Premium
Synthesis of [ 11 C](−)‐α,α‐dideutero‐phenylephrine for in vivo kinetic isotope studies
Author(s) -
Del Rosario R. B.,
Wieland D. M.
Publication year - 1995
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.2580360703
Subject(s) - chemistry , phenylephrine , in vivo , octopamine (neurotransmitter) , kinetic isotope effect , deuterium , stereochemistry , biochemistry , medicine , receptor , serotonin , microbiology and biotechnology , blood pressure , biology , physics , quantum mechanics
(−)‐[ 11 C]Phenylephrine and positron emission tomography could potentially be used to assess neuronal monoamine oxidase activity in the heart. Previous data for (−)‐( 11 C]phenylephrine indicate that, although its retention and neuronal selectivity parallel that of the neuronal mapping agent (−)‐[ 11 C]hydroxyephedrine, its neuronal storage and clearance properties are quite different. In order to study the in vivo kinetics of (−)‐[ 11 C]phenylephrine in greater detail, the dideutero analog [ 11 C]‐(−)‐α,α‐dideutero‐phenylephrine, 1 , was synthesized by [ 11 C]methylation of the precursor (−)‐α,α‐dideutero‐ m ‐octopamine. The key step in the procedure was BD 3 reduction of the cyanohydrin derived from 3‐hydroxybenzaldehyde. Deuterium incorporation at the alpha positions of m ‐octopamine was confirmed by NMR and mass spectroscopy of the deuterated product and by comparison of spectral data with undeuterated m ‐octopamine. (−)‐α,α‐Dideutero‐ m ‐octopamine was methylated with CF 3 SO 3 11 CH 3 to give 1 suitable for animal and clinical studies.