Urinary excretion of the enantiomers of 1-methyl-1,2,3,4-tetrahydro-beta-carboline in unequal abundance implies enzymatic metabolism in man.

Abstract

1-Methyl-1,2,3,4-tetrahydro-beta-carboline, a condensation product of tryptamine and acetaldehyde, is one of the neuropharmacologically active alkaloids in mammals. Its enantiomers excreted in human urine were independently analyzed by gas chromatography-negative ion chemical ionization mass spectrometry. Mass fragmentograms of the racemic 1-methyl-1,2,3,4-tetrahydro-beta-carboline offered two peaks with (S)-(-)- and (R)-(+)-configurations which were eluted in this retention order. When the racemic tetradeuterated 1-methyl-1,2,3,4-tetrahydro-beta-carboline was orally administered to a human subject, the urinary tetradeuterated enantiomers were found to be of unequal abundance. The deuterated (R)-(+)-1-methyl-1,2,3,4-tetrahydro-beta-carboline was predominantly excreted in human urine about 3-times over the deuterated (S)-(-)-one. The stereoselective difference in the urinary excretion of 1-methyl-1,2,3,4-tetrahydro-beta-carboline administered exogenously implies that it is enzymatically metabolized, but not that its biosynthesis is associated with an enzymatic reaction.