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- W2014033462 abstract "Cyanide anion was used to attempt to trap possible imine intermediates in the oxidative N-dealkylation of propranolol (1). Reaction of 3-(1-naphthoxy)-1-amino-2-propanol (desisopropylpropranolol, 2) with acetone provided this expected intermediate in an ∼7:1 ratio of oxazolidine 6 to imine 5, as determined by 1H NMR. The mixture when treated with sodium cyanide gave the expected α-aminonitrile 7. Microsomal oxidation of propranolol in the presence of sodium cyanide gave two cyanide-containing adducts as shown by GC-MS (12a and 12b). Using specifically deuterated propranolols (8, 9, 10, and 11) as substrates showed both of these cyanide-containing adducts to have lost the N-isopropyl group. Compounds 12a and 12b were shown to be diastereomeric αaL-aminonitriles arising from the reaction of 2 with propionaldehyde, a contaminant from the ether used for extraction, and cyanide anion. Authentic 7, stable to derivatization and GC-MS conditions, rapidly decomposed under the conditions of the metabolic experiments." @default.
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- W2014033462 date "1985-09-01" @default.
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- W2014033462 title "Attempts to Use Cyanide Ion to Trap Imine Intermediates in the Microsomal N-Dealkylation of Propranolol: Formation of α-Aminonitriles as Artifacts When Using Ether for Extraction" @default.
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- W2014033462 doi "https://doi.org/10.1002/jps.2600740912" @default.
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