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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="#__NBK23133_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23133_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/AFE11C/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/BF227-11C/" 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="_NBK23133_"><span class="title" itemprop="name">[<sup>11</sup>C]2-(2-(Dimethylaminomethyl)phenylthio)-5-fluoromethylphenylamine</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">[<sup>11</sup>C]AFM</div><p class="contrib-group"><span itemprop="author">The MICAD Research Team</span>.</p><p class="small">Created: <span itemprop="datePublished">February 7, 2006</span>; Last Update: <span itemprop="dateModified">February 14, 2006</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="AFM11C.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23133/table/AFM11C.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__AFM11C.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>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<sup>11</sup>C]2-(2-(Dimethylaminomethyl)phenylthio)-5-fluoromethylphenylamine</td><td rowspan="10" colspan="1" style="text-align:left;vertical-align:middle;">
|
||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/8139829" 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=8139829" alt="image 8139829 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;">
|
||
<b>Abbreviated name:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<sup>11</sup>C]AFM</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Synonym:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"></td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Agent Category:</b>
|
||
</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;">
|
||
<b>Target:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Serotonin transporter (SERT)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Target Category:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Ligand binding</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Method of detection:</b>
|
||
</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;">
|
||
<b>Source of signal:</b>
|
||
</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;">
|
||
<b>Activation:</b>
|
||
</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;">
|
||
<b>Studies:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
|
||
<ul class="simple-list"><li id="A490" class="half_rhythm"><div>
|
||
<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
|
||
<i>In vitro</i>
|
||
|
||
</div></li><li id="A491" class="half_rhythm"><div>
|
||
<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Rodents
|
||
</div></li><li id="A492" class="half_rhythm"><div>
|
||
<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Non-human primates
|
||
</div></li></ul>
|
||
</td></tr></tbody></table></div></div><div id="AFM11C.Background"><h2 id="_AFM11C_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%5BAll%20Fields%5D%20AND%20AFM%5BAll%20Fields%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a><a href="/entrez/query.fcgi?CMD=search&DB=pubmed" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri"></a>]</p><p>The neurotransmitter serotonin (5-HT) plays a major role in a variety of brain functions such as appetite, sleep, and mood. Neuropsychiatric disorders, including major depression, schizophrenia, and Alzheimer’s and Parkinson’s diseases (<a class="bk_pop" href="#AFM11C.EXTYLES.1">1-3</a>), involve a dysfunction of the brain’s serotonin system. The serotonergic neurons – present in wide areas of the brain, including the hypothalamus, thalamus, and cerebral cortex – bear a protein called “serotonin transporter” (SERT) (<a class="bk_pop" href="#AFM11C.EXTYLES.4">4</a>).</p><p>The SERT, located on the cell bodies and terminals of 5-HT neurons, is a specific marker for the number and integrity of presynaptic terminals of serotonin-producing neurons. It regulates neurotransmission by removing released serotonin from the extracellular space back into the presynaptic neuron. Commonly prescribed antidepressants are selective serotonin reuptake inhibitors (SSRIs), and their effects are obtained through interaction with (and inhibition of) the SERT (<a class="bk_pop" href="#AFM11C.EXTYLES.5">5</a>). For that reason, <i>in vivo</i> imaging of the regional brain distribution of the SERT is an important tool to study the 5-HT system and the treatment of neuropsychiatric disorders.