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Alprazolam - Wikipedia
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id="toc-Medical_uses-sublist" class="vector-toc-list"> <li id="toc-Panic_disorder" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Panic_disorder"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Panic disorder</span> </div> </a> <ul id="toc-Panic_disorder-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Anxiety_disorders" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Anxiety_disorders"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Anxiety disorders</span> </div> </a> <ul id="toc-Anxiety_disorders-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemotherapy-induced_nausea_and_vomiting" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chemotherapy-induced_nausea_and_vomiting"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Chemotherapy-induced nausea and vomiting</span> </div> </a> <ul id="toc-Chemotherapy-induced_nausea_and_vomiting-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Contraindications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Contraindications"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Contraindications</span> </div> </a> <ul id="toc-Contraindications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Side effects</span> </div> </a> <button aria-controls="toc-Side_effects-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Side effects subsection</span> </button> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> <li id="toc-Paradoxical_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Paradoxical_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Paradoxical reactions</span> </div> </a> <ul id="toc-Paradoxical_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Food_and_drug_interactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Food_and_drug_interactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Food and drug interactions</span> </div> </a> <ul id="toc-Food_and_drug_interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pregnancy_and_breastfeeding" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pregnancy_and_breastfeeding"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Pregnancy and breastfeeding</span> </div> </a> <ul id="toc-Pregnancy_and_breastfeeding-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Overdose" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Overdose"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Overdose</span> </div> </a> <ul id="toc-Overdose-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dependence_and_withdrawal" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dependence_and_withdrawal"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Dependence and withdrawal</span> </div> </a> <ul id="toc-Dependence_and_withdrawal-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Pharmacology</span> </div> </a> <button aria-controls="toc-Pharmacology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Pharmacology subsection</span> </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-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"> <span class="vector-toc-numb">4.1</span> <span>Mechanism of action</span> </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Chemistry</span> </div> </a> <button aria-controls="toc-Chemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Chemistry subsection</span> </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Physical_properties" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Physical_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Physical properties</span> </div> </a> <ul id="toc-Physical_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Synthesis</span> </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Detection" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Detection"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Detection</span> </div> </a> <ul id="toc-Detection-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Dosage_forms" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Dosage_forms"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Dosage forms</span> </div> </a> <ul id="toc-Dosage_forms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Legal_status" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Legal_status"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Legal status</span> </div> </a> <ul id="toc-Legal_status-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Availability" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Availability"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Availability</span> </div> </a> <ul id="toc-Availability-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Recreational_use" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Recreational_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Recreational use</span> </div> </a> <button aria-controls="toc-Recreational_use-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Recreational use subsection</span> </button> <ul id="toc-Recreational_use-sublist" class="vector-toc-list"> <li id="toc-Slang_terms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Slang_terms"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1</span> <span>Slang terms</span> </div> </a> <ul id="toc-Slang_terms-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-In_popular_culture" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#In_popular_culture"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>In popular culture</span> </div> </a> <ul id="toc-In_popular_culture-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Alprazolam</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 47 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-47" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">47 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D9%84%D8%A8%D8%B1%D8%A7%D8%B2%D9%88%D9%84%D8%A7%D9%85" title="ألبرازولام – Arabic" lang="ar" hreflang="ar" data-title="ألبرازولام" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Asturian" lang="ast" hreflang="ast" data-title="Alprazolam" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A2%D9%84%D9%BE%D8%B1%D8%A7%D8%B2%D9%88%D9%84%D8%A7%D9%85" title="آلپرازولام – South Azerbaijani" lang="azb" hreflang="azb" data-title="آلپرازولام" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%90%D0%BB%D0%BF%D1%80%D0%B0%D0%B7%D0%BE%D0%BB%D0%B0%D0%BC" title="Алпразолам – Bulgarian" lang="bg" hreflang="bg" data-title="Алпразолам" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Czech" lang="cs" hreflang="cs" data-title="Alprazolam" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Alprasolam" title="Alprasolam – Welsh" lang="cy" hreflang="cy" data-title="Alprasolam" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Danish" lang="da" hreflang="da" data-title="Alprazolam" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Alprazolam" title="Alprazolam – German" lang="de" hreflang="de" data-title="Alprazolam" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BB%CF%80%CF%81%CE%B1%CE%B6%CE%BF%CE%BB%CE%AC%CE%BC%CE%B7" title="Αλπραζολάμη – Greek" lang="el" hreflang="el" data-title="Αλπραζολάμη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Spanish" lang="es" hreflang="es" data-title="Alprazolam" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Alprazolamo" title="Alprazolamo – Esperanto" lang="eo" hreflang="eo" data-title="Alprazolamo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D9%84%D9%BE%D8%B1%D8%A7%D8%B2%D9%88%D9%84%D8%A7%D9%85" title="آلپرازولام – Persian" lang="fa" hreflang="fa" data-title="آلپرازولام" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Alprazolam" title="Alprazolam – French" lang="fr" hreflang="fr" data-title="Alprazolam" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Galician" lang="gl" hreflang="gl" data-title="Alprazolam" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%8C%ED%94%84%EB%9D%BC%EC%A1%B8%EB%9E%8C" title="알프라졸람 – Korean" lang="ko" hreflang="ko" data-title="알프라졸람" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Croatian" lang="hr" hreflang="hr" data-title="Alprazolam" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Indonesian" lang="id" hreflang="id" data-title="Alprazolam" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Italian" lang="it" hreflang="it" data-title="Alprazolam" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%9C%D7%A4%D7%A8%D7%90%D7%96%D7%95%D7%9C%D7%90%D7%9D" title="אלפראזולאם – Hebrew" lang="he" hreflang="he" data-title="אלפראזולאם" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Javanese" lang="jv" hreflang="jv" data-title="Alprazolam" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ks mw-list-item"><a href="https://ks.wikipedia.org/wiki/%D8%A7%D9%84%D9%BE%D8%B1%D8%A7%D8%B2%D9%88%D9%84%D9%85" title="الپرازولم – Kashmiri" lang="ks" hreflang="ks" data-title="الپرازولم" data-language-autonym="कॉशुर / کٲشُر" data-language-local-name="Kashmiri" class="interlanguage-link-target"><span>कॉशुर / کٲشُر</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Alprazolams" title="Alprazolams – Latvian" lang="lv" hreflang="lv" data-title="Alprazolams" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Alprazol%C3%A1m" title="Alprazolám – Hungarian" lang="hu" hreflang="hu" data-title="Alprazolám" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BF%D1%80%D0%B0%D0%B7%D0%BE%D0%BB%D0%B0%D0%BC" title="Алпразолам – Macedonian" lang="mk" hreflang="mk" data-title="Алпразолам" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Malay" lang="ms" hreflang="ms" data-title="Alprazolam" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-min mw-list-item"><a href="https://min.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Minangkabau" lang="min" hreflang="min" data-title="Alprazolam" data-language-autonym="Minangkabau" data-language-local-name="Minangkabau" class="interlanguage-link-target"><span>Minangkabau</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Dutch" lang="nl" hreflang="nl" data-title="Alprazolam" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%AB%E3%83%97%E3%83%A9%E3%82%BE%E3%83%A9%E3%83%A0" title="アルプラゾラム – Japanese" lang="ja" hreflang="ja" data-title="アルプラゾラム" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Alprazolam" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%86%E0%AC%B2%E0%AC%AA%E0%AD%8D%E0%AC%B0%E0%AC%BE%E0%AC%9C%E0%AD%8B%E0%AC%B2%E0%AC%BE%E0%AC%AE" title="ଆଲପ୍ରାଜୋଲାମ – Odia" lang="or" hreflang="or" data-title="ଆଲପ୍ରାଜୋଲାମ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Polish" lang="pl" hreflang="pl" data-title="Alprazolam" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Portuguese" lang="pt" hreflang="pt" data-title="Alprazolam" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Romanian" lang="ro" hreflang="ro" data-title="Alprazolam" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D0%BB%D0%BF%D1%80%D0%B0%D0%B7%D0%BE%D0%BB%D0%B0%D0%BC" title="Алпразолам – Russian" lang="ru" hreflang="ru" data-title="Алпразолам" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Simple English" lang="en-simple" hreflang="en-simple" data-title="Alprazolam" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Slovenian" lang="sl" hreflang="sl" data-title="Alprazolam" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Serbian" lang="sr" hreflang="sr" data-title="Alprazolam" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Alprazolam" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Sundanese" lang="su" hreflang="su" data-title="Alprazolam" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Alpratsolaami" title="Alpratsolaami – Finnish" lang="fi" hreflang="fi" data-title="Alpratsolaami" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Swedish" lang="sv" hreflang="sv" data-title="Alprazolam" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%85%E0%AE%B2%E0%AF%8D%E0%AE%AA%E0%AF%8D%E0%AE%AA%E0%AE%BF%E0%AE%B0%E0%AE%9A%E0%AF%8B%E0%AE%B2%E0%AE%AE%E0%AF%8D" title="அல்ப்பிரசோலம் – Tamil" lang="ta" hreflang="ta" data-title="அல்ப்பிரசோலம்" 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href="https://tr.wikipedia.org/wiki/Alprazolam" title="Alprazolam – Turkish" lang="tr" hreflang="tr" data-title="Alprazolam" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BF%D1%80%D0%B0%D0%B7%D0%BE%D0%BB%D0%B0%D0%BC" title="Алпразолам – Ukrainian" lang="uk" hreflang="uk" data-title="Алпразолам" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%98%BF%E6%99%AE%E5%94%91%E4%BB%91" title="阿普唑仑 – Chinese" lang="zh" hreflang="zh" data-title="阿普唑仑" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet 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For other uses, see <a href="/wiki/Xanax_(disambiguation)" class="mw-disambig" title="Xanax (disambiguation)">Xanax (disambiguation)</a>.</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Alprazolam">Alprazolam</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Alprazolam_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Alprazolam_structure.svg/135px-Alprazolam_structure.svg.png" decoding="async" width="135" height="171" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Alprazolam_structure.svg/203px-Alprazolam_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/31/Alprazolam_structure.svg/270px-Alprazolam_structure.svg.png 2x" data-file-width="512" data-file-height="647" /></a></span></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Alprazolam_ball-and-stick_model.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Alprazolam_ball-and-stick_model.png/135px-Alprazolam_ball-and-stick_model.png" decoding="async" width="135" height="182" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Alprazolam_ball-and-stick_model.png/203px-Alprazolam_ball-and-stick_model.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Alprazolam_ball-and-stick_model.png/270px-Alprazolam_ball-and-stick_model.png 2x" data-file-width="989" data-file-height="1331" /></a></span></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;">Pronunciation</th><td class="infobox-data"><span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/æ/: 'a' in 'bad'">æ</span><span title="'l' in 'lie'">l</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'p' in 'pie'">p</span><span title="'r' in 'rye'">r</span><span title="/æ/: 'a' in 'bad'">æ</span><span title="'z' in 'zoom'">z</span><span title="/ə/: 'a' in 'about'">ə</span><span title="'l' in 'lie'">l</span><span title="/æ/: 'a' in 'bad'">æ</span><span title="'m' in 'my'">m</span></span>/</a></span></span> or <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/æ/: 'a' in 'bad'">æ</span><span title="'l' in 'lie'">l</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'p' in 'pie'">p</span><span title="'r' in 'rye'">r</span><span title="/eɪ/: 'a' in 'face'">eɪ</span><span title="'z' in 'zoom'">z</span><span title="/ə/: 'a' in 'about'">ə</span><span title="'l' in 'lie'">l</span><span title="/æ/: 'a' in 'bad'">æ</span><span title="'m' in 'my'">m</span></span>/</a></span></span> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Xanax, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/alprazolam.html">Monograph</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><span title="medlineplus.gov"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a684001.html">a684001</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><small><abbr class="country-name" title="United States">US</abbr></small> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Alprazolam">Alprazolam</a></span></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> C<sup id="cite_ref-Drugs.com_pregnancy_1-0" class="reference"><a href="#cite_note-Drugs.com_pregnancy-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Substance_dependence" title="Substance dependence">Dependence<br />liability</a></th><td class="infobox-data">Very High<sup id="cite_ref-Ait2018_3-0" class="reference"><a href="#cite_note-Ait2018-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Addiction" title="Addiction">Addiction<br />liability</a></th><td class="infobox-data">High<sup id="cite_ref-Ait2018_3-1" class="reference"><a href="#cite_note-Ait2018-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepine</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/ATC_code_N05" title="ATC code N05">N05BA12</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N05BA12">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_8" title="Standard for the Uniform Scheduling of Medicines and Poisons">S8</a> (Controlled drug)<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="Brazil">BR</abbr>:</small> <a href="/wiki/Brazilian_Controlled_Drugs_and_Substances_Act#Class_B1" title="Brazilian Controlled Drugs and Substances Act">Class B1</a> (Psychoactive drugs)</li> <li><small><abbr class="country-name" title="Canada">CA</abbr></small>: <a href="/wiki/Controlled_Drugs_and_Substances_Act#Schedule_IV" title="Controlled Drugs and Substances Act">Schedule IV</a> Targeted (CDSA IV)<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="Germany">DE</abbr></small>: <a href="/wiki/Drugs_controlled_by_the_German_Narcotic_Drugs_Act#Anlage_III" title="Drugs controlled by the German Narcotic Drugs Act">Anlage III</a> (Special prescription form required) (in doses higher than <span class="nowrap">1 mg</span>)</li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only) / Class C<sup id="cite_ref-Xanax_UK_SmPC_7-0" class="reference"><a href="#cite_note-Xanax_UK_SmPC-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-misuse_of_drugs_legislation_8-0" class="reference"><a href="#cite_note-misuse_of_drugs_legislation-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Boxed_warning" title="Boxed warning"><span style="border:thin solid black;">WARNING</span></a><sup id="cite_ref-FDA-AllBoxedWarnings_4-0" class="reference"><a href="#cite_note-FDA-AllBoxedWarnings-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>Schedule IV<sup id="cite_ref-Xanax_FDA_label_9-0" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Xanax_XR_FDA_label_10-0" class="reference"><a href="#cite_note-Xanax_XR_FDA_label-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="United Nations">UN</abbr>:</small> <a href="/wiki/Convention_on_Psychotropic_Substances#Schedule_IV" title="Convention on Psychotropic Substances">Psychotropic Schedule IV</a></li> <li><small><abbr class="country-name" title="European Union">EU</abbr>:</small> Rx-only<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></li> <li>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">80–90%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">80%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a>, via <a href="/wiki/Cytochrome_P450_3A4" class="mw-redirect" title="Cytochrome P450 3A4">cytochrome P450 3A4</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data"> <ul><li>α-hydroxyalprazolam</li> <li>4-hydroxyalprazolam</li></ul> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Onset_of_action" title="Onset of action">Onset of action</a></th><td class="infobox-data">30~60 minutes<sup id="cite_ref-Lill2016_13-0" class="reference"><a href="#cite_note-Lill2016-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li>Instant-release:</li> <li>11~13 hours<sup id="cite_ref-AHFS2018_14-0" class="reference"><a href="#cite_note-AHFS2018-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><br /></li> <li>Extended-release:</li> <li>11~16 hours<sup id="cite_ref-AHFS2018_14-1" class="reference"><a href="#cite_note-AHFS2018-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pharmacodynamics#Duration_of_action" title="Pharmacodynamics">Duration of action</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li>Instant-release:</li> <li>6 hours<sup id="cite_ref-Lill2016_13-1" class="reference"><a href="#cite_note-Lill2016-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><br /></li> <li>Extended-release:</li> <li>11.3 hours</li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Kidney" title="Kidney">Kidney</a></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%;">8-Chloro-1-methyl-6-phenyl-4<i>H</i>-[1,2,4]triazolo[4,3-a] [1,4]benzodiazepine</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=28981-97-7">28981-97-7</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/2118">2118</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=7111">7111</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00404">DB00404</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.2034.html">2034</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/YU55MQ3IZY">YU55MQ3IZY</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00225">D00225</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2611">CHEBI:2611</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL661">ChEMBL661</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID4022577">DTXSID4022577</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q319877#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.044.849">100.044.849</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q319877#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>17</sub><span title="Hydrogen">H</span><sub>13</sub><span title="Chlorine">Cl</span><span title="Nitrogen">N</span><sub>4</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002308770000000000♠"></span>308.77</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=Cc1nnc2n1-c1ccc%28Cl%29cc1C%28c1ccccc1%29%3DNC2">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Cc1nnc2n1-c1ccc(Cl)cc1C(c1ccccc1)=NC2</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:VREFGVBLTWBCJP-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477164519&page2=Alprazolam">(verify)</a></span></span></td></tr></tbody></table> <p><b>Alprazolam</b>, sold under the brand name <b>Xanax</b> among others, is a fast-acting, potent <a href="/wiki/Tranquilizer" class="mw-redirect" title="Tranquilizer">tranquilizer</a> of moderate duration within the <a href="/wiki/Triazolobenzodiazepine" title="Triazolobenzodiazepine">triazolobenzodiazepine</a> group of chemicals called <a href="/wiki/Benzodiazepine" title="Benzodiazepine">benzodiazepines</a>.