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Synthesis and characterization of [ N ‐methyl‐ 3 H]loperamide
Author(s) -
Filer Crist N.,
Egan Judith A.,
Nugent Richard P.
Publication year - 2014
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.3198
Subject(s) - loperamide , chemistry , methyl iodide , agonist , opiate , thin layer chromatography , imine , high performance liquid chromatography , stereochemistry , organic chemistry , chromatography , receptor , diarrhea , biochemistry , medicine , catalysis
Loperamide is a piperidine butyramide mu‐opiate receptor agonist and currently employed to treat diarrhea. Because a single past report of tritiating loperamide was limited to only a very low specific activity product without technical details or extensive analysis, the synthesis of [ N ‐methyl‐ 3 H]loperamide at high specific activity is now described in detail. An imine precursor was alkylated with [ 3 H]methyl iodide to obtain a quaternary intermediate, which was then reacted with 4‐(4‐chlorophenyl)‐4‐hydroxypiperidine to afford the desired product [ N ‐methyl‐ 3 H]loperamide, characterized by thin layer chromatography (TLC), HPLC, MS, UV, and proton‐decoupled tritium NMR.