</p><p>A variety of <i>in vivo</i> radioligands for positron emission tomography (PET) have been evaluated for imaging the SERT. [<sup>11</sup>C]McN5652 was the first successful and widely used agent (<a class="bk_pop" href="#AFM11C.EXTYLES.6">6</a>, <a class="bk_pop" href="#AFM11C.EXTYLES.7"> 7</a>). However, it does have some limitations; for example, its kinetics in the brain are slow and its binding ratios in humans show low or nonspecificity. It is adequate for regions with high SERT density but often provides insufficient signal-to-noise differentials for imaging brain regions with intermediate to low SERT densities (e.g., limbic and neocortical regions) because of its high nonspecific binding.</p><p>Over recent years, new PET radioligands have been synthesized and evaluated as SERT imaging agents and alternatives to [<sup>11</sup>C]McN5652. Among them, <sup>11</sup>C-labeled <i>N</i>,<i>N</i>-dimethyl-2-(2-amino-4-cyanophenylthio)benzylamine (<a href="/books/n/micad/DASB11C/">[<sup>11</sup>C]DASB</a>), 2-(2-(dimethylaminomethyl)phenylthio)-5-fluoromethylphenylamine ([<sup>11</sup>C]AFM), 5-bromo-2-[2-(dimethylaminomethylphenylthio)]phenylamine ([<sup>11</sup>C]DAPA), 2-[2-(dimethylaminomethylphenylthio)]-5-iodophenylamine ([<sup>11</sup>C]ADAM), and <i>N,N</i>-dimethyl-2-(2´-amino-4´-hydroxymethylphenylthio)benzylamine (<a href="/books/n/micad/HOMADAM11C/">[<sup>11</sup>C]HOMADAM</a>) (<a class="bk_pop" href="#AFM11C.EXTYLES.8">8</a>) are based on a diaryl sulfide motif (<a class="bk_pop" href="#AFM11C.EXTYLES.4">4</a>). [<sup>11</sup>C]AFM has shown high binding affinity and good selectivity for the SERT, and displays signal/noise ratios that may enable more reliable mapping of brain regions with a low density of SERT.</p></div><div id="AFM11C.Synthesis"><h2 id="_AFM11C_Synthesis_">Synthesis</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2811C%29AFA%20AND%20synthesis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a><a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=fluoroflumazenil%5BAll%20Fields%5D%20AND%20synthesis%5BAll%20Fields%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri"></a>]</p><p>AFM and its C-11 radiolabeling precursor can be prepared in a five-step procedure, as described by Huang et al. (<a class="bk_pop" href="#AFM11C.EXTYLES.9">9</a>). Briefly, 4-chloro-3-nitrobenzyl acetate is coupled with thiosalicylic acid to give 2-(4-acetyloxymethyl-2-nitrophenylthio)benzoic acid, which is then converted to 2-(4-acetyloxymethyl-2-nitrophenylthio)-<i>N,N</i>-dimethylbenzamide. Reduction of the amide functionality to the tertiary amine and cleavage of the acetyl group with borane/tetrahydrofuran complex produce 2-(4-hydroxymethyl-2-nitrophenylthio)-<i>N,N</i>-dimethylbenzylamine. Fluorination of this compound with bis(2-methoxyethyl)aminosulfur trifluoride is then performed to produce the benzyl fluoride 2-(4-fluoromethyl-2-nitrophenylthio)-<i>N,N</i>-dimethylbenzylamine. Finally, reduction of the nitro group produces AFM.</p><p>Starting with 2-(4-acetyloxymethyl-2-nitrophenylthio)benzoic acid and replacing <i>N,N</i>-dimethylamine hydrochloride with <i>N</i>-methylamine hydrochloride (in the amide formation step) leads to the formation of the C-11 labeling precursor 5-fluoromethyl-2-(2-methylaminomethylphenylthio)phenylamine. [<sup>11</sup>C]AFM is prepared from this precursor by reaction with [<sup>11</sup>C]iodomethane (in dimethyl formamide, at 80-85 °C).</p><p>The chemical and radiochemical purities of [<sup>11</sup>C]AFM produced by this method are ≥97% (as determined by high-performance liquid chromatography). The radiochemical yield at the end of the synthesis is 12.3 ± 8.1% (decay-corrected, based on [<sup>11</sup>C]iodomethane; <i>n</i> = 14). The specific activity of the radiotracer produced is 64,121 ± 15,836 GBq/mmol (1,733 ± 428 Ci/mmol). The total synthesis time, as reported by Huang et al. (<a class="bk_pop" href="#AFM11C.EXTYLES.9">9</a>), is about 30-37 min.