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<title>[O-methyl-11C]2-{4-[4-(7-Methoxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2H-[1,2,4]triazine-3,5-dione - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf</title>
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<div class="pre-content"><div><div class="bk_prnt"><p class="small">NCBI Bookshelf. A service of the National Library of Medicine, National Institutes of Health.</p><p>Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. </p></div><div class="iconblock clearfix whole_rhythm no_top_margin bk_noprnt"><a class="img_link icnblk_img" title="Table of Contents Page" href="/books/n/micad/"><img class="source-thumb" src="/corehtml/pmc/pmcgifs/bookshelf/thumbs/th-micad-lrg.png" alt="Cover of Molecular Imaging and Contrast Agent Database (MICAD)" height="100px" width="80px" /></a><div class="icnblk_cntnt eight_col"><h2>Molecular Imaging and Contrast Agent Database (MICAD) [Internet].</h2><a data-jig="ncbitoggler" href="#__NBK23187_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23187_dtls__"><div>Bethesda (MD): <a href="https://www.ncbi.nlm.nih.gov/" ref="pagearea=page-banner&targetsite=external&targetcat=link&targettype=publisher">National Center for Biotechnology Information (US)</a>; 2004-2013.</div></div><div class="half_rhythm"><ul class="inline_list"><li style="margin-right:1em"><a class="bk_cntns" href="/books/n/micad/">Contents</a></li></ul></div><div class="bk_noprnt"><form method="get" action="/books/n/micad/" id="bk_srch"><div class="bk_search"><label for="bk_term" class="offscreen_noflow">Search term</label><input type="text" title="Search this book" id="bk_term" name="term" value="" data-jig="ncbiclearbutton" /> <input type="submit" class="jig-ncbibutton" value="Search this book" submit="false" style="padding: 0.1em 0.4em;" /></div></form></div></div><div class="icnblk_cntnt two_col"><div class="pagination bk_noprnt"><a class="active page_link prev" href="/books/n/micad/MMP11C/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/MeS-IMPY11C/" title="Next page in this title">Next ></a></div></div></div></div></div>
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<div class="main-content lit-style" itemscope="itemscope" itemtype="http://schema.org/CreativeWork"><div class="meta-content fm-sec"><h1 id="_NBK23187_"><span class="title" itemprop="name">[<i>O</i>-methyl-<sup>11</sup>C]2-{4-[4-(7-Methoxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2<i>H</i>-[1,2,4]triazine-3,5-dione</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">[<sup>11</sup>C]MPT</div><p class="contrib-group"><span itemprop="author">Kenneth T. Cheng</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK23187_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK23187_ai__"><div class="contrib half_rhythm"><span itemprop="author">Kenneth T. Cheng</span>, PhD<div class="affiliation small">
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National Center for Biotechnology Information, NLM, NIH, Bethesda, MD,
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<span class="before-email-separator"></span><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="vog.hin.mln.ibcn@dacim" class="oemail">vog.hin.mln.ibcn@dacim</a>
|
||
</div></div></div><p class="small">Created: <span itemprop="datePublished">January 30, 2007</span>; Last Update: <span itemprop="dateModified">February 26, 2008</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="MPT11C.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23187/table/MPT11C.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__MPT11C.T1_lrgtbl__"><table><tbody><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Chemical name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<i>O</i>-methyl-<sup>11</sup>C]2-{4-[4-(7-Methoxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2<i>H</i>-[1,2,4]triazine-3,5-dione</td><td rowspan="9" colspan="1" style="text-align:left;vertical-align:middle;">
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<a href="https://pubchem.ncbi.nlm.nih.gov/substance/24429253" title="View this structure in PubChem" class="img_link" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem"><img src="https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?t=l&sid=24429253" alt="image 24429253 in the ncbi pubchem database" /></a>
