RT Journal Article
SR Electronic
T1 THE METABOLISM OF SAFROLE AND 2',3'-EPOXYSAFROLE IN THE RAT AND GUINEA PIG
JF Drug Metabolism and Disposition
JO Drug Metab Dispos
FD American Society for Pharmacology and Experimental Therapeutics
SP 489
OP 498
VO 2
IS 6
A1 W. G. STILLWELL
A1 M. J. CARMAN
A1 L. BELL
A1 M. G. HORNING
YR 1974
UL http://dmd.aspetjournals.org/content/2/6/489.abstract
AB The metabolism of safrole (4-allyl-1,2-methylenedioxybenzene) and safrole epoxide [1,2-methylenedioxy-4-(2,3-epoxypropyl)benzene] was studied in the rat and guinea pig. After intraperitoneal administration of safrole, the major urinary metabolites identified by gas chromatography and mass spectrometry were 1,2-dihydroxy-4-allylbenzene, 1,2-methylenedioxy-4-(1-hydroxyallyl)benzene, 1,2-methylenedioxy-4-(2,3-dihydroxypropyl)benzene, 1,2-dihydroxy-4-(2,3-dihydroxypropyl)benzene, 2-hydroxy-3-(3,4-methylenedioxyphenyl)propanoic acid, and 3,4-methylenedioxybenzoylglycine. The conversion of the allyl side chain to a 2,3-dihydroxypropyl side chain probably involves safrole epoxide as an intermediate. After intraperitoneal administration of safrole epoxide, 1,2-methylenedioxy-4-(2,3-dihydroxypropyl)benzene, 1,2-dihydroxy-4-(2,3-dihydroxypropyl)benzene, 2-hydroxy-3-(3,4-methylenedioxyphenyl)propanoic acid, and 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoic acid were identified in rat and guinea pig urine. A small amount of a triol [1,2-methylenedioxy-4-(1,2,3-trihydroxypropyl)benzene] was found only in rat urine. Unchanged safrole epoxide was also found in the urine of both species, indicating that the epoxide was sufficiently stable in vivo to circulate in the blood and to be excreted in urine. Copyright © 1974 by The American Society for Pharmacology and Experimental Therapeutics