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Synthesis of high specific activity tritium labelled 1 S ,2 S ‐(‐)‐ trans ‐2‐isothiocyanato‐N‐methyl‐N‐[2‐(1‐pyrrolidinyl)‐cyclohexyl]benzeneacetamide, a specific irreversible ligand for kappa opioid receptors
Author(s) -
De Costa Brian R.,
Thurkauf Andew,
Rothman Richard R.,
Jacobson Arthur E.,
Rice Kenner C.
Publication year - 1990
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580281105
Subject(s) - chemistry , tritium , yield (engineering) , aniline , ligand (biochemistry) , medicinal chemistry , catalysis , stereochemistry , kappa , receptor , organic chemistry , biochemistry , materials science , physics , linguistics , philosophy , nuclear physics , metallurgy
Optically pure tritium labeled 1 S ,2 S ‐(‐)‐ trans ‐2‐isothiocyanato‐N‐methyl‐N‐[2‐(1‐pyrrolidinyl)cyclohexyl]benzeneacetamide, an affinity ligand specific for the kappa opioid receptor was synthesized from optically pure 1 S ,2 S ‐(‐)‐ trans ‐2‐amino‐N‐methyl‐N‐[2‐(1‐pyrrolidinyl)cyclohexyl]benzeneacetamide via the sequence of dibromination (57%) followed by catalytic tritiation of the dibromide. The resulting tritium labelled aniline (14% yield, specific activity 31.2 Ci/mmol) was transformed to the title compound in 13.3% yield and 99+% radiochemical purity by treatment with thiophosgene.