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populations </div> </a> <ul id="toc-Specific_populations-sublist" class="vector-toc-list"> <li id="toc-Adults" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Adults"> <div class="vector-toc-text"> 1.3.1 Adults </div> </a> <ul id="toc-Adults-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Children" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Children"> <div class="vector-toc-text"> 1.3.2 Children </div> </a> <ul id="toc-Children-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Adolescents" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Adolescents"> <div class="vector-toc-text"> 1.3.3 Adolescents </div> </a> <ul id="toc-Adolescents-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pregnancy_and_breastfeeding" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Pregnancy_and_breastfeeding"> <div class="vector-toc-text"> 1.3.4 Pregnancy and breastfeeding </div> </a> <ul id="toc-Pregnancy_and_breastfeeding-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </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"> 2 Adverse effects </div> </a> <button aria-controls="toc-Adverse_effects-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Adverse effects subsection </button> <ul id="toc-Adverse_effects-sublist" class="vector-toc-list"> <li id="toc-Physiological" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Physiological"> <div class="vector-toc-text"> 2.1 Physiological </div> </a> <ul id="toc-Physiological-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Psychological" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Psychological"> <div class="vector-toc-text"> 2.2 Psychological </div> </a> <ul id="toc-Psychological-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reinforcement_disorders" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reinforcement_disorders"> <div class="vector-toc-text"> 2.3 Reinforcement disorders </div> </a> <ul id="toc-Reinforcement_disorders-sublist" class="vector-toc-list"> <li id="toc-Addiction" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Addiction"> <div class="vector-toc-text"> 2.3.1 Addiction </div> </a> <ul id="toc-Addiction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dependence_and_withdrawal" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Dependence_and_withdrawal"> <div class="vector-toc-text"> 2.3.2 Dependence and withdrawal </div> </a> <ul id="toc-Dependence_and_withdrawal-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Risk_of_other_diseases" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Risk_of_other_diseases"> <div class="vector-toc-text"> 2.4 Risk of other diseases </div> </a> <ul id="toc-Risk_of_other_diseases-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Energy_crash" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Energy_crash"> <div class="vector-toc-text"> 2.5 Energy crash </div> </a> <ul id="toc-Energy_crash-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"> 3 Overdose </div> </a> <button aria-controls="toc-Overdose-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Overdose subsection </button> <ul id="toc-Overdose-sublist" class="vector-toc-list"> <li id="toc-Energy_drinks" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Energy_drinks"> <div class="vector-toc-text"> 3.1 Energy drinks </div> </a> <ul id="toc-Energy_drinks-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Severe_intoxication" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Severe_intoxication"> <div class="vector-toc-text"> 3.2 Severe intoxication </div> </a> <ul id="toc-Severe_intoxication-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Lethal_dose" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Lethal_dose"> <div class="vector-toc-text"> 3.3 Lethal dose </div> </a> <ul id="toc-Lethal_dose-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Interactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Interactions"> <div class="vector-toc-text"> 4 Interactions </div> </a> <button aria-controls="toc-Interactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Interactions subsection </button> <ul id="toc-Interactions-sublist" class="vector-toc-list"> <li id="toc-Alcohol" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alcohol"> <div class="vector-toc-text"> 4.1 Alcohol </div> </a> <ul id="toc-Alcohol-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Smoking" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Smoking"> <div class="vector-toc-text"> 4.2 Smoking </div> </a> <ul id="toc-Smoking-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Birth_control" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Birth_control"> <div class="vector-toc-text"> 4.3 Birth control </div> </a> <ul id="toc-Birth_control-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Medications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Medications"> <div class="vector-toc-text"> 4.4 Medications </div> </a> <ul id="toc-Medications-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"> 5 Pharmacology </div> </a> <button aria-controls="toc-Pharmacology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Pharmacology subsection </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"> 5.1 Pharmacodynamics </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> <li id="toc-Receptor_and_ion_channel_targets" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Receptor_and_ion_channel_targets"> <div class="vector-toc-text"> 5.1.1 Receptor and ion channel targets </div> </a> <ul id="toc-Receptor_and_ion_channel_targets-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Effects_on_striatal_dopamine" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Effects_on_striatal_dopamine"> <div class="vector-toc-text"> 5.1.2 Effects on striatal dopamine </div> </a> <ul id="toc-Effects_on_striatal_dopamine-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Enzyme_targets" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Enzyme_targets"> <div class="vector-toc-text"> 5.1.3 Enzyme targets </div> </a> <ul id="toc-Enzyme_targets-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"> 5.2 Pharmacokinetics </div> </a> <ul id="toc-Pharmacokinetics-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"> 6 Chemistry </div> </a> <button aria-controls="toc-Chemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Chemistry subsection </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> 6.1 Synthesis </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Decaffeination" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Decaffeination"> <div class="vector-toc-text"> 6.2 Decaffeination </div> </a> <ul id="toc-Decaffeination-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"> 6.3 Detection in body fluids </div> </a> <ul id="toc-Detection_in_body_fluids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Analogs" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Analogs"> <div class="vector-toc-text"> 6.4 Analogs </div> </a> <ul id="toc-Analogs-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precipitation_of_tannins" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precipitation_of_tannins"> <div class="vector-toc-text"> 6.5 Precipitation of tannins </div> </a> <ul id="toc-Precipitation_of_tannins-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"> 7 Natural occurrence </div> </a> <ul id="toc-Natural_occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Products" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Products"> <div class="vector-toc-text"> 8 Products </div> </a> <button aria-controls="toc-Products-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Products subsection </button> <ul id="toc-Products-sublist" class="vector-toc-list"> <li id="toc-Beverages" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Beverages"> <div class="vector-toc-text"> 8.1 Beverages </div> </a> <ul id="toc-Beverages-sublist" class="vector-toc-list"> <li id="toc-Coffee" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Coffee"> <div class="vector-toc-text"> 8.1.1 Coffee </div> </a> <ul id="toc-Coffee-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tea" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Tea"> <div class="vector-toc-text"> 8.1.2 Tea </div> </a> <ul id="toc-Tea-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Soft_drinks_and_energy_drinks" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Soft_drinks_and_energy_drinks"> <div class="vector-toc-text"> 8.1.3 Soft drinks and energy drinks </div> </a> <ul id="toc-Soft_drinks_and_energy_drinks-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_beverages" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Other_beverages"> <div class="vector-toc-text"> 8.1.4 Other beverages </div> </a> <ul id="toc-Other_beverages-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Cacao_solids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cacao_solids"> <div class="vector-toc-text"> 8.2 Cacao solids </div> </a> <ul id="toc-Cacao_solids-sublist" class="vector-toc-list"> <li id="toc-Chocolate" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Chocolate"> <div class="vector-toc-text"> 8.2.1 Chocolate </div> </a> <ul id="toc-Chocolate-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Tablets" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Tablets"> <div class="vector-toc-text"> 8.3 Tablets </div> </a> <ul id="toc-Tablets-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_oral_products" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_oral_products"> <div class="vector-toc-text"> 8.4 Other oral products </div> </a> <ul id="toc-Other_oral_products-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Inhalants" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Inhalants"> <div class="vector-toc-text"> 8.5 Inhalants </div> </a> <ul id="toc-Inhalants-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Combinations_with_other_drugs" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Combinations_with_other_drugs"> <div class="vector-toc-text"> 8.6 Combinations with other drugs </div> </a> <ul id="toc-Combinations_with_other_drugs-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> 9 History </div> </a> <button aria-controls="toc-History-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle History subsection </button> <ul id="toc-History-sublist" class="vector-toc-list"> <li id="toc-Discovery_and_spread_of_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Discovery_and_spread_of_use"> <div class="vector-toc-text"> 9.1 Discovery and spread of use </div> </a> <ul id="toc-Discovery_and_spread_of_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemical_identification,_isolation,_and_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chemical_identification,_isolation,_and_synthesis"> <div class="vector-toc-text"> 9.2 Chemical identification, isolation, and synthesis </div> </a> <ul id="toc-Chemical_identification,_isolation,_and_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Historic_regulations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Historic_regulations"> <div class="vector-toc-text"> 9.3 Historic regulations </div> </a> <ul id="toc-Historic_regulations-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> 10 Society and culture </div> </a> <button aria-controls="toc-Society_and_culture-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Society and culture subsection </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Regulations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Regulations"> <div class="vector-toc-text"> 10.1 Regulations </div> </a> <ul id="toc-Regulations-sublist" class="vector-toc-list"> <li id="toc-United_States" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#United_States"> <div class="vector-toc-text"> 10.1.1 United States </div> </a> <ul id="toc-United_States-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Consumption" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Consumption"> <div class="vector-toc-text"> 10.2 Consumption </div> </a> <ul id="toc-Consumption-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Religions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Religions"> <div class="vector-toc-text"> 10.3 Religions </div> </a> <ul id="toc-Religions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Other_organisms" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Other_organisms"> <div class="vector-toc-text"> 11 Other organisms </div> </a> <ul id="toc-Other_organisms-sublist" class="vector-toc-list"> </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"> 12 Research </div> </a> <ul id="toc-Research-sublist" class="vector-toc-list"> </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"> 13 See also </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"> 14 References </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bibliography" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Bibliography"> <div class="vector-toc-text"> 15 Bibliography </div> </a> <ul id="toc-Bibliography-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"> 16 External links </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Toggle the table of contents </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">Caffeine</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 92 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-92" aria-hidden="true" > 92 languages </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/Kafe%C3%AFen" title="Kafeïen – Afrikaans" lang="af" hreflang="af" data-title="Kafeïen" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target">Afrikaans</a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%83%D8%A7%D9%81%D9%8A%D9%8A%D9%86" title="كافيين – Arabic" lang="ar" hreflang="ar" data-title="كافيين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Cafe%C3%ADna" title="Cafeína – Asturian" lang="ast" hreflang="ast" data-title="Cafeína" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target">Asturianu</a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Kofein" title="Kofein – Azerbaijani" lang="az" hreflang="az" data-title="Kofein" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target">Azərbaycanca</a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%95%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%AB%E0%A7%87%E0%A6%87%E0%A6%A8" title="ক্যাফেইন – Bangla" lang="bn" hreflang="bn" data-title="ক্যাফেইন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target">বাংলা</a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9A%D0%B0%D1%84%D0%B5%D1%96%D0%BD" title="Кафеін – Belarusian" lang="be" hreflang="be" data-title="Кафеін" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target">Беларуская</a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%9A%D0%B0%D1%84%D1%8D%D1%96%D0%BD" title="Кафэін – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Кафэін" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target">Беларуская (тарашкевіца)</a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9A%D0%BE%D1%84%D0%B5%D0%B8%D0%BD" title="Кофеин – Bulgarian" lang="bg" hreflang="bg" data-title="Кофеин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target">Български</a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Kofein" title="Kofein – Bosnian" lang="bs" hreflang="bs" data-title="Kofein" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target">Bosanski</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Cafe%C3%AFna" title="Cafeïna – Catalan" lang="ca" hreflang="ca" data-title="Cafeïna" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Kofein" title="Kofein – Czech" lang="cs" hreflang="cs" data-title="Kofein" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-sn mw-list-item"><a href="https://sn.wikipedia.org/wiki/Kafeni" title="Kafeni – Shona" lang="sn" hreflang="sn" data-title="Kafeni" data-language-autonym="ChiShona" data-language-local-name="Shona" class="interlanguage-link-target">ChiShona</a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Caffein" title="Caffein – Welsh" lang="cy" hreflang="cy" data-title="Caffein" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target">Cymraeg</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Koffein" title="Koffein – Danish" lang="da" hreflang="da" data-title="Koffein" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Coffein" title="Coffein – German" lang="de" hreflang="de" data-title="Coffein" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Kofeiin" title="Kofeiin – Estonian" lang="et" hreflang="et" data-title="Kofeiin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target">Eesti</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CE%B1%CF%86%CE%B5%CE%90%CE%BD%CE%B7" title="Καφεΐνη – Greek" lang="el" hreflang="el" data-title="Καφεΐνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Cafe%C3%ADna" title="Cafeína – Spanish" lang="es" hreflang="es" data-title="Cafeína" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Kafeino" title="Kafeino – Esperanto" lang="eo" hreflang="eo" data-title="Kafeino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target">Esperanto</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Kafeina" title="Kafeina – Basque" lang="eu" hreflang="eu" data-title="Kafeina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target">Euskara</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D8%A7%D9%81%D8%A6%DB%8C%D9%86" title="کافئین – Persian" lang="fa" hreflang="fa" data-title="کافئین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://fr.wikipedia.org/wiki/Caf%C3%A9ine" title="Caféine – French" lang="fr" hreflang="fr" data-title="Caféine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Caif%C3%A9in" title="Caiféin – Irish" lang="ga" hreflang="ga" data-title="Caiféin" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target">Gaeilge</a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Cafe%C3%ADna" title="Cafeína – Galician" lang="gl" hreflang="gl" data-title="Cafeína" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-got mw-list-item"><a href="https://got.wikipedia.org/wiki/%F0%90%8C%BA%F0%90%8C%B0%F0%90%8C%B7%F0%90%8D%85%F0%90%8C%B4%F0%90%8C%B9%F0%90%8C%BD%F0%90%8D%83" title="𐌺𐌰𐌷𐍅𐌴𐌹𐌽𐍃 – Gothic" lang="got" hreflang="got" data-title="𐌺𐌰𐌷𐍅𐌴𐌹𐌽𐍃" data-language-autonym="𐌲𐌿𐍄𐌹𐍃𐌺" data-language-local-name="Gothic" class="interlanguage-link-target">𐌲𐌿𐍄𐌹𐍃𐌺</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%B9%B4%ED%8E%98%EC%9D%B8" title="카페인 – Korean" lang="ko" hreflang="ko" data-title="카페인" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%BF%D5%B8%D6%86%D5%A5%D5%AB%D5%B6" title="Կոֆեին – Armenian" lang="hy" hreflang="hy" data-title="Կոֆեին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target">Հայերեն</a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%95%E0%A5%88%E0%A4%AB%E0%A4%BC%E0%A5%80%E0%A4%A8" title="कैफ़ीन – Hindi" lang="hi" hreflang="hi" data-title="कैफ़ीन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target">हिन्दी</a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Kofein" title="Kofein – Croatian" lang="hr" hreflang="hr" data-title="Kofein" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Kafeino" title="Kafeino – Ido" lang="io" hreflang="io" data-title="Kafeino" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target">Ido</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Kafeina" title="Kafeina – Indonesian" lang="id" hreflang="id" data-title="Kafeina" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-ia mw-list-item"><a href="https://ia.wikipedia.org/wiki/Caffeina" title="Caffeina – Interlingua" lang="ia" hreflang="ia" data-title="Caffeina" data-language-autonym="Interlingua" data-language-local-name="Interlingua" class="interlanguage-link-target">Interlingua</a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Koff%C3%ADn" title="Koffín – Icelandic" lang="is" hreflang="is" data-title="Koffín" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target">Íslenska</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Caffeina" title="Caffeina – Italian" lang="it" hreflang="it" data-title="Caffeina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A7%D7%A4%D7%90%D7%99%D7%9F" title="קפאין – Hebrew" lang="he" hreflang="he" data-title="קפאין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Kaf%C3%A9in" title="Kaféin – Javanese" lang="jv" hreflang="jv" data-title="Kaféin" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target">Jawa</a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%95%E0%B3%86%E0%B2%AB%E0%B3%80%E0%B2%A8%E0%B3%8D" title="ಕೆಫೀನ್ – Kannada" lang="kn" hreflang="kn" data-title="ಕೆಫೀನ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target">ಕನ್ನಡ</a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%99%E1%83%9D%E1%83%A4%E1%83%94%E1%83%98%E1%83%9C%E1%83%98" title="კოფეინი – Georgian" lang="ka" hreflang="ka" data-title="კოფეინი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target">ქართული</a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9A%D0%BE%D1%84%D0%B5%D0%B8%D0%BD" title="Кофеин – Kazakh" lang="kk" hreflang="kk" data-title="Кофеин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target">Қазақша</a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Kafeini" title="Kafeini – Swahili" lang="sw" hreflang="sw" data-title="Kafeini" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target">Kiswahili</a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Caffeinum" title="Caffeinum – Latin" lang="la" hreflang="la" data-title="Caffeinum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target">Latina</a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Kofe%C4%ABns" title="Kofeīns – Latvian" lang="lv" hreflang="lv" data-title="Kofeīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target">Latviešu</a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Kofeinas" title="Kofeinas – Lithuanian" lang="lt" hreflang="lt" data-title="Kofeinas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target">Lietuvių</a></li><li class="interlanguage-link interwiki-lij mw-list-item"><a href="https://lij.wikipedia.org/wiki/Caffeinna" title="Caffeinna – Ligurian" lang="lij" hreflang="lij" data-title="Caffeinna" data-language-autonym="Ligure" data-language-local-name="Ligurian" class="interlanguage-link-target">Ligure</a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Caffeina" title="Caffeina – Lombard" lang="lmo" hreflang="lmo" data-title="Caffeina" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target">Lombard</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Koffein" title="Koffein – Hungarian" lang="hu" hreflang="hu" data-title="Koffein" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9A%D0%BE%D1%84%D0%B5%D0%B8%D0%BD" title="Кофеин – Macedonian" lang="mk" hreflang="mk" data-title="Кофеин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target">Македонски</a></li><li class="interlanguage-link interwiki-mg mw-list-item"><a href="https://mg.wikipedia.org/wiki/Kafeinina" title="Kafeinina – Malagasy" lang="mg" hreflang="mg" data-title="Kafeinina" data-language-autonym="Malagasy" data-language-local-name="Malagasy" class="interlanguage-link-target">Malagasy</a></li><li class="interlanguage-link interwiki-arz mw-list-item"><a href="https://arz.wikipedia.org/wiki/%D9%83%D8%A7%D9%81%D9%8A%D9%8A%D9%86" title="كافيين – Egyptian Arabic" lang="arz" hreflang="arz" data-title="كافيين" data-language-autonym="مصرى" data-language-local-name="Egyptian Arabic" class="interlanguage-link-target">مصرى</a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Kafeina" title="Kafeina – Malay" lang="ms" hreflang="ms" data-title="Kafeina" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%80%E1%80%B1%E1%80%96%E1%80%AD%E1%80%94%E1%80%BA%E1%80%B8" title="ကေဖိန်း – Burmese" lang="my" hreflang="my" data-title="ကေဖိန်း" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target">မြန်မာဘာသာ</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cafe%C3%AFne" title="Cafeïne – Dutch" lang="nl" hreflang="nl" data-title="Cafeïne" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-new mw-list-item"><a href="https://new.wikipedia.org/wiki/%E0%A4%95%E0%A5%8D%E0%A4%AF%E0%A4%BE%E0%A4%AB%E0%A4%BF%E0%A4%A8" title="क्याफिन – Newari" lang="new" hreflang="new" data-title="क्याफिन" data-language-autonym="नेपाल भाषा" data-language-local-name="Newari" class="interlanguage-link-target">नेपाल भाषा</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AB%E3%83%95%E3%82%A7%E3%82%A4%E3%83%B3" title="カフェイン – Japanese" lang="ja" hreflang="ja" data-title="カフェイン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-frr mw-list-item"><a href="https://frr.wikipedia.org/wiki/Coffein" title="Coffein – Northern Frisian" lang="frr" hreflang="frr" data-title="Coffein" data-language-autonym="Nordfriisk" data-language-local-name="Northern Frisian" class="interlanguage-link-target">Nordfriisk</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Koffein" title="Koffein – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Koffein" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Koffein" title="Koffein – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Koffein" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target">Norsk nynorsk</a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Cafe%C3%AFna" title="Cafeïna – Occitan" lang="oc" hreflang="oc" data-title="Cafeïna" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target">Occitan</a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Kofein" title="Kofein – Uzbek" lang="uz" hreflang="uz" data-title="Kofein" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target">Oʻzbekcha / ўзбекча</a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%DA%A9%DB%8C%D9%81%DB%8C%D9%86" title="کیفین – Western Punjabi" lang="pnb" hreflang="pnb" data-title="کیفین" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target">پنجابی</a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%DA%A9%D9%88%D9%81%DB%8C%D9%86" title="کوفین – Pashto" lang="ps" hreflang="ps" data-title="کوفین" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target">پښتو</a></li><li class="interlanguage-link interwiki-km mw-list-item"><a href="https://km.wikipedia.org/wiki/%E1%9E%80%E1%9E%B6%E1%9E%A0%E1%9F%92%E1%9E%9C%E1%9F%81%E1%9E%A2%E1%9F%8A%E1%9E%B8%E1%9E%93" title="កាហ្វេអ៊ីន – Khmer" lang="km" hreflang="km" data-title="កាហ្វេអ៊ីន" data-language-autonym="ភាសាខ្មែរ" data-language-local-name="Khmer" class="interlanguage-link-target">ភាសាខ្មែរ</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kofeina" title="Kofeina – Polish" lang="pl" hreflang="pl" data-title="Kofeina" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Cafe%C3%ADna" title="Cafeína – Portuguese" lang="pt" hreflang="pt" data-title="Cafeína" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Cofein%C4%83" title="Cofeină – Romanian" lang="ro" hreflang="ro" data-title="Cofeină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9A%D0%BE%D1%84%D0%B5%D0%B8%D0%BD" title="Кофеин – Russian" lang="ru" hreflang="ru" data-title="Кофеин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sah mw-list-item"><a href="https://sah.wikipedia.org/wiki/%D0%9A%D0%BE%D1%84%D0%B5%D0%B8%D0%BD" title="Кофеин – Yakut" lang="sah" hreflang="sah" data-title="Кофеин" data-language-autonym="Саха тыла" data-language-local-name="Yakut" class="interlanguage-link-target">Саха тыла</a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Caffeine" title="Caffeine – Scots" lang="sco" hreflang="sco" data-title="Caffeine" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target">Scots</a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Kafeina" title="Kafeina – Albanian" lang="sq" hreflang="sq" data-title="Kafeina" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target">Shqip</a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Caffeine" title="Caffeine – Simple English" lang="en-simple" hreflang="en-simple" data-title="Caffeine" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target">Simple English</a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kofe%C3%ADn" title="Kofeín – Slovak" lang="sk" hreflang="sk" data-title="Kofeín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target">Slovenčina</a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Kofein" title="Kofein – Slovenian" lang="sl" hreflang="sl" data-title="Kofein" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%DA%A9%D8%A7%D9%81%D8%A7%DB%8C%D9%86" title="کافاین – Central Kurdish" lang="ckb" hreflang="ckb" data-title="کافاین" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target">کوردی</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%9A%D0%BE%D1%84%D0%B5%D0%B8%D0%BD" title="Кофеин – Serbian" lang="sr" hreflang="sr" data-title="Кофеин" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Kofein" title="Kofein – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Kofein" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Kaf%C3%A9in" title="Kaféin – Sundanese" lang="su" hreflang="su" data-title="Kaféin" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target">Sunda</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Kofeiini" title="Kofeiini – Finnish" lang="fi" hreflang="fi" data-title="Kofeiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Koffein" title="Koffein – Swedish" lang="sv" hreflang="sv" data-title="Koffein" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Kapeina" title="Kapeina – Tagalog" lang="tl" hreflang="tl" data-title="Kapeina" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target">Tagalog</a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AE%BE%E0%AE%83%E0%AE%B5%E0%AF%80%E0%AE%A9%E0%AF%8D" title="காஃவீன் – Tamil" lang="ta" hreflang="ta" data-title="காஃவீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target">தமிழ்</a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%95%E0%B1%86%E0%B0%AB%E0%B0%BF%E0%B0%A8%E0%B1%8D" title="కెఫిన్ – Telugu" lang="te" hreflang="te" data-title="కెఫిన్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target">తెలుగు</a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%81%E0%B8%B2%E0%B9%80%E0%B8%9F%E0%B8%AD%E0%B8%B5%E0%B8%99" title="กาเฟอีน – Thai" lang="th" hreflang="th" data-title="กาเฟอีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target">ไทย</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Kafein" title="Kafein – Turkish" lang="tr" hreflang="tr" data-title="Kafein" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-tk mw-list-item"><a href="https://tk.wikipedia.org/wiki/Kafein" title="Kafein – Turkmen" lang="tk" hreflang="tk" data-title="Kafein" data-language-autonym="Türkmençe" data-language-local-name="Turkmen" class="interlanguage-link-target">Türkmençe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D0%BE%D1%84%D0%B5%D1%97%D0%BD" title="Кофеїн – Ukrainian" lang="uk" hreflang="uk" data-title="Кофеїн" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%DA%A9%DB%8C%D9%81%DB%8C%D9%86" title="کیفین – Urdu" lang="ur" hreflang="ur" data-title="کیفین" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target">اردو</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Cafein" title="Cafein – Vietnamese" lang="vi" hreflang="vi" data-title="Cafein" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Kafeina" title="Kafeina – Waray" lang="war" hreflang="war" data-title="Kafeina" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target">Winaray</a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E5%92%96%E5%95%A1%E5%9B%A0" title="咖啡因 – Wu" lang="wuu" hreflang="wuu" data-title="咖啡因" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target">吴语</a></li><li class="interlanguage-link interwiki-yi mw-list-item"><a href="https://yi.wikipedia.org/wiki/%D7%A7%D7%90%D7%A4%D7%A2%D7%99%D7%9F" title="קאפעין – Yiddish" lang="yi" hreflang="yi" data-title="קאפעין" data-language-autonym="ייִדיש" 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id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Central nervous system stimulant</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 stimulant drug. For other uses, see <a href="/wiki/Caffeine_(disambiguation)" class="mw-disambig" title="Caffeine (disambiguation)">Caffeine (disambiguation)</a>.</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title">Caffeine</caption><tbody><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Caffeine_structure.svg" class="mw-file-description"><img alt="2D structure of caffeine" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Caffeine_structure.svg/250px-Caffeine_structure.svg.png" decoding="async" width="187" height="182" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Caffeine_structure.svg/330px-Caffeine_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Caffeine_structure.svg/500px-Caffeine_structure.svg.png 2x" data-file-width="512" data-file-height="497" /></a></td></tr><tr><td colspan="2" class="infobox-image"><table style="width:100%; margin:0;"><tbody><tr> <td style="vertical-align:top; text-align:center; width:50%;"><a href="/wiki/File:Caffeine_molecule_ball_from_xtal_(1).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cc/Caffeine_molecule_ball_from_xtal_%281%29.png/120px-Caffeine_molecule_ball_from_xtal_%281%29.png" decoding="async" width="110" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cc/Caffeine_molecule_ball_from_xtal_%281%29.png/250px-Caffeine_molecule_ball_from_xtal_%281%29.png 1.5x" data-file-width="3000" data-file-height="2682" /></a></td> <td style="vertical-align:top; text-align:center; width:50%;"><a href="/wiki/File:Caffeine_molecule_spacefill_from_xtal_(1).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Caffeine_molecule_spacefill_from_xtal_%281%29.png/120px-Caffeine_molecule_spacefill_from_xtal_%281%29.png" decoding="async" width="110" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Caffeine_molecule_spacefill_from_xtal_%281%29.png/250px-Caffeine_molecule_spacefill_from_xtal_%281%29.png 1.5x" data-file-width="3000" data-file-height="2751" /></a></td> </tr></tbody></table></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/kæˈfiːn, ˈkæfiːn/</a> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Guaranine Methyltheobromine 1,3,7-Trimethylxanthine 7-methyltheophylline<a href="#cite_note-1">[1]</a> Theine</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"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/caffeine-caffeine-and-sodium-benzoate-injection-caffeine-citrate.html">Monograph</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><abbr class="country-name" title="United States">US</abbr> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Caffeine">Caffeine</a></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><abbr class="country-name" title="Australia">AU</abbr>: A</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 liability</a></th><td class="infobox-data"><a href="/wiki/Physical_dependence" title="Physical dependence">Physical</a>: Moderate 13% and variable low–high 10–73%<a href="#cite_note-pmid15448977-2">[2]</a> <a href="/wiki/Psychological_dependence" title="Psychological dependence">Psychological</a>: Low–moderate<a href="#cite_note-pmid15448977-2">[2]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Addiction" title="Addiction">Addiction liability</a></th><td class="infobox-data">Relatively low: 9%<a href="#cite_note-pmid24761279-3">[3]</a> [<a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">failed verification</a>]</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 administration</a></th><td class="infobox-data">Common: <a href="/wiki/Oral_administration" title="Oral administration">By mouth</a> Medical: <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">Intravenous</a> Uncommon: <a href="/wiki/Insufflation_(medicine)" title="Insufflation (medicine)">Insufflation</a>, <a href="/wiki/Rectal_administration" title="Rectal administration">rectal</a>, <a href="/wiki/Caffeine_patch" title="Caffeine patch">transdermal</a>, <a href="/wiki/Topical" class="mw-redirect" title="Topical">topical</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/Adenosinergic" title="Adenosinergic">Adenosinergic</a>; <a href="/wiki/Eugeroic" title="Eugeroic">Eugeroic</a>; <a href="/wiki/Nootropic" title="Nootropic">Nootropic</a>; <a href="/wiki/Anxiogenic" title="Anxiogenic">Anxiogenic</a>; <a href="/wiki/Analeptic" title="Analeptic">Analeptic</a>; <a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">PDE inhibitor</a>; <a href="/wiki/Diuretic" title="Diuretic">Diuretic</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_N06B" class="mw-redirect" title="ATC code N06B">N06BC01</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N06BC01">WHO</a>) <a href="/wiki/ATC_code_D11" title="ATC code D11">D11AX26</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=D11AX26">WHO</a>), <a href="/wiki/ATC_code_V04" title="ATC code V04">V04CG30</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=V04CG30">WHO</a>)</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><abbr class="country-name" title="Australia">AU</abbr>: Unscheduled</li> <li><abbr class="country-name" title="Brazil">BR</abbr>: <a href="/wiki/Brazilian_Controlled_Drugs_and_Substances_Act" title="Brazilian Controlled Drugs and Substances Act">Unscheduled</a></li> <li><abbr class="country-name" title="Canada">CA</abbr>: Unscheduled</li> <li><abbr class="country-name" title="Germany">DE</abbr>: Unscheduled</li> <li><abbr class="country-name" title="New Zealand">NZ</abbr>: Unscheduled</li> <li><abbr class="country-name" title="United Kingdom">UK</abbr>: <a href="/wiki/General_sales_list" class="mw-redirect" title="General sales list">General sales list</a> (GSL, OTC)</li> <li><abbr class="country-name" title="United States">US</abbr>: Unscheduled</li> <li><abbr class="country-name" title="United Nations">UN</abbr>: Unscheduled</li> <li><a href="/wiki/China" title="China">CN</a>: <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">OTC</a></li></ul> In general Legal for all uses</div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">99%<a href="#cite_note-Poleszak_2015-4">[4]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">10–36%<a href="#cite_note-Drugbank-Caffeine-5">[5]</a></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">Primary: <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a><a href="#cite_note-Drugbank-Caffeine-5">[5]</a> Minor: <a href="/wiki/CYP2E1" title="CYP2E1">CYP2E1</a>,<a href="#cite_note-Drugbank-Caffeine-5">[5]</a> <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>,<a href="#cite_note-Drugbank-Caffeine-5">[5]</a> <a href="/wiki/CYP2C8" title="CYP2C8">CYP2C8</a>,<a href="#cite_note-Drugbank-Caffeine-5">[5]</a> <a href="/wiki/CYP2C9" title="CYP2C9">CYP2C9</a><a href="#cite_note-Drugbank-Caffeine-5">[5]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data">• <a href="/wiki/Paraxanthine" title="Paraxanthine">Paraxanthine</a> 84% • <a href="/wiki/Theobromine" title="Theobromine">Theobromine</a> 12% • <a href="/wiki/Theophylline" title="Theophylline">Theophylline</a> 4%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Onset_of_action" title="Onset of action">Onset of action</a></th><td class="infobox-data">45 minutes–1 hour<a href="#cite_note-Poleszak_2015-4">[4]</a><a href="#cite_note-6">[6]</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 half-life</a></th><td class="infobox-data">Adults: 3–7 hours<a href="#cite_note-Drugbank-Caffeine-5">[5]</a> Infants (full term): 8 hours<a href="#cite_note-Drugbank-Caffeine-5">[5]</a> Infants (premature): 100 hours<a href="#cite_note-Drugbank-Caffeine-5">[5]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pharmacodynamics#Duration_of_action" title="Pharmacodynamics">Duration of action</a></th><td class="infobox-data">3–4 hours<a href="#cite_note-Poleszak_2015-4">[4]</a></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">Urine (100%)</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione</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><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=58-08-2">58-08-2</a></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> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/2519">2519</a></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><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=407">407</a></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><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00201">DB00201</a></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><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.2424.html">2424</a></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><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/3G6A5W338E">3G6A5W338E</a></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><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00528">D00528</a></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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:27732">CHEBI:27732</a></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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL113">ChEMBL113</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/NIAID_ChemDB" title="NIAID ChemDB">NIAID ChemDB</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemdb.niaid.nih.gov/CompoundDetails.aspx?AIDSNO=none">none</a></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>CFF (<a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=CFF">PDBe</a>, <a rel="nofollow" class="external text" href="https://www.rcsb.org/ligand/CFF">RCSB PDB</a>)</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> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID0020232">DTXSID0020232</a> <a href="https://www.wikidata.org/wiki/Q60235#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></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">ECHA InfoCard</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.329">100.000.329</a> <a href="https://www.wikidata.org/wiki/Q60235#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></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data">C8H10N4O2</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">194.194 g·mol−1</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><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CN1C%3DNC2%3DC1C%28%3DO%29N%28C%28%3DO%29N2C%29C">Interactive image</a></li></ul></div></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">1.23 g/cm3</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">235 to 238 °C (455 to 460 °F) (anhydrous)<a href="#cite_note-Pubchem_properties-7">[7]</a><a href="#cite_note-ChemSpider-8">[8]</a></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%;">CN1C=NC2=C1C(=O)N(C(=O)N2C)C</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/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3</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:RYYVLZVUVIJVGH-UHFFFAOYSA-N</div></li></ul> </div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Data page</th></tr><tr><td colspan="2" class="infobox-full-data"><a href="/wiki/Caffeine_(data_page)" title="Caffeine (data page)">Caffeine (data page)</a></td></tr></tbody></table> Caffeine is a <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> (CNS) <a href="/wiki/Stimulant" title="Stimulant">stimulant</a> of the <a href="/wiki/Methylxanthine" class="mw-redirect" title="Methylxanthine">methylxanthine</a> <a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">class</a> and is the most commonly consumed <a href="/wiki/Psychoactive_drug" title="Psychoactive drug">psychoactive</a> substance globally.<a href="#cite_note-pmid1356551-9">[9]</a><a href="#cite_note-:4-10">[10]</a> It is mainly used for its <a href="/wiki/Eugeroic" title="Eugeroic">eugeroic</a> (<a href="/wiki/Wakefulness" title="Wakefulness">wakefulness</a> promoting), <a href="/wiki/Ergogenic" class="mw-redirect" title="Ergogenic">ergogenic</a> (physical performance-enhancing), or <a href="/wiki/Nootropic" title="Nootropic">nootropic</a> (cognitive-enhancing) properties.<a href="#cite_note-caffeine_&_theanine-11">[11]</a><a href="#cite_note-Continuum-12">[12]</a> Caffeine acts by blocking binding of <a href="/wiki/Adenosine" title="Adenosine">adenosine</a> at a number of <a href="/wiki/Adenosine_receptor" title="Adenosine receptor">adenosine receptor</a> types, inhibiting the centrally <a href="/wiki/Depressant" title="Depressant">depressant</a> effects of adenosine and enhancing the release of <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a>.<a href="#cite_note-13">[13]</a> Caffeine has a three-dimensional structure similar to that of adenosine, which allows it to bind and block its receptors.<a href="#cite_note-14">[14]</a> Caffeine also increases <a href="/wiki/Cyclic_adenosine_monophosphate" title="Cyclic adenosine monophosphate">cyclic AMP</a> levels through nonselective <a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">inhibition of phosphodiesterase</a>, increases calcium release from intracellular stores, and <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonizes</a> <a href="/wiki/GABA_receptor" title="GABA receptor">GABA receptors</a>, although these mechanisms typically occur at concentrations beyond usual human consumption.<a href="#cite_note-:4-10">[10]</a><a href="#cite_note-15">[15]</a> Caffeine is a bitter, white crystalline <a href="/wiki/Purine" title="Purine">purine</a>, a methylxanthine <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a>, and is chemically related to the <a href="/wiki/Adenine" title="Adenine">adenine</a> and <a href="/wiki/Guanine" title="Guanine">guanine</a> <a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">bases</a> of <a href="/wiki/DNA" title="DNA">deoxyribonucleic acid</a> (DNA) and <a href="/wiki/RNA" title="RNA">ribonucleic acid</a> (RNA). It is found in the seeds, fruits, nuts, or leaves of a number of plants native to Africa, East Asia and South America<a href="#cite_note-Caballero_Finglas_Toldra_2015-16">[16]</a> and helps to protect them against herbivores and from competition by preventing the germination of nearby seeds,<a href="#cite_note-Myers_2007-17">[17]</a> as well as encouraging consumption by select animals such as <a href="/wiki/Honey_bees" class="mw-redirect" title="Honey bees">honey bees</a>.<a href="#cite_note-pmid23471406-18">[18]</a> The best-known source of caffeine is the <a href="/wiki/Coffee_bean" title="Coffee bean">coffee bean</a>, the seed of the <a href="/wiki/Coffea" title="Coffea">Coffea</a> plant. People may drink <a href="/wiki/Beverages" class="mw-redirect" title="Beverages">beverages</a> containing caffeine to relieve or prevent drowsiness and to improve cognitive performance. To make these drinks, caffeine is extracted by <a href="/wiki/Steeping" title="Steeping">steeping</a> the plant product in water, a process called <a href="/wiki/Infusion" title="Infusion">infusion</a>. Caffeine-containing drinks, such as <a href="/wiki/Coffee" title="Coffee">coffee</a>, <a href="/wiki/Tea" title="Tea">tea</a>, and <a href="/wiki/Cola" title="Cola">cola</a>, are consumed globally in high volumes. In 2020, almost 10 million tonnes of coffee beans were consumed globally.<a href="#cite_note-19">[19]</a> Caffeine is the world's most widely consumed <a href="/wiki/Psychoactive_drug" title="Psychoactive drug">psychoactive drug</a>.<a href="#cite_note-abc.net-20">[20]</a><a href="#cite_note-21">[21]</a> Unlike most other psychoactive substances, caffeine remains largely unregulated and legal in nearly all parts of the world. Caffeine is also an outlier as its use is seen as socially acceptable in most cultures with it even being encouraged. Caffeine has both positive and negative <a href="/wiki/Health_effects_of_coffee" title="Health effects of coffee">health effects</a>. It can treat and prevent the premature infant breathing disorders <a href="/wiki/Bronchopulmonary_dysplasia" title="Bronchopulmonary dysplasia">bronchopulmonary dysplasia</a> of prematurity and <a href="/wiki/Apnea_of_prematurity" title="Apnea of prematurity">apnea of prematurity</a>. <a href="/wiki/Caffeine_citrate" title="Caffeine citrate">Caffeine citrate</a> is on the <a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO Model List of Essential Medicines</a>.<a href="#cite_note-WHOMedList-22">[22]</a> It may confer a modest protective effect against some diseases,<a href="#cite_note-23">[23]</a> including <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a>.<a href="#cite_note-Qi_2014-24">[24]</a> Some people experience <a href="/wiki/Insomnia" title="Insomnia">sleep disruption</a> or anxiety if they consume caffeine,<a href="#cite_note-25">[25]</a> but others show little disturbance. Evidence of a risk during pregnancy is equivocal; some authorities recommend that pregnant women limit caffeine to the equivalent of two cups of coffee per day or less.<a href="#cite_note-Jah2015-26">[26]</a><a href="#cite_note-ACOG_policy_462_caffeine-27">[27]</a> Caffeine can produce a mild form of <a href="/wiki/Drug_dependence" class="mw-redirect" title="Drug dependence">drug dependence</a> – associated with <a href="/wiki/Drug_withdrawal" title="Drug withdrawal">withdrawal symptoms</a> such as sleepiness, headache, and irritability – when an individual stops using caffeine after repeated daily intake.<a href="#cite_note-Nestler_caffeine_dependence-addiction-28">[28]</a><a href="#cite_note-DSM-5_definitions_+_addiction-dependence_distinction_+_Caffeine_use_disorder-29">[29]</a><a href="#cite_note-pmid15448977-2">[2]</a> <a href="/wiki/Drug_tolerance" title="Drug tolerance">Tolerance</a> to the autonomic effects of increased blood pressure and heart rate, and increased urine output, develops with chronic use (i.e., these symptoms become less pronounced or do not occur following consistent use).<a href="#cite_note-30">[30]</a> Caffeine is classified by the U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) as <a href="/wiki/Generally_recognized_as_safe" title="Generally recognized as safe">generally recognized as safe</a>. Toxic doses, over 10 grams per day for an adult, are much higher than the typical dose of under 500 milligrams per day.<a href="#cite_note-31">[31]</a> The <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> reported that up to 400 mg of caffeine per day (around 5.7 mg/kg of body mass per day) does not raise safety concerns for non-pregnant adults, while intakes up to 200 mg per day for pregnant and lactating women do not raise safety concerns for the fetus or the breast-fed infants.<a href="#cite_note-32">[32]</a> A cup of coffee contains 80–175 mg of caffeine, depending on what "bean" (seed) is used, how it is roasted, and how it is prepared (e.g., <a href="/wiki/Drip_brew" class="mw-redirect" title="Drip brew">drip</a>, <a href="/wiki/Coffee_percolator" title="Coffee percolator">percolation</a>, or <a href="/wiki/Espresso" title="Espresso">espresso</a>).