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<script type="text/javascript" src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/jr.boots.min.js"> </script><title>[11C](+)-4-N-Propyl-,3,4a,5,6,10b-hexahydro-2H-naphth[1,2-b][1,4]-oxazin-9-ol - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf</title>
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<meta name="citation_inbook_title" content="Molecular Imaging and Contrast Agent Database (MICAD) [Internet]">
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<meta name="citation_title" content="[11C](+)-4-N-Propyl-,3,4a,5,6,10b-hexahydro-2H-naphth[1,2-b][1,4]-oxazin-9-ol">
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<meta name="citation_publisher" content="National Center for Biotechnology Information (US)">
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<meta name="citation_date" content="2011/10/06">
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<meta name="citation_author" content="Kam Leung">
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<meta name="DC.Title" content="[11C](+)-4-N-Propyl-,3,4a,5,6,10b-hexahydro-2H-naphth[1,2-b][1,4]-oxazin-9-ol">
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<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 subtypes are classified into two subfamilies: D1-like (D1 and D5) and D2-like (D2, D3, and D4) dopamine receptors. D1-like and D2-like receptors exert synergistic as well as opposite effects at both the biochemical and overall system level. A great majority of striatal D1 and D2 receptors are localized postsynaptically on caudate-putamen neurons and to a lesser extent presynaptically on nigrostriatal axons.">
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<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 subtypes are classified into two subfamilies: D1-like (D1 and D5) and D2-like (D2, D3, and D4) dopamine receptors. D1-like and D2-like receptors exert synergistic as well as opposite effects at both the biochemical and overall system level. A great majority of striatal D1 and D2 receptors are localized postsynaptically on caudate-putamen neurons and to a lesser extent presynaptically on nigrostriatal axons.">
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id="jr-fip-info-p"><a id="jr-fip-prev" class="wsprkl btn" title="Jump to previuos match">◀</a><button id="jr-fip-matches">no matches yet</button><a id="jr-fip-next" class="wsprkl btn" title="Jump to next match">▶</a></nav></nav></div><div id="jr-epub-interstitial" class="hidden"></div><div id="jr-content"><article data-type="main"><div class="main-content lit-style" itemscope="itemscope" itemtype="http://schema.org/CreativeWork"><div class="meta-content fm-sec"><div class="fm-sec"><h1 id="_NBK23408_"><span class="title" itemprop="name">[<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</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">[<sup>11</sup>C](+)-PHNO</div><p class="contribs">Leung K.</p><p class="fm-aai"><a href="#_NBK23408_pubdet_">Publication Details</a></p></div></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div class="iconblock whole_rhythm clearfix ten_col table-wrap" id="figPHNO11CTncchemicalname11c4npropyl3"><a href="/books/NBK23408/table/PHNO11C.T.nc_chemical_name11c4npropyl3/?report=objectonly" target="object" title="Table" class="img_link icnblk_img" rid-ob="figobPHNO11CTncchemicalname11c4npropyl3"><img class="small-thumb" src="/corehtml/pmc/css/bookshelf/2.26/img/table-icon.gif" alt="Table Icon" /></a><div class="icnblk_cntnt"><h4 id="PHNO11C.T.nc_chemical_name11c4npropyl3"><a href="/books/NBK23408/table/PHNO11C.T.nc_chemical_name11c4npropyl3/?report=objectonly" target="object" rid-ob="figobPHNO11CTncchemicalname11c4npropyl3">Table</a></h4><p class="float-caption no_bottom_margin">
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<i>In vitro</i>
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Rodents
