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href="#Biological_role"> <div class="vector-toc-text"> 3 Biological role </div> </a> <button aria-controls="toc-Biological_role-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Biological role subsection </button> <ul id="toc-Biological_role-sublist" class="vector-toc-list"> <li id="toc-Cellular_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cellular_effects"> <div class="vector-toc-text"> 3.1 Cellular effects </div> </a> <ul id="toc-Cellular_effects-sublist" class="vector-toc-list"> <li id="toc-Receptors" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Receptors"> <div class="vector-toc-text"> 3.1.1 Receptors </div> </a> <ul id="toc-Receptors-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Termination" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Termination"> <div class="vector-toc-text"> 3.1.2 Termination </div> </a> <ul id="toc-Termination-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Serotonylation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Serotonylation"> <div class="vector-toc-text"> 3.1.3 Serotonylation </div> </a> <ul id="toc-Serotonylation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Nervous_system" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nervous_system"> <div class="vector-toc-text"> 3.2 Nervous system </div> </a> <ul id="toc-Nervous_system-sublist" class="vector-toc-list"> <li id="toc-Ultrastructure_and_function" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Ultrastructure_and_function"> <div class="vector-toc-text"> 3.2.1 Ultrastructure and function </div> </a> <ul id="toc-Ultrastructure_and_function-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Microanatomy" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Microanatomy"> <div class="vector-toc-text"> 3.2.2 Microanatomy </div> </a> <ul id="toc-Microanatomy-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Outside_the_nervous_system" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Outside_the_nervous_system"> <div class="vector-toc-text"> 3.3 Outside the nervous system </div> </a> <ul id="toc-Outside_the_nervous_system-sublist" class="vector-toc-list"> <li id="toc-Digestive_tract_(emetic)" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Digestive_tract_(emetic)"> <div class="vector-toc-text"> 3.3.1 Digestive tract (emetic) </div> </a> <ul id="toc-Digestive_tract_(emetic)-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Lungs" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Lungs"> <div class="vector-toc-text"> 3.3.2 Lungs </div> </a> <ul id="toc-Lungs-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Skin" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Skin"> <div class="vector-toc-text"> 3.3.3 Skin </div> </a> <ul id="toc-Skin-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bone_metabolism" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Bone_metabolism"> <div class="vector-toc-text"> 3.3.4 Bone metabolism </div> </a> <ul id="toc-Bone_metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Organ_development" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Organ_development"> <div class="vector-toc-text"> 3.3.5 Organ development </div> </a> <ul id="toc-Organ_development-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cardiovascular_growth_factor" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cardiovascular_growth_factor"> <div class="vector-toc-text"> 3.3.6 Cardiovascular growth factor </div> </a> <ul id="toc-Cardiovascular_growth_factor-sublist" class="vector-toc-list"> </ul> </li> </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"> 4 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-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> 4.1 Mechanism of action </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Antidepressants" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Antidepressants"> <div class="vector-toc-text"> 4.2 Antidepressants </div> </a> <ul id="toc-Antidepressants-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Anxiolytics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Anxiolytics"> <div class="vector-toc-text"> 4.3 Anxiolytics </div> </a> <ul id="toc-Anxiolytics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Antipsychotics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Antipsychotics"> <div class="vector-toc-text"> 4.4 Antipsychotics </div> </a> <ul id="toc-Antipsychotics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Antimigraine_agents" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Antimigraine_agents"> <div class="vector-toc-text"> 4.5 Antimigraine agents </div> </a> <ul id="toc-Antimigraine_agents-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Antiemetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Antiemetics"> <div class="vector-toc-text"> 4.6 Antiemetics </div> </a> <ul id="toc-Antiemetics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Appetite_suppressants" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Appetite_suppressants"> <div class="vector-toc-text"> 4.7 Appetite suppressants </div> </a> <ul id="toc-Appetite_suppressants-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Anticonvulsants" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Anticonvulsants"> <div class="vector-toc-text"> 4.8 Anticonvulsants </div> </a> <ul id="toc-Anticonvulsants-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Psychedelics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Psychedelics"> <div class="vector-toc-text"> 4.9 Psychedelics </div> </a> <ul id="toc-Psychedelics-sublist" class="vector-toc-list"> <li id="toc-Methyltryptamines_and_hallucinogens" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Methyltryptamines_and_hallucinogens"> <div class="vector-toc-text"> 4.9.1 Methyltryptamines and hallucinogens </div> </a> <ul id="toc-Methyltryptamines_and_hallucinogens-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Entactogens" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Entactogens"> <div class="vector-toc-text"> 4.10 Entactogens </div> </a> <ul id="toc-Entactogens-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Serotonin_syndrome" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Serotonin_syndrome"> <div class="vector-toc-text"> 4.11 Serotonin syndrome </div> </a> <ul id="toc-Serotonin_syndrome-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cardiac_fibrosis_and_other_fibroses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cardiac_fibrosis_and_other_fibroses"> <div class="vector-toc-text"> 4.12 Cardiac fibrosis and other fibroses </div> </a> <ul id="toc-Cardiac_fibrosis_and_other_fibroses-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Comparative_biology_and_evolution" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Comparative_biology_and_evolution"> <div class="vector-toc-text"> 5 Comparative biology and evolution </div> </a> <button aria-controls="toc-Comparative_biology_and_evolution-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Comparative biology and evolution subsection </button> <ul id="toc-Comparative_biology_and_evolution-sublist" class="vector-toc-list"> <li id="toc-Unicellular_organisms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Unicellular_organisms"> <div class="vector-toc-text"> 5.1 Unicellular organisms </div> </a> <ul id="toc-Unicellular_organisms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Edible_plants_and_mushrooms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Edible_plants_and_mushrooms"> <div class="vector-toc-text"> 5.2 Edible plants and mushrooms </div> </a> <ul id="toc-Edible_plants_and_mushrooms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Invertebrates" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Invertebrates"> <div class="vector-toc-text"> 5.3 Invertebrates </div> </a> <ul id="toc-Invertebrates-sublist" class="vector-toc-list"> <li id="toc-Nematodes" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Nematodes"> <div class="vector-toc-text"> 5.3.1 Nematodes </div> </a> <ul id="toc-Nematodes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Decapods" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Decapods"> <div class="vector-toc-text"> 5.3.2 Decapods </div> </a> <ul id="toc-Decapods-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_venoms" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#In_venoms"> <div class="vector-toc-text"> 5.3.3 In venoms </div> </a> <ul id="toc-In_venoms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Insects" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Insects"> <div class="vector-toc-text"> 5.3.4 Insects </div> </a> <ul id="toc-Insects-sublist" class="vector-toc-list"> <li id="toc-Acrididae" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Acrididae"> <div class="vector-toc-text"> 5.3.4.1 Acrididae </div> </a> <ul id="toc-Acrididae-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Role_in_insecticides" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Role_in_insecticides"> <div class="vector-toc-text"> 5.3.4.2 Role in insecticides </div> </a> <ul id="toc-Role_in_insecticides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hymenopterans" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Hymenopterans"> <div class="vector-toc-text"> 5.3.4.3 Hymenopterans </div> </a> <ul id="toc-Hymenopterans-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dipterans" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Dipterans"> <div class="vector-toc-text"> 5.3.4.4 Dipterans </div> </a> <ul id="toc-Dipterans-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Vertebrates" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Vertebrates"> <div class="vector-toc-text"> 5.4 Vertebrates </div> </a> <ul id="toc-Vertebrates-sublist" class="vector-toc-list"> <li id="toc-5-HT_system_in_vertebrates" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#5-HT_system_in_vertebrates"> <div class="vector-toc-text"> 5.4.1 5-HT system in vertebrates </div> </a> <ul id="toc-5-HT_system_in_vertebrates-sublist" class="vector-toc-list"> <li id="toc-Dogs_/_canine_species" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Dogs_/_canine_species"> <div class="vector-toc-text"> 5.4.1.1 Dogs / canine species </div> </a> <ul id="toc-Dogs_/_canine_species-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Teleost_fish" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Teleost_fish"> <div class="vector-toc-text"> 5.4.1.2 Teleost fish </div> </a> <ul id="toc-Teleost_fish-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mice" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Mice"> <div class="vector-toc-text"> 5.4.1.3 Mice </div> </a> <ul id="toc-Mice-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Behavior" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Behavior"> <div class="vector-toc-text"> 5.4.2 Behavior </div> </a> <ul id="toc-Behavior-sublist" class="vector-toc-list"> <li id="toc-Social_interaction" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Social_interaction"> <div class="vector-toc-text"> 5.4.2.1 Social interaction </div> </a> <ul id="toc-Social_interaction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Response_to_stimuli" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Response_to_stimuli"> <div class="vector-toc-text"> 5.4.2.2 Response to stimuli </div> </a> <ul id="toc-Response_to_stimuli-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mood" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Mood"> <div class="vector-toc-text"> 5.4.2.3 Mood </div> </a> <ul id="toc-Mood-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Growth_and_reproduction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Growth_and_reproduction"> <div class="vector-toc-text"> 5.5 Growth and reproduction </div> </a> <ul id="toc-Growth_and_reproduction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Aging_and_age-related_phenotypes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Aging_and_age-related_phenotypes"> <div class="vector-toc-text"> 5.6 Aging and age-related phenotypes </div> </a> <ul id="toc-Aging_and_age-related_phenotypes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biochemical_mechanisms" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biochemical_mechanisms"> <div class="vector-toc-text"> 6 Biochemical mechanisms </div> </a> <button aria-controls="toc-Biochemical_mechanisms-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Biochemical mechanisms subsection </button> <ul id="toc-Biochemical_mechanisms-sublist" class="vector-toc-list"> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> 6.1 Biosynthesis </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Analytical_chemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Analytical_chemistry"> <div class="vector-toc-text"> 7 Analytical chemistry </div> </a> <ul id="toc-Analytical_chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History_and_etymology" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History_and_etymology"> <div class="vector-toc-text"> 8 History and etymology </div> </a> <ul id="toc-History_and_etymology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Notes"> <div class="vector-toc-text"> 9 Notes </div> </a> <ul id="toc-Notes-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"> 10 References </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> 11 Further reading </div> </a> <ul id="toc-Further_reading-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"> 12 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" > <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">Serotonin</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 68 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-68" aria-hidden="true" > 68 languages </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B3%D9%8A%D8%B1%D9%88%D8%AA%D9%88%D9%86%D9%8A%D9%86" title="سيروتونين – Arabic" lang="ar" hreflang="ar" data-title="سيروتونين" 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/Serotonina" title="Serotonina – Asturian" lang="ast" hreflang="ast" data-title="Serotonina" 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/Serotonin" title="Serotonin – Azerbaijani" lang="az" hreflang="az" data-title="Serotonin" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target">Azərbaycanca</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%D8%B1%D9%88%D8%AA%D9%88%D9%86%DB%8C%D9%86" title="سروتونین – South Azerbaijani" lang="azb" hreflang="azb" data-title="سروتونین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B8%E0%A7%87%E0%A6%B0%E0%A7%8B%E0%A6%9F%E0%A7%8B%E0%A6%A8%E0%A6%BF%E0%A6%A8" title="সেরোটোনিন – Bangla" lang="bn" hreflang="bn" data-title="সেরোটোনিন" 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%A1%D0%B5%D1%80%D0%B0%D1%82%D0%B0%D0%BD%D1%96%D0%BD" title="Сератанін – Belarusian" lang="be" hreflang="be" data-title="Сератанін" 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%A1%D1%8D%D1%80%D0%B0%D1%82%D0%B0%D0%BD%D1%96%D0%BD" title="Сэратанін – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Сэратанін" 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%A1%D0%B5%D1%80%D0%BE%D1%82%D0%BE%D0%BD%D0%B8%D0%BD" title="Серотонин – Bulgarian" lang="bg" hreflang="bg" data-title="Серотонин" 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/Serotonin" title="Serotonin – Bosnian" lang="bs" hreflang="bs" data-title="Serotonin" 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/Serotonina" title="Serotonina – Catalan" lang="ca" hreflang="ca" data-title="Serotonina" 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/Serotonin" title="Serotonin – Czech" lang="cs" hreflang="cs" data-title="Serotonin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Serotonin" title="Serotonin – Danish" lang="da" hreflang="da" data-title="Serotonin" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://de.wikipedia.org/wiki/Serotonin" title="Serotonin – German" lang="de" hreflang="de" data-title="Serotonin" 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/Serotoniin" title="Serotoniin – Estonian" lang="et" hreflang="et" data-title="Serotoniin" 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%A3%CE%B5%CF%81%CE%BF%CF%84%CE%BF%CE%BD%CE%AF%CE%BD%CE%B7" title="Σεροτονίνη – Greek" lang="el" hreflang="el" data-title="Σεροτονίνη" 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/Serotonina" title="Serotonina – Spanish" lang="es" hreflang="es" data-title="Serotonina" 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/Serotonino" title="Serotonino – Esperanto" lang="eo" hreflang="eo" data-title="Serotonino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target">Esperanto</a></li><li class="interlanguage-link interwiki-ext mw-list-item"><a href="https://ext.wikipedia.org/wiki/Serotonina" title="Serotonina – Extremaduran" lang="ext" hreflang="ext" data-title="Serotonina" data-language-autonym="Estremeñu" data-language-local-name="Extremaduran" class="interlanguage-link-target">Estremeñu</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Serotonina" title="Serotonina – Basque" lang="eu" hreflang="eu" data-title="Serotonina" 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/%D8%B3%D8%B1%D9%88%D8%AA%D9%88%D9%86%DB%8C%D9%86" title="سروتونین – Persian" lang="fa" hreflang="fa" data-title="سروتونین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/S%C3%A9rotonine" title="Sérotonine – French" lang="fr" hreflang="fr" data-title="Sérotonine" 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/S%C3%A9ireatoinin" title="Séireatoinin – Irish" lang="ga" hreflang="ga" data-title="Séireatoinin" 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/Serotonina" title="Serotonina – Galician" lang="gl" hreflang="gl" data-title="Serotonina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%84%B8%EB%A1%9C%ED%86%A0%EB%8B%8C" title="세로토닌 – Korean" lang="ko" hreflang="ko" data-title="세로토닌" 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/%D5%8D%D5%A5%D6%80%D5%B8%D5%BF%D5%B8%D5%B6%D5%AB%D5%B6" title="Սերոտոնին – Armenian" lang="hy" hreflang="hy" data-title="Սերոտոնին" 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/5-%E0%A4%B9%E0%A4%BE%E0%A4%87%E0%A4%A1%E0%A5%8D%E0%A4%B0%E0%A5%89%E0%A4%95%E0%A5%8D%E0%A4%B8%E0%A4%BF%E0%A4%9F%E0%A5%8D%E0%A4%B0%E0%A4%BF%E0%A4%AA%E0%A5%8D%E0%A4%9F%E0%A4%BE%E0%A4%AE%E0%A4%BF%E0%A4%A8" title="5-हाइड्रॉक्सिट्रिप्टामिन – Hindi" lang="hi" hreflang="hi" data-title="5-हाइड्रॉक्सिट्रिप्टामिन" 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/Serotonin" title="Serotonin – Croatian" lang="hr" hreflang="hr" data-title="Serotonin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Serotonin" title="Serotonin – Indonesian" lang="id" hreflang="id" data-title="Serotonin" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Ser%C3%B3t%C3%B3n%C3%ADn" title="Serótónín – Icelandic" lang="is" hreflang="is" data-title="Serótónín" 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/Serotonina" title="Serotonina – Italian" lang="it" hreflang="it" data-title="Serotonina" 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%A1%D7%A8%D7%95%D7%98%D7%95%D7%A0%D7%99%D7%9F" title="סרוטונין – Hebrew" lang="he" hreflang="he" data-title="סרוטונין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A1%D0%B5%D1%80%D0%BE%D1%82%D0%BE%D0%BD%D0%B8%D0%BD" title="Серотонин – Kazakh" lang="kk" hreflang="kk" data-title="Серотонин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target">Қазақша</a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A1%D0%B5%D1%80%D0%BE%D1%82%D0%BE%D0%BD%D0%B8%D0%BD" title="Серотонин – Kyrgyz" lang="ky" hreflang="ky" data-title="Серотонин" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target">Кыргызча</a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Serotoninum" title="Serotoninum – Latin" lang="la" hreflang="la" data-title="Serotoninum" 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/Seroton%C4%ABns" title="Serotonīns – Latvian" lang="lv" hreflang="lv" data-title="Serotonīns" 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/Serotoninas" title="Serotoninas – Lithuanian" lang="lt" hreflang="lt" data-title="Serotoninas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target">Lietuvių</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Szerotonin" title="Szerotonin – Hungarian" lang="hu" hreflang="hu" data-title="Szerotonin" 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%A1%D0%B5%D1%80%D0%BE%D1%82%D0%BE%D0%BD%D0%B8%D0%BD" title="Серотонин – Macedonian" lang="mk" hreflang="mk" data-title="Серотонин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target">Македонски</a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B8%E0%B5%86%E0%B4%B1%E0%B5%8B%E0%B4%9F%E0%B5%8B%E0%B4%A3%E0%B4%BF%E0%B5%BB" title="സെറോടോണിൻ – Malayalam" lang="ml" hreflang="ml" data-title="സെറോടോണിൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target">മലയാളം</a></li><li class="interlanguage-link interwiki-mr mw-list-item"><a href="https://mr.wikipedia.org/wiki/%E0%A4%B8%E0%A5%87%E0%A4%B0%E0%A5%8B%E0%A4%9F%E0%A5%8B%E0%A4%A8%E0%A4%BF%E0%A4%A8" title="सेरोटोनिन – Marathi" lang="mr" hreflang="mr" data-title="सेरोटोनिन" data-language-autonym="मराठी" data-language-local-name="Marathi" class="interlanguage-link-target">मराठी</a></li><li class="interlanguage-link interwiki-arz mw-list-item"><a href="https://arz.wikipedia.org/wiki/%D8%B3%D9%8A%D8%B1%D9%88%D8%AA%D9%88%D9%86%D9%8A%D9%86" title="سيروتونين – Egyptian Arabic" lang="arz" hreflang="arz" data-title="سيروتونين" 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/Serotonin" title="Serotonin – Malay" lang="ms" hreflang="ms" data-title="Serotonin" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Serotonine" title="Serotonine – Dutch" lang="nl" hreflang="nl" data-title="Serotonine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%BB%E3%83%AD%E3%83%88%E3%83%8B%E3%83%B3" title="セロトニン – Japanese" lang="ja" hreflang="ja" data-title="セロトニン" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Serotonin" title="Serotonin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Serotonin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Serotonina" title="Serotonina – Occitan" lang="oc" hreflang="oc" data-title="Serotonina" 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/Serotonin" title="Serotonin – Uzbek" lang="uz" hreflang="uz" data-title="Serotonin" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target">Oʻzbekcha / ўзбекча</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Serotonina" title="Serotonina – Polish" lang="pl" hreflang="pl" data-title="Serotonina" 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/Serotonina" title="Serotonina – Portuguese" lang="pt" hreflang="pt" data-title="Serotonina" 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/Serotonin%C4%83" title="Serotonină – Romanian" lang="ro" hreflang="ro" data-title="Serotonină" 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%A1%D0%B5%D1%80%D0%BE%D1%82%D0%BE%D0%BD%D0%B8%D0%BD" title="Серотонин – Russian" lang="ru" hreflang="ru" data-title="Серотонин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Serotonin" title="Serotonin – Simple English" lang="en-simple" hreflang="en-simple" data-title="Serotonin" 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/S%C3%A9roton%C3%ADn" title="Sérotonín – Slovak" lang="sk" hreflang="sk" data-title="Sérotonín" 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/Serotonin" title="Serotonin – Slovenian" lang="sl" hreflang="sl" data-title="Serotonin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A1%D0%B5%D1%80%D0%BE%D1%82%D0%BE%D0%BD%D0%B8%D0%BD" title="Серотонин – Serbian" lang="sr" hreflang="sr" data-title="Серотонин" 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/Serotonin" title="Serotonin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Serotonin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Serotoniini" title="Serotoniini – Finnish" lang="fi" hreflang="fi" data-title="Serotoniini" 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/Serotonin" title="Serotonin – Swedish" lang="sv" hreflang="sv" data-title="Serotonin" 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/Serotonin" title="Serotonin – Tagalog" lang="tl" hreflang="tl" data-title="Serotonin" 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%9A%E0%AF%86%E0%AE%B0%E0%AF%8B%E0%AE%9F%E0%AF%8B%E0%AE%A9%E0%AE%BF%E0%AE%A9%E0%AF%8D" title="செரோடோனின் – Tamil" lang="ta" hreflang="ta" data-title="செரோடோனின்" 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%B8%E0%B1%86%E0%B0%B0%E0%B0%9F%E0%B1%8B%E0%B0%A8%E0%B0%BF%E0%B0%A8%E0%B1%8D" title="సెరటోనిన్ – Telugu" lang="te" hreflang="te" data-title="సెరటోనిన్" 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%B9%80%E0%B8%8B%E0%B9%82%E0%B8%A3%E0%B9%82%E0%B8%97%E0%B8%99%E0%B8%B4%E0%B8%99" title="เซโรโทนิน – Thai" lang="th" hreflang="th" data-title="เซโรโทนิน" 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/Serotonin" title="Serotonin – Turkish" lang="tr" hreflang="tr" data-title="Serotonin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A1%D0%B5%D1%80%D0%BE%D1%82%D0%BE%D0%BD%D1%96%D0%BD" title="Серотонін – Ukrainian" lang="uk" hreflang="uk" data-title="Серотонін" 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Monoamine neurotransmitter</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">For other uses, see <a href="/wiki/Serotonin_(disambiguation)" class="mw-disambig" title="Serotonin (disambiguation)">Serotonin (disambiguation)</a>.</div> <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">Serotonin</caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Serotonin-2D-skeletal.svg" class="mw-file-description"><img alt="Skeletal formula of serotonin" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Serotonin-2D-skeletal.svg/220px-Serotonin-2D-skeletal.svg.png" decoding="async" width="220" height="159" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Serotonin-2D-skeletal.svg/330px-Serotonin-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Serotonin-2D-skeletal.svg/440px-Serotonin-2D-skeletal.svg.png 2x" data-file-width="512" data-file-height="371" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">5-HT, 5-Hydroxytryptamine, Enteramine, Thrombocytin, 3-(β-Aminoethyl)-5-hydroxyl solution , Thrombotonin</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Physiological" class="mw-redirect" title="Physiological">Physiological</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Source <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a></th><td class="infobox-data"><a href="/wiki/Raphe_nuclei" title="Raphe nuclei">raphe nuclei</a>, <a href="/wiki/Enterochromaffin_cell" title="Enterochromaffin cell">enterochromaffin cells</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Target tissues</th><td class="infobox-data">system-wide</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptors</a></th><td class="infobox-data"><a href="/wiki/5-HT1_receptor" title="5-HT1 receptor">5-HT1</a>, <a href="/wiki/5-HT2_receptor" title="5-HT2 receptor">5-HT2</a>, <a href="/wiki/5-HT3_receptor" title="5-HT3 receptor">5-HT3</a>, <a href="/wiki/5-HT4_receptor" title="5-HT4 receptor">5-HT4</a>, <a href="/wiki/5-HT5_receptor" class="mw-redirect" title="5-HT5 receptor">5-HT5</a>, <a href="/wiki/5-HT6_receptor" title="5-HT6 receptor">5-HT6</a>, <a href="/wiki/5-HT7_receptor" title="5-HT7 receptor">5-HT7</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Agonist" title="Agonist">Agonists</a></th><td class="infobox-data">Indirectly: <a href="/wiki/SSRI" class="mw-redirect" title="SSRI">SSRIs</a>, <a href="/wiki/MAOI" class="mw-redirect" title="MAOI">MAOIs</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursor</a></th><td class="infobox-data"><a href="/wiki/5-HTP" class="mw-redirect" title="5-HTP">5-HTP</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biosynthesis" title="Biosynthesis">Biosynthesis</a></th><td class="infobox-data"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">Aromatic L-amino acid decarboxylase</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"><a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">MAO</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">3-(2-Aminoethyl)-1H-indol-5-ol</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"><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><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=50-67-9">50-67-9</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/5202">5202</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=5">5</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.5013.html">5013</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/C00780">C00780</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>SRO (<a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=SRO">PDBe</a>, <a rel="nofollow" class="external text" href="https://www.rcsb.org/ligand/SRO">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/DTXSID8075330">DTXSID8075330</a> <a href="https://www.wikidata.org/wiki/Q167934#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/100.000.054">100.000.054</a> <a href="https://www.wikidata.org/wiki/Q167934#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></tbody></table> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Serotonin </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:Serotonin-Spartan-HF-based-on-xtal-3D-balls-web.png" class="mw-file-description" title="Ball-and-stick model of the serotonin molecule"><img alt="Ball-and-stick model of the serotonin molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Serotonin-Spartan-HF-based-on-xtal-3D-balls-web.png/220px-Serotonin-Spartan-HF-based-on-xtal-3D-balls-web.png" decoding="async" width="220" height="174" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Serotonin-Spartan-HF-based-on-xtal-3D-balls-web.png/330px-Serotonin-Spartan-HF-based-on-xtal-3D-balls-web.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/24/Serotonin-Spartan-HF-based-on-xtal-3D-balls-web.png/440px-Serotonin-Spartan-HF-based-on-xtal-3D-balls-web.png 2x" data-file-width="2000" data-file-height="1585" /></a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">5-Hydroxytryptamine</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">3-(2-Aminoethyl)-1H-indol-5-ol</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">5-Hydroxytryptamine, 5-HT, Enteramine; Thrombocytin, 3-(β-Aminoethyl)-5-hydroxyindole, 3-(2-Aminoethyl)indol-5-ol, Thrombotonin</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><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=50-67-9">50-67-9</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C1%3DCC2%3DC%28C%3DC1O%29C%28%3DCN2%29CCN">Interactive image</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=28790">CHEBI:28790</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL39">ChEMBL39</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5013.html">5013</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.054">100.000.054</a> <a href="https://www.wikidata.org/wiki/Q167934#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> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=5">5</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00780">C00780</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Serotonin">Serotonin</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5202">5202</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/333DO1RDJY">333DO1RDJY</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</div> </td> <td><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/DTXSID8075330">DTXSID8075330</a> <a href="https://www.wikidata.org/wiki/Q167934#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> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2 <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: QZAYGJVTTNCVMB-UHFFFAOYSA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: QZAYGJVTTNCVMB-UHFFFAOYAX</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C1=CC2=C(C=C1O)C(=CN2)CCN</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C10H12N2O </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>176.215 g/mol </td></tr> <tr> <td>Appearance </td> <td>White powder </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>167.7 °C (333.9 °F; 440.8 K) 121–122 °C (ligroin)<a href="#cite_note-MP-3">[3]</a> </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>416 ± 30 °C (at 760 Torr)<a href="#cite_note-CAPLUS-1">[1]</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>slightly soluble </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (pKa) </td> <td>10.16 in water at 23.5 °C<a href="#cite_note-pK-2">[2]</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>2.98 <a href="/wiki/Debye" title="Debye">D</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;">Lethal dose or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD50 (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>750 mg/kg (subcutaneous, rat),<a href="#cite_note-rat2-4">[4]</a> 4500 mg/kg (intraperitoneal, rat),<a href="#cite_note-rat-5">[5]</a> 60 mg/kg (oral, rat) </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="http://www.chemcas.com/msds/cas/msds70/50-67-9.asp">External MSDS</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477173047&page2=Serotonin">verify</a> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y<img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> Serotonin (<a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˌsɛrəˈtoʊnɪn, ˌsɪərə-/</a>)<a href="#cite_note-6">[6]</a><a href="#cite_note-7">[7]</a><a href="#cite_note-8">[8]</a> or 5-hydroxytryptamine (5-HT) is a <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitter</a>. Its biological function is complex, touching on diverse functions including <a href="/wiki/Mood_(psychology)" title="Mood (psychology)">mood</a>, <a href="/wiki/Cognition" title="Cognition">cognition</a>, <a href="/wiki/Reward_system" title="Reward system">reward</a>, <a href="/wiki/Learning" title="Learning">learning</a>, <a href="/wiki/Memory" title="Memory">memory</a>, and numerous physiological processes such as <a href="/wiki/Vomiting" title="Vomiting">vomiting</a> and <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstriction</a>.