6-Hydroxymethtryptoline is naturally occurring in mammalian urine: identification by combined chiral capillary gas chromatography and high resolution mass spectrometry.

The tricyclic indole derivative 6-hydroxymethtryptoline (7-hydroxy-1-methyltetrahydro-beta-carboline) was identified as a normal constituent of human and cat urine. The identification was based on the correct retention time on a chiral capillary gas chromatographic column and on selected ion monitoring of the molecular ion with the mass spectrometer set at high resolving power (RP 10,000). The quantitation utilized a 13C-labeled analog as internal standard and demonstrated levels of 135 +/- 35 and 174 +/- 42 (pmol ml-1, mean +/- SEM) for the S(-) and R(+) enantiomers, respectively, in human urine. In cat urine, the levels were 203 +/- 55 and 108 +/- 44 (pmol ml-1, mean +/- SEM) for the S(-) and R(+) enantiomers, respectively. In human urine, the compound occurred predominantly in a conjugated form while in cat urine the free compound predominated. It was concluded that 6-hydroxymethtryptoline is naturally occurring in mammalian urine and that it most likely constitutes a metabolite of endogenous methtryptoline (1-methyltetrahydro-beta-carboline).