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<meta name="robots" content="INDEX,FOLLOW,NOARCHIVE" /><meta name="citation_inbook_title" content="Molecular Imaging and Contrast Agent Database (MICAD) [Internet]" /><meta name="citation_title" content="(+/-)-2-(N-Phenethyl-N-1'-[11C]propyl)amino-5-hydroxytetralin" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2008/02/04" /><meta name="citation_author" content="Kam Leung" /><meta name="citation_pmid" content="20641291" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK23086/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="(+/-)-2-(N-Phenethyl-N-1'-[11C]propyl)amino-5-hydroxytetralin" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="National Center for Biotechnology Information (US)" /><meta name="DC.Contributor" content="Kam Leung" /><meta name="DC.Date" content="2008/02/04" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK23086/" /><meta name="description" content="Dopamine, a neurotransmitter, plays an important role in the mediation of movement, cognition, and emotion (1, 2). Dopamine receptors are involved in the pathophysiology of neuropsychiatric diseases, such as Parkinson’s disease, Alzheimer's disease, Huntington’s disease, and schizophrenia (3). Five subtypes of dopamine receptors, D1 through D5, have been well characterized pharmacologically and biochemically (4). These five dopamine receptor subtypes are classified into two subfamilies: D1-like (D1 and D5) and D2-like (D2, D3, and D4). D1-like and D2-like receptors exert synergistic as well as opposite effects at both the biochemical and overall system levels. Most striatal D1 and D2 receptors are localized postsynaptically on caudate-putamen neurons and to a lesser extent presynaptically on nigrostriatal axons." /><meta name="og:title" content="(+/-)-2-(N-Phenethyl-N-1'-[11C]propyl)amino-5-hydroxytetralin" /><meta name="og:type" content="book" /><meta name="og:description" content="Dopamine, a neurotransmitter, plays an important role in the mediation of movement, cognition, and emotion (1, 2). Dopamine receptors are involved in the pathophysiology of neuropsychiatric diseases, such as Parkinson’s disease, Alzheimer's disease, Huntington’s disease, and schizophrenia (3). Five subtypes of dopamine receptors, D1 through D5, have been well characterized pharmacologically and biochemically (4). These five dopamine receptor subtypes are classified into two subfamilies: D1-like (D1 and D5) and D2-like (D2, D3, and D4). D1-like and D2-like receptors exert synergistic as well as opposite effects at both the biochemical and overall system levels. Most striatal D1 and D2 receptors are localized postsynaptically on caudate-putamen neurons and to a lesser extent presynaptically on nigrostriatal axons." /><meta name="og:url" content="https://www.ncbi.nlm.nih.gov/books/NBK23086/" /><meta name="og:site_name" content="NCBI Bookshelf" /><meta name="og:image" content="https://www.ncbi.nlm.nih.gov/corehtml/pmc/pmcgifs/bookshelf/thumbs/th-micad-lrg.png" /><meta name="twitter:card" content="summary" /><meta name="twitter:site" content="@ncbibooks" /><meta name="bk-non-canon-loc" content="/books/n/micad/PPHT11C/" /><link rel="canonical" href="https://www.ncbi.nlm.nih.gov/books/NBK23086/" /><link rel="stylesheet" href="/corehtml/pmc/css/figpopup.css" type="text/css" media="screen" /><link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books.min.css" type="text/css" /><link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books_print.min.css" type="text/css" media="print" /><style type="text/css">p a.figpopup{display:inline !important} .bk_tt {font-family: monospace} .first-line-outdent .bk_ref {display: inline} .body-content h2, .body-content .h2 {border-bottom: 1px solid #97B0C8} .body-content h2.inline {border-bottom: none} a.page-toc-label , .jig-ncbismoothscroll a {text-decoration:none;border:0 !important} .temp-labeled-list .graphic {display:inline-block !important} .temp-labeled-list img{width:100%}</style><script type="text/javascript" src="/corehtml/pmc/js/jquery.hoverIntent.min.js"> </script><script type="text/javascript" src="/corehtml/pmc/js/common.min.js?_=3.18"> </script><script type="text/javascript" src="/corehtml/pmc/js/large-obj-scrollbars.min.js"> </script><script type="text/javascript">window.name="mainwindow";</script><script type="text/javascript" src="/corehtml/pmc/js/bookshelf/2.26/book-toc.min.js"> </script><script type="text/javascript" src="/corehtml/pmc/js/bookshelf/2.26/books.min.js"> </script><meta name="book-collection" content="NONE" />
