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Available in 9 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-9" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">9 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%BE%DB%8C%D9%88%D9%85%D8%A7%D8%AC%D8%AF%DB%8C%D9%86" title="پیوماجدین – South Azerbaijani" lang="azb" hreflang="azb" data-title="پیوماجدین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Aminoguanidin" title="Aminoguanidin – German" lang="de" hreflang="de" data-title="Aminoguanidin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BC%CE%B9%CE%BD%CE%BF%CE%B3%CE%BF%CF%85%CE%B1%CE%BD%CE%B9%CE%B4%CE%AF%CE%BD%CE%B7" title="Αμινογουανιδίνη – Greek" lang="el" hreflang="el" data-title="Αμινογουανιδίνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Aminoguanidina" title="Aminoguanidina – Basque" lang="eu" hreflang="eu" data-title="Aminoguanidina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%BE%DB%8C%D9%85%D8%A7%D8%AC%D8%AF%DB%8C%D9%86" title="پیماجدین – Persian" lang="fa" hreflang="fa" data-title="پیماجدین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%9F%E3%83%8E%E3%82%B0%E3%82%A2%E3%83%8B%E3%82%B8%E3%83%B3" title="アミノグアニジン – Japanese" lang="ja" hreflang="ja" data-title="アミノグアニジン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Pimagedin" title="Pimagedin – Serbian" lang="sr" hreflang="sr" data-title="Pimagedin" 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/Pimagedin" title="Pimagedin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Pimagedin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Pimagediini" title="Pimagediini – Finnish" lang="fi" hreflang="fi" data-title="Pimagediini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</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/Q409583#sitelinks-wikipedia" title="Edit 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page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" 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"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=Aminoguanidine&redirect=no" class="mw-redirect" title="Aminoguanidine">Aminoguanidine</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><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>Pimagedine </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Aminoguanidin.svg" class="mw-file-description" title="Skeletal formula of a pimagedine"><img alt="Skeletal formula of a pimagedine" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Aminoguanidin.svg/110px-Aminoguanidin.svg.png" decoding="async" width="110" height="67" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Aminoguanidin.svg/165px-Aminoguanidin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/62/Aminoguanidin.svg/220px-Aminoguanidin.svg.png 2x" data-file-width="512" data-file-height="312" /></a><figcaption>Skeletal formula of a pimagedine</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Aminoguanidine_sf.png" class="mw-file-description" title="Spacefill model of a pimagedine"><img alt="Spacefill model of a pimagedine" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Aminoguanidine_sf.png/110px-Aminoguanidine_sf.png" decoding="async" width="110" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Aminoguanidine_sf.png/165px-Aminoguanidine_sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Aminoguanidine_sf.png/220px-Aminoguanidine_sf.png 2x" data-file-width="639" data-file-height="514" /></a><figcaption>Spacefill model of a pimagedine</figcaption></figure> </td></tr></tbody></table> </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;">2-Aminoguanidine</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;"><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>Aminoguanidine</li><li>Guanyl hydrazine</li><li>Hydrazinecarboximidamide</li><li>Imino semicarbazide</li><li>Monoaminoguanidine</li></ul></div></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><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=79-17-4">79-17-4</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=NC%28N%29N%3DN">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/ChEMBL225304">ChEMBL225304</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.2061.html">2061</a></span><sup> <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></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/100.001.076">100.001.076</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q409583#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><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=5135">5135</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D05479">D05479</a></span></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/2146">2146</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/SCQ4EZQ113">SCQ4EZQ113</a></span><sup> <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></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/DTXSID5040964">DTXSID5040964</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q409583#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/CH6N4/c2-1(3)5-4/h1,4H,2-3H2<sup> <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 style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: DRCHNMARIZRTKI-UHFFFAOYSA-N<sup> <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></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%;">NC(N)N=N</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><span title="Carbon">C</span><span title="Hydrogen">H</span><sub>6</sub><span title="Nitrogen">N</span><sub>4</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>74.085 g/mol    </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.72 g/ml </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>261 °C (502 °F; 534 K) </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>−1.475 </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Guanidine" title="Guanidine">Guanidine</a> </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="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=403348066&page2=Pimagedine">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>Pimagedine</b>, also known as <b>aminoguanidine</b>, is an investigational <a href="/wiki/Drug" title="Drug">drug</a> for the treatment of <a href="/wiki/Diabetic_nephropathy" title="Diabetic nephropathy">diabetic nephropathy</a> that is no longer under development as a drug.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Pimagedine functions as an <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitor</a> of <a href="/wiki/Diamine_oxidase" title="Diamine oxidase">diamine oxidase</a> and <a href="/wiki/Nitric_oxide_synthase" title="Nitric oxide synthase">nitric oxide synthase</a>. It acts to reduce levels of <a href="/wiki/Advanced_glycation_end_product" class="mw-redirect" title="Advanced glycation end product">advanced glycation end products</a> (AGEs) through interacting with <a href="/wiki/3-deoxyglucosone" class="mw-redirect" title="3-deoxyglucosone">3-deoxyglucosone</a>, <a href="/wiki/Glyoxal" title="Glyoxal">glyoxal</a>, <a href="/wiki/Methylglyoxal" title="Methylglyoxal">methylglyoxal</a>, and related dicarbonyls. These reactive species are converted to less reactive heterocycles by this condensation reaction. </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=Pimagedine&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pimagedine was under development as a drug for kidney diseases by the pharmaceutical company Alteon (now known Synvista Therapeutics Inc.) that was founded in 1986.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> In 1987, Alteon acquired a license to intellectual property relating to AGE inhibition from Rockefeller University.<sup id="cite_ref-Alteon10K1996_3-0" class="reference"><a href="#cite_note-Alteon10K1996-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In 1989, Alteon and Marion Merrell Dow Inc (MMD) entered into a joint development program for pimagedine.<sup id="cite_ref-Lancet_4-0" class="reference"><a href="#cite_note-Lancet-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> In 1992, Alteon licensed a patent from Rockefeller University relating to the use of pimagedine to inhibit AGE formation.<sup id="cite_ref-Alteon10K1996_3-1" class="reference"><a href="#cite_note-Alteon10K1996-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In 1995, Hoechst AG (now Sanofi-Aventis) acquired MMD and subsequently terminated its agreement with Alteon, which led Alteon to stop clinical trials, which caused some controversy.