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<div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Effects</span> </div> </a> <ul id="toc-Effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Exposure_routes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Exposure_routes"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Exposure routes</span> </div> </a> <ul id="toc-Exposure_routes-sublist" class="vector-toc-list"> <li id="toc-Oral" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Oral"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.1</span> <span>Oral</span> </div> </a> <ul id="toc-Oral-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dermal" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Dermal"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.2</span> <span>Dermal</span> </div> </a> <ul id="toc-Dermal-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Inhalation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Inhalation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.3</span> <span>Inhalation</span> </div> </a> <ul id="toc-Inhalation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Mechanism_of_toxicity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mechanism_of_toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Mechanism of toxicity</span> </div> </a> <ul id="toc-Mechanism_of_toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cases_of_toxicity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cases_of_toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Cases of toxicity</span> </div> </a> <ul id="toc-Cases_of_toxicity-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Synthesis</span> </div> </a> <button aria-controls="toc-Synthesis-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 Synthesis subsection</span> </button> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> <li id="toc-Laboratory_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Laboratory_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Laboratory synthesis</span> </div> </a> <ul id="toc-Laboratory_synthesis-sublist" class="vector-toc-list"> <li id="toc-Cyclic_expansion_of_tropanes" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cyclic_expansion_of_tropanes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.1</span> <span>Cyclic expansion of tropanes</span> </div> </a> <ul id="toc-Cyclic_expansion_of_tropanes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyclization_of_cyclooctenes" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cyclization_of_cyclooctenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.2</span> <span>Cyclization of cyclooctenes</span> </div> </a> <ul id="toc-Cyclization_of_cyclooctenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Enantioselective_enolization_strategy" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Enantioselective_enolization_strategy"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.3</span> <span>Enantioselective enolization strategy</span> </div> </a> <ul id="toc-Enantioselective_enolization_strategy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Intramolecular_cyclization_of_iminium_ions" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Intramolecular_cyclization_of_iminium_ions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.4</span> <span>Intramolecular cyclization of iminium ions</span> </div> </a> <ul id="toc-Intramolecular_cyclization_of_iminium_ions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Enyne_metathesis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Enyne_metathesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.5</span> <span>Enyne metathesis</span> </div> </a> <ul id="toc-Enyne_metathesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Stability_and_degradation" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Stability_and_degradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Stability and degradation</span> </div> </a> <ul id="toc-Stability_and_degradation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Detection" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Detection"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Detection</span> </div> </a> <ul id="toc-Detection-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Public_health" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Public_health"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Public health</span> </div> </a> <button aria-controls="toc-Public_health-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 Public health subsection</span> </button> <ul id="toc-Public_health-sublist" class="vector-toc-list"> <li id="toc-Water_regulations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Water_regulations"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1</span> <span>Water regulations</span> </div> </a> <ul id="toc-Water_regulations-sublist" class="vector-toc-list"> <li id="toc-United_States" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#United_States"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1.1</span> <span>United States</span> </div> </a> <ul id="toc-United_States-sublist" class="vector-toc-list"> <li id="toc-Drinking_water_advisory_levels" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Drinking_water_advisory_levels"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1.1.1</span> <span>Drinking water advisory levels</span> </div> </a> <ul id="toc-Drinking_water_advisory_levels-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Recreational_water_advisory_levels" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Recreational_water_advisory_levels"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1.1.2</span> <span>Recreational water advisory levels</span> </div> </a> <ul id="toc-Recreational_water_advisory_levels-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Canada" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Canada"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1.2</span> <span>Canada</span> </div> </a> <ul id="toc-Canada-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-New_Zealand" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#New_Zealand"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1.3</span> <span>New Zealand</span> </div> </a> <ul id="toc-New_Zealand-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Water_treatment" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Water_treatment"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.2</span> <span>Water treatment</span> </div> </a> <ul id="toc-Water_treatment-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Laboratory_uses" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Laboratory_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Laboratory uses</span> </div> </a> <ul id="toc-Laboratory_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Genera_of_cyanobacteria_that_produce_anatoxin-a" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Genera_of_cyanobacteria_that_produce_anatoxin-a"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Genera of cyanobacteria that produce anatoxin-a</span> </div> </a> <ul id="toc-Genera_of_cyanobacteria_that_produce_anatoxin-a-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">13</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">14</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">15</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" 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interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Anatoxin-a" title="Anatoxin-a – Czech" lang="cs" hreflang="cs" data-title="Anatoxin-a" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Anatoxin_A" title="Anatoxin A – German" lang="de" hreflang="de" data-title="Anatoxin A" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D9%86%D8%A7%D8%AA%D9%88%DA%A9%D8%B3%DB%8C%D9%86-%D8%A7%DB%8C" title="آناتوکسین-ای – Persian" lang="fa" hreflang="fa" data-title="آناتوکسین-ای" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%84%EB%82%98%ED%86%A1%EC%8B%A0-a" title="아나톡신-a – Korean" lang="ko" hreflang="ko" data-title="아나톡신-a" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Anatoxina-a" title="Anatoxina-a – Portuguese" lang="pt" hreflang="pt" data-title="Anatoxina-a" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Anatoksin-a" title="Anatoksin-a – Serbian" lang="sr" hreflang="sr" data-title="Anatoksin-a" 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/Anatoksin-a" title="Anatoksin-a – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Anatoksin-a" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q3303006#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected 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class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Anatoxin-a(S)" class="mw-redirect" title="Anatoxin-a(S)">Anatoxin-a(S)</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Anatoxin-a </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Anatoxin-a.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Anatoxin-a.png/150px-Anatoxin-a.png" decoding="async" width="150" height="146" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Anatoxin-a.png/225px-Anatoxin-a.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/36/Anatoxin-a.png/300px-Anatoxin-a.png 2x" data-file-width="1116" data-file-height="1085" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Very_Fast_Death_Factor_molecule_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of the anatoxin-a molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Very_Fast_Death_Factor_molecule_ball.png/160px-Very_Fast_Death_Factor_molecule_ball.png" decoding="async" width="160" height="141" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Very_Fast_Death_Factor_molecule_ball.png/240px-Very_Fast_Death_Factor_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/Very_Fast_Death_Factor_molecule_ball.png/320px-Very_Fast_Death_Factor_molecule_ball.png 2x" data-file-width="2000" data-file-height="1765" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">1-(9-azabicyclo[4.2.1]non-2-en-2-yl)ethan-1-one</div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Anatoxin A</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><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><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=64285-06-9">64285-06-9</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> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28%3DO%29C1%3DCCCC2CCC1N2">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL25619">ChEMBL25619</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> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.381822.html">381822</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> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.215.761">100.215.761</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q3303006#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> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C10841">C10841</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> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/3034748">3034748</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/80023A73NK">80023A73NK</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> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><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/DTXSID50867064,">DTXSID301338831 