Rapid hydroxylation of methtryptoline (1-methyltetrahydro-beta-carboline) in rat: identification of metabolites by chiral gas chromatography-mass spectrometry.
Rapid hydroxylation of methtryptoline (1-methyltetrahydro-beta-carboline) in rat: identification of metabolites by chiral gas chromatography-mass spectrometry.
复制标题
大鼠体内甲基色氨酸（1-甲基四氢-β-咔啉）的快速羟基化：通过手性气相色谱-质谱法鉴定代谢物。
DOI：
10.1007/bf00512946
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发表时间：
1986
期刊：
影响因子：
--
通讯作者：
Repke,DB
中科院分区：
文献类型：
--
作者：
Beck,O;Faull,KF;Repke,DB
用手性气相色谱-质谱联用技术研究了大鼠腹腔注射外消旋甲基四氢-β-咔啉（1-methyltetrahydro-β-carboline，1-methyltetrahydro-β-carboline）和5-羟基甲基四氢-β-咔啉-9-羧酸（5-hydroxymethytoline-9-carboline-1-carboline-1-carboline-1-carboline-1-carboline）后尿液中的化学成分。甲色托林在5位和6位迅速羟基化，并经尿液排泄。在5-羟基化物质中，S（-）对映体的优势约为其他对映体的9倍，而6-羟基化产生了少量过量的R（+）对映体。在前24小时内，约75%的注射剂量的甲色托林以5-和6-羟基化化合物的形式在尿液中回收，表明羟基化是主要的代谢途径。用6-羟甲色托林-9-羧酸处理导致前24小时内5-羟甲色托林的尿排泄增加5倍，主要是S（−）-对映体，表明转化率远低于甲色托林。由此得出结论，甲色托林的羟基化可能是5-羟基甲色托林天然形成的途径。
Racemic methtryptoline (1-methyltetrahydro-β-carboline) and 5-hydroxymethtryptoline-9-carboxylic acid (6-hydroxy-1-methyltetrahydro-β-carboline-1-carboxylic acid) were administeredintraperitoneallyto 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.