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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="#__NBK23385_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23385_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/HOMADAM11C/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/Erlotinib11C/" 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="_NBK23385_"><span class="title" itemprop="name">[<sup>11</sup>C]<i>N</i>,<i>N</i>-Dimethyl-2-(2-amino-4-cyanophenylthio)benzylamine </span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">[<sup>11</sup>C]DASB</div><p class="contrib-group"><span itemprop="author">Kam Leung</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK23385_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK23385_ai__"><div class="contrib half_rhythm"><span itemprop="author">Kam Leung</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">May 18, 2005</span>; Last Update: <span itemprop="dateModified">June 24, 2008</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="DASB11C.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23385/table/DASB11C.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__DASB11C.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;">[<sup>11</sup>C]<i>N</i>,<i>N</i>-Dimethyl-2-(2-amino-4-cyanophenylthio)benzylamine</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/853768" 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=853768" alt="image 853768 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]DASB</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]3-Amino-4-(2-dimethylaminomethylphenylsulfanyl)-benzonitrile</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;">Serotonin transporter</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;">Serotonin transporter 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;">PET</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Source of signal\contrast:</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>
|
||
<ul class="simple-list"><li class="half_rhythm"><div>
|
||
<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Rodents
|
||
</div></li></ul>
|
||
<ul class="simple-list"><li class="half_rhythm"><div>
|
||
<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Non-primate non-rodent mammals
|
||
</div></li></ul>
|
||
<ul class="simple-list"><li class="half_rhythm"><div>
|
||
<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Non-human primates
|
||
</div></li></ul>
|
||
<ul class="simple-list"><li class="half_rhythm"><div>
|
||
<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Humans
|
||
</div></li></ul>
|
||
</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="DASB11C.Background"><h2 id="_DASB11C_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=DASB%5BAll%20Fields%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Serotonin (5-hydroxytryptamine, 5-HT) has diverse physiological roles as a neurotransmitter in the central nervous system (<a class="bk_pop" href="#DASB11C.REF.1">1</a>). It also is a regulator of smooth muscle function and platelet aggregation. The brain 5-HT system has been implicated in several neuropsychiatric disorders, including major depression, anxiety, obsessive-compulsive disorder, and schizophrenia (<a class="bk_pop" href="#DASB11C.REF.2">2</a>, <a class="bk_pop" href="#DASB11C.REF.3">3</a>). The serotonergic transmission is controlled in part by the serotonin transporter (SERT), which regulates the concentration of free, active 5-HT in the synaptic cleft. Citalopram, paroxetine, and fluoxetine were developed as selective SERT inhibitors to treat depression and anxiety disorders by blocking the reuptake of 5-HT [<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28Citalopram%2C%20paroxetine%20and%20fluoxetine%20%29%20and%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]. The blockade led to a higher 5-HT concentration in the synaptic cleft, and subsequently an improved well-being of the patients.