title: Metabolism of amphetamines by Mycobacterium smegmatis.
abstract: Amphetamine and five N-alkylated homologues were readily metabolized by Mycobacterium smegmatis and the products obtained were identified by gas-liquid chromatography and mass spectrometry. The N-aklylsubstituent had a considerable influence on the degree and mechanism of biotransformation. With the exception of the N-isopropyl derivative, all of the N-alkylated homologues were deaklylated to amphetamine which was then conjugated to the N-acetyl derivative. The degree of N-oxygenation of these substrates was significantly different from that observed in mammalian and fungal systems where four products are generally recovered. Mycobacterium smegmatis N-oxygenation of amphetamine did not occur, whereas all N-alkylated amphetamines were converted to the corresponding nitrones or, in the case of methamphetamine, to 1-phenyl-2-propanone oxime. No other N-oxygenated products were isolated. Mycobacterium smegmatis metabolism of 1-phenyl-2-propanone oxime, N-hydroxy-amphetamine. N-hydroxy-N-(n-proply)amphetamine, and the nitrone, alpha-methyl-N-(n-propyl-idene)benzeneethanamine N-oxide, was also studied. Some hydrolysis of the oxime to 1-phenyl-2-propanone was observed. The other three substrates were metabolized to amphetamine and N-acetylamphetamine.
mesh_terms: D000662:Amphetamines / Q000378:metabolism*; D001711:Biotransformation; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D013058:Mass Spectrometry; D009161:Mycobacterium / Q000378:metabolism*; D012988:Soil Microbiology
chemical_list: D000662:Amphetamines