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<script type="text/javascript" src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/jr.boots.min.js"> </script><title>[7-methyl-11C]-(E)-8-(3,4,5-Trimethoxystyryl)-1,3,7-trimethylxanthine - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf</title>
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<meta name="citation_inbook_title" content="Molecular Imaging and Contrast Agent Database (MICAD) [Internet]">
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<meta name="citation_title" content="[7-methyl-11C]-(E)-8-(3,4,5-Trimethoxystyryl)-1,3,7-trimethylxanthine">
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<meta name="citation_publisher" content="National Center for Biotechnology Information (US)">
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<meta name="citation_date" content="2008/07/08">
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<meta name="citation_author" content="Kam Leung">
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<meta name="citation_pmid" content="20641402">
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<meta name="DC.Title" content="[7-methyl-11C]-(E)-8-(3,4,5-Trimethoxystyryl)-1,3,7-trimethylxanthine">
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<meta name="DC.Contributor" content="Kam Leung">
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<meta name="description" content="Adenosine is an endogenous nucleoside that modulates a number of physiologic functions in the central nervous system (CNS) and in peripheral organs such as the heart, kidney, and muscle (1, 2). The effect is mediated by two major subtypes of receptors (A1 and A2A receptors) and two minor subtypes (A2B and A3). In the CNS, A1 receptors are present both pre- and postsynaptically in the hippocampus, cerebral cortex, thalamus, striatum, and cerebellum. A2A receptors are highly concentrated and co-localized with dopamine D1 and D2 receptors in the striatum, nucleus accumbens, and olfactory tubercle. A2A receptors are also present in low amounts in the hippocampus and cortex. A2B receptors are widely distributed, but the density is higher in the gastrointestinal tract. A3 receptors are also widely distributed but with higher density in the testis. A1 and A3 receptors mediate inhibition of adenylyl cyclase, whereas A2A and A2B receptors mediate stimulation. Changes in the adenosine receptor functions are implicated in epilepsy, ischemic cerebral stroke, movement disorders, sleep disorders, and psychiatric disorders (3-5).">
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<meta name="og:description" content="Adenosine is an endogenous nucleoside that modulates a number of physiologic functions in the central nervous system (CNS) and in peripheral organs such as the heart, kidney, and muscle (1, 2). The effect is mediated by two major subtypes of receptors (A1 and A2A receptors) and two minor subtypes (A2B and A3). In the CNS, A1 receptors are present both pre- and postsynaptically in the hippocampus, cerebral cortex, thalamus, striatum, and cerebellum. A2A receptors are highly concentrated and co-localized with dopamine D1 and D2 receptors in the striatum, nucleus accumbens, and olfactory tubercle. A2A receptors are also present in low amounts in the hippocampus and cortex. A2B receptors are widely distributed, but the density is higher in the gastrointestinal tract. A3 receptors are also widely distributed but with higher density in the testis. A1 and A3 receptors mediate inhibition of adenylyl cyclase, whereas A2A and A2B receptors mediate stimulation. Changes in the adenosine receptor functions are implicated in epilepsy, ischemic cerebral stroke, movement disorders, sleep disorders, and psychiatric disorders (3-5).">