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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="#__NBK23086_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23086_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/ZYY-339-11C/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/CP99994C11/" 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="_NBK23086_"><span class="title" itemprop="name">(+/-)-2-(<i>N</i>-Phenethyl-<i>N</i>-1'-[<sup>11</sup>C]propyl)amino-5-hydroxytetralin </span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">[<sup>11</sup>C]PPHT</div><p class="contrib-group"><span itemprop="author">Kam Leung</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK23086_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK23086_ai__"><div class="contrib half_rhythm"><span itemprop="author">Kam Leung</span>, PhD<div class="affiliation small">
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National 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>
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</div></div></div><p class="small">Created: <span itemprop="datePublished">August 16, 2006</span>; Last Update: <span itemprop="dateModified">February 4, 2008</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="PPHT11C.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23086/table/PPHT11C.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__PPHT11C.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;">(+/-)-2-(<i>N</i>-Phenethyl-<i>N</i>-1'-[<sup>11</sup>C]propyl)amino-5-hydroxytetralin</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/14710624" 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=14710624" alt="image 14710624 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]PPHT</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;"></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;">D<sub>2</sub> dopamine receptors</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Target Category:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Receptor binding</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Method of detection:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">PET</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Source of signal:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>11</sup>C</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Activation:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">No</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Studies:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
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<i>In vitro</i>
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</div></li></ul>
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Rodents
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</div></li></ul>
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Non-human primates
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</div></li></ul>
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</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="PPHT11C.Background"><h2 id="_PPHT11C_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20PPHT" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Dopamine, a neurotransmitter, plays an important role in the mediation of movement, cognition, and emotion (<a class="bk_pop" href="#PPHT11C.REF.1">1</a>, <a class="bk_pop" href="#PPHT11C.REF.2">2</a>). Dopamine receptors are involved in the pathophysiology of neuropsychiatric diseases, such as Parkinson’s disease, Alzheimer's disease, Huntington’s disease, and schizophrenia (<a class="bk_pop" href="#PPHT11C.REF.3">3</a>). Five subtypes of dopamine receptors, D<sub>1</sub> through D<sub>5</sub>, have been well characterized pharmacologically and biochemically (<a class="bk_pop" href="#PPHT11C.REF.4">4</a>). These five dopamine receptor subtypes are classified into two subfamilies: D<sub>1</sub>-like (D<sub>1</sub> and D<sub>5</sub>) and D<sub>2</sub>-like (D<sub>2</sub>, D<sub>3</sub>, and D<sub>4</sub>). D<sub>1</sub>-like and D<sub>2</sub>-like receptors exert synergistic as well as opposite effects at both the biochemical and overall system levels. Most striatal D<sub>1</sub> and D<sub>2</sub> receptors are localized postsynaptically on caudate-putamen neurons and to a lesser extent presynaptically on nigrostriatal axons.