<sup id="cite_ref-Lancet_4-1" class="reference"><a href="#cite_note-Lancet-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> In 1997, Alteon and Genentech announced a collaboration under which Genentech would fund development of pimagedine and would have the rights to sell the drug if it would be approved.<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> </p><p>In March 1998, Alteon announced that it had been advised that it should discontinue its Phase III trial of pimagedine in non-insulin-dependent (type II) diabetes patients with overt nephropathy, after the trial's external safety monitoring committee found an increased risk of side effects in the treatment group.<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> In November 1998, Alteon announced that its Phase III trial for pimagedine as a treatment for end stage renal disease had failed to prove efficacy, which led Carl Gordon, a leading biotech analyst, to say: "It looks like pimagedine is probably finished."<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> In February, 1999, Genentech ended its collaboration with Alteon to develop pimagedine.<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> In April 1999 Alteon announced that it would cease development of pimagedine as a treatment for end stage renal disease but might consider continuing development in type 1 diabetic patients with overt nephropathy or progressive kidney disease.<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> Alteon's 2000, 2001, 2002 annual reports indicated that it was not running any clinical trials on pimagedine but was seeking co-development partners.<sup id="cite_ref-Alteon10K2000_10-0" class="reference"><a href="#cite_note-Alteon10K2000-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><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> Alteon's 2003 and subsequent annual reports did not mention that Alteon was seeking partners for pimagedine,<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> which indicated that efforts to interest other companies and investors had failed and which signaled that commercial efforts to develop pimagedine as a drug were indeed finished.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2021)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pimagedine&action=edit&section=2" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pimagedine&action=edit&section=3" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The industrial synthesis uses the reaction between <a href="/wiki/Cyanamide" title="Cyanamide">cyanamide</a> and <a href="/wiki/Hydrazine" title="Hydrazine">hydrazine</a> in aqueous solution.<sup id="cite_ref-Ullmann_14-0" class="reference"><a href="#cite_note-Ullmann-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Aminoguanidine_synthesis01.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Aminoguanidine_synthesis01.svg/583px-Aminoguanidine_synthesis01.svg.png" decoding="async" width="583" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Aminoguanidine_synthesis01.svg/875px-Aminoguanidine_synthesis01.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/01/Aminoguanidine_synthesis01.svg/1166px-Aminoguanidine_synthesis01.svg.png 2x" data-file-width="583" data-file-height="134" /></a></span></dd></dl> <p>The compound can also be obtained from the reduction of <a href="/wiki/Nitroguanidine" title="Nitroguanidine">nitroguanidine</a> with <a href="/wiki/Zinc" title="Zinc">zinc</a> in <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Properties">Properties</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pimagedine&action=edit&section=4" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aminoguanidine is a colorless solid that is soluble in water and ethanol. It is basic, producing salts when reacted with organic acids. As established by many <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">crystallographic studies</a>, protonation of aminoguanidine occurs at the imino nitrogen.<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> With formic acid, condensation occurs, leading to cyclization to give <a href="/wiki/3-Amino-1,2,4-triazole" title="3-Amino-1,2,4-triazole">3-amino-1,2,4-triazole</a>.<sup id="cite_ref-Ullmann_14-1" class="reference"><a href="#cite_note-Ullmann-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:3-Amino-1,2,4-triazole_synthesis01.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/3-Amino-1%2C2%2C4-triazole_synthesis01.svg/600px-3-Amino-1%2C2%2C4-triazole_synthesis01.svg.png" decoding="async" width="600" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/3-Amino-1%2C2%2C4-triazole_synthesis01.svg/900px-3-Amino-1%2C2%2C4-triazole_synthesis01.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0d/3-Amino-1%2C2%2C4-triazole_synthesis01.svg/1200px-3-Amino-1%2C2%2C4-triazole_synthesis01.svg.png 2x" data-file-width="672" data-file-height="111" /></a></span></dd></dl> <p>The compound reacts with <a href="/wiki/Nitrous_acid" title="Nitrous acid">nitrous acid</a> in acidic medium to give <a href="/wiki/5-Aminotetrazole" title="5-Aminotetrazole">5-aminotetrazole</a> via the intermediate guanylazide.<sup id="cite_ref-Ullmann_14-2" class="reference"><a href="#cite_note-Ullmann-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> At neutral pH, the reaction leads to <a href="/wiki/Tetrazene_explosive" title="Tetrazene explosive">tetrazene</a>.<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> <a href="/wiki/Diazotization" class="mw-redirect" title="Diazotization">Diazotization</a> in <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> yields 1,3-di-(tetrazolyl)-triazene.<sup id="cite_ref-Ullmann_14-3" class="reference"><a href="#cite_note-Ullmann-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:5-Aminotetrazole_synthesis01.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/5-Aminotetrazole_synthesis01.svg/700px-5-Aminotetrazole_synthesis01.svg.png" decoding="async" width="700" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/5-Aminotetrazole_synthesis01.svg/1050px-5-Aminotetrazole_synthesis01.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/5-Aminotetrazole_synthesis01.svg/1400px-5-Aminotetrazole_synthesis01.svg.png 2x" data-file-width="883" data-file-height="111" /></a></span></dd></dl> <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=Pimagedine&action=edit&section=5" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFThornalley2003" class="citation journal cs1">Thornalley, Paul J. (2003). 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(March 2022)">bare URL plain text file</span></a></i>]</sup></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external free" href="https://www.sec.gov/Archives/edgar/data/878903/000089322002000222/0000893220-02-000222.txt">https://www.sec.gov/Archives/edgar/data/878903/000089322002000222/0000893220-02-000222.txt</a> <sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Bare_URLs" title="Wikipedia:Bare URLs"><span title="A full citation of this plain text file is required to prevent link rot. (March 2022)">bare URL plain text file</span></a></i>]</sup></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external free" href="https://www.sec.gov/Archives/edgar/data/878903/000089322003000272/0000893220-03-000272.txt">https://www.sec.gov/Archives/edgar/data/878903/000089322003000272/0000893220-03-000272.txt</a> <sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Bare_URLs" title="Wikipedia:Bare URLs"><span title="A full citation of this plain text file is required to prevent link rot. (March 2022)">bare URL plain text file</span></a></i>]</sup></span> </li> <li id="cite_note-Ullmann-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_14-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ullmann_14-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Ullmann_14-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGüthnerMertschenkSchulz2006" class="citation cs2">Güthner, Thomas; Mertschenk, Bernd; Schulz, Bernd (2006), "Guanidine and Derivatives", <i>Ullmann's Encyclopedia of Industrial Chemistry</i>, American Cancer Society, <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%2F14356007.a12_545.pub2">10.1002/14356007.a12_545.pub2</a>, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-30673-2" title="Special:BookSources/978-3-527-30673-2"><bdi>978-3-527-30673-2</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Guanidine+and+Derivatives&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.pub=American+Cancer+Society&rft.date=2006&rft_id=info%3Adoi%2F10.1002%2F14356007.a12_545.pub2&rft.isbn=978-3-527-30673-2&rft.aulast=G%C3%BCthner&rft.aufirst=Thomas&rft.au=Mertschenk%2C+Bernd&rft.au=Schulz%2C+Bernd&rfr_id=info%3Asid%2Fen.wikipedia.org%3APimagedine" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSmithAnzelmi1935" class="citation journal cs1">Smith, G. B. L.; Anzelmi, Edward (1935-12-01). "Reduction of Nitroguanidine. III. Synthesis of Aminoguanidine1". <i>Journal of the American Chemical Society</i>. <b>57</b> (12): 2730. <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/1935JAChS..57.2730S">1935JAChS..57.2730S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01315a510">10.1021/ja01315a510</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0002-7863">0002-7863</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+the+American+Chemical+Society&rft.atitle=Reduction+of+Nitroguanidine.