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id="jr-fip-info-p"><a id="jr-fip-prev" class="wsprkl btn" title="Jump to previuos match">◀</a><button id="jr-fip-matches">no matches yet</button><a id="jr-fip-next" class="wsprkl btn" title="Jump to next match">▶</a></nav></nav></div><div id="jr-epub-interstitial" class="hidden"></div><div id="jr-content"><article data-type="main"><div class="main-content lit-style" itemscope="itemscope" itemtype="http://schema.org/CreativeWork"><div class="meta-content fm-sec"><div class="fm-sec"><h1 id="_NBK23199_"><span class="title" itemprop="name">[7-<i>methyl</i>-<sup>11</sup>C]-(<i>E</i>)-8-(3,4,5-Trimethoxystyryl)-1,3,7-trimethylxanthine</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">[<sup>11</sup>C]TMSX</div><p class="contribs">Leung K.</p><p class="fm-aai"><a href="#_NBK23199_pubdet_">Publication Details</a></p></div></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div class="iconblock whole_rhythm clearfix ten_col table-wrap" id="figTMSX11CTncchemicalname7methyl11ce83"><a href="/books/NBK23199/table/TMSX11C.T.nc_chemical_name7methyl11ce83/?report=objectonly" target="object" title="Table" class="img_link icnblk_img" rid-ob="figobTMSX11CTncchemicalname7methyl11ce83"><img class="small-thumb" src="/corehtml/pmc/css/bookshelf/2.26/img/table-icon.gif" alt="Table Icon" /></a><div class="icnblk_cntnt"><h4 id="TMSX11C.T.nc_chemical_name7methyl11ce83"><a href="/books/NBK23199/table/TMSX11C.T.nc_chemical_name7methyl11ce83/?report=objectonly" target="object" rid-ob="figobTMSX11CTncchemicalname7methyl11ce83">Table</a></h4><p class="float-caption no_bottom_margin">
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<i>In vitro</i>
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Rodents
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</p></div></div><div id="TMSX11C.Background"><h2 id="_TMSX11C_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%22KF18446%22%5BSubstance%20Name%5D%20OR%2011C-TMSX%5BText%20Word%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Adenosine is an endogenous nucleoside that modulates a number of physiologic functions in the central nervous system (CNS) and in peripheral organs such as the heart, kidney, and muscle (<a class="bibr" href="#TMSX11C.REF.1" rid="TMSX11C.REF.1 TMSX11C.REF.2">1, 2</a>). The effect is mediated by two major subtypes of receptors (A<sub>1</sub> and A<sub>2A</sub> receptors) and two minor subtypes (A<sub>2B</sub> and A<sub>3</sub>). In the CNS, A<sub>1</sub> receptors are present both pre- and postsynaptically in the hippocampus, cerebral cortex, thalamus, striatum, and cerebellum. A<sub>2A</sub> receptors are highly concentrated and co-localized with dopamine D<sub>1</sub> and D<sub>2</sub> receptors in the striatum, nucleus accumbens, and olfactory tubercle. A<sub>2A</sub> receptors are also present in low amounts in the hippocampus and cortex. A<sub>2B</sub> receptors are widely distributed, but the density is higher in the gastrointestinal tract. A<sub>3</sub> receptors are also widely distributed but with higher density in the testis. A<sub>1</sub> and A<sub>3</sub> receptors mediate inhibition of adenylyl cyclase, whereas A<sub>2A</sub> and A<sub>2B</sub> receptors mediate stimulation. Changes in the adenosine receptor functions are implicated in epilepsy, ischemic cerebral stroke, movement disorders, sleep disorders, and psychiatric disorders (<a class="bibr" href="#TMSX11C.REF.3" rid="TMSX11C.REF.3 TMSX11C.REF.4 TMSX11C.REF.5">3-5</a>).</p><p>A<sub>2A</sub> receptors have been studied <i>in vivo</i> by positron emission tomography (PET) using [7-<i>methyl</i>-<sup>11</sup>C]-(<i>E</i>)-8-(3,4,5-trimethoxystyryl)-1,3,7-trimethylxanthine ([<sup>11</sup>C]TMSX), a methylxanthine analog of KF17387 with selective A<sub>2A</sub> antagonistic activity (<a class="bibr" href="#TMSX11C.REF.6" rid="TMSX11C.REF.6">6</a>). TMSX showed better selectivity for A<sub>2A</sub> over A<sub>1</sub> receptors than KF17387 and had little affinity in various neuroreceptor-binding assays (<a class="bibr" href="#TMSX11C.REF.7" rid="TMSX11C.REF.7">7</a>). [<sup>11</sup>C]TMSX is being developed as a PET agent for the non-invasive study of A<sub>2A</sub> receptors in the human brain and heart.