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Alprazolam is most commonly prescribed in the management of <a href="/wiki/Anxiety_disorder" title="Anxiety disorder">anxiety disorders</a>, especially <a href="/wiki/Panic_disorder" title="Panic disorder">panic disorder</a> and <a href="/wiki/Generalized_anxiety_disorder" title="Generalized anxiety disorder">generalized anxiety disorder</a> (GAD).<sup id="cite_ref-Xanax_FDA_label_9-1" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Other uses include the treatment of <a href="/wiki/Chemotherapy-induced_nausea_and_vomiting" title="Chemotherapy-induced nausea and vomiting">chemotherapy-induced nausea</a>, together with other treatments.<sup id="cite_ref-AHFS2018_14-2" class="reference"><a href="#cite_note-AHFS2018-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> GAD improvement occurs generally within a week.<sup id="cite_ref-Verster2004_16-0" class="reference"><a href="#cite_note-Verster2004-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Alprazolam is generally taken <a href="/wiki/Oral_administration" title="Oral administration">orally</a>.<sup id="cite_ref-AHFS2018_14-3" class="reference"><a href="#cite_note-AHFS2018-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Common side effects include <a href="/wiki/Sleepiness" class="mw-redirect" title="Sleepiness">sleepiness</a>, <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>, <a href="/wiki/Reduced_affect_display" title="Reduced affect display">suppressed emotions</a>, mild to severe <a href="/wiki/Ataxia" title="Ataxia">decreases in motor skills</a>, <a href="/wiki/Hiccup" title="Hiccup">hiccups</a>, dulling or declining of <a href="/wiki/Cognition" title="Cognition">cognition</a>, decreased <a href="/wiki/Alertness" title="Alertness">alertness</a>, <a href="/wiki/Xerostomia" title="Xerostomia">dry mouth</a> (mildly), <a href="/wiki/Bradycardia" title="Bradycardia">decreased heart rate</a>, <a href="/wiki/CNS_depression" class="mw-redirect" title="CNS depression">suppression</a> of <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> activity, impairment of judgment (usually in higher than therapeutic doses), marginal to severe decreases in memory formation, decreased ability to <a href="/wiki/Information_processing_(psychology)" title="Information processing (psychology)">process new information</a>, as well as partial to complete <a href="/wiki/Anterograde_amnesia" title="Anterograde amnesia">anterograde amnesia</a>,<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> depending on dosage.<sup id="cite_ref-AHFS2018_14-4" class="reference"><a href="#cite_note-AHFS2018-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Some of the sedation and drowsiness may improve within a few days.<sup id="cite_ref-Pav10_19-0" class="reference"><a href="#cite_note-Pav10-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Benzodiazepine_withdrawal_syndrome" title="Benzodiazepine withdrawal syndrome">Benzodiazepine withdrawal</a> symptoms may occur if use is suddenly decreased.<sup id="cite_ref-AHFS2018_14-5" class="reference"><a href="#cite_note-AHFS2018-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Verster2004_16-1" class="reference"><a href="#cite_note-Verster2004-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Alprazolam was invented by Jackson Hester Jr. at the <a href="/wiki/Upjohn" title="Upjohn">Upjohn Company</a><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> and patented in 1971 and approved for medical use in the United States in 1981.<sup id="cite_ref-AHFS2018_14-6" class="reference"><a href="#cite_note-AHFS2018-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fis2006_21-0" class="reference"><a href="#cite_note-Fis2006-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Alprazolam is a <a href="/wiki/Controlled_Substances_Act#Schedule_IV_controlled_substances" title="Controlled Substances Act">Schedule IV</a> controlled substance and is a common drug of abuse.<sup id="cite_ref-Ait2018_3-2" class="reference"><a href="#cite_note-Ait2018-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> It is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a>.<sup id="cite_ref-Xanax_FDA_label_9-2" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In 2022, it was the 41st most commonly prescribed medication in the United States, with more than 14<span class="nowrap"> </span>million prescriptions.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Boites_d%27alprazolam444.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Boites_d%27alprazolam444.jpg/220px-Boites_d%27alprazolam444.jpg" decoding="async" width="220" height="200" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Boites_d%27alprazolam444.jpg/330px-Boites_d%27alprazolam444.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/Boites_d%27alprazolam444.jpg/440px-Boites_d%27alprazolam444.jpg 2x" data-file-width="1648" data-file-height="1497" /></a><figcaption>Alprazolam pills in boxes, as sold in <a href="/wiki/France" title="France">France</a>; both the original <a href="/wiki/Pfizer" title="Pfizer">Pfizer</a> brand product Xanax and various <a href="/wiki/Generic_drug" title="Generic drug">generic forms</a> of alprazolam are depicted here.</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Xanax_2_mg.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Xanax_2_mg.jpg/220px-Xanax_2_mg.jpg" decoding="async" width="220" height="326" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Xanax_2_mg.jpg/330px-Xanax_2_mg.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Xanax_2_mg.jpg/440px-Xanax_2_mg.jpg 2x" data-file-width="997" data-file-height="1477" /></a><figcaption>A prescription bottle of Xanax</figcaption></figure> <p>Alprazolam is used in the management of <a href="/wiki/Anxiety_disorder" title="Anxiety disorder">anxiety disorders</a> and <a href="/wiki/Nausea" title="Nausea">nausea</a> due to <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapy</a>.<sup id="cite_ref-AHFS2018_14-7" class="reference"><a href="#cite_note-AHFS2018-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Alprazolam is <a href="/wiki/Indicated" class="mw-redirect" title="Indicated">indicated</a> for the treatment of <a href="/wiki/Generalized_anxiety_disorder" title="Generalized anxiety disorder">generalized anxiety disorder</a> (GAD) and <a href="/wiki/Panic_disorder" title="Panic disorder">panic disorder</a> with or without <a href="/wiki/Agoraphobia" title="Agoraphobia">agoraphobia</a> in adults.<sup id="cite_ref-Xanax_FDA_label_9-3" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Panic_disorder">Panic disorder</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=2" title="Edit section: Panic disorder"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alprazolam is effective in the relief of moderate to severe <a href="/wiki/Anxiety" title="Anxiety">anxiety</a> and <a href="/wiki/Panic_attack" title="Panic attack">panic attacks</a>.<sup id="cite_ref-Xanax_FDA_label_9-4" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In <a href="/wiki/Australia" title="Australia">Australia</a>, alprazolam is not recommended for the treatment of <a href="/wiki/Panic_disorder" title="Panic disorder">panic disorder</a> because of concerns regarding <a href="/wiki/Drug_tolerance" title="Drug tolerance">tolerance</a>, <a href="/wiki/Substance_dependence" title="Substance dependence">dependence</a>, and <a href="/wiki/Substance_abuse" title="Substance abuse">abuse</a>.<sup id="cite_ref-Moy2012_25-0" class="reference"><a href="#cite_note-Moy2012-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Most evidence shows that the benefits of alprazolam in treating panic disorder last only four to ten weeks. However, people with panic disorder have been treated on an open basis for up to eight months without apparent loss of benefit.<sup id="cite_ref-Xanax_FDA_label_9-5" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Alprazolam is recommended by the World Federation of Societies of Biological Psychiatry (WFSBP) for treatment-resistant cases of panic disorder where there is no history of tolerance or dependence.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>A 2023 <a href="/wiki/Meta-analysis" title="Meta-analysis">meta-analysis</a> of published and unpublished FDA-submitted regulatory trials of alprazolam extended-release for panic disorder found that only one of five clinical trials showed a positive efficacy outcome (20%), while the rest were negative and did not demonstrate effectiveness.<sup id="cite_ref-pmid37853797_27-0" class="reference"><a href="#cite_note-pmid37853797-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> In the published literature, three trials were published conveying a positive outcome (100%), but of these, only one was actually positive and the other two were considered to have been inappropriately spun as positive.<sup id="cite_ref-pmid37853797_27-1" class="reference"><a href="#cite_note-pmid37853797-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Effect_size" title="Effect size">effect size</a> (<a href="/wiki/Hedges%27s_g" class="mw-redirect" title="Hedges's g">Hedges's g</a>) of alprazolam for treatment of panic disorder based on the five clinical trials was 0.33 (a small effect) and based on the published trials was 0.47 (a moderate effect), equating to an increase of 0.14 or 42%.<sup id="cite_ref-pmid37853797_27-2" class="reference"><a href="#cite_note-pmid37853797-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> The authors concluded that <a href="/wiki/Publication_bias" title="Publication bias">publication bias</a> substantially inflated the effectiveness of alprazolam for panic disorder.<sup id="cite_ref-pmid37853797_27-3" class="reference"><a href="#cite_note-pmid37853797-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Anxiety_disorders">Anxiety disorders</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=3" title="Edit section: Anxiety disorders"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Anxiety" title="Anxiety">Anxiety</a> associated with <a href="/wiki/Major_depressive_disorder" title="Major depressive disorder">depression</a> is responsive to alprazolam. Clinical studies have shown that the effectiveness is limited to four months for <a href="/wiki/Anxiety_disorder" title="Anxiety disorder">anxiety disorders</a>.<sup id="cite_ref-Xanax_FDA_label_9-6" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> However, the research into <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a> properties of alprazolam is poor and has only assessed its short-term effects against depression.<sup id="cite_ref-van_Marwijk-2012_28-0" class="reference"><a href="#cite_note-van_Marwijk-2012-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> In one study, some long term, high-dosage users of alprazolam developed reversible depression.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>In the US, alprazolam is <a href="/wiki/Indicated" class="mw-redirect" title="Indicated">indicated</a> for the treatment of <a href="/wiki/Generalized_anxiety_disorder" title="Generalized anxiety disorder">generalized anxiety disorder</a> and <a href="/wiki/Panic_disorder" title="Panic disorder">panic disorder</a> with or without <a href="/wiki/Agoraphobia" title="Agoraphobia">agoraphobia</a>.<sup id="cite_ref-Xanax_FDA_label_9-7" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Xanax_XR_FDA_label_10-1" class="reference"><a href="#cite_note-Xanax_XR_FDA_label-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>In the UK, alprazolam is indicated for short-term symptomatic treatment of anxiety in adults.<sup id="cite_ref-Xanax_UK_SmPC_7-1" class="reference"><a href="#cite_note-Xanax_UK_SmPC-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Chemotherapy-induced_nausea_and_vomiting">Chemotherapy-induced nausea and vomiting</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=4" title="Edit section: Chemotherapy-induced nausea and vomiting"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alprazolam may be used in combination with other medications for <a href="/wiki/Chemotherapy-induced_nausea_and_vomiting" title="Chemotherapy-induced nausea and vomiting">chemotherapy-induced nausea and vomiting</a>.<sup id="cite_ref-AHFS2018_14-8" class="reference"><a href="#cite_note-AHFS2018-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=5" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Benzodiazepines require special precaution if used in children and in alcohol- or drug-dependent individuals. Particular care should be taken in pregnant or elderly people, people with <a href="/wiki/Substance_use_disorder" title="Substance use disorder">substance use disorder</a> history, particularly <a href="/wiki/Alcohol_dependence" title="Alcohol dependence">alcohol dependence</a>, and people with <a href="/wiki/Comorbid" class="mw-redirect" title="Comorbid">comorbid</a> <a href="/wiki/Mental_disorder" title="Mental disorder">psychiatric disorders</a>.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p><p>Alprazolam should be avoided or carefully monitored by medical professionals in individuals with <a href="/wiki/Myasthenia_gravis" title="Myasthenia gravis">myasthenia gravis</a>, acute narrow-angle <a href="/wiki/Glaucoma" title="Glaucoma">glaucoma</a>, severe liver deficiencies such as <a href="/wiki/Cirrhosis" title="Cirrhosis">cirrhosis</a>, severe <a href="/wiki/Sleep_apnea" title="Sleep apnea">sleep apnea</a>, pre-existing respiratory depression, marked <a href="/wiki/Neuromuscular" class="mw-redirect" title="Neuromuscular">neuromuscular</a> <a href="/wiki/Respiratory" class="mw-redirect" title="Respiratory">respiratory</a>, acute <a href="/wiki/Pulmonary_insufficiency" class="mw-redirect" title="Pulmonary insufficiency">pulmonary insufficiency</a>, chronic <a href="/wiki/Psychosis" title="Psychosis">psychosis</a>, <a href="/wiki/Hypersensitivity" title="Hypersensitivity">hypersensitivity</a>, <a href="/wiki/Allergy" title="Allergy">allergy</a> to alprazolam or other benzodiazepines, and <a href="/wiki/Borderline_personality_disorder" title="Borderline personality disorder">borderline personality disorder</a>, where it may induce <a href="/wiki/Suicidality" class="mw-redirect" title="Suicidality">suicidality</a> and <a href="/wiki/Episodic_dyscontrol_syndrome" class="mw-redirect" title="Episodic dyscontrol syndrome">dyscontrol</a>.<sup id="cite_ref-bnf_31-0" class="reference"><a href="#cite_note-bnf-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-hori_32-0" class="reference"><a href="#cite_note-hori-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>Like all <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> <a href="/wiki/Depressant" title="Depressant">depressants</a>, alprazolam in larger-than-normal doses can cause significant deterioration in <a href="/wiki/Alertness" title="Alertness">alertness</a> and increase <a href="/wiki/Drowsiness" class="mw-redirect" title="Drowsiness">drowsiness</a>, especially in those unaccustomed to the drug's effects.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=6" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Side_effects_of_alprazolam.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Side_effects_of_alprazolam.svg/220px-Side_effects_of_alprazolam.svg.png" decoding="async" width="220" height="164" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Side_effects_of_alprazolam.svg/330px-Side_effects_of_alprazolam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Side_effects_of_alprazolam.svg/440px-Side_effects_of_alprazolam.svg.png 2x" data-file-width="1525" data-file-height="1138" /></a><figcaption><a href="/wiki/Side_effect" title="Side effect">Side effects</a> from alprazolam</figcaption></figure> <p><a href="/wiki/Sedative" title="Sedative">Sedative</a> drugs, including alprazolam, have been associated with an increased risk of death.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>Possible <a href="/wiki/Side_effects" class="mw-redirect" title="Side effects">side effects</a> include: </p> <ul><li><a href="/wiki/Anterograde_amnesia" title="Anterograde amnesia">Anterograde amnesia</a><sup id="cite_ref-Barbee95_36-0" class="reference"><a href="#cite_note-Barbee95-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Attention" title="Attention">Concentration</a> problems</li> <li><a href="/wiki/Ataxia" title="Ataxia">Ataxia</a></li> <li><a href="/wiki/Dysarthria" title="Dysarthria">Dysarthria</a><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Disinhibition" title="Disinhibition">Disinhibition</a><sup id="cite_ref-Michel_L,_Lang_JP_2003_479–85_38-0" class="reference"><a href="#cite_note-Michel_L,_Lang_JP_2003_479–85-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Somnolence" title="Somnolence">Drowsiness</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, <a href="/wiki/Lightheadedness" title="Lightheadedness">lightheadedness</a>, <a href="/wiki/Fatigue" title="Fatigue">fatigue</a>, <a href="/wiki/Ataxia" title="Ataxia">ataxia</a>, and <a href="/wiki/Vertigo" title="Vertigo">vertigo</a><sup id="cite_ref-drftb_39-0" class="reference"><a href="#cite_note-drftb-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-acmirttoadom_40-0" class="reference"><a href="#cite_note-acmirttoadom-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Xerostomia" title="Xerostomia">Dry mouth</a> (infrequent)<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Hallucination" title="Hallucination">Hallucinations</a> (rare)<sup id="cite_ref-ase_42-0" class="reference"><a href="#cite_note-ase-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Jaundice" title="Jaundice">Jaundice</a> (very rare)<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Seizure" title="Seizure">Seizure</a> (less common)<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Rash" title="Rash">Skin rash</a></li> <li><a href="/wiki/Hypoventilation" title="Hypoventilation">Respiratory depression</a></li> <li><a href="/wiki/Constipation" title="Constipation">Constipation</a><sup id="cite_ref-drftb_39-1" class="reference"><a href="#cite_note-drftb-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-acmirttoadom_40-1" class="reference"><a href="#cite_note-acmirttoadom-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Suicidal_ideation" title="Suicidal ideation">Suicidal ideation</a> or <a href="/wiki/Suicide" title="Suicide">suicide</a><sup id="cite_ref-Dobb2017_45-0" class="reference"><a href="#cite_note-Dobb2017-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Urinary_retention" title="Urinary retention">Urinary retention</a> (infrequent)<sup id="cite_ref-ase_42-1" class="reference"><a href="#cite_note-ase-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Muscle_weakness" title="Muscle weakness">Muscle weakness</a><sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (August 2023)">medical citation needed</span></a></i>]</sup></li></ul> <p>In September 2020, the U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) required that <a href="/wiki/Boxed_warning" title="Boxed warning">boxed warnings</a> for all benzodiazepine medications be updated to describe the risks of abuse, misuse, addiction, physical dependence, and withdrawal reactions consistently across all the medicines in the class.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Paradoxical_reactions">Paradoxical reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=7" title="Edit section: Paradoxical reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although unusual, the following <a href="/wiki/Paradoxical_reaction" title="Paradoxical reaction">paradoxical reactions</a> have been shown to occur: </p> <ul><li><a href="/wiki/Aggression" title="Aggression">Aggression</a><sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Mania" title="Mania">Mania</a>, <a href="/wiki/Psychomotor_agitation" title="Psychomotor agitation">agitation</a>, <a href="/wiki/Attention_deficit_hyperactivity_disorder" title="Attention deficit hyperactivity disorder">hyperactivity</a>, and <a href="/wiki/Psychomotor_agitation" title="Psychomotor agitation">restlessness</a><sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Rage_(emotion)" title="Rage (emotion)">Rage</a> and hostility<sup id="cite_ref-Michel_L,_Lang_JP_2003_479–85_38-1" class="reference"><a href="#cite_note-Michel_L,_Lang_JP_2003_479–85-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Fasciculation" title="Fasciculation">Twitches</a> and <a href="/wiki/Tremor" title="Tremor">tremor</a><sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Food_and_drug_interactions">Food and drug interactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=8" title="Edit section: Food and drug interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alprazolam is primarily <a href="/wiki/Metabolised" class="mw-redirect" title="Metabolised">metabolized</a> via <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>.