<a href="#cite_note-33">[33]</a> Thus it requires roughly 50–100 ordinary cups of coffee to reach the toxic dose. However, pure powdered caffeine, which is available as a <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a>, can be lethal in tablespoon-sized amounts. <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>[<a href="/w/index.php?title=Caffeine&action=edit&section=1" title="Edit section: Uses">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Medical">Medical</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=2" title="Edit section: Medical">edit</a>]</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/Caffeine_citrate" title="Caffeine citrate">Caffeine citrate</a></div> Caffeine is used for both prevention<a href="#cite_note-pmid21815280-34">[34]</a> and treatment<a href="#cite_note-pmid16210843-35">[35]</a> of <a href="/wiki/Bronchopulmonary_dysplasia" title="Bronchopulmonary dysplasia">bronchopulmonary dysplasia</a> in <a href="/wiki/Premature_birth" class="mw-redirect" title="Premature birth">premature</a> infants. It may improve weight gain during therapy<a href="#cite_note-pmid16707748-36">[36]</a> and reduce the incidence of <a href="/wiki/Cerebral_palsy" title="Cerebral palsy">cerebral palsy</a> as well as reduce language and cognitive delay.<a href="#cite_note-caffeine_for_AOP_NEJM-37">[37]</a><a href="#cite_note-caffeine_for_AOP_JAMA_2012-38">[38]</a> On the other hand, subtle long-term side effects are possible.<a href="#cite_note-Funk-39">[39]</a> Caffeine is used as a primary treatment for <a href="/wiki/Apnea_of_prematurity" title="Apnea of prematurity">apnea of prematurity</a>,<a href="#cite_note-pmid21127467-40">[40]</a> but not prevention.<a href="#cite_note-41">[41]</a><a href="#cite_note-IUPHAR-42">[42]</a> It is also used for <a href="/wiki/Orthostatic_hypotension" title="Orthostatic hypotension">orthostatic hypotension</a> treatment.<a href="#cite_note-43">[43]</a><a href="#cite_note-IUPHAR-42">[42]</a><a href="#cite_note-44">[44]</a> Some people use caffeine-containing beverages such as coffee or tea to try to treat their <a href="/wiki/Asthma" title="Asthma">asthma</a>.<a href="#cite_note-Alf2017-45">[45]</a> Evidence to support this practice is poor.<a href="#cite_note-Alf2017-45">[45]</a> It appears that caffeine in low doses improves airway function in people with asthma, increasing <a href="/wiki/Forced_expiratory_volume" class="mw-redirect" title="Forced expiratory volume">forced expiratory volume</a> (FEV1) by 5% to 18% for up to four hours.<a href="#cite_note-pmid20091514-46">[46]</a> The addition of caffeine (100–130 mg) to commonly prescribed pain relievers such as <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol</a> or <a href="/wiki/Ibuprofen" title="Ibuprofen">ibuprofen</a> modestly improves the proportion of people who achieve <a href="/wiki/Analgesia" class="mw-redirect" title="Analgesia">pain relief</a>.<a href="#cite_note-Derry-47">[47]</a> Consumption of caffeine after abdominal surgery shortens the time to recovery of normal bowel function and shortens length of hospital stay.<a href="#cite_note-48">[48]</a> Caffeine was formerly used as a second-line treatment for <a href="/wiki/ADHD" class="mw-redirect" title="ADHD">ADHD</a>. It is considered less effective than <a href="/wiki/Methylphenidate" title="Methylphenidate">methylphenidate</a> or <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a> but more so than placebo for children with ADHD.<a href="#cite_note-49">[49]</a><a href="#cite_note-Downs-50">[50]</a> Children, adolescents, and adults with ADHD are more likely to consume caffeine, perhaps as a form of <a href="/wiki/Self-medication" title="Self-medication">self-medication</a>.<a href="#cite_note-Downs-50">[50]</a><a href="#cite_note-51">[51]</a> <div class="mw-heading mw-heading3"><h3 id="Enhancing_performance">Enhancing performance</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=3" title="Edit section: Enhancing performance">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Cognitive_performance">Cognitive performance</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=4" title="Edit section: Cognitive performance">edit</a>]</div> Caffeine is a <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> stimulant that may reduce <a href="/wiki/Fatigue_(medical)" class="mw-redirect" title="Fatigue (medical)">fatigue</a> and <a href="/wiki/Drowsiness" class="mw-redirect" title="Drowsiness">drowsiness</a>.<a href="#cite_note-pmid1356551-9">[9]</a> At normal doses, caffeine has variable <a href="/wiki/Effect_of_caffeine_on_memory" title="Effect of caffeine on memory">effects on learning and memory</a>, but it generally improves <a href="/wiki/Reaction_time" class="mw-redirect" title="Reaction time">reaction time</a>, <a href="/wiki/Wakefulness" title="Wakefulness">wakefulness</a>, concentration, and <a href="/wiki/Motor_coordination" title="Motor coordination">motor coordination</a>.<a href="#cite_note-effects-52">[52]</a><a href="#cite_note-Cog10-53">[53]</a> The amount of caffeine needed to produce these effects varies from person to person, depending on body size and degree of tolerance.<a href="#cite_note-effects-52">[52]</a> The desired effects arise approximately one hour after consumption, and the desired effects of a moderate dose usually subside after about three or four hours.<a href="#cite_note-Poleszak_2015-4">[4]</a> Caffeine can delay or prevent <a href="/wiki/Sleep" title="Sleep">sleep</a> and improves task performance during sleep deprivation.<a href="#cite_note-pmid21531247-54">[54]</a> <a href="/wiki/Shift_work" title="Shift work">Shift workers</a> who use caffeine make fewer mistakes that could result from drowsiness.<a href="#cite_note-pmid20464765-55">[55]</a> Caffeine in a dose dependent manner increases alertness in both fatigued and normal individuals.<a href="#cite_note-pmid27612937-56">[56]</a> A <a href="/wiki/Systematic_review" title="Systematic review">systematic review</a> and <a href="/wiki/Meta-analysis" title="Meta-analysis">meta-analysis</a> from 2014 found that concurrent caffeine and <a href="/wiki/L-theanine" class="mw-redirect" title="L-theanine">L-theanine</a> use has synergistic psychoactive effects that promote alertness, attention, and <a href="/wiki/Task_switching_(psychology)" title="Task switching (psychology)">task switching</a>;<a href="#cite_note-caffeine_and_theanine-57">[57]</a> these effects are most pronounced during the first hour post-dose.<a href="#cite_note-caffeine_and_theanine-57">[57]</a> <div class="mw-heading mw-heading4"><h4 id="Physical_performance">Physical performance</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=5" title="Edit section: Physical performance">edit</a>]</div> Caffeine is a proven <a href="/wiki/Ergogenic_aid" class="mw-redirect" title="Ergogenic aid">ergogenic aid</a> in humans.<a href="#cite_note-Peripheral_and_central_ergogenic_effects-58">[58]</a> Caffeine improves athletic performance in <a href="/wiki/Aerobic_exercise" title="Aerobic exercise">aerobic</a> (especially <a href="/wiki/Endurance_sports" class="mw-redirect" title="Endurance sports">endurance sports</a>) and <a href="/wiki/Anaerobic_exercise" title="Anaerobic exercise">anaerobic</a> conditions.<a href="#cite_note-Peripheral_and_central_ergogenic_effects-58">[58]</a> Moderate doses of caffeine (around 5 mg/kg<a href="#cite_note-Peripheral_and_central_ergogenic_effects-58">[58]</a>) can improve sprint performance,<a href="#cite_note-pmid21058748-59">[59]</a> cycling and running time trial performance,<a href="#cite_note-Peripheral_and_central_ergogenic_effects-58">[58]</a> endurance (i.e., it delays the onset of <a href="/wiki/Muscle_fatigue" title="Muscle fatigue">muscle fatigue</a> and <a href="/wiki/Central_fatigue" class="mw-redirect" title="Central fatigue">central fatigue</a>),<a href="#cite_note-Peripheral_and_central_ergogenic_effects-58">[58]</a><a href="#cite_note-pmid21411838-60">[60]</a><a href="#cite_note-Ergogenics-61">[61]</a> and cycling power output.<a href="#cite_note-Peripheral_and_central_ergogenic_effects-58">[58]</a> Caffeine increases <a href="/wiki/Basal_metabolic_rate" title="Basal metabolic rate">basal metabolic rate</a> in adults.<a href="#cite_note-pmid7369170-62">[62]</a><a href="#cite_note-pmid2912010-63">[63]</a><a href="#cite_note-pmid7486839-64">[64]</a> Caffeine ingestion prior to aerobic exercise increases fat oxidation, particularly in persons with low physical fitness.<a href="#cite_note-65">[65]</a> Caffeine improves muscular strength and power,<a href="#cite_note-66">[66]</a> and may enhance muscular endurance.<a href="#cite_note-67">[67]</a> Caffeine also enhances performance on anaerobic tests.<a href="#cite_note-68">[68]</a> Caffeine consumption before constant load exercise is associated with reduced perceived exertion. While this effect is not present during exercise-to-exhaustion exercise, performance is significantly enhanced. This is congruent with caffeine reducing perceived exertion, because exercise-to-exhaustion should end at the same point of fatigue.<a href="#cite_note-69">[69]</a> Caffeine also improves power output and reduces time to completion in aerobic time trials,<a href="#cite_note-70">[70]</a> an effect positively (but not exclusively) associated with longer duration exercise.<a href="#cite_note-71">[71]</a> <div class="mw-heading mw-heading3"><h3 id="Specific_populations">Specific populations</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=6" title="Edit section: Specific populations">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Adults">Adults</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=7" title="Edit section: Adults">edit</a>]</div> For the general population of healthy adults, <a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a> advises a daily intake of no more than 400 mg.<a href="#cite_note-healthcanada-72">[72]</a> This limit was found to be safe by a 2017 systematic review on caffeine toxicology.<a href="#cite_note-Wikoff2017-73">[73]</a> <div class="mw-heading mw-heading4"><h4 id="Children">Children</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=8" title="Edit section: Children">edit</a>]</div> In healthy children, moderate caffeine intake under 400 mg produces effects that are "modest and typically innocuous".<a href="#cite_note-Temple2019-74">[74]</a><a href="#cite_note-75">[75]</a> As early as six months old, infants can metabolize caffeine at the same rate as that of adults.<a href="#cite_note-76">[76]</a> Higher doses of caffeine (>400 mg) can cause physiological, psychological and behavioral harm, particularly for children with psychiatric or cardiac conditions.<a href="#cite_note-Temple2019-74">[74]</a> There is no evidence that coffee stunts a child's growth.<a href="#cite_note-77">[77]</a> The <a href="/wiki/American_Academy_of_Pediatrics" title="American Academy of Pediatrics">American Academy of Pediatrics</a> recommends that caffeine consumption, particularly in the case of energy and sports drinks, is not appropriate for children and adolescents and should be avoided.<a href="#cite_note-Committee_on_Nutrition_and_the_Council_on_Sports_Medicine_and_Fitness_1182–1189-78">[78]</a> This recommendation is based on a clinical report released by American Academy of Pediatrics in 2011 with a review of 45 publications from 1994 to 2011 and includes inputs from various stakeholders (Pediatricians, Committee on nutrition, Canadian Pediatric Society, <a href="/wiki/Centers_for_Disease_Control_%26_Prevention" class="mw-redirect" title="Centers for Disease Control & Prevention">Centers for Disease Control & Prevention</a>, <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a>, Sports Medicine & Fitness committee, National Federations of High School Associations).<a href="#cite_note-Committee_on_Nutrition_and_the_Council_on_Sports_Medicine_and_Fitness_1182–1189-78">[78]</a> For children age 12 and under, <a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a> recommends a maximum daily caffeine intake of no more than 2.5 milligrams per kilogram of body weight. Based on average body weights of children, this translates to the following age-based intake limits:<a href="#cite_note-healthcanada-72">[72]</a> <table class="wikitable"> <tbody><tr> <th scope="col">Age range </th> <th scope="col">Maximum recommended daily caffeine intake </th></tr> <tr> <td>4–6 </td> <td>45 mg (slightly more than in 355 ml (12 fl. oz) of a typical caffeinated soft drink) </td></tr> <tr> <td>7–9 </td> <td>62.5 mg </td></tr> <tr> <td>10–12 </td> <td>85 mg (about <style data-mw-deduplicate="TemplateStyles:r1154941027">.mw-parser-output .frac{white-space:nowrap}.mw-parser-output .frac .num,.mw-parser-output .frac .den{font-size:80%;line-height:0;vertical-align:super}.mw-parser-output .frac .den{vertical-align:sub}.mw-parser-output .sr-only{border:0;clip:rect(0,0,0,0);clip-path:polygon(0px 0px,0px 0px,0px 0px);height:1px;margin:-1px;overflow:hidden;padding:0;position:absolute;width:1px}</style>1⁄2 cup of coffee) </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Adolescents">Adolescents</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=9" title="Edit section: Adolescents">edit</a>]</div> Health Canada has not developed advice for adolescents because of insufficient data. However, they suggest that daily caffeine intake for this age group be no more than 2.5 mg/kg body weight. This is because the maximum adult caffeine dose may not be appropriate for light-weight adolescents or for younger adolescents who are still growing. The daily dose of 2.5 mg/kg body weight would not cause adverse health effects in the majority of adolescent caffeine consumers. This is a conservative suggestion since older and heavier-weight adolescents may be able to consume adult doses of caffeine without experiencing adverse effects.<a href="#cite_note-healthcanada-72">[72]</a> <div class="mw-heading mw-heading4"><h4 id="Pregnancy_and_breastfeeding">Pregnancy and breastfeeding</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=10" title="Edit section: Pregnancy and breastfeeding">edit</a>]</div> The metabolism of caffeine is reduced in pregnancy, especially in the third trimester, and the half-life of caffeine during pregnancy can be increased up to 15 hours (as compared to 2.5 to 4.5 hours in non-pregnant adults).<a href="#cite_note-Van_Dam-79">[79]</a> Evidence regarding the effects of caffeine on pregnancy and for breastfeeding are inconclusive.<a href="#cite_note-Jah2015-26">[26]</a> There is limited primary and secondary advice for, or against, <a href="/wiki/Nutrition_and_pregnancy#Caffeine" title="Nutrition and pregnancy">caffeine use during pregnancy</a> and its effects on the fetus or newborn.<a href="#cite_note-Jah2015-26">[26]</a> The UK <a href="/wiki/Food_Standards_Agency" title="Food Standards Agency">Food Standards Agency</a> has recommended that pregnant women should limit their caffeine intake, out of prudence, to less than 200 mg of caffeine a day – the equivalent of two cups of instant coffee, or one and a half to two cups of fresh coffee.<a href="#cite_note-80">[80]</a> The <a href="/wiki/American_Congress_of_Obstetricians_and_Gynecologists" class="mw-redirect" title="American Congress of Obstetricians and Gynecologists">American Congress of Obstetricians and Gynecologists</a> (ACOG) concluded in 2010 that caffeine consumption is safe up to 200 mg per day in pregnant women.<a href="#cite_note-ACOG_policy_462_caffeine-27">[27]</a> For women who breastfeed, are pregnant, or may become pregnant, Health Canada recommends a maximum daily caffeine intake of no more than 300 mg, or a little over two 8 oz (237 mL) cups of coffee.<a href="#cite_note-healthcanada-72">[72]</a> A 2017 systematic review on caffeine toxicology found evidence supporting that caffeine consumption up to 300 mg/day for pregnant women is generally not associated with adverse reproductive or developmental effect.<a href="#cite_note-Wikoff2017-73">[73]</a> There are conflicting reports in the scientific literature about caffeine use during pregnancy.<a href="#cite_note-pmid19238414-81">[81]</a> A 2011 review found that caffeine during pregnancy does not appear to increase the risk of <a href="/wiki/Congenital_malformations" class="mw-redirect" title="Congenital malformations">congenital malformations</a>, <a href="/wiki/Miscarriage" title="Miscarriage">miscarriage</a> or <a href="/wiki/Growth_retardation" class="mw-redirect" title="Growth retardation">growth retardation</a> even when consumed in moderate to high amounts.<a href="#cite_note-pmid21370398-82">[82]</a> Other reviews, however, concluded that there is some evidence that higher caffeine intake by pregnant women may be associated with a higher risk of giving birth to a <a href="/wiki/Low_birth_weight" title="Low birth weight">low birth weight</a> baby,<a href="#cite_note-83">[83]</a> and may be associated with a higher risk of pregnancy loss.<a href="#cite_note-84">[84]</a> A systematic review, analyzing the results of observational studies, suggests that women who consume large amounts of caffeine (greater than 300 mg/day) prior to becoming pregnant may have a higher risk of experiencing pregnancy loss.<a href="#cite_note-85">[85]</a> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects">Adverse effects</h2>[<a href="/w/index.php?title=Caffeine&action=edit&section=11" title="Edit section: Adverse effects">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Physiological">Physiological</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=12" title="Edit section: Physiological">edit</a>]</div> Caffeine in coffee and other <a href="/wiki/Caffeinated_drink" title="Caffeinated drink">caffeinated drinks</a> can affect <a href="/wiki/Gastrointestinal_motility" class="mw-redirect" title="Gastrointestinal motility">gastrointestinal motility</a> and <a href="/wiki/Gastric_acid" title="Gastric acid">gastric acid</a> secretion.<a href="#cite_note-Boekema1999-86">[86]</a><a href="#cite_note-Cohen1975-87">[87]</a><a href="#cite_note-Sherwood2004-88">[88]</a> In postmenopausal women, high caffeine consumption can accelerate <a href="/wiki/Osteoporosis" title="Osteoporosis">bone loss</a>.<a href="#cite_note-mp-89">[89]</a><a href="#cite_note-Caffeine_intake_increases_the_rate_of_bone_loss_in_elderly_women_and_interacts_with_vitamin_D_receptor_genotypes-90">[90]</a> Caffeine, alongside other factors such as stress and fatigue, can also increase the pressure in various muscles, including the <a href="/wiki/Eyelid" title="Eyelid">eyelids</a>.<a href="#cite_note-91">[91]</a> Acute ingestion of caffeine in large doses (at least 250–300 mg, equivalent to the amount found in 2–3 cups of coffee or 5–8 cups of tea) results in a short-term stimulation of urine output in individuals who have been deprived of caffeine for a period of days or weeks.<a href="#cite_note-diuretic-92">[92]</a> This increase is due to both a <a href="/wiki/Polyuria" title="Polyuria">diuresis</a> (increase in water excretion) and a <a href="/wiki/Natriuresis" title="Natriuresis">natriuresis</a> (increase in saline excretion); it is mediated via proximal tubular adenosine receptor blockade.<a href="#cite_note-93">[93]</a> The acute increase in urinary output may increase the risk of <a href="/wiki/Dehydration" title="Dehydration">dehydration</a>. However, chronic users of caffeine develop a <a href="/wiki/Drug_tolerance" title="Drug tolerance">tolerance</a> to this effect and experience no increase in urinary output.<a href="#cite_note-really-94">[94]</a><a href="#cite_note-armstrong2007-95">[95]</a><a href="#cite_note-96">[96]</a> <div class="mw-heading mw-heading3"><h3 id="Psychological">Psychological</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=13" title="Edit section: Psychological">edit</a>]</div> Minor undesired symptoms from caffeine ingestion not sufficiently severe to warrant a psychiatric diagnosis are common and include mild anxiety, jitteriness, insomnia, increased sleep latency, and reduced coordination.<a href="#cite_note-effects-52">[52]</a><a href="#cite_note-pmid21346331-97">[97]</a> Caffeine can have negative effects on <a href="/wiki/Anxiety_disorders" class="mw-redirect" title="Anxiety disorders">anxiety disorders</a>.<a href="#cite_note-Winston_2005-98">[98]</a> According to a 2011 literature review, caffeine use may induce anxiety and panic disorders in people with <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a>.<a href="#cite_note-99">[99]</a> At high doses, typically greater than 300 mg, caffeine can both cause and worsen anxiety.<a href="#cite_note-pmid12204388-100">[100]</a> For some people, discontinuing caffeine use can significantly reduce anxiety.<a href="#cite_note-pmid2727208-101">[101]</a> In moderate doses, caffeine has been associated with reduced symptoms of <a href="/wiki/Clinical_depression" class="mw-redirect" title="Clinical depression">depression</a> and lower <a href="/wiki/Suicide" title="Suicide">suicide</a> risk.<a href="#cite_note-Psyc10-102">[102]</a> Two reviews indicate that increased consumption of coffee and caffeine may reduce the risk of depression.<a href="#cite_note-Wang_2016-103">[103]</a><a href="#cite_note-Grosso_2016-104">[104]</a> Some textbooks state that caffeine is a mild euphoriant,<a href="#cite_note-105">[105]</a><a href="#cite_note-106">[106]</a><a href="#cite_note-107">[107]</a> while others state that it is not a euphoriant.<a href="#cite_note-108">[108]</a><a href="#cite_note-109">[109]</a> <a href="/wiki/Caffeine-induced_anxiety_disorder" title="Caffeine-induced anxiety disorder">Caffeine-induced anxiety disorder</a> is a subclass of the <a href="/wiki/DSM-5" title="DSM-5">DSM-5</a> diagnosis of substance/medication-induced anxiety disorder.<a href="#cite_note-Add2014-110">[110]</a> <div class="mw-heading mw-heading3"><h3 id="Reinforcement_disorders">Reinforcement disorders</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=14" title="Edit section: Reinforcement disorders">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Addiction">Addiction</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=15" title="Edit section: Addiction">edit</a>]</div> Whether caffeine can result in an addictive disorder depends on how addiction is defined. Compulsive caffeine consumption under any circumstances has not been observed, and caffeine is therefore not generally considered addictive.<a href="#cite_note-111">[111]</a> Some diagnostic sources, such as the <a href="/wiki/International_Statistical_Classification_of_Diseases_and_Related_Health_Problems#ICDM-9" class="mw-redirect" title="International Statistical Classification of Diseases and Related Health Problems">ICDM-9</a> and <a href="/wiki/ICD-10" title="ICD-10">ICD-10</a>, include a classification of caffeine addiction under a broader diagnostic model.<a href="#cite_note-112">[112]</a> Some state that certain users can become addicted and therefore unable to decrease use even though they know there are negative health effects.<a href="#cite_note-pmid24761279-3">[3]</a><a href="#cite_note-113">[113]</a> Caffeine does not appear to be a reinforcing stimulus, and some degree of aversion may actually occur, with people preferring placebo over caffeine in a study on drug abuse liability published in an <a href="/wiki/National_Institute_on_Drug_Abuse" title="National Institute on Drug Abuse">NIDA</a> research monograph.<a href="#cite_note-114">[114]</a> Some state that research does not provide support for an underlying biochemical mechanism for caffeine addiction.<a href="#cite_note-Nestler_caffeine_dependence-addiction-28">[28]</a><a href="#cite_note-Cellular_basis-115">[115]</a><a href="#cite_note-Human-caffeine_NAcc_neuroimaging-116">[116]</a><a href="#cite_note-Paper_cited_by_preceding_book_ref-117">[117]</a> Other research states it can affect the reward system.<a href="#cite_note-118">[118]</a> "Caffeine addiction" was added to the ICDM-9 and ICD-10. However, its addition was contested with claims that this diagnostic model of caffeine addiction is not supported by evidence.<a href="#cite_note-Nestler_caffeine_dependence-addiction-28">[28]</a><a href="#cite_note-Clinical_addiction_&_dependence-119">[119]</a><a href="#cite_note-ICD-10_F15.2-120">[120]</a> The <a href="/wiki/American_Psychiatric_Association" title="American Psychiatric Association">American Psychiatric Association</a>'s <a href="/wiki/DSM-5" title="DSM-5">DSM-5</a> does not include the diagnosis of a caffeine addiction but proposes criteria for the disorder for more study.<a href="#cite_note-Add2014-110">[110]</a><a href="#cite_note-:2-121">[121]</a> <div class="mw-heading mw-heading4"><h4 id="Dependence_and_withdrawal">Dependence and withdrawal</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=16" title="Edit section: Dependence and withdrawal">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Caffeine_dependence" title="Caffeine dependence">Caffeine dependence</a> and <a href="/wiki/Caffeine_withdrawal" title="Caffeine withdrawal">Caffeine withdrawal</a></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/Caffeine-induced_anxiety_disorder" title="Caffeine-induced anxiety disorder">Caffeine-induced anxiety disorder</a>, <a href="/wiki/Caffeine-induced_sleep_disorder" title="Caffeine-induced sleep disorder">caffeine-induced sleep disorder</a>, and <a href="/wiki/Caffeinism" title="Caffeinism">caffeinism</a></div> <a href="/wiki/Caffeine_withdrawal" title="Caffeine withdrawal">Caffeine withdrawal</a> can cause mild to clinically significant distress or impairment in daily functioning. The frequency at which this occurs is self-reported at 11%, but in lab tests only half of the people who report withdrawal actually experience it, casting doubt on many claims of dependence.<a href="#cite_note-pmid19428492-122">[122]</a> and most cases of caffeine withdrawal were 13% in the moderate sense. Moderately <a href="/wiki/Physical_dependence" title="Physical dependence">physical dependence</a> and withdrawal symptoms may occur upon abstinence, with greater than 100 mg caffeine per day, although these symptoms last no longer than a day.<a href="#cite_note-Nestler_caffeine_dependence-addiction-28">[28]</a> Some symptoms associated with <a href="/wiki/Psychological_dependence" title="Psychological dependence">psychological dependence</a> may also occur during withdrawal.<a href="#cite_note-pmid15448977-2">[2]</a> The diagnostic criteria for caffeine withdrawal require a previous prolonged daily use of caffeine.<a href="#cite_note-:02-123">[123]</a> Following 24 hours of a marked reduction in consumption, a minimum of 3 of these signs or symptoms is required to meet withdrawal criteria: difficulty concentrating, <a href="/wiki/Depression_(mood)" title="Depression (mood)">depressed mood</a>/<a href="/wiki/Irritability" title="Irritability">irritability</a>, <a href="/wiki/Influenza" title="Influenza">flu</a>-like symptoms, <a href="/wiki/Headache" title="Headache">headache</a>, and <a href="/wiki/Fatigue" title="Fatigue">fatigue</a>.<a href="#cite_note-:02-123">[123]</a> Additionally, the signs and symptoms must disrupt important areas of functioning and are not associated with effects of another condition.<a href="#cite_note-:02-123">[123]</a> The ICD-11 includes <a href="/wiki/Caffeine_dependence" title="Caffeine dependence">caffeine dependence</a> as a distinct diagnostic category, which closely mirrors the <a href="/wiki/DSM-5" title="DSM-5">DSM-5</a>'s proposed set of criteria for "caffeine-use disorder".<a href="#cite_note-:2-121">[121]</a><a href="#cite_note-:1-124">[124]</a>  Caffeine use disorder refers to dependence on caffeine characterized by failure to control caffeine consumption despite negative physiological consequences.<a href="#cite_note-:2-121">[121]</a><a href="#cite_note-:1-124">[124]</a> The <a href="/wiki/American_Psychiatric_Association" title="American Psychiatric Association">APA</a>, which published the DSM-5, acknowledged that there was sufficient evidence in order to create a diagnostic model of caffeine dependence for the DSM-5, but they noted that the <a href="/wiki/Clinical_significance" title="Clinical significance">clinical significance</a> of the disorder is unclear.<a href="#cite_note-125">[125]</a> Due to this inconclusive evidence on clinical significance, the DSM-5 classifies caffeine-use disorder as a "condition for further study".<a href="#cite_note-:2-121">[121]</a> <a href="/wiki/Drug_tolerance" title="Drug tolerance">Tolerance</a> to the effects of caffeine occurs for caffeine-induced elevations in <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a> and the subjective feelings of nervousness though the effects are not drastic. <a href="/wiki/Sensitization" title="Sensitization">Sensitization</a>, the process whereby effects become more prominent with use, may occur for positive effects such as feelings of alertness and wellbeing.<a href="#cite_note-pmid19428492-122">[122]</a> Tolerance varies for daily, regular caffeine users and high caffeine users. High doses of caffeine (750 to 1200 mg/day spread throughout the day) have been shown to produce complete tolerance to some, but not all of the effects of caffeine. Doses as low as 100 mg/day, such as a 6 oz (170 g) cup of coffee or two to three 12 oz (340 g) servings of caffeinated soft-drink, may continue to cause sleep disruption, among other intolerances. Non-regular caffeine users have the least caffeine tolerance for sleep disruption.<a href="#cite_note-Caffeinedependence_JohnHopkins-126">[126]</a> Some coffee drinkers develop tolerance to its undesired sleep-disrupting effects, but others apparently do not.<a href="#cite_note-Fredholm-127">[127]</a> <div class="mw-heading mw-heading3"><h3 id="Risk_of_other_diseases">Risk of other diseases</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=17" title="Edit section: Risk of other diseases">edit</a>]</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/Health_effects_of_coffee" title="Health effects of coffee">Health effects of coffee</a></div> A <a href="/wiki/Neuroprotection" title="Neuroprotection">neuroprotective</a> effect of caffeine against <a href="/wiki/Alzheimer%27s_disease" title="Alzheimer's disease">Alzheimer's disease</a> and dementia is possible but the evidence is inconclusive.<a href="#cite_note-pmid20182026-128">[128]</a><a href="#cite_note-129">[129]</a> Caffeine may lessen the severity of <a href="/wiki/Acute_mountain_sickness" class="mw-redirect" title="Acute mountain sickness">acute mountain sickness</a> if taken a few hours prior to attaining a high altitude.<a href="#cite_note-pmid20367483-130">[130]</a> One meta analysis has found that caffeine consumption is associated with a reduced risk of <a href="/wiki/Type_2_diabetes" title="Type 2 diabetes">type 2 diabetes</a>.<a href="#cite_note-131">[131]</a> Regular caffeine consumption may reduce the risk of developing <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a> and may slow the progression of Parkinson's disease.<a href="#cite_note-132">[132]</a><a href="#cite_note-133">[133]</a><a href="#cite_note-Qi_2014-24">[24]</a> Caffeine increases <a href="/wiki/Intraocular_pressure" title="Intraocular pressure">intraocular pressure</a> in those with <a href="/wiki/Glaucoma" title="Glaucoma">glaucoma</a> but does not appear to affect normal individuals.<a href="#cite_note-pmid20706731-134">[134]</a> The DSM-5 also includes other caffeine-induced disorders consisting of caffeine-induced anxiety disorder, caffeine-induced sleep disorder and unspecified caffeine-related disorders. The first two disorders are classified under "Anxiety Disorder" and "Sleep-Wake Disorder" because they share similar characteristics. Other disorders that present with significant distress and impairment of daily functioning that warrant clinical attention but do not meet the criteria to be diagnosed under any specific disorders are listed under "Unspecified Caffeine-Related Disorders".<a href="#cite_note-135">[135]</a> <div class="mw-heading mw-heading3"><h3 id="Energy_crash">Energy crash</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=18" title="Edit section: Energy crash">edit</a>]</div> Caffeine is reputed to cause a fall in energy several hours after drinking, but this is not well researched.<a href="#cite_note-136">[136]</a><a href="#cite_note-137">[137]</a><a href="#cite_note-138">[138]</a><a href="#cite_note-139">[139]</a> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2>[<a href="/w/index.php?title=Caffeine&action=edit&section=19" title="Edit section: Overdose">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid 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.mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Expand_section plainlinks metadata ambox mbox-small-left ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><a href="/wiki/File:Wiki_letter_w_cropped.svg" class="mw-file-description"><img alt="[icon]" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/20px-Wiki_letter_w_cropped.svg.png" decoding="async" width="20" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/40px-Wiki_letter_w_cropped.svg.png 1.5x" data-file-width="44" data-file-height="31" /></a></td><td class="mbox-text"><div class="mbox-text-span">This section needs expansion with: practical management of overdose, see <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 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.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><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/30893206">30893206</a>. You can help by <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Caffeine&action=edit&section=">adding to it</a>. (November 2019)</div></td></tr></tbody></table> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Main_symptoms_of_Caffeine_overdose.svg" class="mw-file-description"><img alt="Torso of a young man with overlaid text of main side-effects of caffeine overdose." src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Main_symptoms_of_Caffeine_overdose.svg/290px-Main_symptoms_of_Caffeine_overdose.svg.png" decoding="async" width="290" height="317" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Main_symptoms_of_Caffeine_overdose.svg/435px-Main_symptoms_of_Caffeine_overdose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/66/Main_symptoms_of_Caffeine_overdose.svg/580px-Main_symptoms_of_Caffeine_overdose.svg.png 2x" data-file-width="1111" data-file-height="1216" /></a><figcaption>Primary symptoms of caffeine intoxication<a href="#cite_note-Medline-140">[140]</a></figcaption></figure> Consumption of 1–1.5 grams (1,000–1,500 mg) per day is associated with a condition known as <dfn><a href="/wiki/Caffeinism" title="Caffeinism">caffeinism</a></dfn>.<a href="#cite_note-141">[141]</a> Caffeinism usually combines <a href="/wiki/Caffeine_dependence" title="Caffeine dependence">caffeine dependency</a> with a wide range of unpleasant symptoms including nervousness, <a href="/wiki/Irritability" title="Irritability">irritability</a>, restlessness, <a href="/wiki/Insomnia" title="Insomnia">insomnia</a>, <a href="/wiki/Headache" title="Headache">headaches</a>, and palpitations after caffeine use.<a href="#cite_note-142">[142]</a> Caffeine overdose can result in a state of central nervous system overstimulation known as caffeine intoxication, a clinically significant temporary condition that develops during, or shortly after, the consumption of caffeine.<a href="#cite_note-:3-143">[143]</a> This syndrome typically occurs only after ingestion of large amounts of caffeine, well over the amounts found in typical caffeinated beverages and caffeine tablets (e.g., more than 400–500 mg at a time). According to the DSM-5, caffeine intoxication may be diagnosed if five (or more) of the following symptoms develop after recent consumption of caffeine: restlessness, nervousness, excitement, insomnia, flushed face, <a href="/wiki/Diuresis" title="Diuresis">diuresis</a>, gastrointestinal disturbance, muscle twitching, rambling flow of thought and speech, <a href="/wiki/Tachycardia" title="Tachycardia">tachycardia</a> or cardiac <a href="/wiki/Arrhythmia" title="Arrhythmia">arrhythmia</a>, periods of inexhaustibility, and <a href="/wiki/Psychomotor_agitation" title="Psychomotor agitation">psychomotor agitation</a>.<a href="#cite_note-144">[144]</a> According to the International Classification of Diseases (ICD-11), cases of very high caffeine intake (e.g. > 5 g) may result in caffeine intoxication with symptoms including mania, depression, lapses in judgment, disorientation, disinhibition, delusions, hallucinations or psychosis, and <a href="/wiki/Rhabdomyolysis" title="Rhabdomyolysis">rhabdomyolysis</a>.<a href="#cite_note-:3-143">[143]</a> <div class="mw-heading mw-heading3"><h3 id="Energy_drinks">Energy drinks</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=20" title="Edit section: Energy drinks">edit</a>]</div> High caffeine consumption in energy drinks (at least one liter or 320 mg of caffeine) was associated with short-term cardiovascular side effects including hypertension, prolonged <a href="/wiki/QT_interval" title="QT interval">QT interval</a>, and heart palpitations. These cardiovascular side effects were not seen with smaller amounts of caffeine consumption in energy drinks (less than 200 mg).<a href="#cite_note-Van_Dam-79">[79]</a> <div class="mw-heading mw-heading3"><h3 id="Severe_intoxication">Severe intoxication</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=21" title="Edit section: Severe intoxication">edit</a>]</div> As of 2007<a class="external text" href="https://en.wikipedia.org/w/index.php?title=Caffeine&action=edit">[update]</a> there is no known antidote or reversal agent for caffeine intoxication. Treatment of mild caffeine intoxication is directed toward symptom relief; severe intoxication may require <a href="/wiki/Peritoneal_dialysis" title="Peritoneal dialysis">peritoneal dialysis</a>, <a href="/wiki/Hemodialysis" title="Hemodialysis">hemodialysis</a>, or <a href="/wiki/Hemofiltration" title="Hemofiltration">hemofiltration</a>.<a href="#cite_note-Medline-140">[140]</a><a href="#cite_note-145">[145]</a><a href="#cite_note-:03-146">[146]</a> <a href="/wiki/Intralipid" class="mw-redirect" title="Intralipid">Intralipid</a> infusion therapy is indicated in cases of imminent risk of cardiac arrest in order to scavenge the free serum caffeine.<a href="#cite_note-:03-146">[146]</a> <div class="mw-heading mw-heading3"><h3 id="Lethal_dose">Lethal dose</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=22" title="Edit section: Lethal dose">edit</a>]</div> Death from caffeine ingestion appears to be rare, and most commonly caused by an intentional overdose of medications.<a href="#cite_note-Murray2019-147">[147]</a> In 2016, 3702 caffeine-related exposures were reported to Poison Control Centers in the United States, of which 846 required treatment at a medical facility, and 16 had a major outcome; and several caffeine-related deaths are reported in case studies.<a href="#cite_note-Murray2019-147">[147]</a> The <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD50</a> of caffeine in rats is 192 milligrams per kilogram of body mass. The fatal dose in humans is estimated to be 150–200 milligrams per kilogram, which is 10.5–14 grams for a typical 70 kg (150 lb) adult, equivalent to about 75–100 cups of coffee.<a href="#cite_note-148">[148]</a><a href="#cite_note-ld50-149">[149]</a> There are cases where doses as low as 57 milligrams per kilogram have been fatal.<a href="#cite_note-150">[150]</a> A number of fatalities have been caused by overdoses of readily available powdered caffeine supplements, for which the estimated lethal amount is less than a tablespoon.<a href="#cite_note-151">[151]</a> The lethal dose is lower in individuals whose ability to metabolize caffeine is impaired due to genetics or chronic liver disease.<a href="#cite_note-liver-damage-152">[152]</a> A death was reported in 2013 of a man with <a href="/wiki/Liver_cirrhosis" class="mw-redirect" title="Liver cirrhosis">liver cirrhosis</a> who overdosed on caffeinated mints.<a href="#cite_note-independent-2013-10-11-153">[153]</a><a href="#cite_note-telegraph-2013-10-13-154">[154]</a> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2>[<a href="/w/index.php?title=Caffeine&action=edit&section=23" title="Edit section: Interactions">edit</a>]</div> Caffeine is a substrate for <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a>, and interacts with many substances through this and other mechanisms.<a href="#cite_note-UTD-155">[155]</a> <div class="mw-heading mw-heading3"><h3 id="Alcohol">Alcohol</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=24" title="Edit section: Alcohol">edit</a>]</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/Caffeinated_alcoholic_drink" title="Caffeinated alcoholic drink">Caffeinated alcoholic drink</a></div> According to <a href="/wiki/DSST_(standardized_test)" title="DSST (standardized test)">DSST</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">alcohol</a> causes a decrease in performance on their standardized tests, and caffeine causes a significant improvement.<a href="#cite_note-Mackay2002-156">[156]</a> When alcohol and caffeine are consumed jointly, the effects of the caffeine are changed, but the alcohol effects remain the same.<a href="#cite_note-Liguori2001-157">[157]</a> For example, consuming additional caffeine does not reduce the effect of alcohol.<a href="#cite_note-Liguori2001-157">[157]</a> However, the jitteriness and alertness given by caffeine is decreased when additional alcohol is consumed.<a href="#cite_note-Liguori2001-157">[157]</a> Alcohol consumption alone reduces both inhibitory and activational aspects of behavioral control. Caffeine antagonizes the effect of alcohol on the activational aspect of behavioral control, but has no effect on the inhibitory behavioral control.<a href="#cite_note-Marczinski2003-158">[158]</a> The <a href="/wiki/Dietary_Guidelines_for_Americans" title="Dietary Guidelines for Americans">Dietary Guidelines for Americans</a> recommend avoidance of concomitant consumption of alcohol and caffeine, as taking them together may lead to increased alcohol consumption, with a higher risk of alcohol-associated injury. <div class="mw-heading mw-heading3"><h3 id="Smoking">Smoking</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=25" title="Edit section: Smoking">edit</a>]</div> <a href="/wiki/Tobacco_smoking" title="Tobacco smoking">Smoking tobacco</a> has been shown to increase caffeine clearance by 56% as a result of polycyclic aromatic hydrocarbons inducing the CYP1A2 enzyme.<a href="#cite_note-159">[159]</a><a href="#cite_note-:4-10">[10]</a> The CYP1A2 enzyme that is induced by smoking is responsible for the metabolism of caffeine; increased enzyme activity leads to increased caffeine clearance, and is associated with greater coffee consumption for regular smokers.<a href="#cite_note-Bjørngaard_2017-160">[160]</a> <div class="mw-heading mw-heading3"><h3 id="Birth_control">Birth control</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=26" title="Edit section: Birth control">edit</a>]</div> <a href="/wiki/Birth_control_pills" class="mw-redirect" title="Birth control pills">Birth control pills</a> can extend the half-life of caffeine by as much as 40%, requiring greater attention to caffeine consumption.<a href="#cite_note-Benowitz1990-161">[161]</a><a href="#cite_note-162">[162]</a> <div class="mw-heading mw-heading3"><h3 id="Medications">Medications</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=27" title="Edit section: Medications">edit</a>]</div> Caffeine sometimes increases the effectiveness of some medications, such as those for <a href="/wiki/Headaches" class="mw-redirect" title="Headaches">headaches</a>.<a href="#cite_note-pmid21302868-163">[163]</a> Caffeine was determined to increase the potency of some over-the-counter <a href="/wiki/Analgesic" title="Analgesic">analgesic</a> medications by 40%.<a href="#cite_note-164">[164]</a> The pharmacological effects of adenosine may be blunted in individuals taking large quantities of <a href="/wiki/Methylxanthines" title="Methylxanthines">methylxanthines</a> like caffeine.<a href="#cite_note-165">[165]</a> Some other examples of methylxanthines include the medications <a href="/wiki/Theophylline" title="Theophylline">theophylline</a> and <a href="/wiki/Aminophylline" title="Aminophylline">aminophylline</a>, which are prescribed to relieve symptoms of asthma or <a href="/wiki/Chronic_obstructive_pulmonary_disease" title="Chronic obstructive pulmonary disease">COPD</a>.<a href="#cite_note-166">[166]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Caffeine&action=edit&section=28" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=29" title="Edit section: Pharmacodynamics">edit</a>]</div> <div class="thumb tright" style=""><div class="thumbinner" style="width:-moz-fit-content; width:fit-content;"><div class="thumbimage noresize" style="width:auto;"> <div style="position: relative;"><a href="/wiki/File:SynapseSchematic_lines.svg" class="mw-file-description"><img alt="An illustrated chemical synapse" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/SynapseSchematic_lines.svg/400px-SynapseSchematic_lines.svg.png" decoding="async" width="400" height="213" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/SynapseSchematic_lines.svg/600px-SynapseSchematic_lines.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d7/SynapseSchematic_lines.svg/800px-SynapseSchematic_lines.svg.png 2x" data-file-width="2000" data-file-height="1064" /></a> <div style="position:absolute; left:-1px; top:160px"><a href="/wiki/Postsynaptic_density" title="Postsynaptic density">Postsynaptic density</a></div> <div style="position:absolute; left:6px; top:97px"><a href="/wiki/Voltage-dependent_calcium_channel" class="mw-redirect" title="Voltage-dependent calcium channel">Voltage- gated Ca++ channel</a></div> <div style="position:absolute; left:19px; top:54px"><a href="/wiki/Synaptic_vesicle" title="Synaptic vesicle">Synaptic vesicle</a></div> <div style="position:absolute; left:206px; top:22px"><a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">Neurotransmitter transporter</a></div> <div style="position:absolute; left:250px; top:153px"><a href="/wiki/Neurotransmitter_receptor" title="Neurotransmitter receptor">Receptor</a></div> <div style="position:absolute; left:8px; top:7px"><a href="/wiki/Neurotransmitter" title="Neurotransmitter">Neurotransmitter</a></div> <div style="position:absolute; left:332px; top:55px"><a href="/wiki/Axon_terminal" title="Axon terminal">Axon terminal</a></div> <div style="position:absolute; left:330px; top:137px"><a href="/wiki/Synaptic_cleft" class="mw-redirect" title="Synaptic cleft">Synaptic cleft</a></div> <div style="position:absolute; left:342px; top:182px"><a href="/wiki/Dendrite" title="Dendrite">Dendrite</a></div></div></div><div class="thumbcaption">Structure of a typical <a href="/wiki/Chemical_synapse" title="Chemical synapse">chemical synapse</a></div></div></div> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Caffeine_and_adenosine.svg" class="mw-file-description"><img alt="Two skeletal formulas: left – caffeine, right – adenosine." src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Caffeine_and_adenosine.svg/250px-Caffeine_and_adenosine.svg.png" decoding="async" width="220" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Caffeine_and_adenosine.svg/330px-Caffeine_and_adenosine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Caffeine_and_adenosine.svg/500px-Caffeine_and_adenosine.svg.png 2x" data-file-width="512" data-file-height="326" /></a><figcaption>Caffeine's primary mechanism of action is as an <a href="/wiki/Adenosine_receptor_antagonist" title="Adenosine receptor antagonist">adenosine receptor antagonist</a> in the brain.</figcaption></figure> In the absence of caffeine and when a person is awake and alert, little <a href="/wiki/Adenosine" title="Adenosine">adenosine</a> is present in CNS neurons. With a continued wakeful state, over time adenosine accumulates in the neuronal <a href="/wiki/Synapse" title="Synapse">synapse</a>, in turn binding to and activating <a href="/wiki/Adenosine_receptor" title="Adenosine receptor">adenosine receptors</a> found on certain CNS neurons; when activated, these receptors produce a cellular response that ultimately increases <a href="/wiki/Drowsiness" class="mw-redirect" title="Drowsiness">drowsiness</a>. When caffeine is consumed, it <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonizes</a> adenosine receptors; in other words, caffeine prevents adenosine from activating the receptor by blocking the location on the receptor where adenosine binds to it. As a result, caffeine temporarily prevents or relieves drowsiness, and thus maintains or restores alertness.<a href="#cite_note-Drugbank-Caffeine-5">[5]</a> <div class="mw-heading mw-heading4"><h4 id="Receptor_and_ion_channel_targets">Receptor and ion channel targets</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=30" title="Edit section: Receptor and ion channel targets">edit</a>]</div> Caffeine is an <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of <a href="/wiki/Adenosine_A2A_receptor" title="Adenosine A2A receptor">adenosine A2A receptors</a>, and <a href="/wiki/Knockout_mouse" title="Knockout mouse">knockout mouse</a> studies have specifically implicated antagonism of the A2A receptor as responsible for the wakefulness-promoting effects of caffeine.<a href="#cite_note-pmid22886028-167">[167]</a> Antagonism of A2A receptors in the <a href="/wiki/Ventrolateral_preoptic_area" class="mw-redirect" title="Ventrolateral preoptic area">ventrolateral preoptic area</a> (VLPO) reduces inhibitory <a href="/wiki/GABA" title="GABA">GABA</a> <a href="/wiki/Neurotransmission" title="Neurotransmission">neurotransmission</a> to the <a href="/wiki/Tuberomammillary_nucleus" title="Tuberomammillary nucleus">tuberomammillary nucleus</a>, a <a href="/wiki/Histamine" title="Histamine">histaminergic</a> projection nucleus that activation-dependently promotes arousal.<a href="#cite_note-Ferre_2008-168">[168]</a> This disinhibition of the tuberomammillary nucleus is the downstream mechanism by which caffeine produces wakefulness-promoting effects.<a href="#cite_note-Ferre_2008-168">[168]</a> Caffeine is an antagonist of all four <a href="/wiki/Adenosine_receptor" title="Adenosine receptor">adenosine receptor</a> subtypes (<a href="/wiki/Adenosine_receptor_A1" class="mw-redirect" title="Adenosine receptor A1">A1</a>, <a href="/wiki/Adenosine_receptor_A2a" class="mw-redirect" title="Adenosine receptor A2a">A2A</a>, <a href="/wiki/Adenosine_receptor_A2b" class="mw-redirect" title="Adenosine receptor A2b">A2B</a>, and <a href="/wiki/Adenosine_receptor_A3" class="mw-redirect" title="Adenosine receptor A3">A3</a>), although with varying <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potencies</a>.<a href="#cite_note-Drugbank-Caffeine-5">[5]</a><a href="#cite_note-pmid22886028-167">[167]</a> The <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> (<a href="/wiki/Dissociation_constant" title="Dissociation constant">KD</a>) values of caffeine for the human adenosine receptors are 12 μM at <a href="/wiki/Adenosine_A1_receptor" title="Adenosine A1 receptor">A1</a>, 2.4 μM at <a href="/wiki/Adenosine_A2A_receptor" title="Adenosine A2A receptor">A2A</a>, 13 μM at <a href="/wiki/Adenosine_A2B_receptor" title="Adenosine A2B receptor">A2B</a>, and 80 μM at <a href="/wiki/Adenosine_A3_receptor" title="Adenosine A3 receptor">A3</a>.<a href="#cite_note-pmid22886028-167">[167]</a> Antagonism of adenosine receptors by caffeine also stimulates the <a href="/wiki/Medulla_oblongata" title="Medulla oblongata">medullary</a> vagal, vasomotor, and <a href="/wiki/Respiratory_center" title="Respiratory center">respiratory centers</a>, which increases respiratory rate, reduces heart rate, and constricts blood vessels.