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Nicotine - Wikipedia
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vector-toc-level-2"> <a class="vector-toc-link" href="#Medical"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Medical</span> </div> </a> <ul id="toc-Medical-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pesticide" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pesticide"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Pesticide</span> </div> </a> <ul id="toc-Pesticide-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Performance" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Performance"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Performance</span> </div> </a> <ul id="toc-Performance-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Recreational" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Recreational"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Recreational</span> </div> </a> <ul id="toc-Recreational-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-Sleep" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sleep"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Sleep</span> </div> </a> <ul id="toc-Sleep-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cardiovascular_system" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cardiovascular_system"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Cardiovascular system</span> </div> </a> <ul id="toc-Cardiovascular_system-sublist" class="vector-toc-list"> <li id="toc-Blood_pressure" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Blood_pressure"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2.1</span> <span>Blood pressure</span> </div> </a> <ul id="toc-Blood_pressure-sublist" class="vector-toc-list"> </ul> </li> </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">3.3</span> <span>Reinforcement disorders</span> </div> </a> <ul id="toc-Reinforcement_disorders-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cancer" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cancer"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Cancer</span> </div> </a> <ul id="toc-Cancer-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Genotoxicity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Genotoxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Genotoxicity</span> </div> </a> <ul id="toc-Genotoxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pregnancy_and_breastfeeding" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pregnancy_and_breastfeeding"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.6</span> <span>Pregnancy and breastfeeding</span> </div> </a> <ul id="toc-Pregnancy_and_breastfeeding-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Overdose" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Overdose"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Overdose</span> </div> </a> <button aria-controls="toc-Overdose-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 Overdose subsection</span> </button> <ul id="toc-Overdose-sublist" class="vector-toc-list"> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Toxicity</span> </div> </a> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Drug_interactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Drug_interactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Drug interactions</span> </div> </a> <button aria-controls="toc-Drug_interactions-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 Drug interactions subsection</span> </button> <ul id="toc-Drug_interactions-sublist" class="vector-toc-list"> <li id="toc-Pharmacodynamic" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamic"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Pharmacodynamic</span> </div> </a> <ul id="toc-Pharmacodynamic-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacokinetic" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetic"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Pharmacokinetic</span> </div> </a> <ul id="toc-Pharmacokinetic-sublist" class="vector-toc-list"> </ul> </li> </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">6</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">6.1</span> <span>Pharmacodynamics</span> </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> <li id="toc-Central_nervous_system" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Central_nervous_system"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1.1</span> <span>Central nervous system</span> </div> </a> <ul id="toc-Central_nervous_system-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Sympathetic_nervous_system" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Sympathetic_nervous_system"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1.2</span> <span>Sympathetic nervous system</span> </div> </a> <ul id="toc-Sympathetic_nervous_system-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Adrenal_medulla" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Adrenal_medulla"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1.3</span> <span>Adrenal medulla</span> </div> </a> <ul id="toc-Adrenal_medulla-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">6.2</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Metabolism</span> </div> </a> <ul id="toc-Metabolism-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-Preparation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Preparation"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Preparation</span> </div> </a> <ul id="toc-Preparation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Detection_in_body_fluids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Detection_in_body_fluids"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Detection in body fluids</span> </div> </a> <ul id="toc-Detection_in_body_fluids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Methods_for_analysis_of_enantiomers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Methods_for_analysis_of_enantiomers"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.4</span> <span>Methods for analysis of enantiomers</span> </div> </a> <ul id="toc-Methods_for_analysis_of_enantiomers-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">8</span> <span>Natural occurrence</span> </div> </a> <ul id="toc-Natural_occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History,_society_and_culture" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History,_society_and_culture"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>History, society and culture</span> </div> </a> <button aria-controls="toc-History,_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 History, society and culture subsection</span> </button> <ul id="toc-History,_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">9.1</span> <span>Legal status</span> </div> </a> <ul id="toc-Legal_status-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_media" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_media"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.2</span> <span>In media</span> </div> </a> <ul id="toc-In_media-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Research</span> </div> </a> <button aria-controls="toc-Research-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 Research subsection</span> </button> <ul id="toc-Research-sublist" class="vector-toc-list"> <li id="toc-Central_nervous_system_2" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Central_nervous_system_2"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.1</span> <span>Central nervous system</span> </div> </a> <ul id="toc-Central_nervous_system_2-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Immune_system" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Immune_system"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.2</span> <span>Immune system</span> </div> </a> <ul id="toc-Immune_system-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Optopharmacology" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Optopharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.3</span> <span>Optopharmacology</span> </div> </a> <ul id="toc-Optopharmacology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oral_health" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oral_health"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.4</span> <span>Oral health</span> </div> </a> <ul id="toc-Oral_health-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </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" > <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">Nicotine</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 107 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-107" 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">107 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/Nikotien" title="Nikotien – Afrikaans" lang="af" hreflang="af" data-title="Nikotien" 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/Nicotin" title="Nicotin – Alemannic" lang="gsw" hreflang="gsw" data-title="Nicotin" 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%86%D9%8A%D9%83%D9%88%D8%AA%D9%8A%D9%86" title="نيكوتين – Arabic" lang="ar" hreflang="ar" data-title="نيكوتين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-an mw-list-item"><a href="https://an.wikipedia.org/wiki/Nicotina" title="Nicotina – Aragonese" lang="an" hreflang="an" data-title="Nicotina" data-language-autonym="Aragonés" data-language-local-name="Aragonese" class="interlanguage-link-target"><span>Aragonés</span></a></li><li class="interlanguage-link interwiki-as mw-list-item"><a href="https://as.wikipedia.org/wiki/%E0%A6%A8%E0%A6%BF%E0%A6%95%27%E0%A6%9F%E0%A6%BF%E0%A6%A8" title="নিক'টিন – Assamese" lang="as" hreflang="as" data-title="নিক'টিন" data-language-autonym="অসমীয়া" data-language-local-name="Assamese" class="interlanguage-link-target"><span>অসমীয়া</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Nicotina" title="Nicotina – Asturian" lang="ast" hreflang="ast" data-title="Nicotina" 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/Nikotin" title="Nikotin – Azerbaijani" lang="az" hreflang="az" data-title="Nikotin" 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%86%DB%8C%DA%A9%D9%88%D8%AA%DB%8C%D9%86" title="نیکوتین – South Azerbaijani" lang="azb" hreflang="azb" data-title="نیکوتین" 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%A8%E0%A6%BF%E0%A6%95%E0%A7%8B%E0%A6%9F%E0%A6%BF%E0%A6%A8" title="নিকোটিন – Bangla" lang="bn" hreflang="bn" data-title="নিকোটিন" 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/N%C3%AE-ko-tin" title="Nî-ko-tin – Minnan" lang="nan" hreflang="nan" data-title="Nî-ko-tin" 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-ba mw-list-item"><a href="https://ba.wikipedia.org/wiki/%D0%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD" title="Никотин – Bashkir" lang="ba" hreflang="ba" data-title="Никотин" data-language-autonym="Башҡортса" data-language-local-name="Bashkir" class="interlanguage-link-target"><span>Башҡортса</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9D%D1%96%D0%BA%D0%B0%D1%86%D1%96%D0%BD" title="Нікацін – Belarusian" lang="be" hreflang="be" data-title="Нікацін" 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%9D%D1%96%D0%BA%D0%B0%D1%82%D1%8B%D0%BD" title="Нікатын – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Нікатын" 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%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD" title="Никотин – Bulgarian" lang="bg" hreflang="bg" data-title="Никотин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://bs.wikipedia.org/wiki/Nikotin" title="Nikotin – Bosnian" lang="bs" hreflang="bs" data-title="Nikotin" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-br mw-list-item"><a href="https://br.wikipedia.org/wiki/Nikotin" title="Nikotin – Breton" lang="br" hreflang="br" data-title="Nikotin" data-language-autonym="Brezhoneg" data-language-local-name="Breton" class="interlanguage-link-target"><span>Brezhoneg</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Nicotina" title="Nicotina – Catalan" lang="ca" hreflang="ca" data-title="Nicotina" 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/Nikotin" title="Nikotin – Czech" lang="cs" hreflang="cs" data-title="Nikotin" 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/Nicotin" title="Nicotin – Welsh" lang="cy" hreflang="cy" data-title="Nicotin" 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/Nikotin" title="Nikotin – Danish" lang="da" hreflang="da" data-title="Nikotin" 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/Nicotin" title="Nicotin – German" lang="de" hreflang="de" data-title="Nicotin" 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/Nikotiin" title="Nikotiin – Estonian" lang="et" hreflang="et" data-title="Nikotiin" 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%9D%CE%B9%CE%BA%CE%BF%CF%84%CE%AF%CE%BD%CE%B7" title="Νικοτίνη – Greek" lang="el" hreflang="el" data-title="Νικοτίνη" 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/Nicotina" title="Nicotina – Spanish" lang="es" hreflang="es" data-title="Nicotina" 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/Nikotino" title="Nikotino – Esperanto" lang="eo" hreflang="eo" data-title="Nikotino" 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/Nikotina" title="Nikotina – Basque" lang="eu" hreflang="eu" data-title="Nikotina" 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%86%DB%8C%DA%A9%D9%88%D8%AA%DB%8C%D9%86" title="نیکوتین – Persian" lang="fa" hreflang="fa" data-title="نیکوتین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-hif mw-list-item"><a href="https://hif.wikipedia.org/wiki/Nicotine" title="Nicotine – Fiji Hindi" lang="hif" hreflang="hif" data-title="Nicotine" data-language-autonym="Fiji Hindi" data-language-local-name="Fiji Hindi" class="interlanguage-link-target"><span>Fiji Hindi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Nicotine" title="Nicotine – French" lang="fr" hreflang="fr" data-title="Nicotine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Nicit%C3%ADn" title="Nicitín – Irish" lang="ga" hreflang="ga" data-title="Nicitín" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gv mw-list-item"><a href="https://gv.wikipedia.org/wiki/Nicoteen" title="Nicoteen – Manx" lang="gv" hreflang="gv" data-title="Nicoteen" data-language-autonym="Gaelg" data-language-local-name="Manx" class="interlanguage-link-target"><span>Gaelg</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Nicotina" title="Nicotina – Galician" lang="gl" hreflang="gl" data-title="Nicotina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-gu mw-list-item"><a href="https://gu.wikipedia.org/wiki/%E0%AA%A8%E0%AA%BF%E0%AA%95%E0%AB%8B%E0%AA%9F%E0%AA%BF%E0%AA%A8" title="નિકોટિન – Gujarati" lang="gu" hreflang="gu" data-title="નિકોટિન" data-language-autonym="ગુજરાતી" data-language-local-name="Gujarati" class="interlanguage-link-target"><span>ગુજરાતી</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%8B%88%EC%BD%94%ED%8B%B4" title="니코틴 – Korean" lang="ko" hreflang="ko" data-title="니코틴" 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%86%D5%AB%D5%AF%D5%B8%D5%BF%D5%AB%D5%B6" title="Նիկոտին – Armenian" lang="hy" hreflang="hy" data-title="Նիկոտին" 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%A8%E0%A4%BF%E0%A4%95%E0%A5%8B%E0%A4%9F%E0%A5%80%E0%A4%A8" title="निकोटीन – Hindi" lang="hi" hreflang="hi" data-title="निकोटीन" 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/Nikotin" title="Nikotin – Croatian" lang="hr" hreflang="hr" data-title="Nikotin" 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/Nikotino" title="Nikotino – Ido" lang="io" hreflang="io" data-title="Nikotino" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Nikotin" title="Nikotin – Indonesian" lang="id" hreflang="id" data-title="Nikotin" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Nik%C3%B3t%C3%ADn" title="Nikótín – Icelandic" lang="is" hreflang="is" data-title="Nikótín" 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/Nicotina" title="Nicotina – Italian" lang="it" hreflang="it" data-title="Nicotina" 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%A0%D7%99%D7%A7%D7%95%D7%98%D7%99%D7%9F" title="ניקוטין – Hebrew" lang="he" hreflang="he" data-title="ניקוטין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Nikotin" title="Nikotin – Javanese" lang="jv" hreflang="jv" data-title="Nikotin" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%A8%E0%B2%BF%E0%B2%95%E0%B3%8B%E0%B2%9F%E0%B2%BF%E0%B2%A8%E0%B3%8D" title="ನಿಕೋಟಿನ್ – Kannada" lang="kn" hreflang="kn" data-title="ನಿಕೋಟಿನ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9C%E1%83%98%E1%83%99%E1%83%9D%E1%83%A2%E1%83%98%E1%83%9C%E1%83%98" title="ნიკოტინი – Georgian" lang="ka" hreflang="ka" data-title="ნიკოტინი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD" title="Никотин – Kazakh" lang="kk" hreflang="kk" data-title="Никотин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-kw mw-list-item"><a href="https://kw.wikipedia.org/wiki/Nikotin" title="Nikotin – Cornish" lang="kw" hreflang="kw" data-title="Nikotin" data-language-autonym="Kernowek" data-language-local-name="Cornish" class="interlanguage-link-target"><span>Kernowek</span></a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Nikotini" title="Nikotini – Swahili" lang="sw" hreflang="sw" data-title="Nikotini" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target"><span>Kiswahili</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/N%C3%AEkot%C3%AEn" title="Nîkotîn – Kurdish" lang="ku" hreflang="ku" data-title="Nîkotîn" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD" title="Никотин – Kyrgyz" lang="ky" hreflang="ky" data-title="Никотин" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Nicotinum" title="Nicotinum – Latin" lang="la" hreflang="la" data-title="Nicotinum" 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/Nikot%C4%ABns" title="Nikotīns – Latvian" lang="lv" hreflang="lv" data-title="Nikotīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lez mw-list-item"><a href="https://lez.wikipedia.org/wiki/%D0%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD" title="Никотин – Lezghian" lang="lez" hreflang="lez" data-title="Никотин" data-language-autonym="Лезги" data-language-local-name="Lezghian" class="interlanguage-link-target"><span>Лезги</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Nikotinas" title="Nikotinas – Lithuanian" lang="lt" hreflang="lt" data-title="Nikotinas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-li mw-list-item"><a href="https://li.wikipedia.org/wiki/Nicotien" title="Nicotien – Limburgish" lang="li" hreflang="li" data-title="Nicotien" data-language-autonym="Limburgs" data-language-local-name="Limburgish" class="interlanguage-link-target"><span>Limburgs</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Nikotin" title="Nikotin – Hungarian" lang="hu" hreflang="hu" data-title="Nikotin" 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%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD" title="Никотин – Macedonian" lang="mk" hreflang="mk" data-title="Никотин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-mg mw-list-item"><a href="https://mg.wikipedia.org/wiki/Nik%C3%B4tinina" title="Nikôtinina – Malagasy" lang="mg" hreflang="mg" data-title="Nikôtinina" data-language-autonym="Malagasy" data-language-local-name="Malagasy" class="interlanguage-link-target"><span>Malagasy</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%A8%E0%B4%BF%E0%B4%95%E0%B5%8D%E0%B4%95%E0%B5%8B%E0%B4%9F%E0%B5%8D%E0%B4%9F%E0%B4%BF%E0%B5%BB" title="നിക്കോട്ടിൻ – Malayalam" lang="ml" hreflang="ml" data-title="നിക്കോട്ടിൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-arz mw-list-item"><a href="https://arz.wikipedia.org/wiki/%D9%86%D9%8A%D9%83%D9%88%D8%AA%D9%8A%D9%86" title="نيكوتين – Egyptian Arabic" lang="arz" hreflang="arz" data-title="نيكوتين" 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/Nikotin" title="Nikotin – Malay" lang="ms" hreflang="ms" data-title="Nikotin" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD" title="Никотин – Mongolian" lang="mn" hreflang="mn" data-title="Никотин" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Nicotine" title="Nicotine – Dutch" lang="nl" hreflang="nl" data-title="Nicotine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ne mw-list-item"><a href="https://ne.wikipedia.org/wiki/%E0%A4%A8%E0%A4%BF%E0%A4%95%E0%A5%8B%E0%A4%9F%E0%A5%80%E0%A4%A8" title="निकोटीन – Nepali" lang="ne" hreflang="ne" data-title="निकोटीन" data-language-autonym="नेपाली" data-language-local-name="Nepali" class="interlanguage-link-target"><span>नेपाली</span></a></li><li class="interlanguage-link interwiki-new mw-list-item"><a href="https://new.wikipedia.org/wiki/%E0%A4%A8%E0%A4%BF%E0%A4%95%E0%A5%8B%E0%A4%9F%E0%A4%BF%E0%A4%A8" title="निकोटिन – Newari" lang="new" hreflang="new" data-title="निकोटिन" data-language-autonym="नेपाल भाषा" data-language-local-name="Newari" class="interlanguage-link-target"><span>नेपाल भाषा</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%8B%E3%82%B3%E3%83%81%E3%83%B3" title="ニコチン – Japanese" lang="ja" hreflang="ja" data-title="ニコチン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-ce mw-list-item"><a href="https://ce.wikipedia.org/wiki/%D0%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD" title="Никотин – Chechen" lang="ce" hreflang="ce" data-title="Никотин" data-language-autonym="Нохчийн" data-language-local-name="Chechen" class="interlanguage-link-target"><span>Нохчийн</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Nikotin" title="Nikotin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Nikotin" 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/Nikotin" title="Nikotin – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Nikotin" 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/Nicotina" title="Nicotina – Occitan" lang="oc" hreflang="oc" data-title="Nicotina" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Nikotin" title="Nikotin – Uzbek" lang="uz" hreflang="uz" data-title="Nikotin" 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%A8%E0%A8%BF%E0%A8%95%E0%A9%8B%E0%A8%9F%E0%A9%80%E0%A8%A8" title="ਨਿਕੋਟੀਨ – Punjabi" lang="pa" hreflang="pa" data-title="ਨਿਕੋਟੀਨ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D9%86%DA%A9%D9%88%D9%B9%DB%8C%D9%86" title="نکوٹین – Western Punjabi" lang="pnb" hreflang="pnb" data-title="نکوٹین" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D9%86%DB%8C%DA%A9%D9%88%D8%AA%DB%8C%D9%86" title="نیکوتین – Pashto" lang="ps" hreflang="ps" data-title="نیکوتین" 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/Nikotyna" title="Nikotyna – Polish" lang="pl" hreflang="pl" data-title="Nikotyna" 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/Nicotina" title="Nicotina – Portuguese" lang="pt" hreflang="pt" data-title="Nicotina" 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/Nicotin%C4%83" title="Nicotină – Romanian" lang="ro" hreflang="ro" data-title="Nicotină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-rue mw-list-item"><a href="https://rue.wikipedia.org/wiki/%D0%9D%D1%96%D0%BA%D0%BE%D1%82%D1%96%D0%BD" title="Нікотін – Rusyn" lang="rue" hreflang="rue" data-title="Нікотін" data-language-autonym="Русиньскый" data-language-local-name="Rusyn" class="interlanguage-link-target"><span>Русиньскый</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD" title="Никотин – Russian" lang="ru" hreflang="ru" data-title="Никотин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sah mw-list-item"><a href="https://sah.wikipedia.org/wiki/%D0%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD" title="Никотин – Yakut" lang="sah" hreflang="sah" data-title="Никотин" data-language-autonym="Саха тыла" data-language-local-name="Yakut" class="interlanguage-link-target"><span>Саха тыла</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Nikotina" title="Nikotina – Albanian" lang="sq" hreflang="sq" data-title="Nikotina" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B6%B1%E0%B7%92%E0%B6%9A%E0%B7%9C%E0%B6%A7%E0%B7%92%E0%B6%B1%E0%B7%8A" title="නිකොටින් – Sinhala" lang="si" hreflang="si" data-title="නිකොටින්" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target"><span>සිංහල</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Nicotine" title="Nicotine – Simple English" lang="en-simple" hreflang="en-simple" data-title="Nicotine" 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-sd mw-list-item"><a href="https://sd.wikipedia.org/wiki/%D9%86%DA%AA%D9%88%D9%BD%D9%8A%D9%86" title="نڪوٽين – Sindhi" lang="sd" hreflang="sd" data-title="نڪوٽين" data-language-autonym="سنڌي" data-language-local-name="Sindhi" class="interlanguage-link-target"><span>سنڌي</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Nikot%C3%ADn" title="Nikotín – Slovak" lang="sk" hreflang="sk" data-title="Nikotín" 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/Nikotin" title="Nikotin – Slovenian" lang="sl" hreflang="sl" data-title="Nikotin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-so mw-list-item"><a href="https://so.wikipedia.org/wiki/Niikotiin" title="Niikotiin – Somali" lang="so" hreflang="so" data-title="Niikotiin" data-language-autonym="Soomaaliga" data-language-local-name="Somali" class="interlanguage-link-target"><span>Soomaaliga</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D9%86%DB%8C%DA%A9%DB%86%D8%AA%DB%8C%D9%86" title="نیکۆتین – Central Kurdish" lang="ckb" hreflang="ckb" data-title="نیکۆتین" 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%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD" title="Никотин – Serbian" lang="sr" hreflang="sr" data-title="Никотин" 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/Nikotin" title="Nikotin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Nikotin" 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-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Nikotin" title="Nikotin – Sundanese" lang="su" hreflang="su" data-title="Nikotin" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Nikotiini" title="Nikotiini – Finnish" lang="fi" hreflang="fi" data-title="Nikotiini" 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/Nikotin" title="Nikotin – Swedish" lang="sv" hreflang="sv" data-title="Nikotin" 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%A8%E0%AE%BF%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AE%BE%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AF%80%E0%AE%A9%E0%AF%8D" title="நிக்காட்டீன் – Tamil" lang="ta" hreflang="ta" data-title="நிக்காட்டீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD" title="Никотин – Tatar" lang="tt" hreflang="tt" data-title="Никотин" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%A8%E0%B0%BF%E0%B0%95%E0%B1%8B%E0%B0%9F%E0%B0%BF%E0%B0%A8%E0%B1%8D" title="నికోటిన్ – Telugu" lang="te" hreflang="te" data-title="నికోటిన్" 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%99%E0%B8%B4%E0%B9%82%E0%B8%84%E0%B8%95%E0%B8%B4%E0%B8%99" title="นิโคติน – Thai" lang="th" hreflang="th" data-title="นิโคติน" 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/Nikotin" title="Nikotin – Turkish" lang="tr" hreflang="tr" data-title="Nikotin" 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%9D%D1%96%D0%BA%D0%BE%D1%82%D0%B8%D0%BD" title="Нікотин – Ukrainian" lang="uk" hreflang="uk" data-title="Нікотин" 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%86%DA%A9%D9%88%D9%B9%DB%8C%D9%86" title="نکوٹین – Urdu" lang="ur" hreflang="ur" data-title="نکوٹین" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-za mw-list-item"><a href="https://za.wikipedia.org/wiki/Ndaengq%27ien" title="Ndaengq'ien – Zhuang" lang="za" hreflang="za" data-title="Ndaengq'ien" data-language-autonym="Vahcuengh" data-language-local-name="Zhuang" class="interlanguage-link-target"><span>Vahcuengh</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Nicotin" title="Nicotin – Vietnamese" lang="vi" hreflang="vi" data-title="Nicotin" 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-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Nikotina" title="Nikotina – Waray" lang="war" hreflang="war" data-title="Nikotina" 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%B0%BC%E5%8F%A4%E4%B8%81" title="尼古丁 – Wu" lang="wuu" hreflang="wuu" data-title="尼古丁" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-yi mw-list-item"><a href="https://yi.wikipedia.org/wiki/%D7%A0%D7%99%D7%A7%D7%90%D7%98%D7%99%D7%9F" title="ניקאטין – Yiddish" lang="yi" hreflang="yi" data-title="ניקאטין" data-language-autonym="ייִדיש" data-language-local-name="Yiddish" class="interlanguage-link-target"><span>ייִדיש</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E5%B0%BC%E5%8F%A4%E4%B8%81" title="尼古丁 – Cantonese" lang="yue" hreflang="yue" data-title="尼古丁" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%B0%BC%E5%8F%A4%E4%B8%81" title="尼古丁 – Chinese" lang="zh" hreflang="zh" data-title="尼古丁" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q28086552#sitelinks-wikipedia" title="Edit interlanguage links" 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searchaux" style="display:none">Chemical stimulant produced by some plants</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. For other uses, see <a href="/wiki/Nicotine_(disambiguation)" class="mw-disambig" title="Nicotine (disambiguation)">Nicotine (disambiguation)</a>.</div> <p class="mw-empty-elt"> </p> <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): Nicotine">Nicotine</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Nikotin_-_Nicotine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/Nikotin_-_Nicotine.svg/220px-Nikotin_-_Nicotine.svg.png" decoding="async" width="220" height="161" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/Nikotin_-_Nicotine.svg/330px-Nikotin_-_Nicotine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/81/Nikotin_-_Nicotine.svg/440px-Nikotin_-_Nicotine.svg.png 2x" data-file-width="224" data-file-height="164" /></a></span></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><table style="width:100%; margin:0;"><tbody><tr> <td style="vertical-align:top; text-align:center; width:50%;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Nicotine_molecule_ball_from_xtal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/08/Nicotine_molecule_ball_from_xtal.png/110px-Nicotine_molecule_ball_from_xtal.png" decoding="async" width="110" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/08/Nicotine_molecule_ball_from_xtal.png/165px-Nicotine_molecule_ball_from_xtal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/08/Nicotine_molecule_ball_from_xtal.png/220px-Nicotine_molecule_ball_from_xtal.png 2x" data-file-width="2772" data-file-height="3000" /></a></span></td> <td style="vertical-align:top; text-align:center; width:50%;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Nicotine_molecule_spacefill_from_xtal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Nicotine_molecule_spacefill_from_xtal.png/110px-Nicotine_molecule_spacefill_from_xtal.png" decoding="async" width="110" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Nicotine_molecule_spacefill_from_xtal.png/165px-Nicotine_molecule_spacefill_from_xtal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Nicotine_molecule_spacefill_from_xtal.png/220px-Nicotine_molecule_spacefill_from_xtal.png 2x" data-file-width="2823" data-file-height="3000" /></a></span></td> </tr></tbody></table></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></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">Nicorette, others</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/nicotine.html">Monograph</a></span></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"><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="Australia">AU</abbr>:</small> D</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"><a href="/wiki/Physical_dependence" title="Physical dependence">Physical</a>: Low–moderate<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Psychological_dependence" title="Psychological dependence">Psychological</a>: High<sup id="cite_ref-Dependence-withdrawal_2-0" class="reference"><a href="#cite_note-Dependence-withdrawal-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></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">Very high in susceptible individuals<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></td></tr><tr><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_route" class="mw-redirect" title="Oral route">oral</a> – buccal, sublingual, and ingestion; <a href="/wiki/Transdermal" title="Transdermal">transdermal</a>; <a href="/wiki/Suppository" title="Suppository">rectal</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/Stimulant" title="Stimulant">Stimulant</a>; <a href="/wiki/Nootropic" title="Nootropic">Nootropic</a>; <a href="/wiki/Euphoriant" class="mw-redirect" title="Euphoriant">Euphoriant</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_N07" title="ATC code N07">N07BA01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N07BA01">WHO</a></span>) <a href="/wiki/ATC_code_P53" class="mw-redirect" title="ATC code P53">QP53AX13</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QP53AX13">WHO</a></span>)</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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> <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_7" title="Standard for the Uniform Scheduling of Medicines and Poisons">S7</a> (Dangerous drug)</li> <li><small><abbr class="country-name" title="Brazil">BR</abbr>:</small> <a href="/wiki/Brazilian_Controlled_Drugs_and_Substances_Act" title="Brazilian Controlled Drugs and Substances Act">Unscheduled</a></li> <li><small><abbr class="country-name" title="Canada">CA</abbr></small>: Unscheduled</li> <li><small><abbr class="country-name" title="Germany">DE</abbr></small>: Unscheduled</li> <li><small><abbr class="country-name" title="New Zealand">NZ</abbr></small>: Unscheduled</li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> <a href="/wiki/General_sales_list" class="mw-redirect" title="General sales list">General sales list</a> (GSL, OTC)<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Boxed_warning" title="Boxed warning"><span style="border:thin solid black;">WARNING</span></a><sup id="cite_ref-FDA-AllBoxedWarnings_5-0" class="reference"><a href="#cite_note-FDA-AllBoxedWarnings-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>OTC and <a href="/wiki/Prescription_drug" title="Prescription drug">prescription</a></li></ul> <p><sup id="cite_ref-PubChem_Nicotine_7-0" class="reference"><a href="#cite_note-PubChem_Nicotine-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <ul><li><small><abbr class="country-name" title="United Nations">UN</abbr>:</small> Unscheduled</li> <li>In general legal for all uses for tobacco and nicotine products as electronic cigarettes, OTC for nicotine gums and lozenges.</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><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/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data"><5%</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">Primarily <a href="/wiki/Hepatic" class="mw-redirect" title="Hepatic">hepatic</a>: <a href="/wiki/CYP2A6" title="CYP2A6">CYP2A6</a>, <a href="/wiki/CYP2B6" title="CYP2B6">CYP2B6</a>, <a href="/wiki/FMO3" class="mw-redirect" title="FMO3">FMO3</a>, others</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/Cotinine" title="Cotinine">Cotinine</a></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">1–2 hours; 20 hours active metabolite</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/Renal" class="mw-redirect" title="Renal">Renal</a>, <a href="/wiki/Urine_pH" class="mw-redirect" title="Urine pH">urine pH</a>-dependent;<sup id="cite_ref-inchem_8-0" class="reference"><a href="#cite_note-inchem-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><br /> <span class="nowrap">10–20%</span> (gum), 30% (inhaled); <span class="nowrap">10–30%</span> (intranasal)</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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%;">3-[(2S)-1-methylpyrrolidin-2-yl]pyridine</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=54-11-5">54-11-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><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/89594">89594</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=2585">2585</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/DB00184">DB00184</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><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.80863.html">80863</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><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/6M3C89ZY6R">6M3C89ZY6R</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/D03365">D03365</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><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:18723">CHEBI:18723</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><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/chembldb/index.php/compound/inspect/ChEMBL3">ChEMBL3</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><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>NCT (<span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=NCT">PDBe</a></span>, <span title="www.rcsb.org"><a rel="nofollow" class="external text" href="https://www.rcsb.org/ligand/NCT">RCSB 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/DTXSID1020930">DTXSID1020930</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q28086552#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/100.000.177">100.000.177</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q28086552#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">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>10</sub><span title="Hydrogen">H</span><sub>14</sub><span title="Nitrogen">N</span><sub>2</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="7002162236000000000♠"></span>162.236</span> 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=c1ncccc1%5BC%40%40H%5D2CCCN2C">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">Chirality</a></th><td class="infobox-data"><a href="/wiki/Chiral" class="mw-redirect" title="Chiral">Chiral</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Density" title="Density">Density</a></th><td class="infobox-data">1.01 g/cm<sup>3</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">−79 °C (−110 °F)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a></th><td class="infobox-data">247 °C (477 °F)</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%;">c1ncccc1[C@@H]2CCCN2C</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/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></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:SNICXCGAKADSCV-JTQLQIEISA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr></tbody></table> <style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist 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0.2em;font-size:125%;line-height:1.2em;font-weight:bold}.mw-parser-output .sidebar-top-image{padding:0.4em}.mw-parser-output .sidebar-top-caption,.mw-parser-output .sidebar-pretitle-with-top-image,.mw-parser-output .sidebar-caption{padding:0.2em 0.4em 0;line-height:1.2em}.mw-parser-output .sidebar-pretitle{padding:0.4em 0.4em 0;line-height:1.2em}.mw-parser-output .sidebar-title,.mw-parser-output .sidebar-title-with-pretitle{padding:0.2em 0.8em;font-size:145%;line-height:1.2em}.mw-parser-output .sidebar-title-with-pretitle{padding:0.1em 0.4em}.mw-parser-output .sidebar-image{padding:0.2em 0.4em 0.4em}.mw-parser-output .sidebar-heading{padding:0.1em 0.4em}.mw-parser-output .sidebar-content{padding:0 0.5em 0.4em}.mw-parser-output .sidebar-content-with-subgroup{padding:0.1em 0.4em 0.2em}.mw-parser-output .sidebar-above,.mw-parser-output .sidebar-below{padding:0.3em 0.8em;font-weight:bold}.mw-parser-output .sidebar-collapse .sidebar-above,.mw-parser-output .sidebar-collapse .sidebar-below{border-top:1px solid #aaa;border-bottom:1px solid #aaa}.mw-parser-output .sidebar-navbar{text-align:right;font-size:115%;padding:0 0.4em 0.4em}.mw-parser-output .sidebar-list-title{padding:0 0.4em;text-align:left;font-weight:bold;line-height:1.6em;font-size:105%}.mw-parser-output .sidebar-list-title-c{padding:0 0.4em;text-align:center;margin:0 3.3em}@media(max-width:640px){body.mediawiki .mw-parser-output .sidebar{width:100%!important;clear:both;float:none!important;margin-left:0!important;margin-right:0!important}}body.skin--responsive .mw-parser-output .sidebar a>img{max-width:none!important}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sidebar:not(.notheme) .sidebar-list-title,html.skin-theme-clientpref-night .