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Title: Synthesis of Stable Isotope Labeled Chloroquine, Amodiaquine and Their Metabolites

Abstract

Anti–malaria drugs chloroquine, amodiaquine and their metabolites were stable isotope labeled with 13C and 15N starting from uniformly 13C labeled benzene and 15N labeled potassium nitrate to give M+7 isotopomers. Here, chloroquine, and its metabolites were prepared from 7–chloro–1,2,3,4–tetrahydroquinolin–4–one through addition to the carbonyl with the corresponding amines; and the amodiaquine and its metabolites were prepared from 4,7–dichloroquinoline in a selective aryl–halogen exchange with the corresponding amines.

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]
  1. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Publication Date:
Research Org.:
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1511624
Report Number(s):
LA-UR-18-31663
Journal ID: ISSN 0362-4803
Grant/Contract Number:  
89233218CNA000001
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Labelled Compounds and Radiopharmaceuticals
Additional Journal Information:
Journal Volume: 62; Journal Issue: 5; Journal ID: ISSN 0362-4803
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
07 ISOTOPE AND RADIATION SOURCES; chloroquine; amodiaquine; [U-13C]benzene; mass spectral standards

Citation Formats

Wu, Ruilian, Williams, Robert F., Silks, III, Louis A. “Pete”, and Schmidt, Jurgen G. Synthesis of Stable Isotope Labeled Chloroquine, Amodiaquine and Their Metabolites. United States: N. p., 2019. Web. doi:10.1002/jlcr.3721.
Wu, Ruilian, Williams, Robert F., Silks, III, Louis A. “Pete”, & Schmidt, Jurgen G. Synthesis of Stable Isotope Labeled Chloroquine, Amodiaquine and Their Metabolites. United States. doi:10.1002/jlcr.3721.
Wu, Ruilian, Williams, Robert F., Silks, III, Louis A. “Pete”, and Schmidt, Jurgen G. Mon . "Synthesis of Stable Isotope Labeled Chloroquine, Amodiaquine and Their Metabolites". United States. doi:10.1002/jlcr.3721. https://www.osti.gov/servlets/purl/1511624.
@article{osti_1511624,
title = {Synthesis of Stable Isotope Labeled Chloroquine, Amodiaquine and Their Metabolites},
author = {Wu, Ruilian and Williams, Robert F. and Silks, III, Louis A. “Pete” and Schmidt, Jurgen G.},
abstractNote = {Anti–malaria drugs chloroquine, amodiaquine and their metabolites were stable isotope labeled with 13C and 15N starting from uniformly 13C labeled benzene and 15N labeled potassium nitrate to give M+7 isotopomers. Here, chloroquine, and its metabolites were prepared from 7–chloro–1,2,3,4–tetrahydroquinolin–4–one through addition to the carbonyl with the corresponding amines; and the amodiaquine and its metabolites were prepared from 4,7–dichloroquinoline in a selective aryl–halogen exchange with the corresponding amines.},
doi = {10.1002/jlcr.3721},
journal = {Journal of Labelled Compounds and Radiopharmaceuticals},
number = 5,
volume = 62,
place = {United States},
year = {2019},
month = {3}
}

Journal Article:
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