</p><p>Dopamine receptors are G-protein–coupled receptors that exist in high- and low-affinity states with respect to agonist binding. The two states are inter-convertible. In the high-affinity state, dopamine receptors are coupled to G-proteins, whereas in the low-affinity state they are not. Dopamine has a dissociation constant (<i>K</i><sub>d</sub>) of 7 nM for the high-affinity state (<i>K</i><sub>high</sub>) and a <i>K</i><sub>d</sub> of 1,720 nM for the low-affinity state (<i>K</i><sub>low</sub>) (<a class="bk_pop" href="#PPHT11C.REF.5">5</a>). Under physiologic conditions, dopamine binds predominately to receptors in the high-affinity state. The high-affinity state was suggested to be the functional form of the dopamine receptors (<a class="bk_pop" href="#PPHT11C.REF.6">6</a>).</p><p>Substituted benzamides, such as sulpiride, raclopride, and iodobenzamide, are specific ligands with only moderate affinity for the D<sub>2</sub> receptors, making study of extrastriatal D<sub>2</sub> receptors difficult (<a class="bk_pop" href="#PPHT11C.REF.7">7-9</a>). In binding studies, [<sup>123</sup>I]epidepride, an analog of isoremoxipride, was found to have high potency and low nonspecific binding, and to be selective for striatal and extrastriatal D<sub>2</sub> receptors (<a class="bk_pop" href="#PPHT11C.REF.10">10</a>). Epidepride exhibits marginal binding to D<sub>4</sub> receptors, with little affinity for other known neurotransmitter receptors. (S)-<i>N</i>-((1-Allyl-2-pyrrolidinyl)methyl)-5-(3-[<sup>18</sup>F]fluoropropyl)-2,3-dimethoxybenzamide (<a href="/books/n/micad/Fallypride18F/">[<sup>18</sup>F]fallypride</a>), an analog of epidepride, was found to be a selective high-affinity antagonist of D<sub>2/3</sub> receptors (<a class="bk_pop" href="#PPHT11C.REF.11">11</a>), and in positron emission tomography (PET) <i>in vivo</i> studies (<a class="bk_pop" href="#PPHT11C.REF.12">12-14</a>) it identified extrastriatal D<sub>2/3</sub> receptors. However, none of these antagonists distinguishes between the high- and low-affinity states of the D<sub>2</sub> receptors. (–)-<i>N</i>-[<sup>11</sup>C]Propyl-norapomorphine (<a href="/books/n/micad/NPA11C/">[<sup>11</sup>C]NPA</a>) and [<sup>11</sup>C](+)-4-<i>N</i>-propyl-,3,4a,5,6,10b-hexahydro-2<i>H</i>-naphth[1,2-<i>b</i>][1,4]oxazin-9-ol (<a href="/books/n/micad/PHNO11C/">[<sup>11</sup>C](+)-PHNO</a>) have been developed as radiolabeled dopamine agonists for the non-invasive study of the high-affinity state of the D<sub>2/3</sub> receptors in the brain.</p><p>Various hydroxytetralin analogs with different binding affinities for the D<sub>2</sub> receptors have been developed as agonist radiotracers (<a class="bk_pop" href="#PPHT11C.REF.15">15</a>). (+/-)-2-(<i>N</i>-Phenethyl-<i>N</i>-1’-[<sup>11</sup>C]propyl)amino-5-hydroxytetralin ([<sup>11</sup>C]PPHT) is being evaluated as a PET agent for the high-affinity state of D<sub>2/3</sub> receptors.</p></div><div id="PPHT11C.Synthesis"><h2 id="_PPHT11C_Synthesis_">Synthesis</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20PPHT%20and%20synthesis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Shi et al. (<a class="bk_pop" href="#PPHT11C.REF.15">15</a>) reported a two-step synthesis of [<sup>11</sup>C]PPHT in which [<sup>11</sup>C]propionyl chloride was reacted with 5-hydroxy-2-[<i>N</i>-(2-phenethyl)amino]tetralin and followed by LiAlH<sub>4</sub> reduction, with a radiochemical yield of 5–10% (based on [<sup>11</sup>C]CO<sub>2</sub> at the end of bombardment) and an average specific activity of 9–37 GBq/μmol (250–1,000 mCi/μmol) at end of synthesis after purification by high-performance liquid chromatography. [<sup>11</sup>C]Propionyl chloride was prepared by reacting [<sup>11</sup>C]CO<sub>2</sub> with ethylmagnesium bromide, followed by reaction with phthaloyl chloride. Total synthesis time was 60–75 min.</p></div><div id="PPHT11C.In_Vitro_Studies_Tes"><h2 id="_PPHT11C_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%20PPHT%20and%20in%20vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>In a binding study of dopamine receptors in membranes of the rat striatum with [<sup>3</sup>H]spiperone, PPHT had an IC<sub>50</sub> of 0.65 nM (<a class="bk_pop" href="#PPHT11C.REF.15">15</a>). <i>In vitro</i> autoradiography studies of rat brain slices indicated selective binding of [<sup>11</sup>C]PPHT to the striata, which was completely inhibited by co-incubation with 10 μM sulpiride. Gpp(NH)p decreased the striatum/cerebellum ratio from 2.0 to 1.1 by converting the high-affinity state to the low-affinity state. There was significant nonspecific binding in the cortex.</p></div><div id="PPHT11C.Animal_Studies"><h2 id="_PPHT11C_Animal_Studies_">Animal Studies</h2><div id="PPHT11C.