DTXSID50867064, DTXSID301338831</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q3303006#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> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C10H15NO/c1-7(12)9-4-2-3-8-5-6-10(9)11-8/h4,8,10-11H,2-3,5-6H2,1H3<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><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: SGNXVBOIDPPRJJ-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></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C10H15NO/c1-7(12)9-4-2-3-8-5-6-10(9)11-8/h4,8,10-11H,2-3,5-6H2,1H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: SGNXVBOIDPPRJJ-UHFFFAOYAZ</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC(=O)C1=CCCC2CCC1N2</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C<sub>10</sub>H<sub>15</sub>NO  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>165.232    </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=408396032&page2=Anatoxin-a">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <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><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Anatoxin-a</b>, also known as <b>Very Fast Death Factor</b> (<b>VFDF</b>), is a secondary, bicyclic <a href="/wiki/Amine" title="Amine">amine</a> <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> and <a href="/wiki/Cyanotoxin" title="Cyanotoxin">cyanotoxin</a> with acute <a href="/wiki/Neurotoxicity" title="Neurotoxicity">neurotoxicity</a>. It was first discovered in the early 1960s in Canada, and was isolated in 1972. The toxin is produced by multiple genera of <a href="/wiki/Cyanobacteria" title="Cyanobacteria">cyanobacteria</a> and has been reported in North America, South America, Central America, Europe, Africa, Asia, and Oceania. Symptoms of anatoxin-a toxicity include <a href="/wiki/Ataxia" title="Ataxia">loss of coordination</a>, <a href="/wiki/Fasciculation" title="Fasciculation">muscular fasciculations</a>, <a href="/wiki/Convulsion" title="Convulsion">convulsions</a> and death by <a href="/wiki/Respiratory_paralysis" class="mw-redirect" title="Respiratory paralysis">respiratory paralysis</a>. Its <a href="/wiki/Mode_of_action" title="Mode of action">mode of action</a> is through the <a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">nicotinic acetylcholine receptor</a> (nAchR) where it mimics the binding of the receptor's natural <a href="/wiki/Ligand" title="Ligand">ligand</a>, <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a>. As such, anatoxin-a has been used for medicinal purposes to investigate diseases characterized by low acetylcholine levels. Due to its high toxicity and potential presence in drinking water, anatoxin-a poses a threat to animals, including humans. While methods for detection and water treatment exist, scientists have called for more research to improve reliability and efficacy. Anatoxin-a is not to be confused with <a href="/wiki/Guanitoxin" title="Guanitoxin">guanitoxin</a> (formerly anatoxin-a(S)), another potent cyanotoxin that has a similar mechanism of action to that of anatoxin-a and is produced by many of the same cyanobacteria genera, but is structurally unrelated.<sup id="cite_ref-Aráoz_1-0" class="reference"><a href="#cite_note-Aráoz-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anatoxin-a was first discovered by P.R. Gorham in the early 1960s, after several herds of cattle died as a result of drinking water from <a href="/wiki/Saskatchewan_Lake" title="Saskatchewan Lake">Saskatchewan Lake</a> in Ontario, Canada, which contained toxic <a href="/wiki/Algal_blooms" class="mw-redirect" title="Algal blooms">algal blooms</a>. It was isolated in 1972 by J.P. Devlin from the cyanobacteria <i><a href="/wiki/Anabaena_flos-aquae" class="mw-redirect" title="Anabaena flos-aquae">Anabaena flos-aquae</a></i>.<sup id="cite_ref-Botana_2-0" class="reference"><a href="#cite_note-Botana-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=2" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anatoxin-a is a neurotoxin produced by multiple genera of freshwater cyanobacteria that are found in water bodies globally.<sup id="cite_ref-:0_3-0" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Some freshwater cyanobacteria are known to be salt tolerant and thus it is possible for anatoxin-a to be found in estuarine or other saline environments.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Blooms of cyanobacteria that produce anatoxin-a among other cyanotoxins are increasing in frequency due to increasing temperatures, <a href="/wiki/Stratification_(water)" title="Stratification (water)">stratification</a>, and <a href="/wiki/Eutrophication" title="Eutrophication">eutrophication</a> due to nutrient runoff.<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> These expansive cyanobacterial <a href="/wiki/Harmful_algal_bloom" title="Harmful algal bloom">harmful algal blooms</a>, known as cyanoHABs, increase the amount of cyanotoxins in the surrounding water, threatening the health of both aquatic and terrestrial organisms.<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> Some species of cyanobacteria that produce anatoxin-a don't produce surface water blooms but instead form <a href="/wiki/Benthic_zone" title="Benthic zone">benthic</a> mats. Many cases of anatoxin-a related animal deaths have occurred due to ingestion of detached benthic cyanobacterial mats that have washed ashore.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Anatoxin-a producing cyanobacteria have also been found in soils and aquatic plants. Anatoxin-a sorbs well to negatively charged sites in clay-like, organic-rich soils and weakly to sandy soils. One study found both bound and free anatoxin-a in 38% of aquatic plants sampled across 12 Nebraskan reservoirs, with much higher incidence of bound anatoxin-a than free.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Experimental_studies">Experimental studies</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=3" title="Edit section: Experimental studies"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1977, Carmichael, Gorham, and Biggs experimented with anatoxin-a. They introduced toxic cultures of <i>A. flos-aquae</i> into the stomachs of two young male calves, and observed that muscular fasciculations and loss of coordination occurred in a matter of minutes, while death due to respiratory failure occurred anywhere between several minutes and a few hours. They also established that extensive periods of <a href="/wiki/Artificial_respiration" class="mw-redirect" title="Artificial respiration">artificial respiration</a> did not allow for detoxification to occur and natural neuromuscular functioning to resume. From these experiments, they calculated that the oral minimum lethal dose (MLD) (of the algae, not the anatoxin molecule), for calves is roughly 420 mg/kg body weight.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>In the same year, Devlin and colleagues discovered the bicyclic secondary amine structure of anatoxin-a. They also performed experiments similar to those of Carmichael et al. on mice. They found that anatoxin-a kills mice 2–5 minutes after <a href="/wiki/Intraperitoneal_injection" title="Intraperitoneal injection">intraperitoneal injection</a> preceded by twitching, muscle spasms, paralysis and respiratory arrest, hence the name Very Fast Death Factor.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> They determined the <a href="/wiki/LD50" class="mw-redirect" title="LD50">LD50</a> for mice to be 250 μg/kg body weight.<sup id="cite_ref-Aráoz_1-1" class="reference"><a href="#cite_note-Aráoz-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Electrophysiological experiments done by Spivak et al. (1980) on frogs showed that anatoxin-a is a potent agonist of the muscle-type (α<sub>1</sub>)<sub>2</sub>βγδ nAChR. Anatoxin-a induced depolarizing neuromuscular blockade, contracture of the frog's rectus abdominis muscle, depolarization of the frog sartorius muscle, desensitization, and alteration of the action potential. Later, Thomas et al., (1993) through his work with chicken α<sub>4</sub>β<sub>2</sub> nAChR subunits expressed on mouse M 10 cells and chicken α<sub>7</sub> nAChR expressed in oocytes from <i><a href="/wiki/Xenopus_laevis" class="mw-redirect" title="Xenopus laevis">Xenopus laevis</a></i>, showed that anatoxin-a is also a potent agonist of neuronal nAChR.<sup id="cite_ref-Aráoz_1-2" class="reference"><a href="#cite_note-Aráoz-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=4" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Effects">Effects</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=5" title="Edit section: Effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Laboratory studies using mice showed that characteristic effects of acute anatoxin-a poisoning via <a href="/wiki/Intraperitoneal_injection" title="Intraperitoneal injection">intraperitoneal injection</a> include <a href="/wiki/Fasciculation" title="Fasciculation">muscle fasciculations</a>, tremors, staggering, gasping, respiratory paralysis, and death within minutes. Zebrafish exposed to anatoxin-a contaminated water had altered heart rates.<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> </p><p>There have been cases of non-lethal poisoning in humans who have ingested water from streams and lakes that contain various genera of cyanobacteria that are capable of producing anatoxin-a. The effects of non-lethal poisoning were primarily gastrointestinal: nausea, vomiting, diarrhea, and abdominal pain.<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> A case of lethal poisoning was reported in Wisconsin after a teen jumped into a pond contaminated with cyanobacteria.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Exposure_routes">Exposure routes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=6" title="Edit section: Exposure routes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Oral">Oral</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=7" title="Edit section: Oral"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ingestion of drinking water or recreational water that is contaminated with anatoxin-a can pose fatal consequences since anatoxin-a was found to be quickly absorbed through the gastrointestinal tract in animal studies.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Dozens of cases of animal deaths due to ingestion of anatoxin-a contaminated water from lakes or rivers have been recorded, and it is suspected to have also been the cause of death of one human.