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</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Abbreviated name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<sup>11</sup>C]MPT</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Synonym:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<sup>11</sup>C]F1146</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Agent Category:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Compound</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Target:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">5-HT<sub>1A</sub> serotonin receptors</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Target Category:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Receptor binding</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Method of detection:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Positron Emission Tomography (PET)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Source of signal:</b>
|
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>11</sup>C</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Activation:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">No</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Studies:</b>
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||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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||
<ul class="simple-list"><li class="half_rhythm"><div>
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||
<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
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<i>In vitro</i>
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</div></li></ul>
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||
<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Non-human primates
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</div></li></ul>
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<br />
|
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Click on the above structure for additional information in <a href="http://pubchem.ncbi.nlm.nih.gov" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubChem</a>.</td></tr></tbody></table></div></div><div id="MPT11C.Background"><h2 id="_MPT11C_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28A%20novel%205-HT1A%20receptor%20agonist%20positron%20emission%20tomography%20ligand%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>[<i>O</i>-methyl-<sup>11</sup>C]2-{4-[4-(7-Methoxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2<i>H</i>-[1,2,4]triazine-3,5-dione ([<sup>11</sup>C]MPT) is a radioligand developed for positron emission tomography (PET) imaging of serotonin-1A (5-hydroxytryptamine 1A (5-HT<sub>1A</sub>)) receptors in the central nervous system (<a class="bk_pop" href="#MPT11C.REF.1">1</a>). It is a selective 5-HT<sub>1A</sub> agonist labeled with <sup>11</sup>C, a positron emitter with a physical half-life (<i>t</i><sub>½</sub>) of 20.4 min (<a class="bk_pop" href="#MPT11C.REF.1">1</a>, <a class="bk_pop" href="#MPT11C.REF.2">2</a>).</p><p>The 5-HT neurotransmission system comprises mainly neurons in the brainstem, with nerve tracts extending from these neurons to many areas of the brain and spinal cord (<a class="bk_pop" href="#MPT11C.REF.3">3</a>). The effects of 5-HT are mediated by as many as seven classes of receptor populations (5-HT<sub>1</sub> to 5-HT<sub>7</sub>), many of which also contain several subtypes (<a class="bk_pop" href="#MPT11C.REF.4">4</a>). There are five receptor subtypes within the G-protein–coupled 5-HT<sub>1</sub> receptor family, with the 5-HT<sub>1A</sub> subtype located primarily in the limbic forebrain (the hippocampus, entorhinal cortex ,septum, and raphe) (<a class="bk_pop" href="#MPT11C.REF.4">4</a>, <a class="bk_pop" href="#MPT11C.REF.5">5</a>). 5-HT<sub>1A</sub> receptors appear to function both as presynaptic (somatodendritic) autoreceptors in the raphe nuclei and as postsynaptic receptors in the terminal fields. This receptor subtype is involved in the modulation of emotion and the function of the hypothalamus, and it is implicated in the pathogenesis of anxiety, depression, hallucinogenic behavior, motion sickness, dementia, schizophrenia, and eating disorders (<a class="bk_pop" href="#MPT11C.REF.6">6</a>). A radioligand that can be used to assess the <i>in vivo</i> densities of 5-HT<sub>1A</sub> receptors and their changes may facilitate investigation of the relationship of these receptors to various neuropsychiatric diseases and aid in the design of novel drugs for their treatment.