Synthesis, dopamine and serotonin transporter binding affinities of novel analogues of meperidine.
A series of meperidine analogues was synthesized and the binding affinities for the dopamine and serotonin transporters were determined. The substituents on the phenyl ring greatly influenced the potency and selectivity of these compounds for the transporter binding sites. In general, meperidine (3) and its analogues were more selective for serotonin transporter binding sites and the esters 9 were more potent than the corresponding nitriles 8. The 3,4-dichloro derivative 9e was the most potent ligand of the series for dopamine transporter binding sites while the 2-naphthyl derivative 9g exhibited the most potent binding affinity and was highly selective for serotonin transporter binding sites.
Lomenzo
S A
SA
Department of Chemistry, University of New Orleans, LA 70148, USA.
Izenwasser
S
S
Gerdes
R M
RM
Katz
J L
JL
Kopajtic
T
T
Trudell
M L
ML
D002352:Carrier Proteins / Q000378:metabolism*; D004298:Dopamine / Q000378:metabolism; D050483:Dopamine Plasma Membrane Transport Proteins; D008562:Membrane Glycoproteins / Q000378:metabolism*; D026901:Membrane Transport Proteins; D008614:Meperidine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism; D009419:Nerve Tissue Proteins; D011485:Protein Binding; D012701:Serotonin / Q000378:metabolism; D050486:Serotonin Plasma Membrane Transport Proteins
D002352:Carrier Proteins; D050483:Dopamine Plasma Membrane Transport Proteins; D008562:Membrane Glycoproteins; D026901:Membrane Transport Proteins; D009419:Nerve Tissue Proteins; D050486:Serotonin Plasma Membrane Transport Proteins; D012701:Serotonin; D008614:Meperidine; D004298:Dopamine