;redlink=1" class="new" title="4-hydroxyquinoline-3-carboxylic acid (page does not exist)">4-hydroxyquinoline-3-carboxylic acid</a>, <a href="/w/index.php?title=5,7-dichloro-4-hydroxyquinoline-3-carboxylic_acid&amp;action=edit&amp;redlink=1" class="new" title="5,7-dichloro-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">5,7-CIQA</a>, <a href="/w/index.php?title=7-chloro-4-hydroxyquinoline&amp;action=edit&amp;redlink=1" class="new" title="7-chloro-4-hydroxyquinoline (page does not exist)">7-CIQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline&amp;action=edit&amp;redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline (page does not exist)">7-TFQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic_acid&amp;action=edit&amp;redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">7-TFQA</a>)</li> <li><a href="/w/index.php?title=RU-5135&amp;action=edit&amp;redlink=1" class="new" title="RU-5135 (page does not exist)">RU-5135</a></li> <li><a href="/wiki/Sinomenine" title="Sinomenine">Sinomenine</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Tutin_(toxin)" title="Tutin (toxin)">Tutin</a></li></ul> <ul><li><b>Negative modulators:</b> <a href="/wiki/Amiloride" title="Amiloride">Amiloride</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a> (e.g., <a href="/wiki/Bromazepam" title="Bromazepam">bromazepam</a>, <a href="/wiki/Clonazepam" title="Clonazepam">clonazepam</a>, <a href="/wiki/Diazepam" title="Diazepam">diazepam</a>, <a href="/wiki/Flunitrazepam" title="Flunitrazepam">flunitrazepam</a>, <a href="/wiki/Flurazepam" title="Flurazepam">flurazepam</a>)</li> <li><a href="/wiki/Corymine" title="Corymine">Corymine</a></li> <li><a href="/w/index.php?title=Cyanotriphenylborate&amp;action=edit&amp;redlink=1" class="new" title="Cyanotriphenylborate (page does not exist)">Cyanotriphenylborate</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a> (e.g., <a href="/wiki/Nicardipine" title="Nicardipine">nicardipine</a>, <a href="/wiki/Nifedipine" title="Nifedipine">nifedipine</a>, <a href="/wiki/Nitrendipine" title="Nitrendipine">nitrendipine</a>)</li> <li><a href="/wiki/Furosemide" title="Furosemide">Furosemide</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Ginkgo_biloba" title="Ginkgo biloba">Ginkgo</a> constituents (e.g., <a href="/wiki/Bilobalide" title="Bilobalide">bilobalide</a>, <a href="/wiki/Ginkgolide" title="Ginkgolide">ginkgolides</a> (e.g., <a href="/w/index.php?title=Ginkgolide_A&amp;action=edit&amp;redlink=1" class="new" title="Ginkgolide A (page does not exist)">ginkgolide A</a>, <a href="/wiki/Ginkgolide_B" class="mw-redirect" title="Ginkgolide B">ginkgolide B</a>, <a href="/w/index.php?title=Ginkgolide_C&amp;action=edit&amp;redlink=1" class="new" title="Ginkgolide C (page does not exist)">ginkgolide C</a>, <a href="/w/index.php?title=Ginkgolide_J&amp;action=edit&amp;redlink=1" class="new" title="Ginkgolide J (page does not exist)">ginkgolide J</a>, <a href="/w/index.php?title=Ginkgolide_M&amp;action=edit&amp;redlink=1" class="new" title="Ginkgolide M (page does not exist)">ginkgolide M</a>))</li> <li><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a></li> <li><a href="/wiki/NBQX" title="NBQX">NBQX</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/3%CE%B1-androsterone_sulfate" class="mw-redirect" title="3α-androsterone sulfate">3α-androsterone sulfate</a>, <a href="/w/index.php?title=3%CE%B2-androsterone_sulfate&amp;action=edit&amp;redlink=1" class="new" title="3β-androsterone sulfate (page does not exist)">3β-androsterone sulfate</a>, <a href="/wiki/11-deoxycorticosterone" class="mw-redirect" title="11-deoxycorticosterone">deoxycorticosterone</a>, <a href="/wiki/DHEA_sulfate" class="mw-redirect" title="DHEA sulfate">DHEA sulfate</a>, <a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">pregnenolone sulfate</a>, <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>)</li> <li><a href="/wiki/Opioid" title="Opioid">Opioids</a> (e.g., <a href="/wiki/Codeine" title="Codeine">codeine</a>, <a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a>, <a