<sup id="cite_ref-Otani-2003_52-0" class="reference"><a href="#cite_note-Otani-2003-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> Combining CYP3A4 inhibitors such as <a href="/wiki/Cimetidine" title="Cimetidine">cimetidine</a>, <a href="/wiki/Erythromycin" title="Erythromycin">erythromycin</a>, <a href="/wiki/Norfluoxetine" class="mw-redirect" title="Norfluoxetine">norfluoxetine</a>, <a href="/wiki/Fluvoxamine" title="Fluvoxamine">fluvoxamine</a>, <a href="/wiki/Itraconazole" title="Itraconazole">itraconazole</a>, <a href="/wiki/Ketoconazole" title="Ketoconazole">ketoconazole</a>, <a href="/wiki/Nefazodone" title="Nefazodone">nefazodone</a>, <a href="/wiki/Propoxyphene" class="mw-redirect" title="Propoxyphene">propoxyphene</a>, and <a href="/wiki/Ritonavir" title="Ritonavir">ritonavir</a> delay the <a href="/wiki/Hepatic" class="mw-redirect" title="Hepatic">hepatic</a> clearance of alprazolam, which may result in its accumulation<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> and increased severity of its side effects.<sup id="cite_ref-cpoati_54-0" class="reference"><a href="#cite_note-cpoati-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a> and <a href="/wiki/Desipramine" title="Desipramine">desipramine</a> have been reported to increase an average of 31% and 20% respectively by the <a href="/wiki/Concomitant_drug" title="Concomitant drug">concomitant</a> administration of alprazolam tablets.<sup id="cite_ref-Xanax_FDA_label_9-8" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Combined_oral_contraceptive_pill" title="Combined oral contraceptive pill">Combined oral contraceptive pills</a> reduce the clearance of alprazolam, which may lead to increased plasma levels of alprazolam and accumulation.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Alcohol</a> is one of the most common interactions; alcohol and alprazolam taken in combination have a <a href="/wiki/Synergistic" class="mw-redirect" title="Synergistic">synergistic</a> effect on one another, which can cause severe sedation, behavioral changes, and intoxication. The more alcohol and alprazolam taken, the worse the interaction.<sup id="cite_ref-Michel_L,_Lang_JP_2003_479–85_38-2" class="reference"><a href="#cite_note-Michel_L,_Lang_JP_2003_479–85-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Combination of alprazolam with the herb <a href="/wiki/Kava" title="Kava">kava</a> can result in the development of a semi-<a href="/wiki/Coma" title="Coma">comatose</a> state.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> Plants in the genus <i><a href="/wiki/Hypericum" title="Hypericum">Hypericum</a></i>, including <a href="/wiki/St._John%27s_wort" class="mw-redirect" title="St. John's wort">St. John's wort</a>, conversely can lower the plasma levels of alprazolam and reduce its therapeutic effect.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pregnancy_and_breastfeeding">Pregnancy and breastfeeding</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=9" title="Edit section: Pregnancy and breastfeeding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Benzodiazepines cross the <a href="/wiki/Placenta" title="Placenta">placenta</a>, enter the <a href="/wiki/Fetus" title="Fetus">fetus</a>, and are also excreted in <a href="/wiki/Breast_milk" title="Breast milk">breast milk</a>.<sup id="cite_ref-Xanax_FDA_label_9-9" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The use of alprazolam during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> is associated with <a href="/wiki/Congenital_abnormalities" class="mw-redirect" title="Congenital abnormalities">congenital abnormalities</a>,<sup id="cite_ref-Xanax_FDA_label_9-10" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> and use in the last trimester may cause fetal <a href="/wiki/Drug_dependence" class="mw-redirect" title="Drug dependence">drug dependence</a> and <a href="/wiki/Withdrawal_symptoms" class="mw-redirect" title="Withdrawal symptoms">withdrawal symptoms</a> in the post-natal period as well as neonatal flaccidity and respiratory problems.<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> However, in long-term users of benzodiazepines, abrupt discontinuation due to concerns of <a href="/wiki/Teratogenesis" class="mw-redirect" title="Teratogenesis">teratogenesis</a> has a high risk of causing extreme withdrawal symptoms and a severe <a href="/wiki/Rebound_effect" title="Rebound effect">rebound effect</a> of the underlying <a href="/wiki/Mental_health_disorder" class="mw-redirect" title="Mental health disorder">mental health disorder</a>. <a href="/wiki/Spontaneous_abortions" class="mw-redirect" title="Spontaneous abortions">Spontaneous abortions</a> may also result from abrupt withdrawal of psychotropic medications, including benzodiazepines.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Overdose">Overdose</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=10" title="Edit section: Overdose"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Benzodiazepine_overdose" title="Benzodiazepine overdose">Benzodiazepine overdose</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Xanax_0.25,_0.5_%26_1_mg.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Xanax_0.25%2C_0.5_%26_1_mg.jpg/220px-Xanax_0.25%2C_0.5_%26_1_mg.jpg" decoding="async" width="220" height="208" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Xanax_0.25%2C_0.5_%26_1_mg.jpg/330px-Xanax_0.25%2C_0.5_%26_1_mg.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Xanax_0.25%2C_0.5_%26_1_mg.jpg/440px-Xanax_0.25%2C_0.5_%26_1_mg.jpg 2x" data-file-width="685" data-file-height="649" /></a><figcaption>Xanax 0.25 mg. (top row), 0.5 mg. (middle row), and 1 mg. (bottom row) tablets</figcaption></figure> <p>The maximum recommended daily dose is 10 milligrams per day.<sup id="cite_ref-Xanax_FDA_label_9-11" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Overdoses of alprazolam can be mild to severe depending on the quantity ingested and if other drugs are taken in combination.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </p><p>Alprazolam overdoses cause excess <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> (CNS) depression.<sup id="cite_ref-ase_42-2" class="reference"><a href="#cite_note-ase-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Dependence_and_withdrawal">Dependence and withdrawal</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=11" title="Edit section: Dependence and withdrawal"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Benzodiazepine_dependence" title="Benzodiazepine dependence">Benzodiazepine dependence</a> and <a href="/wiki/Benzodiazepine_withdrawal_syndrome" title="Benzodiazepine withdrawal syndrome">Benzodiazepine withdrawal syndrome</a></div> <p>The potential for misuse among those taking it for medical reasons is controversial, with some expert reviews stating that the risk is low and similar to that of other benzodiazepine drugs.<sup id="cite_ref-APAguide_66-0" class="reference"><a href="#cite_note-APAguide-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> Others state that there is a substantial risk of misuse and dependence in both patients and non-medical users and that the short half-life and rapid onset of action may increase the risk of misuse.<sup id="cite_ref-AHFS2018_14-9" class="reference"><a href="#cite_note-AHFS2018-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Moy2012_25-1" class="reference"><a href="#cite_note-Moy2012-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Compared to the large number of prescriptions, relatively few individuals increase their dose on their own initiative or engage in <a href="/wiki/Drug-seeking_behavior" class="mw-redirect" title="Drug-seeking behavior">drug-seeking behavior</a>.<sup id="cite_ref-DEAbrief_67-0" class="reference"><a href="#cite_note-DEAbrief-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> </p><p>Alprazolam, like other benzodiazepines, binds to specific sites on the GABA<sub>A</sub> (<a href="/wiki/%CE%93-Aminobutyric_acid" class="mw-redirect" title="Γ-Aminobutyric acid">gamma-aminobutyric acid</a>) receptor. When bound to these sites, which are referred to as benzodiazepine receptors, it modulates the effect of GABA<sub>A</sub> receptors and, thus, of GABAergic neurons.<sup id="cite_ref-:0_68-0" class="reference"><a href="#cite_note-:0-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag may rely on an unreliable or less reliable medical source. (April 2024)">unreliable medical source?</span></a></i>]</sup> Long-term use causes adaptive changes in the benzodiazepine receptors, making them less sensitive to stimulation and thus making the drugs less potent.<sup id="cite_ref-:1_69-0" class="reference"><a href="#cite_note-:1-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Drug_withdrawal" title="Drug withdrawal">Withdrawal</a> and <a href="/wiki/Rebound_symptoms" class="mw-redirect" title="Rebound symptoms">rebound symptoms</a> commonly occur and necessitate a gradual reduction in dosage to minimize withdrawal effects when discontinuing.<sup id="cite_ref-Verster2004_16-2" class="reference"><a href="#cite_note-Verster2004-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Not all withdrawal effects are evidence of true dependence or withdrawal. Recurrence of symptoms such as anxiety may simply indicate that the drug was having its expected anti-anxiety effect and that, in the absence of the drug, the symptom has returned to pretreatment levels. If the symptoms are more severe or frequent, the person may be experiencing a <a href="/wiki/Rebound_effect" title="Rebound effect">rebound effect</a> due to the removal of the drug. Either of these can occur without the person actually being drug dependent.<sup id="cite_ref-:1_69-1" class="reference"><a href="#cite_note-:1-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> </p><p>Alprazolam and other benzodiazepines may also cause the development of <a href="/wiki/Physical_dependence" title="Physical dependence">physical dependence</a>, <a href="/wiki/Drug_tolerance" title="Drug tolerance">tolerance</a>, and <a href="/wiki/Benzodiazepine_withdrawal_symptoms" class="mw-redirect" title="Benzodiazepine withdrawal symptoms">benzodiazepine withdrawal symptoms</a> during rapid dose reduction or cessation of therapy after long-term treatment.<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> There is a higher chance of withdrawal reactions if the drug is administered in a higher dosage than recommended, or if a person stops taking the medication altogether without slowly allowing the body to adjust to a lower-dosage regimen.<sup id="cite_ref-Ashton_manual_72-0" class="reference"><a href="#cite_note-Ashton_manual-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-73" class="reference"><a href="#cite_note-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> </p><p>In 1992, Romach and colleagues reported that dose escalation is not a characteristic of long-term alprazolam users and that the majority of long-term alprazolam users change their initial pattern of regular use to one of symptom control only when required.<sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> </p><p>Some common symptoms of alprazolam discontinuation include <a href="/wiki/Malaise" title="Malaise">malaise</a>, weakness, <a href="/wiki/Insomnia" title="Insomnia">insomnia</a>, <a href="/wiki/Tachycardia" title="Tachycardia">tachycardia</a>, lightheadedness, and dizziness.<sup id="cite_ref-75" class="reference"><a href="#cite_note-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> </p><p>Those taking more than 4 mg per day have an increased potential for dependence. This medication may cause withdrawal symptoms upon abrupt withdrawal or rapid tapering, which in some cases have been known to cause seizures, as well as marked <a href="/wiki/Delirium" title="Delirium">delirium</a> similar to that produced by the <a href="/wiki/Anticholinergic" title="Anticholinergic">anticholinergic</a> tropane alkaloids of Datura (<a href="/wiki/Hyoscine_hydrobromide" class="mw-redirect" title="Hyoscine hydrobromide">scopolamine</a> and <a href="/wiki/Atropine" title="Atropine">atropine</a>).<sup id="cite_ref-76" class="reference"><a href="#cite_note-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-77" class="reference"><a href="#cite_note-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-78" class="reference"><a href="#cite_note-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> The discontinuation of this medication may also cause rebound anxiety.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (August 2023)">medical citation needed</span></a></i>]</sup> </p><p>In a 1983 study, only 5% of patients who abruptly ceased taking long-acting benzodiazepines after less than eight months demonstrated withdrawal symptoms, but 43% who had been taking them for more than eight months did. With alprazolam, a short-acting benzodiazepine, taken for eight weeks, 65% of patients experienced significant rebound anxiety. To some degree, these older benzodiazepines are self-tapering.<sup id="cite_ref-Schatzberg_79-0" class="reference"><a href="#cite_note-Schatzberg-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> </p><p>The benzodiazepines <a href="/wiki/Diazepam" title="Diazepam">diazepam</a> and <a href="/wiki/Oxazepam" title="Oxazepam">oxazepam</a> have been found to produce fewer withdrawal reactions than alprazolam, <a href="/wiki/Temazepam" title="Temazepam">temazepam</a>, or <a href="/wiki/Lorazepam" title="Lorazepam">lorazepam</a>. Factors that determine the risk of <a href="/wiki/Substance_dependence" title="Substance dependence">psychological dependence</a> or <a href="/wiki/Physical_dependence" title="Physical dependence">physical dependence</a> and the severity of the <a href="/wiki/Benzodiazepine_withdrawal_symptoms" class="mw-redirect" title="Benzodiazepine withdrawal symptoms">benzodiazepine withdrawal symptoms</a> during dose reduction of alprazolam include: dosage used, length of use, frequency of dosing, personality characteristics of the individual, previous use of cross-dependent/cross-tolerant drugs (alcohol or other sedative-hypnotic drugs), current use of cross-dependent/-tolerant drugs, use of other short-acting, high-potency benzodiazepines,<sup id="cite_ref-wolf1991_80-0" class="reference"><a href="#cite_note-wolf1991-80"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-81" class="reference"><a href="#cite_note-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup> and method of discontinuation.<sup id="cite_ref-Ashton_manual_72-1" class="reference"><a href="#cite_note-Ashton_manual-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=12" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:6huo_GABAA-Rezeptorstruktur.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/6huo_GABAA-Rezeptorstruktur.png/220px-6huo_GABAA-Rezeptorstruktur.png" decoding="async" width="220" height="305" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/6huo_GABAA-Rezeptorstruktur.png/330px-6huo_GABAA-Rezeptorstruktur.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/aa/6huo_GABAA-Rezeptorstruktur.png/440px-6huo_GABAA-Rezeptorstruktur.png 2x" data-file-width="677" data-file-height="938" /></a><figcaption>Alprazolam binds at the α1β3γ2 <a href="/wiki/GABAA_receptor" title="GABAA receptor">GABAA receptor</a>. Alprazolam with red space-filling <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms. γ2 receptor subunit in mint green. The α1' subunit is hidden.<sup id="cite_ref-Masiulis_2019_82-0" class="reference"><a href="#cite_note-Masiulis_2019-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Alprazolam is a <a href="/wiki/GABAA_receptor_positive_allosteric_modulators" class="mw-redirect" title="GABAA receptor positive allosteric modulators">positive allosteric modulator of the gamma-aminobutyric acid (GABA) type A receptor</a>.<sup id="cite_ref-:0_68-1" class="reference"><a href="#cite_note-:0-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag may rely on an unreliable or less reliable medical source. (April 2024)">unreliable medical source?</span></a></i>]</sup> When it binds to the receptor, effects of GABA are enhanced leading to inhibition of neurons in the brain. This results in effects including reduced anxiety, muscle relaxant, antidepressant and anticonvulsant activity.<sup id="cite_ref-83" class="reference"><a href="#cite_note-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> The activity of alprazolam in the central nervous system is dose dependent.<sup id="cite_ref-Xanax_FDA_label_9-12" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Mechanism_of_action">Mechanism of action</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=13" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alprazolam is classed as a high-potency <a href="/wiki/Triazolobenzodiazepine" title="Triazolobenzodiazepine">triazolobenzodiazepine</a>:<sup id="cite_ref-84" class="reference"><a href="#cite_note-84"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-85" class="reference"><a href="#cite_note-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> a benzodiazepine with a <a href="/wiki/1,2,4-Triazole" title="1,2,4-Triazole">triazole ring</a> attached to its structure. As a benzodiazepine, alprazolam produces a variety of therapeutic and adverse effects by binding to the <a href="/wiki/GABA_A_receptor" class="mw-redirect" title="GABA A receptor">GABA<sub>A</sub></a> benzodiazepine receptor site and modulating its function; <a href="/wiki/GABA_receptor" title="GABA receptor">GABA receptors</a> are the most prolific inhibitory receptor within the brain. The GABA chemical and receptor system mediates inhibitory or calming effects of alprazolam on the nervous system. Binding of alprazolam to the GABA<sub>A</sub> receptor, a chloride ion channel, enhances the effects of GABA, a <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a>. When GABA binds the GABA<sub>A</sub> receptor the channel opens and chloride enters the cell which makes it more resistant to depolarisation. Therefore, alprazolam has a depressant effect on synaptic transmission to reduce anxiety.<sup id="cite_ref-86" class="reference"><a href="#cite_note-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-87" class="reference"><a href="#cite_note-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> </p><p>The GABA<sub>A</sub> receptor is made up of 5 subunits out of a possible 19, and GABA<sub>A</sub> receptors made up of different combinations of subunits have different properties, different locations within the brain, and, importantly, different activities with regard to benzodiazepines. Alprazolam and other triazolobenzodiazepines such as <a href="/wiki/Triazolam" title="Triazolam">triazolam</a> that have a triazole ring fused to their diazepine ring appear to have <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a> properties.<sup id="cite_ref-Barbee95_36-1" class="reference"><a href="#cite_note-Barbee95-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-88" class="reference"><a href="#cite_note-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> This is perhaps due to the similarities shared with <a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">tricyclic antidepressants</a>, as they have two benzene rings fused to a diazepine ring. Alprazolam causes a marked suppression of the <a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93adrenal_axis" title="Hypothalamic–pituitary–adrenal axis">hypothalamic–pituitary–adrenal axis</a>. The therapeutic properties of alprazolam are similar to other benzodiazepines and include <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a>, <a href="/wiki/Anticonvulsant" title="Anticonvulsant">anticonvulsant</a>, <a href="/wiki/Muscle_relaxant" title="Muscle relaxant">muscle relaxant</a>, <a href="/wiki/Hypnotic" title="Hypnotic">hypnotic</a><sup id="cite_ref-89" class="reference"><a href="#cite_note-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Amnesia" title="Amnesia">amnesic</a>; however, it is used mainly as an anxiolytic.<sup id="cite_ref-90" class="reference"><a href="#cite_note-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup> </p><p>Giving alprazolam, as compared to <a href="/wiki/Lorazepam" title="Lorazepam">lorazepam</a>, has been demonstrated to elicit a statistically significant increase in extracellular <a href="/wiki/Dopamine" title="Dopamine">dopamine</a> <a href="/wiki/Dopamine_receptor_D1" title="Dopamine receptor D1">D1</a> and <a href="/wiki/Dopamine_receptor_D2" title="Dopamine receptor D2">D2</a> concentrations in the <a href="/wiki/Striatum" title="Striatum">striatum</a>.<sup id="cite_ref-91" class="reference"><a href="#cite_note-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-92" class="reference"><a href="#cite_note-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=14" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Alprazolam_metabolism.