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<div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic compound (C11H10Cl2N4)</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Metoprine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png/220px-Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png" decoding="async" width="220" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png/330px-Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png/440px-Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png 2x" data-file-width="1274" data-file-height="854" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">5-(3,4-dichlorophenyl)-6-methylpyrimidine-2,4-diamine</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=7761-45-7">7761-45-7</a></span></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=CC1%3DC%28C%28%3DNC%28%3DN1%29N%29N%29C2%3DCC%28%3DC%28C%3DC2%29Cl%29Cl">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/ChEMBL264373">ChEMBL264373</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.22874.html">22874</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB04655">DB04655</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/D00309">D00309</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/24466">24466</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/2L9RKX796Q">2L9RKX796Q</a></span></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/DTXSID0057831">DTXSID0057831</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q27085870#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/C11H10Cl2N4/c1-5-9(10(14)17-11(15)16-5)6-2-3-7(12)8(13)4-6/h2-4H,1H3,(H4,14,15,16,17)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: VQJHOPSWBGJHQS-UHFFFAOYSA-N</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%;">CC1=C(C(=NC(=N1)N)N)C2=CC(=C(C=C2)Cl)Cl</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><sub>11</sub><span title="Hydrogen">H</span><sub>10</sub><span title="Chlorine">Cl</span><sub>2</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><span class="nowrap"><span data-sort-value="7002269130000000000♠"></span>269.13</span> g·mol<sup>−1</sup>   </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> <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>Metoprine</b> (2,4-diamino-5-(3′,4′-dichlorophenyl)-6-methylpyrimidine) is a dihydrofolate reductase (DHFR) inhibitor initially developed for potential applications in cancer treatment. Although it never achieved widespread clinical adoption, its properties have made it an important research tool in oncology, neurobiology, and parasitology. Other synonyms for metoprine include BW-197U, DDMP, Methodichlorophen, NSC-19494, NSC7364, and TCMDC-123931. </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=Metoprine&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metoprine was developed in the 1970s as a lipid-soluble antifolate with improved cellular penetration compared to methotrexate (MTX), which requires carrier-mediated transport. Early studies demonstrated its efficacy in inhibiting tumor growth. However, its clinical use was limited due to its long half-life (~10 days in humans) and significant toxicity, including hematological, neurological, cutaneous, and gastrointestinal side effects. </p><p>Beyond its anticancer potential, metoprine was later discovered to inhibit histamine-N-methyltransferase (HNMT), an enzyme involved in histamine degradation. This led to its use as a research tool for studying histamine's role in neurological and immune functions. Additionally, its ability to disrupt folate metabolism made it a candidate for treating parasitic infections.<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> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png/220px-Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png" decoding="async" width="220" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png/330px-Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png/440px-Sk%C3%A6rmbillede_2025-03-11_kl._17.45.10.png 2x" data-file-width="1274" data-file-height="854" /></a><figcaption>Chemical structure</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Structure_and_reactivity">Structure and reactivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metoprine&action=edit&section=2" title="Edit section: Structure and reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metoprine belongs to the 2,4-diaminopyrimidine class and shares structural similarities with other antifolates. Its pyrimidine core, with amino groups at the 2 and 4 positions, is essential for DHFR inhibition. The benzyl group at the 6-position increases lipophilicity, aiding in membrane permeability. The molecule's basicity allows it to engage in hydrogen bonding interactions with DHFR, contributing to its biological activity.<sup id="cite_ref-:1_2-0" class="reference"><a href="#cite_note-:1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Available_forms">Available forms</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metoprine&action=edit&section=3" title="Edit section: Available forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metoprine is not a commercially available drug but is used in research settings. It is typically supplied as a powder for laboratory studies, with some solvent-based formulations also available for experimental applications.<sup id="cite_ref-:1_2-1" class="reference"><a href="#cite_note-:1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metoprine&action=edit&section=4" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metoprine acts as a competitive inhibitor of DHFR by mimicking dihydrofolate (DHF) and thereby occupying the enzyme's active site.<sup id="cite_ref-:0_3-0" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> This prevents the conversion of DHF to tetrahydrofolate (THF), which is an essential cofactor for purine, thymidylate, and amino acid synthesis. Consequently, metoprine disrupts DNA and RNA synthesis, impairing cell proliferation.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><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> This mechanism underlies its potential use in chemotherapy. </p><p>In addition to DHFR inhibition, metoprine blocks HNMT, leading to increased histamine levels in the brain. This enhances histaminergic neurotransmission, which has been implicated in cognitive function, wakefulness, and behavioral modulation.<sup id="cite_ref-:2_6-0" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Metoprine is a potent HNMT inhibitor, with a Ki value of 100 nM.