<a href="#cite_note-Drugbank-Caffeine-5">[5]</a> Adenosine receptor antagonism also promotes <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> release (e.g., <a href="/wiki/Monoamines" class="mw-redirect" title="Monoamines">monoamines</a> and <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a>), which endows caffeine with its stimulant effects;<a href="#cite_note-Drugbank-Caffeine-5">[5]</a><a href="#cite_note-169">[169]</a> <a href="/wiki/Adenosine" title="Adenosine">adenosine</a> acts as an inhibitory neurotransmitter that suppresses activity in the central nervous system. <a href="/wiki/Heart_palpitation" class="mw-redirect" title="Heart palpitation">Heart palpitations</a> are caused by blockade of the A1 receptor.<a href="#cite_note-Drugbank-Caffeine-5">[5]</a> Because caffeine is both water- and lipid-soluble, it readily crosses the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> that separates the bloodstream from the interior of the brain. Once in the brain, the principal mode of action is as a nonselective <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of adenosine receptors (in other words, an agent that reduces the effects of adenosine). The caffeine molecule is structurally similar to adenosine, and is capable of binding to adenosine receptors on the surface of cells without activating them, thereby acting as a <a href="/wiki/Competitive_antagonist" class="mw-redirect" title="Competitive antagonist">competitive antagonist</a>.<a href="#cite_note-pmid15095008-170">[170]</a> In addition to its activity at adenosine receptors, caffeine is an <a href="/wiki/Inositol_trisphosphate_receptor" title="Inositol trisphosphate receptor">inositol trisphosphate receptor 1</a> antagonist and a voltage-independent activator of the <a href="/wiki/Ryanodine_receptor" title="Ryanodine receptor">ryanodine receptors</a> (<a href="/wiki/RYR1" class="mw-redirect" title="RYR1">RYR1</a>, <a href="/wiki/RYR2" class="mw-redirect" title="RYR2">RYR2</a>, and <a href="/wiki/RYR3" class="mw-redirect" title="RYR3">RYR3</a>).<a href="#cite_note-IUPHAR_caffeine-171">[171]</a> It is also a competitive antagonist of the <a href="/wiki/Glycine_receptor" title="Glycine receptor">ionotropic glycine receptor</a>.<a href="#cite_note-pmid19564396-172">[172]</a> <div class="mw-heading mw-heading4"><h4 id="Effects_on_striatal_dopamine">Effects on striatal dopamine</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=31" title="Edit section: Effects on striatal dopamine">edit</a>]</div> While caffeine does not directly bind to any <a href="/wiki/Dopamine_receptor" title="Dopamine receptor">dopamine receptors</a>, it influences the binding activity of <a href="/wiki/Dopamine" title="Dopamine">dopamine</a> at its receptors in the <a href="/wiki/Striatum" title="Striatum">striatum</a> by binding to adenosine receptors that have formed <a href="/wiki/GPCR_oligomer" title="GPCR oligomer">GPCR heteromers</a> with dopamine receptors, specifically the <a href="/wiki/Adenosine_receptor_A1" class="mw-redirect" title="Adenosine receptor A1">A1</a>–<a href="/wiki/DRD1" class="mw-redirect" title="DRD1">D1</a> receptor <a href="/wiki/Heterodimer" class="mw-redirect" title="Heterodimer">heterodimer</a> (this is a receptor complex with one adenosine A1 receptor and one dopamine D1 receptor) and the <a href="/wiki/Adenosine_receptor_A2a" class="mw-redirect" title="Adenosine receptor A2a">A2A</a>–<a href="/wiki/DRD2" class="mw-redirect" title="DRD2">D2</a> receptor <a href="/wiki/Heterotetramer" class="mw-redirect" title="Heterotetramer">heterotetramer</a> (this is a receptor complex with two adenosine A2A receptors and two dopamine D2 receptors).<a href="#cite_note-A1-DRD1_and_A2a-DRD2_review-173">[173]</a><a href="#cite_note-Caffeine_heterotetramer_review-174">[174]</a><a href="#cite_note-Caffeine_psychostimulant_effects-175">[175]</a><a href="#cite_note-Caffeine_SUD_interactions-176">[176]</a> The A2A–D2 receptor heterotetramer has been identified as a primary pharmacological target of caffeine, primarily because it mediates some of its psychostimulant effects and its pharmacodynamic interactions with dopaminergic psychostimulants.<a href="#cite_note-Caffeine_heterotetramer_review-174">[174]</a><a href="#cite_note-Caffeine_psychostimulant_effects-175">[175]</a><a href="#cite_note-Caffeine_SUD_interactions-176">[176]</a> Caffeine also causes the release of dopamine in the <a href="/wiki/Dorsal_striatum" class="mw-redirect" title="Dorsal striatum">dorsal striatum</a> and <a href="/wiki/Nucleus_accumbens_core" class="mw-redirect" title="Nucleus accumbens core">nucleus accumbens core</a> (a substructure within the <a href="/wiki/Ventral_striatum" class="mw-redirect" title="Ventral striatum">ventral striatum</a>), but not the <a href="/wiki/Nucleus_accumbens_shell" class="mw-redirect" title="Nucleus accumbens shell">nucleus accumbens shell</a>, by antagonizing <a href="/wiki/Adenosine_receptor_A1" class="mw-redirect" title="Adenosine receptor A1">A1</a> receptors in the <a href="/wiki/Axon_terminal" title="Axon terminal">axon terminal</a> of dopamine neurons and <a href="/wiki/Adenosine_receptor_A1" class="mw-redirect" title="Adenosine receptor A1">A1</a>–<a href="/wiki/Adenosine_receptor_A2a" class="mw-redirect" title="Adenosine receptor A2a">A2A</a> heterodimers (a receptor complex composed of one adenosine A1 receptor and one adenosine A2A receptor) in the axon terminal of glutamate neurons.<a href="#cite_note-A1-DRD1_and_A2a-DRD2_review-173">[173]</a><a href="#cite_note-Ferre_2008-168">[168]</a> During chronic caffeine use, caffeine-induced dopamine release within the nucleus accumbens core is markedly reduced due to <a href="/wiki/Drug_tolerance" title="Drug tolerance">drug tolerance</a>.<a href="#cite_note-A1-DRD1_and_A2a-DRD2_review-173">[173]</a><a href="#cite_note-Ferre_2008-168">[168]</a> <div class="mw-heading mw-heading4"><h4 id="Enzyme_targets">Enzyme targets</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=32" title="Edit section: Enzyme targets">edit</a>]</div> Caffeine, like other <a href="/wiki/Xanthine" title="Xanthine">xanthines</a>, also acts as a <a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">phosphodiesterase inhibitor</a>.<a href="#cite_note-pmid20164566-177">[177]</a> As a competitive nonselective phosphodiesterase inhibitor,<a href="#cite_note-PDEs-Essayan-178">[178]</a> caffeine raises intracellular <a href="/wiki/Cyclic_adenosine_monophosphate" title="Cyclic adenosine monophosphate">cyclic AMP</a>, activates <a href="/wiki/Protein_kinase_A" title="Protein kinase A">protein kinase A</a>, <a href="/wiki/TNF_inhibitor" title="TNF inhibitor">inhibits TNF-alpha</a><a href="#cite_note-PTX-Deree-179">[179]</a><a href="#cite_note-pmid9927365-180">[180]</a> and <a href="/wiki/Leukotriene" title="Leukotriene">leukotriene</a><a href="#cite_note-LT-Peters-Golden-181">[181]</a> synthesis, and <a href="/wiki/Anti-inflammatory" title="Anti-inflammatory">reduces inflammation</a> and <a href="/wiki/Innate_immunity" class="mw-redirect" title="Innate immunity">innate immunity</a>.<a href="#cite_note-LT-Peters-Golden-181">[181]</a> Caffeine also affects the <a href="/wiki/Cholinergic_system" class="mw-redirect" title="Cholinergic system">cholinergic system</a> where it is a moderate inhibitor of the enzyme <a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase">acetylcholinesterase</a>.<a href="#cite_note-182">[182]</a><a href="#cite_note-183">[183]</a> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=33" title="Edit section: Pharmacokinetics">edit</a>]</div> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Caffeine_metabolites.svg" class="mw-file-description"><img alt="A diagram featuring 4 skeletal chemical formulas. Top (caffeine) relates to similar compounds paraxanthine, theobromine and theophylline." src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Caffeine_metabolites.svg/290px-Caffeine_metabolites.svg.png" decoding="async" width="290" height="245" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Caffeine_metabolites.svg/435px-Caffeine_metabolites.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/32/Caffeine_metabolites.svg/580px-Caffeine_metabolites.svg.png 2x" data-file-width="4296" data-file-height="3627" /></a><figcaption>Caffeine is metabolized in the liver via a single <a href="/wiki/Demethylation" title="Demethylation">demethylation</a>, resulting in three primary metabolites, <a href="/wiki/Paraxanthine" title="Paraxanthine">paraxanthine</a> (84%), <a href="/wiki/Theobromine" title="Theobromine">theobromine</a> (12%), and <a href="/wiki/Theophylline" title="Theophylline">theophylline</a> (4%), depending on which methyl group is removed.</figcaption></figure> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Caffeine_metabolism.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/08/Caffeine_metabolism.png/290px-Caffeine_metabolism.png" decoding="async" width="290" height="329" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/08/Caffeine_metabolism.png/435px-Caffeine_metabolism.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/08/Caffeine_metabolism.png/580px-Caffeine_metabolism.png 2x" data-file-width="3006" data-file-height="3412" /></a><figcaption>Urinary metabolites of caffeine in humans at 48 hours post-dose<a href="#cite_note-pmid20859793-184">[184]</a></figcaption></figure> Caffeine from coffee or other beverages is absorbed by the small intestine within 45 minutes of ingestion and distributed throughout all bodily tissues.<a href="#cite_note-pmid9329065-185">[185]</a> Peak blood concentration is reached within 1–2 hours.<a href="#cite_note-186">[186]</a> It is eliminated by <a href="/wiki/Rate_equation#First-order_reactions" title="Rate equation">first-order kinetics</a>.<a href="#cite_note-pmid7333346-187">[187]</a> Caffeine can also be absorbed rectally, evidenced by suppositories of <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a> <a href="/wiki/Tartrate" title="Tartrate">tartrate</a> and caffeine (for the relief of <a href="/wiki/Migraine" title="Migraine">migraine</a>)<a href="#cite_note-pmid13165929-188">[188]</a> and of <a href="/wiki/Chlorobutanol" title="Chlorobutanol">chlorobutanol</a> and caffeine (for the treatment of <a href="/wiki/Hyperemesis" class="mw-redirect" title="Hyperemesis">hyperemesis</a>).<a href="#cite_note-pmid17553397-189">[189]</a> However, rectal absorption is less efficient than oral: the maximum concentration (<a href="/wiki/Cmax_(pharmacology)" title="Cmax (pharmacology)">Cmax</a>) and total amount absorbed (<a href="/wiki/Area_under_the_curve_(pharmacokinetics)" title="Area under the curve (pharmacokinetics)">AUC</a>) are both about 30% (i.e., 1/3.5) of the oral amounts.<a href="#cite_note-190">[190]</a> Caffeine's <a href="/wiki/Biological_half-life" title="Biological half-life">biological half-life</a> – the time required for the body to eliminate one-half of a dose – varies widely among individuals according to factors such as pregnancy, other drugs, <a href="/wiki/Liver_enzymes" class="mw-redirect" title="Liver enzymes">liver enzyme</a> function level (needed for caffeine metabolism) and age. In healthy adults, caffeine's half-life is between 3 and 7 hours.<a href="#cite_note-Drugbank-Caffeine-5">[5]</a> The half-life is decreased by 30-50% in adult male <a href="/wiki/Smoking" title="Smoking">smokers</a>, approximately doubled in women taking <a href="/wiki/Oral_contraceptives" class="mw-redirect" title="Oral contraceptives">oral contraceptives</a>, and prolonged in the <a href="/wiki/Pregnancy#Trimesters" title="Pregnancy">last trimester of pregnancy</a>.<a href="#cite_note-Fredholm-127">[127]</a> In newborns the half-life can be 80 hours or more, dropping rapidly with age, possibly to less than the adult value by age 6 months.<a href="#cite_note-Fredholm-127">[127]</a> The antidepressant <a href="/wiki/Fluvoxamine" title="Fluvoxamine">fluvoxamine</a> (Luvox) reduces the clearance of caffeine by more than 90%, and increases its elimination half-life more than tenfold, from 4.9 hours to 56 hours.<a href="#cite_note-half-life-191">[191]</a> Caffeine is <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> in the <a href="/wiki/Liver" title="Liver">liver</a> by the <a href="/wiki/Cytochrome_P450_oxidase" class="mw-redirect" title="Cytochrome P450 oxidase">cytochrome P450 oxidase</a> enzyme system (particularly by the <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a> isozyme) into three dimethyl<a href="/wiki/Xanthine" title="Xanthine">xanthines</a>,<a href="#cite_note-192">[192]</a> each of which has its own effects on the body: <ul><li><a href="/wiki/Paraxanthine" title="Paraxanthine">Paraxanthine</a> (84%): Increases <a href="/wiki/Lipolysis" title="Lipolysis">lipolysis</a>, leading to elevated <a href="/wiki/Glycerol" title="Glycerol">glycerol</a> and free <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acid</a> levels in <a href="/wiki/Blood_plasma" title="Blood plasma">blood plasma</a>.</li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a> (12%): Dilates <a href="/wiki/Blood_vessel" title="Blood vessel">blood vessels</a> and increases <a href="/wiki/Urine" title="Urine">urine</a> volume. Theobromine is also the principal <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> in the <a href="/wiki/Cocoa_bean" title="Cocoa bean">cocoa bean</a> (<a href="/wiki/Chocolate" title="Chocolate">chocolate</a>).</li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a> (4%): Relaxes <a href="/wiki/Smooth_muscle" title="Smooth muscle">smooth muscles</a> of the <a href="/wiki/Bronchus" title="Bronchus">bronchi</a>, and is used to treat <a href="/wiki/Asthma" title="Asthma">asthma</a>. The <a href="/wiki/Therapeutic_dose" class="mw-redirect" title="Therapeutic dose">therapeutic dose</a> of theophylline, however, is many times greater than the levels attained from caffeine metabolism.<a href="#cite_note-pmid20091514-46">[46]</a></li></ul> <a href="/wiki/1,3,7-Trimethyluric_acid" title="1,3,7-Trimethyluric acid">1,3,7-Trimethyluric acid</a> is a minor caffeine metabolite.<a href="#cite_note-Drugbank-Caffeine-5">[5]</a> <a href="/wiki/7-Methylxanthine" title="7-Methylxanthine">7-Methylxanthine</a> is also a metabolite of caffeine.<a href="#cite_note-InxightDrugs-193">[193]</a><a href="#cite_note-pmid35918918-194">[194]</a> Each of the above metabolites is further metabolized and then excreted in the urine. Caffeine can accumulate in individuals with severe <a href="/wiki/Liver_disease" title="Liver disease">liver disease</a>, increasing its half-life.<a href="#cite_note-pmid18762933-195">[195]</a> A 2011 review found that increased caffeine intake was associated with a variation in two genes that increase the rate of caffeine <a href="/wiki/Catabolism" title="Catabolism">catabolism</a>. Subjects who had this <a href="/wiki/Mutation" title="Mutation">mutation</a> on both <a href="/wiki/Chromosomes" class="mw-redirect" title="Chromosomes">chromosomes</a> consumed 40 mg more caffeine per day than others.<a href="#cite_note-Gibson2011-196">[196]</a> This is presumably due to the need for a higher intake to achieve a comparable desired effect, not that the gene led to a disposition for greater incentive of habituation. <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Caffeine&action=edit&section=34" title="Edit section: Chemistry">edit</a>]</div> Pure <a href="/wiki/Anhydrous" title="Anhydrous">anhydrous</a> caffeine is a bitter-tasting, white, odorless powder with a melting point of 235–238 °C.<a href="#cite_note-Pubchem_properties-7">[7]</a><a href="#cite_note-ChemSpider-8">[8]</a> Caffeine is moderately soluble in water at room temperature (2 g/100 mL), but quickly soluble in boiling water (66 g/100 mL).<a href="#cite_note-solu-197">[197]</a> It is also moderately soluble in ethanol (1.5 g/100 mL).<a href="#cite_note-solu-197">[197]</a> It is weakly basic (pKa of <a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">conjugate acid</a> = ~0.6) requiring strong acid to protonate it.<a href="#cite_note-pKa-198">[198]</a> Caffeine does not contain any <a href="/wiki/Stereogenic" class="mw-redirect" title="Stereogenic">stereogenic</a> centers<a href="#cite_note-isbn0-7614-2242-0-199">[199]</a> and hence is classified as an <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">achiral</a> molecule.<a href="#cite_note-isbn1-58409-016-2-200">[200]</a> The <a href="/wiki/Xanthine" title="Xanthine">xanthine</a> core of caffeine contains two fused rings, a <a href="/wiki/Pyrimidinedione" title="Pyrimidinedione">pyrimidinedione</a> and <a href="/wiki/Imidazole" title="Imidazole">imidazole</a>. The pyrimidinedione in turn contains two <a href="/wiki/Amide" title="Amide">amide</a> functional groups that exist predominantly in a <a href="/wiki/Zwitterion" title="Zwitterion">zwitterionic</a> <a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">resonance</a> the location from which the nitrogen atoms are double bonded to their adjacent amide carbons atoms. Hence all six of the atoms within the pyrimidinedione ring system are sp2 <a href="/wiki/Orbital_hybridization" class="mw-redirect" title="Orbital hybridization">hybridized</a> and planar. The imidazole ring also has a <a href="/wiki/Imidazole#Structure_and_properties" title="Imidazole">resonance</a>. Therefore, the fused 5,6 ring core of caffeine contains a total of ten <a href="/wiki/Pi_bond" title="Pi bond">pi electrons</a> and hence according to <a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a> is <a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a>.<a href="#cite_note-urlquantum.esu.edu-201">[201]</a> <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=35" title="Edit section: Synthesis">edit</a>]</div> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Caffeine_biosynthesis.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Caffeine_biosynthesis.tif/lossy-page1-290px-Caffeine_biosynthesis.tif.jpg" decoding="async" width="290" height="156" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Caffeine_biosynthesis.tif/lossy-page1-435px-Caffeine_biosynthesis.tif.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Caffeine_biosynthesis.tif/lossy-page1-580px-Caffeine_biosynthesis.tif.jpg 2x" data-file-width="2537" data-file-height="1361" /></a><figcaption>One <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthetic route</a> of caffeine, as performed by <a href="/wiki/Camellia" title="Camellia">Camellia</a> and <a href="/wiki/Coffea" title="Coffea">Coffea</a> species<a href="#cite_note-urlcaffeine_biosynthesis-202">[202]</a><a href="#cite_note-203">[203]</a></figcaption></figure> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Caffeine_synthesis-en.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Caffeine_synthesis-en.svg/290px-Caffeine_synthesis-en.svg.png" decoding="async" width="290" height="126" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Caffeine_synthesis-en.svg/435px-Caffeine_synthesis-en.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Caffeine_synthesis-en.svg/580px-Caffeine_synthesis-en.svg.png 2x" data-file-width="3263" data-file-height="1421" /></a><figcaption>One <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">laboratory synthesis</a> of caffeine<a href="#cite_note-isbn1-58829-173-1-204">[204]</a><a href="#cite_note-US2785162-205">[205]</a></figcaption></figure> The <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> of caffeine is an example of <a href="/wiki/Convergent_evolution" title="Convergent evolution">convergent evolution</a> among different species.<a href="#cite_note-206">[206]</a><a href="#cite_note-207">[207]</a><a href="#cite_note-208">[208]</a> Caffeine may be synthesized in the lab starting with <a href="/wiki/1,3-dimethylurea" class="mw-redirect" title="1,3-dimethylurea">1,3-dimethylurea</a> and <a href="/wiki/Malonic_acid" title="Malonic acid">malonic acid</a>.[<a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify">clarification needed</a>]<a href="#cite_note-isbn1-58829-173-1-204">[204]</a><a href="#cite_note-US2785162-205">[205]</a><a href="#cite_note-Zajac_2003-209">[209]</a> Production of synthesized caffeine largely takes place in pharmaceutical plants in China. Synthetic and natural caffeine are chemically identical and nearly indistinguishable. The primary distinction is that synthetic caffeine is manufactured from urea and chloroacetic acid, while natural caffeine is extracted from plant sources, a process known as <a href="/wiki/Decaffeination" title="Decaffeination">decaffeination</a>.<a href="#cite_note-:0-210">[210]</a> Despite the different production methods, the final product and its effects on the body are identical. Research on synthetic caffeine supports that it has the same stimulating effects on the body as natural caffeine.<a href="#cite_note-:04-211">[211]</a> And although many claim that natural caffeine is absorbed slower and therefore leads to a gentler caffeine crash, there is little scientific evidence supporting the notion.<a href="#cite_note-:0-210">[210]</a> <div class="mw-heading mw-heading3"><h3 id="Decaffeination">Decaffeination</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=36" title="Edit section: Decaffeination">edit</a>]</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/Decaffeination" title="Decaffeination">Decaffeination</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:CaffeineCrystals_Fibrous_10xDarkField.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/CaffeineCrystals_Fibrous_10xDarkField.jpg/330px-CaffeineCrystals_Fibrous_10xDarkField.jpg" decoding="async" width="290" height="176" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/CaffeineCrystals_Fibrous_10xDarkField.jpg/500px-CaffeineCrystals_Fibrous_10xDarkField.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/CaffeineCrystals_Fibrous_10xDarkField.jpg/960px-CaffeineCrystals_Fibrous_10xDarkField.jpg 2x" data-file-width="7362" data-file-height="4476" /></a><figcaption>Fibrous <a href="/wiki/Crystal" title="Crystal">crystals</a> of purified caffeine. <a href="/wiki/Dark-field_microscopy" title="Dark-field microscopy">Dark-field microscopy</a> image, about 7 mm × 11 mm.</figcaption></figure> Germany, the birthplace of decaffeinated coffee, is home to several decaffeination plants, including the world's largest, Coffein Compagnie.<a href="#cite_note-212">[212]</a> Over half of the decaf coffee sold in the U.S. first travels from the tropics to Germany for caffeine removal before making its way to American consumers.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Extraction of caffeine from coffee, to produce caffeine and decaffeinated coffee, can be performed using various solvents. Following are main methods: <ul><li>Water extraction: Coffee beans are soaked in water. The water, which contains many other compounds in addition to caffeine and contributes to the flavor of coffee, is then passed through <a href="/wiki/Activated_carbon" title="Activated carbon">activated charcoal</a>, which removes the caffeine. The water can then be put back with the beans and evaporated dry, leaving decaffeinated coffee with its original flavor. Coffee manufacturers recover the caffeine and resell it for use in soft drinks and over-the-counter caffeine tablets.<a href="#cite_note-Decaffeination-213">[213]</a></li> <li>Supercritical carbon dioxide extraction: <a href="/wiki/Supercritical_carbon_dioxide" title="Supercritical carbon dioxide">Supercritical carbon dioxide</a> is an excellent nonpolar <a href="/wiki/Solvent" title="Solvent">solvent</a> for caffeine, and is safer than the organic solvents that are otherwise used. The extraction process is simple: CO2 is forced through the green coffee beans at temperatures above 31.1 °C and pressures above 73 <a href="/wiki/Atmosphere_(unit)" class="mw-redirect" title="Atmosphere (unit)">atm</a>. Under these conditions, CO2 is in a "<a href="/wiki/Supercritical_fluid" title="Supercritical fluid">supercritical</a>" <a href="/wiki/Phase_(matter)" title="Phase (matter)">state</a>: It has gaslike properties that allow it to penetrate deep into the beans but also liquid-like properties that dissolve 97–99% of the caffeine. The caffeine-laden CO2 is then sprayed with high-pressure water to remove the caffeine. The caffeine can then be isolated by <a href="/wiki/Activated_carbon" title="Activated carbon">charcoal</a> <a href="/wiki/Adsorption" title="Adsorption">adsorption</a> (as above) or by <a href="/wiki/Distillation" title="Distillation">distillation</a>, <a href="/wiki/Recrystallization_(chemistry)" title="Recrystallization (chemistry)">recrystallization</a>, or <a href="/wiki/Reverse_osmosis" title="Reverse osmosis">reverse osmosis</a>.<a href="#cite_note-Decaffeination-213">[213]</a></li> <li>Extraction by organic solvents: Certain organic solvents such as <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a> present much less health and environmental hazard than chlorinated and aromatic organic solvents used formerly. Another method is to use triglyceride oils obtained from spent coffee grounds.<a href="#cite_note-Decaffeination-213">[213]</a></li></ul> "Decaffeinated" coffees do in fact contain caffeine in many cases – some commercially available decaffeinated coffee products contain considerable levels. One study found that decaffeinated coffee contained 10 mg of caffeine per cup, compared to approximately 85 mg of caffeine per cup for regular coffee.<a href="#cite_note-pmid17132260-214">[214]</a> <div class="mw-heading mw-heading3"><h3 id="Detection_in_body_fluids">Detection in body fluids</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=37" title="Edit section: Detection in body fluids">edit</a>]</div> Caffeine can be quantified in blood, plasma, or serum to monitor therapy in <a href="/wiki/Neonates" class="mw-redirect" title="Neonates">neonates</a>, confirm a diagnosis of poisoning, or facilitate a medicolegal death investigation. Plasma caffeine levels are usually in the range of 2–10 mg/L in coffee drinkers, 12–36 mg/L in neonates receiving treatment for apnea, and 40–400 mg/L in victims of acute overdosage. Urinary caffeine concentration is frequently measured in competitive sports programs, for which a level in excess of 15 mg/L is usually considered to represent abuse.<a href="#cite_note-215">[215]</a> <div class="mw-heading mw-heading3"><h3 id="Analogs">Analogs</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=38" title="Edit section: Analogs">edit</a>]</div> Some analog substances have been created which mimic caffeine's properties with either function or structure or both. Of the latter group are the <a href="/wiki/Xanthine" title="Xanthine">xanthines</a> <a href="/wiki/DMPX" title="DMPX">DMPX</a><a href="#cite_note-DMPX-216">[216]</a> and <a href="/wiki/8-chlorotheophylline" class="mw-redirect" title="8-chlorotheophylline">8-chlorotheophylline</a>, which is an ingredient in <a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">dramamine</a>. Members of a class of nitrogen substituted xanthines are often proposed as potential alternatives to caffeine.<a href="#cite_note-217">[217]</a>[<a href="/wiki/Wikipedia:Reliable_sources" title="Wikipedia:Reliable sources">unreliable source?</a>] Many other xanthine analogues constituting the adenosine receptor antagonist class have also been elucidated.<a href="#cite_note-218">[218]</a> Some other caffeine analogs: <ul><li><a href="/wiki/Dipropylcyclopentylxanthine" title="Dipropylcyclopentylxanthine">Dipropylcyclopentylxanthine</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dimethylxanthine" title="8-Cyclopentyl-1,3-dimethylxanthine">8-Cyclopentyl-1,3-dimethylxanthine</a></li> <li><a href="/wiki/8-Phenyltheophylline" title="8-Phenyltheophylline">8-Phenyltheophylline</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="Precipitation_of_tannins">Precipitation of tannins</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=39" title="Edit section: Precipitation of tannins">edit</a>]</div> Caffeine, as do other alkaloids such as <a href="/wiki/Cinchonine" title="Cinchonine">cinchonine</a>, <a href="/wiki/Quinine" title="Quinine">quinine</a> or <a href="/wiki/Strychnine" title="Strychnine">strychnine</a>, precipitates polyphenols and <a href="/wiki/Tannin" title="Tannin">tannins</a>. This property can be used in a quantitation method.[<a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify">clarification needed</a>]<a href="#cite_note-219">[219]</a> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2>[<a href="/w/index.php?title=Caffeine&action=edit&section=40" title="Edit section: Natural occurrence">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Coffee_beans2.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Coffee_beans2.jpg/220px-Coffee_beans2.jpg" decoding="async" width="220" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Coffee_beans2.jpg/330px-Coffee_beans2.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Coffee_beans2.jpg/440px-Coffee_beans2.jpg 2x" data-file-width="8688" data-file-height="5792" /></a><figcaption>Roasted coffee beans</figcaption></figure> Around thirty plant species are known to contain caffeine.<a href="#cite_note-220">[220]</a> Common sources are the "beans" (seeds) of the two cultivated coffee plants, <a href="/wiki/Coffea_arabica" title="Coffea arabica">Coffea arabica</a> and <a href="/wiki/Coffea_canephora" title="Coffea canephora">Coffea canephora</a> (the quantity varies, but 1.3% is a typical value); and of the cocoa plant, <a href="/wiki/Theobroma_cacao" title="Theobroma cacao">Theobroma cacao</a>; the leaves of the <a href="/wiki/Camellia_sinensis" title="Camellia sinensis">tea plant</a>; and <a href="/wiki/Kola_nut" title="Kola nut">kola nuts</a>. Other sources include the leaves of <a href="/wiki/Ilex_vomitoria" title="Ilex vomitoria">yaupon holly</a>, South American holly <a href="/wiki/Yerba_mate" title="Yerba mate">yerba mate</a>, and Amazonian holly <a href="/wiki/Ilex_guayusa" title="Ilex guayusa">guayusa</a>; and seeds from Amazonian maple <a href="/wiki/Guarana" title="Guarana">guarana</a> berries. Temperate climates around the world have produced unrelated caffeine-containing plants. Caffeine in plants acts as a natural <a href="/wiki/Pesticide" title="Pesticide">pesticide</a>: it can paralyze and kill predator insects feeding on the plant.<a href="#cite_note-insecticide-221">[221]</a> High caffeine levels are found in coffee seedlings when they are developing foliage and lack mechanical protection.<a href="#cite_note-222">[222]</a> In addition, high caffeine levels are found in the surrounding soil of coffee seedlings, which inhibits seed germination of nearby coffee seedlings, thus giving seedlings with the highest caffeine levels fewer competitors for existing resources for survival.<a href="#cite_note-223">[223]</a> Caffeine is stored in tea leaves in two places. Firstly, in the cell <a href="/wiki/Vacuole" title="Vacuole">vacuoles</a> where it is complexed with <a href="/wiki/Polyphenol" title="Polyphenol">polyphenols</a>. This caffeine probably is released into the mouth parts of insects, to discourage herbivory. Secondly, around the vascular bundles, where it probably inhibits pathogenic fungi from entering and colonizing the vascular bundles.<a href="#cite_note-224">[224]</a> Caffeine in nectar may improve the reproductive success of the <a href="/wiki/Pollen" title="Pollen">pollen</a> producing plants by enhancing the reward memory of pollinators such as <a href="/wiki/Honey_bee" title="Honey bee">honey bees</a>.<a href="#cite_note-pmid23471406-18">[18]</a> The differing perceptions in the effects of ingesting beverages made from various plants containing caffeine could be explained by the fact that these beverages also contain varying mixtures of other <a href="/wiki/Methylxanthine" class="mw-redirect" title="Methylxanthine">methylxanthine</a> <a href="/wiki/Alkaloid" title="Alkaloid">alkaloids</a>, including the <a href="/wiki/Cardiac" class="mw-redirect" title="Cardiac">cardiac</a> stimulants <a href="/wiki/Theophylline" title="Theophylline">theophylline</a> and <a href="/wiki/Theobromine" title="Theobromine">theobromine</a>, and polyphenols that can form insoluble complexes with caffeine.<a href="#cite_note-Ref-1-225">[225]</a> <div class="mw-heading mw-heading2"><h2 id="Products">Products</h2>[<a href="/w/index.php?title=Caffeine&action=edit&section=41" title="Edit section: Products">edit</a>]</div> <table class="sortable wikitable" style="width:35%; float:right; clear:right; margin:0 0 0.5em 1em; font-size:85%;"> <caption>Caffeine content in select food and drugs<a href="#cite_note-Content-226">[226]</a><a href="#cite_note-Erowid-227">[227]</a><a href="#cite_note-228">[228]</a><a href="#cite_note-JAT-229">[229]</a><a href="#cite_note-Richardson-230">[230]</a> </caption> <tbody><tr> <th scope="col">Product </th> <th scope="col" style="width:26%;">Serving size </th> <th scope="col" style="width:12%;">Caffeine per serving (<a href="/wiki/Milligrams" class="mw-redirect" title="Milligrams">mg</a>) </th> <th scope="col" style="width:12%;">Caffeine (mg/<a href="/wiki/Litre" title="Litre">L</a>) </th></tr> <tr> <td>Caffeine tablet (regular-strength) </td> <td>1 tablet </td> <td>100 </td> <td>— </td></tr> <tr> <td>Caffeine tablet (extra-strength) </td> <td>1 tablet </td> <td>200 </td> <td>— </td></tr> <tr> <td><a href="/wiki/Excedrin" class="mw-redirect" title="Excedrin">Excedrin</a> tablet </td> <td>1 tablet </td> <td>65 </td> <td>— </td></tr> <tr> <td><a href="/wiki/Coffee_percolator" title="Coffee percolator">Percolated</a> <a href="/wiki/Coffee" title="Coffee">coffee</a> </td> <td>207 <a href="/wiki/Millilitre" class="mw-redirect" title="Millilitre">mL</a> (7.0 <a href="/wiki/US_fluid_ounce" class="mw-redirect" title="US fluid ounce">US fl oz</a>) </td> <td>80–135 </td> <td>386–652 </td></tr> <tr> <td><a href="/wiki/Drip_brew" class="mw-redirect" title="Drip brew">Drip</a> coffee </td> <td>207 mL (7.0 US fl oz) </td> <td>115–175 </td> <td>555–845 </td></tr> <tr> <td>Coffee, <a href="/wiki/Decaffeinated" class="mw-redirect" title="Decaffeinated">decaffeinated</a> </td> <td>207 mL (7.0 US fl oz) </td> <td>5–15 </td> <td>24–72 </td></tr> <tr> <td>Coffee, <a href="/wiki/Espresso" title="Espresso">espresso</a> </td> <td>44–60 mL (1.5–2.0 US fl oz) </td> <td>100 </td> <td>1,691–2,254 </td></tr> <tr> <td><a href="/wiki/Tea" title="Tea">Tea</a> – black, green, and other <a href="/wiki/Tea#Processing_and_classification" title="Tea">types</a>, – steeped for 3 min. </td> <td>177 mL (6.0 US fl oz) </td> <td>22–74<a href="#cite_note-JAT-229">[229]</a><a href="#cite_note-Richardson-230">[230]</a> </td> <td>124–418 </td></tr> <tr> <td>Guayakí <a href="/wiki/Yerba_mate" title="Yerba mate">yerba mate</a> (loose leaf) </td> <td>6 g (0.21 oz) </td> <td>85<a href="#cite_note-Guayakí-231">[231]</a> </td> <td>approx. 358 </td></tr> <tr> <td><a href="/wiki/Coca-Cola" title="Coca-Cola">Coca-Cola</a> </td> <td>355 mL (12.0 US fl oz) </td> <td>34 </td> <td>96 </td></tr> <tr> <td><a href="/wiki/Mountain_Dew" title="Mountain Dew">Mountain Dew</a> </td> <td>355 mL (12.0 US fl oz) </td> <td>54 </td> <td>154 </td></tr> <tr> <td><a href="/wiki/Pepsi_Zero_Sugar" title="Pepsi Zero Sugar">Pepsi Zero Sugar</a> </td> <td>355 mL (12.0 US fl oz) </td> <td>69 </td> <td>194 </td></tr> <tr> <td><a href="/wiki/Guaran%C3%A1_Antarctica" title="Guaraná Antarctica">Guaraná Antarctica</a> </td> <td>350 mL (12 US fl oz) </td> <td>30 </td> <td>100 </td></tr> <tr> <td><a href="/wiki/Jolt_Cola" title="Jolt Cola">Jolt Cola</a> </td> <td>695 mL (23.5 US fl oz) </td> <td>280 </td> <td>403 </td></tr> <tr> <td><a href="/wiki/Red_Bull" title="Red Bull">Red Bull</a> </td> <td>250 mL (8.5 US fl oz) </td> <td>80 </td> <td>320 </td></tr> <tr> <td>Coffee-flavored milk drink </td> <td>300–600 mL (10–20 US fl oz) </td> <td>33–197<a href="#cite_note-Desbrow-232">[232]</a> </td> <td>66–354<a href="#cite_note-Desbrow-232">[232]</a> </td></tr> <tr> <td><a href="/wiki/Cocoa_solids" title="Cocoa solids">Cocoa, dry powder, unsweetened [unspecified strain]</a> </td> <td>100 g </td> <td>230<a href="#cite_note-USDA_Food_Central_item_169593-233">[233]</a> </td> <td>— </td></tr> <tr> <td>Cocoa solids, defatted, Criollo strain </td> <td>100 g </td> <td>1130<a href="#cite_note-caffeine_content_in_cocoa_solids_by_strain-234">[234]</a> </td> <td>— </td></tr> <tr> <td>Cocoa solids, defatted, Forastero strain </td> <td>100 g </td> <td>130<a href="#cite_note-caffeine_content_in_cocoa_solids_by_strain-234">[234]</a> </td> <td>— </td></tr> <tr> <td>Cocoa solids, defatted, Nacional strain </td> <td>100 g </td> <td>240<a href="#cite_note-caffeine_content_in_cocoa_solids_by_strain-234">[234]</a> </td> <td>— </td></tr> <tr> <td>Cocoa solids, defatted, Trinitario strain </td> <td>100 g </td> <td>630<a href="#cite_note-caffeine_content_in_cocoa_solids_by_strain-234">[234]</a> </td> <td>— </td></tr> <tr> <td><a href="/wiki/Dark_chocolate" title="Dark chocolate">Chocolate, dark</a>, 70-85% cacao solids </td> <td>100 g </td> <td>80<a href="#cite_note-USDA_Food_Central_item_170273-235">[235]</a> </td> <td>— </td></tr> <tr> <td>Chocolate, dark, 60-69% cacao solids </td> <td>100 g </td> <td>86<a href="#cite_note-USDA_Food_Central_item_170272-236">[236]</a> </td> <td>— </td></tr> <tr> <td>Chocolate, dark, 45- 59% cacao solids </td> <td>100 g </td> <td>43<a href="#cite_note-USDA_Food_Central_item_170271-237">[237]</a> </td> <td>— </td></tr> <tr> <td><a href="/wiki/Milk_chocolate" title="Milk chocolate">Candies, milk chocolate</a> </td> <td>100 g </td> <td>20<a href="#cite_note-USDA_Food_Central_item_167587-238">[238]</a> </td> <td>— </td></tr> <tr> <td><a href="/wiki/Hershey%27s_Special_Dark" title="Hershey's Special Dark">Hershey's Special Dark</a> (45% cacao content) </td> <td>1 bar (43 g or 1.5 oz) </td> <td>31 </td> <td>— </td></tr> <tr> <td><a href="/wiki/Hershey%27s_Milk_Chocolate" class="mw-redirect" title="Hershey's Milk Chocolate">Hershey's Milk Chocolate</a> (11% cacao content) </td> <td>1 bar (43 g or 1.5 oz) </td> <td>10 </td> <td>— </td></tr></tbody></table> Products containing caffeine include coffee, tea, <a href="/wiki/Soft_drink" title="Soft drink">soft drinks</a> ("colas"), <a href="/wiki/Energy_drink" title="Energy drink">energy drinks</a>, other beverages, <a href="/wiki/Chocolate" title="Chocolate">chocolate</a>,<a href="#cite_note-Matissek_R_1997_175–84-239">[239]</a> caffeine tablets, other oral products, and inhalation products. According to a 2020 study in the United States, coffee is the major source of caffeine intake in middle-aged adults, while soft drinks and tea are the major sources in adolescents.<a href="#cite_note-Van_Dam-79">[79]</a> Energy drinks are more commonly consumed as a source of caffeine in adolescents as compared to adults.<a href="#cite_note-Van_Dam-79">[79]</a> <div class="mw-heading mw-heading3"><h3 id="Beverages">Beverages</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=42" title="Edit section: Beverages">edit</a>]</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/Caffeinated_drink" title="Caffeinated drink">Caffeinated drink</a></div> <div class="mw-heading mw-heading4"><h4 id="Coffee">Coffee</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=43" title="Edit section: Coffee">edit</a>]</div> The world's primary source of caffeine is the coffee "bean" (the seed of the <a href="/wiki/Coffea" title="Coffea">coffee plant</a>), from which coffee is brewed. Caffeine content in coffee varies widely depending on the type of <a href="/wiki/Coffee_bean" title="Coffee bean">coffee bean</a> and the method of preparation used;<a href="#cite_note-ICO-240">[240]</a> even beans within a given bush can show variations in concentration. In general, one serving of coffee ranges from 80 to 100 milligrams, for a single shot (30 milliliters) of arabica-variety <a href="/wiki/Espresso" title="Espresso">espresso</a>, to approximately 100–125 milligrams for a cup (120 milliliters) of <a href="/wiki/Drip_coffee" title="Drip coffee">drip coffee</a>.<a href="#cite_note-caffaq_roast-241">[241]</a><a href="#cite_note-jeremiahspick-242">[242]</a> <a href="/wiki/Coffea_arabica" title="Coffea arabica">Arabica</a> coffee typically contains half the caffeine of the <a href="/wiki/Coffea_canephora" title="Coffea canephora">robusta</a> variety.<a href="#cite_note-ICO-240">[240]</a> In general, dark-roast coffee has slightly less caffeine than lighter roasts because the roasting process reduces caffeine content of the bean by a small amount.<a href="#cite_note-caffaq_roast-241">[241]</a><a href="#cite_note-jeremiahspick-242">[242]</a> <div class="mw-heading mw-heading4"><h4 id="Tea">Tea</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=44" title="Edit section: Tea">edit</a>]</div> Tea contains more caffeine than coffee by dry weight. A typical serving, however, contains much less, since less of the product is used as compared to an equivalent serving of coffee. Also contributing to caffeine content are growing conditions, processing techniques, and other variables. Thus, teas contain varying amounts of caffeine.<a href="#cite_note-FRI-243">[243]</a> Tea contains small amounts of <a href="/wiki/Theobromine" title="Theobromine">theobromine</a> and slightly higher levels of <a href="/wiki/Theophylline" title="Theophylline">theophylline</a> than coffee. Preparation and many other factors have a significant impact on tea, and color is a poor indicator of caffeine content. Teas like the pale Japanese <a href="/wiki/Green_tea" title="Green tea">green tea</a>, <a href="/wiki/Gyokuro" title="Gyokuro">gyokuro</a>, for example, contain far more caffeine than much darker teas like <a href="/wiki/Lapsang_souchong" title="Lapsang souchong">lapsang souchong</a>, which has minimal caffeine content.<a href="#cite_note-FRI-243">[243]</a> <div class="mw-heading mw-heading4"><h4 id="Soft_drinks_and_energy_drinks">Soft drinks and energy drinks</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=45" title="Edit section: Soft drinks and energy drinks">edit</a>]</div> Caffeine is also a common ingredient of <a href="/wiki/Soft_drink" title="Soft drink">soft drinks</a>, such as <a href="/wiki/Cola" title="Cola">cola</a>, originally prepared from <a href="/wiki/Kola_nut" title="Kola nut">kola nuts</a>. Soft drinks typically contain 0 to 55 milligrams of caffeine per 12 ounce (350 mL) serving.<a href="#cite_note-244">[244]</a> By contrast, <a href="/wiki/Energy_drink" title="Energy drink">energy drinks</a>, such as <a href="/wiki/Red_Bull" title="Red Bull">Red Bull</a>, can start at 80 milligrams of caffeine per serving. The caffeine in these drinks either originates from the ingredients used or is an additive derived from the product of <a href="/wiki/Decaffeination" title="Decaffeination">decaffeination</a> or from chemical synthesis. Guarana, a primary ingredient of energy drinks, contains large amounts of caffeine with small amounts of theobromine and theophylline in a naturally occurring <a href="/wiki/Slow-release" class="mw-redirect" title="Slow-release">slow-release</a> <a href="/wiki/Excipient" title="Excipient">excipient</a>.<a href="#cite_note-245">[245]</a> <div class="mw-heading mw-heading4"><h4 id="Other_beverages">Other beverages</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=46" title="Edit section: Other beverages">edit</a>]</div> <ul><li><a href="/wiki/Mat%C3%A9" class="mw-redirect" title="Maté">Maté</a> is a drink popular in many parts of South America. Its preparation consists of filling a gourd with the leaves of the South American holly <a href="/wiki/Yerba_mate" title="Yerba mate">yerba mate</a>, pouring hot but not boiling water over the leaves, and drinking with a straw, the bombilla, which acts as a filter so as to draw only the liquid and not the yerba leaves.<a href="#cite_note-246">[246]</a></li> <li><a href="/wiki/Guaran%C3%A1_(soft_drink)" title="Guaraná (soft drink)">Guaraná</a> is a soft drink originating in Brazil made from the seeds of the <a href="/wiki/Guaran%C3%A1" class="mw-redirect" title="Guaraná">Guaraná</a> fruit.</li> <li>The leaves of <a href="/wiki/Ilex_guayusa" title="Ilex guayusa">Ilex guayusa</a>, the Ecuadorian holly tree, are placed in boiling water to make a guayusa tea.<a href="#cite_note-247">[247]</a></li> <li>The leaves of <a href="/wiki/Ilex_vomitoria" title="Ilex vomitoria">Ilex vomitoria</a>, the yaupon holly tree, are placed in boiling water to make a yaupon tea.</li> <li>Commercially prepared coffee-<a href="/wiki/Flavoured_milk" class="mw-redirect" title="Flavoured milk">flavoured milk</a> beverages are popular in Australia.<a href="#cite_note-248">[248]</a> Examples include <a href="/wiki/Oak_(flavoured_milk)" title="Oak (flavoured milk)">Oak's Ice Coffee</a> and <a href="/wiki/Farmers_Union_Iced_Coffee" title="Farmers Union Iced Coffee">Farmers Union Iced Coffee</a>. The amount of caffeine in these beverages can vary widely. Caffeine concentrations can differ significantly from the manufacturer's claims.<a href="#cite_note-Desbrow-232">[232]</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="Cacao_solids">Cacao solids</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=47" title="Edit section: Cacao solids">edit</a>]</div> <a href="/wiki/Cocoa_solids" title="Cocoa solids">Cocoa solids</a> (derived from <a href="/wiki/Cocoa_bean" title="Cocoa bean">cocoa bean</a>) contain 230 mg caffeine per 100 g.<a href="#cite_note-USDA_Food_Central_item_169593-233">[233]</a> The caffeine content varies between cocoa bean strains. Caffeine content mg/g (sorted by lowest caffeine content):<a href="#cite_note-caffeine_content_in_cocoa_solids_by_strain-234">[234]</a> <ul><li>Forastero (defatted): 1.3 mg/g</li> <li>Nacional (defatted): 2.4 mg/g</li> <li>Trinitario (defatted): 6.3/g</li> <li>Criollo (defatted): 11.3 mg/g</li></ul> <div class="mw-heading mw-heading4"><h4 id="Chocolate">Chocolate</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=48" title="Edit section: Chocolate">edit</a>]</div> Caffeine per 100 g: <ul><li><a href="/wiki/Dark_chocolate" title="Dark chocolate">Dark chocolate</a>, 70-85% cacao solids: 80 mg<a href="#cite_note-USDA_Food_Central_item_170273-235">[235]</a></li> <li>Dark chocolate, 60-69% cacao solids: 86 mg<a href="#cite_note-USDA_Food_Central_item_170272-236">[236]</a></li> <li>Dark chocolate, 45- 59% cacao solids: 43 mg<a href="#cite_note-USDA_Food_Central_item_170271-237">[237]</a></li> <li><a href="/wiki/Milk_chocolate" title="Milk chocolate">Milk chocolate</a>: 20 mg<a href="#cite_note-USDA_Food_Central_item_167587-238">[238]</a></li></ul> The stimulant effect of chocolate may be due to a combination of <a href="/wiki/Theobromine" title="Theobromine">theobromine</a> and <a href="/wiki/Theophylline" title="Theophylline">theophylline</a>, as well as caffeine.<a href="#cite_note-pmid15549276-249">[249]</a> <div class="mw-heading mw-heading3"><h3 id="Tablets">Tablets</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=49" title="Edit section: Tablets">edit</a>]</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:No-Doz.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/No-Doz.jpg/250px-No-Doz.jpg" decoding="async" width="220" height="295" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/No-Doz.jpg/330px-No-Doz.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/69/No-Doz.jpg/500px-No-Doz.jpg 2x" data-file-width="1475" data-file-height="1975" /></a><figcaption>No-Doz 100 mg caffeine tablets</figcaption></figure> Tablets offer several advantages over coffee, tea, and other caffeinated beverages, including convenience, known dosage, and avoidance of concomitant intake of sugar, acids, and fluids. The use of caffeine in this form is said to improve mental alertness.<a href="#cite_note-250">[250]</a> These tablets are commonly used by students studying for their exams and by people who work or drive for long hours.<a href="#cite_note-251">[251]</a> <div class="mw-heading mw-heading3"><h3 id="Other_oral_products">Other oral products</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=50" title="Edit section: Other oral products">edit</a>]</div> One U.S. company is marketing oral dissolvable caffeine strips.<a href="#cite_note-252">[252]</a> Another intake route is <a href="/wiki/SpazzStick" title="SpazzStick">SpazzStick</a>, a caffeinated <a href="/wiki/Lip_balm" title="Lip balm">lip balm</a>.<a href="#cite_note-253">[253]</a> Alert Energy Caffeine Gum was introduced in the United States in 2013, but was voluntarily withdrawn after an announcement of an investigation by the FDA of the health effects of added caffeine in foods.<a href="#cite_note-NYT5813-254">[254]</a> <div class="mw-heading mw-heading3"><h3 id="Inhalants">Inhalants</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=51" title="Edit section: Inhalants">edit</a>]</div> Similar to an <a href="/wiki/E-cigarette" class="mw-redirect" title="E-cigarette">e-cigarette</a>, a caffeine inhaler may be used to deliver caffeine or a stimulant like <a href="/wiki/Guarana" title="Guarana">guarana</a> by <a href="/wiki/Vaping" class="mw-redirect" title="Vaping">vaping</a>.<a href="#cite_note-255">[255]</a> In 2012, the FDA sent a <a href="/wiki/FDA_warning_letter" title="FDA warning letter">warning letter</a> to one of the companies marketing an inhaler, expressing concerns for the lack of safety information available about inhaled caffeine.<a href="#cite_note-256">[256]</a><a href="#cite_note-257">[257]</a> <div class="mw-heading mw-heading3"><h3 id="Combinations_with_other_drugs">Combinations with other drugs</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=52" title="Edit section: Combinations with other drugs">edit</a>]</div> <ul><li>Some beverages combine <a href="/wiki/Ethanol" title="Ethanol">alcohol</a> with caffeine to create a <a href="/wiki/Caffeinated_alcoholic_drink" title="Caffeinated alcoholic drink">caffeinated alcoholic drink</a>. The stimulant effects of caffeine may mask the <a href="/wiki/Depressant" title="Depressant">depressant</a> effects of alcohol, potentially reducing the user's awareness of their level of <a href="/wiki/Alcohol_intoxication" title="Alcohol intoxication">intoxication</a>. Such beverages have been the subject of <a href="/wiki/Ban_on_caffeinated_alcoholic_beverages" class="mw-redirect" title="Ban on caffeinated alcoholic beverages">bans</a> due to safety concerns. In particular, the <a href="/wiki/United_States_Food_and_Drug_Administration" class="mw-redirect" title="United States Food and Drug Administration">United States Food and Drug Administration</a> has classified caffeine added to malt liquor beverages as an "unsafe food additive".<a href="#cite_note-258">[258]</a></li> <li><a href="/wiki/Ya_ba" title="Ya ba">Ya ba</a> contains a combination of <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a> and caffeine.</li> <li>Painkillers such as <a href="/wiki/Propyphenazone/paracetamol/caffeine" title="Propyphenazone/paracetamol/caffeine">propyphenazone/paracetamol/caffeine</a> combine caffeine with an <a href="/wiki/Analgesic" title="Analgesic">analgesic</a>.