The Analytical and Pharmacological Characterization of alpha-Benzyl-N-Methylphenethylamine, an Impurity in Illicit Methamphetamine Synthesis.
AIR FORCE INST OF TECH WRIGHT-PATTERSON AFB OH
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Methamphetamine METH is a popular drug of abuse, readily synthesized in clandestine laboratories. Illicit synthesis results in various contaminants, one of which is a-benzyl-N-methylphenethylamine BNMPA. This dissertation investigates the hypotheses that contaminants like BNMPA may contribute to the toxicity of METH and that detection of BNMPNmetabolites in biological fluids may be utilized as markers of illicit METH consumption. Based on metabolic studies of benzphetamine a structurally similar compound, we predicted the four major metabolites of BNMPA to be N- demethyl-BNMPA, diphenyl-2-propanone, para-hydroxy-N-demethyl-BNMPA para-hydroxy-BNMPA, and diphenyl-2-propanol. We synthesized these compounds and developed a gas chromatographymass spectrometry detection method. We confirmed these as true metabolites in humans following ingestion. para-Hydroxy-BNMPA and para-hydrnxy-N-demethyl-BNMPA as conjugates were the major metabolites detected.