</p><p>Many psychiatric drugs modulate serotonergic transmission or specifically target the 5-HT<sub>1A</sub> receptors (<a class="bk_pop" href="#MPT11C.REF.2">2</a>). Various compounds have been radiolabeled for visualization and quantification of these receptors (<a class="bk_pop" href="#MPT11C.REF.7">7</a>). 5-HT<sub>1A</sub> receptors appear to exist in the high (HA) and low (LA) agonist affinity states. Antagonist ligands bind to both the HA and LA conformations, whereas agonist ligands bind to the HA state, which is coupled to G-protein. WAY 100635 was developed as a highly selective, silent antagonist (possessing no intrinsic agonist activity) of 5-HT<sub>1A</sub> receptors at both pre- and postsynaptic sites. <a href="/books/n/micad/Carbonyl11C-WAY/">WAY 100635</a> radiolabeled with <sup>11</sup>C at the carbonyl position is an effective radioligand but it is rapidly cleared and metabolized. Analogs of WAY 100635 that bear bulkier cycloalkylcarbonyl groups appear to be more resistant to amide hydrolysis. However, the added lipophilicity also reduces receptor affinity (<a class="bk_pop" href="#MPT11C.REF.8">8</a>). Although 5-HT<sub>1A</sub> receptor agonist ligands can elicit pharmacologic effects, there are some distinct potential applications of radiolabeled 5-HT<sub>1A</sub> receptor agonist ligands because they behave like serotonin, which binds preferentially to the HA sites (<a class="bk_pop" href="#MPT11C.REF.1">1</a>, <a class="bk_pop" href="#MPT11C.REF.9">9</a>). Kumar et al. (<a class="bk_pop" href="#MPT11C.REF.1">1</a>) selected MPT for development as a radiolabeled 5-HT<sub>1A</sub> receptor agonist probe because of its high affinity (p<i>K</i><sub>i</sub> = 10.49) and favorable calculated lipophilicity (clog<i>P</i> = 1.8) (<a class="bk_pop" href="#MPT11C.REF.10">10</a>, <a class="bk_pop" href="#MPT11C.REF.11">11</a>)</p></div><div id="MPT11C.Synthesis"><h2 id="_MPT11C_Synthesis_">Synthesis</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28A%20novel%205-HT1A%20receptor%20agonist%20positron%20emission%20tomography%20ligand%29%20AND%20synthesis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Kumar et al. (<a class="bk_pop" href="#MPT11C.REF.1">1</a>) designed the synthesis of MPT in five steps from the starting material of commercially available 6-azauracil. Briefly, 6-azauracil was selectively acetylated at the 2-position by refluxing in acetic anhydride. The resulting product was methylated at the 4-position by sodium hydride in <i>N</i>,<i>N</i>-dimethylformamide (DMF) and methyl iodide followed by treatment with catalytic <i>p</i>-TsOH in refluxing ethanol. This methylated compound was alkylated with 1-bromo-4-chlorobutane in DMF and sodium hydride to produce 2-(4-chlorobutyl)-4-methyl-2<i>H</i>-[1,2,4]triazine-3,5-dione. This compound was used to prepare the precursors for MPT and [<sup>11</sup>C]MPT. To prepare the radiolabeling precursor, 8-aminonaphthalen-2-ol and bis-(2-chloroethyl)amine in poly(ethylene glycol) were reacted in microwave conditions to yield 8-piperazin-1-ylnaphthalen-2-ol. This was coupled with 2-(4-chlorobutyl)-4-methyl-2<i>H</i>-[1,2,4]triazine-3,5-dione to yield the desmethyl precursor 2-{4-[4-(7-hydroxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2<i>H</i>-[1,2,4]triazine-3,5-dione, which was used for radiolabeling. This precursor was treated with [<sup>11</sup>C]CH<sub>3</sub>OTf in acetone in the presence of 10 μl of 5 <span class="small-caps">M</span> sodium hydroxide at room temperature. The radiolabeled MPT was purified by high-performance liquid chromatography (HPLC) and passed through a C-18 Sep-Pak cartridge. The radiochemical yield at the end of synthesis was 25 ± 5% (<i>n</i> = 15), and the chemical and radiochemical purities were >99%. The specific activity of [<sup>11</sup>C]MPT was 55.5 ± 11.1 TBq/mmol (1,500 ± 300 Ci/mmol; <i>n</i> = 10) at the end of bombardment (EOB). The average time of labeling was 30 min from the time of EOB.