</p><p><i>Trans-</i>1,2,3,5,6,10-β-Hexahydro-6-[4-([<sup>11</sup>C]methylthio)phenyl[pyrrolo-[2,1-a]isoquinoline ([<sup>11</sup>C]McN5652) binds selectively to the SERT, and its regional distribution of binding in humans correlates well with the known distribution of the SERT in human brain (<a class="bk_pop" href="#DASB11C.REF.4">4</a>). However, usefulness of [<sup>11</sup>C]McN5652 may be limited by its nonspecific binding and slow release from specific binding sites (<a class="bk_pop" href="#DASB11C.REF.5">5</a>). [<sup>11</sup>C]<i>N</i>,<i>N</i>-Dimethyl-2-(2-amino-4-cyanophenylthio)benzylamine ([<sup>11</sup>C]DASB) was found to be a promising tracer for SERT imaging in animals and humans (<a class="bk_pop" href="#DASB11C.REF.6">6-9</a>). It displayed a nanomolar affinity for SERT and a greater than 1000-fold affinity for SERT over dopamine transporter (DAT) and norepinephrine transporter (NET). The uptake in the SERT-rich brain regions was both saturable and selective for SERT.</p></div><div id="DASB11C.Synthesis"><h2 id="_DASB11C_Synthesis_">Synthesis</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=DASB%5BAll%20Fields%5D%20AND%20synthesis%5BAll%20Fields%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>[<sup>11</sup>C]DASB was synthesized by alkylation of its <i>N</i>-normethyl precursor using [<sup>11</sup>C]iodomethane in 30-55% radiochemical yield (not corrected for decay) in 25-30 min (<a class="bk_pop" href="#DASB11C.REF.6">6</a>). Chemical and radiochemical purities were >98% with specific activities of 25-55 GBq/μmol (0.68-1.49 Ci/μmol) at the end of synthesis.</p></div><div id="DASB11C.In_Vitro_Studies_Tes"><h2 id="_DASB11C_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=DASB%5BAll%20Fields%5D%20AND%20in%20vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>[<sup>11</sup>C]DASB was reported to bind specifically to the serotonergic transporter in homogenates of rat forebrain membrane (<a class="bk_pop" href="#DASB11C.REF.8">8</a>). The transporter-binding affinity of DASB was evaluated by competitive radioaffinity assays for serotonin (SERT), norepinephrine (NET), and dopamine (DAT). Binding affinity (<i>K</i><sub>i</sub>, n<span class="small-caps">m</span>) of DASB at SERT, NET, and DAT were 0.97, 6,000, and 1,180 n<span class="small-caps">m</span>, respectively. DASB binding selectively to SERT over other monoamine transporters was also reported previously using cloned human transporters (<a class="bk_pop" href="#DASB11C.REF.6">6</a>). DASB inhibited selectively [<sup>3</sup>H]5-HT re-uptake into rat brain synaptic vesicles. <i>K</i><sub>d</sub>, obtained from saturation data, was 0.54 n<span class="small-caps">m</span>, and <i>B</i><sub>max</sub> was 1.4 pmol/mg protein (<a class="bk_pop" href="#DASB11C.REF.10">10</a>). The IC<sub>50</sub> of serotonin to displace 50% of binding of 1.0 n<span class="small-caps">m</span> [<sup>11</sup>C]DASB was 3.47 μ<span class="small-caps">m</span>.</p></div><div id="DASB11C.Animal_Studies"><h2 id="_DASB11C_Animal_Studies_">Animal Studies</h2><div id="DASB11C.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=DASB%5BAll%20Fields%5D%20AND%20%28%22rodentia%22%5BMeSH%20Terms%5D%20OR%20rodentia%5BText%20Word%5D%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Intravenous injection of [<sup>11</sup>C]DASB in rats resulted in high uptake of radioactivity in the lungs (5.99% injected dose (ID/g)) and kidneys (2.62% ID/g) at 5 min after injection (<a class="bk_pop" href="#DASB11C.REF.8">8</a>). Less pronounced uptake was seen in the whole brain (0.79% ID/g). The uptake in the hypothalamus (0.8% ID/g), thalamus (0.64% ID/g), hippocampus (0.5% ID/g), striatum (0.55% ID/g), and cortex (0.5% ID/g) was higher than the cerebellum (0.13% ID/g) at 45 min (<a class="bk_pop" href="#DASB11C.REF.6">6</a>). The brain regional radioactivity was blocked by pretreatment of paroxetine and fluoxetine (SERT inhibitors), except in the cerebellum, indicating that SERT is low and the cerebellum can be used as a reference region (<a class="bk_pop" href="#DASB11C.REF.8">8</a>). The [<sup>11</sup>C]DASB uptake in the SERT-rich brain regions returned to >90% baseline levels in 24-48 h after paroxetine treatment. Pretreatment of rats with unlabeled DASB reduced binding of [<sup>11</sup>C]DASB in a dose-dependent manner. The mean ED<sub>50</sub> for the whole brain is 56 nmol/kg. Elimination of [<sup>11</sup>C]DASB was via the hepatobiliary and renal systems.