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Alprazolam_metabolism.svg/220px-Alprazolam_metabolism.svg.png" decoding="async" width="220" height="179" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Alprazolam_metabolism.svg/330px-Alprazolam_metabolism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/Alprazolam_metabolism.svg/440px-Alprazolam_metabolism.svg.png 2x" data-file-width="313" data-file-height="254" /></a><figcaption>Alprazolam metabolized into 4-hydroxyalprazolam (top) and α-hydroxyalprazolam (bottom)</figcaption></figure> <p>Alprazolam is taken orally, and is absorbed well – 80% of alprazolam binds to <a href="/wiki/Blood_proteins" class="mw-redirect" title="Blood proteins">proteins in the serum</a> (the majority binding to <a href="/wiki/Albumin" title="Albumin">albumin</a>). The concentration of alprazolam peaks after one to two hours.<sup id="cite_ref-Xanax_FDA_label_9-13" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Alprazolam is metabolized in the liver, mostly by the <a href="/wiki/Cytochrome" title="Cytochrome">cytochrome</a> enzyme <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>. Two major metabolites are produced: 4-hydroxyalprazolam and α-hydroxyalprazolam, as well as an inactive <a href="/wiki/Benzophenone" title="Benzophenone">benzophenone</a>. The low concentrations and low potencies of 4-hydroxyalprazolam and α-hydroxyalprazolam indicate that they have little to no contribution to the effects of alprazolam.<sup id="cite_ref-Xanax_FDA_label_9-14" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The metabolites and some unmetabolized alprazolam are filtered out by the kidneys and are excreted in the urine.<sup id="cite_ref-Xanax_FDA_label_9-15" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=15" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Physical_properties">Physical properties</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=16" title="Edit section: Physical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alprazolam is a <a href="/wiki/Triazole" title="Triazole">triazole</a> and <a href="/wiki/Benzodiazepine" title="Benzodiazepine">benzodiazepine</a> derivative substituted with a <a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a> group at position 6, with a <a href="/wiki/Chlorine" title="Chlorine">chlorine</a> atom at position 8 and with a <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> group at position 1. It is an analogue of <a href="/wiki/Triazolam" title="Triazolam">triazolam</a>, the difference between them being the absence of a chlorine atom in the ortho position of the phenyl ring.<sup id="cite_ref-SED_93-0" class="reference"><a href="#cite_note-SED-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup> It is slightly soluble in <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, soluble in <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>, slightly soluble in <a href="/wiki/Acetone" title="Acetone">acetone</a> and insoluble in water.<sup id="cite_ref-merck_94-0" class="reference"><a href="#cite_note-merck-94"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup> It has a <a href="/wiki/Melting_point" title="Melting point">melting point</a> of 228–229.5 °C (442.4–445.1 °F; 501.1–502.6 K).<sup id="cite_ref-merck_94-1" class="reference"><a href="#cite_note-merck-94"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Patent3_95-0" class="reference"><a href="#cite_note-Patent3-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=17" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>For the synthesis of alprazolam the same method can be used as for <a href="/wiki/Triazolam" title="Triazolam">triazolam</a>, excepting that it starts from 2-amino-5-chlorobenzophenone.<sup id="cite_ref-Patent_96-0" class="reference"><a href="#cite_note-Patent-96"><span class="cite-bracket">[</span>96<span class="cite-bracket">]</span></a></sup> However, an alternative easier synthesis starting with 2,6-dichloro-4-phenylquinoline has been suggested, in which it reacts with <a href="/wiki/Hydrazine" title="Hydrazine">hydrazine</a> giving 6-chloro-2-hydrazino-4-phenylquinoline. Boiling the mixture with <a href="/wiki/Triethyl_orthoacetate" title="Triethyl orthoacetate">triethyl orthoacetate</a> results in cyclization with the formation of the <a href="/wiki/Triazole" title="Triazole">triazole</a> ring. The product undergoes oxidative degradation in the presence of <a href="/wiki/Periodate" title="Periodate">periodate</a> and <a href="/wiki/Ruthenium_dioxide" class="mw-redirect" title="Ruthenium dioxide">ruthenium dioxide</a> in <a href="/wiki/Acetone" title="Acetone">acetone</a> solution, giving 2-[4-(3'-methyl-1,2,4-triazolo)]-5-chlorobenzophenone. Oxy-methylation with <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> results in a product that is treated with phosphorus tribromide, when 2-[4-(3'-methyl-5'-bromomethyl-1,2,4-triazolo)]-5-chlorobenzophenone is obtained. By substituting the <a href="/wiki/Bromine" title="Bromine">bromine</a> atom with an amino group conferred by ammonia, it forms <a href="/wiki/Alprazolam_triazolobenzophenone" title="Alprazolam triazolobenzophenone">alprazolam triazolobenzophenone</a>, following which an intramolecular heterocyclization takes place to obtain alprazolam.<sup id="cite_ref-SED_93-1" class="reference"><a href="#cite_note-SED-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Synthesis_97-0" class="reference"><a href="#cite_note-Synthesis-97"><span class="cite-bracket">[</span>97<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Patent3_95-1" class="reference"><a href="#cite_note-Patent3-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Detection">Detection</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=18" title="Edit section: Detection"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Quantification of alprazolam in blood and plasma samples may be necessary to confirm a diagnosis of intoxication in hospitalized patients, or to provide evidence in the case of crimes e.g., impaired driving arrest, or to assist in a thorough forensic investigation, e.g., in a <a href="/wiki/Medical_jurisprudence" title="Medical jurisprudence">medicolegal</a> death investigation. Blood or plasma alprazolam concentrations are usually in a range of 10–100 μg/L in persons receiving the drug therapeutically, 100–300 μg/L in those arrested for impaired driving, and 300–2,000 μg/L in victims of acute overdosage. Most of the commercial <a href="/wiki/Immunoassays" class="mw-redirect" title="Immunoassays">immunoassays</a> used for the benzodiazepine class of drugs cross-react with alprazolam, but confirmation and quantitative determination are usually done by <a href="/wiki/Chromatographic" class="mw-redirect" title="Chromatographic">chromatographic</a> techniques.<sup id="cite_ref-98" class="reference"><a href="#cite_note-98"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Dosage_forms">Dosage forms</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=19" title="Edit section: Dosage forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alprazolam regular release and <a href="/wiki/Orally_disintegrating_tablet" title="Orally disintegrating tablet">orally disintegrating tablets</a> are available as 0.25 mg, 0.5 mg, 1 mg, and 2 mg tablets.<sup id="cite_ref-Xanax_FDA_label_9-16" class="reference"><a href="#cite_note-Xanax_FDA_label-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Extended-release tablets are available as 0.5 mg, 1 mg, 2 mg, and 3 mg tablets.<sup id="cite_ref-Xanax_XR_FDA_label_10-2" class="reference"><a href="#cite_note-Xanax_XR_FDA_label-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Liquid alprazolam is available in a 1 mg/mL oral concentrate.<sup id="cite_ref-99" class="reference"><a href="#cite_note-99"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Legal_status">Legal status</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=20" title="Edit section: Legal status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alprazolam has varied legal status depending on jurisdiction: </p> <ul><li>In the United States, alprazolam is a prescription drug and is assigned to <a href="/wiki/Controlled_Substances_Act#Schedule_IV_controlled_substances" title="Controlled Substances Act">Schedule IV</a> of the <a href="/wiki/Controlled_Substances_Act" title="Controlled Substances Act">Controlled Substances Act</a> by the <a href="/wiki/Drug_Enforcement_Administration" title="Drug Enforcement Administration">Drug Enforcement Administration</a> (DEA).<sup id="cite_ref-100" class="reference"><a href="#cite_note-100"><span class="cite-bracket">[</span>100<span class="cite-bracket">]</span></a></sup></li> <li>Under the UK drug misuse classification system, alprazolam is a <a href="/wiki/Drugs_controlled_by_the_UK_Misuse_of_Drugs_Act" class="mw-redirect" title="Drugs controlled by the UK Misuse of Drugs Act">Class C</a> drug.<sup id="cite_ref-misuse_of_drugs_legislation_8-1" class="reference"><a href="#cite_note-misuse_of_drugs_legislation-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-101" class="reference"><a href="#cite_note-101"><span class="cite-bracket">[</span>101<span class="cite-bracket">]</span></a></sup> In the UK, alprazolam is not available on the <a href="/wiki/National_Health_Service" title="National Health Service">National Health Service</a> (NHS) and can only be obtained on a private prescription.<sup id="cite_ref-BNF60_102-0" class="reference"><a href="#cite_note-BNF60-102"><span class="cite-bracket">[</span>102<span class="cite-bracket">]</span></a></sup></li> <li>In Ireland, alprazolam is a Schedule 4 medicine.<sup id="cite_ref-103" class="reference"><a href="#cite_note-103"><span class="cite-bracket">[</span>103<span class="cite-bracket">]</span></a></sup></li> <li>In Sweden, alprazolam is a prescription drug in List IV (Schedule 4) under the Narcotics Drugs Act (1968).<sup id="cite_ref-104" class="reference"><a href="#cite_note-104"><span class="cite-bracket">[</span>104<span class="cite-bracket">]</span></a></sup></li> <li>In the Netherlands, alprazolam is a List 2 substance of the <a href="/wiki/Opium_Law" title="Opium Law">Opium Law</a> and is available for prescription.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (April 2024)">citation needed</span></a></i>]</sup></li> <li>In Germany, alprazolam can be prescribed normally in doses up to 1 mg. Higher doses are scheduled as <a href="/wiki/Anlage_III" class="mw-redirect" title="Anlage III">Anlage III</a> drugs and require a <a href="/wiki/Special_prescription_form" title="Special prescription form">special prescription form</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (April 2024)">citation needed</span></a></i>]</sup></li> <li>In Australia, alprazolam, as of February 2014, is a Schedule 8 medication.<sup id="cite_ref-105" class="reference"><a href="#cite_note-105"><span class="cite-bracket">[</span>105<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-106" class="reference"><a href="#cite_note-106"><span class="cite-bracket">[</span>106<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-107" class="reference"><a href="#cite_note-107"><span class="cite-bracket">[</span>107<span class="cite-bracket">]</span></a></sup></li> <li>In the Philippines, alprazolam is legally classified as a "dangerous drug" under the <a href="/wiki/Comprehensive_Dangerous_Drugs_Act_of_2002" title="Comprehensive Dangerous Drugs Act of 2002">Comprehensive Dangerous Drugs Act of 2002</a>, along with other schedule drugs listed in the <a href="/wiki/Convention_on_Psychotropic_Substances" title="Convention on Psychotropic Substances">1971 Convention on Psychotropic Substances</a>.<sup id="cite_ref-108" class="reference"><a href="#cite_note-108"><span class="cite-bracket">[</span>108<span class="cite-bracket">]</span></a></sup> The importation of dangerous drugs including alprazolam, requires authorization from the <a href="/wiki/Philippine_Drug_Enforcement_Agency" title="Philippine Drug Enforcement Agency">Philippine Drug Enforcement Agency</a>.<sup id="cite_ref-109" class="reference"><a href="#cite_note-109"><span class="cite-bracket">[</span>109<span class="cite-bracket">]</span></a></sup></li></ul> <p>Internationally, alprazolam is included under the United Nations <a href="/wiki/Convention_on_Psychotropic_Substances" title="Convention on Psychotropic Substances">Convention on Psychotropic Substances</a> as Schedule IV.<sup id="cite_ref-110" class="reference"><a href="#cite_note-110"><span class="cite-bracket">[</span>110<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Availability">Availability</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=21" title="Edit section: Availability"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In December 2013, in anticipation of the rescheduling of alprazolam to Schedule 8 in Australia, Pfizer Australia announced they would be discontinuing the Xanax brand in Australia as it was no longer commercially viable.<sup id="cite_ref-111" class="reference"><a href="#cite_note-111"><span class="cite-bracket">[</span>111<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Recreational_use">Recreational use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=22" title="Edit section: Recreational use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Benzodiazepine_use_disorder" title="Benzodiazepine use disorder">Benzodiazepine use disorder</a></div> <p>There is a risk of misuse and dependence in both patients and <a href="/wiki/Recreational_drug_use" title="Recreational drug use">non-medical users</a> of alprazolam; alprazolam's high affinity binding, high potency, and rapid onset increase its abuse potential. The <a href="/wiki/Physical_dependence" title="Physical dependence">physical dependence</a> and <a href="/wiki/Drug_withdrawal" title="Drug withdrawal">withdrawal syndrome</a> of alprazolam also add to its <a href="/wiki/Addiction" title="Addiction">addictive nature</a>. In the small subgroup of individuals who escalate their doses there is usually a history of <a href="/wiki/Alcohol_abuse" title="Alcohol abuse">alcohol</a> or other <a href="/wiki/Substance_use_disorder" title="Substance use disorder">substance use disorders</a>.<sup id="cite_ref-Moy2012_25-2" class="reference"><a href="#cite_note-Moy2012-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>Despite this, most prescribed alprazolam users do not use their medication recreationally, and the long-term use of benzodiazepines does not generally correlate with the need for dose escalation.<sup id="cite_ref-112" class="reference"><a href="#cite_note-112"><span class="cite-bracket">[</span>112<span class="cite-bracket">]</span></a></sup> However, based on US findings from the Treatment Episode Data Set (TEDS), an annual compilation of patient characteristics in substance abuse treatment facilities in the United States, admissions due to "primary tranquilizer" (including, but not limited to, benzodiazepine-type) drug use increased 79% from 1992 to 2002, suggesting that misuse of benzodiazepines may be on the rise.<sup id="cite_ref-113" class="reference"><a href="#cite_note-113"><span class="cite-bracket">[</span>113<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Centers_for_Disease_Control_and_Prevention" title="Centers for Disease Control and Prevention">Centers for Disease Control and Prevention</a> (CDC) reported an 89 percent increase in emergency room visits nationwide related to nonmedical benzodiazepine use between 2004 and 2008.<sup id="cite_ref-114" class="reference"><a href="#cite_note-114"><span class="cite-bracket">[</span>114<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-115" class="reference"><a href="#cite_note-115"><span class="cite-bracket">[</span>115<span class="cite-bracket">]</span></a></sup> </p><p>Alprazolam is one of the most commonly prescribed and misused benzodiazepines in the United States.<sup id="cite_ref-APPT_116-0" class="reference"><a href="#cite_note-APPT-116"><span class="cite-bracket">[</span>116<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-dawn2neodredv_117-0" class="reference"><a href="#cite_note-dawn2neodredv-117"><span class="cite-bracket">[</span>117<span class="cite-bracket">]</span></a></sup> A large-scale nationwide <a href="/wiki/Federal_government_of_the_United_States" title="Federal government of the United States">U.S. government</a> study conducted by the <a href="/wiki/Substance_Abuse_and_Mental_Health_Services_Administration" title="Substance Abuse and Mental Health Services Administration">Substance Abuse and Mental Health Services Administration</a> concluded that, in the US, benzodiazepines are recreationally the most frequently used pharmaceuticals due to their widespread availability, accounting for 35% of all drug-related visits to hospital <a href="/wiki/Emergency_department" title="Emergency department">emergency</a> and <a href="/wiki/Urgent_care_facilities" class="mw-redirect" title="Urgent care facilities">urgent care facilities</a>. Men and women are equally likely to use benzodiazepines recreationally. The report found that alprazolam is the most common benzodiazepine for recreational use, followed by <a href="/wiki/Clonazepam" title="Clonazepam">clonazepam</a>, <a href="/wiki/Lorazepam" title="Lorazepam">lorazepam</a>, and <a href="/wiki/Diazepam" title="Diazepam">diazepam</a>. The number of emergency department visits due to benzodiazepines increased by 36% between 2004 and 2006.<sup id="cite_ref-dawn2neodredv_117-1" class="reference"><a href="#cite_note-dawn2neodredv-117"><span class="cite-bracket">[</span>117<span class="cite-bracket">]</span></a></sup> </p> <style data-mw-deduplicate="TemplateStyles:r1244412712">.mw-parser-output .templatequote{overflow:hidden;margin:1em 0;padding:0 32px}.mw-parser-output .templatequotecite{line-height:1.5em;text-align:left;margin-top:0}@media(min-width:500px){.mw-parser-output .templatequotecite{padding-left:1.6em}}</style><blockquote class="templatequote"><p>Regarding the significant increases detected, it is worthwhile to consider that the number of pharmaceuticals dispensed for legitimate therapeutic uses may be increasing over time, and DAWN estimates are not adjusted to take such increases into account. Nor do DAWN estimates take into account the increases in the population or in ED use between 2004 and 2006.<sup id="cite_ref-dawn2neodredv_117-2" class="reference"><a href="#cite_note-dawn2neodredv-117"><span class="cite-bracket">[</span>117<span class="cite-bracket">]</span></a></sup></p></blockquote> <p>Those at a particularly high risk for misuse and dependence are people with a history of alcoholism or drug abuse and/or dependence<sup id="cite_ref-118" class="reference"><a href="#cite_note-118"><span class="cite-bracket">[</span>118<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-119" class="reference"><a href="#cite_note-119"><span class="cite-bracket">[</span>119<span class="cite-bracket">]</span></a></sup> and people with <a href="/wiki/Borderline_personality_disorder" title="Borderline personality disorder">borderline personality disorder</a>.<sup id="cite_ref-120" class="reference"><a href="#cite_note-120"><span class="cite-bracket">[</span>120<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Poly-drug_use" class="mw-redirect" title="Poly-drug use">poly-drug use</a> of powerful depressant drugs poses the highest level of health concerns due to a significant increase in the likelihood of experiencing an <a href="/wiki/Drug_overdose" title="Drug overdose">overdose</a>, which may cause fatal <a href="/wiki/Respiratory_depression" class="mw-redirect" title="Respiratory depression">respiratory depression</a>.<sup id="cite_ref-121" class="reference"><a href="#cite_note-121"><span class="cite-bracket">[</span>121<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-122" class="reference"><a href="#cite_note-122"><span class="cite-bracket">[</span>122<span class="cite-bracket">]</span></a></sup> </p><p>A 1990 study found that diazepam has a higher misuse potential relative to many other benzodiazepines and that some data suggest that alprazolam and lorazepam resemble diazepam in this respect.<sup id="cite_ref-griffiths1990_123-0" class="reference"><a href="#cite_note-griffiths1990-123"><span class="cite-bracket">[</span>123<span class="cite-bracket">]</span></a></sup> </p><p>Anecdotally, injection of alprazolam has been reported, causing dangerous damage to blood vessels, closure of blood vessels (<a href="/wiki/Embolization" title="Embolization">embolization</a>), and decay of muscle tissue (<a href="/wiki/Rhabdomyolysis" title="Rhabdomyolysis">rhabdomyolysis</a>).<sup id="cite_ref-124" class="reference"><a href="#cite_note-124"><span class="cite-bracket">[</span>124<span class="cite-bracket">]</span></a></sup> Alprazolam is not very soluble in water; when crushed in water, it does not fully <a href="/wiki/Solubility" title="Solubility">dissolve</a> (40 μg/ml of <a href="/wiki/Properties_of_water" title="Properties of water">H<sub>2</sub>O</a> at pH 7).<sup id="cite_ref-DB00404_Alprazolam_125-0" class="reference"><a href="#cite_note-DB00404_Alprazolam-125"><span class="cite-bracket">[</span>125<span class="cite-bracket">]</span></a></sup> There are also reports of alprazolam being <a href="/wiki/Insufflation_(medicine)" title="Insufflation (medicine)">snorted</a>.