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle{background:transparent!important}html.skin-theme-clientpref-night .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle a{color:var(--color-progressive)!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-list-title,html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle{background:transparent!important}html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle a{color:var(--color-progressive)!important}}@media print{body.ns-0 .mw-parser-output .sidebar{display:none!important}}</style><table class="sidebar sidebar-collapse nomobile nowraplinks hlist" style="width:16.0em"><tbody><tr><td class="sidebar-pretitle">Part of <a href="/wiki/Category:Tobacco" title="Category:Tobacco">a series</a> on</td></tr><tr><th class="sidebar-title-with-pretitle"><a href="/wiki/Tobacco" title="Tobacco">Tobacco</a></th></tr><tr><td class="sidebar-image"><span typeof="mw:File"><a href="/wiki/File:DunhillEarlyMorningPipeMurrays.jpg" class="mw-file-description" title="Dunhill Early Morning Pipe Tobacco"><img alt="Dunhill Early Morning Pipe Tobacco" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/DunhillEarlyMorningPipeMurrays.jpg/150px-DunhillEarlyMorningPipeMurrays.jpg" decoding="async" width="150" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/DunhillEarlyMorningPipeMurrays.jpg/225px-DunhillEarlyMorningPipeMurrays.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/DunhillEarlyMorningPipeMurrays.jpg/300px-DunhillEarlyMorningPipeMurrays.jpg 2x" data-file-width="2592" data-file-height="1944" /></a></span></td></tr><tr><td class="sidebar-content"> <div class="sidebar-list mw-collapsible mw-collapsed"><div class="sidebar-list-title" style="color: var(--color-base)">History</div><div class="sidebar-list-content mw-collapsible-content hlist"> <ul><li><a href="/wiki/History_of_tobacco" title="History of tobacco">History of tobacco</a></li></ul></div></div></td> </tr><tr><td class="sidebar-content"> <div class="sidebar-list mw-collapsible mw-collapsed"><div class="sidebar-list-title" style="color: var(--color-base)">Chemistry</div><div class="sidebar-list-content mw-collapsible-content hlist"> <ul><li><a href="/wiki/Tobacco" title="Tobacco">Tobacco</a></li> <li><a href="/wiki/Tobacco_smoke" title="Tobacco smoke"> Smoke</a></li></ul></div></div></td> </tr><tr><td class="sidebar-content"> <div class="sidebar-list mw-collapsible mw-collapsed"><div class="sidebar-list-title" style="color: var(--color-base)">Biology</div><div class="sidebar-list-content mw-collapsible-content hlist"> <ul><li><i><a href="/wiki/Nicotiana" title="Nicotiana">Nicotiana</a></i> (<i><a href="/wiki/Nicotiana_tabacum" title="Nicotiana tabacum">Nicotiana tabacum</a></i>)</li> <li><a class="mw-selflink selflink">Nicotine</a></li> <li><a href="/wiki/List_of_tobacco_diseases" title="List of tobacco diseases">Tobacco diseases</a></li> <li><a href="/wiki/Types_of_tobacco" title="Types of tobacco"> Types</a></li></ul></div></div></td> </tr><tr><td class="sidebar-content"> <div class="sidebar-list mw-collapsible mw-collapsed"><div class="sidebar-list-title" style="color: var(--color-base)">Personal and social effects</div><div class="sidebar-list-content mw-collapsible-content hlist"> <ul><li><a href="/wiki/Health_effects_of_tobacco" title="Health effects of tobacco">Health effects</a></li> <li><a href="/wiki/Prevalence_of_tobacco_consumption" class="mw-redirect" title="Prevalence of tobacco consumption">Prevalence of consumption</a></li> <li><a href="/wiki/Nicotine_marketing" title="Nicotine marketing"> Marketing</a></li> <li><a href="/wiki/Tobacco_and_art" title="Tobacco and art"> Art</a></li> <li><a href="/wiki/Tobacco_and_other_drugs" title="Tobacco and other drugs">Tobacco and other drugs</a></li> <li><a href="/wiki/Tobacco_control" title="Tobacco control"> Control</a></li> <li><a href="/wiki/Religious_views_on_smoking" title="Religious views on smoking">Religious views</a></li> <li><a href="/wiki/Tobacco_politics" title="Tobacco politics"> Politics</a></li> <li><a href="/wiki/Tobacco_smoking" title="Tobacco smoking"> Smoking</a></li> <li><a href="/wiki/Tobacconist" title="Tobacconist">Tobacconist</a></li></ul></div></div></td> </tr><tr><td class="sidebar-content"> <div class="sidebar-list mw-collapsible mw-collapsed"><div class="sidebar-list-title" style="color: var(--color-base)">Production</div><div class="sidebar-list-content mw-collapsible-content hlist" style="border-bottom:1px solid #7E3517;"> <ul><li><a href="/wiki/Cultivation_of_tobacco" title="Cultivation of tobacco"> Cultivation </a></li> <li><a href="/wiki/Curing_of_tobacco" title="Curing of tobacco"> Curing</a></li> <li><a href="/wiki/Tobacco_industry" title="Tobacco industry"> Industry</a></li> <li><a href="/wiki/Tobacco_products" class="mw-redirect" title="Tobacco products"> Products</a></li></ul></div></div></td> </tr><tr><td class="sidebar-navbar"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar 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:Tobacco" title="Template:Tobacco"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tobacco" title="Template talk:Tobacco"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tobacco" title="Special:EditPage/Template:Tobacco"><abbr title="Edit this template">e</abbr></a></li></ul></div></td></tr></tbody></table> <p><b>Nicotine</b> is a <a href="/wiki/Natural_product" title="Natural product">naturally produced</a> <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> in the <a href="/wiki/Nightshade" class="mw-redirect" title="Nightshade">nightshade</a> family of plants (most predominantly in <a href="/wiki/Tobacco" title="Tobacco">tobacco</a> and <i><a href="/wiki/Duboisia_hopwoodii" title="Duboisia hopwoodii">Duboisia hopwoodii</a></i>)<sup id="cite_ref-FagerströmReview_9-0" class="reference"><a href="#cite_note-FagerströmReview-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> and is widely used <a href="/wiki/Recreational_drug_use" title="Recreational drug use">recreationally</a> as a <a href="/wiki/Stimulant" title="Stimulant">stimulant</a> and <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a>. As a <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">pharmaceutical drug</a>, it is used for <a href="/wiki/Smoking_cessation" title="Smoking cessation">smoking cessation</a> to relieve <a href="/wiki/Drug_withdrawal" title="Drug withdrawal">withdrawal symptoms</a>.<sup id="cite_ref-SajjaRahman2016_10-0" class="reference"><a href="#cite_note-SajjaRahman2016-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PubChem_Nicotine_7-1" class="reference"><a href="#cite_note-PubChem_Nicotine-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IUPHAR_nicotine_clinical_data_11-0" class="reference"><a href="#cite_note-IUPHAR_nicotine_clinical_data-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Abou-Donia2015_12-0" class="reference"><a href="#cite_note-Abou-Donia2015-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Nicotine acts as a <a href="/wiki/Receptor_agonist" class="mw-redirect" title="Receptor agonist">receptor agonist</a> at most <a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">nicotinic acetylcholine receptors</a> (nAChRs),<sup id="cite_ref-IUPHAR_13-0" class="reference"><a href="#cite_note-IUPHAR-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MalenkaNicotine_14-0" class="reference"><a href="#cite_note-MalenkaNicotine-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kishioka_2014_15-0" class="reference"><a href="#cite_note-Kishioka_2014-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> except at two <a href="/wiki/Nicotinic_receptor_subunits" class="mw-redirect" title="Nicotinic receptor subunits">nicotinic receptor subunits</a> (<a href="/wiki/NAChR%CE%B19" class="mw-redirect" title="NAChRα9">nAChRα9</a> and <a href="/wiki/NAChR%CE%B110" class="mw-redirect" title="NAChRα10">nAChRα10</a>) where it acts as a <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">receptor antagonist</a>.<sup id="cite_ref-IUPHAR_13-1" class="reference"><a href="#cite_note-IUPHAR-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Nicotine constitutes approximately 0.6–3.0% of the dry weight of tobacco.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Nicotine is also present at <a href="/wiki/Parts-per_notation" title="Parts-per notation">ppb</a> concentrations in edible plants in the family <a href="/wiki/Solanaceae" title="Solanaceae">Solanaceae</a>, including <a href="/wiki/Potato" title="Potato">potatoes</a>, <a href="/wiki/Tomato" title="Tomato">tomatoes</a>, and <a href="/wiki/Eggplant" title="Eggplant">eggplants</a>,<sup id="cite_ref-SiegmundLeitner1999_17-0" class="reference"><a href="#cite_note-SiegmundLeitner1999-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> though sources disagree on whether this has any biological significance to human consumers.<sup id="cite_ref-SiegmundLeitner1999_17-1" class="reference"><a href="#cite_note-SiegmundLeitner1999-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> It functions as an <a href="/wiki/Plant_defense_against_herbivory" title="Plant defense against herbivory">antiherbivore toxin</a>; consequently, nicotine was widely used as an <a href="/wiki/Insecticide" title="Insecticide">insecticide</a> in the past,<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ujvary_19-0" class="reference"><a href="#cite_note-Ujvary-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Neonicotinoid" title="Neonicotinoid">neonicotinoids</a> (structurally similar to nicotine), such as <a href="/wiki/Imidacloprid" title="Imidacloprid">imidacloprid</a>, are some of the most effective and widely used insecticides. </p><p>Nicotine is highly <a href="/wiki/Addictive" class="mw-redirect" title="Addictive">addictive</a>.<sup id="cite_ref-pmid23494236_20-0" class="reference"><a href="#cite_note-pmid23494236-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Grana2014_21-0" class="reference"><a href="#cite_note-Grana2014-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Siqueira2016_22-0" class="reference"><a href="#cite_note-Siqueira2016-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Slow-release forms (gums and patches, when used correctly) can be less addictive and help in quitting.<sup id="cite_ref-pmid17640334_23-0" class="reference"><a href="#cite_note-pmid17640334-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-assets.publishing.service.gov.uk_25-0" class="reference"><a href="#cite_note-assets.publishing.service.gov.uk-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Animal research suggests that <a href="/wiki/Monoamine_oxidase_inhibitors" class="mw-redirect" title="Monoamine oxidase inhibitors">monoamine oxidase inhibitors</a> present in tobacco smoke may enhance nicotine's addictive properties.<sup id="cite_ref-RCP_27-0" class="reference"><a href="#cite_note-RCP-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SmithMAO_28-0" class="reference"><a href="#cite_note-SmithMAO-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> An average <a href="/wiki/Cigarette" title="Cigarette">cigarette</a> yields about 2 mg of absorbed nicotine.<sup id="cite_ref-MayerNewLethalDose2013_29-0" class="reference"><a href="#cite_note-MayerNewLethalDose2013-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> The estimated lower dose limit for fatal outcomes is 500–1,000 mg of ingested nicotine for an adult (6.5–13 mg/kg).<sup id="cite_ref-RCP_27-1" class="reference"><a href="#cite_note-RCP-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MayerNewLethalDose2013_29-1" class="reference"><a href="#cite_note-MayerNewLethalDose2013-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Nicotine addiction involves drug-reinforced behavior, compulsive use, and relapse following abstinence.<sup id="cite_ref-Caponnetto2012_30-0" class="reference"><a href="#cite_note-Caponnetto2012-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Nicotine <a href="/wiki/Drug_dependence" class="mw-redirect" title="Drug dependence">dependence</a> involves tolerance, sensitization,<sup id="cite_ref-JainMukherjee2008_31-0" class="reference"><a href="#cite_note-JainMukherjee2008-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Physical_dependence" title="Physical dependence">physical dependence</a>, <a href="/wiki/Psychological_dependence" title="Psychological dependence">psychological dependence</a>,<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> and can cause distress.<sup id="cite_ref-Parrott2015_33-0" class="reference"><a href="#cite_note-Parrott2015-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-psych_addiction_34-0" class="reference"><a href="#cite_note-psych_addiction-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Nicotine_withdrawal" title="Nicotine withdrawal">Nicotine withdrawal</a> symptoms include depressed mood, stress, anxiety, irritability, difficulty concentrating, and sleep disturbances.<sup id="cite_ref-Dependence-withdrawal_2-1" class="reference"><a href="#cite_note-Dependence-withdrawal-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Mild nicotine withdrawal symptoms are measurable in unrestricted smokers, who experience normal moods only as their blood nicotine levels peak, with each cigarette.<sup id="cite_ref-Parrott2003_35-0" class="reference"><a href="#cite_note-Parrott2003-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> On quitting, withdrawal symptoms worsen sharply, then gradually improve to a normal state.<sup id="cite_ref-Parrott2003_35-1" class="reference"><a href="#cite_note-Parrott2003-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>Nicotine use as a tool for <a href="/wiki/Quitting_smoking" class="mw-redirect" title="Quitting smoking">quitting smoking</a> has a good safety history.<sup id="cite_ref-Schraufnage2014_36-0" class="reference"><a href="#cite_note-Schraufnage2014-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Animal studies suggest that nicotine may adversely affect cognitive development in adolescence, but the relevance of these findings to human brain development is disputed.<sup id="cite_ref-2016_SGR_37-0" class="reference"><a href="#cite_note-2016_SGR-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RCP_27-2" class="reference"><a href="#cite_note-RCP-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> At low amounts, it has a mild <a href="/wiki/Analgesic" title="Analgesic">analgesic</a> effect.<sup id="cite_ref-Schraufnagel2015_38-0" class="reference"><a href="#cite_note-Schraufnagel2015-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> According to the <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a>, "nicotine is not generally considered to be a carcinogen".<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IARCCancerStatement_40-0" class="reference"><a href="#cite_note-IARCCancerStatement-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Surgeon_General_of_the_United_States" title="Surgeon General of the United States">Surgeon General of the United States</a> indicates that evidence is inadequate to infer the presence or absence of a causal relationship between exposure to nicotine and risk for cancer.<sup id="cite_ref-SGUS2014_41-0" class="reference"><a href="#cite_note-SGUS2014-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Nicotine has been shown to produce birth defects in humans and is considered a <a href="/wiki/Teratogen" class="mw-redirect" title="Teratogen">teratogen</a>.<sup id="cite_ref-Kohlmeier2015_42-0" class="reference"><a href="#cite_note-Kohlmeier2015-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TOXNET_Nicotine_entry_43-0" class="reference"><a href="#cite_note-TOXNET_Nicotine_entry-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Median_lethal_dose" title="Median lethal dose">median lethal dose</a> of nicotine in humans is unknown.<sup id="cite_ref-ECHA_nicotine_monograph_44-0" class="reference"><a href="#cite_note-ECHA_nicotine_monograph-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> High doses are known to cause <a href="/wiki/Nicotine_poisoning" title="Nicotine poisoning">nicotine poisoning</a>, organ failure, and death through paralysis of respiratory muscles,<sup id="cite_ref-SGUS2014_41-1" class="reference"><a href="#cite_note-SGUS2014-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Effah2022_45-0" class="reference"><a href="#cite_note-Effah2022-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> though serious or fatal overdoses are rare.<sup id="cite_ref-Lavoie_46-0" class="reference"><a href="#cite_note-Lavoie-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</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="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=1" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Medical">Medical</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=2" title="Edit section: Medical"><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/Nicotine_replacement_therapy" title="Nicotine replacement therapy">Nicotine replacement therapy</a></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Nicoderm.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Nicoderm.JPG/220px-Nicoderm.JPG" decoding="async" width="220" height="146" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Nicoderm.JPG/330px-Nicoderm.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/94/Nicoderm.JPG/440px-Nicoderm.JPG 2x" data-file-width="3008" data-file-height="2000" /></a><figcaption>A <a href="/wiki/Nicotine_patch" title="Nicotine patch">nicotine patch</a> applied to the left arm. The <a href="/wiki/Cochrane_Collaboration" class="mw-redirect" title="Cochrane Collaboration">Cochrane Collaboration</a> finds that <a href="/wiki/Nicotine_replacement_therapy" title="Nicotine replacement therapy">nicotine replacement therapy</a> increases a quitter's chance of success by <span class="nowrap">50–60%</span>, regardless of setting.<sup id="cite_ref-Cochrane_NRT_2018_47-0" class="reference"><a href="#cite_note-Cochrane_NRT_2018-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>The primary <a href="/wiki/Pharmacotherapy" title="Pharmacotherapy">therapeutic use</a> of nicotine is treating nicotine dependence to eliminate <a href="/wiki/Smoking" title="Smoking">smoking</a> and the damage it does to health. Controlled levels of nicotine are given to patients through <a href="/wiki/Nicotine_gum" title="Nicotine gum">gums</a>, <a href="/wiki/Nicotine_patches" class="mw-redirect" title="Nicotine patches">dermal patches</a>, lozenges, inhalers, or nasal sprays to wean them off their dependence. A 2018 <a href="/wiki/Cochrane_Collaboration" class="mw-redirect" title="Cochrane Collaboration">Cochrane Collaboration</a> review found high-quality evidence that all current forms of nicotine replacement therapy (gum, patch, lozenges, inhaler, and nasal spray) increase the chances of successfully quitting smoking by <span class="nowrap">50–60%</span>, regardless of setting.<sup id="cite_ref-Cochrane_NRT_2018_47-1" class="reference"><a href="#cite_note-Cochrane_NRT_2018-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p><p>Combining <a href="/wiki/Nicotine_patch" title="Nicotine patch">nicotine patch</a> use with a faster acting nicotine replacement, like gum or spray, improves the odds of treatment success.<sup id="cite_ref-:3_48-0" class="reference"><a href="#cite_note-:3-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>In contrast to recreational nicotine products, which have been designed to maximize the likelihood of addiction, nicotine replacement products (NRTs) are designed to minimize addictiveness.<sup id="cite_ref-SGUS2014_41-2" class="reference"><a href="#cite_note-SGUS2014-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 112">: 112 </span></sup> The more quickly a dose of nicotine is delivered and absorbed, the higher the addiction risk.<sup id="cite_ref-Parrott2015_33-1" class="reference"><a href="#cite_note-Parrott2015-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p><b>Investigative</b> </p><p>Nicotine is being researched in clinical trials for possible benefit in treating <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a>, <a href="/wiki/Dementia" title="Dementia">dementia</a>, <a href="/wiki/Attention_deficit_hyperactivity_disorder" title="Attention deficit hyperactivity disorder">attention deficit hyperactivity disorder</a> (ADHD), and <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>.<sup id="cite_ref-MIND_Study_49-0" class="reference"><a href="#cite_note-MIND_Study-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p><p>Nicotine may partly attenuate <a href="/wiki/Sensory_gating" title="Sensory gating">sensory gating</a> and attentional deficits associated with <a href="/wiki/Schizophrenia" title="Schizophrenia">schizophrenia</a>. Short-term use of <a href="/wiki/Transdermal" title="Transdermal">transdermal</a> nicotine was found to improve subjects’ reaction time and <a href="/wiki/Vigilance_(psychology)" title="Vigilance (psychology)">alertness</a> in given tasks. Nicotine was not found to improve <a href="/wiki/Negative_symptoms_of_schizophrenia" class="mw-redirect" title="Negative symptoms of schizophrenia">negative</a>, <a href="/wiki/Psychosis" title="Psychosis">positive</a>, or other cognitive symptoms of schizophrenia.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pesticide">Pesticide</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=3" title="Edit section: Pesticide"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nicotine has been used as an <a href="/wiki/Insecticide" title="Insecticide">insecticide</a> since at least 1690, in the form of tobacco extracts<sup id="cite_ref-Ujvary_19-1" class="reference"><a href="#cite_note-Ujvary-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-neonic_mechanisms_51-0" class="reference"><a href="#cite_note-neonic_mechanisms-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> (although other components of tobacco also seem to have pesticide effects).<sup id="cite_ref-modern_pesticide_53-0" class="reference"><a href="#cite_note-modern_pesticide-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> Nicotine pesticides have not been commercially available in the US since 2014,<sup id="cite_ref-epacancel2_54-0" class="reference"><a href="#cite_note-epacancel2-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> homemade pesticides are banned on organic crops,<sup id="cite_ref-prohibited_dust_55-0" class="reference"><a href="#cite_note-prohibited_dust-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> and caution is recommended for small gardeners.<sup id="cite_ref-homemade_pesticide_56-0" class="reference"><a href="#cite_note-homemade_pesticide-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> Nicotine pesticides have been banned in the EU since 2009.<sup id="cite_ref-pesticide_contam_57-0" class="reference"><a href="#cite_note-pesticide_contam-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> Foods are imported from countries in which nicotine pesticides are allowed, such as China, but foods may not exceed maximum nicotine levels.<sup id="cite_ref-pesticide_contam_57-1" class="reference"><a href="#cite_note-pesticide_contam-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Neonicotinoids" class="mw-redirect" title="Neonicotinoids">Neonicotinoids</a>, such as <a href="/wiki/Imidacloprid" title="Imidacloprid">imidacloprid</a>, which are derived from and structurally similar to nicotine, are widely used as agricultural and veterinary pesticides as of 2016.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-neonic_mechanisms_51-1" class="reference"><a href="#cite_note-neonic_mechanisms-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Performance">Performance</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=4" title="Edit section: Performance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nicotine-containing products are sometimes used for the <a href="/wiki/Performance-enhancing_substance" title="Performance-enhancing substance">performance-enhancing</a> effects of nicotine on cognition.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> A 2010 meta-analysis of 41 <a href="/wiki/Double-blind" class="mw-redirect" title="Double-blind">double-blind</a>, <a href="/wiki/Placebo" title="Placebo">placebo</a>-controlled studies concluded that nicotine or smoking had significant positive effects on aspects of fine motor abilities, alerting and orienting attention, and episodic and working memory.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> A 2015 review noted that stimulation of the <a href="/wiki/%CE%914%CE%B22_nicotinic_receptor" class="mw-redirect" title="Α4β2 nicotinic receptor">α4β2 nicotinic receptor</a> is responsible for certain improvements in attentional performance;<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> among the <a href="/wiki/Nicotinic_receptor" class="mw-redirect" title="Nicotinic receptor">nicotinic receptor</a> subtypes, nicotine has the highest <a href="/wiki/Binding_affinity" class="mw-redirect" title="Binding affinity">binding affinity</a> at the α4β2 receptor (k<sub>i</sub>=1 <abbr title="nanomolar">nM</abbr>), which is also the biological target that mediates nicotine's <a href="/wiki/Addictive" class="mw-redirect" title="Addictive">addictive</a> properties.<sup id="cite_ref-Nicotine_IUPHAR_63-0" class="reference"><a href="#cite_note-Nicotine_IUPHAR-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> Nicotine has potential beneficial effects, but it also has <a href="/wiki/Paradoxical_reaction" title="Paradoxical reaction">paradoxical effects</a>, which may be due to the <a href="/wiki/Yerkes%E2%80%93Dodson_law" title="Yerkes–Dodson law">inverted U-shape of the dose-response curve</a> or <a href="/wiki/Pharmacokinetic" class="mw-redirect" title="Pharmacokinetic">pharmacokinetic</a> features.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Recreational">Recreational</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=5" title="Edit section: Recreational"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nicotine is used as a <a href="/wiki/Recreational_drug" class="mw-redirect" title="Recreational drug">recreational drug</a>.<sup id="cite_ref-UbanHorton2018_65-0" class="reference"><a href="#cite_note-UbanHorton2018-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> It is widely used, highly addictive and hard to discontinue.<sup id="cite_ref-Siqueira2016_22-1" class="reference"><a href="#cite_note-Siqueira2016-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Nicotine is often <a href="/wiki/Addiction" title="Addiction">used compulsively</a>,<sup id="cite_ref-addictive_66-0" class="reference"><a href="#cite_note-addictive-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Substance_dependence" title="Substance dependence">dependence</a> can develop within days.<sup id="cite_ref-addictive_66-1" class="reference"><a href="#cite_note-addictive-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wilder2016_67-0" class="reference"><a href="#cite_note-Wilder2016-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> Recreational drug users commonly use nicotine for its mood-altering effects.<sup id="cite_ref-Parrott2015_33-2" class="reference"><a href="#cite_note-Parrott2015-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Recreational nicotine products include <a href="/wiki/Chewing_tobacco" title="Chewing tobacco">chewing tobacco</a>, <a href="/wiki/Cigars" class="mw-redirect" title="Cigars">cigars</a>,<sup id="cite_ref-ElSayedSylvester2007_68-0" class="reference"><a href="#cite_note-ElSayedSylvester2007-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Cigarettes" class="mw-redirect" title="Cigarettes">cigarettes</a>,<sup id="cite_ref-ElSayedSylvester2007_68-1" class="reference"><a href="#cite_note-ElSayedSylvester2007-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> <a href="/wiki/E-cigarettes" class="mw-redirect" title="E-cigarettes">e-cigarettes</a>,<sup id="cite_ref-Rahman2014_69-0" class="reference"><a href="#cite_note-Rahman2014-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Snuff_(tobacco)" title="Snuff (tobacco)">snuff</a>, <a href="/wiki/Pipe_smoking" title="Pipe smoking">pipe tobacco</a>,<sup id="cite_ref-ElSayedSylvester2007_68-2" class="reference"><a href="#cite_note-ElSayedSylvester2007-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Snus" title="Snus">snus</a>, and <a href="/wiki/Nicotine_pouch" class="mw-redirect" title="Nicotine pouch">nicotine pouches</a>. </p><p><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Alcohol</a> infused with nicotine is called <a href="/wiki/Nicotini" title="Nicotini">nicotini</a>.<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> </p> <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=Nicotine&action=edit&section=6" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nicotine use for tobacco cessation has few contraindications.<sup id="cite_ref-nrt_safety_71-0" class="reference"><a href="#cite_note-nrt_safety-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> </p><p>It is not known whether nicotine replacement therapy is effective for smoking cessation in adolescents, as of 2014.<sup id="cite_ref-pharmacotherapy_72-0" class="reference"><a href="#cite_note-pharmacotherapy-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> It is therefore not recommended to adolescents.<sup id="cite_ref-adolescents_73-0" class="reference"><a href="#cite_note-adolescents-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> It is not safe to use nicotine during pregnancy or breastfeeding, although it is safer than smoking. The desirability of NRT use in pregnancy is therefore debated.<sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-75" class="reference"><a href="#cite_note-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pregnancy_controversy_76-0" class="reference"><a href="#cite_note-pregnancy_controversy-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup> </p><p>Randomized trials and observational studies of nicotine replacement therapy in cardiovascular patients show no increase in adverse cardiovascular events compared to those treated with placebo.<sup id="cite_ref-ACC_Consensus_77-0" class="reference"><a href="#cite_note-ACC_Consensus-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> Using nicotine products during cancer treatment may be contraindicated, as nicotine may promote tumour growth, but temporary use of NRTs to quit smoking may be advised for <a href="/wiki/Harm_reduction" title="Harm reduction">harm reduction</a>.<sup id="cite_ref-carcinogenicity_78-0" class="reference"><a href="#cite_note-carcinogenicity-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Nicotine_gum" title="Nicotine gum">Nicotine gum</a> is contraindicated in individuals with <a href="/wiki/Temporomandibular_joint_disease" class="mw-redirect" title="Temporomandibular joint disease">temporomandibular joint disease</a>.<sup id="cite_ref-Nicotine_AHFS_monograph_79-0" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> People with chronic nasal disorders and severe reactive airway disease require additional precautions when using nicotine nasal sprays.<sup id="cite_ref-adolescents_73-1" class="reference"><a href="#cite_note-adolescents-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> Nicotine in any form is <a href="/wiki/Contraindicated" class="mw-redirect" title="Contraindicated">contraindicated</a> in individuals with a known <a href="/wiki/Hypersensitivity" title="Hypersensitivity">hypersensitivity</a> to nicotine.<sup id="cite_ref-Nicotine_AHFS_monograph_79-1" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-adolescents_73-2" class="reference"><a href="#cite_note-adolescents-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> </p> <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=Nicotine&action=edit&section=7" title="Edit section: Adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Side_effects_of_nicotine.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Side_effects_of_nicotine.png/330px-Side_effects_of_nicotine.png" decoding="async" width="330" height="354" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Side_effects_of_nicotine.png/495px-Side_effects_of_nicotine.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/34/Side_effects_of_nicotine.png/660px-Side_effects_of_nicotine.png 2x" data-file-width="2277" data-file-height="2442" /></a><figcaption>Possible <a href="/wiki/Side_effect" title="Side effect">side effects</a> of nicotine<sup id="cite_ref-80" class="reference"><a href="#cite_note-80"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Nicotine is classified as a poison,<sup id="cite_ref-81" class="reference"><a href="#cite_note-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-82" class="reference"><a href="#cite_note-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup> and it is "extremely hazardous".<sup id="cite_ref-:4_83-0" class="reference"><a href="#cite_note-:4-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> However, at doses typically used by consumers, it presents little if any hazard to the user.<sup id="cite_ref-RCP_report_84-0" class="reference"><a href="#cite_note-RCP_report-84"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-85" class="reference"><a href="#cite_note-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-86" class="reference"><a href="#cite_note-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup> A 2018 <a href="/wiki/Cochrane_Collaboration" class="mw-redirect" title="Cochrane Collaboration">Cochrane Collaboration</a> review lists nine main adverse events related to nicotine replacement therapy: <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, <a href="/wiki/Lightheadedness" title="Lightheadedness">lightheadedness</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, gastrointestinal symptoms, <a href="/wiki/Insomnia" title="Insomnia">insomnia</a>, abnormal <a href="/wiki/Dream" title="Dream">dreams</a>, non-<a href="/wiki/Ischemic" class="mw-redirect" title="Ischemic">ischemic</a> <a href="/wiki/Palpitations" title="Palpitations">palpitations</a> and chest pain, skin reactions, oral/nasal reactions, and <a href="/wiki/Hiccup" title="Hiccup">hiccups</a>.<sup id="cite_ref-Cochrane_NRT_2018_AEs_87-0" class="reference"><a href="#cite_note-Cochrane_NRT_2018_AEs-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> Many of these were also common in the placebo group without nicotine.<sup id="cite_ref-Cochrane_NRT_2018_AEs_87-1" class="reference"><a href="#cite_note-Cochrane_NRT_2018_AEs-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> Palpitations and chest pain were deemed "rare" and there was no evidence of an increased number of serious cardiac problems compared to the placebo group, even in people with established cardiac disease.<sup id="cite_ref-Cochrane_NRT_2018_47-2" class="reference"><a href="#cite_note-Cochrane_NRT_2018-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> The common side effects from nicotine exposure are listed in the table below. Serious adverse events due to the use of nicotine replacement therapy are extremely rare.<sup id="cite_ref-Cochrane_NRT_2018_47-3" class="reference"><a href="#cite_note-Cochrane_NRT_2018-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> At low amounts, it has a mild <a href="/wiki/Analgesic" title="Analgesic">analgesic</a> effect.<sup id="cite_ref-Schraufnagel2015_38-1" class="reference"><a href="#cite_note-Schraufnagel2015-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> However, at sufficiently high doses, nicotine may result in nausea, vomiting, <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>, <a href="/wiki/Salivation" class="mw-redirect" title="Salivation">salivation</a>, <a href="/wiki/Bradycardia" title="Bradycardia">bradycardia</a>, and possibly <a href="/wiki/Seizure" title="Seizure">seizures</a>, <a href="/wiki/Hypoventilation" title="Hypoventilation">hypoventilation</a>, and death.<sup id="cite_ref-England2015_88-0" class="reference"><a href="#cite_note-England2015-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable sortable"> <caption><i>Common</i> side effects of nicotine use according to route of administration and dosage form </caption> <tbody><tr> <th class="sortable"><a href="/wiki/Route_of_administration" title="Route of administration">Route of administration</a> </th> <th class="sortable"><a href="/wiki/Dosage_form" title="Dosage form">Dosage form</a> </th> <th class="unsortable">Associated side effects of nicotine </th> <th class="unsortable"><small>Sources</small> </th></tr> <tr> <td style="text-align:center" rowspan="2"><a href="/wiki/Buccal_administration" title="Buccal administration">Buccal</a> </td> <td style="text-align:center"><a href="/wiki/Nicotine_gum" title="Nicotine gum">Nicotine gum</a> </td> <td><a href="/wiki/Indigestion" title="Indigestion">Indigestion</a>, nausea, hiccups, traumatic injury to oral mucosa or teeth, irritation or <a href="/wiki/Tingling" class="mw-redirect" title="Tingling">tingling</a> of the mouth and throat, <a href="/wiki/Mouth_ulcer" title="Mouth ulcer">oral mucosal ulceration</a>, jaw-<a href="/wiki/Muscle_ache" class="mw-redirect" title="Muscle ache">muscle ache</a>, burping, gum sticking to teeth, unpleasant taste, dizziness, lightheadedness, headache, and <a href="/wiki/Insomnia" title="Insomnia">insomnia</a>. </td> <td style="text-align:center"><sup id="cite_ref-Cochrane_NRT_2018_47-4" class="reference"><a href="#cite_note-Cochrane_NRT_2018-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nicotine_AHFS_monograph_79-2" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="text-align:center"><a href="/wiki/Nicotine_lozenge" title="Nicotine lozenge">Lozenge</a> </td> <td>Nausea, <a href="/wiki/Dyspepsia" class="mw-redirect" title="Dyspepsia">dyspepsia</a>, <a href="/wiki/Flatulence" title="Flatulence">flatulence</a>, headache, <a href="/wiki/Upper_respiratory_tract_infection" title="Upper respiratory tract infection">upper respiratory tract infections</a>, irritation (i.e., a burning sensation), hiccups, sore throat, coughing, dry lips, and oral mucosal ulceration. </td> <td style="text-align:center"><sup id="cite_ref-Cochrane_NRT_2018_47-5" class="reference"><a href="#cite_note-Cochrane_NRT_2018-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nicotine_AHFS_monograph_79-3" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="text-align:center"><a href="/wiki/Transdermal" title="Transdermal">Transdermal</a> </td> <td style="text-align:center"><a href="/wiki/Nicotine_patch" title="Nicotine patch">Transdermal<br />patch</a> </td> <td><a href="/wiki/Application_site_reaction" title="Application site reaction">Application site reactions</a> (i.e., <a href="/wiki/Pruritus" class="mw-redirect" title="Pruritus">pruritus</a>, burning, or <a href="/wiki/Erythema" title="Erythema">erythema</a>), diarrhea, dyspepsia, abdominal pain, dry mouth, nausea, dizziness, nervousness or restlessness, headache, vivid dreams or other sleep disturbances, and irritability. </td> <td style="text-align:center"><sup id="cite_ref-Cochrane_NRT_2018_47-6" class="reference"><a href="#cite_note-Cochrane_NRT_2018-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nicotine_AHFS_monograph_79-4" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FDA_transdermal_patch_89-0" class="reference"><a href="#cite_note-FDA_transdermal_patch-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="text-align:center"><a href="/wiki/Intranasal" class="mw-redirect" title="Intranasal">Intranasal</a> </td> <td style="text-align:center"><a href="/wiki/Nicotine_nasal_spray" title="Nicotine nasal spray">Nasal spray</a> </td> <td>Runny nose, nasopharyngeal and ocular irritation, watery eyes, sneezing, and coughing. </td> <td style="text-align:center"><sup id="cite_ref-Cochrane_NRT_2018_47-7" class="reference"><a href="#cite_note-Cochrane_NRT_2018-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nicotine_AHFS_monograph_79-5" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nicotrol_NS_90-0" class="reference"><a href="#cite_note-Nicotrol_NS-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="text-align:center">Oral inhalation </td> <td style="text-align:center"><a href="/wiki/Nicotine_inhaler" class="mw-redirect" title="Nicotine inhaler">Inhaler</a> </td> <td>Dyspepsia, oropharyngeal irritation (e.g., coughing, irritation of the mouth and throat), <a href="/wiki/Rhinitis" title="Rhinitis">rhinitis</a>, and headache. </td> <td style="text-align:center"><sup id="cite_ref-Cochrane_NRT_2018_47-8" class="reference"><a href="#cite_note-Cochrane_NRT_2018-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nicotine_AHFS_monograph_79-6" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nicotrol_91-0" class="reference"><a href="#cite_note-Nicotrol-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="text-align:center" colspan="2">All (nonspecific) </td> <td>Peripheral <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstriction</a>, <a href="/wiki/Tachycardia" title="Tachycardia">tachycardia</a> (i.e., fast heart rate), elevated <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>, increased <a href="/wiki/Alertness" title="Alertness">alertness</a> and <a href="#Performance">cognitive performance</a>. </td> <td style="text-align:center"><sup id="cite_ref-Nicotine_AHFS_monograph_79-7" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nicotrol_NS_90-1" class="reference"><a href="#cite_note-Nicotrol_NS-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Sleep">Sleep</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=8" title="Edit section: Sleep"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nicotine reduces the amount of <a href="/wiki/Rapid_eye_movement_sleep" title="Rapid eye movement sleep">rapid eye movement</a> (REM) sleep, <a href="/wiki/Slow-wave_sleep" title="Slow-wave sleep">slow-wave sleep</a> (SWS), and total sleep time in healthy nonsmokers given nicotine via a <a href="/wiki/Transdermal_patch" title="Transdermal patch">transdermal patch</a>, and the reduction is <a href="/wiki/Dose%E2%80%93response_relationship" title="Dose–response relationship">dose-dependent</a>.