</p></div><div id="DASB11C.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=DASB%20and%20%28pig%20or%20cat%20or%20dog%20or%20rabbit%20or%20sheep%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>[<sup>11</sup>C]DASB (200 MBq or 5.4 mCi) was injected in pigs to study its positron emission tomography (PET) imaging properties of brain SERT (<a class="bk_pop" href="#DASB11C.REF.11">11</a>). The fraction of intact tracer in plasma at 10 min after injection was 35%. Citalopram pretreatment reduced the binding potential and distribution volume of [<sup>11</sup>C]DASB markedly in the mesencephalon, striatum, and frontal cortex. There was substantial agreement between results of several methods of kinetic analysis. There was a uniform displacement of 80% of [<sup>11</sup>C]DASB specific binding after citalopram <i>in vivo</i>.</p></div><div id="DASB11C.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=DASB%20AND%20%28primate%20not%20human%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>In monkeys, [<sup>11</sup>C]DASB uptake was greatest in lungs, followed by the urinary bladder, gallbladder, brain, and other organs at 7-95 min (<a class="bk_pop" href="#DASB11C.REF.12">12</a>). The tracer was eliminated via the hepatobiliary and renal systems. Paroxetine (SERT inhibitor) and 3,4-methylenedioxymethamphetamine (5-HT neurotoxicity) reduced the uptake of [<sup>11</sup>C]DASB in brain regions with high SERT density (<a class="bk_pop" href="#DASB11C.REF.13">13</a>). The biological half-life in plasma was 30 min. The metabolism led to very polar metabolites (19% of total [<sup>11</sup>C]DASB radioactivity in 30 min) and one or more lipophilic metabolites in the plasma.</p></div></div><div id="DASB11C.Human_Studies"><h2 id="_DASB11C_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=DASB%20and%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Nine healthy volunteers received intravenous injections of 350 MBq (9.7 mCi) [<sup>11</sup>C]DASB (<a class="bk_pop" href="#DASB11C.REF.7">7</a>). Sequential images of the brain were taken over a 90-min period. The highest uptake was in the mid-brain, thalamus, hypothalamus, and striatum. The peak uptake occurred at 30-40 min. After pretreatment with an oral dose of 40 mg of citalopram, there was an 80% reduction in specific binding of [<sup>11</sup>C]DASB in SERT-rich regions. The metabolism of [<sup>11</sup>C]DASB was rapid, with about 50% of the intact compound remaining in plasma at 20 min after injection.</p><p>No difference in regional SERT binding potential was found between major depressive episodes and normal subjects as measured by [<sup>11</sup>C]DASB PET (<a class="bk_pop" href="#DASB11C.REF.9">9</a>). In a subgroup of patients with major depressive episodes patients and with more negativistic dysfunctional attitudes, there was a significantly higher SERT binding potential, which led to low extracellular 5-HT. It was suggested that the lower 5-HT level caused these patients to feel more negativistic. [<sup>11</sup>C]DASB PET is being evaluated as a useful tool for antidepressant development (<a class="bk_pop" href="#DASB11C.REF.14">14</a>), obsessive-compulsive disorder studies (<a class="bk_pop" href="#DASB11C.REF.15">15</a>) and alcoholism (<a class="bk_pop" href="#DASB11C.REF.16">16</a>).</p><p>Human dosimetry of [<sup>11</sup>C]DASB was estimated in seven normal volunteers (<a class="bk_pop" href="#DASB11C.REF.17">17</a>). Dynamic whole-body PET scans were acquired after the injection of 669 ± 97 MBq (18.1 ± 2.6 mCi) of [<sup>11</sup>C]DASB. Uptake of [<sup>11</sup>C]DASB in the lungs was rapid and high, with a peak of 53.1%ID within 18-46 s after injection. About 12% ID was excreted in urine. The organs that received the highest absorbed doses were found to be the lungs (0.0328 mGy/MBq or 121 mrad/mCi), the urinary bladder (0.012 mGy/MBq or 44 mrad/mCi), the kidneys (0.0093 mGy/MBq or 34 mrad/mCi), the gallbladder (0.0093 mGy/MBq or 34 mrad/mCi), and the liver (0.0064 mGy/MBq or 24 mrad/mCi). The effective dose was calculated as 0.0070 mSv/MBq (26 mrem/mCi) for a 70-kg-standard man.</p></div><div id="DASB11C.NIH_Support"><h2 id="_DASB11C_NIH_Support_">NIH Support</h2><p>MH62185, MH40695, MH01997, DA05707, DA06275, AG14400, AA11653, intramural research program</p></div><div id="DASB11C.references"><h2 id="_DASB11C_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="DASB11C.REF.1">Lucki I. The spectrum of behaviors influenced by serotonin. <span><span class="ref-journal">Biol Psychiatry. </span>1998;<span class="ref-vol">