</p></div><div id="MPT11C.In_Vitro_Studies_Tes"><h2 id="_MPT11C_In_Vitro_Studies_Tes_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28A%20novel%205-HT1A%20receptor%20agonist%20positron%20emission%20tomography%20ligand%29%20AND%20in%20vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The partition coefficient (log<i>P</i><sub>OCT</sub>) of [<sup>11</sup>C]MPT was determined to be 2.2 by the standard shake-flask method by mixing the radioligand in 1-octanol and phosphate-buffered saline (pH 7.4) (<a class="bk_pop" href="#MPT11C.REF.1">1</a>). The inhibitory constant value (<i>K</i><sub>i</sub>) of unlabeled MPT for 5-HT<sub>1A</sub> was found to be 1.36 ± 0.16 nM by use of the competition binding studies with [<sup>3</sup>H]8-OH-DPAT (5-HT<sub>1A</sub> receptor agonist) in membrane fractions from Chinese hamster ovary (CHO) cells that had a density of 8 pmol/mg 5-HT<sub>1A</sub> receptors. The <i>K</i><sub>i</sub> of MPT for other 5-HT receptor subtypes (5-HT<sub>2A</sub> to 5-HT<sub>7</sub>) ranged from 9.1 (5-HT<sub>7</sub>) to >10,000 nM (5-HT<sub>3</sub>). In comparison, serotonin had a <i>K</i><sub>i</sub> value of 1.58 nM for the 5-HT<sub>1A</sub> receptors. An <i>in vitro</i> agonist-stimulated [<sup>35</sup>S]GTPγS binding assay indicated that MPT was a 5-HT<sub>1A</sub> receptor agonist with an affinity greater than that of endogenous serotonin. The EC<sub>50</sub> values of MPT and serotonin were determined to be 0.05 nM and 0.5 nM, respectively. In the inhibition assay of forskolin-stimulated cAMP accumulation, the EC<sub>50</sub> values of MPT and serotonin were 0.01 nM and 1 nM, respectively.</p></div><div id="MPT11C.Animal_Studies"><h2 id="_MPT11C_Animal_Studies_">Animal Studies</h2><div id="MPT11C.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28A%20novel%205-HT1A%20receptor%20agonist%20positron%20emission%20tomography%20ligand%29%20AND%20rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="MPT11C.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28A%20novel%205-HT1A%20receptor%20agonist%20positron%20emission%20tomography%20ligand%29%20AND%20%28dog%20OR%20rabbit%20OR%20pig%20OR%20sheep%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="MPT11C.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28A%20novel%205-HT1A%20receptor%20agonist%20positron%20emission%20tomography%20ligand%29%20AND%20%28primate%20NOT%20human%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Kumar et al. (<a class="bk_pop" href="#MPT11C.REF.1">1</a>) evaluated the <i>in vivo</i> properties of [<sup>11</sup>C]MPT in baboons. For each study, a single male baboon received an i.v. dose of 185 ± 18.5 MBq (5 ± 0.5 mCi) for PET imaging studies. The PET imaging showed that [<sup>11</sup>C]MPT rapidly penetrated the blood–brain barrier and accumulated in brain regions known to have high densities of 5-HT<sub>1A</sub> receptors. The cerebellum had the lowest radioactivity level of [<sup>11</sup>C]MPT. There was a high correlation between the volume of distribution (<i>V</i><sub>T</sub>) of [<sup>11</sup>C]WAY 100635 and the <i>V</i><sub>T</sub> of [<sup>11</sup>C]MPT. When 0.5 mg/kg unlabeled WAY 100635 or 2 mg/kg 8-OH-DPAT was given 20 min before [<sup>11</sup>C]MPT administration, the radioactivity levels in all brain regions were reduced to the same level as the cerebellar reference region. Blocking studies with a 5-HT<sub>2A</sub> antagonist and a dopamine antagonist showed that [<sup>11</sup>C]MPT did not have significant affinity for 5-HT<sub>2A</sub> or dopamine receptors.</p><p>HPLC analysis of [<sup>11</sup>C]MPT metabolite in baboons indicated that [<sup>11</sup>C]MPT underwent fast metabolism, and the percentages (<i>n</i> = 15) of unchanged [<sup>11</sup>C]MPT in the total plasma radioactivity were 90 ± 2% (2 min), 87 ± 3% (4 min), 65 ± 5% (12 min), 30 ± 5% (30 min), 20 ± 3% (60 min), and 12 ± 3% (90 min) (<a class="bk_pop" href="#MPT11C.REF.1">1</a>). Only polar metabolites were discovered in the plasma samples.</p></div></div><div id="MPT11C.Human_Studies"><h2 id="_MPT11C_Human_Studies_">Human Studies</h2><p><a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28A%20novel%205-HT1A%20receptor%20agonist%20positron%20emission%20tomography%20ligand%29%20AND%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="MPT11C.NIH_Support"><h2 id="_MPT11C_NIH_Support_">NIH Support</h2><p>NIH P50 MH62185.</p></div><div id="MPT11C.references"><h2 id="_MPT11C_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="MPT11C.REF.1">Kumar J.S. , Majo V.J. , Hsiung S.C. , Millak M.S. , Liu K.P. , Tamir H. , Prabhakaran J. , Simpson N.R. , Van Heertum R.L. , Mann J.J. , Parsey R.V. Synthesis and in vivo validation of [O-methyl-11C]2-{4-[4-(7-methoxynaphthalen-1-yl)piperazin- 1-yl]butyl}-4-methyl-2H-[1,2,4]triazine-3,5-dione: a novel 5-HT1A receptor agonist positron emission tomography ligand. <span><span class="ref-journal">J Med Chem. </span>2006;<span class="ref-vol">