+III.+Synthesis+of+Aminoguanidine1&rft.volume=57&rft.issue=12&rft.pages=2730&rft.date=1935-12-01&rft.issn=0002-7863&rft_id=info%3Adoi%2F10.1021%2Fja01315a510&rft_id=info%3Abibcode%2F1935JAChS..57.2730S&rft.aulast=Smith&rft.aufirst=G.+B.+L.&rft.au=Anzelmi%2C+Edward&rfr_id=info%3Asid%2Fen.wikipedia.org%3APimagedine" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAdams1977" class="citation journal cs1">Adams, J. M. (1977). "The Crystal Structure of Aminoguanidinium Dihydrogen Orthophosphate". <i>Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry</i>. <b>33</b> (5): <span class="nowrap">1513–</span>1515. <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/1977AcCrB..33.1513A">1977AcCrB..33.1513A</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1107%2FS0567740877006402">10.1107/S0567740877006402</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Crystallographica+Section+B+Structural+Crystallography+and+Crystal+Chemistry&rft.atitle=The+Crystal+Structure+of+Aminoguanidinium+Dihydrogen+Orthophosphate&rft.volume=33&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1513-%3C%2Fspan%3E1515&rft.date=1977&rft_id=info%3Adoi%2F10.1107%2FS0567740877006402&rft_id=info%3Abibcode%2F1977AcCrB..33.1513A&rft.aulast=Adams&rft.aufirst=J.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APimagedine" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPatinkinHorwitzLieber1955" class="citation journal cs1">Patinkin, Seymour H.; Horwitz, Jerome P.; Lieber, Eugene (1955-02-01). "The Structure of Tetracene1,2". <i>Journal of the American Chemical Society</i>. <b>77</b> (3): <span class="nowrap">562–</span>567. <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/1955JAChS..77..562P">1955JAChS..77..562P</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01608a014">10.1021/ja01608a014</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0002-7863">0002-7863</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+the+American+Chemical+Society&rft.atitle=The+Structure+of+Tetracene1%2C2&rft.volume=77&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E562-%3C%2Fspan%3E567&rft.date=1955-02-01&rft.issn=0002-7863&rft_id=info%3Adoi%2F10.1021%2Fja01608a014&rft_id=info%3Abibcode%2F1955JAChS..77..562P&rft.aulast=Patinkin&rft.aufirst=Seymour+H.&rft.au=Horwitz%2C+Jerome+P.&rft.au=Lieber%2C+Eugene&rfr_id=info%3Asid%2Fen.wikipedia.org%3APimagedine" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline 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href="/wiki/Template:Nitric_oxide_signaling_modulators" title="Template:Nitric oxide signaling modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nitric_oxide_signaling_modulators" title="Template talk:Nitric oxide signaling modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nitric_oxide_signaling_modulators" title="Special:EditPage/Template:Nitric oxide signaling modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nitric_oxide_signaling_modulators330" style="font-size:114%;margin:0 4em"><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a> <a href="/wiki/Cell_signaling" title="Cell signaling">signaling</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/Nitric_oxide" title="Nitric oxide">Forms</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl anion (NO<sup>−</sup>; oxonitrate(1-), hyponitrite anion)</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide (NO<sup>⋅</sup>; nitrogen monoxide)</a></li> <li><a href="/wiki/Nitrosonium" title="Nitrosonium">Nitrosonium (NO<sup>+</sup>; nitrosyl cation)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Biological_target" title="Biological target">Targets</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="sGC33" scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Soluble_guanylate_cyclase" class="mw-redirect" title="Soluble guanylate cyclase">sGC</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><i>Activators/stimulators:</i> <a href="/w/index.php?title=Ataciguat&action=edit&redlink=1" class="new" title="Ataciguat (page does not exist)">Ataciguat</a></li> <li><a href="/w/index.php?title=BAY_41-2272&action=edit&redlink=1" class="new" title="BAY 41-2272 (page does not exist)">BAY 41-2272</a></li> <li><a href="/w/index.php?title=BAY_41-8543&action=edit&redlink=1" class="new" title="BAY 41-8543 (page does not exist)">BAY 41-8543</a></li> <li><a href="/w/index.php?title=BAY_60-4552&action=edit&redlink=1" class="new" title="BAY 60-4552 (page does not exist)">BAY 60-4552</a></li> <li><a href="/w/index.php?title=BI-703704&action=edit&redlink=1" class="new" title="BI-703704 (page does not exist)">BI-703704</a></li> <li><a href="/wiki/Cinaciguat" title="Cinaciguat">Cinaciguat (BAY 58-2667)</a></li> <li><a href="/w/index.php?title=GSK-2181236A&action=edit&redlink=1" class="new" title="GSK-2181236A (page does not exist)">GSK-2181236A</a></li> <li><a href="/w/index.php?title=Praliciguat&action=edit&redlink=1" class="new" title="Praliciguat (page does not exist)">Praliciguat</a></li> <li><a href="/wiki/Riociguat" title="Riociguat">Riociguat</a></li> <li><a href="/wiki/Vericiguat" title="Vericiguat">Vericiguat</a></li></ul> <ul><li><i>Inhibitors:</i> <a href="/w/index.php?title=1H-(1,2,4)Oxadiazolo(4,3-a)quinoxalin-1-one&action=edit&redlink=1" class="new" title="1H-(1,2,4)Oxadiazolo(4,3-a)quinoxalin-1-one (page does not exist)">ODQ</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/NO_donor" class="mw-redirect" title="NO donor">NO donors</a><br /><small>(<a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Nitrate" title="Nitrate">Nitrates</a>:</i> <a href="/wiki/Diethylene_glycol_dinitrate" title="Diethylene glycol dinitrate">Diethylene glycol dinitrate (DEGDN)</a></li> <li><a href="/wiki/Erythritol_tetranitrate" title="Erythritol tetranitrate">Erythritol tetranitrate (ETN)</a></li> <li><a href="/wiki/Ethylene_glycol_dinitrate" title="Ethylene glycol dinitrate">Ethylene glycol dinitrate (EGDN; nitroglycol)</a></li> <li><a href="/wiki/Isosorbide_mononitrate" title="Isosorbide mononitrate">Isosorbide mononitrate (ISMN)</a></li> <li><a href="/wiki/Isosorbide_dinitrate" title="Isosorbide dinitrate">Isosorbide dinitrate (ISDN)</a></li> <li><a href="/wiki/Itramin_tosilate" title="Itramin tosilate">Itramin tosilate</a></li> <li><a href="/wiki/Mannitol_hexanitrate" title="Mannitol hexanitrate">Mannitol hexanitrate</a></li> <li><a href="/wiki/Naproxcinod" title="Naproxcinod">Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)</a></li> <li><a href="/w/index.php?title=NCX-466&action=edit&redlink=1" class="new" title="NCX-466 (page does not exist)">NCX-466</a></li> <li><a href="/w/index.php?title=NCX-2216&action=edit&redlink=1" class="new" title="NCX-2216 (page does not exist)">NCX-2216</a></li> <li><a href="/w/index.php?title=NCX-4016&action=edit&redlink=1" class="new" title="NCX-4016 (page does not exist)">NCX-4016</a></li> <li><a href="/w/index.php?title=NCX_4040&action=edit&redlink=1" class="new" title="NCX 4040 (page does not exist)">NCX 4040</a></li> <li><a href="/w/index.php?title=NCX-4215&action=edit&redlink=1" class="new" title="NCX-4215 (page does not exist)">NCX-4215</a></li> <li><a href="/wiki/Nicorandil" title="Nicorandil">Nicorandil</a></li> <li><a href="/wiki/Nipradilol" title="Nipradilol">Nipradilol (K-351)</a></li> <li><a href="/wiki/Nitrate" title="Nitrate">Nitrate (NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>)</a></li> <li><a href="/w/index.php?title=Nitroatorvastatin&action=edit&redlink=1" class="new" title="Nitroatorvastatin (page does not exist)">Nitroatorvastatin (NCX-6560)</a></li> <li><a href="/w/index.php?title=Nitroflurbiprofen&action=edit&redlink=1" class="new" title="Nitroflurbiprofen (page does not exist)">Nitroflurbiprofen (HCT-1026)</a></li> <li><a href="/w/index.php?title=Nitrofluvastatin&action=edit&redlink=1" class="new" title="Nitrofluvastatin (page does not exist)">Nitrofluvastatin</a></li> <li><a href="/wiki/Nitroglycerin_(drug)" class="mw-redirect" title="Nitroglycerin (drug)">Nitroglycerin (glyceryl trinitrate (GTN))</a></li> <li><a href="/w/index.php?title=Nitropravastatin&action=edit&redlink=1" class="new" title="Nitropravastatin (page does not exist)">Nitropravastatin (NCX-6550)</a></li> <li><a href="/wiki/Pentaerithrityl_tetranitrate" class="mw-redirect" title="Pentaerithrityl tetranitrate">Pentaerithrityl tetranitrate (PETN)</a></li> <li><a href="/wiki/Propatylnitrate" title="Propatylnitrate">Propatylnitrate</a></li> <li><a href="/wiki/Propylene_glycol_dinitrate" title="Propylene glycol dinitrate">Propylene glycol dinitrate (PGDN)</a></li> <li><a href="/w/index.php?title=Sodium_trioxodinitrate&action=edit&redlink=1" class="new" title="Sodium trioxodinitrate (page does not exist)">Sodium trioxodinitrate (Angeli's salt)</a></li> <li>Tenitramine</li> <li><a href="/wiki/Trolnitrate" title="Trolnitrate">Trolnitrate</a></li></ul> <ul><li><i><a href="/wiki/Nitroso_compound" class="mw-redirect" title="Nitroso compound">Nitroso compounds</a>/<a href="/wiki/Nitrite" title="Nitrite">nitrites</a>:</i> <a href="/wiki/Nitrite" title="Nitrite">Nitrite (NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>)</a>; <i>O-Nitroso compounds (<a href="/wiki/Alkyl_nitrite" title="Alkyl nitrite">alkyl nitrites</a>):</i> <a href="/wiki/Amyl_nitrite" title="Amyl nitrite">Amyl nitrite (isoamyl nitrite, isopentyl nitrite)</a></li> <li><a href="/wiki/Cyclohexyl_nitrite" title="Cyclohexyl nitrite">Cyclohexyl nitrite</a></li> <li><a href="/wiki/Ethyl_nitrite" title="Ethyl nitrite">Ethyl nitrite</a></li> <li><a href="/wiki/Hexyl_nitrite" title="Hexyl nitrite">Hexyl nitrite</a></li> <li><a href="/wiki/Isobutyl_nitrite" title="Isobutyl nitrite">Isobutyl nitrite (2-methylpropyl nitrite)</a></li> <li><a href="/wiki/Isopropyl_nitrite" title="Isopropyl nitrite">Isopropyl nitrite</a></li> <li><a href="/wiki/Methyl_nitrite" title="Methyl nitrite">Methyl nitrite</a></li> <li><a href="/wiki/Butyl_nitrite" title="Butyl nitrite"><i>n</i>-Butyl nitrite</a></li> <li><a href="/wiki/Pentyl_nitrite" title="Pentyl nitrite">Pentyl nitrite</a></li> <li><a href="/wiki/Tert-Butyl_nitrite" title="Tert-Butyl nitrite"><i>tert</i>-Butyl nitrite</a>; <i><a href="/wiki/S-Nitrosothiol" title="S-Nitrosothiol">S-Nitroso compounds</a> (thionitrites):</i> <a href="/w/index.php?title=LA810&action=edit&redlink=1" class="new" title="LA810 (page does not exist)">LA810</a></li> <li><a href="/w/index.php?title=S-Nitrosoalbumin&action=edit&redlink=1" class="new" title="S-Nitrosoalbumin (page does not exist)">S-Nitrosoalbumin (SNALB)</a></li> <li><a href="/w/index.php?title=S-Nitrosated_AR545C&action=edit&redlink=1" class="new" title="S-Nitrosated AR545C (page does not exist)">S-Nitrosated AR545C</a></li> <li><a href="/w/index.php?title=S-Nitroso-N-acetylcysteine&action=edit&redlink=1" class="new" title="S-Nitroso-N-acetylcysteine (page does not exist)">S-Nitroso-N-acetylcysteine (SNAC)</a></li> <li><a href="/wiki/S-Nitroso-N-acetylpenicillamine" title="S-Nitroso-N-acetylpenicillamine">S-Nitroso-N-acetylpenicillamine (SNAP)</a></li> <li><a href="/w/index.php?title=S-Nitroso-N-valerylpenicillamine&action=edit&redlink=1" class="new" title="S-Nitroso-N-valerylpenicillamine (page does not exist)">S-Nitroso-N-valerylpenicillamine (SNVP)</a></li> <li><a href="/w/index.php?title=S-Nitrosocaptopril&action=edit&redlink=1" class="new" title="S-Nitrosocaptopril (page does not exist)">S-Nitrosocaptopril (SNO-Cap)</a></li> <li><a href="/w/index.php?title=S-Nitrosocysteine&action=edit&redlink=1" class="new" title="S-Nitrosocysteine (page does not exist)">S-Nitrosocysteine (SNC, CysNO, SNO-Cys)</a></li> <li><a href="/w/index.php?title=S-Nitrosodiclofenac&action=edit&redlink=1" class="new" title="S-Nitrosodiclofenac (page does not exist)">S-Nitrosodiclofenac</a></li> <li><a href="/wiki/S-Nitrosoglutathione" title="S-Nitrosoglutathione">S-Nitrosoglutathione (GSNO, SNOG)</a></li> <li><a href="/w/index.php?title=S-Nitrosated_tissue-type_plasminogen_activator&action=edit&redlink=1" class="new" title="S-Nitrosated tissue-type plasminogen activator (page does not exist)">SNO-t-PA</a></li> <li><a href="/w/index.php?title=S-Nitrosated_von_Willebrand_factor&action=edit&redlink=1" class="new" title="S-Nitrosated von Willebrand factor (page does not exist)">SNO-vWF</a>; <i>N-Nitroso compounds (e.g., <a href="/wiki/Nitrosamine" title="Nitrosamine">nitrosamines</a>):</i> <a href="/w/index.php?title=SIN-1A&action=edit&redlink=1" class="new" title="SIN-1A (page does not exist)">SIN-1A</a></li></ul> <ul><li><i>Nitrosyl compounds:</i> <i><a href="/wiki/Metal_nitrosyl_complex" title="Metal nitrosyl complex">Metal nitrosyl complexes</a>:</i> <a href="/wiki/Roussin%27s_black_salt" title="Roussin's black salt">Roussin's black salt</a></li> <li><a href="/wiki/Roussin%27s_red_salt" title="Roussin's red salt">Roussin's red salt</a></li> <li><a href="/wiki/Sodium_nitroprusside" title="Sodium nitroprusside">Sodium nitroprusside (SNP)</a></li></ul> <ul><li><i><a href="/wiki/NONOate" title="NONOate">NONOates</a> (diazeniumdiolates):</i> <a href="/w/index.php?title=Diethylamine/NO&action=edit&redlink=1" class="new" title="Diethylamine/NO (page does not exist)">Diethylamine/NO (DEA/NO)</a></li> <li><a href="/w/index.php?title=Diethylenetriamine/NO&action=edit&redlink=1" class="new" title="Diethylenetriamine/NO (page does not exist)">Diethylenetriamine/NO (DETA/NO)</a></li> <li><a href="/w/index.php?title=GLO/NO&action=edit&redlink=1" class="new" title="GLO/NO (page does not exist)">GLO/NO</a></li> <li><a href="/w/index.php?title=JS-K&action=edit&redlink=1" class="new" title="JS-K (page does not exist)">JS-K</a></li> <li><a href="/w/index.php?title=Methylamine_hexamethylene_methylamine/NO&action=edit&redlink=1" class="new" title="Methylamine hexamethylene methylamine/NO (page does not exist)">Methylamine hexamethylene methylamine/NO (MAHMA/NO)</a></li> <li><a href="/w/index.php?title=PROLI/NO&action=edit&redlink=1" class="new" title="PROLI/NO (page does not exist)">PROLI/NO</a></li> <li><a href="/w/index.php?title=Spermine/NO&action=edit&redlink=1" class="new" title="Spermine/NO (page does not exist)">Spermine/NO (SPER/NO)</a></li> <li><a href="/w/index.php?title=V-PYRRO/NO&action=edit&redlink=1" class="new" title="V-PYRRO/NO (page does not exist)">V-PYRRO/NO</a></li></ul> <ul><li><i>Heterocyclic compounds:</i> <i><a href="/wiki/Furoxan" title="Furoxan">Furoxans</a>:</i> <a href="/wiki/Furoxan" title="Furoxan">Furoxan</a></li> <li><a href="/w/index.php?title=REC15/2739&action=edit&redlink=1" class="new" title="REC15/2739 (page does not exist)">REC15/2739</a>; <i><a href="/w/index.php?title=Sydnonimine&action=edit&redlink=1" class="new" title="Sydnonimine (page does not exist)">Sydnonimines</a>:</i> <a href="/wiki/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Linsidomine" title="Linsidomine">Linsidomine (SIN-1)</a></li> <li><a href="/wiki/Molsidomine" title="Molsidomine">Molsidomine (SIN-10)</a></li> <li><a href="/w/index.php?title=Sydnonimine&action=edit&redlink=1" class="new" title="Sydnonimine (page does not exist)">Sydnonimine</a></li></ul> <ul><li><i>Unsorted:</i> <a href="/wiki/Cimlanod" title="Cimlanod">Cimlanod</a></li> <li><a href="/w/index.php?title=FK-409&action=edit&redlink=1" class="new" title="FK-409 (page does not exist)">FK-409</a></li> <li><a href="/w/index.php?title=FR144220&action=edit&redlink=1" class="new" title="FR144220 (page does not exist)">FR144220</a></li> <li><a href="/w/index.php?title=FR146881&action=edit&redlink=1" class="new" title="FR146881 (page does not exist)">FR146881</a></li> <li><a href="/w/index.php?title=N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide&action=edit&redlink=1" class="new" title="N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide (page does not exist)">N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Nitric_oxide_synthase" title="Nitric oxide