href="/wiki/Dextrorphan" title="Dextrorphan">dextrorphan</a>, <a href="/wiki/Levomethadone" title="Levomethadone">levomethadone</a>, <a href="/wiki/Levorphanol" title="Levorphanol">levorphanol</a>, <a class="mw-selflink selflink">morphine</a>, <a href="/wiki/Oripavine" title="Oripavine">oripavine</a>, <a href="/wiki/Pethidine" title="Pethidine">pethidine</a>, <a href="/wiki/Thebaine" title="Thebaine">thebaine</a>)</li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a> (i.e., <a href="/wiki/Picrotin" class="mw-redirect" title="Picrotin">picrotin</a> and <a href="/wiki/Picrotoxinin" class="mw-redirect" title="Picrotoxinin">picrotoxinin</a>)</li> <li><a href="/w/index.php?title=Phenylbenzene_%CF%89-phosphono-%CE%B1-amino_acid&amp;action=edit&amp;redlink=1" class="new" title="Phenylbenzene ω-phosphono-α-amino acid (page does not exist)">PMBA</a></li> <li><a href="/wiki/Riluzole" title="Riluzole">Riluzole</a></li> <li><a href="/w/index.php?title=Tropeine&amp;action=edit&amp;redlink=1" class="new" title="Tropeine (page does not exist)">Tropeines</a> (e.g., <a href="/wiki/Bemesetron" title="Bemesetron">bemesetron</a>, <a href="/w/index.php?title=LY-278584&amp;action=edit&amp;redlink=1" class="new" title="LY-278584 (page does not exist)">LY-278584</a>, <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, <a href="/wiki/Zatosetron" title="Zatosetron">zatosetron</a>)</li> <li><a href="/wiki/Verapamil" title="Verapamil">Verapamil</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/N-Methyl-D-aspartate_receptor" class="mw-redirect" title="N-Methyl-D-aspartate receptor"><abbr title="N-Methyl-D-aspartate receptor">NMDAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip N-Methyl-D-aspartate receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">here</a> instead.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">Transporter</a><br /><small>(<a href="/wiki/Reuptake_inhibitor" title="Reuptake inhibitor">blockers</a>)</small></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:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_1" class="mw-redirect" title="Glycine transporter 1"><abbr title="Glycine transporter 1">GlyT1</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine transporter 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=ACPPB&amp;action=edit&amp;redlink=1" class="new" title="ACPPB (page does not exist)">ACPPB</a></li> <li><a href="/w/index.php?title=ALX-5407&amp;action=edit&amp;redlink=1" class="new" title="ALX-5407 (page does not exist)">ALX-5407 (NFPS)</a></li> <li><a href="/wiki/ASP2535" title="ASP2535">ASP2535</a></li> <li><a href="/wiki/Bitopertin" title="Bitopertin">Bitopertin (RG1678/RO4917838)</a></li> <li><a href="/w/index.php?title=CP-802079&amp;action=edit&amp;redlink=1" class="new" title="CP-802079 (page does not exist)">CP-802079</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Glycyldodecylamide&amp;action=edit&amp;redlink=1" class="new" title="Glycyldodecylamide (page does not exist)">Glycyldodecylamide</a></li> <li><a href="/w/index.php?title=GSK1018921&amp;action=edit&amp;redlink=1" class="new" title="GSK1018921 (page does not exist)">GSK1018921</a></li> <li><a href="/wiki/Iclepertin" title="Iclepertin">Iclepertin</a></li> <li><a href="/wiki/LY-2365109" title="LY-2365109">LY-2365109</a></li> <li><a href="/wiki/Mardepodect" title="Mardepodect">Mardepodect</a></li> <li><a href="/wiki/ORG-24598" title="ORG-24598">ORG-24598</a></li> <li><a href="/wiki/ORG-25935" title="ORG-25935">ORG-25935 (SCH-900435)</a></li> <li><a href="/wiki/Pesampator" title="Pesampator">Pesampator (BIIB-104, PF-04958242)</a></li> <li><a href="/w/index.php?title=PF-03463275&amp;action=edit&amp;redlink=1" class="new" title="PF-03463275 (page does not exist)">PF-03463275</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/SNG-12" title="SNG-12">SNG-12 (Synapsinae)</a></li> <li><a href="/w/index.php?title=SSR-103,800&amp;action=edit&amp;redlink=1" class="new" title="SSR-103,800 (page does not