United States Department of Transportation
i
Stereochemical Determination of Selegiline Metabolites in Postmortem Biological Specimens
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1997-07-01
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Edition:Final Report
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Abstract:The Federal Aviation Administration's Toxicology and Accident Research Laboratory determines the presence of drugs, volatiles, and primary combustion gases in biological samples from aircraft accident victims and also establishes any medical condition for which the drugs might have been taken. In this study, findings related to an aircraft accident are reported. Along with biological specimens from the pilot of this fatal accident, two types of tablets found at the accident scene were submitted for analysis. These tablets were identified as levodopa and selegiline, commonly prescribed for the treatment of Parkinson's disease. Selegiline, a stereospecific compound, is biotransformed into (-)-N-desmethylselegiline, (-)-methamphetamine, and (-)-amphetamine. During this process, the chiral center of the parent molecule is not affected. The latter two levorotatory metabolites cannot be easily distinguished by routine analysis from their dextrorotary isomers, which are controlled substances. Therefore, it was prudent to differentiate these isomers to prove or disprove the controlled substance categorization. Initial immunoassay drug screenings revealed the presence of amphetamine class drugs (867 ng/ml) and amphetamine/methamphetamine (261 ng/ml) in urine and methamphetamine (46 ng/ml) in blood. The gas chromatography-mass spectrometry (GC/MS) results revealed the presence of methamphetamine in the concentrations of 76 ng/ml of blood and 685 ng/ml of urine. The level of amphetamine was 52 ng/ml in blood and 320 ng/ml in urine. To determine the stereospecificity of these amines, the isolated amines from the biosamples were derivatized by a stereospecific agent, (S)-(-)-N-(trifluoroacetyl)prolyl chloride, and characterized by a GC/MS method to be levorotatory. The 2.14 ratio of (-)-methamphetamine to (-)-amphetamine concentrations in the urine was consistent with a selegiline study in the recent literature. The stereospecific analysis, in conjunction with the history of the pilot being on Parkinson's medications, suggests that the source of these amines was selegiline. This conclusion substantiates the importance of the identification of enantiomers in evaluating and interpreting related analytical results for accident investigations.
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