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Synthesis of Quaternary Ammonium Salts of Tricyclic Cationic Drugs: A One-Pot Synthesis for the Bioorganic Chemistry Laboratory
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Abstract
A one-pot conversion of tricyclic cationic drugs to their quaternary ammonium forms is described for a widely used bioactive drug: chlorpromazine, a phenothiazine-based antipsychotic. After conversion to its free base, the parent drug was methylated using substoichiometric amounts of methyl iodide dissolved in ether; the charged quaternary ammonium derivative precipitated and parent drug was removed by successive washes with ether. The synthesis is quick, simple, and yields a single methylated product that is readily analyzed by IR, NMR, and TLC. In addition to these standard analytical protocols, the conversion of parent drug to the methylated form was evaluated in a simple biological system by qualitatively measuring the ability of the drug to induce alterations in the shape of mammalian erythrocytes via light microscopy of treated cells. The experiment successfully links aspects of synthetic organic chemistry and biology and is thus suitable for second-year organic chemistry and upper-division bioorganic chemistry laboratory courses.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
BiochemistryKeywords (Feature):
The Microscale LaboratoryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
Amines / Ammonium CompoundsCiting Articles
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This article has been cited by 1 ACS Journal articles (1 most recent appear below).
Citrus Peel Additives for One-Pot Triazole Formation by Decarboxylation, Nucleophilic Substitution, and Azide–Alkyne Cycloaddition Reactions
Desiree E. Mendes and Allen M. SchoffstallJournal of Chemical Education2011 88 (11), 1582-1585Citrus Peel Additives for One-Pot Triazole Formation by Decarboxylation, Nucleophilic Substitution, and Azide–Alkyne Cycloaddition Reactions
Desiree E. Mendes and Allen M. SchoffstallJournal of Chemical Education2011 88 (11), 1582-1585This undergraduate organic laboratory experiment consists of three different reactions occurring in the same flask: a cycloaddition reaction, preceded by decarboxylation and nucleophilic substitution reactions. The decarboxylation and cycloaddition ...
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- Received: August 03, 2009
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