<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> Studies in rodents have demonstrated that metoprine increases locomotor activity and induces transient stereotyped behaviors.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biotransformation">Biotransformation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metoprine&action=edit&section=5" title="Edit section: Biotransformation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>While the pharmacodynamics of metoprine have been extensively studied, details on its metabolic pathways remain limited. Biotransformation and primary metabolites are not well-documented.<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> Metoprine interacts with several genes, including HNMT, androgen receptor (AR), cytochrome c oxidase subunit 4I1 (COX4I1), estrogen receptor 1 (ESR1), and tumor protein p53 (TP53).<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Absorption_and_distribution">Absorption and distribution</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metoprine&action=edit&section=6" title="Edit section: Absorption and distribution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metoprine is well-absorbed and widely distributed across various tissues. Highest tissue-to-plasma ratios are obtained in the brain, lung, pancreas, and skin, attributed to its lipophilicity and ability to cross the blood-brain barrier.<sup id="cite_ref-:0_3-1" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:3_11-0" class="reference"><a href="#cite_note-:3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> A 1981 study suggested complex pharmacokinetics, including non-linear elimination patterns and prolonged retention in tissues. Only 5-17% of an administered dose is excreted in the urine within a 120-hour period, indicating extensive metabolism or tissue accumulation.<sup id="cite_ref-:0_3-2" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><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> The exact elimination pathways—whether renal, biliary, or other routes—are not well-documented. </p> <div class="mw-heading mw-heading2"><h2 id="Indications">Indications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metoprine&action=edit&section=7" title="Edit section: Indications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metoprine has been explored for multiple therapeutic applications, including: </p> <ul><li><b>Cancer treatment</b>: As a DHFR inhibitor, metoprine showed promise in early trials for conditions such as central nervous system leukemia, malignant melanoma, and epidermoid carcinoma. However, its development was halted due to CNS and hematological toxicity.<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></li> <li><b>Neurological research</b>: Due to its ability to elevate brain histamine levels, metoprine has been investigated for its effects on cognition and wakefulness. In narcoleptic mouse models, it prolonged wakefulness and suppressed cataplexy, suggesting potential in sleep disorder therapy.<sup id="cite_ref-:2_6-1" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Efficacy_and_side_effects">Efficacy and side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metoprine&action=edit&section=8" title="Edit section: Efficacy and side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metoprine has been investigated for its antitumor effects in various cancers. Clinical trials assessed metoprine's efficacy in cancer treatment, with phase I studies administering doses between 20-65 mg/m² without leucovorin and 100-300 mg/m² with leucovorin rescue. Responses were observed in mycosis fungoides, non-Hodgkin's lymphoma, and adenocarcinoma of unknown origin. However, no objective tumor regression was noted in colorectal carcinoma patients.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Metoprine has also been linked to memory enhancement by inhibiting histamine breakdown. In a 2000 study, treatment with metoprine reversed scopolamine-induced amnesia in mice via histaminergic mechanisms activating histamine H1 receptors.<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><p>Common side effects include nausea, vomiting, leukopenia, and thrombocytopenia.<sup id="cite_ref-:0_3-3" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metoprine&action=edit&section=9" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metoprine's clinical development was discontinued primarily due to CNS and hematological toxicity. In phase I trials, CNS toxicity manifested as seizures, drowsiness, and dizziness, which were significant at high doses (300 mg/m²). Hematologic toxicity, including thrombocytopenia and leukopenia, was dose-limiting at 65 mg/m² without leucovorin.<sup id="cite_ref-:3_11-1" class="reference"><a href="#cite_note-:3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:4_16-0" class="reference"><a href="#cite_note-:4-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>In a phase II colorectal carcinoma trial, CNS toxicity occurred in 54% of patients, further discouraging continued development.<sup id="cite_ref-:3_11-2" class="reference"><a href="#cite_note-:3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:4_16-1" class="reference"><a href="#cite_note-:4-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Effects_in_animals">Effects in animals</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metoprine&action=edit&section=10" title="Edit section: Effects in animals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metoprine exhibits species-specific toxicity profiles. In rats, the intraperitoneal LD₅₀ is 7 mg/kg, whereas in mice, the subcutaneous LD₅₀ is 50 mg/kg. Behavioral studies in mice indicate that metoprine alters histaminergic and dopaminergic signaling, affecting locomotor activity and neurotransmitter turnover. It also modulates methamphetamine-induced hyperlocomotion, suggesting potential interactions with stimulant drugs.<sup id="cite_ref-:0_3-4" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:2_6-2" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <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=Metoprine&action=edit&section=11" 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="CITEREFGrivskyLeeSigelDuch1980" class="citation journal cs1">Grivsky, Eugene M.; Lee, Shuliang; Sigel, Carl W.; Duch, David S.; Nichol, Charles A. 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