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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
24
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pubmed:dateCreated |
1997-1-6
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pubmed:abstractText |
A series of 9-methyl-3 beta-phenyl-2-substituted-9-azabicyclo[3.3.1]nonane derivatives were synthesized and evaluated as cocaine-binding site ligands at the dopamine transporter (DAT). The conformation of the bicyclic structures and the stereochemistry of the substituents were determined by NMR and X-ray crystallography. The in vitro binding affinity (Ki) of the 9-azabicyclo[3.3.1]nonane derivatives was measured in rat caudate-putamen tissue, and they were found to be 100-fold (Ki = 2-14 microM) less potent than cocaine and other tropane analogs. From these results it is evident that the cocaine-binding site at the DAT is very sensitive to structural modifications of the unsubstituted methylene bridge [C(6)-C(7)] of cocaine and cocaine-like compounds.
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pubmed:grant |
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Aza Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Bicyclo Compounds, Heterocyclic,
http://linkedlifedata.com/resource/pubmed/chemical/Carrier Proteins,
http://linkedlifedata.com/resource/pubmed/chemical/Cocaine,
http://linkedlifedata.com/resource/pubmed/chemical/Dopamine Plasma Membrane Transport...,
http://linkedlifedata.com/resource/pubmed/chemical/Membrane Glycoproteins,
http://linkedlifedata.com/resource/pubmed/chemical/Membrane Transport Proteins,
http://linkedlifedata.com/resource/pubmed/chemical/Nerve Tissue Proteins,
http://linkedlifedata.com/resource/pubmed/chemical/Receptors, Drug,
http://linkedlifedata.com/resource/pubmed/chemical/Slc6a3 protein, rat,
http://linkedlifedata.com/resource/pubmed/chemical/cocaine receptor
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pubmed:status |
MEDLINE
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pubmed:month |
Nov
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pubmed:issn |
0022-2623
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:day |
22
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pubmed:volume |
39
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
4744-9
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pubmed:dateRevised |
2007-11-14
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pubmed:meshHeading |
pubmed-meshheading:8941387-Animals,
pubmed-meshheading:8941387-Aza Compounds,
pubmed-meshheading:8941387-Bicyclo Compounds, Heterocyclic,
pubmed-meshheading:8941387-Binding Sites,
pubmed-meshheading:8941387-Carrier Proteins,
pubmed-meshheading:8941387-Cocaine,
pubmed-meshheading:8941387-Crystallography, X-Ray,
pubmed-meshheading:8941387-Dopamine Plasma Membrane Transport Proteins,
pubmed-meshheading:8941387-Magnetic Resonance Spectroscopy,
pubmed-meshheading:8941387-Membrane Glycoproteins,
pubmed-meshheading:8941387-Membrane Transport Proteins,
pubmed-meshheading:8941387-Molecular Conformation,
pubmed-meshheading:8941387-Molecular Structure,
pubmed-meshheading:8941387-Nerve Tissue Proteins,
pubmed-meshheading:8941387-Protein Binding,
pubmed-meshheading:8941387-Rats,
pubmed-meshheading:8941387-Receptors, Drug
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pubmed:year |
1996
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pubmed:articleTitle |
Synthesis and dopamine transporter affinity of 2-(methoxycarbonyl)-9-methyl-3-phenyl-9-azabicyclo[3.3.1]nonane derivatives.
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pubmed:affiliation |
Department of Chemistry, University of New Orleans, Louisiana 70148, USA.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.
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