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In vitro stereoselective metabolism of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane. An apparent enantiomeric interaction. 1977

N P McGraw, and S C Callery, and N Castagnoli

The stereoselective metabolism [R/S (metabolized) less than 1] of the psychotomimetic amine (R,S)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane in 10 000g rabbit liver homogenate supernatant and 100 000g microsomal fractions has been demonstrated with the aid of the chiral reagent (S)-N-pentafluorobenzoylprolyl-1-imidazolide and GLC analyses. In contrast to the enantiomeric discrimination observed with racemic amine, the individual isomers were metabolized at approximately the same rate. This apparent enantiomeric interaction illustrates the fact that racemates should be viewed as unique chemical species with pharmacodynamic and toxicologic profiles potentially different from the individual antipodes.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008099 Liver A large lobed glandular organ in the abdomen of vertebrates that is responsible for detoxification, metabolism, synthesis and storage of various substances. Livers
D008297 Male Males
D008862 Microsomes, Liver Closed vesicles of fragmented endoplasmic reticulum created when liver cells or tissue are disrupted by homogenization. They may be smooth or rough. Liver Microsomes,Liver Microsome,Microsome, Liver
D011817 Rabbits A burrowing plant-eating mammal with hind limbs that are longer than its fore limbs. It belongs to the family Leporidae of the order Lagomorpha, and in contrast to hares, possesses 22 instead of 24 pairs of chromosomes. Belgian Hare,New Zealand Rabbit,New Zealand Rabbits,New Zealand White Rabbit,Rabbit,Rabbit, Domestic,Chinchilla Rabbits,NZW Rabbits,New Zealand White Rabbits,Oryctolagus cuniculus,Chinchilla Rabbit,Domestic Rabbit,Domestic Rabbits,Hare, Belgian,NZW Rabbit,Rabbit, Chinchilla,Rabbit, NZW,Rabbit, New Zealand,Rabbits, Chinchilla,Rabbits, Domestic,Rabbits, NZW,Rabbits, New Zealand,Zealand Rabbit, New,Zealand Rabbits, New,cuniculus, Oryctolagus
D004290 DOM 2,5-Dimethoxy-4-Methylamphetamine A psychedelic phenyl isopropylamine derivative, commonly called DOM, whose mood-altering effects and mechanism of action may be similar to those of LSD. 2,5-Dimethoxy-4-Methylamphetamine,2,5-Dimethoxy-4-Methylamphetamine (DOM),1-(2,5-Dimethoxy-4-Methylphenyl)-2-Aminopropane,2 5 DOM,2,5-Dimethoxy-4-Methylamphetamine Hydrochloride, (+,-)-Isomer,2,5-Dimethoxy-4-Methylamphetamine Hydrochloride, (R)-Isomer,2,5-Dimethoxy-4-Methylamphetamine Hydrochloride, (S)-Isomer,2,5-Dimethoxy-4-Methylamphetamine, (+,-)-Isomer,2,5-Dimethoxy-4-Methylamphetamine, (R)-Isomer,2,5-Dimethoxy-4-Methylamphetamine, (S)-Isomer,2,5-Dimethoxy-4-Methylamphetamine, Hydrochloride,2,5 Dimethoxy 4 Methylamphetamine,2,5-Dimethoxy-4-Methylamphetamine, DOM,DOM 2,5 Dimethoxy 4 Methylamphetamine
D000662 Amphetamines Analogs or derivatives of AMPHETAMINE. Many are sympathomimetics and central nervous system stimulators causing excitation, vasopressin, bronchodilation, and to varying degrees, anorexia, analepsis, nasal decongestion, and some smooth muscle relaxation.
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013347 Subcellular Fractions Components of a cell produced by various separation techniques which, though they disrupt the delicate anatomy of a cell, preserve the structure and physiology of its functioning constituents for biochemical and ultrastructural analysis. (From Alberts et al., Molecular Biology of the Cell, 2d ed, p163) Fraction, Subcellular,Fractions, Subcellular,Subcellular Fraction

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