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Synthesis of [ 2 H 5 ]arecoline for use as internal standard in mass spectrometric assay
Author(s) -
Umesha Shetty H.,
Soncrant Timothy T.,
Greig Nigel H.,
Rapoport Stanley I.
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.2580280906
Subject(s) - chemistry , arecoline , carboxylate , deuterium , sodium iodide , sodium , yield (engineering) , pyridinium , nuclear chemistry , methyl iodide , radiochemistry , chromatography , medicinal chemistry , organic chemistry , biochemistry , physics , receptor , muscarinic acetylcholine receptor , materials science , quantum mechanics , metallurgy
Five deuterium atoms, three in the N ‐methyl group and one each in positions 2 and 6, were incorporated into the cholinergic agonist, arecoline ( 1 ), methyl 1‐methyl‐1,2,5,6‐tetrahydropyridine‐3‐carboxylate, with 96% efficiency. Trideuterated pyridinium iodide ( 2 ) was reduced with sodium borodeuteride or sodium cyanoborodeuteride in acidic medium to yield [ 2 H 5 ]arecoline ( 3 ). Significantly greater deuterium incorporation occurred when 2 was reduced with sodium cyanoborodeuteride. This reduction process is discussed. The synthesized labelled compound was determined to be a suitable internal standard for mass spectrometric assays.