|
||
<strong>44</strong>
|
||
</span>(3):151–62.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9693387" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9693387</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="DASB11C.REF.2">Abi-Dargham A. , Laruelle M. , Aghajanian G.K. , Charney D. , Krystal J. The role of serotonin in the pathophysiology and treatment of schizophrenia. <span><span class="ref-journal">J Neuropsychiatry Clin Neurosci. </span>1997;<span class="ref-vol">
|
||
<strong>9</strong>
|
||
</span>(1):1–17.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9017523" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9017523</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="DASB11C.REF.3">Charney D.S. Monoamine dysfunction and the pathophysiology and treatment of depression. <strong>Suppl 14</strong><span><span class="ref-journal">J Clin Psychiatry. </span>1998;<span class="ref-vol">
|
||
<strong>59</strong>
|
||
</span>:11–4.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9818625" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9818625</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="DASB11C.REF.4">Parsey R.V. , Kegeles L.S. , Hwang D.R. , Simpson N. , Abi-Dargham A. , Mawlawi O. , Slifstein M. , Van Heertum R.L. , Mann J.J. , Laruelle M. In vivo quantification of brain serotonin transporters in humans using [11C]McN 5652. <span><span class="ref-journal">J Nucl Med. </span>2000;<span class="ref-vol">
|
||
<strong>41</strong>
|
||
</span>(9):1465–77.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10994724" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10994724</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="DASB11C.REF.5">Szabo Z. , Scheffel U. , Mathews W.B. , Ravert H.T. , Szabo K. , Kraut M. , Palmon S. , Ricaurte G.A. , Dannals R.F. Kinetic analysis of [11C]McN5652: a serotonin transporter radioligand. <span><span class="ref-journal">J Cereb Blood Flow Metab. </span>1999;<span class="ref-vol">
|
||
<strong>19</strong>
|
||
</span>(9):967–81.</span> [<a href="/pmc/articles/PMC2034412/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2034412</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/10478648" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10478648</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="DASB11C.REF.6">Wilson A.A. , Ginovart N. , Schmidt M. , Meyer J.H. , Threlkeld P.G. , Houle S. Novel radiotracers for imaging the serotonin transporter by positron emission tomography: synthesis, radiosynthesis, and in vitro and ex vivo evaluation of (11)C-labeled 2-(phenylthio)araalkylamines. <span><span class="ref-journal">J Med Chem. </span>2000;<span class="ref-vol">
|
||
<strong>43</strong>
|
||
</span>(16):3103–10.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10956218" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10956218</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="DASB11C.REF.7">Houle S. , Ginovart N. , Hussey D. , Meyer J.H. , Wilson A.A. Imaging the serotonin transporter with positron emission tomography: initial human studies with [11C]DAPP and [11C]DASB. <span><span class="ref-journal">Eur J Nucl Med. </span>2000;<span class="ref-vol">
|
||
<strong>27</strong>
|
||
</span>(11):1719–22.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11105830" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11105830</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="DASB11C.REF.8">Wilson A.A. , Ginovart N. , Hussey D. , Meyer J. , Houle S. In vitro and in vivo characterisation of [11C]-DASB: a probe for in vivo measurements of the serotonin transporter by positron emission tomography. <span><span class="ref-journal">Nucl Med Biol. </span>2002;<span class="ref-vol">