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</p></div></div><div id="PHNO11C.Background"><h2 id="_PHNO11C_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20PHNO" 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="bibr" href="#PHNO11C.REF.1" rid="PHNO11C.REF.1 PHNO11C.REF.2">1, 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="bibr" href="#PHNO11C.REF.3" rid="PHNO11C.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="bibr" href="#PHNO11C.REF.4" rid="PHNO11C.REF.4">4</a>). These five 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>) dopamine receptors. 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 level. A great majority of 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 and exist in high- and low-affinity states, with respect to agonist binding. The two states are interconvertible. The high-affinity state is coupled to G-proteins, whereas the low-affinity state is 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="bibr" href="#PHNO11C.REF.5" rid="PHNO11C.REF.5">5</a>). Under physiologic conditions, dopamine is expected to bind predominately to the high-affinity state, which is ~50% occupied by 10 nM dopamine. The high-affinity state has been suggested to be the functional form of the dopamine receptors.</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 studies of extrastriatal D<sub>2</sub> receptors difficult (<a class="bibr" href="#PHNO11C.REF.6" rid="PHNO11C.REF.6 PHNO11C.REF.7 PHNO11C.REF.8">6-8</a>). In binding studies, [<sup>123</sup>I]-labeled 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="bibr" href="#PHNO11C.REF.9" rid="PHNO11C.REF.9">9</a>). Epidepride has 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/?report=reader">[<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="bibr" href="#PHNO11C.REF.10" rid="PHNO11C.REF.10">10</a>), and in positron emission tomography (PET) <i>in vivo</i> studies (<a class="bibr" href="#PHNO11C.REF.11" rid="PHNO11C.REF.11 PHNO11C.REF.12 PHNO11C.REF.13">11-13</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>-Propyl-norapomorphine (NPA), an agonist of the D<sub>2/3</sub> receptors, was reported to have <i>K</i><sub>high</sub> and <i>K</i><sub>low</sub> values of 0.07-0.4 and 20-200 nM, respectively (<a class="bibr" href="#PHNO11C.REF.5" rid="PHNO11C.REF.5 PHNO11C.REF.14 PHNO11C.REF.15">5, 14, 15</a>). This provides a >50-fold selectivity for the high-affinity over the low-affinity receptors. NPA has good affinity (<i>K</i><sub>i</sub> = 0.3 nM) for D<sub>3</sub> receptors but not other neurotransmitters (<a class="bibr" href="#PHNO11C.REF.16" rid="PHNO11C.REF.16">16</a>). <a href="/books/n/micad/NPA11C/?report=reader">[<sup>11</sup>C]NPA</a> is being developed as a PET agent for the non-invasive study of the high-affinity state of the D<sub>2/3</sub> receptors in the brain.</p><p> (+)-4-Propyl-3,4,4a,5,6,10b-hexahydro-2<i>H</i>-naphtho[1,2-<i>b</i>][1,4]oxazin-9-ol (PHNO) is an agonist of the D<sub>2</sub> receptors with a reported <i>K</i><sub>d</sub> of 0.56 nM in the canine striatum and a >10,000-fold selectivity for D<sub>2</sub> over D<sub>1</sub> receptors (<a class="bibr" href="#PHNO11C.REF.17" rid="PHNO11C.REF.17">17</a>). PHNO has a high affinity for human cloned D<sub>2</sub> (<i>K</i><sub>i</sub> = 8.5 nM) and D<sub>3</sub> (<i>K</i><sub>i</sub> = 0.16 nM) receptors (<a class="bibr" href="#PHNO11C.REF.18" rid="PHNO11C.REF.18">18</a>). [<sup>11</sup>C]PHNO showed robust specific binding in the striatum of rodents with insensitivity to displacement by D<sub>1</sub>, norepinephrine, or serotonin ligands (<a class="bibr" href="#PHNO11C.REF.19" rid="PHNO11C.REF.19">19</a>). [<sup>11</sup>C]PHNO is being developed as a PET agent for the non-invasive study of the high-affinity state of the D<sub>2/3</sub> receptors in the brain.</p><p>.</p><div id="PHNO11C.Related_Resource_Links"><h3>Related Resource Links:</h3><ul><li class="half_rhythm"><div>Chapters in MICAD (<a href="/sites/entrez?Db=books&Cmd=DetailsSearch&Term=dopamine%20(receptors%20OR%20receptor)+%20AND+Table+AND+micad%5Bbook%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Dopamine receptors</a>)</div></li><li class="half_rhythm"><div>Gene information in NCBI (<a href="/gene/1813" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">D<sub>2</sub> receptor,</a><a href="/gene/1814" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">D<sub>3</sub> receptor</a>)</div></li><li class="half_rhythm"><div>Articles in Online Mendelian Inheritance in Man (OMIM) (<a href="/omim/126450" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">D<sub>2</sub> receptor</a>, <a