title: Synthesis and dopaminergic properties of the two enantiomers of 3-(3,4-dimethylphenyl)-1-propylpiperidine, a potent and selective dopamine D4 receptor ligand.
abstract: The synthesis of the two enantiomers of 3-(3,4-dimethylphenyl)-1-propylpiperidine 1, a potent and selective D4 dopaminergic ligand, was performed. The 3-(3,4-dimethylphenyl)- 1-propylpiperidine with the R configuration showed an affinity for the D4 receptors 6-fold higher than the corresponding enantiomer with the S configuration. Furthermore, the (R)-1 enantiomer proved to be highly selective for D4 receptors with respect to D2-D3 receptors, with a Ki ratio higher than 25,000, while the (S)-1 enantiomer was about 100-fold less selective than the (R)-1 one.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università di Pisa, Italy. bmacchia@farm.unipi.it
authors.forename: B
authors.initials: B
authors.lastname: Macchia
authors.forename: L
authors.initials: L
authors.lastname: Cervetto
authors.forename: G C
authors.initials: GC
authors.lastname: Demontis
authors.forename: P
authors.initials: P
authors.lastname: Domiano
authors.forename: B
authors.initials: B
authors.lastname: Longoni
authors.forename: M
authors.initials: M
authors.lastname: Macchia
authors.forename: F
authors.initials: F
authors.lastname: Minutolo
authors.forename: E
authors.initials: E
authors.lastname: Orlandini
authors.forename: G
authors.initials: G
authors.lastname: Ortore
authors.forename: C
authors.initials: C
authors.lastname: Papi
mesh_terms: D001479:Basal Ganglia / Q000737:chemistry; D015259:Dopamine Agents / Q000138:chemical synthesis* / Q000378:metabolism; D006801:Humans; D008024:Ligands; D008968:Molecular Conformation; D010880:Piperidines / Q000138:chemical synthesis / Q000378:metabolism*; D011485:Protein Binding; D017448:Receptors, Dopamine D2 / Q000378:metabolism; D050638:Receptors, Dopamine D4; D012160:Retina / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C116268:3-(3,4-dimethylphenyl)-N-n-propylpiperidine; C493599:DRD4 protein, human; D015259:Dopamine Agents; D008024:Ligands; D010880:Piperidines; D017448:Receptors, Dopamine D2; D050638:Receptors, Dopamine D4