Structural studies on McN-5652-X, a high-affinity ligand for the serotonin transporter in mammalian brain.
McN-5652-X, (+)-1, is a potent, selective inhibitor of serotonin reuptake in mammalian brain. When radiolabeled with (11)C, it has served as a positron-emission tomography (PET) radiotracer for in vivo imaging of central serotonin transporters. We have determined the solid-state structures of (+)-1.HClO(4) and (+)-1.(+)-(2R,3R)-tartrate by single-crystal X-ray diffraction, thereby confirming the trans relative configuration (Chemical Abstracts Service rules of nomenclature) and the 6S,10bR absolute configuration for (+)-1. Results from a vibrational circular dichroism (VCD) study on (+)-1 in CDCl(3) are consistent with the 6S,10bR absolute configuration.
Johnson & Johnson Pharmaceutical Research & Development, Spring House, PA 19477-0776, USA. bmaryano@prdus.jnj.com
Bruce E
BE
Maryanoff
David F
DF
McComsey
Rina K
RK
Dukor
Laurence A
LA
Nafie
Teresa B
TB
Freedman
Xiaolin
X
Cao
Victor W
VW
Day
D002352:Carrier Proteins / Q000378:metabolism; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D007546:Isoquinolines / Q000737:chemistry* / Q000378:metabolism; D007700:Kinetics; D008562:Membrane Glycoproteins / Q000378:metabolism; D026901:Membrane Transport Proteins; D008958:Models, Molecular; D009419:Nerve Tissue Proteins; D050486:Serotonin Plasma Membrane Transport Proteins; D017367:Selective Serotonin Reuptake Inhibitors / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism
D002352:Carrier Proteins; D007546:Isoquinolines; D008562:Membrane Glycoproteins; D026901:Membrane Transport Proteins; D009419:Nerve Tissue Proteins; D050486:Serotonin Plasma Membrane Transport Proteins; D017367:Selective Serotonin Reuptake Inhibitors; C058079:McN 5652