|
||
<strong>29</strong>
|
||
</span>(5):509–15.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12088720" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12088720</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="DASB11C.REF.9">Meyer J.H. , Houle S. , Sagrati S. , Carella A. , Hussey D.F. , Ginovart N. , Goulding V. , Kennedy J. , Wilson A.A. Brain serotonin transporter binding potential measured with carbon 11-labeled DASB positron emission tomography: effects of major depressive episodes and severity of dysfunctional attitudes. <span><span class="ref-journal">Arch Gen Psychiatry. </span>2004;<span class="ref-vol">
|
||
<strong>61</strong>
|
||
</span>(12):1271–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15583118" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15583118</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="DASB11C.REF.10">Lundquist P. , Wilking H. , Hoglund A.U. , Sandell J. , Bergstrom M. , Hartvig P. , Langstrom B. Potential of [(11)C]DASB for measuring endogenous serotonin with PET: binding studies. <span><span class="ref-journal">Nucl Med Biol. </span>2005;<span class="ref-vol">
|
||
<strong>32</strong>
|
||
</span>(2):129–36.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15721758" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15721758</span></a>]</div></dd><dt>11.</dt><dd><div class="bk_ref" id="DASB11C.REF.11">Jensen S.B. , Smith D.F. , Bender D. , Jakobsen S. , Peters D. , Nielsen E.O. , Olsen G.M. , Scheel-Kruger J. , Wilson A. , Cumming P. [11C]-NS 4194 versus [11C]-DASB for PET imaging of serotonin transporters in living porcine brain. <span><span class="ref-journal">Synapse. </span>2003;<span class="ref-vol">
|
||
<strong>49</strong>
|
||
</span>(3):170–7.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12774301" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12774301</span></a>]</div></dd><dt>12.</dt><dd><div class="bk_ref" id="DASB11C.REF.12">Belanger M.J. , Simpson N.R. , Wang T. , Van Heertum R.L. , Mann J.J. , Parsey R.V. Biodistribution and radiation dosimetry of [11C]DASB in baboons. <span><span class="ref-journal">Nucl Med Biol. </span>2004;<span class="ref-vol">
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||
<strong>31</strong>
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||
</span>(8):1097–102.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15607492" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15607492</span></a>]</div></dd><dt>13.</dt><dd><div class="bk_ref" id="DASB11C.REF.13">Szabo Z. , McCann U.D. , Wilson A.A. , Scheffel U. , Owonikoko T. , Mathews W.B. , Ravert H.T. , Hilton J. , Dannals R.F. , Ricaurte G.A. Comparison of (+)-(11)C-McN5652 and (11)C-DASB as serotonin transporter radioligands under various experimental conditions. <span><span class="ref-journal">J Nucl Med. </span>2002;<span class="ref-vol">
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<strong>43</strong>
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</span>(5):678–92.</span> [<a href="/pmc/articles/PMC2078607/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2078607</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/11994534" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11994534</span></a>]</div></dd><dt>14.</dt><dd><div class="bk_ref" id="DASB11C.REF.14">Meyer J.H. Imaging the serotonin transporter during major depressive disorder and antidepressant treatment. <span><span class="ref-journal">J Psychiatry Neurosci. </span>2007;<span class="ref-vol">
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<strong>32</strong>
