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Slow-onset, long-duration, alkyl analogues of methylphenidate with enhanced selectivity for the dopamine transporter.
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Slow-onset, long-duration, alkyl analogues of methylphenidate with enhanced selectivity for the dopamine transporter.

Author: M Froimowitz Affiliation: Massachusetts College of Pharmacy and Health Sciences, Boston, Massachusetts 02115, USA. mfroimowitz@mcphs.eduY GuLA DakinPM NagafujiCJ KelleyAll authors
Edition/Format: Article Article : English
Publication:Journal of medicinal chemistry, 2007 Jan 25; 50(2): 219-32
Database:From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.
Other Databases: British Library SerialsArticleFirst
Summary:
Methylphenidate analogues, in which the carbomethoxy has been replaced by an alkyl group and with different phenyl substituents, have been synthesized and tested in monoamine transporter assays. As predicted from a pharmacophore model, most of the RR/SS diastereomers showed high potency as dopamine reuptake inhibitors. Analogues with a 4-chlorophenyl group and an unbranched initial alkyl atom had consistently  Read more...
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Document Type: Article
All Authors / Contributors: M Froimowitz Affiliation: Massachusetts College of Pharmacy and Health Sciences, Boston, Massachusetts 02115, USA. mfroimowitz@mcphs.edu; Y Gu; LA Dakin; PM Nagafuji; CJ Kelley; D Parrish; JR Deschamps; A Janowsky
ISSN:0022-2623
Language Note: English
Unique Identifier: 110081487
Awards:

Abstract:

Methylphenidate analogues, in which the carbomethoxy has been replaced by an alkyl group and with different phenyl substituents, have been synthesized and tested in monoamine transporter assays. As predicted from a pharmacophore model, most of the RR/SS diastereomers showed high potency as dopamine reuptake inhibitors. Analogues with a 4-chlorophenyl group and an unbranched initial alkyl atom had consistently enhanced selectivity for the dopamine transporter. The most potent compounds were those with a three- or four-carbon chain. The "inactive" RS/SR diastereomers showed substantial activity when the phenyl substituent was 3,4-dichloro. On a locomotor assay, one compound was found to have a slow onset and a long duration of action. The activity of these compounds provides additional evidence for a conformational/superposition model of methylphenidate with cocaine-like structures. A ketone analogue, obtained by hydrogenating a previously described vinylogous amide, had activity similar to that of methylphenidate.

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