RT Journal Article
SR Electronic
T1 In vivo phenolic metabolites of N-alkylamphetamines in the rat. Evidence in favor of catechol formation.
JF Drug Metabolism and Disposition
JO Drug Metab Dispos
FD American Society for Pharmacology and Experimental Therapeutics
SP 256
OP 261
VO 4
IS 3
A1 Coutts, R T
A1 Dawson, G W
A1 Kazakoff, C W
A1 Wong, J Y
YR 1976
UL http://dmd.aspetjournals.org/content/4/3/256.abstract
AB The major in vivo metabolites of 1-phenyl-2-(n-propylamino)propane (N-n-propylamphetamine) in the rat were phenolic compounds, identified as 1-(4-hydroxyphenyl)-2-(n-propylamino)-propane (metabolite A) and 1-(4-hydroxy-3-methoxyphenyl)-2-(n-propylamino)propane (metabolite B) by gas chromatography-mass spectrometry, and by comparison with authentic synthetic samples of A and B. Metabolites A and B were formed from the substrate in 18.3% and 3.3% yields, respectively, and are excreted in the urine mainly in conjugated form. In vivo metabolism in the rat of the homolog, 1-phenyl-2-(n-butylamino)propane (N-n-butylamphetamine) resulted in the formation of two homologous metabolites in similar yields, which were tentatively identified, from their gas chromatographic and mass spectrometric behav-propane (metabolite A) and 1-(4-hydroxy-3-methoxyphenyl)-2-(n-propylamino)propane (metaboior and by comparison with metabolites A and B, as 2-(n-butylamino)-1-(4-hydroxyphenyl)propane (metabolite C) and 2-(n-butylamino)-1-(4-hydroxy-3-methoxyphenyl)propane (metabolite D). It is suggested that the methylated metabolites B and D were formed from metabolites A and C, respectively, via catecholamine intermediates.