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</span>(2):86–102.</span> [<a href="/pmc/articles/PMC1810585/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC1810585</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/17353938" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17353938</span></a>]</div></dd><dt>15.</dt><dd><div class="bk_ref" id="DASB11C.REF.15">Reimold M. , Smolka M.N. , Zimmer A. , Batra A. , Knobel A. , Solbach C. , Mundt A. , Smoltczyk H.U. , Goldman D. , Mann K. , Reischl G. , Machulla H.J. , Bares R. , Heinz A. Reduced availability of serotonin transporters in obsessive-compulsive disorder correlates with symptom severity - a [11C]DASB PET study. <span><span class="ref-journal">J Neural Transm. </span>2007;<span class="ref-vol">
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<strong>114</strong>
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</span>(12):1603–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17713719" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17713719</span></a>]</div></dd><dt>16.</dt><dd><div class="bk_ref" id="DASB11C.REF.16">Brown A.K. , George D.T. , Fujita M. , Liow J.S. , Ichise M. , Hibbeln J. , Ghose S. , Sangare J. , Hommer D. , Innis R.B. PET [11C]DASB imaging of serotonin transporters in patients with alcoholism. <span><span class="ref-journal">Alcohol Clin Exp Res. </span>2007;<span class="ref-vol">
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<strong>31</strong>
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</span>(1):28–32.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17207098" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17207098</span></a>]</div></dd><dt>17.</dt><dd><div class="bk_ref" id="DASB11C.REF.17">Lu J.Q. , Ichise M. , Liow J.S. , Ghose S. , Vines D. , Innis R.B. Biodistribution and radiation dosimetry of the serotonin transporter ligand 11C-DASB determined from human whole-body PET. <span><span class="ref-journal">J Nucl Med. </span>2004;<span class="ref-vol">
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<strong>45</strong>
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</span>(9):1555–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15347724" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15347724</span></a>]</div></dd></dl></div><div id="bk_toc_contnr"></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/NBK23385/?report=reader">PubReader</a></li><li><a href="/books/NBK23385/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23385" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23385" style="display:none" title="Cite this Page"><div class="bk_tt">Leung K. [11C]N,N-Dimethyl-2-(2-amino-4-cyanophenylthio)benzylamine. 2005 May 18 [Updated 2008 Jun 24]. 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/NBK23385/pdf/Bookshelf_NBK23385.pdf">PDF version of this page</a> (143K)</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="#DASB11C.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#DASB11C.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#DASB11C.In_Vitro_Studies_Tes" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#DASB11C.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#DASB11C.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#DASB11C.NIH_Support" ref="log$=inpage&link_id=inpage">NIH Support</a></li><li><a href="#DASB11C.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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2004</em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/20641424" ref="ordinalpos=1&linkpos=3&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> 2-((2-Amino-4-chloro-5-[(18)F]fluorophenyl)thio)-N,N-dimethylbenzenmethanamine.</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> 2-((2-Amino-4-chloro-5-[(18)F]fluorophenyl)thio)-N,N-dimethylbenzenmethanamine.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">The MICAD Research Team. </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 class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/23856117" ref="ordinalpos=1&linkpos=4&log$=relatedarticles&logdbfrom=pubmed">Characterization of FlipIDAM as a SERT-selective SPECT imaging agent.</a><span class="source">[Nucl Med Biol. 2013]</span><div class="brieflinkpop offscreen_noflow">Characterization of FlipIDAM as a SERT-selective SPECT imaging agent.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Lemoine L, Lieberman BP, Ploessl K, Zheng P, Kung HF. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Nucl Med Biol. 2013 Oct; 40(7):879-86. Epub 2013 Jul 12.