<sup id="cite_ref-GarciaSalloum2015_92-0" class="reference"><a href="#cite_note-GarciaSalloum2015-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup> Acute nicotine intoxication has been found to significantly reduce total sleep time and increase REM latency, <a href="/wiki/Sleep_onset_latency" title="Sleep onset latency">sleep onset latency</a>, and <a href="/wiki/NREM#Stages_of_NREM_sleep" class="mw-redirect" title="NREM">non-rapid eye movement</a> (NREM) stage 2 sleep time.<sup id="cite_ref-GarciaSalloum2015_92-1" class="reference"><a href="#cite_note-GarciaSalloum2015-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Neuropharmacology_review_93-0" class="reference"><a href="#cite_note-Neuropharmacology_review-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup> Depressive non-smokers experience mood and sleep improvements under nicotine administration; however, subsequent nicotine withdrawal has a negative effect on both mood and sleep.<sup id="cite_ref-Jaehne2009_94-0" class="reference"><a href="#cite_note-Jaehne2009-94"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cardiovascular_system">Cardiovascular system</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=9" title="Edit section: Cardiovascular system"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nicotine exerts several significant effects on the <a href="/wiki/Cardiovascular_system" class="mw-redirect" title="Cardiovascular system">cardiovascular system</a>. Primarily, it stimulates the <a href="/wiki/Sympathetic_nervous_system" title="Sympathetic nervous system">sympathetic nervous system</a>, leading to the release of <a href="/wiki/Catecholamine" title="Catecholamine">catecholamines</a>. This activation results in an increase in <a href="/wiki/Heart_rate" title="Heart rate">heart rate</a> and <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>, as well as enhanced <a href="/wiki/Myocardial_contractility" title="Myocardial contractility">myocardial contractility</a>, which raises the workload on the heart. Additionally, nicotine causes systemic <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstriction</a>, including constriction of coronary arteries, which can reduce blood flow to the heart. Long-term exposure to nicotine may impair <a href="/wiki/Endothelial" class="mw-redirect" title="Endothelial">endothelial</a> function, potentially contributing to <a href="/wiki/Atherosclerosis" title="Atherosclerosis">atherosclerosis</a>. Furthermore, nicotine has been associated with the development of <a href="/wiki/Cardiac_arrhythmia" class="mw-redirect" title="Cardiac arrhythmia">cardiac arrhythmias</a>, particularly in individuals who already have underlying heart disease.<sup id="cite_ref-Benowitz_2016_95-0" class="reference"><a href="#cite_note-Benowitz_2016-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup> </p><p>The effects of nicotine can be differentiated between short-term and long-term use. Short-term nicotine use, such as that associated with <a href="/wiki/Nicotine_replacement_therapy" title="Nicotine replacement therapy">nicotine replacement therapy</a> (NRT) for smoking cessation, appears to pose little cardiovascular risk, even for patients with known cardiovascular conditions. In contrast, longer-term nicotine use may not accelerate atherosclerosis but could contribute to acute cardiovascular events in those with pre-existing cardiovascular disease. Many severe cardiovascular effects traditionally associated with smoking may not be solely attributable to nicotine itself. Cigarette smoke contains numerous other potentially cardiotoxic substances, including <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> and oxidant gases.<sup id="cite_ref-Benowitz_2016_95-1" class="reference"><a href="#cite_note-Benowitz_2016-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup> </p><p>A 2016 review of the cardiovascular toxicity of nicotine concluded, "Based on current knowledge, we believe that the cardiovascular risks of nicotine from e-cigarette use in people without cardiovascular disease are quite low. We have concerns that nicotine from e-cigarettes could pose some risk for users with cardiovascular disease."<sup id="cite_ref-Benowitz_2016_95-2" class="reference"><a href="#cite_note-Benowitz_2016-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup> </p><p>A 2018 <a href="/wiki/Cochrane_(organisation)" title="Cochrane (organisation)">Cochrane</a> review found that, in rare cases, nicotine replacement therapy can cause non-<a href="/wiki/Ischemic" class="mw-redirect" title="Ischemic">ischemic</a> chest pain (i.e., chest pain that is unrelated to a <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">heart attack</a>) and <a href="/wiki/Heart_palpitation" class="mw-redirect" title="Heart palpitation">heart palpitations</a>, but does not increase the incidence of serious cardiac adverse events (i.e., myocardial infarction, <a href="/wiki/Stroke" title="Stroke">stroke</a>, and <a href="/wiki/Cardiac_death" class="mw-redirect" title="Cardiac death">cardiac death</a>) relative to controls.<sup id="cite_ref-Cochrane_NRT_2018_47-9" class="reference"><a href="#cite_note-Cochrane_NRT_2018-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Blood_pressure">Blood pressure</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=10" title="Edit section: Blood pressure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the short term, nicotine causes a transient increase in <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>. Long term, epidemiological studies generally show increased blood pressure and <a href="/wiki/Hypertension" title="Hypertension">hypertension</a> among nicotine users.<sup id="cite_ref-Benowitz_2016_95-3" class="reference"><a href="#cite_note-Benowitz_2016-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup> </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=Nicotine&action=edit&section=11" title="Edit section: Reinforcement disorders"><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/Nicotine_withdrawal" title="Nicotine withdrawal">Nicotine withdrawal</a> and <a href="/wiki/Smoking_cessation" title="Smoking cessation">Smoking cessation</a></div> <table role="presentation" cellpadding="0" style="border-spacing:0; clear:right; float:right;"> <tbody><tr> <td><div class="thumb tright"> <div class="thumbinner" style="width:402px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: aliceblue;margin-bottom:3px;">ΔFosB accumulation from excessive drug use</div> <div style="position:relative; width:400px; height:440px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:0px; top:0px; width:400px; position:absolute"> <span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/File:%CE%94FosB_accumulation.svg" title="commons:File:ΔFosB accumulation.svg"><img alt="ΔFosB accumulation graph" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/%CE%94FosB_accumulation.svg/400px-%CE%94FosB_accumulation.svg.png" decoding="async" width="400" height="440" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/%CE%94FosB_accumulation.svg/600px-%CE%94FosB_accumulation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4b/%CE%94FosB_accumulation.svg/800px-%CE%94FosB_accumulation.svg.png 2x" data-file-width="400" data-file-height="440" /></a></span> </div> <div style="text-align:center; line-height:110%;"> <div style="background-color:transparent; color:black"></div> </div> </div> <div class="thumbcaption" style="clear:left">Top: this depicts the initial effects of high dose exposure to an addictive drug on <a href="/wiki/Gene_expression" title="Gene expression">gene expression</a> in the <a href="/wiki/Nucleus_accumbens" title="Nucleus accumbens">nucleus accumbens</a> for various Fos family proteins (i.e., <a href="/wiki/C-Fos" class="mw-redirect" title="C-Fos">c-Fos</a>, <a href="/wiki/FosB" class="mw-redirect" title="FosB">FosB</a>, <a href="/wiki/%CE%94FosB" class="mw-redirect" title="ΔFosB">ΔFosB</a>, <a href="/wiki/Fra1" class="mw-redirect" title="Fra1">Fra1</a>, and <a href="/wiki/Fra2" class="mw-redirect" title="Fra2">Fra2</a>).<br />Bottom: this illustrates the progressive increase in ΔFosB expression in the nucleus accumbens following repeated twice daily drug binges, where these <a href="/wiki/Phosphorylated" class="mw-redirect" title="Phosphorylated">phosphorylated</a> (35–37 <a href="/wiki/Kilodalton" class="mw-redirect" title="Kilodalton">kilodalton</a>) ΔFosB <a href="/wiki/Isoform" class="mw-redirect" title="Isoform">isoforms</a> persist in the <a href="/wiki/D1-type" class="mw-redirect" title="D1-type">D1-type</a> <a href="/wiki/Medium_spiny_neurons" class="mw-redirect" title="Medium spiny neurons">medium spiny neurons</a> of the nucleus accumbens for up to 2 months.<sup id="cite_ref-pmid11572966_96-0" class="reference"><a href="#cite_note-pmid11572966-96"><span class="cite-bracket">[</span>96<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nestler2_97-0" class="reference"><a href="#cite_note-Nestler2-97"><span class="cite-bracket">[</span>97<span class="cite-bracket">]</span></a></sup></div> </div> </div> </td></tr></tbody></table> <p>Nicotine is highly <a href="/wiki/Addictive" class="mw-redirect" title="Addictive">addictive</a> but paradoxically has quite weak reinforcing property compared to other drugs of abuse in various animals.<sup id="cite_ref-Grana2014_21-1" class="reference"><a href="#cite_note-Grana2014-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Siqueira2016_22-2" class="reference"><a href="#cite_note-Siqueira2016-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-98" class="reference"><a href="#cite_note-98"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Belluzzi_Wang_Leslie_2005_99-0" class="reference"><a href="#cite_note-Belluzzi_Wang_Leslie_2005-99"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup> Its addictiveness depends on how it is administered and also depends upon form in which nicotine is used.<sup id="cite_ref-assets.publishing.service.gov.uk_25-1" class="reference"><a href="#cite_note-assets.publishing.service.gov.uk-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Animal research suggests that <a href="/wiki/Monoamine_oxidase_inhibitors" class="mw-redirect" title="Monoamine oxidase inhibitors">monoamine oxidase inhibitors</a>, <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a><sup id="cite_ref-Belluzzi_Wang_Leslie_2005_99-1" class="reference"><a href="#cite_note-Belluzzi_Wang_Leslie_2005-99"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-100" class="reference"><a href="#cite_note-100"><span class="cite-bracket">[</span>100<span class="cite-bracket">]</span></a></sup> and other constituents in tobacco smoke may enhance its addictiveness.<sup id="cite_ref-RCP_27-3" class="reference"><a href="#cite_note-RCP-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SmithMAO_28-1" class="reference"><a href="#cite_note-SmithMAO-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Nicotine_dependence" title="Nicotine dependence">Nicotine dependence</a> involves aspects of both <a href="/wiki/Psychological_dependence" title="Psychological dependence">psychological dependence</a> and <a href="/wiki/Physical_dependence" title="Physical dependence">physical dependence</a>, since discontinuation of extended use has been shown to produce both <a href="/wiki/Affect_(psychology)" title="Affect (psychology)">affective</a> (e.g., anxiety, irritability, craving, <a href="/wiki/Anhedonia" title="Anhedonia">anhedonia</a>) and <a href="/wiki/Somatic_nervous_system" title="Somatic nervous system">somatic</a> (mild motor dysfunctions such as <a href="/wiki/Tremor" title="Tremor">tremor</a>) withdrawal symptoms.<sup id="cite_ref-Dependence-withdrawal_2-2" class="reference"><a href="#cite_note-Dependence-withdrawal-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Withdrawal symptoms peak in one to three days<sup id="cite_ref-DasProchaska2017_101-0" class="reference"><a href="#cite_note-DasProchaska2017-101"><span class="cite-bracket">[</span>101<span class="cite-bracket">]</span></a></sup> and can persist for several weeks.<sup id="cite_ref-HKS2010_102-0" class="reference"><a href="#cite_note-HKS2010-102"><span class="cite-bracket">[</span>102<span class="cite-bracket">]</span></a></sup> Even though other drugs of dependence can have withdrawal states lasting 6 months or longer, this does not appear to occur with cigarette withdrawal.<sup id="cite_ref-103" class="reference"><a href="#cite_note-103"><span class="cite-bracket">[</span>103<span class="cite-bracket">]</span></a></sup> </p><p>Normal between-cigarettes discontinuation, in unrestricted smokers, causes mild but measurable nicotine withdrawal symptoms.<sup id="cite_ref-Parrott2003_35-2" class="reference"><a href="#cite_note-Parrott2003-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> These include mildly worse mood, stress, anxiety, cognition, and sleep, all of which briefly return to normal with the next cigarette.<sup id="cite_ref-Parrott2003_35-3" class="reference"><a href="#cite_note-Parrott2003-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Smokers have a worse mood than they typically would have if they were not nicotine-dependent; they experience normal moods only immediately after smoking.<sup id="cite_ref-Parrott2003_35-4" class="reference"><a href="#cite_note-Parrott2003-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Nicotine dependence is associated with poor sleep quality and shorter sleep duration among smokers.<sup id="cite_ref-104" class="reference"><a href="#cite_note-104"><span class="cite-bracket">[</span>104<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-105" class="reference"><a href="#cite_note-105"><span class="cite-bracket">[</span>105<span class="cite-bracket">]</span></a></sup> </p><p>In dependent smokers, withdrawal causes impairments in memory and attention, and smoking during withdrawal returns these cognitive abilities to pre-withdrawal levels.<sup id="cite_ref-Bruijnzeel2012_106-0" class="reference"><a href="#cite_note-Bruijnzeel2012-106"><span class="cite-bracket">[</span>106<span class="cite-bracket">]</span></a></sup> The temporarily increased cognitive levels of smokers after inhaling smoke are offset by periods of cognitive decline during nicotine withdrawal.<sup id="cite_ref-Parrott2003_35-5" class="reference"><a href="#cite_note-Parrott2003-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Therefore, the overall daily cognitive levels of smokers and non-smokers are roughly similar.<sup id="cite_ref-Parrott2003_35-6" class="reference"><a href="#cite_note-Parrott2003-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>Nicotine activates the <a href="/wiki/Mesolimbic_pathway" title="Mesolimbic pathway">mesolimbic pathway</a> and <a href="/wiki/Inducible_gene" class="mw-redirect" title="Inducible gene">induces</a> long-term <a href="/wiki/%CE%94FosB" class="mw-redirect" title="ΔFosB">ΔFosB</a> expression (i.e., produces <a href="/wiki/Phosphorylated" class="mw-redirect" title="Phosphorylated">phosphorylated</a> ΔFosB <a href="/wiki/Isoform" class="mw-redirect" title="Isoform">isoforms</a>) in the <a href="/wiki/Nucleus_accumbens" title="Nucleus accumbens">nucleus accumbens</a> when inhaled or injected frequently or at high doses, but not necessarily when ingested.<sup id="cite_ref-Nestler_2013Rev_107-0" class="reference"><a href="#cite_note-Nestler_2013Rev-107"><span class="cite-bracket">[</span>107<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Addiction_molecular_neurobiology_108-0" class="reference"><a href="#cite_note-Addiction_molecular_neurobiology-108"><span class="cite-bracket">[</span>108<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RouteDFosB_Primary_109-0" class="reference"><a href="#cite_note-RouteDFosB_Primary-109"><span class="cite-bracket">[</span>109<span class="cite-bracket">]</span></a></sup> Consequently, high daily exposure (possibly excluding <a href="/wiki/Oral_route" class="mw-redirect" title="Oral route">oral route</a>) to nicotine can cause ΔFosB overexpression in the nucleus accumbens, resulting in nicotine addiction.<sup id="cite_ref-Nestler_2013Rev_107-1" class="reference"><a href="#cite_note-Nestler_2013Rev-107"><span class="cite-bracket">[</span>107<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Addiction_molecular_neurobiology_108-1" class="reference"><a href="#cite_note-Addiction_molecular_neurobiology-108"><span class="cite-bracket">[</span>108<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cancer">Cancer</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=12" title="Edit section: Cancer"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Contrary to <a href="/wiki/List_of_common_misconceptions" title="List of common misconceptions">popular belief</a>, nicotine itself does not cause cancer in humans,<sup id="cite_ref-IARCCancerStatement_40-1" class="reference"><a href="#cite_note-IARCCancerStatement-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-110" class="reference"><a href="#cite_note-110"><span class="cite-bracket">[</span>110<span class="cite-bracket">]</span></a></sup> although it is unclear whether it functions as a <a href="/wiki/Tumor_promoter" class="mw-redirect" title="Tumor promoter">tumor promoter</a> as of 2012<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Nicotine&action=edit">[update]</a></sup>.<sup id="cite_ref-111" class="reference"><a href="#cite_note-111"><span class="cite-bracket">[</span>111<span class="cite-bracket">]</span></a></sup> A 2018 report by the US <a href="/wiki/National_Academies_of_Sciences,_Engineering,_and_Medicine" title="National Academies of Sciences, Engineering, and Medicine">National Academies of Sciences, Engineering, and Medicine</a> concludes, "[w]hile it is biologically plausible that nicotine can act as a tumor promoter, the existing body of evidence indicates this is unlikely to translate into increased risk of human cancer."<sup id="cite_ref-112" class="reference"><a href="#cite_note-112"><span class="cite-bracket">[</span>112<span class="cite-bracket">]</span></a></sup> </p><p>Although nicotine is classified as a non-carcinogenic substance, it can still promote tumor growth and metastasis. It induces several processes that contribute to cancer progression, including <a href="/wiki/Cell_cycle" title="Cell cycle">cell cycle</a> progression, <a href="/wiki/Epithelial-to-mesenchymal_transition" class="mw-redirect" title="Epithelial-to-mesenchymal transition">epithelial-to-mesenchymal transition</a>, <a href="/wiki/Cellular_migration" class="mw-redirect" title="Cellular migration">migration</a>, invasion, <a href="/wiki/Angiogenesis" title="Angiogenesis">angiogenesis</a>, and evasion of <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>.<sup id="cite_ref-Schaal_2014_113-0" class="reference"><a href="#cite_note-Schaal_2014-113"><span class="cite-bracket">[</span>113<span class="cite-bracket">]</span></a></sup> These effects are primarily mediated through <a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">nicotinic acetylcholine receptors</a> (nAChRs), particularly the <a href="/wiki/Alpha-7_nicotinic_receptor" title="Alpha-7 nicotinic receptor">α7 subtype</a>, and to a lesser extent, <a href="/wiki/%CE%92-adrenergic_receptor" class="mw-redirect" title="Β-adrenergic receptor">β-adrenergic receptors</a> (β-ARs). Activation of these receptors triggers several <a href="/wiki/Signaling_cascade" class="mw-redirect" title="Signaling cascade">signaling cascades</a> crucial in cancer biology, notably the <a href="/wiki/MAPK/ERK_pathway" title="MAPK/ERK pathway">MAPK/ERK pathway</a>, <a href="/wiki/PI3K/AKT_pathway" class="mw-redirect" title="PI3K/AKT pathway">PI3K/AKT pathway</a>, and <a href="/wiki/JAK-STAT_signaling" class="mw-redirect" title="JAK-STAT signaling">JAK-STAT signaling</a>.<sup id="cite_ref-Schaal_2014_113-1" class="reference"><a href="#cite_note-Schaal_2014-113"><span class="cite-bracket">[</span>113<span class="cite-bracket">]</span></a></sup> </p><p>Nicotine promotes lung cancer development by enhancing proliferation, angiogenesis, migration, invasion, and epithelial–mesenchymal transition (EMT) via nAChRs, which are present in lung cancer cells.<sup id="cite_ref-Merecz-SadowskaSitarek2020_114-0" class="reference"><a href="#cite_note-Merecz-SadowskaSitarek2020-114"><span class="cite-bracket">[</span>114<span class="cite-bracket">]</span></a></sup> Additionally, nicotine-induced EMT contributes to drug resistance in cancer cells.<sup id="cite_ref-115" class="reference"><a href="#cite_note-115"><span class="cite-bracket">[</span>115<span class="cite-bracket">]</span></a></sup> </p><p>Nicotine in tobacco can form carcinogenic <a href="/wiki/Tobacco-specific_nitrosamines" title="Tobacco-specific nitrosamines">tobacco-specific nitrosamines</a> through a <a href="/wiki/Nitrosation" class="mw-redirect" title="Nitrosation">nitrosation</a> reaction. This occurs mostly in the curing and processing of tobacco. However, nicotine in the mouth and stomach can react to form <a href="/wiki/N-Nitrosonornicotine" title="N-Nitrosonornicotine">N-nitrosonornicotine</a>,<sup id="cite_ref-:1_116-0" class="reference"><a href="#cite_note-:1-116"><span class="cite-bracket">[</span>116<span class="cite-bracket">]</span></a></sup> a known type 1 carcinogen,<sup id="cite_ref-:2_117-0" class="reference"><a href="#cite_note-:2-117"><span class="cite-bracket">[</span>117<span class="cite-bracket">]</span></a></sup> suggesting that consumption of non-tobacco forms of nicotine may still play a role in carcinogenesis.<sup id="cite_ref-118" class="reference"><a href="#cite_note-118"><span class="cite-bracket">[</span>118<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Genotoxicity">Genotoxicity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=13" title="Edit section: Genotoxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nicotine causes <a href="/wiki/DNA_damage_(naturally_occurring)" title="DNA damage (naturally occurring)">DNA damage</a> in several types of human cells as judged by assays for <a href="/wiki/Genotoxicity" title="Genotoxicity">genotoxicity</a> such as the <a href="/wiki/Comet_assay" title="Comet assay">comet assay</a>, cytokinesis-block <a href="/wiki/Micronucleus_test" title="Micronucleus test">micronucleus test</a> and <a href="/wiki/Chromosome_abnormality" title="Chromosome abnormality">chromosome aberrations</a> test. In humans, this damage can happen in primary <a href="/wiki/Parotid_gland" title="Parotid gland">parotid gland</a> cells,<sup id="cite_ref-119" class="reference"><a href="#cite_note-119"><span class="cite-bracket">[</span>119<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Lymphocyte" title="Lymphocyte">lymphocytes</a>,<sup id="cite_ref-120" class="reference"><a href="#cite_note-120"><span class="cite-bracket">[</span>120<span class="cite-bracket">]</span></a></sup> and respiratory tract cells.<sup id="cite_ref-121" class="reference"><a href="#cite_note-121"><span class="cite-bracket">[</span>121<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pregnancy_and_breastfeeding">Pregnancy and breastfeeding</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=14" title="Edit section: Pregnancy and breastfeeding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nicotine has been shown to produce birth defects in some animal species, but not others;<sup id="cite_ref-TOXNET_Nicotine_entry_43-1" class="reference"><a href="#cite_note-TOXNET_Nicotine_entry-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> consequently, it is considered to be a possible <a href="/wiki/Teratogen" class="mw-redirect" title="Teratogen">teratogen</a> in humans.<sup id="cite_ref-TOXNET_Nicotine_entry_43-2" class="reference"><a href="#cite_note-TOXNET_Nicotine_entry-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> In <a href="/wiki/Animal_studies" title="Animal studies">animal studies</a> that resulted in birth defects, researchers found that nicotine negatively affects fetal <a href="/wiki/Brain_development" class="mw-redirect" title="Brain development">brain development</a> and pregnancy outcomes;<sup id="cite_ref-TOXNET_Nicotine_entry_43-3" class="reference"><a href="#cite_note-TOXNET_Nicotine_entry-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SGUS2014_41-3" class="reference"><a href="#cite_note-SGUS2014-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> the negative effects on early brain development are associated with abnormalities in <a href="/wiki/Brain_metabolism" class="mw-redirect" title="Brain metabolism">brain metabolism</a> and <a href="/wiki/Neurotransmitter_system" class="mw-redirect" title="Neurotransmitter system">neurotransmitter system</a> function.<sup id="cite_ref-122" class="reference"><a href="#cite_note-122"><span class="cite-bracket">[</span>122<span class="cite-bracket">]</span></a></sup> Nicotine crosses the <a href="/wiki/Placenta" title="Placenta">placenta</a> and is found in the breast milk of mothers who smoke as well as mothers who inhale <a href="/wiki/Passive_smoke" class="mw-redirect" title="Passive smoke">passive smoke</a>.<sup id="cite_ref-Chapman2015_123-0" class="reference"><a href="#cite_note-Chapman2015-123"><span class="cite-bracket">[</span>123<span class="cite-bracket">]</span></a></sup> </p><p>Nicotine exposure <i><a href="/wiki/Uterus" title="Uterus">in utero</a></i> is responsible for several complications of pregnancy and birth: pregnant women who smoke are at greater risk for both <a href="/wiki/Miscarriage" title="Miscarriage">miscarriage</a> and <a href="/wiki/Stillbirth" title="Stillbirth">stillbirth</a> and infants exposed to nicotine <i>in utero</i> tend to have lower <a href="/wiki/Birth_weight" title="Birth weight">birth weights</a>.<sup id="cite_ref-Holbrook2016_124-0" class="reference"><a href="#cite_note-Holbrook2016-124"><span class="cite-bracket">[</span>124<span class="cite-bracket">]</span></a></sup> A <a href="/wiki/McMaster_University" title="McMaster University">McMaster University</a> research group observed in 2010 that rats exposed to nicotine in the womb (via parenteral infusion) later in life had conditions including <a href="/wiki/Type_2_diabetes" title="Type 2 diabetes">type 2 diabetes</a>, <a href="/wiki/Obesity" title="Obesity">obesity</a>, <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, neurobehavioral defects, respiratory dysfunction, and <a href="/wiki/Infertility" title="Infertility">infertility</a>.<sup id="cite_ref-125" class="reference"><a href="#cite_note-125"><span class="cite-bracket">[</span>125<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=15" title="Edit section: Overdose"><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/Nicotine_poisoning" title="Nicotine poisoning">Nicotine poisoning</a></div> <p>It is unlikely that a person would overdose on nicotine through smoking alone. The US <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) stated in 2013 that there are no significant safety concerns associated with the use of more than one form of <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">over-the-counter</a> (OTC) <a href="/wiki/Nicotine_replacement_therapy" title="Nicotine replacement therapy">nicotine replacement therapy</a> at the same time, or using OTC NRT at the same time as another nicotine-containing product, like cigarettes.<sup id="cite_ref-FDANRTLabels_126-0" class="reference"><a href="#cite_note-FDANRTLabels-126"><span class="cite-bracket">[</span>126<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Median_lethal_dose" title="Median lethal dose">median lethal dose</a> of nicotine in humans is unknown.<sup id="cite_ref-ECHA_nicotine_monograph_44-1" class="reference"><a href="#cite_note-ECHA_nicotine_monograph-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MayerNewLethalDose2013_29-2" class="reference"><a href="#cite_note-MayerNewLethalDose2013-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Nevertheless, nicotine has a relatively high <a href="/wiki/Toxicity" title="Toxicity">toxicity</a> in comparison to many other alkaloids such as <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>, which has an LD<sub>50</sub> of 127 mg/kg when administered to mice.<sup id="cite_ref-127" class="reference"><a href="#cite_note-127"><span class="cite-bracket">[</span>127<span class="cite-bracket">]</span></a></sup> At sufficiently high doses, it is associated with nicotine poisoning,<sup id="cite_ref-SGUS2014_41-4" class="reference"><a href="#cite_note-SGUS2014-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> which, while common in children (in whom poisonous and lethal levels occur at lower doses per kilogram of body weight<sup id="cite_ref-Schraufnagel2015_38-2" class="reference"><a href="#cite_note-Schraufnagel2015-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup>) rarely results in significant morbidity or death.<sup id="cite_ref-TOXNET_Nicotine_entry_43-4" class="reference"><a href="#cite_note-TOXNET_Nicotine_entry-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> The estimated lower dose limit for fatal outcomes is 500–1,000 mg of ingested nicotine for an adult (6.5–13 mg/kg).<sup id="cite_ref-RCP_27-4" class="reference"><a href="#cite_note-RCP-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MayerNewLethalDose2013_29-3" class="reference"><a href="#cite_note-MayerNewLethalDose2013-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>The initial symptoms of a nicotine overdose typically include <a href="/wiki/Nausea" title="Nausea">nausea</a>, vomiting, diarrhea, <a href="/wiki/Hypersalivation" title="Hypersalivation">hypersalivation</a>, abdominal pain, <a href="/wiki/Tachycardia" title="Tachycardia">tachycardia</a> (rapid heart rate), <a href="/wiki/Hypertension" title="Hypertension">hypertension</a> (high blood pressure), <a href="/wiki/Tachypnea" title="Tachypnea">tachypnea</a> (rapid breathing), headache, dizziness, <a href="/wiki/Pallor" title="Pallor">pallor</a> (pale skin), auditory or visual disturbances, and perspiration, followed shortly after by marked <a href="/wiki/Bradycardia" title="Bradycardia">bradycardia</a> (slow heart rate), <a href="/wiki/Bradypnea" title="Bradypnea">bradypnea</a> (slow breathing), and <a href="/wiki/Hypotension" title="Hypotension">hypotension</a> (low blood pressure).<sup id="cite_ref-TOXNET_Nicotine_entry_43-5" class="reference"><a href="#cite_note-TOXNET_Nicotine_entry-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> An increased respiratory rate (i.e., <a href="/wiki/Tachypnea" title="Tachypnea">tachypnea</a>) is one of the primary <a href="/wiki/Medical_sign" class="mw-redirect" title="Medical sign">signs</a> of nicotine poisoning.<sup id="cite_ref-TOXNET_Nicotine_entry_43-6" class="reference"><a href="#cite_note-TOXNET_Nicotine_entry-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> At sufficiently high doses, <a href="/wiki/Somnolence" title="Somnolence">somnolence</a> (sleepiness or drowsiness), <a href="/wiki/Confusion" title="Confusion">confusion</a>, <a href="/wiki/Syncope_(medicine)" title="Syncope (medicine)">syncope</a> (loss of consciousness from fainting), <a href="/wiki/Shortness_of_breath" title="Shortness of breath">shortness of breath</a>, marked <a href="/wiki/Weakness" title="Weakness">weakness</a>, <a href="/wiki/Seizure" title="Seizure">seizures</a>, and <a href="/wiki/Coma" title="Coma">coma</a> may occur.<sup id="cite_ref-inchem_8-1" class="reference"><a href="#cite_note-inchem-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TOXNET_Nicotine_entry_43-7" class="reference"><a href="#cite_note-TOXNET_Nicotine_entry-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Lethal nicotine poisoning rapidly produces seizures, and death – which may occur within minutes – is believed to be due to <a href="/wiki/Respiratory_paralysis" class="mw-redirect" title="Respiratory paralysis">respiratory paralysis</a>.<sup id="cite_ref-TOXNET_Nicotine_entry_43-8" class="reference"><a href="#cite_note-TOXNET_Nicotine_entry-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Toxicity">Toxicity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=16" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Today nicotine is less commonly used in agricultural <a href="/wiki/Insecticide" title="Insecticide">insecticides</a>, which was a main source of poisoning. More recent cases of poisoning typically appear to be in the form of <a href="/wiki/Green_Tobacco_Sickness" title="Green Tobacco Sickness">Green Tobacco Sickness</a> (GTS),<sup id="cite_ref-TOXNET_Nicotine_entry_43-9" class="reference"><a href="#cite_note-TOXNET_Nicotine_entry-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> accidental ingestion of <a href="/wiki/Tobacco" title="Tobacco">tobacco</a> or <a href="/wiki/Tobacco_products" class="mw-redirect" title="Tobacco products">tobacco products</a>, or ingestion of nicotine-containing plants.<sup id="cite_ref-Schep_128-0" class="reference"><a href="#cite_note-Schep-128"><span class="cite-bracket">[</span>128<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Smolinske_129-0" class="reference"><a href="#cite_note-Smolinske-129"><span class="cite-bracket">[</span>129<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Furer_130-0" class="reference"><a href="#cite_note-Furer-130"><span class="cite-bracket">[</span>130<span class="cite-bracket">]</span></a></sup> People who harvest or cultivate tobacco may experience GTS, a type of nicotine poisoning caused by dermal exposure to wet tobacco leaves. This occurs most commonly in young, inexperienced tobacco harvesters who do not consume tobacco.<sup id="cite_ref-Schep_128-1" class="reference"><a href="#cite_note-Schep-128"><span class="cite-bracket">[</span>128<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-131" class="reference"><a href="#cite_note-131"><span class="cite-bracket">[</span>131<span class="cite-bracket">]</span></a></sup> People can be exposed to nicotine in the workplace by breathing it in, skin absorption, swallowing it, or eye contact. The <a href="/wiki/Occupational_Safety_and_Health_Administration" title="Occupational Safety and Health Administration">Occupational Safety and Health Administration</a> (OSHA) has set the legal limit (<a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">permissible exposure limit</a>) for nicotine exposure in the workplace as 0.5 mg/m<sup>3</sup> skin exposure over an 8-hour workday. The US <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH) has set a <a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">recommended exposure limit</a> (REL) of 0.5 mg/m<sup>3</sup> skin exposure over an 8-hour workday. At environmental levels of 5 mg/m<sup>3</sup>, nicotine is <a href="/wiki/IDLH" class="mw-redirect" title="IDLH">immediately dangerous to life and health</a>.<sup id="cite_ref-132" class="reference"><a href="#cite_note-132"><span class="cite-bracket">[</span>132<span class="cite-bracket">]</span></a></sup> </p> <div style="clear:right;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Drug_interactions">Drug interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=17" title="Edit section: Drug interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamic">Pharmacodynamic</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=18" title="Edit section: Pharmacodynamic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Potential interaction with <a href="/wiki/Sympathomimetic_drug" title="Sympathomimetic drug">sympathomimetic drugs</a> (<a href="/wiki/Adrenergic_agonist" title="Adrenergic agonist">adrenergic agonists</a>) and <a href="/wiki/Sympatholytic_drug" class="mw-redirect" title="Sympatholytic drug">sympatholytic drugs</a> (<a href="/wiki/Alpha-blocker" class="mw-redirect" title="Alpha-blocker">alpha-blockers</a> and <a href="/wiki/Beta-blockers" class="mw-redirect" title="Beta-blockers">beta-blockers</a>).<sup id="cite_ref-Nicotine_AHFS_monograph_79-8" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetic">Pharmacokinetic</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=19" title="Edit section: Pharmacokinetic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nicotine and cigarette smoke both <a href="/wiki/Inducible_gene" class="mw-redirect" title="Inducible gene">induce</a> the <a href="/wiki/Gene_expression" title="Gene expression">expression</a> of liver enzymes (e.g., certain <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> proteins) which metabolize drugs, leading to the potential for alterations in <a href="/wiki/Drug_metabolism" title="Drug metabolism">drug metabolism</a>.<sup id="cite_ref-Nicotine_AHFS_monograph_79-9" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> </p> <ul><li><i>Smoking cessation</i> may decrease the metabolism of <a href="/wiki/Acetaminophen" class="mw-redirect" title="Acetaminophen">acetaminophen</a>, <a href="/wiki/Beta-blockers" class="mw-redirect" title="Beta-blockers">beta-blockers</a>, <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>, <a href="/wiki/Oxazepam" title="Oxazepam">oxazepam</a>, <a href="/wiki/Pentazocine" title="Pentazocine">pentazocine</a>, <a href="/wiki/Propoxyphene" class="mw-redirect" title="Propoxyphene">propoxyphene</a>, <a href="/wiki/Theophylline" title="Theophylline">theophylline</a>, and <a href="/wiki/Tricyclic_antidepressants" class="mw-redirect" title="Tricyclic antidepressants">tricyclic antidepressants</a>, leading to higher <a href="/wiki/Blood_plasma" title="Blood plasma">plasma</a> concentrations of these drugs.<sup id="cite_ref-Nicotine_AHFS_monograph_79-10" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup></li> <li>Possible alteration of nicotine <a href="/wiki/Drug_absorption" class="mw-redirect" title="Drug absorption">absorption</a> through the skin from the transdermal nicotine patch by drugs that cause <a href="/wiki/Vasodilation" title="Vasodilation">vasodilation</a> or <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstriction</a>.<sup id="cite_ref-Nicotine_AHFS_monograph_79-11" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup></li> <li>Possible alteration of nicotine absorption through the nasal cavity from the nicotine nasal spray by nasal vasoconstrictors (e.g., <a href="/wiki/Xylometazoline" title="Xylometazoline">xylometazoline</a>).<sup id="cite_ref-Nicotine_AHFS_monograph_79-12" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup></li> <li>Possible alteration of nicotine absorption through <a href="/wiki/Oral_mucosa" title="Oral mucosa">oral mucosa</a> from nicotine gum and lozenges by food and drink that modify <a href="/wiki/Saliva" title="Saliva">salivary</a> <a href="/wiki/PH" title="PH">pH</a>.