<a href="#cite_note-pmid18043762-9">[9]</a> Serotonin is produced in the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> (CNS), specifically in the <a href="/wiki/Brainstem" title="Brainstem">brainstem</a>'s <a href="/wiki/Raphe_nuclei" title="Raphe nuclei">raphe nuclei</a>, the skin's <a href="/wiki/Merkel_cells" class="mw-redirect" title="Merkel cells">Merkel cells</a>, <a href="/wiki/Pulmonary_neuroendocrine_cell" class="mw-redirect" title="Pulmonary neuroendocrine cell">pulmonary neuroendocrine cells</a> and the tongue's <a href="/wiki/Taste_bud" title="Taste bud">taste receptor cells</a>. Approximately 90% of the serotonin the <a href="/wiki/Human_body" title="Human body">human body</a> produces is in the <a href="/wiki/Gastrointestinal_tract" title="Gastrointestinal tract">gastrointestinal tract</a>'s <a href="/wiki/Enterochromaffin_cell" title="Enterochromaffin cell">enterochromaffin cells</a>, where it regulates intestinal movements.<a href="#cite_note-Caltech_2015-10">[10]</a><a href="#cite_note-urlthemedicalbiochemistrypage.org-11">[11]</a><a href="#cite_note-pmid19630576-12">[12]</a> Additionally, it is stored in blood <a href="/wiki/Platelet" title="Platelet">platelets</a> and is released during agitation and vasoconstriction, where it then acts as an <a href="/wiki/Agonist" title="Agonist">agonist</a> to other platelets.<a href="#cite_note-pmid14727927-13">[13]</a> About 8% is found in platelets and 1–2% in the CNS.<a href="#cite_note-thesis-14">[14]</a> The serotonin is secreted <a href="/wiki/Lumen_(anatomy)" title="Lumen (anatomy)">luminally</a> and <a href="/wiki/Basolateral" class="mw-redirect" title="Basolateral">basolaterally</a>, which leads to increased serotonin uptake by circulating platelets and activation after stimulation, which gives increased stimulation of <a href="/wiki/Myenteric" class="mw-redirect" title="Myenteric">myenteric</a> neurons and <a href="/wiki/Gastrointestinal_motility" class="mw-redirect" title="Gastrointestinal motility">gastrointestinal motility</a>.<a href="#cite_note-15">[15]</a> The remainder is synthesized in serotonergic <a href="/wiki/Neuron" title="Neuron">neurons</a> of the CNS, where it has various functions, including the regulation of mood, <a href="/wiki/Appetite" title="Appetite">appetite</a>, and <a href="/wiki/Sleep" title="Sleep">sleep</a>.<a href="#cite_note-16">[16]</a>[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">unreliable medical source</a>]<a href="#cite_note-17">[17]</a>[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">unreliable medical source</a>] Serotonin secreted from the enterochromaffin cells eventually finds its way out of tissues into the blood. There, it is actively taken up by blood platelets, which store it. When the platelets bind to a <a href="/wiki/Clot" class="mw-redirect" title="Clot">clot</a>, they release serotonin, where it can serve as a <a href="/wiki/Vasoconstrictor" class="mw-redirect" title="Vasoconstrictor">vasoconstrictor</a> or a vasodilator while regulating <a href="/wiki/Hemostasis" title="Hemostasis">hemostasis</a> and blood clotting. In high concentrations, serotonin acts as a vasoconstrictor by contracting <a href="/wiki/Endothelial" class="mw-redirect" title="Endothelial">endothelial</a> <a href="/wiki/Smooth_muscle" title="Smooth muscle">smooth muscle</a> directly or by potentiating the effects of other vasoconstrictors (e.g. angiotensin II and norepinephrine). The vasoconstrictive property is mostly seen in pathologic states affecting the endothelium – such as <a href="/wiki/Atherosclerosis" title="Atherosclerosis">atherosclerosis</a> or chronic <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>. In normal physiologic states, vasodilation occurs through the serotonin mediated release of nitric oxide from endothelial cells, and the inhibition of release of norepinephrine from <a href="/wiki/Adrenergic_nerve_fibre" title="Adrenergic nerve fibre">adrenergic nerves</a>.<a href="#cite_note-18">[18]</a> Serotonin is also a <a href="/wiki/Growth_factor" title="Growth factor">growth factor</a> for some types of cells, which may give it a role in wound healing. There are various <a href="/wiki/5-HT_receptor" title="5-HT receptor">serotonin receptors</a>. Biochemically, the <a href="/wiki/Indoleamine" class="mw-redirect" title="Indoleamine">indoleamine</a> molecule derives from the amino acid <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a>. Serotonin is metabolized mainly to <a href="/wiki/5-hydroxyindoleacetic_acid" class="mw-redirect" title="5-hydroxyindoleacetic acid">5-hydroxyindoleacetic acid</a> (5-HIAA), chiefly by the <a href="/wiki/Liver" title="Liver">liver</a>. Several classes of <a href="/wiki/Antidepressant" title="Antidepressant">antidepressants</a>, such as <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">selective serotonin reuptake inhibitors</a> (SSRIs) and <a href="/wiki/Serotonin%E2%80%93norepinephrine_reuptake_inhibitor" title="Serotonin–norepinephrine reuptake inhibitor">serotonin–norepinephrine reuptake inhibitors</a> (SNRIs), interfere with the normal <a href="/wiki/Reuptake" title="Reuptake">reabsorption</a> of serotonin after it is done with the transmission of the signal, therefore augmenting the neurotransmitter levels in the <a href="/wiki/Synapse" title="Synapse">synapses</a>. Besides mammals, serotonin is found in all <a href="/wiki/Bilateral_animals" class="mw-redirect" title="Bilateral animals">bilateral animals</a> including worms and insects,<a href="#cite_note-Huser_2012-19">[19]</a> as well as in <a href="/wiki/Fungi" class="mw-redirect" title="Fungi">fungi</a> and in <a href="/wiki/Plant" title="Plant">plants</a>.<a href="#cite_note-Ramakrishna_2011-20">[20]</a> Serotonin's presence in insect venoms and plant spines serves to cause pain, which is a side-effect of serotonin injection.<a href="#cite_note-Chen_2010-21">[21]</a><a href="#cite_note-Erspamer-1966-22">[22]</a> Serotonin is produced by pathogenic amoebae, causing <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a> in the human gut.<a href="#cite_note-pmid6308760-23">[23]</a> Its widespread presence in many seeds and fruits may serve to stimulate the digestive tract into expelling the seeds.<a href="#cite_note-feld-24">[24]</a>[<a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">failed verification</a>] <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Molecular_structure">Molecular structure</h2>[<a href="/w/index.php?title=Serotonin&action=edit&section=1" title="Edit section: Molecular structure">edit</a>]</div> Biochemically, the <a href="/wiki/Indoleamine" class="mw-redirect" title="Indoleamine">indoleamine</a> molecule derives from the amino acid <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a>, via the (rate-limiting) <a href="/wiki/Tryptophan_hydroxylase" title="Tryptophan hydroxylase">hydroxylation</a> of the 5 position on the ring (forming the intermediate <a href="/wiki/5-hydroxytryptophan" class="mw-redirect" title="5-hydroxytryptophan">5-hydroxytryptophan</a>), and then <a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">decarboxylation</a> to produce serotonin.<a href="#cite_note-25">[25]</a> Preferable conformations are defined via ethylamine chain, resulting in six different conformations.<a href="#cite_note-26">[26]</a> <div class="mw-heading mw-heading2"><h2 id="Crystal_structure">Crystal structure</h2>[<a href="/w/index.php?title=Serotonin&action=edit&section=2" title="Edit section: Crystal structure">edit</a>]</div> Serotonin crystallizes in P212121 chiral space group forming different hydrogen-bonding interactions between serotonin molecules via N-H...O and O-H...N intermolecular bonds.<a href="#cite_note-27">[27]</a> Serotonin also forms several salts, including pharmaceutical formulation of serotonin adipate.<a href="#cite_note-28">[28]</a> <div class="mw-heading mw-heading2"><h2 id="Biological_role">Biological role</h2>[<a href="/w/index.php?title=Serotonin&action=edit&section=3" title="Edit section: Biological role">edit</a>]</div> Serotonin is involved in numerous physiological processes,<a href="#cite_note-29">[29]</a> including <a href="/wiki/Sleep" title="Sleep">sleep</a>,<a href="#cite_note-Vaseghi_2022-30">[30]</a> <a href="/wiki/Thermoregulation" title="Thermoregulation">thermoregulation</a>, <a href="/wiki/Learning" title="Learning">learning</a> and <a href="/wiki/Memory" title="Memory">memory</a>, <a href="/wiki/Pain" title="Pain">pain</a>, (social) behavior,<a href="#cite_note-pmid2902685-31">[31]</a> <a href="/wiki/Sexual_activity" class="mw-redirect" title="Sexual activity">sexual activity</a>, feeding, motor activity, neural development,<a href="#cite_note-Sinclair-Wilson_Lawrence_Ferezou_Cartonnet-32">[32]</a> and <a href="/wiki/Chronobiology" title="Chronobiology">biological rhythms</a>.<a href="#cite_note-Zifa_1992-33">[33]</a> In less complex animals, such as some <a href="/wiki/Invertebrates" class="mw-redirect" title="Invertebrates">invertebrates</a>, serotonin regulates feeding and other processes.<a href="#cite_note-pmid18522834-34">[34]</a> In plants serotonin synthesis seems to be associated with stress signals.<a href="#cite_note-Ramakrishna_2011-20">[20]</a><a href="#cite_note-Akula-Ravishankar-2011-35">[35]</a> Despite its longstanding prominence in pharmaceutical advertising, the claim that low serotonin levels cause depression is not supported by scientific evidence.<a href="#cite_note-WhitakerCosgrove2015-36">[36]</a><a href="#cite_note-37">[37]</a><a href="#cite_note-38">[38]</a> <div class="mw-heading mw-heading3"><h3 id="Cellular_effects">Cellular effects</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=4" title="Edit section: Cellular effects">edit</a>]</div> Serotonin primarily acts through its receptors and its effects depend on which cells and tissues express these receptors.<a href="#cite_note-Zifa_1992-33">[33]</a> Metabolism involves first <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> by <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidase</a> to <a href="/wiki/5-Hydroxyindoleacetaldehyde" title="5-Hydroxyindoleacetaldehyde">5-hydroxyindoleacetaldehyde</a> (5-HIAL).<a href="#cite_note-BortolatoChenShih2010-39">[39]</a><a href="#cite_note-MatthesMosienkoBashammakh2010-40">[40]</a> The rate-limiting step is hydride transfer from serotonin to the flavin cofactor.<a href="#cite_note-41">[41]</a> There follows oxidation by <a href="/wiki/Aldehyde_dehydrogenase" title="Aldehyde dehydrogenase">aldehyde dehydrogenase</a> (ALDH) to <a href="/wiki/5-hydroxyindoleacetic_acid" class="mw-redirect" title="5-hydroxyindoleacetic acid">5-hydroxyindoleacetic acid</a> (5-HIAA), the <a href="/wiki/Indole" title="Indole">indole</a> acetic-acid derivative. The latter is then excreted by the kidneys. <div class="mw-heading mw-heading4"><h4 id="Receptors">Receptors</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=5" title="Edit section: Receptors">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/Serotonin_receptor" class="mw-redirect" title="Serotonin receptor">Serotonin receptor</a></div> The 5-HT receptors, the <a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">receptors</a> for serotonin, are located on the cell membrane of <a href="/wiki/Neuron" title="Neuron">nerve cells</a> and other cell types in animals, and mediate the effects of serotonin as the <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> <a href="/wiki/Ligand" title="Ligand">ligand</a> and of a broad range of pharmaceutical and <a href="/wiki/Psychedelics" class="mw-redirect" title="Psychedelics">psychedelic drugs</a>. Except for the <a href="/wiki/5-HT3" class="mw-redirect" title="5-HT3">5-HT3 receptor</a>, a ligand-gated <a href="/wiki/Ion_channel" title="Ion channel">ion channel</a>, all other 5-HT receptors are <a href="/wiki/G-protein-coupled_receptors" class="mw-redirect" title="G-protein-coupled receptors">G-protein-coupled receptors</a> (also called seven-transmembrane, or heptahelical receptors) that activate an <a href="/wiki/Intracellular" class="mw-redirect" title="Intracellular">intracellular</a> <a href="/wiki/Second_messenger" class="mw-redirect" title="Second messenger">second messenger</a> cascade.<a href="#cite_note-pmid18571247-42">[42]</a> <div class="mw-heading mw-heading4"><h4 id="Termination">Termination</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=6" title="Edit section: Termination">edit</a>]</div> Serotonergic action is terminated primarily via <a href="/wiki/Reuptake" title="Reuptake">uptake</a> of 5-HT from the synapse. This is accomplished through the specific <a href="/wiki/Monoamine_transporter" title="Monoamine transporter">monoamine transporter</a> for 5-HT, <a href="/wiki/Serotonin_transporter" title="Serotonin transporter">SERT</a>, on the presynaptic neuron. Various agents can inhibit 5-HT reuptake, including <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a> (an <a href="/wiki/Antitussive" class="mw-redirect" title="Antitussive">antitussive</a>), <a href="/wiki/Tricyclic_antidepressants" class="mw-redirect" title="Tricyclic antidepressants">tricyclic antidepressants</a> and <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">selective serotonin reuptake inhibitors</a> (SSRIs). A 2006 study found that a significant portion of 5-HT's synaptic clearance is due to the selective activity of the <a href="/wiki/Plasma_membrane_monoamine_transporter" title="Plasma membrane monoamine transporter">plasma membrane monoamine transporter</a> (PMAT) which actively transports the molecule across the membrane and back into the presynaptic cell.<a href="#cite_note-pmid_1828907-43">[43]</a> In contrast to the high affinity of SERT, the PMAT has been identified as a low-affinity transporter, with an apparent Km of 114 micromoles/l for serotonin, which is approximately 230 times higher than that of SERT. However, the PMAT, despite its relatively low serotonergic affinity, has a considerably higher transport "capacity" than SERT, "resulting in roughly comparable uptake efficiencies to SERT ... in heterologous expression systems."<a href="#cite_note-pmid_1828907-43">[43]</a> The study also suggests that the administration of SSRIs such as <a href="/wiki/Fluoxetine" title="Fluoxetine">fluoxetine</a> and <a href="/wiki/Sertraline" title="Sertraline">sertraline</a> may be associated with an inhibitory effect on PMAT activity when used at higher than normal dosages (<a href="/wiki/IC50" title="IC50">IC50</a> test values used in trials were 3–4 fold higher than typical prescriptive dosage). <div class="mw-heading mw-heading4"><h4 id="Serotonylation">Serotonylation</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=7" title="Edit section: Serotonylation">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/Serotonylation" title="Serotonylation">Serotonylation</a></div> Serotonin can also signal through a nonreceptor mechanism called serotonylation, in which serotonin modifies proteins.<a href="#cite_note-pmid19859528-44">[44]</a> This process underlies serotonin's effects upon platelet-forming cells (<a href="/wiki/Thrombocyte" class="mw-redirect" title="Thrombocyte">thrombocytes</a>) in which it links to the modification of signaling enzymes called <a href="/wiki/GTPase" title="GTPase">GTPases</a> that then trigger the release of vesicle contents by <a href="/wiki/Exocytosis" title="Exocytosis">exocytosis</a>.<a href="#cite_note-pmid14697203-45">[45]</a> A similar process underlies the pancreatic release of insulin.<a href="#cite_note-pmid19859528-44">[44]</a> The effects of serotonin upon vascular smooth <a href="/wiki/Muscle_tone" title="Muscle tone">muscle tone</a> – the biological function after which serotonin was originally named – depend upon the serotonylation of proteins involved in the contractile apparatus of muscle cells.<a href="#cite_note-pmid19479059-46">[46]</a> <table class="wikitable"> <caption><big>Binding profile of serotonin</big> </caption> <tbody><tr> <th>Receptor</th> <th>Ki (nM)<a href="#cite_note-47">[47]</a></th> <th>Receptor function<a href="#cite_note-48">[Note 1]</a> </th></tr> <tr> <td colspan="3" align="center">5-HT1 receptor family signals via <a href="/wiki/Gi_alpha_subunit" title="Gi alpha subunit">Gi/o</a> inhibition of <a href="/wiki/Adenylyl_cyclase" title="Adenylyl cyclase">adenylyl cyclase</a>. </td></tr> <tr> <td><a href="/wiki/5-HT1A_receptor" title="5-HT1A receptor">5-HT1A</a></td> <td>3.17</td> <td>Memory[<a href="/wiki/Wikipedia:Vagueness" title="Wikipedia:Vagueness">vague</a>] (agonists ↓); learning[<a href="/wiki/Wikipedia:Vagueness" title="Wikipedia:Vagueness">vague</a>] (agonists ↓); anxiety (agonists ↓); depression (agonists ↓); positive, negative, and cognitive symptoms of schizophrenia (partial agonists ↓); analgesia (agonists ↑); <a href="/wiki/Aggression" title="Aggression">aggression</a> (agonists ↓); dopamine release in the prefrontal cortex (agonists ↑); serotonin release and synthesis (agonists ↓) </td></tr> <tr> <td><a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT1B</a></td> <td>4.32</td> <td>Vasoconstriction (agonists ↑); aggression (agonists ↓); bone mass (↓). Serotonin autoreceptor. </td></tr> <tr> <td><a href="/wiki/5-HT1D_receptor" title="5-HT1D receptor">5-HT1D</a></td> <td>5.03</td> <td>Vasoconstriction (agonists ↑) </td></tr> <tr> <td><a href="/wiki/5-HT1E_receptor" title="5-HT1E receptor">5-HT1E</a></td> <td>7.53</td> <td> </td></tr> <tr> <td><a href="/wiki/5-HT1F_receptor" title="5-HT1F receptor">5-HT1F</a></td> <td>10</td> <td> </td></tr> <tr> <td colspan="3" align="center">5-HT2 receptor family signals via <a href="/wiki/Gq_alpha_subunit" title="Gq alpha subunit">Gq</a> activation of <a href="/wiki/Phospholipase_C" title="Phospholipase C">phospholipase C</a>. </td></tr> <tr> <td><a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A</a></td> <td>11.55</td> <td>Psychedelia (agonists ↑); depression (agonists & antagonists ↓); anxiety (antagonists ↓); positive and negative symptoms of schizophrenia (antagonists ↓); norepinephrine release from the <a href="/wiki/Locus_coeruleus" title="Locus coeruleus">locus coeruleus</a> (antagonists ↑); glutamate release in the <a href="/wiki/Prefrontal_cortex" title="Prefrontal cortex">prefrontal cortex</a> (agonists ↑); dopamine in the prefrontal cortex (agonists ↑);<a href="#cite_note-49">[48]</a> urinary bladder contractions (agonists ↑)<a href="#cite_note-MoroEdwards2016-50">[49]</a> </td></tr> <tr> <td><a href="/wiki/5-HT2B_receptor" title="5-HT2B receptor">5-HT2B</a></td> <td>8.71</td> <td>Cardiovascular functioning (agonists increase risk of pulmonary hypertension), empathy (via <a href="/wiki/Von_Economo_neurons" class="mw-redirect" title="Von Economo neurons">von Economo neurons</a><a href="#cite_note-51">[50]</a>) </td></tr> <tr> <td><a href="/wiki/5-HT2C_receptor" title="5-HT2C receptor">5-HT2C</a></td> <td>5.02</td> <td>Dopamine release into the mesocorticolimbic pathway (agonists ↓); acetylcholine release in the prefrontal cortex (agonists ↑); dopaminergic and noradrenergic activity in the <a href="/wiki/Frontal_cortex" class="mw-redirect" title="Frontal cortex">frontal cortex</a> (antagonists ↑);<a href="#cite_note-52">[51]</a> appetite (agonists ↓); antipsychotic effects (agonists ↑); antidepressant effects (agonists & antagonists ↑) </td></tr> <tr> <td colspan="3" align="center">Other 5-HT receptors </td></tr> <tr> <td><a href="/wiki/5-HT3_receptor" title="5-HT3 receptor">5-HT3</a></td> <td>593</td> <td>Emesis (agonists ↑); anxiolysis (antagonists ↑). </td></tr> <tr> <td><a href="/wiki/5-HT4_receptor" title="5-HT4 receptor">5-HT4</a></td> <td>125.89</td> <td>Movement of food across the GI tract (agonists ↑); memory & learning (agonists ↑); antidepressant effects (agonists ↑). Signalling via <a href="/wiki/Gs_alpha_subunit" title="Gs alpha subunit">Gαs</a> activation of adenylyl cyclase. </td></tr> <tr> <td><a href="/wiki/5-HT5A_receptor" title="5-HT5A receptor">5-HT5A</a></td> <td>251.2</td> <td>Memory consolidation.<a href="#cite_note-53">[52]</a> Signals via <a href="/wiki/Gi_alpha_subunit" title="Gi alpha subunit">Gi/o</a> inhibition of <a href="/wiki/Adenylyl_cyclase" title="Adenylyl cyclase">adenylyl cyclase</a>. </td></tr> <tr> <td><a href="/wiki/5-HT6_receptor" title="5-HT6 receptor">5-HT6</a></td> <td>98.41</td> <td>Cognition (antagonists ↑); antidepressant effects (agonists & antagonists ↑); <a href="/wiki/Anxiogenic" title="Anxiogenic">anxiogenic</a> effects (antagonists ↑<a href="#cite_note-54">[53]</a>). <a href="/wiki/Gs_alpha_subunit" title="Gs alpha subunit">Gs</a> signalling via activating <a href="/wiki/Adenylyl_cyclase" title="Adenylyl cyclase">adenylyl cyclase</a>. </td></tr> <tr> <td><a href="/wiki/5-HT7_receptor" title="5-HT7 receptor">5-HT7</a></td> <td>8.11</td> <td>Cognition (antagonists ↑); antidepressant effects (antagonists ↑). Acts by <a href="/wiki/Gs_alpha_subunit" title="Gs alpha subunit">Gs</a> signalling via activating <a href="/wiki/Adenylyl_cyclase" title="Adenylyl cyclase">adenylyl cyclase</a>. </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Nervous_system">Nervous system</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=8" title="Edit section: Nervous system">edit</a>]</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Pubmed_equitativa_hormonal.png" class="mw-file-description"><img alt="In this drawing of the brain, the serotonergic system is red and the mesolimbic dopamine pathway is blue. There is one collection of serotonergic neurons in the upper brainstem that sends axons upwards to the whole cerebrum, and one collection next to the cerebellum that sends axons downward to the spinal cord. Slightly forward the upper serotonergic neurons is the ventral tegmental area (VTA), which contains dopaminergic neurons. These neurons' axons then connect to the nucleus accumbens, hippocampus, and the frontal cortex. Over the VTA is another collection of dopaminergic cells, the substansia nigra, which send axons to the striatum." src="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Pubmed_equitativa_hormonal.png/220px-Pubmed_equitativa_hormonal.png" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Pubmed_equitativa_hormonal.png/330px-Pubmed_equitativa_hormonal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Pubmed_equitativa_hormonal.png/440px-Pubmed_equitativa_hormonal.png 2x" data-file-width="714" data-file-height="536" /></a><figcaption>Serotonin system, contrasted with the <a href="/wiki/Mesolimbic_pathway" title="Mesolimbic pathway">dopamine system</a></figcaption></figure> The neurons of the <a href="/wiki/Raphe_nuclei" title="Raphe nuclei">raphe nuclei</a> are the principal source of 5-HT release in the brain.<a href="#cite_note-55">[54]</a> There are nine raphe nuclei, designated B1–B9, which contain the majority of serotonin-containing neurons (some scientists chose to group the nuclei raphes lineares into one nucleus), all of which are located along the midline of the <a href="/wiki/Brainstem" title="Brainstem">brainstem</a>, and centered on the <a href="/wiki/Reticular_formation" title="Reticular formation">reticular formation</a>.<a href="#cite_note-56">[55]</a><a href="#cite_note-57">[56]</a> Axons from the neurons of the raphe nuclei form a <a href="/wiki/Neurotransmitter_system" class="mw-redirect" title="Neurotransmitter system">neurotransmitter system</a> reaching almost every part of the central nervous system. Axons of neurons in the lower raphe nuclei terminate in the <a href="/wiki/Cerebellum" title="Cerebellum">cerebellum</a> and <a href="/wiki/Spinal_cord" title="Spinal cord">spinal cord</a>, while the axons of the higher nuclei spread out in the entire brain. <div class="mw-heading mw-heading4"><h4 id="Ultrastructure_and_function">Ultrastructure and function</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=9" title="Edit section: Ultrastructure and function">edit</a>]</div> The serotonin nuclei may also be divided into two main groups, the rostral and caudal containing three and four nuclei respectively. The rostral group consists of the caudal linear nuclei (B8), the dorsal raphe nuclei (B6 and B7) and the median raphe nuclei (B5, B8 and B9), that project into multiple cortical and subcortical structures. The caudal group consists of the nucleus raphe magnus (B3), raphe obscurus nucleus (B2), raphe pallidus nucleus (B1), and lateral medullary reticular formation, that project into the brainstem.<a href="#cite_note-58">[57]</a> The serotonergic pathway is involved in sensorimotor function, with pathways projecting both into cortical (Dorsal and Median Raphe Nuclei), subcortical, and spinal areas involved in motor activity. Pharmacological manipulation suggests that serotonergic activity increases with motor activity while firing rates of serotonergic neurons increase with intense visual stimuli. Animal models suggest that kainate signaling negatively regulates serotonin actions in the retina, with possible implications for the control of the visual system.<a href="#cite_note-59">[58]</a> The descending projections form a pathway that inhibits pain called the "descending inhibitory pathway" that may be relevant to a disorder such as fibromyalgia, migraine, and other pain disorders, and the efficacy of antidepressants in them.<a href="#cite_note-60">[59]</a> Serotonergic projections from the caudal nuclei are involved in regulating mood and emotion, and hypo-<a href="#cite_note-61">[60]</a> or hyper-serotonergic<a href="#cite_note-62">[61]</a> states may be involved in depression and sickness behavior. <div class="mw-heading mw-heading4"><h4 id="Microanatomy">Microanatomy</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=10" title="Edit section: Microanatomy">edit</a>]</div> Serotonin is released into the synapse, or space between neurons, and diffuses over a relatively wide gap (>20 nm) to activate <a href="/wiki/5-HT_receptor" title="5-HT receptor">5-HT receptors</a> located on the <a href="/wiki/Dendrite" title="Dendrite">dendrites</a>, cell bodies, and <a href="/wiki/Presynaptic_terminal" class="mw-redirect" title="Presynaptic terminal">presynaptic terminals</a> of adjacent neurons. When humans smell food, dopamine is released to <a href="/wiki/Incentive_salience" class="mw-redirect" title="Incentive salience">increase the appetite</a>. But, unlike in worms, serotonin does not increase anticipatory behaviour in humans; instead, the serotonin released while consuming activates <a href="/wiki/5-HT2C_receptor" title="5-HT2C receptor">5-HT2C receptors</a> on dopamine-producing cells. This halts their dopamine release, and thereby serotonin decreases appetite. Drugs that block 5-HT2C receptors make the body unable to recognize when it is no longer hungry or otherwise in need of nutrients, and are associated with weight gain,<a href="#cite_note-pmid19178394-63">[62]</a> especially in people with a low number of receptors.<a href="#cite_note-pmid15741483-64">[63]</a> The expression of 5-HT2C receptors in the <a href="/wiki/Hippocampus" title="Hippocampus">hippocampus</a> follows a <a href="/wiki/Circadian_rhythm" title="Circadian rhythm">diurnal rhythm</a>,<a href="#cite_note-pmid9151722-65">[64]</a> just as the serotonin release in the <a href="/wiki/Ventromedial_nucleus" class="mw-redirect" title="Ventromedial nucleus">ventromedial nucleus</a>, which is characterised by a peak at morning when the motivation to eat is strongest.<a href="#cite_note-pmid2197074-66">[65]</a> In <a href="/wiki/Macaque" title="Macaque">macaques</a>, alpha males have twice the level of serotonin in the brain as subordinate males and females (measured by the concentration of <a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a> in the <a href="/wiki/Cerebrospinal_fluid" title="Cerebrospinal fluid">cerebrospinal fluid</a> (CSF)). Dominance status and CSF serotonin levels appear to be positively correlated. When dominant males were removed from such groups, subordinate males begin competing for dominance. Once new dominance hierarchies were established, serotonin levels of the new dominant individuals also increased to double those in subordinate males and females. The reason why serotonin levels are only high in dominant males, but not dominant females has not yet been established.<a href="#cite_note-67">[66]</a> In humans, levels of 5-HT1A receptor inhibition in the brain show negative correlation with aggression,<a href="#cite_note-68">[67]</a> and a mutation in the gene that codes for the <a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A</a> receptor may double the risk of suicide for those with that genotype.<a href="#cite_note-Basky_2000-69">[68]</a> Serotonin in the brain is not usually degraded after use, but is collected by serotonergic neurons by <a href="/wiki/Serotonin_transporter" title="Serotonin transporter">serotonin transporters</a> on their cell surfaces. Studies have revealed nearly 10% of total variance in anxiety-related personality depends on variations in the <a href="/wiki/5-HTTLPR" title="5-HTTLPR">description of where, when and how many</a> serotonin transporters the neurons should deploy.<a href="#cite_note-pmid8929413-70">[69]</a> <div class="mw-heading mw-heading3"><h3 id="Outside_the_nervous_system">Outside the nervous system</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=11" title="Edit section: Outside the nervous system">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Digestive_tract_(emetic)">Digestive tract (emetic)</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=12" title="Edit section: Digestive tract (emetic)">edit</a>]</div> Serotonin regulates gastrointestinal (GI) function. The gut is surrounded by <a href="/wiki/Enterochromaffin_cell" title="Enterochromaffin cell">enterochromaffin cells</a>, which release serotonin in response to food in the <a href="/wiki/Lumen_(anatomy)" title="Lumen (anatomy)">lumen</a>. This makes the gut contract around the food. Platelets in the <a href="/wiki/Hepatic_portal_system" title="Hepatic portal system">veins draining the gut</a> collect excess serotonin. There are often serotonin abnormalities in gastrointestinal disorders such as constipation and irritable bowel syndrome.<a href="#cite_note-ReferenceA-71">[70]</a> If irritants are present in the food, the enterochromaffin cells release more serotonin to make the gut move faster, i.e., to cause diarrhea, so the gut is emptied of the noxious substance. If serotonin is released in the blood faster than the platelets can absorb it, the level of free serotonin in the blood is increased. This activates <a href="/wiki/5-HT3_receptor" title="5-HT3 receptor">5-HT3 receptors</a> in the <a href="/wiki/Chemoreceptor_trigger_zone" title="Chemoreceptor trigger zone">chemoreceptor trigger zone</a> that stimulate <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>.<a href="#cite_note-72">[71]</a> Thus, drugs and toxins stimulate serotonin release from enterochromaffin cells in the gut wall can induce emesis. The enterochromaffin cells not only react to bad food but are also very sensitive to <a href="/wiki/Radiation_therapy" title="Radiation therapy">irradiation</a> and <a href="/wiki/Chemotherapy" title="Chemotherapy">cancer chemotherapy</a>. Drugs that <a href="/wiki/5-HT_antagonist" class="mw-redirect" title="5-HT antagonist">block 5HT3</a> are very effective in controlling the nausea and vomiting produced by cancer treatment, and are considered the gold standard for this purpose.<a href="#cite_note-73">[72]</a> <div class="mw-heading mw-heading4"><h4 id="Lungs">Lungs</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=13" title="Edit section: Lungs">edit</a>]</div> The <a href="/wiki/Lung" title="Lung">lung</a>,<a href="#cite_note-Lauweryns_1973-74">[73]</a> including that of reptiles,<a href="#cite_note-Pastor_Ballesta_Perez-Tomas_Marin_1987_pp._713–715-75">[74]</a> contains specialized <a href="/wiki/Epithelial_cells" class="mw-redirect" title="Epithelial cells">epithelial cells</a> that occur as solitary cells or as clusters called neuroepithelial bodies or bronchial Kulchitsky cells or alternatively K cells.<a href="#cite_note-Sonstegard_1982-76">[75]</a> These are enterochromaffin cells that like those in the gut release serotonin.<a href="#cite_note-Sonstegard_1982-76">[75]</a> Their function is probably <a href="/wiki/Hypoxic_pulmonary_vasoconstriction" title="Hypoxic pulmonary vasoconstriction">vasoconstriction during hypoxia</a>.<a href="#cite_note-Lauweryns_1973-74">[73]</a> <div class="mw-heading mw-heading4"><h4 id="Skin">Skin</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=14" title="Edit section: Skin">edit</a>]</div> Serotonin is also produced by <a href="/wiki/Merkel_cell" title="Merkel cell">Merkel cells</a> which are part of the <a href="/wiki/Somatosensory" class="mw-redirect" title="Somatosensory">somatosensory</a> system.<a href="#cite_note-77">[76]</a> <div class="mw-heading mw-heading4"><h4 id="Bone_metabolism">Bone metabolism</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=15" title="Edit section: Bone metabolism">edit</a>]</div> In mice and humans, alterations in serotonin levels and signalling have been shown to regulate bone mass.