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20PPHT%20and%20rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Biodistribution studies in rats showed a marked accumulation of the tracer in the striata within the first 2 min [1.2% injected dose per gram (ID/g)], followed by a decrease of radioactivity to 0.5% ID/g at 30 min and 0.2% ID/g at 60 min (<a class="bk_pop" href="#PPHT11C.REF.16">16</a>). The striatum/cerebellum ratios were 1.27 at 2 min, 1.52 at 30 min, and 1.42 at 60 min after injection. Haloperidol pretreatment (1 mg/kg, 15 min before radiotracer injection) effectively reduced specific binding of [<sup>11</sup>C]PPHT to the striatum with some residual binding relative to the cerebellum at 30 min. Little inhibition was seen in the cerebellum. [<sup>11</sup>C]PPHT thus displays uptake and washout kinetics characteristic of reversible radiotracers.</p></div><div id="PPHT11C.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20PPHT%20and%20%28dog%20or%20pig%20or%20sheep%20or%20rabbit%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="PPHT11C.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20PPHT%20and%20monkey" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Mukherjee et al. (<a class="bk_pop" href="#PPHT11C.REF.16">16</a>) showed selective accumulation (0.03% ID/ml) in the striata of two rhesus monkeys with striatum/cerebellum ratios of 1.5 at 30 min and 1.4 at 60 min after injection of 26–93 MBq (0.7–2.5 mCi) of [<sup>11</sup>C]PPHT. Thalamus/cerebellum ratios were 1.3 at 30 min and 1.2 at 60 min. However, there was a substantial nonspecific binding in the cortex and cerebellum. The authors suggested that the use of the more active <i>S</i>-isomer may provide higher striatum/cerebellum and thalamus/cerebellum ratios.</p></div></div><div id="PPHT11C.Human_Studies"><h2 id="_PPHT11C_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20PPHT%20and%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No relevant publication is currently available.</p></div><div id="PPHT11C.references"><h2 id="_PPHT11C_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="PPHT11C.REF.1">Carbon M. , Ghilardi M.F. , Feigin A. , Fukuda M. , Silvestri G. , Mentis M.J. , Ghez C. , Moeller J.R. , Eidelberg D. Learning networks in health and Parkinson's disease: reproducibility and treatment effects. <span><span class="ref-journal">Hum Brain Mapp. </span>2003;<span class="ref-vol">19</span>(3):197–211.</span> [<a href="/pmc/articles/PMC6871830/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC6871830</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/12811735" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12811735</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="PPHT11C.REF.2">Chesselet M.F. , Delfs J.M. Basal ganglia and movement disorders: an update. <span><span class="ref-journal">Trends Neurosci. </span>1996;<span class="ref-vol">19</span>(10):417–22.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/8888518" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 8888518</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="PPHT11C.REF.3">Seeman P. , Bzowej N.H. , Guan H.C. , Bergeron C. , Reynolds G.P. , Bird E.D. , Riederer P. , Jellinger K. , Tourtellotte W.W. Human brain D1 and D2 dopamine receptors in schizophrenia, Alzheimer's, Parkinson's, and Huntington's diseases. <span><span class="ref-journal">Neuropsychopharmacology. </span>1987;<span class="ref-vol">1</span>(1):5–15.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/2908095" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 2908095</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="PPHT11C.REF.4">Stoof J.C. , Kebabian J.W. Two dopamine receptors: biochemistry, physiology and pharmacology. <span><span class="ref-journal">Life Sci. </span>1984;<span class="ref-vol">35</span>(23):2281–96.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/6390056" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 6390056</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="PPHT11C.REF.5">Sunahara R.K. , Guan H.C. , O'Dowd B.F. , Seeman P. , Laurier L.G. , Ng G. , George S.R. , Torchia J. , Van Tol H.H. , Niznik H.B. Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1. <span><span class="ref-journal">Nature. </span>1991;<span class="ref-vol">350</span>(6319):614–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/1826762" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 1826762</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="PPHT11C.REF.6">Sibley D.R. , De Lean A. , Creese I. Anterior pituitary dopamine receptors. Demonstration of interconvertible high and low affinity states of the D-2 dopamine receptor. <span><span class="ref-journal">J Biol Chem. </span>1982;<span class="ref-vol">257</span>(11):6351–61.