<sup id="cite_ref-126" class="reference"><a href="#cite_note-126"><span class="cite-bracket">[</span>126<span class="cite-bracket">]</span></a></sup> Due to the low weight of a dose, alprazolam, in one case, was distributed on <a href="/wiki/Blotting_paper#Drugs" title="Blotting paper">blotter paper</a> in a manner similar to LSD.<sup id="cite_ref-127" class="reference"><a href="#cite_note-127"><span class="cite-bracket">[</span>127<span class="cite-bracket">]</span></a></sup> </p><p>Misuse of alprazolam and other benzodiazepines has been shown to cause <a href="/wiki/Cognitive_impairment" title="Cognitive impairment">cognitive impairment</a>.<sup id="cite_ref-The_Effect_of_Chronic_Alprazolam_In_128-0" class="reference"><a href="#cite_note-The_Effect_of_Chronic_Alprazolam_In-128"><span class="cite-bracket">[</span>128<span class="cite-bracket">]</span></a></sup> Alprazolam has typically caused <a href="/wiki/Anterograde_amnesia" title="Anterograde amnesia">anterograde amnesia</a> effects (inability to recall new events), but a study conducted on mice by the Department of Pharmaceutical Sciences and Drug Research at <a href="/wiki/Punjabi_University" title="Punjabi University">Punjabi University</a> has also determined that alprazolam can produce retrograde amnesic effects (inability to remember events occurring before amnesia). One 2016 study found that "chronic administration of alprazolam affects memory but attentive and psychomotor performance remained unaffected".<sup id="cite_ref-129" class="reference"><a href="#cite_note-129"><span class="cite-bracket">[</span>129<span class="cite-bracket">]</span></a></sup> </p><p>A 2016 randomized controlled trial stated that "overall, long-term benzodiazepine users may not be in their full cognitive state upon withdrawal".<sup id="cite_ref-The_Effect_of_Chronic_Alprazolam_In_128-1" class="reference"><a href="#cite_note-The_Effect_of_Chronic_Alprazolam_In-128"><span class="cite-bracket">[</span>128<span class="cite-bracket">]</span></a></sup> Similarly, a 2017 meta-analysis concluded that "a range of neuropsychological functions are impaired as a result of long-term benzodiazepine use, and that these are likely to persist even following withdrawal".<sup id="cite_ref-130" class="reference"><a href="#cite_note-130"><span class="cite-bracket">[</span>130<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Slang_terms">Slang terms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=23" title="Edit section: Slang terms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Slang terms for alprazolam vary by geographic location. Some of the more common terms are modified versions of the trade name "Xanax", such as Xannies (or Xanies) and the phonetic equivalent of Zannies;<sup id="cite_ref-131" class="reference"><a href="#cite_note-131"><span class="cite-bracket">[</span>131<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-132" class="reference"><a href="#cite_note-132"><span class="cite-bracket">[</span>132<span class="cite-bracket">]</span></a></sup> references to their drug classes, such as benzos or downers; or remark upon their shape or color (most commonly a straight, perforated tablet or an oval-shaped pill): bars, ladders, Xanbars, Xans, Z-bars, handle bars, beans, footballs, planks, poles, sticks, blues, or blue footballs.<sup id="cite_ref-133" class="reference"><a href="#cite_note-133"><span class="cite-bracket">[</span>133<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-134" class="reference"><a href="#cite_note-134"><span class="cite-bracket">[</span>134<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-135" class="reference"><a href="#cite_note-135"><span class="cite-bracket">[</span>135<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MPR_Xanax_Slang_136-0" class="reference"><a href="#cite_note-MPR_Xanax_Slang-136"><span class="cite-bracket">[</span>136<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="In_popular_culture">In popular culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=24" title="Edit section: In popular culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><i>Take Your Pills: Xanax</i>, a 2022 <a href="/wiki/Netflix" title="Netflix">Netflix</a> documentary, provides an overview of the drug's history and usage.<sup id="cite_ref-137" class="reference"><a href="#cite_note-137"><span class="cite-bracket">[</span>137<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-138" class="reference"><a href="#cite_note-138"><span class="cite-bracket">[</span>138<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=25" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Drugs.com_pregnancy-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Drugs.com_pregnancy_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output 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.mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" 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Retrieved <span class="nowrap">20 November</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=GOV.UK&rft.atitle=List+of+most+commonly+encountered+drugs+currently+controlled+under+the+misuse+of+drugs+legislation&rft.date=2016-10-20&rft_id=https%3A%2F%2Fwww.gov.uk%2Fgovernment%2Fpublications%2Fcontrolled-drugs-list--2%2Flist-of-most-commonly-encountered-drugs-currently-controlled-under-the-misuse-of-drugs-legislation&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-Xanax_FDA_label-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-Xanax_FDA_label_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-13"><sup><i><b>n</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-14"><sup><i><b>o</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-15"><sup><i><b>p</b></i></sup></a> <a href="#cite_ref-Xanax_FDA_label_9-16"><sup><i><b>q</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=388e249d-b9b6-44c3-9f8f-880eced0239f">"Xanax- alprazolam tablet"</a>. <i>DailyMed</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210117223138/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=388e249d-b9b6-44c3-9f8f-880eced0239f">Archived</a> from the original on 17 January 2021<span class="reference-accessdate">. Retrieved <span class="nowrap">19 February</span> 2021</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Xanax-+alprazolam+tablet&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3D388e249d-b9b6-44c3-9f8f-880eced0239f&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-Xanax_XR_FDA_label-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-Xanax_XR_FDA_label_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Xanax_XR_FDA_label_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Xanax_XR_FDA_label_10-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aa58fff3-c297-49be-838b-599c32ad9835">"Xanax XR- alprazolam tablet, extended release"</a>. <i>DailyMed</i>. 12 March 2021. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210417013226/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aa58fff3-c297-49be-838b-599c32ad9835">Archived</a> from the original on 17 April 2021<span class="reference-accessdate">. Retrieved <span class="nowrap">2 June</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Xanax+XR-+alprazolam+tablet%2C+extended+release&rft.date=2021-03-12&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3Daa58fff3-c297-49be-838b-599c32ad9835&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c8990714-c2f5-4b0c-9f1c-91d77156d962">"Xanax XR- alprazolam tablet, extended release"</a>. <i>DailyMed</i>. 12 April 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">17 June</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Xanax+XR-+alprazolam+tablet%2C+extended+release&rft.date=2023-04-12&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3Dc8990714-c2f5-4b0c-9f1c-91d77156d962&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.ema.europa.eu/en/documents/psusa/alprazolam-list-nationally-authorised-medicinal-products-psusa00000109202203_en.pdf">"List of nationally authorised medicinal products"</a> <span class="cs1-format">(PDF)</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=List+of+nationally+authorised+medicinal+products&rft_id=https%3A%2F%2Fwww.ema.europa.eu%2Fen%2Fdocuments%2Fpsusa%2Falprazolam-list-nationally-authorised-medicinal-products-psusa00000109202203_en.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-Lill2016-13"><span class="mw-cite-backlink">^ <a href="#cite_ref-Lill2016_13-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Lill2016_13-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLilleySnyderCollins2016" class="citation book cs1">Lilley LL, Snyder JS, Collins SR (2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=dNgoDwAAQBAJ&pg=PA329"><i>Pharmacology for Canadian Health Care Practice</i></a>. Elsevier Health Sciences. p. 329. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781771720663" title="Special:BookSources/9781771720663"><bdi>9781771720663</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220510111235/https://books.google.com/books?id=dNgoDwAAQBAJ&pg=PA329">Archived</a> from the original on 10 May 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">13 September</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmacology+for+Canadian+Health+Care+Practice&rft.pages=329&rft.pub=Elsevier+Health+Sciences&rft.date=2016&rft.isbn=9781771720663&rft.aulast=Lilley&rft.aufirst=LL&rft.au=Snyder%2C+JS&rft.au=Collins%2C+SR&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DdNgoDwAAQBAJ%26pg%3DPA329&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-AHFS2018-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-AHFS2018_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-AHFS2018_14-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-AHFS2018_14-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-AHFS2018_14-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-AHFS2018_14-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-AHFS2018_14-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-AHFS2018_14-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-AHFS2018_14-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-AHFS2018_14-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-AHFS2018_14-9"><sup><i><b>j</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAmerican_Society_of_Health-System_Pharmacists2017" class="citation web cs1">American Society of Health-System Pharmacists (13 November 2017). <a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/alprazolam.html">"Alprazolam Monograph for Professionals"</a>. <i>Drugs.com</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20101207030717/https://www.drugs.com/monograph/alprazolam.html">Archived</a> from the original on 7 December 2010<span class="reference-accessdate">. Retrieved <span class="nowrap">25 October</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Drugs.com&rft.atitle=Alprazolam+Monograph+for+Professionals&rft.date=2017-11-13&rft.au=American+Society+of+Health-System+Pharmacists&rft_id=https%3A%2F%2Fwww.drugs.com%2Fmonograph%2Falprazolam.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGoldberg2009" class="citation book cs1">Goldberg R (2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=EZlsCgAAQBAJ&pg=PA195"><i>Drugs Across the Spectrum</i></a>. Cengage Learning. p. 195. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781111782009" title="Special:BookSources/9781111782009"><bdi>9781111782009</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200604135538/https://books.google.com/books?id=EZlsCgAAQBAJ&pg=PA195%2F">Archived</a> from the original on 4 June 2020<span class="reference-accessdate">. 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Philadelphia, PA: Wolters Kluwer Health/ Lippincott Williams & Wilkins. p. 535. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60547-565-3" title="Special:BookSources/978-1-60547-565-3"><bdi>978-1-60547-565-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200717220547/https://books.google.com/books?id=_ePK9wwcQUMC&pg=PA535">Archived</a> from the original on 17 July 2020<span class="reference-accessdate">. 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href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWork_Group_on_Panic_Disorder2009" class="citation book cs1">Work Group on Panic Disorder (January 2009). <a rel="nofollow" class="external text" href="https://psychiatryonline.org/pb/assets/raw/sitewide/practice_guidelines/guidelines/panicdisorder.pdf"><i>APA Practice Guideline for the Treatment of Patients With Panic Disorder</i></a> <span class="cs1-format">(PDF)</span>. Vol. 1 (2nd ed.). <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1176%2Fappi.books.9780890423905.154688">10.1176/appi.books.9780890423905.154688</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-89042-385-1" title="Special:BookSources/978-0-89042-385-1"><bdi>978-0-89042-385-1</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190607004900/http://psychiatryonline.org/pb/assets/raw/sitewide/practice_guidelines/guidelines/panicdisorder.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 7 June 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">25 October</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=APA+Practice+Guideline+for+the+Treatment+of+Patients+With+Panic+Disorder&rft.edition=2nd&rft.date=2009-01&rft_id=info%3Adoi%2F10.1176%2Fappi.books.9780890423905.154688&rft.isbn=978-0-89042-385-1&rft.au=Work+Group+on+Panic+Disorder&rft_id=https%3A%2F%2Fpsychiatryonline.org%2Fpb%2Fassets%2Fraw%2Fsitewide%2Fpractice_guidelines%2Fguidelines%2Fpanicdisorder.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-DEAbrief-67"><span class="mw-cite-backlink"><b><a href="#cite_ref-DEAbrief_67-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20090312084246/http://www.justice.gov/dea/concern/b.html">"DEA Brief Benzodiazepines"</a>. Archived from <a rel="nofollow" class="external text" href="https://www.justice.gov/dea/concern/b.html">the original</a> on 12 March 2009<span class="reference-accessdate">. Retrieved <span class="nowrap">1 October</span> 2011</span>. <q>Given the millions of prescriptions written for benzodiazepines (about 100 million in 1999), relatively few individuals increase their dose on their own initiative or engage in drug-seeking behavior.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=DEA+Brief+Benzodiazepines&rft_id=https%3A%2F%2Fwww.justice.gov%2Fdea%2Fconcern%2Fb.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-:0-68"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_68-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_68-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://thedrugclassroom.com/video/alprazolam/">"Alprazolam"</a>. <i>The Drug Classroom</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190122094609/https://thedrugclassroom.com/video/alprazolam/">Archived</a> from the original on 22 January 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">21 January</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=The+Drug+Classroom&rft.atitle=Alprazolam&rft_id=https%3A%2F%2Fthedrugclassroom.com%2Fvideo%2Falprazolam%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-:1-69"><span class="mw-cite-backlink">^ <a href="#cite_ref-:1_69-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:1_69-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStahl2000" class="citation book cs1">Stahl SM (June 2000). <a rel="nofollow" class="external text" href="https://www.worldcat.org/oclc/43051626"><i>Essential psychopharmacology : neuroscientific basis and practical application</i></a> (2nd ed.). 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"Dopamine receptors in the striatum of rats exposed to repeated restraint stress and alprazolam treatment". <i>European Journal of Pharmacology</i>. <b>344</b> (2–3): 143–7. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0014-2999%2897%2901608-7">10.1016/s0014-2999(97)01608-7</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/9600648">9600648</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Pharmacology&rft.atitle=Dopamine+receptors+in+the+striatum+of+rats+exposed+to+repeated+restraint+stress+and+alprazolam+treatment&rft.volume=344&rft.issue=2%E2%80%933&rft.pages=143-7&rft.date=1998-03&rft_id=info%3Adoi%2F10.1016%2Fs0014-2999%2897%2901608-7&rft_id=info%3Apmid%2F9600648&rft.aulast=Giardino&rft.aufirst=L&rft.au=Zanni%2C+M&rft.au=Pozza%2C+M&rft.au=Bettelli%2C+C&rft.au=Covelli%2C+V&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-SED-93"><span class="mw-cite-backlink">^ <a href="#cite_ref-SED_93-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-SED_93-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRubenHruby2006" class="citation book cs1">Ruben V, Hruby V (2006). <i>Synthesis of Essential Drugs</i> (1 ed.). <a href="/wiki/Elsevier" title="Elsevier">Elsevier</a> Science. pp. 76–77. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780444521668" title="Special:BookSources/9780444521668"><bdi>9780444521668</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Synthesis+of+Essential+Drugs&rft.pages=76-77&rft.edition=1&rft.pub=Elsevier+Science&rft.date=2006&rft.isbn=9780444521668&rft.aulast=Ruben&rft.aufirst=V&rft.au=Hruby%2C+V&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-merck-94"><span class="mw-cite-backlink">^ <a href="#cite_ref-merck_94-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-merck_94-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFO'NeilSmithHeckelmanBudavari2013" class="citation book cs1">O'Neil MJ, Smith A, Heckelman PE, Budavari S (2013). <i>The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals</i> (Fifteenth ed.). 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Archived from <a rel="nofollow" class="external text" href="https://patents.google.com/patent/US3709898A/en%3Foq%3D3.709.898%2B">the original</a> on 21 February 2020<span class="reference-accessdate">. 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Xulon Press. p. 213. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781594675041" title="Special:BookSources/9781594675041"><bdi>9781594675041</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210426222507/https://books.google.com/books?id=uUb_lkQQ24kC&pg=PA213">Archived</a> from the original on 26 April 2021<span class="reference-accessdate">. Retrieved <span class="nowrap">18 July</span> 2017</span>. <q>Some people sell Xanax on the street for ten or fifteen dollars a pill. 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Archived from <a rel="nofollow" class="external text" href="http://www.alprazolamaddictionhelp.com/street-names-for-alprazolam">the original</a> on 22 February 2014<span class="reference-accessdate">. Retrieved <span class="nowrap">14 February</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Alprazolamaddictionhelp.com&rft.atitle=Street+Names+for+Alprazolam&rft_id=http%3A%2F%2Fwww.alprazolamaddictionhelp.com%2Fstreet-names-for-alprazolam&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-135"><span class="mw-cite-backlink"><b><a href="#cite_ref-135">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFDA2017" class="citation web cs1">FDA (2017). <a rel="nofollow" class="external text" href="https://www.fda.gov/Drugs/DrugSafety/ucm518473.htm">"Both opioids and benzodiazepines depress the central nervous system (CNS). FDA Drug Safety Communication: FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines; requires its strongest warning"</a>. <i>U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA)</i>. ("Additional Information for Patients > bullet 5"). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20171101170452/https://www.fda.gov/Drugs/DrugSafety/ucm518473.htm">Archived</a> from the original on 1 November 2017<span class="reference-accessdate">. Retrieved <span class="nowrap">15 October</span> 2017</span>. <q>Do not take opioid pain medicines with benzodiazepines or other medicines that depress the CNS without discussing it with your health Do not take opioid pain medicines with benzodiazepines or other medicines that depress the CNS without discussing it with your health care professional. Do not take opioid cough medicines with benzodiazepines or other medicines that depress the CNS professional. Do not take opioid cough medicines with benzodiazepines or other medicines that depress the CNS</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=U.S.+Food+and+Drug+Administration+%28FDA%29&rft.atitle=Both+opioids+and+benzodiazepines+depress+the+central+nervous+system+%28CNS%29.+FDA+Drug+Safety+Communication%3A+FDA+warns+about+serious+risks+and+death+when+combining+opioid+pain+or+cough+medicines+with+benzodiazepines%3B+requires+its+strongest+warning&rft.date=2017&rft.au=FDA&rft_id=https%3A%2F%2Fwww.fda.gov%2FDrugs%2FDrugSafety%2Fucm518473.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-MPR_Xanax_Slang-136"><span class="mw-cite-backlink"><b><a href="#cite_ref-MPR_Xanax_Slang_136-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.empr.com/home/drug-slang-code-words/xanax-alprazolam-drug-slang-code-words/">"Xanax (Alprazolam) Drug Slang/Code Words"</a>. <i>MPR</i>. 2 August 2017. