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Paper | Regular issue | Vol 34, No. 12, 1992, pp.2281-2292
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6075
Chiral, Potentially Irreversible Ligands for the Sigma Receptor Based on the Structure of 3-(3-Hydroxyphenyl)-N-propylpiperidine (3-PPP)

Neile A. Grayson, Wayne D. Bowen, and Kenner C. Rice*

*Laboratory of Medicinal Chemistry, Bldg 8, Rm B1-22, NIDDK, National Institutes of Health, Bethesda, MD 20892, U.S.A.


(+)-3-PPP is an optically active, highly potent and selective ligand for sigma receptors. The resolved enantiomeric pairs of potential irreversible sigma ligands (5a,b) and (9a,b) were designed and synthesized based on the structure of 3-PPP. An improved method of resolution was developed for the common intermediate (2a,b).