Probes for narcotic receptor mediated phenomena. 12. cis-(+)-3-Methylfentanyl isothiocyanate, a potent site-directed acylating agent for. delta. opioid receptors. …

…, JV Silverton, WF Simonds, RA Streaty…

Index: Burke Jr.; Jacobson; Rice; Silverton; Simonds; Streaty; Klee Journal of Medicinal Chemistry, 1986 , vol. 29, # 6 p. 1087 - 1093

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Citation Number: 52

Abstract

The first enantiomeric pair of irreversible opioid ligands [(+)-and (-)-41 were synthesized in> 99.6% optical purity as determined by HPLC analysis of diastereoisomeric derivatives of the intermediate 3-methyl-N-phenyl-4-piperidinamine (9) enantiomers. Single-crystal X-ray analysis of the (R, R)-L-(+)-tartaric acid salt of (-)-9 revealed the absolute configuration to be 3S, 4R. The absolute configuration of (-)-3 [cis-(-)-3-methylfentanyl] and (-)-4 derived from ...