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Pyrazolopyrimidine - Wikipedia

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class="mw-page-title-main">Pyrazolopyrimidine</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%BE%DB%8C%D8%B1%D8%A7%D8%B2%D9%88%D9%84%D9%88_%D9%BE%DB%8C%D8%B1%D8%A7%D9%85%DB%8C%D8%AF%DB%8C%D9%86" title="پیرازولو پیرامیدین – Persian" lang="fa" hreflang="fa" data-title="پیرازولو پیرامیدین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Pirazolopirimidin" title="Pirazolopirimidin – Serbian" lang="sr" hreflang="sr" data-title="Pirazolopirimidin" 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/Pirazolopirimidin" title="Pirazolopirimidin – Serbo-Croatian" 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<div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Pyrazolo[1,5-<i>a</i>]pyrimidine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Pyrazolopyrimidine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Pyrazolopyrimidine.svg/150px-Pyrazolopyrimidine.svg.png" decoding="async" width="150" height="108" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Pyrazolopyrimidine.svg/225px-Pyrazolopyrimidine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Pyrazolopyrimidine.svg/300px-Pyrazolopyrimidine.svg.png 2x" data-file-width="512" data-file-height="369" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Pyrazolo[1,5-<i>a</i>]pyrimidine</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=274-71-5">274-71-5</a></span><sup>&#160;<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=n1cccn2nccc12">Interactive image</a></span></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.9811537.html">9811537</a></span></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/100.227.461">100.227.461</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q7263418#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/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/11636795">11636795</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/NX2KR7M4A4">NX2KR7M4A4</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID70469781">DTXSID70469781</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q7263418#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; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C6H5N3/c1-3-7-6-2-4-8-9(6)5-1/h1-5H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key:&#160;LDIJKUBTLZTFRG-UHFFFAOYSA-N</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C6H5N3/c1-3-7-6-2-4-8-9(6)5-1/h1-5H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key:&#160;LDIJKUBTLZTFRG-UHFFFAOYAL</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">n1cccn2nccc12</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>6</sub><span title="Hydrogen">H</span><sub>5</sub><span title="Nitrogen">N</span><sub>3</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002119127000000000♠"></span>119.127</span>&#160;g·mol<sup>−1</sup> &#x20; </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25&#160;°C [77&#160;°F], 100&#160;kPa).</div> <div style="margin-top: 0.3em;"></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>Pyrazolopyrimidines</b> are a series of <a href="/wiki/Isomer" title="Isomer">isomeric</a> <a href="/wiki/Heterocyclic" class="mw-redirect" title="Heterocyclic">heterocyclic</a> <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compounds</a> with the molecular formula C<sub>6</sub>H<sub>5</sub>N<sub>3</sub>. <sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> They form the central core of a variety of more complex chemical compounds including some pharmaceuticals and pesticides. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Pharmaceuticals">Pharmaceuticals</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrazolopyrimidine&amp;action=edit&amp;section=1" title="Edit section: Pharmaceuticals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>One isomer of pyrazolopyrimidines, known as pyrazolo[1,5-<i>a</i>]pyrimidine, is the basis for a class of <a href="/wiki/Sedative" title="Sedative">sedative</a> and <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a> <a href="/wiki/Medication" title="Medication">drugs</a> related (in terms of their effect) to <a href="/wiki/Benzodiazepine" title="Benzodiazepine">benzodiazepines</a>. </p><p>Most of the drugs from this class marketed to date are intended to induce <a href="/wiki/Sleep" title="Sleep">sleep</a>, and are prescribed for people suffering <a href="/wiki/Insomnia" title="Insomnia">insomnia</a>, however some newer compounds produce <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a> effects with relatively little sedation, and are being developed for use as non-sedating anti-anxiety drugs. </p><p>They include: </p> <ul><li><a