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/6176582" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 6176582</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="PPHT11C.REF.7">Gehlert D.R. , Wamsley J.K. Autoradiographic localization of [3H]sulpiride binding sites in the rat brain. <span><span class="ref-journal">Eur J Pharmacol. </span>1984;<span class="ref-vol">98</span>(2):311–2.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/6714315" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 6714315</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="PPHT11C.REF.8">Lidow M.S. , Goldman-Rakic P.S. , Rakic P. , Innis R.B. Dopamine D2 receptors in the cerebral cortex: distribution and pharmacological characterization with [3H]raclopride. <span><span class="ref-journal">Proc Natl Acad Sci U S A. </span>1989;<span class="ref-vol">86</span>(16):6412–6.</span> [<a href="/pmc/articles/PMC297850/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC297850</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/2548214" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 2548214</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="PPHT11C.REF.9">Brucke T. , Tsai Y.F. , McLellan C. , Singhanyom W. , Kung H.F. , Cohen R.M. , Chiueh C.C. In vitro binding properties and autoradiographic imaging of 3-iodobenzamide ([125I]-IBZM): a potential imaging ligand for D-2 dopamine receptors in SPECT. <span><span class="ref-journal">Life Sci. </span>1988;<span class="ref-vol">42</span>(21):2097–104.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/3260318" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 3260318</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="PPHT11C.REF.10">Kessler R.M. , Ansari M.S. , Schmidt D.E. , de Paulis T. , Clanton J.A. , Innis R. , al-Tikriti M. , Manning R.G. , Gillespie D. High affinity dopamine D2 receptor radioligands. 2. [125I]epidepride, a potent and specific radioligand for the characterization of striatal and extrastriatal dopamine D2 receptors. <span><span class="ref-journal">Life Sci. </span>1991;<span class="ref-vol">49</span>(8):617–28.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/1830917" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 1830917</span></a>]</div></dd><dt>11.</dt><dd><div class="bk_ref" id="PPHT11C.REF.11">Mukherjee J. , Yang Z.Y. , Das M.K. , Brown T. Fluorinated benzamide neuroleptics--III. Development of (S)-N-[(1-allyl-2-pyrrolidinyl)methyl]-5-(3-[18F]fluoropropyl)-2, 3-dimethoxybenzamide as an improved dopamine D-2 receptor tracer. <span><span class="ref-journal">Nucl Med Biol. </span>1995;<span class="ref-vol">22</span>(3):283–96.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/7627142" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 7627142</span></a>]</div></dd><dt>12.</dt><dd><div class="bk_ref" id="PPHT11C.REF.12">Grunder G. , Landvogt C. , Vernaleken I. , Buchholz H.G. , Ondracek J. , Siessmeier T. , Hartter S. , Schreckenberger M. , Stoeter P. , Hiemke C. , Rosch F. , Wong D.F. , Bartenstein P. <span><span class="ref-journal">and , The Striatal and Extrastriatal D2/D3 Receptor-Binding Profile of Clozapine in Patients with Schizophrenia. Neuropsychopharmacology. </span>2005</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16237387" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16237387</span></a>]</div></dd><dt>13.</dt><dd><div class="bk_ref" id="PPHT11C.REF.13">Mukherjee J. , Christian B.T. , Narayanan T.K. , Shi B. , Collins D. Measurement of d-amphetamine-induced effects on the binding of dopamine D-2/D-3 receptor radioligand, 18F-fallypride in extrastriatal brain regions in non-human primates using PET. <span><span class="ref-journal">Brain Res. </span>2005;<span class="ref-vol">1032</span>(1-2):77–84.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15680944" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15680944</span></a>]</div></dd><dt>14.</dt><dd><div class="bk_ref" id="PPHT11C.REF.14">Kessler R.M. , Ansari M.S. , Riccardi P. , Li R. , Jayathilake K. , Dawant B. , Meltzer H.Y. Occupancy of striatal and extrastriatal dopamine d(2)/d(3) receptors by olanzapine and haloperidol. <span><span class="ref-journal">Neuropsychopharmacology. </span>2005;<span class="ref-vol">30</span>(12):2283–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16123775" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16123775</span></a>]</div></dd><dt>15.</dt><dd><div class="bk_ref" id="PPHT11C.REF.15">Shi B. , Narayanan T.K. , Yang Z.Y. , Christian B.T. , Mukherjee J. Radiosynthesis and in vitro evaluation of 2-(N-alkyl-N-1'-11C-propyl)amino-5-hydroxytetralin analogs as high affinity agonists for dopamine D-2 receptors. <span><span class="ref-journal">Nucl Med Biol. </span>1999;<span class="ref-vol">26</span>(7):725–35.