<sup id="cite_ref-Nicotine_AHFS_monograph_79-13" class="reference"><a href="#cite_note-Nicotine_AHFS_monograph-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup></li></ul> <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=Nicotine&action=edit&section=20" 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=Nicotine&action=edit&section=21" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nicotine acts as a <a href="/wiki/Receptor_agonist" class="mw-redirect" title="Receptor agonist">receptor agonist</a> at most <a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">nicotinic acetylcholine receptors</a> (nAChRs),<sup id="cite_ref-IUPHAR_13-2" class="reference"><a href="#cite_note-IUPHAR-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MalenkaNicotine_14-1" class="reference"><a href="#cite_note-MalenkaNicotine-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> except at two <a href="/wiki/Nicotinic_receptor_subunits" class="mw-redirect" title="Nicotinic receptor subunits">nicotinic receptor subunits</a> (<a href="/wiki/NAChR%CE%B19" class="mw-redirect" title="NAChRα9">nAChRα9</a> and <a href="/wiki/NAChR%CE%B110" class="mw-redirect" title="NAChRα10">nAChRα10</a>) where it acts as a <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">receptor antagonist</a>.<sup id="cite_ref-IUPHAR_13-3" class="reference"><a href="#cite_note-IUPHAR-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Such antagonism results in mild <a href="/wiki/Analgesic" title="Analgesic">analgesia</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Central_nervous_system">Central nervous system</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=22" title="Edit section: Central nervous system"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:NicotineDopaminergic_WP1602.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/NicotineDopaminergic_WP1602.png/220px-NicotineDopaminergic_WP1602.png" decoding="async" width="220" height="210" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/NicotineDopaminergic_WP1602.png/330px-NicotineDopaminergic_WP1602.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cf/NicotineDopaminergic_WP1602.png/440px-NicotineDopaminergic_WP1602.png 2x" data-file-width="914" data-file-height="873" /></a><figcaption>Effect of nicotine on dopaminergic neurons</figcaption></figure> <p>By binding to <a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">nicotinic acetylcholine receptors</a> in the brain, nicotine elicits its psychoactive effects and increases the levels of several <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitters</a> in various brain structures – acting as a sort of "volume control".<sup id="cite_ref-Pomerleau1984_133-0" class="reference"><a href="#cite_note-Pomerleau1984-133"><span class="cite-bracket">[</span>133<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-134" class="reference"><a href="#cite_note-134"><span class="cite-bracket">[</span>134<span class="cite-bracket">]</span></a></sup> Nicotine has a higher affinity for nicotinic receptors in the brain than those in <a href="/wiki/Skeletal_muscle" title="Skeletal muscle">skeletal muscle</a>, though at toxic doses it can induce contractions and respiratory paralysis.<sup id="cite_ref-135" class="reference"><a href="#cite_note-135"><span class="cite-bracket">[</span>135<span class="cite-bracket">]</span></a></sup> Nicotine's selectivity is thought to be due to a particular amino acid difference on these receptor subtypes.<sup id="cite_ref-pmid19252481_136-0" class="reference"><a href="#cite_note-pmid19252481-136"><span class="cite-bracket">[</span>136<span class="cite-bracket">]</span></a></sup> Nicotine is unusual in comparison to most drugs, as its profile changes from <a href="/wiki/Stimulant" title="Stimulant">stimulant</a> to <a href="/wiki/Sedative" title="Sedative">sedative</a> with increasing <a href="/wiki/Dose_(biochemistry)" title="Dose (biochemistry)">dosages</a>, a phenomenon known as "Nesbitt's paradox" after the doctor who first described it in 1969.<sup id="cite_ref-137" class="reference"><a href="#cite_note-137"><span class="cite-bracket">[</span>137<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Parrott1998_138-0" class="reference"><a href="#cite_note-Parrott1998-138"><span class="cite-bracket">[</span>138<span class="cite-bracket">]</span></a></sup> At very high doses it dampens <a href="/wiki/Neuronal_activity" class="mw-redirect" title="Neuronal activity">neuronal activity</a>.<sup id="cite_ref-Wadgave2016_139-0" class="reference"><a href="#cite_note-Wadgave2016-139"><span class="cite-bracket">[</span>139<span class="cite-bracket">]</span></a></sup> Nicotine induces both behavioral stimulation and anxiety in animals.<sup id="cite_ref-inchem_8-2" class="reference"><a href="#cite_note-inchem-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Research into nicotine's most predominant metabolite, <a href="/wiki/Cotinine" title="Cotinine">cotinine</a>, suggests that some of nicotine's psychoactive effects are mediated by cotinine.<sup id="cite_ref-140" class="reference"><a href="#cite_note-140"><span class="cite-bracket">[</span>140<span class="cite-bracket">]</span></a></sup> </p><p>Nicotine activates nicotinic receptors (particularly <a href="/wiki/%CE%914%CE%B22_nicotinic_receptor" class="mw-redirect" title="Α4β2 nicotinic receptor">α4β2 nicotinic receptors</a>, but also <a href="/wiki/Alpha5_Nicotinic_Acetylcholine_Receptor" class="mw-redirect" title="Alpha5 Nicotinic Acetylcholine Receptor">α5 nAChRs</a>) on neurons that innervate the <a href="/wiki/Ventral_tegmental_area" title="Ventral tegmental area">ventral tegmental area</a> and within the <a href="/wiki/Mesolimbic_pathway" title="Mesolimbic pathway">mesolimbic pathway</a> where it appears to cause the release of <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>.<sup id="cite_ref-Nicotine_reinforcement_and_euphoria_141-0" class="reference"><a href="#cite_note-Nicotine_reinforcement_and_euphoria-141"><span class="cite-bracket">[</span>141<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Cholinergic-dopaminergic_reward_link_142-0" class="reference"><a href="#cite_note-Cholinergic-dopaminergic_reward_link-142"><span class="cite-bracket">[</span>142<span class="cite-bracket">]</span></a></sup> This nicotine-induced dopamine release occurs at least partially through activation of the <a href="/wiki/Cholinergic%E2%80%93dopaminergic_reward_link" class="mw-redirect" title="Cholinergic–dopaminergic reward link">cholinergic–dopaminergic reward link</a> in the <a href="/wiki/Ventral_tegmental_area" title="Ventral tegmental area">ventral tegmental area</a>.<sup id="cite_ref-Cholinergic-dopaminergic_reward_link_142-1" class="reference"><a href="#cite_note-Cholinergic-dopaminergic_reward_link-142"><span class="cite-bracket">[</span>142<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Picciotto2014_143-0" class="reference"><a href="#cite_note-Picciotto2014-143"><span class="cite-bracket">[</span>143<span class="cite-bracket">]</span></a></sup> Nicotine can modulate the firing rate of the ventral tegmental area neurons.<sup id="cite_ref-Picciotto2014_143-1" class="reference"><a href="#cite_note-Picciotto2014-143"><span class="cite-bracket">[</span>143<span class="cite-bracket">]</span></a></sup> These actions are largely responsible for the strongly reinforcing effects of nicotine, which often occur in the absence of <a href="/wiki/Euphoria" title="Euphoria">euphoria</a>;<sup id="cite_ref-Nicotine_reinforcement_and_euphoria_141-1" class="reference"><a href="#cite_note-Nicotine_reinforcement_and_euphoria-141"><span class="cite-bracket">[</span>141<span class="cite-bracket">]</span></a></sup> however, mild euphoria from nicotine use can occur in some individuals.<sup id="cite_ref-Nicotine_reinforcement_and_euphoria_141-2" class="reference"><a href="#cite_note-Nicotine_reinforcement_and_euphoria-141"><span class="cite-bracket">[</span>141<span class="cite-bracket">]</span></a></sup> Chronic nicotine use inhibits class I and II <a href="/wiki/Histone_deacetylases" class="mw-redirect" title="Histone deacetylases">histone deacetylases</a> in the <a href="/wiki/Striatum" title="Striatum">striatum</a>, where this effect plays a role in nicotine addiction.<sup id="cite_ref-144" class="reference"><a href="#cite_note-144"><span class="cite-bracket">[</span>144<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-145" class="reference"><a href="#cite_note-145"><span class="cite-bracket">[</span>145<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Sympathetic_nervous_system">Sympathetic nervous system</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=23" title="Edit section: Sympathetic nervous system"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:NicotineChromaffinCells_WP1603.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/NicotineChromaffinCells_WP1603.png/300px-NicotineChromaffinCells_WP1603.png" decoding="async" width="300" height="193" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/NicotineChromaffinCells_WP1603.png/450px-NicotineChromaffinCells_WP1603.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/NicotineChromaffinCells_WP1603.png/600px-NicotineChromaffinCells_WP1603.png 2x" data-file-width="780" data-file-height="501" /></a><figcaption>Effect of nicotine on chromaffin cells</figcaption></figure> <p>Nicotine also activates the <a href="/wiki/Sympathetic_nervous_system" title="Sympathetic nervous system">sympathetic nervous system</a>,<sup id="cite_ref-146" class="reference"><a href="#cite_note-146"><span class="cite-bracket">[</span>146<span class="cite-bracket">]</span></a></sup> acting via <a href="/wiki/Splanchnic_nerves" title="Splanchnic nerves">splanchnic nerves</a> to the adrenal medulla, stimulating the release of epinephrine. Acetylcholine released by preganglionic sympathetic fibers of these nerves acts on nicotinic acetylcholine receptors, causing the release of epinephrine (and norepinephrine) into the <a href="/wiki/Bloodstream" class="mw-redirect" title="Bloodstream">bloodstream</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Adrenal_medulla">Adrenal medulla</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=24" title="Edit section: Adrenal medulla"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>By binding to <a href="/wiki/Ganglion_type_nicotinic_receptor" class="mw-redirect" title="Ganglion type nicotinic receptor">ganglion type nicotinic receptors</a> in the adrenal medulla, nicotine increases flow of <a href="/wiki/Adrenaline" title="Adrenaline">adrenaline</a> (epinephrine), a stimulating <a href="/wiki/Hormone" title="Hormone">hormone</a> and neurotransmitter. By binding to the receptors, it causes cell depolarization and an influx of <a href="/wiki/Calcium" title="Calcium">calcium</a> through voltage-gated calcium channels. Calcium triggers the <a href="/wiki/Exocytosis" title="Exocytosis">exocytosis</a> of <a href="/wiki/Chromaffin_cell" title="Chromaffin cell">chromaffin granules</a> and thus the release of <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a> (and norepinephrine) into the <a href="/wiki/Bloodstream" class="mw-redirect" title="Bloodstream">bloodstream</a>. The release of <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a> (adrenaline) causes an increase in <a href="/wiki/Heart_rate" title="Heart rate">heart rate</a>, <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a> and <a href="/wiki/Breathing" title="Breathing">respiration</a>, as well as higher <a href="/wiki/Blood_glucose" class="mw-redirect" title="Blood glucose">blood glucose</a> levels.<sup id="cite_ref-Marieb_147-0" class="reference"><a href="#cite_note-Marieb-147"><span class="cite-bracket">[</span>147<span class="cite-bracket">]</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=Nicotine&action=edit&section=25" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Nicotine_metabolism.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/d/d1/Nicotine_metabolism.png/600px-Nicotine_metabolism.png" decoding="async" width="600" height="488" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/d/d1/Nicotine_metabolism.png/900px-Nicotine_metabolism.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/d/d1/Nicotine_metabolism.png/1200px-Nicotine_metabolism.png 2x" data-file-width="3148" data-file-height="2558" /></a><figcaption>Urinary metabolites of nicotine, quantified as average percentage of total urinary nicotine<sup id="cite_ref-148" class="reference"><a href="#cite_note-148"><span class="cite-bracket">[</span>148<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>As nicotine enters the body, it is distributed quickly through the <a href="/wiki/Blood" title="Blood">bloodstream</a> and crosses the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> reaching the <a href="/wiki/Human_brain" title="Human brain">brain</a> within 10–20 seconds after inhalation.<sup id="cite_ref-pmid12971663_149-0" class="reference"><a href="#cite_note-pmid12971663-149"><span class="cite-bracket">[</span>149<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of nicotine in the body is around two hours.<sup id="cite_ref-150" class="reference"><a href="#cite_note-150"><span class="cite-bracket">[</span>150<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid7077531_151-0" class="reference"><a href="#cite_note-pmid7077531-151"><span class="cite-bracket">[</span>151<span class="cite-bracket">]</span></a></sup> Nicotine is primarily <a href="/wiki/Excretion" title="Excretion">excreted</a> in <a href="/wiki/Urine" title="Urine">urine</a> and urinary concentrations vary depending upon <a href="/wiki/Urine_flow_rate" title="Urine flow rate">urine flow rate</a> and <a href="/wiki/Urine_pH" class="mw-redirect" title="Urine pH">urine pH</a>.<sup id="cite_ref-inchem_8-3" class="reference"><a href="#cite_note-inchem-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>The amount of nicotine absorbed by the body from smoking can depend on many factors, including the types of tobacco, whether the smoke is inhaled, and whether a filter is used. However, it has been found that the nicotine yield of individual products has only a small effect (4.4%) on the blood concentration of nicotine,<sup id="cite_ref-Russell_1980_152-0" class="reference"><a href="#cite_note-Russell_1980-152"><span class="cite-bracket">[</span>152<span class="cite-bracket">]</span></a></sup> suggesting "the assumed health advantage of switching to lower-tar and lower-nicotine cigarettes may be largely offset by the tendency of smokers to compensate by increasing inhalation". </p><p>Nicotine has a half-life of 1–2 hours. <a href="/wiki/Cotinine" title="Cotinine">Cotinine</a> is an active metabolite of nicotine that remains in the blood with a half-life of 18–20 hours, making it easier to analyze.<sup id="cite_ref-153" class="reference"><a href="#cite_note-153"><span class="cite-bracket">[</span>153<span class="cite-bracket">]</span></a></sup> </p><p>Nicotine is <a href="/wiki/Metabolized" class="mw-redirect" title="Metabolized">metabolized</a> in the <a href="/wiki/Liver" title="Liver">liver</a> by <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> enzymes (mostly <a href="/wiki/CYP2A6" title="CYP2A6">CYP2A6</a>, and also by <a href="/wiki/CYP2B6" title="CYP2B6">CYP2B6</a>) and <a href="/wiki/FMO3" class="mw-redirect" title="FMO3">FMO3</a>, which selectively metabolizes (<i>S</i>)-nicotine. A major metabolite is <a href="/wiki/Cotinine" title="Cotinine">cotinine</a>. Other primary metabolites include nicotine <i>N</i>-oxide, nornicotine, nicotine isomethonium ion, 2-hydroxynicotine and nicotine glucuronide.<sup id="cite_ref-pmid15734728_154-0" class="reference"><a href="#cite_note-pmid15734728-154"><span class="cite-bracket">[</span>154<span class="cite-bracket">]</span></a></sup> Under some conditions, other substances may be formed such as <a href="/wiki/Myosmine" title="Myosmine">myosmine</a>.<sup id="cite_ref-Petrick_2011_155-0" class="reference"><a href="#cite_note-Petrick_2011-155"><span class="cite-bracket">[</span>155<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-156" class="reference"><a href="#cite_note-156"><span class="cite-bracket">[</span>156<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Glucuronidation" title="Glucuronidation">Glucuronidation</a> and oxidative metabolism of nicotine to cotinine are both inhibited by <a href="/wiki/Menthol" title="Menthol">menthol</a>, an additive to <a href="/wiki/Menthol_cigarettes" class="mw-redirect" title="Menthol cigarettes">mentholated cigarettes</a>, thus increasing the half-life of nicotine <i><a href="/wiki/In_vivo" title="In vivo">in vivo</a></i>.<sup id="cite_ref-157" class="reference"><a href="#cite_note-157"><span class="cite-bracket">[</span>157<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism">Metabolism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=26" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nicotine decreases hunger and as a consequence food consumption, alongside increasing <a href="/wiki/Energy_expenditure" title="Energy expenditure">energy expenditure</a>.<sup id="cite_ref-158" class="reference"><a href="#cite_note-158"><span class="cite-bracket">[</span>158<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HuYang2018_159-0" class="reference"><a href="#cite_note-HuYang2018-159"><span class="cite-bracket">[</span>159<span class="cite-bracket">]</span></a></sup> The majority of research shows that nicotine reduces body weight, but some researchers have found that nicotine may result in weight gain under specific types of eating habits in animal models.<sup id="cite_ref-HuYang2018_159-1" class="reference"><a href="#cite_note-HuYang2018-159"><span class="cite-bracket">[</span>159<span class="cite-bracket">]</span></a></sup> Nicotine effect on weight appears to result from nicotine's stimulation of α3β4 nAChR receptors located in the <a href="/wiki/Proopiomelanocortin" title="Proopiomelanocortin">POMC neurons</a> in the arcuate nucleus and subsequently the <a href="/wiki/Central_melanocortin_system" title="Central melanocortin system">melanocortin system</a>, especially the melanocortin-4 receptors on second-order neurons in the paraventricular nucleus of the hypothalamus, thus modulating feeding inhibition.<sup id="cite_ref-Picciotto2014_143-2" class="reference"><a href="#cite_note-Picciotto2014-143"><span class="cite-bracket">[</span>143<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HuYang2018_159-2" class="reference"><a href="#cite_note-HuYang2018-159"><span class="cite-bracket">[</span>159<span class="cite-bracket">]</span></a></sup> POMC neurons are a precursor of the melanocortin system, a critical regulator of body weight and peripheral tissue such as skin and hair.<sup id="cite_ref-HuYang2018_159-3" class="reference"><a href="#cite_note-HuYang2018-159"><span class="cite-bracket">[</span>159<span class="cite-bracket">]</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=Nicotine&action=edit&section=27" 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:r1257001546"><table class="infobox" style="width: 12em;"><tbody><tr><th colspan="2" class="infobox-above" style="background:#FFCB66; font-size: 98%;"><a href="/wiki/NFPA_704" title="NFPA 704">NFPA 704</a><br /><i>safety square</i></th></tr><tr><td colspan="2" class="infobox-image"><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_8a72be159ebe5ef6" /></span><map name="ImageMap_8a72be159ebe5ef6"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" title="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" class="notheme mw-no-invert">4</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div><div class="infobox-caption"><div style="clear:both;" class=""></div>The fire diamond hazard sign for nicotine<sup id="cite_ref-160" class="reference"><a href="#cite_note-160"><span class="cite-bracket">[</span>160<span class="cite-bracket">]</span></a></sup></div></td></tr></tbody></table> <p>Nicotine is a <a href="/wiki/Hygroscopy" title="Hygroscopy">hygroscopic</a>, colorless<sup id="cite_ref-:4_83-1" class="reference"><a href="#cite_note-:4-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> to yellow-brown, oily liquid, that is readily soluble in alcohol, ether or light petroleum. It is <a href="/wiki/Miscible" class="mw-redirect" title="Miscible">miscible</a> with <a href="/wiki/Water_(molecule)" class="mw-redirect" title="Water (molecule)">water</a> in its neutral amine <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a> form between 60 °C and 210 °C. It is a dibasic <a href="/wiki/Nitrogenous_base" class="mw-redirect" title="Nitrogenous base">nitrogenous base</a>, having K<sub>b1</sub>=1×10<sup>−6</sup>, K<sub>b2</sub>=1×10<sup>−11</sup>.<sup id="cite_ref-metcalf_161-0" class="reference"><a href="#cite_note-metcalf-161"><span class="cite-bracket">[</span>161<span class="cite-bracket">]</span></a></sup> It readily forms ammonium <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> with <a href="/wiki/Acid" title="Acid">acids</a> that are usually solid and water-soluble. Its <a href="/wiki/Flash_point" title="Flash point">flash point</a> is 95 °C and its auto-ignition temperature is 244 °C.<sup id="cite_ref-SLMSDS_162-0" class="reference"><a href="#cite_note-SLMSDS-162"><span class="cite-bracket">[</span>162<span class="cite-bracket">]</span></a></sup> Nicotine is readily volatile (<a href="/wiki/Vapor_pressure" title="Vapor pressure">vapor pressure</a> 5.5 Pa at 25 °C)<sup id="cite_ref-metcalf_161-1" class="reference"><a href="#cite_note-metcalf-161"><span class="cite-bracket">[</span>161<span class="cite-bracket">]</span></a></sup> On exposure to ultraviolet light or various oxidizing agents, nicotine is converted to nicotine oxide, <a href="/wiki/Nicotinic_acid" class="mw-redirect" title="Nicotinic acid">nicotinic acid</a> (niacin, vitamin B3), and <a href="/wiki/Methylamine" title="Methylamine">methylamine</a>.<sup id="cite_ref-library.sciencemadness.org_163-0" class="reference"><a href="#cite_note-library.sciencemadness.org-163"><span class="cite-bracket">[</span>163<span class="cite-bracket">]</span></a></sup> </p><p>Nicotine is <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a> and hence <a href="/wiki/Optically_active" class="mw-redirect" title="Optically active">optically active</a>, having two <a href="/wiki/Enantiomer" title="Enantiomer">enantiomeric</a> forms. The naturally occurring form of nicotine is <a href="/wiki/Levorotatory" class="mw-redirect" title="Levorotatory">levorotatory</a> with a <a href="/wiki/Specific_rotation" title="Specific rotation">specific rotation</a> of [α]<sub>D</sub>=–166.4° ((−)-nicotine). The <a href="/wiki/Dextrorotatory" class="mw-redirect" title="Dextrorotatory">dextrorotatory</a> form, (+)-nicotine is physiologically less active than (−)-nicotine. (−)-nicotine is more toxic than (+)-nicotine.<sup id="cite_ref-164" class="reference"><a href="#cite_note-164"><span class="cite-bracket">[</span>164<span class="cite-bracket">]</span></a></sup> The salts of (−)-nicotine are usually dextrorotatory; this conversion between levorotatory and dextrorotatory upon protonation is common among alkaloids.<sup id="cite_ref-library.sciencemadness.org_163-1" class="reference"><a href="#cite_note-library.sciencemadness.org-163"><span class="cite-bracket">[</span>163<span class="cite-bracket">]</span></a></sup> The hydrochloride and sulfate salts become optically inactive if heated in a closed vessel above 180 °C.<sup id="cite_ref-library.sciencemadness.org_163-2" class="reference"><a href="#cite_note-library.sciencemadness.org-163"><span class="cite-bracket">[</span>163<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Anabasine" title="Anabasine">Anabasine</a> is a <a href="/wiki/Structural_isomer" title="Structural isomer">structural isomer</a> of nicotine, as both compounds have the <a href="/wiki/Molecular_formula" class="mw-redirect" title="Molecular formula">molecular formula</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap"><a href="/wiki/Carbon" title="Carbon">C</a><sub class="template-chem2-sub">10</sub><a href="/wiki/Hydrogen" title="Hydrogen">H</a><sub class="template-chem2-sub">14</sub><a href="/wiki/Nitrogen" title="Nitrogen">N</a><sub class="template-chem2-sub">2</sub></span>. </p><p> Nicotine that is found in natural tobacco is primarily (99%) the S-enantiomer.<sup id="cite_ref-Enantiomeric_composition_of_nicotin_165-0" class="reference"><a href="#cite_note-Enantiomeric_composition_of_nicotin-165"><span class="cite-bracket">[</span>165<span class="cite-bracket">]</span></a></sup>  Conversely, the most common chemistry synthetic methods for generating nicotine yields a product that is approximately equal proportions of the S- and R-enantiomers.<sup id="cite_ref-166" class="reference"><a href="#cite_note-166"><span class="cite-bracket">[</span>166<span class="cite-bracket">]</span></a></sup> This suggests that tobacco-derived and synthetic nicotine can be determined by measuring the ratio of the two different enantiomers, although means exist for adjusting the relative levels of the enantiomers or performing a synthesis that only leads to the S-enantiomer. There is limited data on the relative physiological effects of these two enantiomers, especially in people. However, the studies to date indicate that (S)-nicotine is more potent than (R)-nicotine and (S)-nicotine causes stronger sensations or irritation than (R)-nicotine. Studies have not been adequate to determine the relative addictiveness of the two enantiomers in people. </p><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Nicotine_benzoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Nicotine_benzoate.svg/220px-Nicotine_benzoate.svg.png" decoding="async" width="220" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Nicotine_benzoate.svg/330px-Nicotine_benzoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Nicotine_benzoate.svg/440px-Nicotine_benzoate.svg.png 2x" data-file-width="715" data-file-height="270" /></a><figcaption>Structure of protonated nicotine (left) and structure of the counterion benzoate (right). This combination is used in some vaping products to increase nicotine delivery to the lung.</figcaption></figure> <p><a href="/wiki/Construction_of_electronic_cigarettes#Pod_mods" title="Construction of electronic cigarettes">Pod mod</a> electronic cigarettes use nicotine in the form of a <a href="/wiki/Nicotine_salt" title="Nicotine salt">protonated nicotine</a>, rather than <a href="/wiki/Free_base" title="Free base">free-base</a> nicotine found in earlier generations.<sup id="cite_ref-JenssenBoykan2019_167-0" class="reference"><a href="#cite_note-JenssenBoykan2019-167"><span class="cite-bracket">[</span>167<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Preparation">Preparation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=28" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first laboratory preparation of nicotine (as its <a href="/wiki/Racemate" class="mw-redirect" title="Racemate">racemate</a>) was described in 1904.<sup id="cite_ref-Pictet_168-0" class="reference"><a href="#cite_note-Pictet-168"><span class="cite-bracket">[</span>168<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Nicotine_synthesis_1904.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Nicotine_synthesis_1904.svg/650px-Nicotine_synthesis_1904.svg.png" decoding="async" width="650" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Nicotine_synthesis_1904.svg/975px-Nicotine_synthesis_1904.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Nicotine_synthesis_1904.svg/1300px-Nicotine_synthesis_1904.svg.png 2x" data-file-width="512" data-file-height="76" /></a></span></dd></dl> <p>The starting material was an N-substituted <a href="/wiki/Pyrrole" title="Pyrrole">pyrrole</a> derivative, which was heated to convert it by a <a href="/wiki/Sigmatropic_reaction" title="Sigmatropic reaction">[1,5] sigmatropic shift</a> to the <a href="/wiki/Isomer" title="Isomer">isomer</a> with a carbon bond between the pyrrole and pyridine rings, followed by <a href="/wiki/Methylation" title="Methylation">methylation</a> and selective reduction of the pyrrole ring using tin and hydrochloric acid.<sup id="cite_ref-Pictet_168-1" class="reference"><a href="#cite_note-Pictet-168"><span class="cite-bracket">[</span>168<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-169" class="reference"><a href="#cite_note-169"><span class="cite-bracket">[</span>169<span class="cite-bracket">]</span></a></sup> Many other syntheses of nicotine, in both racemic and chiral forms have since been published.<sup id="cite_ref-170" class="reference"><a href="#cite_note-170"><span class="cite-bracket">[</span>170<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=29" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Nicotine_biosynthesis_june_2012.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/Nicotine_biosynthesis_june_2012.png/300px-Nicotine_biosynthesis_june_2012.png" decoding="async" width="300" height="262" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/Nicotine_biosynthesis_june_2012.png/450px-Nicotine_biosynthesis_june_2012.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/81/Nicotine_biosynthesis_june_2012.png/600px-Nicotine_biosynthesis_june_2012.png 2x" data-file-width="2103" data-file-height="1837" /></a><figcaption>Nicotine biosynthesis</figcaption></figure> <p>The biosynthetic pathway of nicotine involves a coupling reaction between the two cyclic structures that comprise nicotine. Metabolic studies show that the <a href="/wiki/Pyridine" title="Pyridine">pyridine</a> ring of nicotine is derived from <a href="/wiki/Niacin" title="Niacin">niacin</a> (nicotinic acid) while the <a href="/wiki/Pyrrolidine" title="Pyrrolidine">pyrrolidine</a> is derived from <i>N</i>-methyl-Δ<sup>1</sup>-pyrrollidium cation.<sup id="cite_ref-171" class="reference"><a href="#cite_note-171"><span class="cite-bracket">[</span>171<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-172" class="reference"><a href="#cite_note-172"><span class="cite-bracket">[</span>172<span class="cite-bracket">]</span></a></sup> Biosynthesis of the two component structures proceeds via two independent syntheses, the NAD pathway for niacin and the tropane pathway for <i>N</i>-methyl-Δ<sup>1</sup>-pyrrollidium cation. </p><p>The NAD pathway in the genus <i><a href="/wiki/Nicotiana" title="Nicotiana">Nicotiana</a></i> begins with the oxidation of aspartic acid into α-amino succinate by aspartate oxidase (AO). This is followed by a condensation with <a href="/wiki/Glyceraldehyde-3-phosphate" class="mw-redirect" title="Glyceraldehyde-3-phosphate">glyceraldehyde-3-phosphate</a> and a cyclization catalyzed by quinolinate synthase (QS) to give <a href="/wiki/Quinolinic_acid" title="Quinolinic acid">quinolinic acid</a>. Quinolinic acid then reacts with phosphoribosyl pyrophosphate catalyzed by quinolinic acid phosphoribosyl transferase (QPT) to form niacin mononucleotide (NaMN). The reaction now proceeds via the NAD salvage cycle to produce niacin via the conversion of <a href="/wiki/Nicotinamide" title="Nicotinamide">nicotinamide</a> by the enzyme <a href="/wiki/Nicotinamidase" title="Nicotinamidase">nicotinamidase</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (May 2021)">citation needed</span></a></i>]</sup> </p><p>The <i>N</i>-methyl-Δ<sup>1</sup>-pyrrollidium cation used in the synthesis of nicotine is an intermediate in the synthesis of tropane-derived alkaloids. Biosynthesis begins with <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> of <a href="/wiki/Ornithine" title="Ornithine">ornithine</a> by <a href="/wiki/Ornithine_decarboxylase" title="Ornithine decarboxylase">ornithine decarboxylase</a> (ODC) to produce <a href="/wiki/Putrescine" title="Putrescine">putrescine</a>. Putrescine is then converted into <i>N</i>-methyl putrescine via <a href="/wiki/Methylation" title="Methylation">methylation</a> by SAM catalyzed by <a href="/wiki/Putrescine_N-methyltransferase" title="Putrescine N-methyltransferase">putrescine <i>N</i>-methyltransferase</a> (PMT). <i>N</i>-methyl putrescine then undergoes <a href="/wiki/Deamination" title="Deamination">deamination</a> into 4-methylaminobutanal by the <i>N</i>-methyl putrescine oxidase (MPO) enzyme, 4-methylaminobutanal then spontaneously cyclize into <i>N</i>-methyl-Δ<sup>1</sup>-pyrrollidium cation.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (May 2021)">citation needed</span></a></i>]</sup> </p><p>The final step in the synthesis of nicotine is the coupling between <i>N</i>-methyl-Δ<sup>1</sup>-pyrrollidium cation and niacin. Although studies conclude some form of coupling between the two component structures, the definite process and mechanism remains undetermined. The current agreed theory involves the conversion of niacin into 2,5-dihydropyridine through 3,6-dihydronicotinic acid. The 2,5-dihydropyridine intermediate would then react with <i>N</i>-methyl-Δ<sup>1</sup>-pyrrollidium cation to form <a href="/wiki/Enantiomer" title="Enantiomer">enantiomerically</a> pure (−)-nicotine.<sup id="cite_ref-plant-meta_173-0" class="reference"><a href="#cite_note-plant-meta-173"><span class="cite-bracket">[</span>173<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Detection_in_body_fluids">Detection in body fluids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=30" title="Edit section: Detection in body fluids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nicotine can be quantified in blood, plasma, or urine to confirm a diagnosis of poisoning or to facilitate a medicolegal death investigation. Urinary or salivary cotinine concentrations are frequently measured for the purposes of pre-employment and health insurance medical screening programs. Careful interpretation of results is important, since passive exposure to cigarette smoke can result in significant accumulation of nicotine, followed by the appearance of its metabolites in various body fluids.<sup id="cite_ref-174" class="reference"><a href="#cite_note-174"><span class="cite-bracket">[</span>174<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-175" class="reference"><a href="#cite_note-175"><span class="cite-bracket">[</span>175<span class="cite-bracket">]</span></a></sup> Nicotine use is not regulated in competitive sports programs.<sup id="cite_ref-176" class="reference"><a href="#cite_note-176"><span class="cite-bracket">[</span>176<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Methods_for_analysis_of_enantiomers">Methods for analysis of enantiomers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=31" title="Edit section: Methods for analysis of enantiomers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Methods for measuring the two enantiomers are straightforward and include normal-phase liquid chromatography,<sup id="cite_ref-Enantiomeric_composition_of_nicotin_165-1" class="reference"><a href="#cite_note-Enantiomeric_composition_of_nicotin-165"><span class="cite-bracket">[</span>165<span class="cite-bracket">]</span></a></sup> liquid chromatography with a chiral column.<sup id="cite_ref-177" class="reference"><a href="#cite_note-177"><span class="cite-bracket">[</span>177<span class="cite-bracket">]</span></a></sup> However, since methods can be used to alter the two enantiomers, it may not be possible to distinguish tobacco-derived from synthetic nicotine simply by measuring the levels of the two enantiomers. A new approach uses hydrogen and deuterium nuclear magnetic resonance to distinguish tobacco-derived and synthetic nicotine based on differences the substrates used in the natural synthetic pathway performed in the tobacco plant and the substrates most used in synthesis.<sup id="cite_ref-178" class="reference"><a href="#cite_note-178"><span class="cite-bracket">[</span>178<span class="cite-bracket">]</span></a></sup> Another approach measures the carbon-14 content which also differs between natural and laboratory-based tobacco.<sup id="cite_ref-179" class="reference"><a href="#cite_note-179"><span class="cite-bracket">[</span>179<span class="cite-bracket">]</span></a></sup> These methods remain to be fully evaluated and validated using a wide range of samples. </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=Nicotine&action=edit&section=32" title="Edit section: Natural occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nicotine is a <a href="/wiki/Secondary_metabolite" title="Secondary metabolite">secondary metabolite</a> produced in a variety of plants in the family <a href="/wiki/Solanaceae" title="Solanaceae">Solanaceae</a>, most notably in tobacco <i><a href="/wiki/Nicotiana_tabacum" title="Nicotiana tabacum">Nicotiana tabacum</a></i>, where it can be found at high concentrations of 0.5 to 7.5%.<sup id="cite_ref-180" class="reference"><a href="#cite_note-180"><span class="cite-bracket">[</span>180<span class="cite-bracket">]</span></a></sup> Nicotine is also found in the leaves of other tobacco species, such as <i><a href="/wiki/Nicotiana_rustica" title="Nicotiana rustica">Nicotiana rustica</a></i> (in amounts of 2–14%). Nicotine production is strongly induced in response to wounding as part of a <a href="/wiki/Jasmonate" title="Jasmonate">jasmonate</a>-dependent reaction.<sup id="cite_ref-181" class="reference"><a href="#cite_note-181"><span class="cite-bracket">[</span>181<span class="cite-bracket">]</span></a></sup> Specialist insects on tobacco, such as the tobacco hornworm (<i><a href="/wiki/Manduca_sexta" title="Manduca sexta">Manduca sexta</a></i>), have a number of adaptations to the detoxification and even adaptive re-purposing of nicotine.<sup id="cite_ref-182" class="reference"><a href="#cite_note-182"><span class="cite-bracket">[</span>182<span class="cite-bracket">]</span></a></sup> Nicotine is also found at low concentrations in the nectar of tobacco plants, where it may promote <a href="/wiki/Outcrossing" title="Outcrossing">outcrossing</a> by affecting the behavior of hummingbird pollinators.<sup id="cite_ref-183" class="reference"><a href="#cite_note-183"><span class="cite-bracket">[</span>183<span class="cite-bracket">]</span></a></sup> </p><p>Nicotine occurs in smaller amounts (varying from 2–7 <a href="/wiki/Microgram" title="Microgram">μg</a>/<a href="/wiki/Kilogram" title="Kilogram">kg</a>, or 20–70 millionths of a percent wet weight<sup id="cite_ref-SiegmundLeitner1999_17-2" class="reference"><a href="#cite_note-SiegmundLeitner1999-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup>) in other <a href="/wiki/Solanaceae" title="Solanaceae">Solanaceaeous</a> plants, including some crop species such as <a href="/wiki/Potato" title="Potato">potatoes</a>, <a href="/wiki/Tomato" title="Tomato">tomatoes</a>, <a href="/wiki/Eggplant" title="Eggplant">eggplant</a>, and <a href="/wiki/Capsicum" title="Capsicum">peppers</a>,<sup id="cite_ref-SiegmundLeitner1999_17-3" class="reference"><a href="#cite_note-SiegmundLeitner1999-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Domino1993_184-0" class="reference"><a href="#cite_note-Domino1993-184"><span class="cite-bracket">[</span>184<span class="cite-bracket">]</span></a></sup> as well as non-crop species such as <i><a href="/wiki/Duboisia_hopwoodii" title="Duboisia hopwoodii">Duboisia hopwoodii</a></i>.<sup id="cite_ref-metcalf_161-2" class="reference"><a href="#cite_note-metcalf-161"><span class="cite-bracket">[</span>161<span class="cite-bracket">]</span></a></sup> The amounts of nicotine in tomatoes lowers substantially as the fruit ripens.<sup id="cite_ref-SiegmundLeitner1999_17-4" class="reference"><a href="#cite_note-SiegmundLeitner1999-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> A 1999 report found "In some papers it is suggested that the contribution of dietary nicotine intake is significant when compared with exposure to ETS [environmental tobacco smoke] or by active smoking of small numbers of cigarettes. Others consider the dietary intake to be negligible unless inordinately large amounts of specific vegetables are consumed."<sup id="cite_ref-SiegmundLeitner1999_17-5" class="reference"><a href="#cite_note-SiegmundLeitner1999-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The amount of nicotine eaten per day is roughly around 1.4 and 2.25 <a href="/wiki/Microgram" title="Microgram">μg</a>/day at the 95th percentile.<sup id="cite_ref-SiegmundLeitner1999_17-6" class="reference"><a href="#cite_note-SiegmundLeitner1999-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> These numbers may be low due to insufficient food intake data.