<a href="#cite_note-pmid20200960-78">[77]</a><a href="#cite_note-pmid19197289-79">[78]</a><a href="#cite_note-pmid19594297-80">[79]</a><a href="#cite_note-pmid21351148-81">[80]</a> Mice that lack brain serotonin have <a href="/wiki/Osteopenia" title="Osteopenia">osteopenia</a>, while mice that lack gut serotonin have high bone density. In humans, increased blood serotonin levels have been shown to be a significant negative predictor of low bone density. Serotonin can also be synthesized, albeit at very low levels, in the bone cells. It mediates its actions on bone cells using three different receptors. Through <a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT1B receptors</a>, it negatively regulates bone mass, while it does so positively through <a href="/wiki/5-HT2B_receptor" title="5-HT2B receptor">5-HT2B receptors</a> and <a href="/wiki/5-HT2C_receptor" title="5-HT2C receptor">5-HT2C receptors</a>. There is very delicate balance between physiological role of gut serotonin and its pathology. Increase in the extracellular content of serotonin results in a complex relay of signals in the osteoblasts culminating in FoxO1/ Creb and ATF4 dependent transcriptional events.<a href="#cite_note-pmid22945629-82">[81]</a> Following the 2008 findings that gut serotonin regulates bone mass, the mechanistic investigations into what regulates serotonin synthesis from the gut in the regulation of bone mass have started. <a href="/wiki/PIEZO1" title="PIEZO1">Piezo1</a> has been shown to sense RNA in the gut and relay this information through serotonin synthesis to the bone by acting as a sensor of single-stranded RNA (ssRNA) governing 5-HT production. Intestinal epithelium-specific deletion of mouse Piezo1 profoundly disturbed gut peristalsis, impeded experimental colitis, and suppressed serum 5-HT levels. Because of systemic 5-HT deficiency, conditional knockout of Piezo1 increased bone formation. Notably, fecal ssRNA was identified as a natural Piezo1 ligand, and ssRNA-stimulated 5-HT synthesis from the gut was evoked in a MyD88/TRIF-independent manner. Colonic infusion of RNase A suppressed gut motility and increased bone mass. These findings suggest gut ssRNA as a master determinant of systemic 5-HT levels, indicating the ssRNA-Piezo1 axis as a potential prophylactic target for treatment of bone and gut disorders. Studies in 2008, 2010 and 2019 have opened the potential for serotonin research to treat bone mass disorders.<a href="#cite_note-pmid20139991-83">[82]</a><a href="#cite_note-pmid32640190-84">[83]</a> <div class="mw-heading mw-heading4"><h4 id="Organ_development">Organ development</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=16" title="Edit section: Organ development">edit</a>]</div> Since serotonin signals resource availability it is not surprising that it affects organ development. Many human and animal studies have shown that nutrition in early life can influence, in adulthood, such things as body fatness, blood lipids, blood pressure, <a href="/wiki/Atherosclerosis" title="Atherosclerosis">atherosclerosis</a>, behavior, learning, and longevity.<a href="#cite_note-85">[84]</a><a href="#cite_note-86">[85]</a><a href="#cite_note-Hahn1984-87">[86]</a> Rodent experiment shows that neonatal exposure to SSRIs makes persistent changes in the serotonergic transmission of the brain resulting in behavioral changes,<a href="#cite_note-pmid18385313-88">[87]</a><a href="#cite_note-pmid16012532-89">[88]</a> which are reversed by treatment with antidepressants.<a href="#cite_note-pmid16483567-90">[89]</a> By treating normal and <a href="/wiki/Knockout_mouse" title="Knockout mouse">knockout mice</a> lacking the serotonin transporter with fluoxetine scientists showed that normal emotional reactions in adulthood, like a short latency to escape foot shocks and inclination to explore new environments were dependent on active serotonin transporters during the neonatal period.<a href="#cite_note-91">[90]</a><a href="#cite_note-92">[91]</a> Human serotonin can also act as a <a href="/wiki/Growth_factor" title="Growth factor">growth factor</a> directly. Liver damage increases cellular expression of <a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A</a> and <a href="/wiki/5-HT2B_receptor" title="5-HT2B receptor">5-HT2B receptors</a>, mediating liver compensatory regrowth (see <a href="/wiki/Liver#Regeneration_and_transplantation" title="Liver">Liver § Regeneration and transplantation</a>)<a href="#cite_note-pmid16601191-93">[92]</a> Serotonin present in the blood then stimulates cellular growth to repair liver damage.<a href="#cite_note-pmid19246633-94">[93]</a> 5-HT2B receptors also activate <a href="/wiki/Osteocyte" title="Osteocyte">osteocytes</a>, which build up bone<a href="#cite_note-pmid17846081-95">[94]</a> However, serotonin also inhibits <a href="/wiki/Osteoblast" title="Osteoblast">osteoblasts</a>, through 5-HT1B receptors.<a href="#cite_note-pmid19041748-96">[95]</a> <div class="mw-heading mw-heading4"><h4 id="Cardiovascular_growth_factor">Cardiovascular growth factor</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=17" title="Edit section: Cardiovascular growth factor">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/Cardiac_fibrosis" title="Cardiac fibrosis">Cardiac fibrosis</a></div> Serotonin, in addition, evokes <a href="/wiki/Endothelium" title="Endothelium">endothelial</a> <a href="/wiki/Nitric_oxide_synthase" title="Nitric oxide synthase">nitric oxide synthase</a> activation and stimulates, through a <a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT1B receptor</a>-mediated mechanism, the phosphorylation of p44/p42 mitogen-activated protein kinase activation in bovine aortic endothelial cell cultures.[<a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify">clarification needed</a>]<a href="#cite_note-pmid10710124-97">[96]</a> In blood, serotonin is collected from plasma by platelets, which store it. It is thus active wherever platelets bind in damaged tissue, as a vasoconstrictor to stop bleeding, and also as a fibrocyte mitotic (growth factor), to aid healing.<a href="#cite_note-98">[97]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Serotonin&action=edit&section=18" title="Edit section: Pharmacology">edit</a>]</div> Several classes of <a href="/wiki/Drugs" class="mw-redirect" title="Drugs">drugs</a> target the serotonin system, including some <a href="/wiki/Antidepressant" title="Antidepressant">antidepressants</a>, <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytics</a>, <a href="/wiki/Antipsychotic" title="Antipsychotic">antipsychotics</a>, <a href="/wiki/Analgesic" title="Analgesic">analgesics</a>, <a href="/wiki/Antimigraine_drug" title="Antimigraine drug">antimigraine drugs</a>, <a href="/wiki/Antiemetic" title="Antiemetic">antiemetics</a>, <a href="/wiki/Appetite_suppressant" class="mw-redirect" title="Appetite suppressant">appetite suppressants</a>, and <a href="/wiki/Anticonvulsant" title="Anticonvulsant">anticonvulsants</a>, as well as <a href="/wiki/Psychedelic_drug" title="Psychedelic drug">psychedelics</a> and <a href="/wiki/Entactogen" class="mw-redirect" title="Entactogen">entactogens</a>. <div class="mw-heading mw-heading3"><h3 id="Mechanism_of_action">Mechanism of action</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=19" title="Edit section: Mechanism of action">edit</a>]</div> At rest, serotonin is stored within the vesicles of presynaptic neurons. When stimulated by nerve impulses, serotonin is released as a neurotransmitter into the synapse, reversibly binding to the postsynaptic receptor to induce a nerve impulse on the postsynaptic neuron. Serotonin can also bind to auto-receptors on the presynaptic neuron to regulate the synthesis and release of serotonin. Normally serotonin is taken back into the presynaptic neuron to stop its action, then reused or broken down by monoamine oxidase.<a href="#cite_note-99">[98]</a> <div class="mw-heading mw-heading3"><h3 id="Antidepressants">Antidepressants</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=20" title="Edit section: Antidepressants">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/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">Selective serotonin reuptake inhibitor</a> and <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">Monoamine oxidase inhibitor</a></div> Drugs that alter serotonin levels are used in treating <a href="/wiki/Major_depressive_disorder" title="Major depressive disorder">depression</a>, <a href="/wiki/Generalized_anxiety_disorder" title="Generalized anxiety disorder">generalized anxiety disorder</a>, and <a href="/wiki/Social_anxiety_disorder" title="Social anxiety disorder">social phobia</a>. <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">Monoamine oxidase inhibitors</a> (MAOIs) prevent the breakdown of <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitters</a> (including serotonin), and therefore increase concentrations of the neurotransmitter in the brain. MAOI therapy is associated with many adverse drug reactions, and patients are at risk of <a href="/wiki/Hypertensive_emergency" title="Hypertensive emergency">hypertensive emergency</a> triggered by foods with high <a href="/wiki/Tyramine" title="Tyramine">tyramine</a> content, and certain drugs. Some drugs inhibit the re-uptake of serotonin, making it stay in the synaptic cleft longer. The <a href="/wiki/Tricyclic_antidepressants" class="mw-redirect" title="Tricyclic antidepressants">tricyclic antidepressants</a> (TCAs) inhibit the reuptake of both serotonin and <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>. The newer <a href="/wiki/Selective_and_non-selective" class="mw-redirect" title="Selective and non-selective">selective</a> serotonin reuptake inhibitors (<a href="/wiki/SSRI" class="mw-redirect" title="SSRI">SSRIs</a>) have fewer side-effects and fewer interactions with other drugs.<a href="#cite_note-100">[99]</a> Certain SSRI medications have been shown to lower serotonin levels below the baseline after chronic use, despite initial increases.<a href="#cite_note-pmid10575045-101">[100]</a> The <a href="/wiki/5-HTTLPR" title="5-HTTLPR">5-HTTLPR</a> gene codes for the number of serotonin transporters in the brain, with more serotonin transporters causing decreased duration and magnitude of serotonergic signaling.<a href="#cite_note-102">[101]</a> The 5-HTTLPR polymorphism (l/l) causing more serotonin transporters to be formed is also found to be more resilient against depression and anxiety.<a href="#cite_note-103">[102]</a><a href="#cite_note-104">[103]</a> Besides their use in treating depression and anxiety, certain serotonergic antidepressants are also approved and used to treat <a href="/wiki/Fibromyalgia" title="Fibromyalgia">fibromyalgia</a>, <a href="/wiki/Neuropathic_pain" title="Neuropathic pain">neuropathic pain</a>, and <a href="/wiki/Chronic_fatigue_syndrome" class="mw-redirect" title="Chronic fatigue syndrome">chronic fatigue syndrome</a>.<a href="#cite_note-O'MalleyJacksonSantoro1999-105">[104]</a><a href="#cite_note-WelschÜçeylerKlose2018-106">[105]</a> <div class="mw-heading mw-heading3"><h3 id="Anxiolytics">Anxiolytics</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=21" title="Edit section: Anxiolytics">edit</a>]</div> <a href="/wiki/Azapirone" title="Azapirone">Azapirone</a> <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytics</a> like <a href="/wiki/Buspirone" title="Buspirone">buspirone</a> and <a href="/wiki/Tandospirone" title="Tandospirone">tandospirone</a> act as serotonin <a href="/wiki/5-HT1A_receptor" title="5-HT1A receptor">5-HT1A receptor</a> <a href="/wiki/Agonist" title="Agonist">agonists</a>.<a href="#cite_note-TaylorMoon1991-107">[106]</a><a href="#cite_note-KishiMeltzerMatsuda2014-108">[107]</a> <div class="mw-heading mw-heading3"><h3 id="Antipsychotics">Antipsychotics</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=22" title="Edit section: Antipsychotics">edit</a>]</div> Many <a href="/wiki/Antipsychotic" title="Antipsychotic">antipsychotics</a> bind to and modulate <a href="/wiki/Serotonin_receptor" class="mw-redirect" title="Serotonin receptor">serotonin receptors</a>, including the serotonin <a href="/wiki/5-HT1A_receptor" title="5-HT1A receptor">5-HT1A</a>, <a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A</a>, <a href="/wiki/5-HT2B_receptor" title="5-HT2B receptor">5-HT2B</a>, <a href="/wiki/5-HT2C_receptor" title="5-HT2C receptor">5-HT2C</a>, <a href="/wiki/5-HT6_receptor" title="5-HT6 receptor">5-HT6</a>, and <a href="/wiki/5-HT7_receptor" title="5-HT7 receptor">5-HT7 receptors</a>, among others.<a href="#cite_note-Meltzer1999-109">[108]</a><a href="#cite_note-Meltzer2012-110">[109]</a> Activation of serotonin 5-HT1A receptors and blockade of serotonin 5-HT2A receptors may contribute to the therapeutic antipsychotic effects of these agents, whereas antagonism of serotonin 5-HT2C receptors has been especially implicated in <a href="/wiki/Side_effect" title="Side effect">side effects</a> of antipsychotics.<a href="#cite_note-Meltzer1999-109">[108]</a><a href="#cite_note-Meltzer2012-110">[109]</a> <div class="mw-heading mw-heading3"><h3 id="Antimigraine_agents">Antimigraine agents</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=23" title="Edit section: Antimigraine agents">edit</a>]</div> <a href="/wiki/Antimigraine_agent" class="mw-redirect" title="Antimigraine agent">Antimigraine agents</a> such as the <a href="/wiki/Triptan" title="Triptan">triptans</a> like <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a> act as <a href="/wiki/Agonist" title="Agonist">agonists</a> of the serotonin <a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT1B</a>, <a href="/wiki/5-HT1D_receptor" title="5-HT1D receptor">5-HT1D</a>, and/or <a href="/wiki/5-HT1F_receptor" title="5-HT1F receptor">5-HT1F receptors</a>.<a href="#cite_note-Tfelt-HansenDeVriesSaxena2000-111">[110]</a><a href="#cite_note-RamírezRosasLabruijereVillalón2013-112">[111]</a> Earlier antimigraine agents were the <a href="/wiki/Ergoline" title="Ergoline">ergoline</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivatives</a> and <a href="/wiki/Ergot" title="Ergot">ergot</a>-related drugs such as <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, and <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, which act as <a href="/wiki/Binding_selectivity" title="Binding selectivity">non-selective</a> <a href="/wiki/Serotonin_receptor_agonist" title="Serotonin receptor agonist">serotonin receptor agonists</a>.<a href="#cite_note-RamírezRosasLabruijereVillalón2013-112">[111]</a><a href="#cite_note-SaxenaDenBoer1991-113">[112]</a><a href="#cite_note-WhealyBecker2024-114">[113]</a> <div class="mw-heading mw-heading3"><h3 id="Antiemetics">Antiemetics</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=24" title="Edit section: Antiemetics">edit</a>]</div> Some serotonin <a href="/wiki/5-HT3_antagonist" title="5-HT3 antagonist">5-HT3 receptor antagonists</a>, such as <a href="/wiki/Ondansetron" title="Ondansetron">ondansetron</a>, <a href="/wiki/Granisetron" title="Granisetron">granisetron</a>, and <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, are important <a href="/wiki/Antiemetic" title="Antiemetic">antiemetic</a> agents.<a href="#cite_note-HoGan2006-115">[114]</a><a href="#cite_note-SeynaeveVerweijdeMulder1991-116">[115]</a> They are particularly important in treating the <a href="/wiki/Nausea" title="Nausea">nausea</a> and <a href="/wiki/Vomiting" title="Vomiting">vomiting</a> that <a href="/wiki/Chemotherapy-induced_nausea_and_vomiting" title="Chemotherapy-induced nausea and vomiting">occur during anticancer chemotherapy</a> using <a href="/wiki/Cytotoxic_drugs" class="mw-redirect" title="Cytotoxic drugs">cytotoxic drugs</a>.<a href="#cite_note-SeynaeveVerweijdeMulder1991-116">[115]</a> Another application is in the treatment of <a href="/wiki/Postoperative_nausea_and_vomiting" title="Postoperative nausea and vomiting">postoperative nausea and vomiting</a>.<a href="#cite_note-HoGan2006-115">[114]</a> <div class="mw-heading mw-heading3"><h3 id="Appetite_suppressants">Appetite suppressants</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=25" title="Edit section: Appetite suppressants">edit</a>]</div> Some <a href="/wiki/Serotonin_releasing_agent" title="Serotonin releasing agent">serotonin releasing agents</a>, <a href="/wiki/Serotonin_reuptake_inhibitor" title="Serotonin reuptake inhibitor">serotonin reuptake inhibitors</a>, and/or serotonin <a href="/wiki/5-HT2C_receptor" title="5-HT2C receptor">5-HT2C receptor</a> <a href="/wiki/Agonist" title="Agonist">agonists</a>, such as <a href="/wiki/Fenfluramine" title="Fenfluramine">fenfluramine</a>, <a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">dexfenfluramine</a>, <a href="/wiki/Chlorphentermine" title="Chlorphentermine">chlorphentermine</a>, <a href="/wiki/Sibutramine" title="Sibutramine">sibutramine</a>, and <a href="/wiki/Lorcaserin" title="Lorcaserin">lorcaserin</a>, have been approved and used as <a href="/wiki/Appetite_suppressant" class="mw-redirect" title="Appetite suppressant">appetite suppressants</a> for purposes of <a href="/wiki/Weight_loss" title="Weight loss">weight loss</a> in the treatment of <a href="/wiki/Overweightness" class="mw-redirect" title="Overweightness">overweightness</a> or <a href="/wiki/Obesity" title="Obesity">obesity</a>.<a href="#cite_note-HalfordHarroldBoyland2007-117">[116]</a><a href="#cite_note-HurrenBerlie2011-118">[117]</a><a href="#cite_note-HalfordBoylandLawton2011-119">[118]</a><a href="#cite_note-HalfordHarrold2012-120">[119]</a><a href="#cite_note-PrzegalińskiWitekWydra2023-121">[120]</a> Several of the preceding agents have been <a href="/wiki/Withdrawn_drug" class="mw-redirect" title="Withdrawn drug">withdrawn from the market</a> due to <a href="/wiki/Toxicity" title="Toxicity">toxicity</a>, such as <a href="/wiki/Cardiac_fibrosis" title="Cardiac fibrosis">cardiac fibrosis</a> or <a href="/wiki/Pulmonary_hypertension" title="Pulmonary hypertension">pulmonary hypertension</a>.<a href="#cite_note-PrzegalińskiWitekWydra2023-121">[120]</a> <div class="mw-heading mw-heading3"><h3 id="Anticonvulsants">Anticonvulsants</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=26" title="Edit section: Anticonvulsants">edit</a>]</div> Although it was previously <a href="/wiki/Withdrawn_drug" class="mw-redirect" title="Withdrawn drug">withdrawn from the market</a> as an appetite suppressant, fenfluramine was reintroduced as an <a href="/wiki/Anticonvulsant" title="Anticonvulsant">anticonvulsant</a> for treatment of <a href="/wiki/Seizure" title="Seizure">seizures</a> in certain rare forms of <a href="/wiki/Epilepsy" title="Epilepsy">epilepsy</a> like <a href="/wiki/Dravet_syndrome" title="Dravet syndrome">Dravet syndrome</a> and <a href="/wiki/Lennox%E2%80%93Gastaut_syndrome" title="Lennox–Gastaut syndrome">Lennox–Gastaut syndrome</a>.<a href="#cite_note-DiniDiCaraFerrara2023-122">[121]</a> Selective serotonin 5-HT2C receptor agonists, like lorcaserin, <a href="/wiki/Bexicaserin" title="Bexicaserin">bexicaserin</a>, and <a href="/wiki/BMB-101" title="BMB-101">BMB-101</a>, are also being developed for this use.<a href="#cite_note-DiniDiCaraFerrara2023-122">[121]</a><a href="#cite_note-BialerPerucca2022-123">[122]</a><a href="#cite_note-Dell'isolaVerrottiSciaccaluga2024-124">[123]</a><a href="#cite_note-AdisInsight-BMB-101-125">[124]</a> <div class="mw-heading mw-heading3"><h3 id="Psychedelics">Psychedelics</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=27" title="Edit section: Psychedelics">edit</a>]</div> <a href="/wiki/Serotonergic_psychedelic" class="mw-redirect" title="Serotonergic psychedelic">Serotonergic psychedelics</a>, including drugs like <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a> (found in <a href="/wiki/Psilocybin_mushroom" title="Psilocybin mushroom">psilocybin mushrooms</a>), <a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">dimethyltryptamine</a> (DMT) (found in <a href="/wiki/Ayahuasca" title="Ayahuasca">ayahuasca</a>), <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">lysergic acid diethylamide</a> (LSD), and <a href="/wiki/Mescaline" title="Mescaline">mescaline</a> (found in <a href="/wiki/Peyote" title="Peyote">peyote cactus</a>), are <a href="/wiki/Binding_selectivity" title="Binding selectivity">non-selective</a> <a href="/wiki/Agonist" title="Agonist">agonists</a> of the <a href="/wiki/Serotonin_receptor" class="mw-redirect" title="Serotonin receptor">serotonin receptors</a> and mediate their <a href="/wiki/Hallucinogen" title="Hallucinogen">hallucinogenic</a> effects specifically by activation of the serotonin <a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A receptor</a>.<a href="#cite_note-SlocumDiBertoRoth2022-126">[125]</a><a href="#cite_note-DuanCaoWang2024-127">[126]</a><a href="#cite_note-Nichols2018-128">[127]</a> This is evidenced by the fact that serotonin 5-HT2A receptor antagonists and so-called "<a href="/wiki/Trip_killer" title="Trip killer">trip killers</a>" like <a href="/wiki/Ketanserin" title="Ketanserin">ketanserin</a> block the hallucinogenic effects of serotonergic psychedelics in humans, among many other findings.<a href="#cite_note-SlocumDiBertoRoth2022-126">[125]</a><a href="#cite_note-DuanCaoWang2024-127">[126]</a><a href="#cite_note-HalmanKongSarris2024-129">[128]</a> Some serotonergic psychedelics, like <a href="/wiki/Psilocin" title="Psilocin">psilocin</a> and DMT, are <a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">substituted tryptamines</a> and are very similar in <a href="/wiki/Chemical_structure" title="Chemical structure">chemical structure</a> to serotonin.<a href="#cite_note-Nichols2018-128">[127]</a> Serotonin itself, despite acting as a serotonin 5-HT2A receptor agonist, is thought to be non-hallucinogenic.<a href="#cite_note-VargasDunlapDong2023-130">[129]</a> The hallucinogenic effects of serotonergic psychedelics appear to be mediated specifically by activation of serotonin 5-HT2A receptors expressed in a population of <a href="/wiki/Cortex" class="mw-disambig" title="Cortex">cortical</a> <a href="/wiki/Neuron" title="Neuron">neurons</a> in the <a href="/wiki/Medial_prefrontal_cortex" class="mw-redirect" title="Medial prefrontal cortex">medial prefrontal cortex</a> (mPFC).<a href="#cite_note-Sapienza2023-131">[130]</a><a href="#cite_note-VargasDunlapDong2023-130">[129]</a> These serotonin 5-HT2A receptors, unlike most serotonin and related receptors, are expressed <a href="/wiki/Intracellular" class="mw-redirect" title="Intracellular">intracellularly</a>.<a href="#cite_note-Sapienza2023-131">[130]</a><a href="#cite_note-VargasDunlapDong2023-130">[129]</a> In addition, the neurons containing them lack <a href="/wiki/Gene_expression" title="Gene expression">expression</a> of the <a href="/wiki/Serotonin_transporter" title="Serotonin transporter">serotonin transporter</a> (SERT), which normally <a href="/wiki/Active_transport" title="Active transport">transports</a> serotonin from the <a href="/wiki/Extracellular" class="mw-redirect" title="Extracellular">extracellular</a> space to the intracellular space within neurons.<a href="#cite_note-Sapienza2023-131">[130]</a><a href="#cite_note-VargasDunlapDong2023-130">[129]</a> Serotonin itself is too <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> to enter serotonergic neurons without the SERT, and hence these serotonin 5-HT2A receptors are inaccessible to serotonin.<a href="#cite_note-Sapienza2023-131">[130]</a><a href="#cite_note-VargasDunlapDong2023-130">[129]</a> Conversely, serotonergic psychedelics are more <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> than serotonin and readily enter these neurons.<a href="#cite_note-Sapienza2023-131">[130]</a><a href="#cite_note-VargasDunlapDong2023-130">[129]</a> In addition to explaining why serotonin does not show psychedelic effects, these findings may explain why drugs that increase serotonin levels, like <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">selective serotonin reuptake inhibitors</a> (SSRIs) and various other types of serotonergic agents, do not produce psychedelic effects.<a href="#cite_note-Sapienza2023-131">[130]</a><a href="#cite_note-VargasDunlapDong2023-130">[129]</a> Artificial expression of the SERT in these medial prefrontal cortex neurons resulted in the <a href="/wiki/Serotonin_releasing_agent" title="Serotonin releasing agent">serotonin releasing agent</a> <a href="/wiki/Para-chloroamphetamine" class="mw-redirect" title="Para-chloroamphetamine">para-chloroamphetamine</a> (PCA), which does not normally show psychedelic-like effects, being able to produce psychedelic-like effects in animals.<a href="#cite_note-VargasDunlapDong2023-130">[129]</a> Although serotonin itself is non-hallucinogenic, administration of very high doses of a <a href="/wiki/Serotonin_precursor" class="mw-redirect" title="Serotonin precursor">serotonin precursor</a>, like <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a> or <a href="/wiki/5-hydroxytryptophan" class="mw-redirect" title="5-hydroxytryptophan">5-hydroxytryptophan</a> (5-HTP), or <a href="/wiki/Intracerebroventricular_injection" title="Intracerebroventricular injection">intracerebroventricular injection</a> of high doses of serotonin directly into the brain, can produce psychedelic-like effects in animals.<a href="#cite_note-SchmidBohn2018-132">[131]</a><a href="#cite_note-KozlenkovGonzález-Maeso2013-133">[132]</a><a href="#cite_note-SchmidBohn2010-134">[133]</a> These psychedelic-like effects can be abolished by <a href="/wiki/Indolethylamine_N-methyltransferase" class="mw-redirect" title="Indolethylamine N-methyltransferase">indolethylamine N-methyltransferase</a> (INMT) <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a>, which block conversion of serotonin and other endogenous tryptamines into N-<a href="/wiki/Methyl_group" title="Methyl group">methylated</a> tryptamines, including <a href="/wiki/N-Methylserotonin" title="N-Methylserotonin">N-methylserotonin</a> (NMS; norbufotenin), <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a> (5-hydroxy-N,N-dimethyltryptamine; 5-HO-DMT), <a href="/wiki/N-methyltryptamine" class="mw-redirect" title="N-methyltryptamine">N-methyltryptamine</a> (NMT), and <a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">N,N-dimethyltryptamine</a> (DMT).<a href="#cite_note-KozlenkovGonzález-Maeso2013-133">[132]</a><a href="#cite_note-HalberstadtGeyer2018-135">[134]</a><a href="#cite_note-SchmidBohn2010-134">[133]</a> These N-methyltryptamines are much more lipophilic than serotonin and, in contrast, are able to <a href="/wiki/Passive_diffusion" class="mw-redirect" title="Passive diffusion">diffuse</a> into serotonergic neurons and activate intracellular serotonin 5-HT2A receptors.<a href="#cite_note-KozlenkovGonzález-Maeso2013-133">[132]</a><a href="#cite_note-SchmidBohn2010-134">[133]</a><a href="#cite_note-Sapienza2023-131">[130]</a><a href="#cite_note-VargasDunlapDong2023-130">[129]</a> DMT is a <a href="/wiki/Natural_product" title="Natural product">naturally occurring</a> <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> compound in the body.<a href="#cite_note-JiménezBouso2022-136">[135]</a><a href="#cite_note-Barker2018-137">[136]</a><a href="#cite_note-CameronOlson2018-138">[137]</a> In relation to the fact that serotonin itself is unable to activate intracellular serotonin 5-HT2A receptors, it is possible that DMT might be the endogenous <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligand</a> of these receptors rather than serotonin.<a href="#cite_note-Sapienza2023-131">[130]</a><a href="#cite_note-VargasDunlapDong2023-130">[129]</a> <div class="mw-heading mw-heading4"><h4 id="Methyltryptamines_and_hallucinogens">Methyltryptamines and hallucinogens</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=28" title="Edit section: Methyltryptamines and hallucinogens">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">For details on tryptamine neurotransmitters in humans, see <a href="/wiki/Trace_amine" title="Trace amine">Trace amine</a>.</div> Several plants contain serotonin together with a family of related <a href="/wiki/Tryptamine" title="Tryptamine">tryptamines</a> that are <a href="/wiki/Methylation" title="Methylation">methylated</a> at the <a href="/wiki/Amine" title="Amine">amino</a> (NH2) and <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">(OH) groups</a>, are <a href="/wiki/Amine_oxide" title="Amine oxide">N-oxides</a>, or miss the OH group. These compounds do reach the brain, although some portion of them are metabolized by <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidase</a> enzymes (mainly <a href="/wiki/MAO-A" class="mw-redirect" title="MAO-A">MAO-A</a>) in the liver. Examples are plants from the genus <a href="/wiki/Anadenanthera" title="Anadenanthera">Anadenanthera</a> that are used in the <a href="/wiki/Hallucinogen" title="Hallucinogen">hallucinogenic</a> <a href="/wiki/Yopo" class="mw-redirect" title="Yopo">yopo</a> snuff. These compounds are widely present in the leaves of many plants, and may serve as deterrents for animal ingestion. Serotonin occurs in several mushrooms of the genus <a href="/wiki/Panaeolus" title="Panaeolus">Panaeolus</a>.<a href="#cite_note-139">[138]</a> <div class="mw-heading mw-heading3"><h3 id="Entactogens">Entactogens</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=29" title="Edit section: Entactogens">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/Entactogen#Mechanism_of_action" class="mw-redirect" title="Entactogen">Entactogen § Mechanism of action</a></div> The <a href="/wiki/Entactogen" class="mw-redirect" title="Entactogen">entactogen</a> <a href="/wiki/MDMA" title="MDMA">MDMA</a> is a <a href="/wiki/Serotonin_releasing_agent" title="Serotonin releasing agent">serotonin releasing agent</a> and, while it also possesses other actions such as concomitant <a href="/wiki/Norepinephrine_releasing_agent" title="Norepinephrine releasing agent">release of norepinephrine</a> and <a href="/wiki/Dopamine_releasing_agent" title="Dopamine releasing agent">dopamine</a> and weak direct <a href="/wiki/Receptor_agonist" class="mw-redirect" title="Receptor agonist">agonism</a> of the serotonin <a href="/wiki/5-HT2_receptor" title="5-HT2 receptor">5-HT2 receptors</a>, its serotonin release plays a key role in its unique entactogenic effects.<a href="#cite_note-DunlapAndrewsOlson2018-140">[139]</a> Entactogens like MDMA should be distinguished from other drugs such as <a href="/wiki/Stimulant" title="Stimulant">stimulants</a> like <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a> and psychedelics like <a href="/wiki/LSD" title="LSD">LSD</a>, although MDMA itself also has some characteristics of both of these types of agents.<a href="#cite_note-DunlapAndrewsOlson2018-140">[139]</a><a href="#cite_note-Nichols2022-141">[140]</a> Coadministration of <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">selective serotonin reuptake inhibitors</a> (SSRIs), which block the <a href="/wiki/Serotonin_transporter" title="Serotonin transporter">serotonin transporter</a> (SERT) and prevent MDMA from inducing serotonin release, markedly reduce the subjective effects of MDMA, demonstrating the key role of serotonin in the effects of the drug.<a href="#cite_note-SarparastThomasMalcolm2022-142">[141]</a> Serotonin releasing agents like MDMA achieve much greater increases in serotonin levels than SSRIs and have far more robust of subjective effects.<a href="#cite_note-RothmanBaumann2006-143">[142]</a><a href="#cite_note-ScorzaSilveiraNichols1999-144">[143]</a><a href="#cite_note-Marona-LewickaNichols1997-145">[144]</a><a href="#cite_note-Marona-LewickaNichols1998-146">[145]</a> Besides MDMA, many other entactogens also exist and are known.<a href="#cite_note-SimmlerLiechti2018-147">[146]</a><a href="#cite_note-Oeri2021-148">[147]</a><a href="#cite_note-Nichols2022-141">[140]</a> <div class="mw-heading mw-heading3"><h3 id="Serotonin_syndrome">Serotonin syndrome</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=30" title="Edit section: Serotonin syndrome">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/Serotonin_syndrome" title="Serotonin syndrome">Serotonin syndrome</a></div> Extremely high levels of serotonin or activation of certain serotonin receptors can cause a condition known as <a href="/wiki/Serotonin_syndrome" title="Serotonin syndrome">serotonin syndrome</a>, with toxic and potentially fatal effects. In practice, such toxic levels are essentially impossible to reach through an <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a> of a single antidepressant drug, but require a combination of serotonergic agents, such as an <a href="/wiki/SSRI" class="mw-redirect" title="SSRI">SSRI</a> with a <a href="/wiki/MAOI" class="mw-redirect" title="MAOI">MAOI</a>, which may occur in therapeutic doses.<a href="#cite_note-New_285–293-149">[148]</a><a href="#cite_note-150">[149]</a> However, serotonin syndrome can occur with overdose of certain serotonin receptor agonists, like the <a href="/wiki/25-NB" title="25-NB">NBOMe</a> series of serotonergic psychedelics.<a href="#cite_note-ScottonHillWilliams2019-151">[150]</a><a href="#cite_note-OrdakZmysłowskaBielski2021-152">[151]</a><a href="#cite_note-JacbosAkersVohra2020-153">[152]</a> The intensity of the symptoms of serotonin syndrome vary over a wide spectrum, and the milder forms are seen even at nontoxic levels.