synthase">NOS</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/NOS1" title="NOS1">nNOS</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="/w/index.php?title=3-Bromo-7-nitroindazole&action=edit&redlink=1" class="new" title="3-Bromo-7-nitroindazole (page does not exist)">3-Bromo-7-nitroindazole</a></li> <li><a href="/w/index.php?title=3-Chloroindazole&action=edit&redlink=1" class="new" title="3-Chloroindazole (page does not exist)">3-Chloroindazole</a></li> <li><a href="/w/index.php?title=3-Chloro-5-nitroindazole&action=edit&redlink=1" class="new" title="3-Chloro-5-nitroindazole (page does not exist)">3-Chloro-5-nitroindazole</a></li> <li><a href="/w/index.php?title=5-Nitroindazole&action=edit&redlink=1" class="new" title="5-Nitroindazole (page does not exist)">5-Nitroindazole</a></li> <li><a href="/w/index.php?title=6-Nitroindazole&action=edit&redlink=1" class="new" title="6-Nitroindazole (page does not exist)">6-Nitroindazole</a></li> <li><a href="/wiki/7-Nitroindazole" title="7-Nitroindazole">7-Nitroindazole</a></li> <li><a href="/w/index.php?title=A-84643&action=edit&redlink=1" class="new" title="A-84643 (page does not exist)">A-84643</a></li> <li><a href="/wiki/Aminoguanidine" class="mw-redirect" title="Aminoguanidine">Aminoguanidine (pimagedine)</a></li> <li><a href="/w/index.php?title=ARL-17477&action=edit&redlink=1" class="new" title="ARL-17477 (page does not exist)">ARL-17477</a></li> <li><a href="/wiki/Indazole" title="Indazole">Indazole</a></li> <li><a href="/w/index.php?title=N5-(1-Iminoethyl)-L-ornithine&action=edit&redlink=1" class="new" title="N5-(1-Iminoethyl)-L-ornithine (page does not exist)">N<sup>5</sup>-(1-Iminoethyl)-L-ornithine (<small>L</small>-NIO)</a></li> <li><a href="/w/index.php?title=N%CF%89-Methyl-L-arginine&action=edit&redlink=1" class="new" title="Nω-Methyl-L-arginine (page does not exist)">N<sup>ω</sup>-Methyl-<small>L</small>-arginine (<small>L</small>-NMA)</a></li> <li><a href="/w/index.php?title=N%CF%89-Propyl-L-arginine&action=edit&redlink=1" class="new" title="Nω-Propyl-L-arginine (page does not exist)">N<sup>ω</sup>-Propyl-<small>L</small>-arginine (<small>L</small>-NPA)</a></li> <li><a href="/wiki/Nitroarginine" title="Nitroarginine">Nitroarginine (NNA, NOARG)</a></li> <li><a href="/wiki/Pentamidine_isethionate" class="mw-redirect" title="Pentamidine isethionate">Pentamidine isethionate</a></li> <li><a href="/w/index.php?title=1-(2-Trifluoromethylphenyl)imidazole&action=edit&redlink=1" class="new" title="1-(2-Trifluoromethylphenyl)imidazole (page does not exist)">TRIM</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Nitric_oxide_synthase_2_(inducible)" title="Nitric oxide synthase 2 (inducible)">iNOS</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="/w/index.php?title=1-Amino-2-hydroxyguanidine&action=edit&redlink=1" class="new" title="1-Amino-2-hydroxyguanidine (page does not exist)">1-Amino-2-hydroxyguanidine</a></li> <li><a href="/w/index.php?title=2-Ethylaminoguanidine&action=edit&redlink=1" class="new" title="2-Ethylaminoguanidine (page does not exist)">2-Ethylaminoguanidine</a></li> <li><a href="/w/index.php?title=2-Iminopiperidine&action=edit&redlink=1" class="new" title="2-Iminopiperidine (page does not exist)">2-Iminopiperidine</a></li> <li><a href="/w/index.php?title=1400W&action=edit&redlink=1" class="new" title="1400W (page does not exist)">1400W</a></li> <li><a href="/w/index.php?title=S-aminoethylisothiourea&action=edit&redlink=1" class="new" title="S-aminoethylisothiourea (page does not exist)">AEITU</a></li> <li><a href="/wiki/Aminoguanidine" class="mw-redirect" title="Aminoguanidine">Aminoguanidine (pimagedine)</a></li> <li><a href="/w/index.php?title=2-Amino-5,6-dihydro-6-methyl-4H-1,3-thiazine&action=edit&redlink=1" class="new" title="2-Amino-5,6-dihydro-6-methyl-4H-1,3-thiazine (page does not exist)">AMT</a></li> <li><a href="/w/index.php?title=AR-C_102222&action=edit&redlink=1" class="new" title="AR-C 102222 (page does not exist)">AR-C 102222</a></li> <li><a href="/w/index.php?title=BYK-191023&action=edit&redlink=1" class="new" title="BYK-191023 (page does not exist)">BYK-191023</a></li> <li><a href="/wiki/Canavanine" title="Canavanine">Canavanine</a></li> <li><a href="/w/index.php?title=Cindunistat&action=edit&redlink=1" class="new" title="Cindunistat (page does not exist)">Cindunistat (SD-6010)</a></li> <li><a href="/w/index.php?title=S-Ethylisothiourea&action=edit&redlink=1" class="new" title="S-Ethylisothiourea (page does not exist)">EITU</a></li> <li><a href="/w/index.php?title=S-Isopropylisothiourea&action=edit&redlink=1" class="new" title="S-Isopropylisothiourea (page does not exist)">IPTU</a></li> <li><a href="/w/index.php?title=S-Methylisothiourea&action=edit&redlink=1" class="new" title="S-Methylisothiourea (page does not exist)">MITU</a></li> <li><a href="/w/index.php?title=N5-(1-Iminoethyl)-L-ornithine&action=edit&redlink=1" class="new" title="N5-(1-Iminoethyl)-L-ornithine (page does not exist)">N<sup>5</sup>-(1-Iminoethyl)-<small>L</small>-ornithine (<small>L</small>-NIO)</a></li> <li><a href="/w/index.php?title=N6-(1-Iminoethyl)-L-lysine&action=edit&redlink=1" class="new" title="N6-(1-Iminoethyl)-L-lysine (page does not exist)">N<sup>6</sup>-(1-Iminoethyl)-<small>L</small>-lysine (<small>L</small>-NIL)</a></li> <li><a href="/w/index.php?title=N%CF%89-Methyl-L-arginine&action=edit&redlink=1" class="new" title="Nω-Methyl-L-arginine (page does not exist)">N<sup>ω</sup>-Methyl-<small>L</small>-arginine (<small>L</small>-NMA)</a></li> <li><a href="/w/index.php?title=Ronopterin&action=edit&redlink=1" class="new" title="Ronopterin (page does not exist)">Ronopterin (VAS-203)</a></li> <li><a href="/w/index.php?title=1-(2-Trifluoromethylphenyl)imidazole&action=edit&redlink=1" class="new" title="1-(2-Trifluoromethylphenyl)imidazole (page does not exist)">TRIM</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Endothelial_NOS" title="Endothelial NOS">eNOS</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/Aminoguanidine" class="mw-redirect" title="Aminoguanidine">Aminoguanidine (pimagedine)</a></li> <li><a href="/w/index.php?title=N5-(1-Iminoethyl)-L-ornithine&action=edit&redlink=1" class="new" title="N5-(1-Iminoethyl)-L-ornithine (page does not exist)">N<sup>5</sup>-(1-Iminoethyl)-<small>L</small>-ornithine (<small>L</small>-NIO)</a></li> <li><a href="/w/index.php?title=N%CF%89-Methyl-L-arginine&action=edit&redlink=1" class="new" title="Nω-Methyl-L-arginine (page does not exist)">N<sup>ω</sup>-Methyl-<small>L</small>-arginine (<small>L</small>-NMA)</a></li> <li><a href="/wiki/Nitroarginine" title="Nitroarginine">Nitroarginine (NNA, NOARG)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Unsorted</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Asymmetric_dimethylarginine" title="Asymmetric dimethylarginine">Asymmetric dimethylarginine (ADMA)</a></li> <li><a href="/w/index.php?title=CKD-712&action=edit&redlink=1" class="new" title="CKD-712 (page does not exist)">CKD-712</a></li> <li><a href="/w/index.php?title=Guanidinoethyldisulfide&action=edit&redlink=1" class="new" title="Guanidinoethyldisulfide (page does not exist)">Guanidinoethyldisulfide (GED)</a></li> <li><a href="/w/index.php?title=GW-273629&action=edit&redlink=1" class="new" title="GW-273629 (page does not exist)">GW-273629</a></li> <li><a href="/wiki/Indospicine" title="Indospicine">Indospicine</a></li> <li><a href="/w/index.php?title=KD-7040&action=edit&redlink=1" class="new" title="KD-7040 (page does not exist)">KD-7040</a></li> <li><a href="/w/index.php?title=Nitroarginine_methyl_ester&action=edit&redlink=1" class="new" title="Nitroarginine methyl ester (page does not exist)">Nitroarginine methyl ester (NAME)</a></li> <li><a href="/w/index.php?title=NCX-456&action=edit&redlink=1" class="new" title="NCX-456 (page does not exist)">NCX-456</a></li> <li><a href="/w/index.php?title=NXN-462&action=edit&redlink=1" class="new" title="NXN-462 (page does not exist)">NXN-462</a></li> <li><a href="/w/index.php?title=ONO-1714&action=edit&redlink=1" class="new" title="ONO-1714 (page does not exist)">ONO-1714</a></li> <li><a href="/w/index.php?title=VAS-2381&action=edit&redlink=1" class="new" title="VAS-2381 (page does not exist)">VAS-2381</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/Arginase" title="Arginase">Arginase</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="/w/index.php?title=2S-Amino-6-boronohexonic_acid&action=edit&redlink=1" class="new" title="2S-Amino-6-boronohexonic acid (page does not