<sup id="cite_ref-SiegmundLeitner1999_17-7" class="reference"><a href="#cite_note-SiegmundLeitner1999-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The concentrations of nicotine in vegetables are difficult to measure accurately, since they are very low (parts per billion range).<sup id="cite_ref-MoldoveanuScott2016_185-0" class="reference"><a href="#cite_note-MoldoveanuScott2016-185"><span class="cite-bracket">[</span>185<span class="cite-bracket">]</span></a></sup> Pure nicotine tastes "terrible".<sup id="cite_ref-:4_83-2" class="reference"><a href="#cite_note-:4-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History,_society_and_culture"><span id="History.2C_society_and_culture"></span>History, society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=33" title="Edit section: History, society and culture"><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/History_of_tobacco" title="History of tobacco">History of tobacco</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Joe_dimaggio_camel_ad.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Joe_dimaggio_camel_ad.jpg/220px-Joe_dimaggio_camel_ad.jpg" decoding="async" width="220" height="285" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Joe_dimaggio_camel_ad.jpg/330px-Joe_dimaggio_camel_ad.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Joe_dimaggio_camel_ad.jpg/440px-Joe_dimaggio_camel_ad.jpg 2x" data-file-width="1200" data-file-height="1553" /></a><figcaption><a href="/wiki/Cigarette_advertising" class="mw-redirect" title="Cigarette advertising">Cigarette ad</a> featuring baseball player <a href="/wiki/Joe_DiMaggio" title="Joe DiMaggio">Joe DiMaggio</a> in 1941</figcaption></figure> <p>Nicotine was originally isolated from the tobacco plant in 1828 by chemists Wilhelm Heinrich Posselt and Karl Ludwig Reimann from <a href="/wiki/Germany" title="Germany">Germany</a>, who believed it was a poison.<sup id="cite_ref-186" class="reference"><a href="#cite_note-186"><span class="cite-bracket">[</span>186<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-187" class="reference"><a href="#cite_note-187"><span class="cite-bracket">[</span>187<span class="cite-bracket">]</span></a></sup> Its chemical <a href="/wiki/Empirical_formula" title="Empirical formula">empirical formula</a> was described by <a href="/wiki/Louis_Melsens" title="Louis Melsens">Melsens</a> in 1843,<sup id="cite_ref-188" class="reference"><a href="#cite_note-188"><span class="cite-bracket">[</span>188<span class="cite-bracket">]</span></a></sup> its structure was discovered by <a href="/wiki/Adolf_Pinner" title="Adolf Pinner">Adolf Pinner</a> and <a href="/wiki/Richard_Wolffenstein_(chemist)" title="Richard Wolffenstein (chemist)">Richard Wolffenstein</a> in 1893,<sup id="cite_ref-189" class="reference"><a href="#cite_note-189"><span class="cite-bracket">[</span>189<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-190" class="reference"><a href="#cite_note-190"><span class="cite-bracket">[</span>190<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-191" class="reference"><a href="#cite_note-191"><span class="cite-bracket">[</span>191<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="It's not clear that Wolffenstein should be attributed credit for identifying the structure of nicotine. Please see the talk page. (March 2013)">clarification needed</span></a></i>]</sup> and it was first synthesized by <a href="/wiki/Am%C3%A9_Pictet" title="Amé Pictet">Amé Pictet</a> and A. Rotschy in 1904.<sup id="cite_ref-Pictet_168-2" class="reference"><a href="#cite_note-Pictet-168"><span class="cite-bracket">[</span>168<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-192" class="reference"><a href="#cite_note-192"><span class="cite-bracket">[</span>192<span class="cite-bracket">]</span></a></sup> </p><p>Nicotine is named after the tobacco plant <i><a href="/wiki/Nicotiana_tabacum" title="Nicotiana tabacum">Nicotiana tabacum</a>,</i> which in turn is named after the <a href="/wiki/France" title="France">French</a> ambassador in <a href="/wiki/Portugal" title="Portugal">Portugal</a>, <a href="/wiki/Jean_Nicot" title="Jean Nicot">Jean Nicot de Villemain</a>, who sent tobacco and seeds to <a href="/wiki/Paris" title="Paris">Paris</a> in 1560, presented to the French King,<sup id="cite_ref-Rang_H._P_2007,_page_598_193-0" class="reference"><a href="#cite_note-Rang_H._P_2007,_page_598-193"><span class="cite-bracket">[</span>193<span class="cite-bracket">]</span></a></sup> and who promoted their medicinal use. Smoking was believed to protect against illness, particularly the plague.<sup id="cite_ref-Rang_H._P_2007,_page_598_193-1" class="reference"><a href="#cite_note-Rang_H._P_2007,_page_598-193"><span class="cite-bracket">[</span>193<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Tobacco" title="Tobacco">Tobacco</a> was introduced to <a href="/wiki/Europe" title="Europe">Europe</a> in 1559, and by the late 17th century, it was used not only for <a href="/wiki/Smoking" title="Smoking">smoking</a> but also as an <a href="/wiki/Insecticide" title="Insecticide">insecticide</a>. After <a href="/wiki/World_War_II" title="World War II">World War II</a>, over 2,500 tons of nicotine insecticide were used worldwide, but by the 1980s the use of nicotine insecticide had declined below 200 tons. This was due to the availability of other insecticides that are cheaper and less harmful to <a href="/wiki/Mammal" title="Mammal">mammals</a>.<sup id="cite_ref-Ujvary_19-2" class="reference"><a href="#cite_note-Ujvary-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>The nicotine content of popular American-brand cigarettes has increased over time, and one study found that there was an average increase of 1.78% per year between the years of 1998 and 2005.<sup id="cite_ref-194" class="reference"><a href="#cite_note-194"><span class="cite-bracket">[</span>194<span class="cite-bracket">]</span></a></sup> </p><p>Although methods of production of synthetic nicotine have existed for decades,<sup id="cite_ref-195" class="reference"><a href="#cite_note-195"><span class="cite-bracket">[</span>195<span class="cite-bracket">]</span></a></sup> it was believed that the cost of making nicotine by laboratory synthesis was cost prohibitive compared to extracting nicotine from tobacco.<sup id="cite_ref-196" class="reference"><a href="#cite_note-196"><span class="cite-bracket">[</span>196<span class="cite-bracket">]</span></a></sup> However, recently synthetic nicotine started to be found in different brands of e-cigarettes and oral pouches and marketed as "tobacco-free."<sup id="cite_ref-197" class="reference"><a href="#cite_note-197"><span class="cite-bracket">[</span>197<span class="cite-bracket">]</span></a></sup> </p><p>The US FDA is tasked with reviewing tobacco products such as e-cigarettes and determining which can be authorized for sale. In response to the likelihood that FDA would not authorize many e-cigarettes to be marketed, e-cigarette companies began marketing products that they claimed to contain nicotine that were not made or derived from tobacco, but contained synthetic nicotine instead, and thus, would be outside FDA's tobacco regulatory authority.<sup id="cite_ref-198" class="reference"><a href="#cite_note-198"><span class="cite-bracket">[</span>198<span class="cite-bracket">]</span></a></sup> Similarly, nicotine pouches that claimed to contain non-tobacco (synthetic) nicotine were also introduced. The cost of synthetic nicotine has decreased as the market for the product increased. In March 2022, the U.S. Congress passed a law (the <a href="/wiki/Consolidated_Appropriations_Act,_2022" title="Consolidated Appropriations Act, 2022">Consolidated Appropriations Act, 2022</a>) that expanded FDA's tobacco regulatory authority to include tobacco products containing nicotine from any source, thereby including products made with synthetic nicotine. </p> <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=Nicotine&action=edit&section=34" title="Edit section: Legal status"><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">Further information: <a href="/wiki/Smoking_in_the_United_Kingdom" title="Smoking in the United Kingdom">Smoking in the United Kingdom</a> and <a href="/wiki/Tobacco_in_the_United_States" title="Tobacco in the United States">Tobacco in the United States</a></div> <p>In the United States, nicotine products and <a href="/wiki/Nicotine_replacement_therapy" title="Nicotine replacement therapy">nicotine replacement therapy</a> products like Nicotrol are only available to people 18 and above; proof of age is required; not for sale in vending machine or from any source where proof of age cannot be verified. As of 2019, the minimum age to purchase tobacco in the US is 21 at the federal level.<sup id="cite_ref-199" class="reference"><a href="#cite_note-199"><span class="cite-bracket">[</span>199<span class="cite-bracket">]</span></a></sup> </p><p>In the European Union, the minimum age to purchase nicotine products is 18. However, there is no minimum age requirement to use tobacco or nicotine products.<sup id="cite_ref-200" class="reference"><a href="#cite_note-200"><span class="cite-bracket">[</span>200<span class="cite-bracket">]</span></a></sup> </p><p>In the United Kingdom, the Tobacco and Related Products Regulations 2016 implemented the European directive 2014/40/EU, amended by Tobacco Products and Nicotine Inhaling Products (Amendment etc.) (EU Exit) Regulations 2019 and the Tobacco Products and Nicotine Inhaling Products (Amendment) (EU Exit) Regulations 2020. Additionally other regulations limit advertising, sale and display of tobacco products and other products containing nicotine for human consumption. The Sunak government proposed banning disposable vapes to limit their appeal and affordability for children and to reduce the amount of waste generated. </p> <div class="mw-heading mw-heading3"><h3 id="In_media">In media</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=35" title="Edit section: In media"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1257001546"><table class="infobox" style="width: 300px; clear: right; float:right;margin:0 0 1.5em 1.5em"><tbody><tr><th colspan="2" class="infobox-above" style="font-size:115%">External image</th></tr><tr><td colspan="2" class="infobox-full-data" style="text-align: left"><span typeof="mw:File"><span><img alt="image icon" src="//upload.wikimedia.org/wikipedia/en/thumb/6/61/Searchtool.svg/16px-Searchtool.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/6/61/Searchtool.svg/24px-Searchtool.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/6/61/Searchtool.svg/32px-Searchtool.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span> <a rel="nofollow" class="external text" href="http://www.comicvine.com/nick-oteen/29-67121/">An image showing Nick O'Teen fleeing from Superman</a>, Comic Vine</td></tr></tbody></table> <p>In some <a href="/wiki/Anti-smoking" class="mw-redirect" title="Anti-smoking">anti-smoking</a> literature, the harm that tobacco smoking and nicotine addiction does is personified as <a href="/wiki/Nick_O%27Teen" title="Nick O'Teen">Nick O'Teen</a>, represented as a humanoid with some aspect of a cigarette or cigarette butt about him or his clothes and hat.<sup id="cite_ref-HEC_201-0" class="reference"><a href="#cite_note-HEC-201"><span class="cite-bracket">[</span>201<span class="cite-bracket">]</span></a></sup> Nick O'Teen was a villain that was created for the <a href="/w/index.php?title=Health_Education_Council&action=edit&redlink=1" class="new" title="Health Education Council (page does not exist)">Health Education Council</a>. The character was featured in three animated anti-smoking <a href="/wiki/Public_service_announcements" class="mw-redirect" title="Public service announcements">public service announcements</a> in which he tries to get kids addicted to cigarettes before being foiled by the <a href="/wiki/DC_Comics" title="DC Comics">DC Comics</a> character <a href="/wiki/Superman" title="Superman">Superman</a>.<sup id="cite_ref-HEC_201-1" class="reference"><a href="#cite_note-HEC-201"><span class="cite-bracket">[</span>201<span class="cite-bracket">]</span></a></sup> </p><p>Nicotine was often compared to caffeine in advertisements in the 1980s by the tobacco industry, and later in the 2010s by the electronic cigarettes industry, in an effort to reduce the stigmatization and the public perception of the risks associated with nicotine use.<sup id="cite_ref-202" class="reference"><a href="#cite_note-202"><span class="cite-bracket">[</span>202<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=36" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Central_nervous_system_2">Central nervous system</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=37" title="Edit section: Central nervous system"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>While acute/initial nicotine intake causes activation of neuronal nicotine receptors, chronic low doses of nicotine use leads to desensitization of those receptors (due to the development of tolerance) and results in an antidepressant effect, with early research showing low dose nicotine patches could be an effective treatment of <a href="/wiki/Major_depressive_disorder" title="Major depressive disorder">major depressive disorder</a> in non-smokers.<sup id="cite_ref-pmid20965579_203-0" class="reference"><a href="#cite_note-pmid20965579-203"><span class="cite-bracket">[</span>203<span class="cite-bracket">]</span></a></sup> </p><p>Though tobacco smoking is associated with an increased risk of <a href="/wiki/Alzheimer%27s_disease" title="Alzheimer's disease">Alzheimer's disease</a>,<sup id="cite_ref-pmid19105840_204-0" class="reference"><a href="#cite_note-pmid19105840-204"><span class="cite-bracket">[</span>204<span class="cite-bracket">]</span></a></sup> there is evidence that nicotine itself has the potential to prevent and treat Alzheimer's disease.<sup id="cite_ref-pmid19184661_205-0" class="reference"><a href="#cite_note-pmid19184661-205"><span class="cite-bracket">[</span>205<span class="cite-bracket">]</span></a></sup> </p><p>Smoking is associated with a decreased risk of Parkinson's disease; however, it is unknown whether this is due to people with healthier brain dopaminergic reward centers (the area of the brain affected by Parkinson's) being more likely to enjoy smoking and thus pick up the habit, nicotine directly acting as a <a href="/wiki/Neuroprotection" title="Neuroprotection">neuroprotective agent</a>, or other compounds in cigarette smoke acting as neuroprotective agents.<sup id="cite_ref-206" class="reference"><a href="#cite_note-206"><span class="cite-bracket">[</span>206<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Immune_system">Immune system</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=38" title="Edit section: Immune system"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Immune cells of both the <a href="/wiki/Innate" title="Innate">innate immune system</a> and <a href="/wiki/Adaptive_immune_system" title="Adaptive immune system">adaptive immune systems</a> frequently express the α<sub>2</sub>, α<sub>5</sub>, α<sub>6</sub>, α<sub>7</sub>, α<sub>9</sub>, and α<sub>10</sub> <a href="/wiki/Nicotinic_acetylcholine_receptor#Subunits" title="Nicotinic acetylcholine receptor">subunits of nicotinic acetylcholine receptors</a>.<sup id="cite_ref-:0_207-0" class="reference"><a href="#cite_note-:0-207"><span class="cite-bracket">[</span>207<span class="cite-bracket">]</span></a></sup> Evidence suggests that nicotinic receptors which contain these subunits are involved in the regulation of <a href="/wiki/Immune_function" class="mw-redirect" title="Immune function">immune function</a>.<sup id="cite_ref-:0_207-1" class="reference"><a href="#cite_note-:0-207"><span class="cite-bracket">[</span>207<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Optopharmacology">Optopharmacology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=39" title="Edit section: Optopharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A <a href="/wiki/Photoactivatable_probes" title="Photoactivatable probes">photoactivatable</a> form of nicotine, which releases nicotine when exposed to <a href="/wiki/Ultraviolet_light" class="mw-redirect" title="Ultraviolet light">ultraviolet light</a> with certain conditions, has been developed for studying nicotinic acetylcholine receptors in brain tissue.<sup id="cite_ref-pmid29578537_208-0" class="reference"><a href="#cite_note-pmid29578537-208"><span class="cite-bracket">[</span>208<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Oral_health">Oral health</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=40" title="Edit section: Oral health"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several <i>in vitro</i> studies have investigated the potential effects of nicotine on a range of oral cells. A recent systematic review concluded that nicotine was unlikely to be cytotoxic to oral cells <i>in vitro</i> in most physiological conditions but further research is needed.<sup id="cite_ref-209" class="reference"><a href="#cite_note-209"><span class="cite-bracket">[</span>209<span class="cite-bracket">]</span></a></sup> Understanding the potential role of nicotine in oral health has become increasingly important given the recent introduction of novel nicotine products and their potential role in helping smokers quit.<sup id="cite_ref-210" class="reference"><a href="#cite_note-210"><span class="cite-bracket">[</span>210<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotine&action=edit&section=41" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/6-Chloronicotine" title="6-Chloronicotine">6-Chloronicotine</a></li> <li><a href="/wiki/Nicotine_marketing" title="Nicotine marketing">Nicotine marketing</a></li></ul> <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=Nicotine&action=edit&section=42" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMcLaughlinDaniDe_Biasi2015" class="citation book cs1">McLaughlin I, Dani JA, De Biasi M (2015). "Nicotine Withdrawal". <i>The Neuropharmacology of Nicotine Dependence</i>. Current Topics in Behavioral Neurosciences. Vol. 24. pp. 99–123. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-319-13482-6_4">10.1007/978-3-319-13482-6_4</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-319-13481-9" title="Special:BookSources/978-3-319-13481-9"><bdi>978-3-319-13481-9</bdi></a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4542051">4542051</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25638335">25638335</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Nicotine+Withdrawal&rft.btitle=The+Neuropharmacology+of+Nicotine+Dependence&rft.series=Current+Topics+in+Behavioral+Neurosciences&rft.pages=99-123&rft.date=2015&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4542051%23id-name%3DPMC&rft_id=info%3Apmid%2F25638335&rft_id=info%3Adoi%2F10.1007%2F978-3-319-13482-6_4&rft.isbn=978-3-319-13481-9&rft.aulast=McLaughlin&rft.aufirst=I&rft.au=Dani%2C+JA&rft.au=De+Biasi%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-Dependence-withdrawal-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Dependence-withdrawal_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Dependence-withdrawal_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Dependence-withdrawal_2-2"><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="CITEREFD'SouzaMarkou2011" class="citation journal cs1">D'Souza MS, Markou A (July 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3188825">"Neuronal mechanisms underlying development of nicotine dependence: implications for novel smoking-cessation treatments"</a>. <i>Addiction Science & Clinical Practice</i>. <b>6</b> (1): 4–16. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3188825">3188825</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22003417">22003417</a>. <q>Withdrawal symptoms upon cessation of nicotine intake: Chronic nicotine use induces neuroadaptations in the brain's reward system that result in the development of nicotine dependence. Thus, nicotine-dependent smokers must continue nicotine intake to avoid distressing somatic and affective withdrawal symptoms. Newly abstinent smokers experience symptoms such as depressed mood, anxiety, irritability, difficulty concentrating, craving, bradycardia, insomnia, gastrointestinal discomfort, and weight gain (Shiffman and Jarvik, 1976; Hughes et al., 1991). Experimental animals, such as rats and mice, exhibit a nicotine withdrawal syndrome that, like the human syndrome, includes both somatic signs and a negative affective state (Watkins et al., 2000; Malin et al., 2006). The somatic signs of nicotine withdrawal include rearing, jumping, shakes, abdominal constrictions, chewing, scratching, and facial tremors. The negative affective state of nicotine withdrawal is characterized by decreased responsiveness to previously rewarding stimuli, a state called anhedonia.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Addiction+Science+%26+Clinical+Practice&rft.atitle=Neuronal+mechanisms+underlying+development+of+nicotine+dependence%3A+implications+for+novel+smoking-cessation+treatments&rft.volume=6&rft.issue=1&rft.pages=4-16&rft.date=2011-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3188825%23id-name%3DPMC&rft_id=info%3Apmid%2F22003417&rft.aulast=D%27Souza&rft.aufirst=MS&rft.au=Markou%2C+A&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3188825&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" 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="CITEREFCosciPistelliLazzariniCarrozzi2011" class="citation journal cs1">Cosci F, Pistelli F, Lazzarini N, Carrozzi L (2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3218785">"Nicotine dependence and psychological distress: outcomes and clinical implications in smoking cessation"</a>. <i>Psychology Research and Behavior Management</i>. <b>4</b>: 119–128. <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/10.2147%2Fprbm.s14243">10.2147/prbm.s14243</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3218785">3218785</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22114542">22114542</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Psychology+Research+and+Behavior+Management&rft.atitle=Nicotine+dependence+and+psychological+distress%3A+outcomes+and+clinical+implications+in+smoking+cessation&rft.volume=4&rft.pages=119-128&rft.date=2011&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3218785%23id-name%3DPMC&rft_id=info%3Apmid%2F22114542&rft_id=info%3Adoi%2F10.2147%2Fprbm.s14243&rft.aulast=Cosci&rft.aufirst=F&rft.au=Pistelli%2C+F&rft.au=Lazzarini%2C+N&rft.au=Carrozzi%2C+L&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3218785&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" 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 id="CITEREFHollinger2007" class="citation book cs1">Hollinger MA (19 October 2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=qfrLBQAAQBAJ&pg=PA222"><i>Introduction to Pharmacology</i></a> (Third ed.). Abingdon: CRC Press. pp. 222–223. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4200-4742-4" title="Special:BookSources/978-1-4200-4742-4"><bdi>978-1-4200-4742-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Introduction+to+Pharmacology&rft.place=Abingdon&rft.pages=222-223&rft.edition=Third&rft.pub=CRC+Press&rft.date=2007-10-19&rft.isbn=978-1-4200-4742-4&rft.aulast=Hollinger&rft.aufirst=MA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DqfrLBQAAQBAJ%26pg%3DPA222&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-FDA-AllBoxedWarnings-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-FDA-AllBoxedWarnings_5-0">^</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="https://nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802">"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"</a>. <i>nctr-crs.fda.gov</i>. <a href="/wiki/FDA" class="mw-redirect" title="FDA">FDA</a><span class="reference-accessdate">. Retrieved <span class="nowrap">22 October</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=nctr-crs.fda.gov&rft.atitle=FDA-sourced+list+of+all+drugs+with+black+box+warnings+%28Use+Download+Full+Results+and+View+Query+links.%29&rft_id=https%3A%2F%2Fnctr-crs.fda.gov%2Ffdalabel%2Fui%2Fspl-summaries%2Fcriteria%2F343802&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" 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.legislation.gov.uk/uksi/2001/2068/note/made?view=plain">"The Medicines (Products Other Than Veterinary Drugs) (General Sale List) Amendment Order 2001"</a>. <i>legislation.gov.uk</i><span class="reference-accessdate">. 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NRTs increase the rate of quitting by 50% to 60%, regardless of setting, and further research is very unlikely to change our confidence in the estimate of the effect. The relative effectiveness of NRT appears to be largely independent of the intensity of additional support provided to the individual.<br />A meta-analysis of adverse events associated with NRT included 92 RCTs and 28 observational studies, and addressed a possible excess of chest pains and heart palpitations among users of NRT compared with placebo groups (Mills 2010). The authors report an OR of 2.06 (95% CI 1.51 to 2.82) across 12 studies. We replicated this data collection exercise and analysis where data were available (included and excluded) in this review, and detected a similar but slightly lower estimate, OR 1.88 (95% CI 1.37 to 2.57; 15 studies; 11,074 participants; OR rather than RR calculated for comparison; Analysis 6.1). 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Opinion+on+Drug+Safety&rft.atitle=The+safety+of+treatments+for+tobacco+use+disorder&rft.volume=15&rft.issue=3&rft.pages=333-41&rft.date=2016&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A12064318%23id-name%3DS2CID&rft_id=info%3Apmid%2F26715118&rft_id=info%3Adoi%2F10.1517%2F14740338.2016.1131817&rft.aulast=Little&rft.aufirst=MA&rft.au=Ebbert%2C+JO&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-pharmacotherapy-72"><span class="mw-cite-backlink"><b><a href="#cite_ref-pharmacotherapy_72-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAubinLuquiensBerlin2014" class="citation journal cs1">Aubin HJ, Luquiens A, Berlin I (February 2014). <a rel="nofollow" class="external text" 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=British+Journal+of+Clinical+Pharmacology&rft.atitle=Pharmacotherapy+for+smoking+cessation%3A+pharmacological+principles+and+clinical+practice&rft.volume=77&rft.issue=2&rft.pages=324-36&rft.date=2014-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4014023%23id-name%3DPMC&rft_id=info%3Apmid%2F23488726&rft_id=info%3Adoi%2F10.1111%2Fbcp.12116&rft.aulast=Aubin&rft.aufirst=HJ&rft.au=Luquiens%2C+A&rft.au=Berlin%2C+I&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4014023&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-adolescents-73"><span class="mw-cite-backlink">^ <a href="#cite_ref-adolescents_73-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-adolescents_73-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-adolescents_73-2"><sup><i><b>c</b></i></sup></a></span> <span 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href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22248234">22248234</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Paediatric+Drugs&rft.atitle=Efficacy+and+tolerability+of+pharmacotherapies+to+aid+smoking+cessation+in+adolescents&rft.volume=14&rft.issue=2&rft.pages=91-108&rft.date=2012-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3319092%23id-name%3DPMC&rft_id=info%3Apmid%2F22248234&rft_id=info%3Adoi%2F10.2165%2F11594370-000000000-00000&rft.aulast=Bailey&rft.aufirst=SR&rft.au=Crew%2C+EE&rft.au=Riske%2C+EC&rft.au=Ammerman%2C+S&rft.au=Robinson%2C+TN&rft.au=Killen%2C+JD&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3319092&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-74"><span class="mw-cite-backlink"><b><a href="#cite_ref-74">^</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.cdc.gov/tobacco/basic_information/e-cigarettes/pdfs/Electronic-Cigarettes-Infographic-508.pdf">"Electronic Cigarettes – What are the health effects of using e-cigarettes?"</a> <span class="cs1-format">(PDF)</span>. Centers for Disease Control and Prevention. 22 February 2018. <a rel="nofollow" class="external text" href="https://ghostarchive.org/archive/20221009/https://www.cdc.gov/tobacco/basic_information/e-cigarettes/pdfs/Electronic-Cigarettes-Infographic-508.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 9 October 2022. <q>Nicotine is a health danger for pregnant women and their developing babies.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Electronic+Cigarettes+%E2%80%93+What+are+the+health+effects+of+using+e-cigarettes%3F&rft.pub=Centers+for+Disease+Control+and+Prevention&rft.date=2018-02-22&rft_id=https%3A%2F%2Fwww.cdc.gov%2Ftobacco%2Fbasic_information%2Fe-cigarettes%2Fpdfs%2FElectronic-Cigarettes-Infographic-508.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-75"><span class="mw-cite-backlink"><b><a href="#cite_ref-75">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBruinGersteinHolloway2010" class="citation journal cs1">Bruin JE, Gerstein HC, Holloway AC (August 2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2905398">"Long-term consequences of fetal and neonatal nicotine exposure: a critical review"</a>. <i>Toxicological Sciences</i>. <b>116</b> (2): 364–74. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Ftoxsci%2Fkfq103">10.1093/toxsci/kfq103</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2905398">2905398</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20363831">20363831</a>. <q>there is no safe dose of nicotine during pregnancy... The general consensus among clinicians is that more information is needed about the risks of NRT use during pregnancy before well-informed definitive recommendations can be made to pregnant women... Overall, the evidence provided in this review overwhelmingly indicates that nicotine should no longer be considered the <i>safe</i> component of cigarette smoke. 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Elsevier Health Sciences. p. 525. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-81-312-3623-9" title="Special:BookSources/978-81-312-3623-9"><bdi>978-81-312-3623-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Textbook+of+Forensic+Medicine+%26+Toxicology%3A+Principles+%26+Practice&rft.pages=525&rft.edition=5th&rft.pub=Elsevier+Health+Sciences&rft.date=2014&rft.isbn=978-81-312-3623-9&rft.aulast=Vij&rft.aufirst=K&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DIp1rAwAAQBAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span> <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Ip1rAwAAQBAJ&pg=PA525">Extract of page 525</a></span> </li> <li id="cite_note-82"><span class="mw-cite-backlink"><b><a href="#cite_ref-82">^</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.cdc.gov/niosh/ershdb/emergencyresponsecard_29750028.html">"NICOTINE: Systemic Agent"</a>. 8 July 2021.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=NICOTINE%3A+Systemic+Agent&rft.date=2021-07-08&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fershdb%2Femergencyresponsecard_29750028.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-:4-83"><span class="mw-cite-backlink">^ <a href="#cite_ref-:4_83-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:4_83-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:4_83-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><a rel="nofollow" class="external text" href="https://link.springer.com/10.1007/978-981-99-9283-6_1860">"Nicotine"</a>, <i>Dictionary of Toxicology</i>, Singapore: <a href="/wiki/Springer_Nature" title="Springer Nature">Springer Nature</a>, p. 691, 2024, <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-981-99-9283-6_1860">10.1007/978-981-99-9283-6_1860</a>, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-981-99-9282-9" title="Special:BookSources/978-981-99-9282-9"><bdi>978-981-99-9282-9</bdi></a><span class="reference-accessdate">, retrieved <span class="nowrap">19 October</span> 2024</span>, <q>Nicotine is a colorless, water-soluble, and extremely hazardous alkaloid. It also has a terrible taste.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Dictionary+of+Toxicology&rft.atitle=Nicotine&rft.pages=691&rft.date=2024&rft_id=info%3Adoi%2F10.1007%2F978-981-99-9283-6_1860&rft.isbn=978-981-99-9282-9&rft_id=https%3A%2F%2Flink.springer.com%2F10.1007%2F978-981-99-9283-6_1860&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-RCP_report-84"><span class="mw-cite-backlink"><b><a href="#cite_ref-RCP_report_84-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRoyal_College_of_Physicians" class="citation web cs1">Royal College of Physicians. <a rel="nofollow" class="external text" href="https://www.rcplondon.ac.uk/file/3563/download?token=Mu0K_ZR0">"Nicotine Without Smoke -- Tobacco Harm Reduction"</a>. p. 125<span class="reference-accessdate">. Retrieved <span class="nowrap">30 September</span> 2020</span>. <q>Use of nicotine alone, in the doses used by smokers, represents little if any hazard to the user.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Nicotine+Without+Smoke+--+Tobacco+Harm+Reduction&rft.pages=125&rft.au=Royal+College+of+Physicians&rft_id=https%3A%2F%2Fwww.rcplondon.ac.uk%2Ffile%2F3563%2Fdownload%3Ftoken%3DMu0K_ZR0&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-85"><span class="mw-cite-backlink"><b><a href="#cite_ref-85">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDouglasHensonDropeWender2018" class="citation journal cs1">Douglas CE, Henson R, Drope J, Wender RC (July 2018). <a rel="nofollow" class="external text" href="https://doi.org/10.3322%2Fcaac.21455">"The American Cancer Society public health statement on eliminating combustible tobacco use in the United States"</a>. <i>CA</i>. <b>68</b> (4): 240–245. <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/10.3322%2Fcaac.21455">10.3322/caac.21455</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29889305">29889305</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:47016482">47016482</a>. <q>It is the smoke from combustible tobacco products—not nicotine—that injures and kills millions of smokers.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=CA&rft.atitle=The+American+Cancer+Society+public+health+statement+on+eliminating+combustible+tobacco+use+in+the+United+States&rft.volume=68&rft.issue=4&rft.pages=240-245&rft.date=2018-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A47016482%23id-name%3DS2CID&rft_id=info%3Apmid%2F29889305&rft_id=info%3Adoi%2F10.3322%2Fcaac.21455&rft.aulast=Douglas&rft.aufirst=CE&rft.au=Henson%2C+R&rft.au=Drope%2C+J&rft.au=Wender%2C+RC&rft_id=https%3A%2F%2Fdoi.org%2F10.3322%252Fcaac.21455&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-86"><span class="mw-cite-backlink"><b><a href="#cite_ref-86">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDinakarO'Connor2016" class="citation journal cs1">Dinakar C, O'Connor GT (October 2016). 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+England+Journal+of+Medicine&rft.atitle=The+Health+Effects+of+Electronic+Cigarettes&rft.volume=375&rft.issue=14&rft.pages=1372-1381&rft.date=2016-10&rft_id=info%3Adoi%2F10.1056%2FNEJMra1502466&rft_id=info%3Apmid%2F27705269&rft.aulast=Dinakar&rft.aufirst=C&rft.au=O%27Connor%2C+GT&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-Cochrane_NRT_2018_AEs-87"><span class="mw-cite-backlink">^ <a href="#cite_ref-Cochrane_NRT_2018_AEs_87-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Cochrane_NRT_2018_AEs_87-1"><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="CITEREFHartmann-BoyceChepkinYeBullen2018" class="citation journal cs1">Hartmann-Boyce J, Chepkin SC, Ye W, Bullen C, Lancaster T (May 2018). <a rel="nofollow" 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Smoking during the acute withdrawal phase reduces craving for cigarettes and returns cognitive abilities to pre-smoking cessation level</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neuroscience+and+Biobehavioral+Reviews&rft.atitle=Tobacco+addiction+and+the+dysregulation+of+brain+stress+systems&rft.volume=36&rft.issue=5&rft.pages=1418-41&rft.date=2012-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3340450%23id-name%3DPMC&rft_id=info%3Apmid%2F22405889&rft_id=info%3Adoi%2F10.1016%2Fj.neubiorev.2012.02.015&rft.aulast=Bruijnzeel&rft.aufirst=AW&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3340450&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-Nestler_2013Rev-107"><span class="mw-cite-backlink">^ <a href="#cite_ref-Nestler_2013Rev_107-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Nestler_2013Rev_107-1"><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="CITEREFNestler2013" class="citation journal cs1">Nestler EJ (December 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3898681">"Cellular basis of memory for addiction"</a>. <i>Dialogues in Clinical Neuroscience</i>. <b>15</b> (4): 431–443. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.31887%2FDCNS.2013.15.4%2Fenestler">10.31887/DCNS.2013.15.4/enestler</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3898681">3898681</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24459410">24459410</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Dialogues+in+Clinical+Neuroscience&rft.atitle=Cellular+basis+of+memory+for+addiction&rft.volume=15&rft.issue=4&rft.pages=431-443&rft.date=2013-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3898681%23id-name%3DPMC&rft_id=info%3Apmid%2F24459410&rft_id=info%3Adoi%2F10.31887%2FDCNS.2013.15.4%2Fenestler&rft.aulast=Nestler&rft.aufirst=EJ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3898681&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-Addiction_molecular_neurobiology-108"><span class="mw-cite-backlink">^ <a href="#cite_ref-Addiction_molecular_neurobiology_108-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Addiction_molecular_neurobiology_108-1"><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="CITEREFRuffle2014" class="citation journal cs1">Ruffle JK (November 2014). 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Xiong et al. used this premise to evaluate the potential addictive profile of propofol (119). Propofol is a general anaesthetic, however its abuse for recreational purpose has been documented (120). Using control drugs implicated in both ΔFosB induction and addiction (ethanol and nicotine), ...<br /><br />Conclusions<br />ΔFosB is an essential transcription factor implicated in the molecular and behavioral pathways of addiction following repeated drug exposure. The formation of ΔFosB in multiple brain regions, and the molecular pathway leading to the formation of AP-1 complexes is well understood. The establishment of a functional purpose for ΔFosB has allowed further determination as to some of the key aspects of its molecular cascades, involving effectors such as GluR2 (87,88), Cdk5 (93) and NFkB (100). Moreover, many of these molecular changes identified are now directly linked to the structural, physiological and behavioral changes observed following chronic drug exposure (60,95,97,102). New frontiers of research investigating the molecular roles of ΔFosB have been opened by epigenetic studies, and recent advances have illustrated the role of ΔFosB acting on DNA and histones, truly as a <i>molecular switch</i> (34). 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Archived from <a rel="nofollow" class="external text" href="https://gupea.ub.gu.se/bitstream/2077/26318/1/gupea_2077_26318_1.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 4 August 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">23 September</span> 2019</span>. <q>This reward link comprises a dopamine projection from the ventral tegmental area (VTA) to the nucleus accumbens together with a cholinergic input, arising primarily from the laterodorsal tegmental area.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+and+Cellular+Endocrinology&rft.atitle=The+role+of+the+central+ghrelin+system+in+reward+from+food+and+chemical+drugs&rft.volume=340&rft.issue=1&rft.pages=80-7&rft.date=2011-06&rft_id=info%3Ahdl%2F2077%2F26318&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A206815322%23id-name%3DS2CID&rft_id=info%3Apmid%2F21354264&rft_id=info%3Adoi%2F10.1016%2Fj.mce.2011.02.017&rft.aulast=Dickson&rft.aufirst=SL&rft.au=Egecioglu%2C+E&rft.au=Landgren%2C+S&rft.au=Skibicka%2C+KP&rft.au=Engel%2C+JA&rft.au=Jerlhag%2C+E&rft_id=https%3A%2F%2Fgupea.ub.gu.se%2Fbitstream%2F2077%2F26318%2F1%2Fgupea_2077_26318_1.