N-8-Substituted benztropinamine analogs as selective dopamine transporter ligands.
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.
Grundt
Peter
P
Medicinal Chemistry Section, National Institute on Drug Abuse--Intramural Research Program, National Institutes of Health, 5500 Nathan Shock Drive, Baltimore, MD 21224, USA.
Kopajtic
Theresa A
TA
Katz
Jonathan L
JL
Newman
Amy Hauck
AH
D000588:Amines; D001590:Benztropine / Q000737:chemistry*; D001665:Binding Sites; D015283:Citalopram / Q000737:chemistry; D003042:Cocaine / Q000737:chemistry; D050483:Dopamine Plasma Membrane Transport Proteins / Q000737:chemistry* / Q000378:metabolism; D005473:Fluoxetine / Q000031:analogs & derivatives / Q000737:chemistry; D007700:Kinetics; D008024:Ligands; D008958:Models, Molecular; D008968:Molecular Conformation; D018727:Muscarinic Antagonists / Q000737:chemistry; D010276:Parasympatholytics / Q000737:chemistry; D010890:Pirenzepine / Q000737:chemistry
D000588:Amines; D050483:Dopamine Plasma Membrane Transport Proteins; D008024:Ligands; D018727:Muscarinic Antagonists; D010276:Parasympatholytics; D005473:Fluoxetine; D015283:Citalopram; C011386:nisoxetine; D001590:Benztropine; D010890:Pirenzepine; D003042:Cocaine