</li></ul> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Caffeine&action=edit&section=53" title="Edit section: History">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Discovery_and_spread_of_use">Discovery and spread of use</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=54" title="Edit section: Discovery and spread of use">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Kahvihuone.jpg" class="mw-file-description"><img alt="An old photo of a dozen old and middle-aged men sitting on the ground around a mat. A man in front sits next to a mortar and holds a bat, ready for grinding. A man opposite to him holds a long spoon." src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Kahvihuone.jpg/220px-Kahvihuone.jpg" decoding="async" width="220" height="201" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Kahvihuone.jpg/330px-Kahvihuone.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Kahvihuone.jpg/440px-Kahvihuone.jpg 2x" data-file-width="597" data-file-height="545" /></a><figcaption><a href="/wiki/Coffeehouse" title="Coffeehouse">Coffeehouse</a> in <a href="/wiki/History_of_Palestine#Ottoman_period" title="History of Palestine">Palestine</a>, <abbr title="circa">c.</abbr> 1900</figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/History_of_chocolate" title="History of chocolate">History of chocolate</a>, <a href="/wiki/History_of_coffee" title="History of coffee">History of coffee</a>, <a href="/wiki/History_of_tea" title="History of tea">History of tea</a>, and <a href="/wiki/History_of_yerba_mate" title="History of yerba mate">History of yerba mate</a></div> According to Chinese legend, the <a href="/wiki/Emperor_of_China" title="Emperor of China">Chinese emperor</a> <a href="/wiki/Shennong" title="Shennong">Shennong</a>, reputed to have reigned in about 3000 BCE, inadvertently discovered tea when he noted that when certain leaves fell into boiling water, a fragrant and restorative drink resulted.<a href="#cite_note-259">[259]</a> Shennong is also mentioned in Lu Yu's <a href="/wiki/Cha_Jing" class="mw-redirect" title="Cha Jing">Cha Jing</a>, a famous early work on the subject of tea.<a href="#cite_note-260">[260]</a> The earliest credible evidence of either coffee drinking or knowledge of the coffee plant appears in the middle of the fifteenth century, in the <a href="/wiki/Sufi" class="mw-redirect" title="Sufi">Sufi</a> monasteries of the <a href="/wiki/Yemen" title="Yemen">Yemen</a> in southern Arabia.<a href="#cite_note-Bennett-261">[261]</a> From <a href="/wiki/Mokha" title="Mokha">Mokha</a>, coffee spread to <a href="/wiki/Mamluk_Sultanate_(Cairo)" class="mw-redirect" title="Mamluk Sultanate (Cairo)">Egypt</a> and North Africa, and by the 16th century, it had reached the rest of the Middle East, <a href="/wiki/Safavid_Empire" class="mw-redirect" title="Safavid Empire">Persia</a> and <a href="/wiki/Ottoman_Empire" title="Ottoman Empire">Turkey</a>. From the Middle East, coffee drinking spread to Italy, then to the rest of Europe, and coffee plants were transported by the Dutch to the <a href="/wiki/East_Indies" title="East Indies">East Indies</a> and to the Americas.<a href="#cite_note-Meyers-262">[262]</a> <a href="/wiki/Kola_nut" title="Kola nut">Kola nut</a> use appears to have ancient origins. It is chewed in many <a href="/wiki/West_Africa" title="West Africa">West African</a> cultures, in both private and social settings, to restore vitality and ease hunger pangs.<a href="#cite_note-263">[263]</a> The earliest evidence of <a href="/wiki/Cocoa_bean" title="Cocoa bean">cocoa bean</a> use comes from residue found in an <a href="/wiki/Maya_civilization" title="Maya civilization">ancient Mayan</a> pot dated to 600 BCE. Also, <a href="/wiki/Chocolate" title="Chocolate">chocolate</a> was consumed in a bitter and spicy drink called xocolatl, often seasoned with <a href="/wiki/Vanilla" title="Vanilla">vanilla</a>, <a href="/wiki/Chile_pepper" class="mw-redirect" title="Chile pepper">chile pepper</a>, and <a href="/wiki/Achiote" class="mw-redirect" title="Achiote">achiote</a>. Xocolatl was believed to fight fatigue, a belief probably attributable to the theobromine and caffeine content. Chocolate was an important luxury good throughout <a href="/wiki/Pre-Columbian" class="mw-redirect" title="Pre-Columbian">pre-Columbian</a> <a href="/wiki/Mesoamerica" title="Mesoamerica">Mesoamerica</a>, and cocoa beans were often used as currency.<a href="#cite_note-264">[264]</a> Xocolatl was introduced to <a href="/wiki/Europe" title="Europe">Europe</a> by the <a href="/wiki/Spanish_people" class="mw-redirect" title="Spanish people">Spaniards</a>, and became a popular beverage by 1700. The Spaniards also introduced the <a href="/wiki/Theobroma_cacao" title="Theobroma cacao">cacao tree</a> into the <a href="/wiki/West_Indies" title="West Indies">West Indies</a><a href="#cite_note-265">[265]</a> and the <a href="/wiki/Philippines" title="Philippines">Philippines</a>.<a href="#cite_note-:5-266">[266]</a> The leaves and stems of the yaupon holly (<a href="/wiki/Ilex_vomitoria" title="Ilex vomitoria">Ilex vomitoria</a>) were used by <a href="/wiki/Indigenous_peoples_of_the_Americas" title="Indigenous peoples of the Americas">Native Americans</a> to brew a <a href="/wiki/Tea" title="Tea">tea</a> called asi or the "<a href="/wiki/Black_drink" class="mw-redirect" title="Black drink">black drink</a>".<a href="#cite_note-Fairbanks-267">[267]</a> Archaeologists have found evidence of this use far into antiquity,<a href="#cite_note-268">[268]</a> possibly dating to <a href="/wiki/Archaic_period_in_the_Americas" class="mw-redirect" title="Archaic period in the Americas">Late Archaic times</a>.<a href="#cite_note-Fairbanks-267">[267]</a> <div class="mw-heading mw-heading3"><h3 id="Chemical_identification,_isolation,_and_synthesis">Chemical identification, isolation, and synthesis</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=55" title="Edit section: Chemical identification, isolation, and synthesis">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Friedlieb_Ferdinand_Runge.jpeg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Friedlieb_Ferdinand_Runge.jpeg/170px-Friedlieb_Ferdinand_Runge.jpeg" decoding="async" width="170" height="226" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/a/af/Friedlieb_Ferdinand_Runge.jpeg 1.5x" data-file-width="200" data-file-height="266" /></a><figcaption>Friedlieb Ferdinand Runge, discoverer of caffeine</figcaption></figure> In 1819, the German chemist <a href="/wiki/Friedlieb_Ferdinand_Runge" title="Friedlieb Ferdinand Runge">Friedlieb Ferdinand Runge</a> isolated relatively pure[<a href="/wiki/Wikipedia:Vagueness" title="Wikipedia:Vagueness">vague</a>] caffeine for the first time; he called it "Kaffebase" (i.e., a <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a> that exists in coffee).<a href="#cite_note-269">[269]</a><a href="#cite_note-weinberg-270">[270]</a> In 1821, caffeine was isolated both by the French chemist <a href="/wiki/Pierre_Jean_Robiquet" title="Pierre Jean Robiquet">Pierre Jean Robiquet</a> and by another pair of French chemists, <a href="/wiki/Pierre_Joseph_Pelletier" title="Pierre Joseph Pelletier">Pierre-Joseph Pelletier</a> and <a href="/wiki/Joseph_Bienaim%C3%A9_Caventou" title="Joseph Bienaimé Caventou">Joseph Bienaimé Caventou</a>, according to Swedish chemist <a href="/wiki/J%C3%B6ns_Jacob_Berzelius" title="Jöns Jacob Berzelius">Jöns Jacob Berzelius</a> in his yearly journal. Furthermore, Berzelius stated that the French chemists had made their discoveries independently of any knowledge of Runge's or each other's work.<a href="#cite_note-271">[271]</a> However, Berzelius later acknowledged Runge's priority in the extraction of caffeine, stating:<a href="#cite_note-272">[272]</a> "However, at this point, it should not remain unmentioned that Runge (in his Phytochemical Discoveries, 1820, pages 146–147) specified the same method and described caffeine under the name Caffeebase a year earlier than Robiquet, to whom the discovery of this substance is usually attributed, having made the first oral announcement about it at a meeting of the Pharmacy Society in Paris." Pelletier's article on caffeine was the first to use the term in print (in the French form Caféine from the French word for coffee: café).<a href="#cite_note-273">[273]</a> It corroborates Berzelius's account: <style data-mw-deduplicate="TemplateStyles:r1244412712">.mw-parser-output .templatequote{overflow:hidden;margin:1em 0;padding:0 32px}.mw-parser-output .templatequotecite{line-height:1.5em;text-align:left;margin-top:0}@media(min-width:500px){.mw-parser-output .templatequotecite{padding-left:1.6em}}</style><blockquote class="templatequote">Caffeine, noun (feminine). Crystallizable substance discovered in coffee in 1821 by Mr. Robiquet. During the same period – while they were searching for quinine in coffee because coffee is considered by several doctors to be a medicine that reduces fevers and because coffee belongs to the same family as the cinchona [quinine] tree – on their part, Messrs. Pelletier and Caventou obtained caffeine; but because their research had a different goal and because their research had not been finished, they left priority on this subject to Mr. Robiquet. We do not know why Mr. Robiquet has not published the analysis of coffee which he read to the Pharmacy Society. Its publication would have allowed us to make caffeine better known and give us accurate ideas of coffee's composition ...</blockquote> Robiquet was one of the first to isolate and describe the properties of pure caffeine,<a href="#cite_note-274">[274]</a> whereas Pelletier was the first to perform an <a href="/wiki/Elemental_analysis" title="Elemental analysis">elemental analysis</a>.<a href="#cite_note-275">[275]</a> In 1827, M. Oudry isolated "théine" from tea,<a href="#cite_note-276">[276]</a> but in 1838 it was proved by <a href="/wiki/Gerardus_Johannes_Mulder" title="Gerardus Johannes Mulder">Mulder</a><a href="#cite_note-277">[277]</a> and by Carl Jobst<a href="#cite_note-278">[278]</a> that theine was actually the same as caffeine. In 1895, German chemist <a href="/wiki/Hermann_Emil_Fischer" class="mw-redirect" title="Hermann Emil Fischer">Hermann Emil Fischer</a> (1852–1919) first synthesized caffeine from its chemical components (i.e. a "<a href="/wiki/Total_synthesis" title="Total synthesis">total synthesis</a>"), and two years later, he also derived the structural formula of the compound.<a href="#cite_note-279">[279]</a> This was part of the work for which Fischer was awarded the <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize</a> in 1902.<a href="#cite_note-280">[280]</a> <div class="mw-heading mw-heading3"><h3 id="Historic_regulations">Historic regulations</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=56" title="Edit section: Historic regulations">edit</a>]</div> Because it was recognized that coffee contained some compound that acted as a stimulant, first coffee and later also caffeine has sometimes been subject to regulation. For example, in the 16th century <a href="/wiki/Islamist" class="mw-redirect" title="Islamist">Islamists</a> in <a href="/wiki/Mecca" title="Mecca">Mecca</a> and in the <a href="/wiki/Ottoman_Empire" title="Ottoman Empire">Ottoman Empire</a> made coffee illegal for some classes.<a href="#cite_note-281">[281]</a><a href="#cite_note-agostonmasters2009-282">[282]</a><a href="#cite_note-hopkins2006-283">[283]</a> <a href="/wiki/Charles_II_of_England" title="Charles II of England">Charles II of England</a> tried to ban it in 1676,<a href="#cite_note-284">[284]</a><a href="#cite_note-Pendergrast13-285">[285]</a> <a href="/wiki/Frederick_II_of_Prussia" class="mw-redirect" title="Frederick II of Prussia">Frederick II of Prussia</a> banned it in 1777,<a href="#cite_note-Pendergrast11-286">[286]</a><a href="#cite_note-287">[287]</a> and coffee was banned in <a href="/wiki/Sweden" title="Sweden">Sweden</a> at various times between 1756 and 1823. In 1911, caffeine became the focus of one of the earliest documented health scares, when the US government seized 40 barrels and 20 kegs of <a href="/wiki/Coca-Cola" title="Coca-Cola">Coca-Cola</a> syrup in <a href="/wiki/Chattanooga,_Tennessee" title="Chattanooga, Tennessee">Chattanooga, Tennessee</a>, alleging the caffeine in its drink was "injurious to health".<a href="#cite_note-pmid2010614-288">[288]</a> Although the <a href="/wiki/Supreme_Court_of_the_United_States" title="Supreme Court of the United States">Supreme Court</a> later ruled in favor of Coca-Cola in <a href="/wiki/United_States_v._Forty_Barrels_and_Twenty_Kegs_of_Coca-Cola" title="United States v. Forty Barrels and Twenty Kegs of Coca-Cola">United States v. Forty Barrels and Twenty Kegs of Coca-Cola</a>, two bills were introduced to the <a href="/wiki/United_States_House_of_Representatives" title="United States House of Representatives">U.S. House of Representatives</a> in 1912 to amend the <a href="/wiki/Pure_Food_and_Drug_Act" title="Pure Food and Drug Act">Pure Food and Drug Act</a>, adding caffeine to the list of "habit-forming" and "deleterious" substances, which must be listed on a product's label.<a href="#cite_note-289">[289]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Caffeine&action=edit&section=57" title="Edit section: Society and culture">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Regulations">Regulations</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=58" title="Edit section: Regulations">edit</a>]</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/Energy_drink#Regulations" title="Energy drink">Energy drink § Regulations</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444" /><table class="box-Globalize plainlinks metadata ambox ambox-content ambox-globalize" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><img alt="Globe icon." src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Ambox_globe_content.svg/48px-Ambox_globe_content.svg.png" decoding="async" width="48" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Ambox_globe_content.svg/73px-Ambox_globe_content.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Ambox_globe_content.svg/97px-Ambox_globe_content.svg.png 2x" data-file-width="350" data-file-height="290" /></div></td><td class="mbox-text"><div class="mbox-text-span">The examples and perspective in this section deal primarily with the United States and do not represent a <a href="/wiki/Wikipedia:WikiProject_Countering_systemic_bias" title="Wikipedia:WikiProject Countering systemic bias">worldwide view</a> of the subject. You may <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Caffeine&action=edit">improve this section</a>, discuss the issue on the <a href="/wiki/Talk:Caffeine" title="Talk:Caffeine">talk page</a>, or create a new section, as appropriate. (October 2020) (<a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a>)</div></td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="United_States">United States</h4>[<a href="/w/index.php?title=Caffeine&action=edit&section=59" title="Edit section: United States">edit</a>]</div> The US Food and Drug Administration (FDA) considers safe beverages containing less than 0.02% caffeine;<a href="#cite_note-290">[290]</a> but caffeine powder, which is sold as a dietary supplement, is unregulated.<a href="#cite_note-291">[291]</a> It is a regulatory requirement that the label of most prepackaged foods must declare a list of ingredients, including food additives such as caffeine, in descending order of proportion. However, there is no regulatory provision for mandatory quantitative labeling of caffeine, (e.g., milligrams caffeine per stated serving size). There are a number of food ingredients that naturally contain caffeine. These ingredients must appear in food ingredient lists. However, as is the case for "food additive caffeine", there is no requirement to identify the quantitative amount of caffeine in composite foods containing ingredients that are natural sources of caffeine. While coffee or chocolate are broadly recognized as caffeine sources, some ingredients (e.g., <a href="/wiki/Guarana" title="Guarana">guarana</a>, <a href="/wiki/Yerba_mat%C3%A9" class="mw-redirect" title="Yerba maté">yerba maté</a>) are likely less recognized as caffeine sources. For these natural sources of caffeine, there is no regulatory provision requiring that a food label identify the presence of caffeine nor state the amount of caffeine present in the food.<a href="#cite_note-292">[292]</a> The FDA guidance was updated in 2018.<a href="#cite_note-293">[293]</a> <div class="mw-heading mw-heading3"><h3 id="Consumption">Consumption</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=60" title="Edit section: Consumption">edit</a>]</div> Global consumption of caffeine has been estimated at 120,000 tonnes per year, making it the world's most popular psychoactive substance.<a href="#cite_note-abc.net-20">[20]</a> The consumption of caffeine has remained stable between 1997 and 2015.<a href="#cite_note-Verster2018-294">[294]</a> Coffee, tea and soft drinks are the most common caffeine sources, with energy drinks contributing little to the total caffeine intake across all age groups.<a href="#cite_note-Verster2018-294">[294]</a> <div class="mw-heading mw-heading3"><h3 id="Religions">Religions</h3>[<a href="/w/index.php?title=Caffeine&action=edit&section=61" title="Edit section: Religions">edit</a>]</div> The <a href="/wiki/Seventh-day_Adventist_Church" title="Seventh-day Adventist Church">Seventh-day Adventist Church</a> asked for its members to "abstain from caffeinated drinks", but has removed this from <a href="/wiki/Baptismal_vows" title="Baptismal vows">baptismal vows</a> (while still recommending abstention as policy).<a href="#cite_note-295">[295]</a> Some from these religions believe that one is not supposed to consume a non-medical, psychoactive substance, or believe that one is not supposed to consume a substance that is addictive. <a href="/wiki/The_Church_of_Jesus_Christ_of_Latter-day_Saints" title="The Church of Jesus Christ of Latter-day Saints">The Church of Jesus Christ of Latter-day Saints</a> has said the following with regard to caffeinated beverages: "... the Church revelation spelling out health practices (Doctrine and Covenants 89) does not mention the use of caffeine. The Church's health guidelines prohibit alcoholic drinks, smoking or chewing of tobacco, and 'hot drinks' – taught by Church leaders to refer specifically to tea and coffee."<a href="#cite_note-296">[296]</a> <a href="/wiki/Gaudiya_Vaishnavism" title="Gaudiya Vaishnavism">Gaudiya Vaishnavas</a> generally also abstain from caffeine, because they believe it clouds the mind and overstimulates the senses.<a href="#cite_note-297">[297]</a> To be initiated under a guru, one must have had no caffeine, alcohol, nicotine or other drugs, for at least a year.<a href="#cite_note-298">[298]</a> Caffeinated beverages are widely consumed by <a href="/wiki/Muslims" title="Muslims">Muslims</a>. In the 16th century, some Muslim authorities made unsuccessful attempts to ban them as forbidden "intoxicating beverages" under <a href="/wiki/Islamic_dietary_laws" title="Islamic dietary laws">Islamic dietary laws</a>.<a href="#cite_note-Campo2009-299">[299]</a><a href="#cite_note-Brown2011-300">[300]</a> <div class="mw-heading mw-heading2"><h2 id="Other_organisms">Other organisms</h2>[<a href="/w/index.php?title=Caffeine&action=edit&section=62" title="Edit section: Other organisms">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Caffeinated_spiderwebs_modified.jpg" class="mw-file-description"><img alt="Caffeine effects on spider webs" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Caffeinated_spiderwebs_modified.jpg/220px-Caffeinated_spiderwebs_modified.jpg" decoding="async" width="220" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Caffeinated_spiderwebs_modified.jpg/330px-Caffeinated_spiderwebs_modified.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Caffeinated_spiderwebs_modified.jpg/440px-Caffeinated_spiderwebs_modified.jpg 2x" data-file-width="555" data-file-height="240" /></a><figcaption>Caffeine effects on <a href="/wiki/Spider_web" title="Spider web">spider webs</a></figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Effect_of_psychoactive_drugs_on_animals" title="Effect of psychoactive drugs on animals">Effect of psychoactive drugs on animals</a></div> The bacteria <a href="/wiki/Pseudomonas_putida" title="Pseudomonas putida">Pseudomonas putida</a> CBB5 can live on pure caffeine and can cleave caffeine into carbon dioxide and ammonia.<a href="#cite_note-301">[301]</a> Caffeine is toxic to birds<a href="#cite_note-302">[302]</a> and to dogs and cats,<a href="#cite_note-303">[303]</a> and has a pronounced adverse effect on <a href="/wiki/Mollusk" class="mw-redirect" title="Mollusk">mollusks</a>, various insects, and <a href="/wiki/Spider" title="Spider">spiders</a>.<a href="#cite_note-304">[304]</a> This is at least partly due to a poor ability to metabolize the compound, causing higher levels for a given dose per unit weight.<a href="#cite_note-pmid20859793-184">[184]</a> Caffeine has also been found to enhance the reward memory of <a href="/wiki/Honey_bee" title="Honey bee">honey bees</a>.<a href="#cite_note-pmid23471406-18">[18]</a> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2>[<a href="/w/index.php?title=Caffeine&action=edit&section=63" title="Edit section: Research">edit</a>]</div> Caffeine has been used to double chromosomes in <a href="/wiki/Haploid" class="mw-redirect" title="Haploid">haploid</a> <a href="/wiki/Wheat" title="Wheat">wheat</a>.<a href="#cite_note-pmid18464846-305">[305]</a> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2>[<a href="/w/index.php?title=Caffeine&action=edit&section=64" title="Edit section: See also">edit</a>]</div> <ul><li><a href="/wiki/Adderall" title="Adderall">Adderall</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Health_effects_of_coffee" title="Health effects of coffee">Health effects of coffee</a></li> <li><a href="/wiki/Health_effects_of_tea" title="Health effects of tea">Health effects of tea</a></li> <li><a href="/wiki/List_of_chemical_compounds_in_coffee" title="List of chemical compounds in coffee">List of chemical compounds in coffee</a></li> <li><a href="/wiki/Low_caffeine_coffee" title="Low caffeine coffee">Low caffeine coffee</a></li> <li><a href="/wiki/Methylliberine" title="Methylliberine">Methylliberine</a></li> <li><a href="/wiki/Nootropic" title="Nootropic">Nootropic</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li> <li><a href="/wiki/Wakefulness-promoting_agent" title="Wakefulness-promoting agent">Wakefulness-promoting agent</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Caffeine&action=edit&section=65" title="Edit section: References">edit</a>]</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"><a href="#cite_ref-1">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.chemspider.com/Chemical-Structure.2424.html">"Caffeine"</a>. ChemSpider. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190514141609/http://www.chemspider.com/Chemical-Structure.2424.html">Archived</a> from the original on 14 May 2019. Retrieved 16 November 2021.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ChemSpider&rft.atitle=Caffeine&rft_id=http%3A%2F%2Fwww.chemspider.com%2FChemical-Structure.2424.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-pmid15448977-2">^ <a href="#cite_ref-pmid15448977_2-0">a</a> <a href="#cite_ref-pmid15448977_2-1">b</a> <a href="#cite_ref-pmid15448977_2-2">c</a> <a href="#cite_ref-pmid15448977_2-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJulianoGriffiths2004" class="citation journal cs1">Juliano LM, Griffiths RR (October 2004). "A critical review of caffeine withdrawal: empirical validation of symptoms and signs, incidence, severity, and associated features". Psychopharmacology. 176 (1): 1–29. <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%2Fs00213-004-2000-x">10.1007/s00213-004-2000-x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15448977">15448977</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:5572188">5572188</a>. <q>Results: Of 49 symptom categories identified, the following 10 fulfilled validity criteria: headache, fatigue, decreased energy/ activeness, decreased alertness, drowsiness, decreased contentedness, depressed mood, difficulty concentrating, irritability, and foggy/not clearheaded. In addition, flu-like symptoms, nausea/vomiting, and muscle pain/stiffness were judged likely to represent valid symptom categories. In experimental studies, the incidence of headache was 50% and the incidence of clinically significant distress or functional impairment was 13%. Typically, onset of symptoms occurred 12–24 h after abstinence, with peak intensity at 20–51 h, and for a duration of 2–9 days.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Psychopharmacology&rft.atitle=A+critical+review+of+caffeine+withdrawal%3A+empirical+validation+of+symptoms+and+signs%2C+incidence%2C+severity%2C+and+associated+features&rft.volume=176&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E29&rft.date=2004-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A5572188%23id-name%3DS2CID&rft_id=info%3Apmid%2F15448977&rft_id=info%3Adoi%2F10.1007%2Fs00213-004-2000-x&rft.aulast=Juliano&rft.aufirst=LM&rft.au=Griffiths%2C+RR&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-pmid24761279-3">^ <a href="#cite_ref-pmid24761279_3-0">a</a> <a href="#cite_ref-pmid24761279_3-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMeredithJulianoHughesGriffiths2013" class="citation journal cs1">Meredith SE, Juliano LM, Hughes JR, Griffiths RR (September 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3777290">"Caffeine Use Disorder: A Comprehensive Review and Research Agenda"</a>. 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Elsevier. p. 214. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-091455-8" title="Special:BookSources/978-0-08-091455-8"><bdi>978-0-08-091455-8</bdi></a>. <q>Therefore, caffeine and other adenosine antagonists, while weakly euphoria-like on their own, may potentiate the positive hedonic efficacy of acute drug intoxication and reduce the negative hedonic consequences of drug withdrawal.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Brain+stimulation+and+addiction&rft.btitle=Encyclopedia+of+Behavioral+Neuroscience&rft.pages=214&rft.pub=Elsevier&rft.date=2010&rft.isbn=978-0-08-091455-8&rft.aulast=Schulteis&rft.aufirst=G&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DDfV-BwAAQBAJ%26pg%3DPA214&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-108"><a href="#cite_ref-108">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSalernoKnights2010" class="citation book cs1">Salerno BB, Knights EK (2010). 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Chatswood, N.S.W.: Elsevier Australia. p. 433. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7295-3929-6" title="Special:BookSources/978-0-7295-3929-6"><bdi>978-0-7295-3929-6</bdi></a>. <q>In contrast to the amphetamines, caffeine does not cause euphoria, stereotyped behaviors or psychoses.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmacology+for+health+professionals&rft.place=Chatswood%2C+N.S.W.&rft.pages=433&rft.edition=3rd&rft.pub=Elsevier+Australia&rft.date=2010&rft.isbn=978-0-7295-3929-6&rft.aulast=Salerno&rft.aufirst=BB&rft.au=Knights%2C+EK&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-109"><a href="#cite_ref-109">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEbenezer2015" class="citation book cs1">Ebenezer I (2015). Neuropsychopharmacology and Therapeutics. John Wiley & Sons. p. 18. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-118-38578-4" title="Special:BookSources/978-1-118-38578-4"><bdi>978-1-118-38578-4</bdi></a>. <q>However, in contrast to other psychoactive stimulants, such as amphetamine and cocaine, caffeine and the other methylxanthines do not produce euphoria, stereotyped behaviors or psychotic like symptoms in large doses.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Neuropsychopharmacology+and+Therapeutics&rft.pages=18&rft.pub=John+Wiley+%26+Sons&rft.date=2015&rft.isbn=978-1-118-38578-4&rft.aulast=Ebenezer&rft.aufirst=I&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-Add2014-110">^ <a href="#cite_ref-Add2014_110-0">a</a> <a href="#cite_ref-Add2014_110-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAddicott2014" class="citation journal cs1">Addicott MA (September 2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4115451">"Caffeine Use Disorder: A Review of the Evidence and Future Implications"</a>. Current Addiction Reports. 1 (3): 186–192. <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%2Fs40429-014-0024-9">10.1007/s40429-014-0024-9</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4115451">4115451</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25089257">25089257</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Addiction+Reports&rft.atitle=Caffeine+Use+Disorder%3A+A+Review+of+the+Evidence+and+Future+Implications&rft.volume=1&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E186-%3C%2Fspan%3E192&rft.date=2014-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4115451%23id-name%3DPMC&rft_id=info%3Apmid%2F25089257&rft_id=info%3Adoi%2F10.1007%2Fs40429-014-0024-9&rft.aulast=Addicott&rft.aufirst=MA&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4115451&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-111"><a href="#cite_ref-111">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNestlerHymenHoltzmannMalenka" class="citation book cs1">Nestler EJ, Hymen SE, Holtzmann DM, Malenka RC. "16". Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (3rd ed.). McGraw-Hill Education. <q>True compulsive use of caffeine has not been documented, and, consequently, these drugs are not considered addictive.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=16&rft.btitle=Molecular+Neuropharmacology%3A+A+Foundation+for+Clinical+Neuroscience&rft.edition=3rd&rft.pub=McGraw-Hill+Education.&rft.aulast=Nestler&rft.aufirst=EJ&rft.au=Hymen%2C+SE&rft.au=Holtzmann%2C+DM&rft.au=Malenka%2C+RC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-112"><a href="#cite_ref-112">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBudneyEmond2014" class="citation journal cs1">Budney AJ, Emond JA (November 2014). "Caffeine addiction? Caffeine for youth? Time to act!". Addiction. 109 (11): 1771–2. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fadd.12594">10.1111/add.12594</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24984891">24984891</a>. <q>Academics and clinicians, however, have not yet reached consensus about the potential clinical importance of caffeine addiction (or 'use disorder')</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Addiction&rft.atitle=Caffeine+addiction%3F+Caffeine+for+youth%3F+Time+to+act%21&rft.volume=109&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1771-%3C%2Fspan%3E2&rft.date=2014-11&rft_id=info%3Adoi%2F10.1111%2Fadd.12594&rft_id=info%3Apmid%2F24984891&rft.aulast=Budney&rft.aufirst=AJ&rft.au=Emond%2C+JA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-113"><a href="#cite_ref-113">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRibaTasmanKayLieberman2014" class="citation book cs1">Riba A, Tasman J, Kay JS, Lieberman MB, First MB (2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=l2KRBgAAQBAJ&pg=PA1446">Psychiatry</a> (Fourth ed.). John Wiley & Sons. p. 1446. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-118-75336-1" title="Special:BookSources/978-1-118-75336-1"><bdi>978-1-118-75336-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Psychiatry&rft.pages=1446&rft.edition=Fourth&rft.pub=John+Wiley+%26+Sons&rft.date=2014&rft.isbn=978-1-118-75336-1&rft.aulast=Riba&rft.aufirst=A&rft.au=Tasman%2C+J&rft.au=Kay%2C+JS&rft.au=Lieberman%2C+MB&rft.au=First%2C+MB&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dl2KRBgAAQBAJ%26pg%3DPA1446&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-114"><a href="#cite_ref-114">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFishchmanMello" class="citation book cs1">Fishchman N, Mello N. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161222041641/http://ww1.drugabuse.gov/pdf/monographs/92.pdf">Testing for Abuse Liability of Drugs in Humans</a> (PDF). 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Dialogues in Clinical Neuroscience. 15 (4): 431–43. <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> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3898681">3898681</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/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=%3Cspan+class%3D%22nowrap%22%3E431-%3C%2Fspan%3E43&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%3ACaffeine" class="Z3988"> </li> <li id="cite_note-Human-caffeine_NAcc_neuroimaging-116"><a href="#cite_ref-Human-caffeine_NAcc_neuroimaging_116-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMiller2013" class="citation book cs1">Miller PM (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=5gRNl3oIwWEC&pg=PA784">"Chapter III: Types of Addiction"</a>. 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Boca Raton: CRC Press. pp. 229–230. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8493-7881-2" title="Special:BookSources/978-0-8493-7881-2"><bdi>978-0-8493-7881-2</bdi></a>. <q>All of these observations strongly suggest that caffeine does not act on the dopaminergic structures related to addiction, nor does it improve performance by alleviating any symptoms of withdrawal</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Karch%27s+pathology+of+drug+abuse&rft.place=Boca+Raton&rft.pages=%3Cspan+class%3D%22nowrap%22%3E229-%3C%2Fspan%3E230&rft.edition=4th&rft.pub=CRC+Press&rft.date=2009&rft.isbn=978-0-8493-7881-2&rft.aulast=Karch&rft.aufirst=SB&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DG9E7gfJq0KkC%26pg%3DPA229&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-ICD-10_F15.2-120"><a href="#cite_ref-ICD-10_F15.2_120-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://apps.who.int/classifications/icd10/browse/2015/en#/F15.2">"ICD-10 Version:2015"</a>. 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Cahiers d'Études Africaines. 20 (77/78): 97–134. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3406%2Fcea.1980.2353">10.3406/cea.1980.2353</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0008-0055">0008-0055</a>. <a href="/wiki/JSTOR_(identifier)" class="mw-redirect" title="JSTOR (identifier)">JSTOR</a> <a rel="nofollow" class="external text" href="https://www.jstor.org/stable/4391682">4391682</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cahiers+d%27%C3%89tudes+Africaines&rft.atitle=Kola+in+the+History+of+West+Africa+%28La+kola+dans+l%27histoire+de+l%27Afrique+occidentale%29&rft.volume=20&rft.issue=77%2F78&rft.pages=%3Cspan+class%3D%22nowrap%22%3E97-%3C%2Fspan%3E134&rft.date=1980&rft.issn=0008-0055&rft_id=https%3A%2F%2Fwww.jstor.org%2Fstable%2F4391682%23id-name%3DJSTOR&rft_id=info%3Adoi%2F10.3406%2Fcea.1980.2353&rft.aulast=Lovejoy&rft.aufirst=PE&rft_id=https%3A%2F%2Fwww.jstor.org%2Fstable%2F4391682&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-264"><a href="#cite_ref-264">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRied2012" class="citation book cs1">Ried K (21 June 2012). "Dark Chocolate and (Pre-)Hypertension". In Watson RR, Preedy VR, Zibadi S (eds.). Chocolate in Health and Nutrition. Humana Press. pp. 313–325. <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%2F978-1-61779-803-0_23">10.1007/978-1-61779-803-0_23</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-61779-802-3" title="Special:BookSources/978-1-61779-802-3"><bdi>978-1-61779-802-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Dark+Chocolate+and+%28Pre-%29Hypertension&rft.btitle=Chocolate+in+Health+and+Nutrition&rft.pages=%3Cspan+class%3D%22nowrap%22%3E313-%3C%2Fspan%3E325&rft.pub=Humana+Press&rft.date=2012-06-21&rft_id=info%3Adoi%2F10.1007%2F978-1-61779-803-0_23&rft.isbn=978-1-61779-802-3&rft.aulast=Ried&rft.aufirst=K&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-265"><a href="#cite_ref-265">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBekele" class="citation web cs1">Bekele FL. <a rel="nofollow" class="external text" href="https://sta.uwi.edu/cru/sites/default/files/cru/HistoryCocoaProductionTT.pdf">"The History of Cocoa Production in Trinidad and Tobago"</a> (PDF). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20201201212420/https://sta.uwi.edu/cru/sites/default/files/cru/HistoryCocoaProductionTT.pdf">Archived</a> (PDF) from the original on 1 December 2020. Retrieved 21 May 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=The+History+of+Cocoa+Production+in+Trinidad+and+Tobago&rft.aulast=Bekele&rft.aufirst=FL&rft_id=https%3A%2F%2Fsta.uwi.edu%2Fcru%2Fsites%2Fdefault%2Ffiles%2Fcru%2FHistoryCocoaProductionTT.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-:5-266"><a href="#cite_ref-:5_266-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation report cs1"><a rel="nofollow" class="external text" href="http://pef.ph/wp-content/uploads/2016/03/Industry-Study_Cacao.pdf">A primer on PEF's Priority Commodities: an Industry Study on Cacao</a> (PDF). Peace and Equity Foundation (Report). Philippines. 2016. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210502162122/https://pef.ph/wp-content/uploads/2016/03/Industry-Study_Cacao.pdf">Archived</a> (PDF) from the original on 2 May 2021. Retrieved 21 May 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=report&rft.btitle=A+primer+on+PEF%27s+Priority+Commodities%3A+an+Industry+Study+on+Cacao&rft.place=Philippines&rft.date=2016&rft_id=http%3A%2F%2Fpef.ph%2Fwp-content%2Fuploads%2F2016%2F03%2FIndustry-Study_Cacao.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-Fairbanks-267">^ <a href="#cite_ref-Fairbanks_267-0">a</a> <a href="#cite_ref-Fairbanks_267-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFairbanks2004" class="citation book cs1">Fairbanks CH (2004). "The function of black drink among the Creeks". In <a href="/wiki/Charles_M._Hudson_(author)" class="mw-redirect" title="Charles M. Hudson (author)">Hudson MC</a> (ed.). Black Drink. University of Georgia Press. p. 123. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8203-2696-2" title="Special:BookSources/978-0-8203-2696-2"><bdi>978-0-8203-2696-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=The+function+of+black+drink+among+the+Creeks&rft.btitle=Black+Drink&rft.pages=123&rft.pub=University+of+Georgia+Press&rft.date=2004&rft.isbn=978-0-8203-2696-2&rft.aulast=Fairbanks&rft.aufirst=CH&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-268"><a href="#cite_ref-268">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCrownEmersonGuHurst2012" class="citation journal cs1">Crown PL, Emerson TE, Gu J, Hurst WJ, Pauketat TR, Ward T (August 2012). <a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.1208404109">"Ritual Black Drink consumption at Cahokia"</a>. Proceedings of the National Academy of Sciences of the United States of America. 109 (35): 13944–9. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2012PNAS..10913944C">2012PNAS..10913944C</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.1208404109">10.1073/pnas.1208404109</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3435207">3435207</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22869743">22869743</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences+of+the+United+States+of+America&rft.atitle=Ritual+Black+Drink+consumption+at+Cahokia&rft.volume=109&rft.issue=35&rft.pages=%3Cspan+class%3D%22nowrap%22%3E13944-%3C%2Fspan%3E9&rft.date=2012-08&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3435207%23id-name%3DPMC&rft_id=info%3Apmid%2F22869743&rft_id=info%3Adoi%2F10.1073%2Fpnas.1208404109&rft_id=info%3Abibcode%2F2012PNAS..10913944C&rft.aulast=Crown&rft.aufirst=PL&rft.au=Emerson%2C+TE&rft.au=Gu%2C+J&rft.au=Hurst%2C+WJ&rft.au=Pauketat%2C+TR&rft.au=Ward%2C+T&rft_id=https%3A%2F%2Fdoi.org%2F10.1073%252Fpnas.1208404109&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-269"><a href="#cite_ref-269">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRunge1820" class="citation book cs1">Runge FF (1820). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=KLg5AAAAcAAJ&pg=P146">Neueste phytochemische Entdeckungen zur Begründung einer wissenschaftlichen Phytochemie</a> [Latest phytochemical discoveries for the founding of a scientific phytochemistry]. Berlin: G. Reimer. pp. 144–159. Retrieved 8 January 2014.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Neueste+phytochemische+Entdeckungen+zur+Begr%C3%BCndung+einer+wissenschaftlichen+Phytochemie&rft.place=Berlin&rft.pages=%3Cspan+class%3D%22nowrap%22%3E144-%3C%2Fspan%3E159&rft.pub=G.+Reimer&rft.date=1820&rft.aulast=Runge&rft.aufirst=FF&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DKLg5AAAAcAAJ%26pg%3DP146&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-weinberg-270"><a href="#cite_ref-weinberg_270-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWeinbergBealer2001" class="citation book cs1">Weinberg BA, Bealer BK (2001). <a rel="nofollow" class="external text" href="https://archive.org/details/worldofcaffeines00benn">The World of Caffeine: The Science and Culture of the World's Most Popular Drug</a>. Routledge. pp. xvii–xxi. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-415-92723-9" title="Special:BookSources/978-0-415-92723-9"><bdi>978-0-415-92723-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+World+of+Caffeine%3A+The+Science+and+Culture+of+the+World%27s+Most+Popular+Drug&rft.pages=%3Cspan+class%3D%22nowrap%22%3Exvii-%3C%2Fspan%3Exxi&rft.pub=Routledge&rft.date=2001&rft.isbn=978-0-415-92723-9&rft.aulast=Weinberg&rft.aufirst=BA&rft.au=Bealer%2C+BK&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fworldofcaffeines00benn&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-271"><a href="#cite_ref-271">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBerzelius1825" class="citation book cs1 cs1-prop-foreign-lang-source">Berzelius JJ (1825). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=XJI8AAAAIAAJ&pg=PA1">Jahres-Bericht über die Fortschritte der physischen Wissenschaften von Jacob Berzelius</a> [Annual report on the progress of the physical sciences by Jacob Berzelius] (in German). Vol. 4. p. 180: <q>Caféin ist eine Materie im Kaffee, die zu gleicher Zeit, 1821, von Robiquet und Pelletier und Caventou entdekt wurde, von denen aber keine etwas darüber im Drucke bekannt machte.</q> [Caffeine is a material in coffee, which was discovered at the same time, 1821, by Robiquet and [by] Pelletier and Caventou, by whom however nothing was made known about it in the press.]</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Jahres-Bericht+%C3%BCber+die+Fortschritte+der+physischen+Wissenschaften+von+Jacob+Berzelius&rft.pages=180&rft.date=1825&rft.aulast=Berzelius&rft.aufirst=JJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DXJI8AAAAIAAJ%26pg%3DPA1&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-272"><a href="#cite_ref-272">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBerzelius1828" class="citation book cs1 cs1-prop-foreign-lang-source">Berzelius JJ (1828). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=iGs1AAAAcAAJ&pag">Jahres-Bericht über die Fortschritte der physischen Wissenschaften von Jacob Berzelius</a> [Annual Report on the Progress of the Physical Sciences by Jacob Berzelius] (in German). Vol. 7. p. 270: <q>Es darf indessen hierbei nicht unerwähnt bleiben, dass Runge (in seinen phytochemischen Entdeckungen 1820, p. 146-7.) dieselbe Methode angegeben, und das Caffein unter dem Namen Caffeebase ein Jahr eher beschrieben hat, als Robiquet, dem die Entdeckung dieser Substanz gewöhnlich zugeschrieben wird, in einer Zusammenkunft der Societé de Pharmacie in Paris die erste mündliche Mittheilung darüber gab.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Jahres-Bericht+%C3%BCber+die+Fortschritte+der+physischen+Wissenschaften+von+Jacob+Berzelius&rft.pages=270&rft.date=1828&rft.aulast=Berzelius&rft.aufirst=JJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DiGs1AAAAcAAJ%26pag&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-273"><a href="#cite_ref-273">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPelletier1822" class="citation encyclopaedia cs1 cs1-prop-foreign-lang-source"><a href="/wiki/Pierre_Joseph_Pelletier" title="Pierre Joseph Pelletier">Pelletier PJ</a> (1822). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=rFw_AAAAcAAJ&pg=PA35">"Cafeine"</a>. Dictionnaire de Médecine (in French). Vol. 4. Paris: Béchet Jeune. pp. 35–36. Retrieved 3 March 2011.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Cafeine&rft.btitle=Dictionnaire+de+M%C3%A9decine&rft.place=Paris&rft.pages=%3Cspan+class%3D%22nowrap%22%3E35-%3C%2Fspan%3E36&rft.pub=B%C3%A9chet+Jeune&rft.date=1822&rft.aulast=Pelletier&rft.aufirst=PJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DrFw_AAAAcAAJ%26pg%3DPA35&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-274"><a href="#cite_ref-274">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRobiquet1823" class="citation encyclopaedia cs1 cs1-prop-foreign-lang-source"><a href="/wiki/Robiquet" title="Robiquet">Robiquet PJ</a> (1823). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=vDdRAAAAYAAJ">"Café"</a>. Dictionnaire Technologique, ou Nouveau Dictionnaire Universel des Arts et Métiers (in French). Vol. 4. Paris: Thomine et Fortic. pp. 50–61. Retrieved 3 March 2011.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Caf%C3%A9&rft.btitle=Dictionnaire+Technologique%2C+ou+Nouveau+Dictionnaire+Universel+des+Arts+et+M%C3%A9tiers&rft.place=Paris&rft.pages=%3Cspan+class%3D%22nowrap%22%3E50-%3C%2Fspan%3E61&rft.pub=Thomine+et+Fortic&rft.date=1823&rft.aulast=Robiquet&rft.aufirst=PJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DvDdRAAAAYAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-275"><a href="#cite_ref-275">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDumas1823" class="citation journal cs1 cs1-prop-foreign-lang-source">Dumas P (1823). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=-BIAAAAAMAAJ&pg=PA182">"Recherches sur la composition élémentaire et sur quelques propriétés caractéristiques des bases salifiables organiques"</a> [Studies into the elemental composition and some characteristic properties of organic bases]. Annales de Chimie et de Physique (in French). 24: 163–191.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie+et+de+Physique&rft.atitle=Recherches+sur+la+composition+%C3%A9l%C3%A9mentaire+et+sur+quelques+propri%C3%A9t%C3%A9s+caract%C3%A9ristiques+des+bases+salifiables+organiques&rft.volume=24&rft.pages=%3Cspan+class%3D%22nowrap%22%3E163-%3C%2Fspan%3E191&rft.date=1823&rft.aulast=Dumas&rft.aufirst=P&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D-BIAAAAAMAAJ%26pg%3DPA182&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-276"><a href="#cite_ref-276">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOudry1827" class="citation journal cs1 cs1-prop-foreign-lang-source">Oudry M (1827). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=cGpEAAAAcAAJ&pg=PA477">"Note sur la Théine"</a> [Note on Theine]. Nouvelle Bibliothèque Médicale (in French). 1: 477–479.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nouvelle+Biblioth%C3%A8que+M%C3%A9dicale&rft.atitle=Note+sur+la+Th%C3%A9ine&rft.volume=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E477-%3C%2Fspan%3E479&rft.date=1827&rft.aulast=Oudry&rft.aufirst=M&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DcGpEAAAAcAAJ%26pg%3DPA477&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-277"><a href="#cite_ref-277">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMulder1838" class="citation journal cs1">Mulder GJ (1838). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=HQHzAAAAMAAJ&pg=PA280">"Ueber Theïn und Caffeïn"</a> [Concerning theine and caffeine]. Journal für Praktische Chemie. 15: 280–284. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fprac.18380150124">10.1002/prac.18380150124</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+f%C3%BCr+Praktische+Chemie&rft.atitle=Ueber+The%C3%AFn+und+Caffe%C3%AFn&rft.volume=15&rft.pages=%3Cspan+class%3D%22nowrap%22%3E280-%3C%2Fspan%3E284&rft.date=1838&rft_id=info%3Adoi%2F10.1002%2Fprac.18380150124&rft.aulast=Mulder&rft.aufirst=GJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DHQHzAAAAMAAJ%26pg%3DPA280&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-278"><a href="#cite_ref-278">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJobst1838" class="citation journal cs1">Jobst C (1838). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=teJSAAAAcAAJ&pg=PA63">"Thein identisch mit Caffein"</a> [Theine is identical to caffeine]. Liebig's Annalen der Chemie und Pharmacie. 25: 63–66. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18380250106">10.1002/jlac.18380250106</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Liebig%27s+Annalen+der+Chemie+und+Pharmacie&rft.atitle=Thein+identisch+mit+Caffein&rft.volume=25&rft.pages=%3Cspan+class%3D%22nowrap%22%3E63-%3C%2Fspan%3E66&rft.date=1838&rft_id=info%3Adoi%2F10.1002%2Fjlac.18380250106&rft.aulast=Jobst&rft.aufirst=C&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DteJSAAAAcAAJ%26pg%3DPA63&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"> </li> <li id="cite_note-279"><a href="#cite_ref-279">^</a> Fischer began his studies of caffeine in 1881; however, understanding of the molecule's structure long eluded him. In 1895 he synthesized caffeine, but only in 1897 did he finally fully determine its molecular structure. <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1 cs1-prop-foreign-lang-source">Fischer E (1881). <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k90692z/f640.image.langEN">"Ueber das Caffeïn"</a> [On caffeine]. Berichte der Deutschen Chemischen Gesellschaft zu Berlin (in German). 14: 637–644. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.188101401142">10.1002/cber.188101401142</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151015213939/http://gallica.bnf.fr/ark:/12148/bpt6k90692z/f640.image.langEN">Archived</a> from the original on 15 October 2015. Retrieved 17 June 2013.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft+zu+Berlin&rft.atitle=Ueber+das+Caffe%C3%AFn&rft.volume=14&rft.pages=%3Cspan+class%3D%22nowrap%22%3E637-%3C%2Fspan%3E644&rft.date=1881&rft_id=info%3Adoi%2F10.1002%2Fcber.188101401142&rft.aulast=Fischer&rft.aufirst=E&rft_id=http%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k90692z%2Ff640.image.langEN&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1 cs1-prop-foreign-lang-source">Fischer E (1881). <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k906939/f316.image.langEN">"Ueber das Caffeïn. Zweite Mitteilung"</a> [On caffeine. Second communication.]. Berichte der Deutschen Chemischen Gesellschaft zu Berlin (in German). 14 (2): 1905–1915. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.18810140283">10.1002/cber.18810140283</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150903215226/http://gallica.bnf.fr/ark:/12148/bpt6k906939/f316.image.langEN">Archived</a> from the original on 3 September 2015. Retrieved 17 June 2013.