Further evidence for a dopamine reuptake pharmacophore. The effect of N-methylation on threo-methylphenidate and its analogs

Mark Froimowitz; Howard M. Deutsch; Quing Shi; Kuo Ming Wu; Robert Glaser; Itay Adin; Clifford George; Margaret M. Schweri

doi:10.1016/S0960-894X(97)00193-5

Further evidence for a dopamine reuptake pharmacophore. The effect of N-methylation on threo-methylphenidate and its analogs

Mark Froimowitz, Howard M. Deutsch, Quing Shi, Kuo Ming Wu, Robert Glaser, Itay Adin, Clifford George, Margaret M. Schweri

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

N-methyl derivatives of methylphenidate and four analogs were synthesized and assayed for affinity at the dopamine transporter. The binding affinities of the N-methyl compounds were consistently lower by a factor ranging from 4 to 30 as compared with the corresponding secondary amine. This is consistent with the predictions of a pharmacophore model of compounds that bind to the dopamine transporter.

Original language	English
Pages (from-to)	1213-1218
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	7
Issue number	9
DOIs	https://doi.org/10.1016/S0960-894X(97)00193-5
State	Published - 6 May 1997

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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abstract = "N-methyl derivatives of methylphenidate and four analogs were synthesized and assayed for affinity at the dopamine transporter. The binding affinities of the N-methyl compounds were consistently lower by a factor ranging from 4 to 30 as compared with the corresponding secondary amine. This is consistent with the predictions of a pharmacophore model of compounds that bind to the dopamine transporter.",

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AU - Wu, Kuo Ming

AU - Glaser, Robert

AU - Adin, Itay

AU - George, Clifford

AU - Schweri, Margaret M.

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AB - N-methyl derivatives of methylphenidate and four analogs were synthesized and assayed for affinity at the dopamine transporter. The binding affinities of the N-methyl compounds were consistently lower by a factor ranging from 4 to 30 as compared with the corresponding secondary amine. This is consistent with the predictions of a pharmacophore model of compounds that bind to the dopamine transporter.

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Further evidence for a dopamine reuptake pharmacophore. The effect of N-methylation on threo-methylphenidate and its analogs

Abstract

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