Synthesis and dopaminergic properties of the two enantiomers of 3-(3,4-dimethylphenyl)-1-propylpiperidine, a potent and selective dopamine D4 receptor ligand.

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Macchia B, Cervetto L, Demontis GC, Domiano P, Longoni B, Macchia M, Minutolo F, Orlandini E, Ortore G, Papi C

Synthesis and dopaminergic properties of the two enantiomers of 3-(3,4-dimethylphenyl)-1-propylpiperidine, a potent and selective dopamine D4 receptor ligand.

Bioorg Med Chem Lett. 2001 Jan 22;11(2):223-6.

PubMed ID

11206464 [ View in PubMed

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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.

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Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Dopamine	Dopamine D4 receptor	Ki (nM)	15	N/A	N/A	Details