</p></div><div id="AFM11C.In_Vitro_Studies_Tes"><h2 id="_AFM11C_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=11C%5BAll%20Fields%5D%20AND%20AFM%20AND%20in%20vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Huang et al. (<a class="bk_pop" href="#AFM11C.EXTYLES.9">9</a>) assayed the affinity of AFM for the SERT, norepinephrine transporter (NET), and dopamine transporter (DAT), using cloned human receptors expressed on HEK-293 cells and the radioligands [<sup>3</sup>H]paroxetine (for SERT), [<sup>3</sup>H]nisoxetine (for NET), and [<sup>3</sup>H]<a href="/protein/2281712181/?report=GenPept" class="bk_tag" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=genpept">GBR12935</a> (for DAT). Experiments were performed according to previously published procedures (<a class="bk_pop" href="#AFM11C.EXTYLES.10">10</a>, <a class="bk_pop" href="#AFM11C.EXTYLES.11"> 11</a>). Results showed that AFM had a high affinity and a good selectivity for SERT over NET and DAT. The authors reported the following inhibition coefficients (<i>K</i><sub>i</sub>s): 1.04 ± 0.13, 663.8 ± 79.5, and >10,000 nM for SERT, NET, and DAT, respectively.</p><p>In comparative studies between various SERT radiotracers, Huang et al. (<a class="bk_pop" href="#AFM11C.EXTYLES.12">12</a>) found no significant difference between the <i>K</i><sub>i</sub>s of McN5652, ADAM, DASB, and AFM. Temperature had no significant effect on the inhibition coefficients for AFM, McN5652, and ADAM, but significantly decreased the affinity of DASB for SERT.</p></div><div id="AFM11C.Animal_Studies"><h2 id="_AFM11C_Animal_Studies_">Animal Studies</h2><div id="AFM11C.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20AND%20AFM%20AND%20%22rodentia%22%5BMeSH%20Terms%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a><a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=HOMADAM%20AND%20%22rodentia%22" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri"></a>]</p><p>Biodistribution studies in Sprague-Dawley rats were performed by Huang et al. (<a class="bk_pop" href="#AFM11C.EXTYLES.9">9</a>). The experimental procedure involved injecting 3.7 MBq (100 µCi) of [<sup>11</sup>C]AFM per animal (via the tail vein) and measuring the uptake of the radiotracer at 10, 30, and 60 min post injection, after sacrifice.</p><p>Results showed rapid uptake of [<sup>11</sup>C]AFM into the brain, with accumulation in regions rich in SERTs, such as the thalamus, hypothalamus, and cortex. The reported total brain uptakes of [<sup>11</sup>C]AFM at 10, 30, and 60 min post injection were 0.70, 1.06, and 1.00% of injected dose (ID)/g of tissue, respectively. The thalamus/cerebellum and hypothalamus/cerebellum activity ratios were 6.06 ± 0.17 and 6.05 ± 1.01, respectively, at 60 min post injection. When pretreated with either cold AFM (2mg/kg of tissue) or citalopram (a SSRI), the brain uptake was significantly reduced.</p></div><div id="AFM11C.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20AND%20AFM%20AND%20%28dog%20OR%20sheep%20OR%20pig%20OR%20rabbit%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a><a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=HOMADAM%20AND%20%28dog%20OR%20sheep%20OR%20pig%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri"></a>]</p><p>No publication is currently available.</p></div><div id="AFM11C.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%5BAll%20Fields%5D%20AND%20AFM%20AND%20%28primate%20NOT%20human%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>PET brain imaging studies of three adult male baboons were performed by Huang et al. (<a class="bk_pop" href="#AFM11C.EXTYLES.9">9</a>), for time periods ranging from 0 to 90 min after administration of [<sup>11</sup>C]AFM. Results showed rapid distribution of the radiotracer in the brain, consistent with the regional concentrations of SERT. High uptakes were observed in the midbrain and thalamus, moderate uptakes were seen in the hippocampus and striatum, and low levels of radioactivity were detected in the cortical regions.</p><p>In all brain regions, the measured activity reached a peak followed by a substantial wash-out (e.g., maximum activity obtained at 41 ± 12 min with a wash-out of 21 ± 14% for the hippocampus). At 45 min post injection, the measured total brain uptake was 0.015 ± 0.001% ID/g of tissue, a result consistent with values obtained in rats. The reported thalamus/cerebellum, striatum/cerebellum, and hippocampus/cerebellum activity ratios were 3.3 ± 0.4, 2.4 ± 0.4, and 1.7 ± 0.3, respectively, at 90 min post injection. Significant differences in clearance were observed between the several baboons used in the study.