<sup id="cite_ref-ofmpub.epa.gov_15-0" class="reference"><a href="#cite_note-ofmpub.epa.gov-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> One study found that anatoxin-a is capable of binding to acetylcholine receptors and inducing toxic effects with concentrations in the nano-molar (nM) range if ingested.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Dermal">Dermal</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=8" title="Edit section: Dermal"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Dermal exposure is the most likely form of contact with cyanotoxins in the environment. Recreational exposure to river, stream, and lake waters contaminated with algal blooms has been known to cause skin irritation and rashes.<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> The first study that looked at <i><a href="/wiki/In_vitro" title="In vitro">in vitro</a></i> <a href="/wiki/Cytotoxicity" title="Cytotoxicity">cytotoxic</a> effects of anatoxin-a on human <a href="/wiki/Keratinocyte" title="Keratinocyte">skin cell</a> proliferation and migration found that anatoxin-a exerted no effect at 0.1 μg/mL or 1 μg/mL, and a weak toxic effect at 10 μg/mL only after an extended period of contact (48 hours).<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> </p> <div class="mw-heading mw-heading4"><h4 id="Inhalation">Inhalation</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=9" title="Edit section: Inhalation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>No data on inhalation toxicity of anatoxin-a is currently available, though severe <a href="/wiki/Shortness_of_breath" title="Shortness of breath">respiratory distress</a> occurred in a water skier after they inhaled water spray containing a fellow cyanobacterial neurotoxin, <a href="/wiki/Saxitoxin" title="Saxitoxin">saxitoxin</a>.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> It is possible that inhalation of water spray containing anatoxin-a could pose similar consequences. </p> <div class="mw-heading mw-heading3"><h3 id="Mechanism_of_toxicity">Mechanism of toxicity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=10" title="Edit section: Mechanism of toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anatoxin-a is an agonist of both neuronal α<sub>4</sub>β<sub>2</sub> and α<sub>4</sub> <a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">nicotinic acetylcholine receptors</a> present in the CNS as well as the (α<sub>1</sub>)<sub>2</sub>βγδ muscle-type nAchRs that are present at the <a href="/wiki/Neuromuscular_junction" title="Neuromuscular junction">neuromuscular junction</a>.<sup id="cite_ref-Aráoz_1-3" class="reference"><a href="#cite_note-Aráoz-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> (Anatoxin-a has an affinity for these muscle-type receptors that is about 20 times greater than that of <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a>.<sup id="cite_ref-Botana_2-1" class="reference"><a href="#cite_note-Botana-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>) However, the cyanotoxin has little effect on <a href="/wiki/Muscarinic_acetylcholine_receptors" class="mw-redirect" title="Muscarinic acetylcholine receptors">muscarinic acetylcholine receptors</a>; it has a 100 fold lesser selectivity for these types of receptors than it has for nAchRs.<sup id="cite_ref-Osswald_20-0" class="reference"><a href="#cite_note-Osswald-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Anatoxin-a also shows much less potency in the CNS than in neuromuscular junctions. In hippocampal and brain stem neurons, a 5 to 10 times greater concentration of anatoxin-a was necessary to activate nAchRs than what was required in the PNS.<sup id="cite_ref-Osswald_20-1" class="reference"><a href="#cite_note-Osswald-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>In normal circumstances, <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a> binds to nAchRs in the post-synaptic neuronal membrane, causing a conformational change in the extracellular domain of the receptor which in turn opens the channel pore. This allows Na<sup>+</sup> and Ca<sup>2+</sup> ions to move into the neuron, causing cell <a href="/wiki/Depolarization" title="Depolarization">depolarization</a> and inducing the generation of <a href="/wiki/Action_potential" title="Action potential">action potentials</a>, which allows for muscle contraction. The acetylcholine neurotransmitter then dissociates from the nAchR, where it is rapidly cleaved into <a href="/wiki/Acetate" title="Acetate">acetate</a> and <a href="/wiki/Choline" title="Choline">choline</a> by <a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase">acetylcholinesterase</a>.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Anatoxina.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Anatoxina.png/220px-Anatoxina.png" decoding="async" width="220" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Anatoxina.png/330px-Anatoxina.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Anatoxina.png/440px-Anatoxina.png 2x" data-file-width="687" data-file-height="373" /></a><figcaption>The effects of anatoxin-a on nicotinic acetylcholine receptors at the neuromuscular junction</figcaption></figure> <p>Anatoxin-a binding to these nAchRs cause the same effects in neurons. However, anatoxin-a <a href="/wiki/Irreversible_agonist" title="Irreversible agonist">binding is irreversible</a>, and the anatoxin-a nAchR complex cannot be broken down by <a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase">acetylcholinesterase</a>. Thus, the nAchR is temporarily locked open, which leads to overstimulation due to the constant generation of action potentials.<sup id="cite_ref-Osswald_20-2" class="reference"><a href="#cite_note-Osswald-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Two enantiomers of anatoxin-a, the positive <a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a>, (+)-anatoxin-a, is 150 fold more potent than the synthetic negative enantiomer, (−)-anatoxin-a.<sup id="cite_ref-Osswald_20-3" class="reference"><a href="#cite_note-Osswald-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> This is because (+)-anatoxin-a, the s-<i>cis</i> enone conformation, has a distance a 6.0 <a href="/wiki/Angstrom_(unit)" class="mw-redirect" title="Angstrom (unit)">Å</a> between its <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> and <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> group, which corresponds well to the 5.9 Å distance that separate the nitrogen and oxygen in acetylcholine.<sup id="cite_ref-Aráoz_1-4" class="reference"><a href="#cite_note-Aráoz-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Respiratory_arrest" title="Respiratory arrest">Respiratory arrest</a>, which results in a lack of an oxygen supply to the brain, is the most evident and lethal effect of anatoxin-a.<sup id="cite_ref-Osswald_20-4" class="reference"><a href="#cite_note-Osswald-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Injections of mice, rats, birds, dogs, and calves with lethal doses of anatoxin-a have demonstrated that death is preceded by a sequence of muscle <a href="/wiki/Fasciculations" class="mw-redirect" title="Fasciculations">fasciculations</a>, decreased movement, collapse, exaggerated abdominal breathing, <a href="/wiki/Cyanosis" title="Cyanosis">cyanosis</a> and <a href="/wiki/Convulsions" class="mw-redirect" title="Convulsions">convulsions</a>.<sup id="cite_ref-Botana_2-2" class="reference"><a href="#cite_note-Botana-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> In mice, anatoxin-a also seriously impacted blood pressure and heart rate, and caused severe <a href="/wiki/Acidosis" title="Acidosis">acidosis</a>.<sup id="cite_ref-Aráoz_1-5" class="reference"><a href="#cite_note-Aráoz-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cases_of_toxicity">Cases of toxicity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=11" title="Edit section: Cases of toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Flickr_-_Rainbirder_-_Born_of_Fire.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Flickr_-_Rainbirder_-_Born_of_Fire.jpg/220px-Flickr_-_Rainbirder_-_Born_of_Fire.jpg" decoding="async" width="220" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Flickr_-_Rainbirder_-_Born_of_Fire.jpg/330px-Flickr_-_Rainbirder_-_Born_of_Fire.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Flickr_-_Rainbirder_-_Born_of_Fire.jpg/440px-Flickr_-_Rainbirder_-_Born_of_Fire.jpg 2x" data-file-width="900" data-file-height="614" /></a><figcaption>Flamingos at Lake Bogoria</figcaption></figure> <p>Many cases of wildlife and livestock deaths due to anatoxin-a have been reported since its discovery. Domestic dog deaths due to the cyanotoxin, as determined by analysis of stomach contents, have been observed at the lower North Island in New Zealand in 2005,<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> in eastern France in 2003,<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> in California of the United States in 2002 and 2006,<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> in Scotland in 1992, in Ireland in 1997 and 2005,<sup id="cite_ref-Botana_2-3" class="reference"><a href="#cite_note-Botana-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> in Germany in 2017<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> and 2020.<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> In each case, the dogs began showing muscle convulsions within minutes, and were dead within a matter of hours. Numerous cattle fatalities arising from the consumption of water contaminated with cyanobacteria that produce anatoxin-a have been reported in the United States, Canada, and Finland between 1980 and the present.<sup id="cite_ref-Botana_2-4" class="reference"><a href="#cite_note-Botana-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>A particularly interesting case of anatoxin-a poisoning is that of <a href="/wiki/Lesser_flamingos" class="mw-redirect" title="Lesser flamingos">lesser flamingos</a> at <a href="/wiki/Lake_Bogoria" title="Lake Bogoria">Lake Bogoria</a> in <a href="/wiki/Kenya" title="Kenya">Kenya</a>. The cyanotoxin, which was identified in the stomachs and fecal pellets of the birds, killed roughly 30,000 flamingos in the second half of 1999, and continues to cause mass fatalities annually, devastating the flamingo population. The toxin is introduced into the birds via water contaminated with cyanobacterial mat communities that arise from the hot springs in the lake bed.