href="/omim/126451" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">D<sub>3</sub> receptor</a>)</div></li><li class="half_rhythm"><div>Clinical trials (<a href="http://www.clinicaltrials.gov/ct2/results?term=dopamine+receptor" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Dopamine receptors</a>)</div></li><li class="half_rhythm"><div>Drug information in Food and Drug Administration (<a href="http://google2.fda.gov/search?q=dopamine+receptor&client=FDAgov&site=FDAgov&lr=&proxystylesheet=FDAgov&output=xml_no_dtd&getfields=*&x=6&y=12" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Dopamine receptors</a>)</div></li></ul></div></div><div id="PHNO11C.Synthesis"><h2 id="_PHNO11C_Synthesis_">Synthesis</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20PHNO%20and%20synthesis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Wilson et al. (<a class="bibr" href="#PHNO11C.REF.19" rid="PHNO11C.REF.19">19</a>) reported a one-pot synthesis of [<sup>11</sup>C]PHNO in which [<sup>11</sup>C]propionyl chloride was reacted with (+)-3,4,4a,5,6,10b-hexahydro-2<i>H</i>-naphtho[1,2-<i>b</i>][1,4]oxazin-9-ol followed by LiAlH<sub>4</sub> reduction, with an average radiochemical yield of 10% (based on [<sup>11</sup>C]CO<sub>2</sub>, uncorrected, at the end of synthesis). Specific activities were 33-67 GBq/μmol (900-1,800 mCi/μmol at end of synthesis) after high-performance liquid chromatographic purification, with radiochemical purities >99%. [<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. The total synthesis time was 40 min.</p></div><div id="PHNO11C.In_Vitro_Studies_Testing_in_Cell"><h2 id="_PHNO11C_In_Vitro_Studies_Testing_in_Cell_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20PHNO%20and%20in%20vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>In studies of binding to dopamine receptors in membranes of canine striatum, [<sup>3</sup>H]PHNO had an average <i>K</i><sub>d</sub> of 0.56 ± 0.08 nM and a <i>B</i><sub>max</sub> of 30.1 ± 2.0 pmol/g tissue (<a class="bibr" href="#PHNO11C.REF.20" rid="PHNO11C.REF.20">20</a>). Guanilylimidodiphosphate significantly reduced the density of [<sup>3</sup>H]PHNO binding sites, suggesting that [<sup>3</sup>H]PHNO was binding mainly to the high-affinity state of dopamine D<sub>2</sub> receptors and not to D<sub>3</sub> receptors.</p></div><div id="PHNO11C.Animal_Studies"><h2 id="_PHNO11C_Animal_Studies_">Animal Studies</h2><div id="PHNO11C.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20PHNO%20and%20rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Biodistribution studies in rats by Wilson et al. (<a class="bibr" href="#PHNO11C.REF.19" rid="PHNO11C.REF.19">19</a>) showed high accumulation of radioactivity in the striatum (2% of injected dose(ID)/g) within the first 5 min after injection, followed by a gradual decrease of radioactivity to ~0.7% ID/g at 60 min. Accumulation (~1% ID/g) in all other brain regions was similar to that in the cerebellum at 5 min and was only 0.2% ID/g at 60 min. The striatum specific binding ratios (cerebellum as a reference) were 1.1, 2.8, 3.9, and 4.6 at 5, 15, 30, and 60 min after injection, respectively. Haloperidol (D<sub>2</sub>), raclopride (D<sub>2</sub>), PHNO, and RTI-32 (dopamine transporter) pretreatment effectively blocked specific binding of [<sup>11</sup>C]PHNO to the striatum by 73-95%. On the other hand, WAY 100635 (5-HT<sub>1A</sub>), SCH 23390 (D<sub>1</sub>), clonidine (α<sub>2</sub>), and MK-912 (α<sub>2A</sub>) showed little inhibition. Amphetamine (a dopamine releaser) pretreatment revealed dose-dependent inhibition of [<sup>11</sup>C]PHNO binding to the striatum, indicating that [<sup>11</sup>C]PHNO binding is sensitive to endogenous dopamine levels in the striatum. At 40 min post injection, 26% of [<sup>11</sup>C]PHNO radioactivity remained intact in the plasma, with 74% as polar metabolites. However, >98% of the radioactivity in the rat brain was intact [<sup>11</sup>C]PHNO, suggesting that the polar metabolites cannot cross the blood-brain barrier. [<sup>11</sup>C]PHNO thus displays uptake and washout kinetics characteristic of reversible radiotracers as well as excellent selectivity toward D<sub>2/3</sub> receptors.</p></div><div id="PHNO11C.