|
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<strong>49</strong>
|
||
</span>(1):125–34.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16392798" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16392798</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="MPT11C.REF.2">Bantick R.A. , Rabiner E.A. , Hirani E. , de Vries M.H. , Hume S.P. , Grasby P.M. Occupancy of agonist drugs at the 5-HT1A receptor. <span><span class="ref-journal">Neuropsychopharmacology. </span>2004;<span class="ref-vol">
|
||
<strong>29</strong>
|
||
</span>(5):847–59.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/14985704" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14985704</span></a>]</div></dd><li><div class="bk_ref" id="MPT11C.REF.3">3. Sunderland, P.M., Structure and function of the nervous system, in Pathophysiology: The biologic basis for disease in adults and children, K.L. McCance, and S.H. Huether, Editor. 1994, Mosby-Year Book, Inc.: St. Louis, MO. p. 397-436.</div></li><dt>4.</dt><dd><div class="bk_ref" id="MPT11C.REF.4">Lanfumey L. , Hamon M. 5-HT1 receptors. <span><span class="ref-journal">Curr Drug Targets CNS Neurol Disord. </span>2004;<span class="ref-vol">
|
||
<strong>3</strong>
|
||
</span>(1):1–10.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/14965240" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14965240</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="MPT11C.REF.5">Passchier J. , van Waarde A. Visualisation of serotonin-1A (5-HT1A) receptors in the central nervous system. <span><span class="ref-journal">Eur J Nucl Med. </span>2001;<span class="ref-vol">
|
||
<strong>28</strong>
|
||
</span>(1):113–29.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11202445" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11202445</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="MPT11C.REF.6">Lang L. , Jagoda E. , Schmall B. , Vuong B.K. , Adams H.R. , Nelson D.L. , Carson R.E. , Eckelman W.C. Development of fluorine-18-labeled 5-HT1A antagonists. <span><span class="ref-journal">J Med Chem. </span>1999;<span class="ref-vol">
|
||
<strong>42</strong>
|
||
</span>(9):1576–86.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10229627" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10229627</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="MPT11C.REF.7">Tauscher J. , Verhoeff N.P. , Christensen B.K. , Hussey D. , Meyer J.H. , Kecojevic A. , Javanmard M. , Kasper S. , Kapur S. Serotonin 5-HT1A receptor binding potential declines with age as measured by [11C]WAY-100635 and PET. <span><span class="ref-journal">Neuropsychopharmacology. </span>2001;<span class="ref-vol">
|
||
<strong>24</strong>
|
||
</span>(5):522–30.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11282252" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11282252</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="MPT11C.REF.8">Houle S. , DaSilva J.N. , Wilson A.A. Imaging the 5-HT(1A) receptors with PET: WAY-100635 and analogues. <span><span class="ref-journal">Nucl Med Biol. </span>2000;<span class="ref-vol">
|
||
<strong>27</strong>
|
||
</span>(5):463–6.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10962251" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10962251</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="MPT11C.REF.9">Watson J. , Collin L. , Ho M. , Riley G. , Scott C. , Selkirk J.V. , Price G.W. 5-HT(1A) receptor agonist-antagonist binding affinity difference as a measure of intrinsic activity in recombinant and native tissue systems. <span><span class="ref-journal">Br J Pharmacol. </span>2000;<span class="ref-vol">
|
||
<strong>130</strong>
|
||
</span>(5):1108–14.</span> [<a href="/pmc/articles/PMC1572157/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC1572157</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/10882396" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10882396</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="MPT11C.REF.10">Koek W. , Vacher B. , Cosi C. , Assie M.B. , Patoiseau J.F. , Pauwels P.J. , Colpaert F.C. 5-HT1A receptor activation and antidepressant-like effects: F 13714 has high efficacy and marked antidepressant potential. <span><span class="ref-journal">Eur J Pharmacol. </span>2001;<span class="ref-vol">
