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Matin SB, Callery PS, Zweig JS, O'Brien A, Rapoport R, Castagnoli N Jr. 
“Stereochemical aspects and metabolite formation in the in vivo metabolism of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane”. 
J Med Chem. 1974 Aug;17(8):877-82.
Our interest in structure-metabolism relationships of pharmacologically active 1-phenyl-2-aminopropanes has led to in vivo investigations of the fate of the psychotomimetic amine l-(2,5-dimethoxy-4-methylphenyl)-2-aminopro- pane (1). Compound 1 was resolved via its o-nitrotartranilate salts.and the absolute configurations were found to be (S)-( +) and ( R )-( -). Determination of the enantiomeric composition of unmetabolized amine excreted in the urine of rabbits treated with racemic 1 established the R / S ratio to be equal to or greater than 1. With the aid of 1-14C (labeled at the benzylic position) it has been established that 1 was extensively metabolized by the rabbit and that of several suspected metabolites only 1-(2,5-dimethoxy-4-carboxyphenyl)-2-aminopropane was excreted to any great extent.
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