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=12" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Laboratory_synthesis">Laboratory synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=13" title="Edit section: Laboratory synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Cyclic_expansion_of_tropanes">Cyclic expansion of tropanes</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=14" title="Edit section: Cyclic expansion of tropanes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div><p> The first biologically occurring initial substance for <a href="/wiki/Tropane" title="Tropane">tropane</a> expansion into anatoxin-a was <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, which has similar stereochemistry to anatoxin-a. Cocaine is first converted into the endo isomer of a cyclopropane, which is then photolytically cleaved to obtain an alpha, beta unsaturated ketone. Through the use of diethyl azodicarboxylate, the ketone is demethylated and anatoxin-a is formed. A similar, more recent synthesis pathway involves producing 2-tropinone from cocaine and treating the product with ethyl chloroformate producing a bicyclic ketone. This product is combined with trimethylsilyldiazylmethane, an organoaluminum Lewis acid and trimethylsinyl enol ether to produce tropinone. This method undergoes several more steps, producing useful intermediates as well as anatoxin-a as a final product.<sup id="cite_ref-Botana_2-5" class="reference"><a href="#cite_note-Botana-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Kokain_-_Cocaine.svg" class="mw-file-description"><img alt="Cocaine, a precursor for anatoxin-a synthesis." src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Kokain_-_Cocaine.svg/220px-Kokain_-_Cocaine.svg.png" decoding="async" width="220" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Kokain_-_Cocaine.svg/330px-Kokain_-_Cocaine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/66/Kokain_-_Cocaine.svg/440px-Kokain_-_Cocaine.svg.png 2x" data-file-width="332" data-file-height="164" /></a><figcaption>Cocaine, a precursor for anatoxin-a synthesis</figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Cyclization_of_cyclooctenes">Cyclization of cyclooctenes</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=15" title="Edit section: Cyclization of cyclooctenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first and most extensively explored approach used to synthesize anatoxin-a in vitro, cyclooctene cyclization involves 1,5-cyclooctadiene as its initial source. This starting substance is reacted to form methyl amine and combined with hypobromous acid to form anatoxin-a. Another method developed in the same laboratory uses aminoalcohol in conjunction with mercuric (II) acetate and sodium borohydride. The product of this reaction was transformed into an alpha, beta ketone and oxidized by ethyl azodicarboxylate to form anatoxin-a.<sup id="cite_ref-Botana_2-6" class="reference"><a href="#cite_note-Botana-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Enantioselective_enolization_strategy">Enantioselective enolization strategy</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=16" title="Edit section: Enantioselective enolization strategy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>This method for anatoxin-a production was one of the first used that does not utilize a chimerically analogous starting substance for anatoxin formation. Instead, a racemic mixture of 3-tropinone is used with a chiral lithium amide base and additional ring expansion reactions in order to produce a ketone intermediate. Addition of an organocuprate to the ketone produces an enol triflate derivative, which is then lysed hydrogenously and treated with a deprotecting agent in order to produce anatoxin-a. Similar strategies have also been developed and utilized by other laboratories.<sup id="cite_ref-Botana_2-7" class="reference"><a href="#cite_note-Botana-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Intramolecular_cyclization_of_iminium_ions">Intramolecular cyclization of iminium ions</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=17" title="Edit section: Intramolecular cyclization of iminium ions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Iminium ion cyclization utilizes several different pathways to create anatoxin-a, but each of these produces and progresses with a pyrrolidine iminium ion. The major differences in each pathway relate to the precursors used to produce the imium ion and the total yield of anatoxin-a at the end of the process. These separate pathways include production of alkyl iminium salts, acyl iminium salts and tosyl iminium salts.<sup id="cite_ref-Botana_2-8" class="reference"><a href="#cite_note-Botana-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Enyne_metathesis">Enyne metathesis</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=18" title="Edit section: Enyne metathesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Enyne metathesis of anatoxin-a involves the use of a ring closing mechanism and is one of the more recent advances in anatoxin-a synthesis. In all methods involving this pathway, pyroglutamic acid is used as a starting material in conjunction with a Grubb's catalyst. Similar to iminium cyclization, the first attempted synthesis of anatoxin-a using this pathway used a 2,5-cis-pyrrolidine as an intermediate.<sup id="cite_ref-Botana_2-9" class="reference"><a href="#cite_note-Botana-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=19" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anatoxin-a is synthesized <i>in vivo</i> in the species <i>Anabaena flos-aquae</i>,<sup id="cite_ref-Botana_2-10" class="reference"><a href="#cite_note-Botana-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> as well as several other genera of cyanobacteria. Anatoxin-a and related chemical structures are produced using acetate and glutamate. Further enzymatic reduction of these precursors results in the formation of anatoxin-a. Homoanatoxin, a similar chemical, is produced by <i>Oscillatoria formosa</i> and utilizes the same precursor. However, homoanatoxin undergoes a methyl addition by S-adenosyl-L-methionine instead of an addition of electrons, resulting in a similar analogue.<sup id="cite_ref-Aráoz_1-6" class="reference"><a href="#cite_note-Aráoz-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The biosynthetic gene cluster (BGC) for anatoxin-a was described from <i><a href="/wiki/Oscillatoria" title="Oscillatoria">Oscillatoria</a></i> PCC 6506 in 2009.<sup id="cite_ref-Méjean2009_28-0" class="reference"><a href="#cite_note-Méjean2009-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Stability_and_degradation">Stability and degradation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=20" title="Edit section: Stability and degradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anatoxin-a is unstable in water and other natural conditions, and in the presence of UV light undergoes <a href="/wiki/Photodegradation" title="Photodegradation">photodegradation</a>, being converted to the less toxic products dihydroanatoxin-a and epoxyanatoxin-a. The photodegradation of anatoxin-a is dependent on pH and sunlight intensity but independent of oxygen, indicating that the degradation by light is not achieved through the process of photo-oxidation.<sup id="cite_ref-Osswald_20-5" class="reference"><a href="#cite_note-Osswald-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Studies have shown that some microorganisms are capable of degrading anatoxin-a. A study done by Kiviranta and colleagues in 1991 showed that the bacterial genus <i><a href="/wiki/Pseudomonas" title="Pseudomonas">Pseudomonas</a></i> was capable of degrading anatoxin-a at a rate of 2–10 μg/ml per day.<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> Later experiments done by Rapala and colleagues (1994) supported these results. They compared the effects of sterilized and non-sterilized sediments on anatoxin-a degradation over the course of 22 days, and found that after that time vials with the sterilized sediments showed similar levels of anatoxin-a as at the commencement of the experiment, while vials with non-sterilized sediment showed a 25-48% decrease.<sup id="cite_ref-Osswald_20-6" class="reference"><a href="#cite_note-Osswald-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Detection">Detection</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=21" title="Edit section: Detection"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are two categories of anatoxin-a detection methods. Biological methods have involved administration of samples to mice and other organisms more commonly used in ecotoxicological testing, such as <a href="/wiki/Brine_shrimp" title="Brine shrimp">brine shrimp</a> (<i>Artemia salina</i>), larvae of the freshwater crustacean <i><a href="/w/index.php?title=Thamnocephalus_platyurus&action=edit&redlink=1" class="new" title="Thamnocephalus platyurus (page does not exist)">Thamnocephalus platyurus</a></i>, and various insect larvae. Problems with this methodology include an inability to determine whether it is anatoxin-a or another neurotoxin that causes the resulting deaths. Large amounts of sample material are also needed for such testing. In addition to the biological methods, scientists have used <a href="/wiki/Chromatography" title="Chromatography">chromatography</a> to detect anatoxin-a. This is complicated by the rapid degradation of the toxin and the lack of commercially available standards for anatoxin-a.<sup id="cite_ref-Osswald_20-7" class="reference"><a href="#cite_note-Osswald-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Public_health">Public health</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=22" title="Edit section: Public health"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Despite the relatively low frequency of anatoxin-a relative to other cyanotoxins, its high toxicity (the lethal dose is not known for humans, but is estimated to be less than 5 mg for an adult male<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>) means that it is still considered a serious threat to terrestrial and aquatic organisms, most significantly to livestock and to humans. Anatoxin-a is suspected to have been involved in the death of at least one person.<sup id="cite_ref-ofmpub.epa.gov_15-1" class="reference"><a href="#cite_note-ofmpub.epa.gov-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> The threat posed by anatoxin-a and other cyanotoxins is increasing as both fertilizer runoff, leading to <a href="/wiki/Eutrophication" title="Eutrophication">eutrophication</a> in lakes and rivers, and higher global temperatures contribute to a greater frequency and prevalence of cyanobacterial blooms.<sup id="cite_ref-Osswald_20-8" class="reference"><a href="#cite_note-Osswald-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Water_regulations">Water regulations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=23" title="Edit section: Water regulations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> in 1999 and <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">EPA</a> in 2006 both came to the conclusion that there was not enough toxicity data for anatoxin-a to establish a formal tolerable daily intake (TDI) level, though some places have implemented levels of their own.