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20PHNO%20and%20%28pig%20or%20dog%20or%20sheep%20or%20rabbit%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Ginovart et al. (<a class="bibr" href="#PHNO11C.REF.21" rid="PHNO11C.REF.21">21</a>) reported on [<sup>11</sup>C]PHNO PET study in cats. [<sup>11</sup>C]PHNO displayed high uptake in the striatum with a mean striatal binding potential (BP) of 3.95 ± 0.85. Pretreatment with the specific antagonists SCH 23390 (D<sub>1</sub> antagonist), raclopride (D<sub>2</sub> antagonist), haloperidol (D<sub>2</sub> antagonist), and SB-277011 (D<sub>3</sub> antagonist) indicated that [<sup>11</sup>C]PHNO binding in the striatum is specific to D<sub>2</sub> receptors because raclopride and haloperidol showed >89% inhibition, whereas SCH 23390 and SB-277011 showed no inhibition. The BP of [<sup>11</sup>C]PHNO in the striatum was 2.5-fold higher than that measured with [<sup>11</sup>C]NPA. The BP of [<sup>11</sup>C]raclopride was reduced by 13, 39, and 57% after amphetamine doses of 0.1, 0.5, and 2.0 mg/kg, respectively. The BP of [<sup>11</sup>C]PHNO was reduced by 21, 67, and 83% after amphetamine doses of 0.1, 0.5, and 2.0 mg/kg, respectively. Amphetamine induced up to 83 ± 4% inhibition of the [<sup>11</sup>C]PHNO BP, but only up to 57 ± 8% inhibition of the [<sup>11</sup>C]raclopride BP. Thus, [<sup>11</sup>C]PHNO was more sensitive to the dopamine-releasing effect of amphetamine than [<sup>11</sup>C]raclopride. Because raclopride binds to receptors in both the high- and low-affinity states and dopamine binds with high affinity mainly to receptors in the high-affinity state, the percentage reduction is greater when an agonist is used than when an antagonist is used. This large proportion of high-affinity sites might explain the vulnerability of D<sub>2</sub> radiotracers to competition by endogenous dopamine and is consistent with the reported <i>in vivo</i> binding of the agonist radiotracer [<sup>11</sup>C]PHNO. Scatchard analyses of [<sup>11</sup>C]PHNO and [<sup>11</sup>C]raclopride binding in two cats revealed that the <i>B</i><sub>max</sub> values obtained with the agonist (29.6 and 32.9 pmol/ml) were similar to those obtained with the antagonist (30.6 and 33.4 pmol/ml).</p></div><div id="PHNO11C.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20PHNO%20and%20%28primate%20not%20human%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div></div><div id="PHNO11C.Human_Studies"><h2 id="_PHNO11C_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%20PHNO%20and%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Willeit et al. (<a class="bibr" href="#PHNO11C.REF.22" rid="PHNO11C.REF.22">22</a>) performed preliminary PET studies of two male and two female healthy volunteers with [<sup>11</sup>C]PHNO under baseline conditions and after haloperidol pretreatment. The simplified reference tissue method of Lammertsma and Hume (<a class="bibr" href="#PHNO11C.REF.23" rid="PHNO11C.REF.23">23</a>) was used to derive BPs for each region of interest. The [<sup>11</sup>C]PHNO BPs in the caudate, putamen, and globus pallidus were 3.00 ± 0.4, 3.10 ± 0.2, and 4.17 ± 1.2, respectively. Small but detectable binding was identified in the substantia nigra/ventral tegmental area. Preliminary test-retest data in two subjects suggested that the BP estimates were reliable. Pretreatment of two subjects with haloperidol (2 mg) reduced the BPs in the caudate, putamen, and globus pallidus by 14-49% with no detectable changes in the cerebellum. [<sup>11</sup>C]Raclopride binding was studied in two of the subjects. The [<sup>11</sup>C]raclopride BPs in the caudate, putamen, and globus pallidus were 3.3 ± 0.7, 4.1 ± 0.4, and 1.4 ± 0.2, respectively. [<sup>11</sup>C]PHNO binding compared with [<sup>11</sup>C]raclopride binding was lower in the caudate (–8.8%) and putamen (–23.5%) but higher in the globus pallidus (+200%). [<sup>11</sup>C]PHNO showed favorable kinetics and may allow reliable quantitation of high-affinity D<sub>2/3</sub> receptors in the brain.</p></div><div id="PHNO11C.References"><h2 id="_PHNO11C_References_">References</h2><dl class="temp-labeled-list"><dl class="bkr_refwrap"><dt>1.</dt><dd><div class="bk_ref" id="PHNO11C.REF.1">Carbon M., Ghilardi M.F., Feigin A., Fukuda M., Silvestri G., Mentis M.J., Ghez C., Moeller J.R., Eidelberg D.