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft+zu+Berlin&rft.atitle=Ueber+das+Caffe%C3%AFn.+Zweite+Mitteilung&rft.volume=14&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1905-%3C%2Fspan%3E1915&rft.date=1881&rft_id=info%3Adoi%2F10.1002%2Fcber.18810140283&rft.aulast=Fischer&rft.aufirst=E&rft_id=http%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k906939%2Ff316.image.langEN&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1 cs1-prop-foreign-lang-source">Fischer E (1882). <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k90694n/f32.image.langEN">"Ueber das Caffeïn. Dritte Mitteilung"</a> [On caffeine. Third communication.]. Berichte der Deutschen Chemischen Gesellschaft zu Berlin (in German). 15: 29–33. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.18820150108">10.1002/cber.18820150108</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151015213939/http://gallica.bnf.fr/ark:/12148/bpt6k90694n/f32.image.langEN">Archived</a> from the original on 15 October 2015. Retrieved 17 June 2013.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft+zu+Berlin&rft.atitle=Ueber+das+Caffe%C3%AFn.+Dritte+Mitteilung&rft.volume=15&rft.pages=%3Cspan+class%3D%22nowrap%22%3E29-%3C%2Fspan%3E33&rft.date=1882&rft_id=info%3Adoi%2F10.1002%2Fcber.18820150108&rft.aulast=Fischer&rft.aufirst=E&rft_id=http%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k90694n%2Ff32.image.langEN&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1 cs1-prop-foreign-lang-source">Fischer E, Ach L (1895). <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k907400/f806.image.langEN">"Synthese des Caffeïns"</a> [Synthesis of caffeine]. Berichte der Deutschen Chemischen Gesellschaft zu Berlin (in German). 28 (3): 3135–3143. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.189502803156">10.1002/cber.189502803156</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151015213939/http://gallica.bnf.fr/ark:/12148/bpt6k907400/f806.image.langEN">Archived</a> from the original on 15 October 2015. 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Coffee, Sex & Health: A history of anti-coffee crusaders and sexual hysteria. Sydney: Helian Books. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-9577581-0-0" title="Special:BookSources/978-0-9577581-0-0"><bdi>978-0-9577581-0-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Coffee%2C+Sex+%26+Health%3A+A+history+of+anti-coffee+crusaders+and+sexual+hysteria&rft.place=Sydney&rft.pub=Helian+Books&rft.date=1999&rft.isbn=978-0-9577581-0-0&rft.aulast=Bersten&rft.aufirst=I&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeine" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1">Carpenter M (2015). Caffeinated: How Our Daily Habit Helps, Hurts, and Hooks Us. 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src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/40px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/60px-Commons-logo.svg.png 1.5x" data-file-width="1024" data-file-height="1376" /></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <a href="https://commons.wikimedia.org/wiki/Tea" class="extiw" title="c:Tea">Caffeine</a>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://gmd.mpimp-golm.mpg.de/Spectrums/43595824-4FD6-4B29-AFC2-2771E487F6F3.aspx">GMD MS Spectrum</a></li> <li><a rel="nofollow" class="external text" href="http://chemsub.online.fr/name/Caffeine.html">Caffeine: ChemSub Online</a></li> <li><a rel="nofollow" class="external text" href="http://www.periodicvideos.com/videos/mv_caffeine.htm">Caffeine</a> at <a href="/wiki/The_Periodic_Table_of_Videos" class="mw-redirect" title="The Periodic 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.navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Coffee512" 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" /><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:Coffee" title="Template:Coffee"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Coffee" title="Template talk:Coffee"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Coffee" title="Special:EditPage/Template:Coffee"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Coffee512" class="hrecipe fn ingredient" style="font-size:114%;margin:0 4em"><a href="/wiki/Coffee" title="Coffee">Coffee</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Topics</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/Economics_of_coffee" title="Economics of coffee">Economics</a></li> <li><a href="/wiki/Fair_trade_coffee" title="Fair trade coffee">Fair trade</a></li> <li><a href="/wiki/History_of_coffee" title="History of coffee">History</a></li> <li><a href="/wiki/International_Coffee_Day" title="International Coffee Day">International Coffee Day</a></li> <li><a href="/wiki/Single-origin_coffee" title="Single-origin coffee">Single-origin coffee</a></li> <li><a href="/wiki/Third-wave_coffee" title="Third-wave coffee">Third-wave coffee</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Production</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/Coffee_production" title="Coffee production">Coffee production</a> <ul><li><a href="/wiki/Organic_coffee" title="Organic coffee">Organic coffee</a></li> <li><a href="/wiki/Shade-grown_coffee" title="Shade-grown coffee">Shade-grown coffee</a></li> <li><a href="/wiki/Sustainable_coffee" title="Sustainable coffee">Sustainable coffee</a></li></ul></li> <li><a href="/wiki/List_of_countries_by_coffee_production" title="List of countries by coffee production">List of countries by coffee production</a></li> <li><a href="/wiki/Coffee_roasting" title="Coffee roasting">Coffee roasting</a></li> <li><a href="/wiki/Coffee_wastewater" title="Coffee wastewater">Coffee wastewater</a></li> <li><a href="/wiki/Decaffeination" title="Decaffeination">Decaffeination</a></li> <li><a href="/wiki/Home_roasting_coffee" title="Home roasting coffee">Home roasting</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Coffea" title="Coffea">Species</a> and <a href="/wiki/List_of_coffee_varieties" title="List of coffee varieties">varieties</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/Coffea_arabica" title="Coffea arabica">Arabica</a> <ul><li><a href="/wiki/Benguet_coffee" title="Benguet coffee">Benguet</a></li> <li><a href="/wiki/Jamaican_Blue_Mountain_Coffee" title="Jamaican Blue Mountain Coffee">Blue Mountain</a></li> <li><a href="/wiki/Guadeloupe_Bonifieur" title="Guadeloupe Bonifieur">Bonifieur</a></li> <li><a href="/wiki/Bourbon_coffee" title="Bourbon coffee">Bourbon</a></li> <li><a href="/wiki/Geisha_(coffee)" title="Geisha (coffee)">Geisha</a></li> <li><a href="/wiki/Kona_coffee" title="Kona coffee">Kona</a></li> <li><a href="/wiki/Maracaturra_coffee" title="Maracaturra coffee">Maracaturra</a></li> <li><a href="/wiki/Maragogipe_Coffee" title="Maragogipe Coffee">Maragogipe</a></li> <li><a href="/wiki/Molokai_coffee" title="Molokai coffee">Molokai</a></li> <li><a href="/wiki/S795_coffee" title="S795 coffee">S795</a></li> <li><a href="/wiki/Sagada_coffee" title="Sagada coffee">Sagada</a></li></ul></li> <li><a href="/wiki/Coffea_charrieriana" title="Coffea charrieriana">Charrieriana</a></li> <li><a href="/wiki/Coffea_liberica" title="Coffea liberica">Liberica</a> <ul><li><a href="/wiki/Kapeng_barako" title="Kapeng barako">Barako</a></li></ul></li> <li><a href="/wiki/Coffea_racemosa" title="Coffea racemosa">Racemosa</a></li> <li><a href="/wiki/Robusta_coffee" class="mw-redirect" title="Robusta coffee">Robusta</a> <ul><li><a href="/wiki/Kahawa_Sug" title="Kahawa Sug">Sulu</a></li></ul></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/Cafestol" title="Cafestol">Cafestol</a></li> <li><a href="/wiki/Caffeic_acid" title="Caffeic acid">Caffeic acid</a></li> <li><a class="mw-selflink selflink">Caffeine</a></li> <li><a href="/wiki/Coffee_bean" title="Coffee bean">Coffee bean</a></li> <li><a href="/wiki/Furan-2-ylmethanethiol" title="Furan-2-ylmethanethiol">Furan-2-ylmethanethiol</a></li> <li><a href="/wiki/Kahweol" title="Kahweol">Kahweol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Coffee_preparation" title="Coffee preparation">Preparation</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/AeroPress" title="AeroPress">AeroPress</a></li> <li><a href="/wiki/Arabic_coffee" title="Arabic coffee">Arabic coffee</a></li> <li><a href="/wiki/Jebena" title="Jebena">Jebena</a></li> <li><a href="/wiki/Brewed_coffee" class="mw-redirect" title="Brewed coffee">Brewed coffee</a></li> <li><a href="/wiki/Chemex_Coffeemaker" title="Chemex Coffeemaker">Chemex</a></li> <li><a href="/wiki/Cezve" title="Cezve">Cezve</a></li> <li><a href="/wiki/Chorreador" title="Chorreador">Chorreador</a></li> <li><a href="/wiki/Coffeemaker" title="Coffeemaker">Coffeemaker</a></li> <li><a href="/wiki/Cold_brew_coffee" title="Cold brew coffee">Cold brew</a> <ul><li><a href="/wiki/Nitro_cold_brew_coffee" class="mw-redirect" title="Nitro cold brew coffee">nitro</a></li></ul></li> <li><a href="/wiki/Drip_coffee" title="Drip coffee">Drip coffee</a></li> <li><a href="/wiki/Espresso" title="Espresso">Espresso</a> <ul><li><a href="/wiki/Doppio" title="Doppio">doppio</a></li> <li><a href="/wiki/Lungo" title="Lungo">lungo</a></li> <li><a href="/wiki/Ristretto" title="Ristretto">ristretto</a></li></ul></li> <li><a href="/wiki/Espresso_machine" title="Espresso machine">Espresso machine</a></li> <li><a href="/wiki/French_drip" class="mw-redirect" title="French drip">French drip</a> <ul><li><a href="/wiki/Karlsbad_coffee_maker" class="mw-redirect" title="Karlsbad coffee maker">Karlsbad coffee maker</a></li></ul></li> <li><a href="/wiki/French_press" title="French press">French press</a></li> <li><a href="/wiki/Instant_coffee" title="Instant coffee">Instant coffee</a> <ul><li><a href="/wiki/Coffee_syrup" class="mw-redirect" title="Coffee syrup">Coffee syrup</a></li></ul></li> <li><a href="/wiki/Knockbox" title="Knockbox">Knockbox</a></li> <li><a href="/wiki/Moka_pot" title="Moka pot">Moka pot</a></li> <li><a href="/wiki/Neapolitan_flip_coffee_pot" title="Neapolitan flip coffee pot">Neapolitan flip coffee pot</a></li> <li><a href="/wiki/Coffee_percolator" title="Coffee percolator">Percolator</a></li> <li><a href="/wiki/Turkish_coffee" title="Turkish coffee">Turkish coffee</a></li> <li><a href="/wiki/Yazdi_coffee" title="Yazdi coffee">Yazdi coffee</a></li> <li><a href="/wiki/Vacuum_coffee_maker" title="Vacuum coffee maker">Vacuum maker</a></li> <li><a href="/wiki/Single-serve_coffee_container" title="Single-serve coffee container">Single-serve coffee container</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_coffee_drinks" title="List of coffee drinks">Coffee drinks</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/Affogato" title="Affogato">Affogato</a></li> <li><a href="/wiki/Caff%C3%A8_Americano" class="mw-redirect" title="Caffè Americano">Americano</a></li> <li><a href="/wiki/Beaten_coffee" title="Beaten coffee">Beaten coffee</a></li> <li><a href="/wiki/Bica_(coffee)" title="Bica (coffee)">Bica</a></li> <li><a href="/wiki/Bicerin" title="Bicerin">Bicerin</a></li> <li><a href="/wiki/Black_Russian" title="Black Russian">Black Russian</a></li> <li><a href="/wiki/Vietnamese_iced_coffee" title="Vietnamese iced coffee">Cà phê sữa đá</a></li> <li><a href="/wiki/Caf%C3%A9_au_lait" title="Café au lait">Café au lait</a></li> <li><a href="/wiki/Caf%C3%A9_com_cheirinho" title="Café com cheirinho">Café com cheirinho</a></li> <li><a href="/wiki/Caf%C3%A9_con_leche" title="Café con leche">Café con leche</a></li> <li><a href="/wiki/Caf%C3%A9_de_olla" title="Café de olla">Café de olla</a></li> <li><a href="/wiki/Caf%C3%A9_Touba" title="Café Touba">Café Touba</a></li> <li><a href="/wiki/Caff%C3%A8_corretto" title="Caffè corretto">Caffè corretto</a></li> <li><a href="/wiki/Caff%C3%A8_crema" title="Caffè crema">Caffè crema</a></li> <li><a href="/wiki/Caff%C3%A8_macchiato" title="Caffè macchiato">Caffè macchiato</a></li> <li><a href="/wiki/Caff%C3%A8_mocha" title="Caffè mocha">Caffè mocha</a></li> <li><a href="/wiki/Cappuccino" title="Cappuccino">Cappuccino</a></li> <li><a href="/wiki/Carajillo" title="Carajillo">Carajillo</a></li> <li><a href="/wiki/Coffee_cabinet" title="Coffee cabinet">Coffee cabinet</a></li> <li><a href="/wiki/Coffee_milk" title="Coffee milk">Coffee milk</a></li> <li><a href="/wiki/Cortado" title="Cortado">Cortado</a></li> <li><a href="/wiki/Cuban_espresso" title="Cuban espresso">Café Cubano</a></li> <li><a href="/wiki/Dalgona_coffee" title="Dalgona coffee">Dalgona coffee</a></li> <li><a href="/wiki/Egg_coffee" title="Egg coffee">Egg coffee</a></li> <li><a href="/wiki/Espresso" title="Espresso">Espresso</a></li> <li><a href="/wiki/Flat_white" title="Flat white">Flat white</a></li> <li><a href="/wiki/Frapp%C3%A9_coffee" title="Frappé coffee">Frappé coffee</a></li> <li><a href="/wiki/Frappuccino" title="Frappuccino">Frappuccino</a></li> <li><a href="/wiki/Gal%C3%A3o" title="Galão">Galão</a></li> <li><a href="/wiki/List_of_coffee_drinks#Garoto" title="List of coffee drinks">Garoto</a></li> <li><a href="/wiki/Gassosa_al_caff%C3%A8" title="Gassosa al caffè">Gassosa al caffè</a></li> <li><a href="/wiki/Iced_coffee" title="Iced coffee">Iced coffee</a></li> <li><a href="/wiki/Indian_filter_coffee" title="Indian filter coffee">Indian filter coffee</a></li> <li><a href="/wiki/Ipoh_white_coffee" title="Ipoh white coffee">Ipoh white coffee</a></li> <li><a href="/wiki/Irish_coffee" title="Irish coffee">Irish coffee</a></li> <li><a href="/wiki/Karsk" title="Karsk">Karsk</a></li> <li><a href="/wiki/Kopi_(drink)" title="Kopi (drink)">Kopi</a></li> <li><a href="/wiki/Kopi_luwak" title="Kopi luwak">Kopi luwak</a></li> <li><a href="/wiki/Kopi_tubruk" title="Kopi tubruk">Kopi tubruk</a></li> <li><a href="/wiki/Kurdish_coffee" title="Kurdish coffee">Kurdish coffee</a></li> <li><a href="/wiki/Latte_macchiato" title="Latte macchiato">Latte macchiato</a></li> <li><a href="/wiki/Latte" title="Latte">Latte</a></li> <li><a href="/wiki/Liqueur_coffee" title="Liqueur coffee">Liqueur coffee</a></li> <li><a href="/wiki/Long_black" title="Long black">Long black</a></li> <li><a href="/wiki/Lungo" title="Lungo">Lungo</a></li> <li><a href="/wiki/Marocchino" title="Marocchino">Marocchino</a></li> <li><a href="/wiki/Mazagran_(drink)" title="Mazagran (drink)">Mazagran</a></li> <li><a href="/wiki/Moretta_(coffee)" title="Moretta (coffee)">Moretta</a></li> <li><a href="/wiki/Oliang" title="Oliang">Oliang</a></li> <li><a href="/wiki/Raf_coffee" title="Raf coffee">Raf coffee</a></li> <li><a href="/wiki/List_of_coffee_drinks#Red_eye" title="List of coffee drinks">Red eye</a></li> <li><a href="/wiki/Ristretto" title="Ristretto">Ristretto</a></li> <li><a href="/wiki/R%C3%BCdesheimer_Kaffee" title="Rüdesheimer Kaffee">Rüdesheimer Kaffee</a></li> <li><a href="/wiki/Tenom_coffee" class="mw-redirect" title="Tenom coffee">Tenom coffee</a></li> <li><a href="/wiki/Turkish_coffee" title="Turkish coffee">Turkish coffee</a></li> <li><a href="/wiki/White_coffee" title="White coffee">White coffee</a></li> <li><a href="/wiki/White_Russian_(cocktail)" title="White Russian (cocktail)">White Russian</a></li> <li><a href="/wiki/Wiener_Melange" title="Wiener Melange">Wiener Melange</a></li> <li><a href="/wiki/Yazdi_coffee" title="Yazdi coffee">Yazdi coffee</a></li> <li><a href="/wiki/Yuenyeung" title="Yuenyeung">Yuenyeung</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Organization lists</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_bakery_caf%C3%A9s" class="mw-redirect" title="List of bakery cafés">Bakery cafés</a></li> <li><a href="/wiki/List_of_coffee_companies" title="List of coffee companies">Coffee companies</a></li> <li><a href="/wiki/List_of_coffeehouse_chains" title="List of coffeehouse chains">Coffeehouses</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Lifestyle</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/Barista" title="Barista">Barista</a></li> <li><a href="/wiki/Bikini_barista" title="Bikini barista">Bikini barista</a></li> <li><a href="/wiki/Caff%C3%A8_sospeso" title="Caffè sospeso">Caffè sospeso</a></li> <li><a href="/wiki/Break_(work)#Coffee_break" title="Break (work)">Coffee break</a></li> <li><a href="/wiki/Coffee_ceremony_of_Ethiopia_and_Eritrea" title="Coffee ceremony of Ethiopia and Eritrea">Coffee ceremony of Ethiopia and Eritrea</a></li> <li><a href="/wiki/CoffeeCon" title="CoffeeCon">CoffeeCon</a></li> <li><a href="/wiki/Coffee_culture" title="Coffee culture">Coffee culture</a> <ul><li><a href="/wiki/Coffee_culture_in_Australia" title="Coffee culture in Australia">Australia</a></li> <li><a href="/wiki/Coffee_culture_in_the_former_Yugoslavia" title="Coffee culture in the former Yugoslavia">Former Yugoslavia</a></li></ul></li> <li><a href="/wiki/Coffee_cupping" title="Coffee cupping">Coffee cupping</a></li> <li><a href="/wiki/Coffee_palace" title="Coffee palace">Coffee palace</a></li> <li><a href="/wiki/Coffeehouse" title="Coffeehouse">Coffeehouse</a></li> <li><a href="/wiki/English_coffeehouses_in_the_17th_and_18th_centuries" title="English coffeehouses in the 17th and 18th centuries">Historical coffeehouses</a></li> <li><a href="/wiki/Kopi_tiam" title="Kopi tiam">Kopi tiam</a></li> <li><a href="/wiki/Latte_art" title="Latte art">Latte art</a></li> <li><a href="/wiki/Viennese_coffee_house" class="mw-redirect" title="Viennese coffee house">Viennese coffee house</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Coffee_substitute" title="Coffee substitute">Substitutes</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/Caff%C3%A8_d%27orzo" title="Caffè d'orzo">Barley coffee</a></li> <li><a href="/wiki/Barley_tea" title="Barley tea">Barley tea</a></li> <li><a href="/wiki/Barleycup" title="Barleycup">Barleycup</a></li> <li><a href="/wiki/Caro_(drink)" title="Caro (drink)">Caro</a></li> <li><a href="/wiki/Cereal_coffee" title="Cereal coffee">Cereal coffee</a></li> <li><a href="/wiki/Chicory" title="Chicory">Chicory</a></li> <li><a href="/wiki/Dandelion_coffee" title="Dandelion coffee">Dandelion coffee</a></li> <li><a href="/wiki/Inka_(drink)" title="Inka (drink)">Inka</a></li> <li><a href="/wiki/Brosimum_alicastrum" title="Brosimum alicastrum">Maya nut</a></li> <li><a href="/wiki/Postum" title="Postum">Postum</a></li> <li><a href="/wiki/Qishr" title="Qishr">Qishr</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Serving vessels</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/Coffee_cup" title="Coffee cup">Coffee cup</a> <ul><li><a href="/wiki/Coffee_cup_sleeve" title="Coffee cup sleeve">sleeve</a></li></ul></li> <li><a href="/wiki/Cezve" title="Cezve">Cezve</a></li> <li><a href="/wiki/Demitasse" title="Demitasse">Demitasse</a> <ul><li><a href="/wiki/Demitasse_spoon" title="Demitasse spoon">spoon</a></li></ul></li> <li><a href="/wiki/Tasse_%C3%A0_caf%C3%A9" title="Tasse à café">Tasse à café</a></li> <li><a href="/wiki/Zarf" title="Zarf">Zarf</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Competitions</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_States_Barista_Championship" title="United States Barista Championship">United States Barista Championship</a></li> <li><a href="/wiki/World_Barista_Championship" title="World Barista Championship">World Barista Championship</a></li> <li><a href="/wiki/World_Brewers_Cup" title="World Brewers Cup">World Brewers Cup</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Misc.</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/Coffee_and_doughnuts" title="Coffee and doughnuts">Coffee and doughnuts</a></li> <li><a href="/wiki/Coffee_bag" title="Coffee bag">Coffee bag</a></li> <li><a href="/wiki/Coffee_service" title="Coffee service">Coffee service</a></li> <li><a href="/wiki/Coffee_leaf_rust" class="mw-redirect" title="Coffee leaf rust">Coffee leaf rust</a></li> <li><a href="/wiki/Coffee_wars" title="Coffee wars">Coffee wars</a></li> <li><a href="/wiki/Gustav_III_of_Sweden%27s_coffee_experiment" title="Gustav III of Sweden's coffee experiment">Gustav III of Sweden's coffee experiment</a></li> <li><a href="/wiki/Canned_coffee" title="Canned coffee">Canned coffee</a></li> <li><a href="/wiki/Coffee_vending_machine" title="Coffee vending machine">Coffee vending machine</a></li> <li><a href="/wiki/Used_coffee_grounds" title="Used coffee grounds">Used coffee grounds</a></li> <li><a href="/wiki/Sustainable_coffee" title="Sustainable coffee">Sustainable coffee</a></li> <li><a href="/wiki/Low_acid_coffee" title="Low acid coffee">Low acid coffee</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><a href="/wiki/File:Emblem-relax.svg" class="mw-file-description"><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Emblem-relax.svg/15px-Emblem-relax.svg.png" decoding="async" width="15" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Emblem-relax.svg/23px-Emblem-relax.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/Emblem-relax.svg/30px-Emblem-relax.svg.png 2x" data-file-width="60" data-file-height="60" /></a> <a href="/wiki/Portal:Coffee" title="Portal:Coffee">Coffee portal</a></li> <li><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" /> <a href="/wiki/Category:Coffee" title="Category:Coffee">Category: Coffee</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /></div><div role="navigation" class="navbox" aria-labelledby="Chocolate749" 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" style="background: #7B3F00; color: white;"><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:Chocolate" title="Template:Chocolate"><abbr title="View this template" style="color: white">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chocolate" title="Template talk:Chocolate"><abbr title="Discuss this template" style="color: white">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chocolate" title="Special:EditPage/Template:Chocolate"><abbr title="Edit this template" style="color: white">e</abbr></a></li></ul></div><div id="Chocolate749" style="font-size:114%;margin:0 4em"><a href="/wiki/Chocolate" title="Chocolate">Chocolate</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;"><a href="/wiki/Cocoa_bean" title="Cocoa bean">Cocoa bean</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/Chocolate_liquor" title="Chocolate liquor">Chocolate liquor</a></li> <li><a href="/wiki/Cocoa_butter" title="Cocoa butter">Cocoa butter</a></li> <li><a href="/wiki/Cocoa_solids" title="Cocoa solids">Cocoa solids</a></li> <li><a href="/wiki/Theobroma_cacao" title="Theobroma cacao">Theobroma cacao</a></li> <li><a href="/wiki/Types_of_cocoa_beans" title="Types of cocoa beans">Types</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Components</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anandamide" title="Anandamide">Anandamide</a></li> <li><a class="mw-selflink selflink">Caffeine</a></li> <li><a href="/wiki/Endorphins" title="Endorphins">Endorphins</a></li> <li><a href="/wiki/Enkephalin" title="Enkephalin">Enkephalin</a></li> <li><a href="/wiki/Flavan-3-ol" title="Flavan-3-ol">Flavan-3-ol</a></li> <li><a href="/wiki/Lecithin" title="Lecithin">Lecithin</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li> <li><a href="/wiki/Salsolinol" title="Salsolinol">Salsolinol</a></li> <li><a href="/wiki/Tetramethylpyrazine" title="Tetramethylpyrazine">Tetramethylpyrazine</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li> <li><a href="/wiki/Valeric_acid" title="Valeric acid">Valeric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;"><a href="/wiki/Types_of_chocolate" title="Types of chocolate">Types</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/Baking_chocolate" title="Baking chocolate">Baking</a></li> <li><a href="/wiki/Compound_chocolate" title="Compound chocolate">Compound</a></li> <li><a href="/wiki/Couverture_chocolate" title="Couverture chocolate">Couverture</a></li> <li><a href="/wiki/Dark_chocolate" title="Dark chocolate">Dark</a></li> <li><a href="/wiki/Gianduja_(chocolate)" title="Gianduja (chocolate)">Gianduja</a></li> <li><a href="/wiki/Milk_chocolate" title="Milk chocolate">Milk</a></li> <li><a href="/wiki/Organic_chocolate" title="Organic chocolate">Organic</a></li> <li><a href="/wiki/Raw_chocolate" title="Raw chocolate">Raw</a></li> <li><a href="/wiki/Ruby_chocolate" title="Ruby chocolate">Ruby</a></li> <li><a href="/wiki/White_chocolate" title="White chocolate">White</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Products</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/List_of_chocolate_drinks" title="List of chocolate drinks">Beverages</a> <ul><li><a href="/wiki/Caff%C3%A8_mocha" title="Caffè mocha">Caffè mocha</a></li> <li><a href="/wiki/Chocolate_milk" title="Chocolate milk">Milk</a></li> <li><a href="/wiki/Hot_chocolate" title="Hot chocolate">Hot chocolate</a></li> <li><a href="/wiki/Chocolate_liqueur" title="Chocolate liqueur">Liqueur</a></li></ul></li> <li><a href="/wiki/Chocolate_biscuit" title="Chocolate biscuit">Biscuit</a></li> <li><a href="/wiki/Chocolate_brownie" title="Chocolate brownie">Brownie</a></li> <li><a href="/wiki/Chocolate_cake" title="Chocolate cake">Cake</a></li> <li><a href="/wiki/Chocolate_bar" title="Chocolate bar">Chocolate bar</a> <ul><li><a href="/wiki/List_of_chocolate_bar_brands" title="List of chocolate bar brands">Brands</a></li></ul></li> <li><a href="/wiki/Chocolate_chip" title="Chocolate chip">Chocolate chip</a></li> <li><a href="/wiki/Chocolate_chip_cookie" title="Chocolate chip cookie">Chocolate chip cookie</a></li> <li><a href="/wiki/List_of_chocolate-covered_foods" title="List of chocolate-covered foods">Chocolate-covered foods</a></li> <li><a href="/wiki/Chocolate_crackles" title="Chocolate crackles">Chocolate crackles</a></li> <li><a href="/wiki/Cioccolato_di_Modica" title="Cioccolato di Modica">Cioccolato di Modica</a></li> <li><a href="/wiki/Chocolate_coin" title="Chocolate coin">Coins</a></li> <li><a href="/wiki/Fudge" title="Fudge">Fudge</a></li> <li><a href="/wiki/Ganache" title="Ganache">Ganache</a></li> <li><a href="/wiki/Chocolate_gravy" title="Chocolate gravy">Gravy</a></li> <li><a href="/wiki/Chocolate_ice_cream" title="Chocolate ice cream">Ice cream</a></li> <li><a href="/wiki/Mole_(sauce)" title="Mole (sauce)">Mole</a></li> <li><a href="/wiki/Chocolate_pudding" title="Chocolate pudding">Pudding</a></li> <li><a href="/wiki/Chocolate_spread" title="Chocolate spread">Spread</a></li> <li><a href="/wiki/Chocolate_syrup" title="Chocolate syrup">Syrup</a></li> <li><a href="/wiki/Chocolate_truffle" title="Chocolate truffle">Truffle</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Processes</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/Aerated_chocolate" title="Aerated chocolate">Aeration</a></li> <li><a href="/wiki/Broma_process" title="Broma process">Broma process</a></li> <li><a href="/wiki/Conching" title="Conching">Conching</a></li> <li><a href="/wiki/Dutch_process_cocoa" title="Dutch process cocoa">Dutch process</a></li> <li><a href="/wiki/Enrober" title="Enrober">Enrober</a></li> <li><a href="/wiki/Sugar_crust" title="Sugar crust">Sugar crust</a></li> <li><a href="/wiki/Tempered_chocolate" title="Tempered chocolate">Tempering</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Industry</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bean-to-bar" title="Bean-to-bar">Bean-to-bar</a> <ul><li><a href="/wiki/List_of_bean-to-bar_chocolate_manufacturers" title="List of bean-to-bar chocolate manufacturers">Manufacturers</a></li></ul></li> <li><a href="/wiki/Big_Chocolate" title="Big Chocolate">Big Chocolate</a></li> <li><a href="/wiki/Chocolaterie" title="Chocolaterie">Chocolaterie</a></li> <li><a href="/wiki/Chocolatier" title="Chocolatier">Chocolatier</a></li> <li><a href="/wiki/C%C3%B4te_d%27Ivoire%E2%80%93Ghana_Cocoa_Initiative" title="Côte d'Ivoire–Ghana Cocoa Initiative">Côte d'Ivoire–Ghana Cocoa Initiative</a></li> <li><a href="/wiki/Environmental_impact_of_cocoa_production" title="Environmental impact of cocoa production">Environmental impact</a></li> <li><a href="/wiki/Fair_trade_cocoa" title="Fair trade cocoa">Fair trade cocoa</a> <ul><li><a href="/wiki/Child_labour_in_cocoa_production" title="Child labour in cocoa production">Child labour in cocoa production</a></li></ul></li> <li><a href="/wiki/Harkin%E2%80%93Engel_Protocol" title="Harkin–Engel Protocol">Harkin–Engel Protocol</a></li> <li><a href="/wiki/International_Cocoa_Organization" title="International Cocoa Organization">International Cocoa Organization</a></li> <li><a href="/wiki/International_Cocoa_Quarantine_Centre" title="International Cocoa Quarantine Centre">International Cocoa Quarantine Centre</a></li> <li><a href="/wiki/Cocoa_production_in_Ghana" title="Cocoa production in Ghana">Production in Ghana</a> <ul><li><a href="/wiki/Ghana_Cocoa_Board" title="Ghana Cocoa Board">Ghana Cocoa Board</a></li></ul></li> <li><a href="/wiki/Cocoa_production_in_Ivory_Coast" title="Cocoa production in Ivory Coast">Production in Ivory Coast</a></li> <li><a href="/wiki/Cocoa_production_in_Nigeria" title="Cocoa production in Nigeria">Production in Nigeria</a></li> <li><a href="/wiki/Cocoa_production_in_S%C3%A3o_Tom%C3%A9_and_Pr%C3%ADncipe" title="Cocoa production in São Tomé and Príncipe">Production in São Tomé and Príncipe</a></li> <li><a href="/wiki/World_Cocoa_Foundation" title="World Cocoa Foundation">World Cocoa Foundation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">By country</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/Belgian_chocolate" title="Belgian chocolate">Belgium</a></li> <li><a href="/wiki/French_chocolate" title="French chocolate">France</a></li> <li><a href="/wiki/Swiss_chocolate" title="Swiss chocolate">Switzerland</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Other topics</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chocolate_bloom" title="Chocolate bloom">Chocolate bloom</a></li> <li><a href="/wiki/Chocolate_fountain" title="Chocolate fountain">Chocolate fountain</a></li> <li><a href="/wiki/List_of_chocolate_museums" title="List of chocolate museums">Chocolate museums</a></li> <li><a href="/wiki/List_of_chocolatiers" title="List of chocolatiers">Chocolatiers</a></li> <li><a href="/wiki/Cocoa_smuggling" title="Cocoa smuggling">Cocoa smuggling</a></li> <li><a href="/wiki/History_of_chocolate" title="History of chocolate">History</a></li> <li><a href="/wiki/Chocolate_in_savory_cooking" title="Chocolate in savory cooking">In savory cooking</a></li> <li>Military chocolate <ul><li><a href="/wiki/Military_chocolate_(Switzerland)" title="Military chocolate (Switzerland)">Switzerland</a></li> <li><a href="/wiki/Military_chocolate_(United_States)" title="Military chocolate (United States)">United States</a></li></ul></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: #7B3F00; color: white;"><div><div class="plainlist"> <ul><li><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" /> <a href="/wiki/Category:Chocolate" title="Category:Chocolate">Category</a></li> <li><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/20px-Global_thinking.svg.png" decoding="async" width="10" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/40px-Global_thinking.svg.png 2x" data-file-width="130" data-file-height="200" /> <a href="/wiki/Outline_of_chocolate" title="Outline of chocolate">Outline</a></li> <li><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/e/e0/Symbol_question.svg/20px-Symbol_question.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/e/e0/Symbol_question.svg/40px-Symbol_question.svg.png 1.5x" data-file-width="180" data-file-height="185" /> <a href="/wiki/Glossary_of_chocolate_terms" title="Glossary of chocolate terms">Glossary</a></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Tea_(Camellia_sinensis)324" 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:Teas" title="Template:Teas"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Teas" title="Template talk:Teas"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Teas" title="Special:EditPage/Template:Teas"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Tea_(Camellia_sinensis)324" style="font-size:114%;margin:0 4em"><a href="/wiki/Tea" title="Tea">Tea</a> (<a href="/wiki/Camellia_sinensis" title="Camellia sinensis">Camellia sinensis</a>)</div></th></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><a href="/wiki/History_of_tea" title="History of tea">History</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Common varieties</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Black_tea" title="Black tea">Black tea</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/Assam_tea" title="Assam tea">Assam</a></li> <li><a href="/wiki/Wuyi_tea" title="Wuyi tea">Bohea</a></li> <li><a href="/wiki/Tea_production_in_Sri_Lanka#Ceylon_black_tea" title="Tea production in Sri Lanka">Ceylon</a></li> <li><a href="/wiki/Congou" title="Congou">Congou</a></li> <li><a href="/wiki/Darjeeling_tea" title="Darjeeling tea">Darjeeling</a></li> <li><a href="/wiki/Dianhong" title="Dianhong">Dianhong</a></li> <li><a href="/wiki/Golden_Monkey_tea" title="Golden Monkey tea">Golden Monkey</a></li> <li><a href="/wiki/Jin_Jun_Mei_tea" title="Jin Jun Mei tea">Jin Jun Mei</a></li> <li><a href="/wiki/Kangra_tea" title="Kangra tea">Kangra</a></li> <li><a href="/wiki/Keemun" title="Keemun">Keemun</a></li> <li><a href="/wiki/Nilgiri_tea" title="Nilgiri tea">Nilgiri</a></li> <li><a href="/wiki/Sikkim_tea" title="Sikkim tea">Sikkim</a></li> <li><a href="/wiki/Tibeti" title="Tibeti">Tibeti</a></li> <li><a href="/wiki/Rize_tea" title="Rize tea">Rize</a></li> <li><a href="/wiki/Yingdehong_tea" title="Yingdehong tea">Yingdehong</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oolong" title="Oolong">Oolong tea</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/Bai_Jiguan_tea" title="Bai Jiguan tea">Bai Jiguan</a></li> <li><a href="/wiki/Ban_Tian_Yao_tea" title="Ban Tian Yao tea">Ban Tian Yao</a></li> <li><a href="/wiki/Baozhong_tea" title="Baozhong tea">Baozhong</a></li> <li><a href="/wiki/Bu_Zhi_Chun_tea" title="Bu Zhi Chun tea">Bu Zhi Chun</a></li> <li><a href="/wiki/Da_Hong_Pao" title="Da Hong Pao">Da Hong Pao</a></li> <li><a href="/wiki/Dong_Ding_tea" title="Dong Ding tea">Dong ding</a></li> <li><a href="/wiki/Dongfang_meiren" title="Dongfang meiren">Dongfang meiren</a></li> <li><a href="/wiki/Fo_Shou_tea" title="Fo Shou tea">Fo Shou</a></li> <li><a href="/wiki/High-mountain_tea" title="High-mountain tea">Gaoshan</a></li> <li><a href="/wiki/Huangjin_Gui" title="Huangjin Gui">Huangjin Gui</a></li> <li><a href="/wiki/Huang_Meigui_tea" title="Huang Meigui tea">Huang Meigui</a></li> <li><a href="/wiki/Jin_Xuan_tea" title="Jin Xuan tea">Jin Xuan</a></li> <li><a href="/wiki/Qilan_tea" title="Qilan tea">Qilan</a></li> <li><a href="/wiki/Rougui_tea" title="Rougui tea">Rougui</a></li> <li><a href="/wiki/Ruan_zhi" title="Ruan zhi">Ruan zhi</a></li> <li><a href="/wiki/Shui_Jin_Gui_tea" title="Shui Jin Gui tea">Shui Jin Gui</a></li> <li><a href="/wiki/Shui_Xian" title="Shui Xian">Shui Xian</a></li> <li><a href="/wiki/Tieluohan_tea" title="Tieluohan tea">Tieluohan</a></li> <li><a href="/wiki/Tieguanyin" title="Tieguanyin">Tieguanyin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Green_tea" title="Green tea">Green tea</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/Anji_bai_cha" title="Anji bai cha">Anji bai cha</a></li> <li><a href="/wiki/Aracha" title="Aracha">Aracha</a></li> <li><a href="/wiki/Baimao_Hou" title="Baimao Hou">Baimao Hou</a></li> <li><a href="/wiki/Bancha" title="Bancha">Bancha</a></li> <li><a href="/wiki/Biluochun" title="Biluochun">Biluochun</a></li> <li><a href="/wiki/Chun_Mee" title="Chun Mee">Chun Mee</a></li> <li><a href="/wiki/Dafang_tea" title="Dafang tea">Dafang</a></li> <li><a href="/wiki/Genmaicha" title="Genmaicha">Genmaicha</a></li> <li><a href="/wiki/Lu%27an_Melon_Seed_tea" title="Lu'an Melon Seed tea">Lu'an Melon Seed</a></li> <li><a href="/wiki/Gunpowder_tea" title="Gunpowder tea">Gunpowder</a></li> <li><a href="/wiki/Gyokuro" title="Gyokuro">Gyokuro</a></li> <li><a href="/wiki/H%C5%8Djicha" title="Hōjicha">Hōjicha</a></li> <li><a href="/wiki/Taiping_houkui" title="Taiping houkui">Taiping houkui</a></li> <li><a href="/wiki/Huangshan_Maofeng" title="Huangshan Maofeng">Huangshan Maofeng</a></li> <li><a href="/wiki/Hyson" title="Hyson">Hyson</a></li> <li><a href="/wiki/Sencha#Kabusecha" title="Sencha">Kabusecha</a></li> <li><a href="/wiki/Kamairicha" title="Kamairicha">Kamairicha</a></li> <li><a href="/wiki/Konacha" title="Konacha">Konacha</a></li> <li><a href="/wiki/Kukicha" title="Kukicha">Kukicha</a></li> <li><a href="/wiki/Longjing_tea" title="Longjing tea">Longjing</a></li> <li><a href="/wiki/Matcha" title="Matcha">Matcha</a></li> <li><a href="/wiki/Xinyang_Maojian_tea" title="Xinyang Maojian tea">Maojian</a></li> <li><a href="/wiki/Mecha_(tea)" title="Mecha (tea)">Mecha</a></li> <li><a href="/wiki/Mengding_Ganlu_tea" title="Mengding Ganlu tea">Mengding Ganlu</a></li> <li><a href="/wiki/Sencha" title="Sencha">Sencha</a></li> <li><a href="/wiki/Sencha#Shincha" title="Sencha">Shincha</a></li> <li><a href="/wiki/Tamaryokucha" title="Tamaryokucha">Tamaryokucha</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/White_tea" title="White tea">White tea</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/Baimudan_tea" title="Baimudan tea">Bai Mudan</a></li> <li><a href="/wiki/Baihao_Yinzhen" title="Baihao Yinzhen">Baihao Yinzhen</a></li> <li><a href="/wiki/Shoumei_tea" title="Shoumei tea">Shoumei</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Yellow_tea" title="Yellow tea">Yellow tea</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/Junshan_Yinzhen" title="Junshan Yinzhen">Junshan Yinzhen</a></li> <li><a href="/wiki/Huoshan_Huangya_tea" title="Huoshan Huangya tea">Huoshan Huangya</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Fermented_tea" title="Fermented tea">Fermented tea</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/Pu%27er_tea" title="Pu'er tea">Pu-erh</a></li> <li><a href="/wiki/Doncha" title="Doncha">Doncha</a></li> <li><a href="/wiki/Lahpet" title="Lahpet">Lahpet</a></li> <li><a href="/wiki/Kombucha" title="Kombucha">Kombucha</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tea_blending_and_additives" title="Tea blending and additives">Blended or flavoured teas</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/Earl_Grey_tea" title="Earl Grey tea">Earl Grey</a> (<a href="/wiki/Lady_Grey_(tea)" title="Lady Grey (tea)">Lady Grey</a>)</li> <li>Breakfast tea (<a href="/wiki/English_breakfast_tea" title="English breakfast tea">English</a>, <a href="/wiki/Irish_breakfast_tea" title="Irish breakfast tea">Irish</a>)</li> <li><a href="/wiki/Jasmine_tea" title="Jasmine tea">Jasmine tea</a></li> <li><a href="/wiki/Lapsang_souchong" title="Lapsang souchong">Lapsang souchong</a></li> <li><a href="/wiki/Masala_chai" title="Masala chai">Masala chai</a></li> <li><a href="/wiki/Maghrebi_mint_tea" title="Maghrebi mint tea">Maghrebi mint tea</a></li> <li><a href="/wiki/Prince_of_Wales_tea_blend" title="Prince of Wales tea blend">Prince of Wales</a></li> <li><a href="/wiki/Russian_Caravan" title="Russian Caravan">Russian Caravan</a></li> <li><a href="/wiki/Strobilanthes_tonkinensis" title="Strobilanthes tonkinensis">Strobilanthes tonkinensis</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">General</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/Tea_in_Australia" title="Tea in Australia">Australian</a></li> <li><a href="/wiki/Arabic_tea" title="Arabic tea">Arabic</a></li> <li><a href="/wiki/Tea_in_the_United_Kingdom" title="Tea in the United Kingdom">British</a></li> <li><a href="/wiki/Ceylon_tea" title="Ceylon tea">Ceylon</a></li> <li><a href="/wiki/Chinese_tea" title="Chinese tea">Chinese</a></li> <li><a href="/wiki/Korean_tea" title="Korean tea">Korean</a></li> <li><a href="/wiki/Nepali_tea" title="Nepali tea">Nepali</a></li> <li><a href="/wiki/Tea_in_New_Zealand" title="Tea in New Zealand">New Zealand</a></li> <li><a href="/wiki/Taiwanese_tea" title="Taiwanese tea">Taiwanese</a></li> <li><a href="/wiki/Tea_in_Turkey" title="Tea in Turkey">Turkish</a></li> <li><a href="/wiki/Vietnamese_tea" title="Vietnamese tea">Vietnamese</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tea_culture" title="Tea culture">Culture</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%">Customs</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/Tea_(meal)" title="Tea (meal)">Afternoon/High tea/Evening meal</a></li> <li><a href="/wiki/Tea_party" title="Tea party">Tea party</a></li> <li><a href="/wiki/Tasseography" title="Tasseography">Tasseography</a></li> <li><a href="/wiki/East_Asian_tea_ceremony" title="East Asian tea ceremony">East Asian tea ceremony</a> <ul><li><a href="/wiki/Gongfu_tea" title="Gongfu tea">Chinese</a> <ul><li><a href="/wiki/Yum_cha" title="Yum cha">Yum cha</a></li></ul></li> <li><a href="/wiki/Japanese_tea_ceremony" title="Japanese tea ceremony">Japanese</a></li> <li><a href="/wiki/Korean_tea_ceremony" title="Korean tea ceremony">Korean</a></li> <li><a href="/wiki/Taiwanese_tea_culture" title="Taiwanese tea culture">Taiwanese</a></li> <li><a href="/wiki/Ryukyuan_tea_ceremony" title="Ryukyuan tea ceremony">Ryukyuan</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Areas</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/Tea_garden" title="Tea garden">Tea garden</a></li> <li><a href="/wiki/Teahouse" title="Teahouse">Teahouse or tearoom</a></li> <li><a href="/wiki/Cha_chaan_teng" title="Cha chaan teng">Cha chaan teng</a></li> <li><a href="/wiki/Chashitsu" title="Chashitsu">Chashitsu</a> <ul><li><a href="/wiki/Mizuya" title="Mizuya">Mizuya</a></li> <li><a href="/wiki/Sukiya-zukuri" title="Sukiya-zukuri">Sukiya-zukuri</a></li> <li><a href="/wiki/Roji" title="Roji">Roji</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">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/American_tea_culture" title="American tea culture">American</a></li> <li><a href="/wiki/Argentine_tea_culture" title="Argentine tea culture">Argentine</a></li> <li><a href="/wiki/Azerbaijani_tea_culture" title="Azerbaijani tea culture">Azerbaijani</a></li> <li><a href="/wiki/Brazilian_tea_culture" title="Brazilian tea culture">Brazilian</a></li> <li><a href="/wiki/Chinese_tea_culture" title="Chinese tea culture">Chinese</a></li> <li><a href="/wiki/Dominican_tea_culture" title="Dominican tea culture">Dominican</a></li> <li><a href="/wiki/Hong_Kong_tea_culture" title="Hong Kong tea culture">Hong Kong</a></li> <li><a href="/wiki/Indian_tea_culture" title="Indian tea culture">Indian</a></li> <li><a href="/wiki/Tea_culture_in_Japan" title="Tea culture in Japan">Japanese</a></li> <li><a href="/wiki/Mexican_tea_culture" title="Mexican tea culture">Mexican</a></li> <li><a href="/wiki/Pakistani_tea_culture" class="mw-redirect" title="Pakistani tea culture">Pakistani</a></li> <li><a href="/wiki/Russian_tea_culture" title="Russian tea culture">Russian</a></li> <li><a href="/wiki/Senegalese_tea_culture" title="Senegalese tea culture">Senegalese</a></li> <li><a href="/wiki/Taiwanese_tea_culture" title="Taiwanese tea culture">Taiwanese</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/History_of_tea" title="History of tea">History</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/History_of_tea_in_China" class="mw-redirect" title="History of tea in China">China</a></li> <li><a href="/wiki/History_of_tea_in_India" title="History of tea in India">India</a></li> <li><a href="/wiki/History_of_tea_in_Japan" title="History of tea in Japan">Japan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Production and distribution</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/Tea_leaf_grading" title="Tea leaf grading">Leaf grading</a></li> <li><a href="/wiki/Tea_processing" title="Tea processing">Processing</a> <ul><li><a href="/wiki/Decaffeination" title="Decaffeination">Decaffeination</a></li></ul></li> <li><a href="/wiki/Tea_tasting" title="Tea tasting">Tasting</a></li> <li>Cultivation <ul><li><a href="/wiki/List_of_tea_diseases" title="List of tea diseases">Diseases</a></li></ul></li> <li><a href="/wiki/List_of_tea_companies" title="List of tea companies">Companies</a></li> <li><a href="/wiki/List_of_countries_by_tea_consumption_per_capita" title="List of countries by tea consumption per capita">Consumption by country</a></li> <li>Auctions <ul><li><a href="/wiki/London_Tea_Auction" title="London Tea Auction">London</a></li> <li><a href="/wiki/Chittagong_Tea_Auction" title="Chittagong Tea Auction">Chittagong</a></li> <li><a href="/wiki/Guwahati_Tea_Auction_Centre" title="Guwahati Tea Auction Centre">Guwahati</a></li></ul></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="By_country10" 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/Tea_production_in_Bangladesh" title="Tea production in Bangladesh">Bangladesh</a></li> <li><a href="/wiki/Tea_production_in_Indonesia" title="Tea production in Indonesia">Indonesia</a></li> <li><a href="/wiki/Tea_production_in_Kenya" title="Tea production in Kenya">Kenya</a></li> <li><a href="/wiki/Tea_production_in_Rwanda" title="Tea production in Rwanda">Rwanda</a></li> <li><a href="/wiki/Tea_production_in_Sri_Lanka" title="Tea production in Sri Lanka">Sri Lanka</a></li> <li><a href="/wiki/Tea_production_in_the_United_States" title="Tea production 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%">Preparation</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/Flowering_tea" title="Flowering tea">Flowering teas</a></li> <li><a href="/wiki/Infusion" title="Infusion">Infusion</a></li> <li><a href="/wiki/Compressed_tea" title="Compressed tea">Compressed tea</a></li> <li><a href="/wiki/Decoction" title="Decoction">Decoction</a></li> <li><a href="/wiki/ISO_3103" title="ISO 3103">ISO procedure</a></li> <li><a href="/wiki/Steeping" title="Steeping">Steeping</a></li> <li><a href="/wiki/Tea_bag" title="Tea bag">Tea bag</a></li> <li><a href="/wiki/Tea_lady" title="Tea lady">Tea lady</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Health</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/Health_effects_of_tea" title="Health effects of tea">Health effects</a></li> <li><a href="/wiki/Phenolic_content_in_tea" title="Phenolic content in tea">Phenolic content</a></li> <li>Compounds <ul><li><a class="mw-selflink selflink">Caffeine</a></li> <li><a href="/wiki/Theanine" title="Theanine">Theanine</a></li> <li><a href="/wiki/Flavan-3-ol" title="Flavan-3-ol">Flavan-3-ol</a> <ul><li><a href="/wiki/Catechin" title="Catechin">Catechin</a></li></ul></li> <li><a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">Epigallocatechin gallate</a></li> <li><a href="/wiki/Theaflavin" title="Theaflavin">Theaflavin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tea-based drinks</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/Bubble_tea" title="Bubble tea">Bubble tea</a></li> <li><a href="/wiki/Builder%27s_tea" title="Builder's tea">Builder's tea</a></li> <li><a href="/wiki/Burmese_milk_tea" title="Burmese milk tea">Burmese milk tea</a></li> <li><a href="/wiki/Butter_tea" title="Butter tea">Butter tea</a></li> <li><a href="/wiki/Cheese_tea" title="Cheese tea">Cheese tea</a></li> <li><a href="/wiki/Chifir" title="Chifir">Chifir</a></li> <li><a href="/wiki/Doodh_pati_chai" title="Doodh pati chai">Doodh pati chai</a></li> <li><a href="/wiki/Hong_Kong%E2%80%93style_milk_tea" title="Hong Kong–style milk tea">Hong Kong–style milk tea</a></li> <li><a href="/wiki/Iced_tea" title="Iced tea">Iced tea</a> <ul><li><a href="/wiki/Arnold_Palmer_(drink)" title="Arnold Palmer (drink)">Arnold Palmer</a></li></ul></li> <li><a href="/wiki/Jagertee" title="Jagertee">Jagertee</a></li> <li><a href="/wiki/Kahwah" title="Kahwah">Kahwah</a></li> <li><a href="/wiki/Lei_cha" title="Lei cha">Lei cha</a></li> <li><a href="/wiki/Milk_tea" title="Milk tea">Milk tea</a></li> <li><a href="/wiki/Noon_chai" title="Noon chai">Noon chai</a></li> <li><a href="/wiki/Seven-color_tea" title="Seven-color tea">Seven-color tea</a></li> <li><a href="/wiki/Shahi_haleeb" title="Shahi haleeb">Shahi haleeb</a></li> <li><a href="/wiki/Suutei_tsai" title="Suutei tsai">Suutei tsai</a></li> <li><a href="/wiki/Sweet_tea" title="Sweet tea">Sweet tea</a></li> <li><a href="/wiki/Teh_tarik" title="Teh tarik">Teh tarik</a></li> <li><a href="/wiki/Thai_tea" title="Thai tea">Thai tea</a></li> <li><a href="/wiki/Yuenyeung" title="Yuenyeung">Yuenyeung</a></li></ul> </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-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Teaware" title="Teaware">Teaware</a> <ul><li><a href="/wiki/Tea_chest" title="Tea chest">Chest</a></li> <li><a href="/wiki/Tea_caddy" title="Tea caddy">Caddy</a></li> <li><a href="/wiki/Chawan" title="Chawan">Chawan</a></li> <li><a href="/wiki/Infuser" title="Infuser">Infuser</a></li> <li><a href="/wiki/Tea_strainer" title="Tea strainer">Strainer</a></li> <li><a href="/wiki/Teacup" title="Teacup">Teacup</a></li> <li><a href="/wiki/Teapot" title="Teapot">Teapot</a></li> <li><a href="/wiki/Gaiwan" title="Gaiwan">Gaiwan</a></li> <li><a href="/wiki/Tea_set" title="Tea set">Tea set</a></li></ul></li> <li>Literature <ul><li><a href="/wiki/Tea_classics" title="Tea classics">Tea classics</a></li></ul></li> <li><a href="/wiki/Coffee" title="Coffee">Coffee</a></li> <li><a href="/wiki/List_of_Chinese_teas" title="List of Chinese teas">List of Chinese teas</a></li> <li>Teas of related species <ul><li><a href="/wiki/Camellia_japonica" title="Camellia japonica">Camellia japonica</a></li> <li><a href="/wiki/Camellia_sasanqua" title="Camellia sasanqua">Camellia sasanqua</a></li> <li><a href="/wiki/Camellia_taliensis" title="Camellia taliensis">Camellia taliensis</a></li></ul></li> <li>Tea research <ul><li><a href="/wiki/Lipton_Institute_of_Tea" title="Lipton Institute of Tea">Lipton Institute of Tea</a></li> <li><a href="/wiki/Tea_Research_and_Extension_Station" title="Tea Research and Extension Station">Tea Research and Extension Station</a></li></ul></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Herbal_tea14" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Herbal_tea" title="Herbal tea">Herbal tea</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/Cannabis_tea" title="Cannabis tea">Cannabis tea</a></li> <li><a href="/wiki/Chamomile" title="Chamomile">Chamomile</a></li> <li><a href="/wiki/Dried_lime_tea" title="Dried lime tea">Dried lime</a></li> <li><a href="/wiki/Ginger_tea" title="Ginger tea">Ginger</a></li> <li><a href="/wiki/Ilex_guayusa" title="Ilex guayusa">Guayusa</a></li> <li><a href="/wiki/Koththamalli" title="Koththamalli">Koththamalli</a></li> <li><a href="/wiki/Kuding" title="Kuding">Kuding</a></li> <li><a href="/wiki/Mate_(drink)" title="Mate (drink)">Mate</a></li> <li><a href="/wiki/Rooibos" title="Rooibos">Rooibos</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><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" /> <a href="/wiki/Category:Tea" title="Category:Tea">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="Soft_drinks314" 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:Soft_drink" title="Template:Soft drink"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Soft_drink" title="Template talk:Soft drink"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Soft_drink" title="Special:EditPage/Template:Soft drink"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Soft_drinks314" style="font-size:114%;margin:0 4em"><a href="/wiki/Soft_drink" title="Soft drink">Soft drinks</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Brands</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_brand_name_soft_drink_products" title="List of brand name soft drink products">List of brand name soft drink products</a></li> <li><a href="/wiki/List_of_soft_drink_flavors" title="List of soft drink flavors">List of soft drink flavors</a></li> <li><a href="/wiki/List_of_soft_drinks_by_country" title="List of soft drinks by country">List of soft drinks by country</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Types</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/Cola" title="Cola">Cola</a> <ul><li><a href="/wiki/Cherry_cola" title="Cherry cola">Cherry cola</a></li></ul></li> <li><a href="/wiki/Cream_soda" title="Cream soda">Cream soda</a></li> <li><a href="/wiki/Diet_drink" class="mw-redirect" title="Diet drink">Diet</a></li> <li><a href="/wiki/Ginger_ale" title="Ginger ale">Ginger ale</a></li> <li><a href="/wiki/Ginger_beer" title="Ginger beer">Ginger beer</a></li> <li><a href="/wiki/Grape_drink" title="Grape drink">Grape</a></li> <li><a href="/wiki/Lemon-lime_drink" class="mw-redirect" title="Lemon-lime drink">Lemon-lime drink</a></li> <li><a href="/wiki/Orange_soft_drink" title="Orange soft drink">Orange</a></li> <li><a href="/wiki/Root_beer" title="Root beer">Root beer</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Health</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/Sugary_drink_tax" title="Sugary drink tax">Sugary drink tax</a></li> <li><a href="/wiki/Fat_tax" title="Fat tax">Fat tax</a></li> <li><a class="mw-selflink selflink">Caffeine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Companies</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/The_Coca-Cola_Company" title="The Coca-Cola Company">The Coca-Cola Company</a></li> <li><a href="/wiki/Dr_Pepper_Snapple_Group" title="Dr Pepper Snapple Group">Dr Pepper Snapple Group</a></li> <li><a href="/wiki/National_Beverage" title="National Beverage">National Beverage</a></li> <li><a href="/wiki/PepsiCo" title="PepsiCo">PepsiCo</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Misc.