<sup id="cite_ref-:1_31-0" class="reference"><a href="#cite_note-:1-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="United_States">United States</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=24" title="Edit section: United States"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading5"><h5 id="Drinking_water_advisory_levels">Drinking water advisory levels</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=25" title="Edit section: Drinking water advisory levels"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anatoxin-a is not regulated under the <a href="/wiki/Safe_Drinking_Water_Act" title="Safe Drinking Water Act">Safe Drinking Water Act</a>, but states are allowed to create their own standards for contaminants that are unregulated. Currently there are four states that have set drinking water advisory levels for anatoxin-a as seen in the table below.<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> On October 8, 2009 the EPA published the third Drinking Water <a href="/wiki/Contaminant_candidate_list" class="mw-redirect" title="Contaminant candidate list">Contaminant Candidate List</a> (CCL) which included anatoxin-a (among other cyanotoxins), indicating that anatoxin-a may be present in public water systems but is not regulated by the EPA. Anatoxin-a's presence on the CCL means that it may need to be regulated by the EPA in the future, pending further information on its health effects in humans.<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><sup id="cite_ref-:1_31-1" class="reference"><a href="#cite_note-:1-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption>Drinking Water Advisory Levels </caption> <tbody><tr> <th>State </th> <th>Concentration (μg/L) </th></tr> <tr> <td>Minnesota </td> <td>0.1 </td></tr> <tr> <td>Ohio </td> <td>20 </td></tr> <tr> <td>Oregon </td> <td>0.7 </td></tr> <tr> <td>Vermont </td> <td>0.5 </td></tr></tbody></table> <div class="mw-heading mw-heading5"><h5 id="Recreational_water_advisory_levels">Recreational water advisory levels</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=26" title="Edit section: Recreational water advisory levels"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2008 the state of Washington implemented a recreational advisory level for anatoxin-a of 1 μg/L in order to better manage algal blooms in lakes and protect users from exposure to the blooms.<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> <div class="mw-heading mw-heading4"><h4 id="Canada">Canada</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=27" title="Edit section: Canada"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Canadian province of Québec has a drinking water Maximum Accepted Value for anatoxin-a of 3.7 μg/L.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="New_Zealand">New Zealand</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=28" title="Edit section: New Zealand"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>New Zealand has a drinking water Maximum Accepted Value for anatoxin-a of 6 μg/L.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Water_treatment">Water treatment</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=29" title="Edit section: Water treatment"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As of now, there is no official guideline level for anatoxin-a,<sup id="cite_ref-Ho_38-0" class="reference"><a href="#cite_note-Ho-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> although scientists estimate that a level of 1 μg l<sup>−1</sup> would be sufficiently low.<sup id="cite_ref-pmid10215107_39-0" class="reference"><a href="#cite_note-pmid10215107-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Likewise, there are no official guidelines regarding testing for anatoxin-a. Among methods of reducing the risk for cyanotoxins, including anatoxin-a, scientists look favorably on biological treatment methods because they do not require complicated technology, are low maintenance, and have low running costs. Few biological treatment options have been tested for anatoxin-a specifically, although a species of <i>Pseudomonas</i>, capable of biodegrading anatoxin-a at a rate of 2–10 μg ml<sup>−1</sup> d<sup>−1</sup>, has been identified. Biological (granular) <a href="/wiki/Activated_carbon" title="Activated carbon">activated carbon</a> (BAC) has also been tested as a method of biodegradation, but it is inconclusive whether biodegradation occurred or if anatoxin-a was simply adsorbing the activated carbon.<sup id="cite_ref-Ho_38-1" class="reference"><a href="#cite_note-Ho-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Others have called for additional studies to determine more about how to use activated carbon effectively.<sup id="cite_ref-Westrick_40-0" class="reference"><a href="#cite_note-Westrick-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>Chemical treatment methods are more common in drinking water treatment compared to biological treatment, and numerous processes have been suggested for anatoxin-a. <a href="/wiki/Oxidizing_agent" title="Oxidizing agent">Oxidants</a> such as <a href="/wiki/Potassium_permanganate" title="Potassium permanganate">potassium permanganate</a>, <a href="/wiki/Ozone" title="Ozone">ozone</a>, and advanced oxidation processes (<a href="/wiki/Advanced_oxidation_process" title="Advanced oxidation process">AOPs</a>) have worked in lowering levels of anatoxin-a, but others, including photocatalysis, UV <a href="/wiki/Photolysis" class="mw-redirect" title="Photolysis">photolysis</a>,<sup id="cite_ref-Westrick_40-1" class="reference"><a href="#cite_note-Westrick-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Water_chlorination" title="Water chlorination">chlorination</a>,<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> have not shown great efficacy. </p><p>Directly removing the cyanobacteria in the water treatment process through physical treatment (e.g., <a href="/wiki/Membrane_technology" title="Membrane technology">membrane filtration</a>) is another option because most of the anatoxin-a is contained within the cells when the bloom is growing. However, anatoxin-a is released from cyanobacteria into water when they <a href="/wiki/Senescence" title="Senescence">senesce</a> and lyse, so physical treatment may not remove all of the anatoxin-a present.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Additional research needs to be done to find more reliable and efficient methods of both detection and treatment.<sup id="cite_ref-Westrick_40-2" class="reference"><a href="#cite_note-Westrick-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Laboratory_uses">Laboratory uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=30" title="Edit section: Laboratory uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anatoxin-a is a very powerful nicotinic acetylcholine receptor agonist and as such has been extensively studied for medicinal purposes. It is mainly used as a pharmacological probe in order to investigate diseases characterized by low acetylcholine levels, such as <a href="/wiki/Muscular_dystrophy" title="Muscular dystrophy">muscular dystrophy</a>, <a href="/wiki/Myasthenia_gravis" title="Myasthenia gravis">myasthenia gravis</a>, <a href="/wiki/Alzheimer_disease" class="mw-redirect" title="Alzheimer disease">Alzheimer disease</a>, and <a href="/wiki/Parkinson_disease" class="mw-redirect" title="Parkinson disease">Parkinson disease</a>. Further research on anatoxin-a and other less potent analogues are being tested as possible replacements for acetylcholine.<sup id="cite_ref-Botana_2-11" class="reference"><a href="#cite_note-Botana-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Genera_of_cyanobacteria_that_produce_anatoxin-a">Genera of cyanobacteria that produce anatoxin-a</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=31" title="Edit section: Genera of cyanobacteria that produce anatoxin-a"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><i><a href="/wiki/Anabaena" title="Anabaena">Anabaena</a> (Dolichospermum)</i><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><i><a href="/wiki/Aphanizomenon" title="Aphanizomenon">Aphanizomenon</a></i><sup id="cite_ref-:1_31-2" class="reference"><a href="#cite_note-:1-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Cylindrospermopsis" title="Cylindrospermopsis">Cylindrospermopsis</a></i><sup id="cite_ref-:0_3-1" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Cylindrospermum" title="Cylindrospermum">Cylindrospermum</a></i></li> <li><i><a href="/wiki/Lyngbya" title="Lyngbya">Lyngbya</a></i><sup id="cite_ref-Paerl_2013_44-0" class="reference"><a href="#cite_note-Paerl_2013-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Microcystis" title="Microcystis">Microcystis</a></i><sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Nostoc" title="Nostoc">Nostoc</a></i><sup id="cite_ref-:0_3-2" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Oscillatoria" title="Oscillatoria">Oscillatoria</a></i><sup id="cite_ref-Paerl_2013_44-1" class="reference"><a href="#cite_note-Paerl_2013-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup></li> <li><i>Microcoleus (Phormidium)</i><sup id="cite_ref-Paerl_2013_44-2" class="reference"><a href="#cite_note-Paerl_2013-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Planktothrix" title="Planktothrix">Planktothrix</a></i><sup id="cite_ref-Paerl_2013_44-3" class="reference"><a href="#cite_note-Paerl_2013-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup></li> <li><i>Raphidiopsis</i><sup id="cite_ref-Paerl_2013_44-4" class="reference"><a href="#cite_note-Paerl_2013-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup></li> <li><i>Tychonema</i><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></li> <li><i>Woronichinia</i><sup id="cite_ref-Paerl_2013_44-5" class="reference"><a href="#cite_note-Paerl_2013-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=32" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Guanitoxin" title="Guanitoxin">Guanitoxin</a></li> <li><a href="/wiki/Epibatidine" title="Epibatidine">Epibatidine</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=33" 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-Aráoz-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Aráoz_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Aráoz_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Aráoz_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Aráoz_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Aráoz_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Aráoz_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Aráoz_1-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFAráozMolgóTandeau_de_Marsac2010" class="citation journal cs1">Aráoz R, Molgó J, Tandeau de Marsac N (October 2010). "Neurotoxic cyanobacterial toxins". <i>Toxicon</i>. <b>56</b> (5): <span class="nowrap">813–</span>28. