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Synthesis of [13C 2 ]‐amitriptyline, nortriptyline and desmethylnortriptyline
Author(s) -
Midgley I.,
Pryor R. W.,
Hawkins D. R.
Publication year - 1978
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.2580150159
Subject(s) - nortriptyline , amitriptyline , chemistry , nitrogen atom , tricyclic , ring (chemistry) , tricyclic antidepressant , side chain , bromide , antidepressant , stereochemistry , pharmacology , organic chemistry , medicine , polymer , hippocampus
The syntheses of the antidepressant drug, amitriptyline, and its metabolites nortriptyline and desmethylnortriptyline, doubly labelled with carbon‐13 have been accomplished in thirteen stages. Ba 13 CO 3 was used for the carbonation of o ‐tolylmagnesium bromide, which subsequently provided a 13 C‐label distributed between positions 5, 10 and 11 in the tricyclic ring. A second carbon‐13 atom was introduced at the terminal side‐chain carbon, adjacent to nitrogen, using Na 13 CN.