</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/Cola_wars" title="Cola wars">Cola wars</a></li> <li><a href="/wiki/Space_Cola_Wars" title="Space Cola Wars">Space Cola Wars</a></li> <li><a href="/wiki/Craft_soda" title="Craft soda">Craft soda</a></li> <li><a href="/wiki/List_of_soft_drink_producers" title="List of soft drink producers">List of soft drink producers</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Goblet_Glass_%28Banquet%29.svg/9px-Goblet_Glass_%28Banquet%29.svg.png" decoding="async" width="9" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Goblet_Glass_%28Banquet%29.svg/13px-Goblet_Glass_%28Banquet%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Goblet_Glass_%28Banquet%29.svg/17px-Goblet_Glass_%28Banquet%29.svg.png 2x" data-file-width="239" data-file-height="408" /> <a href="/wiki/Portal:Drink" title="Portal:Drink">Drink portal</a> <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" /> <a href="/wiki/Category:Soft_drinks" title="Category:Soft drinks">Category: Soft drinks</a></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="Stimulants535" 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:Stimulants" title="Template:Stimulants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Stimulants" title="Template talk:Stimulants"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Stimulants" title="Special:EditPage/Template:Stimulants"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Stimulants535" style="font-size:114%;margin:0 4em"><a href="/wiki/Stimulant" title="Stimulant">Stimulants</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adamantane" title="Adamantane">Adamantanes</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/Adapromine" title="Adapromine">Adapromine</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/wiki/Bromantane" title="Bromantane">Bromantane</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Rimantadine" title="Rimantadine">Rimantadine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adenosine_receptor" title="Adenosine receptor">Adenosine antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/8-Chlorotheophylline" title="8-Chlorotheophylline">8-Chlorotheophylline</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dimethylxanthine" title="8-Cyclopentyl-1,3-dimethylxanthine">8-Cyclopentyltheophylline</a></li> <li><a href="/wiki/8-Phenyltheophylline" title="8-Phenyltheophylline">8-Phenyltheophylline</a></li> <li><a href="/wiki/Aminophylline" title="Aminophylline">Aminophylline</a></li> <li><a class="mw-selflink selflink">Caffeine</a></li> <li><a href="/wiki/CGS-15943" title="CGS-15943">CGS-15943</a></li> <li><a href="/wiki/Dimethazan" title="Dimethazan">Dimethazan</a></li> <li><a href="/wiki/Istradefylline" title="Istradefylline">Istradefylline</a></li> <li><a href="/wiki/Paraxanthine" title="Paraxanthine">Paraxanthine</a></li> <li><a href="/wiki/SCH-58261" title="SCH-58261">SCH-58261</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Psychotropic_alkylamines" title="Psychotropic alkylamines">Alkylamines</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/Cyclopentamine" title="Cyclopentamine">Cyclopentamine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexaneamine</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li> <li><a href="/wiki/Tuaminoheptane" title="Tuaminoheptane">Tuaminoheptane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ampakine" title="Ampakine">Ampakines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CX-516" title="CX-516">CX-516</a></li> <li><a href="/wiki/CX-546" title="CX-546">CX-546</a></li> <li><a href="/wiki/CX-614" class="mw-redirect" title="CX-614">CX-614</a></li> <li><a href="/wiki/Farampator" title="Farampator">CX-691</a></li> <li><a href="/wiki/CX717" title="CX717">CX-717</a></li> <li><a href="/wiki/IDRA-21" title="IDRA-21">IDRA-21</a></li> <li><a href="/wiki/LY-404,187" class="mw-redirect" title="LY-404,187">LY-404,187</a></li> <li><a href="/wiki/LY-503,430" class="mw-redirect" title="LY-503,430">LY-503,430</a></li> <li><a href="/wiki/Nooglutyl" title="Nooglutyl">Nooglutyl</a></li> <li><a href="/wiki/Org_26576" class="mw-redirect" title="Org 26576">Org 26576</a></li> <li><a href="/wiki/PEPA_(drug)" title="PEPA (drug)">PEPA</a></li> <li><a href="/wiki/S-18986" title="S-18986">S-18986</a></li> <li><a href="/wiki/Sunifiram" title="Sunifiram">Sunifiram</a></li> <li><a href="/wiki/Unifiram" title="Unifiram">Unifiram</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclohexylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benocyclidine" title="Benocyclidine">Benocyclidine</a></li> <li><a href="/wiki/Dieticyclidine" title="Dieticyclidine">Dieticyclidine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Eticyclidine" title="Eticyclidine">Eticyclidine</a></li> <li><a href="/wiki/Gacyclidine" title="Gacyclidine">Gacyclidine</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Phencyclamine" class="mw-redirect" title="Phencyclamine">Phencyclamine</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Rolicyclidine" title="Rolicyclidine">Rolicyclidine</a></li> <li><a href="/wiki/Tenocyclidine" title="Tenocyclidine">Tenocyclidine</a></li> <li><a href="/wiki/Tiletamine" title="Tiletamine">Tiletamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzazepine" title="Benzazepine">Benzazepines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Br-APB" title="6-Br-APB">6-Br-APB</a></li> <li><a href="/wiki/SKF-77434" class="mw-redirect" title="SKF-77434">SKF-77434</a></li> <li><a href="/wiki/SKF-81297" class="mw-redirect" title="SKF-81297">SKF-81297</a></li> <li><a href="/wiki/SKF-82958" class="mw-redirect" title="SKF-82958">SKF-82958</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Cathinones</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/3-FMC" class="mw-redirect" title="3-FMC">3-FMC</a></li> <li><a href="/wiki/3-MMC" class="mw-redirect" title="3-MMC">3-MMC</a></li> <li><a href="/wiki/3,4-Dimethylmethcathinone" title="3,4-Dimethylmethcathinone">3,4-DMMC</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">4-BMC</a></li> <li><a href="/wiki/4-Chloromethcathinone" title="4-Chloromethcathinone">4-CMC</a></li> <li><a href="/wiki/4-Methylbuphedrone" title="4-Methylbuphedrone">4-Methylbuphedrone</a></li> <li><a href="/wiki/4-Methylcathinone" title="4-Methylcathinone">4-Methylcathinone</a></li> <li><a href="/wiki/4-Methyl-%CE%B1-ethylaminopentiophenone" title="4-Methyl-α-ethylaminopentiophenone">4-MEAP</a></li> <li><a href="/wiki/4-Methylpentedrone" title="4-Methylpentedrone">4-Methylpentedrone</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Benzedrone" title="Benzedrone">Benzedrone</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Dimethylcathinone" title="Dimethylcathinone">Dimethylcathinone</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Hexedrone" title="Hexedrone">Hexedrone</a></li> <li><a href="/wiki/Isoethcathinone" title="Isoethcathinone">Isoethcathinone</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylenedioxycathinone" title="Methylenedioxycathinone">Methylenedioxycathinone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Mexedrone" title="Mexedrone">Mexedrone</a></li> <li><a href="/wiki/N-Ethylbuphedrone" title="N-Ethylbuphedrone">N-Ethylbuphedrone</a></li> <li><a href="/wiki/N-Ethylhexedrone" title="N-Ethylhexedrone">N-Ethylhexedrone</a></li> <li><a href="/wiki/Pentedrone" title="Pentedrone">Pentedrone</a></li> <li><a href="/wiki/Pentylone" title="Pentylone">Pentylone</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Acetylcholine" title="Acetylcholine">Cholinergics</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/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="/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="/wiki/AR-R17779" title="AR-R17779">AR-R17779</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/Arecoline" title="Arecoline">Arecoline</a></li> <li><a href="/wiki/Bradanicline" title="Bradanicline">Bradanicline</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/Dianicline" title="Dianicline">Dianicline</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/GTS-21" title="GTS-21">GTS-21</a></li> <li><a href="/wiki/Ispronicline" title="Ispronicline">Ispronicline</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/PHA-543,613" title="PHA-543,613">PHA-543,613</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/Rivanicline" title="Rivanicline">Rivanicline</a></li> <li><a href="/wiki/Sazetidine_A" title="Sazetidine A">Sazetidine A</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="/wiki/TC-1698" title="TC-1698">TC-1698</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/Tebanicline" title="Tebanicline">Tebanicline</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></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Convulsion" title="Convulsion">Convulsants</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/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/wiki/DMCM" title="DMCM">DMCM</a></li> <li><a href="/wiki/Flurothyl" title="Flurothyl">Flurothyl</a></li> <li><a href="/wiki/Gabazine" title="Gabazine">Gabazine</a></li> <li><a href="/wiki/Pentylenetetrazol" title="Pentylenetetrazol">Pentetrazol</a></li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Thujone" title="Thujone">Thujone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Eugeroic" title="Eugeroic">Eugeroics</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adrafinil" title="Adrafinil">Adrafinil</a></li> <li><a href="/wiki/Armodafinil" title="Armodafinil">Armodafinil</a></li> <li><a href="/wiki/CRL-40,940" class="mw-redirect" title="CRL-40,940">CRL-40,940</a></li> <li><a href="/wiki/CRL-40,941" class="mw-redirect" title="CRL-40,941">CRL-40,941</a></li> <li><a href="/wiki/Fluorenol" title="Fluorenol">Fluorenol</a></li> <li><a href="/wiki/Modafinil" title="Modafinil">Modafinil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oxazoline" title="Oxazoline">Oxazolines</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/4-Methylaminorex" title="4-Methylaminorex">4-Methylaminorex</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Cyclazodone" title="Cyclazodone">Cyclazodone</a></li> <li><a href="/wiki/Fenozolone" title="Fenozolone">Fenozolone</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li> <li><a href="/wiki/Pemoline" title="Pemoline">Pemoline</a></li> <li><a href="/wiki/Thozalinone" title="Thozalinone">Thozalinone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Methylphenylisobutylamine" title="4-Methylphenylisobutylamine">1-(4-Methylphenyl)-2-aminobutane</a></li> <li><a href="/wiki/1-Methylamino-1-(3,4-methylenedioxyphenyl)propane" title="1-Methylamino-1-(3,4-methylenedioxyphenyl)propane">1-Methylamino-1-(3,4-methylenedioxyphenyl)propane</a></li> <li><a href="/wiki/2-Fluoroamphetamine" title="2-Fluoroamphetamine">2-Fluoroamphetamine</a></li> <li><a href="/wiki/2-FMA" class="mw-redirect" title="2-FMA">2-Fluoromethamphetamine</a></li> <li><a href="/wiki/2-Hydroxyphenethylamine" class="mw-redirect" title="2-Hydroxyphenethylamine">2-OH-PEA</a></li> <li><a href="/wiki/2-Phenyl-3-aminobutane" title="2-Phenyl-3-aminobutane">2-Phenyl-3-aminobutane</a></li> <li><a href="/wiki/2,3-Methylenedioxyamphetamine" title="2,3-Methylenedioxyamphetamine">2,3-MDA</a></li> <li><a href="/wiki/3-FA" class="mw-redirect" title="3-FA">3-Fluoroamphetamine</a></li> <li><a href="/wiki/3-Fluoroethamphetamine" title="3-Fluoroethamphetamine">3-Fluoroethamphetamine</a></li> <li><a href="/wiki/3-Methoxyamphetamine" title="3-Methoxyamphetamine">3-Methoxyamphetamine</a></li> <li><a href="/wiki/3-Methylamphetamine" title="3-Methylamphetamine">3-Methylamphetamine</a></li> <li><a href="/wiki/4-FA" class="mw-redirect" title="4-FA">4-Fluoroamphetamine</a></li> <li><a href="/wiki/4-FMA" class="mw-redirect" title="4-FMA">4-Fluoromethamphetamine</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/AL-1095" title="AL-1095">AL-1095</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Alpha-Ethylphenethylamine" class="mw-redirect" title="Alpha-Ethylphenethylamine">a-Ethylphenethylamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-Amino-1,2-dihydronaphthalene</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-Aminoindane</a></li> <li><a href="/wiki/5-(2-Aminopropyl)indole" title="5-(2-Aminopropyl)indole">5-(2-Aminopropyl)indole</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-Aminotetralin</a></li> <li><a href="/wiki/Acridorex" title="Acridorex">Acridorex</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a>, <a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/%CE%92-Phenylmethamphetamine" title="Β-Phenylmethamphetamine">β-Phenylmethamphetamine</a></li> <li><a href="/wiki/Benfluorex" title="Benfluorex">Benfluorex</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/3-Benzhydrylmorpholine" title="3-Benzhydrylmorpholine">3-Benzhydrylmorpholine</a></li> <li><a href="/wiki/Benzofuranylpropylaminopentane" title="Benzofuranylpropylaminopentane">BPAP</a></li> <li><a href="/wiki/Camfetamine" title="Camfetamine">Camfetamine</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cilobamine" title="Cilobamine">Cilobamine</a></li> <li><a href="/wiki/Cinnamedrine" title="Cinnamedrine">Cinnamedrine</a></li> <li><a href="/wiki/Clenbuterol" title="Clenbuterol">Clenbuterol</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">Dimethoxyamphetamine</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">DOPA</a> (<a href="/wiki/D-DOPA" title="D-DOPA">Dextrodopa</a>, <a href="/wiki/L-DOPA" title="L-DOPA">Levodopa</a>)</li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/L-DOPS" class="mw-redirect" title="L-DOPS">Droxidopa</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li> <li><a href="/wiki/Epinine" class="mw-redirect" title="Epinine">Epinine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fencamfamin" title="Fencamfamin">Fencamfamin</a></li> <li><a href="/wiki/Fencamine" title="Fencamine">Fencamine</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a> (<a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a>)</li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Formetorex" title="Formetorex">Formetorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Gepefrine" title="Gepefrine">Gepefrine</a></li> <li><a href="/wiki/Hexapradol" title="Hexapradol">Hexapradol</a></li> <li><a href="/wiki/4-Hydroxy-3-methoxymethamphetamine" title="4-Hydroxy-3-methoxymethamphetamine">HMMA</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-Iodo-2-aminoindane</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">Indanylamphetamine</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">L-Deprenyl</a> (Selegiline)</li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylbenzodioxolylbutanamine" class="mw-redirect" title="Methylbenzodioxolylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxybutylamphetamine" title="Methylenedioxybutylamphetamine">MDBU</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxypropylamphetamine" class="mw-redirect" title="Methylenedioxypropylamphetamine">MDPR</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Mesocarb" title="Mesocarb">Mesocarb</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> (<a href="/wiki/Methamphetamine" title="Methamphetamine">Dextromethamphetamine</a>, <a href="/wiki/Levomethamphetamine" title="Levomethamphetamine">Levomethamphetamine</a>)</li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/3-Methoxymethamphetamine" title="3-Methoxymethamphetamine">MMMA</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/N,alpha-Diethylphenylethylamine" class="mw-redirect" title="N,alpha-Diethylphenylethylamine">N,alpha-Diethylphenylethylamine</a></li> <li><a href="/wiki/N,N-Dimethylphenethylamine" title="N,N-Dimethylphenethylamine">N,N-Dimethylphenethylamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylamphetamine</a></li> <li><a href="/wiki/Nisoxetine" title="Nisoxetine">Nisoxetine</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/L-Norpseudoephedrine" title="L-Norpseudoephedrine">L-Norpseudoephedrine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine">Octopamine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Oxifentorex" title="Oxifentorex">Oxifentorex</a></li> <li><a href="/wiki/Oxilofrine" title="Oxilofrine">Oxilofrine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">PBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">PCA</a></li> <li><a href="/wiki/Para-Chloromethamphetamine" title="Para-Chloromethamphetamine">PCMA</a></li> <li><a href="/wiki/Norpholedrine" class="mw-redirect" title="Norpholedrine">PHA</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phenatine" title="Phenatine">Phenatine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">PIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxyethylamphetamine" class="mw-redirect" title="Para-Methoxyethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxymethamphetamine" title="Para-Methoxymethamphetamine">PMMA</a></li> <li><a href="/wiki/Phenylpropylaminopentane" title="Phenylpropylaminopentane">PPAP</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Ropinirole" title="Ropinirole">Ropinirole</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a> (<a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a>)</li> <li><a href="/wiki/Sibutramine" title="Sibutramine">Sibutramine</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenylmorpholine" title="Substituted phenylmorpholine">Phenylmorpholines</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/3-Fluorophenmetrazine" title="3-Fluorophenmetrazine">3-Fluorophenmetrazine</a></li> <li><a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</a></li> <li><a href="/wiki/G-130" title="G-130">G-130</a></li> <li><a href="/wiki/Manifaxine" title="Manifaxine">Manifaxine</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/PD-128,907" title="PD-128,907">PD-128,907</a></li> <li><a href="/wiki/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/2-Phenyl-3,6-dimethylmorpholine" title="2-Phenyl-3,6-dimethylmorpholine">2-Phenyl-3,6-dimethylmorpholine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/1-(3-chlorophenyl)-4-(2-phenylethyl)piperazine" class="mw-redirect" title="1-(3-chlorophenyl)-4-(2-phenylethyl)piperazine">3C-PEP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/CM156" title="CM156">CM156</a></li> <li><a href="/wiki/DBL-583" title="DBL-583">DBL-583</a></li> <li><a href="/wiki/GBR-12783" title="GBR-12783">GBR-12783</a></li> <li><a href="/wiki/GBR-12935" title="GBR-12935">GBR-12935</a></li> <li><a href="/wiki/GBR-13069" title="GBR-13069">GBR-13069</a></li> <li><a href="/wiki/GBR-13098" title="GBR-13098">GBR-13098</a></li> <li><a href="/wiki/GBR-13119" title="GBR-13119">GBR-13119</a></li> <li><a href="/wiki/JJC8-088" title="JJC8-088">JJC8-088</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Piperidine" title="Piperidine">Piperidines</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/1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine" title="1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine">1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine</a></li> <li><a href="/wiki/2-Benzylpiperidine" title="2-Benzylpiperidine">2-Benzylpiperidine</a></li> <li><a href="/wiki/2-Methyl-3-phenylpiperidine" title="2-Methyl-3-phenylpiperidine">2-Methyl-3-phenylpiperidine</a></li> <li><a href="/wiki/3,4-Dichloromethylphenidate" title="3,4-Dichloromethylphenidate">3,4-Dichloromethylphenidate</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-Benzylpiperidine</a></li> <li><a href="/wiki/4-Fluoromethylphenidate" title="4-Fluoromethylphenidate">4-Fluoromethylphenidate</a></li> <li><a href="/wiki/4-Methylmethylphenidate" title="4-Methylmethylphenidate">4-Methylmethylphenidate</a></li> <li><a href="/wiki/Desoxypipradrol" title="Desoxypipradrol">Desoxypipradrol</a></li> <li><a href="/wiki/Difemetorex" title="Difemetorex">Difemetorex</a></li> <li><a href="/wiki/Diphenylpyraline" title="Diphenylpyraline">Diphenylpyraline</a></li> <li><a href="/wiki/HDEP-28" title="HDEP-28">Ethylnaphthidate</a></li> <li><a href="/wiki/Ethylphenidate" title="Ethylphenidate">Ethylphenidate</a></li> <li><a href="/wiki/HDMP-28" title="HDMP-28">Methylnaphthidate</a></li> <li><a href="/wiki/Isopropylphenidate" title="Isopropylphenidate">Isopropylphenidate</a></li> <li><a href="/wiki/JZ-IV-10" title="JZ-IV-10">JZ-IV-10</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a> (<a href="/wiki/Dexmethylphenidate" title="Dexmethylphenidate">Dexmethylphenidate</a>)</li> <li><a href="/wiki/(%2B)-CPCA" title="(+)-CPCA">Nocaine</a></li> <li><a href="/wiki/Levophacetoperane" title="Levophacetoperane">Phacetoperane</a></li> <li><a href="/wiki/Pipradrol" title="Pipradrol">Pipradrol</a></li> <li><a href="/wiki/Propylphenidate" title="Propylphenidate">Propylphenidate</a></li> <li><a href="/wiki/Serdexmethylphenidate" title="Serdexmethylphenidate">Serdexmethylphenidate</a></li> <li><a href="/wiki/SCH-5472" title="SCH-5472">SCH-5472</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrrolidine" title="Pyrrolidine">Pyrrolidines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Diphenylmethylpyrrolidine" title="2-Diphenylmethylpyrrolidine">2-Diphenylmethylpyrrolidine</a></li> <li><a href="/wiki/4-Chloro-alpha-pyrrolidinovalerophenone" class="mw-redirect" title="4-Chloro-alpha-pyrrolidinovalerophenone">4-Cl-PVP</a></li> <li><a href="/wiki/5-DBFPV" title="5-DBFPV">5-DBFPV</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopropiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopropiophenone">α-PPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinobutiophenone" class="mw-redirect" title="Alpha-Pyrrolidinobutiophenone">α-PBP</a></li> <li><a href="/wiki/%CE%91-PCYP" title="Α-PCYP">α-PCYP</a></li> <li><a href="/wiki/%CE%91-PHiP" title="Α-PHiP">α-PHiP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinohexiophenone" class="mw-redirect" title="Alpha-Pyrrolidinohexiophenone">α-PHP</a></li> <li><a href="/wiki/%CE%91-Pyrrolidinoheptaphenone" title="Α-Pyrrolidinoheptaphenone">α-PHPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiophenone">α-PVP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiothiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiothiophenone">α-PVT</a></li> <li><a href="/wiki/Diphenylprolinol" title="Diphenylprolinol">Diphenylprolinol</a></li> <li><a href="/wiki/3%27,4%27-Dimethoxy-%CE%B1-Pyrrolidinopentiophenone" class="mw-redirect" title="3',4'-Dimethoxy-α-Pyrrolidinopentiophenone">DMPVP</a></li> <li><a href="/wiki/4%27-Fluoro-%CE%B1-Pyrrolidinooctanophenone" class="mw-redirect" title="4'-Fluoro-α-Pyrrolidinooctanophenone">FPOP</a></li> <li><a href="/wiki/4%27-Fluoro-%CE%B1-Pyrrolidinopentiophenone" class="mw-redirect" title="4'-Fluoro-α-Pyrrolidinopentiophenone">FPVP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinopropiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinopropiophenone">MDPPP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinobutiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinobutiophenone">MDPBP</a></li> <li><a href="/wiki/4%27-Methyl-a-pyrrolidinobutiophenone" class="mw-redirect" title="4'-Methyl-a-pyrrolidinobutiophenone">MPBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">MPHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">MPPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-Pyrrolidinopentiophenone" class="mw-redirect" title="4'-Methoxy-α-Pyrrolidinopentiophenone">MOPVP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopropiophenone" title="4'-Methoxy-α-pyrrolidinopropiophenone">MOPPP</a></li> <li><a href="/wiki/Indapyrophenidone" title="Indapyrophenidone">Indapyrophenidone</a></li> <li><a href="/wiki/Methylenedioxypyrovalerone" title="Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">PEP</a></li> <li><a href="/wiki/Picilorex" title="Picilorex">Picilorex</a></li> <li><a href="/wiki/Prolintane" title="Prolintane">Prolintane</a></li> <li><a href="/wiki/Pyrovalerone" title="Pyrovalerone">Pyrovalerone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Racetam" title="Racetam">Racetams</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Oxiracetam" title="Oxiracetam">Oxiracetam</a></li> <li><a href="/wiki/Phenylpiracetam" title="Phenylpiracetam">Phenylpiracetam</a></li> <li><a href="/wiki/Phenylpiracetam_hydrazide" title="Phenylpiracetam hydrazide">Phenylpiracetam hydrazide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tropane" title="Tropane">Tropanes</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-fluorotropacocaine" class="mw-redirect" title="4-fluorotropacocaine">4-fluorotropacocaine</a></li> <li><a href="/wiki/4%27-Fluorococaine" class="mw-redirect" title="4'-Fluorococaine">4'-Fluorococaine</a></li> <li><a href="/wiki/Altropane" title="Altropane">Altropane (IACFT)</a></li> <li><a href="/wiki/Brasofensine" title="Brasofensine">Brasofensine</a></li> <li><a href="/wiki/WIN_35428" class="mw-redirect" title="WIN 35428">CFT (WIN 35,428)</a></li> <li><a href="/wiki/RTI-55" title="RTI-55">β-CIT (RTI-55)</a></li> <li><a href="/wiki/Cocaethylene" title="Cocaethylene">Cocaethylene</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Dichloropane" title="Dichloropane">Dichloropane (RTI-111)</a></li> <li><a href="/wiki/Difluoropine" title="Difluoropine">Difluoropine</a></li> <li><a href="/wiki/FE-%CE%B2-CPPIT" title="FE-β-CPPIT">FE-β-CPPIT</a></li> <li><a href="/wiki/FP-%CE%B2-CPPIT" title="FP-β-CPPIT">FP-β-CPPIT</a></li> <li><a href="/wiki/Ioflupane_(123I)" title="Ioflupane (123I)">Ioflupane (123I)</a></li> <li><a href="/wiki/Norcocaine" title="Norcocaine">Norcocaine</a></li> <li><a href="/wiki/2-Propanoyl-3-(4-isopropylphenyl)-tropane" title="2-Propanoyl-3-(4-isopropylphenyl)-tropane">PIT</a></li> <li><a href="/wiki/2%CE%B2-Propanoyl-3%CE%B2-(4-tolyl)-tropane" title="2β-Propanoyl-3β-(4-tolyl)-tropane">PTT</a></li> <li><a href="/wiki/RTI-31" title="RTI-31">RTI-31</a></li> <li><a href="/wiki/RTI-32" title="RTI-32">RTI-32</a></li> <li><a href="/wiki/RTI-51" title="RTI-51">RTI-51</a></li> <li><a href="/wiki/RTI-112" title="RTI-112">RTI-112</a></li> <li><a href="/wiki/RTI-113" title="RTI-113">RTI-113</a></li> <li><a href="/wiki/RTI-120" title="RTI-120">RTI-120</a></li> <li><a href="/wiki/RTI-121" title="RTI-121">RTI-121 (IPCIT)</a></li> <li><a href="/wiki/RTI-126" title="RTI-126">RTI-126</a></li> <li><a href="/wiki/RTI-150" title="RTI-150">RTI-150</a></li> <li><a href="/wiki/RTI-177" title="RTI-177">RTI-177</a></li> <li><a href="/wiki/RTI-229" title="RTI-229">RTI-229</a></li> <li><a href="/wiki/(-)-2%CE%B2-(3-(4-Methylphenyl)isoxazol-5-yl)-3%CE%B2-(4-chlorophenyl)tropane" class="mw-redirect" title="(-)-2β-(3-(4-Methylphenyl)isoxazol-5-yl)-3β-(4-chlorophenyl)tropane">RTI-336</a></li> <li><a href="/wiki/RTI-354" class="mw-redirect" title="RTI-354">RTI-354</a></li> <li><a href="/wiki/RTI-371" title="RTI-371">RTI-371</a></li> <li><a href="/wiki/RTI-386" class="mw-redirect" title="RTI-386">RTI-386</a></li> <li><a href="/wiki/Salicylmethylecgonine" title="Salicylmethylecgonine">Salicylmethylecgonine</a></li> <li><a href="/wiki/Tesofensine" title="Tesofensine">Tesofensine</a></li> <li><a href="/wiki/Troparil" title="Troparil">Troparil (β-CPT, WIN 35,065-2)</a></li> <li><a href="/wiki/Tropoxane" title="Tropoxane">Tropoxane</a></li> <li><a href="/wiki/2%CE%B2-Propanoyl-3%CE%B2-(2-naphthyl)-tropane" title="2β-Propanoyl-3β-(2-naphthyl)-tropane">WF-23</a></li> <li><a href="/wiki/2%CE%B1-(Propanoyl)-3%CE%B2-(2-(6-methoxynaphthyl))-tropane" title="2α-(Propanoyl)-3β-(2-(6-methoxynaphthyl))-tropane">WF-33</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-HO-%CE%B1MT" title="4-HO-αMT">4-HO-αMT</a></li> <li><a href="/wiki/4-Methyl-%CE%B1ET" class="mw-redirect" title="4-Methyl-αET">4-Methyl-αET</a></li> <li><a href="/wiki/4-Methyl-%CE%B1MT" class="mw-redirect" title="4-Methyl-αMT">4-Methyl-αMT</a></li> <li><a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Chloro-αMT</a></li> <li><a href="/wiki/5-Fluoro-%CE%B1MT" class="mw-redirect" title="5-Fluoro-αMT">5-Fluoro-αMT</a></li> <li><a href="/wiki/5-MeO-%CE%B1ET" class="mw-redirect" title="5-MeO-αET">5-MeO-αET</a></li> <li><a href="/wiki/5-MeO-%CE%B1MT" class="mw-redirect" title="5-MeO-αMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DIPT</a></li> <li><a href="/wiki/6-Fluoro-%CE%B1MT" class="mw-redirect" title="6-Fluoro-αMT">6-Fluoro-αMT</a></li> <li><a href="/wiki/7-Methyl-%CE%B1ET" class="mw-redirect" title="7-Methyl-αET">7-Methyl-αET</a></li> <li><a href="/wiki/%CE%91-Ethyltryptamine" title="Α-Ethyltryptamine">αET</a></li> <li><a href="/wiki/%CE%91-Methyltryptamine" title="Α-Methyltryptamine">αMT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-MDP" title="2-MDP">2-MDP</a></li> <li><a href="/wiki/3,3-Diphenylcyclobutanamine" title="3,3-Diphenylcyclobutanamine">3,3-Diphenylcyclobutanamine</a></li> <li><a href="/wiki/Amfonelic_acid" title="Amfonelic acid">Amfonelic acid</a></li> <li><a href="/wiki/Amineptine" title="Amineptine">Amineptine</a></li> <li><a href="/wiki/Amiphenazole" title="Amiphenazole">Amiphenazole</a></li> <li><a href="/wiki/Atipamezole" title="Atipamezole">Atipamezole</a></li> <li><a href="/wiki/Atomoxetine" title="Atomoxetine">Atomoxetine</a></li> <li><a href="/wiki/Bemegride" title="Bemegride">Bemegride</a></li> <li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Butyltolylquinuclidine" title="Butyltolylquinuclidine">BTQ</a></li> <li><a href="/wiki/BTS_74,398" title="BTS 74,398">BTS 74,398</a></li> <li><a href="/wiki/Centanafadine" title="Centanafadine">Centanafadine</a></li> <li><a href="/wiki/Ciclazindol" title="Ciclazindol">Ciclazindol</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <li><a href="/wiki/Cropropamide" class="mw-redirect" title="Cropropamide">Cropropamide</a></li> <li><a href="/wiki/Crotetamide" class="mw-redirect" title="Crotetamide">Crotetamide</a></li> <li><a href="/wiki/D-161" title="D-161">D-161</a></li> <li><a href="/wiki/Desipramine" title="Desipramine">Desipramine</a></li> <li><a href="/wiki/Diclofensine" title="Diclofensine">Diclofensine</a></li> <li><a href="/wiki/Dimethocaine" title="Dimethocaine">Dimethocaine</a></li> <li><a href="/wiki/Efaroxan" title="Efaroxan">Efaroxan</a></li> <li><a href="/wiki/Etamivan" title="Etamivan">Etamivan</a></li> <li><a href="/wiki/Fenisorex" title="Fenisorex">Fenisorex</a></li> <li><a href="/wiki/Fenpentadiol" title="Fenpentadiol">Fenpentadiol</a></li> <li><a href="/wiki/Gamfexine" title="Gamfexine">Gamfexine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/GSK1360707F" title="GSK1360707F">GSK1360707F</a></li> <li><a href="/wiki/GYKI-52895" class="mw-redirect" title="GYKI-52895">GYKI-52895</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Idazoxan" title="Idazoxan">Idazoxan</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Indatraline" title="Indatraline">Indatraline</a></li> <li><a href="/wiki/JNJ-7925476" title="JNJ-7925476">JNJ-7925476</a></li> <li><a href="/wiki/Lazabemide" title="Lazabemide">Lazabemide</a></li> <li><a href="/wiki/Leptacline" title="Leptacline">Leptacline</a></li> <li><a href="/wiki/Lomevactone" title="Lomevactone">Lomevactone</a></li> <li><a href="/wiki/LR-5182" title="LR-5182">LR-5182</a></li> <li><a href="/wiki/Mazindol" title="Mazindol">Mazindol</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Mefexamide" title="Mefexamide">Mefexamide</a></li> <li><a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/Methastyridone" title="Methastyridone">Methastyridone</a></li> <li><a href="/wiki/Methiopropamine" title="Methiopropamine">Methiopropamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/Nikethamide" title="Nikethamide">Nikethamide</a></li> <li><a href="/wiki/Nomifensine" title="Nomifensine">Nomifensine</a></li> <li><a href="/wiki/O-2172" title="O-2172">O-2172</a></li> <li><a href="/wiki/Oxaprotiline" title="Oxaprotiline">Oxaprotiline</a></li> <li><a href="/wiki/PNU-99,194" title="PNU-99,194">PNU-99,194</a></li> <li><a href="/wiki/PRC200" class="mw-redirect" title="PRC200">PRC200-SS</a></li> <li><a href="/wiki/Rasagiline" title="Rasagiline">Rasagiline</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Rubidium_chloride" title="Rubidium chloride">Rubidium chloride</a></li> <li><a href="/wiki/Setazindol" title="Setazindol">Setazindol</a></li> <li><a href="/wiki/Tametraline" title="Tametraline">Tametraline</a></li> <li><a href="/wiki/Tandamine" title="Tandamine">Tandamine</a></li> <li><a href="/wiki/Thiopropamine" title="Thiopropamine">Thiopropamine</a></li> <li><a href="/wiki/Thiothinone" title="Thiothinone">Thiothinone</a></li> <li><a href="/wiki/Trazium" title="Trazium">Trazium</a></li> <li><a href="/wiki/UH-232" title="UH-232">UH-232</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-style:italic"><div><a href="/wiki/ATC_code" class="mw-redirect" title="ATC code">ATC code</a>: <a href="/wiki/ATC_code_N06#N06B" title="ATC code N06">N06B</a></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="Other_dermatological_preparations_(D11)246" 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:Other_dermatological_preparations" title="Template:Other dermatological preparations"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Other_dermatological_preparations" title="Template talk:Other dermatological preparations"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Other_dermatological_preparations" title="Special:EditPage/Template:Other dermatological preparations"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Other_dermatological_preparations_(D11)246" style="font-size:114%;margin:0 4em">Other <a href="/wiki/Dermatological" class="mw-redirect" title="Dermatological">dermatological</a> preparations (<a href="/wiki/ATC_code_D11" title="ATC code D11">D11</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anti-seborrheic" title="Anti-seborrheic">Anti-seborrheics</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/Antiandrogen" title="Antiandrogen">Antiandrogens</a> <ul><li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul></li> <li><a href="/wiki/Antifungal" title="Antifungal">Antifungals</a> <ul><li><a href="/wiki/Bifonazole" title="Bifonazole">Bifonazole</a></li> <li><a href="/wiki/Cetrimonium_bromide" title="Cetrimonium bromide">Cetrimonium bromide</a> (<a href="/wiki/Cetrimide" title="Cetrimide">cetrimide</a>)</li> <li><a href="/wiki/Ciclopirox_olamine" class="mw-redirect" title="Ciclopirox olamine">Ciclopirox olamine (ciclopirox)</a></li> <li><a href="/wiki/Climbazole" title="Climbazole">Climbazole</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Miconazole" title="Miconazole">Miconazole</a></li> <li><a href="/wiki/Piroctone_olamine" title="Piroctone olamine">Piroctone olamine</a></li> <li><a href="/wiki/Selenium_disulfide" title="Selenium disulfide">Selenium disulfide (selenium sulfide)</a></li> <li><a href="/w/index.php?title=Xenysalate&action=edit&redlink=1" class="new" title="Xenysalate (page does not exist)">Xenysalate</a></li> <li><a href="/wiki/Zinc_pyrithione" title="Zinc pyrithione">Zinc pyrithione (pyrithione zinc)</a></li></ul></li> <li><a href="/wiki/Antihistamine" title="Antihistamine">Antihistamines</a></li> <li><a href="/wiki/Calcineurin_inhibitor" class="mw-redirect" title="Calcineurin inhibitor">Calcineurin inhibitors</a> <ul><li><a href="/wiki/Cyclosporin" class="mw-redirect" title="Cyclosporin">Cyclosporin</a></li> <li><a href="/wiki/Pimecrolimus" title="Pimecrolimus">Pimecrolimus</a></li> <li><a href="/wiki/Tacrolimus" title="Tacrolimus">Tacrolimus</a></li></ul></li> <li><a href="/wiki/Isotretinoin" title="Isotretinoin">Isotretinoin</a></li> <li><a href="/wiki/Keratolytic" title="Keratolytic">Keratolytics</a> <ul><li><a href="/wiki/Coal_tar" title="Coal tar">Coal tar</a></li> <li><a href="/wiki/Resorcinol" title="Resorcinol">Resorcinol</a></li> <li><a href="/wiki/Salicylic_acid" title="Salicylic acid">Salicylic acid</a></li> <li><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></li> <li><a href="/wiki/Urea" title="Urea">Urea</a> (<a href="/wiki/Urea-containing_cream" title="Urea-containing cream">urea-containing cream</a>)</li></ul></li> <li><a href="/wiki/Lithium_(medication)" title="Lithium (medication)">Lithium salts</a> <ul><li><a href="/wiki/Lithium_gluconate" class="mw-redirect" title="Lithium gluconate">Lithium gluconate</a></li> <li><a href="/wiki/Lithium_succinate" title="Lithium succinate">Lithium succinate</a></li></ul></li> <li><a href="/wiki/Topical_steroid" title="Topical steroid">Topical corticosteroids</a> (e.g., <a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Skin_whitening" title="Skin whitening">Skin lightening</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hydroquinone" title="Hydroquinone">Hydroquinone</a></li> <li><a href="/wiki/Mequinol" title="Mequinol">Mequinol</a></li> <li><a href="/wiki/Monobenzone" title="Monobenzone">Monobenzone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sun_tanning" title="Sun tanning">Skin darkening</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/Afamelanotide" title="Afamelanotide">Afamelanotide</a></li> <li><a href="/wiki/Melanotan_II" title="Melanotan II">Melanotan II</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anti-inflammatories" class="mw-redirect" title="Anti-inflammatories">Anti-inflammatories</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alitretinoin" title="Alitretinoin">Alitretinoin</a></li> <li><a href="/wiki/%CE%93-Linolenic_acid" title="Γ-Linolenic acid">Gamolenic acid</a></li> <li><a href="/wiki/Oxaceprol" title="Oxaceprol">Oxaceprol</a></li> <li><a href="/wiki/Pimecrolimus" title="Pimecrolimus">Pimecrolimus</a></li> <li><a href="/wiki/Tacrolimus" title="Tacrolimus">Tacrolimus</a></li></ul> <ul><li><a href="/wiki/Topical_steroid" title="Topical steroid">Topical corticosteroids</a> (e.g., <a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Management_of_hair_loss" title="Management of hair loss">Alopecia treatments</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/5%CE%B1-Reductase_inhibitor" title="5α-Reductase inhibitor">5α-Reductase inhibitors</a> <ul><li><a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li><a href="/wiki/Dutasteride" title="Dutasteride">Dutasteride</a></li> <li><a href="/wiki/Finasteride" title="Finasteride">Finasteride</a></li> <li><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto extract</a></li></ul></li> <li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> <ul><li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li></ul></li> <li><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Potassium channel openers</a> <ul><li><a href="/wiki/Minoxidil" title="Minoxidil">Minoxidil</a></li></ul></li> <li>Others <ul><li><a href="/wiki/Nepidermin" title="Nepidermin">Nepidermin</a></li> <li><a href="/wiki/Ritlecitinib" title="Ritlecitinib">Ritlecitinib</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hair_growth_inhibitor" class="mw-redirect" title="Hair growth inhibitor">Hair growth inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5%CE%B1-Reductase_inhibitor" title="5α-Reductase inhibitor">5α-Reductase inhibitors</a> <ul><li><a href="/wiki/Dutasteride" title="Dutasteride">Dutasteride</a></li> <li><a href="/wiki/Finasteride" title="Finasteride">Finasteride</a></li></ul></li> <li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> <ul><li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul></li> <li><a href="/wiki/Eflornithine" title="Eflornithine">Eflornithine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abrocitinib" title="Abrocitinib">Abrocitinib</a></li> <li><a href="/wiki/Aminobenzoate" class="mw-redirect" title="Aminobenzoate">Aminobenzoate potassium</a></li> <li><a href="/wiki/Androgen" title="Androgen">Androgens</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>)</li> <li><a href="/wiki/Benzoylperoxide" class="mw-redirect" title="Benzoylperoxide">Benzoylperoxide</a></li> <li><a href="/wiki/Brimonidine" title="Brimonidine">Brimonidine</a></li> <li><a class="mw-selflink selflink">Caffeine</a></li> <li><a href="/wiki/Calcium_gluconate" title="Calcium gluconate">Calcium gluconate</a></li> <li><a href="/wiki/Collagen" title="Collagen">Collagen</a></li> <li><a href="/wiki/Crisaborole" title="Crisaborole">Crisaborole</a></li> <li><a href="/wiki/Cromoglicic_acid" title="Cromoglicic acid">Cromoglicic acid</a></li> <li><a href="/wiki/Delgocitinib" title="Delgocitinib">Delgocitinib</a></li> <li><a href="/wiki/Deoxycholic_acid" title="Deoxycholic acid">Deoxycholic acid</a></li> <li><a href="/wiki/Diclofenac" title="Diclofenac">Diclofenac</a></li> <li><a href="/wiki/Dupilumab" title="Dupilumab">Dupilumab</a></li> <li><a href="/wiki/Estrogen" title="Estrogen">Estrogens</a> (e.g., <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>)</li> <li><a href="/wiki/Glycopyrronium_bromide" title="Glycopyrronium bromide">Glycopyrronium bromide</a></li> <li><a href="/wiki/Glycopyrronium_tosylate" title="Glycopyrronium tosylate">Glycopyrronium tosylate</a></li> <li><a href="/wiki/Hyaluronic_acid" title="Hyaluronic acid">Hyaluronic acid</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Lebrikizumab" title="Lebrikizumab">Lebrikizumab</a></li> <li><a href="/wiki/Lokivetmab" title="Lokivetmab">Lokivetmab</a></li> <li><a href="/wiki/Medical_uses_of_magnesium_sulfate" title="Medical uses of magnesium sulfate">Magnesium sulfate</a></li> <li><a href="/wiki/Metandienone" title="Metandienone">Metandienone</a></li> <li><a href="/wiki/Nemolizumab" title="Nemolizumab">Nemolizumab</a></li> <li><a href="/wiki/Oclacitinib" title="Oclacitinib">Oclacitinib</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Povidone-iodine" title="Povidone-iodine">Povidone-iodine</a></li> <li><a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">Pregnenolone acetate</a></li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (e.g., <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a>)</li> <li><a href="/wiki/Ruxolitinib" title="Ruxolitinib">Ruxolitinib</a></li> <li><a href="/wiki/Sofpironium_bromide" title="Sofpironium bromide">Sofpironium bromide</a></li> <li><a href="/wiki/Tiratricol" title="Tiratricol">Tiratricol</a></li> <li><a href="/wiki/Tralokinumab" title="Tralokinumab">Tralokinumab</a></li></ul> </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="Pharmacodynamics87" 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;"><div id="Pharmacodynamics87" 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="Acetylcholine_metabolism_and_transport_modulators653" 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:Acetylcholine_metabolism_and_transport_modulators" title="Template:Acetylcholine metabolism and transport modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Acetylcholine_metabolism_and_transport_modulators" title="Template talk:Acetylcholine metabolism and transport modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Acetylcholine_metabolism_and_transport_modulators" title="Special:EditPage/Template:Acetylcholine metabolism and transport modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Acetylcholine_metabolism_and_transport_modulators653" style="font-size:114%;margin:0 4em"><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and <a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">transport</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/Enzyme" title="Enzyme">Enzyme</a> (<a href="/wiki/Enzyme_modulator" title="Enzyme modulator">modulators</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:6em;;text-align:center;"><a href="/wiki/Choline_acetyltransferase" title="Choline acetyltransferase"><abbr title="Choline acetyltransferase">ChAT</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 Choline acetyltransferase</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Inhibitors: <a href="/w/index.php?title=1-(-Benzoylethyl)pyridinium&action=edit&redlink=1" class="new" title="1-(-Benzoylethyl)pyridinium (page does not exist)">1-(-Benzoylethyl)pyridinium</a></li> <li><a href="/w/index.php?title=2-(%CE%B1-Naphthoyl)ethyltrimethylammonium&action=edit&redlink=1" class="new" title="2-(α-Naphthoyl)ethyltrimethylammonium (page does not exist)">2-(α-Naphthoyl)ethyltrimethylammonium</a></li> <li><a href="/w/index.php?title=3-Chloro-4-stillbazole&action=edit&redlink=1" class="new" title="3-Chloro-4-stillbazole (page does not exist)">3-Chloro-4-stillbazole</a></li> <li><a href="/w/index.php?title=4-(1-Naphthylvinyl)pyridine&action=edit&redlink=1" class="new" title="4-(1-Naphthylvinyl)pyridine (page does not exist)">4-(1-Naphthylvinyl)pyridine</a></li> <li><a href="/w/index.php?title=Acetylseco_hemicholinium-3&action=edit&redlink=1" class="new" title="Acetylseco hemicholinium-3 (page does not exist)">Acetylseco hemicholinium-3</a></li> <li><a href="/w/index.php?title=Acryloylcholine&action=edit&redlink=1" class="new" title="Acryloylcholine (page does not exist)">Acryloylcholine</a></li> <li><a href="/wiki/AF64A" class="mw-redirect" title="AF64A">AF64A</a></li> <li><a href="/w/index.php?title=(E)-1-Methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine&action=edit&redlink=1" class="new" title="(E)-1-Methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine (page does not exist)">B115</a></li> <li><a href="/w/index.php?title=(2-Benzoylethyl)trimethylammonium&action=edit&redlink=1" class="new" title="(2-Benzoylethyl)trimethylammonium (page does not exist)">BETA</a></li> <li><a href="/w/index.php?title=N,N-Dimethylamino-2-ethoxyimino-2-adamantane&action=edit&redlink=1" class="new" title="N,N-Dimethylamino-2-ethoxyimino-2-adamantane (page does not exist)">CM-54,903</a></li> <li><a href="/w/index.php?title=N,N-Dimethylaminoethylacrylate&action=edit&redlink=1" class="new" title="N,N-Dimethylaminoethylacrylate (page does not exist)">N,N-Dimethylaminoethylacrylate</a></li> <li><a href="/w/index.php?title=N,N-Dimethylaminoethylchloroacetate&action=edit&redlink=1" class="new" title="N,N-Dimethylaminoethylchloroacetate (page does not exist)">N,N-Dimethylaminoethylchloroacetate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase"><abbr title="Acetylcholinesterase">AChE</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 Acetylcholinesterase</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylcholinesterase_inhibitor" title="Acetylcholinesterase inhibitor">Inhibitors</a>: Reversible: Carbamates: <a href="/wiki/Aldicarb" title="Aldicarb">Aldicarb</a></li> <li><a href="/wiki/Aminocarb" title="Aminocarb">Aminocarb</a></li> <li><a href="/wiki/Bendiocarb" title="Bendiocarb">Bendiocarb</a></li> <li><a href="/w/index.php?title=Bufencarb&action=edit&redlink=1" class="new" title="Bufencarb (page does not exist)">Bufencarb</a></li> <li><a href="/wiki/Carbaryl" title="Carbaryl">Carbaryl</a></li> <li><a href="/wiki/Carbendazim" title="Carbendazim">Carbendazim</a></li> <li><a href="/w/index.php?title=Carbetamide&action=edit&redlink=1" class="new" title="Carbetamide (page does not exist)">Carbetamide</a></li> <li><a href="/wiki/Carbofuran" title="Carbofuran">Carbofuran</a></li> <li><a href="/wiki/Carbosulfan" title="Carbosulfan">Carbosulfan</a></li> <li><a href="/w/index.php?title=Chlorbufam&action=edit&redlink=1" class="new" title="Chlorbufam (page does not exist)">Chlorbufam</a></li> <li><a href="/w/index.php?title=Chloropropham&action=edit&redlink=1" class="new" title="Chloropropham (page does not exist)">Chloropropham</a></li> <li><a href="/wiki/Dimetilan" title="Dimetilan">Dimetilan</a></li> <li><a href="/wiki/Ethienocarb" class="mw-redirect" title="Ethienocarb">Ethienocarb</a></li> <li><a href="/wiki/Ethiofencarb" title="Ethiofencarb">Ethiofencarb</a></li> <li><a href="/wiki/Fenobucarb" title="Fenobucarb">Fenobucarb</a></li> <li><a href="/wiki/Formetanate" title="Formetanate">Formetanate</a></li> <li><a href="/wiki/Formparanate" title="Formparanate">Formparanate</a></li> <li><a href="/wiki/Methiocarb" title="Methiocarb">Methiocarb</a></li> <li><a href="/wiki/Methomyl" title="Methomyl">Methomyl</a></li> <li><a href="/wiki/Metolcarb" title="Metolcarb">Metolcarb</a></li> <li><a href="/wiki/Miotine" title="Miotine">Miotine</a></li> <li><a href="/wiki/Oxamyl" title="Oxamyl">Oxamyl</a></li> <li><a href="/w/index.php?title=Phenmedipham&action=edit&redlink=1" class="new" title="Phenmedipham (page does not exist)">Phenmedipham</a></li> <li><a href="/w/index.php?title=Pinmicarb&action=edit&redlink=1" class="new" title="Pinmicarb (page does not exist)">Pinmicarb</a></li> <li><a href="/wiki/Pirimicarb" title="Pirimicarb">Pirimicarb</a></li> <li><a href="/wiki/Promecarb" title="Promecarb">Promecarb</a></li> <li><a href="/wiki/Propamocarb" title="Propamocarb">Propamocarb</a></li> <li><a href="/w/index.php?title=Propham&action=edit&redlink=1" class="new" title="Propham (page does not exist)">Propham</a></li> <li><a href="/wiki/Propoxur" title="Propoxur">Propoxur</a></li> <li><a href="/w/index.php?title=Thiodicarb&action=edit&redlink=1" class="new" title="Thiodicarb (page does not exist)">Thiodicarb</a></li> <li><a href="/wiki/Thiofanox" title="Thiofanox">Thiofanox</a>; Stigmines: <a href="/wiki/Distigmine" title="Distigmine">Distigmine</a></li> <li><a href="/w/index.php?title=Eptastigmine&action=edit&redlink=1" class="new" title="Eptastigmine (page does not exist)">Eptastigmine</a></li> <li><a href="/w/index.php?title=Ganstigmine&action=edit&redlink=1" class="new" title="Ganstigmine (page does not exist)">Ganstigmine</a></li> <li><a