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20191214023324/https://www.empr.com/home/drug-slang-code-words/xanax-alprazolam-drug-slang-code-words/">Archived</a> from the original on 14 December 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">17 March</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=MPR&rft.atitle=Xanax+%28Alprazolam%29+Drug+Slang%2FCode+Words&rft.date=2017-08-02&rft_id=https%3A%2F%2Fwww.empr.com%2Fhome%2Fdrug-slang-code-words%2Fxanax-alprazolam-drug-slang-code-words%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-137"><span class="mw-cite-backlink"><b><a href="#cite_ref-137">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCarroll2022" class="citation web cs1">Carroll L (8 December 2022). <a rel="nofollow" class="external text" href="https://www.today.com/health/mind-body/take-your-pills-xanax-netflix-rcna60645">"New Netflix documentary calls out Xanax overuse: What doctors want you to know"</a>. <i>Today</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221212182607/https://www.today.com/health/mind-body/take-your-pills-xanax-netflix-rcna60645">Archived</a> from the original on 12 December 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">12 December</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Today&rft.atitle=New+Netflix+documentary+calls+out+Xanax+overuse%3A+What+doctors+want+you+to+know&rft.date=2022-12-08&rft.aulast=Carroll&rft.aufirst=L&rft_id=https%3A%2F%2Fwww.today.com%2Fhealth%2Fmind-body%2Ftake-your-pills-xanax-netflix-rcna60645&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> <li id="cite_note-138"><span class="mw-cite-backlink"><b><a href="#cite_ref-138">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVillarreal2023" class="citation web cs1">Villarreal R (20 September 2023). <a rel="nofollow" class="external text" href="https://www.netflix.com/tudum/articles/take-your-pills-xanax-release-date-trailer">"Everything You Need to Know About 'Take Your Pills: Xanax'<span class="cs1-kern-right"></span>"</a>. <i>Netflix Tudum</i><span class="reference-accessdate">. Retrieved <span class="nowrap">17 June</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Netflix+Tudum&rft.atitle=Everything+You+Need+to+Know+About+%27Take+Your+Pills%3A+Xanax%27&rft.date=2023-09-20&rft.aulast=Villarreal&rft.aufirst=Ryan&rft_id=https%3A%2F%2Fwww.netflix.com%2Ftudum%2Farticles%2Ftake-your-pills-xanax-release-date-trailer&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlprazolam" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alprazolam&action=edit&section=26" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid 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4em"><a href="/wiki/Anxiolytic" title="Anxiolytic">Anxiolytics</a> (<a href="/wiki/ATC_code_N05#N05B" title="ATC code N05">N05B</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1A_receptor" title="5-HT1A receptor"><abbr title="5-HT1A receptor">5-HT<sub>1A</sub>R</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 5-HT1A receptor</span> <a href="/wiki/Agonist" title="Agonist">agonists</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/Buspirone" title="Buspirone">Buspirone</a></li> <li><a href="/wiki/Gepirone" title="Gepirone">Gepirone</a></li> <li><a href="/wiki/Tandospirone" title="Tandospirone">Tandospirone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/GABAA_receptor" title="GABAA receptor"><abbr title="GABAA receptor">GABA<sub>A</sub>R</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 GABAA receptor</span> <a href="/wiki/Positive_allosteric_modulators" class="mw-redirect" title="Positive allosteric modulators"><abbr title="positive allosteric modulators">PAMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip positive allosteric modulators</span></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a>:</i> <a href="/wiki/Adinazolam" title="Adinazolam">Adinazolam</a></li> <li><a class="mw-selflink selflink">Alprazolam</a></li> <li><a href="/wiki/Bromazepam" title="Bromazepam">Bromazepam</a></li> <li><a href="/wiki/Camazepam" title="Camazepam">Camazepam</a></li> <li><a href="/wiki/Chlordiazepoxide" title="Chlordiazepoxide">Chlordiazepoxide</a></li> <li><a href="/wiki/Clobazam" title="Clobazam">Clobazam</a></li> <li><a href="/wiki/Clonazepam" title="Clonazepam">Clonazepam</a></li> <li><a href="/wiki/Clorazepate" title="Clorazepate">Clorazepate</a></li> <li><a href="/wiki/Clotiazepam" title="Clotiazepam">Clotiazepam</a></li> <li><a href="/wiki/Cloxazolam" title="Cloxazolam">Cloxazolam</a></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a><sup>#</sup></li> <li><a href="/wiki/Ethyl_loflazepate" title="Ethyl loflazepate">Ethyl loflazepate</a></li> <li><a href="/wiki/Etizolam" title="Etizolam">Etizolam</a></li> <li><a href="/wiki/Fludiazepam" title="Fludiazepam">Fludiazepam</a></li> <li><a href="/wiki/Halazepam" title="Halazepam">Halazepam</a></li> <li><a href="/wiki/Ketazolam" title="Ketazolam">Ketazolam</a></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a><sup>#</sup></li> <li><a href="/wiki/Medazepam" title="Medazepam">Medazepam</a></li> <li><a href="/wiki/Nordazepam" title="Nordazepam">Nordazepam</a></li> <li><a href="/wiki/Oxazepam" title="Oxazepam">Oxazepam</a></li> <li><a href="/wiki/Pinazepam" title="Pinazepam">Pinazepam</a></li> <li><a href="/wiki/Prazepam" title="Prazepam">Prazepam</a>; <i>Others:</i> <a href="/wiki/Alpidem" title="Alpidem">Alpidem</a><sup>‡</sup></li> <li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a> (e.g., <a href="/wiki/Phenobarbital" title="Phenobarbital">phenobarbital</a>)</li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a> (e.g., <a href="/wiki/Meprobamate" title="Meprobamate">meprobamate</a>)</li> <li><a href="/wiki/Carisoprodol" title="Carisoprodol">Carisoprodol</a></li> <li><a href="/wiki/Chlormezanone" title="Chlormezanone">Chlormezanone</a><sup>‡</sup></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/Etifoxine" title="Etifoxine">Etifoxine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Hypnotic" title="Hypnotic">Hypnotics</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/Zopiclone" title="Zopiclone">Zopiclone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Gabapentinoid" title="Gabapentinoid">Gabapentinoids</a><br /><span style="font-size:85%;">(<a href="/wiki/Voltage-dependent_calcium_channel#.CE.B12.CE.B4_Subunit" class="mw-redirect" title="Voltage-dependent calcium channel"><abbr title="alpha2delta subunit">α<sub>2</sub>δ</abbr> <abbr title="voltage-dependent calcium channel">VDCC</abbr></a> <a href="/wiki/Channel_blocker" title="Channel blocker">blockers</a>)</span></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/Gabapentin" title="Gabapentin">Gabapentin</a></li> <li><a href="/wiki/Gabapentin_enacarbil" title="Gabapentin enacarbil">Gabapentin enacarbil</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a href="/wiki/Pregabalin" title="Pregabalin">Pregabalin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antidepressant" title="Antidepressant">Antidepressants</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/Selective_serotonin_reuptake_inhibitors" class="mw-redirect" title="Selective serotonin reuptake inhibitors"><abbr title="Selective serotonin reuptake inhibitors">SSRIs</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 Selective serotonin reuptake inhibitors</span> (e.g., <a href="/wiki/Escitalopram" title="Escitalopram">escitalopram</a>)</li> <li><a href="/wiki/Serotonin-norepinephrine_reuptake_inhibitors" class="mw-redirect" title="Serotonin-norepinephrine reuptake inhibitors"><abbr title="Serotonin-norepinephrine reuptake inhibitors">SNRIs</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-norepinephrine reuptake inhibitors</span> (e.g., <a href="/wiki/Duloxetine" title="Duloxetine">duloxetine</a>)</li> <li><a href="/wiki/Serotonin_antagonist_and_reuptake_inhibitors" class="mw-redirect" title="Serotonin antagonist and reuptake inhibitors"><abbr title="Serotonin antagonist and reuptake inhibitors">SARIs</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 antagonist and reuptake inhibitors</span> (e.g., <a href="/wiki/Trazodone" title="Trazodone">trazodone</a>)</li> <li><a href="/wiki/Tricyclic_antidepressants" class="mw-redirect" title="Tricyclic antidepressants"><abbr title="Tricyclic antidepressants">TCAs</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 Tricyclic antidepressants</span> (e.g., <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a><sup>#</sup>)</li> <li><a href="/wiki/Tetracyclic_antidepressants" class="mw-redirect" title="Tetracyclic antidepressants"><abbr title="Tetracyclic antidepressants">TeCAs</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 Tetracyclic antidepressants</span> (e.g., <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Monoamine_oxidase_inhibitors" class="mw-redirect" title="Monoamine oxidase inhibitors"><abbr title="Monoamine oxidase inhibitors">MAOIs</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 Monoamine oxidase inhibitors</span> (e.g., <a href="/wiki/Phenelzine" title="Phenelzine">phenelzine</a>); <i>Others:</i> <a href="/wiki/Agomelatine" title="Agomelatine">Agomelatine</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Tianeptine" title="Tianeptine">Tianeptine</a></li> <li><a href="/wiki/Vilazodone" title="Vilazodone">Vilazodone</a></li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antipsychotic" title="Antipsychotic">Antipsychotics</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/Quetiapine" title="Quetiapine">Quetiapine</a></li> <li><a href="/wiki/Flupentixol" title="Flupentixol">Flupentixol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Sympatholytic" title="Sympatholytic">Sympatholytics</a><br /><span style="font-size:85%;">(<a href="/wiki/Antiadrenergic" class="mw-redirect" title="Antiadrenergic">Antiadrenergics</a>)</span></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/Alpha-1_blocker" title="Alpha-1 blocker">Alpha-1 blockers</a> (e.g., <a href="/wiki/Prazosin" title="Prazosin">prazosin</a>)</li> <li><a href="/wiki/Alpha-2_agonist" class="mw-redirect" title="Alpha-2 agonist">Alpha-2 agonists</a> (e.g., <a href="/wiki/Clonidine" title="Clonidine">clonidine</a>, <a href="/wiki/Dexmedetomidine" title="Dexmedetomidine">dexmedetomidine</a>, <a href="/wiki/Guanfacine" title="Guanfacine">guanfacine</a>)</li> <li><a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> (e.g., <a href="/wiki/Propranolol" title="Propranolol">propranolol</a>)</li></ul> </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><a href="/wiki/Benzoctamine" title="Benzoctamine">Benzoctamine</a></li> <li><a href="/wiki/Cycloserine" title="Cycloserine">Cycloserine</a></li> <li><a href="/wiki/Fabomotizole" title="Fabomotizole">Fabomotizole</a></li> <li><a href="/wiki/Hydroxyzine" title="Hydroxyzine">Hydroxyzine</a></li> <li><a href="/wiki/Lorpiprazole" title="Lorpiprazole">Lorpiprazole</a></li> <li><a href="/wiki/Mebicar" class="mw-redirect" title="Mebicar">Mebicar</a></li> <li><a href="/wiki/Mepiprazole" title="Mepiprazole">Mepiprazole</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/Opipramol" title="Opipramol">Opipramol</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a><sup>‡</sup></li> <li><a href="/wiki/Phenaglycodol" title="Phenaglycodol">Phenaglycodol</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a href="/wiki/Picamilon" title="Picamilon">Picamilon</a></li> <li><a href="/wiki/Selank" title="Selank">Selank</a></li> <li><a href="/wiki/Tiagabine" title="Tiagabine">Tiagabine</a></li> <li><a href="/wiki/Tofisopam" title="Tofisopam">Tofisopam</a></li> <li><a href="/wiki/Validolum" class="mw-redirect" title="Validolum">Validolum</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Benzodiazepines" 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:Benzodiazepines" title="Template:Benzodiazepines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Benzodiazepines" title="Template talk:Benzodiazepines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Benzodiazepines" title="Special:EditPage/Template:Benzodiazepines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Benzodiazepines" style="font-size:114%;margin:0 4em"><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">1,4-Benzodiazepines</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-Oxoquazepam" title="2-Oxoquazepam">2-Oxoquazepam</a></li> <li><a href="/wiki/3-Hydroxyphenazepam" title="3-Hydroxyphenazepam">3-Hydroxyphenazepam</a></li> <li><a href="/wiki/Bromazepam" title="Bromazepam">Bromazepam</a></li> <li><a href="/wiki/BMS-906024" title="BMS-906024">BMS-906024</a>*</li> <li><a href="/wiki/Camazepam" title="Camazepam">Camazepam</a></li> <li><a href="/wiki/Carburazepam" title="Carburazepam">Carburazepam</a></li> <li><a href="/wiki/Chlordiazepoxide" title="Chlordiazepoxide">Chlordiazepoxide</a></li> <li><a href="/wiki/Cinazepam" title="Cinazepam">Cinazepam</a></li> <li><a href="/wiki/Cinolazepam" title="Cinolazepam">Cinolazepam</a></li> <li><a href="/wiki/Clonazepam" title="Clonazepam">Clonazepam</a></li> <li><a href="/wiki/Cloniprazepam" title="Cloniprazepam">Cloniprazepam</a></li> <li><a href="/wiki/Clorazepate" title="Clorazepate">Clorazepate</a></li> <li><a href="/wiki/Cyprazepam" title="Cyprazepam">Cyprazepam</a></li> <li><a href="/wiki/Delorazepam" title="Delorazepam">Delorazepam</a></li> <li><a href="/wiki/Demoxepam" title="Demoxepam">Demoxepam</a></li> <li><a href="/wiki/Desmethylflunitrazepam" title="Desmethylflunitrazepam">Desmethylflunitrazepam</a></li> <li><a href="/wiki/Devazepide" title="Devazepide">Devazepide</a>*</li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a></li> <li><a href="/wiki/Diclazepam" title="Diclazepam">Diclazepam</a></li> <li><a href="/wiki/Difludiazepam" title="Difludiazepam">Difludiazepam</a></li> <li><a href="/wiki/Doxefazepam" title="Doxefazepam">Doxefazepam</a></li> <li><a href="/wiki/Elfazepam" title="Elfazepam">Elfazepam</a></li> <li><a href="/wiki/Ethyl_carfluzepate" title="Ethyl carfluzepate">Ethyl carfluzepate</a></li> <li><a href="/wiki/Ethyl_dirazepate" title="Ethyl dirazepate">Ethyl dirazepate</a></li> <li><a href="/wiki/Ethyl_loflazepate" title="Ethyl loflazepate">Ethyl loflazepate</a></li> <li><a href="/wiki/Flubromazepam" title="Flubromazepam">Flubromazepam</a></li> <li><a href="/wiki/Fletazepam" title="Fletazepam">Fletazepam</a></li> <li><a href="/wiki/Fludiazepam" title="Fludiazepam">Fludiazepam</a></li> <li><a href="/wiki/Flunitrazepam" title="Flunitrazepam">Flunitrazepam</a></li> <li><a href="/wiki/Flurazepam" title="Flurazepam">Flurazepam</a></li> <li><a href="/wiki/Flutemazepam" title="Flutemazepam">Flutemazepam</a></li> <li><a href="/wiki/Flutoprazepam" title="Flutoprazepam">Flutoprazepam</a></li> <li><a href="/wiki/Fosazepam" title="Fosazepam">Fosazepam</a></li> <li><a href="/wiki/Gidazepam" title="Gidazepam">Gidazepam</a></li> <li><a href="/wiki/Halazepam" title="Halazepam">Halazepam</a></li> <li><a href="/wiki/Iclazepam" title="Iclazepam">Iclazepam</a></li> <li><a href="/wiki/Irazepine" title="Irazepine">Irazepine</a>*</li> <li><a href="/w/index.php?title=Kenazepine&action=edit&redlink=1" class="new" title="Kenazepine (page does not exist)">Kenazepine</a></li> <li><a href="/wiki/Ketazolam" title="Ketazolam">Ketazolam</a></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a></li> <li><a href="/wiki/Lormetazepam" title="Lormetazepam">Lormetazepam</a></li> <li><a href="/wiki/Lufuradom" title="Lufuradom">Lufuradom</a>*</li> <li><a href="/wiki/Meclonazepam" title="Meclonazepam">Meclonazepam</a></li> <li><a href="/wiki/Medazepam" title="Medazepam">Medazepam</a></li> <li><a href="/wiki/Menitrazepam" title="Menitrazepam">Menitrazepam</a></li> <li><a href="/wiki/Metaclazepam" title="Metaclazepam">Metaclazepam</a></li> <li><a href="/wiki/Motrazepam" title="Motrazepam">Motrazepam</a></li> <li><a href="/wiki/N-Desalkylflurazepam" title="N-Desalkylflurazepam"><i>N</i>-Desalkylflurazepam</a></li> <li><a href="/wiki/Nifoxipam" title="Nifoxipam">Nifoxipam</a></li> <li><a href="/wiki/Nimetazepam" title="Nimetazepam">Nimetazepam</a></li> <li><a href="/wiki/Nitemazepam" title="Nitemazepam">Nitemazepam</a></li> <li><a href="/wiki/Nitrazepam" title="Nitrazepam">Nitrazepam</a></li> <li><a href="/wiki/Nitrazepate" title="Nitrazepate">Nitrazepate</a></li> <li><a href="/wiki/Nordazepam" title="Nordazepam">Nordazepam</a></li> <li><a href="/wiki/Nortetrazepam" title="Nortetrazepam">Nortetrazepam</a></li> <li><a href="/wiki/Oxazepam" title="Oxazepam">Oxazepam</a></li> <li><a href="/wiki/Phenazepam" title="Phenazepam">Phenazepam</a></li> <li><a href="/wiki/Pinazepam" title="Pinazepam">Pinazepam</a></li> <li><a href="/wiki/Pivoxazepam" title="Pivoxazepam">Pivoxazepam</a></li> <li><a href="/wiki/Prazepam" title="Prazepam">Prazepam</a></li> <li><a href="/wiki/Proflazepam" title="Proflazepam">Proflazepam</a></li> <li><a href="/wiki/Quazepam" title="Quazepam">Quazepam</a></li> <li><a href="/wiki/QH-II-66" title="QH-II-66">QH-II-66</a></li> <li><a href="/wiki/Reclazepam" title="Reclazepam">Reclazepam</a></li> <li><a href="/wiki/RO4491533" title="RO4491533">RO4491533</a>*</li> <li><a href="/wiki/Ro05-4082" title="Ro05-4082">Ro05-4082</a></li> <li><a href="/wiki/Ro5-4864" title="Ro5-4864">Ro5-4864</a>*</li> <li><a href="/wiki/Ro07-5220" title="Ro07-5220">Ro07-5220</a></li> <li><a href="/wiki/Ro07-9749" title="Ro07-9749">Ro07-9749</a></li> <li><a href="/wiki/Ro20-8065" title="Ro20-8065">Ro20-8065</a></li> <li><a href="/wiki/Ro20-8552" title="Ro20-8552">Ro20-8552</a></li> <li><a href="/wiki/SH-I-048A" title="SH-I-048A">SH-I-048A</a></li> <li><a href="/wiki/Sulazepam" title="Sulazepam">Sulazepam</a></li> <li><a href="/wiki/Temazepam" title="Temazepam">Temazepam</a></li> <li><a href="/wiki/Tetrazepam" title="Tetrazepam">Tetrazepam</a></li> <li><a href="/wiki/Tifluadom" title="Tifluadom">Tifluadom</a>*</li> <li><a href="/wiki/Timelotem" title="Timelotem">Timelotem</a>*</li> <li><a href="/wiki/Tolufazepam" class="mw-redirect" title="Tolufazepam">Tolufazepam</a></li> <li><a href="/wiki/Triflunordazepam" title="Triflunordazepam">Triflunordazepam</a></li> <li><a href="/wiki/Tuclazepam" title="Tuclazepam">Tuclazepam</a></li> <li><a href="/wiki/Uldazepam" title="Uldazepam">Uldazepam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">1,5-Benzodiazepines</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/Arfendazam" title="Arfendazam">Arfendazam</a></li> <li><a href="/wiki/Clobazam" title="Clobazam">Clobazam</a></li> <li><a href="/wiki/CP-1414S" title="CP-1414S">CP-1414S</a></li> <li><a href="/wiki/Lofendazam" title="Lofendazam">Lofendazam</a></li> <li><a href="/wiki/Triflubazam" title="Triflubazam">Triflubazam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">2,3-Benzodiazepines*</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/Girisopam" title="Girisopam">Girisopam</a></li> <li><a href="/wiki/GYKI-52,466" class="mw-redirect" title="GYKI-52,466">GYKI-52466</a></li> <li><a href="/wiki/GYKI-52895" class="mw-redirect" title="GYKI-52895">GYKI-52895</a></li> <li><a href="/wiki/Nerisopam" title="Nerisopam">Nerisopam</a></li> <li><a href="/wiki/Talampanel" title="Talampanel">Talampanel</a></li> <li><a href="/wiki/Tofisopam" title="Tofisopam">Tofisopam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triazolobenzodiazepine" title="Triazolobenzodiazepine">Triazolobenzodiazepines</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/Adinazolam" title="Adinazolam">Adinazolam</a></li> <li><a class="mw-selflink selflink">Alprazolam</a></li> <li><a href="/wiki/Balovaptan" title="Balovaptan">Balovaptan</a>*</li> <li><a href="/wiki/Bromazolam" title="Bromazolam">Bromazolam</a></li> <li><a href="/wiki/Clonazolam" title="Clonazolam">Clonazolam</a></li> <li><a href="/wiki/Estazolam" title="Estazolam">Estazolam</a></li> <li><a href="/wiki/Fluadinazolam" title="Fluadinazolam">Fluadinazolam</a></li> <li><a href="/wiki/Flualprazolam" title="Flualprazolam">Flualprazolam</a></li> <li><a href="/wiki/Flubromazolam" title="Flubromazolam">Flubromazolam</a></li> <li><a href="/wiki/Flunitrazolam" title="Flunitrazolam">Flunitrazolam</a></li> <li><a href="/wiki/Nitrazolam" title="Nitrazolam">Nitrazolam</a></li> <li><a href="/wiki/Phenazolam" title="Phenazolam">Phenazolam</a></li> <li><a href="/wiki/Pyrazolam" title="Pyrazolam">Pyrazolam</a></li> <li><a href="/wiki/Rilmazolam" title="Rilmazolam">Rilmazolam</a> (active metabolite of <a href="/wiki/Rilmazafone" title="Rilmazafone">Rilmazafone</a>)</li> <li><a href="/wiki/Triazolam" title="Triazolam">Triazolam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Imidazobenzodiazepines</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/Bretazenil" title="Bretazenil">Bretazenil</a></li> <li><a href="/wiki/Climazolam" title="Climazolam">Climazolam</a></li> <li><a href="/wiki/EVT-201" class="mw-redirect" title="EVT-201">EVT-201</a></li> <li><a href="/wiki/FG-8205" title="FG-8205">FG-8205</a></li> <li><a href="/wiki/Flumazenil" title="Flumazenil">Flumazenil</a></li> <li><a href="/wiki/GL-II-73" title="GL-II-73">GL-II-73</a></li> <li><a href="/wiki/Imidazenil" title="Imidazenil">Imidazenil</a></li> <li><a href="/wiki/Iomazenil" title="Iomazenil"><sup>123</sup>I-Iomazenil</a></li> <li><a href="/wiki/L-655,708" title="L-655,708">L-655,708</a></li> <li><a href="/wiki/Loprazolam" title="Loprazolam">Loprazolam</a></li> <li><a href="/wiki/Midazolam" title="Midazolam">Midazolam</a></li> <li><a href="/wiki/PWZ-029" title="PWZ-029">PWZ-029</a></li> <li><a href="/wiki/Remimazolam" title="Remimazolam">Remimazolam</a></li> <li><a