</p></div><div id="TMSX11C.Synthesis"><h2 id="_TMSX11C_Synthesis_">Synthesis</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C-TMSX%20and%20synthesis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>In the report by Ishiwata et al. (<a class="bibr" href="#TMSX11C.REF.8" rid="TMSX11C.REF.8">8</a>), [<sup>11</sup>C]TMSX was synthesized by alkylation of the 7-desmethyl precursor ((<i>E</i>)-8-(3,4,5-trimethoxystyryl)-1,3-dimethylxanthine) with [<sup>11</sup>C]methyl iodide. Purification by high-performance liquid chromatography (HPLC) provided a decay-corrected radiochemical yield of 25-46%, radiochemical purity >99%, and specific activity of 10-72 GBq/μmol (0.27-1.95 Ci/μmol) in 20-25 min.</p><p>Kawamura et al. (<a class="bibr" href="#TMSX11C.REF.9" rid="TMSX11C.REF.9">9</a>) described the synthesis of [<sup>11</sup>C]TMSX from the desmethyl precursor with [<sup>11</sup>C]methyl triflate in the presence of Cs<sub>2</sub>CO<sub>3</sub>. This procedure provided improved radiochemical yield (decay-corrected) of 55.3 ± 5.2% based on [<sup>11</sup>C]methyl triflate. No time of synthesis or specific activity was reported.</p></div><div id="TMSX11C.In_Vitro_Studies_Testing_in_Cell"><h2 id="_TMSX11C_In_Vitro_Studies_Testing_in_Cell_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C-TMSX%20and%20in%20vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>In the study by Ishiwata et al. (<a class="bibr" href="#TMSX11C.REF.8" rid="TMSX11C.REF.8">8</a>), the <i>K</i><sub>i</sub> values of TMSX and KF17837 were 5.9 and 1.0 nM, respectively, for the A<sub>2A</sub> receptors and 1,600 and 62 nM for the A<sub>1</sub> receptors. Hence, TMSX showed better selectivity for A<sub>2A</sub> over A<sub>1</sub> receptors than KF17387. <i>In vitro</i> autoradiography (ARG) studies of brain sections with [<sup>11</sup>C]TMSX showed high binding in the caudate putamen, nucleus accumbens, and olfactory tubercle with a striatum/cortex ratio of 8.4 ± 2.2. TMSX (20 μM) blocked 91% of [<sup>11</sup>C]TMSX binding in the striatum but only 54% in the cortex. Saturation binding experiments of [<sup>11</sup>C]TMSX in the rat striatum and cortex gave estimated <i>K</i><sub>d</sub> values of 9.8 and 16.4 nM, with <i>B</i><sub>max</sub> values of 170 and 33 fmol/mm<sup>3</sup> tissue, respectively (<a class="bibr" href="#TMSX11C.REF.7" rid="TMSX11C.REF.7">7</a>).</p></div><div id="TMSX11C.Animal_Studies"><h2 id="_TMSX11C_Animal_Studies_">Animal Studies</h2><div id="TMSX11C.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C-TMSX%20and%20rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Biodistribution studies in normal mice showed high initial accumulation of radioactivity in the liver, followed by the kidney (12.08% injected dose (ID)/g), heart (10.94% ID/g), liver (4.42% ID/g), pancreas (4.23%ID/g), and lung (3.92% ID/g) at 1 min after injection of [<sup>11</sup>C]TMSX (<a class="bibr" href="#TMSX11C.REF.10" rid="TMSX11C.REF.10">10</a>). The levels of radioactivity were low in the brain (2.49% ID/g) and blood (1.58% ID/g). Radioactivity levels decreased gradually in all studied organs, with the exception of the liver, which showed an increase for the first 15 min followed by a gradual decrease. E<i>x vivo</i> ARG indicated that uptake of [<sup>11</sup>C]TMSX was higher in the striatum than the cortex and cerebellum with a striatum/cortex ratio of 3.16 ±0.24 (<a class="bibr" href="#TMSX11C.REF.8" rid="TMSX11C.REF.8">8</a>). This high, selective binding of [<sup>11</sup>C]TMSX in the striatum was also confirmed by <i>in vitro</i> ARG and <i>iv vivo</i> regional brain distribution studies. Coadiministration of the A<sub>2A</sub> antagonist KF17837, but not the A<sub>1</sub> antagonist KF15372, decreased the accumulation in the brain in a dose-dependent manner at 15 min post injection. Pretreatment with 10 and 100 mg/kg theophylline (a low-affinity adenosine antagonist) 15 min before [<sup>11</sup>C]TMSX injection in mice significantly reduced striatal accumulation. About 80% and >98% of radioactivity in the plasma and striatum, respectively, was intact [<sup>11</sup>C]TMSX at 30 min post injection.