href="/wiki/Neostigmine" title="Neostigmine">Neostigmine</a> <a href="/wiki/Neostigmine/glycopyrronium_bromide" title="Neostigmine/glycopyrronium bromide">+glycopyrronium bromide</a></li> <li><a href="/wiki/Phenserine" title="Phenserine">Phenserine</a></li> <li><a href="/wiki/Physostigmine" title="Physostigmine">Physostigmine</a></li> <li><a href="/wiki/Pyridostigmine" title="Pyridostigmine">Pyridostigmine</a></li> <li><a href="/w/index.php?title=Quilostigmine&action=edit&redlink=1" class="new" title="Quilostigmine (page does not exist)">Quilostigmine</a></li> <li><a href="/wiki/Rivastigmine" title="Rivastigmine">Rivastigmine</a></li> <li><a href="/w/index.php?title=Terestigmine&action=edit&redlink=1" class="new" title="Terestigmine (page does not exist)">Terestigmine</a>; Others: <a href="/wiki/Acotiamide" title="Acotiamide">Acotiamide</a></li> <li><a href="/wiki/Ambenonium" class="mw-redirect" title="Ambenonium">Ambenonium</a></li> <li><a class="mw-selflink selflink">Caffeine</a></li> <li><a href="/wiki/Donepezil" title="Donepezil">Donepezil</a></li> <li><a href="/wiki/EA-3990" title="EA-3990">EA-3990</a></li> <li><a href="/wiki/EA-4056" title="EA-4056">EA-4056</a></li> <li><a href="/wiki/Edrophonium" title="Edrophonium">Edrophonium</a></li> <li><a href="/wiki/Galantamine" title="Galantamine">Galantamine</a></li> <li><a href="/wiki/Huperzine_A" title="Huperzine A">Huperzine A</a></li> <li><a href="/w/index.php?title=Huprine_W&action=edit&redlink=1" class="new" title="Huprine W (page does not exist)">Huprine W</a></li> <li><a href="/wiki/Huprine_X" title="Huprine X">Huprine X</a></li> <li><a href="/w/index.php?title=Huprine_Y&action=edit&redlink=1" class="new" title="Huprine Y (page does not exist)">Huprine Y</a></li> <li><a href="/wiki/Ipidacrine" title="Ipidacrine">Ipidacrine</a></li> <li><a href="/wiki/Itopride" title="Itopride">Itopride</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Minaprine" title="Minaprine">Minaprine</a></li> <li><a href="/wiki/Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium_bromide)" title="Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)">Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)</a></li> <li><a href="/wiki/T-1123" title="T-1123">T-1123</a></li> <li><a href="/wiki/T-1152" title="T-1152">T-1152</a></li> <li><a href="/wiki/T-1194" title="T-1194">T-1194</a></li> <li><a href="/wiki/TL-599" title="TL-599">TL-599</a></li> <li><a href="/wiki/TL-1238" title="TL-1238">TL-1238</a></li> <li><a href="/wiki/Tacrine" title="Tacrine">Tacrine</a></li> <li><a href="/w/index.php?title=Zanapezil&action=edit&redlink=1" class="new" title="Zanapezil (page does not exist)">Zanapezil</a></li></ul> <ul><li>Irreversible: Organophosphates: <a href="/wiki/2-Ethoxycarbonyl-1-methylvinyl_cyclohexyl_methylphosphonate" title="2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate">2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate</a></li> <li><a href="/wiki/Acephate" title="Acephate">Acephate</a></li> <li><a href="/wiki/Armine_(chemical)" title="Armine (chemical)">Armine</a></li> <li><a href="/wiki/Azinphos-ethyl" title="Azinphos-ethyl">Azinphos-ethyl</a></li> <li><a href="/wiki/Azinphos-methyl" title="Azinphos-methyl">Azinphos-methyl</a></li> <li><a href="/wiki/BAY-29952" title="BAY-29952">BAY-29952</a></li> <li><a href="/wiki/Bensulide" title="Bensulide">Bensulide</a></li> <li><a href="/wiki/Cadusafos" title="Cadusafos">Cadusafos</a></li> <li><a href="/wiki/Carbophenothion" title="Carbophenothion">Carbophenothion</a></li> <li><a href="/wiki/Chlorethoxyfos" title="Chlorethoxyfos">Chlorethoxyfos</a></li> <li><a href="/wiki/Chlorfenvinphos" title="Chlorfenvinphos">Chlorfenvinphos</a></li> <li><a href="/wiki/Chlorpyrifos" title="Chlorpyrifos">Chlorpyrifos</a></li> <li><a href="/wiki/Chlorpyrifos-methyl" class="mw-redirect" title="Chlorpyrifos-methyl">Chlorpyrifos-methyl</a></li> <li><a href="/wiki/Coumaphos" title="Coumaphos">Coumaphos</a></li> <li><a href="/wiki/Crotylsarin" title="Crotylsarin">Crotylsarin</a></li> <li><a href="/wiki/Cyanophos" title="Cyanophos">Cyanophos</a></li> <li><a href="/wiki/Cyclosarin" title="Cyclosarin">Cyclosarin (GF)</a></li> <li><a href="/wiki/Demephion" title="Demephion">Demephion</a></li> <li><a href="/wiki/Demeton" title="Demeton">Demeton</a></li> <li><a href="/wiki/Demeton-S-methyl" title="Demeton-S-methyl">Demeton-S-methyl</a></li> <li><a href="/wiki/Dialifor" title="Dialifor">Dialifor</a></li> <li><a href="/wiki/Diazinon" title="Diazinon">Diazinon</a></li> <li><a href="/wiki/Dichlorvos" title="Dichlorvos">Dichlorvos</a></li> <li><a href="/wiki/Dicrotophos" title="Dicrotophos">Dicrotophos</a></li> <li><a href="/wiki/Dicyclohexyl_phosphorofluoridate" title="Dicyclohexyl phosphorofluoridate">Dicyclohexyl phosphorofluoridate</a></li> <li><a href="/wiki/Diisopropylphosphate" title="Diisopropylphosphate">Diisopropylphosphate</a></li> <li><a href="/wiki/Diisopropyl_fluorophosphate" title="Diisopropyl fluorophosphate">Diisopropyl fluorophosphate</a></li> <li><a href="/wiki/Dimefox" title="Dimefox">Dimefox</a></li> <li><a href="/wiki/Dimethoate" title="Dimethoate">Dimethoate</a></li> <li><a href="/wiki/Dimethyl_4-(methylthio)phenyl_phosphate" title="Dimethyl 4-(methylthio)phenyl phosphate">Dimethyl 4-(methylthio)phenyl phosphate</a></li> <li><a href="/wiki/Dioxathion" title="Dioxathion">Dioxathion</a></li> <li><a href="/wiki/Disulfoton" title="Disulfoton">Disulfoton</a></li> <li><a href="/wiki/EA-2012" title="EA-2012">EA-2012</a></li> <li><a href="/wiki/EA-2054" title="EA-2054">EA-2054</a></li> <li><a href="/wiki/EA-2098" title="EA-2098">EA-2098</a></li> <li><a href="/wiki/EA-2192" title="EA-2192">EA-2192</a></li> <li><a href="/wiki/EA-2613" title="EA-2613">EA-2613</a></li> <li><a href="/wiki/EA-3148" title="EA-3148">EA-3148</a></li> <li><a href="/wiki/EA-4352" title="EA-4352">EA-4352</a></li> <li><a href="/wiki/Echothiophate" title="Echothiophate">Echothiophate</a></li> <li><a href="/wiki/Ethylsarin" title="Ethylsarin">Ethylsarin (GE)</a></li> <li><a href="/wiki/Endothion" title="Endothion">Endothion</a></li> <li><a href="/wiki/EPN_(insecticide)" title="EPN (insecticide)">EPN</a></li> <li><a href="/wiki/Ethion" title="Ethion">Ethion</a></li> <li><a href="/wiki/Ethoprop" class="mw-redirect" title="Ethoprop">Ethoprop</a></li> <li><a href="/wiki/Fenamiphos" title="Fenamiphos">Fenamiphos</a></li> <li><a href="/wiki/Fenitrothion" title="Fenitrothion">Fenitrothion</a></li> <li><a href="/wiki/Fenthion" title="Fenthion">Fenthion</a></li> <li><a href="/wiki/Fluorotabun" title="Fluorotabun">Fluorotabun</a></li> <li><a href="/wiki/Fonofos" title="Fonofos">Fonofos</a></li> <li><a href="/wiki/Formothion" title="Formothion">Formothion</a></li> <li><a href="/w/index.php?title=Fosthiazate&action=edit&redlink=1" class="new" title="Fosthiazate (page does not exist)">Fosthiazate</a></li> <li><a href="/wiki/GD-42" title="GD-42">GD-42</a></li> <li><a href="/wiki/GH_(nerve_agent)" title="GH (nerve agent)">GH</a></li> <li><a href="/w/index.php?title=GT-45&action=edit&redlink=1" class="new" title="GT-45 (page does not exist)">GT-45</a></li> <li><a href="/wiki/GV_(nerve_agent)" title="GV (nerve agent)">GV</a></li> <li><a href="/wiki/Guanitoxin" title="Guanitoxin">Guanitoxin</a></li> <li><a href="/wiki/Hexaethyl_tetraphosphate" title="Hexaethyl tetraphosphate">Hexaethyl tetraphosphate (HETP)</a></li> <li><a href="/wiki/Isofluorophate" class="mw-redirect" title="Isofluorophate">Isofluorophate</a></li> <li><a href="/wiki/Isoxathion" title="Isoxathion">Isoxathion</a></li> <li><a href="/wiki/Leptophos" title="Leptophos">Leptophos</a></li> <li><a href="/wiki/Malaoxon" title="Malaoxon">Malaoxon</a></li> <li><a href="/wiki/Malathion" title="Malathion">Malathion</a></li> <li><a href="/w/index.php?title=Mazidox&action=edit&redlink=1" class="new" title="Mazidox (page does not exist)">Mazidox</a></li> <li><a href="/wiki/Methamidophos" title="Methamidophos">Methamidophos</a></li> <li><a href="/wiki/Methidathion" title="Methidathion">Methidathion</a></li> <li><a href="/wiki/Methyl_phenkapton" title="Methyl phenkapton">Methyl phenkapton</a></li> <li><a href="/wiki/Methylfluorophosphonylcholine" title="Methylfluorophosphonylcholine">Methylfluorophosphonylcholine (MFPCh)</a></li> <li><a href="/wiki/Metrifonate" title="Metrifonate">Metrifonate</a></li> <li><a href="/wiki/Mevinphos" title="Mevinphos">Mevinphos</a></li> <li><a href="/wiki/Mipafox" title="Mipafox">Mipafox</a></li> <li><a href="/wiki/Monocrotophos" title="Monocrotophos">Monocrotophos</a></li> <li><a href="/wiki/MSPI_(nerve_agent)" title="MSPI (nerve agent)">MSPI</a></li> <li><a href="/wiki/Naled" title="Naled">Naled</a></li> <li><a href="/wiki/Novichok_agent" class="mw-redirect" title="Novichok agent">Novichok agent</a></li> <li><a href="/wiki/Omethoate" title="Omethoate">Omethoate</a></li> <li><a href="/wiki/Oxydemeton-methyl" title="Oxydemeton-methyl">Oxydemeton-methyl</a></li> <li><a href="/wiki/Paraoxon" title="Paraoxon">Paraoxon</a></li> <li><a href="/wiki/Parathion" title="Parathion">Parathion</a></li> <li><a href="/wiki/Parathion-methyl" class="mw-redirect" title="Parathion-methyl">Parathion-methyl</a></li> <li><a href="/wiki/Phorate" title="Phorate">Phorate</a></li> <li><a href="/wiki/Phosalone" title="Phosalone">Phosalone</a></li> <li><a href="/wiki/Phosfolan" title="Phosfolan">Phosfolan</a></li> <li><a href="/wiki/Phosmet" title="Phosmet">Phosmet</a></li> <li><a href="/wiki/Phosphamidon" title="Phosphamidon">Phosphamidon</a></li> <li><a href="/wiki/Phoxim" title="Phoxim">Phoxim</a></li> <li><a href="/wiki/Pirimiphos-methyl" title="Pirimiphos-methyl">Pirimiphos-methyl</a></li> <li><a href="/wiki/Profenofos" title="Profenofos">Profenofos</a></li> <li><a href="/wiki/Prothoate" title="Prothoate">Prothoate</a></li> <li><a href="/wiki/R-16661" title="R-16661">R-16661</a></li> <li><a href="/w/index.php?title=Ro_3-0340&action=edit&redlink=1" class="new" title="Ro 3-0340 (page does not exist)">Ro 3-0340</a></li> <li><a href="/w/index.php?title=Ro_3-0346&action=edit&redlink=1" class="new" title="Ro 3-0346 (page does not exist)">Ro 3-0346</a></li> <li><a href="/w/index.php?title=Ro_3-0347&action=edit&redlink=1" class="new" title="Ro 3-0347 (page does not exist)">Ro 3-0347</a></li> <li><a href="/w/index.php?title=Ro_3-0351&action=edit&redlink=1" class="new" title="Ro 3-0351 (page does not exist)">Ro 3-0351</a></li> <li><a href="/w/index.php?title=Ro_3-0352&action=edit&redlink=1" class="new" title="Ro 3-0352 (page does not exist)">Ro 3-0352</a></li> <li><a href="/w/index.php?title=Ro_3-0397&action=edit&redlink=1" class="new" title="Ro 3-0397 (page does not exist)">Ro 3-0397</a></li> <li><a href="/w/index.php?title=Ro_3-0411&action=edit&redlink=1" class="new" title="Ro 3-0411 (page does not exist)">Ro 3-0411</a></li> <li><a href="/wiki/Ro_3-0412" title="Ro 3-0412">Ro 3-0412</a></li> <li><a href="/w/index.php?title=Ro_3-0417&action=edit&redlink=1" class="new" title="Ro 3-0417 (page does not exist)">Ro 3-0417</a></li> <li><a href="/wiki/Ro_3-0419" title="Ro 3-0419">Ro 3-0419</a></li> <li><a href="/wiki/Ro_3-0422" title="Ro 3-0422">Ro 3-0422</a></li> <li><a href="/w/index.php?title=Ro_3-0433&action=edit&redlink=1" class="new" title="Ro 3-0433 (page does not exist)">Ro 3-0433</a></li> <li><a href="/w/index.php?title=Ronnel&action=edit&redlink=1" class="new" title="Ronnel (page does not exist)">Ronnel</a></li> <li><a href="/wiki/Sarin" title="Sarin">Sarin (GB)</a></li> <li><a href="/wiki/Schradan" title="Schradan">Schradan</a></li> <li><a href="/wiki/Soman" title="Soman">Soman (GD)</a></li> <li><a href="/wiki/Sulfotep" title="Sulfotep">Sulfotep (TEDP)</a></li> <li><a href="/wiki/Tabun_(nerve_agent)" title="Tabun (nerve agent)">Tabun (GA)</a></li> <li><a href="/wiki/Tebupirimfos" title="Tebupirimfos">Tebupirimfos</a></li> <li><a href="/wiki/Temefos" title="Temefos">Temefos</a></li> <li><a href="/wiki/Terbufos" title="Terbufos">Terbufos</a></li> <li><a href="/wiki/Tetrachlorvinphos" title="Tetrachlorvinphos">Tetrachlorvinphos</a></li> <li><a href="/wiki/Tetraethyl_pyrophosphate" title="Tetraethyl pyrophosphate">Tetraethyl pyrophosphate (TEPP)</a></li> <li><a href="/wiki/Triazofos" title="Triazofos">Triazofos</a></li> <li><a href="/w/index.php?title=Tribufos&action=edit&redlink=1" class="new" title="Tribufos (page does not exist)">Tribufos</a></li> <li><a href="/wiki/Trichlorfon" class="mw-redirect" title="Trichlorfon">Trichlorfon</a></li> <li><a href="/wiki/Trichloronate" title="Trichloronate">Trichloronate</a></li> <li><a href="/wiki/Tricresyl_phosphate" title="Tricresyl phosphate">Tricresyl phosphate</a></li> <li><a href="/wiki/VE_(nerve_agent)" title="VE (nerve agent)">VE</a></li> <li><a href="/wiki/VG_(nerve_agent)" title="VG (nerve agent)">VG</a></li> <li><a href="/wiki/VM_(nerve_agent)" title="VM (nerve agent)">VM</a></li> <li><a href="/wiki/VP_(nerve_agent)" class="mw-redirect" title="VP (nerve agent)">VP</a></li> <li><a href="/wiki/VS_(nerve_agent)" title="VS (nerve agent)">VS</a></li> <li><a href="/wiki/VR_(nerve_agent)" title="VR (nerve agent)">VR</a></li> <li><a href="/wiki/VX_(nerve_agent)" title="VX (nerve agent)">VX</a>; Others: <a href="/wiki/Demecarium" class="mw-redirect" title="Demecarium">Demecarium</a></li> <li><a href="/wiki/Fasciculin" title="Fasciculin">Fasciculins (green mamba toxins)</a> (<a href="/w/index.php?title=Fasciculin_1&action=edit&redlink=1" class="new" title="Fasciculin 1 (page does not exist)">1</a>, <a href="/w/index.php?title=Fasciculin_2&action=edit&redlink=1" class="new" title="Fasciculin 2 (page does not exist)">2</a>, <a href="/w/index.php?title=Fasciculin_3&action=edit&redlink=1" class="new" title="Fasciculin 3 (page does not exist)">3</a>, <a href="/w/index.php?title=Fasciculin_4&action=edit&redlink=1" class="new" title="Fasciculin 4 (page does not exist)">4</a>)</li> <li><a href="/wiki/Onchidal" title="Onchidal">Onchidal</a> (<a href="/wiki/Onchidella_binneyi" title="Onchidella binneyi">Onchidella binneyi</a>)</li> <li><a href="/wiki/Methanesulfonyl_fluoride" title="Methanesulfonyl fluoride">Methanesulfonyl fluoride</a></li></ul> <ul><li>Unsorted: <a href="/wiki/%CE%91-Pinene" title="Α-Pinene">α-Pinene</a></li> <li><a href="/wiki/%CE%91-Viniferin" title="Α-Viniferin">α-Viniferin</a></li> <li><a href="/wiki/Affinine" title="Affinine">Affinine</a></li> <li><a href="/wiki/Affinisine" title="Affinisine">Affinisine</a></li> <li><a href="/wiki/Arisugacin_A" title="Arisugacin A">Arisugacin A</a></li> <li><a href="/wiki/Bulbocapnine" title="Bulbocapnine">Bulbocapnine</a></li> <li><a href="/wiki/Conodurine" title="Conodurine">Conodurine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Corydaline" title="Corydaline">Corydaline</a></li> <li><a href="/wiki/Corynoline" title="Corynoline">Corynoline</a></li> <li><a href="/wiki/Crimidine" title="Crimidine">Crimidine</a></li> <li><a href="/wiki/Cyclanoline" title="Cyclanoline">Cyclanoline</a></li> <li><a href="/wiki/Cymserine" title="Cymserine">Cymserine</a></li> <li><a href="/wiki/Harmaline" title="Harmaline">Harmaline</a></li> <li><a href="/wiki/Kobophenol_A" title="Kobophenol A">Kobophenol A</a></li> <li><a href="/wiki/Lactucopicrin" title="Lactucopicrin">Lactucopicrin</a></li> <li><a href="/wiki/Lycorine" title="Lycorine">Lycorine</a></li> <li><a href="/wiki/Phosacetim" title="Phosacetim">Phosacetim</a></li> <li><a href="/wiki/Rosmarinic_acid" title="Rosmarinic acid">Rosmarinic acid</a></li> <li><a href="/wiki/Stercuronium_iodide" title="Stercuronium iodide">Stercuronium iodide</a></li> <li><a href="/wiki/Taspine" title="Taspine">Taspine</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a></li> <li><a href="/wiki/Ungeremine" title="Ungeremine">Ungeremine</a></li> <li><a href="/wiki/Ungiminorine" title="Ungiminorine">Ungiminorine</a></li> <li><a href="/wiki/Dimethylcarbamoyl_fluoride" title="Dimethylcarbamoyl fluoride">Dimethylcarbamoyl fluoride</a></li> <li><a href="/wiki/BW284C51" title="BW284C51">BW284C51</a></li> <li><a href="/wiki/TMTFA" title="TMTFA">TMTFA</a></li> <li><a href="/wiki/3152_CT" title="3152 CT">3152 CT</a></li></ul> <ul><li><a href="/wiki/Cholinesterase_reactivator" title="Cholinesterase reactivator">Reactivators</a>: <a href="/wiki/Asoxime_chloride" title="Asoxime chloride">Asoxime chloride</a></li> <li><a href="/w/index.php?title=Methoxime&action=edit&redlink=1" class="new" title="Methoxime (page does not exist)">Methoxime</a></li> <li><a href="/wiki/Obidoxime" title="Obidoxime">Obidoxime</a></li> <li><a href="/wiki/Pralidoxime" title="Pralidoxime">Pralidoxime</a></li> <li><a href="/wiki/Trimedoxime_bromide" title="Trimedoxime bromide">Trimedoxime bromide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Butyrylcholinesterase" title="Butyrylcholinesterase"><abbr title="Butyrylcholinesterase">BChE</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 Butyrylcholinesterase</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Inhibitors: <a href="/wiki/Affinine" title="Affinine">Affinine</a></li> <li><a href="/wiki/Affinisine" title="Affinisine">Affinisine</a></li> <li><a href="/wiki/Conodurine" title="Conodurine">Conodurine</a></li> <li><a href="/wiki/Cymserine" title="Cymserine">Cymserine</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Profenamine" title="Profenamine">Profenamine (ethopropazine)</a></li> <li><a href="/wiki/Rivastigmine" title="Rivastigmine">Rivastigmine</a></li> <li><a href="/wiki/Tacrine" title="Tacrine">Tacrine</a></li> <li><a href="/w/index.php?title=ZINC-12613047&action=edit&redlink=1" class="new" title="ZINC-12613047 (page does not exist)">ZINC-12613047</a></li> <li>Many of the other AChE inhibitors listed above</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">Transporter</a> (<a href="/wiki/Transporter_modulator" class="mw-redirect" title="Transporter modulator">modulators</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:6em;;text-align:center;"><a href="/wiki/Choline_transporter" title="Choline transporter"><abbr title="Choline transporter">CHT</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 Choline transporter</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Inhibitors: <a href="/wiki/Hemicholinium-3" title="Hemicholinium-3">Hemicholinium-3 (hemicholine)</a></li> <li><a href="/wiki/Triethylcholine" title="Triethylcholine">Triethylcholine</a></li></ul> <ul><li>Enhancers: <a href="/wiki/Coluracetam" title="Coluracetam">Coluracetam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Vesicular_acetylcholine_transporter" title="Vesicular acetylcholine transporter"><abbr title="Vesicular acetylcholine transporter">VAChT</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 Vesicular acetylcholine transporter</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Inhibitors: <a href="/wiki/Vesamicol" title="Vesamicol">Vesamicol</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/Neurotransmitter_release" class="mw-redirect" title="Neurotransmitter release">Release</a> (<a href="/wiki/Release_modulator" title="Release modulator">modulators</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:6em;;text-align:center;"><a href="/wiki/Release_inhibitor" class="mw-redirect" title="Release inhibitor">Inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Synaptosomal-associated_protein_25" class="mw-redirect" title="Synaptosomal-associated protein 25"><abbr title="Synaptosomal-associated protein 25">SNAP-25</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 Synaptosomal-associated protein 25 inactivators: <a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a> (<a href="/wiki/Botulinum_toxin_A" class="mw-redirect" title="Botulinum toxin A">A</a>, <a href="/wiki/Botulinum_toxin_C" class="mw-redirect" title="Botulinum toxin C">C</a>, <a href="/wiki/Botulinum_toxin_E" class="mw-redirect" title="Botulinum toxin E">E</a>)</li></ul> <ul><li><a href="/wiki/Vesicle-associated_membrane_protein" title="Vesicle-associated membrane protein"><abbr title="Vesicle-associated membrane protein">VAMP</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 Vesicle-associated membrane protein inactivators: <a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a> (<a href="/wiki/Botulinum_toxin_B" class="mw-redirect" title="Botulinum toxin B">B</a>, <a href="/wiki/Botulinum_toxin_D" class="mw-redirect" title="Botulinum toxin D">D</a>, <a href="/wiki/Botulinum_toxin_F" class="mw-redirect" title="Botulinum toxin F">F</a>, <a href="/wiki/Botulinum_toxin_G" class="mw-redirect" title="Botulinum toxin G">G</a>)</li></ul> <ul><li>Others: <a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxins</a> (<a href="/wiki/Beta-Bungarotoxin" class="mw-redirect" title="Beta-Bungarotoxin">β-bungarotoxin</a>, <a href="/wiki/%CE%93-bungarotoxin" class="mw-redirect" title="Γ-bungarotoxin">γ-bungarotoxin</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Release_enhancer" class="mw-redirect" title="Release enhancer">Enhancers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Latrophilin" title="Latrophilin"><abbr title="Latrophilin">LPHN</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 Latrophilin agonists: <a href="/wiki/Alpha-Latrotoxin" class="mw-redirect" title="Alpha-Latrotoxin">α-Latrotoxin</a></li></ul> <ul><li>Others: Atracotoxins (e.g., <a href="/wiki/Robustoxin" class="mw-redirect" title="Robustoxin">robustoxin</a>, <a href="/wiki/Versutoxin" title="Versutoxin">versutoxin</a>)</li> <li><a href="/wiki/Crotoxin" title="Crotoxin">Crotoxin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><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:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators">Nicotinic acetylcholine receptor 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="Glycine_receptor_modulators592" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Glycine_receptor_modulators" title="Template:Glycine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glycine_receptor_modulators" title="Template talk:Glycine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glycine_receptor_modulators" title="Special:EditPage/Template:Glycine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glycine_receptor_modulators592" style="font-size:114%;margin:0 4em"><a href="/wiki/Glycine_receptor" title="Glycine receptor">Glycine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a> (<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</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:4em;;text-align:center;"><a href="/wiki/Glycine_receptor" title="Glycine receptor"><abbr title="Glycine receptor">GlyR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Beta-Aminobutyric_acid" class="mw-redirect" title="Beta-Aminobutyric acid">β-ABA (BABA)</a></li> <li><a href="/wiki/%CE%92-Aminoisobutyric_acid" class="mw-redirect" title="Β-Aminoisobutyric acid">β-AIBA</a></li> <li><a href="/wiki/Caesium" title="Caesium">Caesium</a></li> <li><a href="/wiki/Alanine" title="Alanine">D-Alanine</a></li> <li><a href="/wiki/Serine" title="Serine">D-Serine</a></li> <li><a href="/wiki/Gamma-Aminobutyric_acid" class="mw-redirect" title="Gamma-Aminobutyric acid">GABA</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Hypotaurine" title="Hypotaurine">Hypotaurine</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Alanine" title="Alanine">L-Alanine</a></li> <li><a href="/wiki/Proline" title="Proline">L-Proline</a></li> <li><a href="/wiki/Serine" title="Serine">L-Serine</a></li> <li><a href="/wiki/Threonine" title="Threonine">L-Threonine</a></li> <li><a href="/w/index.php?title=MDL-27531&action=edit&redlink=1" class="new" title="MDL-27531 (page does not exist)">MDL-27531</a></li> <li><a href="/wiki/Milacemide" title="Milacemide">Milacemide</a></li> <li><a href="/wiki/Picolinic_acid" title="Picolinic acid">Picolinic acid</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Quisqualamine" title="Quisqualamine">Quisqualamine</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li></ul> <ul><li>Positive modulators: <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> (e.g., <a href="/w/index.php?title=Brometone&action=edit&redlink=1" class="new" title="Brometone (page does not exist)">brometone</a>, <a href="/wiki/Chlorobutanol" title="Chlorobutanol">chlorobutanol (chloretone)</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">ethanol (alcohol)</a>, <a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol">tert-butanol (2M2P)</a>, <a href="/wiki/Tribromoethanol" title="Tribromoethanol">tribromoethanol</a>, <a href="/wiki/Trichloroethanol" class="mw-redirect" title="Trichloroethanol">trichloroethanol</a>, <a href="/wiki/Trifluoroethanol" class="mw-redirect" title="Trifluoroethanol">trifluoroethanol</a>)</li> <li><a href="/wiki/Alkylbenzene_sulfonate" title="Alkylbenzene sulfonate">Alkylbenzene sulfonate</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/Chlormethiazole" class="mw-redirect" title="Chlormethiazole">Chlormethiazole</a></li> <li><a href="/w/index.php?title=D12-116&action=edit&redlink=1" class="new" title="D12-116 (page does not exist)">D12-116</a></li> <li><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a> (e.g., <a href="/wiki/Nicardipine" title="Nicardipine">nicardipine</a>)</li> <li><a href="/wiki/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">Ginseng</a> constituents (e.g., <a href="/wiki/Ginsenoside" title="Ginsenoside">ginsenosides</a> (e.g., <a href="/w/index.php?title=Ginsenoside-Rf&action=edit&redlink=1" class="new" title="Ginsenoside-Rf (page does not exist)">ginsenoside-Rf</a>))</li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid (glutamate)</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/Alfaxolone" class="mw-redirect" title="Alfaxolone">alfaxolone</a>, <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone (eltanolone)</a>, <a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">pregnenolone acetate</a>, <a href="/wiki/Minaxolone" title="Minaxolone">minaxolone</a>, <a href="/wiki/ORG-20599" title="ORG-20599">ORG-20599</a>)</li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Penicillin_G" class="mw-redirect" title="Penicillin G">Penicillin G</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a></li> <li><a href="/wiki/Triclofos" title="Triclofos">Triclofos</a></li> <li><a href="/w/index.php?title=Tropeine&action=edit&redlink=1" class="new" title="Tropeine (page does not exist)">Tropeines</a> (e.g., <a href="/wiki/Atropine" title="Atropine">atropine</a>, <a href="/wiki/Bemesetron" title="Bemesetron">bemesetron</a>, <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/w/index.php?title=LY-278584&action=edit&redlink=1" class="new" title="LY-278584 (page does not exist)">LY-278584</a>, <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, <a href="/wiki/Zatosetron" title="Zatosetron">zatosetron</a>)</li> <li><a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">Volatiles</a>/<a href="/wiki/Gas" title="Gas">gases</a> (e.g., <a href="/wiki/Chloral_hydrate" title="Chloral hydrate">chloral hydrate</a>, <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, <a href="/wiki/Desflurane" title="Desflurane">desflurane</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether (ether)</a>, <a href="/wiki/Enflurane" title="Enflurane">enflurane</a>, <a href="/wiki/Halothane" title="Halothane">halothane</a>, <a href="/wiki/Isoflurane" title="Isoflurane">isoflurane</a>, <a href="/wiki/Methoxyflurane" title="Methoxyflurane">methoxyflurane</a>, <a href="/wiki/Sevoflurane" title="Sevoflurane">sevoflurane</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/1,1,1-trichloroethane" class="mw-redirect" title="1,1,1-trichloroethane">trichloroethane (methyl chloroform)</a>, <a href="/wiki/Trichloroethylene" title="Trichloroethylene">trichloroethylene</a>)</li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=2-Aminostrychnine&action=edit&redlink=1" class="new" title="2-Aminostrychnine (page does not exist)">2-Aminostrychnine</a></li> <li><a href="/w/index.php?title=2-Nitrostrychnine&action=edit&redlink=1" class="new" title="2-Nitrostrychnine (page does not exist)">2-Nitrostrychnine</a></li> <li><a href="/w/index.php?title=4-Phenyl-4-formyl-N-methylpiperidine&action=edit&redlink=1" class="new" title="4-Phenyl-4-formyl-N-methylpiperidine (page does not exist)">4-Phenyl-4-formyl-N-methylpiperidine</a></li> <li><a href="/w/index.php?title=%CE%91-Ethyl-%CE%B1-methyl-%CE%B3-thiobutyrolactone&action=edit&redlink=1" class="new" title="Α-Ethyl-α-methyl-γ-thiobutyrolactone (page does not exist)">αEMBTL</a></li> <li><a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/wiki/Brucine" title="Brucine">Brucine</a></li> <li><a href="/wiki/Cacotheline" title="Cacotheline">Cacotheline</a></li> <li><a class="mw-selflink selflink">Caffeine</a></li> <li><a href="/wiki/Colchicine" title="Colchicine">Colchicine</a></li> <li><a href="/wiki/Colubrine" class="mw-redirect" title="Colubrine">Colubrine</a></li> <li><a href="/w/index.php?title=Cyanotriphenylborate&action=edit&redlink=1" class="new" title="Cyanotriphenylborate (page does not exist)">Cyanotriphenylborate</a></li> <li><a href="/wiki/Dendrobine" title="Dendrobine">Dendrobine</a></li> <li><a href="/w/index.php?title=Diaboline&action=edit&redlink=1" class="new" title="Diaboline (page does not exist)">Diaboline</a></li> <li><a href="/wiki/Endocannabinoid" class="mw-redirect" title="Endocannabinoid">Endocannabinoids</a> (e.g., <a href="/wiki/2-arachidonylglycerol" class="mw-redirect" title="2-arachidonylglycerol">2-AG</a>, <a href="/wiki/Anandamide" title="Anandamide">anandamide (AEA)</a>)</li> <li><a href="/wiki/Gaboxadol" title="Gaboxadol">Gaboxadol (THIP)</a></li> <li><a href="/wiki/Gelsemine" title="Gelsemine">Gelsemine</a></li> <li><a href="/w/index.php?title=Iso-THAZ&action=edit&redlink=1" class="new" title="Iso-THAZ (page does not exist)">iso-THAZ</a></li> <li><a href="/wiki/Isobutyric_acid" title="Isobutyric acid">Isobutyric acid</a></li> <li><a href="/wiki/Isonipecotic_acid" title="Isonipecotic acid">Isonipecotic acid</a></li> <li><a href="/w/index.php?title=Isostrychnine&action=edit&redlink=1" class="new" title="Isostrychnine (page does not exist)">Isostrychnine</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/w/index.php?title=N-Methylbicuculline&action=edit&redlink=1" class="new" title="N-Methylbicuculline (page does not exist)">N-Methylbicuculline</a></li> <li><a href="/w/index.php?title=N-Methylstrychnine&action=edit&redlink=1" class="new" title="N-Methylstrychnine (page does not exist)">N-Methylstrychnine</a></li> <li><a href="/w/index.php?title=N,N-Dimethylmuscimol&action=edit&redlink=1" class="new" title="N,N-Dimethylmuscimol (page does not exist)">N,N-Dimethylmuscimol</a></li> <li><a href="/wiki/Nipecotic_acid" title="Nipecotic acid">Nipecotic acid</a></li> <li><a href="/wiki/Pitrazepin" title="Pitrazepin">Pitrazepin</a></li> <li><a href="/w/index.php?title=Pseudostrychnine&action=edit&redlink=1" class="new" title="Pseudostrychnine (page does not exist)">Pseudostrychnine</a></li> <li><a href="/wiki/Quinoline" title="Quinoline">Quinolines</a> (e.g., <a href="/w/index.php?title=4-hydroxyquinoline&action=edit&redlink=1" class="new" title="4-hydroxyquinoline (page does not exist)">4-hydroxyquinoline</a>, <a href="/w/index.php?title=4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="4-hydroxyquinoline-3-carboxylic acid (page does not exist)">4-hydroxyquinoline-3-carboxylic acid</a>, <a href="/w/index.php?title=5,7-dichloro-4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="5,7-dichloro-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">5,7-CIQA</a>, <a href="/w/index.php?title=7-chloro-4-hydroxyquinoline&action=edit&redlink=1" class="new" title="7-chloro-4-hydroxyquinoline (page does not exist)">7-CIQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline&action=edit&redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline (page does not exist)">7-TFQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">7-TFQA</a>)</li> <li><a href="/w/index.php?title=RU-5135&action=edit&redlink=1" class="new" title="RU-5135 (page does not exist)">RU-5135</a></li> <li><a href="/wiki/Sinomenine" title="Sinomenine">Sinomenine</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Tutin_(toxin)" title="Tutin (toxin)">Tutin</a></li></ul> <ul><li>Negative modulators: <a href="/wiki/Amiloride" title="Amiloride">Amiloride</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a> (e.g., <a href="/wiki/Bromazepam" title="Bromazepam">bromazepam</a>, <a href="/wiki/Clonazepam" title="Clonazepam">clonazepam</a>, <a href="/wiki/Diazepam" title="Diazepam">diazepam</a>, <a href="/wiki/Flunitrazepam" title="Flunitrazepam">flunitrazepam</a>, <a href="/wiki/Flurazepam" title="Flurazepam">flurazepam</a>)</li> <li><a href="/wiki/Corymine" title="Corymine">Corymine</a></li> <li><a href="/w/index.php?title=Cyanotriphenylborate&action=edit&redlink=1" class="new" title="Cyanotriphenylborate (page does not exist)">Cyanotriphenylborate</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a> (e.g., <a href="/wiki/Nicardipine" title="Nicardipine">nicardipine</a>, <a href="/wiki/Nifedipine" title="Nifedipine">nifedipine</a>, <a href="/wiki/Nitrendipine" title="Nitrendipine">nitrendipine</a>)</li> <li><a href="/wiki/Furosemide" title="Furosemide">Furosemide</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Ginkgo_biloba" title="Ginkgo biloba">Ginkgo</a> constituents (e.g., <a href="/wiki/Bilobalide" title="Bilobalide">bilobalide</a>, <a href="/wiki/Ginkgolide" title="Ginkgolide">ginkgolides</a> (e.g., <a href="/w/index.php?title=Ginkgolide_A&action=edit&redlink=1" class="new" title="Ginkgolide A (page does not exist)">ginkgolide A</a>, <a href="/wiki/Ginkgolide_B" class="mw-redirect" title="Ginkgolide B">ginkgolide B</a>, <a href="/w/index.php?title=Ginkgolide_C&action=edit&redlink=1" class="new" title="Ginkgolide C (page does not exist)">ginkgolide C</a>, <a href="/w/index.php?title=Ginkgolide_J&action=edit&redlink=1" class="new" title="Ginkgolide J (page does not exist)">ginkgolide J</a>, <a href="/w/index.php?title=Ginkgolide_M&action=edit&redlink=1" class="new" title="Ginkgolide M (page does not exist)">ginkgolide M</a>))</li> <li><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a></li> <li><a href="/wiki/NBQX" title="NBQX">NBQX</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/3%CE%B1-androsterone_sulfate" class="mw-redirect" title="3α-androsterone sulfate">3α-androsterone sulfate</a>, <a href="/w/index.php?title=3%CE%B2-androsterone_sulfate&action=edit&redlink=1" class="new" title="3β-androsterone sulfate (page does not exist)">3β-androsterone sulfate</a>, <a href="/wiki/11-deoxycorticosterone" class="mw-redirect" title="11-deoxycorticosterone">deoxycorticosterone</a>, <a href="/wiki/DHEA_sulfate" class="mw-redirect" title="DHEA sulfate">DHEA sulfate</a>, <a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">pregnenolone sulfate</a>, <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>)</li> <li><a href="/wiki/Opioid" title="Opioid">Opioids</a> (e.g., <a href="/wiki/Codeine" title="Codeine">codeine</a>, <a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a>, <a href="/wiki/Dextrorphan" title="Dextrorphan">dextrorphan</a>, <a href="/wiki/Levomethadone" title="Levomethadone">levomethadone</a>, <a href="/wiki/Levorphanol" title="Levorphanol">levorphanol</a>, <a href="/wiki/Morphine" title="Morphine">morphine</a>, <a href="/wiki/Oripavine" title="Oripavine">oripavine</a>, <a href="/wiki/Pethidine" title="Pethidine">pethidine</a>, <a href="/wiki/Thebaine" title="Thebaine">thebaine</a>)</li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a> (i.e., <a href="/wiki/Picrotin" class="mw-redirect" title="Picrotin">picrotin</a> and <a href="/wiki/Picrotoxinin" class="mw-redirect" title="Picrotoxinin">picrotoxinin</a>)</li> <li><a href="/w/index.php?title=Phenylbenzene_%CF%89-phosphono-%CE%B1-amino_acid&action=edit&redlink=1" class="new" title="Phenylbenzene ω-phosphono-α-amino acid (page does not exist)">PMBA</a></li> <li><a href="/wiki/Riluzole" title="Riluzole">Riluzole</a></li> <li><a href="/w/index.php?title=Tropeine&action=edit&redlink=1" class="new" title="Tropeine (page does not exist)">Tropeines</a> (e.g., <a href="/wiki/Bemesetron" title="Bemesetron">bemesetron</a>, <a href="/w/index.php?title=LY-278584&action=edit&redlink=1" class="new" title="LY-278584 (page does not exist)">LY-278584</a>, <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, <a href="/wiki/Zatosetron" title="Zatosetron">zatosetron</a>)</li> <li><a href="/wiki/Verapamil" title="Verapamil">Verapamil</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/N-Methyl-D-aspartate_receptor" class="mw-redirect" title="N-Methyl-D-aspartate receptor"><abbr title="N-Methyl-D-aspartate receptor">NMDAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip N-Methyl-D-aspartate receptor</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">here</a> instead.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">Transporter</a> (<a href="/wiki/Reuptake_inhibitor" title="Reuptake inhibitor">blockers</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:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_1" class="mw-redirect" title="Glycine transporter 1"><abbr title="Glycine transporter 1">GlyT1</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine transporter 1</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=ACPPB&action=edit&redlink=1" class="new" title="ACPPB (page does not exist)">ACPPB</a></li> <li><a href="/w/index.php?title=ALX-5407&action=edit&redlink=1" class="new" title="ALX-5407 (page does not exist)">ALX-5407 (NFPS)</a></li> <li><a href="/wiki/ASP2535" title="ASP2535">ASP2535</a></li> <li><a href="/wiki/Bitopertin" title="Bitopertin">Bitopertin (RG1678/RO4917838)</a></li> <li><a href="/w/index.php?title=CP-802079&action=edit&redlink=1" class="new" title="CP-802079 (page does not exist)">CP-802079</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Glycyldodecylamide&action=edit&redlink=1" class="new" title="Glycyldodecylamide (page does not exist)">Glycyldodecylamide</a></li> <li><a href="/w/index.php?title=GSK1018921&action=edit&redlink=1" class="new" title="GSK1018921 (page does not exist)">GSK1018921</a></li> <li><a href="/wiki/Iclepertin" title="Iclepertin">Iclepertin</a></li> <li><a href="/wiki/LY-2365109" title="LY-2365109">LY-2365109</a></li> <li><a href="/wiki/Mardepodect" title="Mardepodect">Mardepodect</a></li> <li><a href="/wiki/ORG-24598" title="ORG-24598">ORG-24598</a></li> <li><a href="/wiki/ORG-25935" title="ORG-25935">ORG-25935 (SCH-900435)</a></li> <li><a href="/wiki/Pesampator" title="Pesampator">Pesampator (BIIB-104, PF-04958242)</a></li> <li><a href="/w/index.php?title=PF-03463275&action=edit&redlink=1" class="new" title="PF-03463275 (page does not exist)">PF-03463275</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/SNG-12" title="SNG-12">SNG-12 (Synapsinae)</a></li> <li><a href="/w/index.php?title=SSR-103,800&action=edit&redlink=1" class="new" title="SSR-103,800 (page does not exist)">SSR-103,800</a></li> <li><a href="/w/index.php?title=SSR-504,734&action=edit&redlink=1" class="new" title="SSR-504,734 (page does not exist)">SSR-504,734</a></li> <li><a href="/wiki/Tilapertin" title="Tilapertin">Tilapertin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_2" class="mw-redirect" title="Glycine transporter 2"><abbr title="Glycine transporter 2">GlyT2</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine transporter 2</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/ALX-1393" title="ALX-1393">ALX-1393</a></li> <li><a href="/wiki/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/N-Arachidonylglycine" title="N-Arachidonylglycine">NAGly</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/w/index.php?title=ORG-25543&action=edit&redlink=1" class="new" title="ORG-25543 (page does not exist)">ORG-25543</a></li> <li><a href="/w/index.php?title=VVZ-368&action=edit&redlink=1" class="new" title="VVZ-368 (page does not exist)">VVZ-368</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a></dd> <dd><a href="/wiki/Template:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators">GABAA receptor positive modulators</a></dd> <dd><a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">Ionotropic glutamate receptor 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="Phosphodiesterase_inhibitors344" 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:Phosphodiesterase_inhibitors" title="Template:Phosphodiesterase inhibitors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phosphodiesterase_inhibitors" title="Template talk:Phosphodiesterase inhibitors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phosphodiesterase_inhibitors" title="Special:EditPage/Template:Phosphodiesterase inhibitors"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Phosphodiesterase_inhibitors344" style="font-size:114%;margin:0 4em"><a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">Phosphodiesterase inhibitors</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE1" title="PDE1">PDE1</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/8-Methoxymethyl-3-isobutyl-1-methylxanthine" title="8-Methoxymethyl-3-isobutyl-1-methylxanthine">MMPX</a></li> <li><a href="/wiki/SCH-51866" title="SCH-51866">SCH-51866</a></li> <li><a href="/wiki/Vinpocetine" title="Vinpocetine">Vinpocetine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE2" class="mw-redirect" title="PDE2">PDE2</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/BAY_60-7550" title="BAY 60-7550">BAY 60-7550</a></li> <li><a href="/w/index.php?title=Carbazeran&action=edit&redlink=1" class="new" title="Carbazeran (page does not exist)">Carbazeran</a></li> <li><a href="/wiki/EHNA" title="EHNA">EHNA</a></li> <li><a href="/wiki/Oxindole" title="Oxindole">Oxindole</a></li> <li><a href="/w/index.php?title=9-(6-Phenyl-2-oxohex-3-yl)-2-(3,4-dimethoxybenzyl)-purin-6-one&action=edit&redlink=1" class="new" title="9-(6-Phenyl-2-oxohex-3-yl)-2-(3,4-dimethoxybenzyl)-purin-6-one (page does not exist)">PDP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE3_inhibitor" title="PDE3 inhibitor">PDE3</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/Adibendan" title="Adibendan">Adibendan</a></li> <li><a href="/wiki/Amrinone" title="Amrinone">Amrinone (inamrinone)</a></li> <li><a href="/wiki/Anagrelide" title="Anagrelide">Anagrelide</a></li> <li><a href="/w/index.php?title=Benafentrine&action=edit&redlink=1" class="new" title="Benafentrine (page does not exist)">Benafentrine</a></li> <li><a href="/wiki/Bucladesine" title="Bucladesine">Bucladesine</a></li> <li><a href="/w/index.php?title=Carbazeran&action=edit&redlink=1" class="new" title="Carbazeran (page does not exist)">Carbazeran</a></li> <li><a href="/wiki/Cilostamide" title="Cilostamide">Cilostamide</a></li> <li><a href="/wiki/Cilostazol" title="Cilostazol">Cilostazol</a></li> <li><a href="/wiki/Enoximone" title="Enoximone">Enoximone</a></li> <li><a href="/wiki/Ensifentrine" title="Ensifentrine">Ensifentrine</a></li> <li><a href="/w/index.php?title=Imazodan&action=edit&redlink=1" class="new" title="Imazodan (page does not exist)">Imazodan</a></li> <li><a href="/wiki/KMUP-1" title="KMUP-1">KMUP-1</a></li> <li><a href="/w/index.php?title=Meribendan&action=edit&redlink=1" class="new" title="Meribendan (page does not exist)">Meribendan</a></li> <li><a href="/wiki/Milrinone" title="Milrinone">Milrinone</a></li> <li><a href="/wiki/Olprinone" title="Olprinone">Olprinone</a></li> <li><a href="/w/index.php?title=Parogrelil&action=edit&redlink=1" class="new" title="Parogrelil (page does not exist)">Parogrelil</a></li> <li><a href="/wiki/Pimobendan" title="Pimobendan">Pimobendan</a></li> <li><a href="/w/index.php?title=Pumafentrine&action=edit&redlink=1" class="new" title="Pumafentrine (page does not exist)">Pumafentrine</a></li> <li><a href="/wiki/Quazinone" title="Quazinone">Quazinone</a></li> <li><a href="/wiki/RPL-554" class="mw-redirect" title="RPL-554">RPL-554</a></li> <li><a href="/wiki/Siguazodan" title="Siguazodan">Siguazodan</a></li> <li><a href="/wiki/Trequinsin" title="Trequinsin">Trequinsin</a></li> <li><a href="/wiki/Vesnarinone" title="Vesnarinone">Vesnarinone</a></li> <li><a href="/wiki/Zardaverine" title="Zardaverine">Zardaverine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE4_inhibitor" title="PDE4 inhibitor">PDE4</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apremilast" title="Apremilast">Apremilast</a></li> <li><a href="/wiki/Arofylline" title="Arofylline">Arofylline</a></li> <li><a href="/wiki/Atizoram" title="Atizoram">Atizoram</a></li> <li><a href="/w/index.php?title=Benafentrine&action=edit&redlink=1" class="new" title="Benafentrine (page does not exist)">Benafentrine</a></li> <li><a href="/w/index.php?title=Catramilast&action=edit&redlink=1" class="new" title="Catramilast (page does not exist)">Catramilast</a></li> <li><a href="/wiki/CC-1088" title="CC-1088">CC-1088</a></li> <li><a href="/w/index.php?title=CDP-840&action=edit&redlink=1" class="new" title="CDP-840 (page does not exist)">CDP-840</a></li> <li><a href="/w/index.php?title=CGH-2466&action=edit&redlink=1" class="new" title="CGH-2466 (page does not exist)">CGH-2466</a></li> <li><a href="/wiki/Cilomilast" title="Cilomilast">Cilomilast</a></li> <li><a href="/w/index.php?title=Cipamfylline&action=edit&redlink=1" class="new" title="Cipamfylline (page does not exist)">Cipamfylline</a></li> <li><a href="/wiki/Crisaborole" title="Crisaborole">Crisaborole</a></li> <li><a href="/w/index.php?title=Denbutylline&action=edit&redlink=1" class="new" title="Denbutylline (page does not exist)">Denbutylline</a></li> <li><a href="/w/index.php?title=Difamilast&action=edit&redlink=1" class="new" title="Difamilast (page does not exist)">Difamilast</a></li> <li><a href="/wiki/Drotaverine" title="Drotaverine">Drotaverine</a></li> <li><a href="/wiki/Ensifentrine" title="Ensifentrine">Ensifentrine</a></li> <li><a href="/wiki/Etazolate" title="Etazolate">Etazolate</a></li> <li><a href="/wiki/Filaminast" title="Filaminast">Filaminast</a></li> <li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/wiki/HT-0712" title="HT-0712">HT-0712</a></li> <li><a href="/wiki/ICI-63197" title="ICI-63197">ICI-63197</a></li> <li><a href="/w/index.php?title=Indimilast&action=edit&redlink=1" class="new" title="Indimilast (page does not exist)">Indimilast</a></li> <li><a href="/wiki/Irsogladine" title="Irsogladine">Irsogladine</a></li> <li><a href="/w/index.php?title=Lavamilast&action=edit&redlink=1" class="new" title="Lavamilast (page does not exist)">Lavamilast</a></li> <li><a href="/w/index.php?title=Lirimilast&action=edit&redlink=1" class="new" title="Lirimilast (page does not exist)">Lirimilast</a></li> <li><a href="/w/index.php?title=Lotamilast&action=edit&redlink=1" class="new" title="Lotamilast (page does not exist)">Lotamilast</a></li> <li><a href="/wiki/Luteolin" title="Luteolin">Luteolin</a></li> <li><a href="/wiki/Mesembrenone" title="Mesembrenone">Mesembrenone</a></li> <li><a href="/wiki/Mesembrine" title="Mesembrine">Mesembrine</a></li> <li><a href="/w/index.php?title=Mesopram&action=edit&redlink=1" class="new" title="Mesopram (page does not exist)">Mesopram</a></li> <li><a href="/w/index.php?title=Oglemilast&action=edit&redlink=1" class="new" title="Oglemilast (page does not exist)">Oglemilast</a></li> <li><a href="/wiki/Piclamilast" title="Piclamilast">Piclamilast</a></li> <li><a href="/w/index.php?title=Pumafentrine&action=edit&redlink=1" class="new" title="Pumafentrine (page does not exist)">Pumafentrine</a></li> <li><a href="/w/index.php?title=Revamilast&action=edit&redlink=1" class="new" title="Revamilast (page does not exist)">Revamilast</a></li> <li><a href="/w/index.php?title=Ro_20-1724&action=edit&redlink=1" class="new" title="Ro 20-1724 (page does not exist)">Ro 20-1724</a></li> <li><a href="/wiki/Roflumilast" title="Roflumilast">Roflumilast</a></li> <li><a href="/wiki/Rolipram" title="Rolipram">Rolipram</a></li> <li><a href="/w/index.php?title=Ronomilast&action=edit&redlink=1" class="new" title="Ronomilast (page does not exist)">Ronomilast</a></li> <li><a href="/wiki/RPL-554" class="mw-redirect" title="RPL-554">RPL-554</a></li> <li><a href="/w/index.php?title=RS-25344&action=edit&redlink=1" class="new" title="RS-25344 (page does not exist)">RS-25344</a></li> <li><a href="/w/index.php?title=Tetomilast&action=edit&redlink=1" class="new" title="Tetomilast (page does not exist)">Tetomilast</a></li> <li><a href="/w/index.php?title=Tofimilast&action=edit&redlink=1" class="new" title="Tofimilast (page does not exist)">Tofimilast</a></li> <li><a href="/wiki/YM-976" title="YM-976">YM-976</a></li> <li><a href="/wiki/Zardaverine" title="Zardaverine">Zardaverine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE5_inhibitor" title="PDE5 inhibitor">PDE5</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/Acetildenafil" title="Acetildenafil">Acetildenafil</a></li> <li><a href="/wiki/Aildenafil" title="Aildenafil">Aildenafil</a></li> <li><a href="/wiki/Avanafil" title="Avanafil">Avanafil</a></li> <li><a href="/w/index.php?title=Beminafil&action=edit&redlink=1" class="new" title="Beminafil (page does not exist)">Beminafil</a></li> <li><a href="/wiki/Benzamidenafil" title="Benzamidenafil">Benzamidenafil</a></li> <li><a href="/w/index.php?title=Dasantafil&action=edit&redlink=1" class="new" title="Dasantafil (page does not exist)">Dasantafil</a></li> <li><a href="/wiki/Icariin" title="Icariin">Icariin</a></li> <li><a href="/w/index.php?title=Gisadenafil&action=edit&redlink=1" class="new" title="Gisadenafil (page does not exist)">Gisadenafil</a></li> <li><a href="/wiki/Homosildenafil" title="Homosildenafil">Homosildenafil</a></li> <li><a href="/wiki/Lodenafil" title="Lodenafil">Lodenafil</a></li> <li><a href="/wiki/Mirodenafil" title="Mirodenafil">Mirodenafil</a></li> <li><a href="/wiki/MY-5445" title="MY-5445">MY-5445</a></li> <li><a href="/wiki/Nitrosoprodenafil" title="Nitrosoprodenafil">Nitrosoprodenafil</a></li> <li><a href="/w/index.php?title=Norcarbodenafil&action=edit&redlink=1" class="new" title="Norcarbodenafil (page does not exist)">Norcarbodenafil</a></li> <li><a href="/wiki/SCH-51866" title="SCH-51866">SCH-51866</a></li> <li><a href="/wiki/Sildenafil" title="Sildenafil">Sildenafil</a></li> <li><a href="/wiki/Sulfoaildenafil" title="Sulfoaildenafil">Sulfoaildenafil</a></li> <li><a href="/wiki/T-0156" title="T-0156">T-0156</a></li> <li><a href="/wiki/Tadalafil" title="Tadalafil">Tadalafil</a></li> <li><a href="/wiki/Udenafil" title="Udenafil">Udenafil</a></li> <li><a href="/wiki/Vardenafil" title="Vardenafil">Vardenafil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE7" class="mw-redirect" title="PDE7">PDE7</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/BRL-50481" title="BRL-50481">BRL-50481</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE9" title="PDE9">PDE9</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/BAY_73-6691" title="BAY 73-6691">BAY 73-6691</a></li> <li><a href="/w/index.php?title=PF-04447943&action=edit&redlink=1" class="new" title="PF-04447943 (page does not exist)">PF-04447943</a></li> <li><a href="/wiki/Paraxanthine" title="Paraxanthine">Paraxanthine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE10" title="PDE10">PDE10</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Balipodect" title="Balipodect">Balipodect</a></li> <li><a href="/wiki/Mardepodect" title="Mardepodect">Mardepodect</a></li> <li><a href="/wiki/MK-8189" title="MK-8189">MK-8189</a></li> <li><a