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<em>Learning networks in health and Parkinson's disease: reproducibility and treatment effects.</em>
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<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></dl><dl class="bkr_refwrap"><dt>2.</dt><dd><div class="bk_ref" id="PHNO11C.REF.2">Chesselet M.F., Delfs J.M.
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<em>Basal ganglia and movement disorders: an update.</em>
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<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></dl><dl class="bkr_refwrap"><dt>3.</dt><dd><div class="bk_ref" id="PHNO11C.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.
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<em>Human brain D1 and D2 dopamine receptors in schizophrenia, Alzheimer's, Parkinson's, and Huntington's diseases.</em>
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<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></dl><dl class="bkr_refwrap"><dt>4.</dt><dd><div class="bk_ref" id="PHNO11C.REF.4">Stoof J.C., Kebabian J.W.
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<em>Two dopamine receptors: biochemistry, physiology and pharmacology.</em>
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<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></dl><dl class="bkr_refwrap"><dt>5.</dt><dd><div class="bk_ref" id="PHNO11C.REF.5">George S.R., Watanabe M., Di Paolo T., Falardeau P., Labrie F., Seeman P.
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<em>The functional state of the dopamine receptor in the anterior pituitary is in the high affinity form.</em>
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|
<span><span class="ref-journal">Endocrinology. </span>1985;<span class="ref-vol">117</span>(2):690–7.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/4017954" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 4017954</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>6.</dt><dd><div class="bk_ref" id="PHNO11C.REF.6">Gehlert D.R., Wamsley J.K.
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|
<em>Autoradiographic localization of [3H]sulpiride binding sites in the rat brain.</em>
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|
<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></dl><dl class="bkr_refwrap"><dt>7.</dt><dd><div class="bk_ref" id="PHNO11C.REF.7">Lidow M.S., Goldman-Rakic P.S., Rakic P., Innis R.B.
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<em>Dopamine D2 receptors in the cerebral cortex: distribution and pharmacological characterization with [3H]raclopride.</em>
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|
<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></dl><dl class="bkr_refwrap"><dt>8.</dt><dd><div class="bk_ref" id="PHNO11C.REF.8">Brucke T., Tsai Y.F., McLellan C., Singhanyom W., Kung H.F., Cohen R.M., Chiueh C.C.
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|
<em>In vitro binding properties and autoradiographic imaging of 3-iodobenzamide ([125I]-IBZM): a potential imaging ligand for D-2 dopamine receptors in SPECT.</em>
|
|
<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></dl><dl class="bkr_refwrap"><dt>9.</dt><dd><div class="bk_ref" id="PHNO11C.REF.9">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.
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<em>High affinity dopamine D2 receptor radioligands. 2. [125I]epidepride, a potent and specific radioligand for the characterization of striatal and extrastriatal dopamine D2 receptors.</em>
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<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></dl><dl class="bkr_refwrap"><dt>10.</dt><dd><div class="bk_ref" id="PHNO11C.REF.10">Mukherjee J., Yang Z.Y., Das M.K., Brown T.
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<em>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.</em>
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<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></dl><dl class="bkr_refwrap"><dt>11.</dt><dd><div class="bk_ref" id="PHNO11C.REF.11">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.
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<em>The striatal and extrastriatal D2/D3 receptor-binding profile of clozapine in patients with schizophrenia.</em>
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<span><span class="ref-journal">Neuropsychopharmacology. </span>2006;<span class="ref-vol">31</span>(5):1027–35.</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></dl><dl class="bkr_refwrap"><dt>12.</dt><dd><div class="bk_ref" id="PHNO11C.REF.12">Mukherjee J., Christian B.T., Narayanan T.K., Shi B., Collins D.