</p><p>Ishiwata et al. (<a class="bibr" href="#TMSX11C.REF.11" rid="TMSX11C.REF.11">11</a>) reported <i>ex vivo</i> ARG studies in the rat globus pallidus. The highest uptake by the globus pallidus was for [<sup>11</sup>C]SCH 23390 (dopamine D<sub>1</sub> receptor) followed by [<sup>18</sup>F]fluorodeoxyglucose (FDG), [<sup>11</sup>C]TMSX, and [<sup>11</sup>C]raclopride (dopamine D<sub>2</sub> receptor). Receptor-specific uptake by the globus pallidus was observed for [<sup>11</sup>C]TMSX and [<sup>11</sup>C]SCH 23390, but not for [<sup>11</sup>C]raclopride. The globus pallidus/striatum uptake ratios for FDG and [<sup>11</sup>C]TMSX were ~0.6, which was twice as large as that for [<sup>11</sup>C]SCH 23390. In a rat model of degeneration of gamma-aminobutyric acid-ergic-enkephalin neurons induced by intrastriatal injection of quinolinic acid, the accumulation and binding potentials of [<sup>11</sup>C]TMSX and [<sup>11</sup>C]raclopride in the lesioned striatum were remarkably reduced but were higher than the values for [<sup>11</sup>C]SCH 23390 (<a class="bibr" href="#TMSX11C.REF.11" rid="TMSX11C.REF.11 TMSX11C.REF.12">11, 12</a>).</p></div><div id="TMSX11C.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C-TMSX%20and%20%28dog%20or%20or%20rabbit%20or%20sheep%20or%20pig%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publications are currently available.</p></div><div id="TMSX11C.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C-TMSX%20and%20%28primate%20not%20human%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Using PET, Ishiwata et al. (<a class="bibr" href="#TMSX11C.REF.8" rid="TMSX11C.REF.8">8</a>) obtained serial brain scans in 1 monkey after injection of 102 MBq (2.8 mCi) of [<sup>11</sup>C]TMSX. The accumulation of radioactivity in the striatum peaked at 5-10 min and then decreased for the final 60 min of study. The uptake was the highest in the striatum, followed by the thalamus, cerebellum, and cortex. The striatum/cortex and striatum/cerebellum ratios gradually increased from 1.3 and 1.2, respectively, at 5 min to 1.56 and 1.46 at 60 min.</p></div></div><div id="TMSX11C.Human_Studies"><h2 id="_TMSX11C_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C-TMSX%20and%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Ishiwata et al. (<a class="bibr" href="#TMSX11C.REF.13" rid="TMSX11C.REF.13">13</a>) reported on PET myocardial imaging in 1 healthy volunteer after injection of 590 MBq (16 mCi) of [<sup>11</sup>C]TMSX. The levels in the left ventricular wall, left ventricular anterior wall, and interventricular septum increased during the first 3 min after injection and then decreased gradually. In contrast, the radioactivity in the lung decreased rapidly. The fraction of unchanged [<sup>11</sup>C]TMSX in blood samples, as determined by HPLC, was 97, 94, and 95% at 10, 30, and 60 min, respectively. In other studies of 2 subjects, infusion of theophylline (3.3 mg/kg) reduced the distribution volumes (DVs; baseline values, 3.62-3.73) of the three heart regions by 18-22% as determined by Logan analysis (<a class="bibr" href="#TMSX11C.REF.14" rid="TMSX11C.REF.14">14</a>). The DV (1.57) of the brachii muscle was reduced by 10%. The A<sub>2A</sub> receptors have also been preliminarily visualized in human brain with relatively high DVs in the caudate (1.72) and putamen (1.72), followed by the thalamus (1.64), cerebellum (1.52), brainstem (1.42), and cerebral cortex (1.26) (<a class="bibr" href="#TMSX11C.REF.15" rid="TMSX11C.REF.15">15</a>). Mishina et al. (<a class="bibr" href="#TMSX11C.REF.16" rid="TMSX11C.REF.16">16</a>) was