exist)">SSR-103,800</a></li> <li><a href="/w/index.php?title=SSR-504,734&amp;action=edit&amp;redlink=1" class="new" title="SSR-504,734 (page does not exist)">SSR-504,734</a></li> <li><a href="/wiki/Tilapertin" title="Tilapertin">Tilapertin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_2" class="mw-redirect" title="Glycine transporter 2"><abbr title="Glycine transporter 2">GlyT2</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine transporter 2</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/ALX-1393" title="ALX-1393">ALX-1393</a></li> <li><a href="/wiki/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/N-Arachidonylglycine" title="N-Arachidonylglycine">NAGly</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/w/index.php?title=ORG-25543&amp;action=edit&amp;redlink=1" class="new" title="ORG-25543 (page does not exist)">ORG-25543</a></li> <li><a href="/w/index.php?title=VVZ-368&amp;action=edit&amp;redlink=1" class="new" title="VVZ-368 (page does not exist)">VVZ-368</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd> <dd><i><a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a></i></dd> <dd><i><a href="/wiki/Template:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators">GABA<sub>A</sub> receptor positive modulators</a></i></dd> <dd><i><a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">Ionotropic glutamate receptor modulators</a></i></dd></dl> </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 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.portal-bar-content-related{border-top:none;margin:0;list-style:none}}.mw-parser-output .navbox+link+.portal-bar,.mw-parser-output .navbox+style+.portal-bar,.mw-parser-output .navbox+link+.portal-bar-bordered,.mw-parser-output .navbox+style+.portal-bar-bordered,.mw-parser-output .sister-bar+link+.portal-bar,.mw-parser-output .sister-bar+style+.portal-bar,.mw-parser-output .portal-bar+.navbox-styles+.navbox,.mw-parser-output .portal-bar+.navbox-styles+.sister-bar{margin-top:-1px}</style><div class="portal-bar noprint metadata noviewer portal-bar-bordered" role="navigation" aria-label="Portals"><span class="portal-bar-header"><a href="/wiki/Wikipedia:Contents/Portals" title="Wikipedia:Contents/Portals">Portal</a>:</span><ul class="portal-bar-content"><li class="portal-bar-item"><span class="nowrap"><span typeof="mw:File"><span><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/8px-WHO_Rod.svg.png" decoding="async" width="8" height="19" 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aria-labelledby="Authority_control_databases_frameless&amp;#124;text-top&amp;#124;10px&amp;#124;alt=Edit_this_at_Wikidata&amp;#124;link=https&amp;#58;//www.wikidata.org/wiki/Q81225#identifiers&amp;#124;class=noprint&amp;#124;Edit_this_at_Wikidata1612" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="Authority_control_databases_frameless&amp;#124;text-top&amp;#124;10px&amp;#124;alt=Edit_this_at_Wikidata&amp;#124;link=https&amp;#58;//www.wikidata.org/wiki/Q81225#identifiers&amp;#124;class=noprint&amp;#124;Edit_this_at_Wikidata1612" style="font-size:114%;margin:0 4em"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q81225#identifiers" 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></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">International</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="http://id.worldcat.org/fast/1026429/">FAST</a></span></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">National</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4040284-8">Germany</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85087342">United States</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Morphine"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb11979266z">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Morphine"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb11979266z">BnF data</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/01035412">Japan</a></span></li><li><span 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