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.toxicon.2009.07.036">10.1016/j.toxicon.2009.07.036</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/19660486">19660486</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Toxicon&rft.atitle=Neurotoxic+cyanobacterial+toxins&rft.volume=56&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E813-%3C%2Fspan%3E28&rft.date=2010-10&rft_id=info%3Adoi%2F10.1016%2Fj.toxicon.2009.07.036&rft_id=info%3Apmid%2F19660486&rft.aulast=Ar%C3%A1oz&rft.aufirst=R&rft.au=Molg%C3%B3%2C+J&rft.au=Tandeau+de+Marsac%2C+N&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnatoxin-a" class="Z3988"></span></span> </li> <li id="cite_note-Botana-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Botana_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Botana_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Botana_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Botana_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Botana_2-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Botana_2-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Botana_2-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Botana_2-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Botana_2-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Botana_2-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-Botana_2-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-Botana_2-11"><sup><i><b>l</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBotanaJamesCrowleyDuphard2007" class="citation book cs1">Botana LM, James K, Crowley J, Duphard J, Lehane M, Furey A (March 2007). 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(1993). "Hepatotoxin (microcystin) and neurotoxin (anatoxin-a) contained in natural blooms and strains of cyanobacteria from Japanese freshwaters". <i>Natural Toxins</i>. <b>1</b> (6): <span class="nowrap">353–</span>60. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fnt.2620010606">10.1002/nt.2620010606</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/8167957">8167957</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Natural+Toxins&rft.atitle=Hepatotoxin+%28microcystin%29+and+neurotoxin+%28anatoxin-a%29+contained+in+natural+blooms+and+strains+of+cyanobacteria+from+Japanese+freshwaters&rft.volume=1&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E353-%3C%2Fspan%3E60&rft.date=1993&rft_id=info%3Adoi%2F10.1002%2Fnt.2620010606&rft_id=info%3Apmid%2F8167957&rft.aulast=Park&rft.aufirst=HD&rft.au=Watanabe%2C+MF&rft.au=Harda%2C+K&rft.au=Nagai%2C+H&rft.au=Suzuki%2C+M&rft.au=Watanabe%2C+M&rft.au=Hayashi%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnatoxin-a" class="Z3988"></span></span> </li> <li id="cite_note-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-46">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShamsCapelliCerasinoBallot2015" class="citation journal cs1">Shams S, Capelli C, Cerasino L, Ballot A, Dietrich DR, Sivonen K, et al. (February 2015). <a rel="nofollow" class="external text" href="http://nbn-resolving.de/urn:nbn:de:bsz:352-0-286858">"Anatoxin-a producing Tychonema (Cyanobacteria) in European waterbodies"</a>. <i>Water Research</i>. <b>69</b>: <span class="nowrap">68–</span>79. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2015WatRe..69...68S">2015WatRe..69...68S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.watres.2014.11.006">10.1016/j.watres.2014.11.006</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/25437339">25437339</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Water+Research&rft.atitle=Anatoxin-a+producing+Tychonema+%28Cyanobacteria%29+in+European+waterbodies&rft.volume=69&rft.pages=%3Cspan+class%3D%22nowrap%22%3E68-%3C%2Fspan%3E79&rft.date=2015-02&rft_id=info%3Apmid%2F25437339&rft_id=info%3Adoi%2F10.1016%2Fj.watres.2014.11.006&rft_id=info%3Abibcode%2F2015WatRe..69...68S&rft.aulast=Shams&rft.aufirst=S&rft.au=Capelli%2C+C&rft.au=Cerasino%2C+L&rft.au=Ballot%2C+A&rft.au=Dietrich%2C+DR&rft.au=Sivonen%2C+K&rft.au=Salmaso%2C+N&rft_id=http%3A%2F%2Fnbn-resolving.de%2Furn%3Anbn%3Ade%3Absz%3A352-0-286858&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnatoxin-a" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anatoxin-a&action=edit&section=34" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin" style=""> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWoodRasmussenHollandCampbell2007" class="citation journal cs1">Wood SA, Rasmussen JP, Holland PT, Campbell R, Crowe AL (2007). "First Report of the Cyanotoxin Anatoxin-A from Aphanizomenon issatschenkoi (cyanobacteria)". <i>Journal of Phycology</i>. <b>43</b> (2): <span class="nowrap">356–</span>365. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1529-8817.2007.00318.x">10.1111/j.1529-8817.2007.00318.x</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:84284928">84284928</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Phycology&rft.atitle=First+Report+of+the+Cyanotoxin+Anatoxin-A+from+Aphanizomenon+issatschenkoi+%28cyanobacteria%29&rft.volume=43&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E356-%3C%2Fspan%3E365&rft.date=2007&rft_id=info%3Adoi%2F10.1111%2Fj.1529-8817.2007.00318.x&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A84284928%23id-name%3DS2CID&rft.aulast=Wood&rft.aufirst=SA&rft.au=Rasmussen%2C+JP&rft.au=Holland%2C+PT&rft.au=Campbell%2C+R&rft.au=Crowe%2C+AL&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnatoxin-a" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWonnacottGallagher2006" class="citation journal cs1">Wonnacott S, Gallagher T (April 2006). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3663412">"The Chemistry and Pharmacology of Anatoxin-a and Related Homotropanes with respect to Nicotinic Acetylcholine Receptors"</a>. <i>Marine Drugs</i>. <b>4</b> (3): <span class="nowrap">228–</span>254. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fmd403228">10.3390/md403228</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3663412">3663412</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Marine+Drugs&rft.atitle=The+Chemistry+and+Pharmacology+of+Anatoxin-a+and+Related+Homotropanes+with+respect+to+Nicotinic+Acetylcholine+Receptors.&rft.volume=4&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E228-%3C%2Fspan%3E254&rft.date=2006-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3663412%23id-name%3DPMC&rft_id=info%3Adoi%2F10.3390%2Fmd403228&rft.aulast=Wonnacott&rft.aufirst=S&rft.au=Gallagher%2C+T&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3663412&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnatoxin-a" class="Z3988"></span></li></ul> </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=Anatoxin-a&action=edit&section=35" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.periodicvideos.com/videos/mv_veryfastdeathfactor.htm">Very Fast Death Factor (Anatoxin-a)</a> at <i><a href="/wiki/The_Periodic_Table_of_Videos" class="mw-redirect" title="The Periodic Table of Videos">The Periodic Table of Videos</a></i> (University of Nottingham)</li> <li><a rel="nofollow" class="external text" href="http://www.chm.bris.ac.uk/motm/antx/antx.htm">Molecule of the Month: Anatoxin</a> at the School of Chemistry, Physics, and Environmental Studies, University of Sussex at Brighton</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline 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title="Antillatoxin">Antillatoxin</a></li> <li><a href="/wiki/Beta-Methylamino-L-alanine" class="mw-redirect" title="Beta-Methylamino-L-alanine">BMAA</a></li> <li><a href="/wiki/Kalkitoxin" title="Kalkitoxin">Kalkitoxin</a></li> <li><a href="/wiki/Saxitoxin" title="Saxitoxin">Saxitoxin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hepatotoxin" title="Hepatotoxin">Hepatotoxins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cylindrospermopsin" title="Cylindrospermopsin">Cylindrospermopsin</a></li> <li><a href="/wiki/Microcystin" title="Microcystin">Microcystins</a> (e.g. <a href="/wiki/Microcystin-LR" title="Microcystin-LR">Microcystin-LR</a>)</li> <li><a href="/wiki/Nodularin" title="Nodularin">Nodularin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aplysiatoxin" title="Aplysiatoxin">Aplysiatoxin</a></li> <li><a href="/wiki/Apratoxin_A" title="Apratoxin A">Apratoxin A</a></li> <li><a href="/wiki/Caldoramide" title="Caldoramide">Caldoramide</a></li> <li><a href="/wiki/Coibamide_A" title="Coibamide A">Coibamide A</a></li> <li><a href="/wiki/Cyanobacterin" title="Cyanobacterin">Cyanobacterin</a></li> <li><a href="/wiki/Cyanopeptolin" title="Cyanopeptolin">Cyanopeptolin</a></li> <li><a href="/wiki/Cyclamide" title="Cyclamide">Cyclamide</a></li> <li><a href="/wiki/Debromoaplysiatoxin" title="Debromoaplysiatoxin">Debromoaplysiatoxin</a></li> <li><a href="/wiki/Lyngbyatoxin-a" title="Lyngbyatoxin-a">Lyngbyatoxin-a</a></li> <li><a href="/wiki/Microviridin" title="Microviridin">Microviridin</a></li> <li><a href="/wiki/Aetokthonotoxin" title="Aetokthonotoxin">Aetokthonotoxin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Cyanotoxins" title="Category:Cyanotoxins">Category</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Neurotoxins205" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Neurotoxins" title="Template:Neurotoxins"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Neurotoxins" title="Template talk:Neurotoxins"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Neurotoxins" title="Special:EditPage/Template:Neurotoxins"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Neurotoxins205" style="font-size:114%;margin:0 4em"><a href="/wiki/Neurotoxin" title="Neurotoxin">Neurotoxins</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Animal toxins</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Batrachotoxin" title="Batrachotoxin">Batrachotoxin</a></li> <li><a href="/wiki/Bestoxin" title="Bestoxin">Bestoxin</a></li> <li><a href="/wiki/Birtoxin" title="Birtoxin">Birtoxin</a></li> <li><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxin</a></li> <li><a href="/wiki/Charybdotoxin" title="Charybdotoxin">Charybdotoxin</a></li> <li><a href="/wiki/Conotoxin" title="Conotoxin">Conotoxin</a></li> <li><a href="/wiki/Fasciculin" title="Fasciculin">Fasciculin</a></li> <li><a href="/wiki/Huwentoxin" title="Huwentoxin">Huwentoxin</a></li> <li><a href="/wiki/Poneratoxin" title="Poneratoxin">Poneratoxin</a></li> <li><a href="/wiki/Saxitoxin" title="Saxitoxin">Saxitoxin</a></li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</a></li> <li><a href="/wiki/Vanillotoxin" title="Vanillotoxin">Vanillotoxin</a></li> <li><a href="/wiki/Ssm_spooky_toxin" title="Ssm spooky toxin">Spooky toxin (SsTx)</a></li> <li><a href="/wiki/Epibatidine" title="Epibatidine">Epibatidine</a></li> <li><a href="/wiki/Zetekitoxin_AB" title="Zetekitoxin AB">Zetekitoxin AB</a></li> <li><a href="/wiki/Dendrotoxin" title="Dendrotoxin">Dendrotoxin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bacterial_toxin" class="mw-redirect" title="Bacterial toxin">Bacterial</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a></li> <li><a href="/wiki/Tetanospasmin" class="mw-redirect" title="Tetanospasmin">Tetanospasmin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cyanotoxin" title="Cyanotoxin">Cyanotoxins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Anatoxin-a</a></li> <li><a