</p><p>When the baboons were pretreated with citalopram (a SSRI; 4 and 6 mg/kg of tissue) 10 min before injection of [<sup>11</sup>C]AFM, a significant reduction in the brain distribution volumes was observed (30.8 ± 6.4 mL/g reduced to 15.2 mL/g (baboon A) and 29.4 ± 3.2 mL/g reduced to 21.3 mL/g (baboon B), under control conditions).</p><p>In comparative studies between the SERT radiotracers [<sup>11</sup>C]ADAM, [<sup>11</sup>C]AFM, [<sup>11</sup>C]DASB, [<sup>11</sup>C]DAPA, and [<sup>11</sup>C]McN5652, Huang et al. (<a class="bk_pop" href="#AFM11C.EXTYLES.12">12</a>) showed that the regional-specific-to-nonspecific equilibrium partition coefficient was the highest for [<sup>11</sup>C]AFM, followed by [<sup>11</sup>C]DASB, [<sup>11</sup>C]DAPA, [<sup>11</sup>C]ADAM, and [<sup>11</sup>C]McN5652. [<sup>11</sup>C]AFM was shown to provide higher signal/noise ratios, which might enable more reliable measurement of SERT availability in regions of low SERT density.</p></div></div><div id="AFM11C.Human_Studies"><h2 id="_AFM11C_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%5BAll%20Fields%5D%20AND%20AFM%5BAll%20Fields%5D%20AND%20%28human%20NOT%20baboon%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="AFM11C.references"><h2 id="_AFM11C_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="AFM11C.EXTYLES.1">Owens MJ , Nemeroff CB . <span class="ref-title">The serotonin transporter and depression </span><span class="ref-journal">Depress Anxiety</span> 19988Suppl 15–12. [<a href="https://pubmed.ncbi.nlm.nih.gov/9809208" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9809208</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="AFM11C.EXTYLES.2">Palmer AM , Francis PT , Benton JS , Sims NR , Mann DM , Neary D , Snowden JS , Bowen DM . Presynaptic serotonergic dysfunction in patients with Alzheimer's disease. <span><span class="ref-journal">J Neurochem. </span>1987;<span class="ref-vol">48</span>(1):8–15.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/2432177" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 2432177</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="AFM11C.EXTYLES.3">Roth BL , Xia Z . Molecular and cellular mechanisms for the polarized sorting of serotonin receptors: relevance for genesis and treatment of psychosis. <span><span class="ref-journal">Crit Rev Neurobiol. </span>2004;<span class="ref-vol">16</span>(4):229–236.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15862107" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15862107</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="AFM11C.EXTYLES.4">Laakso A , Hietala J . PET studies of brain monoamine transporters. <span><span class="ref-journal">Curr Pharm Des. </span>2000;<span class="ref-vol">6</span>(16):1611–1623.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10974156" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10974156</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="AFM11C.EXTYLES.5">White KJ , Walline CC , Barker EL . Serotonin transporters: implications for antidepressant drug development. <span><span class="ref-journal">Aaps J. </span>2005;<span class="ref-vol">7</span>(2):E421–E433.</span> [<a href="/pmc/articles/PMC2750979/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2750979</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/16353921" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16353921</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="AFM11C.EXTYLES.6">Ichimiya T , Suhara T , Sudo Y , Okubo Y , Nakayama K , Nankai M , Inoue M , Yasuno F , Takano A , Maeda J , Shibuya H . Serotonin transporter binding in patients with mood disorders: a PET study with [11C](+)McN5652. <span><span class="ref-journal">Biol Psychiatry. </span>2002;<span class="ref-vol">51</span>(9):715–722.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11983185" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11983185</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="AFM11C.EXTYLES.7">Suehiro M , Scheffel U , Ravert HT , Dannals RF , Wagner HN . [11C](+)McN5652 as a radiotracer for imaging serotonin uptake sites with PET. <span><span class="ref-journal">Life Sci. </span>1993;<span class="ref-vol">53</span>(11):883–892.