used a two-tissue, three-compartment model to estimate the distribution of A<sub>2A</sub> receptors in the brain (<i>n</i> = 5) using metabolite-correction arterial input function. The binding potential (BP) was the largest in the anterior (1.25) and posterior putamen (1.20), followed by la the head of caudate nucleus (1.05), thalamus (1.03), and frontal cortex lobe (0.46). On the other hand, Naganawa et al. (<a class="bibr" href="#TMSX11C.REF.17" rid="TMSX11C.REF.17">17</a>) showed that Logan plot estimated BPs matching those derived from compartment analysis (<i>n</i> = 5) with or without arterial blood sampling. Without the metabolite correction, the estimate of BP underestimated the true value by only 5%. Internal dosimetry data for [<sup>11</sup>C]TMSX in humans are not available in the literature.</p></div><div id="TMSX11C.References"><h2 id="_TMSX11C_References_">References</h2><dl class="temp-labeled-list"><dl class="bkr_refwrap"><dt>1.</dt><dd><div class="bk_ref" id="TMSX11C.REF.1">Fredholm B.B., Abbracchio M.P., Burnstock G., Daly J.W., Harden T.K., Jacobson K.A., Leff P., Williams M.
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<em>Nomenclature and classification of purinoceptors.</em>
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<span><span class="ref-journal">Pharmacol Rev. </span>1994;<span class="ref-vol">46</span>(2):143–56.</span> [<a href="/pmc/articles/PMC4976594/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC4976594</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/7938164" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 7938164</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>2.</dt><dd><div class="bk_ref" id="TMSX11C.REF.2">Palmer T.M., Stiles G.L.
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<em>Adenosine receptors.</em>
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<span><span class="ref-journal">Neuropharmacology. </span>1995;<span class="ref-vol">34</span>(7):683–94.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/8532135" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 8532135</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>3.</dt><dd><div class="bk_ref" id="TMSX11C.REF.3">Dunwiddie T.V., Masino S.A.
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<em>The role and regulation of adenosine in the central nervous system.</em>
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<span><span class="ref-journal">Annu Rev Neurosci. </span>2001;<span class="ref-vol">24</span>:31–55.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11283304" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11283304</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>4.</dt><dd><div class="bk_ref" id="TMSX11C.REF.4">El Yacoubi M., Costentin J., Vaugeois J.M.
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<em>Adenosine A2A receptors and depression.</em>
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<span><span class="ref-journal">Neurology. </span>2003;<span class="ref-vol">61</span>(11) Suppl 6:S82–7.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/14663017" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14663017</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>5.</dt><dd><div class="bk_ref" id="TMSX11C.REF.5">von Lubitz D.K.
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<em>Adenosine in the treatment of stroke: yes, maybe, or absolutely not?</em>
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<span><span class="ref-journal">Expert Opin Investig Drugs. </span>2001;<span class="ref-vol">10</span>(4):619–32.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11281813" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11281813</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>6.</dt><dd><div class="bk_ref" id="TMSX11C.REF.6">Noguchi J., Ishiwata K., Wakabayashi S., Nariai T., Shumiya S., Ishii S., Toyama H., Endo K., Suzuki F., Senda M.