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotine" class="Z3988"></span></span> </li> <li id="cite_note-Picciotto2014-143"><span class="mw-cite-backlink">^ <a href="#cite_ref-Picciotto2014_143-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Picciotto2014_143-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Picciotto2014_143-2"><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="CITEREFPicciottoMineur2014" class="citation journal cs1">Picciotto MR, Mineur YS (January 2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3772953">"Molecules and circuits involved in nicotine addiction: The many faces of smoking"</a>. <i>Neuropharmacology</i> (Review). <b>76</b> (Pt B): 545–53. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.neuropharm.2013.04.028">10.1016/j.neuropharm.2013.04.028</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3772953">3772953</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23632083">23632083</a>. <q>Rat studies have shown that nicotine administration can decrease food intake and body weight, with greater effects in female animals (Grunberg et al., 1987). 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<ul><li><a rel="nofollow" class="external text" href="http://toxnet.nlm.nih.gov/cgi-bin/sis/search2/r?dbs+hsdb:@term+@DOCNO+1107">Toxicology monograph for Nicotine</a> from the <a href="/wiki/Hazardous_Substances_Data_Bank" title="Hazardous Substances Data Bank">Hazardous Substances Data Bank</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0446.html">Chemical Hazards monograph for Nicotine</a> from the <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a></li> <li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/nicotine#datasheet=lcss&section=Top">Laboratory Chemical Safety Summary for Nicotine</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a></li></ul> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" 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.navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Cigarettes" 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:Cigarettes" title="Template:Cigarettes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cigarettes" title="Template talk:Cigarettes"><abbr title="Discuss this 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cigarette">Menthol</a></li> <li><a href="/wiki/Beedi" title="Beedi">Beedi</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Components</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/Tobacco" title="Tobacco">Tobacco</a></li> <li><a href="/wiki/Rolling_paper" title="Rolling paper">Rolling paper</a></li> <li><a href="/wiki/Cigarette_filter" title="Cigarette filter">Filter</a></li> <li><a href="/wiki/List_of_additives_in_cigarettes" title="List of additives in cigarettes">Additives</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Peripherals</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/Ashtray" title="Ashtray">Ashtray</a></li> <li><a href="/wiki/Cigarette_case" title="Cigarette case">Case</a></li> <li><a href="/wiki/Cigarette_holder" title="Cigarette holder">Holder</a></li> <li><a href="/wiki/Lighter" title="Lighter">Lighter</a></li> <li><a href="/wiki/Cigarette_pack" title="Cigarette pack">Pack</a></li> <li><a href="/wiki/Cigarette_receptacle" title="Cigarette receptacle">Receptacles</a></li> <li><a href="/wiki/Cigarette_machine" title="Cigarette machine">Vending machine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Smoking_culture" class="mw-redirect" title="Smoking culture">Culture</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/Cigarette_card" title="Cigarette card">Cigarette card</a></li> <li><a href="/wiki/Cigarette_smoking_among_college_students" title="Cigarette smoking among college students">Cigarette smoking among college students</a></li> <li><a href="/wiki/Loosie" title="Loosie">Loosie</a></li> <li><a href="/wiki/Smoking_in_association_football" title="Smoking in association football">Smoking in association football</a></li> <li><a href="/wiki/Smoking_fetishism" title="Smoking fetishism">Smoking fetishism</a></li> <li><a href="/wiki/Tobacco_smoking" title="Tobacco smoking">Tobacco smoking</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Health_effects_of_tobacco" title="Health effects of tobacco">Health issues</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/Chain_smoking" title="Chain smoking">Chain smoking</a></li> <li><a href="/wiki/Cigarette_smoking_for_weight_loss" title="Cigarette smoking for weight loss">Cigarette smoking for weight loss</a></li> <li><a href="/wiki/Nicotine_dependence" title="Nicotine dependence">Nicotine dependence</a></li> <li><a href="/wiki/Nicotine_poisoning" title="Nicotine poisoning">Nicotine poisoning</a></li> <li><a href="/wiki/Passive_smoking" title="Passive smoking">Passive smoking</a></li> <li><a href="/wiki/Third-hand_smoke" title="Third-hand smoke">Third-hand smoke</a></li> <li><a href="/wiki/Schizophrenia_and_tobacco_smoking" title="Schizophrenia and tobacco smoking">Schizophrenia and smoking</a></li> <li><a href="/wiki/Sidestream_smoke" title="Sidestream smoke">Sidestream smoke</a></li> <li><a href="/wiki/Smoking_cessation" title="Smoking cessation">Smoking cessation</a></li> <li><a href="/wiki/Tobacco_harm_reduction" title="Tobacco harm reduction">Tobacco harm reduction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related products</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/Candy_cigarette" title="Candy cigarette">Candy cigarette</a></li> <li><a href="/wiki/Herbal_cigarette" title="Herbal cigarette">Herbal cigarette</a></li> <li><a href="/wiki/Heated_tobacco_product" title="Heated tobacco product">Heated tobacco product</a> <ul><li><a href="/wiki/Composition_of_heated_tobacco_product_emissions" title="Composition of heated tobacco product emissions">Composition</a></li> <li><a href="/wiki/List_of_heated_tobacco_products" title="List of heated tobacco products">List</a></li></ul></li> <li><a href="/wiki/Snus" title="Snus">Snus</a></li> <li><a href="/wiki/Electronic_cigarette" title="Electronic cigarette">Electronic cigarette</a></li> <li><a href="/wiki/Nicotine_pouch" class="mw-redirect" title="Nicotine pouch">Nicotine pouch</a></li> <li><a href="/wiki/Nicotine_replacement_therapy" title="Nicotine replacement therapy">Nicotine replacement therapy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tobacco_industry" title="Tobacco industry">Tobacco industry</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/Cultivation_of_tobacco" title="Cultivation of tobacco">Cultivation of tobacco</a></li> <li><a href="/wiki/Nicotine_marketing" title="Nicotine marketing">Tobacco advertising</a></li> <li><a href="/wiki/Tobacco_industry_playbook" title="Tobacco industry playbook">Disinformation playbook</a></li> <li>"<a href="/wiki/Big_Tobacco" title="Big Tobacco">Big Tobacco</a>"</li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="By_country" scope="row" class="navbox-group" style="width:1%">By country</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/Tobacco_industry_in_Argentina" title="Tobacco industry in Argentina">Argentina</a></li> <li><a href="/wiki/Egyptian_cigarette_industry" title="Egyptian cigarette industry">Egypt</a></li> <li><a href="/wiki/Tobacco_industry_in_Malawi" title="Tobacco industry in Malawi">Malawi</a></li> <li><a href="/wiki/Tobacco_industry_in_Pakistan" title="Tobacco industry in Pakistan">Pakistan</a></li> <li><a href="/wiki/Tobacco_production_in_the_Philippines" title="Tobacco production in the Philippines">Philippines</a></li> <li><a href="/wiki/History_of_commercial_tobacco_in_the_United_States" title="History of commercial tobacco in the United States">United States</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Government<br />and the law</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/Illicit_cigarette_trade" title="Illicit cigarette trade">Cigarette smuggling</a></li> <li><a href="/wiki/Plain_tobacco_packaging" title="Plain tobacco packaging">Plain cigarette packaging</a></li> <li><a href="/wiki/Legal_smoking_age" title="Legal smoking age">Legal smoking age</a></li> <li><a href="/wiki/Smoking_bans_in_private_vehicles" title="Smoking bans in private vehicles">Smoking bans in private vehicles</a></li> <li><a href="/wiki/Tobacco_control" title="Tobacco control">Tobacco control movement</a></li> <li><a href="/wiki/Tobacco_Master_Settlement_Agreement" title="Tobacco Master Settlement Agreement">Tobacco Master Settlement Agreement</a></li> <li><a href="/wiki/Tobacco_packaging_warning_messages" title="Tobacco packaging warning messages">Tobacco packaging warning messages</a></li> <li><a href="/wiki/Tobacco_politics" title="Tobacco politics">Tobacco politics</a></li> <li><a href="/wiki/WHO_Framework_Convention_on_Tobacco_Control" title="WHO Framework Convention on Tobacco Control">WHO Framework Convention on Tobacco Control</a> <ul><li><a href="/wiki/MPOWER_tobacco_control" title="MPOWER tobacco control">MPOWER</a></li> <li><a href="/wiki/Protocol_to_Eliminate_Illicit_Trade_in_Tobacco_Products" title="Protocol to Eliminate Illicit Trade in Tobacco Products">Protocol to Eliminate Illicit Trade in Tobacco Products</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Lists</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/List_of_cigarette_brands" title="List of cigarette brands">Cigarette brands</a></li> <li><a href="/wiki/List_of_cigarette_smoke_carcinogens" title="List of cigarette smoke carcinogens">Cigarette smoke carcinogens</a></li> <li><a href="/wiki/Prevalence_of_tobacco_use" title="Prevalence of tobacco use">Countries by tobacco consumption</a></li> <li><a href="/wiki/List_of_rolling_papers" title="List of rolling papers">Rolling papers</a></li> <li><a href="/wiki/List_of_smoking_bans" title="List of smoking bans">Smoking bans</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Cigarettes" title="Category:Cigarettes">Category</a></li> <li><span class="noviewer" typeof="mw:File"><span title="Commons page"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span> <a href="https://commons.wikimedia.org/wiki/Category:Cigarettes" class="extiw" title="c:Category:Cigarettes">Commons</a></li> <li><a href="/wiki/Template:Smoking_nav" title="Template:Smoking nav">Smoking</a></li> <li><a href="/wiki/Template:Electronic_cigarettes" title="Template:Electronic cigarettes">Electronic cigarettes</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Drugs_which_induce_euphoria" 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_euphoria" 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 href="/wiki/Morphine" title="Morphine">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 class="mw-selflink selflink">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:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Pharmacodynamics" 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" style="background:#e8e8ff;background:#ccccff"><div id="Pharmacodynamics" style="font-size:114%;margin:0 4em"><a href="/wiki/Pharmacodynamics" title="Pharmacodynamics">Pharmacodynamics</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;font-size:114%"><div style="padding:0px"> <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="Nicotinic_acetylcholine_receptor_modulators" 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:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nicotinic_acetylcholine_receptor_modulators" title="Template talk:Nicotinic acetylcholine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nicotinic_acetylcholine_receptor_modulators" title="Special:EditPage/Template:Nicotinic acetylcholine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nicotinic_acetylcholine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">Nicotinic acetylcholine 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/Nicotinic_acetylcholine_receptors" class="mw-redirect" title="Nicotinic acetylcholine receptors"><abbr title="Nicotinic acetylcholine receptors">nAChRs</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 Nicotinic acetylcholine receptors</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_agonist" class="mw-redirect" title="Receptor agonist">Agonists</a><br />(and <a href="/wiki/Positive_allosteric_modulators" class="mw-redirect" title="Positive allosteric modulators"><abbr title="positive allosteric modulators">PAMs</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 positive allosteric modulators</span>)</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/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li> <li><a href="/wiki/6-Chloronicotine" title="6-Chloronicotine">6-Chloronicotine</a></li> <li><a href="/wiki/A-84,543" title="A-84,543">A-84,543</a></li> <li><a href="/wiki/A-366,833" title="A-366,833">A-366,833</a></li> <li><a href="/w/index.php?title=A-582,941&action=edit&redlink=1" class="new" title="A-582,941 (page does not exist)">A-582,941</a></li> <li><a href="/w/index.php?title=A-867,744&action=edit&redlink=1" class="new" title="A-867,744 (page does not exist)">A-867,744</a></li> <li><a href="/wiki/ABT-202" title="ABT-202">ABT-202</a></li> <li><a href="/wiki/ABT-418" title="ABT-418">ABT-418</a></li> <li><a href="/w/index.php?title=ABT-560&action=edit&redlink=1" class="new" title="ABT-560 (page does not exist)">ABT-560</a></li> <li><a href="/w/index.php?title=ABT-894&action=edit&redlink=1" class="new" title="ABT-894 (page does not exist)">ABT-894</a></li> <li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li> <li><a href="/wiki/Altinicline" title="Altinicline">Altinicline</a></li> <li><a href="/wiki/Anabasine" title="Anabasine">Anabasine</a></li> <li><a href="/wiki/Anatabine" title="Anatabine">Anatabine</a></li> <li><a href="/wiki/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/AR-R17779" title="AR-R17779">AR-R17779</a></li> <li><a href="/wiki/Bephenium_hydroxynaphthoate" title="Bephenium hydroxynaphthoate">Bephenium hydroxynaphthoate</a></li> <li><a href="/wiki/Butinoline" title="Butinoline">Butinoline</a></li> <li><a href="/wiki/Butyrylcholine" title="Butyrylcholine">Butyrylcholine</a></li> <li><a href="/wiki/Carbachol" title="Carbachol">Carbachol</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Cotinine" title="Cotinine">Cotinine</a></li> <li><a href="/wiki/Cytisine" title="Cytisine">Cytisine</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Dianicline" title="Dianicline">Dianicline</a></li> <li><a href="/wiki/Dimethylphenylpiperazinium" title="Dimethylphenylpiperazinium">Dimethylphenylpiperazinium</a></li> <li><a href="/wiki/Epibatidine" title="Epibatidine">Epibatidine</a></li> <li><a href="/wiki/Epiboxidine" title="Epiboxidine">Epiboxidine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Ethoxysebacylcholine&action=edit&redlink=1" class="new" title="Ethoxysebacylcholine (page does not exist)">Ethoxysebacylcholine</a></li> <li><a href="/w/index.php?title=EVP-4473&action=edit&redlink=1" class="new" title="EVP-4473 (page does not exist)">EVP-4473</a></li> <li><a href="/wiki/EVP-6124" class="mw-redirect" title="EVP-6124">EVP-6124</a></li> <li><a href="/wiki/Galantamine" title="Galantamine">Galantamine</a></li> <li><a href="/wiki/GTS-21" title="GTS-21">GTS-21</a></li> <li><a href="/wiki/Ispronicline" title="Ispronicline">Ispronicline</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/JNJ-39393406" title="JNJ-39393406">JNJ-39393406</a></li> <li><a href="/wiki/Levamisole" title="Levamisole">Levamisole</a></li> <li><a href="/wiki/Lobeline" title="Lobeline">Lobeline</a></li> <li><a href="/w/index.php?title=MEM-63,908&action=edit&redlink=1" class="new" title="MEM-63,908 (page does not exist)">MEM-63,908 (RG-3487)</a></li> <li><a href="/wiki/Morantel" title="Morantel">Morantel</a></li> <li><a class="mw-selflink selflink">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/w/index.php?title=NS-1738&action=edit&redlink=1" class="new" title="NS-1738 (page does not exist)">NS-1738</a></li> <li><a href="/wiki/PHA-543,613" title="PHA-543,613">PHA-543,613</a></li> <li><a href="/w/index.php?title=PHA-709,829&action=edit&redlink=1" class="new" title="PHA-709,829 (page does not exist)">PHA-709,829</a></li> <li><a href="/wiki/PNU-120,596" title="PNU-120,596">PNU-120,596</a></li> <li><a href="/wiki/PNU-282,987" title="PNU-282,987">PNU-282,987</a></li> <li><a href="/wiki/Pozanicline" title="Pozanicline">Pozanicline</a></li> <li><a href="/wiki/Pyrantel" title="Pyrantel">Pyrantel</a></li> <li><a href="/wiki/Rivanicline" title="Rivanicline">Rivanicline</a></li> <li><a href="/wiki/RJR-2429" title="RJR-2429">RJR-2429</a></li> <li><a href="/wiki/Sazetidine_A" title="Sazetidine A">Sazetidine A</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/w/index.php?title=Sebacylcholine&action=edit&redlink=1" class="new" title="Sebacylcholine (page does not exist)">Sebacylcholine</a></li> <li><a href="/wiki/SIB-1508Y" class="mw-redirect" title="SIB-1508Y">SIB-1508Y</a></li> <li><a href="/wiki/SIB-1553A" title="SIB-1553A">SIB-1553A</a></li> <li><a href="/wiki/SSR-180,711" title="SSR-180,711">SSR-180,711</a></li> <li><a href="/w/index.php?title=Suberyldicholine&action=edit&redlink=1" class="new" title="Suberyldicholine (page does not exist)">Suberyldicholine</a></li> <li><a href="/wiki/Suxamethonium" class="mw-redirect" title="Suxamethonium">Suxamethonium (succinylcholine)</a></li> <li><a href="/wiki/Suxethonium_chloride" title="Suxethonium chloride">Suxethonium (succinyldicholine)</a></li> <li><a href="/wiki/TC-1698" title="TC-1698">TC-1698</a></li> <li><a href="/w/index.php?title=TC-1734&action=edit&redlink=1" class="new" title="TC-1734 (page does not exist)">TC-1734</a></li> <li><a href="/wiki/TC-1827" title="TC-1827">TC-1827</a></li> <li><a href="/wiki/TC-2216" title="TC-2216">TC-2216</a></li> <li><a href="/wiki/TC-5214" class="mw-redirect" title="TC-5214">TC-5214</a></li> <li><a href="/wiki/TC-5619" class="mw-redirect" title="TC-5619">TC-5619</a></li> <li><a href="/w/index.php?title=TC-6683&action=edit&redlink=1" class="new" title="TC-6683 (page does not exist)">TC-6683</a></li> <li><a href="/wiki/Tebanicline" title="Tebanicline">Tebanicline</a></li> <li><a href="/wiki/Tribendimidine" title="Tribendimidine">Tribendimidine</a></li> <li><a href="/wiki/Tropisetron" title="Tropisetron">Tropisetron</a></li> <li><a href="/wiki/UB-165" title="UB-165">UB-165</a></li> <li><a href="/wiki/Varenicline" title="Varenicline">Varenicline</a></li> <li><a href="/wiki/WAY-317,538" class="mw-redirect" title="WAY-317,538">WAY-317,538</a></li> <li><a href="/w/index.php?title=XY-4083&action=edit&redlink=1" class="new" title="XY-4083 (page does not exist)">XY-4083</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Antagonists</a><br />(and <a href="/wiki/Negative_allosteric_modulators" class="mw-redirect" title="Negative allosteric modulators"><abbr title="negative allosteric modulators">NAMs</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 negative allosteric modulators</span>)</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/18-Methylaminocoronaridine" title="18-Methylaminocoronaridine">18-MAC</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/%CE%91-Neurotoxin" title="Α-Neurotoxin">α-Neurotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%91-cobratoxin" class="mw-redirect" title="Α-cobratoxin">α-cobratoxin</a>, <a href="/wiki/%CE%91-conotoxin" class="mw-redirect" title="Α-conotoxin">α-conotoxin</a>, many others)</li> <li><a href="/w/index.php?title=ABT-126&action=edit&redlink=1" class="new" title="ABT-126 (page does not exist)">ABT-126</a></li> <li><a href="/wiki/Alcuronium" class="mw-redirect" title="Alcuronium">Alcuronium</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/w/index.php?title=Anatruxonium&action=edit&redlink=1" class="new" title="Anatruxonium (page does not exist)">Anatruxonium</a></li> <li><a href="/w/index.php?title=AQW051&action=edit&redlink=1" class="new" title="AQW051 (page does not exist)">AQW051</a></li> <li><a href="/wiki/Atracurium" class="mw-redirect" title="Atracurium">Atracurium</a></li> <li><a href="/wiki/Barbiturates" class="mw-redirect" title="Barbiturates">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/BNC-210" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%9A-bungarotoxin" class="mw-redirect" title="Κ-bungarotoxin">κ-bungarotoxin</a>)</li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/BW284C51" title="BW284C51">BW284C51</a></li> <li><a href="/wiki/BW-A444" title="BW-A444">BW-A444</a></li> <li><a href="/wiki/Candocuronium_iodide" title="Candocuronium iodide">Candocuronium iodide (chandonium iodide)</a></li> <li><a href="/wiki/Chlorisondamine" title="Chlorisondamine">Chlorisondamine</a></li> <li><a href="/wiki/Cisatracurium" class="mw-redirect" title="Cisatracurium">Cisatracurium</a></li> <li><a href="/wiki/Coclaurine" title="Coclaurine">Coclaurine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Curare" title="Curare">Curare</a></li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Dacuronium_bromide" title="Dacuronium bromide">Dacuronium bromide</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Dehydronorketamine" title="Dehydronorketamine">Dehydronorketamine</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/w/index.php?title=Diadonium&action=edit&redlink=1" class="new" title="Diadonium (page does not exist)">Diadonium</a></li> <li><a href="/w/index.php?title=Dihydro-beta-erythroidine&action=edit&redlink=1" class="new" title="Dihydro-beta-erythroidine (page does not exist)">DHβE</a></li> <li><a href="/wiki/Dihydrochandonium" title="Dihydrochandonium">Dihydrochandonium</a></li> <li><a href="/wiki/Dimethyltubocurarine" class="mw-redirect" title="Dimethyltubocurarine">Dimethyltubocurarine (metocurine)</a></li> <li><a href="/wiki/Dioscorine" title="Dioscorine">Dioscorine</a></li> <li><a href="/wiki/Dipyrandium" title="Dipyrandium">Dipyrandium</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine (MK-801)</a></li> <li><a href="/wiki/Doxacurium" class="mw-redirect" title="Doxacurium">Doxacurium</a></li> <li><a href="/wiki/Encenicline" title="Encenicline">Encenicline</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Erythravine" title="Erythravine">Erythravine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Fazadinium" class="mw-redirect" title="Fazadinium">Fazadinium</a></li> <li><a href="/wiki/Gallamine" class="mw-redirect" title="Gallamine">Gallamine</a></li> <li><a href="/wiki/Gantacurium_chloride" title="Gantacurium chloride">Gantacurium chloride</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Hexafluronium" class="mw-redirect" title="Hexafluronium">Hexafluronium</a></li> <li><a href="/wiki/Hexamethonium" title="Hexamethonium">Hexamethonium (benzohexonium)</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Hydroxynorketamine" title="Hydroxynorketamine">Hydroxynorketamine</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/wiki/Laudexium" class="mw-redirect" title="Laudexium">Laudexium (laudolissin)</a></li> <li><a href="/wiki/Levacetylmethadol" title="Levacetylmethadol">Levacetylmethadol</a></li> <li><a href="/wiki/Levomethadone" title="Levomethadone">Levomethadone</a></li> <li><a href="/wiki/Malouetine" title="Malouetine">Malouetine</a></li> <li><a href="/wiki/2-Methoxyethyl-18-methoxycoronaridinate" title="2-Methoxyethyl-18-methoxycoronaridinate">ME-18-MC</a></li> <li><a href="/wiki/Mecamylamine" title="Mecamylamine">Mecamylamine</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Methorphan" title="Methorphan">Methorphan (racemethorphan)</a></li> <li><a href="/wiki/Methyllycaconitine" title="Methyllycaconitine">Methyllycaconitine</a></li> <li><a href="/wiki/Metocurine" title="Metocurine">Metocurine</a></li> <li><a href="/wiki/Mivacurium" class="mw-redirect" title="Mivacurium">Mivacurium</a></li> <li><a href="/wiki/Morphanol" class="mw-redirect" title="Morphanol">Morphanol (racemorphan)</a></li> <li><a href="/wiki/Neramexane" title="Neramexane">Neramexane</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Pancuronium_bromide" title="Pancuronium bromide">Pancuronium bromide</a></li> <li><a href="/wiki/Pempidine" title="Pempidine">Pempidine</a></li> <li><a href="/wiki/Pentamine" title="Pentamine">Pentamine</a></li> <li><a href="/wiki/Pentolinium" title="Pentolinium">Pentolinium</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Pipecuronium_bromide" title="Pipecuronium bromide">Pipecuronium bromide</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li> <li><a href="/wiki/Rapacuronium_bromide" title="Rapacuronium bromide">Rapacuronium bromide</a></li> <li><a href="/wiki/Reboxetine" title="Reboxetine">Reboxetine</a></li> <li><a href="/wiki/Rocuronium_bromide" title="Rocuronium bromide">Rocuronium bromide</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Stercuronium_iodide" title="Stercuronium iodide">Stercuronium iodide</a></li> <li><a href="/wiki/Surugatoxin" title="Surugatoxin">Surugatoxin</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Threohydrobupropion" title="Threohydrobupropion">Threohydrobupropion</a></li> <li><a href="/wiki/Toxiferine" title="Toxiferine">Toxiferine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Trimetaphan_camsilate" title="Trimetaphan camsilate">Trimetaphan camsilate (trimethaphan camsylate)</a></li> <li><a href="/w/index.php?title=Tropeinium&action=edit&redlink=1" class="new" title="Tropeinium (page does not exist)">Tropeinium</a></li> <li><a href="/wiki/Tubocurarine" class="mw-redirect" title="Tubocurarine">Tubocurarine</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li> <li><a href="/wiki/Vecuronium_bromide" title="Vecuronium bromide">Vecuronium bromide</a></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</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/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a><br /><small>(and <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>)</small></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/Acetyl-coA" class="mw-redirect" title="Acetyl-coA">Acetyl-coA</a></li> <li><a href="/wiki/Adafenoxate" title="Adafenoxate">Adafenoxate</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a> (<a href="/wiki/Lecithin" title="Lecithin">lecithin</a>)</li> <li><a href="/wiki/Citicoline" title="Citicoline">Citicoline</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a href="/wiki/Glycerophosphocholine" class="mw-redirect" title="Glycerophosphocholine">Glycerophosphocholine</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate (centrophenoxine)</a></li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a></li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a></li> <li><a href="/wiki/Phosphorylcholine" title="Phosphorylcholine">Phosphorylcholine</a></li> <li><a href="/wiki/Pirisudanol" title="Pirisudanol">Pirisudanol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Muscarinic_acetylcholine_receptor_modulators" title="Template:Muscarinic acetylcholine receptor modulators">Muscarinic acetylcholine receptor modulators</a></dd> <dd><a href="/wiki/Template:Acetylcholine_metabolism_and_transport_modulators" title="Template:Acetylcholine metabolism and transport modulators">Acetylcholine metabolism/transport modulators</a></dd></dl> </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="TRP_channel_modulators" 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:Transient_receptor_potential_channel_modulators" title="Template:Transient receptor potential channel modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Transient_receptor_potential_channel_modulators" title="Template talk:Transient receptor potential channel modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Transient_receptor_potential_channel_modulators" title="Special:EditPage/Template:Transient receptor potential channel modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="TRP_channel_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Transient_receptor_potential_channel" title="Transient receptor potential channel"><abbr title="Transient receptor potential">TRP</abbr> channel</a> <a href="/wiki/Channel_modulator" title="Channel modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><abbr title="Transient receptor potential ankyrin channel"><a href="/wiki/TRPA_(ion_channel)" title="TRPA (ion channel)">TRPA</a></abbr></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%;text-align:center;">Activators</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/4-Hydroxynonenal" title="4-Hydroxynonenal">4-Hydroxynonenal</a></li> <li><a href="/wiki/4-Oxo-2-nonenal" title="4-Oxo-2-nonenal">4-Oxo-2-nonenal</a></li> <li><a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">4,5-EET</a></li> <li><a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">12S-HpETE</a></li> <li><a href="/wiki/Cyclopentenone_prostaglandins" title="Cyclopentenone prostaglandins">15-Deoxy-Δ<sup>12,14</sup>-prostaglandin J2</a></li> <li><a href="/wiki/Hydroxy_alpha_sanshool" class="mw-redirect" title="Hydroxy alpha sanshool">α-Sanshool</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>, <a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan</a> and <a href="/wiki/Grains_of_paradise" title="Grains of paradise">melegueta peppers</a>)</li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li> <li><a href="/wiki/Allicin" title="Allicin">Allicin</a> (<a href="/wiki/Garlic" title="Garlic">garlic</a>)</li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">Allyl isothiocyanate</a> (<a href="/wiki/Mustard_plant" title="Mustard plant">mustard</a>, <a href="/wiki/Radish" title="Radish">radish</a>, <a href="/wiki/Horseradish" title="Horseradish">horseradish</a>, <a href="/wiki/Wasabi" title="Wasabi">wasabi</a>)</li> <li><a href="/wiki/AM404" title="AM404">AM404</a></li> <li><a href="/wiki/ASP-7663" title="ASP-7663">ASP-7663</a></li> <li><a href="/wiki/Bradykinin" title="Bradykinin">Bradykinin</a></li> <li><a href="/wiki/Cannabichromene" title="Cannabichromene">Cannabichromene</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabigerol" title="Cannabigerol">Cannabigerol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">Cinnamaldehyde</a> (<a href="/wiki/Cinnamon" title="Cinnamon">cinnamon</a>)</li> <li><a href="/wiki/CR_gas" title="CR gas">CR gas (dibenzoxazepine; DBO)</a></li> <li><a href="/wiki/CS_gas" title="CS gas">CS gas (2-chlorobenzal malononitrile)</a></li> <li><a href="/wiki/Cuminaldehyde" title="Cuminaldehyde">Cuminaldehyde</a> (<a href="/wiki/Cumin" title="Cumin">cumin</a>)</li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a> (<a href="/wiki/Turmeric" title="Turmeric">turmeric</a>)</li> <li><a href="/w/index.php?title=Dehydroligustilide&action=edit&redlink=1" class="new" title="Dehydroligustilide (page does not exist)">Dehydroligustilide</a> (<a href="/wiki/Celery" title="Celery">celery</a>)</li> <li><a href="/wiki/Diallyl_disulfide" title="Diallyl disulfide">Diallyl disulfide</a></li> <li><a href="/wiki/Dicentrine" title="Dicentrine">Dicentrine</a> (<i><a href="/wiki/Lindera" title="Lindera">Lindera</a></i> spp.)</li> <li><a href="/w/index.php?title=Farnesyl_thiosalicylic_acid&action=edit&redlink=1" class="new" title="Farnesyl thiosalicylic acid (page does not exist)">Farnesyl thiosalicylic acid</a></li> <li><a href="/wiki/Formalin" class="mw-redirect" title="Formalin">Formalin</a></li> <li><a href="/wiki/Gingerol" title="Gingerol">Gingerols</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>)</li> <li><a href="/wiki/Hepoxilin_A3" class="mw-redirect" title="Hepoxilin A3">Hepoxilin A3</a></li> <li><a href="/wiki/Hepoxilin_B3" class="mw-redirect" title="Hepoxilin B3">Hepoxilin B3</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/wiki/Icilin" title="Icilin">Icilin</a></li> <li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/JT-010" title="JT-010">JT-010</a></li> <li><a href="/wiki/Ligustilide" title="Ligustilide">Ligustilide</a> (<a href="/wiki/Celery" title="Celery">celery</a>, <i><a href="/wiki/Angelica_acutiloba" title="Angelica acutiloba">Angelica acutiloba</a></i>)</li> <li><a href="/wiki/Linalool" title="Linalool">Linalool</a> (<a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan pepper</a>, <a href="/wiki/Thyme" title="Thyme">thyme</a>)</li> <li><a href="/wiki/Methylglyoxal" title="Methylglyoxal">Methylglyoxal</a></li> <li><a href="/wiki/Methyl_salicylate" title="Methyl salicylate">Methyl salicylate</a> (<a href="/wiki/Wintergreen" title="Wintergreen">wintergreen</a>)</li> <li><a href="/wiki/N-Methylmaleimide" title="N-Methylmaleimide">N-Methylmaleimide</a></li> <li><a class="mw-selflink selflink">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/wiki/Oleocanthal" title="Oleocanthal">Oleocanthal</a> (<a href="/wiki/Olive_oil" title="Olive oil">olive oil</a>)</li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a> (<a href="/wiki/Taxus_brevifolia" title="Taxus brevifolia">Pacific yew</a>)</li> <li><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol (acetaminophen)</a></li> <li><a href="/wiki/PF-4840154" title="PF-4840154">PF-4840154</a></li> <li><a href="/wiki/Phenacyl_chloride" title="Phenacyl chloride">Phenacyl chloride</a></li> <li><a href="/wiki/Polygodial" title="Polygodial">Polygodial</a> (<a href="/wiki/Tasmannia_stipitata" title="Tasmannia stipitata">Dorrigo pepper</a>)</li> <li><a href="/wiki/Shogaol" title="Shogaol">Shogaols</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>, <a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan</a> and <a href="/wiki/Grains_of_paradise" title="Grains of paradise">melegueta peppers</a>)</li> <li><a href="/wiki/Tear_gas" title="Tear gas">Tear gases</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Tetrahydrocannabiorcol" title="Tetrahydrocannabiorcol">Tetrahydrocannabiorcol</a></li> <li><a href="/wiki/Syn-Propanethial-S-oxide" title="Syn-Propanethial-S-oxide">Thiopropanal S-oxide</a> (<a href="/wiki/Onion" title="Onion">onion</a>)</li> <li><a href="/wiki/Umbellulone" title="Umbellulone">Umbellulone</a> (<i>Umbellularia californica</i>)</li> <li><a href="/wiki/WIN_55,212-2" title="WIN 55,212-2">WIN 55,212-2</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/A-967079" title="A-967079">A-967079</a></li> <li><a href="/wiki/AM-0902" title="AM-0902">AM-0902</a></li> <li><a href="/w/index.php?title=Dehydroligustilide&action=edit&redlink=1" class="new" title="Dehydroligustilide (page does not exist)">Dehydroligustilide</a> (<a href="/wiki/Celery" title="Celery">celery</a>)</li> <li><a href="/wiki/HC-030031" title="HC-030031">HC-030031</a></li> <li><a class="mw-selflink selflink">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/wiki/PF-04745637" title="PF-04745637">PF-04745637</a></li> <li><a href="/wiki/Ruthenium_red" title="Ruthenium red">Ruthenium red</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;"><abbr title="Transient receptor potential canonical channel"><a href="/wiki/TRPC" title="TRPC">TRPC</a></abbr></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%;text-align:center;">Activators</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/Adhyperforin" title="Adhyperforin">Adhyperforin</a> (<a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum">St John's wort</a>)</li> <li><a href="/wiki/Diglyceride" title="Diglyceride">Diacyl glycerol</a></li> <li><a href="/wiki/GSK1702934A" title="GSK1702934A">GSK1702934A</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a> (<a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum">St John's wort</a>)</li> <li><a href="/wiki/Substance_P" title="Substance P">Substance P</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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=3%E2%80%B2-5-Dichlorodiphenylamine-2-carboxylic_acid&action=edit&redlink=1" class="new" title="3′-5-Dichlorodiphenylamine-2-carboxylic acid (page does not exist)">DCDPC</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/GSK417651A" title="GSK417651A">GSK417651A</a></li> <li><a href="/w/index.php?title=GSK2293017A&action=edit&redlink=1" class="new" title="GSK2293017A (page does not exist)">GSK2293017A</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><a href="/wiki/N-(p-Amylcinnamoyl)anthranilic_acid" title="N-(p-Amylcinnamoyl)anthranilic acid">N-(p-Amylcinnamoyl)anthranilic acid</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/w/index.php?title=Pyr3&action=edit&redlink=1" class="new" title="Pyr3 (page does not exist)">Pyr3</a></li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</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;"><abbr title="Transient receptor potential melastatin channel"><a href="/wiki/TRPM" title="TRPM">TRPM</a></abbr></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%;text-align:center;">Activators</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/Adenosine_diphosphate_ribose" title="Adenosine diphosphate ribose">ADP-ribose</a></li> <li><a href="/w/index.php?title=BCTC_(drug)&action=edit&redlink=1" class="new" title="BCTC (drug) (page does not exist)">BCTC</a></li> <li><a href="/wiki/Calcium" title="Calcium">Calcium</a> (intracellular)</li> <li><a href="/wiki/CIM-0216" title="CIM-0216">CIM-0216</a></li> <li><a href="/wiki/Cold" title="Cold">Cold</a></li> <li><a href="/w/index.php?title=Coolact_P&action=edit&redlink=1" class="new" title="Coolact P (page does not exist)">Coolact P</a></li> <li><a href="/wiki/Cooling_Agent_10" class="mw-redirect" title="Cooling Agent 10">Cooling Agent 10</a></li> <li><a href="/wiki/Eucalyptol" title="Eucalyptol">Eucalyptol</a> (<a href="/wiki/Eucalyptus" title="Eucalyptus">eucalyptus</a>)</li> <li><a href="/w/index.php?title=Frescolat_MGA&action=edit&redlink=1" class="new" title="Frescolat MGA (page does not exist)">Frescolat MGA</a></li> <li><a href="/w/index.php?title=Frescolat_ML&action=edit&redlink=1" class="new" title="Frescolat ML (page does not exist)">Frescolat ML</a></li> <li><a href="/wiki/Geraniol" title="Geraniol">Geraniol</a></li> <li><a href="/wiki/Hydroxycitronellal" title="Hydroxycitronellal">Hydroxycitronellal</a></li> <li><a href="/wiki/Icilin" title="Icilin">Icilin</a></li> <li><a href="/wiki/Linalool" title="Linalool">Linalool</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a> (<a href="/wiki/Mentha" title="Mentha">mint</a>)</li> <li><a href="/w/index.php?title=PMD_38&action=edit&redlink=1" class="new" title="PMD 38 (page does not exist)">PMD 38</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/w/index.php?title=Rutamarin&action=edit&redlink=1" class="new" title="Rutamarin (page does not exist)">Rutamarin</a> (<i><a href="/wiki/Ruta_graveolens" title="Ruta graveolens">Ruta graveolens</a></i>)</li> <li><a href="/wiki/Steviol_glycoside" title="Steviol glycoside">Steviol glycosides</a> (e.g., <a href="/wiki/Stevioside" title="Stevioside">stevioside</a>) (<i><a href="/wiki/Stevia_rebaudiana" title="Stevia rebaudiana">Stevia rebaudiana</a></i>)</li> <li>Sweet <a href="/wiki/Taste" title="Taste">tastants</a> (e.g., <a href="/wiki/Glucose" title="Glucose">glucose</a>, <a href="/wiki/Fructose" title="Fructose">fructose</a>, <a href="/wiki/Sucrose" title="Sucrose">sucrose</a>; indirectly)</li> <li><a href="/w/index.php?title=Thio-BCTC&action=edit&redlink=1" class="new" title="Thio-BCTC (page does not exist)">Thio-BCTC</a></li> <li><a href="/wiki/WS-12" class="mw-redirect" title="WS-12">WS-12</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/AMG-333" title="AMG-333">AMG-333</a></li> <li><a href="/wiki/Capsazepine" title="Capsazepine">Capsazepine</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/w/index.php?title=3%E2%80%B2-5-Dichlorodiphenylamine-2-carboxylic_acid&action=edit&redlink=1" class="new" title="3′-5-Dichlorodiphenylamine-2-carboxylic acid (page does not exist)">DCDPC</a></li> <li><a href="/w/index.php?title=Elismetrep&action=edit&redlink=1" class="new" title="Elismetrep (page does not exist)">Elismetrep</a></li> <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/N-(p-Amylcinnamoyl)anthranilic_acid" title="N-(p-Amylcinnamoyl)anthranilic acid">N-(p-Amylcinnamoyl)anthranilic acid</a></li> <li><a class="mw-selflink selflink">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/wiki/Ononetin" title="Ononetin">Ononetin</a></li> <li><a href="/wiki/PF-05105679" title="PF-05105679">PF-05105679</a></li> <li><a href="/wiki/RQ-00203078" title="RQ-00203078">RQ-00203078</a></li> <li><a href="/wiki/Ruthenium_red" title="Ruthenium red">Ruthenium