N-8-substituted benztropinamine analogs as selective dopamine transporter ligands

Peter Grundt; Theresa A. Kopajtic; Jonathan L. Katz; Amy Hauck Newman

doi:10.1016/j.bmcl.2005.08.111

N-8-substituted benztropinamine analogs as selective dopamine transporter ligands

Peter Grundt
, Theresa A. Kopajtic
, Jonathan L. Katz
, Amy Hauck Newman

Chemistry & Biochemistry

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

7 Scopus citations

Abstract

A series of N-8-substituted benztropinamines was synthesized and evaluated for binding at the dopamine (DAT), serotonin (SERT), norepinephrine (NET) transporters, and muscarinic M1 receptors. In general, the isosteric replacement of the C-3 benzhydrol ether of benztropine by a benzhydryl amino group was well tolerated at the DAT. However, for certain N-8 substituted derivatives, selectivity over muscarinic M1 receptor affinity was reduced.

Original language	English (US)
Pages (from-to)	5419-5423
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	15
Issue number	24
DOIs	https://doi.org/10.1016/j.bmcl.2005.08.111
State	Published - Dec 15 2005

Bibliographical note

Funding Information:
This work was funded by the National Institute on Drug Abuse-Intramural Research Program. P.G. was supported by a NIH Visiting Fellowship.

Keywords

Benztropinamine
Benztropine
Cocaine
Dopamine transporters
Ligand binding
Monoamine transporters
Muscarinic M1 receptor

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10.1016/j.bmcl.2005.08.111

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title = "N-8-substituted benztropinamine analogs as selective dopamine transporter ligands",

abstract = "A series of N-8-substituted benztropinamines was synthesized and evaluated for binding at the dopamine (DAT), serotonin (SERT), norepinephrine (NET) transporters, and muscarinic M1 receptors. In general, the isosteric replacement of the C-3 benzhydrol ether of benztropine by a benzhydryl amino group was well tolerated at the DAT. However, for certain N-8 substituted derivatives, selectivity over muscarinic M1 receptor affinity was reduced.",

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T1 - N-8-substituted benztropinamine analogs as selective dopamine transporter ligands

AU - Grundt, Peter

AU - Kopajtic, Theresa A.

AU - Katz, Jonathan L.

AU - Newman, Amy Hauck

N1 - Funding Information: This work was funded by the National Institute on Drug Abuse-Intramural Research Program. P.G. was supported by a NIH Visiting Fellowship.

PY - 2005/12/15

Y1 - 2005/12/15

N2 - A series of N-8-substituted benztropinamines was synthesized and evaluated for binding at the dopamine (DAT), serotonin (SERT), norepinephrine (NET) transporters, and muscarinic M1 receptors. In general, the isosteric replacement of the C-3 benzhydrol ether of benztropine by a benzhydryl amino group was well tolerated at the DAT. However, for certain N-8 substituted derivatives, selectivity over muscarinic M1 receptor affinity was reduced.

AB - A series of N-8-substituted benztropinamines was synthesized and evaluated for binding at the dopamine (DAT), serotonin (SERT), norepinephrine (NET) transporters, and muscarinic M1 receptors. In general, the isosteric replacement of the C-3 benzhydrol ether of benztropine by a benzhydryl amino group was well tolerated at the DAT. However, for certain N-8 substituted derivatives, selectivity over muscarinic M1 receptor affinity was reduced.

KW - Benztropinamine

KW - Benztropine

KW - Cocaine

KW - Dopamine transporters

KW - Ligand binding

KW - Monoamine transporters

KW - Muscarinic M1 receptor

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M3 - Article

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SN - 0960-894X

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EP - 5423

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JF - Bioorganic and Medicinal Chemistry Letters

IS - 24

ER -

N-8-substituted benztropinamine analogs as selective dopamine transporter ligands

Abstract

Bibliographical note

Keywords

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