href="/wiki/Guanitoxin" title="Guanitoxin">Guanitoxin</a></li> <li><a href="/wiki/Beta-Methylamino-L-alanine" class="mw-redirect" title="Beta-Methylamino-L-alanine">BMAA</a></li> <li><a href="/wiki/Saxitoxin" title="Saxitoxin">Saxitoxin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Plant_toxin" class="mw-redirect" title="Plant toxin">Plant toxins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aconitine" title="Aconitine">Aconitine</a></li> <li><a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/wiki/Penitrem_A" title="Penitrem A">Penitrem A</a></li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Tutin_(toxin)" title="Tutin (toxin)">Tutin</a></li> <li><a href="/wiki/Rotenone" title="Rotenone">Rotenone</a></li> <li><a href="/wiki/Ginkgotoxin" title="Ginkgotoxin">Ginkgotoxin</a></li> <li><a href="/wiki/Cicutoxin" title="Cicutoxin">Cicutoxin</a></li> <li><a href="/wiki/Oenanthotoxin" title="Oenanthotoxin">Oenanthotoxin</a></li> <li><a href="/wiki/Thujone" title="Thujone">Thujone</a></li> <li><a href="/wiki/Volkensin" title="Volkensin">Volkensin</a></li> <li><a href="/wiki/Veratridine" title="Veratridine">Veratridine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mycotoxin" title="Mycotoxin">Mycotoxins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/Muscarine" title="Muscarine">Muscarine</a></li> <li><a href="/wiki/Muscimol" title="Muscimol">Muscimol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fenpropathrin" title="Fenpropathrin">Fenpropathrin</a></li> <li><a href="/wiki/Tetramethylenedisulfotetramine" title="Tetramethylenedisulfotetramine">Tetramethylenedisulfotetramine</a></li> <li><a href="/wiki/Bromethalin" title="Bromethalin">Bromethalin</a></li> <li><a href="/wiki/Crimidine" title="Crimidine">Crimidine</a></li> <li><a href="/wiki/Methamidophos" title="Methamidophos">Methamidophos</a></li> <li><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></li> <li><a href="/wiki/Fipronil" title="Fipronil">Fipronil</a></li> <li><a href="/wiki/Phenylsilatrane" title="Phenylsilatrane">Phenylsilatrane</a></li> <li><a href="/wiki/Chlorophenylsilatrane" title="Chlorophenylsilatrane">Chlorophenylsilatrane</a></li> <li><a href="/wiki/Sulfuryl_fluoride" title="Sulfuryl fluoride">Sulfuryl fluoride</a></li> <li><a href="/wiki/Mipafox" title="Mipafox">Mipafox</a></li> <li><a href="/wiki/Schradan" title="Schradan">Schradan</a></li> <li><a href="/wiki/Dimefox" title="Dimefox">Dimefox</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nerve_agent" title="Nerve agent">Nerve agents</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclosarin" title="Cyclosarin">Cyclosarin</a></li> <li><a href="/wiki/EA-3148" title="EA-3148">EA-3148</a></li> <li><a href="/wiki/Novichok_agent" class="mw-redirect" title="Novichok agent">Novichok agent</a></li> <li><a href="/wiki/Sarin" title="Sarin">Sarin</a></li> <li><a href="/wiki/Soman" title="Soman">Soman</a></li> <li><a href="/wiki/Tabun_(nerve_agent)" title="Tabun (nerve agent)">Tabun</a></li> <li><a href="/wiki/VE_(nerve_agent)" title="VE (nerve agent)">VE</a></li> <li><a href="/wiki/VG_(nerve_agent)" title="VG (nerve agent)">VG</a></li> <li><a href="/wiki/VM_(nerve_agent)" title="VM (nerve agent)">VM</a></li> <li><a href="/wiki/VP_(nerve_agent)" class="mw-redirect" title="VP (nerve agent)">VP</a></li> <li><a href="/wiki/VR_(nerve_agent)" title="VR (nerve agent)">VR</a></li> <li><a href="/wiki/VX_(nerve_agent)" title="VX (nerve agent)">VX</a></li> <li><a href="/wiki/GV_(nerve_agent)" title="GV (nerve agent)">GV</a></li> <li><a href="/wiki/EA-3990" title="EA-3990">EA-3990</a></li> <li><a href="/wiki/EA-4056" title="EA-4056">EA-4056</a></li> <li><a href="/wiki/T-1123" title="T-1123">T-1123</a></li> <li><a href="/wiki/Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium_bromide)" title="Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)">Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)</a></li> <li><a href="/wiki/Fluorotabun" title="Fluorotabun">Fluorotabun</a></li> <li><a href="/wiki/Chinese_VX" title="Chinese VX">Chinese VX</a></li> <li><a href="/wiki/EA-2192" title="EA-2192">EA-2192</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bicyclic_phosphate" title="Bicyclic phosphate">Bicyclic phosphates</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/TBPS" title="TBPS">TBPS</a></li> <li><a href="/wiki/TBPO" title="TBPO">TBPO</a></li> <li><a href="/wiki/IPTBO" title="IPTBO">IPTBO</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Cholinergic neurotoxins</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Acetylcholine_mustard&action=edit&redlink=1" class="new" title="Acetylcholine mustard (page does not exist)">Acetylcholine mustard</a></li> <li><a href="/w/index.php?title=Catecholine&action=edit&redlink=1" class="new" title="Catecholine (page does not exist)">Catecholine</a></li> <li><a href="/w/index.php?title=Choline_mustard&action=edit&redlink=1" class="new" title="Choline mustard (page does not exist)">Choline mustard</a></li> <li><a href="/wiki/Ethylcholine_mustard" title="Ethylcholine mustard">Ethylcholine mustard</a></li> <li><a href="/w/index.php?title=Hemicholinium_mustard&action=edit&redlink=1" class="new" title="Hemicholinium mustard (page does not exist)">Hemicholinium mustard</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Psychoactive_drug" title="Psychoactive drug">Psychoactive drugs</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Alcohol</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dimethylcadmium" title="Dimethylcadmium">Dimethylcadmium</a></li> <li><a href="/wiki/Dimethylmercury" title="Dimethylmercury">Dimethylmercury</a></li> <li><a href="/wiki/Toxopyrimidine" title="Toxopyrimidine">Toxopyrimidine</a></li> <li><a href="/wiki/IDPN_(chemical)" title="IDPN (chemical)">IDPN</a></li> <li><a href="/wiki/Tetraethyllead" title="Tetraethyllead">Tetraethyllead</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Nicotinic_acetylcholine_receptor_modulators859" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nicotinic_acetylcholine_receptor_modulators" title="Template talk:Nicotinic acetylcholine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nicotinic_acetylcholine_receptor_modulators" title="Special:EditPage/Template:Nicotinic acetylcholine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nicotinic_acetylcholine_receptor_modulators859" style="font-size:114%;margin:0 4em"><a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">Nicotinic acetylcholine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Nicotinic_acetylcholine_receptors" class="mw-redirect" title="Nicotinic acetylcholine receptors"><abbr title="Nicotinic acetylcholine receptors">nAChRs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Nicotinic acetylcholine receptors</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_agonist" class="mw-redirect" title="Receptor agonist">Agonists</a><br />(and <a href="/wiki/Positive_allosteric_modulators" class="mw-redirect" title="Positive allosteric modulators"><abbr title="positive allosteric modulators">PAMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip positive allosteric modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li> <li><a href="/wiki/6-Chloronicotine" title="6-Chloronicotine">6-Chloronicotine</a></li> <li><a href="/wiki/A-84,543" title="A-84,543">A-84,543</a></li> <li><a href="/wiki/A-366,833" title="A-366,833">A-366,833</a></li> <li><a href="/w/index.php?title=A-582,941&action=edit&redlink=1" class="new" title="A-582,941 (page does not exist)">A-582,941</a></li> <li><a href="/w/index.php?title=A-867,744&action=edit&redlink=1" class="new" title="A-867,744 (page does not exist)">A-867,744</a></li> <li><a href="/wiki/ABT-202" title="ABT-202">ABT-202</a></li> <li><a href="/wiki/ABT-418" title="ABT-418">ABT-418</a></li> <li><a href="/w/index.php?title=ABT-560&action=edit&redlink=1" class="new" title="ABT-560 (page does not exist)">ABT-560</a></li> <li><a href="/w/index.php?title=ABT-894&action=edit&redlink=1" class="new" title="ABT-894 (page does not exist)">ABT-894</a></li> <li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li> <li><a href="/wiki/Altinicline" title="Altinicline">Altinicline</a></li> <li><a href="/wiki/Anabasine" title="Anabasine">Anabasine</a></li> <li><a href="/wiki/Anatabine" title="Anatabine">Anatabine</a></li> <li><a class="mw-selflink selflink">Anatoxin-a</a></li> <li><a href="/wiki/AR-R17779" title="AR-R17779">AR-R17779</a></li> <li><a href="/wiki/Bephenium_hydroxynaphthoate" title="Bephenium hydroxynaphthoate">Bephenium hydroxynaphthoate</a></li> <li><a href="/wiki/Butinoline" title="Butinoline">Butinoline</a></li> <li><a href="/wiki/Butyrylcholine" title="Butyrylcholine">Butyrylcholine</a></li> <li><a href="/wiki/Carbachol" title="Carbachol">Carbachol</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Choline_m-bromophenyl_ether" title="Choline m-bromophenyl ether">Choline m-bromophenyl ether</a></li> <li><a href="/wiki/Cotinine" title="Cotinine">Cotinine</a></li> <li><a href="/wiki/Cytisine" title="Cytisine">Cytisine</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Dianicline" title="Dianicline">Dianicline</a></li> <li><a href="/wiki/Dimethylphenylpiperazinium" title="Dimethylphenylpiperazinium">Dimethylphenylpiperazinium</a></li> <li><a href="/wiki/Epibatidine" title="Epibatidine">Epibatidine</a></li> <li><a href="/wiki/Epiboxidine" title="Epiboxidine">Epiboxidine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Ethoxysebacylcholine&action=edit&redlink=1" class="new" title="Ethoxysebacylcholine (page does not exist)">Ethoxysebacylcholine</a></li> <li><a href="/w/index.php?title=EVP-4473&action=edit&redlink=1" class="new" title="EVP-4473 (page does not exist)">EVP-4473</a></li> <li><a href="/wiki/EVP-6124" class="mw-redirect" title="EVP-6124">EVP-6124</a></li> <li><a href="/wiki/Galantamine" title="Galantamine">Galantamine</a></li> <li><a href="/wiki/GTS-21" title="GTS-21">GTS-21</a></li> <li><a href="/wiki/Ispronicline" title="Ispronicline">Ispronicline</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/JNJ-39393406" title="JNJ-39393406">JNJ-39393406</a></li> <li><a href="/wiki/Levamisole" title="Levamisole">Levamisole</a></li> <li><a href="/wiki/Lobeline" title="Lobeline">Lobeline</a></li> <li><a href="/w/index.php?title=MEM-63,908&action=edit&redlink=1" class="new" title="MEM-63,908 (page does not exist)">MEM-63,908 (RG-3487)</a></li> <li><a href="/wiki/Morantel" title="Morantel">Morantel</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/w/index.php?title=NS-1738&action=edit&redlink=1" class="new" title="NS-1738 (page does not exist)">NS-1738</a></li> <li><a href="/wiki/PHA-543,613" title="PHA-543,613">PHA-543,613</a></li> <li><a href="/w/index.php?title=PHA-709,829&action=edit&redlink=1" class="new" title="PHA-709,829 (page does not exist)">PHA-709,829</a></li> <li><a href="/wiki/PNU-120,596" title="PNU-120,596">PNU-120,596</a></li> <li><a href="/wiki/PNU-282,987" title="PNU-282,987">PNU-282,987</a></li> <li><a