<a href="#cite_note-pmid12925718-154">[153]</a> It is estimated that 14% of patients experiencing serotonin syndrome overdose on SSRIs; meanwhile the fatality rate is between 2% and 12%.<a href="#cite_note-New_285–293-149">[148]</a><a href="#cite_note-pmid18625822-155">[154]</a><a href="#cite_note-pmid15784664-156">[155]</a> <div class="mw-heading mw-heading3"><h3 id="Cardiac_fibrosis_and_other_fibroses">Cardiac fibrosis and other fibroses</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=31" title="Edit section: Cardiac fibrosis and other fibroses">edit</a>]</div> Some serotonergic agonist drugs cause fibrosis anywhere in the body, particularly the syndrome of <a href="/wiki/Retroperitoneal_fibrosis" title="Retroperitoneal fibrosis">retroperitoneal fibrosis</a>, as well as <a href="/wiki/Cardiac_fibrosis" title="Cardiac fibrosis">cardiac valve fibrosis</a>.<a href="#cite_note-Baskin-157">[156]</a> In the past, three groups of serotonergic drugs have been epidemiologically linked with these syndromes. These are the serotonergic vasoconstrictive antimigraine drugs (<a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a> and <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>),<a href="#cite_note-Baskin-157">[156]</a> the serotonergic appetite suppressant drugs (<a href="/wiki/Fenfluramine" title="Fenfluramine">fenfluramine</a>, <a href="/wiki/Chlorphentermine" title="Chlorphentermine">chlorphentermine</a>, and <a href="/wiki/Aminorex" title="Aminorex">aminorex</a>), and certain anti-Parkinsonian dopaminergic agonists, which also stimulate serotonergic 5-HT2B receptors. These include <a href="/wiki/Pergolide" title="Pergolide">pergolide</a> and <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, but not the more dopamine-specific <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>.<a href="#cite_note-urluserpage.fu-berlin.de-158">[157]</a> As with fenfluramine, some of these drugs have been withdrawn from the market after groups taking them showed a statistical increase of one or more of the side effects described. An example is <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>. The drug was declining in use since it was reported in 2003 to be associated with cardiac fibrosis.<a href="#cite_note-ADRAC_2004-159">[158]</a> Two independent studies published in <a href="/wiki/The_New_England_Journal_of_Medicine" title="The New England Journal of Medicine">The New England Journal of Medicine</a> in January 2007 implicated pergolide, along with <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, in causing <a href="/wiki/Valvular_heart_disease" title="Valvular heart disease">valvular heart disease</a>.<a href="#cite_note-pmid17202453-160">[159]</a><a href="#cite_note-pmid17202454-161">[160]</a> As a result of this, the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">FDA</a> removed pergolide from the United States market in March 2007.<a href="#cite_note-162">[161]</a> (Since cabergoline is not approved in the United States for Parkinson's Disease, but for hyperprolactinemia, the drug remains on the market. Treatment for hyperprolactinemia requires lower doses than that for Parkinson's Disease, diminishing the risk of valvular heart disease).<a href="#cite_note-FDAwithdraw-163">[162]</a> <div class="mw-heading mw-heading2"><h2 id="Comparative_biology_and_evolution">Comparative biology and evolution</h2>[<a href="/w/index.php?title=Serotonin&action=edit&section=32" title="Edit section: Comparative biology and evolution">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Unicellular_organisms">Unicellular organisms</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=33" title="Edit section: Unicellular organisms">edit</a>]</div> Serotonin is used by a variety of single-cell organisms for various purposes. <a href="/wiki/SSRIs" class="mw-redirect" title="SSRIs">SSRIs</a> have been found to be toxic to algae.<a href="#cite_note-pmid16753215-164">[163]</a> The gastrointestinal parasite <a href="/wiki/Entamoeba_histolytica" title="Entamoeba histolytica">Entamoeba histolytica</a> secretes serotonin, causing a sustained secretory diarrhea in some people.<a href="#cite_note-pmid6308760-23">[23]</a><a href="#cite_note-pmid2861068-165">[164]</a> Patients infected with E. histolytica have been found to have highly elevated serum serotonin levels, which returned to normal following resolution of the infection.<a href="#cite_note-Banu_2005-166">[165]</a> E. histolytica also responds to the presence of serotonin by becoming more virulent.<a href="#cite_note-pmid2561282-167">[166]</a> This means serotonin secretion not only serves to increase the spread of <a href="/wiki/Entamoeba" title="Entamoeba">entamoebas</a> by giving the host diarrhea but also serves to coordinate their behaviour according to their population density, a phenomenon known as <a href="/wiki/Quorum_sensing" title="Quorum sensing">quorum sensing</a>. Outside the gut of a host, there is nothing that the entamoebas provoke to release serotonin, hence the serotonin concentration is very low. Low serotonin signals to the entamoebas they are outside a host and they become less virulent to conserve energy. When they enter a new host, they multiply in the gut, and become more virulent as the enterochromaffine cells get provoked by them and the serotonin concentration increases. <div class="mw-heading mw-heading3"><h3 id="Edible_plants_and_mushrooms">Edible plants and mushrooms</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=34" title="Edit section: Edible plants and mushrooms">edit</a>]</div> In drying <a href="/wiki/Seed" title="Seed">seeds</a>, serotonin production is a way to get rid of the buildup of poisonous <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>. The ammonia is collected and placed in the <a href="/wiki/Indole" title="Indole">indole</a> part of L-<a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a>, which is then <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylated</a> by <a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">tryptophan decarboxylase</a> to give tryptamine, which is then <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylated</a> by a <a href="/wiki/Cytochrome_P450_monooxygenase" class="mw-redirect" title="Cytochrome P450 monooxygenase">cytochrome P450 monooxygenase</a>, yielding serotonin.<a href="#cite_note-Schröder_et_al.-168">[167]</a> However, since serotonin is a major gastrointestinal tract modulator, it may be produced in the fruits of plants as a way of speeding the passage of seeds through the digestive tract, in the same way as many well-known seed and fruit associated laxatives. Serotonin is found in <a href="/wiki/Edible_mushroom" title="Edible mushroom">mushrooms</a>, <a href="/wiki/Fruit" title="Fruit">fruits</a>, and <a href="/wiki/Vegetable" title="Vegetable">vegetables</a>. The highest values of 25–400 mg/kg have been found in nuts of the <a href="/wiki/Walnut" title="Walnut">walnut</a> (Juglans) and <a href="/wiki/Hickory" title="Hickory">hickory</a> (Carya) genera. Serotonin concentrations of 3–30 mg/kg have been found in <a href="/wiki/Plantain_(cooking)" class="mw-redirect" title="Plantain (cooking)">plantains</a>, <a href="/wiki/Pineapple" title="Pineapple">pineapples</a>, <a href="/wiki/Banana" title="Banana">banana</a>, <a href="/wiki/Kiwifruit" title="Kiwifruit">kiwifruit</a>, <a href="/wiki/Plum" title="Plum">plums</a>, and <a href="/wiki/Tomato" title="Tomato">tomatoes</a>. Moderate levels from 0.1–3 mg/kg have been found in a wide range of tested vegetables.<a href="#cite_note-feld-24">[24]</a><a href="#cite_note-Ramakrishna_2011-20">[20]</a> Serotonin is one compound of the poison contained in <a href="/wiki/Stinging_nettle" class="mw-redirect" title="Stinging nettle">stinging nettles</a> (Urtica dioica), where it causes pain on injection in the same manner as its presence in insect venoms.<a href="#cite_note-Erspamer-1966-22">[22]</a> It is also naturally found in <a href="/wiki/Paramuricea_clavata" title="Paramuricea clavata">Paramuricea clavata</a>, or the Red Sea Fan.<a href="#cite_note-169">[168]</a> Serotonin and tryptophan have been found in chocolate with varying cocoa contents. The highest serotonin content (2.93 μg/g) was found in chocolate with 85% cocoa, and the highest tryptophan content (13.27–13.34 μg/g) was found in 70–85% cocoa. The intermediate in the synthesis from tryptophan to serotonin, 5-hydroxytryptophan, was not found.<a href="#cite_note-170">[169]</a> Root development in <a href="/wiki/Arabidopsis_thaliana" title="Arabidopsis thaliana">Arabidopsis thaliana</a> is stimulated and modulated by serotonin – in various ways at various concentrations.<a href="#cite_note-Pelagio-Flores-et-al-2011-171">[170]</a> Serotonin serves as a plant defense chemical against fungi. When infected with <a href="/wiki/Fusarium_crown_rot_of_wheat" title="Fusarium crown rot of wheat">Fusarium crown rot</a> (Fusarium pseudograminearum), <a href="/wiki/Wheat" title="Wheat">wheat</a> (Triticum aestivum) greatly increases its production of tryptophan to synthesize new serotonin.<a href="#cite_note-Powell-et-al-2016-172">[171]</a> The function of this is poorly understood<a href="#cite_note-Powell-et-al-2016-172">[171]</a> but wheat also produces serotonin when infected by <a href="/wiki/Stagonospora_nodorum" class="mw-redirect" title="Stagonospora nodorum">Stagonospora nodorum</a> – in that case to retard spore production.<a href="#cite_note-Du-Fall-Solomon-2013-173">[172]</a> The model <a href="/wiki/Cereal" title="Cereal">cereal</a> <a href="/wiki/Brachypodium_distachyon" title="Brachypodium distachyon">Brachypodium distachyon</a> – used as a research substitute for wheat and other production cereals – also produces serotonin, <a href="/wiki/Coumaroyl" class="mw-redirect" title="Coumaroyl">coumaroyl</a>-serotonin, and <a href="/wiki/Feruloyl" class="mw-redirect" title="Feruloyl">feruloyl</a>-serotonin in response to <a href="/wiki/Fusarium_graminearum" class="mw-redirect" title="Fusarium graminearum">F. graminearum</a>. This produces a slight <a href="/wiki/Antimicrobial" title="Antimicrobial">antimicrobial</a> effect. B. distachyon produces more serotonin (and conjugates) in response to <a href="/wiki/Deoxynivalenol" class="mw-redirect" title="Deoxynivalenol">deoxynivalenol</a> (DON)-producing F. graminearum than non-DON-producing.<a href="#cite_note-Pasquet-et-al-2014-174">[173]</a> <a href="/wiki/Solanum_lycopersicum" class="mw-redirect" title="Solanum lycopersicum">Solanum lycopersicum</a> produces many <a href="/wiki/Amino_acid" title="Amino acid">AA</a> conjugates – including several of serotonin – in its leaves, stems, and roots in response to <a href="/wiki/Ralstonia_solanacearum" title="Ralstonia solanacearum">Ralstonia solanacearum</a> infection.<a href="#cite_note-Zeiss-et-al-2021-175">[174]</a> <div class="mw-heading mw-heading3"><h3 id="Invertebrates">Invertebrates</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=35" title="Edit section: Invertebrates">edit</a>]</div> Serotonin functions as a neurotransmitter in the nervous systems of most animals. <div class="mw-heading mw-heading4"><h4 id="Nematodes">Nematodes</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=36" title="Edit section: Nematodes">edit</a>]</div> For example, in the roundworm <a href="/wiki/Caenorhabditis_elegans" title="Caenorhabditis elegans">Caenorhabditis elegans</a>, which feeds on bacteria, serotonin is released as a signal in response to positive events, such as finding a new source of food or in male animals finding a female with which to mate.<a href="#cite_note-176">[175]</a> When a well-fed worm feels bacteria on its <a href="/wiki/Cuticle" title="Cuticle">cuticle</a>, <a href="/wiki/Dopamine" title="Dopamine">dopamine</a> is released, which slows it down; if it is starved, serotonin also is released, which slows the animal down further. This mechanism increases the amount of time animals spend in the presence of food.<a href="#cite_note-pmid10896158-177">[176]</a> The released serotonin activates the muscles used for feeding, while <a href="/wiki/Octopamine" title="Octopamine">octopamine</a> suppresses them.<a href="#cite_note-pmid12477893-178">[177]</a><a href="#cite_note-Rosso-et-al-2009-179">[178]</a> Serotonin diffuses to serotonin-sensitive neurons, which control the animal's perception of nutrient availability. <div class="mw-heading mw-heading4"><h4 id="Decapods">Decapods</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=37" title="Edit section: Decapods">edit</a>]</div> If <a href="/wiki/Lobster" title="Lobster">lobsters</a> are injected with serotonin, they behave like dominant individuals whereas octopamine causes <a href="/wiki/Dominance_hierarchy" title="Dominance hierarchy">subordinate behavior</a>.<a href="#cite_note-pmid2902685-31">[31]</a> A <a href="/wiki/Crayfish" title="Crayfish">crayfish</a> that is frightened may <a href="/wiki/Caridoid_escape_reaction" title="Caridoid escape reaction">flip its tail</a> to flee, and the effect of serotonin on this behavior depends largely on the animal's social status. Serotonin inhibits the fleeing reaction in subordinates, but enhances it in socially dominant or isolated individuals. The reason for this is social experience alters the proportion between <a href="/wiki/Serotonin_receptor" class="mw-redirect" title="Serotonin receptor">serotonin receptors</a> (5-HT receptors) that have opposing effects on the <a href="/wiki/Fight-or-flight_response" title="Fight-or-flight response">fight-or-flight response</a>.[<a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify">clarification needed</a>] The effect of <a href="/wiki/5-HT1_receptor" title="5-HT1 receptor">5-HT1 receptors</a> predominates in subordinate animals, while <a href="/wiki/5-HT2_receptor" title="5-HT2 receptor">5-HT2 receptors</a> predominates in dominants.<a href="#cite_note-pmid8553075-180">[179]</a> <div class="mw-heading mw-heading4"><h4 id="In_venoms">In venoms</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=38" title="Edit section: In venoms">edit</a>]</div> Serotonin is a common component of invertebrate venoms, salivary glands, nervous tissues, and various other tissues, across molluscs, insects, crustaceans, scorpions, various kinds of worms, and jellyfish.<a href="#cite_note-Erspamer-1966-22">[22]</a> Adult <a href="/wiki/Rhodnius_prolixus" title="Rhodnius prolixus">Rhodnius prolixus</a> – <a href="/wiki/Hematophagous" class="mw-redirect" title="Hematophagous">hematophagous</a> on vertebrates – secrete <a href="/wiki/Lipocalin" title="Lipocalin">lipocalins</a> into the wound during feeding. In 2003 these lipocalins were demonstrated to sequester serotonin to prevent vasoconstriction (and possibly coagulation) in the host.<a href="#cite_note-Fry-et-al-2009-181">[180]</a> <div class="mw-heading mw-heading4"><h4 id="Insects">Insects</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=39" title="Edit section: Insects">edit</a>]</div> Serotonin is evolutionarily conserved and appears across the animal kingdom. It is seen in insect processes in roles similar to in the human central nervous system, such as memory, appetite, sleep, and behavior.<a href="#cite_note-182">[181]</a><a href="#cite_note-Huser_2012-19">[19]</a> Some circuits in <a href="/wiki/Mushroom_bodies" title="Mushroom bodies">mushroom bodies</a> are serotonergic.<a href="#cite_note-Schoofs-et-al-2017-183">[182]</a> (See specific Drosophila example below, <a href="#Dipterans">§Dipterans</a>.) <div class="mw-heading mw-heading5"><h5 id="Acrididae">Acrididae</h5>[<a href="/w/index.php?title=Serotonin&action=edit&section=40" title="Edit section: Acrididae">edit</a>]</div> Locust swarming is initiated but not maintained by serotonin,<a href="#cite_note-Wang-Kang-2014-184">[183]</a> with release being triggered by tactile contact between individuals.<a href="#cite_note-Zhang-et-al-2019-185">[184]</a> This transforms social preference from aversion to a gregarious state that enables coherent groups.<a href="#cite_note-Anstey-186">[185]</a><a href="#cite_note-Zhang-et-al-2019-185">[184]</a><a href="#cite_note-Wang-Kang-2014-184">[183]</a> Learning in flies and honeybees is affected by the presence of serotonin.<a href="#cite_note-187">[186]</a><a href="#cite_note-188">[187]</a> <div class="mw-heading mw-heading5"><h5 id="Role_in_insecticides">Role in insecticides</h5>[<a href="/w/index.php?title=Serotonin&action=edit&section=41" title="Edit section: Role in insecticides">edit</a>]</div> Insect 5-HT receptors have similar sequences to the vertebrate versions, but pharmacological differences have been seen. Invertebrate drug response has been far less characterized than mammalian pharmacology and the potential for species selective insecticides has been discussed.<a href="#cite_note-189">[188]</a> <div class="mw-heading mw-heading5"><h5 id="Hymenopterans">Hymenopterans</h5>[<a href="/w/index.php?title=Serotonin&action=edit&section=42" title="Edit section: Hymenopterans">edit</a>]</div> <a href="/wiki/Wasp" title="Wasp">Wasps</a> and <a href="/wiki/Hornets" class="mw-redirect" title="Hornets">hornets</a> have serotonin in their venom,<a href="#cite_note-190">[189]</a> which causes pain and inflammation<a href="#cite_note-Chen_2010-21">[21]</a><a href="#cite_note-Erspamer-1966-22">[22]</a> as do <a href="/wiki/Scorpion" title="Scorpion">scorpions</a>.<a href="#cite_note-191">[190]</a><a href="#cite_note-Erspamer-1966-22">[22]</a> <a href="/wiki/Pheidole_dentata" title="Pheidole dentata">Pheidole dentata</a> takes on more and more tasks in <a href="/wiki/Ant_colony" title="Ant colony">the colony</a> as it gets older, which requires it to respond to more and more <a href="/wiki/Olfaction" class="mw-redirect" title="Olfaction">olfactory</a> cues in the course of performing them. This olfactory response broadening was demonstrated to go along with increased serotonin and <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, but not <a href="/wiki/Octopamine" title="Octopamine">octopamine</a> in 2006.<a href="#cite_note-Gadenne-et-al-2016-192">[191]</a> <div class="mw-heading mw-heading5"><h5 id="Dipterans">Dipterans</h5>[<a href="/w/index.php?title=Serotonin&action=edit&section=43" title="Edit section: Dipterans">edit</a>]</div> If flies are fed serotonin, they are more aggressive; flies depleted of serotonin still exhibit aggression, but they do so much less frequently.<a href="#cite_note-Dierick-193">[192]</a> In <a href="/wiki/Dipteran_crop" class="mw-redirect" title="Dipteran crop">their crops</a> it plays a vital role in digestive motility produced by contraction. Serotonin that acts on the crop is exogenous to the crop itself and 2012 research suggested that it probably originated in the serotonin neural plexus in the thoracic-abdominal synganglion.<a href="#cite_note-Stoffolano-Haselton-2013-194">[193]</a> In 2011 a <a href="/wiki/Drosophila" title="Drosophila">Drosophila</a> serotonergic mushroom body was found to work in concert with <a href="/wiki/Amnesiac_gene" title="Amnesiac gene">Amnesiac</a> to form memories.<a href="#cite_note-Schoofs-et-al-2017-183">[182]</a> In 2007 serotonin was found to promote aggression in <a href="/wiki/Diptera" class="mw-redirect" title="Diptera">Diptera</a>, which was counteracted by <a href="/w/index.php?title=Neuropeptide_F&action=edit&redlink=1" class="new" title="Neuropeptide F (page does not exist)">neuropeptide F</a> – a surprising find given that they both promote <a href="/wiki/Insect_courtship" class="mw-redirect" title="Insect courtship">courtship</a>, which is usually similar to aggression in most respects.<a href="#cite_note-Schoofs-et-al-2017-183">[182]</a> <div class="mw-heading mw-heading3"><h3 id="Vertebrates">Vertebrates</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=44" title="Edit section: Vertebrates">edit</a>]</div> Serotonin, also referred to as 5-hydroxytryptamine (5-HT), is a neurotransmitter most known for its involvement in mood disorders in humans. It is also a widely present neuromodulator among vertebrates and invertebrates.<a href="#cite_note-Bacqué-Cazenave_2020-195">[194]</a> Serotonin has been found having associations with many physiological systems such as cardiovascular, <a href="/wiki/Thermoregulation" title="Thermoregulation">thermoregulation</a>, and behavioral functions, including: <a href="/wiki/Circadian_rhythm" title="Circadian rhythm">circadian rhythm</a>, appetite, aggressive and sexual behavior, sensorimotor reactivity and learning, and pain sensitivity.<a href="#cite_note-Lucki_1998-196">[195]</a> Serotonin's function in neurological systems along with specific behaviors among vertebrates found to be strongly associated with serotonin will be further discussed. Two relevant case studies are also mentioned regarding serotonin development involving <a href="/wiki/Teleost" title="Teleost">teleost fish</a> and <a href="/wiki/Mouse" title="Mouse">mice</a>. In mammals, 5-HT is highly concentrated in the <a href="/wiki/Substantia_nigra" title="Substantia nigra">substantia nigra</a>, <a href="/wiki/Ventral_tegmental_area" title="Ventral tegmental area">ventral tegmental area</a> and <a href="/wiki/Raphe_nuclei" title="Raphe nuclei">raphe nuclei</a>. Lesser concentrated areas include other brain regions and the spinal cord.<a href="#cite_note-Bacqué-Cazenave_2020-195">[194]</a> 5-HT neurons are also shown to be highly branched, indicating that they are structurally prominent for influencing multiple areas of the <a href="/wiki/Central_nervous_system" title="Central nervous system">CNS</a> at the same time, although this trend is exclusive solely to mammals.<a href="#cite_note-Lucki_1998-196">[195]</a> <div class="mw-heading mw-heading4"><h4 id="5-HT_system_in_vertebrates">5-HT system in vertebrates</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=45" title="Edit section: 5-HT system in vertebrates">edit</a>]</div> <a href="/wiki/Vertebrate" title="Vertebrate">Vertebrates</a> are multicellular organisms in the <a href="/wiki/Chordate" title="Chordate">phylum Chordata</a> that possess a backbone and a <a href="/wiki/Nervous_system" title="Nervous system">nervous system</a>. This includes mammals, fish, reptiles, birds, etc. In humans, the nervous system is composed of the <a href="/wiki/Central_nervous_system" title="Central nervous system">central</a> and <a href="/wiki/Peripheral_nervous_system" title="Peripheral nervous system">peripheral nervous system</a>, with little known about the specific mechanisms of neurotransmitters in most other vertebrates. However, it is known that while serotonin is involved in stress and behavioral responses, it is also important in <a href="/wiki/Cognitive_functions" class="mw-redirect" title="Cognitive functions">cognitive functions</a>.<a href="#cite_note-Bacqué-Cazenave_2020-195">[194]</a> Brain organization in most vertebrates includes 5-HT cells in the <a href="/wiki/Hindbrain" title="Hindbrain">hindbrain</a>.<a href="#cite_note-Bacqué-Cazenave_2020-195">[194]</a> In addition to this, 5-HT is often found in other sections of the brain in non-placental vertebrates, including the <a href="/wiki/Basal_forebrain" title="Basal forebrain">basal forebrain</a> and <a href="/wiki/Pretectal_area" title="Pretectal area">pretectum</a>.<a href="#cite_note-Backström_2017-197">[196]</a> Since location of serotonin receptors contribute to behavioral responses, this suggests serotonin is part of specific pathways in non-placental vertebrates that are not present in amniotic organisms.<a href="#cite_note-198">[197]</a> Teleost fish and mice are organisms most often used to study the connection between serotonin and vertebrate behavior. Both organisms show similarities in the effect of serotonin on behavior, but differ in the mechanism in which the responses occur. <div class="mw-heading mw-heading5"><h5 id="Dogs_/_canine_species">Dogs / canine species</h5>[<a href="/w/index.php?title=Serotonin&action=edit&section=46" title="Edit section: Dogs / canine species">edit</a>]</div> There are few studies of serotonin in dogs. One study reported serotonin values were higher at dawn than at dusk.<a href="#cite_note-199">[198]</a> In another study, serum 5-HT levels did not seem to be associated with dogs' behavioural response to a stressful situation.<a href="#cite_note-200">[199]</a> Urinary serotonin/creatinine ratio in bitches tended to be higher 4 weeks after surgery. In addition, serotonin was positively correlated with both cortisol and progesterone but not with testosterone after ovariohysterectomy.<a href="#cite_note-201">[200]</a> <div class="mw-heading mw-heading5"><h5 id="Teleost_fish">Teleost fish</h5>[<a href="/w/index.php?title=Serotonin&action=edit&section=47" title="Edit section: Teleost fish">edit</a>]</div> Like non-placental vertebrates, teleost fish also possess 5-HT cells in other sections of the brain, including the <a href="/wiki/Basal_forebrain" title="Basal forebrain">basal forebrain</a>.<a href="#cite_note-Backström_2017-197">[196]</a> <a href="/wiki/Zebrafish" title="Zebrafish">Danio rerio</a> (zebra fish) are a species of teleost fish often used for studying serotonin within the brain. Despite much being unknown about serotonergic systems in vertebrates, the importance in moderating stress and social interaction is known.<a href="#cite_note-Winberg_2016-202">[201]</a> It is hypothesized that AVT and CRF cooperate with serotonin in the <a rel="nofollow" class="external text" href="https://link.springer.com/referenceworkentry/10.1007%2F978-1-4419-1005-9_460">hypothalamic-pituitary-interrenal axis</a>.<a href="#cite_note-Backström_2017-197">[196]</a> These <a href="/wiki/Neuropeptide" title="Neuropeptide">neuropeptides</a> influence the <a href="/wiki/Neuroplasticity" title="Neuroplasticity">plasticity</a> of the teleost, affecting its ability to change and respond to its environment. Subordinate fish in social settings show a drastic increase in 5-HT concentrations.<a href="#cite_note-Winberg_2016-202">[201]</a> High levels of 5-HT long term influence the inhibition of aggression in subordinate fish.<a href="#cite_note-Winberg_2016-202">[201]</a> <div class="mw-heading mw-heading5"><h5 id="Mice">Mice</h5>[<a href="/w/index.php?title=Serotonin&action=edit&section=48" title="Edit section: Mice">edit</a>]</div> Researchers at the Department of Pharmacology and Medical Chemistry used serotonergic drugs on male mice to study the effects of selected drugs on their behavior.<a href="#cite_note-Olivier_1989-203">[202]</a> Mice in isolation exhibit increased levels of <a href="/wiki/Agonistic_behaviour" title="Agonistic behaviour">agonistic behavior</a> towards one another. Results found that serotonergic drugs reduce aggression in isolated mice while simultaneously increasing social interaction.<a href="#cite_note-Olivier_1989-203">[202]</a> Each of the treatments use a different mechanism for targeting aggression, but ultimately all have the same outcome. While the study shows that serotonergic drugs successfully target serotonin receptors, it does not show specifics of the mechanisms that affect behavior, as all types of drugs tended to reduce aggression in isolated male mice.<a href="#cite_note-Olivier_1989-203">[202]</a> Aggressive mice kept out of isolation may respond differently to changes in serotonin reuptake. <div class="mw-heading mw-heading4"><h4 id="Behavior">Behavior</h4>[<a href="/w/index.php?title=Serotonin&action=edit&section=49" title="Edit section: Behavior">edit</a>]</div> Like in humans, serotonin is extremely involved in regulating behavior in most other vertebrates. This includes not only response and social behaviors, but also influencing mood. Defects in serotonin pathways can lead to intense variations in mood, as well as symptoms of mood disorders, which can be present in more than just humans. <div class="mw-heading mw-heading5"><h5 id="Social_interaction">Social interaction</h5>[<a href="/w/index.php?title=Serotonin&action=edit&section=50" title="Edit section: Social interaction">edit</a>]</div> One of the most researched aspects of social interaction in which serotonin is involved is aggression. Aggression is regulated by the 5-HT system, as serotonin levels can both induce or inhibit aggressive behaviors, as seen in mice (see section on Mice) and crabs.<a href="#cite_note-Olivier_1989-203">[202]</a> While this is widely accepted, it is unknown if serotonin interacts directly or indirectly with parts of the brain influencing aggression and other behaviors.<a href="#cite_note-Bacqué-Cazenave_2020-195">[194]</a> Studies of serotonin levels show that they drastically increase and decrease during social interactions, and they generally correlate with inhibiting or inciting aggressive behavior.<a href="#cite_note-204">[203]</a> The exact mechanism of serotonin influencing social behaviors is unknown, as pathways in the 5-HT system in various vertebrates can differ greatly.<a href="#cite_note-Bacqué-Cazenave_2020-195">[194]</a> <div class="mw-heading mw-heading5"><h5 id="Response_to_stimuli">Response to stimuli</h5>[<a href="/w/index.php?title=Serotonin&action=edit&section=51" title="Edit section: Response to stimuli">edit</a>]</div> Serotonin is important in environmental response pathways, along with other <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitters</a>.<a href="#cite_note-205">[204]</a> Specifically, it has been found to be involved in auditory processing in social settings, as primary sensory systems are connected to social interactions.<a href="#cite_note-Petersen_2017-206">[205]</a> Serotonin is found in the <a href="/wiki/Inferior_colliculus" title="Inferior colliculus">IC structure</a> of the midbrain, which processes specie specific and non-specific social interactions and vocalizations.<a href="#cite_note-Petersen_2017-206">[205]</a> It also receives acoustic projections that convey signals to auditory processing regions.<a href="#cite_note-Petersen_2017-206">[205]</a> Research has proposed that serotonin shapes the auditory information being received by the IC and therefore is influential in the responses to auditory stimuli.<a href="#cite_note-Petersen_2017-206">[205]</a> This can influence how an organism responds to the sounds of predatory or other impactful species in their environment, as serotonin uptake can influence aggression or social interaction. <div class="mw-heading mw-heading5"><h5 id="Mood">Mood</h5>[<a href="/w/index.php?title=Serotonin&action=edit&section=52" title="Edit section: Mood">edit</a>]</div> We can describe mood not as specific to an emotional status, but as associated with a relatively long-lasting emotional state. Serotonin's association with mood is most known for various forms of depression and bipolar disorders in humans.<a href="#cite_note-Lucki_1998-196">[195]</a> Disorders caused by serotonergic activity potentially contribute to the many symptoms of major depression, such as overall mood, activity, suicidal thoughts and sexual and <a href="/wiki/Cognitive_dysfunction" class="mw-redirect" title="Cognitive dysfunction">cognitive dysfunction</a>. <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">Selective serotonin reuptake inhibitors</a> (SSRI's) are a class of drugs demonstrated to be an effective treatment in major depressive disorder and are the most prescribed class of antidepressants. SSRI's function is to block the reuptake of serotonin, making more serotonin available to absorb by the receiving neuron. Animals have been studied for decades in order to understand depressive behavior among species. One of the most familiar studies, the forced swimming test (FST), was performed to measure potential antidepressant activity.<a href="#cite_note-Lucki_1998-196">[195]</a> Rats were placed in an inescapable container of water, at which point time spent immobile and number of active behaviors (such as splashing or climbing) were compared before and after a panel of anti-depressant drugs were administered. Antidepressants that selectively inhibit NE reuptake were shown to reduce immobility and selectively increase climbing without affecting swimming. However, results of the SSRI's also show reduced immobility but increased swimming without affecting climbing. This study demonstrated the importance of behavioral tests for antidepressants, as they can detect drugs with an effect on core behavior along with behavioral components of species.<a href="#cite_note-Lucki_1998-196">[195]</a> <div class="mw-heading mw-heading3"><h3 id="Growth_and_reproduction">Growth and reproduction</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=53" title="Edit section: Growth and reproduction">edit</a>]</div> In the nematode <a href="/wiki/Caenorhabditis_elegans" title="Caenorhabditis elegans">C. elegans</a>, artificial depletion of serotonin or the increase of octopamine cues behavior typical of a low-food environment: C. elegans becomes more active, and mating and egg-laying are suppressed, while the opposite occurs if serotonin is increased or octopamine is decreased in this animal.<a href="#cite_note-pmid18522834-34">[34]</a> Serotonin is necessary for normal nematode male mating behavior,<a href="#cite_note-pmid8254383-207">[206]</a> and the inclination to leave food to search for a mate.<a href="#cite_note-pmid15329389-208">[207]</a> The serotonergic signaling used to adapt the worm's behaviour to fast changes in the environment affects <a href="/wiki/Insulin" title="Insulin">insulin</a>-like signaling and the <a href="/wiki/TGF_beta_signaling_pathway" title="TGF beta signaling pathway">TGF beta signaling pathway</a>,<a href="#cite_note-Murakami_H_2007-209">[208]</a> which control long-term adaption. In the <a href="/wiki/Drosophila_melanogaster" title="Drosophila melanogaster">fruit fly</a> insulin both regulates <a href="/wiki/Blood_sugar" class="mw-redirect" title="Blood sugar">blood sugar</a> as well as acting as a <a href="/wiki/Growth_factor" title="Growth factor">growth factor</a>. Thus, in the fruit fly, serotonergic neurons regulate the adult body size by affecting insulin secretion.