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<em>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.</em>
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<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></dl><dl class="bkr_refwrap"><dt>13.</dt><dd><div class="bk_ref" id="PHNO11C.REF.13">Riccardi P., Li R., Ansari M.S., Zald D., Park S., Dawant B., Anderson S., Doop M., Woodward N., Schoenberg E., Schmidt D., Baldwin R., Kessler R.
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<em>Amphetamine-induced displacement of [18F] fallypride in striatum and extrastriatal regions in humans.</em>
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<span><span class="ref-journal">Neuropsychopharmacology. </span>2006;<span class="ref-vol">31</span>(5):1016–26.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16237395" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16237395</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>14.</dt><dd><div class="bk_ref" id="PHNO11C.REF.14">Gardner B., Strange P.G.
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<em>Agonist action at D2(long) dopamine receptors: ligand binding and functional assays.</em>
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<span><span class="ref-journal">Br J Pharmacol. </span>1998;<span class="ref-vol">124</span>(5):978–84.</span> [<a href="/pmc/articles/PMC1565475/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC1565475</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/9692784" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9692784</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>15.</dt><dd><div class="bk_ref" id="PHNO11C.REF.15">Lahti R.A., Mutin A., Cochrane E.V., Tepper P.G., Dijkstra D., Wikstrom H., Tamminga C.A.
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<em>Affinities and intrinsic activities of dopamine receptor agonists for the hD21 and hD4.4 receptors.</em>
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<span><span class="ref-journal">Eur J Pharmacol. </span>1996;<span class="ref-vol">301</span>(1-3):R11–3.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/8773470" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 8773470</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>16.</dt><dd><div class="bk_ref" id="PHNO11C.REF.16">Neumeyer J.L., Neustadt B.R., Oh K.H., Weinhardt K.K., Boyce C.B., Rosenberg F.J., Teiger D.G.
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<em>Aporphines. 8. Total synthesis and pharmacological evaluation of (plus or minus)-apomorphine, (plus or minus)-apocodeine, (plus or minus)-N-n-propylnorapomorphine, and (plus or minus)-N-n-propylnorapocodeine.</em>
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<span><span class="ref-journal">J Med Chem. </span>1973;<span class="ref-vol">16</span>(11):1223–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/4201182" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 4201182</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>17.</dt><dd><div class="bk_ref" id="PHNO11C.REF.17">Seeman P., Ulpian C., Larsen R.D., Anderson P.S.
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<em>Dopamine receptors labelled by PHNO.</em>
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<span><span class="ref-journal">Synapse. </span>1993;<span class="ref-vol">14</span>(4):254–62.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/7902615" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 7902615</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>18.</dt><dd><div class="bk_ref" id="PHNO11C.REF.18">Freedman S.B., Patel S., Marwood R., Emms F., Seabrook G.R., Knowles M.R., McAllister G.
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<em>Expression and pharmacological characterization of the human D3 dopamine receptor.</em>
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<span><span class="ref-journal">J Pharmacol Exp Ther. </span>1994;<span class="ref-vol">268</span>(1):417–26.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/8301582" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 8301582</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>19.</dt><dd><div class="bk_ref" id="PHNO11C.REF.19">Wilson A.A., McCormick P., Kapur S., Willeit M., Garcia A., Hussey D., Houle S., Seeman P., Ginovart N.
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<em>Radiosynthesis and evaluation of [11C]-(+)-4-propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazin-9 -ol as a potential radiotracer for in vivo imaging of the dopamine D2 high-affinity state with positron emission tomography.</em>
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<span><span class="ref-journal">J Med Chem. </span>2005;<span class="ref-vol">48</span>(12):4153–60.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15943487" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15943487</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>20.</dt><dd><div class="bk_ref" id="PHNO11C.REF.20">Nobrega J.N., Seeman P.
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<em>Dopamine D2 receptors mapped in rat brain with [3H](+)PHNO.</em>
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<span><span class="ref-journal">Synapse. </span>1994;<span class="ref-vol">17</span>(3):167–72.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/7974199" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 7974199</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>21.</dt><dd><div class="bk_ref" id="PHNO11C.REF.21">Ginovart N., Galineau L., Willeit M., Mizrahi R., Bloomfield P.M., Seeman P., Houle S., Kapur S., Wilson A.A.