|
||
<strong>420</strong>
|
||
</span>(2-3):103–12.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11408031" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11408031</span></a>]</div></dd><dt>11.</dt><dd><div class="bk_ref" id="MPT11C.REF.11">Bruins Slot L.A. , Koek W. , Tarayre J.P. , Colpaert F.C. Tolerance and inverse tolerance to the hyperalgesic and analgesic actions, respectively, of the novel analgesic, F 13640. <span><span class="ref-journal">Eur J Pharmacol. </span>2003;<span class="ref-vol">
|
||
<strong>466</strong>
|
||
</span>(3):271–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12694810" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12694810</span></a>]</div></dd></dl></div><div id="bk_toc_contnr"></div></div></div>
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<div class="post-content"><div><div class="half_rhythm"><a href="/books/about/copyright/">Copyright Notice</a></div><div class="small"><span class="label">Bookshelf ID: NBK23187</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20641390" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20641390</a></span></div><div style="margin-top:2em" class="bk_noprnt"><a class="bk_cntns" href="/books/n/micad/">Contents</a><div class="pagination bk_noprnt"><a class="active page_link prev" href="/books/n/micad/MMP11C/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/MeS-IMPY11C/" title="Next page in this title">Next ></a></div></div></div></div>
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<div xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance"></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Views</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="PDF_download" id="Shutter"></a></div><div class="portlet_content"><ul xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="simple-list"><li><a href="/books/NBK23187/?report=reader">PubReader</a></li><li><a href="/books/NBK23187/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23187" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23187" style="display:none" title="Cite this Page"><div class="bk_tt">Cheng KT. [O-methyl-11C]2-{4-[4-(7-Methoxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2H-[1,2,4]triazine-3,5-dione. 2007 Jan 30 [Updated 2008 Feb 26]. In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. <span class="bk_cite_avail"></span></div></div></li><li><a href="/books/NBK23187/pdf/Bookshelf_NBK23187.pdf">PDF version of this page</a> (142K)</li><li><a href="/books/n/micad/toc/bin/micad.csv">MICAD summary (CSV file)</a></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>In this page</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="page-toc" id="Shutter"></a></div><div class="portlet_content"><ul xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="simple-list"><li><a href="#MPT11C.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#MPT11C.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#MPT11C.In_Vitro_Studies_Tes" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#MPT11C.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#MPT11C.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#MPT11C.NIH_Support" ref="log$=inpage&link_id=inpage">NIH Support</a></li><li><a href="#MPT11C.references" ref="log$=inpage&link_id=inpage">References</a></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Search MICAD</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="source-application" id="Shutter"></a></div><div class="portlet_content"><form xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" name="frmSearch" method="get" action="/books/NBK5330/" id="frmSearch"><script type="text/javascript" src="/corehtml/pmc//js/bookshelf/micad.js">/**/</script><label class="offscreen_noflow" for="txtfield">Search term</label><input id="txtfield" type="text" name="f1_term" size="22" onKeyPress="KeyPress('micad',event,'/books/NBK5330/','')" /><button name="f1_search" type="submit">Go</button><button onclick="this.form.reset();" type="reset">Clear</button><p><b>Limit my Search:</b></p><div class="clearfix"><label for="detection">Method of detection:</label><div