href="/wiki/Pozanicline" title="Pozanicline">Pozanicline</a></li> <li><a href="/wiki/Pyrantel" title="Pyrantel">Pyrantel</a></li> <li><a href="/wiki/Rivanicline" title="Rivanicline">Rivanicline</a></li> <li><a href="/wiki/RJR-2429" title="RJR-2429">RJR-2429</a></li> <li><a href="/wiki/Sazetidine_A" title="Sazetidine A">Sazetidine A</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/w/index.php?title=Sebacylcholine&action=edit&redlink=1" class="new" title="Sebacylcholine (page does not exist)">Sebacylcholine</a></li> <li><a href="/wiki/SIB-1508Y" class="mw-redirect" title="SIB-1508Y">SIB-1508Y</a></li> <li><a href="/wiki/SIB-1553A" title="SIB-1553A">SIB-1553A</a></li> <li><a href="/wiki/SSR-180,711" title="SSR-180,711">SSR-180,711</a></li> <li><a href="/w/index.php?title=Suberyldicholine&action=edit&redlink=1" class="new" title="Suberyldicholine (page does not exist)">Suberyldicholine</a></li> <li><a href="/wiki/Suxamethonium" class="mw-redirect" title="Suxamethonium">Suxamethonium (succinylcholine)</a></li> <li><a href="/wiki/Suxethonium_chloride" title="Suxethonium chloride">Suxethonium (succinyldicholine)</a></li> <li><a href="/wiki/TC-1698" title="TC-1698">TC-1698</a></li> <li><a href="/w/index.php?title=TC-1734&action=edit&redlink=1" class="new" title="TC-1734 (page does not exist)">TC-1734</a></li> <li><a href="/wiki/TC-1827" title="TC-1827">TC-1827</a></li> <li><a href="/wiki/TC-2216" title="TC-2216">TC-2216</a></li> <li><a href="/wiki/TC-5214" class="mw-redirect" title="TC-5214">TC-5214</a></li> <li><a href="/wiki/TC-5619" class="mw-redirect" title="TC-5619">TC-5619</a></li> <li><a href="/w/index.php?title=TC-6683&action=edit&redlink=1" class="new" title="TC-6683 (page does not exist)">TC-6683</a></li> <li><a href="/wiki/Tebanicline" title="Tebanicline">Tebanicline</a></li> <li><a href="/wiki/Tribendimidine" title="Tribendimidine">Tribendimidine</a></li> <li><a href="/wiki/Tropisetron" title="Tropisetron">Tropisetron</a></li> <li><a href="/wiki/UB-165" title="UB-165">UB-165</a></li> <li><a href="/wiki/Varenicline" title="Varenicline">Varenicline</a></li> <li><a href="/wiki/WAY-317,538" class="mw-redirect" title="WAY-317,538">WAY-317,538</a></li> <li><a href="/w/index.php?title=XY-4083&action=edit&redlink=1" class="new" title="XY-4083 (page does not exist)">XY-4083</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Antagonists</a><br />(and <a href="/wiki/Negative_allosteric_modulators" class="mw-redirect" title="Negative allosteric modulators"><abbr title="negative allosteric modulators">NAMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip negative allosteric modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/18-Methylaminocoronaridine" title="18-Methylaminocoronaridine">18-MAC</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/%CE%91-Neurotoxin" title="Α-Neurotoxin">α-Neurotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%91-cobratoxin" class="mw-redirect" title="Α-cobratoxin">α-cobratoxin</a>, <a href="/wiki/%CE%91-conotoxin" class="mw-redirect" title="Α-conotoxin">α-conotoxin</a>, many others)</li> <li><a href="/w/index.php?title=ABT-126&action=edit&redlink=1" class="new" title="ABT-126 (page does not exist)">ABT-126</a></li> <li><a href="/wiki/Alcuronium" class="mw-redirect" title="Alcuronium">Alcuronium</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/w/index.php?title=Anatruxonium&action=edit&redlink=1" class="new" title="Anatruxonium (page does not exist)">Anatruxonium</a></li> <li><a href="/w/index.php?title=AQW051&action=edit&redlink=1" class="new" title="AQW051 (page does not exist)">AQW051</a></li> <li><a href="/wiki/Atracurium" class="mw-redirect" title="Atracurium">Atracurium</a></li> <li><a href="/wiki/Barbiturates" class="mw-redirect" title="Barbiturates">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/BNC-210" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%9A-bungarotoxin" class="mw-redirect" title="Κ-bungarotoxin">κ-bungarotoxin</a>)</li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/BW284C51" title="BW284C51">BW284C51</a></li> <li><a href="/wiki/BW-A444" title="BW-A444">BW-A444</a></li> <li><a href="/wiki/Candocuronium_iodide" title="Candocuronium iodide">Candocuronium iodide (chandonium iodide)</a></li> <li><a href="/wiki/Chlorisondamine" title="Chlorisondamine">Chlorisondamine</a></li> <li><a href="/wiki/Cisatracurium" class="mw-redirect" title="Cisatracurium">Cisatracurium</a></li> <li><a href="/wiki/Coclaurine" title="Coclaurine">Coclaurine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Curare" title="Curare">Curare</a></li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Dacuronium_bromide" title="Dacuronium bromide">Dacuronium bromide</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Dehydronorketamine" title="Dehydronorketamine">Dehydronorketamine</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/w/index.php?title=Diadonium&action=edit&redlink=1" class="new" title="Diadonium (page does not exist)">Diadonium</a></li> <li><a href="/w/index.php?title=Dihydro-beta-erythroidine&action=edit&redlink=1" class="new" title="Dihydro-beta-erythroidine (page does not exist)">DHβE</a></li> <li><a href="/wiki/Dihydrochandonium" title="Dihydrochandonium">Dihydrochandonium</a></li> <li><a href="/wiki/Dimethyltubocurarine" class="mw-redirect" title="Dimethyltubocurarine">Dimethyltubocurarine (metocurine)</a></li> <li><a href="/wiki/Dioscorine" title="Dioscorine">Dioscorine</a></li> <li><a href="/wiki/Dipyrandium" title="Dipyrandium">Dipyrandium</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine (MK-801)</a></li> <li><a href="/wiki/Doxacurium" class="mw-redirect" title="Doxacurium">Doxacurium</a></li> <li><a href="/wiki/Encenicline" title="Encenicline">Encenicline</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Erythravine" title="Erythravine">Erythravine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Fazadinium" class="mw-redirect" title="Fazadinium">Fazadinium</a></li> <li><a href="/wiki/Gallamine" class="mw-redirect" title="Gallamine">Gallamine</a></li> <li><a href="/wiki/Gantacurium_chloride" title="Gantacurium chloride">Gantacurium chloride</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Hexafluronium" class="mw-redirect" title="Hexafluronium">Hexafluronium</a></li> <li><a href="/wiki/Hexamethonium" title="Hexamethonium">Hexamethonium (benzohexonium)</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Hydroxynorketamine" title="Hydroxynorketamine">Hydroxynorketamine</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/wiki/Laudexium" class="mw-redirect" title="Laudexium">Laudexium (laudolissin)</a></li> <li><a href="/wiki/Levacetylmethadol" title="Levacetylmethadol">Levacetylmethadol</a></li> <li><a href="/wiki/Levomethadone" title="Levomethadone">Levomethadone</a></li> <li><a href="/wiki/Malouetine" title="Malouetine">Malouetine</a></li> <li><a href="/wiki/2-Methoxyethyl-18-methoxycoronaridinate" title="2-Methoxyethyl-18-methoxycoronaridinate">ME-18-MC</a></li> <li><a href="/wiki/Mecamylamine" title="Mecamylamine">Mecamylamine</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Methorphan" title="Methorphan">Methorphan (racemethorphan)</a></li> <li><a href="/wiki/Methyllycaconitine" title="Methyllycaconitine">Methyllycaconitine</a></li> <li><a href="/wiki/Metocurine" title="Metocurine">Metocurine</a></li> <li><a href="/wiki/Mivacurium" class="mw-redirect" title="Mivacurium">Mivacurium</a></li> <li><a href="/wiki/Morphanol" class="mw-redirect" title="Morphanol">Morphanol (racemorphan)</a></li> <li><a href="/wiki/Neramexane" title="Neramexane">Neramexane</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Pancuronium_bromide" title="Pancuronium bromide">Pancuronium bromide</a></li> <li><a href="/wiki/Pempidine" title="Pempidine">Pempidine</a></li> <li><a href="/wiki/Pentamine" title="Pentamine">Pentamine</a></li> <li><a href="/wiki/Pentolinium" title="Pentolinium">Pentolinium</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Pipecuronium_bromide" title="Pipecuronium bromide">Pipecuronium bromide</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li> <li><a href="/wiki/Rapacuronium_bromide" title="Rapacuronium bromide">Rapacuronium bromide</a></li> <li><a href="/wiki/Reboxetine" title="Reboxetine">Reboxetine</a></li> <li><a href="/wiki/Rocuronium_bromide" title="Rocuronium bromide">Rocuronium bromide</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Stercuronium_iodide" title="Stercuronium iodide">Stercuronium iodide</a></li> <li><a href="/wiki/Surugatoxin" title="Surugatoxin">Surugatoxin</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Threohydrobupropion" title="Threohydrobupropion">Threohydrobupropion</a></li> <li><a href="/wiki/Toxiferine" title="Toxiferine">Toxiferine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Trimetaphan_camsilate" title="Trimetaphan camsilate">Trimetaphan camsilate (trimethaphan camsylate)</a></li> <li><a href="/w/index.php?title=Tropeinium&action=edit&redlink=1" class="new" title="Tropeinium (page does not exist)">Tropeinium</a></li> <li><a href="/wiki/Tubocurarine" class="mw-redirect" title="Tubocurarine">Tubocurarine</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li> <li><a href="/wiki/Vecuronium_bromide" title="Vecuronium bromide">Vecuronium bromide</a></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a><br /><small>(and <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetyl-coA" class="mw-redirect" title="Acetyl-coA">Acetyl-coA</a></li> <li><a href="/wiki/Adafenoxate" title="Adafenoxate">Adafenoxate</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a> (<a href="/wiki/Lecithin" title="Lecithin">lecithin</a>)</li> <li><a href="/wiki/Citicoline" title="Citicoline">Citicoline</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a href="/wiki/Glycerophosphocholine" class="mw-redirect" title="Glycerophosphocholine">Glycerophosphocholine</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate (centrophenoxine)</a></li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a></li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a></li> <li><a href="/wiki/Phosphorylcholine" title="Phosphorylcholine">Phosphorylcholine</a></li> <li><a href="/wiki/Pirisudanol" title="Pirisudanol">Pirisudanol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Muscarinic_acetylcholine_receptor_modulators" title="Template:Muscarinic acetylcholine receptor modulators">Muscarinic acetylcholine receptor modulators</a></dd> <dd><a href="/wiki/Template:Acetylcholine_metabolism_and_transport_modulators" title="Template:Acetylcholine metabolism and transport modulators">Acetylcholine metabolism/transport modulators</a></dd></dl> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Anatoxin-a&oldid=1268917889">https://en.wikipedia.org/w/index.php?title=Anatoxin-a&oldid=1268917889</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Neurotoxins" title="Category:Neurotoxins">Neurotoxins</a></li><li><a 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