href="/wiki/Zaleplon" title="Zaleplon">Zaleplon</a> - hypnotic (trade name <b>Sonata</b>)</li> <li><a href="/wiki/Indiplon" title="Indiplon">Indiplon</a> - hypnotic</li> <li><a href="/wiki/Ocinaplon" title="Ocinaplon">Ocinaplon</a> - anxiolytic</li> <li><a href="/wiki/Lorediplon" title="Lorediplon">Lorediplon</a> - hypnotic</li></ul> <p>As they are not chemically related to the benzodiazepines despite their similar effect, such drugs—as well as the <a href="/wiki/Imidazopyridine" title="Imidazopyridine">imidazopyridines</a> and <a href="/wiki/Cyclopyrrone" class="mw-redirect" title="Cyclopyrrone">cyclopyrrones</a>—are sometimes grouped together and referred to as "<a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">nonbenzodiazepines</a>". </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Zaleplon_skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Zaleplon_skeletal.svg/100px-Zaleplon_skeletal.svg.png" decoding="async" width="100" height="193" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Zaleplon_skeletal.svg/150px-Zaleplon_skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/26/Zaleplon_skeletal.svg/200px-Zaleplon_skeletal.svg.png 2x" data-file-width="512" data-file-height="986" /></a><figcaption>Zaleplon</figcaption></figure><div style="clear:left;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Pesticides">Pesticides</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrazolopyrimidine&amp;action=edit&amp;section=2" title="Edit section: Pesticides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A related use is in pyrazolopyrimidine <a href="/wiki/Organothiophosphate" title="Organothiophosphate">organothiophosphate</a> <a href="/wiki/Pesticide" title="Pesticide">pesticides</a> including chlorprazophos (<a href="/wiki/Insecticide" title="Insecticide">insecticide</a>) and <a href="/wiki/Pyrazophos" title="Pyrazophos">pyrazophos</a> (fungicide, insecticide). </p> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Pyrazophos.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Pyrazophos.svg/220px-Pyrazophos.svg.png" decoding="async" width="220" height="115" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Pyrazophos.svg/330px-Pyrazophos.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/de/Pyrazophos.svg/440px-Pyrazophos.svg.png 2x" data-file-width="552" data-file-height="289" /></a><figcaption>Pyrazophos</figcaption></figure><div style="clear:left;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrazolopyrimidine&amp;action=edit&amp;section=3" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">Nonbenzodiazepine</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrazolopyrimidine&amp;action=edit&amp;section=4" 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"><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 class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.chemspider.com/Chemical-Structure.10466972.html">"Note that according to other sources, the structure is different, and the sum formula is C5H4N4: see pyrazolopyrimidine on"</a>. <i>ChemSpider</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2018-11-07</span></span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=ChemSpider&amp;rft.atitle=Note+that+according+to+other+sources%2C+the+structure+is+different%2C+and+the+sum+formula+is+C5H4N4%3A+see+pyrazolopyrimidine+on&amp;rft_id=http%3A%2F%2Fwww.chemspider.com%2FChemical-Structure.10466972.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3APyrazolopyrimidine" class="Z3988"></span></span> </li> </ol></div></div> <!-- NewPP limit report Parsed by mw‐web.eqiad.main‐5dc468848‐bv4gd Cached time: 20241122145203 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 0.514 seconds Real time usage: 0.937 seconds Preprocessor visited node count: 5730/1000000 Post‐expand include size: 56116/2097152 bytes Template argument size: 16516/2097152 bytes Highest expansion depth: 25/100 Expensive parser function count: 2/500 Unstrip recursion depth: 1/20 Unstrip post‐expand size: 6623/5000000 bytes Lua time usage: 0.224/10.000 seconds Lua memory usage: 4986088/52428800 bytes Number of Wikibase entities loaded: 1/400 --> <!-- Transclusion expansion time report (%,ms,calls,template) 100.00% 663.862 1 -total 82.01% 544.410 1 Template:Chembox 44.64% 296.319 1 Template:Chembox_Identifiers 21.88% 145.240 3 Template:Chembox_headerbar 20.67% 137.222 9 Template:Trim 16.84% 111.805 1 Template:Reflist 14.97% 99.409 1 Template:Cite_web 14.55% 96.588 9 Template:Main_other 14.20% 94.278 14 Template:Unbulleted_list 13.78% 91.490 1 Template:Chembox_Properties --> <!-- Saved in parser cache with key enwiki:pcache:idhash:2013521-0!canonical and timestamp 20241122145203 and revision id 1227234976. 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