<a href="#cite_note-pmid18628395-210">[209]</a><a href="#cite_note-pmid18628391-211">[210]</a> Serotonin has also been identified as the trigger for <a href="/wiki/Swarm_behavior" class="mw-redirect" title="Swarm behavior">swarm behavior</a> in locusts.<a href="#cite_note-Anstey-186">[185]</a> In humans, though insulin regulates blood sugar and <a href="/wiki/Insulin-like_growth_factor" title="Insulin-like growth factor">IGF</a> regulates growth, serotonin controls the release of both hormones, modulating insulin release from the <a href="/wiki/Beta_cell" title="Beta cell">beta cells</a> in the <a href="/wiki/Pancreas" title="Pancreas">pancreas</a> through serotonylation of GTPase signaling proteins.<a href="#cite_note-pmid19859528-44">[44]</a> Exposure to <a href="/wiki/SSRI" class="mw-redirect" title="SSRI">SSRIs</a> during <a href="/wiki/Gestation" title="Gestation">pregnancy</a> reduces fetal growth.<a href="#cite_note-pmid19262294-212">[211]</a> Genetically altered C. elegans worms that lack serotonin have an increased reproductive lifespan, may become obese, and sometimes present with arrested development at a <a href="/wiki/Dauer_larva" title="Dauer larva">dormant larval state</a>.<a href="#cite_note-pmid19851507-213">[212]</a><a href="#cite_note-pmid10676966-214">[213]</a> <div class="mw-heading mw-heading3"><h3 id="Aging_and_age-related_phenotypes">Aging and age-related phenotypes</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=54" title="Edit section: Aging and age-related phenotypes">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/Aging_brain#Serotonin" title="Aging brain">Aging brain § Serotonin</a></div> Serotonin is known to regulate aging, learning, and memory. The first evidence comes from the study of longevity in <a href="/wiki/Caenorhabditis_elegans" title="Caenorhabditis elegans">C. elegans</a>.<a href="#cite_note-Murakami_H_2007-209">[208]</a> During early phase of aging[<a href="/wiki/Wikipedia:Vagueness" title="Wikipedia:Vagueness">vague</a>], the level of serotonin increases, which alters locomotory behaviors and associative memory.<a href="#cite_note-215">[214]</a> The effect is restored by mutations and drugs (including <a href="/wiki/Mianserin" title="Mianserin">mianserin</a> and <a href="/wiki/Methiothepin" class="mw-redirect" title="Methiothepin">methiothepin</a>) that inhibit <a href="/wiki/Serotonin_receptors" class="mw-redirect" title="Serotonin receptors">serotonin receptors</a>. The observation does not contradict with the notion that the serotonin level goes down in mammals and humans, which is typically seen in late but not early[<a href="/wiki/Wikipedia:Vagueness" title="Wikipedia:Vagueness">vague</a>] phase of aging. <div class="mw-heading mw-heading2"><h2 id="Biochemical_mechanisms">Biochemical mechanisms</h2>[<a href="/w/index.php?title=Serotonin&action=edit&section=55" title="Edit section: Biochemical mechanisms">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3>[<a href="/w/index.php?title=Serotonin&action=edit&section=56" title="Edit section: Biosynthesis">edit</a>]</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Serotonin_biosynthesis.svg" class="mw-file-description"><img alt="On top an L-tryptophan molecule with an arrow down to a 5-HTP molecule. Tryptophan hydroxylase catalyses this reaction with help of O2 and tetrahydrobiopterin, which becomes water and dihydrobiopterin. From the 5-HTP molecule goes an arrow down to a serotonin molecule. Aromatic L-amino acid decarboxylase or 5-Hydroxytryptophan decarboxylase catalyses this reaction with help of pyridoxal phosphate. From the serotonin molecule goes an arrow to a 5-HIAA molecule at the bottom of the image. Monoamine oxidase catalyses this reaction, in the process O2 and water is consumed, and ammonia and hydrogen peroxide is produced." src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Serotonin_biosynthesis.svg/340px-Serotonin_biosynthesis.svg.png" decoding="async" width="340" height="583" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Serotonin_biosynthesis.svg/510px-Serotonin_biosynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Serotonin_biosynthesis.svg/680px-Serotonin_biosynthesis.svg.png 2x" data-file-width="789" data-file-height="1354" /></a><figcaption>The pathway for the synthesis of serotonin from tryptophan</figcaption></figure> In animals and humans, serotonin is <a href="/wiki/Biosynthesis" title="Biosynthesis">synthesized</a> from the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> L-<a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a> by a short <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathway</a> consisting of two <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>, <a href="/wiki/Tryptophan_hydroxylase" title="Tryptophan hydroxylase">tryptophan hydroxylase</a> (TPH) and <a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">aromatic amino acid decarboxylase</a> (DDC), and the coenzyme <a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">pyridoxal phosphate</a>. The TPH-mediated reaction is the rate-limiting step in the pathway. TPH has been shown to exist in two forms: <a href="/wiki/TPH1" title="TPH1">TPH1</a>, found in several <a href="/wiki/Biological_tissue" class="mw-redirect" title="Biological tissue">tissues</a>, and <a href="/wiki/TPH2" title="TPH2">TPH2</a>, which is a neuron-specific <a href="/wiki/Protein_isoform" title="Protein isoform">isoform</a>.<a href="#cite_note-pmid14597720-216">[215]</a> Serotonin can be synthesized from tryptophan in the lab using <a href="/wiki/Aspergillus_niger" title="Aspergillus niger">Aspergillus niger</a> and <a href="/wiki/Psilocybe_coprophila" class="mw-redirect" title="Psilocybe coprophila">Psilocybe coprophila</a> as catalysts. The first phase to 5-hydroxytryptophan would require letting tryptophan sit in ethanol and water for 7 days, then mixing in enough HCl (or other acid) to bring the pH to 3, and then adding NaOH to make a pH of 13 for 1 hour. Aspergillus niger would be the catalyst for this first phase. The second phase to synthesizing tryptophan itself from the 5-hydroxytryptophan intermediate would require adding ethanol and water, and letting sit for 30 days this time. The next two steps would be the same as the first phase: adding HCl to make the pH = 3, and then adding NaOH to make the pH very basic at 13 for 1 hour. This phase uses the Psilocybe coprophila as the catalyst for the reaction.<a href="#cite_note-217">[216]</a> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Biosynthesis_and_breakdown_of_serotonin_and_the_catecholamines,_and_the_metabolic_block_in_AADC_deficiency.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Biosynthesis_and_breakdown_of_serotonin_and_the_catecholamines%2C_and_the_metabolic_block_in_AADC_deficiency.png/220px-Biosynthesis_and_breakdown_of_serotonin_and_the_catecholamines%2C_and_the_metabolic_block_in_AADC_deficiency.png" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Biosynthesis_and_breakdown_of_serotonin_and_the_catecholamines%2C_and_the_metabolic_block_in_AADC_deficiency.png/330px-Biosynthesis_and_breakdown_of_serotonin_and_the_catecholamines%2C_and_the_metabolic_block_in_AADC_deficiency.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Biosynthesis_and_breakdown_of_serotonin_and_the_catecholamines%2C_and_the_metabolic_block_in_AADC_deficiency.png/440px-Biosynthesis_and_breakdown_of_serotonin_and_the_catecholamines%2C_and_the_metabolic_block_in_AADC_deficiency.png 2x" data-file-width="778" data-file-height="583" /></a><figcaption>Process</figcaption></figure> Serotonin taken orally does not pass into the serotonergic pathways of the central nervous system, because it does not cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a>.<a href="#cite_note-pmid18043762-9">[9]</a> However, <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a> and its <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> <a href="/wiki/5-hydroxytryptophan" class="mw-redirect" title="5-hydroxytryptophan">5-hydroxytryptophan</a> (5-HTP), from which serotonin is synthesized, do cross the blood–brain barrier. These agents are available as <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplements</a> and in various foods, and may be effective serotonergic agents. One product of serotonin breakdown is <a href="/wiki/5-hydroxyindoleacetic_acid" class="mw-redirect" title="5-hydroxyindoleacetic acid">5-hydroxyindoleacetic acid</a> (5-HIAA), which is excreted in the <a href="/wiki/Urine" title="Urine">urine</a>. Serotonin and 5-HIAA are sometimes produced in excess amounts by certain <a href="/wiki/Tumor" class="mw-redirect" title="Tumor">tumors</a> or <a href="/wiki/Cancer" title="Cancer">cancers</a>, and levels of these substances may be measured in the urine to test for these tumors. <div class="mw-heading mw-heading2"><h2 id="Analytical_chemistry">Analytical chemistry</h2>[<a href="/w/index.php?title=Serotonin&action=edit&section=57" title="Edit section: Analytical chemistry">edit</a>]</div> <a href="/wiki/Indium_tin_oxide" title="Indium tin oxide">Indium tin oxide</a> is recommended for the <a href="/wiki/Electrode" title="Electrode">electrode</a> material in <a href="/wiki/Electrochemistry" title="Electrochemistry">electrochemical</a> investigation of concentrations produced, detected, or consumed by <a href="/wiki/Microbe" class="mw-redirect" title="Microbe">microbes</a>.<a href="#cite_note-Sismaet-Goluch-2018-218">[217]</a> A mass spectrometry technique was developed in 1994 to measure the <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a> of both natural and synthetic serotonins.<a href="#cite_note-Henson-et-al-1999-219">[218]</a> <div class="mw-heading mw-heading2"><h2 id="History_and_etymology">History and etymology</h2>[<a href="/w/index.php?title=Serotonin&action=edit&section=58" title="Edit section: History and etymology">edit</a>]</div> It had been known to physiologists for over a century that a vasoconstrictor material appears in serum when blood was allowed to clot.<a href="#cite_note-Anthony_1984-220">[219]</a> In 1935, Italian <a href="/wiki/Vittorio_Erspamer" title="Vittorio Erspamer">Vittorio Erspamer</a>, working in Pavia, showed an extract from enterochromaffin cells made intestines contract. Some believed it contained <a href="/wiki/Adrenaline" title="Adrenaline">adrenaline</a>, but two years later, Erspamer was able to show it was a previously unknown <a href="/wiki/Amine" title="Amine">amine</a>, which he named "enteramine".<a href="#cite_note-Erspamer_1954-221">[220]</a><a href="#cite_note-pmid17526278-222">[221]</a> In 1948, <a href="/wiki/Maurice_M._Rapport" title="Maurice M. Rapport">Maurice M. Rapport</a>, <a href="/wiki/Arda_Green" title="Arda Green">Arda Green</a>, and <a href="/wiki/Irvine_Page" title="Irvine Page">Irvine Page</a> of the <a href="/wiki/Cleveland_Clinic" title="Cleveland Clinic">Cleveland Clinic</a> discovered a vasoconstrictor substance in <a href="/wiki/Blood_plasma" title="Blood plasma">blood serum</a>, and since it was a serum agent affecting vascular tone, they named it serotonin.<a href="#cite_note-pmid18100415-223">[222]</a> In 1952, enteramine was shown to be the same substance as serotonin, and as the broad range of physiological roles was elucidated, the abbreviation 5-HT of the proper chemical name 5-hydroxytryptamine became the preferred name in the pharmacological field.<a href="#cite_note-pmid13035756-224">[223]</a> Synonyms of serotonin include: 5-hydroxytriptamine, enteramine, substance DS, and 3-(β-aminoethyl)-5-hydroxyindole.<a href="#cite_note-225">[224]</a> In 1953, <a href="/wiki/Betty_Twarog" title="Betty Twarog">Betty Twarog</a> and Page discovered serotonin in the central nervous system.<a href="#cite_note-226">[225]</a> Page regarded Erspamer's work on <a href="/wiki/Octopus_vulgaris" class="mw-redirect" title="Octopus vulgaris">Octopus vulgaris</a>, <a href="/wiki/Discoglossus_pictus" title="Discoglossus pictus">Discoglossus pictus</a>, <a href="/wiki/Hexaplex_trunculus" title="Hexaplex trunculus">Hexaplex trunculus</a>, <a href="/wiki/Bolinus_brandaris" title="Bolinus brandaris">Bolinus brandaris</a>, <a href="/wiki/Sepia_(cephalopod)" title="Sepia (cephalopod)">Sepia</a>, <a href="/wiki/Mytilus_(bivalve)" title="Mytilus (bivalve)">Mytilus</a>, and <a href="/wiki/Ostrea" title="Ostrea">Ostrea</a> as valid and fundamental to understanding this newly identified substance, but regarded his earlier results in various models – especially those from rat blood – to be too confounded by the presence of other bioactive chemicals, including some other vasoactives.<a href="#cite_note-Page-1954-227">[226]</a> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2>[<a href="/w/index.php?title=Serotonin&action=edit&section=59" title="Edit section: Notes">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"><ol class="references"> <li id="cite_note-48"><a href="#cite_ref-48">^</a> References for the functions of these receptors are available on the wikipedia pages for the specific receptor in question </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Serotonin&action=edit&section=60" title="Edit section: References">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-CAPLUS-1"><a href="#cite_ref-CAPLUS_1-0">^</a> Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994–2011 ACD/Labs) </li> <li id="cite_note-pK-2"><a 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no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output 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F1000Research. 6: 123. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.12688%2Ff1000research.9736.1">10.12688/f1000research.9736.1</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/PMC5302148">5302148</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/28232871">28232871</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=F1000Research&rft.atitle=Serotonin+receptors+in+depression%3A+from+A+to+B&rft.volume=6&rft.pages=123&rft.date=2017&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5302148%23id-name%3DPMC&rft_id=info%3Apmid%2F28232871&rft_id=info%3Adoi%2F10.12688%2Ff1000research.9736.1&rft.aulast=Nautiyal&rft.aufirst=KM&rft.au=Hen%2C+R&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5302148&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASerotonin" class="Z3988"> </li> <li id="cite_note-55"><a href="#cite_ref-55">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFrazerHensler1999" class="citation book cs1">Frazer A, Hensler JG (1999). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Search&db=books&doptcmdl=GenBookHL&term=raphe+AND+serotonin+release+AND+bnchm%5Bbook%5D+AND+160428%5Buid%5D&rid=bnchm.section.946#949">"Understanding the neuroanatomical organization of serotonergic cells in the brain provides insight into the functions of this neurotransmitter"</a>. In <a href="/w/index.php?title=George_J._Siegel&action=edit&redlink=1" class="new" title="George J. Siegel (page does not exist)">Siegel GJ</a>, Agranoff, Bernard W, Fisher SK, Albers RW, Uhler MD (eds.). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/bv.fcgi?rid=bnchm">Basic Neurochemistry</a> (Sixth ed.). Lippincott Williams & Wilkins. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-397-51820-3" title="Special:BookSources/978-0-397-51820-3"><bdi>978-0-397-51820-3</bdi></a>. <q>In 1964, Dahlstrom and Fuxe (discussed in [2]), using the <a href="/wiki/Falck-Hillarp_technique" class="mw-redirect" title="Falck-Hillarp technique">Falck-Hillarp technique</a> of histofluorescence, observed that the majority of serotonergic soma are found in cell body groups, which previously had been designated as the Raphe nuclei.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Understanding+the+neuroanatomical+organization+of+serotonergic+cells+in+the+brain+provides+insight+into+the+functions+of+this+neurotransmitter&rft.btitle=Basic+Neurochemistry&rft.edition=Sixth&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=1999&rft.isbn=978-0-397-51820-3&rft.aulast=Frazer&rft.aufirst=A&rft.au=Hensler%2C+JG&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fentrez%2Fquery.fcgi%3Fcmd%3DSearch%26db%3Dbooks%26doptcmdl%3DGenBookHL%26term%3Draphe%2BAND%2Bserotonin%2Brelease%2BAND%2Bbnchm%255Bbook%255D%2BAND%2B160428%255Buid%255D%26rid%3Dbnchm.section.946%23949&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASerotonin" class="Z3988"> </li> <li id="cite_note-56"><a href="#cite_ref-56">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBinderHirokawa2009" class="citation book cs1">Binder MD, Hirokawa N (2009). encyclopedia of neuroscience. Berlin: Springer. p. 705. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-23735-8" title="Special:BookSources/978-3-540-23735-8"><bdi>978-3-540-23735-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=encyclopedia+of+neuroscience&rft.place=Berlin&rft.pages=705&rft.pub=Springer&rft.date=2009&rft.isbn=978-3-540-23735-8&rft.aulast=Binder&rft.aufirst=MD&rft.au=Hirokawa%2C+N&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASerotonin" class="Z3988"> </li> <li id="cite_note-57"><a href="#cite_ref-57">^</a> The raphe nuclei group of <a href="/wiki/Neurons" class="mw-redirect" title="Neurons">neurons</a> are located along the <a href="/wiki/Reticular_formation" title="Reticular formation">brain stem</a> from the labels '<a href="/wiki/Mesencephalon" class="mw-redirect" title="Mesencephalon">Mid Brain</a>' to '<a href="/wiki/Medulla_oblongata" title="Medulla oblongata">Oblongata</a>', centered on the <a href="/wiki/Pons" title="Pons">pons</a>. (<a href="/wiki/File:Gray715.png" title="File:Gray715.png">See relevant image</a>.) </li> <li id="cite_note-58"><a href="#cite_ref-58">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMüllerJacobs2009" class="citation book cs1">Müller CP, Jacobs BL, eds. (2009). Handbook of the behavioral neurobiology of serotonin (1st ed.). London: Academic. pp. 51–59. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-374634-4" title="Special:BookSources/978-0-12-374634-4"><bdi>978-0-12-374634-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Handbook+of+the+behavioral+neurobiology+of+serotonin&rft.place=London&rft.pages=51-59&rft.edition=1st&rft.pub=Academic&rft.date=2009&rft.isbn=978-0-12-374634-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASerotonin" class="Z3988"> </li> <li id="cite_note-59"><a href="#cite_ref-59">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPassosHerculanoOliveirade_Lima2019" class="citation journal cs1">Passos AD, Herculano AM, Oliveira KR, de Lima SM, Rocha FA, Freitas HR, et al. (October 2019). "Regulation of the Serotonergic System by Kainate in the Avian Retina". 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Chem Rev. 124 (1): 124–163. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.chemrev.3c00375">10.1021/acs.chemrev.3c00375</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/38033123">38033123</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem+Rev&rft.atitle=Serotonin+2A+Receptor+%285-HT2AR%29+Agonists%3A+Psychedelics+and+Non-Hallucinogenic+Analogues+as+Emerging+Antidepressants&rft.volume=124&rft.issue=1&rft.pages=124-163&rft.date=2024-01&rft_id=info%3Adoi%2F10.1021%2Facs.chemrev.3c00375&rft_id=info%3Apmid%2F38033123&rft.aulast=Duan&rft.aufirst=W&rft.au=Cao%2C+D&rft.au=Wang%2C+S&rft.au=Cheng%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASerotonin" class="Z3988"> </li> <li id="cite_note-Nichols2018-128">^ <a href="#cite_ref-Nichols2018_128-0">a</a> <a href="#cite_ref-Nichols2018_128-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNichols2018" class="citation journal cs1">Nichols DE (2018). 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J Psychopharmacol. 38 (1): 3–18. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F02698811231211219">10.1177/02698811231211219</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/PMC10851641">10851641</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/37982394">37982394</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Psychopharmacol&rft.atitle=Drug-drug+interactions+involving+classic+psychedelics%3A+A+systematic+review&rft.volume=38&rft.issue=1&rft.pages=3-18&rft.date=2024-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10851641%23id-name%3DPMC&rft_id=info%3Apmid%2F37982394&rft_id=info%3Adoi%2F10.1177%2F02698811231211219&rft.aulast=Halman&rft.aufirst=A&rft.au=Kong%2C+G&rft.au=Sarris%2C+J&rft.au=Perkins%2C+D&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10851641&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASerotonin" class="Z3988"> </li> <li id="cite_note-VargasDunlapDong2023-130">^ <a href="#cite_ref-VargasDunlapDong2023_130-0">a</a> <a href="#cite_ref-VargasDunlapDong2023_130-1">b</a> <a href="#cite_ref-VargasDunlapDong2023_130-2">c</a> <a href="#cite_ref-VargasDunlapDong2023_130-3">d</a> <a href="#cite_ref-VargasDunlapDong2023_130-4">e</a> <a href="#cite_ref-VargasDunlapDong2023_130-5">f</a> <a href="#cite_ref-VargasDunlapDong2023_130-6">g</a> <a href="#cite_ref-VargasDunlapDong2023_130-7">h</a> <a href="#cite_ref-VargasDunlapDong2023_130-8">i</a> <a href="#cite_ref-VargasDunlapDong2023_130-9">j</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVargasDunlapDongCarter2023" class="citation journal cs1">Vargas MV, Dunlap LE, Dong C, Carter SJ, Tombari RJ, Jami SA, et al. (February 2023). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10108900">"Psychedelics promote neuroplasticity through the activation of intracellular 5-HT2A receptors"</a>. Science. 379 (6633): 700–706. <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/2023Sci...379..700V">2023Sci...379..700V</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.adf0435">10.1126/science.adf0435</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/PMC10108900">10108900</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/36795823">36795823</a>. <q>In addition to promoting psychedelic-induced structural neuroplasticity, the intracellular population of 5-HT2ARs might also contribute to the hallucinogenic effects of psychedelics. When we administered a serotonin-releasing agent to wild type mice, we did not observe a HTR. However, the same drug was able to induce a HTR in mice expressing SERT on cortical neurons of the mPFC—a brain region known to be essential for the HTR (49). Thus, activation of intracellular cortical 5-HT2ARs may play a role in the subjective effects of psychedelics. This hypothesis is further supported by previous work demonstrating that a high dose of the serotonin precursor 5-hydroxytryptophan (5-HTP) induces a HTR in WT mice, which can be blocked by an N-methyltransferase inhibitor that prevents the metabolism of 5-HTP to N-methyltryptamines (50). Inhibition of N-methyltransferase failed to block the HTR induced by 5-MeO-DMT (50). Taken together, this work emphasizes that accessing intracellular 5-HT2ARs is important for 5-HT2AR agonists to produce a HTR.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Psychedelics+promote+neuroplasticity+through+the+activation+of+intracellular+5-HT2A+receptors&rft.volume=379&rft.issue=6633&rft.pages=700-706&rft.date=2023-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10108900%23id-name%3DPMC&rft_id=info%3Apmid%2F36795823&rft_id=info%3Adoi%2F10.1126%2Fscience.adf0435&rft_id=info%3Abibcode%2F2023Sci...379..700V&rft.aulast=Vargas&rft.aufirst=MV&rft.au=Dunlap%2C+LE&rft.au=Dong%2C+C&rft.au=Carter%2C+SJ&rft.au=Tombari%2C+RJ&rft.au=Jami%2C+SA&rft.au=Cameron%2C+LP&rft.au=Patel%2C+SD&rft.au=Hennessey%2C+JJ&rft.au=Saeger%2C+HN&rft.au=McCorvy%2C+JD&rft.au=Gray%2C+JA&rft.au=Tian%2C+L&rft.au=Olson%2C+DE&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10108900&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASerotonin" class="Z3988"> </li> <li id="cite_note-Sapienza2023-131">^ <a href="#cite_ref-Sapienza2023_131-0">a</a> <a href="#cite_ref-Sapienza2023_131-1">b</a> <a href="#cite_ref-Sapienza2023_131-2">c</a> <a href="#cite_ref-Sapienza2023_131-3">d</a> <a href="#cite_ref-Sapienza2023_131-4">e</a> <a href="#cite_ref-Sapienza2023_131-5">f</a> <a href="#cite_ref-Sapienza2023_131-6">g</a> <a href="#cite_ref-Sapienza2023_131-7">h</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSapienza2023" class="citation journal cs1">Sapienza J (13 October 2023). <a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fpsychoactives2040018">"The Key Role of Intracellular 5-HT2A Receptors: A Turning Point in Psychedelic Research?"</a>. Psychoactives. 2 (4): 287–293. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fpsychoactives2040018">10.3390/psychoactives2040018</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/2813-1851">2813-1851</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Psychoactives&rft.atitle=The+Key+Role+of+Intracellular+5-HT2A+Receptors%3A+A+Turning+Point+in+Psychedelic+Research%3F&rft.volume=2&rft.issue=4&rft.pages=287-293&rft.date=2023-10-13&rft_id=info%3Adoi%2F10.3390%2Fpsychoactives2040018&rft.issn=2813-1851&rft.aulast=Sapienza&rft.aufirst=J&rft_id=https%3A%2F%2Fdoi.org%2F10.3390%252Fpsychoactives2040018&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASerotonin" class="Z3988"> </li> <li id="cite_note-SchmidBohn2018-132"><a href="#cite_ref-SchmidBohn2018_132-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchmidBohn2018" class="citation book cs1">Schmid CL, Bohn LM (2018). 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J Neurosci. 30 (40): 13513–24. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1523%2FJNEUROSCI.1665-10.2010">10.1523/JNEUROSCI.1665-10.2010</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/PMC3001293">3001293</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/20926677">20926677</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Neurosci&rft.atitle=Serotonin%2C+but+not+N-methyltryptamines%2C+activates+the+serotonin+2A+receptor+via+a+%CE%B2-arrestin2%2FSrc%2FAkt+signaling+complex+in+vivo&rft.volume=30&rft.issue=40&rft.pages=13513-24&rft.date=2010-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3001293%23id-name%3DPMC&rft_id=info%3Apmid%2F20926677&rft_id=info%3Adoi%2F10.1523%2FJNEUROSCI.1665-10.2010&rft.aulast=Schmid&rft.aufirst=CL&rft.au=Bohn%2C+LM&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3001293&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASerotonin" class="Z3988"> </li> <li id="cite_note-HalberstadtGeyer2018-135"><a href="#cite_ref-HalberstadtGeyer2018_135-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHalberstadtGeyer2018" class="citation journal cs1">Halberstadt AL, Geyer MA (2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5787039">"Effect of Hallucinogens on Unconditioned Behavior"</a>. 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The American Journal of Physiology. 175 (1): 157–161. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1152%2Fajplegacy.1953.175.1.157">10.1152/ajplegacy.1953.175.1.157</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/13114371">13114371</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Physiology&rft.atitle=Serotonin+content+of+some+mammalian+tissues+and+urine+and+a+method+for+its+determination&rft.volume=175&rft.issue=1&rft.pages=157-161&rft.date=1953-10&rft_id=info%3Adoi%2F10.1152%2Fajplegacy.1953.175.1.157&rft_id=info%3Apmid%2F13114371&rft.aulast=Twarog&rft.aufirst=BM&rft.au=Page%2C+IH&rft_id=https%3A%2F%2Fdoi.org%2F10.1152%252Fajplegacy.1953.175.1.157&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASerotonin" class="Z3988"> </li> <li id="cite_note-Page-1954-227"><a href="#cite_ref-Page-1954_227-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPage1954" class="citation journal cs1"><a href="/wiki/Irvine_Page" title="Irvine Page">Page IH</a> (July 1954). "Serotonin (5-hydroxytryptamine)". Physiological Reviews. 34 (3). <a href="/wiki/American_Physiological_Society" title="American Physiological Society">American Physiological Society</a>: 563–588. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1152%2Fphysrev.1954.34.3.563">10.1152/physrev.1954.34.3.563</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/13185755">13185755</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Physiological+Reviews&rft.atitle=Serotonin+%285-hydroxytryptamine%29&rft.volume=34&rft.issue=3&rft.pages=563-588&rft.date=1954-07&rft_id=info%3Adoi%2F10.1152%2Fphysrev.1954.34.3.563&rft_id=info%3Apmid%2F13185755&rft.aulast=Page&rft.aufirst=IH&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASerotonin" class="Z3988"> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2>[<a href="/w/index.php?title=Serotonin&action=edit&section=61" title="Edit section: Further reading">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin" style=""> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGutknechtJacobStrobelKriegebaum2007" class="citation journal cs1">Gutknecht L, Jacob C, Strobel A, Kriegebaum C, Müller J, Zeng Y, et al. (June 2007). <a rel="nofollow" class="external text" href="https://doi.org/10.1017%2FS1461145706007437">"Tryptophan hydroxylase-2 gene variation influences personality traits and disorders related to emotional dysregulation"</a>. The International Journal of Neuropsychopharmacology. 10 (3): 309–320. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1017%2FS1461145706007437">10.1017/S1461145706007437</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/17176492">17176492</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+International+Journal+of+Neuropsychopharmacology&rft.atitle=Tryptophan+hydroxylase-2+gene+variation+influences+personality+traits+and+disorders+related+to+emotional+dysregulation&rft.volume=10&rft.issue=3&rft.pages=309-320&rft.date=2007-06&rft_id=info%3Adoi%2F10.1017%2FS1461145706007437&rft_id=info%3Apmid%2F17176492&rft.aulast=Gutknecht&rft.aufirst=L&rft.au=Jacob%2C+C&rft.au=Strobel%2C+A&rft.au=Kriegebaum%2C+C&rft.au=M%C3%BCller%2C+J&rft.au=Zeng%2C+Y&rft.au=Markert%2C+C&rft.au=Escher%2C+A&rft.au=Wendland%2C+J&rft.au=Reif%2C+A&rft.au=M%C3%B6ssner%2C+R&rft.au=Gross%2C+C&rft.au=Brocke%2C+B&rft.au=Lesch%2C+KP&rft_id=https%3A%2F%2Fdoi.org%2F10.1017%252FS1461145706007437&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASerotonin" class="Z3988"></li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2>[<a href="/w/index.php?title=Serotonin&action=edit&section=62" title="Edit section: External links">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-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/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" 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/Category:Serotonin" class="extiw" title="commons:Category:Serotonin">Serotonin</a>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://gmd.mpimp-golm.mpg.de/Spectrums/a1a3167e-cbab-45fd-adb6-9addc14e0ec2.aspx">5-Hydroxytryptamine MS Spectrum</a></li> <li><a rel="nofollow" class="external text" href="http://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=SRO">Serotonin bound to proteins</a> in the <a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB</a></li> <li><a rel="nofollow" class="external text" href="https://www.psychotropical.com/">PsychoTropicalResearch</a> Extensive reviews on serotonergic drugs and Serotonin Syndrome.</li> <li><a rel="nofollow" class="external text" href="https://www.chm.bris.ac.uk/motm/serotonin/home1.htm">Molecule of the Month: Serotonin</a> at <a href="/wiki/University_of_Bristol" title="University of Bristol">University of Bristol</a></li> <li>60-Second Psych: <a rel="nofollow" class="external text" href="https://www.scientificamerican.com/podcast/episode/68FC98F1-E48A-251D-8F65277181DB9A4E/">No Fair! My Serotonin Level Is Low</a>, <a href="/wiki/Scientific_American" title="Scientific American">Scientific American</a></li> <li><a rel="nofollow" class="external text" href="http://www.clinlabnavigator.com/Tests/Serotonin.html">Serotonin Test Interpretation on ClinLab Navigator</a>.