class="right"><select name="detection" id="detection" style="width:200px"><option value="" selected="selected">Any</option><option value="(MRI OR "Magnetic resonance imaging" OR MRS)">MRI</option><option value="Multimodal">Multimodal imaging</option><option value="Optical">Optical imaging</option><option value="PET">PET</option><option value="Photoacoustic">Photoacoustic imaging</option><option value="(SPECT OR planar)">SPECT</option><option value="Ultrasound">Ultrasound</option><option value="(x-ray OR ct)">X-ray, CT</option></select></div></div><div class="clearfix"><label for="signal">Source of signal/contrast:</label><div class="right"><select name="signal" id="signal" style="width:200px"><option value="" selected="selected">Any</option><optgroup label="MRI agents"><option value="(Copper OR Cu)">Copper</option><option value="(Europium OR Eu3+)">Europium</option><option value="(Fluorine OR 19F)">Fluorine</option><option value="(Gadolinium OR Gd3+)">Gadolinium</option><option value=""Hyperpolarized 13C"">Hyperpolarized 13C</option><option value=""Iron oxide"">Iron oxide</option><option value=""Nitroxide radicals"">Nitroxide radicals</option><option value="(Oxygen OR 17O)">Oxygen</option><option value="Thulium">Thulium</option></optgroup><optgroup label="Multimodal agents"><option value="((Gadolinium OR Gd3+) AND Optical)">Gadolinium and optical</option><option value="((Gadolinium OR Gd3+) AND (Gold OR Au))">Gadolinium and Gold</option><option value="("Iron oxide" AND (64Cu OR 124I OR 111In))">Iron oxide and
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europium</option><option value="(166Ho OR 67Ga OR 68Ga OR 123I OR 124I OR 125I)">Radionuclides</option></optgroup><optgroup label="Optical agents"><option value="("Fluorescent dyes" OR protein)">Fluorescent dyes or proteins</option><option value=""Luminescent agents"">Luminescent agents</option><option value="(Metals OR Metal OR Gold OR Au)">Metals (Au)</option><option value="Nanotubes">Nanotubes</option><option value=""Quantum dots"">Quantum dots</option></optgroup><optgroup label="PET radionuclides"><option value="("Arsenic 74" OR 74As)">Arsenic-74</option><option value="("Bromine 76" OR 76Br)">Bromine-76</option><option value="("Carbon 11" OR 11C)">Carbon-11</option><option value="(Copper-60 OR Copper-61 OR Copper-62 OR Copper-64 OR 60Cu OR 61Cu OR 62Cu OR 64Cu)">Copper-60, 61, 62, 64</option><option value="("Fluorine 18" OR 18F)">Fluorine-18</option><option value="(Gallium-68 OR 68Ga)">Gallium-68</option><option value="("Iodine 124" OR 124I)">Iodine-124</option><option value="("Nitrogen 13" OR 13N)">Nitrogen-13</option><option value="("Yttrium 86" OR 86Y)">Yttrium-86</option><option value="("Zirconium 89" OR 89Zr)">Zirconium-89</option></optgroup><optgroup label="Photoacoustic agents"><option value="(Gold OR Au)">Gold</option><option value="("Indocyanine green" OR ICG)">Indocyanine green</option></optgroup><optgroup label="SPECT radionuclides"><option value="(Gallium-67 OR 67Ga)">Gallium-67</option><option value="("Indium 111" OR 111In)">Indium-111</option><option value="("Iodine 123" OR "Iodine 125" OR "Iodine 131" OR 123I OR 125I OR 131I)">Iodine-123, 125, 131</option><option value="("Lutetium 177" OR 177Lu)">Lutetium-177</option><option value="(Rhenium OR 186Re OR 188Re)">Rhenium</option><option value="("Technetium 99m" OR 99mTc)">Technetium-99m</option><option value="("Tellurium 125m" OR 125mTe)">Tellurium-125m</option></optgroup><optgroup label="Ultrasound agents"><option value="Microbubbles">Microbubbles</option><option value="Nanobubbles">Nanobubbles</option></optgroup><optgroup label="X-ray and CT agents"><option value="(Bismuth OR Bi)">Bismuth</option><option value="(Gold OR Au)">Gold</option><option value="Iodine">Iodine</option></optgroup></select></div></div><div class="clearfix"><label for="agent">Agent Category:</label><div class="right"><select name="agent" id="agent" style="width:200px"><option value="" selected="selected">Any</option><option value="(antibody OR trastuzumab OR immunoglobulin)">Antibodies</option><option value="(bacteria OR bacteriophage OR coli)">Bacteria</option><option value="cell">Cells</option><option value="(compound OR "amino acid" OR "folic acid" OR "cage molecule" OR carbohydrate OR copolymers OR polymer OR "small molecule" OR macromolecule OR triiodobenzoate OR estradiol OR glycosaminoglycan)">Compounds</option><option