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<em>Evaluation of carbon-11-labeled KF17837: a potential CNS adenosine A2a receptor ligand.</em>
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<span><span class="ref-journal">J Nucl Med. </span>1998;<span class="ref-vol">39</span>(3):498–503.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9529299" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9529299</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>7.</dt><dd><div class="bk_ref" id="TMSX11C.REF.7">Ishiwata K., Ogi N., Shimada J., Nonaka H., Tanaka A., Suzuki F., Senda M.
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<em>Further characterization of a CNS adenosine A2a receptor ligand [11C]KF18446 with in vitro autoradiography and in vivo tissue uptake.</em>
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<span><span class="ref-journal">Ann Nucl Med. </span>2000;<span class="ref-vol">14</span>(2):81–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10830524" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10830524</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>8.</dt><dd><div class="bk_ref" id="TMSX11C.REF.8">Ishiwata K., Noguchi J., Wakabayashi S., Shimada J., Ogi N., Nariai T., Tanaka A., Endo K., Suzuki F., Senda M.
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<em>11C-labeled KF18446: a potential central nervous system adenosine A2a receptor ligand.</em>
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<span><span class="ref-journal">J Nucl Med. </span>2000;<span class="ref-vol">41</span>(2):345–54.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10688121" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10688121</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>9.</dt><dd><div class="bk_ref" id="TMSX11C.REF.9">Kawamura K., Ishiwata K.
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<em>Improved synthesis of [11C]SA4503, [11C]MPDX and [11C]TMSX by use of [11C]methyl triflate.</em>
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<span><span class="ref-journal">Ann Nucl Med. </span>2004;<span class="ref-vol">18</span>(2):165–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15195766" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15195766</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>10.</dt><dd><div class="bk_ref" id="TMSX11C.REF.10">Ishiwata K., Wang W.F., Kimura Y., Kawamura K., Ishii K.
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<em>Preclinical studies on [11C]TMSX for mapping adenosine A2A receptors by positron emission tomography.</em>
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<span><span class="ref-journal">Ann Nucl Med. </span>2003;<span class="ref-vol">17</span>(3):205–11.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12846542" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12846542</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>11.</dt><dd><div class="bk_ref" id="TMSX11C.REF.11">Ishiwata K., Ogi N., Shimada J., Wang W., Ishii K., Tanaka A., Suzuki F., Senda M.
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<em>Search for PET probes for imaging the globus pallidus studied with rat brain ex vivo autoradiography.</em>
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<span><span class="ref-journal">Ann Nucl Med. </span>2000;<span class="ref-vol">14</span>(6):461–6.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11210099" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11210099</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>12.</dt><dd><div class="bk_ref" id="TMSX11C.REF.12">Ishiwata K., Ogi N., Hayakawa N., Oda K., Nagaoka T., Toyama H., Suzuki F., Endo K., Tanaka A., Senda M.
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<em>Adenosine A2A receptor imaging with [11C]KF18446 PET in the rat brain after quinolinic acid lesion: comparison with the dopamine receptor imaging.</em>
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<span><span class="ref-journal">Ann Nucl Med. </span>2002;<span class="ref-vol">16</span>(7):467–75.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12508837" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12508837</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>13.</dt><dd><div class="bk_ref" id="TMSX11C.REF.13">Ishiwata K., Kawamura K., Kimura Y., Oda K., Ishii K.
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<em>Potential of an adenosine A2A receptor antagonist [11C]TMSX for myocardial imaging by positron emission tomography: a first human study.</em>
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<span><span class="ref-journal">Ann Nucl Med. </span>2003;<span class="ref-vol">17</span>(6):457–62.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/14575379" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14575379</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>14.</dt><dd><div class="bk_ref" id="TMSX11C.REF.14">Ishiwata K., Mizuno M., Kimura Y., Kawamura K., Oda K., Sasaki T., Nakamura Y., Muraoka I., Ishii K.
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<em>Potential of [11C]TMSX for the evaluation of adenosine A2A receptors in the skeletal muscle by positron emission tomography.</em>
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<span><span class="ref-journal">Nucl Med Biol. </span>2004;<span class="ref-vol">31</span>(7):949–56.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15464397" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15464397</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>15.</dt><dd><div class="bk_ref" id="TMSX11C.REF.15">Ishiwata K., Mishina M., Kimura Y., Oda K., Sasaki T., Ishii K.