exist)">ABH</a></li> <li><a href="/w/index.php?title=N%CF%89-Hydroxy-L-arginine&action=edit&redlink=1" class="new" title="Nω-Hydroxy-L-arginine (page does not exist)">N<sup>ω</sup>-Hydroxy-<small>L</small>-arginine (NOHA)</a></li> <li><a href="/wiki/Chlorogenic_acid" title="Chlorogenic acid">chlorogenic acid</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">ginseng</a></li> <li><a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a></li> <li><a href="/wiki/Ornithine" title="Ornithine">ornithine</a></li> <li><a href="/wiki/Norvaline" title="Norvaline">norvaline</a></li> <li><a href="/wiki/Lysine" title="Lysine">lysine</a></li> <li><a href="/w/index.php?title=Alpha_aminoacids&action=edit&redlink=1" class="new" title="Alpha aminoacids (page does not exist)">alpha aminoacids</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/CAMK" title="CAMK">CAMK</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="/w/index.php?title=Calmidazolium&action=edit&redlink=1" class="new" title="Calmidazolium (page does not exist)">Calmidazolium</a></li> <li><a href="/w/index.php?title=W-7_(drug)&action=edit&redlink=1" class="new" title="W-7 (drug) (page does not exist)">W-7</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Precursors:</i> <a href="/wiki/Arginine" title="Arginine"><small>L</small>-Arginine</a></li> <li><a href="/w/index.php?title=N%CF%89-Hydroxy-L-arginine&action=edit&redlink=1" class="new" title="Nω-Hydroxy-L-arginine (page does not exist)">N<sup>ω</sup>-Hydroxy-<small>L</small>-arginine (NOHA)</a></li></ul> <ul><li><i>Cofactors:</i> <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NADPH</a></li> <li><a href="/wiki/Flavin_adenine_dinucleotide" title="Flavin adenine dinucleotide">FAD</a></li> <li><a href="/wiki/Flavin_mononucleotide" title="Flavin mononucleotide">FMN</a></li> <li><a href="/wiki/Heme" title="Heme">Heme</a></li> <li><a href="/wiki/Tetrahydrobiopterin" title="Tetrahydrobiopterin">BH<sub>4</sub></a></li> <li><a href="/wiki/Calmodulin" title="Calmodulin">CaM</a></li> <li><a href="/wiki/Oxygen" title="Oxygen">O<sub>2</sub></a></li> <li><a href="/wiki/Calcium" title="Calcium">Ca<sup>2+</sup></a></li></ul> <ul><li><i>Indirect/downstream NO modulators:</i> <a href="/wiki/ACE_inhibitor" title="ACE inhibitor">ACE inhibitors</a>/<a href="/wiki/Angiotensin_II_receptor_antagonist" class="mw-redirect" title="Angiotensin II receptor antagonist">AT-II receptor antagonists</a> (e.g., <a href="/wiki/Captopril" title="Captopril">captopril</a>, <a href="/wiki/Losartan" title="Losartan">losartan</a>)</li> <li><a href="/wiki/Endothelin_receptor_antagonist" title="Endothelin receptor antagonist">ET<sub>B</sub> receptor antagonists</a> (e.g., <a href="/wiki/Bosentan" title="Bosentan">bosentan</a>)</li> <li><a href="/wiki/L-Type_calcium_channel" class="mw-redirect" title="L-Type calcium channel">L-Type calcium channel</a> <a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">blockers</a> (e.g., <a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">dihydropyridines</a>: <a href="/wiki/Nifedipine" title="Nifedipine">nifedipine</a>)</li> <li><a href="/wiki/Nebivolol" title="Nebivolol">Nebivolol</a> (<a href="/wiki/Beta_blocker" title="Beta blocker">beta blocker</a>)</li> <li><a href="/wiki/PDE5_inhibitor" title="PDE5 inhibitor">PDE5 inhibitors</a> (e.g., <a href="/wiki/Sildenafil" title="Sildenafil">sildenafil</a>)</li> <li>non-selective PDE inhibitors (e.g., <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>)</li> <li>PDE9 inhibitors (e.g., <a href="/wiki/Paraxanthine" title="Paraxanthine">paraxanthine</a>)</li> <li>cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)</li> <li><a href="/wiki/Statin" title="Statin">Statins</a> (e.g., <a href="/wiki/Simvastatin" title="Simvastatin">simvastatin</a>)</li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Monoamine_metabolism_modulators806" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoamine_metabolism_modulators" title="Template talk:Monoamine metabolism modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoamine_metabolism_modulators" title="Special:EditPage/Template:Monoamine metabolism modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoamine_metabolism_modulators806" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">Monoamine</a> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> <a href="/wiki/Enzyme_modulator" title="Enzyme modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Non-specific</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase"><abbr title="Aromatic L-amino acid decarboxylase">AAAD</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 Aromatic L-amino acid decarboxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/L-DOPA" title="L-DOPA"><small>L</small>-DOPA (levodopa)</a>→<a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/5-HTP" class="mw-redirect" title="5-HTP">5-HTP</a>→<a href="/wiki/Serotonin" title="Serotonin">Serotonin</a></li> <li><a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><small>L</small>-Histidine</a>→<a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a>→<a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/L-Tyrosine" class="mw-redirect" title="L-Tyrosine"><small>L</small>-Tyrosine</a>→<a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a>→<a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/Benserazide" title="Benserazide">Benserazide</a></li> <li><a href="/wiki/Carbidopa" title="Carbidopa">Carbidopa</a></li> <li><a href="/wiki/Alpha-Difluoromethyl-DOPA" class="mw-redirect" title="Alpha-Difluoromethyl-DOPA">DFMD</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase"><abbr title="Monoamine oxidase">MAO</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Monoamine oxidase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products (with <a href="/wiki/Aldehyde_dehydrogenase" title="Aldehyde dehydrogenase"><abbr title="Aldehyde dehydrogenase">ALDH</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 Aldehyde dehydrogenase</span>/<a href="/wiki/Aldehyde_reductase" class="mw-redirect" title="Aldehyde reductase"><abbr title="Aldehyde reductase">ALR</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 ALR</span>):</b> <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a>→<a href="/wiki/3,4-Dihydroxymandelic_acid" title="3,4-Dihydroxymandelic acid">DHMA</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a>→<a href="/wiki/3-Methoxy-4-hydroxyphenylglycol" title="3-Methoxy-4-hydroxyphenylglycol">MHPG</a>/<a href="/wiki/Vanillylmandelic_acid" title="Vanillylmandelic acid">VMA</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a>→<a href="/wiki/3,4-Dihydroxymandelic_acid" title="3,4-Dihydroxymandelic acid">DHMA</a></li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a>→<a href="/wiki/3-Methoxy-4-hydroxyphenylglycol" title="3-Methoxy-4-hydroxyphenylglycol">MHPG</a>/<a href="/wiki/Vanillylmandelic_acid" title="Vanillylmandelic acid">VMA</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a>→<a href="/wiki/3,4-Dihydroxyphenylacetic_acid" title="3,4-Dihydroxyphenylacetic acid">DOPAC</a></li> <li><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a>→<a href="/wiki/Homovanillic_acid" title="Homovanillic acid">HVA</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a>→<a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li></ul> <ul><li><b>Inhibitors:</b> <i>Non-selective:</i> <a href="/wiki/Benmoxin" title="Benmoxin">Benmoxin</a></li> <li><a href="/wiki/Caroxazone" title="Caroxazone">Caroxazone</a></li> <li><a href="/wiki/Echinopsidine" title="Echinopsidine">Echinopsidine</a></li> <li><a href="/wiki/Furazolidone" title="Furazolidone">Furazolidone</a></li> <li><a href="/wiki/Guineesine" title="Guineesine">Guineesine</a></li> <li><a href="/wiki/Hydralazine" title="Hydralazine">Hydralazine</a></li> <li><a href="/wiki/Indantadol" title="Indantadol">Indantadol</a></li> <li><a href="/wiki/Iproclozide" title="Iproclozide">Iproclozide</a></li> <li><a href="/wiki/Iproniazid" title="Iproniazid">Iproniazid</a></li> <li><a href="/wiki/Isocarboxazid" title="Isocarboxazid">Isocarboxazid</a></li> <li><a href="/wiki/Isoniazid" title="Isoniazid">Isoniazid</a></li> <li><a href="/wiki/Linezolid" title="Linezolid">Linezolid</a></li> <li><a href="/wiki/Mebanazine" title="Mebanazine">Mebanazine</a></li> <li><a href="/wiki/Metfendrazine" title="Metfendrazine">Metfendrazine</a></li> <li><a href="/wiki/Nialamide" title="Nialamide">Nialamide</a></li> <li><a