value="ligand">Ligands</option><option value="(lipid OR liposome OR liposomes">Lipids</option><option value="metal">Metal</option><option value="(nanoparticle OR nanoparticles OR nanotubes OR "iron oxide")">Nanoparticles</option><option value="(siRNA OR "nucleic acid" OR oligonucleotide)">Nucleic acids</option><option value="peptide">Peptides</option><option value="polyeptide">Polyeptides</option><option value="(protein OR albumin OR chemokin OR immunoprotein OR luciferase OR albumin)">Proteins</option><option value="(virus OR adenovirus)">Viruses</option></select></div></div><div class="clearfix"><label for="target">Target Category:</label><div class="right"><select name="target" id="target" style="width:200px"><option value="" selected="selected">Any</option><option value="acceptor">Acceptors</option><option value=""adhesion molecule"">Adhesion molecules</option><option value="(antigen OR antibody-antigen)">Antigens</option><option value="(enzyme OR enzymes OR enzyme-substrate)">Enzymes</option><option value="(lipids OR lipophilic cation)">Lipids</option><option value="(receptor OR receptors OR receptor-ligand OR receptor-antibody OR antibody-receptor)">Receptors</option><option value="transporter">Transporters</option><option value="non-targeted">Non-targeted</option><option value=""nucleic acid"">Nucleic acids</option><option value="(non-targeted OR "unknown binding site")">Others</option></select></div></div><div><input id="__micad_btn_1" type="radio" name="stage" value="vitro" /><label for="__micad_btn_1"><i>In vitro</i></label><input id="__micad_btn_2" type="radio" name="stage" value="rodents" /><label for="__micad_btn_2">Rodents</label><input id="__micad_btn_3" type="radio" name="stage" value="mammals" /><label for="__micad_btn_3">Non-primate non-rodent mammals</label><br /><input id="__micad_btn_4" type="radio" name="stage" value="primates" /><label for="__micad_btn_4">Non-human primates</label><input id="__micad_btn_5" type="radio" name="stage" value="humans" /><label for="__micad_btn_5">Humans</label><input id="__micad_btn_6" type="radio" name="stage" value="any" checked="checked" /><label for="__micad_btn_6">Any</label></div></form><form xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" name="frmGo" method="get" action="javascript:alert('frmGo:_@action_was_not_set')" id="frmGo"><input name="term" value="." type="hidden" /></form></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Related information</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="discovery_db_links" id="Shutter"></a></div><div class="portlet_content"><ul><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pmc&DbFrom=books&Cmd=Link&LinkName=books_pmc_refs&IdsFromResult=1513128" ref="log$=recordlinks">PMC</a><div class="brieflinkpop offscreen_noflow">PubMed Central citations</div></li><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pcsubstance&DbFrom=books&Cmd=Link&LinkName=books_pcsubstance&IdsFromResult=1513128" ref="log$=recordlinks">PubChem Substance</a><div class="brieflinkpop offscreen_noflow">Related PubChem Substances</div></li><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pubmed&DbFrom=books&Cmd=Link&LinkName=books_pubmed_refs&IdsFromResult=1513128" ref="log$=recordlinks">PubMed</a><div class="brieflinkpop offscreen_noflow">Links to PubMed</div></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Similar articles in PubMed</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="PBooksDiscovery_RA" id="Shutter"></a></div><div class="portlet_content"><ul><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/20641557" ref="ordinalpos=1&linkpos=1&log$=relatedreviews&logdbfrom=pubmed"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> [carbonyl-(11)C](R,S)-(N-(2-(1-(4-(2-Methoxyphenyl)piperazinyl)(2-methylethyl)))-N-pyridinyl)cyclohexanecarboxamide.</a><span class="source">[Molecular Imaging and Contrast...]</span><div class="brieflinkpop offscreen_noflow"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> [carbonyl-(11)C](R,S)-(N-(2-(1-(4-(2-Methoxyphenyl)piperazinyl)(2-methylethyl)))-N-pyridinyl)cyclohexanecarboxamide.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Cheng KT. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Molecular Imaging and Contrast Agent Database (MICAD). 2004</em></div></div></li><li 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