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/8366755" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 8366755</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="AFM11C.EXTYLES.8">Jarkas N , Votaw JR , Voll RJ , Williams L , Camp VM , Owens MJ , Purselle DC , Bremner JD , Kilts CD , Nemeroff CB , Goodman MM . Carbon-11 HOMADAM: a novel PET radiotracer for imaging serotonin transporters. <span><span class="ref-journal">Nucl Med Biol. </span>2005;<span class="ref-vol">32</span>(3):211–224.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15820756" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15820756</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="AFM11C.EXTYLES.9">Huang Y , Hwang DR , Bae SA , Sudo Y , Guo N , Zhu Z , Narendran R , Laruelle M . A new positron emission tomography imaging agent for the serotonin transporter: synthesis, pharmacological characterization, and kinetic analysis of [11C]2-[2-(dimethylaminomethyl)phenylthio]-5-fluoromethylphenylamine ([11C]AFM). <span><span class="ref-journal">Nucl Med Biol. </span>2004;<span class="ref-vol">31</span>(5):543–556.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15219271" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15219271</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="AFM11C.EXTYLES.10">Huang Y , Hwang DR , Zhu Z , Bae SA , Guo N , Sudo Y , Kegeles LS , Laruelle M . Synthesis and pharmacological characterization of a new PET ligand for the serotonin transporter: [11C]5-bromo-2-[2-(dimethylaminomethylphenylsulfanyl)]phenylamine ([11C]DAPA). <span><span class="ref-journal">Nucl Med Biol. </span>2002;<span class="ref-vol">29</span>(7):741–751.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12381454" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12381454</span></a>]</div></dd><dt>11.</dt><dd><div class="bk_ref" id="AFM11C.EXTYLES.11">Laruelle M , Vanisberg MA , Maloteaux JM . Regional and subcellular localization in human brain of [3H]paroxetine binding, a marker of serotonin uptake sites. <span><span class="ref-journal">Biol Psychiatry. </span>1988;<span class="ref-vol">24</span>(3):299–309.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/2969755" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 2969755</span></a>]</div></dd><dt>12.</dt><dd><div class="bk_ref" id="AFM11C.EXTYLES.12">Huang Y , Hwang DR , Narendran R , Sudo Y , Chatterjee R , Bae SA , Mawlawi O , Kegeles LS , Wilson AA , Kung HF , Laruelle M . Comparative evaluation in nonhuman primates of five PET radiotracers for imaging the serotonin transporters: [11C]McN 5652, [11C]ADAM, [11C]DASB, [11C]DAPA, and [11C]AFM. <span><span class="ref-journal">J Cereb Blood Flow Metab. </span>2002;<span class="ref-vol">22</span>(11):1377–1398.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12439295" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12439295</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: NBK23133</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20641336" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20641336</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/AFE11C/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/BF227-11C/" 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/NBK23133/?report=reader">PubReader</a></li><li><a href="/books/NBK23133/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23133" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23133" style="display:none" title="Cite this Page"><div class="bk_tt">The MICAD Research Team. [11C]2-(2-(Dimethylaminomethyl)phenylthio)-5-fluoromethylphenylamine. 2006 Feb 7 [Updated 2006 Feb 14]. 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/NBK23133/pdf/Bookshelf_NBK23133.pdf">PDF version of this page</a> (135K)</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="#AFM11C.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#AFM11C.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#AFM11C.In_Vitro_Studies_Tes" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#AFM11C.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#AFM11C.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#AFM11C.references" ref="log$=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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