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<em>Binding characteristics and sensitivity to endogenous dopamine of [C]-(+)-PHNO, a new agonist radiotracer for imaging the high-affinity state of D receptors in vivo using positron emission tomography.</em>
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<span><span class="ref-journal">J Neurochem. </span>2006;<span class="ref-vol">97</span>(4):1089–103.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16606355" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16606355</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>22.</dt><dd><div class="bk_ref" id="PHNO11C.REF.22">Willeit M., Ginovart N., Kapur S., Houle S., Hussey D., Seeman P., Wilson A.A.
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<em>High-affinity states of human brain dopamine D2/3 receptors imaged by the agonist [11C]-(+)-PHNO.</em>
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<span><span class="ref-journal">Biol Psychiatry. </span>2006;<span class="ref-vol">59</span>(5):389–94.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16373068" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16373068</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>23.</dt><dd><div class="bk_ref" id="PHNO11C.REF.23">Lammertsma A.A., Hume S.P.
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<em>Simplified reference tissue model for PET receptor studies.</em>
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<span><span class="ref-journal">Neuroimage. </span>1996;<span class="ref-vol">4</span>(3 Pt 1):153–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9345505" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9345505</span></a>]</div></dd></dl></dl></div><div id="bk_toc_contnr"></div></div></div><div class="fm-sec"><h2 id="_NBK23408_pubdet_">Publication Details</h2><h3>Author Information and Affiliations</h3><div class="contrib half_rhythm"><span itemprop="author">Kam Leung</span>, PhD<div class="affiliation small">National Center for Biotechnology Information, NLM, NIH<div><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="vog.hin.mln.ibcn@DACIM" class="oemail">vog.hin.mln.ibcn@DACIM</a></div></div><div class="small">Corresponding author.</div></div><h3>Publication History</h3><p class="small">Created: <span itemprop="datePublished">May 2, 2006</span>; Last Update: <span itemprop="dateModified">October 6, 2011</span>.</p><h3>Copyright</h3><div><div class="half_rhythm"><a href="/books/about/copyright/">Copyright Notice</a></div></div><h3>Publisher</h3><p><a href="http://www.ncbi.nlm.nih.gov/" ref="pagearea=page-banner&targetsite=external&targetcat=link&targettype=publisher">National Center for Biotechnology Information (US)</a>, Bethesda (MD)</p><h3>NLM Citation</h3><p>Leung K. [11C](+)-4-N-Propyl-,3,4a,5,6,10b-hexahydro-2H-naphth[1,2-b][1,4]-oxazin-9-ol. 2006 May 2 [Updated 2011 Oct 6]. In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. <span class="bk_cite_avail"></span></p></div><div class="small-screen-prev"><a href="/books/n/micad/FLB457-11C/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M75,30 c-80,60 -80,0 0,60 c-30,-60 -30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Prev</text></svg></a></div><div class="small-screen-next"><a href="/books/n/micad/Befloxatone11C/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M25,30c80,60 80,0 0,60 c30,-60 30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Next</text></svg></a></div></article><article data-type="table-wrap" id="figobPHNO11CTncchemicalname11c4npropyl3"><div id="PHNO11C.T.nc_chemical_name11c4npropyl3" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23408/table/PHNO11C.T.nc_chemical_name11c4npropyl3/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__PHNO11C.T.nc_chemical_name11c4npropyl3_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](+)-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</td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;">
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<a href="https://pubchem.ncbi.nlm.nih.gov/substance/10323029" 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=10323029" alt="image 10323029 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](+)-PHNO</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](+)-4-Propyl-9-hydroxy-1,2,3,4a,5,6-hexahydronaphthoxazine, [<sup>11</sup>C](+)-4-propyl-9-hydroxynaphthoxazine</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;">Dopamine receptors (D<sub>2</sub> and D<sub>3</sub>)</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:middle;">Receptor</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Method of detection:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:middle;">Positron emission tomography (PET)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Source of signal / contrast:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:middle;"><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:middle;">No</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Studies:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
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<i>In vitro</i>
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</div></li><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Rodents
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</div></li><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Non-primate non-rodent mammals
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</div></li><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Humans
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</div></li></ul>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Click on the above structure for additional information in <a href="http://pubchem.ncbi.nlm.nih.gov/" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubChem</a>.</td></tr></tbody></table></div></div></article></div><div id="jr-scripts"><script src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/libs.min.js"> </script><script src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/jr.min.js"> </script></div></div>
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