ISSN:
1432-1912
Keywords:
Tryptolines
;
Tetrahydro-β-carbolines
;
Aromatic hydroxylation
;
Chiral gas chromatography
;
Gas chromatography-mass spectrometry
Source:
Springer Online Journal Archives 1860-2000
Topics:
Medicine
Notes:
Summary Racemic methtryptoline (1-methyltetrahydro-β-carboline) and 5-hydroxymethtryptoline-9-carboxylic acid (6-hydroxy-1-methyltetrahydro-β-carboline-1-carboxylic acid) were administered intraperitoneally to rats and the components of their urine was subsequently investigated by chiral gas chromatography-mass spectrometry. Methtryptoline rapidly became hydroxylated in the 5- and 6-position and excreted in urine. There was about a ninefold predominance of the S(−) enantiomer over the other in the 5-hydroxylated species, while the 6-hydroxylation produced a small excess of the R(+) enantiomer. About 75% of the injected dose of methtryptoline was recovered in the urine as 5- and 6-hydroxylated compounds during the first 24 h period, demonstrating that hydroxylation represents the major metabolic pathway. Treatment with 6-hydroxymethtryptoline-9-carboxylic acid led to a fivefold increase in the urinary excretion of 5-hydroxymethtryptoline during the first 24 h period with a predominance of the S(−)-enantiomer, indicating a much smaller conversion rate than from methtryptoline. It was concluded that hydroxylation of methtryptoline is a likely pathway for the natural formation of 5-hydroxymethtryptoline.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00512946
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