</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul 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class="navbox-group" style="width:1%;font-weight:normal;">Glutamate system</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/Agmatine" title="Agmatine">Agmatine</a></li> <li><a href="/wiki/Aspartic_acid" title="Aspartic acid">Aspartic acid (aspartate)</a></li> <li><a href="/wiki/Glutamate_(neurotransmitter)" title="Glutamate (neurotransmitter)">Glutamic acid (glutamate)</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">Glutathione</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/S-Nitrosoglutathione" title="S-Nitrosoglutathione">GSNO</a></li> <li><a href="/wiki/Oxidized_glutathione" class="mw-redirect" title="Oxidized glutathione">GSSG</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/N-Acetylaspartic_acid" title="N-Acetylaspartic acid">NAA</a></li> <li><a href="/wiki/N-Acetylaspartylglutamic_acid" title="N-Acetylaspartylglutamic acid">NAAG</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">GABA system</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/Gamma-Aminobutyric_acid" class="mw-redirect" title="Gamma-Aminobutyric acid">GABA</a></li> <li><a href="/wiki/Gamma-Amino-beta-hydroxybutyric_acid" class="mw-redirect" title="Gamma-Amino-beta-hydroxybutyric acid">GABOB</a></li> <li><a href="/wiki/Gamma-Hydroxybutyric_acid" class="mw-redirect" title="Gamma-Hydroxybutyric acid">GHB</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">Glycine system</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/Alanine" title="Alanine">α-Alanine</a></li> <li><a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</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/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;"><a href="/wiki/GHB_receptor" title="GHB receptor">GHB system</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/Gamma-Hydroxybutyric_acid" class="mw-redirect" title="Gamma-Hydroxybutyric acid">GHB</a></li> <li><a href="/wiki/T-HCA" title="T-HCA">T-HCA (GHC)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Biogenic_amine" title="Biogenic amine">Biogenic amines</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;font-weight:normal; text-align: center;">Monoamines</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/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-OHM</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Adrenaline" title="Adrenaline">Epinephrine (adrenaline)</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">NAS (normelatonin)</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Trace amines</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/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine">N-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methyltryptamine" title="N-Methyltryptamine">N-Methyltryptamine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">m-Octopamine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine">p-Octopamine</a></li> <li><a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine">m-Tyramine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">p-Tyramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; 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/Histamine" title="Histamine">Histamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Neuropeptide" title="Neuropeptide">Neuropeptides</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Neuropeptides" title="Template:Neuropeptides">here</a> instead.</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="text-align: center;;width:1%"><a href="/wiki/Lipid" title="Lipid">Lipid</a>-derived</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Endocannabinoids" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Endocannabinoids</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Arachidonoylglycerol" title="2-Arachidonoylglycerol">2-AG</a></li> <li><a href="/wiki/2-Arachidonyl_glyceryl_ether" title="2-Arachidonyl glyceryl ether">2-AGE (noladin ether)</a></li> <li><a href="/w/index.php?title=2-Arachidonoyl_lysophosphatidylinositol&action=edit&redlink=1" class="new" title="2-Arachidonoyl lysophosphatidylinositol (page does not exist)">2-ALPI</a></li> <li><a href="/wiki/2-Oleoylglycerol" title="2-Oleoylglycerol">2-OG</a></li> <li><a href="/wiki/Arachidonoyl_serotonin" title="Arachidonoyl serotonin">AA-5-HT</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide (AEA)</a></li> <li><a href="/wiki/Docosatetraenoylethanolamide" title="Docosatetraenoylethanolamide">DEA</a></li> <li><a href="/wiki/Lysophosphatidylinositol" title="Lysophosphatidylinositol">LPI</a></li> <li><a href="/wiki/N-Arachidonoyl_dopamine" title="N-Arachidonoyl dopamine">NADA</a></li> <li><a href="/wiki/N-Arachidonylglycine" title="N-Arachidonylglycine">NAGly</a></li> <li><a href="/wiki/Oleoylethanolamide" title="Oleoylethanolamide">OEA</a></li> <li><a href="/wiki/Oleamide" title="Oleamide">Oleamide</a></li> <li><a href="/wiki/Palmitoylethanolamide" title="Palmitoylethanolamide">PEA</a></li> <li><a href="/wiki/RVD-Hp%CE%B1" title="RVD-Hpα">RVD-Hpα</a></li> <li><a href="/wiki/Stearoylethanolamide" title="Stearoylethanolamide">SEA</a></li> <li><a href="/wiki/Virodhamine" title="Virodhamine">Virodhamine (O-AEA)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Neurosteroid" title="Neurosteroid">Neurosteroids</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</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="text-align: center;;width:1%"><a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">Nucleobase</a>-derived</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Nucleosides" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Nucleosides</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 id="Adenosine_system" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a> system</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</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="text-align: center;;width:1%"><a href="/wiki/Vitamin" title="Vitamin">Vitamin</a>-derived</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"></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">Miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Cholinergic_system" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Cholinergic system</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/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Gasotransmitters" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Gasotransmitters</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/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide (CO)</a></li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide (H2S)</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide (NO)</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Candidates" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Candidates</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/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia (NH3)</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide (COS)</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide (N2O)</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide (SO2)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Serotonin_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Serotonin_receptor_modulators" title="Template:Serotonin receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Serotonin_receptor_modulators" title="Template talk:Serotonin receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Serotonin_receptor_modulators" title="Special:EditPage/Template:Serotonin receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Serotonin_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/5-HT_receptor" title="5-HT receptor">Serotonin 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/5-HT1_receptor" title="5-HT1 receptor">5-HT1</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1A_receptor" title="5-HT1A receptor">5-HT1A</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/8-OH-DPAT" title="8-OH-DPAT">8-OH-DPAT</a></li> <li><a href="/wiki/Adatanserin" title="Adatanserin">Adatanserin</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/Antidepressant" title="Antidepressant">Antidepressants</a> (e.g., <a href="/wiki/Etoperidone" title="Etoperidone">etoperidone</a>, <a href="/wiki/Hydroxynefazodone" title="Hydroxynefazodone">hydroxynefazodone</a>, <a href="/wiki/Nefazodone" title="Nefazodone">nefazodone</a>, <a href="/wiki/Trazodone" title="Trazodone">trazodone</a>, <a href="/wiki/Triazoledione" title="Triazoledione">triazoledione</a>, <a href="/wiki/Vilazodone" title="Vilazodone">vilazodone</a>, <a href="/wiki/Vortioxetine" title="Vortioxetine">vortioxetine</a>)</li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Cariprazine" title="Cariprazine">cariprazine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Lurasidone" title="Lurasidone">lurasidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>)</li> <li><a href="/wiki/Azapirone" title="Azapirone">Azapirones</a> (e.g., <a href="/wiki/Buspirone" title="Buspirone">buspirone</a>, <a href="/wiki/Eptapirone" title="Eptapirone">eptapirone</a>, <a href="/wiki/Gepirone" title="Gepirone">gepirone</a>, <a href="/wiki/Perospirone" title="Perospirone">perospirone</a>, <a href="/wiki/Tandospirone" title="Tandospirone">tandospirone</a>)</li> <li><a href="/wiki/Bay_R_1531" title="Bay R 1531">Bay R 1531</a></li> <li><a href="/wiki/Befiradol" title="Befiradol">Befiradol</a></li> <li><a href="/wiki/BMY-14802" title="BMY-14802">BMY-14802</a></li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Ebalzotan" title="Ebalzotan">Ebalzotan</a></li> <li><a href="/wiki/Eltoprazine" title="Eltoprazine">Eltoprazine</a></li> <li><a href="/wiki/Enciprazine" title="Enciprazine">Enciprazine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/F-11,461" title="F-11,461">F-11,461</a></li> <li><a href="/w/index.php?title=F-12826&action=edit&redlink=1" class="new" title="F-12826 (page does not exist)">F-12826</a></li> <li><a href="/w/index.php?title=F-13714&action=edit&redlink=1" class="new" title="F-13714 (page does not exist)">F-13714</a></li> <li><a href="/w/index.php?title=F-14679&action=edit&redlink=1" class="new" title="F-14679 (page does not exist)">F-14679</a></li> <li><a href="/wiki/F-15063" title="F-15063">F-15063</a></li> <li><a href="/wiki/F-15,599" title="F-15,599">F-15,599</a></li> <li><a href="/wiki/Flesinoxan" title="Flesinoxan">Flesinoxan</a></li> <li><a href="/wiki/Flibanserin" title="Flibanserin">Flibanserin</a></li> <li><a href="/wiki/Flumexadol" title="Flumexadol">Flumexadol</a></li> <li><a href="/wiki/Hypidone" title="Hypidone">Hypidone</a></li> <li><a href="/wiki/Lesopitron" title="Lesopitron">Lesopitron</a></li> <li><a href="/wiki/LY-293284" title="LY-293284">LY-293284</a></li> <li><a href="/w/index.php?title=LY-301317&action=edit&redlink=1" class="new" title="LY-301317 (page does not exist)">LY-301317</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Osemozotan" title="Osemozotan">MKC-242</a></li> <li><a href="/wiki/Naluzotan" title="Naluzotan">Naluzotan</a></li> <li><a href="/wiki/NBUMP" title="NBUMP">NBUMP</a></li> <li><a href="/wiki/Osemozotan" title="Osemozotan">Osemozotan</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/Pardoprunox" title="Pardoprunox">Pardoprunox</a></li> <li><a href="/wiki/Piclozotan" title="Piclozotan">Piclozotan</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Repinotan" title="Repinotan">Repinotan</a></li> <li><a href="/wiki/Roxindole" title="Roxindole">Roxindole</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/S-14,506" title="S-14,506">S-14,506</a></li> <li><a href="/wiki/S-14671" title="S-14671">S-14671</a></li> <li><a href="/wiki/S-15535" title="S-15535">S-15535</a></li> <li><a href="/wiki/Sarizotan" title="Sarizotan">Sarizotan</a></li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/w/index.php?title=SSR-181507&action=edit&redlink=1" class="new" title="SSR-181507 (page does not exist)">SSR-181507</a></li> <li><a href="/wiki/Sunepitron" title="Sunepitron">Sunepitron</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Indorenate" title="Indorenate">indorenate</a>, <a href="/wiki/N-Methylserotonin" title="N-Methylserotonin">N-Me-5-HT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>)</li> <li><a href="/wiki/TGBA01AD" title="TGBA01AD">TGBA01AD</a></li> <li><a href="/wiki/U-92,016-A" title="U-92,016-A">U-92,016-A</a></li> <li><a href="/wiki/Urapidil" title="Urapidil">Urapidil</a></li> <li><a href="/wiki/Vilazodone" title="Vilazodone">Vilazodone</a></li> <li><a href="/wiki/Xaliproden" title="Xaliproden">Xaliproden</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>)</li> <li><a href="/w/index.php?title=AV965&action=edit&redlink=1" class="new" title="AV965 (page does not exist)">AV965</a></li> <li><a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> (e.g., <a href="/wiki/Alprenolol" title="Alprenolol">alprenolol</a>, <a href="/wiki/Carteolol" title="Carteolol">carteolol</a>, <a href="/wiki/Cyanopindolol" title="Cyanopindolol">cyanopindolol</a>, <a href="/wiki/Iodocyanopindolol" title="Iodocyanopindolol">iodocyanopindolol</a>, <a href="/wiki/Isamoltane" title="Isamoltane">isamoltane</a>, <a href="/wiki/Oxprenolol" title="Oxprenolol">oxprenolol</a>, <a href="/wiki/Penbutolol" title="Penbutolol">penbutolol</a>, <a href="/wiki/Pindobind" title="Pindobind">pindobind</a>, <a href="/wiki/Pindolol" title="Pindolol">pindolol</a>, <a href="/wiki/Propranolol" title="Propranolol">propranolol</a>, <a href="/wiki/Tertatolol" title="Tertatolol">tertatolol</a>)</li> <li><a href="/wiki/BMY-7,378" class="mw-redirect" title="BMY-7,378">BMY-7,378</a></li> <li><a href="/wiki/CSP-2503" title="CSP-2503">CSP-2503</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>)</li> <li><a href="/w/index.php?title=FCE-24379&action=edit&redlink=1" class="new" title="FCE-24379 (page does not exist)">FCE-24379</a></li> <li><a href="/wiki/Flopropione" title="Flopropione">Flopropione</a></li> <li><a href="/w/index.php?title=GR-46611&action=edit&redlink=1" class="new" title="GR-46611 (page does not exist)">GR-46611</a></li> <li><a href="/wiki/Isamoltane" title="Isamoltane">Isamoltane</a></li> <li><a href="/wiki/Lecozotan" title="Lecozotan">Lecozotan</a></li> <li><a href="/wiki/Mefway_(18F)" title="Mefway (18F)">Mefway</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/MIN-117" title="MIN-117">MIN-117 (WF-516)</a></li> <li><a href="/wiki/MPPF" title="MPPF">MPPF</a></li> <li><a href="/wiki/NAN-190" title="NAN-190">NAN-190</a></li> <li><a href="/wiki/Robalzotan" title="Robalzotan">Robalzotan</a></li> <li><a href="/wiki/S-15535" title="S-15535">S-15535</a></li> <li><a href="/wiki/SB-649,915" title="SB-649,915">SB-649,915</a></li> <li><a href="/w/index.php?title=SDZ_216-525&action=edit&redlink=1" class="new" title="SDZ 216-525 (page does not exist)">SDZ 216-525</a></li> <li><a href="/wiki/Spiperone" title="Spiperone">Spiperone</a></li> <li><a href="/wiki/Spiramide" title="Spiramide">Spiramide</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/wiki/UH-301" title="UH-301">UH-301</a></li> <li><a href="/wiki/WAY-100135" title="WAY-100135">WAY-100135</a></li> <li><a href="/wiki/WAY-100635" title="WAY-100635">WAY-100635</a></li> <li><a href="/wiki/Xylamidine" title="Xylamidine">Xylamidine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" title="Ergometrine">ergometrine (ergonovine)</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/5-HT1B_receptor" title="5-HT1B receptor">5-HT1B</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/Anpirtoline" title="Anpirtoline">Anpirtoline</a></li> <li><a href="/wiki/CGS-12066A" title="CGS-12066A">CGS-12066A</a></li> <li><a href="/wiki/CP-93129" title="CP-93129">CP-93129</a></li> <li><a href="/wiki/CP-94253" title="CP-94253">CP-94253</a></li> <li><a href="/wiki/CP-122,288" title="CP-122,288">CP-122,288</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/wiki/Eltoprazine" title="Eltoprazine">Eltoprazine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/Donitriptan" title="Donitriptan">donitriptan</a>, <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>, <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>, <a href="/wiki/Zolmitriptan" title="Zolmitriptan">zolmitriptan</a>)</li> <li><a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>)</li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/AR-A000002" title="AR-A000002">AR-A000002</a></li> <li><a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> (e.g., <a href="/wiki/Alprenolol" title="Alprenolol">alprenolol</a>, <a href="/wiki/Carteolol" title="Carteolol">carteolol</a>, <a href="/wiki/Isamoltane" title="Isamoltane">isamoltane</a>, <a href="/wiki/Oxprenolol" title="Oxprenolol">oxprenolol</a>, <a href="/wiki/Penbutolol" title="Penbutolol">penbutolol</a>, <a href="/wiki/Propranolol" title="Propranolol">propranolol</a>, <a href="/wiki/Tertatolol" title="Tertatolol">tertatolol</a>)</li> <li><a href="/wiki/Elzasonan" title="Elzasonan">Elzasonan</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>)</li> <li><a href="/wiki/GR-127935" title="GR-127935">GR-127935</a></li> <li><a href="/wiki/Isamoltane" title="Isamoltane">Isamoltane</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/SB-216641" title="SB-216641">SB-216641</a></li> <li><a href="/w/index.php?title=SB-224289&action=edit&redlink=1" class="new" title="SB-224289 (page does not exist)">SB-224289</a></li> <li><a href="/wiki/SB-236057" title="SB-236057">SB-236057</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Ergometrine" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</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/5-HT1D_receptor" title="5-HT1D receptor">5-HT1D</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/CP-122,288" title="CP-122,288">CP-122,288</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/w/index.php?title=CP-286601&action=edit&redlink=1" class="new" title="CP-286601 (page does not exist)">CP-286601</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/w/index.php?title=GR-46611&action=edit&redlink=1" class="new" title="GR-46611 (page does not exist)">GR-46611</a></li> <li><a href="/wiki/L-694247" title="L-694247">L-694247</a></li> <li><a href="/w/index.php?title=L-772405&action=edit&redlink=1" class="new" title="L-772405 (page does not exist)">L-772405</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/w/index.php?title=PNU-109291&action=edit&redlink=1" class="new" title="PNU-109291 (page does not exist)">PNU-109291</a></li> <li><a href="/wiki/PNU-142633" title="PNU-142633">PNU-142633</a></li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/wiki/TGBA01AD" title="TGBA01AD">TGBA01AD</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Almotriptan" title="Almotriptan">almotriptan</a>, <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/Donitriptan" title="Donitriptan">donitriptan</a>, <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>, <a href="/wiki/Frovatriptan" title="Frovatriptan">frovatriptan</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>, <a href="/wiki/Rizatriptan" title="Rizatriptan">rizatriptan</a>, <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>, <a href="/wiki/Zolmitriptan" title="Zolmitriptan">zolmitriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Ethyl-DMT" title="5-Ethyl-DMT">5-Et-DMT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/5-(Nonyloxy)tryptamine" title="5-(Nonyloxy)tryptamine">5-(nonyloxy)tryptamine</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Alniditan" title="Alniditan">Alniditan</a></li> <li><a href="/wiki/BRL-15,572" title="BRL-15,572">BRL-15,572</a></li> <li><a href="/wiki/Elzasonan" title="Elzasonan">Elzasonan</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>)</li> <li><a href="/wiki/GR-127935" title="GR-127935">GR-127935</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/LY-310762" title="LY-310762">LY-310762</a></li> <li><a href="/wiki/LY-367642" title="LY-367642">LY-367642</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/LY-456219" title="LY-456219">LY-456219</a></li> <li><a href="/wiki/LY-456220" title="LY-456220">LY-456220</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li> <li><a href="/wiki/Ziprasidone" title="Ziprasidone">Ziprasidone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Lysergol" title="Lysergol">lysergol</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</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/5-HT1E_receptor" title="5-HT1E receptor">5-HT1E</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/BRL-54443" title="BRL-54443">BRL-54443</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Lysergol" title="Lysergol">lysergol</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</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/5-HT1F_receptor" title="5-HT1F receptor">5-HT1F</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/BRL-54443" title="BRL-54443">BRL-54443</a></li> <li><a href="/wiki/CP-122,288" title="CP-122,288">CP-122,288</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Lysergol" title="Lysergol">lysergol</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a> <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Lasmiditan" title="Lasmiditan">Lasmiditan</a></li> <li><a href="/wiki/LY-334370" title="LY-334370">LY-334370</a></li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>, <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</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/5-HT2_receptor" title="5-HT2 receptor">5-HT2</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: 25H/NB series (e.g., <a href="/wiki/25I-NBF" title="25I-NBF">25I-NBF</a>, <a href="/wiki/25I-NBMD" title="25I-NBMD">25I-NBMD</a>, <a href="/wiki/25I-NBOH" title="25I-NBOH">25I-NBOH</a>, <a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a>, <a href="/wiki/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a>, <a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a>, <a href="/wiki/25TFM-NBOMe" title="25TFM-NBOMe">25TFM-NBOMe</a>, <a href="/wiki/2CBCB-NBOMe" title="2CBCB-NBOMe">2CBCB-NBOMe</a>, <a href="/wiki/25CN-NBOH" title="25CN-NBOH">25CN-NBOH</a>, <a href="/wiki/2CBFly-NBOMe" title="2CBFly-NBOMe">2CBFly-NBOMe</a>)</li> <li><a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2Cs</a> (e.g., <a href="/wiki/2C-B" title="2C-B">2C-B</a>, <a href="/wiki/2C-E" title="2C-E">2C-E</a>, <a href="/wiki/2C-I" title="2C-I">2C-I</a>, <a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a>, <a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a>, <a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a>)</li> <li><a href="/wiki/2C-B-FLY" title="2C-B-FLY">2C-B-FLY</a></li> <li><a href="/wiki/2CB-Ind" title="2CB-Ind">2CB-Ind</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamines</a> (<a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a>, <a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a>, <a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a>, <a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>)</li> <li><a href="/wiki/Substituted_alpha-alkyltryptamine" class="mw-redirect" title="Substituted alpha-alkyltryptamine">α-Alkyltryptamines</a> (e.g., <a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Cl-αMT</a>, <a href="/wiki/5-Fluoro-AMT" title="5-Fluoro-AMT">5-Fl-αMT</a>, <a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a>, <a href="/wiki/5-MeO-aMT" title="5-MeO-aMT">5-MeO-αMT</a>, <a href="/wiki/Alpha-Methylserotonin" class="mw-redirect" title="Alpha-Methylserotonin">α-Me-5-HT</a>, <a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a>, <a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a>)</li> <li><a href="/wiki/AL-34662" title="AL-34662">AL-34662</a></li> <li><a href="/wiki/AL-37350A" title="AL-37350A">AL-37350A</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/DMBMPP" title="DMBMPP">DMBMPP</a></li> <li><a href="/wiki/DOx" title="DOx">DOx</a> (e.g., <a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a>, <a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a>, <a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a>, <a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a>)</li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/1P-LSD" title="1P-LSD">1P-LSD</a>, <a href="/wiki/ALD-52" title="ALD-52">ALD-52</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Ergine" title="Ergine">ergine (LSA)</a>, <a href="/wiki/Ergometrine" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">LA-SS-Az</a>, <a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">LSB</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/LSD-Pip" title="LSD-Pip">LSD-Pip</a>, <a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">LSH</a>, <a href="/wiki/Lysergic_acid_3-pentyl_amide" title="Lysergic acid 3-pentyl amide">LSP</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Flumexadol" title="Flumexadol">Flumexadol</a></li> <li><a href="/wiki/IHCH-7113" title="IHCH-7113">IHCH-7113</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MDxx</a> (e.g., <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a>, <a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a>, <a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</a>, <a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a>)</li> <li><a href="/wiki/O-4310" title="O-4310">O-4310</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/PHA-57378" title="PHA-57378">PHA-57378</a></li> <li><a href="/wiki/PNU-22394" title="PNU-22394">PNU-22394</a></li> <li><a href="/wiki/PNU-181731" title="PNU-181731">PNU-181731</a></li> <li><a href="/wiki/RH-34" title="RH-34">RH-34</a></li> <li><a href="/wiki/SCHEMBL5334361" title="SCHEMBL5334361">SCHEMBL5334361</a></li> <li><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a> (e.g., <a href="/wiki/Lophophine" title="Lophophine">lophophine</a>, <a href="/wiki/Mescaline" title="Mescaline">mescaline</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a>, <a href="/wiki/Quipazine" title="Quipazine">quipazine</a>, <a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a>)</li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li> <li><a href="/wiki/TFMFly" title="TFMFly">TFMFly</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a>, <a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/5-I-R91150" title="5-I-R91150">5-I-R91150</a></li> <li><a href="/wiki/5-MeO-NBpBrT" title="5-MeO-NBpBrT">5-MeO-NBpBrT</a></li> <li><a href="/wiki/AC-90179" title="AC-90179">AC-90179</a></li> <li><a href="/wiki/Adatanserin" title="Adatanserin">Adatanserin</a></li> <li><a href="/wiki/Altanserin" title="Altanserin">Altanserin</a></li> <li><a href="/wiki/Antihistamine" title="Antihistamine">Antihistamines</a> (e.g., <a href="/wiki/Cyproheptadine" title="Cyproheptadine">cyproheptadine</a>, <a href="/wiki/Hydroxyzine" title="Hydroxyzine">hydroxyzine</a>, <a href="/wiki/Ketotifen" title="Ketotifen">ketotifen</a>, <a href="/wiki/Perlapine" title="Perlapine">perlapine</a>)</li> <li><a href="/wiki/9-Aminomethyl-9,10-dihydroanthracene" title="9-Aminomethyl-9,10-dihydroanthracene">AMDA</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Amperozide" title="Amperozide">amperozide</a>, <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Blonanserin" title="Blonanserin">blonanserin</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Carpipramine" title="Carpipramine">carpipramine</a>, <a href="/wiki/Clocapramine" title="Clocapramine">clocapramine</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Gevotroline" title="Gevotroline">gevotroline</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Lurasidone" title="Lurasidone">lurasidone</a>, <a href="/wiki/Melperone" title="Melperone">melperone</a>, <a href="/wiki/Mosapramine" title="Mosapramine">mosapramine</a>, <a href="/wiki/Ocaperidone" title="Ocaperidone">ocaperidone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Paliperidone" title="Paliperidone">paliperidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>, <a href="/wiki/Zicronapine" title="Zicronapine">zicronapine</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Chlorprothixene" title="Chlorprothixene">Chlorprothixene</a></li> <li><a href="/wiki/Cinanserin" title="Cinanserin">Cinanserin</a></li> <li><a href="/wiki/CSP-2503" title="CSP-2503">CSP-2503</a></li> <li><a href="/wiki/Deramciclane" title="Deramciclane">Deramciclane</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Eplivanserin" title="Eplivanserin">Eplivanserin</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Sergolexole" title="Sergolexole">sergolexole</a>)</li> <li><a href="/wiki/Fananserin" title="Fananserin">Fananserin</a></li> <li><a href="/wiki/Flibanserin" title="Flibanserin">Flibanserin</a></li> <li><a href="/wiki/Glemanserin" title="Glemanserin">Glemanserin</a></li> <li><a href="/w/index.php?title=Irindalone&action=edit&redlink=1" class="new" title="Irindalone (page does not exist)">Irindalone</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/KML-010" title="KML-010">KML-010</a></li> <li><a href="/w/index.php?title=Landipirdine&action=edit&redlink=1" class="new" title="Landipirdine (page does not exist)">Landipirdine</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/MIN-117" title="MIN-117">MIN-117 (WF-516)</a></li> <li><a href="/wiki/Naftidrofuryl" title="Naftidrofuryl">Naftidrofuryl</a></li> <li><a href="/wiki/Nantenine" title="Nantenine">Nantenine</a></li> <li><a href="/wiki/Nelotanserin" title="Nelotanserin">Nelotanserin</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/wiki/Pelanserin" title="Pelanserin">Pelanserin</a></li> <li><a href="/wiki/Phenoxybenzamine" title="Phenoxybenzamine">Phenoxybenzamine</a></li> <li><a href="/wiki/Pimavanserin" title="Pimavanserin">Pimavanserin</a></li> <li><a href="/wiki/Pirenperone" title="Pirenperone">Pirenperone</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Pruvanserin" title="Pruvanserin">Pruvanserin</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/Roluperidone" title="Roluperidone">Roluperidone</a></li> <li><a href="/wiki/S-14671" title="S-14671">S-14671</a></li> <li><a href="/wiki/Sarpogrelate" title="Sarpogrelate">Sarpogrelate</a></li> <li><a href="/wiki/Serotonin_antagonist_and_reuptake_inhibitor" title="Serotonin antagonist and reuptake inhibitor">Serotonin antagonists and reuptake inhibitors</a> (e.g., <a href="/wiki/Etoperidone" title="Etoperidone">etoperidone</a>, <a href="/wiki/Hydroxynefazodone" title="Hydroxynefazodone">hydroxynefazodone</a>, <a href="/wiki/Lubazodone" title="Lubazodone">lubazodone</a>, <a href="/wiki/Mepiprazole" title="Mepiprazole">mepiprazole</a>, <a href="/wiki/Nefazodone" title="Nefazodone">nefazodone</a>, <a href="/wiki/Triazoledione" title="Triazoledione">triazoledione</a>, <a href="/wiki/Trazodone" title="Trazodone">trazodone</a>)</li> <li><a href="/w/index.php?title=SR-46349B&action=edit&redlink=1" class="new" title="SR-46349B (page does not exist)">SR-46349B</a></li> <li><a href="/wiki/TGBA01AD" title="TGBA01AD">TGBA01AD</a></li> <li><a href="/wiki/Teniloxazine" title="Teniloxazine">Teniloxazine</a></li> <li><a href="/w/index.php?title=Temanogrel&action=edit&redlink=1" class="new" title="Temanogrel (page does not exist)">Temanogrel</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Aptazapine" title="Aptazapine">aptazapine</a>, <a href="/wiki/Esmirtazapine" title="Esmirtazapine">esmirtazapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Perphenazine" title="Perphenazine">perphenazine</a>, <a href="/wiki/Pimozide" title="Pimozide">pimozide</a>, <a href="/wiki/Pipamperone" title="Pipamperone">pipamperone</a>, <a href="/wiki/Prochlorperazine" title="Prochlorperazine">prochlorperazine</a>, <a href="/wiki/Setoperone" title="Setoperone">setoperone</a>, <a href="/wiki/Spiperone" title="Spiperone">spiperone</a>, <a href="/wiki/Spiramide" title="Spiramide">spiramide</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>, <a href="/wiki/Tiotixene" title="Tiotixene">thiothixene</a>, <a href="/wiki/Trifluoperazine" title="Trifluoperazine">trifluoperazine</a>)</li> <li><a href="/wiki/Volinanserin" title="Volinanserin">Volinanserin</a></li> <li><a href="/wiki/Xylamidine" title="Xylamidine">Xylamidine</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Nicergoline" title="Nicergoline">nicergoline</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/5-HT2B_receptor" title="5-HT2B receptor">5-HT2B</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <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/Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</a> (e.g., <a href="/wiki/Chlorphentermine" title="Chlorphentermine">chlorphentermine</a>, <a href="/wiki/Cloforex" title="Cloforex">cloforex</a>, <a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">dexfenfluramine</a>, <a href="/wiki/Fenfluramine" title="Fenfluramine">fenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">levofenfluramine</a>, <a href="/wiki/Norfenfluramine" title="Norfenfluramine">norfenfluramine</a>)</li> <li><a href="/wiki/BW-723C86" title="BW-723C86">BW-723C86</a></li> <li><a href="/wiki/DOx" title="DOx">DOx</a> (e.g., <a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a>, <a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a>, <a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a>, <a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a>)</li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">dihydroergocryptine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MDxx</a> (e.g., <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a>, <a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a>, <a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</a>, <a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a>)</li> <li><a href="/wiki/Substituted_piperazine" title="Substituted piperazine">Piperazines</a> (e.g., <a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a>)</li> <li><a href="/wiki/PNU-22394" title="PNU-22394">PNU-22394</a></li> <li><a href="/wiki/Ro60-0175" title="Ro60-0175">Ro60-0175</a></li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Alpha-Methylserotonin" class="mw-redirect" title="Alpha-Methylserotonin">α-Me-5-HT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a>, <a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Agomelatine" title="Agomelatine">Agomelatine</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Amisulpride" title="Amisulpride">amisulpride</a>, <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Cariprazine" title="Cariprazine">cariprazine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/w/index.php?title=N-desalkylquetiapine&action=edit&redlink=1" class="new" title="N-desalkylquetiapine (page does not exist)">N-desalkylquetiapine (norquetiapine)</a>, <a href="/wiki/Desmethylclozapine" title="Desmethylclozapine">N-desmethylclozapine (norclozapine)</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Pipamperone" title="Pipamperone">pipamperone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>)</li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/EGIS-7625" title="EGIS-7625">EGIS-7625</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-272,015" title="LY-272,015">LY-272015</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>)</li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Metadoxine" title="Metadoxine">Metadoxine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Pirenperone" title="Pirenperone">Pirenperone</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/PRX-08066" title="PRX-08066">PRX-08066</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/RS-127445" title="RS-127445">RS-127445</a></li> <li><a href="/wiki/Sarpogrelate" title="Sarpogrelate">Sarpogrelate</a></li> <li><a href="/wiki/SB-200646" title="SB-200646">SB-200646</a></li> <li><a href="/wiki/SB-204741" title="SB-204741">SB-204741</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/wiki/SB-215505" title="SB-215505">SB-215505</a></li> <li><a href="/w/index.php?title=SB-221284&action=edit&redlink=1" class="new" title="SB-221284 (page does not exist)">SB-221284</a></li> <li><a href="/wiki/SB-228357" title="SB-228357">SB-228357</a></li> <li><a href="/wiki/SDZ_SER-082" title="SDZ SER-082">SDZ SER-082</a></li> <li><a href="/wiki/Tegaserod" title="Tegaserod">Tegaserod</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Trazodone" title="Trazodone">Trazodone</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>)</li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" title="Ergometrine">ergometrine (ergonovine)</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/5-HT2C_receptor" title="5-HT2C receptor">5-HT2C</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2Cs</a> (e.g., <a href="/wiki/2C-B" title="2C-B">2C-B</a>, <a href="/wiki/2C-E" title="2C-E">2C-E</a>, <a href="/wiki/2C-I" title="2C-I">2C-I</a>, <a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a>, <a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a>, <a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a>)</li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamines</a> (<a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a>, <a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a>, <a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a>, <a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>)</li> <li><a href="/wiki/Substituted_alpha-alkyltryptamine" class="mw-redirect" title="Substituted alpha-alkyltryptamine">α-Alkyltryptamines</a> (e.g., <a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Cl-αMT</a>, <a href="/wiki/5-Fluoro-AMT" title="5-Fluoro-AMT">5-Fl-αMT</a>, <a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a>, <a href="/wiki/5-MeO-aMT" title="5-MeO-aMT">5-MeO-αMT</a>, <a href="/wiki/Alpha-Methylserotonin" class="mw-redirect" title="Alpha-Methylserotonin">α-Me-5-HT</a>, <a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a>, <a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a>)</li> <li><a href="/wiki/A-372159" title="A-372159">A-372159</a></li> <li><a href="/wiki/AL-38022A" title="AL-38022A">AL-38022A</a></li> <li><a href="/wiki/Alstonine" title="Alstonine">Alstonine</a></li> <li><a href="/wiki/CP-809101" title="CP-809101">CP-809101</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/DOx" title="DOx">DOx</a> (e.g., <a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a>, <a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a>, <a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a>, <a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a>)</li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/ALD-52" title="ALD-52">ALD-52</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergine" title="Ergine">ergine (LSA)</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">LA-SS-Az</a>, <a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">LSB</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/LSD-Pip" title="LSD-Pip">LSD-Pip</a>, <a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">LSH</a>, <a href="/wiki/Lysergic_acid_3-pentyl_amide" title="Lysergic acid 3-pentyl amide">LSP</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Flumexadol" title="Flumexadol">Flumexadol</a></li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MDxx</a> (e.g., <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a>, <a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a>, <a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</a>, <a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a>)</li> <li><a href="/wiki/MK-212" title="MK-212">MK-212</a></li> <li><a href="/wiki/ORG-12962" title="ORG-12962">ORG-12962</a></li> <li><a href="/wiki/ORG-37684" title="ORG-37684">ORG-37684</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/PHA-57378" title="PHA-57378">PHA-57378</a></li> <li><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a> (e.g., <a href="/wiki/Lophophine" title="Lophophine">lophophine</a>, <a href="/wiki/Mescaline" title="Mescaline">mescaline</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a>, <a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a>, <a href="/wiki/Quipazine" title="Quipazine">quipazine</a>, <a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a>)</li> <li><a href="/wiki/PNU-22394" title="PNU-22394">PNU-22394</a></li> <li><a href="/wiki/PNU-181731" title="PNU-181731">PNU-181731</a></li> <li><a href="/wiki/Ro60-0175" title="Ro60-0175">Ro60-0175</a></li> <li><a href="/wiki/Ro60-0213" title="Ro60-0213">Ro60-0213</a></li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a>, <a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li> <li><a href="/wiki/Vabicaserin" title="Vabicaserin">Vabicaserin</a></li> <li><a href="/wiki/WAY-629" title="WAY-629">WAY-629</a></li> <li><a href="/wiki/WAY-161503" title="WAY-161503">WAY-161503</a></li> <li><a href="/wiki/YM-348" title="YM-348">YM-348</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Adatanserin" title="Adatanserin">Adatanserin</a></li> <li><a href="/wiki/Agomelatine" title="Agomelatine">Agomelatine</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Melperone" title="Melperone">melperone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Paliperidone" title="Paliperidone">paliperidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Captodiame" title="Captodiame">Captodiame</a></li> <li><a href="/wiki/6-Chloro-5-ethoxy-N-(pyridin-2-yl)indoline-1-carboxamide" title="6-Chloro-5-ethoxy-N-(pyridin-2-yl)indoline-1-carboxamide">CEPC</a></li> <li><a href="/wiki/Cinanserin" title="Cinanserin">Cinanserin</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Deramciclane" title="Deramciclane">Deramciclane</a></li> <li><a href="/wiki/Desmetramadol" title="Desmetramadol">Desmetramadol</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Eltoprazine" title="Eltoprazine">Eltoprazine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Sergolexole" title="Sergolexole">sergolexole</a>)</li> <li><a href="/wiki/Etoperidone" title="Etoperidone">Etoperidone</a></li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/w/index.php?title=FR-260010&action=edit&redlink=1" class="new" title="FR-260010 (page does not exist)">FR-260010</a></li> <li><a href="/w/index.php?title=Irindalone&action=edit&redlink=1" class="new" title="Irindalone (page does not exist)">Irindalone</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/Ketotifen" title="Ketotifen">Ketotifen</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine (dimebolin)</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Pirenperone" title="Pirenperone">Pirenperone</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/RS-102221" title="RS-102221">RS-102221</a></li> <li><a href="/wiki/S-14671" title="S-14671">S-14671</a></li> <li><a href="/wiki/SB-200646" title="SB-200646">SB-200646</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/w/index.php?title=SB-221284&action=edit&redlink=1" class="new" title="SB-221284 (page does not exist)">SB-221284</a></li> <li><a href="/wiki/SB-228357" title="SB-228357">SB-228357</a></li> <li><a href="/wiki/SB-242084" title="SB-242084">SB-242084</a></li> <li><a href="/wiki/SB-243213" title="SB-243213">SB-243213</a></li> <li><a href="/wiki/SDZ_SER-082" title="SDZ SER-082">SDZ SER-082</a></li> <li><a href="/wiki/Tedatioxetine" title="Tedatioxetine">Tedatioxetine</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Aptazapine" title="Aptazapine">aptazapine</a>, <a href="/wiki/Esmirtazapine" title="Esmirtazapine">esmirtazapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Trazodone" title="Trazodone">Trazodone</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Pimozide" title="Pimozide">pimozide</a>, <a href="/wiki/Pipamperone" title="Pipamperone">pipamperone</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Xylamidine" title="Xylamidine">Xylamidine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</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/5-HT3_receptor" title="5-HT3 receptor">5-HT3</a>–<a href="/wiki/5-HT7_receptor" title="5-HT7 receptor">7</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT3_receptor" title="5-HT3 receptor">5-HT3</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> (e.g., <a href="/wiki/N-Butanol" class="mw-redirect" title="N-Butanol">butanol</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">ethanol (alcohol)</a>, <a href="/wiki/2,2,2-Trichloroethanol" title="2,2,2-Trichloroethanol">trichloroethanol</a>)</li> <li><a href="/wiki/Chlorophenylbiguanide" title="Chlorophenylbiguanide">m-CPBG</a></li> <li><a href="/wiki/Phenylbiguanide" title="Phenylbiguanide">Phenylbiguanide</a></li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a>, <a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a>, <a href="/wiki/Quipazine" title="Quipazine">quipazine</a>)</li> <li><a href="/wiki/RS-56812" title="RS-56812">RS-56812</a></li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/wiki/SR-57227" title="SR-57227">SR-57227</a></li> <li><a href="/w/index.php?title=SR-57227A&action=edit&redlink=1" class="new" title="SR-57227A (page does not exist)">SR-57227A</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Me-5-HT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/Bufotenidine" title="Bufotenidine">bufotenidine (5-HTQ)</a>)</li> <li><a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">Volatiles/gases</a> (e.g., <a href="/wiki/Halothane" title="Halothane">halothane</a>, <a href="/wiki/Isoflurane" title="Isoflurane">isoflurane</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/1,1,1-Trichloroethane" title="1,1,1-Trichloroethane">trichloroethane</a>)</li> <li><a href="/wiki/YM-31636" title="YM-31636">YM-31636</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Alosetron" title="Alosetron">Alosetron</a></li> <li><a href="/wiki/Anpirtoline" title="Anpirtoline">Anpirtoline</a></li> <li><a href="/w/index.php?title=Arazasetron&action=edit&redlink=1" class="new" title="Arazasetron (page does not exist)">Arazasetron</a></li> <li><a href="/wiki/AS-8112" title="AS-8112">AS-8112</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>)</li> <li><a href="/wiki/Azasetron" title="Azasetron">Azasetron</a></li> <li><a href="/wiki/Batanopride" title="Batanopride">Batanopride</a></li> <li><a href="/wiki/Bemesetron" title="Bemesetron">Bemesetron (MDL-72222)</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Cilansetron" title="Cilansetron">Cilansetron</a></li> <li><a href="/wiki/CSP-2503" title="CSP-2503">CSP-2503</a></li> <li><a href="/wiki/Dazopride" title="Dazopride">Dazopride</a></li> <li><a href="/wiki/Dolasetron" title="Dolasetron">Dolasetron</a></li> <li><a href="/wiki/Galanolactone" title="Galanolactone">Galanolactone</a></li> <li><a href="/wiki/Granisetron" title="Granisetron">Granisetron</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Lerisetron" title="Lerisetron">Lerisetron</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Ondansetron" title="Ondansetron">Ondansetron</a></li> <li><a href="/wiki/Palonosetron" title="Palonosetron">Palonosetron</a></li> <li><a href="/wiki/Ramosetron" title="Ramosetron">Ramosetron</a></li> <li><a href="/wiki/Renzapride" title="Renzapride">Renzapride</a></li> <li><a href="/wiki/Ricasetron" title="Ricasetron">Ricasetron</a></li> <li><a href="/wiki/Tedatioxetine" title="Tedatioxetine">Tedatioxetine</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Thujone" title="Thujone">Thujone</a></li> <li><a href="/wiki/Tropanserin" title="Tropanserin">Tropanserin</a></li> <li><a href="/wiki/Tropisetron" title="Tropisetron">Tropisetron</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>)</li> <li><a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">Volatiles/gases</a> (e.g., <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">nitrous oxide</a>, <a href="/wiki/Sevoflurane" title="Sevoflurane">sevoflurane</a>, <a href="/wiki/Xenon" title="Xenon">xenon</a>)</li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li> <li><a href="/wiki/Zacopride" title="Zacopride">Zacopride</a></li> <li><a href="/wiki/Zatosetron" title="Zatosetron">Zatosetron</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a></li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</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/5-HT4_receptor" title="5-HT4 receptor">5-HT4</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a></li> <li><a href="/wiki/BIMU8" title="BIMU8">BIMU8</a></li> <li><a href="/wiki/Capeserod" title="Capeserod">Capeserod</a></li> <li><a href="/wiki/Cinitapride" title="Cinitapride">Cinitapride</a></li> <li><a href="/wiki/Cisapride" title="Cisapride">Cisapride</a></li> <li><a href="/wiki/CJ-033466" title="CJ-033466">CJ-033466</a></li> <li><a href="/wiki/Dazopride" title="Dazopride">Dazopride</a></li> <li><a href="/wiki/Metoclopramide" title="Metoclopramide">Metoclopramide</a></li> <li><a href="/w/index.php?title=Minesapride&action=edit&redlink=1" class="new" title="Minesapride (page does not exist)">Minesapride</a></li> <li><a href="/wiki/Mosapride" title="Mosapride">Mosapride</a></li> <li><a href="/wiki/Prucalopride" title="Prucalopride">Prucalopride</a></li> <li><a href="/wiki/PRX-03140" title="PRX-03140">PRX-03140</a></li> <li><a href="/wiki/Renzapride" title="Renzapride">Renzapride</a></li> <li><a href="/wiki/RS-67,333" title="RS-67,333">RS-67,333</a></li> <li><a href="/w/index.php?title=RS-67,506&action=edit&redlink=1" class="new" title="RS-67,506 (page does not exist)">RS-67,506</a></li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/wiki/Tegaserod" title="Tegaserod">Tegaserod</a></li> <li><a href="/w/index.php?title=Usmarapride&action=edit&redlink=1" class="new" title="Usmarapride (page does not exist)">Usmarapride</a></li> <li><a href="/wiki/Velusetrag" title="Velusetrag">Velusetrag</a></li> <li><a href="/wiki/Zacopride" title="Zacopride">Zacopride</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/GR-113808" title="GR-113808">GR-113808</a></li> <li><a href="/w/index.php?title=GR-125487&action=edit&redlink=1" class="new" title="GR-125487 (page does not exist)">GR-125487</a></li> <li><a href="/wiki/Lysine" title="Lysine">L-Lysine</a></li> <li><a href="/wiki/Piboserod" title="Piboserod">Piboserod</a></li> <li><a href="/w/index.php?title=RS-39604&action=edit&redlink=1" class="new" title="RS-39604 (page does not exist)">RS-39604</a></li> <li><a href="/w/index.php?title=RS-67532&action=edit&redlink=1" class="new" title="RS-67532 (page does not exist)">RS-67532</a></li> <li><a href="/w/index.php?title=SB-203186&action=edit&redlink=1" class="new" title="SB-203186 (page does not exist)">SB-203186</a></li> <li><a href="/wiki/SB-204070" title="SB-204070">SB-204070</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/5-HT5A_receptor" title="5-HT5A receptor">5-HT5A</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/2-Bromo-LSD" title="2-Bromo-LSD">2-Br-LSD (BOL-148)</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/LSD" title="LSD">LSD</a>)</li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>)</li> <li><a href="/wiki/Valerenic_acid" title="Valerenic acid">Valerenic acid</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Asenapine" title="Asenapine">Asenapine</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine (dimebolin)</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/SB-699551" title="SB-699551">SB-699551</a></li></ul> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</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/5-HT6_receptor" title="5-HT6 receptor">5-HT6</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">dihydroergocryptine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Hypidone" title="Hypidone">Hypidone</a></li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Me-5-HT</a>, <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin</a>, <a href="/wiki/E-6801" title="E-6801">E-6801</a>, <a href="/wiki/E-6837" title="E-6837">E-6837</a>, <a href="/wiki/EMD-386088" title="EMD-386088">EMD-386088</a>, <a href="/wiki/EMDT" title="EMDT">EMDT</a>, <a href="/w/index.php?title=LY-586713&action=edit&redlink=1" class="new" title="LY-586713 (page does not exist)">LY-586713</a>, <a href="/w/index.php?title=N-Methyl-5-HT&action=edit&redlink=1" class="new" title="N-Methyl-5-HT (page does not exist)">N-Me-5-HT</a>, <a href="/wiki/ST-1936" title="ST-1936">ST-1936</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li> <li><a href="/wiki/WAY-181187" title="WAY-181187">WAY-181187</a></li> <li><a href="/wiki/WAY-208466" title="WAY-208466">WAY-208466</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/w/index.php?title=ABT-354&action=edit&redlink=1" class="new" title="ABT-354 (page does not exist)">ABT-354</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Tiospirone" title="Tiospirone">tiospirone</a>)</li> <li><a href="/wiki/AVN-101" title="AVN-101">AVN-101</a></li> <li><a href="/wiki/AVN-211" title="AVN-211">AVN-211</a></li> <li><a href="/wiki/AVN-322" title="AVN-322">AVN-322</a></li> <li><a href="/wiki/AVN-397" title="AVN-397">AVN-397</a></li> <li><a href="/w/index.php?title=BGC20-760&action=edit&redlink=1" class="new" title="BGC20-760 (page does not exist)">BGC20-760</a></li> <li><a href="/w/index.php?title=BVT-5182&action=edit&redlink=1" class="new" title="BVT-5182 (page does not exist)">BVT-5182</a></li> <li><a href="/w/index.php?title=BVT-74316&action=edit&redlink=1" class="new" title="BVT-74316 (page does not exist)">BVT-74316</a></li> <li><a href="/wiki/Cerlapirdine" title="Cerlapirdine">Cerlapirdine</a></li> <li><a href="/wiki/EGIS-12,233" title="EGIS-12,233">EGIS-12,233</a></li> <li><a href="/w/index.php?title=GW-742457&action=edit&redlink=1" class="new" title="GW-742457 (page does not exist)">GW-742457</a></li> <li><a href="/wiki/Idalopirdine" title="Idalopirdine">Idalopirdine</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/w/index.php?title=Landipirdine&action=edit&redlink=1" class="new" title="Landipirdine (page does not exist)">Landipirdine</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine (dimebolin)</a></li> <li><a href="/wiki/Masupirdine" title="Masupirdine">Masupirdine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/MS-245" title="MS-245">MS-245</a></li> <li><a href="/wiki/PRX-07034" title="PRX-07034">PRX-07034</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/Ro_04-6790" title="Ro 04-6790">Ro 04-6790</a></li> <li><a href="/w/index.php?title=Ro_63-0563&action=edit&redlink=1" class="new" title="Ro 63-0563 (page does not exist)">Ro 63-0563</a></li> <li><a href="/wiki/SB-258585" title="SB-258585">SB-258585</a></li> <li><a href="/wiki/SB-271046" title="SB-271046">SB-271046</a></li> <li><a href="/wiki/SB-357134" title="SB-357134">SB-357134</a></li> <li><a href="/wiki/SB-399885" title="SB-399885">SB-399885</a></li> <li><a href="/wiki/Intepirdine" title="Intepirdine">SB-742457</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>)</li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Doxepin" title="Doxepin">doxepin</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/2-Bromo-LSD" title="2-Bromo-LSD">2-Br-LSD (BOL-148)</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Lergotrile" title="Lergotrile">lergotrile</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</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/5-HT7_receptor" title="5-HT7 receptor">5-HT7</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/8-OH-DPAT" title="8-OH-DPAT">8-OH-DPAT</a></li> <li><a href="/wiki/AS-19_(drug)" title="AS-19 (drug)">AS-19</a></li> <li><a href="/wiki/Bifeprunox" title="Bifeprunox">Bifeprunox</a></li> <li><a href="/wiki/E-55888" title="E-55888">E-55888</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/LSD" title="LSD">LSD</a>)</li> <li><a href="/wiki/LP-12" title="LP-12">LP-12</a></li> <li><a href="/wiki/LP-44" title="LP-44">LP-44</a></li> <li><a href="/wiki/LP-211" title="LP-211">LP-211</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/Sarizotan" title="Sarizotan">Sarizotan</a></li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Frovatriptan" title="Frovatriptan">frovatriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/N-Methylserotonin" title="N-Methylserotonin">N-Me-5-HT</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Amisulpride" title="Amisulpride">amisulpride</a>, <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>, <a href="/wiki/Tiospirone" title="Tiospirone">tiospirone</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Butaclamol" title="Butaclamol">Butaclamol</a></li> <li><a href="/wiki/DR-4485" title="DR-4485">DR-4485</a></li> <li><a href="/wiki/EGIS-12,233" title="EGIS-12,233">EGIS-12,233</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/2-Bromo-LSD" title="2-Bromo-LSD">2-Br-LSD (BOL-148)</a>, <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Sergolexole" title="Sergolexole">sergolexole</a>)</li> <li><a href="/wiki/JNJ-18038683" title="JNJ-18038683">JNJ-18038683</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/SB-258719" title="SB-258719">SB-258719</a></li> <li><a href="/w/index.php?title=SB-258741&action=edit&redlink=1" class="new" title="SB-258741 (page does not exist)">SB-258741</a></li> <li><a href="/wiki/SB-269970" title="SB-269970">SB-269970</a></li> <li><a href="/w/index.php?title=SB-656104&action=edit&redlink=1" class="new" title="SB-656104 (page does not exist)">SB-656104</a></li> <li><a href="/w/index.php?title=SB-656104A&action=edit&redlink=1" class="new" title="SB-656104A (page does not exist)">SB-656104A</a></li> <li><a href="/w/index.php?title=SB-691673&action=edit&redlink=1" class="new" title="SB-691673 (page does not exist)">SB-691673</a></li> <li><a href="/w/index.php?title=SLV-313&action=edit&redlink=1" class="new" title="SLV-313 (page does not exist)">SLV-313</a></li> <li><a href="/w/index.php?title=SLV-314&action=edit&redlink=1" class="new" title="SLV-314 (page does not exist)">SLV-314</a></li> <li><a href="/wiki/Spiperone" title="Spiperone">Spiperone</a></li> <li><a href="/w/index.php?title=SSR-181507&action=edit&redlink=1" class="new" title="SSR-181507 (page does not exist)">SSR-181507</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Acetophenazine" title="Acetophenazine">acetophenazine</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Chlorprothixene" title="Chlorprothixene">chlorprothixene</a>, <a href="/wiki/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Pimozide" title="Pimozide">pimozide</a>)</li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li>See also: <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></li> <li><a href="/wiki/Template:Adrenergic_receptor_modulators" title="Template:Adrenergic receptor modulators">Adrenergics</a></li> <li><a href="/wiki/Template:Dopamine_receptor_modulators" title="Template:Dopamine receptor modulators">Dopaminergics</a></li> <li><a href="/wiki/Template:Melatonin_receptor_modulators" title="Template:Melatonin receptor modulators">Melatonergics</a></li> <li><a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> and <a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">releasing agents</a></li> <li><a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></li> <li><a href="/wiki/Template:Monoamine_neurotoxins" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</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="Monoamine_releasing_agents" 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:Monoamine_releasing_agents" title="Template:Monoamine releasing agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoamine_releasing_agents" title="Template talk:Monoamine releasing agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoamine_releasing_agents" title="Special:EditPage/Template:Monoamine releasing agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoamine_releasing_agents" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">Monoamine releasing agents</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Dopamine_releasing_agents" class="mw-redirect" title="Dopamine releasing agents"><abbr title="Dopamine releasing agents">DRAs</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 Dopamine releasing agents</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Morpholines: <a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</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/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Oxazolines: <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-MAR</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Phenethylamines: <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">2-OH-PEA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" class="mw-redirect" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</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/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><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/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Me-PEA</a></li> <li><a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</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/Iofetamine_(123I)" title="Iofetamine (123I)">Iofetamine (123I)</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/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></li></ul></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/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-methylbutanamine" class="mw-redirect" title="1,3-Benzodioxolyl-N-methylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</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/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</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-Iodoamphetamine" title="Para-Iodoamphetamine">pIA</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</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/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Piperazines: <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Others: <a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-ADN</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-AI</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-AT</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-BP</a></li> <li><a href="/wiki/5-APDI" title="5-APDI">5-APDI</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/Amineptine" title="Amineptine">Amineptine</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <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/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexanamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</a></li> <li><a href="/wiki/Phenylbiguanide" title="Phenylbiguanide">Phenylbiguanide</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</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/Norepinephrine_releasing_agents" class="mw-redirect" title="Norepinephrine releasing agents"><abbr title="Norepinephrine releasing agents">NRAs</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 Norepinephrine releasing agents</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Morpholines: <a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</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/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Oxazolines: <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-MAR</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Phenethylamines: <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">2-OH-PEA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" class="mw-redirect" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</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/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> <ul><li><a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a></li></ul></li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Me-PEA</a></li> <li><a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</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/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</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-APDI" title="5-APDI">5-APDI</a> (IAP)</li> <li><a href="/wiki/Iofetamine_(123I)" title="Iofetamine (123I)">Iofetamine (123I)</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/1,3-Benzodioxolyl-N-methylbutanamine" class="mw-redirect" title="1,3-Benzodioxolyl-N-methylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</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/Metamfepramone" title="Metamfepramone">Metamfepramone</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/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></li></ul></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/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</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/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</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/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">pIA</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/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a>)</li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Piperazines: <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Others: <a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-ADN</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-AI</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-AT</a></li> <li><a href="/wiki/2-Benzylpiperidine" title="2-Benzylpiperidine">2-BP</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-BP</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <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/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexanamine</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</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></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Serotonin_releasing_agents" class="mw-redirect" title="Serotonin releasing agents"><abbr title="Serotonin releasing agents">SRAs</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 Serotonin releasing agents</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aminoindanes: <a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/1-Aminomethyl-5-methoxyindane" title="1-Aminomethyl-5-methoxyindane">AMMI</a></li> <li><a href="/wiki/Ethyltrifluoromethylaminoindane" title="Ethyltrifluoromethylaminoindane">ETAI</a></li> <li><a href="/wiki/MDAI" title="MDAI">MDAI</a></li> <li><a href="/wiki/MDMAI" title="MDMAI">MDMAI</a></li> <li><a href="/wiki/MMAI" title="MMAI">MMAI</a></li> <li><a href="/wiki/Trifluoromethylaminoindane" title="Trifluoromethylaminoindane">TAI</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aminotetralins: <a href="/wiki/6-CAT" title="6-CAT">6-CAT</a></li> <li><a href="/wiki/8-OH-DPAT" title="8-OH-DPAT">8-OH-DPAT</a></li> <li><a href="/wiki/MDAT" title="MDAT">MDAT</a></li> <li><a href="/wiki/MDMAT" title="MDMAT">MDMAT</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Oxazolines: <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/Fluminorex" title="Fluminorex">Fluminorex</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Phenethylamines: <a href="/wiki/2-Methyl-MDA" title="2-Methyl-MDA">2-Methyl-MDA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-HA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-Methyl-MDA" title="5-Methyl-MDA">5-Methyl-MDA</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Methyl-MDA" title="6-Methyl-MDA">6-Methyl-MDA</a></li> <li><a href="/wiki/3-Methoxy-4-methyl-%CE%B1-ethylphenethylamine" class="mw-redirect" title="3-Methoxy-4-methyl-α-ethylphenethylamine">AEMMA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</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/4-Bromomethcathinone" title="4-Bromomethcathinone">Brephedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">DCA</a></li> <li><a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a></li> <li><a href="/wiki/DFMDA" title="DFMDA">DFMDA</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/EDMA" title="EDMA">EDMA</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Flucetorex" title="Flucetorex">Flucetorex</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</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/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxymethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxymethamphetamine">MDHMA</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/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</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-Methoxy-4-methylmethamphetamine" class="mw-redirect" title="3-Methoxy-4-methylmethamphetamine">MMMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">NAP</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/4-Trifluoromethylamphetamine" class="mw-redirect" title="4-Trifluoromethylamphetamine">4-TFMA</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-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" class="mw-redirect" title="Para-Methoxymethamphetamine">PMMA</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Piperazines: <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/w/index.php?title=3-Methoxyphenylpiperazine&action=edit&redlink=1" class="new" title="3-Methoxyphenylpiperazine (page does not exist)">3-MeOPP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/3,4-Dichlorophenylpiperazine" class="mw-redirect" title="3,4-Dichlorophenylpiperazine">DCPP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Mepiprazole" title="Mepiprazole">Mepiprazole</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Para-Chlorophenylpiperazine" title="Para-Chlorophenylpiperazine">pCPP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li> <li><a href="/wiki/1-(4-Trifluoromethyl-phenyl)-piperazine" class="mw-redirect" title="1-(4-Trifluoromethyl-phenyl)-piperazine">pTFMPP</a></li> <li><a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Tryptamines: <a href="/wiki/4-Methyl-AET" class="mw-redirect" title="4-Methyl-AET">4-Methyl-αET</a></li> <li><a href="/wiki/4-Methyl-AMT" class="mw-redirect" title="4-Methyl-AMT">4-Methyl-αMT</a></li> <li><a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a></li> <li><a href="/wiki/5-MeO-AMT" class="mw-redirect" title="5-MeO-AMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a></li> <li><a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a></li> <li><a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Others: <a href="/wiki/Indeloxazine" title="Indeloxazine">Indeloxazine</a></li> <li><a href="/wiki/Viqualine" title="Viqualine">Viqualine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>DAT modulators: Agonist-like: <a href="/wiki/SoRI-9804" title="SoRI-9804">SoRI-9804</a></li> <li><a href="/w/index.php?title=SoRI-20040&action=edit&redlink=1" class="new" title="SoRI-20040 (page does not exist)">SoRI-20040</a>; Antagonist-like: <a href="/wiki/SoRI-20041" title="SoRI-20041">SoRI-20041</a></li></ul> <ul><li>Adrenergic release blockers: <a href="/wiki/Bethanidine" title="Bethanidine">Bethanidine</a></li> <li><a href="/wiki/Bretylium" title="Bretylium">Bretylium</a></li> <li><a href="/wiki/Guanadrel" title="Guanadrel">Guanadrel</a></li> <li><a href="/wiki/Guanazodine" title="Guanazodine">Guanazodine</a></li> <li><a href="/wiki/Guanethidine" title="Guanethidine">Guanethidine</a></li> <li><a href="/wiki/Guanoxan" title="Guanoxan">Guanoxan</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> • <a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> • <a href="/wiki/Template:Adrenergics" class="mw-redirect" title="Template:Adrenergics">Adrenergics</a> • <a href="/wiki/Template:Dopaminergics" class="mw-redirect" title="Template:Dopaminergics">Dopaminergics</a> • <a href="/wiki/Template:Serotonergics" class="mw-redirect" title="Template:Serotonergics">Serotonergics</a> • <a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a> • <a href="/wiki/Template:Monoamine_neurotoxins" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</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="Human_trace_amine-associated_receptor_ligands" 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:TAAR_ligands" title="Template:TAAR ligands"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:TAAR_ligands" title="Template talk:TAAR ligands"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:TAAR_ligands" title="Special:EditPage/Template:TAAR ligands"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Human_trace_amine-associated_receptor_ligands" style="font-size:114%;margin:0 4em"><a href="/wiki/Human_trace_amine-associated_receptor" class="mw-redirect" title="Human trace amine-associated receptor">Human trace amine-associated receptor</a> <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center"><a href="/wiki/TAAR1" title="TAAR1">TAAR1</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/Agonist" title="Agonist">Agonists</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:5em;text-align: center"><a href="/wiki/Trace_amine" title="Trace amine">Endogenous</a>†</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0;background:white"><div style="padding:0 0.25em"> <ul><li>Classical <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitters</a> <ul><li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li> <li><a class="mw-selflink selflink">Serotonin</a></li></ul></li> <li><a href="/wiki/Trace_amine" title="Trace amine">Trace amines</a> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li> <li><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine">N-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methyltyramine" title="N-Methyltyramine">N-Methyltyramine</a></li> <li><a href="/wiki/Meta-Octopamine" class="mw-redirect" title="Meta-Octopamine">m-Octopamine</a></li> <li><a href="/wiki/Para-Octopamine" class="mw-redirect" title="Para-Octopamine">p-Octopamine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine">m-Tyramine</a></li> <li><a href="/wiki/Para-Tyramine" class="mw-redirect" title="Para-Tyramine">p-Tyramine</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;text-align: center">Synthetic and natural‡</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0;background:white"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/N,N-Dimethylphenethylamine" title="N,N-Dimethylphenethylamine">N,N-Dimethylphenethylamine</a></li> <li><a href="/wiki/Guanfacine" title="Guanfacine">Guanfacine</a></li> <li><a href="/wiki/Halostachine" title="Halostachine">Halostachine</a></li> <li><a href="/wiki/Higenamine" title="Higenamine">Higenamine</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/Isopropyloctopamine" class="mw-redirect" title="Isopropyloctopamine">Isopropyloctopamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/2-Methylphenethylamine" title="2-Methylphenethylamine">2-Methylphenethylamine</a></li> <li><a href="/wiki/3-Methylphenethylamine" title="3-Methylphenethylamine">3-Methylphenethylamine</a></li> <li><a href="/wiki/4-Methylphenethylamine" title="4-Methylphenethylamine">4-Methylphenethylamine</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/3-Methoxymethamphetamine" title="3-Methoxymethamphetamine">3-MMA</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/O-Phenyl-3-iodotyramine" title="O-Phenyl-3-iodotyramine">o-PIT</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li> <li><a href="/wiki/Ralmitaront" title="Ralmitaront">Ralmitaront (RG-7906, RO-6889450)</a></li> <li><a href="/wiki/RG-7351" title="RG-7351">RG-7351</a></li> <li><a href="/wiki/RG-7410" title="RG-7410">RG-7410</a></li> <li><a href="/wiki/RO5166017" title="RO5166017">RO-5166017</a></li> <li><a href="/wiki/RO5256390" title="RO5256390">RO-5256390</a></li> <li><a href="/wiki/RO5263397" title="RO5263397">RO-5263397</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Ulotaront" title="Ulotaront">Ulotaront (SEP-363856)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center"><a href="/wiki/Neutral_antagonist" class="mw-redirect" title="Neutral antagonist">Neutral antagonists</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/RTI-7470-44" title="RTI-7470-44">RTI-7470-44</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center"><a href="/wiki/Inverse_agonist" title="Inverse agonist">Inverse agonists</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/EPPTB" title="EPPTB">EPPTB (RO-5212773)</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/TAAR2" title="TAAR2">TAAR2</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">Agonists‡</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center">Neutral antagonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li> </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/TAAR5" title="TAAR5">TAAR5</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">Agonists‡</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/N,N-Dimethylethylamine" title="N,N-Dimethylethylamine">N,N-Dimethylethylamine</a></li> <li><a href="/wiki/Trimethylamine" title="Trimethylamine">Trimethylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center">Neutral antagonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li> </li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center">Inverse agonists‡</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/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><div style="float: left;">† References for all endogenous human TAAR1 ligands are provided at <a href="/wiki/Trace_amine#list" title="Trace amine">List of trace amines</a></div> <div style="float: left;">‡ References for synthetic TAAR1 agonists can be found at <a href="/wiki/TAAR1" title="TAAR1">TAAR1</a> or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see <a href="/wiki/Trace_amine-associated_receptor#Receptor_function_and_ligands" title="Trace amine-associated receptor">TAAR</a> for references.</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="Tryptamines" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Tryptamines" title="Template:Tryptamines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tryptamines" title="Template talk:Tryptamines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tryptamines" title="Special:EditPage/Template:Tryptamines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Tryptamines" style="font-size:114%;margin:0 4em"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Methylpsilocin" title="1-Methylpsilocin">1-Methylpsilocin</a></li> <li><a href="/wiki/2-HO-NMT" title="2-HO-NMT">2-HO-NMT</a></li> <li><a href="/wiki/2-Me-DET" title="2-Me-DET">2-Me-DET</a></li> <li><a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Methyl-5-HT</a></li> <li><a href="/wiki/2,N,N-TMT" title="2,N,N-TMT">2,N,N-TMT</a></li> <li><a href="/wiki/1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole" class="mw-redirect" title="1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole">4,5-DHP-DMT</a></li> <li><a href="/wiki/4-AcO-DALT" title="4-AcO-DALT">4-AcO-DALT</a></li> <li><a href="/wiki/4-Acetoxy-DET" class="mw-redirect" title="4-Acetoxy-DET">4-AcO-DET</a></li> <li><a href="/wiki/4-Acetoxy-DiPT" title="4-Acetoxy-DiPT">4-AcO-DiPT</a></li> <li><a href="/wiki/4-AcO-DPT" title="4-AcO-DPT">4-AcO-DPT</a></li> <li><a href="/w/index.php?title=4-AcO-EPT&action=edit&redlink=1" class="new" title="4-AcO-EPT (page does not exist)">4-AcO-EPT</a></li> <li><a href="/w/index.php?title=4-AcO-MALT&action=edit&redlink=1" class="new" title="4-AcO-MALT (page does not exist)">4-AcO-MALT</a></li> <li><a href="/wiki/4-Acetoxy-MET" class="mw-redirect" title="4-Acetoxy-MET">4-AcO-MET</a></li> <li><a href="/wiki/4-Acetoxy-MiPT" class="mw-redirect" title="4-Acetoxy-MiPT">4-AcO-MiPT</a></li> <li><a href="/w/index.php?title=4-AcO-NMT&action=edit&redlink=1" class="new" title="4-AcO-NMT (page does not exist)">4-AcO-NMT</a></li> <li><a href="/w/index.php?title=4-AcO-TMT&action=edit&redlink=1" class="new" title="4-AcO-TMT (page does not exist)">4-AcO-TMT</a></li> <li><a href="/wiki/4-Fluoro-5-methoxy-DMT" title="4-Fluoro-5-methoxy-DMT">4-F-5-MeO-DMT</a></li> <li><a href="/wiki/4-Hydroxy-5-methoxydimethyltryptamine" title="4-Hydroxy-5-methoxydimethyltryptamine">4-HO-5-MeO-DMT</a></li> <li><a href="/w/index.php?title=4-HO-DALT&action=edit&redlink=1" class="new" title="4-HO-DALT (page does not exist)">4-HO-DALT</a></li> <li><a href="/wiki/4-HO-DBT" title="4-HO-DBT">4-HO-DBT</a></li> <li><a href="/wiki/4-HO-DET" title="4-HO-DET">4-HO-DET</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">4-HO-DiPT</a></li> <li><a href="/wiki/4-HO-DPT" title="4-HO-DPT">4-HO-DPT</a></li> <li><a href="/wiki/4-HO-DSBT" title="4-HO-DSBT">4-HO-DSBT</a></li> <li><a href="/wiki/4-HO-EPT" title="4-HO-EPT">4-HO-EPT</a></li> <li><a href="/wiki/4-HO-MALT" title="4-HO-MALT">4-HO-MALT</a></li> <li><a href="/wiki/4-HO-MET" title="4-HO-MET">4-HO-MET</a></li> <li><a href="/wiki/4-HO-McPT" title="4-HO-McPT">4-HO-McPT</a></li> <li><a href="/wiki/4-HO-McPeT" title="4-HO-McPeT">4-HO-McPeT</a></li> <li><a href="/wiki/4-HO-MiPT" title="4-HO-MiPT">4-HO-MiPT</a></li> <li><a href="/wiki/4-HO-MPT" title="4-HO-MPT">4-HO-MPT</a></li> <li><a href="/w/index.php?title=4-HO-MsBT&action=edit&redlink=1" class="new" title="4-HO-MsBT (page does not exist)">4-HO-MsBT</a></li> <li><a href="/wiki/4-HO-NALT" title="4-HO-NALT">4-HO-NALT</a></li> <li><a href="/wiki/4-HO-NMT" class="mw-redirect" title="4-HO-NMT">4-HO-NMT</a></li> <li><a href="/wiki/4-HO-PiPT" title="4-HO-PiPT">4-HO-PiPT</a></li> <li><a href="/wiki/4-HO-pyr-T" title="4-HO-pyr-T">4-HO-pyr-T</a></li> <li><a href="/wiki/4-HO-TMT" title="4-HO-TMT">4-HO-TMT</a></li> <li><a href="/wiki/4-Hydroxytryptamine" title="4-Hydroxytryptamine">4-HT</a></li> <li><a href="/w/index.php?title=4-MeO-DiPT&action=edit&redlink=1" class="new" title="4-MeO-DiPT (page does not exist)">4-MeO-DiPT</a></li> <li><a href="/wiki/4-MeO-DMT" title="4-MeO-DMT">4-MeO-DMT</a></li> <li><a href="/wiki/4-MeO-MiPT" title="4-MeO-MiPT">4-MeO-MiPT</a></li> <li><a href="/wiki/4-PrO-DMT" title="4-PrO-DMT">4-PrO-DMT</a></li> <li><a href="/wiki/4,5-MDO-DMT" title="4,5-MDO-DMT">4,5-MDO-DMT</a></li> <li><a href="/wiki/4,5-MDO-DiPT" title="4,5-MDO-DiPT">4,5-MDO-DiPT</a></li> <li><a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a></li> <li><a href="/wiki/5-Bromo-DMT" title="5-Bromo-DMT">5-Bromo-DMT</a></li> <li><a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a></li> <li><a href="/wiki/5-Chloro-DMT" title="5-Chloro-DMT">5-Chloro-DMT</a></li> <li><a href="/wiki/5-Ethoxy-DMT" title="5-Ethoxy-DMT">5-Ethoxy-DMT</a></li> <li><a href="/wiki/5-Ethyl-DMT" title="5-Ethyl-DMT">5-Ethyl-DMT</a></li> <li><a href="/wiki/5-Fluoro-DET" title="5-Fluoro-DET">5-Fluoro-DET</a></li> <li><a href="/wiki/5-Fluoro-DMT" title="5-Fluoro-DMT">5-Fluoro-DMT</a></li> <li><a href="/wiki/5-Fluoro-EPT" title="5-Fluoro-EPT">5-Fluoro-EPT</a></li> <li><a href="/wiki/5-Fluoro-MET" title="5-Fluoro-MET">5-Fluoro-MET</a></li> <li><a href="/wiki/5-HO-DiPT" title="5-HO-DiPT">5-HO-DiPT</a></li> <li><a href="/wiki/5-Hydroxytryptophan" title="5-Hydroxytryptophan">5-HTP (oxitriptan)</a></li> <li><a href="/wiki/5-MeO-2-TMT" title="5-MeO-2-TMT">5-MeO-2-TMT</a></li> <li><a href="/w/index.php?title=5-MeO-34MPEMT&action=edit&redlink=1" class="new" title="5-MeO-34MPEMT (page does not exist)">5-MeO-34MPEMT</a></li> <li><a href="/wiki/5-Methoxy-7,N,N-trimethyltryptamine" title="5-Methoxy-7,N,N-trimethyltryptamine">5-MeO-7,N,N-TMT</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/5-MeO-DBT" title="5-MeO-DBT">5-MeO-DBT</a></li> <li><a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a></li> <li><a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a></li> <li><a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a></li> <li><a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a></li> <li><a href="/wiki/5-MeO-EiPT" title="5-MeO-EiPT">5-MeO-EiPT</a></li> <li><a href="/wiki/5-MeO-EPT" title="5-MeO-EPT">5-MeO-EPT</a></li> <li><a href="/wiki/5-MeO-MALT" title="5-MeO-MALT">5-MeO-MALT</a></li> <li><a href="/wiki/5-MeO-MET" title="5-MeO-MET">5-MeO-MET</a></li> <li><a href="/wiki/5-MeO-MiPT" title="5-MeO-MiPT">5-MeO-MiPT</a></li> <li><a href="/wiki/5-MeO-NMT" title="5-MeO-NMT">5-MeO-NMT</a></li> <li><a href="/wiki/5-MeO-pyr-T" title="5-MeO-pyr-T">5-MeO-pyr-T</a></li> <li><a href="/wiki/5-MeO-NBpBrT" title="5-MeO-NBpBrT">5-MeO-NBpBrT</a></li> <li><a href="/wiki/5-MeO-T-NBOMe" title="5-MeO-T-NBOMe">5-MeO-T-NBOMe</a></li> <li><a href="/wiki/5-MeS-DMT" title="5-MeS-DMT">5-MeS-DMT</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamine (5-MT; mexamine)</a></li> <li><a href="/wiki/5,N,N-TMT" title="5,N,N-TMT">5-Methyl-DMT</a></li> <li><a href="/w/index.php?title=5-Methyltryptamine&action=edit&redlink=1" class="new" title="5-Methyltryptamine (page does not exist)">5-Methyltryptamine</a></li> <li><a href="/w/index.php?title=5-MT-NB3OMe&action=edit&redlink=1" class="new" title="5-MT-NB3OMe (page does not exist)">5-MT-NB3OMe</a></li> <li><a href="/wiki/5-(Nonyloxy)tryptamine" title="5-(Nonyloxy)tryptamine">5-(Nonyloxy)tryptamine</a></li> <li><a href="/wiki/5,6-MeO-MiPT" title="5,6-MeO-MiPT">5,6-MeO-MiPT</a></li> <li><a href="/wiki/5,6-MDO-DiPT" title="5,6-MDO-DiPT">5,6-MDO-DiPT</a></li> <li><a href="/wiki/5,6-MDO-DMT" title="5,6-MDO-DMT">5,6-MDO-DMT</a></li> <li><a href="/wiki/5,6-MDO-MiPT" title="5,6-MDO-MiPT">5,6-MDO-MiPT</a></li> <li><a href="/wiki/5,6-Dihydroxytryptamine" title="5,6-Dihydroxytryptamine">5,6-DHT</a></li> <li><a href="/wiki/5,7-Dihydroxytryptamine" title="5,7-Dihydroxytryptamine">5,7-DHT</a></li> <li><a href="/wiki/6-Fluoro-DMT" title="6-Fluoro-DMT">6-Fluoro-DMT</a></li> <li><a href="/wiki/6-MeO-DMT" title="6-MeO-DMT">6-MeO-DMT</a></li> <li><a href="/wiki/7,N,N-TMT" title="7,N,N-TMT">7-Methyl-DMT</a></li> <li><a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine (5-AT)</a></li> <li><a href="/wiki/Aeruginascin" title="Aeruginascin">Aeruginascin (4-PO-TMT)</a></li> <li><a href="/wiki/AGH-107" title="AGH-107">AGH-107</a></li> <li><a href="/wiki/AGH-192" title="AGH-192">AGH-192</a></li> <li><a href="/wiki/AH-494" title="AH-494">AH-494</a></li> <li><a href="/w/index.php?title=ALiPT&action=edit&redlink=1" class="new" title="ALiPT (page does not exist)">ALiPT</a></li> <li><a href="/wiki/Alpertine" title="Alpertine">Alpertine</a></li> <li><a href="/wiki/Baeocystin" title="Baeocystin">Baeocystin (4-PO-NMT)</a></li> <li><a href="/wiki/Benzotript" title="Benzotript">Benzotript (4-chlorobenzoyl-L-tryptophan)</a></li> <li><a href="/wiki/Bufotenidine" title="Bufotenidine">Bufotenidine (5-HTQ)</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin (5-HO-DMT)</a></li> <li><a href="/wiki/Convolutindole_A" title="Convolutindole A">Convolutindole A</a></li> <li><a href="/wiki/CP-132,484" title="CP-132,484">CP-132,484</a></li> <li><a href="/wiki/DALT" title="DALT">DALT</a></li> <li><a href="/wiki/Dibutyltryptamine" title="Dibutyltryptamine">DBT</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a></li> <li><a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a></li> <li><a href="/wiki/E-6801" title="E-6801">E-6801</a></li> <li><a href="/wiki/E-6837" title="E-6837">E-6837</a></li> <li><a href="/wiki/Ethylisopropyltryptamine" title="Ethylisopropyltryptamine">EiPT</a></li> <li><a href="/wiki/EMDT" title="EMDT">EMDT</a></li> <li><a href="/wiki/Ethylpropyltryptamine" title="Ethylpropyltryptamine">EPT</a></li> <li><a href="/wiki/Ethocybin" title="Ethocybin">Ethocybin (4-PO-DET)</a></li> <li><a href="/wiki/FGIN-127" title="FGIN-127">FGIN-127</a></li> <li><a href="/wiki/FGIN-143" title="FGIN-143">FGIN-143</a></li> <li><a href="/wiki/FT-104" title="FT-104">FT-104</a></li> <li><a href="/wiki/HIOC" title="HIOC">HIOC</a></li> <li><a href="/wiki/Idalopirdine" title="Idalopirdine">Idalopirdine</a></li> <li><a href="/w/index.php?title=Indolylethylfentanyl&action=edit&redlink=1" class="new" title="Indolylethylfentanyl (page does not exist)">Indolylethylfentanyl</a></li> <li><a href="/wiki/Indorenate" title="Indorenate">Indorenate</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">Iprocin (4-HO-DiPT)</a></li> <li><a href="/wiki/Lespedamine" title="Lespedamine">Lespedamine</a></li> <li><a href="/wiki/N-Methyl-N-ethyltryptamine" title="N-Methyl-N-ethyltryptamine">MET</a></li> <li><a href="/wiki/Methylbutyltryptamine" title="Methylbutyltryptamine">Methylbutyltryptamine</a></li> <li><a href="/wiki/4-HO-MiPT" title="4-HO-MiPT">Miprocin (4-HO-MiPT)</a></li> <li><a href="/wiki/Methylisopropyltryptamine" class="mw-redirect" title="Methylisopropyltryptamine">MiPT</a></li> <li><a href="/wiki/4-Acetoxy-MiPT" class="mw-redirect" title="4-Acetoxy-MiPT">MPT</a></li> <li><a href="/wiki/Milipertine" title="Milipertine">Milipertine</a></li> <li><a href="/wiki/MS-245" title="MS-245">MS-245</a></li> <li><a href="/wiki/Methylbutyltryptamine#MSBT" title="Methylbutyltryptamine">MSBT</a></li> <li><a href="/wiki/N-Feruloylserotonin" title="N-Feruloylserotonin">N-Feruloylserotonin (moschamine)</a></li> <li><a href="/wiki/N-Ethyltryptamine" title="N-Ethyltryptamine">NET</a></li> <li><a href="/wiki/N-Methyltryptamine" title="N-Methyltryptamine">NMT</a></li> <li><a href="/wiki/Norbaeocystin" title="Norbaeocystin">Norbaeocystin (4-PO-T)</a></li> <li><a href="/wiki/N-t-Butyltryptamine" title="N-t-Butyltryptamine">NTBT</a></li> <li><a href="/wiki/O-4310" title="O-4310">O-4310</a></li> <li><a href="/wiki/O-Pivalylbufotenine" title="O-Pivalylbufotenine">O-Pivalylbufotenine</a></li> <li><a href="/wiki/Oxypertine" title="Oxypertine">Oxypertine</a></li> <li><a href="/wiki/Propylisopropyltryptamine" title="Propylisopropyltryptamine">PiPT</a></li> <li><a href="/wiki/Psilacetin" class="mw-redirect" title="Psilacetin">Psilacetin (O-acetylpsilocin; 4-AcO-DMT)</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">Psilocin (4-HO-DMT)</a></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">Psilocybin (4-PO-DMT)</a></li> <li><a href="/wiki/Pyr-T" title="Pyr-T">Pyr-T</a></li> <li><a href="/wiki/RS134-49" title="RS134-49">RS134-49</a></li> <li><a class="mw-selflink selflink">Serotonin (5-HT)</a></li> <li><a href="/wiki/Solypertine" title="Solypertine">Solypertine</a></li> <li><a href="/wiki/ST-1936" title="ST-1936">ST-1936</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/Yuremamine" title="Yuremamine">Yuremamine</a></li> <li><a href="/w/index.php?title=Z2876442907&action=edit&redlink=1" class="new" title="Z2876442907 (page does not exist)">Z2876442907</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine">N-Acetyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Iodomelatonin" title="2-Iodomelatonin">2-Iodomelatonin</a></li> <li><a href="/w/index.php?title=2-Phenylmelatonin&action=edit&redlink=1" class="new" title="2-Phenylmelatonin (page does not exist)">2-Phenylmelatonin</a></li> <li><a href="/w/index.php?title=5-Methoxyluzindole&action=edit&redlink=1" class="new" title="5-Methoxyluzindole (page does not exist)">5-Methoxyluzindole</a></li> <li><a href="/w/index.php?title=6-Chloromelatonin&action=edit&redlink=1" class="new" title="6-Chloromelatonin (page does not exist)">6-Chloromelatonin</a></li> <li><a href="/w/index.php?title=6-Fluoromelatonin&action=edit&redlink=1" class="new" title="6-Fluoromelatonin (page does not exist)">6-Fluoromelatonin</a></li> <li><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-Hydroxymelatonin</a></li> <li><a href="/w/index.php?title=6-Methoxymelatonin&action=edit&redlink=1" class="new" title="6-Methoxymelatonin (page does not exist)">6-Methoxymelatonin</a></li> <li><a href="/w/index.php?title=6,7-Dichloro-2-methylmelatonin&action=edit&redlink=1" class="new" title="6,7-Dichloro-2-methylmelatonin (page does not exist)">6,7-Dichloro-2-methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/Luzindole" title="Luzindole">Luzindole</a></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">Normelatonin (N-acetylserotonin; NAS)</a></li> <li><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine">N-Acetyltryptamine</a></li> <li><a href="/w/index.php?title=N-Butanoylmelatonin&action=edit&redlink=1" class="new" title="N-Butanoylmelatonin (page does not exist)">N-Butanoylmelatonin</a></li> <li><a href="/w/index.php?title=N-Propionylmelatonin&action=edit&redlink=1" class="new" title="N-Propionylmelatonin (page does not exist)">N-Propionylmelatonin</a></li> <li><a href="/wiki/Piromelatine" title="Piromelatine">Piromelatine</a></li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/%CE%91-Alkyltryptamine" class="mw-redirect" title="Α-Alkyltryptamine">α-Alkyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,%CE%B1-Dimethyltryptamine" title="2,α-Dimethyltryptamine">2,α-DMT</a></li> <li><a href="/wiki/4-HO-%CE%B1MT" title="4-HO-αMT">4-HO-αMT</a></li> <li><a href="/wiki/4-HO-MPMI" title="4-HO-MPMI">4-HO-MPMI (lucigenol)</a></li> <li><a href="/wiki/4-Methyl-%CE%B1-ethyltryptamine" title="4-Methyl-α-ethyltryptamine">4-Me-αET</a></li> <li><a href="/wiki/4-Me-%CE%B1MT" class="mw-redirect" title="4-Me-αMT">4-Me-αMT</a></li> <li><a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Chloro-αMT</a></li> <li><a href="/wiki/5-Ethoxy-AMT" class="mw-redirect" title="5-Ethoxy-AMT">5-Ethoxy-αMT</a></li> <li><a href="/wiki/5-Fluoro-AET" title="5-Fluoro-AET">5-Fluoro-αET</a></li> <li><a href="/wiki/5-Fluoro-AMT" title="5-Fluoro-AMT">5-Fluoro-αMT</a></li> <li><a href="/w/index.php?title=5-Isopropoxy-AMT&action=edit&redlink=1" class="new" title="5-Isopropoxy-AMT (page does not exist)">5-iPrO-αMT</a></li> <li><a href="/w/index.php?title=5-MeO-%CE%B1,N,N-TMT&action=edit&redlink=1" class="new" title="5-MeO-α,N,N-TMT (page does not exist)">5-MeO-α,N,N-TMT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET </a></li> <li><a href="/wiki/5-MeO-aMT" title="5-MeO-aMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-MeO-MPMI" title="5-MeO-MPMI">5-MeO-MPMI</a></li> <li><a href="/w/index.php?title=5-Methyl-AET&action=edit&redlink=1" class="new" title="5-Methyl-AET (page does not exist)">5-Methyl-αET</a></li> <li><a href="/wiki/6-Fluoro-AMT" title="6-Fluoro-AMT">6-Fluoro-αMT</a></li> <li><a href="/wiki/7-Chloro-AMT" title="7-Chloro-AMT">7-Chloro-αMT</a></li> <li><a href="/wiki/7-Methyl-%CE%B1-ethyltryptamine" title="7-Methyl-α-ethyltryptamine">7-Methyl-αET</a></li> <li><a href="/wiki/%CE%91-Methyl-5-hydroxytryptophan" title="Α-Methyl-5-hydroxytryptophan">α-Methyl-5-HTP</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylserotonin" title="Α-Methylserotonin">α-Methylserotonin (5-HO-αMT)</a></li> <li><a href="/wiki/%CE%91-Methyltryptophan" title="Α-Methyltryptophan">α-Methyltryptophan (αMTP)</a></li> <li><a href="/wiki/Alpha,N-DMT" class="mw-redirect" title="Alpha,N-DMT">α,N-DMT (N-methyl-αMT)</a></li> <li><a href="/wiki/%CE%91,N,N-Trimethyltryptamine" title="Α,N,N-Trimethyltryptamine">α,N,N-TMT</a></li> <li><a href="/wiki/Alpha,N,O-TMS" class="mw-redirect" title="Alpha,N,O-TMS">α,N,O-TMS</a></li> <li><a href="/wiki/%CE%91-Ethyltryptamine" title="Α-Ethyltryptamine">αET (etryptamine)</a></li> <li><a href="/wiki/%CE%91-Methyltryptamine" title="Α-Methyltryptamine">αMT</a></li> <li><a href="/wiki/AL-37350A" title="AL-37350A">AL-37350A (4,5-DHP-αMT)</a></li> <li><a href="/wiki/BNC-210" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/BW-723C86" title="BW-723C86">BW-723C86</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/wiki/Indolylpropylaminopentane" title="Indolylpropylaminopentane">IPAP (α,N-DPT)</a></li> <li><a href="/wiki/MPMI_(drug)" title="MPMI (drug)">MPMI</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Triptan" title="Triptan">Triptans</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Almotriptan" title="Almotriptan">Almotriptan</a></li> <li><a href="/wiki/Donitriptan" title="Donitriptan">Donitriptan</a></li> <li><a href="/wiki/Eletriptan" title="Eletriptan">Eletriptan</a></li> <li><a href="/wiki/Frovatriptan" title="Frovatriptan">Frovatriptan</a></li> <li><a href="/wiki/L-694247" title="L-694247">L-694247</a></li> <li><a href="/wiki/Rizatriptan" title="Rizatriptan">Rizatriptan</a></li> <li><a href="/wiki/Sumatriptan" title="Sumatriptan">Sumatriptan</a></li> <li><a href="/wiki/Zolmitriptan" title="Zolmitriptan">Zolmitriptan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Cyclic_compound" title="Cyclic compound">Cyclized tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bay_R_1531" title="Bay R 1531">Bay R 1531</a></li> <li><a href="/wiki/Ciclindole" title="Ciclindole">Ciclindole</a></li> <li><a href="/wiki/Cyclic_3-hydroxymelatonin" title="Cyclic 3-hydroxymelatonin">Cyclic 3-OHM</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> and <a href="/wiki/Lysergamide" class="mw-redirect" title="Lysergamide">lysergamides</a> (e.g., <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">LSD</a>)</li> <li><a href="/wiki/Flucindole" title="Flucindole">Flucindole</a></li> <li><a href="/wiki/Harmala_alkaloid" title="Harmala alkaloid">Harmala alkaloids</a> and <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carbolines</a> (e.g., <a href="/wiki/6-MeO-THH" title="6-MeO-THH">6-MeO-THH</a>, <a href="/wiki/9-Methyl-%CE%B2-carboline" title="9-Methyl-β-carboline">9-Me-BC</a>, <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carboline (norharman)</a>, <a href="/wiki/Harmaline" title="Harmaline">harmaline</a>, <a href="/wiki/Harmalol" title="Harmalol">harmalol</a>, <a href="/wiki/Harmane" title="Harmane">harmane</a>, <a href="/wiki/Harmine" title="Harmine">harmine</a>, <a href="/wiki/Pinoline" title="Pinoline">pinoline</a>, <a href="/wiki/Tetrahydroharmine" title="Tetrahydroharmine">tetrahydroharmine</a>, <a href="/wiki/Tryptoline" title="Tryptoline">tryptoline</a>)</li> <li><a href="/wiki/Iboga-type_alkaloid" title="Iboga-type alkaloid">Iboga alkaloids</a> and related (e.g., <a href="/wiki/DM-506" title="DM-506">DM-506 (ibogaminalog)</a>, <a href="/wiki/Ibogaine" title="Ibogaine">ibogaine</a>, <a href="/wiki/Ibogamine" title="Ibogamine">ibogamine</a>, <a href="/wiki/Noribogaine" title="Noribogaine">noribogaine</a>, <a href="/wiki/Tabernanthalog" title="Tabernanthalog">tabernanthalog</a>, <a href="/wiki/Tabernanthine" title="Tabernanthine">tabernanthine</a>)</li> <li><a href="/wiki/Metralindole" title="Metralindole">Metralindole</a></li> <li><a href="/wiki/NDTDI" title="NDTDI">NDTDI</a></li> <li><a href="/wiki/PHA-57378" title="PHA-57378">PHA-57378</a></li> <li><a href="/wiki/PNU-22394" title="PNU-22394">PNU-22394</a></li> <li><a href="/wiki/PNU-181731" title="PNU-181731">PNU-181731</a></li> <li><a href="/wiki/RU-28306" title="RU-28306">RU-28306</a></li> <li><a href="/wiki/Yohimban" title="Yohimban">Yohimbans</a> (e.g., <a href="/wiki/Yohimbine" title="Yohimbine">yohimbine</a>, <a href="/wiki/Rauwolscine" title="Rauwolscine">rauwolscine</a>, <a href="/wiki/Spegatrine" title="Spegatrine">spegatrine</a>, <a href="/wiki/Corynanthine" title="Corynanthine">corynanthine</a>, <a href="/wiki/Ajmalicine" title="Ajmalicine">ajmalicine</a>, <a href="/wiki/Reserpine" title="Reserpine">reserpine</a>, <a href="/wiki/Deserpidine" title="Deserpidine">deserpidine</a>, <a href="/wiki/Rescinnamine" title="Rescinnamine">rescinnamine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Related compounds</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="/w/index.php?title=2-Azapsilocin&action=edit&redlink=1" class="new" title="2-Azapsilocin (page does not exist)">2-Azapsilocin</a></li> <li><a href="/w/index.php?title=4-Aza-5-MeO-DPT&action=edit&redlink=1" class="new" title="4-Aza-5-MeO-DPT (page does not exist)">4-Aza-5-MeO-DPT</a></li> <li><a href="/w/index.php?title=5-Aza-4-MeO-DiPT&action=edit&redlink=1" class="new" title="5-Aza-4-MeO-DiPT (page does not exist)">5-Aza-4-MeO-DiPT</a></li> <li><a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li> <li><a href="/wiki/5-Hydroxyindoleacetaldehyde" title="5-Hydroxyindoleacetaldehyde">5-HIAL</a></li> <li><a href="/w/index.php?title=5-Hydroxyindole_thiazoladine_carboxylic_acid&action=edit&redlink=1" class="new" title="5-Hydroxyindole thiazoladine carboxylic acid (page does not exist)">5-HITCA</a></li> <li><a href="/w/index.php?title=5-Methoxyindoleacetaldehyde&action=edit&redlink=1" class="new" title="5-Methoxyindoleacetaldehyde (page does not exist)">5-MIAL</a></li> <li><a href="/w/index.php?title=7-Aza-5-MeO-DiPT&action=edit&redlink=1" class="new" title="7-Aza-5-MeO-DiPT (page does not exist)">7-Aza-5-MeO-DiPT</a></li> <li><a href="/wiki/AAZ-A-154" title="AAZ-A-154">AAZ-A-154</a></li> <li><a href="/wiki/AL-34662" title="AL-34662">AL-34662</a></li> <li><a href="/wiki/AL-38022A" title="AL-38022A">AL-38022A</a></li> <li><a href="/wiki/BRL-54443" title="BRL-54443">BRL-54443</a></li> <li><a href="/wiki/CP-94253" title="CP-94253">CP-94253</a></li> <li><a href="/wiki/EMD-386088" title="EMD-386088">EMD-386088</a></li> <li><a href="/w/index.php?title=I-32_(drug)&action=edit&redlink=1" class="new" title="I-32 (drug) (page does not exist)">I-32</a></li> <li><a href="/wiki/Indoleacetaldehyde" class="mw-redirect" title="Indoleacetaldehyde">IAL</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine</a></li> <li><a href="/wiki/LY-367,265" title="LY-367,265">LY-367265</a></li> <li><a href="/wiki/Pirlindole" title="Pirlindole">Pirlindole</a></li> <li><a href="/wiki/(R)-69" title="(R)-69">(R)-69 (3IQ)</a></li> <li><a href="/wiki/Ro60-0175" title="Ro60-0175">Ro60-0175</a></li> <li><a href="/wiki/Ro60-0213" title="Ro60-0213">Ro60-0213</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/Sertindole" title="Sertindole">Sertindole</a></li> <li><a href="/wiki/SN-22" title="SN-22">SN-22</a></li> <li><a href="/wiki/Substituted_benzofuran" title="Substituted benzofuran">Substituted benzofurans</a> (e.g., <a href="/w/index.php?title=3-(2-aminopropyl)benzofuran&action=edit&redlink=1" class="new" title="3-(2-aminopropyl)benzofuran (page does not exist)">3-APB</a>, <a href="/wiki/5-MeO-DiBF" title="5-MeO-DiBF">5-MeO-DiBF</a>, <a href="/wiki/Benzofuranylpropylaminopentane" title="Benzofuranylpropylaminopentane">BPAP</a>, <a href="/wiki/Dimemebfe" title="Dimemebfe">dimemebfe</a>, <a href="/w/index.php?title=Mebfap&action=edit&redlink=1" class="new" title="Mebfap (page does not exist)">mebfap</a>)</li> <li><a href="/wiki/Tepirindole" title="Tepirindole">Tepirindole</a></li> <li><a href="/wiki/Tetrindole" title="Tetrindole">Tetrindole</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/LY-334370" title="LY-334370">LY-334370</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>)</li> <li><a href="/wiki/VER-3323" title="VER-3323">VER-3323</a></li> <li><a href="/wiki/VU6067416" title="VU6067416">VU6067416</a></li> <li><a href="/wiki/YM-348" title="YM-348">YM-348</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" 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