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10628551" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10628551</span></a>]</div></dd><dt>16.</dt><dd><div class="bk_ref" id="PPHT11C.REF.16">Mukherjee J. , Narayanan T.K. , Christian B.T. , Shi B. , Yang Z.Y. Binding characteristics of high-affinity dopamine D2/D3 receptor agonists, 11C-PPHT and 11C-ZYY-339 in rodents and imaging in non-human primates by PET. <span><span class="ref-journal">Synapse. </span>2004;<span class="ref-vol">54</span>(2):83–91.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15352133" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15352133</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: NBK23086</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20641291" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20641291</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/ZYY-339-11C/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/CP99994C11/" 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/NBK23086/?report=reader">PubReader</a></li><li><a href="/books/NBK23086/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23086" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23086" style="display:none" title="Cite this Page"><div class="bk_tt">Leung K. (+/-)-2-(N-Phenethyl-N-1'-[11C]propyl)amino-5-hydroxytetralin. 2006 Aug 16 [Updated 2008 Feb 4]. 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/NBK23086/pdf/Bookshelf_NBK23086.pdf">PDF version of this page</a> (138K)</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="#PPHT11C.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#PPHT11C.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#PPHT11C.In_Vitro_Studies_Tes" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#PPHT11C.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#PPHT11C.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#PPHT11C.references" ref="log$=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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value="Nanobubbles">Nanobubbles</option></optgroup><optgroup label="X-ray and CT agents"><option value="(Bismuth OR Bi)">Bismuth</option><option value="(Gold OR Au)">Gold</option><option value="Iodine">Iodine</option></optgroup></select></div></div><div class="clearfix"><label for="agent">Agent Category:</label><div class="right"><select name="agent" id="agent" style="width:200px"><option value="" selected="selected">Any</option><option value="(antibody OR trastuzumab OR immunoglobulin)">Antibodies</option><option value="(bacteria OR bacteriophage OR coli)">Bacteria</option><option value="cell">Cells</option><option value="(compound OR "amino acid" OR "folic acid" OR "cage molecule" OR carbohydrate OR copolymers OR polymer OR "small molecule" OR macromolecule OR triiodobenzoate OR estradiol OR glycosaminoglycan)">Compounds</option><option value="ligand">Ligands</option><option value="(lipid OR liposome OR liposomes">Lipids</option><option value="metal">Metal</option><option value="(nanoparticle OR nanoparticles OR nanotubes OR "iron oxide")">Nanoparticles</option><option value="(siRNA OR "nucleic acid" OR oligonucleotide)">Nucleic acids</option><option value="peptide">Peptides</option><option value="polyeptide">Polyeptides</option><option value="(protein OR albumin OR chemokin OR immunoprotein OR luciferase OR albumin)">Proteins</option><option value="(virus OR adenovirus)">Viruses</option></select></div></div><div class="clearfix"><label for="target">Target Category:</label><div class="right"><select name="target" id="target" style="width:200px"><option value="" selected="selected">Any</option><option value="acceptor">Acceptors</option><option value=""adhesion molecule"">Adhesion molecules</option><option value="(antigen OR antibody-antigen)">Antigens</option><option value="(enzyme OR enzymes OR enzyme-substrate)">Enzymes</option><option value="(lipids OR lipophilic cation)">Lipids</option><option value="(receptor OR receptors OR receptor-ligand OR 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xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> (+/-)-2-(N-Cyclohexylethyl-N-[(11)C]propyl)amino-5-hydroxytetralin.</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-(N-Cyclohexylethyl-N-[(11)C]propyl)amino-5-hydroxytetralin.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Leung K. </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/20641325" 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