Chirality can drastically influence the pharmacological properties of drugs of abuse. One enantiomer may be a potent pharmaceutical drug used to treat diseases whilst the other enantiomer may cause harmful effects or have addictive potential. As a result, it is beneficial for forensic scientists and analytical chemists to be able to distinguish chiral compounds and determine the enantiomeric excess of drug samples and in biological fluids. One of the major issues in determining the chirality of a drug is the similarities in the physical properties of the two enantiomers. One thing that may differ is how chiral compounds interact with one another. Problems associated with common methods of chiral separation include high costs for analysis or poor baseline separation. The use of a chiral derivatizating agent is an attractive solution that can be used to avoid these issues. Derivatization using a chiral substrate allows for the formation of diastereomers, which have unique physicochemical properties, and can be separated using traditional analytical techniques such as achiral gas chromatography-mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR). Using such methods can drastically reduce the cost associated with analyses and are typically widely available to laboratories that do not have chiral instrumentation. Although some common chiral derivatizing agents (CDAs) such as Mosher’s Acid Chloride can be financially burdensome, this research was able to synthesize an inexpensive CDA capable of forming covalent linkages with drugs of abuse. Here, the following experiments are described where trifluoroacetyl-protected alanine (TFA protected-alanine) is used to derivatize chiral amphetamines allowing for the determination of enantiomeric excess using fluorine NMR. Based on these findings, the separation of chiral compounds such as amphetamine, 3,4-methylenedioxyamphetamine (MDA), and alpha-methylbenzylamine was accomplished.
|Advisor:||Olson, David E.|
|Commitee:||Moeller, Benjamin, Rodda, Luke N.|
|School:||University of California, Davis|
|School Location:||United States -- California|
|Source:||MAI 81/3(E), Masters Abstracts International|
|Subjects:||Analytical chemistry, Chemistry|
|Keywords:||Amphetamines, Chiral derivatizing agent, Chiral drugs of abuse, Derivatization, Fluorine NMR, Trifluoroacetyl-protected L-alanine|
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