href="/wiki/Octamoxin" title="Octamoxin">Octamoxin</a></li> <li><a href="/wiki/Paraxazone" title="Paraxazone">Paraxazone</a></li> <li><a href="/wiki/Phenelzine" title="Phenelzine">Phenelzine</a></li> <li><a href="/wiki/Pheniprazine" title="Pheniprazine">Pheniprazine</a></li> <li><a href="/wiki/Phenoxypropazine" title="Phenoxypropazine">Phenoxypropazine</a></li> <li><a href="/wiki/Pivhydrazine" title="Pivhydrazine">Pivhydrazine</a></li> <li><a href="/wiki/Procarbazine" title="Procarbazine">Procarbazine</a></li> <li><a href="/wiki/Safrazine" title="Safrazine">Safrazine</a></li> <li><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <i>MAO-A-selective:</i> <a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/Bazinaprine" title="Bazinaprine">Bazinaprine</a></li> <li><a href="/wiki/Befloxatone" title="Befloxatone">Befloxatone</a></li> <li><a href="/wiki/Brofaromine" title="Brofaromine">Brofaromine</a></li> <li><a href="/wiki/Cimoxatone" title="Cimoxatone">Cimoxatone</a></li> <li><a href="/wiki/Clorgiline" title="Clorgiline">Clorgiline</a></li> <li><a href="/wiki/CX157" title="CX157">CX157 (Tyrima)</a></li> <li><a href="/wiki/Eprobemide" title="Eprobemide">Eprobemide</a></li> <li><a href="/wiki/Esuprone" title="Esuprone">Esuprone</a></li> <li><a href="/wiki/Harmala_alkaloid" title="Harmala alkaloid">Harmala alkaloids</a> (e.g., <a href="/wiki/Harmine" title="Harmine">harmine</a>, <a href="/wiki/Harmaline" title="Harmaline">harmaline</a>, <a href="/wiki/Harmane" title="Harmane">harman</a>, <a href="/wiki/Norharman" class="mw-redirect" title="Norharman">norharman</a>, <a href="/wiki/Tetrahydroharmine" title="Tetrahydroharmine">tetrahydroharmine</a>)</li> <li><a href="/wiki/Methylene_blue" title="Methylene blue">Methylene blue</a></li> <li><a href="/wiki/Metralindole" title="Metralindole">Metralindole</a></li> <li><a href="/wiki/Minaprine" title="Minaprine">Minaprine</a></li> <li><a href="/wiki/Moclobemide" title="Moclobemide">Moclobemide</a></li> <li><a href="/wiki/Pirlindole" title="Pirlindole">Pirlindole</a></li> <li><a href="/wiki/Sercloremine" title="Sercloremine">Sercloremine</a></li> <li><a href="/wiki/Tetrindole" title="Tetrindole">Tetrindole</a></li> <li><a href="/wiki/Toloxatone" title="Toloxatone">Toloxatone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <i>MAO-B selective:</i> <a href="/wiki/Adarigiline" title="Adarigiline">Adarigiline</a></li> <li><a href="/wiki/Almoxatone" title="Almoxatone">Almoxatone</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl"><small>D</small>-Deprenyl</a></li> <li><a href="/wiki/Desmethylselegiline" title="Desmethylselegiline">Desmethylselegiline</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Lazabemide" title="Lazabemide">Lazabemide</a></li> <li><a href="/wiki/Milacemide" title="Milacemide">Milacemide</a></li> <li><a href="/wiki/Mofegiline" title="Mofegiline">Mofegiline</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/Pargyline" title="Pargyline">Pargyline</a><sup>‡</sup></li> <li><a href="/wiki/Rasagiline" title="Rasagiline">Rasagiline</a></li> <li><a href="/wiki/Safinamide" title="Safinamide">Safinamide</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline (<small>L</small>-Deprenyl)</a></li> <li><a href="/wiki/Sembragiline" title="Sembragiline">Sembragiline</a></li> <li><a href="/wiki/Tisolagiline" title="Tisolagiline">Tisolagiline</a></li> <li><a href="/wiki/Vafidemstat" title="Vafidemstat">Vafidemstat</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a><br /><small>(<a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a>,<br /><a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Phenylalanine_hydroxylase" title="Phenylalanine hydroxylase"><abbr title="Phenylalanine hydroxylase">PAH</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 Phenylalanine hydroxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a>→<a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/3,4-Dihydroxystyrene" title="3,4-Dihydroxystyrene">3,4-Dihydroxystyrene</a></li> <li><a href="/wiki/%CE%91-Methylphenylalanine" title="Α-Methylphenylalanine">α-Methylphenylalanine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Tyrosine_hydroxylase" title="Tyrosine hydroxylase"><abbr title="Tyrosine hydroxylase">TH</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 Tyrosine hydroxylase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a>→<a href="/wiki/L-DOPA" title="L-DOPA"><small>L</small>-DOPA (levodopa)</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Iodotyrosine" title="3-Iodotyrosine">3-Iodotyrosine</a></li> <li><a href="/wiki/%CE%91-Methyl-5-hydroxytryptophan" title="Α-Methyl-5-hydroxytryptophan">α-Methyl-5-hydroxytryptophan (α-Me-5-HTP)</a></li> <li><a href="/wiki/%CE%91-Methylphenylalanine" title="Α-Methylphenylalanine">α-Methylphenylalanine</a></li> <li><a href="/wiki/Aquayamycin" title="Aquayamycin">Aquayamycin</a></li> <li><a href="/wiki/Bulbocapnine" title="Bulbocapnine">Bulbocapnine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa (α-methyl-<small>L</small>-DOPA)</a></li> <li><a href="/wiki/Metirosine" class="mw-redirect" title="Metirosine">Metirosine (α-methyl-<i>p</i>-tyrosine)</a></li> <li><a href="/wiki/Oudenone" title="Oudenone">Oudenone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase"><abbr title="Dopamine beta-hydroxylase">DBH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dopamine beta-hydroxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Dopamine" title="Dopamine">Dopamine</a>→<a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (Noradrenaline)</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/Bupicomide" title="Bupicomide">Bupicomide</a></li> <li><a href="/wiki/Disulfiram" title="Disulfiram">Disulfiram</a></li> <li><a href="/wiki/Dopastin" title="Dopastin">Dopastin</a></li> <li><a href="/wiki/Etamicastat" title="Etamicastat">Etamicastat</a></li> <li><a href="/wiki/Fusaric_acid" title="Fusaric acid">Fusaric acid</a></li> <li><a href="/wiki/Nepicastat" title="Nepicastat">Nepicastat</a></li> <li><a href="/wiki/Phenopicolinic_acid" title="Phenopicolinic acid">Phenopicolinic acid</a></li> <li><a href="/wiki/Tropolone" title="Tropolone">Tropolone</a></li> <li><a href="/wiki/Zamicastat" title="Zamicastat">Zamicastat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase"><abbr title="Phenylethanolamine N-methyltransferase">PNMT</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 Phenylethanolamine N-methyltransferase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a>→<a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/w/index.php?title=CGS-19281A&action=edit&redlink=1" class="new" title="CGS-19281A (page does not exist)">CGS-19281A</a></li> <li><a href="/w/index.php?title=SKF-64139&action=edit&redlink=1" class="new" title="SKF-64139 (page does not exist)">SKF-64139</a></li> <li><a href="/w/index.php?title=SKF-7698&action=edit&redlink=1" class="new" title="SKF-7698 (page does not exist)">SKF-7698</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Catechol-O-methyl_transferase" class="mw-redirect" title="Catechol-O-methyl transferase"><abbr title="Catechol-O-methyl transferase">COMT</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 Catechol-O-methyl transferase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Dopamine" title="Dopamine">Dopamine</a>→<a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></li> <li><a href="/wiki/DOPAC" class="mw-redirect" title="DOPAC">DOPAC</a>→<a href="/wiki/Homovanillic_acid" title="Homovanillic acid">Homovanillic acid</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a>→<a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a>→<a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Dihydroxyphenylethylene_glycol" title="Dihydroxyphenylethylene glycol">DOPEG</a>→<a href="/wiki/Methoxyhydroxyphenylglycol" class="mw-redirect" title="Methoxyhydroxyphenylglycol">MOPEG</a></li> <li><a href="/wiki/3,4-Dihydroxymandelic_acid" title="3,4-Dihydroxymandelic acid">DOMA</a>→<a href="/wiki/Vanillylmandelic_acid" title="Vanillylmandelic acid">VMA</a></li> <li><a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a>→<a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a>→<a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a>→<a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a>→<a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/Entacapone" title="Entacapone">Entacapone</a></li> <li><a href="/wiki/Nebicapone" title="Nebicapone">Nebicapone</a></li> <li><a