href="/wiki/Ro15-4513" title="Ro15-4513">Ro15-4513</a></li> <li><a href="/wiki/Ro48-6791" title="Ro48-6791">Ro48-6791</a></li> <li><a href="/wiki/Ro48-8684" title="Ro48-8684">Ro48-8684</a></li> <li><a href="/wiki/Ro4938581" title="Ro4938581">Ro4938581</a></li> <li><a href="/wiki/Sarmazenil" title="Sarmazenil">Sarmazenil</a></li> <li><a href="/wiki/SH-053-R-CH3-2%E2%80%B2F" title="SH-053-R-CH3-2′F">SH-053-R-CH3-2′F</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Oxazolobenzodiazepines</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/Cloxazolam" title="Cloxazolam">Cloxazolam</a></li> <li><a href="/wiki/Flutazolam" title="Flutazolam">Flutazolam</a></li> <li><a href="/wiki/Haloxazolam" title="Haloxazolam">Haloxazolam</a></li> <li><a href="/wiki/Mexazolam" title="Mexazolam">Mexazolam</a></li> <li><a href="/wiki/Oxazolam" title="Oxazolam">Oxazolam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thienodiazepine" title="Thienodiazepine">Thienodiazepines</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/Bentazepam" title="Bentazepam">Bentazepam</a></li> <li><a href="/wiki/Clotiazepam" title="Clotiazepam">Clotiazepam</a></li> <li><a href="/wiki/Ro09-9212" title="Ro09-9212">Ro09-9212</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thienotriazolodiazepine" title="Thienotriazolodiazepine">Thienotriazolodiazepines</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/Alpha-Hydroxyetizolam" class="mw-redirect" title="Alpha-Hydroxyetizolam">α-Hydroxyetizolam</a></li> <li><a href="/wiki/Apafant" title="Apafant">Apafant</a>*</li> <li><a href="/wiki/Brotizolam" title="Brotizolam">Brotizolam</a></li> <li><a href="/wiki/Ciclotizolam" title="Ciclotizolam">Ciclotizolam</a></li> <li><a href="/wiki/Clotizolam" title="Clotizolam">Clotizolam</a></li> <li><a href="/wiki/Deschloroclotizolam" title="Deschloroclotizolam">Deschloroclotizolam</a></li> <li><a href="/wiki/Deschloroetizolam" title="Deschloroetizolam">Deschloroetizolam</a></li> <li><a href="/wiki/Etizolam" title="Etizolam">Etizolam</a></li> <li><a href="/wiki/Flubrotizolam" title="Flubrotizolam">Flubrotizolam</a></li> <li><a href="/wiki/Fluclotizolam" title="Fluclotizolam">Fluclotizolam</a></li> <li><a href="/wiki/Fluetizolam" title="Fluetizolam">Fluetizolam</a></li> <li><a href="/wiki/Israpafant" title="Israpafant">Israpafant</a>*</li> <li><a href="/wiki/JQ1" title="JQ1">JQ1</a>*</li> <li><a href="/wiki/Metizolam" title="Metizolam">Metizolam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thienobenzodiazepine" title="Thienobenzodiazepine">Thienobenzodiazepines</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/Olanzapine" title="Olanzapine">Olanzapine</a></li> <li><a href="/wiki/Telenzepine" title="Telenzepine">Telenzepine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Pyridodiazepines</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/Lopirazepam" title="Lopirazepam">Lopirazepam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyridotriazolodiazepine" class="mw-redirect" title="Pyridotriazolodiazepine">Pyridotriazolodiazepines</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/Zapizolam" title="Zapizolam">Zapizolam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Pyrazolodiazepines</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/Razobazam" title="Razobazam">Razobazam</a>*</li> <li><a href="/wiki/Ripazepam" title="Ripazepam">Ripazepam</a></li> <li><a href="/wiki/Zolazepam" title="Zolazepam">Zolazepam</a></li> <li><a href="/wiki/Zomebazam" title="Zomebazam">Zomebazam</a></li> <li><a href="/wiki/Zometapine" title="Zometapine">Zometapine</a>*</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Pyrrolodiazepines</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/Premazepam" title="Premazepam">Premazepam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tetrahydroisoquinobenzodiazepines</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/Clazolam" title="Clazolam">Clazolam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrrolobenzodiazepine" title="Pyrrolobenzodiazepine">Pyrrolobenzodiazepines</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/Anthramycin" title="Anthramycin">Anthramycin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Benzodiazepine prodrugs</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/Alprazolam_triazolobenzophenone" title="Alprazolam triazolobenzophenone">Alprazolam triazolobenzophenone</a></li> <li><a href="/wiki/Avizafone" title="Avizafone">Avizafone</a></li> <li><a href="/wiki/Rilmazafone" title="Rilmazafone">Rilmazafone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">* atypical activity profile (not <a href="/wiki/GABAA_receptor" title="GABAA receptor">GABA<sub>A</sub> receptor</a> ligands)</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="GABAA_receptor_positive_modulators" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:GABAA_receptor_positive_modulators" title="Template talk:GABAA receptor positive modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:GABAA_receptor_positive_modulators" title="Special:EditPage/Template:GABAA receptor positive modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="GABAA_receptor_positive_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/GABAA_receptor_positive_allosteric_modulator" title="GABAA receptor positive allosteric modulator"><abbr title="γ-Aminobutyric acid">GABA</abbr><sub>A</sub> receptor positive modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Brometone&action=edit&redlink=1" class="new" title="Brometone (page does not exist)">Brometone</a></li> <li><a href="/wiki/1-Butanol" title="1-Butanol">Butanol</a></li> <li><a href="/wiki/Chloralodol" title="Chloralodol">Chloralodol</a></li> <li><a href="/wiki/Chlorobutanol" title="Chlorobutanol">Chlorobutanol (cloretone)</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a> (<a href="/wiki/Alcoholic_drink" class="mw-redirect" title="Alcoholic drink">alcoholic drink</a>)</li> <li><a href="/wiki/Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li> <li><a href="/wiki/Isobutanol" title="Isobutanol">Isobutanol</a></li> <li><a href="/wiki/Isopropanol" class="mw-redirect" title="Isopropanol">Isopropanol</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methylpentynol" title="Methylpentynol">Methylpentynol</a></li> <li><a href="/wiki/1-Pentanol" title="1-Pentanol">Pentanol</a></li> <li><a href="/wiki/Petrichloral" title="Petrichloral">Petrichloral</a></li> <li><a href="/wiki/1-Propanol" title="1-Propanol">Propanol</a></li> <li><a href="/wiki/Tert-Butanol" class="mw-redirect" title="Tert-Butanol"><i>tert</i>-Butanol (2M2P)</a></li> <li><a href="/wiki/Tert-Pentanol" class="mw-redirect" title="Tert-Pentanol"><i>tert</i>-Pentanol (2M2B)</a></li> <li><a href="/wiki/Tribromoethanol" title="Tribromoethanol">Tribromoethanol</a></li> <li><a href="/wiki/Trichloroethanol" class="mw-redirect" title="Trichloroethanol">Trichloroethanol</a></li> <li><a href="/wiki/Triclofos" title="Triclofos">Triclofos</a></li> <li><a href="/wiki/Trifluoroethanol" class="mw-redirect" title="Trifluoroethanol">Trifluoroethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(-)-5-(1,3-Dimethylbutyl)-5-ethylbarbituric_acid" class="mw-redirect" title="(-)-5-(1,3-Dimethylbutyl)-5-ethylbarbituric acid">(-)-DMBB</a></li> <li><a href="/wiki/Allobarbital" title="Allobarbital">Allobarbital</a></li> <li><a href="/wiki/Alphenal" title="Alphenal">Alphenal</a></li> <li><a href="/wiki/Amobarbital" title="Amobarbital">Amobarbital</a></li> <li><a href="/wiki/Aprobarbital" title="Aprobarbital">Aprobarbital</a></li> <li><a href="/wiki/Barbexaclone" title="Barbexaclone">Barbexaclone</a></li> <li><a href="/wiki/Barbital" title="Barbital">Barbital</a></li> <li><a href="/wiki/Benzobarbital" title="Benzobarbital">Benzobarbital</a></li> <li><a href="/wiki/Benzylbutylbarbiturate" title="Benzylbutylbarbiturate">Benzylbutylbarbiturate</a></li> <li><a href="/wiki/Brallobarbital" title="Brallobarbital">Brallobarbital</a></li> <li><a href="/wiki/Brophebarbital" title="Brophebarbital">Brophebarbital</a></li> <li><a href="/wiki/Butabarbital" title="Butabarbital">Butabarbital/Secbutabarbital</a></li> <li><a href="/wiki/Butalbital" title="Butalbital">Butalbital</a></li> <li><a href="/wiki/Buthalital" title="Buthalital">Buthalital</a></li> <li><a href="/wiki/Butobarbital" title="Butobarbital">Butobarbital</a></li> <li><a href="/wiki/Butallylonal" title="Butallylonal">Butallylonal</a></li> <li><a href="/wiki/Carbubarb" title="Carbubarb">Carbubarb</a></li> <li><a href="/wiki/Crotylbarbital" title="Crotylbarbital">Crotylbarbital</a></li> <li><a href="/wiki/Cyclobarbital" title="Cyclobarbital">Cyclobarbital</a></li> <li><a href="/wiki/Cyclopentobarbital" title="Cyclopentobarbital">Cyclopentobarbital</a></li> <li><a href="/wiki/Difebarbamate" title="Difebarbamate">Difebarbamate</a></li> <li><a href="/wiki/Enallylpropymal" title="Enallylpropymal">Enallylpropymal</a></li> <li><a href="/wiki/Ethallobarbital" title="Ethallobarbital">Ethallobarbital</a></li> <li><a href="/wiki/Eterobarb" title="Eterobarb">Eterobarb</a></li> <li><a href="/wiki/Febarbamate" title="Febarbamate">Febarbamate</a></li> <li><a href="/wiki/Heptabarb" title="Heptabarb">Heptabarb</a></li> <li><a href="/wiki/Heptobarbital" title="Heptobarbital">Heptobarbital</a></li> <li><a href="/wiki/Hexethal" title="Hexethal">Hexethal</a></li> <li><a href="/wiki/Hexobarbital" title="Hexobarbital">Hexobarbital</a></li> <li><a href="/wiki/Metharbital" title="Metharbital">Metharbital</a></li> <li><a href="/wiki/Methitural" title="Methitural">Methitural</a></li> <li><a href="/wiki/Methohexital" title="Methohexital">Methohexital</a></li> <li><a href="/wiki/Methylphenobarbital" title="Methylphenobarbital">Methylphenobarbital</a></li> <li><a href="/wiki/Narcobarbital" title="Narcobarbital">Narcobarbital</a></li> <li><a href="/wiki/Nealbarbital" title="Nealbarbital">Nealbarbital</a></li> <li><a href="/wiki/Pentobarbital" title="Pentobarbital">Pentobarbital</a></li> <li><a href="/wiki/Phenallymal" class="mw-redirect" title="Phenallymal">Phenallymal</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Phetharbital" title="Phetharbital">Phetharbital</a></li> <li><a href="/wiki/Primidone" title="Primidone">Primidone</a></li> <li><a href="/wiki/Probarbital" title="Probarbital">Probarbital</a></li> <li><a href="/wiki/Propallylonal" title="Propallylonal">Propallylonal</a></li> <li><a href="/wiki/Propylbarbital" title="Propylbarbital">Propylbarbital</a></li> <li><a href="/wiki/Proxibarbital" title="Proxibarbital">Proxibarbital</a></li> <li><a href="/wiki/Reposal" title="Reposal">Reposal</a></li> <li><a href="/wiki/Secobarbital" title="Secobarbital">Secobarbital</a></li> <li><a href="/wiki/Sigmodal" title="Sigmodal">Sigmodal</a></li> <li><a href="/wiki/Spirobarbital" title="Spirobarbital">Spirobarbital</a></li> <li><a href="/wiki/Talbutal" title="Talbutal">Talbutal</a></li> <li><a href="/wiki/Tetrabamate" title="Tetrabamate">Tetrabamate</a></li> <li><a href="/wiki/Tetrabarbital" title="Tetrabarbital">Tetrabarbital</a></li> <li><a href="/wiki/Thialbarbital" title="Thialbarbital">Thialbarbital</a></li> <li><a href="/wiki/Thiamylal" title="Thiamylal">Thiamylal</a></li> <li><a href="/wiki/Thiobarbital" title="Thiobarbital">Thiobarbital</a></li> <li><a href="/wiki/Thiobutabarbital" title="Thiobutabarbital">Thiobutabarbital</a></li> <li><a href="/wiki/Sodium_thiopental" title="Sodium thiopental">Thiopental</a></li> <li><a href="/wiki/Thiotetrabarbital" title="Thiotetrabarbital">Thiotetrabarbital</a></li> <li><a href="/wiki/Valofane" title="Valofane">Valofane</a></li> <li><a href="/wiki/Vinbarbital" title="Vinbarbital">Vinbarbital</a></li> <li><a href="/wiki/Vinylbital" title="Vinylbital">Vinylbital</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</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-Oxoquazepam" title="2-Oxoquazepam">2-Oxoquazepam</a></li> <li><a href="/wiki/3-Hydroxyphenazepam" title="3-Hydroxyphenazepam">3-Hydroxyphenazepam</a></li> <li><a href="/wiki/Adinazolam" title="Adinazolam">Adinazolam</a></li> <li><a class="mw-selflink selflink">Alprazolam</a></li> <li><a href="/wiki/Arfendazam" title="Arfendazam">Arfendazam</a></li> <li><a href="/wiki/Avizafone" title="Avizafone">Avizafone</a></li> <li><a href="/wiki/Bentazepam" title="Bentazepam">Bentazepam</a></li> <li><a href="/wiki/Bretazenil" title="Bretazenil">Bretazenil</a></li> <li><a href="/wiki/Bromazepam" title="Bromazepam">Bromazepam</a></li> <li><a href="/wiki/Bromazolam" title="Bromazolam">Bromazolam</a></li> <li><a href="/wiki/Brotizolam" title="Brotizolam">Brotizolam</a></li> <li><a href="/wiki/Camazepam" title="Camazepam">Camazepam</a></li> <li><a href="/wiki/Carburazepam" title="Carburazepam">Carburazepam</a></li> <li><a href="/wiki/Chlordiazepoxide" title="Chlordiazepoxide">Chlordiazepoxide</a></li> <li><a href="/wiki/Ciclotizolam" title="Ciclotizolam">Ciclotizolam</a></li> <li><a href="/wiki/Cinazepam" title="Cinazepam">Cinazepam</a></li> <li><a href="/wiki/Cinolazepam" title="Cinolazepam">Cinolazepam</a></li> <li><a href="/wiki/Clazolam" title="Clazolam">Clazolam</a></li> <li><a href="/wiki/Climazolam" title="Climazolam">Climazolam</a></li> <li><a href="/wiki/Clobazam" title="Clobazam">Clobazam</a></li> <li><a href="/wiki/Clonazepam" title="Clonazepam">Clonazepam</a></li> <li><a href="/wiki/Clonazolam" title="Clonazolam">Clonazolam</a></li> <li><a href="/wiki/Cloniprazepam" title="Cloniprazepam">Cloniprazepam</a></li> <li><a href="/wiki/Clorazepate" title="Clorazepate">Clorazepate</a></li> <li><a href="/wiki/Clotiazepam" title="Clotiazepam">Clotiazepam</a></li> <li><a href="/wiki/Cloxazolam" title="Cloxazolam">Cloxazolam</a></li> <li><a href="/wiki/CP-1414S" title="CP-1414S">CP-1414S</a></li> <li><a href="/wiki/Cyprazepam" title="Cyprazepam">Cyprazepam</a></li> <li><a href="/wiki/Delorazepam" title="Delorazepam">Delorazepam</a></li> <li><a href="/wiki/Demoxepam" title="Demoxepam">Demoxepam</a></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a></li> <li><a href="/wiki/Diclazepam" title="Diclazepam">Diclazepam</a></li> <li><a href="/wiki/Dimdazenil" title="Dimdazenil">Dimdazenil</a></li> <li><a href="/wiki/Doxefazepam" title="Doxefazepam">Doxefazepam</a></li> <li><a href="/wiki/Elfazepam" title="Elfazepam">Elfazepam</a></li> <li><a href="/wiki/Estazolam" title="Estazolam">Estazolam</a></li> <li><a href="/wiki/Ethyl_carfluzepate" title="Ethyl carfluzepate">Ethyl carfluzepate</a></li> <li><a href="/wiki/Ethyl_dirazepate" title="Ethyl dirazepate">Ethyl dirazepate</a></li> <li><a href="/wiki/Ethyl_loflazepate" title="Ethyl loflazepate">Ethyl loflazepate</a></li> <li><a href="/wiki/Etizolam" title="Etizolam">Etizolam</a></li> <li><a href="/wiki/FG-8205" title="FG-8205">FG-8205</a></li> <li><a href="/wiki/Fletazepam" title="Fletazepam">Fletazepam</a></li> <li><a href="/wiki/Flubromazepam" title="Flubromazepam">Flubromazepam</a></li> <li><a href="/wiki/Flubromazolam" title="Flubromazolam">Flubromazolam</a></li> <li><a href="/wiki/Fludiazepam" title="Fludiazepam">Fludiazepam</a></li> <li><a href="/wiki/Flunitrazepam" title="Flunitrazepam">Flunitrazepam</a></li> <li><a href="/wiki/Flunitrazolam" title="Flunitrazolam">Flunitrazolam</a></li> <li><a href="/wiki/Flurazepam" title="Flurazepam">Flurazepam</a></li> <li><a href="/wiki/Flutazolam" title="Flutazolam">Flutazolam</a></li> <li><a href="/wiki/Flutemazepam" title="Flutemazepam">Flutemazepam</a></li> <li><a href="/wiki/Flutoprazepam" title="Flutoprazepam">Flutoprazepam</a></li> <li><a href="/wiki/Fosazepam" title="Fosazepam">Fosazepam</a></li> <li><a href="/wiki/Gidazepam" title="Gidazepam">Gidazepam</a></li> <li><a href="/wiki/Halazepam" title="Halazepam">Halazepam</a></li> <li><a href="/wiki/Haloxazolam" title="Haloxazolam">Haloxazolam</a></li> <li><a href="/wiki/Iclazepam" title="Iclazepam">Iclazepam</a></li> <li><a href="/wiki/Imidazenil" title="Imidazenil">Imidazenil</a></li> <li><a href="/wiki/Irazepine" title="Irazepine">Irazepine</a></li> <li><a href="/wiki/Ketazolam" title="Ketazolam">Ketazolam</a></li> <li><a href="/wiki/Lofendazam" title="Lofendazam">Lofendazam</a></li> <li><a href="/wiki/Lopirazepam" title="Lopirazepam">Lopirazepam</a></li> <li><a href="/wiki/Loprazolam" title="Loprazolam">Loprazolam</a></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a></li> <li><a href="/wiki/Lormetazepam" title="Lormetazepam">Lormetazepam</a></li> <li><a href="/wiki/Meclonazepam" title="Meclonazepam">Meclonazepam</a></li> <li><a href="/wiki/Medazepam" title="Medazepam">Medazepam</a></li> <li><a href="/wiki/Menitrazepam" title="Menitrazepam">Menitrazepam</a></li> <li><a href="/wiki/Metaclazepam" title="Metaclazepam">Metaclazepam</a></li> <li><a href="/wiki/Mexazolam" title="Mexazolam">Mexazolam</a></li> <li><a href="/wiki/Midazolam" title="Midazolam">Midazolam</a></li> <li><a href="/wiki/Motrazepam" title="Motrazepam">Motrazepam</a></li> <li><a href="/wiki/N-Desalkylflurazepam" title="N-Desalkylflurazepam">N-Desalkylflurazepam</a></li> <li><a href="/wiki/Nifoxipam" title="Nifoxipam">Nifoxipam</a></li> <li><a href="/wiki/Nimetazepam" title="Nimetazepam">Nimetazepam</a></li> <li><a href="/wiki/Nitrazepam" title="Nitrazepam">Nitrazepam</a></li> <li><a href="/wiki/Nitrazepate" title="Nitrazepate">Nitrazepate</a></li> <li><a href="/wiki/Nitrazolam" title="Nitrazolam">Nitrazolam</a></li> <li><a href="/wiki/Nordazepam" title="Nordazepam">Nordazepam</a></li> <li><a href="/wiki/Nortetrazepam" title="Nortetrazepam">Nortetrazepam</a></li> <li><a href="/wiki/Oxazepam" title="Oxazepam">Oxazepam</a></li> <li><a href="/wiki/Oxazolam" title="Oxazolam">Oxazolam</a></li> <li><a href="/wiki/Phenazepam" title="Phenazepam">Phenazepam</a></li> <li><a href="/wiki/Pinazepam" title="Pinazepam">Pinazepam</a></li> <li><a href="/wiki/Pivoxazepam" title="Pivoxazepam">Pivoxazepam</a></li> <li><a href="/wiki/Prazepam" title="Prazepam">Prazepam</a></li> <li><a href="/wiki/Premazepam" title="Premazepam">Premazepam</a></li> <li><a href="/wiki/Proflazepam" title="Proflazepam">Proflazepam</a></li> <li><a href="/wiki/Pyrazolam" title="Pyrazolam">Pyrazolam</a></li> <li><a href="/wiki/QH-II-66" title="QH-II-66">QH-II-66</a></li> <li><a href="/wiki/Quazepam" title="Quazepam">Quazepam</a></li> <li><a href="/wiki/Reclazepam" title="Reclazepam">Reclazepam</a></li> <li><a href="/wiki/Remimazolam" title="Remimazolam">Remimazolam</a></li> <li><a href="/wiki/Rilmazafone" title="Rilmazafone">Rilmazafone</a></li> <li><a href="/wiki/Ripazepam" title="Ripazepam">Ripazepam</a></li> <li><a href="/wiki/Ro48-6791" title="Ro48-6791">Ro48-6791</a></li> <li><a href="/wiki/Ro48-8684" title="Ro48-8684">Ro48-8684</a></li> <li><a href="/wiki/SH-053-R-CH3-2%E2%80%B2F" title="SH-053-R-CH3-2′F">SH-053-R-CH3-2′F</a></li> <li><a href="/wiki/Sulazepam" title="Sulazepam">Sulazepam</a></li> <li><a href="/wiki/Temazepam" title="Temazepam">Temazepam</a></li> <li><a href="/wiki/Tetrazepam" title="Tetrazepam">Tetrazepam</a></li> <li><a href="/wiki/Tolufazepam" class="mw-redirect" title="Tolufazepam">Tolufazepam</a></li> <li><a href="/wiki/Triazolam" title="Triazolam">Triazolam</a></li> <li><a href="/wiki/Triflubazam" title="Triflubazam">Triflubazam</a></li> <li><a href="/wiki/Triflunordazepam" title="Triflunordazepam">Triflunordazepam (Ro5-2904)</a></li> <li><a href="/wiki/Tuclazepam" title="Tuclazepam">Tuclazepam</a></li> <li><a href="/wiki/Uldazepam" title="Uldazepam">Uldazepam</a></li> <li><a href="/wiki/Zapizolam" title="Zapizolam">Zapizolam</a></li> <li><a href="/wiki/Zolazepam" title="Zolazepam">Zolazepam</a></li> <li><a href="/wiki/Zomebazam" title="Zomebazam">Zomebazam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Carbamate" title="Carbamate">Carbamates</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/Carisbamate" title="Carisbamate">Carisbamate</a></li> <li><a href="/wiki/Carisoprodol" title="Carisoprodol">Carisoprodol</a></li> <li><a href="/wiki/Clocental" title="Clocental">Clocental</a></li> <li><a href="/wiki/Cyclarbamate" title="Cyclarbamate">Cyclarbamate</a></li> <li><a href="/wiki/Difebarbamate" title="Difebarbamate">Difebarbamate</a></li> <li><a href="/wiki/Emylcamate" title="Emylcamate">Emylcamate</a></li> <li><a href="/wiki/Ethinamate" title="Ethinamate">Ethinamate</a></li> <li><a href="/wiki/Febarbamate" title="Febarbamate">Febarbamate</a></li> <li><a href="/wiki/Felbamate" title="Felbamate">Felbamate</a></li> <li><a href="/wiki/Hexapropymate" title="Hexapropymate">Hexapropymate</a></li> <li><a href="/wiki/Hydroxyphenamate" title="Hydroxyphenamate">Hydroxyphenamate</a></li> <li><a href="/wiki/Lorbamate" title="Lorbamate">Lorbamate</a></li> <li><a href="/wiki/Mebutamate" title="Mebutamate">Mebutamate</a></li> <li><a href="/wiki/Meprobamate" title="Meprobamate">Meprobamate</a></li> <li><a href="/wiki/Nisobamate" title="Nisobamate">Nisobamate</a></li> <li><a href="/wiki/Pentabamate" title="Pentabamate">Pentabamate</a></li> <li><a href="/wiki/Phenprobamate" title="Phenprobamate">Phenprobamate</a></li> <li><a href="/wiki/Procymate" title="Procymate">Procymate</a></li> <li><a href="/wiki/Styramate" title="Styramate">Styramate</a></li> <li><a href="/wiki/Tetrabamate" title="Tetrabamate">Tetrabamate</a></li> <li><a href="/wiki/Tybamate" title="Tybamate">Tybamate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</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/6-Methylapigenin" title="6-Methylapigenin">6-Methylapigenin</a></li> <li><a