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<em>First visualization of adenosine A(2A) receptors in the human brain by positron emission tomography with [11C]TMSX.</em>
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<span><span class="ref-journal">Synapse. </span>2005;<span class="ref-vol">55</span>(2):133–6.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15543628" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15543628</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>16.</dt><dd><div class="bk_ref" id="TMSX11C.REF.16">Mishina M., Ishiwata K., Kimura Y., Naganawa M., Oda K., Kobayashi S., Katayama Y., Ishii K.
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<em>Evaluation of distribution of adenosine A2A receptors in normal human brain measured with [11C]TMSX PET.</em>
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<span><span class="ref-journal">Synapse. </span>2007;<span class="ref-vol">61</span>(9):778–84.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17568431" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17568431</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>17.</dt><dd><div class="bk_ref" id="TMSX11C.REF.17">Naganawa M., Kimura Y., Mishina M., Manabe Y., Chihara K., Oda K., Ishii K., Ishiwata K.
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<em>Quantification of adenosine A2A receptors in the human brain using [11C]TMSX and positron emission tomography.</em>
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<span><span class="ref-journal">Eur J Nucl Med Mol Imaging. </span>2007;<span class="ref-vol">34</span>(5):679–87.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17171358" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17171358</span></a>]</div></dd></dl></dl></div><div id="bk_toc_contnr"></div></div></div><div class="fm-sec"><h2 id="_NBK23199_pubdet_">Publication Details</h2><h3>Author Information and Affiliations</h3><div class="contrib half_rhythm"><span itemprop="author">Kam Leung</span>, PhD<div class="affiliation small">National Center for Biotechnology Information, NLM, NIH, Bethesda, MD<div><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 class="small">Corresponding author.</div></div><h3>Publication History</h3><p class="small">Created: <span itemprop="datePublished">February 17, 2006</span>; Last Update: <span itemprop="dateModified">July 8, 2008</span>.</p><h3>Copyright</h3><div><div class="half_rhythm"><a href="/books/about/copyright/">Copyright Notice</a></div></div><h3>Publisher</h3><p><a href="http://www.ncbi.nlm.nih.gov/" ref="pagearea=page-banner&targetsite=external&targetcat=link&targettype=publisher">National Center for Biotechnology Information (US)</a>, Bethesda (MD)</p><h3>NLM Citation</h3><p>Leung K. [7-methyl-11C]-(E)-8-(3,4,5-Trimethoxystyryl)-1,3,7-trimethylxanthine. 2006 Feb 17 [Updated 2008 Jul 8]. 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></p></div><div class="small-screen-prev"><a href="/books/n/micad/DPN11C/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M75,30 c-80,60 -80,0 0,60 c-30,-60 -30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Prev</text></svg></a></div><div class="small-screen-next"><a href="/books/n/micad/JWAY11C/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M25,30c80,60 80,0 0,60 c30,-60 30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Next</text></svg></a></div></article><article data-type="table-wrap" id="figobTMSX11CTncchemicalname7methyl11ce83"><div id="TMSX11C.T.nc_chemical_name7methyl11ce83" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23199/table/TMSX11C.T.nc_chemical_name7methyl11ce83/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__TMSX11C.T.nc_chemical_name7methyl11ce83_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;">[7-<i>methyl</i>-<sup>11</sup>C]-(<i>E</i>)-8-(3,4,5-Trimethoxystyryl)-1,3,7-trimethylxanthine</td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;">
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<a href="https://pubchem.ncbi.nlm.nih.gov/substance/8036876" 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=8036876" alt="image 8036876 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]TMSX</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]KF18446</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;">Adenosine A<sub>2A</sub> receptor</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</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;">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><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Rodents
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</div></li><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><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Humans
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</div></li></ul>
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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></article></div><div id="jr-scripts"><script src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/libs.min.js"> </script><script src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/jr.min.js"> </script></div></div>
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