href="/wiki/Papaverine" title="Papaverine">Papaverine</a></li> <li><a href="/w/index.php?title=TC-E_5005&action=edit&redlink=1" class="new" title="TC-E 5005 (page does not exist)">TC-E 5005</a></li> <li><a href="/wiki/Tofisopam" title="Tofisopam">Tofisopam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/PDE11" title="PDE11">PDE11</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/w/index.php?title=BC11-38&action=edit&redlink=1" class="new" title="BC11-38 (page does not exist)">BC11-38</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Phosphodiesterase_inhibitor#Nonselective_phosphodiesterase_inhibitors" title="Phosphodiesterase inhibitor">Non-selective</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminophylline" title="Aminophylline">Aminophylline</a></li> <li><a class="mw-selflink selflink">Caffeine</a></li> <li><a href="/wiki/Choline_theophyllinate" title="Choline theophyllinate">Choline theophyllinate</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dimethylxanthine" title="8-Cyclopentyl-1,3-dimethylxanthine">CPX</a></li> <li><a href="/wiki/Dipyridamole" title="Dipyridamole">Dipyridamole</a></li> <li><a href="/wiki/Doxofylline" title="Doxofylline">Doxofylline</a></li> <li><a href="/wiki/Enprofylline" title="Enprofylline">Enprofylline</a></li> <li><a href="/wiki/Ibudilast" title="Ibudilast">Ibudilast</a></li> <li><a href="/wiki/IBMX" title="IBMX">IBMX</a></li> <li><a href="/wiki/Luteolin" title="Luteolin">Luteolin</a></li> <li><a href="/wiki/Pentoxifylline" title="Pentoxifylline">Pentoxifylline</a></li> <li><a href="/wiki/Propentofylline" title="Propentofylline">Propentofylline</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li> <li><a href="/wiki/Zaprinast" title="Zaprinast">Zaprinast</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Unsorted</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/Diazepam" title="Diazepam">Diazepam</a></li> <li><a href="/wiki/Diprophylline" title="Diprophylline">Diprophylline</a></li> <li><a href="/wiki/Dipropylcyclopentylxanthine" title="Dipropylcyclopentylxanthine">DPCPX</a></li> <li><a href="/wiki/Furafylline" title="Furafylline">Furafylline</a></li> <li><a href="/wiki/Lisofylline" title="Lisofylline">Lisofylline</a></li> <li><a href="/w/index.php?title=MDL-12330A&action=edit&redlink=1" class="new" title="MDL-12330A (page does not exist)">MDL-12330A</a></li> <li><a href="/wiki/Moxaverine" title="Moxaverine">Moxaverine</a></li> <li><a href="/w/index.php?title=Oxagrelate&action=edit&redlink=1" class="new" title="Oxagrelate (page does not exist)">Oxagrelate</a></li> <li><a href="/wiki/Pentifylline" title="Pentifylline">Pentifylline</a></li> <li><a href="/wiki/Proxyphylline" title="Proxyphylline">Proxyphylline</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/w/index.php?title=Satigrel&action=edit&redlink=1" class="new" title="Satigrel (page does not exist)">Satigrel</a></li> <li><a href="/w/index.php?title=Tolafentrine&action=edit&redlink=1" class="new" title="Tolafentrine (page does not exist)">Tolafentrine</a></li> <li><a href="/wiki/Trapidil" title="Trapidil">Trapidil</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>See also: <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></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="Purine_receptor_modulators393" 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:Purine_receptor_modulators" title="Template:Purine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Purine_receptor_modulators" title="Template talk:Purine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Purine_receptor_modulators" title="Special:EditPage/Template:Purine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Purine_receptor_modulators393" style="font-size:114%;margin:0 4em"><a href="/wiki/Purine_receptor" class="mw-redirect" title="Purine receptor">Purine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a> (<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</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:6em;;text-align:center;"><a href="/wiki/P0_receptor" class="mw-redirect" title="P0 receptor">P0</a> (<a href="/wiki/Adenine" title="Adenine">adenine</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/w/index.php?title=8-Aminoadenine&action=edit&redlink=1" class="new" title="8-Aminoadenine (page does not exist)">8-Aminoadenine</a></li> <li><a href="/wiki/Adenine" title="Adenine">Adenine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Adenosine_receptor" title="Adenosine receptor">P1</a> (<a href="/wiki/Adenosine" title="Adenosine">adenosine</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/w/index.php?title=2-(1-Hexynyl)-N-methyladenosine&action=edit&redlink=1" class="new" title="2-(1-Hexynyl)-N-methyladenosine (page does not exist)">2-(1-Hexynyl)-N-methyladenosine</a></li> <li><a href="/w/index.php?title=2-Cl-IB-MECA&action=edit&redlink=1" class="new" title="2-Cl-IB-MECA (page does not exist)">2-Cl-IB-MECA</a></li> <li><a href="/w/index.php?title=2-Chloroadenosine&action=edit&redlink=1" class="new" title="2-Chloroadenosine (page does not exist)">2-Chloroadenosine</a></li> <li><a href="/w/index.php?title=2%27-MeCCPA&action=edit&redlink=1" class="new" title="2'-MeCCPA (page does not exist)">2'-MeCCPA</a></li> <li><a href="/w/index.php?title=4%27-O-%CE%B2-D-Glucosyl-9-O-(6%27-deoxysaccharosyl)olivil&action=edit&redlink=1" class="new" title="4'-O-β-D-Glucosyl-9-O-(6'-deoxysaccharosyl)olivil (page does not exist)">4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil</a></li> <li><a href="/w/index.php?title=5%27-N-ethylcarboxamidoadenosine&action=edit&redlink=1" class="new" title="5'-N-ethylcarboxamidoadenosine (page does not exist)">5'-N-ethylcarboxamidoadenosine</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/w/index.php?title=Apadenoson&action=edit&redlink=1" class="new" title="Apadenoson (page does not exist)">Apadenoson</a></li> <li><a href="/wiki/ATL-146e" class="mw-redirect" title="ATL-146e">ATL-146e</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/BAY_60%E2%80%936583" title="BAY 60–6583">BAY 60–6583</a></li> <li><a href="/w/index.php?title=Binodenoson&action=edit&redlink=1" class="new" title="Binodenoson (page does not exist)">Binodenoson</a></li> <li><a href="/w/index.php?title=Capadenoson&action=edit&redlink=1" class="new" title="Capadenoson (page does not exist)">Capadenoson</a></li> <li><a href="/wiki/CCPA_(biochemistry)" title="CCPA (biochemistry)">CCPA</a></li> <li><a href="/wiki/CGS-21680" title="CGS-21680">CGS-21680</a></li> <li><a href="/wiki/CP-532,903" title="CP-532,903">CP-532,903</a></li> <li><a href="/w/index.php?title=CV-1808&action=edit&redlink=1" class="new" title="CV-1808 (page does not exist)">CV-1808</a></li> <li><a href="/w/index.php?title=Evodenoson&action=edit&redlink=1" class="new" title="Evodenoson (page does not exist)">Evodenoson</a></li> <li><a href="/w/index.php?title=GR_79236&action=edit&redlink=1" class="new" title="GR 79236 (page does not exist)">GR 79236</a></li> <li><a href="/w/index.php?title=HENECA&action=edit&redlink=1" class="new" title="HENECA (page does not exist)">HENECA</a></li> <li><a href="/w/index.php?title=LUF-5835&action=edit&redlink=1" class="new" title="LUF-5835 (page does not exist)">LUF-5835</a></li> <li><a href="/w/index.php?title=LUF-5845&action=edit&redlink=1" class="new" title="LUF-5845 (page does not exist)">LUF-5845</a></li> <li><a href="/wiki/N6-Cyclopentyladenosine" title="N6-Cyclopentyladenosine">N6-Cyclopentyladenosine</a></li> <li><a href="/wiki/Namodenoson" title="Namodenoson">Namodenoson</a></li> <li><a href="/wiki/NECA_(drug)" class="mw-redirect" title="NECA (drug)">NECA</a></li> <li><a href="/w/index.php?title=Neladenoson_dalanate&action=edit&redlink=1" class="new" title="Neladenoson dalanate (page does not exist)">Neladenoson dalanate</a></li> <li><a href="/w/index.php?title=Piclidenoson&action=edit&redlink=1" class="new" title="Piclidenoson (page does not exist)">Piclidenoson</a></li> <li><a href="/wiki/Regadenoson" title="Regadenoson">Regadenoson</a></li> <li><a href="/w/index.php?title=SDZ_WAG_994&action=edit&redlink=1" class="new" title="SDZ WAG 994 (page does not exist)">SDZ WAG 994</a></li> <li><a href="/w/index.php?title=Selodenoson&action=edit&redlink=1" class="new" title="Selodenoson (page does not exist)">Selodenoson</a></li> <li><a href="/w/index.php?title=Sonedenoson&action=edit&redlink=1" class="new" title="Sonedenoson (page does not exist)">Sonedenoson</a></li> <li><a href="/w/index.php?title=Tecadenoson&action=edit&redlink=1" class="new" title="Tecadenoson (page does not exist)">Tecadenoson</a></li> <li><a href="/w/index.php?title=Trabodenoson&action=edit&redlink=1" class="new" title="Trabodenoson (page does not exist)">Trabodenoson</a></li> <li><a href="/wiki/UK-432,097" title="UK-432,097">UK-432,097</a></li></ul> <ul><li>Antagonists: <a href="/wiki/3-Chlorostyrylcaffeine" title="3-Chlorostyrylcaffeine">3-Chlorostyrylcaffeine (CSC)</a></li> <li><a href="/wiki/7-Methylxanthine" title="7-Methylxanthine">7-Methylxanthine</a></li> <li><a href="/wiki/8-Chlorotheophylline" title="8-Chlorotheophylline">8-Chlorotheophylline</a></li> <li><a href="/w/index.php?title=8-Phenyl-1,3-dipropylxanthine&action=edit&redlink=1" class="new" title="8-Phenyl-1,3-dipropylxanthine (page does not exist)">8-Phenyl-1,3-dipropylxanthine</a></li> <li><a href="/wiki/8-Phenyltheophylline" title="8-Phenyltheophylline">8-Phenyltheophylline</a></li> <li><a href="/wiki/Acefylline" title="Acefylline">Acefylline</a></li> <li><a href="/wiki/Aminophylline" title="Aminophylline">Aminophylline</a></li> <li><a href="/wiki/ATL-444" title="ATL-444">ATL-444</a></li> <li><a href="/w/index.php?title=AZD-4635&action=edit&redlink=1" class="new" title="AZD-4635 (page does not exist)">AZD-4635</a></li> <li><a href="/wiki/Bamifylline" title="Bamifylline">Bamifylline</a></li> <li><a href="/wiki/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a class="mw-selflink selflink">Caffeine</a></li> <li><a href="/wiki/Caffeine_citrate" title="Caffeine citrate">Caffeine citrate</a></li> <li><a href="/wiki/Cartazolate" title="Cartazolate">Cartazolate</a></li> <li><a href="/w/index.php?title=CGH-2466&action=edit&redlink=1" class="new" title="CGH-2466 (page does not exist)">CGH-2466</a></li> <li><a href="/wiki/CGS-15943" title="CGS-15943">CGS-15943</a></li> <li><a href="/wiki/Choline_theophyllinate" title="Choline theophyllinate">Choline theophyllinate</a></li> <li><a href="/w/index.php?title=Ciforadenant&action=edit&redlink=1" class="new" title="Ciforadenant (page does not exist)">Ciforadenant</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dimethylxanthine" title="8-Cyclopentyl-1,3-dimethylxanthine">CPX</a></li> <li><a href="/w/index.php?title=CVT-6883&action=edit&redlink=1" class="new" title="CVT-6883 (page does not exist)">CVT-6883</a></li> <li><a href="/wiki/Dimethazan" title="Dimethazan">Dimethazan</a></li> <li><a href="/wiki/DMPX" title="DMPX">DMPX</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dipropylxanthine" class="mw-redirect" title="8-Cyclopentyl-1,3-dipropylxanthine">DPCPX</a></li> <li><a href="/wiki/Dyphylline" class="mw-redirect" title="Dyphylline">Dyphylline</a></li> <li><a href="/wiki/Enprofylline" title="Enprofylline">Enprofylline</a></li> <li><a href="/wiki/Etazolate" title="Etazolate">Etazolate</a></li> <li><a href="/w/index.php?title=Etrumadenant&action=edit&redlink=1" class="new" title="Etrumadenant (page does not exist)">Etrumadenant</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/IBMX" title="IBMX">IBMX</a></li> <li><a href="/w/index.php?title=Imaradenant&action=edit&redlink=1" class="new" title="Imaradenant (page does not exist)">Imaradenant</a></li> <li><a href="/w/index.php?title=Inupadenant&action=edit&redlink=1" class="new" title="Inupadenant (page does not exist)">Inupadenant</a></li> <li><a href="/wiki/ISAM-140" title="ISAM-140">ISAM-140</a></li> <li><a href="/w/index.php?title=ISAM-R316&action=edit&redlink=1" class="new" title="ISAM-R316 (page does not exist)">ISAM-R316</a></li> <li><a href="/wiki/Isovaleric_acid" title="Isovaleric acid">Isovaleric acid</a></li> <li><a href="/wiki/Istradefylline" title="Istradefylline">Istradefylline</a></li> <li><a href="/wiki/KF-26777" title="KF-26777">KF-26777</a></li> <li><a href="/wiki/Lu_AA41063" title="Lu AA41063">Lu AA41063</a></li> <li><a href="/wiki/Lu_AA47070" title="Lu AA47070">Lu AA47070</a></li> <li><a href="/wiki/MRE3008F20" class="mw-redirect" title="MRE3008F20">MRE3008F20</a></li> <li><a href="/wiki/MRS-1191" class="mw-redirect" title="MRS-1191">MRS-1191</a></li> <li><a href="/w/index.php?title=MRS-1220&action=edit&redlink=1" class="new" title="MRS-1220 (page does not exist)">MRS-1220</a></li> <li><a href="/w/index.php?title=MRS-1334&action=edit&redlink=1" class="new" title="MRS-1334 (page does not exist)">MRS-1334</a></li> <li><a href="/wiki/MRS-1523" class="mw-redirect" title="MRS-1523">MRS-1523</a></li> <li><a href="/wiki/MRS-1706" title="MRS-1706">MRS-1706</a></li> <li><a href="/w/index.php?title=MRS-1754&action=edit&redlink=1" class="new" title="MRS-1754 (page does not exist)">MRS-1754</a></li> <li><a href="/w/index.php?title=MRS-3777&action=edit&redlink=1" class="new" title="MRS-3777 (page does not exist)">MRS-3777</a></li> <li><a href="/wiki/MSX-2" title="MSX-2">MSX-2</a></li> <li><a href="/wiki/MSX-3" title="MSX-3">MSX-3</a></li> <li><a href="/wiki/MSX-4" title="MSX-4">MSX-4</a></li> <li><a href="/w/index.php?title=Muvadenant&action=edit&redlink=1" class="new" title="Muvadenant (page does not exist)">Muvadenant</a></li> <li><a href="/wiki/Paraxanthine" title="Paraxanthine">Paraxanthine</a></li> <li><a href="/wiki/Pentoxifylline" title="Pentoxifylline">Pentoxifylline</a></li> <li><a href="/wiki/Preladenant" title="Preladenant">Preladenant</a></li> <li><a href="/wiki/Propentofylline" title="Propentofylline">Propentofylline</a></li> <li><a href="/wiki/Proxyphylline" title="Proxyphylline">Proxyphylline</a></li> <li><a href="/wiki/PSB-10" title="PSB-10">PSB-10</a></li> <li><a href="/w/index.php?title=PSB-11&action=edit&redlink=1" class="new" title="PSB-11 (page does not exist)">PSB-11</a></li> <li><a href="/w/index.php?title=PSB-36&action=edit&redlink=1" class="new" title="PSB-36 (page does not exist)">PSB-36</a></li> <li><a href="/w/index.php?title=PSB-603&action=edit&redlink=1" class="new" title="PSB-603 (page does not exist)">PSB-603</a></li> <li><a href="/w/index.php?title=PSB-788&action=edit&redlink=1" class="new" title="PSB-788 (page does not exist)">PSB-788</a></li> <li><a href="/w/index.php?title=PSB-1115&action=edit&redlink=1" class="new" title="PSB-1115 (page does not exist)">PSB-1115</a></li> <li><a href="/w/index.php?title=PSB-1901&action=edit&redlink=1" class="new" title="PSB-1901 (page does not exist)">PSB-1901</a></li> <li><a href="/wiki/Reversine" title="Reversine">Reversine</a></li> <li><a href="/wiki/Rolofylline" title="Rolofylline">Rolofylline</a></li> <li><a href="/wiki/SCH-442,416" title="SCH-442,416">SCH-442,416</a></li> <li><a href="/wiki/SCH-58261" title="SCH-58261">SCH-58261</a></li> <li><a href="/wiki/Sipagladenant" title="Sipagladenant">Sipagladenant</a></li> <li><a href="/wiki/Taminadenant" title="Taminadenant">Taminadenant</a></li> <li><a href="/wiki/Theacrine" title="Theacrine">Theacrine</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li> <li><a href="/w/index.php?title=Tozadenant&action=edit&redlink=1" class="new" title="Tozadenant (page does not exist)">Tozadenant</a></li> <li><a href="/wiki/Tracazolate" title="Tracazolate">Tracazolate</a></li> <li><a href="/w/index.php?title=Vipadenant&action=edit&redlink=1" class="new" title="Vipadenant (page does not exist)">Vipadenant</a></li> <li><a href="/w/index.php?title=VUF-5574&action=edit&redlink=1" class="new" title="VUF-5574 (page does not exist)">VUF-5574</a></li> <li><a href="/wiki/ZM-241,385" title="ZM-241,385">ZM-241,385</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/P2_receptor" title="P2 receptor">P2</a> (<a href="/wiki/Nucleotide" title="Nucleotide">nucleotide</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:3em;;text-align:center;"><a href="/wiki/P2X_purinoreceptor" title="P2X purinoreceptor">P2X</a> (<a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate"><abbr title="Adenosine triphosphate">ATP</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 Adenosine triphosphate)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/w/index.php?title=2-Methylthio-ATP&action=edit&redlink=1" class="new" title="2-Methylthio-ATP (page does not exist)">2-Me-SATP</a></li> <li><a href="/w/index.php?title=%CE%91,%CE%B2-Methylene-ATP&action=edit&redlink=1" class="new" title="Α,β-Methylene-ATP (page does not exist)">α,β-Me-ATP</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Diadenosine_tetraphosphate" class="mw-redirect" title="Diadenosine tetraphosphate">Ap4A</a></li> <li><a href="/w/index.php?title=Diadenosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diadenosine pentaphosphate (page does not exist)">Ap5A</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(γ-thio)-triphosphate (page does not exist)">ATPγS</a></li> <li><a href="/w/index.php?title=BzATP&action=edit&redlink=1" class="new" title="BzATP (page does not exist)">BzATP</a></li> <li><a href="/w/index.php?title=Cibacron_blue&action=edit&redlink=1" class="new" title="Cibacron blue (page does not exist)">Cibacron blue</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/w/index.php?title=D-%CE%B2,%CE%B3-Me-ATP&action=edit&redlink=1" class="new" title="D-β,γ-Me-ATP (page does not exist)">D-β,γ-Me-ATP</a></li> <li><a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a></li> <li><a href="/w/index.php?title=HT-AMP&action=edit&redlink=1" class="new" title="HT-AMP (page does not exist)">HT-AMP</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/w/index.php?title=L-%CE%B2,%CE%B3-Me-ATP&action=edit&redlink=1" class="new" title="L-β,γ-Me-ATP (page does not exist)">L-β,γ-Me-ATP</a></li> <li><a href="/w/index.php?title=MRS-2219&action=edit&redlink=1" class="new" title="MRS-2219 (page does not exist)">MRS-2219</a></li> <li><a href="/w/index.php?title=PAPET-ATP&action=edit&redlink=1" class="new" title="PAPET-ATP (page does not exist)">PAPET-ATP</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=5-BDBD&action=edit&redlink=1" class="new" title="5-BDBD (page does not exist)">5-BDBD</a></li> <li><a href="/w/index.php?title=A-317491&action=edit&redlink=1" class="new" title="A-317491 (page does not exist)">A-317491</a></li> <li><a href="/w/index.php?title=A-438079&action=edit&redlink=1" class="new" title="A-438079 (page does not exist)">A-438079</a></li> <li><a href="/w/index.php?title=A-740003&action=edit&redlink=1" class="new" title="A-740003 (page does not exist)">A-740003</a></li> <li><a href="/w/index.php?title=A-804598&action=edit&redlink=1" class="new" title="A-804598 (page does not exist)">A-804598</a></li> <li><a href="/w/index.php?title=A-839977&action=edit&redlink=1" class="new" title="A-839977 (page does not exist)">A-839977</a></li> <li><a href="/wiki/AF-353" title="AF-353">AF-353</a></li> <li><a href="/w/index.php?title=AZ-10606120&action=edit&redlink=1" class="new" title="AZ-10606120 (page does not exist)">AZ-10606120</a></li> <li><a href="/w/index.php?title=AZ-11645373&action=edit&redlink=1" class="new" title="AZ-11645373 (page does not exist)">AZ-11645373</a></li> <li><a href="/wiki/Brilliant_Blue_G" class="mw-redirect" title="Brilliant Blue G">BBG</a></li> <li><a href="/wiki/Calcium" title="Calcium">Calcium</a></li> <li><a href="/w/index.php?title=Calmidazolium&action=edit&redlink=1" class="new" title="Calmidazolium (page does not exist)">Calmidazolium</a></li> <li><a href="/wiki/Chelerythrine" title="Chelerythrine">Chelerythrine</a></li> <li><a href="/wiki/Copper" title="Copper">Copper</a></li> <li><a href="/wiki/Emodin" title="Emodin">Emodin</a> (<a href="/wiki/Rheum_officinale" title="Rheum officinale">Rheum officinale</a>)</li> <li><a href="/wiki/Evans_blue_(dye)" title="Evans blue (dye)">Evans blue</a></li> <li><a href="/wiki/Gefapixant" title="Gefapixant">Gefapixant</a></li> <li><a href="/w/index.php?title=GW-791343&action=edit&redlink=1" class="new" title="GW-791343 (page does not exist)">GW-791343</a></li> <li><a href="/w/index.php?title=5-(N,N-Hexamethylene)amiloride&action=edit&redlink=1" class="new" title="5-(N,N-Hexamethylene)amiloride (page does not exist)">HMA</a></li> <li><a href="/w/index.php?title=Diinosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diinosine pentaphosphate (page does not exist)">Ip5I</a></li> <li><a href="/w/index.php?title=IsoPPADS&action=edit&redlink=1" class="new" title="IsoPPADS (page does not exist)">isoPPADS</a></li> <li><a href="/w/index.php?title=JNJ-47965567&action=edit&redlink=1" class="new" title="JNJ-47965567 (page does not exist)">JNJ-47965567</a></li> <li><a href="/w/index.php?title=KN-04&action=edit&redlink=1" class="new" title="KN-04 (page does not exist)">KN-04</a></li> <li><a href="/wiki/KN-62" title="KN-62">KN-62</a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Magnesium</a></li> <li><a href="/w/index.php?title=MRS-2159&action=edit&redlink=1" class="new" title="MRS-2159 (page does not exist)">MRS-2159</a></li> <li><a href="/w/index.php?title=NF-023&action=edit&redlink=1" class="new" title="NF-023 (page does not exist)">NF-023</a></li> <li><a href="/w/index.php?title=NF-110&action=edit&redlink=1" class="new" title="NF-110 (page does not exist)">NF-110</a></li> <li><a href="/w/index.php?title=NF-157&action=edit&redlink=1" class="new" title="NF-157 (page does not exist)">NF-157</a></li> <li><a href="/w/index.php?title=NF-279&action=edit&redlink=1" class="new" title="NF-279 (page does not exist)">NF-279</a></li> <li><a href="/w/index.php?title=NF-449&action=edit&redlink=1" class="new" title="NF-449 (page does not exist)">NF-449</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/w/index.php?title=Oxidized-ATP&action=edit&redlink=1" class="new" title="Oxidized-ATP (page does not exist)">Oxidized-ATP</a></li> <li><a href="/wiki/Phenol_Red" class="mw-redirect" title="Phenol Red">Phenol Red</a></li> <li><a href="/wiki/Phenolphthalein" title="Phenolphthalein">Phenolphthalein</a></li> <li><a href="/wiki/PPADS" title="PPADS">PPADS</a></li> <li><a href="/w/index.php?title=PPNDS&action=edit&redlink=1" class="new" title="PPNDS (page does not exist)">PPNDS</a></li> <li><a href="/w/index.php?title=PSB-12062&action=edit&redlink=1" class="new" title="PSB-12062 (page does not exist)">PSB-12062</a></li> <li><a href="/wiki/Puerarin" title="Puerarin">Puerarin</a> (<a href="/wiki/Radix_puerariae" class="mw-redirect" title="Radix puerariae">Radix puerariae</a>)</li> <li><a href="/w/index.php?title=Purotoxin_1&action=edit&redlink=1" class="new" title="Purotoxin 1 (page does not exist)">Purotoxin 1</a></li> <li><a href="/w/index.php?title=Reactive_Blue_2&action=edit&redlink=1" class="new" title="Reactive Blue 2 (page does not exist)">RB-2</a></li> <li><a href="/w/index.php?title=Ro_0437626&action=edit&redlink=1" class="new" title="Ro 0437626 (page does not exist)">Ro 0437626</a></li> <li><a href="/w/index.php?title=Ro_51&action=edit&redlink=1" class="new" title="Ro 51 (page does not exist)">Ro 51</a></li> <li><a href="/w/index.php?title=RO-3&action=edit&redlink=1" class="new" title="RO-3 (page does not exist)">RO-3</a></li> <li><a href="/wiki/Sodium_ferulate" title="Sodium ferulate">Sodium ferulate</a> (<a href="/wiki/Angelica_sinensis" title="Angelica sinensis">Angelica sinensis</a>, <a href="/wiki/Ligusticum_wallichii" class="mw-redirect" title="Ligusticum wallichii">Ligusticum wallichii</a>)</li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/w/index.php?title=TC-P_262&action=edit&redlink=1" class="new" title="TC-P 262 (page does not exist)">TC-P 262</a></li> <li><a href="/wiki/Tetramethylpyrazine" title="Tetramethylpyrazine">Tetramethylpyrazine (ligustrazine)</a> (<a href="/wiki/Ligusticum_wallichii" class="mw-redirect" title="Ligusticum wallichii">Ligusticum wallichii</a>)</li> <li><a href="/wiki/TNP-ATP" title="TNP-ATP">TNP-ATP</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:3em;;text-align:center;"><a href="/wiki/P2Y_receptor" title="P2Y receptor">P2Y</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/w/index.php?title=2-Methylthioladenosine_diphosphate&action=edit&redlink=1" class="new" title="2-Methylthioladenosine diphosphate (page does not exist)">2-Me-SADP</a></li> <li><a href="/w/index.php?title=2-Methylthioadenosine_triphosphate&action=edit&redlink=1" class="new" title="2-Methylthioadenosine triphosphate (page does not exist)">2-Me-SATP</a></li> <li><a href="/w/index.php?title=2-Thio-UTP&action=edit&redlink=1" class="new" title="2-Thio-UTP (page does not exist)">2-Thio-UTP</a></li> <li><a href="/w/index.php?title=5-Bromouridine_5%E2%80%B2-diphosphate&action=edit&redlink=1" class="new" title="5-Bromouridine 5′-diphosphate (page does not exist)">5-Br-UDP</a></li> <li><a href="/w/index.php?title=5-OMe-UDP&action=edit&redlink=1" class="new" title="5-OMe-UDP (page does not exist)">5-OMe-UDP</a></li> <li><a href="/w/index.php?title=%CE%91,%CE%B2-Methylene-ATP&action=edit&redlink=1" class="new" title="Α,β-Methylene-ATP (page does not exist)">α,β-Me-ATP</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B2-thio)-diphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(β-thio)-diphosphate (page does not exist)">ADPβS</a></li> <li><a href="/w/index.php?title=Diadenosine_triphosphate&action=edit&redlink=1" class="new" title="Diadenosine triphosphate (page does not exist)">Ap3A</a></li> <li><a href="/w/index.php?title=AR-C_67085MX&action=edit&redlink=1" class="new" title="AR-C 67085MX (page does not exist)">AR-C 67085MX</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(γ-thio)-triphosphate (page does not exist)">ATPγS</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/Deoxyadenosine_triphosphate" title="Deoxyadenosine triphosphate">dATP</a></li> <li><a href="/wiki/Denufosol" title="Denufosol">Denufosol</a></li> <li><a href="/wiki/Diquafosol" title="Diquafosol">Diquafosol</a></li> <li><a href="/w/index.php?title=Inosine_diphosphate&action=edit&redlink=1" class="new" title="Inosine diphosphate (page does not exist)">IDP</a></li> <li><a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a></li> <li><a href="/wiki/INS-365" class="mw-redirect" title="INS-365">INS-365</a></li> <li><a href="/w/index.php?title=INS-37217&action=edit&redlink=1" class="new" title="INS-37217 (page does not exist)">INS-37217</a></li> <li><a href="/w/index.php?title=MRS-2365&action=edit&redlink=1" class="new" title="MRS-2365 (page does not exist)">MRS-2365</a></li> <li><a href="/w/index.php?title=MRS-2690&action=edit&redlink=1" class="new" title="MRS-2690 (page does not exist)">MRS-2690</a></li> <li><a href="/w/index.php?title=MRS-2693&action=edit&redlink=1" class="new" title="MRS-2693 (page does not exist)">MRS-2693</a></li> <li><a href="/w/index.php?title=MRS-2768&action=edit&redlink=1" class="new" title="MRS-2768 (page does not exist)">MRS-2768</a></li> <li><a href="/w/index.php?title=MRS-2957&action=edit&redlink=1" class="new" title="MRS-2957 (page does not exist)">MRS-2957</a></li> <li><a href="/w/index.php?title=MRS-4062&action=edit&redlink=1" class="new" title="MRS-4062 (page does not exist)">MRS-4062</a></li> <li><a href="/w/index.php?title=NF-546&action=edit&redlink=1" class="new" title="NF-546 (page does not exist)">NF-546</a></li> <li><a href="/w/index.php?title=PAPET-ATP&action=edit&redlink=1" class="new" title="PAPET-ATP (page does not exist)">PAPET-ATP</a></li> <li><a href="/w/index.php?title=PSB-0474&action=edit&redlink=1" class="new" title="PSB-0474 (page does not exist)">PSB-0474</a></li> <li><a href="/w/index.php?title=PSB-1114&action=edit&redlink=1" class="new" title="PSB-1114 (page does not exist)">PSB-1114</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li> <li><a href="/w/index.php?title=Uridine_5%C2%B4-(%CE%B2-thio)-diphosphate&action=edit&redlink=1" class="new" title="Uridine 5´-(β-thio)-diphosphate (page does not exist)">UDPβS</a></li> <li><a href="/wiki/Uridine_diphosphate_galactose" title="Uridine diphosphate galactose">UDP-galactose</a></li> <li><a href="/wiki/Uridine_diphosphate_glucose" title="Uridine diphosphate glucose">UDP-glucose</a></li> <li><a href="/wiki/Uridine_diphosphate_N-acetylglucosamine" title="Uridine diphosphate N-acetylglucosamine">UDP-N-acetylglucosamine</a></li> <li><a href="/w/index.php?title=Diuridine_triphosphate&action=edit&redlink=1" class="new" title="Diuridine triphosphate (page does not exist)">Up3U</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li> <li><a href="/w/index.php?title=Uridine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Uridine-5'-(γ-thio)-triphosphate (page does not exist)">UTPγS</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=2-Methylthioladenosine_monophosphate&action=edit&redlink=1" class="new" title="2-Methylthioladenosine monophosphate (page does not exist)">2-Me-SAMP</a></li> <li><a href="/w/index.php?title=A3P5PS&action=edit&redlink=1" class="new" title="A3P5PS (page does not exist)">A3P5PS</a></li> <li><a href="/w/index.php?title=AMP%CE%B1S&action=edit&redlink=1" class="new" title="AMPαS (page does not exist)">AMPαS</a></li> <li><a href="/wiki/Diadenosine_tetraphosphate" class="mw-redirect" title="Diadenosine tetraphosphate">Ap4A</a></li> <li><a href="/w/index.php?title=AR-C_66096&action=edit&redlink=1" class="new" title="AR-C 66096 (page does not exist)">AR-C 66096</a></li> <li><a href="/w/index.php?title=AR-C_67085MX&action=edit&redlink=1" class="new" title="AR-C 67085MX (page does not exist)">AR-C 67085MX</a></li> <li><a href="/w/index.php?title=AR-C_69931MX&action=edit&redlink=1" class="new" title="AR-C 69931MX (page does not exist)">AR-C 69931MX</a></li> <li><a href="/w/index.php?title=AR-C_118925XX&action=edit&redlink=1" class="new" title="AR-C 118925XX (page does not exist)">AR-C 118925XX</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=BzATP&action=edit&redlink=1" class="new" title="BzATP (page does not exist)">BzATP</a></li> <li><a href="/w/index.php?title=C1330-7&action=edit&redlink=1" class="new" title="C1330-7 (page does not exist)">C1330-7</a></li> <li><a href="/wiki/Cangrelor" title="Cangrelor">Cangrelor</a></li> <li><a href="/wiki/Clopidogrel" title="Clopidogrel">Clopidogrel</a></li> <li><a href="/wiki/Elinogrel" title="Elinogrel">Elinogrel</a></li> <li><a href="/w/index.php?title=Diinosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diinosine pentaphosphate (page does not exist)">Ip5I</a></li> <li><a href="/w/index.php?title=MRS-2179&action=edit&redlink=1" class="new" title="MRS-2179 (page does not exist)">MRS-2179</a></li> <li><a href="/w/index.php?title=MRS-2211&action=edit&redlink=1" class="new" title="MRS-2211 (page does not exist)">MRS-2211</a></li> <li><a href="/w/index.php?title=MRS-2279&action=edit&redlink=1" class="new" title="MRS-2279 (page does not exist)">MRS-2279</a></li> <li><a href="/w/index.php?title=MRS-2395&action=edit&redlink=1" class="new" title="MRS-2395 (page does not exist)">MRS-2395</a></li> <li><a href="/w/index.php?title=MRS-2500&action=edit&redlink=1" class="new" title="MRS-2500 (page does not exist)">MRS-2500</a></li> <li><a href="/w/index.php?title=MRS-2578&action=edit&redlink=1" class="new" title="MRS-2578 (page does not exist)">MRS-2578</a></li> <li><a href="/w/index.php?title=NF-157&action=edit&redlink=1" class="new" title="NF-157 (page does not exist)">NF-157</a></li> <li><a href="/w/index.php?title=NF-340&action=edit&redlink=1" class="new" title="NF-340 (page does not exist)">NF-340</a></li> <li><a href="/w/index.php?title=2,2%27-Pyridylisatogen_tosylate&action=edit&redlink=1" class="new" title="2,2'-Pyridylisatogen tosylate (page does not exist)">PIT</a></li> <li><a href="/wiki/PPADS" title="PPADS">PPADS</a></li> <li><a href="/wiki/Prasugrel" title="Prasugrel">Prasugrel</a></li> <li><a href="/w/index.php?title=PSB-0739&action=edit&redlink=1" class="new" title="PSB-0739 (page does not exist)">PSB-0739</a></li> <li><a href="/w/index.php?title=Reactive_Blue_2&action=edit&redlink=1" class="new" title="Reactive Blue 2 (page does not exist)">RB-2</a></li> <li><a href="/wiki/Regrelor" title="Regrelor">Regrelor</a></li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/wiki/Ticagrelor" title="Ticagrelor">Ticagrelor</a></li> <li><a href="/wiki/Ticlopidine" title="Ticlopidine">Ticlopidine</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li></ul> </div></td></tr></tbody></table><div></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/Membrane_transport_protein" title="Membrane transport protein">Transporter</a> (<a href="/wiki/Reuptake_inhibitor" title="Reuptake inhibitor">blockers</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:6em;;text-align:center;"><a href="/wiki/Concentrative_nucleoside_transporters" class="mw-redirect" title="Concentrative nucleoside transporters"><abbr title="Concentrative nucleoside transporters">CNTs</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 Concentrative nucleoside transporters</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=6-Hydroxy-7-methoxyflavone&action=edit&redlink=1" class="new" title="6-Hydroxy-7-methoxyflavone (page does not exist)">6-Hydroxy-7-methoxyflavone</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/w/index.php?title=DMeThPmR&action=edit&redlink=1" class="new" title="DMeThPmR (page does not exist)">dMeThPmR</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/w/index.php?title=KGO-2142&action=edit&redlink=1" class="new" title="KGO-2142 (page does not exist)">KGO-2142</a></li> <li><a href="/w/index.php?title=KGO-2173&action=edit&redlink=1" class="new" title="KGO-2173 (page does not exist)">KGO-2173</a></li> <li><a href="/w/index.php?title=MeThPmR&action=edit&redlink=1" class="new" title="MeThPmR (page does not exist)">MeThPmR</a></li> <li><a href="/wiki/Phloridzin" class="mw-redirect" title="Phloridzin">Phloridzin</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Equilibrative_nucleoside_transporters" class="mw-redirect" title="Equilibrative nucleoside transporters"><abbr title="Equilibrative nucleoside transporters">ENTs</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 Equilibrative nucleoside transporters</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></li> <li><a href="/wiki/Cilostazol" title="Cilostazol">Cilostazol</a></li> <li><a href="/wiki/Dilazep" title="Dilazep">Dilazep</a></li> <li><a href="/wiki/Dipyridamole" title="Dipyridamole">Dipyridamole</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Hexobendine" title="Hexobendine">Hexobendine</a></li> <li><a href="/w/index.php?title=6-S-((4-Nitrophenyl)methyl)-6-thioinosine&action=edit&redlink=1" class="new" title="6-S-((4-Nitrophenyl)methyl)-6-thioinosine (page does not exist)">NBMPR</a></li> <li><a href="/wiki/Pentoxifylline" title="Pentoxifylline">Pentoxifylline</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Propentofylline" title="Propentofylline">Propentofylline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Plasma_membrane_monoamine_transporter" title="Plasma membrane monoamine transporter"><abbr title="Plasma membrane monoamine transporter">PMAT</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 Plasma membrane monoamine transporter</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Decynium-22" title="Decynium-22">Decynium-22</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/Enzyme" title="Enzyme">Enzyme</a> (<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</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:6em;;text-align:center;"><a href="/wiki/Xanthine_oxidase" title="Xanthine oxidase"><abbr title="Xanthine oxidase">XO</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 Xanthine oxidase</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Allopurinol" title="Allopurinol">Allopurinol</a></li> <li><a href="/wiki/Amflutizole" title="Amflutizole">Amflutizole</a></li> <li><a href="/wiki/Benzbromarone" title="Benzbromarone">Benzbromarone</a></li> <li><a href="/wiki/Caffeic_acid" title="Caffeic acid">Caffeic acid</a></li> <li><a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">Cinnamaldehyde</a></li> <li><a href="/wiki/Cinnamomum_osmophloeum" title="Cinnamomum osmophloeum">Cinnamomum osmophloeum</a></li> <li><a href="/wiki/Febuxostat" title="Febuxostat">Febuxostat</a></li> <li><a href="/wiki/Myo-inositol" class="mw-redirect" title="Myo-inositol">Myo-inositol</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/wiki/Myricetin" title="Myricetin">Myricetin</a></li> <li><a href="/w/index.php?title=Niraxostat&action=edit&redlink=1" class="new" title="Niraxostat (page does not exist)">Niraxostat</a></li> <li><a href="/wiki/Oxipurinol" title="Oxipurinol">Oxipurinol</a></li> <li><a href="/wiki/Phytic_acid" title="Phytic acid">Phytic acid</a></li> <li><a href="/wiki/Pistacia_integerrima" title="Pistacia integerrima">Pistacia integerrima</a></li> <li><a href="/wiki/Propolis" title="Propolis">Propolis</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Tisopurine" title="Tisopurine">Tisopurine</a></li> <li><a href="/wiki/Topiroxostat" title="Topiroxostat">Topiroxostat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminopterin" title="Aminopterin">Aminopterin</a></li> <li><a href="/wiki/Azathioprine" title="Azathioprine">Azathioprine</a></li> <li><a href="/wiki/Methotrexate" title="Methotrexate">Methotrexate</a></li> <li><a href="/wiki/Mycophenolic_acid" title="Mycophenolic acid">Mycophenolic acid</a></li> <li><a href="/wiki/Pemetrexed" title="Pemetrexed">Pemetrexed</a></li> <li><a href="/wiki/Pralatrexate" title="Pralatrexate">Pralatrexate</a></li> <li>Many others</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Precursors: <a href="/wiki/Adenine" title="Adenine">Adenine</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Cytosine" title="Cytosine">Cytosine</a></li> <li><a href="/wiki/Cytidine" title="Cytidine">Cytidine</a></li> <li><a href="/wiki/Cytidine_monophosphate" title="Cytidine monophosphate">CMP</a></li> <li><a href="/wiki/Cytidine_diphosphate" title="Cytidine diphosphate">CDP</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/Guanine" title="Guanine">Guanine</a></li> <li><a href="/wiki/Guanosine" title="Guanosine">Guanosine</a></li> <li><a href="/wiki/Guanosine_monophosphate" title="Guanosine monophosphate">GMP</a></li> <li><a href="/wiki/Guanosine_diphosphate" title="Guanosine diphosphate">GDP</a></li> <li><a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a></li> <li><a href="/wiki/Hypoxanthine" title="Hypoxanthine">Hypoxanthine</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/Inosine_monophosphate" class="mw-redirect" title="Inosine monophosphate">IMP</a></li> <li><a href="/w/index.php?title=Inosine_diphosphate&action=edit&redlink=1" class="new" title="Inosine diphosphate (page does not exist)">IDP</a></li> <li><a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a></li> <li><a href="/wiki/Ribose" title="Ribose">Ribose</a></li> <li><a href="/wiki/Uracil" title="Uracil">Uracil</a></li> <li><a href="/wiki/Uridine" title="Uridine">Uridine</a></li> <li><a href="/wiki/Uridine_monophosphate" title="Uridine monophosphate">UMP</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li></ul> <ul><li>Others: <a href="/wiki/Chrysophanol" title="Chrysophanol">Chrysophanol</a> (<a href="/wiki/Rhubarb" title="Rhubarb">rhubarb</a>)</li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>See also: <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></div></td></tr></tbody></table></div></div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output 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class="mw-portlet mw-portlet-dock-bottom emptyPortlet" id="p-dock-bottom"> <ul> </ul> </div> <script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.main-5fb7f6487f-rg8st","wgBackendResponseTime":492,"wgPageParseReport":{"limitreport":{"cputime":"3.645","walltime":"4.136","ppvisitednodes":{"value":27740,"limit":1000000},"postexpandincludesize":{"value":1282347,"limit":2097152},"templateargumentsize":{"value":114448,"limit":2097152},"expansiondepth":{"value":19,"limit":100},"expensivefunctioncount":{"value":36,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":1321348,"limit":5000000},"entityaccesscount":{"value":1,"limit":400},"timingprofile":["100.00% 3274.527 1 -total"," 56.52% 1850.717 1 Template:Reflist"," 25.36% 830.387 167 Template:Cite_journal"," 11.97% 391.880 1 Template:Infobox_drug"," 9.59% 313.942 1 Template:Infobox"," 9.19% 300.974 64 Template:Cite_web"," 7.49% 245.242 56 Template:Cite_book"," 5.55% 181.868 15 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[\"CITEREFBenjaminRogersRosenbaum1991\"] = 1,\n [\"CITEREFBenowitz1990\"] = 1,\n [\"CITEREFBenzon2013\"] = 1,\n [\"CITEREFBersten1999\"] = 1,\n [\"CITEREFBerzelius1825\"] = 1,\n [\"CITEREFBerzelius1828\"] = 1,\n [\"CITEREFBishop2010\"] = 1,\n [\"CITEREFBjørngaardNordestgaardTaylorTreur2017\"] = 1,\n [\"CITEREFBlanchardSawers1983\"] = 1,\n [\"CITEREFBoekemaSamsomvan_Berge_HenegouwenSmout1999\"] = 1,\n [\"CITEREFBoltonNull1981\"] = 1,\n [\"CITEREFBonaventuraNavarroCasadó-AngueraAzdad2015\"] = 1,\n [\"CITEREFBrentChristianDiener2011\"] = 1,\n [\"CITEREFBrown2004\"] = 1,\n [\"CITEREFBrown2011\"] = 1,\n [\"CITEREFBruceLader1989\"] = 1,\n [\"CITEREFBrødbaekDamkier2007\"] = 1,\n [\"CITEREFBudneyEmond2014\"] = 1,\n [\"CITEREFBurchfield1997\"] = 1,\n [\"CITEREFBuxton2010\"] = 1,\n [\"CITEREFCaballeroFinglasToldra2015\"] = 1,\n [\"CITEREFCamfieldStoughFarrimondScholey2014\"] = 2,\n [\"CITEREFCampo2009\"] = 1,\n [\"CITEREFCano-MarquinaTarínCano2013\"] = 1,\n [\"CITEREFCarpenter2015\"] = 1,\n [\"CITEREFCarreonParsh2019\"] = 1,\n [\"CITEREFCarrilloBenitez2000\"] = 1,\n [\"CITEREFCastellanosRapoport2002\"] = 1,\n [\"CITEREFCharles2016\"] = 1,\n [\"CITEREFChenWuNeelakantanChong2014\"] = 1,\n [\"CITEREFChenWuNeelakantanChong2016\"] = 1,\n [\"CITEREFChestonSmith2013\"] = 1,\n [\"CITEREFChinMervesGoldbergerSampson-Cone2008\"] = 1,\n [\"CITEREFCohenBooth1975\"] = 1,\n [\"CITEREFCollado-MateoLavín-PérezMerellano-NavarroCoso2020\"] = 1,\n [\"CITEREFCongerWarrenHardyMillard-Stafford2011\"] = 1,\n [\"CITEREFCornelisMondaYuPaynter2011\"] = 1,\n [\"CITEREFCrownEmersonGuHurst2012\"] = 1,\n [\"CITEREFDenoeudCarretero-PauletDereeperDroc2014\"] = 1,\n [\"CITEREFDereeMartinsMelbostadLoomis2008\"] = 1,\n [\"CITEREFDerryDerryMoore2014\"] = 1,\n [\"CITEREFDesbrow2012\"] = 1,\n [\"CITEREFDohertySmith2005\"] = 1,\n [\"CITEREFDownsGiustDunn2017\"] = 1,\n [\"CITEREFDuanYangSlaughter2009\"] = 1,\n [\"CITEREFDullooGeisslerHortonCollins1989\"] = 1,\n [\"CITEREFDumas1823\"] = 1,\n [\"CITEREFEFSA_Panel_on_Dietetic_Products,_Nutrition_and_Allergies_2015\"] = 1,\n [\"CITEREFEbenezer2015\"] = 1,\n [\"CITEREFEssayan2001\"] = 1,\n [\"CITEREFEvans1992\"] = 1,\n [\"CITEREFEvansRichardsBattisti2019\"] = 1,\n [\"CITEREFFairbanks2004\"] = 1,\n [\"CITEREFFaudoneArifiMerk2021\"] = 1,\n [\"CITEREFFerré2008\"] = 1,\n [\"CITEREFFerré2010\"] = 1,\n [\"CITEREFFerré2013\"] = 1,\n [\"CITEREFFerré2016\"] = 1,\n [\"CITEREFFerréBonaventuraTomasiNavarro2016\"] = 1,\n [\"CITEREFFintelLangerDuenas1984\"] = 1,\n [\"CITEREFFishchmanMello\"] = 1,\n [\"CITEREFFisoneBorgkvistUsiello2004\"] = 1,\n [\"CITEREFFredholmBättigHolménNehlig1999\"] = 1,\n [\"CITEREFFrischknechtUlmer-DufekBaumann1986\"] = 1,\n [\"CITEREFFroestlMuhsPfeifer2012\"] = 1,\n [\"CITEREFFunk2009\"] = 1,\n [\"CITEREFGibbonsSchmidtBiaggioniFrazier-Mills2017\"] = 1,\n [\"CITEREFGilmoreMichael2011\"] = 1,\n [\"CITEREFGottwaltPrasanna2021\"] = 1,\n [\"CITEREFGraham1954\"] = 1,\n [\"CITEREFGreenblatt2012\"] = 1,\n [\"CITEREFGrgic2018\"] = 1,\n [\"CITEREFGrgicTrexlerLazinicaPedisic2018\"] = 1,\n [\"CITEREFGrimesKennedyLabatonHine2015\"] = 1,\n [\"CITEREFGrossoMicekCastellanoPajak2016\"] = 1,\n [\"CITEREFGuptaLipsitz2007\"] = 1,\n [\"CITEREFHackett2010\"] = 1,\n [\"CITEREFHeckmanWeilGonzalez_de_Mejia2010\"] = 1,\n [\"CITEREFHenderson-SmartDe_Paoli2010\"] = 1,\n [\"CITEREFHicksHsiehBell1996\"] = 1,\n [\"CITEREFHillisSadavaHillPrice2015\"] = 1,\n [\"CITEREFHongChanBai2020\"] = 1,\n [\"CITEREFHopkins2006\"] = 1,\n [\"CITEREFHrnčiaroveBarteček2017\"] = 1,\n [\"CITEREFHuangO\u0026#039;DonnellBarbolineBarkman2016\"] = 1,\n [\"CITEREFIancuOlmerStrous2007\"] = 1,\n [\"CITEREFInstitute_of_Medicine_(US)_Committee_on_Military_Nutrition_Research2001\"] = 1,\n [\"CITEREFJahanfarJaafar2015\"] = 1,\n [\"CITEREFJiangZhangJiang2014\"] = 1,\n [\"CITEREFJobst1838\"] = 1,\n [\"CITEREFJulianoGriffiths2004\"] = 1,\n [\"CITEREFKaradshehKussieLinthicum1991\"] = 1,\n [\"CITEREFKarch2009\"] = 1,\n [\"CITEREFKennerly1995\"] = 1,\n [\"CITEREFKerEdwardsFelixBlackhall2010\"] = 1,\n [\"CITEREFKeskineva\"] = 1,\n [\"CITEREFKlosterman2006\"] = 1,\n [\"CITEREFKohnKeller2015\"] = 1,\n [\"CITEREFKootDeurenberg1995\"] = 1,\n [\"CITEREFKuczkowski2009\"] = 1,\n [\"CITEREFKugelmanDurand2011\"] = 1,\n [\"CITEREFLara2010\"] = 1,\n [\"CITEREFLassiImamDeanBhutta2014\"] = 1,\n [\"CITEREFLevounisHerron2014\"] = 1,\n [\"CITEREFLiWangGuoWang2011\"] = 1,\n [\"CITEREFLiddleConnor2013\"] = 1,\n [\"CITEREFLiguoriHughesGrass1997\"] = 1,\n [\"CITEREFLiguoriRobinson2001\"] = 1,\n [\"CITEREFLiuGuoParkHuang2012\"] = 1,\n [\"CITEREFLovejoy1980\"] = 1,\n [\"CITEREFMackayTipladyScholey2002\"] = 1,\n [\"CITEREFMalenkaNestlerHyman2009\"] = 1,\n [\"CITEREFMarczinskiFillmore2003\"] = 1,\n [\"CITEREFMarquesZhengPoulakisGuzman1999\"] = 1,\n [\"CITEREFMartinez-Carter2012\"] = 1,\n [\"CITEREFMathew2011\"] = 1,\n [\"CITEREFMatissek1997\"] = 1,\n [\"CITEREFMaughanGriffin2003\"] = 1,\n [\"CITEREFMaughanWatsonCorderyWalsh2016\"] = 1,\n [\"CITEREFMcCuskerFuehrleinGoldbergerGold2006\"] = 1,\n [\"CITEREFMcLellanCaldwellLieberman2016\"] = 1,\n [\"CITEREFMeredithJulianoHughesGriffiths2013\"] = 1,\n [\"CITEREFMeyers2005\"] = 1,\n [\"CITEREFMiller2013\"] = 1,\n [\"CITEREFMordeSudhakarRambabuShankar2021\"] = 1,\n [\"CITEREFMulder1838\"] = 1,\n [\"CITEREFMurrayTraylor2019\"] = 1,\n [\"CITEREFMyers2007\"] = 1,\n [\"CITEREFMüllerJacobson2010\"] = 1,\n [\"CITEREFNathanson1984\"] = 1,\n [\"CITEREFNehlig2010\"] = 1,\n [\"CITEREFNehligArmspachNamer2010\"] = 1,\n [\"CITEREFNehligDavalDebry1992\"] = 1,\n [\"CITEREFNestler2013\"] = 1,\n [\"CITEREFNestlerHymenHoltzmannMalenka\"] = 1,\n [\"CITEREFNewtonBroughtonLindMorrison1981\"] = 1,\n [\"CITEREFNoeverCroniseRelwani1995\"] = 1,\n [\"CITEREFO\u0026#039;CallaghanMuurlinkReid2018\"] = 1,\n [\"CITEREFO\u0026#039;Connor2008\"] = 1,\n [\"CITEREFOudry1827\"] = 1,\n [\"CITEREFPanzaSolfrizziBarulliBonfiglio2015\"] = 1,\n [\"CITEREFPaul\"] = 1,\n [\"CITEREFPelletier1822\"] = 1,\n [\"CITEREFPendergrast2001\"] = 1,\n [\"CITEREFPestaAngadiBurtscherRoberts2013\"] = 1,\n [\"CITEREFPeters-GoldenCanettiMancusoCoffey2005\"] = 1,\n [\"CITEREFPeters1967\"] = 1,\n [\"CITEREFPohankaDobes2013\"] = 1,\n [\"CITEREFPoleszakSzopaWyskaKukuła-Koch2016\"] = 1,\n [\"CITEREFPrankerd2007\"] = 1,\n [\"CITEREFPrynne2013\"] = 1,\n [\"CITEREFQiLi2014\"] = 1,\n [\"CITEREFRapuriGallagherKinyamuRyschon2001\"] = 1,\n [\"CITEREFReddyShivaManikantanRamakrishna2024\"] = 1,\n [\"CITEREFReissigStrainGriffiths2009\"] = 1,\n [\"CITEREFRibaTasmanKayLieberman2014\"] = 1,\n [\"CITEREFRibeiroSebastião2010\"] = 2,\n [\"CITEREFRichardson2009\"] = 1,\n [\"CITEREFRied2012\"] = 1,\n [\"CITEREFRinker2021\"] = 1,\n [\"CITEREFRobertsonWadeWorkmanWoosley1981\"] = 1,\n [\"CITEREFRobinette2018\"] = 1,\n [\"CITEREFRobiquet1823\"] = 1,\n [\"CITEREFRodopoulosWisénNorman1995\"] = 1,\n [\"CITEREFRunge1820\"] = 1,\n [\"CITEREFRätsch2005\"] = 1,\n [\"CITEREFSalernoKnights2010\"] = 1,\n [\"CITEREFSanner2014\"] = 1,\n [\"CITEREFSantosCostaSantosVaz-Carneiro2010\"] = 1,\n [\"CITEREFSchmidt2005\"] = 1,\n [\"CITEREFSchmidtAndersonDoyleDewey2012\"] = 1,\n [\"CITEREFSchmidtRobertsDavisDoyle2006\"] = 1,\n [\"CITEREFSchmidtRobertsDavisDoyle2007\"] = 1,\n [\"CITEREFSchneiderBenjamin2011\"] = 1,\n [\"CITEREFSchulteis2010\"] = 1,\n [\"CITEREFSealeAblaShamimCarney1988\"] = 1,\n [\"CITEREFSenese2005\"] = 1,\n [\"CITEREFShenBrooksCincottaManjourides2019\"] = 1,\n [\"CITEREFSherwoodKell2009\"] = 1,\n [\"CITEREFShute2007\"] = 1,\n [\"CITEREFSinghSinghLatiefTung2022\"] = 1,\n [\"CITEREFSmitGaffanRogers2004\"] = 1,\n [\"CITEREFSmith2002\"] = 1,\n [\"CITEREFSmith2017\"] = 1,\n [\"CITEREFSnelLorist2011\"] = 1,\n [\"CITEREFSouthwardRutherfurd-MarkwickAli2018\"] = 1,\n [\"CITEREFSpiller2019\"] = 1,\n [\"CITEREFSusan_Budavari1996\"] = 1,\n [\"CITEREFSwidinsky_J,_Baizer_MM1957\"] = 1,\n [\"CITEREFTarnopolsky2010\"] = 1,\n [\"CITEREFTeekachunhateanTosriRojanasthienSrichairatanakool2013\"] = 1,\n [\"CITEREFTemple2009\"] = 2,\n [\"CITEREFTemple2019\"] = 2,\n [\"CITEREFTempleBernardLipshultzCzachor2017\"] = 1,\n [\"CITEREFTempleWilson2003\"] = 1,\n [\"CITEREFThomasChenHowes1997\"] = 1,\n [\"CITEREFVallombroso2001\"] = 1,\n [\"CITEREFVerbeeck2008\"] = 1,\n [\"CITEREFVersterKoenig2018\"] = 1,\n [\"CITEREFVilarimRocha_AraujoNardi2011\"] = 1,\n [\"CITEREFWangShenWuZhang2016\"] = 1,\n [\"CITEREFWarrenParkMarescaMcKibans2010\"] = 1,\n [\"CITEREFWeinbergBealer2001\"] = 3,\n [\"CITEREFWelshBaraBarleyCates2010\"] = 1,\n [\"CITEREFWikoffWelshHendersonBrorby2017\"] = 1,\n [\"CITEREFWilliams2016\"] = 1,\n [\"CITEREFWinston2005\"] = 1,\n [\"CITEREFWinstonHardwickJaberi2005\"] = 1,\n [\"CITEREFWoodSageShumanAnagnostaras2014\"] = 1,\n [\"CITEREFWrightBakerPalmerStabler2013\"] = 1,\n [\"CITEREFYangWangSungTing2022\"] = 1,\n [\"CITEREFYu1995\"] = 1,\n [\"CITEREFZajacZakrzewskiKowalNarayan2003\"] = 1,\n [\"CITEREFZevinBenowitz1999\"] = 1,\n [\"CITEREFvan_Bredavan_der_MerweRobbertseApostolides2013\"] = 1,\n [\"CITEREFvan_DamHuWillett2020\"] = 1,\n [\"CITEREFÁgostonMasters2009\"] = 1,\n [\"Side_effects\"] = 1,\n}\ntemplate_list = table#1 {\n [\"!\"] = 1,\n [\"ATC\"] = 2,\n [\"About\"] = 1,\n [\"Acetylcholine metabolism and transport modulators\"] = 1,\n [\"Anchor\"] = 1,\n [\"As of\"] = 1,\n [\"Authority control\"] = 1,\n [\"Blockquote\"] = 2,\n [\"CO2\"] = 3,\n [\"Cbignore\"] = 1,\n [\"Chocolate\"] = 1,\n [\"Circa\"] = 1,\n [\"Cite book\"] = 56,\n [\"Cite encyclopedia\"] = 2,\n [\"Cite journal\"] = 167,\n [\"Cite magazine\"] = 1,\n [\"Cite news\"] = 15,\n [\"Cite patent\"] = 1,\n [\"Cite report\"] = 1,\n [\"Cite web\"] = 64,\n [\"Clarify\"] = 2,\n [\"Cn\"] = 1,\n [\"Coffee\"] = 1,\n [\"Convert\"] = 17,\n [\"Cs1 config\"] = 1,\n [\"Cvt\"] = 3,\n [\"Drugs.com\"] = 1,\n [\"Expand section\"] = 1,\n [\"Frac\"] = 1,\n [\"Fv\"] = 1,\n [\"Globalize\"] = 1,\n [\"Glycine receptor modulators\"] = 1,\n [\"Google books\"] = 21,\n [\"Harvnb\"] = 3,\n [\"INIST\"] = 1,\n [\"IPAc-en\"] = 1,\n [\"Infobox drug\"] = 1,\n [\"Lang\"] = 2,\n [\"Main\"] = 5,\n [\"Navboxes\"] = 1,\n [\"Not a typo\"] = 4,\n [\"Nowrap\"] = 18,\n [\"Nts\"] = 31,\n [\"Other dermatological preparations\"] = 1,\n [\"PD-notice\"] = 1,\n [\"PMID\"] = 1,\n [\"Page needed\"] = 1,\n [\"Phosphodiesterase inhibitors\"] = 1,\n [\"Portal bar\"] = 1,\n [\"Pp-move-indef\"] = 1,\n [\"Purine receptor modulators\"] = 1,\n [\"Refbegin\"] = 1,\n [\"Refend\"] = 1,\n [\"Reflist\"] = 1,\n [\"See also\"] = 5,\n [\"Short description\"] = 1,\n [\"Sister project links\"] = 1,\n [\"Smallcaps all\"] = 1,\n [\"Soft drink\"] = 1,\n [\"Stimulants\"] = 1,\n [\"Synapse map\"] = 1,\n [\"TOC limit\"] = 1,\n [\"Teas\"] = 1,\n [\"Unreliable source?\"] = 1,\n [\"Use dmy dates\"] = 1,\n [\"Vague\"] = 1,\n [\"•\"] = 6,\n}\narticle_whitelist = table#1 {\n}\nciteref_patterns = table#1 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