Synthesis of Stable Isotope Labeled Chloroquine, Amodiaquine and Their Metabolites

Journal Article · 18 March 2019 · Journal of Labelled Compounds and Radiopharmaceuticals

DOI: https://doi.org/10.1002/jlcr.3721 · OSTI ID:1511624

Wu, Ruilian  ^[1]; Williams, Robert F.  ^[1]; Silks, III, Louis A. “Pete”  ^[1]; Schmidt, Jurgen G.  ^[1]

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1. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

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.

• Research Organization: Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
• Sponsoring Organization: USDOE
• Grant/Contract Number: 89233218CNA000001
• OSTI ID: 1511624
• Report Number(s): LA-UR-18-31663
• Journal Information: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 62, Issue 5; ISSN 0362-4803
• Publisher: WileyCopyright Statement
• Country of Publication: United States
• Language: English