red</a></li> <li><a href="/w/index.php?title=Rutamarin&action=edit&redlink=1" class="new" title="Rutamarin (page does not exist)">Rutamarin</a> (<i><a href="/wiki/Ruta_graveolens" title="Ruta graveolens">Ruta graveolens</a></i>)</li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</a></li> <li><a href="/wiki/Triphenylphosphine_oxide" title="Triphenylphosphine oxide">TPPO</a></li> <li><a href="/wiki/TRPM4-IN-5" title="TRPM4-IN-5">TRPM4-IN-5</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;"><abbr title="Transient receptor potential mucolipin channel"><a href="/wiki/TRPML" title="TRPML">TRPML</a></abbr></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%;text-align:center;">Activators</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=EVP21&action=edit&redlink=1" class="new" title="EVP21 (page does not exist)">EVP21</a></li> <li><a href="/wiki/MK6-83" title="MK6-83">MK6-83</a></li> <li><a href="/wiki/ML-SA1" title="ML-SA1">ML-SA1</a></li> <li><a href="/wiki/ML2-SA1" title="ML2-SA1">ML2-SA1</a></li> <li><a href="/wiki/Phosphatidylinositol_3,5-bisphosphate" title="Phosphatidylinositol 3,5-bisphosphate">PI(3,5)P<sub>2</sub></a></li> <li><a href="/w/index.php?title=SF-22&action=edit&redlink=1" class="new" title="SF-22 (page does not exist)">SF-22</a></li> <li><a href="/wiki/SN-2" title="SN-2">SN-2</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/ML-SI3" title="ML-SI3">ML-SI3</a></li> <li><a href="/wiki/Phosphatidylinositol_4,5-bisphosphate" title="Phosphatidylinositol 4,5-bisphosphate">PI(4,5)P<sub>2</sub></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;"><abbr title="Transient receptor potential polycystin channel"><a href="/wiki/TRPP" title="TRPP">TRPP</a></abbr></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%;text-align:center;">Activators</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/Triptolide" title="Triptolide">Triptolide</a> (<i><a href="/wiki/Tripterygium_wilfordii" title="Tripterygium wilfordii">Tripterygium wilfordii</a></i>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/Ruthenium_red" title="Ruthenium red">Ruthenium red</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;"><abbr title="Transient receptor potential vanilloid channel"><a href="/wiki/TRPV" title="TRPV">TRPV</a></abbr></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%;text-align:center;">Activators</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/2-Aminoethoxydiphenyl_borate" title="2-Aminoethoxydiphenyl borate">2-APB</a></li> <li><a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">5',6'-EET</a></li> <li><a href="/wiki/9-Hydroxyoctadecadienoic_acid" title="9-Hydroxyoctadecadienoic acid">9-HODE</a></li> <li><a href="/wiki/9-Hydroxyoctadecadienoic_acid" title="9-Hydroxyoctadecadienoic acid">9-oxoODE</a></li> <li><a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">12S-HETE</a></li> <li><a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">12S-HpETE</a></li> <li><a href="/wiki/13-Hydroxyoctadecadienoic_acid" title="13-Hydroxyoctadecadienoic acid">13-HODE</a></li> <li><a href="/wiki/13-Hydroxyoctadecadienoic_acid" title="13-Hydroxyoctadecadienoic acid">13-oxoODE</a></li> <li><a href="/wiki/20-Hydroxyeicosatetraenoic_acid" title="20-Hydroxyeicosatetraenoic acid">20-HETE</a></li> <li><a href="/wiki/Hydroxy_alpha_sanshool" class="mw-redirect" title="Hydroxy alpha sanshool">α-Sanshool</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>, <a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan</a> and <a href="/wiki/Grains_of_paradise" title="Grains of paradise">melegueta peppers</a>)</li> <li><a href="/wiki/Allicin" title="Allicin">Allicin</a> (<a href="/wiki/Garlic" title="Garlic">garlic</a>)</li> <li><a href="/wiki/AM404" title="AM404">AM404</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/w/index.php?title=Bisandrographolide&action=edit&redlink=1" class="new" title="Bisandrographolide (page does not exist)">Bisandrographolide</a> (<i><a href="/wiki/Andrographis_paniculata" title="Andrographis paniculata">Andrographis paniculata</a></i>)</li> <li><a href="/wiki/Camphor" title="Camphor">Camphor</a> (<a href="/wiki/Cinnamomum_camphora" class="mw-redirect" title="Cinnamomum camphora">camphor laurel</a>, <a href="/wiki/Rosemary" title="Rosemary">rosemary</a>, <a href="/wiki/Camphorweed" title="Camphorweed">camphorweed</a>, <a href="/wiki/African_blue_basil" title="African blue basil">African blue basil</a>, <a href="/wiki/Ocimum_kilimandscharicum" title="Ocimum kilimandscharicum">camphor basil</a>)</li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabidivarin" title="Cannabidivarin">Cannabidivarin</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Capsaicin" title="Capsaicin">Capsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Carvacrol" title="Carvacrol">Carvacrol</a> (<a href="/wiki/Oregano" title="Oregano">oregano</a>, <a href="/wiki/Thyme" title="Thyme">thyme</a>, <a href="/wiki/Lepidium" title="Lepidium">pepperwort</a>, <a href="/wiki/Monarda_fistulosa" title="Monarda fistulosa">wild bergamot</a>, others)</li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Diglyceride" title="Diglyceride">Diacyl glycerol</a></li> <li><a href="/wiki/Dihydrocapsaicin" title="Dihydrocapsaicin">Dihydrocapsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Eugenol" title="Eugenol">Eugenol</a> (<a href="/wiki/Basil" title="Basil">basil</a>, <a href="/wiki/Clove" title="Clove">clove</a>)</li> <li><a href="/wiki/Evodiamine" title="Evodiamine">Evodiamine</a> (<i><a href="/wiki/Tetradium_ruticarpum" title="Tetradium ruticarpum">Euodia ruticarpa</a></i>)</li> <li><a href="/wiki/Gingerol" title="Gingerol">Gingerols</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>)</li> <li><a href="/wiki/GSK1016790A" title="GSK1016790A">GSK1016790A</a></li> <li><a href="/wiki/Heat" title="Heat">Heat</a></li> <li><a href="/wiki/Hepoxilin_A3" class="mw-redirect" title="Hepoxilin A3">Hepoxilin A3</a></li> <li><a href="/wiki/Hepoxilin_B3" class="mw-redirect" title="Hepoxilin B3">Hepoxilin B3</a></li> <li><a href="/wiki/Homocapsaicin" title="Homocapsaicin">Homocapsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Homodihydrocapsaicin" title="Homodihydrocapsaicin">Homodihydrocapsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Incensole" title="Incensole">Incensole</a> (<a href="/wiki/Incense" title="Incense">incense</a>)</li> <li><a href="/wiki/Lysophosphatidic_acid" title="Lysophosphatidic acid">Lysophosphatidic acid</a></li> <li>Low <a href="/wiki/PH" title="PH">pH</a> (acidic conditions)</li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a> (<a href="/wiki/Mentha" title="Mentha">mint</a>)</li> <li><a href="/wiki/N-Arachidonoyl_dopamine" title="N-Arachidonoyl dopamine">N-Arachidonoyl dopamine</a></li> <li><a href="/w/index.php?title=N-Oleoyldopamine&action=edit&redlink=1" class="new" title="N-Oleoyldopamine (page does not exist)">N-Oleoyldopamine</a></li> <li><a href="/wiki/Oleoylethanolamide" title="Oleoylethanolamide">N-Oleoylethanolamide</a></li> <li><a href="/wiki/Nonivamide" title="Nonivamide">Nonivamide (PAVA)</a> (<a href="/wiki/PAVA_spray" title="PAVA spray">PAVA spray</a>)</li> <li><a href="/wiki/Nordihydrocapsaicin" title="Nordihydrocapsaicin">Nordihydrocapsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a> (<a href="/wiki/Taxus_brevifolia" title="Taxus brevifolia">Pacific yew</a>)</li> <li><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol (acetaminophen)</a></li> <li><a href="/wiki/Phenylacetylrinvanil" title="Phenylacetylrinvanil">Phenylacetylrinvanil</a></li> <li><a href="/wiki/Phorbol_esters" title="Phorbol esters">Phorbol esters</a> (e.g., <a href="/w/index.php?title=4%CE%B1-phorbol_12,13-didecanoate&action=edit&redlink=1" class="new" title="4α-phorbol 12,13-didecanoate (page does not exist)">4α-PDD</a>)</li> <li><a href="/wiki/Piperine" title="Piperine">Piperine</a> (<a href="/wiki/Black_pepper" title="Black pepper">black pepper</a>, <a href="/wiki/Long_pepper" title="Long pepper">long pepper</a>)</li> <li><a href="/wiki/Polygodial" title="Polygodial">Polygodial</a> (<a href="/wiki/Tasmannia_stipitata" title="Tasmannia stipitata">Dorrigo pepper</a>)</li> <li><a href="/wiki/Probenecid" title="Probenecid">Probenecid</a></li> <li><a href="/wiki/Proton" title="Proton">Protons</a></li> <li><a href="/wiki/RhTx" title="RhTx">RhTx</a></li> <li><a href="/w/index.php?title=Rutamarin&action=edit&redlink=1" class="new" title="Rutamarin (page does not exist)">Rutamarin</a> (<i><a href="/wiki/Ruta_graveolens" title="Ruta graveolens">Ruta graveolens</a></i>)</li> <li><a href="/wiki/Resiniferatoxin" title="Resiniferatoxin">Resiniferatoxin</a> (RTX) (<i><a href="/wiki/Euphorbia_resinifera" title="Euphorbia resinifera">Euphorbia resinifera</a>/<a href="/wiki/Euphorbia_poissonii" title="Euphorbia poissonii">pooissonii</a></i>)</li> <li><a href="/wiki/Shogaol" title="Shogaol">Shogaols</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>, <a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan</a> and <a href="/wiki/Grains_of_paradise" title="Grains of paradise">melegueta peppers</a>)</li> <li><a href="/wiki/Tetrahydrocannabivarin" title="Tetrahydrocannabivarin">Tetrahydrocannabivarin</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Thymol" title="Thymol">Thymol</a> (<a href="/wiki/Thyme" title="Thyme">thyme</a>, <a href="/wiki/Oregano" title="Oregano">oregano</a>)</li> <li><a href="/wiki/Tinyatoxin" title="Tinyatoxin">Tinyatoxin</a> (<i><a href="/wiki/Euphorbia_resinifera" title="Euphorbia resinifera">Euphorbia resinifera</a>/<a href="/wiki/Euphorbia_poissonii" title="Euphorbia poissonii">pooissonii</a></i>)</li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Vanillin" title="Vanillin">Vanillin</a> (<a href="/wiki/Vanilla" title="Vanilla">vanilla</a>)</li> <li><a href="/wiki/Zucapsaicin" title="Zucapsaicin">Zucapsaicin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/Spinasterol" title="Spinasterol">α-Spinasterol</a> (<i><a href="/wiki/Vernonia" title="Vernonia">Vernonia tweediana</a></i>)</li> <li><a href="/wiki/AMG-517" title="AMG-517">AMG-517</a></li> <li><a href="/wiki/AMG-9810" title="AMG-9810">AMG-9810</a></li> <li><a href="/w/index.php?title=Asivatrep&action=edit&redlink=1" class="new" title="Asivatrep (page does not exist)">Asivatrep</a></li> <li><a href="/w/index.php?title=BCTC_(drug)&action=edit&redlink=1" class="new" title="BCTC (drug) (page does not exist)">BCTC</a></li> <li><a href="/wiki/Cannabigerol" title="Cannabigerol">Cannabigerol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabigerolic_acid" title="Cannabigerolic acid">Cannabigerolic acid</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabigerovarin" title="Cannabigerovarin">Cannabigerovarin</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabinol" title="Cannabinol">Cannabinol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Capsazepine" title="Capsazepine">Capsazepine</a></li> <li><a href="/w/index.php?title=3%E2%80%B2-5-Dichlorodiphenylamine-2-carboxylic_acid&action=edit&redlink=1" class="new" title="3′-5-Dichlorodiphenylamine-2-carboxylic acid (page does not exist)">DCDPC</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/GRC-6211" title="GRC-6211">GRC-6211</a></li> <li><a href="/wiki/HC-067047" title="HC-067047">HC-067047</a></li> <li><a href="/wiki/Lanthanum" title="Lanthanum">Lanthanum</a></li> <li><a href="/wiki/Mavatrep" title="Mavatrep">Mavatrep</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><a href="/wiki/N-(p-Amylcinnamoyl)anthranilic_acid" title="N-(p-Amylcinnamoyl)anthranilic acid">N-(p-Amylcinnamoyl)anthranilic acid</a></li> <li><a href="/w/index.php?title=NGD-8243&action=edit&redlink=1" class="new" title="NGD-8243 (page does not exist)">NGD-8243</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/w/index.php?title=RN-1734&action=edit&redlink=1" class="new" title="RN-1734 (page does not exist)">RN-1734</a></li> <li><a href="/wiki/RN-9893" title="RN-9893">RN-9893</a></li> <li><a href="/wiki/Ruthenium_red" title="Ruthenium red">Ruthenium red</a></li> <li><a href="/wiki/SB-366791" title="SB-366791">SB-366791</a></li> <li><a href="/wiki/SB-705498" title="SB-705498">SB-705498</a></li> <li><a href="/w/index.php?title=Tivanisiran&action=edit&redlink=1" class="new" title="Tivanisiran (page does not exist)">Tivanisiran</a></li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</a></li> <li><a href="/wiki/TRPV3-74a" title="TRPV3-74a">TRPV3-74a</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Ion_channel_modulators" title="Template:Ion channel modulators">Ion channel modulators</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="Xenobiotic-sensing_receptor_modulators" 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:Xenobiotic-sensing_receptor_modulators" title="Template:Xenobiotic-sensing receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Xenobiotic-sensing_receptor_modulators" title="Template talk:Xenobiotic-sensing receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Xenobiotic-sensing_receptor_modulators" title="Special:EditPage/Template:Xenobiotic-sensing receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Xenobiotic-sensing_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Xenobiotic-sensing_receptor" title="Xenobiotic-sensing receptor">Xenobiotic-sensing 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/Constitutive_androstane_receptor" title="Constitutive androstane receptor"><abbr title="Constitutive androstane receptor">CAR</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 Constitutive androstane receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/w/index.php?title=6,7-Dimethylesculetin&action=edit&redlink=1" class="new" title="6,7-Dimethylesculetin (page does not exist)">6,7-Dimethylesculetin</a></li> <li><a href="/wiki/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/w/index.php?title=Benfuracarb&action=edit&redlink=1" class="new" title="Benfuracarb (page does not exist)">Benfuracarb</a></li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Chrysin" title="Chrysin">Chrysin</a></li> <li><a href="/w/index.php?title=CITCO_(drug)&action=edit&redlink=1" class="new" title="CITCO (drug) (page does not exist)">CITCO</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cypermethrin" title="Cypermethrin">Cypermethrin</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ellagic_acid" title="Ellagic acid">Ellagic acid</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Methoxychlor" title="Methoxychlor">Methoxychlor</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Nevirapine" title="Nevirapine">Nevirapine</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/w/index.php?title=Octicizer&action=edit&redlink=1" class="new" title="Octicizer (page does not exist)">Octicizer</a></li> <li><a href="/wiki/Permethrin" title="Permethrin">Permethrin</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/w/index.php?title=TCPOBOP&action=edit&redlink=1" class="new" title="TCPOBOP (page does not exist)">TCPOBOP</a></li> <li><a href="/wiki/Telmisartan" title="Telmisartan">Telmisartan</a></li> <li><a href="/wiki/Tolnaftate" title="Tolnaftate">Tolnaftate</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=3,17%CE%B2-Estradiol&action=edit&redlink=1" class="new" title="3,17β-Estradiol (page does not exist)">3,17β-Estradiol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B1-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3α-ol (page does not exist)">3α-Androstanol</a></li> <li><a href="/wiki/5%CE%B1-Androst-16-en-3%CE%B1-ol" class="mw-redirect" title="5α-Androst-16-en-3α-ol">3α-Androstenol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B2-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3β-ol (page does not exist)">3β-Androstanol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-17-ol&action=edit&redlink=1" class="new" title="5α-Androstan-17-ol (page does not exist)">17-Androstanol</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">AITC</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/w/index.php?title=Nigramide_J&action=edit&redlink=1" class="new" title="Nigramide J (page does not exist)">Nigramide J</a></li> <li><a href="/wiki/Okadaic_acid" title="Okadaic acid">Okadaic acid</a></li> <li><a href="/wiki/PK-11195" class="mw-redirect" title="PK-11195">PK-11195</a></li> <li><a href="/w/index.php?title=S-07662&action=edit&redlink=1" class="new" title="S-07662 (page does not exist)">S-07662</a></li> <li><a href="/w/index.php?title=T-0901317&action=edit&redlink=1" class="new" title="T-0901317 (page does not exist)">T-0901317</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Pregnane_X_receptor" title="Pregnane X receptor"><abbr title="Pregnane X receptor">PXR</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 Pregnane X receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/%CE%944-Androstenedione" class="mw-redirect" title="Δ4-Androstenedione">Δ<sup>4</sup>-Androstenedione</a></li> <li><a href="/wiki/%CE%945-Androstenediol" class="mw-redirect" title="Δ5-Androstenediol">Δ<sup>5</sup>-Androstenediol</a></li> <li><a href="/wiki/%CE%945-Androstenedione" class="mw-redirect" title="Δ5-Androstenedione">Δ<sup>5</sup>-Androstenedione</a></li> <li><a href="/w/index.php?title=AA-861&action=edit&redlink=1" class="new" title="AA-861 (page does not exist)">AA-861</a></li> <li><a href="/wiki/Allopregnanediol" title="Allopregnanediol">Allopregnanediol</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">Allopregnanedione (5α-dihydroprogesterone)</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone (brexanolone)</a></li> <li><a href="/wiki/Alpha-Lipoic_acid" class="mw-redirect" title="Alpha-Lipoic acid">Alpha-Lipoic acid</a></li> <li><a href="/wiki/Ambrisentan" title="Ambrisentan">Ambrisentan</a></li> <li><a href="/wiki/AMI-193" class="mw-redirect" title="AMI-193">AMI-193</a></li> <li><a href="/wiki/Amlodipine_besylate" class="mw-redirect" title="Amlodipine besylate">Amlodipine besylate</a></li> <li><a href="/wiki/Antimycotic" class="mw-redirect" title="Antimycotic">Antimycotics</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/wiki/Aurothioglucose" title="Aurothioglucose">Aurothioglucose</a></li> <li><a href="/wiki/Bile_acid" title="Bile acid">Bile acids</a></li> <li><a href="/wiki/Bithionol" title="Bithionol">Bithionol</a></li> <li><a href="/wiki/Bosentan" title="Bosentan">Bosentan</a></li> <li><a href="/w/index.php?title=Bumecaine&action=edit&redlink=1" class="new" title="Bumecaine (page does not exist)">Bumecaine</a></li> <li><a href="/wiki/Cafestol" title="Cafestol">Cafestol</a></li> <li><a href="/wiki/Cephaloridine" title="Cephaloridine">Cephaloridine</a></li> <li><a href="/wiki/Cephradine" class="mw-redirect" title="Cephradine">Cephradine</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Ciglitazone" title="Ciglitazone">Ciglitazone</a></li> <li><a href="/wiki/Clindamycin" title="Clindamycin">Clindamycin</a></li> <li><a href="/wiki/Clofenvinfos" class="mw-redirect" title="Clofenvinfos">Clofenvinfos</a></li> <li><a href="/wiki/Chloroxine" title="Chloroxine">Chloroxine</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Colforsin" class="mw-redirect" title="Colforsin">Colforsin</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Demecolcine" title="Demecolcine">Demecolcine</a></li> <li><a href="/wiki/Dexamethasone" title="Dexamethasone">Dexamethasone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a> (<a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">prasterone sulfate</a>)</li> <li><a href="/wiki/Dibunate_sodium" class="mw-redirect" title="Dibunate sodium">Dibunate sodium</a></li> <li><a href="/wiki/Diclazuril" title="Diclazuril">Diclazuril</a></li> <li><a href="/wiki/Dicloxacillin" title="Dicloxacillin">Dicloxacillin</a></li> <li><a href="/wiki/Dimercaprol" title="Dimercaprol">Dimercaprol</a></li> <li><a href="/w/index.php?title=Dinaline&action=edit&redlink=1" class="new" title="Dinaline (page does not exist)">Dinaline</a></li> <li><a href="/wiki/Docetaxel" title="Docetaxel">Docetaxel</a></li> <li><a href="/wiki/Docusate_calcium" class="mw-redirect" title="Docusate calcium">Docusate calcium</a></li> <li><a href="/wiki/Dodecylbenzenesulfonic_acid" class="mw-redirect" title="Dodecylbenzenesulfonic acid">Dodecylbenzenesulfonic acid</a></li> <li><a href="/wiki/Dronabinol" title="Dronabinol">Dronabinol</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa</a></li> <li><a href="/wiki/Eburnamonine" class="mw-redirect" title="Eburnamonine">Eburnamonine</a></li> <li><a href="/wiki/Ecopipam" title="Ecopipam">Ecopipam</a></li> <li><a href="/wiki/Enzacamene" title="Enzacamene">Enzacamene</a></li> <li><a href="/wiki/Epothilone_B" class="mw-redirect" title="Epothilone B">Epothilone B</a></li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/w/index.php?title=Febantel&action=edit&redlink=1" class="new" title="Febantel (page does not exist)">Febantel</a></li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/wiki/Fenbendazole" title="Fenbendazole">Fenbendazole</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a></li> <li><a href="/wiki/Flucloxacillin" title="Flucloxacillin">Flucloxacillin</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/wiki/Haloprogin" title="Haloprogin">Haloprogin</a></li> <li><a href="/wiki/Hetacillin_potassium" class="mw-redirect" title="Hetacillin potassium">Hetacillin potassium</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a></li> <li><a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum"><i>Hypericum perforatum</i> (St John's wort)</a></li> <li><a href="/wiki/Indinavir_sulfate" class="mw-redirect" title="Indinavir sulfate">Indinavir sulfate</a></li> <li><a href="/wiki/Lasalocid_sodium" class="mw-redirect" title="Lasalocid sodium">Lasalocid sodium</a></li> <li><a href="/wiki/Levothyroxine" title="Levothyroxine">Levothyroxine</a></li> <li>Linolenic acid: <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-Linolenic acid</a> and <a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-Linolenic acid">γ-linolenic acid</a></li> <li><a href="/w/index.php?title=LOE-908&action=edit&redlink=1" class="new" title="LOE-908 (page does not exist)">LOE-908</a></li> <li><a href="/wiki/Loratadine" title="Loratadine">Loratadine</a></li> <li><a href="/wiki/Lovastatin" title="Lovastatin">Lovastatin</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/wiki/Metacycline" title="Metacycline">Metacycline</a></li> <li><a href="/wiki/Methylprednisolone" title="Methylprednisolone">Methylprednisolone</a></li> <li><a href="/wiki/Metyrapone" title="Metyrapone">Metyrapone</a></li> <li><a href="/wiki/Mevastatin" title="Mevastatin">Mevastatin</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nafcillin" title="Nafcillin">Nafcillin</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a class="mw-selflink selflink">Nicotine</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Nilvadipine" title="Nilvadipine">Nilvadipine</a></li> <li><a href="/wiki/Nisoldipine" title="Nisoldipine">Nisoldipine</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Omeprazole" title="Omeprazole">Omeprazole</a></li> <li><a href="/wiki/Orlistat" title="Orlistat">Orlistat</a></li> <li><a href="/wiki/Oxatomide" title="Oxatomide">Oxatomide</a></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Piperine" title="Piperine">Piperine</a></li> <li><a href="/wiki/Plicamycin" title="Plicamycin">Plicamycin</a></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a></li> <li><a href="/wiki/Pregnanediol" title="Pregnanediol">Pregnanediol</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Pregnenolone_16%CE%B1-carbonitrile" title="Pregnenolone 16α-carbonitrile">Pregnenolone 16α-carbonitrile</a></li> <li><a href="/wiki/Proadifen" title="Proadifen">Proadifen</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/wiki/Reverse_triiodothyronine" title="Reverse triiodothyronine">Reverse triiodothyronine</a></li> <li><a href="/wiki/Rifampicin" title="Rifampicin">Rifampicin</a></li> <li><a href="/wiki/Rifaximin" title="Rifaximin">Rifaximin</a></li> <li><a href="/wiki/Rimexolone" title="Rimexolone">Rimexolone</a></li> <li><a href="/wiki/Riodipine" title="Riodipine">Riodipine</a></li> <li><a href="/wiki/Ritonavir" title="Ritonavir">Ritonavir</a></li> <li><a href="/wiki/Simvastatin" title="Simvastatin">Simvastatin</a></li> <li><a href="/wiki/Sirolimus" title="Sirolimus">Sirolimus</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/w/index.php?title=SR-12813&action=edit&redlink=1" class="new" title="SR-12813 (page does not exist)">SR-12813</a></li> <li><a href="/w/index.php?title=Suberoylanilide&action=edit&redlink=1" class="new" title="Suberoylanilide (page does not exist)">Suberoylanilide</a></li> <li><a href="/wiki/Sulfisoxazole" class="mw-redirect" title="Sulfisoxazole">Sulfisoxazole</a></li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/wiki/Tacrolimus" title="Tacrolimus">Tacrolimus</a></li> <li><a href="/w/index.php?title=Tenylidone&action=edit&redlink=1" class="new" title="Tenylidone (page does not exist)">Tenylidone</a></li> <li><a href="/wiki/Terconazole" title="Terconazole">Terconazole</a></li> <li><a href="/wiki/Testosterone_isocaproate" title="Testosterone isocaproate">Testosterone isocaproate</a></li> <li><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a></li> <li><a href="/wiki/Thiamylal_sodium" class="mw-redirect" title="Thiamylal sodium">Thiamylal sodium</a></li> <li><a href="/wiki/Thiothixene" class="mw-redirect" title="Thiothixene">Thiothixene</a></li> <li><a href="/wiki/Thonzonium_bromide" title="Thonzonium bromide">Thonzonium bromide</a></li> <li><a href="/wiki/Tianeptine" title="Tianeptine">Tianeptine</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Troleandomycin" title="Troleandomycin">Troleandomycin</a></li> <li><a href="/w/index.php?title=Tropanyl_3,5-dimethulbenzoate&action=edit&redlink=1" class="new" title="Tropanyl 3,5-dimethulbenzoate (page does not exist)">Tropanyl 3,5-dimethulbenzoate</a></li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">Zafirlukast</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Sesamin" title="Sesamin">Sesamin</a></li></ul> </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></dl> </div></td></tr></tbody></table></div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Recreational_drug_use" 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" style="text-align:center;"><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:Drug_use" title="Template:Drug use"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Drug_use" title="Template talk:Drug use"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Drug_use" title="Special:EditPage/Template:Drug use"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Recreational_drug_use" style="font-size:114%;margin:0 4em"><a href="/wiki/Recreational_drug_use" title="Recreational drug use">Recreational drug use</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible mw-collapsed navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="text-align:center;"><div id="Major_recreational_drugs" style="font-size:114%;margin:0 4em">Major recreational drugs</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Depressant" title="Depressant">Depressants</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/Barbiturate" title="Barbiturate">Barbiturates</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a> <ul><li><a href="/wiki/Alcoholic_beverage" title="Alcoholic beverage">Alcoholic beverage</a></li> <li><a href="/wiki/Beer" title="Beer">Beer</a></li> <li><a href="/wiki/Wine" title="Wine">Wine</a></li></ul></li> <li><a href="/wiki/Gabapentinoid" title="Gabapentinoid">Gabapentinoids</a></li> <li><a href="/wiki/Gamma-Hydroxybutyric_acid" class="mw-redirect" title="Gamma-Hydroxybutyric acid">GHB</a></li> <li><a href="/wiki/Inhalant" title="Inhalant">Inhalants</a> <ul><li>Medical <ul><li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a> (<a href="/wiki/Recreational_use_of_nitrous_oxide" title="Recreational use of nitrous oxide">recreational use</a>)</li></ul></li> <li>Hazardous <a href="/wiki/Solvent" title="Solvent">solvents</a> <ul><li><a href="/wiki/Adhesive#Contact" title="Adhesive">contact adhesives</a></li> <li><a href="/wiki/Gasoline" title="Gasoline">Gasoline</a></li> <li><a href="/wiki/Nail_polish#Nail_polish_remover" title="Nail polish">nail polish remover</a></li> <li><a href="/wiki/Paint_thinner" title="Paint thinner">Paint thinner</a></li></ul></li> <li>Other <ul><li><a href="/wiki/Freon" title="Freon">Freon</a></li></ul></li></ul></li> <li><a href="/wiki/Kava" title="Kava">Kava</a></li> <li><a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">Nonbenzodiazepines</a></li> <li><a href="/wiki/Quinazolinone" title="Quinazolinone">Quinazolinones</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-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Buprenorphine" title="Buprenorphine">Buprenorphine</a> <ul><li>Suboxone</li> <li>Subutex</li></ul></li> <li><a href="/wiki/Codeine" title="Codeine">Codeine</a> <ul><li><a href="/wiki/Lean_(drug)" title="Lean (drug)">Lean</a></li></ul></li> <li><a href="/wiki/Desomorphine" title="Desomorphine">Desomorphine</a> <ul><li>Krokodil</li></ul></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a> <ul><li>Darvocet</li> <li>Darvon</li></ul></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a></li> <li><a href="/wiki/Heroin" title="Heroin">Diamorphine</a> <ul><li>Heroin</li></ul></li> <li><a href="/wiki/Hydrocodone" title="Hydrocodone">Hydrocodone</a></li> <li><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone</a> <ul><li>Dilaudid</li></ul></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Mitragyna_speciosa" title="Mitragyna speciosa">Mitragyna speciosa</a> <ul><li><a href="/wiki/Kratom" class="mw-redirect" title="Kratom">Kratom</a></li></ul></li> <li><a href="/wiki/Morphine" title="Morphine">Morphine</a> <ul><li><a href="/wiki/Opium" title="Opium">Opium</a></li></ul></li> <li><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a> <ul><li><a href="/wiki/Oxycodone/paracetamol" title="Oxycodone/paracetamol">/paracetamol</a></li></ul></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Stimulant" title="Stimulant">Stimulants</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/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/Arecoline" title="Arecoline">Arecoline</a> <ul><li><a href="/wiki/Areca" title="Areca">Areca</a></li></ul></li> <li><a href="/wiki/Paan" class="mw-redirect" title="Paan">Betel</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a> <ul><li><a href="/wiki/Coffee" title="Coffee">Coffee</a></li> <li><a href="/wiki/Energy_drink" title="Energy drink">Energy drinks</a></li> <li><a href="/wiki/Tea" title="Tea">Tea</a></li></ul></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a> <ul><li><a href="/wiki/Khat" title="Khat">Khat</a></li></ul></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a> <ul><li><a href="/wiki/Coca" title="Coca">Coca</a></li> <li><a href="/wiki/Crack_cocaine" title="Crack cocaine">Crack</a></li></ul></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a> <ul><li><a href="/wiki/Ephedra_(medicine)" title="Ephedra (medicine)">Ephedra</a></li></ul></li> <li><a href="/wiki/Methylenedioxypyrovalerone" title="Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li> <li><a href="/wiki/Modafinil" title="Modafinil">Modafinil</a></li> <li><a class="mw-selflink selflink">Nicotine</a> <ul><li><a href="/wiki/Nicotine_polacrilex" title="Nicotine polacrilex">Polacrilex</a></li> <li><a href="/wiki/Nicotine_salt" title="Nicotine salt">Salt</a></li> <li><a href="/wiki/Tobacco" title="Tobacco">Tobacco</a></li></ul></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a> <ul><li><a href="/wiki/Cocoa_bean" title="Cocoa bean">Cocoa</a></li> <li><a href="/wiki/Chocolate" title="Chocolate">Chocolate</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Empathogen%E2%80%93entactogen" class="mw-redirect" title="Empathogen–entactogen">Entactogens</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/2C_(psychedelics)" title="2C (psychedelics)">2C series</a></li> <li><a href="/wiki/6-APB" title="6-APB">6-APB</a> <ul><li>Benzofury</li></ul></li> <li><a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">AMT</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA</a> <ul><li><a href="/wiki/MDMA#Forms" title="MDMA">Ecstasy</a></li> <li><a href="/wiki/MDMA#Forms" title="MDMA">Molly</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hallucinogen" title="Hallucinogen">Hallucinogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Psychedelic_drug" title="Psychedelic drug">Psychedelics</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/Bufotenin" title="Bufotenin">Bufotenin</a> <ul><li><a href="/wiki/Colorado_River_toad" title="Colorado River toad">Psychoactive toads</a></li> <li><a href="/wiki/Anadenanthera_colubrina" title="Anadenanthera colubrina">Vilca</a></li> <li><a href="/wiki/Anadenanthera_peregrina" title="Anadenanthera peregrina">Yopo</a></li></ul></li> <li><a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a> <ul><li><a href="/wiki/Ayahuasca" title="Ayahuasca">Ayahuasca</a></li></ul></li> <li><a href="/wiki/Ergine" title="Ergine">LSA</a></li> <li><a href="/wiki/LSD" title="LSD">LSD-25</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a> <ul><li><a href="/wiki/Echinopsis_peruviana" class="mw-redirect" title="Echinopsis peruviana">Peruvian torch</a></li> <li><a href="/wiki/Peyote" title="Peyote">Peyote</a></li> <li><a href="/wiki/Echinopsis_pachanoi" class="mw-redirect" title="Echinopsis pachanoi">San Pedro</a></li></ul></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">Psilocybin</a> / <a href="/wiki/Psilocin" title="Psilocin">Psilocin</a> <ul><li><a href="/wiki/Psilocybin_mushroom" title="Psilocybin mushroom">Psilocybin mushrooms</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Dissociative" title="Dissociative">Dissociatives</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/Dextromethorphan" title="Dextromethorphan">DXM</a> (<a href="/wiki/Recreational_use_of_dextromethorphan" title="Recreational use of dextromethorphan">recreational use</a>)</li> <li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/wiki/Inhalant" title="Inhalant">Inhalants</a> <ul><li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a> (<a href="/wiki/Recreational_use_of_nitrous_oxide" title="Recreational use of nitrous oxide">recreational use</a>)</li> <li><a href="/wiki/Alkyl_nitrites" class="mw-redirect" title="Alkyl nitrites">alkyl nitrites</a></li> <li><a href="/wiki/Poppers" title="Poppers">poppers</a></li> <li><a href="/wiki/Amyl_nitrite" title="Amyl nitrite">amyl nitrite</a></li></ul></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Methoxetamine" title="Methoxetamine">MXE</a></li> <li><a href="/wiki/Muscimol" title="Muscimol">Muscimol</a> <ul><li><a href="/wiki/Amanita_muscaria" title="Amanita muscaria">Amanita muscaria</a></li></ul></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">PCP</a></li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a> <ul><li><a href="/wiki/Salvia_divinorum" title="Salvia divinorum">Salvia divinorum</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Deliriant" title="Deliriant">Deliriants</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/Atropine" title="Atropine">Atropine</a> and <a href="/wiki/Scopolamine" title="Scopolamine">Scopolamine</a> <ul><li><a href="/wiki/Atropa_belladonna" title="Atropa belladonna">Atropa belladonna</a></li> <li><a href="/wiki/Datura" title="Datura">Datura</a></li> <li><a href="/wiki/Hyoscyamus_niger" title="Hyoscyamus niger">Hyoscyamus niger</a></li> <li><a href="/wiki/Mandragora_officinarum" title="Mandragora officinarum">Mandragora officinarum</a></li></ul></li> <li><a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">Dimenhydrinate</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Cannabinoid" title="Cannabinoid">Cannabinoids</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/Tetrahydrocannabinol" title="Tetrahydrocannabinol">THC</a> <ul><li><a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">Cannabis (Marijuana)</a></li> <li><a href="/wiki/Hashish" title="Hashish">Hashish</a></li> <li><a href="/wiki/Hash_oil" title="Hash oil">Hash oil</a></li></ul></li> <li><a href="/wiki/Neocannabinoid" class="mw-redirect" title="Neocannabinoid">Neocannabinoid / synthetic cannabinoids</a> <ul><li><a href="/wiki/JWH-018" title="JWH-018">JWH-018</a></li> <li><a href="/wiki/APICA_(synthetic_cannabinoid_drug)" title="APICA (synthetic cannabinoid drug)">APICA</a></li> <li><a href="/wiki/APINACA" title="APINACA">APINACA</a></li> <li><a href="/wiki/Spice_(drug)" class="mw-redirect" title="Spice (drug)">Spice</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Oneirogen" title="Oneirogen">Oneirogens</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/Calea_ternifolia" title="Calea ternifolia">Calea zacatechichi</a></li> <li><a href="/wiki/Silene_undulata" title="Silene undulata">Silene capensis</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/Club_drug" title="Club drug">Club drugs</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/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Methaqualone" title="Methaqualone">Quaaludes</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA</a> <ul><li><a href="/wiki/MDMA#Forms" title="MDMA">Ecstasy</a></li> <li><a href="/wiki/MDMA#Forms" title="MDMA">Molly</a></li></ul></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a> (<a href="/wiki/Recreational_use_of_nitrous_oxide" title="Recreational use of nitrous oxide">recreational use</a>)</li> <li><a href="/wiki/Poppers" title="Poppers">Poppers</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible mw-collapsed navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="text-align:center;"><div id="Drug_culture" style="font-size:114%;margin:0 4em"><a href="/wiki/Drug_culture" title="Drug culture">Drug culture</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cannabis_culture" title="Cannabis culture">Cannabis culture</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/420_(cannabis_culture)" title="420 (cannabis culture)">420</a></li> <li><a href="/wiki/Cannabis_consumption" title="Cannabis consumption">Cannabis consumption</a></li> <li><a href="/wiki/Cannabis_cultivation" title="Cannabis cultivation">Cannabis cultivation</a></li> <li><a href="/wiki/Cannabis_edible" title="Cannabis edible">Cannabis edible</a></li> <li><a href="/wiki/Cannabis_rights" title="Cannabis rights">Cannabis rights</a></li> <li><a href="/wiki/List_of_cannabis_rights_leaders" title="List of cannabis rights leaders">Cannabis rights leaders</a></li> <li><a href="/wiki/List_of_cannabis_rights_organizations" title="List of cannabis rights organizations">List of cannabis rights organizations</a></li> <li><a href="/wiki/Cannabis_smoking" title="Cannabis smoking">Cannabis smoking</a></li> <li><a href="/wiki/Cannabis_Social_Club" title="Cannabis Social Club">Cannabis Social Club</a></li> <li><a href="/wiki/Cannabis_tea" title="Cannabis tea">Cannabis tea</a></li> <li><a href="/wiki/Vaporizer_(inhalation_device)#Cannabis_vaporizers" title="Vaporizer (inhalation device)">Cannabis vaping</a></li> <li><a href="/wiki/Head_shop" title="Head shop">Head shop</a></li> <li><a href="/wiki/Legal_history_of_cannabis_in_the_United_States" title="Legal history of cannabis in the United States">Legal history of cannabis in the United States</a></li> <li><a href="/wiki/Legality_of_cannabis" title="Legality of cannabis">Legality of cannabis</a></li> <li><a href="/wiki/Marijuana_Policy_Project" title="Marijuana Policy Project">Marijuana Policy Project</a></li> <li><a href="/wiki/Medical_cannabis" title="Medical cannabis">Medical cannabis</a></li> <li><a href="/wiki/National_Organization_for_the_Reform_of_Marijuana_Laws" title="National Organization for the Reform of Marijuana Laws">NORML</a></li> <li><a href="/wiki/Cannabis_and_religion" title="Cannabis and religion">Cannabis and religion</a></li> <li><a href="/wiki/Stoner_film" title="Stoner film">Stoner film</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Coffee_culture" title="Coffee culture">Coffee culture</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/Break_(work)#Coffee_break" title="Break (work)">Coffee break</a></li> <li><a href="/wiki/Coffeehouse" title="Coffeehouse">Coffeehouse</a></li> <li><a href="/wiki/Latte_art" title="Latte art">Latte art</a></li> <li><a href="/wiki/Teahouse" title="Teahouse">Teahouse</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Drinking_culture" title="Drinking