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The synthesis of non‐exchangeable deuterated internal standards for imipramine and its metabolites
Author(s) -
Woodard R. W.,
Craig J. Cymerman
Publication year - 1979
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.2580160212
Subject(s) - chemistry , desipramine , imipramine , deuterium , azepine , reductive amination , derivative (finance) , alkylation , stereochemistry , medicinal chemistry , organic chemistry , catalysis , medicine , physics , alternative medicine , antidepressant , pathology , quantum mechanics , neuroscience , hippocampus , financial economics , economics , biology
The synthesis of 10,11‐dihydro‐5‐(3‐dimethylaminopropyl)‐5 H ‐dibenz[b,f]azepine (imipramine) and its 3‐methylamino analogue (desipramine)labelled with deuterium in either the 1‐ or the 3‐position of the side chain in high isotopic purity is described. The 3,3‐d 2 compounds are obtained from the common precursor 5‐(2‐cyanoethyl)‐10,11‐dihydro‐5 H ‐dibenz[b,f]azepine by reduction and alkylation, while the 1,1‐d 2 products are accessible from the 5‐(3‐chloropropionyl) derivative by amination and reduction. These compounds are required for use as non‐exchangeable mass spectrometric stable isotope internal standards for the simultaneous determination of imipramine and desipramine in biological fluids.