</em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/20641336" ref="ordinalpos=1&linkpos=5&log$=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> [(11)C]2-(2-(Dimethylaminomethyl)phenylthio)-5-fluoromethylphenylamine.</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> [(11)C]2-(2-(Dimethylaminomethyl)phenylthio)-5-fluoromethylphenylamine.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">The MICAD Research Team. </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></ul><a class="seemore" href="/sites/entrez?db=pubmed&cmd=link&linkname=pubmed_pubmed_reviews&uid=20641586" ref="ordinalpos=1&log$=relatedreviews_seeall&logdbfrom=pubmed">See reviews...</a><a class="seemore" href="/sites/entrez?db=pubmed&cmd=link&linkname=pubmed_pubmed&uid=20641586" ref="ordinalpos=1&log$=relatedarticles_seeall&logdbfrom=pubmed">See all...</a></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Recent Activity</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="recent_activity" id="Shutter"></a></div><div class="portlet_content"><div xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" id="HTDisplay" class=""><div class="action"><a href="javascript:historyDisplayState('ClearHT')">Clear</a><a href="javascript:historyDisplayState('HTOff')" class="HTOn">Turn Off</a><a href="javascript:historyDisplayState('HTOn')" class="HTOff">Turn On</a></div><ul id="activity"><li class="ra_rcd ralinkpopper two_line"><a class="htb ralinkpopperctrl" ref="log$=activity&linkpos=1" href="/portal/utils/pageresolver.fcgi?recordid=67d6446767c23b31e029cb06">[11C]N,N-Dimethyl-2-(2-amino-4-cyanophenylthio)benzylamine - Molecular Imaging a...</a><div class="ralinkpop offscreen_noflow">[11C]N,N-Dimethyl-2-(2-amino-4-cyanophenylthio)benzylamine - Molecular Imaging and Contrast Agent Database (MICAD)<div class="brieflinkpopdesc"></div></div><div class="tertiary"></div></li><li class="ra_rcd ralinkpopper two_line"><a class="htb ralinkpopperctrl" ref="log$=activity&linkpos=2" href="/portal/utils/pageresolver.fcgi?recordid=67d6446584f3725e59a3bfba">[11C]N,N-Dimethyl-2-(2´-amino-4´-hydroxymethylphenylthio)benzylamine - Molecular...</a><div class="ralinkpop offscreen_noflow">[11C]N,N-Dimethyl-2-(2´-amino-4´-hydroxymethylphenylthio)benzylamine - Molecular Imaging and Contrast Agent Database (MICAD)<div class="brieflinkpopdesc"></div></div><div class="tertiary"></div></li><li class="ra_rcd ralinkpopper two_line"><a class="htb ralinkpopperctrl" ref="log$=activity&linkpos=3" href="/portal/utils/pageresolver.fcgi?recordid=67d6446484f3725e59a3bb68">[11C]Methylated LY2181308 - Molecular Imaging and Contrast Agent Database (MICAD...</a><div class="ralinkpop offscreen_noflow">[11C]Methylated LY2181308 - Molecular Imaging and Contrast Agent Database (MICAD)<div class="brieflinkpopdesc"></div></div><div class="tertiary"></div></li><li class="ra_rcd ralinkpopper two_line"><a class="htb ralinkpopperctrl" ref="log$=activity&linkpos=4" href="/portal/utils/pageresolver.fcgi?recordid=67d64463cde49f3df753bc0a">[11C]meta-Hydroxyephedrine - Molecular Imaging and Contrast Agent Database (MICA...</a><div class="ralinkpop offscreen_noflow">[11C]meta-Hydroxyephedrine - Molecular Imaging and Contrast Agent Database (MICAD)<div class="brieflinkpopdesc"></div></div><div class="tertiary"></div></li><li class="ra_rcd ralinkpopper two_line"><a class="htb ralinkpopperctrl" ref="log$=activity&linkpos=5" href="/portal/utils/pageresolver.fcgi?recordid=67d644612f30673f7b6e3bb5">[11C]Glycylsarcosine - Molecular Imaging and Contrast Agent Database (MICAD)</a><div class="ralinkpop offscreen_noflow">[11C]Glycylsarcosine - Molecular Imaging and Contrast Agent Database (MICAD)<div class="brieflinkpopdesc"></div></div><div class="tertiary"></div></li></ul><p class="HTOn">Your browsing activity is empty.</p><p class="HTOff">Activity recording is turned off.</p><p id="turnOn" class="HTOff"><a href="javascript:historyDisplayState('HTOn')">Turn recording back on</a></p><a class="seemore" href="/sites/myncbi/recentactivity">See more...</a></div></div></div>
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