href="/wiki/Neluxicapone" title="Neluxicapone">Neluxicapone</a></li> <li><a href="/wiki/Nitecapone" title="Nitecapone">Nitecapone</a></li> <li><a href="/wiki/Opicapone" title="Opicapone">Opicapone</a></li> <li><a href="/wiki/Quinalizarin" title="Quinalizarin">Quinalizarin</a></li> <li><a href="/wiki/Tolcapone" title="Tolcapone">Tolcapone</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/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a><br /><small>(<a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, <a href="/wiki/Melatonin" title="Melatonin">melatonin</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Tryptophan_hydroxylase" title="Tryptophan hydroxylase"><abbr title="Tryptophan hydroxylase">TPH</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 Tryptophan hydroxylase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a>→<a href="/wiki/5-HTP" class="mw-redirect" title="5-HTP">5-HTP</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/AGN-2979" title="AGN-2979">AGN-2979</a></li> <li><a href="/wiki/Fenclonine" title="Fenclonine">Fenclonine (PCPA)</a></li> <li><a href="/wiki/Telotristat_ethyl" title="Telotristat ethyl">Telotristat ethyl</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Serotonin_N-acetyl_transferase" class="mw-redirect" title="Serotonin N-acetyl transferase"><abbr title="Serotonin N-acetyl transferase">AANAT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Serotonin N-acetyl transferase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Serotonin" title="Serotonin">Serotonin</a>→<a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">N-Acetylserotonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Acetylserotonin_O-methyltransferase" title="Acetylserotonin O-methyltransferase"><abbr title="Acetylserotonin O-methyltransferase">ASMT</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 Acetylserotonin O-methyltransferase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">N-Acetylserotonin</a>→<a href="/wiki/Melatonin" title="Melatonin">Melatonin</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/Histamine" title="Histamine">Histamine</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Histidine_decarboxylase" title="Histidine decarboxylase"><abbr title="Histidine decarboxylase">HDC</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 Histidine decarboxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><small>L</small>-Histidine</a>→<a href="/wiki/Histamine" title="Histamine">Histamine</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/(%2B)-Catechin" class="mw-redirect" title="(+)-Catechin">Catechin</a></li> <li><a href="/wiki/Alpha-Fluoromethylhistidine" class="mw-redirect" title="Alpha-Fluoromethylhistidine">Alpha-Fluoromethylhistidine</a></li> <li><a href="/wiki/Histidine_methyl_ester" title="Histidine methyl ester">Histidine methyl ester</a></li> <li><a href="/wiki/Meciadanol" title="Meciadanol">Meciadanol</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/wiki/Tritoqualine" title="Tritoqualine">Tritoqualine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Histamine_N-methyltransferase" title="Histamine N-methyltransferase"><abbr title="Histamine N-methyltransferase">HNMT</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 Histamine N-methyltransferase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Histamine" title="Histamine">Histamine</a>→<a href="/w/index.php?title=N-Methylhistamine&action=edit&redlink=1" class="new" title="N-Methylhistamine (page does not exist)">N-Methylhistamine</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/Amodiaquine" title="Amodiaquine">Amodiaquine</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li> <li><a href="/wiki/Harmaline" title="Harmaline">Harmaline</a></li> <li><a href="/wiki/Metoprine" title="Metoprine">Metoprine</a></li> <li><a href="/wiki/Quinacrine" class="mw-redirect" title="Quinacrine">Quinacrine</a></li> <li><a href="/wiki/SKF-91488" title="SKF-91488">SKF-91488</a></li> <li><a href="/wiki/Tacrine" title="Tacrine">Tacrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Diamine_oxidase" title="Diamine oxidase"><abbr title="Diamine oxidase">DAO</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 Diamine oxidase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Histamine" title="Histamine">Histamine</a>→<a href="/w/index.php?title=Imidazole_acetic_acid&action=edit&redlink=1" class="new" title="Imidazole acetic acid (page does not exist)">Imidazole acetic acid</a></li></ul> <ul><li><b>Inhibitors:</b> <a class="mw-selflink selflink">Pimagedine (aminoguanidine)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><small><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Adrenergics" class="mw-redirect" title="Template:Adrenergics">Adrenergics</a> • <a href="/wiki/Template:Dopaminergics" class="mw-redirect" title="Template:Dopaminergics">Dopaminergics</a> • <a href="/wiki/Template:Melatonergics" class="mw-redirect" title="Template:Melatonergics">Melatonergics</a> • <a href="/wiki/Template:Serotonergics" class="mw-redirect" title="Template:Serotonergics">Serotonergics</a> • <a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> • <a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">Monoamine releasing agents</a> • <a href="/wiki/Template:Monoamine_neurotoxins" class="mw-redirect" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></i></small></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="Hydrazines14" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Hydrazines" title="Template:Hydrazines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hydrazines" title="Template talk:Hydrazines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hydrazines" title="Special:EditPage/Template:Hydrazines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Hydrazines14" style="font-size:114%;margin:0 4em"><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazines</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Phenylthiosemicarbazide" title="4-Phenylthiosemicarbazide">4-PTSC</a></li> <li><a href="/wiki/Acylhydrazine" class="mw-redirect" title="Acylhydrazine">Acylhydrazine</a></li> <li><a href="/wiki/Adipic_acid_dihydrazide" title="Adipic acid dihydrazide">ADH</a></li> <li><a href="/wiki/Adjudin" title="Adjudin">Adjudin</a></li> <li><a href="/wiki/Agaritine" title="Agaritine">Agaritine</a></li> <li><a href="/wiki/Benmoxin" title="Benmoxin">Benmoxin</a></li> <li><a href="/wiki/Cadralazine" title="Cadralazine">Cadralazine</a></li> <li><a href="/wiki/Carbazide" title="Carbazide">Carbazide</a></li> <li><a href="/wiki/Carbidopa" title="Carbidopa">Carbidopa</a></li> <li><a href="/wiki/Carbohydrazide" title="Carbohydrazide">Carbohydrazide</a></li> <li><a href="/wiki/Daminozide" title="Daminozide">Daminozide</a></li> <li><a href="/wiki/Dihydralazine" title="Dihydralazine">Dihydralazine</a></li> <li><a href="/wiki/2,4-Dinitrophenylhydrazine" title="2,4-Dinitrophenylhydrazine">DNPH</a></li> <li><a href="/wiki/Endralazine" title="Endralazine">Endralazine</a></li> <li><a href="/wiki/Gyromitrin" title="Gyromitrin">Gyromitrin</a></li> <li><a href="/wiki/HBT_(explosive)" title="HBT (explosive)">HBT</a></li> <li><a href="/wiki/Hydralazine" title="Hydralazine">Hydralazine</a></li> <li><a href="/wiki/Hydrazide" title="Hydrazide">Hydrazide</a></li> <li><a href="/wiki/Hydrazine" title="Hydrazine">Hydrazine</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Iproclozide" title="Iproclozide">Iproclozide</a></li> <li><a href="/wiki/Iproniazid" title="Iproniazid">Iproniazid</a></li> <li><a href="/wiki/Isocarboxazid" title="Isocarboxazid">Isocarboxazid</a></li> <li><a href="/wiki/Isoniazid" title="Isoniazid">Isoniazid</a></li> <li><a href="/wiki/Mebanazine" title="Mebanazine">Mebanazine</a></li> <li><a href="/wiki/Metfendrazine" title="Metfendrazine">Metfendrazine</a></li> <li><a href="/wiki/Monomethylhydrazine" title="Monomethylhydrazine">MMH</a></li> <li><a href="/wiki/Nialamide" title="Nialamide">Nialamide</a></li> <li><a href="/wiki/Octamoxin" title="Octamoxin">Octamoxin</a></li> <li><a href="/wiki/Phenylethylidenehydrazine" title="Phenylethylidenehydrazine">PEH</a></li> <li><a href="/wiki/Phenelzine" title="Phenelzine">Phenelzine</a></li> <li><a href="/wiki/Pheniprazine" title="Pheniprazine">Pheniprazine</a></li> <li><a href="/wiki/Phenoxypropazine" title="Phenoxypropazine">Phenoxypropazine</a></li> <li><a href="/wiki/Phenylhydrazine" 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