culture">Drinking culture</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/Bartender" title="Bartender">Bartending</a></li> <li><a href="/wiki/Beer#Beer_and_society" title="Beer">Beer culture</a></li> <li><a href="/wiki/Beer_festival" title="Beer festival">Beer festival</a></li> <li><a href="/wiki/Binge_drinking" title="Binge drinking">Binge drinking</a></li> <li><a href="/wiki/Diethyl_ether#Recreational_use" title="Diethyl ether">Diethyl ether</a></li> <li><a href="/wiki/Drinking_game" title="Drinking game">Drinking games</a></li> <li><a href="/wiki/Drinking_song" title="Drinking song">Drinking song</a></li> <li><a href="/wiki/Happy_hour" title="Happy hour">Happy hour</a></li> <li><a href="/wiki/Hip_flask" title="Hip flask">Hip flask</a></li> <li><a href="/wiki/Nightclub" title="Nightclub">Nightclub</a></li> <li><a href="/wiki/Oktoberfest" title="Oktoberfest">Oktoberfest</a></li> <li><a href="/wiki/Pub" title="Pub">Pub</a></li> <li><a href="/wiki/Pub_crawl" title="Pub crawl">Pub crawl</a></li> <li><a href="/wiki/Sommelier" title="Sommelier">Sommelier</a></li> <li><a href="/wiki/Bar_(establishment)" title="Bar (establishment)">Sports bar</a></li> <li><a href="/wiki/Tailgate_party" title="Tailgate party">Tailgate party</a></li> <li><a href="/wiki/Wine_bar" title="Wine bar">Wine bar</a></li> <li><a href="/wiki/Wine_tasting" title="Wine tasting">Wine tasting</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Psychedelia" title="Psychedelia">Psychedelia</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/Psychonautics" title="Psychonautics">Psychonautics</a></li> <li><a href="/wiki/Psychedelic_art" title="Psychedelic art">Art</a></li> <li><a href="/wiki/Psychedelic_drug" title="Psychedelic drug">Drug</a></li> <li><a href="/wiki/Psychedelic_era" title="Psychedelic era">Era</a></li> <li><a href="/wiki/Psychedelic_experience" title="Psychedelic experience">Experience</a></li> <li><a href="/wiki/Psychedelic_literature" class="mw-redirect" title="Psychedelic literature">Literature</a></li> <li><a href="/wiki/Psychedelic_music" title="Psychedelic music">Music</a></li> <li><a href="/wiki/Psychedelic_microdosing" title="Psychedelic microdosing">Microdosing</a></li> <li><a href="/wiki/Smart_shop" title="Smart shop">Smart shop</a></li> <li><a href="/wiki/Psychedelic_therapy" title="Psychedelic therapy">Therapy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Smoking#Society_and_culture" title="Smoking">Smoking culture</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/Cigarette_card" title="Cigarette card">Cigarette card</a></li> <li><a href="/wiki/Fashion_cigarettes" title="Fashion cigarettes">Fashion cigarettes</a></li> <li><a href="/wiki/Cloud-chasing" title="Cloud-chasing">Cloud-chasing</a></li> <li><a href="/wiki/Loosie" title="Loosie">Loosie</a></li> <li><a href="/wiki/Smokeasy" title="Smokeasy">Smokeasy</a></li> <li><a href="/wiki/Smoking_fetishism" title="Smoking fetishism">Smoking fetishism</a></li> <li><a href="/wiki/Tobacco_smoking" title="Tobacco smoking">Tobacco smoking</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chasing_the_dragon" title="Chasing the dragon">Chasing the dragon</a></li> <li><a href="/wiki/Club_drug" title="Club drug">Club drug</a></li> <li><a href="/wiki/Counterculture_of_the_1960s" title="Counterculture of the 1960s">Counterculture of the 1960s</a></li> <li><a href="/wiki/Dance_party" title="Dance party">Dance party</a></li> <li><a href="/wiki/Drug_paraphernalia" title="Drug paraphernalia">Drug paraphernalia</a></li> <li><a href="/wiki/Recreational_drug_tourism" title="Recreational drug tourism">Drug tourism</a></li> <li><a href="/wiki/Entheogen" title="Entheogen">Entheogen</a></li> <li><a href="/wiki/Hippie" title="Hippie">Hippie</a></li> <li><a href="/wiki/Needle_sharing" title="Needle sharing">Needle sharing</a></li> <li><a href="/wiki/Nootropic" title="Nootropic">Nootropic</a></li> <li><a href="/wiki/Party_and_play" title="Party and play">Party and play</a></li> <li><a href="/wiki/Poly_drug_use" class="mw-redirect" title="Poly drug use">Poly drug use</a></li> <li><a href="/wiki/Rave" title="Rave">Rave</a></li> <li><a href="/wiki/Religion_and_drugs" title="Religion and drugs">Religion and drugs</a></li> <li><a href="/wiki/Self-medication" title="Self-medication">Self-medication</a></li> <li><a href="/wiki/Sex_and_drugs" title="Sex and drugs">Sex and drugs</a></li> <li><a href="/wiki/Urban_legends_about_drugs" title="Urban legends about drugs">Urban legends about drugs</a></li> <li><a href="/wiki/Whoonga" title="Whoonga">Whoonga</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible mw-collapsed navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="text-align:center;"><div id="Legality_of_drug_use" style="font-size:114%;margin:0 4em">Legality of drug use</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">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><a href="/wiki/United_Nations_drug_control_conventions" class="mw-redirect" title="United Nations drug control conventions">International drug control conventions</a> <ul><li><a href="/wiki/Single_Convention_on_Narcotic_Drugs" title="Single Convention on Narcotic Drugs">1961 Narcotic Drugs</a></li> <li><a href="/wiki/Convention_on_Psychotropic_Substances" title="Convention on Psychotropic Substances">1971 Psychotropic Substances</a></li> <li><a href="/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances" title="United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances">1988 Drug Trafficking</a></li></ul></li> <li>Other treaties addressing drugs <ul><li><a href="/wiki/United_Nations_Convention_on_the_Law_of_the_Sea" title="United Nations Convention on the Law of the Sea">Law of the Sea Convention</a></li> <li><a href="/wiki/International_Convention_Against_Doping_in_Sport" title="International Convention Against Doping in Sport">Convention Against Doping</a></li> <li><a href="/wiki/Council_of_the_European_Union_decisions_on_designer_drugs" title="Council of the European Union decisions on designer drugs">Council of the European Union decisions on designer drugs</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">State level</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/Drug_policy" title="Drug policy">Drug policy</a> <ul><li><a href="/wiki/Decriminalization" title="Decriminalization">Decriminalization</a></li> <li><a href="/wiki/Legalization" title="Legalization">Legalization</a></li> <li><a href="/wiki/Prohibition_of_drugs" class="mw-redirect" title="Prohibition of drugs">Prohibition</a></li> <li><a href="/wiki/Regulation" title="Regulation">Regulation</a></li> <li><a href="/wiki/Supply_reduction" title="Supply reduction">Supply reduction</a></li></ul></li> <li><a href="/wiki/Drug_policy_reform" class="mw-redirect" title="Drug policy reform">Policy reform</a> <ul><li><a href="/wiki/Demand_reduction" title="Demand reduction">Demand reduction</a></li> <li><a href="/wiki/Drug_Policy_Alliance" title="Drug Policy Alliance">Drug Policy Alliance</a></li> <li><a href="/wiki/Harm_reduction" title="Harm reduction">Harm reduction</a></li> <li><a href="/wiki/Law_Enforcement_Action_Partnership" title="Law Enforcement Action Partnership">Law Enforcement Action Partnership</a></li> <li><a href="/wiki/Drug_liberalization" title="Drug liberalization">Liberalization</a> <ul><li><a href="/wiki/Latin_American_drug_legalization" title="Latin American drug legalization">Latin America</a></li></ul></li> <li><a href="/wiki/Students_for_Sensible_Drug_Policy" title="Students for Sensible Drug Policy">Students for Sensible Drug Policy</a></li> <li><a href="/wiki/Transform_Drug_Policy_Foundation" title="Transform Drug Policy Foundation">Transform Drug Policy Foundation</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Drug policy<br /> by country</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/Drug_policy#Australia" title="Drug policy">Australia</a></li> <li><a href="/wiki/Drug_policy_of_Canada" title="Drug policy of Canada">Canada</a></li> <li><a href="/wiki/Drug_policy_of_the_Czech_Republic" class="mw-redirect" title="Drug policy of the Czech Republic">Czech Republic</a></li> <li><a href="/wiki/Drug_policy#Germany" title="Drug policy">Germany</a></li> <li><a href="/wiki/Drug_policy_of_India" title="Drug policy of India">India</a></li> <li><a href="/wiki/Drug_policy_of_the_Netherlands" title="Drug policy of the Netherlands">Netherlands</a></li> <li><a href="/wiki/Drug_policy_of_Portugal" title="Drug policy of Portugal">Portugal</a></li> <li><a href="/wiki/Drug_policy_of_Slovakia" title="Drug policy of Slovakia">Slovakia</a></li> <li><a href="/wiki/Drug_policy_of_the_Soviet_Union" title="Drug policy of the Soviet Union">Soviet Union</a></li> <li><a href="/wiki/Drug_policy_of_Sweden" title="Drug policy of Sweden">Sweden</a></li> <li><a href="/wiki/Drug_policy#Switzerland" title="Drug policy">Switzerland</a></li> <li><a href="/wiki/Federal_drug_policy_of_the_United_States" title="Federal drug policy of the United States">United States</a> <ul><li><a href="/wiki/Just_Say_No" title="Just Say No">Just Say No</a></li> <li><a href="/wiki/Office_of_National_Drug_Control_Policy" title="Office of National Drug Control Policy">Office of National Drug Control Policy</a></li> <li><a href="/wiki/School_district_drug_policies" title="School district drug policies">School district drug policies</a></li> <li><a href="/wiki/Drug_policy_of_California" title="Drug policy of California">California</a></li> <li><a href="/wiki/Cannabis_in_Colorado" title="Cannabis in Colorado">Colorado</a></li> <li><a href="/wiki/Drug_policy_of_Maryland" title="Drug policy of Maryland">Maryland</a></li> <li><a href="/wiki/Drug_policy_of_Oregon" title="Drug policy of Oregon">Oregon</a></li> <li><a href="/wiki/Drug_policy_of_Virginia" title="Drug policy of Virginia">Virginia</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Drug legality</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_law" title="Alcohol law">Alcohol legality</a></li> <li><a href="/wiki/Anabolic_steroid#Legal_status" title="Anabolic steroid">Anabolic steroid legality</a></li> <li><a href="/wiki/Legality_of_cannabis" title="Legality of cannabis">Cannabis legality</a></li> <li><a href="/wiki/Legal_status_of_cocaine" title="Legal status of cocaine">Cocaine legality</a></li> <li><a href="/wiki/Legal_status_of_methamphetamine" title="Legal status of methamphetamine">Methamphetamine legality</a></li> <li><a href="/wiki/Psilocybin_decriminalization_in_the_United_States" title="Psilocybin decriminalization in the United States">Psilocybin decriminalization in the U.S.</a></li> <li><a href="/wiki/Legal_status_of_psilocybin_mushrooms" title="Legal status of psilocybin mushrooms">Psilocybin mushrooms legality</a></li> <li><a href="/wiki/Legal_status_of_Salvia_divinorum" title="Legal status of Salvia divinorum">Salvia legality</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Arguments_for_and_against_drug_prohibition" title="Arguments for and against drug prohibition">Arguments for and against drug prohibition</a></li> <li><a href="/wiki/Cannabis_rights" title="Cannabis rights">Cannabis rights</a></li> <li><a href="/wiki/Capital_punishment_for_drug_trafficking" title="Capital punishment for drug trafficking">Capital punishment for drug trafficking</a></li> <li><a href="/wiki/Cognitive_liberty" title="Cognitive liberty">Cognitive liberty</a></li> <li><a href="/wiki/Designer_drug" title="Designer drug">Designer drug</a></li> <li><a href="/wiki/Drug_court" title="Drug court">Drug court</a></li> <li><a href="/wiki/Drug_possession" class="mw-redirect" title="Drug possession">Drug possession</a></li> <li><a href="/wiki/Drug_test" title="Drug test">Drug test</a></li> <li><a href="/wiki/Informant" title="Informant">Narc</a></li> <li><a href="/wiki/Politics_of_drug_abuse" title="Politics of drug abuse">Politics of drug abuse</a></li> <li><a href="/wiki/War_on_drugs" title="War on drugs">War on drugs</a> <ul><li><a href="/wiki/Mexican_drug_war" title="Mexican drug war">Mexican drug war</a></li> <li><a href="/wiki/Plan_Colombia" title="Plan Colombia">Plan Colombia</a></li> <li><a href="/wiki/Philippine_drug_war" title="Philippine drug war">Philippine drug war</a></li></ul></li> <li><a href="/wiki/Zero_tolerance" title="Zero tolerance">Zero tolerance</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible mw-collapsed navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="text-align:center;"><div id="Other" style="font-size:114%;margin:0 4em">Other</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Drug<br /> production<br /> and trade</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Drug<br /> production</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/Coca_production_in_Colombia" title="Coca production in Colombia">Coca production in Colombia</a></li> <li><a href="/wiki/Precursor_chemicals" title="Precursor chemicals">Drug precursors</a></li> <li><a href="/wiki/Opium_production_in_Afghanistan" title="Opium production in Afghanistan">Opium production in Afghanistan</a></li> <li><a href="/wiki/Rolling_meth_lab" title="Rolling meth lab">Rolling meth lab</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Drug trade</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/Illegal_drug_trade" title="Illegal drug trade">Illegal drug trade</a> <ul><li><a href="/wiki/Illegal_drug_trade_in_Afghanistan" class="mw-redirect" title="Illegal drug trade in Afghanistan">Afghanistan</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Aruba" title="Illegal drug trade in Aruba">Aruba</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Australia" class="mw-redirect" title="Illegal drug trade in Australia">Australia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Bangladesh" class="mw-redirect" title="Illegal drug trade in Bangladesh">Bangladesh</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Belize" class="mw-redirect" title="Illegal drug trade in Belize">Belize</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Benin" class="mw-redirect" title="Illegal drug trade in Benin">Benin</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Bhutan" class="mw-redirect" title="Illegal drug trade in Bhutan">Bhutan</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Bolivia" class="mw-redirect" title="Illegal drug trade in Bolivia">Bolivia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Brazil" class="mw-redirect" title="Illegal drug trade in Brazil">Brazil</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Burma" class="mw-redirect" title="Illegal drug trade in Burma">Burma</a></li> <li><a href="/wiki/Drugs_in_Cambodia" title="Drugs in Cambodia">Cambodia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Chile" class="mw-redirect" title="Illegal drug trade in Chile">Chile</a></li> <li><a href="/wiki/Illegal_drug_trade_in_China" title="Illegal drug trade in China">China</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Colombia" title="Illegal drug trade in Colombia">Colombia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Costa_Rica" class="mw-redirect" title="Illegal drug trade in Costa Rica">Costa Rica</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Cuba" class="mw-redirect" title="Illegal drug trade in Cuba">Cuba</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Cyprus" class="mw-redirect" title="Illegal drug trade in Cyprus">Cyprus</a></li> <li><a href="/wiki/Illegal_drug_trade_in_the_Dominican_Republic" class="mw-redirect" title="Illegal drug trade in the Dominican Republic">Dominican Republic</a></li> <li><a href="/wiki/Illegal_drug_trade_in_El_Salvador" title="Illegal drug trade in El Salvador">El Salvador</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Estonia" class="mw-redirect" title="Illegal drug trade in Estonia">Estonia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Finland" class="mw-redirect" title="Illegal drug trade in Finland">Finland</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Germany" class="mw-redirect" title="Illegal drug trade in Germany">Germany</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Haiti" title="Illegal drug trade in Haiti">Haiti</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Honduras" class="mw-redirect" title="Illegal drug trade in Honduras">Honduras</a></li> <li><a href="/wiki/Illegal_drug_trade_in_India" class="mw-redirect" title="Illegal drug trade in India">India</a></li> <li><a href="/wiki/Illegal_drug_trade_in_the_Indian_Ocean_region" title="Illegal drug trade in the Indian Ocean region">Indian Ocean region</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Iran" class="mw-redirect" title="Illegal drug trade in Iran">Iran</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Italy" class="mw-redirect" title="Illegal drug trade in Italy">Italy</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Japan" title="Illegal drug trade in Japan">Japan</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Kenya" class="mw-redirect" title="Illegal drug trade in Kenya">Kenya</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Kosovo" class="mw-redirect" title="Illegal drug trade in Kosovo">Kosovo</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Kyrgyzstan" class="mw-redirect" title="Illegal drug trade in Kyrgyzstan">Kyrgyzstan</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Laos" class="mw-redirect" title="Illegal drug trade in Laos">Laos</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Latin_America" title="Illegal drug trade in Latin America">Latin America</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Latvia" class="mw-redirect" title="Illegal drug trade in Latvia">Latvia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Malaysia" class="mw-redirect" title="Illegal drug trade in Malaysia">Malaysia</a></li> <li><a href="/wiki/Drug_trafficking_in_Mauritius" title="Drug trafficking in Mauritius">Mauritius</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Moldova" class="mw-redirect" title="Illegal drug trade in Moldova">Moldova</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Nigeria" class="mw-redirect" title="Illegal drug trade in Nigeria">Nigeria</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Norway" class="mw-redirect" title="Illegal drug trade in Norway">Norway</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Oman" class="mw-redirect" title="Illegal drug trade in Oman">Oman</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Panama" title="Illegal drug trade in Panama">Panama</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Papua_New_Guinea" class="mw-redirect" title="Illegal drug trade in Papua New Guinea">Papua New Guinea</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Paraguay" title="Illegal drug trade in Paraguay">Paraguay</a></li> <li><a href="/wiki/Illegal_drug_trade_in_the_Philippines" title="Illegal drug trade in the Philippines">Philippines</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Poland" class="mw-redirect" title="Illegal drug trade in Poland">Poland</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Portugal" class="mw-redirect" title="Illegal drug trade in Portugal">Portugal</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Puerto_Rico" title="Illegal drug trade in Puerto Rico">Puerto Rico</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Russia" class="mw-redirect" title="Illegal drug trade in Russia">Russia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Saint_Kitts_and_Nevis" class="mw-redirect" title="Illegal drug trade in Saint Kitts and Nevis">Saint Kitts and Nevis</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Seychelles" title="Illegal drug trade in Seychelles">Seychelles</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Slovakia" class="mw-redirect" title="Illegal drug trade in Slovakia">Slovakia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_South_Africa" class="mw-redirect" title="Illegal drug trade in South Africa">South Africa</a></li> <li><a href="/wiki/Illegal_drug_trade_in_South_Korea" class="mw-redirect" title="Illegal drug trade in South Korea">South Korea</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Spain" class="mw-redirect" title="Illegal drug trade in Spain">Spain</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Suriname" class="mw-redirect" title="Illegal drug trade in Suriname">Suriname</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Switzerland" class="mw-redirect" title="Illegal drug trade in Switzerland">Switzerland</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Taiwan" class="mw-redirect" title="Illegal drug trade in Taiwan">Taiwan</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Thailand" class="mw-redirect" title="Illegal drug trade in Thailand">Thailand</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Turkey" title="Illegal drug trade in Turkey">Turkey</a></li> <li><a href="/wiki/Illegal_drug_trade_in_the_Turks_and_Caicos_Islands" title="Illegal drug trade in the Turks and Caicos Islands">Turks and Caicos Islands</a></li> <li><a href="/wiki/Illegal_drug_trade_in_the_United_Arab_Emirates" class="mw-redirect" title="Illegal drug trade in the United Arab Emirates">United Arab Emirates</a></li> <li><a href="/wiki/Illegal_drug_trade_in_the_United_States" title="Illegal drug trade in the United States">United States</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Venezuela" title="Illegal drug trade in Venezuela">Venezuela</a></li></ul></li> <li><a href="/wiki/Darknet_market" title="Darknet market">Darknet market</a></li> <li><a href="/wiki/Pharmaceutical_distribution" title="Pharmaceutical distribution">Pharmaceutical distribution</a> <ul><li><a href="/wiki/Beer_shop" class="mw-redirect" title="Beer shop">Beer shop</a></li> <li><a href="/wiki/Cannabis_shop" class="mw-redirect" title="Cannabis shop">Cannabis shop</a></li> <li><a href="/wiki/Liquor_store" title="Liquor store">Liquor store</a></li> <li><a href="/wiki/Liquor_license" title="Liquor license">Liquor license</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Issues with<br />drug use</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/Substance_abuse" title="Substance abuse">Abuse</a></li> <li><a href="/wiki/Addiction" title="Addiction">Addiction</a></li> <li><a href="/wiki/Date_rape_drug" title="Date rape drug">Date rape drug</a></li> <li><a href="/wiki/Substance_dependence" title="Substance dependence">Dependence</a></li> <li><a href="/wiki/Driving_under_the_influence" title="Driving under the influence">Driving impaired</a></li> <li><a href="/wiki/Drug_harmfulness" class="mw-redirect" title="Drug harmfulness">Drug harmfulness</a> <ul><li><a href="/wiki/Effects_of_cannabis" title="Effects of cannabis">Effects of cannabis</a></li></ul></li> <li><a href="/wiki/Drug-related_crime" title="Drug-related crime">Drug-related crime</a></li> <li><a href="/wiki/Fetal_alcohol_spectrum_disorder" title="Fetal alcohol spectrum disorder">Fetal alcohol spectrum disorder</a></li> <li><a href="/wiki/Long-term_effects_of_cannabis" title="Long-term effects of cannabis">Long-term effects of cannabis</a></li> <li><a href="/wiki/Neurotoxicity" title="Neurotoxicity">Neurotoxicity</a></li> <li><a href="/wiki/Drug_overdose" title="Drug overdose">Overdose</a></li> <li><a href="/wiki/Passive_smoking" title="Passive smoking">Passive smoking</a> <ul><li>of tobacco or other substances</li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Harm reduction</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/Drug_checking" title="Drug checking">Drug checking</a></li> <li><a href="/wiki/Drug_legalization" class="mw-redirect" title="Drug legalization">Drug legalization</a></li> <li><a href="/wiki/Drug_rehabilitation" title="Drug rehabilitation">Drug rehabilitation</a></li> <li><a href="/wiki/Needle_and_syringe_programmes" title="Needle and syringe programmes">Needle and syringe programmes</a></li> <li><a href="/wiki/Opioid_replacement_therapy" class="mw-redirect" title="Opioid replacement therapy">Opioid replacement therapy</a></li> <li><a href="/wiki/Pharmacovigilance" title="Pharmacovigilance">Pharmacovigilance</a></li> <li><a href="/wiki/Reagent_testing" title="Reagent testing">Reagent testing</a></li> <li><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Regulation of therapeutic goods</a></li> <li><a href="/wiki/Responsible_drug_use" title="Responsible drug use">Responsible drug use</a></li> <li><a href="/wiki/Substance_abuse_prevention" title="Substance abuse prevention">Substance abuse prevention</a></li> <li><a href="/wiki/Supervised_injection_site" title="Supervised injection site">Supervised injection site</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Countries by <br /> drug use</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/List_of_countries_by_alcohol_consumption_per_capita" title="List of countries by alcohol consumption per capita">Alcohol consumption</a></li> <li><a href="/wiki/List_of_countries_by_prevalence_of_cocaine_use" title="List of countries by prevalence of cocaine use">Cocaine use</a></li> <li>Cannabis <ul><li><a href="/wiki/Annual_cannabis_use_by_country" class="mw-redirect" title="Annual cannabis use by country">Annual use</a></li> <li><a href="/wiki/Adult_lifetime_cannabis_use_by_country" title="Adult lifetime cannabis use by country">Lifetime use</a></li></ul></li> <li><a href="/wiki/List_of_countries_by_prevalence_of_opiates_use" title="List of countries by prevalence of opiates use">Opiates use</a></li> <li><a href="/wiki/List_of_countries_by_tobacco_consumption" class="mw-redirect" title="List of countries by tobacco consumption">Tobacco consumption</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Reinforcement_disorders:_addiction_and_dependence" 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:Addiction" title="Template:Addiction"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Addiction" title="Template talk:Addiction"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Addiction" title="Special:EditPage/Template:Addiction"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Reinforcement_disorders:_addiction_and_dependence" style="font-size:114%;margin:0 4em"><a href="/wiki/Reinforcement" title="Reinforcement">Reinforcement</a> disorders: <a href="/wiki/Addiction" title="Addiction">addiction</a> and <a href="/wiki/Substance_dependence" title="Substance dependence">dependence</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Addiction" title="Addiction">Addiction</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%;text-align:center;">Drug</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/Alcohol_(drug)" title="Alcohol (drug)">Alcohol</a></li> <li><a href="/wiki/Amphetamine#Addiction" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/Cocaine_addiction" class="mw-redirect" title="Cocaine addiction">Cocaine</a></li> <li><a href="/wiki/Methamphetamine#Addiction" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/Methylphenidate#Addiction_and_dependence" title="Methylphenidate">Methylphenidate</a></li> <li><b>Nicotine</b></li> <li><a href="/wiki/Opioid_use_disorder" title="Opioid use disorder">Opioid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Behavioral_addiction" title="Behavioral addiction">Behavioral</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>Financial <ul><li><a href="/wiki/Problem_gambling" title="Problem gambling">Gambling</a></li> <li><a href="/wiki/Compulsive_buying_disorder" title="Compulsive buying disorder">Shopping</a></li></ul></li> <li><a href="/wiki/Food_addiction" title="Food addiction">Palatable food</a></li> <li>Sex-related <ul><li><a href="/wiki/Sexual_addiction" title="Sexual addiction">Intercourse</a></li> <li><a href="/wiki/Pornography_addiction" title="Pornography addiction">Pornography</a></li></ul></li> <li>Internet-related <ul><li><a href="/wiki/Internet_addiction_disorder" title="Internet addiction disorder">Internet addiction disorder</a></li> <li><a href="/wiki/Internet_sex_addiction" title="Internet sex addiction">Internet sex addiction</a></li></ul></li> <li><a href="/wiki/Video_game_addiction" title="Video game addiction">Video game addiction</a></li> <li><a href="/wiki/Digital_media_use_and_mental_health" title="Digital media use and mental health">Digital media addictions</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Cellular<br />mechanisms</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/Transcription_factor" title="Transcription factor">Transcriptional</a> <ul><li><b><a href="/wiki/FOSB#ΔFosB" title="FOSB">ΔFosB</a></b></li> <li><a href="/wiki/C-Fos" class="mw-redirect" title="C-Fos">c-Fos</a></li> <li><a href="/wiki/Cdk5" class="mw-redirect" title="Cdk5">Cdk5</a></li> <li><a href="/wiki/CREB" title="CREB">CREB</a></li> <li><a href="/wiki/GluR2" class="mw-redirect" title="GluR2">GluR2</a></li> <li><a href="/wiki/NF-%CE%BAB" title="NF-κB">NF-κB</a></li></ul></li></ul> <ul><li><a href="/wiki/Histone-modifying_enzymes" title="Histone-modifying enzymes">Epigenetic</a> <ul><li><b><a href="/wiki/G9a" class="mw-redirect" title="G9a">G9a</a></b></li> <li><a href="/wiki/G9a-like_protein" class="mw-redirect" title="G9a-like protein">G9a-like protein</a></li> <li><b><a href="/wiki/HDAC1" title="HDAC1">HDAC1</a></b></li> <li><b><a href="/wiki/HDAC2" class="mw-redirect" title="HDAC2">HDAC2</a></b></li> <li><b><a href="/wiki/HDAC3" title="HDAC3">HDAC3</a></b></li> <li><a href="/wiki/HDAC4" title="HDAC4">HDAC4</a></li> <li><a href="/wiki/HDAC5" class="mw-redirect" title="HDAC5">HDAC5</a></li> <li><a href="/wiki/HDAC9" title="HDAC9">HDAC9</a></li> <li><a href="/wiki/HDAC10" title="HDAC10">HDAC10</a></li> <li><a href="/wiki/SIRT1" class="mw-redirect" title="SIRT1">SIRT1</a></li> <li><a href="/wiki/SIRT2" class="mw-redirect" title="SIRT2">SIRT2</a></li> <li>...</li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substance_dependence" title="Substance dependence">Dependence</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%;text-align:center;">Concepts</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/Adverse_childhood_experiences" title="Adverse childhood experiences">Adverse childhood experiences</a></li> <li><a href="/wiki/Physical_dependence" title="Physical dependence">Physical dependence</a></li> <li><a href="/wiki/Psychological_dependence" title="Psychological dependence">Psychological dependence</a></li> <li><a href="/wiki/Drug_withdrawal" title="Drug withdrawal">Withdrawal</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Disorders</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Drugs <ul><li><a href="/wiki/Alcoholism" title="Alcoholism">Alcoholism</a></li> <li><a href="/wiki/Amphetamine_dependence" title="Amphetamine dependence">Amphetamine</a></li> <li><a href="/wiki/Barbiturate_dependence" title="Barbiturate dependence">Barbiturate</a></li> <li><a href="/wiki/Benzodiazepine_dependence" title="Benzodiazepine dependence">Benzodiazepine</a></li> <li><a href="/wiki/Caffeine_dependence" title="Caffeine dependence">Caffeine</a></li> <li><a href="/wiki/Cannabis_dependence" class="mw-redirect" title="Cannabis dependence">Cannabis</a></li> <li><a href="/wiki/Cocaine_dependence" title="Cocaine dependence">Cocaine</a></li> <li><a href="/wiki/Nicotine_dependence" title="Nicotine dependence">Nicotine</a></li> <li><a href="/wiki/Opioid_use_disorder" title="Opioid use disorder">Opioid</a></li></ul></li> <li>Non-drug stimuli <ul><li><a href="/wiki/Tanning_dependence" title="Tanning dependence">Tanning dependence</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Treatment_and_management_of_addiction" title="Treatment and management of addiction">Treatment <br />and <br />management</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%;text-align:center;">Detoxification</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alcohol_detoxification" title="Alcohol detoxification">Alcohol detoxification</a></li> <li><a href="/wiki/Drug_detoxification" title="Drug detoxification">Drug detoxification</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Behavioral <br />therapies</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cognitive_behavioral_therapy" title="Cognitive behavioral therapy">Cognitive behavioral therapy</a> <ul><li><a href="/wiki/Relapse_prevention" title="Relapse prevention">Relapse prevention</a></li> <li><a href="/wiki/Contingency_management" title="Contingency management">Contingency management</a></li></ul></li> <li><a href="/wiki/Community_reinforcement_approach_and_family_training" title="Community reinforcement approach and family training">Community reinforcement approach and family training</a></li> <li><a href="/wiki/Motivational_enhancement_therapy" title="Motivational enhancement therapy">Motivational enhancement therapy</a></li> <li><a href="/wiki/Motivational_interviewing" title="Motivational interviewing">Motivational interviewing</a></li> <li><a href="/wiki/Motivational_therapy" title="Motivational therapy">Motivational therapy</a></li> <li><a href="/wiki/Neurobiological_effects_of_physical_exercise#Addiction" title="Neurobiological effects of physical exercise">Physical exercise</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Treatment <br />programs</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Drug_rehab" class="mw-redirect" title="Drug rehab">Drug rehab</a> <ul><li><a href="/wiki/Residential_treatment_center" title="Residential treatment center">Residential treatment center</a></li></ul></li> <li><a href="/wiki/Heroin-assisted_treatment" title="Heroin-assisted treatment">Heroin-assisted treatment</a></li> <li><a href="/wiki/Intensive_outpatient_program" title="Intensive outpatient program">Intensive outpatient program</a></li> <li><a href="/wiki/Methadone_maintenance" class="mw-redirect" title="Methadone maintenance">Methadone maintenance</a></li> <li><a href="/wiki/Smoking_cessation" title="Smoking cessation">Smoking cessation</a> <ul><li><a href="/wiki/Nicotine_replacement_therapy" title="Nicotine replacement therapy">Nicotine replacement therapy</a></li> <li><a href="/wiki/Tobacco_cessation_clinics_in_India" title="Tobacco cessation clinics in India">Tobacco cessation clinics in India</a></li></ul></li> <li><a href="/wiki/Twelve-step_program" title="Twelve-step program">Twelve-step program</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Support groups</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Addiction_recovery_groups" class="mw-redirect" title="Addiction recovery groups">Addiction recovery groups</a></li> <li><a href="/wiki/List_of_twelve-step_groups" title="List of twelve-step groups">List of twelve-step groups</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Harm_reduction" title="Harm reduction">Harm reduction</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Category:Harm_reduction" title="Category:Harm reduction">Category:Harm reduction</a></li> <li><a href="/wiki/Drug_checking" title="Drug checking">Drug checking</a> <ul><li><a href="/wiki/Reagent_testing" title="Reagent testing">Reagent testing</a></li></ul></li> <li><a href="/wiki/Low-threshold_treatment_programs" class="mw-redirect" title="Low-threshold treatment programs">Low-threshold treatment programs</a></li> <li><a href="/wiki/Managed_alcohol_program" title="Managed alcohol program">Managed alcohol program</a></li> <li><a href="/wiki/Moderation_Management" title="Moderation Management">Moderation Management</a></li> <li><a href="/wiki/Needle_exchange_program" class="mw-redirect" title="Needle exchange program">Needle exchange program</a></li> <li><a href="/wiki/Responsible_drug_use" title="Responsible drug use">Responsible drug use</a></li> <li><a href="/wiki/Stimulant_maintenance" title="Stimulant maintenance">Stimulant maintenance</a></li> <li><a href="/wiki/Supervised_injection_site" title="Supervised injection site">Supervised injection site</a></li> <li><a href="/wiki/Tobacco_harm_reduction" title="Tobacco harm reduction">Tobacco harm reduction</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">See also</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/Addiction_medicine" title="Addiction medicine">Addiction medicine</a></li> <li><a href="/wiki/Allen_Carr" title="Allen Carr">Allen Carr</a></li> <li><a href="/wiki/Category:Addiction" title="Category:Addiction">Category:Addiction</a></li> <li><a href="/wiki/Category:Vaccines_against_drugs" title="Category:Vaccines against drugs">Category:Vaccines against drugs</a></li> <li><a href="/wiki/Discrimination_against_drug_addicts" title="Discrimination against drug addicts">Discrimination against drug addicts</a></li> <li><a href="/wiki/Dopamine_dysregulation_syndrome" title="Dopamine dysregulation syndrome">Dopamine dysregulation syndrome</a></li> <li><a href="/wiki/Cognitive_control" class="mw-redirect" title="Cognitive control">Cognitive control</a> <ul><li><a href="/wiki/Inhibitory_control" title="Inhibitory control">Inhibitory control</a></li></ul></li> <li><a href="/wiki/Motivational_salience" title="Motivational salience">Motivational salience</a> <ul><li><a href="/wiki/Motivational_salience#Incentive_salience" title="Motivational salience">Incentive salience</a></li></ul></li> <li><a href="/wiki/Sober_companion" title="Sober companion">Sober companion</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow hlist" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Addiction" title="Category:Addiction">Category</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Treatment_of_drug_dependence_(N07B)" 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:Dependence_treatment" title="Template:Dependence treatment"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Dependence_treatment" title="Template talk:Dependence treatment"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Dependence_treatment" title="Special:EditPage/Template:Dependence treatment"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Treatment_of_drug_dependence_(N07B)" style="font-size:114%;margin:0 4em">Treatment of <a href="/wiki/Substance_dependence" title="Substance dependence">drug dependence</a> (<a href="/wiki/ATC_code_N07#N07B" title="ATC code N07">N07B</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nicotine_dependence" title="Nicotine dependence">Nicotine dependence</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/Bupropion" title="Bupropion">Bupropion</a><sup>#</sup></li> <li><a href="/wiki/Cytisine" title="Cytisine">Cytisine</a></li> <li><a href="/wiki/Lobeline" title="Lobeline">Lobeline</a></li> <li><a href="/wiki/Mecamylamine" title="Mecamylamine">Mecamylamine</a></li> <li><a href="/wiki/Varenicline" title="Varenicline">Varenicline</a></li> <li><i><a href="/wiki/Adrenergic_agonist" title="Adrenergic agonist"><abbr title="Adrenergic agonist">AA</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 Adrenergic agonist</span></i> (<a href="/wiki/Clonidine" title="Clonidine">Clonidine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohol_dependence" title="Alcohol dependence">Alcohol dependence</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Acetaldehyde_dehydrogenase_inhibitor" class="mw-redirect" title="Acetaldehyde dehydrogenase inhibitor"><abbr title="Acetaldehyde dehydrogenase">AD</abbr> inhibitor</a></i> <ul><li><a href="/wiki/Disulfiram" title="Disulfiram">Disulfiram</a></li> <li><a href="/wiki/Acamprosate" title="Acamprosate">Acamprosate</a></li> <li><a href="/wiki/Calcium_carbimide" title="Calcium carbimide">Calcium carbimide</a></li> <li><a href="/wiki/Hydrogen_cyanamide" class="mw-redirect" title="Hydrogen cyanamide">Hydrogen cyanamide</a></li></ul></li> <li><i><a href="/wiki/General_anesthetic" class="mw-redirect" title="General anesthetic">General anesthetics</a></i> <ul><li><a href="/wiki/Nitrous_oxide_(medication)" title="Nitrous oxide (medication)">Nitrous oxide</a></li></ul></li> <li><i><a href="/wiki/Opioid_antagonist" title="Opioid antagonist">Opioid antagonists</a></i> <ul><li><a href="/wiki/Naltrexone" title="Naltrexone">Naltrexone</a></li> <li><a href="/wiki/Nalmefene" title="Nalmefene">Nalmefene</a></li></ul></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><i><a href="/wiki/Adrenergic_agonist" title="Adrenergic agonist"><abbr title="Adrenergic agonist">AA</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 Adrenergic agonist</span></i> (<a href="/wiki/Clonidine" title="Clonidine">Clonidine</a>)</li> <li><a href="/wiki/Baclofen" title="Baclofen">Baclofen</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opioid_dependence" 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