href="/wiki/Ampelopsin" title="Ampelopsin">Ampelopsin (dihydromyricetin)</a></li> <li><a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/Baicalein" title="Baicalein">Baicalein</a></li> <li><a href="/wiki/Baicalin" title="Baicalin">Baicalin</a></li> <li><a href="/wiki/Catechin" title="Catechin">Catechin</a></li> <li><a href="/wiki/Epigallocatechin" class="mw-redirect" title="Epigallocatechin">EGC</a></li> <li><a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a></li> <li><a href="/wiki/Hispidulin" title="Hispidulin">Hispidulin</a></li> <li><a href="/w/index.php?title=Linarin&action=edit&redlink=1" class="new" title="Linarin (page does not exist)">Linarin</a></li> <li><a href="/wiki/Luteolin" title="Luteolin">Luteolin</a></li> <li><a href="/w/index.php?title=Trans-6,4%E2%80%B2-dimethoxyretrochalcone&action=edit&redlink=1" class="new" title="Trans-6,4′-dimethoxyretrochalcone (page does not exist)">Rc-OMe</a></li> <li><a href="/wiki/Scutellaria" title="Scutellaria">Skullcap</a> constituents (e.g., <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>)</li> <li><a href="/wiki/Wogonin" title="Wogonin">Wogonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Imidazole" title="Imidazole">Imidazoles</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/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Metomidate" title="Metomidate">Metomidate</a></li> <li><a href="/wiki/Propoxate" title="Propoxate">Propoxate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Kava" title="Kava">Kava</a> constituents</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=10-Methoxyyangonin&action=edit&redlink=1" class="new" title="10-Methoxyyangonin (page does not exist)">10-Methoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Methoxyyangonin&action=edit&redlink=1" class="new" title="11-Methoxyyangonin (page does not exist)">11-Methoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Hydroxyyangonin&action=edit&redlink=1" class="new" title="11-Hydroxyyangonin (page does not exist)">11-Hydroxyyangonin</a></li> <li><a href="/wiki/Desmethoxyyangonin" title="Desmethoxyyangonin">Desmethoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Methoxy-12-hydroxydehydrokavain&action=edit&redlink=1" class="new" title="11-Methoxy-12-hydroxydehydrokavain (page does not exist)">11-Methoxy-12-hydroxydehydrokavain</a></li> <li><a href="/w/index.php?title=7,8-Dihydroyangonin&action=edit&redlink=1" class="new" title="7,8-Dihydroyangonin (page does not exist)">7,8-Dihydroyangonin</a></li> <li><a href="/wiki/Kavain" title="Kavain">Kavain</a></li> <li><a href="/w/index.php?title=5-Hydroxykavain&action=edit&redlink=1" class="new" title="5-Hydroxykavain (page does not exist)">5-Hydroxykavain</a></li> <li><a href="/w/index.php?title=5,6-Dihydroyangonin&action=edit&redlink=1" class="new" title="5,6-Dihydroyangonin (page does not exist)">5,6-Dihydroyangonin</a></li> <li><a href="/w/index.php?title=7,8-Dihydrokavain&action=edit&redlink=1" class="new" title="7,8-Dihydrokavain (page does not exist)">7,8-Dihydrokavain</a></li> <li><a href="/w/index.php?title=5,6,7,8-Tetrahydroyangonin&action=edit&redlink=1" class="new" title="5,6,7,8-Tetrahydroyangonin (page does not exist)">5,6,7,8-Tetrahydroyangonin</a></li> <li><a href="/w/index.php?title=5,6-Dehydromethysticin&action=edit&redlink=1" class="new" title="5,6-Dehydromethysticin (page does not exist)">5,6-Dehydromethysticin</a></li> <li><a href="/wiki/Methysticin" title="Methysticin">Methysticin</a></li> <li><a href="/w/index.php?title=7,8-Dihydromethysticin&action=edit&redlink=1" class="new" title="7,8-Dihydromethysticin (page does not exist)">7,8-Dihydromethysticin</a></li> <li><a href="/wiki/Yangonin" title="Yangonin">Yangonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Monoureide" class="mw-redirect" title="Monoureide">Monoureides</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/Acecarbromal" title="Acecarbromal">Acecarbromal</a></li> <li><a href="/wiki/Apronal" title="Apronal">Apronal (apronalide)</a></li> <li><a href="/wiki/Bromisoval" title="Bromisoval">Bromisoval</a></li> <li><a href="/wiki/Carbromal" title="Carbromal">Carbromal</a></li> <li><a href="/w/index.php?title=Capuride&action=edit&redlink=1" class="new" title="Capuride (page does not exist)">Capuride</a></li> <li><a href="/w/index.php?title=Ectylurea&action=edit&redlink=1" class="new" title="Ectylurea (page does not exist)">Ectylurea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</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/Acebrochol" title="Acebrochol">Acebrochol</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone (brexanolone)</a></li> <li><a href="/wiki/Alfadolone" title="Alfadolone">Alfadolone</a></li> <li><a href="/wiki/Alfaxalone" title="Alfaxalone">Alfaxalone</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/Androstenol" title="Androstenol">Androstenol</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li>Certain <a href="/wiki/Anabolic-androgenic_steroid" class="mw-redirect" title="Anabolic-androgenic steroid">anabolic-androgenic steroids</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">DHDOC</a></li> <li><a href="/wiki/3%CE%B1-Dihydroprogesterone" title="3α-Dihydroprogesterone">3α-DHP</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-DHP</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-DHP</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">DHT</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li> <li><a href="/wiki/Ganaxolone" title="Ganaxolone">Ganaxolone</a></li> <li><a href="/wiki/Hydroxydione" title="Hydroxydione">Hydroxydione</a></li> <li><a href="/wiki/Minaxolone" title="Minaxolone">Minaxolone</a></li> <li><a href="/wiki/ORG-20599" title="ORG-20599">ORG-20599</a></li> <li><a href="/wiki/ORG-21465" title="ORG-21465">ORG-21465</a></li> <li><a href="/wiki/P1-185" title="P1-185">P1-185</a></li> <li><a href="/wiki/Posovolone" title="Posovolone">Posovolone</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone (eltanolone)</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Renanolone" title="Renanolone">Renanolone</a></li> <li><a href="/w/index.php?title=SAGE-105&action=edit&redlink=1" class="new" title="SAGE-105 (page does not exist)">SAGE-105</a></li> <li><a href="/wiki/SAGE-324" title="SAGE-324">SAGE-324</a></li> <li><a href="/w/index.php?title=SAGE-516&action=edit&redlink=1" class="new" title="SAGE-516 (page does not exist)">SAGE-516</a></li> <li><a href="/w/index.php?title=SAGE-689&action=edit&redlink=1" class="new" title="SAGE-689 (page does not exist)">SAGE-689</a></li> <li><a href="/w/index.php?title=SAGE-872&action=edit&redlink=1" class="new" title="SAGE-872 (page does not exist)">SAGE-872</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li> <li><a href="/wiki/Tetrahydrodeoxycorticosterone" title="Tetrahydrodeoxycorticosterone">THDOC</a></li> <li><a href="/wiki/Zuranolone" title="Zuranolone">Zuranolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">Nonbenzodiazepines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Cyclopyrrolone" class="mw-redirect" title="Cyclopyrrolone">Cyclopyrrolones</a></i>: <a href="/wiki/Eszopiclone" title="Eszopiclone">Eszopiclone</a></li> <li><a href="/wiki/Pagoclone" title="Pagoclone">Pagoclone</a></li> <li><a href="/wiki/Pazinaclone" title="Pazinaclone">Pazinaclone</a></li> <li><a href="/wiki/Suproclone" title="Suproclone">Suproclone</a></li> <li><a href="/wiki/Suriclone" title="Suriclone">Suriclone</a></li> <li><a href="/wiki/Zopiclone" title="Zopiclone">Zopiclone</a></li></ul> <ul><li><i><a href="/wiki/Imidazopyridine" title="Imidazopyridine">Imidazopyridines</a></i>: <a href="/wiki/Alpidem" title="Alpidem">Alpidem</a></li> <li><a href="/wiki/DS-1_(drug)" title="DS-1 (drug)">DS-1</a></li> <li><a href="/wiki/Necopidem" title="Necopidem">Necopidem</a></li> <li><a href="/wiki/Saripidem" title="Saripidem">Saripidem</a></li> <li><a href="/wiki/Zolpidem" title="Zolpidem">Zolpidem</a></li></ul> <ul><li><i><a href="/wiki/Pyrazolopyrimidine" title="Pyrazolopyrimidine">Pyrazolopyrimidines</a></i>: <a href="/wiki/Divaplon" title="Divaplon">Divaplon</a></li> <li><a href="/wiki/Fasiplon" title="Fasiplon">Fasiplon</a></li> <li><a href="/wiki/Indiplon" title="Indiplon">Indiplon</a></li> <li><a href="/wiki/Lorediplon" title="Lorediplon">Lorediplon</a></li> <li><a href="/wiki/Ocinaplon" title="Ocinaplon">Ocinaplon</a></li> <li><a href="/wiki/Panadiplon" title="Panadiplon">Panadiplon</a></li> <li><a href="/wiki/Taniplon" title="Taniplon">Taniplon</a></li> <li><a href="/wiki/Zaleplon" title="Zaleplon">Zaleplon</a></li></ul> <ul><li><i>Others</i>: <a href="/wiki/Adipiplon" title="Adipiplon">Adipiplon</a></li> <li><a href="/wiki/CGS-8216" title="CGS-8216">CGS-8216</a></li> <li><a href="/wiki/CGS-9896" title="CGS-9896">CGS-9896</a></li> <li><a href="/wiki/CGS-13767" title="CGS-13767">CGS-13767</a></li> <li><a href="/wiki/CGS-20625" title="CGS-20625">CGS-20625</a></li> <li><a href="/wiki/CL-218,872" title="CL-218,872">CL-218,872</a></li> <li><a href="/wiki/CP-615,003" title="CP-615,003">CP-615,003</a></li> <li><a href="/w/index.php?title=CTP-354&action=edit&redlink=1" class="new" title="CTP-354 (page does not exist)">CTP-354</a></li> <li><a href="/wiki/ELB-139" title="ELB-139">ELB-139</a></li> <li><a href="/wiki/GBLD-345" title="GBLD-345">GBLD-345</a></li> <li><a href="/wiki/Imepitoin" title="Imepitoin">Imepitoin</a></li> <li><a href="/wiki/JM-1232" title="JM-1232">JM-1232</a></li> <li><a href="/wiki/L-838,417" title="L-838,417">L-838,417</a></li> <li><a href="/wiki/Lirequinil" title="Lirequinil">Lirequinil (Ro41-3696)</a></li> <li><a href="/wiki/NS-2664" title="NS-2664">NS-2664</a></li> <li><a href="/wiki/NS-2710" title="NS-2710">NS-2710</a></li> <li><a href="/wiki/NS-11394" title="NS-11394">NS-11394</a></li> <li><a href="/wiki/Pipequaline" title="Pipequaline">Pipequaline</a></li> <li><a href="/wiki/ROD-188" title="ROD-188">ROD-188</a></li> <li><a href="/wiki/RWJ-51204" title="RWJ-51204">RWJ-51204</a></li> <li><a href="/wiki/SB-205,384" class="mw-redirect" title="SB-205,384">SB-205,384</a></li> <li><a href="/wiki/SX-3228" title="SX-3228">SX-3228</a></li> <li><a href="/w/index.php?title=TGSC01AA&action=edit&redlink=1" class="new" title="TGSC01AA (page does not exist)">TGSC01AA</a></li> <li><a href="/wiki/TP-003" title="TP-003">TP-003</a></li> <li><a href="/wiki/TPA-023" title="TPA-023">TPA-023</a></li> <li><a href="/wiki/TP-13" title="TP-13">TP-13</a></li> <li><a href="/wiki/U-89843A" title="U-89843A">U-89843A</a></li> <li><a href="/wiki/U-90042" title="U-90042">U-90042</a></li> <li><a href="/wiki/Viqualine" title="Viqualine">Viqualine</a></li> <li><a href="/wiki/Y-23684" title="Y-23684">Y-23684</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Phenol" title="Phenol">Phenols</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/Fospropofol" title="Fospropofol">Fospropofol</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Thymol" title="Thymol">Thymol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Piperidinedione" class="mw-redirect" title="Piperidinedione">Piperidinediones</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/Glutethimide" title="Glutethimide">Glutethimide</a></li> <li><a href="/wiki/Methyprylon" title="Methyprylon">Methyprylon</a></li> <li><a href="/wiki/Piperidione" title="Piperidione">Piperidione</a></li> <li><a href="/wiki/Pyrithyldione" title="Pyrithyldione">Pyrithyldione</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Pyrazolopyridine" class="mw-redirect" title="Pyrazolopyridine">Pyrazolopyridines</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/Cartazolate" title="Cartazolate">Cartazolate</a></li> <li><a href="/wiki/Etazolate" title="Etazolate">Etazolate</a></li> <li><a href="/wiki/ICI-190,622" title="ICI-190,622">ICI-190,622</a></li> <li><a href="/wiki/Tracazolate" title="Tracazolate">Tracazolate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Quinazolinone" title="Quinazolinone">Quinazolinones</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/Afloqualone" title="Afloqualone">Afloqualone</a></li> <li><a href="/wiki/Cloroqualone" title="Cloroqualone">Cloroqualone</a></li> <li><a href="/wiki/Diproqualone" title="Diproqualone">Diproqualone</a></li> <li><a href="/wiki/Etaqualone" title="Etaqualone">Etaqualone</a></li> <li><a href="/wiki/Mebroqualone" title="Mebroqualone">Mebroqualone</a></li> <li><a href="/wiki/Mecloqualone" title="Mecloqualone">Mecloqualone</a></li> <li><a href="/wiki/Methaqualone" title="Methaqualone">Methaqualone</a></li> <li><a href="/wiki/Methylmethaqualone" title="Methylmethaqualone">Methylmethaqualone</a></li> <li><a href="/wiki/Nitromethaqualone" title="Nitromethaqualone">Nitromethaqualone</a></li> <li><a href="/wiki/SL-164" title="SL-164">SL-164</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">Volatiles</a>/<a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">gases</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/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Acetophenone" title="Acetophenone">Acetophenone</a></li> <li><a href="/wiki/Acetylglycinamide_chloral_hydrate" title="Acetylglycinamide chloral hydrate">Acetylglycinamide chloral hydrate</a></li> <li><a href="/wiki/Aliflurane" title="Aliflurane">Aliflurane</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Butylene" class="mw-redirect" title="Butylene">Butylene</a></li> <li><a href="/wiki/Centalun" title="Centalun">Centalun</a></li> <li><a href="/wiki/Chloral" title="Chloral">Chloral</a></li> <li><a href="/wiki/Chloral_betaine" title="Chloral betaine">Chloral betaine</a></li> <li><a href="/wiki/Chloral_hydrate" title="Chloral hydrate">Chloral hydrate</a></li> <li><a href="/wiki/Chloroform" title="Chloroform">Chloroform</a></li> <li><a href="/wiki/Cryofluorane" class="mw-redirect" title="Cryofluorane">Cryofluorane</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Dichloralphenazone" title="Dichloralphenazone">Dichloralphenazone</a></li> <li><a href="/wiki/Dichloromethane" title="Dichloromethane">Dichloromethane</a></li> <li><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Chloroethane" title="Chloroethane">Ethyl chloride</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Fluroxene" title="Fluroxene">Fluroxene</a></li> <li><a href="/wiki/Gasoline" title="Gasoline">Gasoline</a></li> <li><a href="/wiki/Halopropane" title="Halopropane">Halopropane</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Kerosene" title="Kerosene">Kerosine</a></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Methoxypropane" title="Methoxypropane">Methoxypropane</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Norflurane" class="mw-redirect" title="Norflurane">Norflurane</a></li> <li><a href="/wiki/Paraldehyde" title="Paraldehyde">Paraldehyde</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propylene</a></li> <li><a href="/wiki/Roflurane" title="Roflurane">Roflurane</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Synthane" title="Synthane">Synthane</a></li> <li><a href="/wiki/Teflurane" title="Teflurane">Teflurane</a></li> <li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li> <li><a href="/wiki/1,1,1-Trichloroethane" title="1,1,1-Trichloroethane">Trichloroethane (methyl chloroform)</a></li> <li><a href="/wiki/Trichloroethylene" title="Trichloroethylene">Trichloroethylene</a></li> <li><a href="/wiki/Divinyl_ether" title="Divinyl ether">Vinyl ether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;">Others/unsorted</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/3-Hydroxybutanal" title="3-Hydroxybutanal">3-Hydroxybutanal</a></li> <li><a href="/w/index.php?title=%CE%91-Ethyl-%CE%B1-methylthiobutyrolactone&action=edit&redlink=1" class="new" title="Α-Ethyl-α-methylthiobutyrolactone (page does not exist)">α-EMTBL</a></li> <li><a href="/w/index.php?title=AA-29504&action=edit&redlink=1" class="new" title="AA-29504 (page does not exist)">AA-29504</a></li> <li><a href="/wiki/Alogabat" title="Alogabat">Alogabat</a></li> <li><a href="/wiki/Avermectin" title="Avermectin">Avermectins</a> (e.g., <a href="/wiki/Ivermectin" title="Ivermectin">ivermectin</a>)</li> <li><a href="/wiki/Bromide" title="Bromide">Bromide</a> compounds (e.g., <a href="/wiki/Lithium_bromide" title="Lithium bromide">lithium bromide</a>, <a href="/wiki/Potassium_bromide" title="Potassium bromide">potassium bromide</a>, <a href="/wiki/Sodium_bromide" title="Sodium bromide">sodium bromide</a>)</li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Chloralose" title="Chloralose">Chloralose</a></li> <li><a href="/wiki/Chlormezanone" title="Chlormezanone">Chlormezanone</a></li> <li><a href="/wiki/Clomethiazole" title="Clomethiazole">Clomethiazole</a></li> <li><a href="/wiki/Darigabat" title="Darigabat">Darigabat</a></li> <li><a href="/wiki/3,3-Diethyl-2-pyrrolidinone" title="3,3-Diethyl-2-pyrrolidinone">DEABL</a></li> <li><a href="/wiki/Deuterated_etifoxine" title="Deuterated etifoxine">Deuterated etifoxine</a></li> <li><a href="/wiki/Dihydroergoline" class="mw-redirect" title="Dihydroergoline">Dihydroergolines</a> (e.g., <a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">dihydroergocryptine</a>, <a href="/w/index.php?title=Dihydroergosine&action=edit&redlink=1" class="new" title="Dihydroergosine (page does not exist)">dihydroergosine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergoloid" title="Ergoloid">ergoloid (dihydroergotoxine)</a>)</li> <li><a href="/w/index.php?title=4-Chloro-N-(2-(2-thienyl)imidazo(1,2-a)pyridin-3-yl)benzamide&action=edit&redlink=1" class="new" title="4-Chloro-N-(2-(2-thienyl)imidazo(1,2-a)pyridin-3-yl)benzamide (page does not exist)">DS2</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Etazepine" title="Etazepine">Etazepine</a></li> <li><a href="/wiki/Etifoxine" title="Etifoxine">Etifoxine</a></li> <li><a href="/wiki/Fenamate" class="mw-redirect" title="Fenamate">Fenamates</a> (e.g., <a href="/wiki/Flufenamic_acid" title="Flufenamic acid">flufenamic acid</a>, <a href="/wiki/Mefenamic_acid" title="Mefenamic acid">mefenamic acid</a>, <a href="/wiki/Niflumic_acid" title="Niflumic acid">niflumic acid</a>, <a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">tolfenamic acid</a>)</li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/wiki/Flupirtine" title="Flupirtine">Flupirtine</a></li> <li><a href="/wiki/Hopantenic_acid" title="Hopantenic acid">Hopantenic acid</a></li> <li><a href="/wiki/KRM-II-81" title="KRM-II-81">KRM-II-81</a></li> <li><a href="/wiki/Lanthanum" title="Lanthanum">Lanthanum</a></li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/4-O-methylhonokiol" class="mw-redirect" title="4-O-methylhonokiol">4-O-methylhonokiol</a>, <a href="/wiki/Honokiol" title="Honokiol">honokiol</a>, <a href="/wiki/Magnolol" title="Magnolol">magnolol</a>, <a href="/wiki/Obovatol" title="Obovatol">obovatol</a>)</li> <li><a href="/wiki/Loreclezole" title="Loreclezole">Loreclezole</a></li> <li><a href="/wiki/Menthyl_isovalerate" title="Menthyl isovalerate">Menthyl isovalerate (validolum)</a></li> <li><a href="/wiki/Monastrol" title="Monastrol">Monastrol</a></li> <li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Org_25435" class="mw-redirect" title="Org 25435">Org 25,435</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/Propanidid" title="Propanidid">Propanidid</a></li> <li><a href="/wiki/Retigabine" title="Retigabine">Retigabine (ezogabine)</a></li> <li><a href="/wiki/Safranal" title="Safranal">Safranal</a></li> <li><a href="/wiki/Seproxetine" title="Seproxetine">Seproxetine</a></li> <li><a href="/wiki/Stiripentol" title="Stiripentol">Stiripentol</a></li> <li><a href="/w/index.php?title=Sulfonylalkane&action=edit&redlink=1" class="new" title="Sulfonylalkane (page does not exist)">Sulfonylalkanes</a> (e.g., <a href="/wiki/Sulfonmethane" title="Sulfonmethane">sulfonmethane (sulfonal)</a>, <a href="/wiki/Tetronal" title="Tetronal">tetronal</a>, <a href="/wiki/Trional" title="Trional">trional</a>)</li> <li><a href="/wiki/Terpenoid" title="Terpenoid">Terpenoids</a> (e.g., <a href="/wiki/Borneol" title="Borneol">borneol</a>)</li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Valerian_(herb)" title="Valerian (herb)">Valerian</a> constituents (e.g., <a href="/wiki/3-methylbutanoic_acid" class="mw-redirect" title="3-methylbutanoic acid">isovaleric acid</a>, <a href="/wiki/Isovaleramide" title="Isovaleramide">isovaleramide</a>, <a href="/wiki/Valerenic_acid" title="Valerenic acid">valerenic acid</a>, <a href="/w/index.php?title=Valerenol&action=edit&redlink=1" class="new" title="Valerenol (page does not exist)">valerenol</a>)</li></ul> <ul><li><i>Unsorted benzodiazepine site positive modulators:</i> <a href="/wiki/%CE%91-Pinene" title="Α-Pinene">α-Pinene</a></li> <li><a href="/wiki/MRK-409_(MK-0343)" class="mw-redirect" title="MRK-409 (MK-0343)">MRK-409 (MK-0343)</a></li> <li><a href="/w/index.php?title=TCS-1105&action=edit&redlink=1" class="new" title="TCS-1105 (page does not exist)">TCS-1105</a></li> <li><a href="/wiki/TCS-1205" title="TCS-1205">TCS-1205</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a> • <a href="/wiki/Template:GABA_metabolism_and_transport_modulators" title="Template:GABA metabolism and transport modulators">GABA metabolism/transport modulators</a></i></div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output 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