ELECTROCHEMICAL OXIDATION OF 5-HYDROXYTRYPTAMINE IN AQUEOUS-SOLUTION AT PHYSIOLOGICAL PH

被引：86

作者：

WRONA, MZ ^{[1
]}

DRYHURST, G ^{[1
]}

机构：

[1] UNIV OKLAHOMA,DEPT CHEM & BIOCHEM,NORMAN,OK 73019

来源：

BIOORGANIC CHEMISTRY | 1990年 / 18卷 / 03期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0045-2068(90)90005-P

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The electrochemical oxidation of the indolic neurotransmitter 5-hydroxytryptamine (5-HT) has been studied in aqueous solution at physiological pH using a pyrolytic graphite electrode. The initial step in the oxidation involves a 2e,1H+ reaction leading to a reactive carbocation intermediate (28b). This intermediate is attacked by 5-HT in an ion-substrate reaction to give 5,5′-dihydroxy-4,4′-bitryptamine (1) as the major product along with the C(4)OC(5′) bridged dimer 9. Alternatively cation 28b is attacked by water to yield, ultimately, tryptamine-4,5-dione (5). Many additional reactions occur between primary dimers 1 and 9 and carbocation 28b such that a very complex mixture of ultimate products are formed. A total of 15 products have been isolated and partially or completely characterized. It is possible that the oxidation reaction pathways and product profile elucidated might have a bearing on, as yet hypothetical, aberrant oxidation reactions of 5-HT in the central nervous system which could play a role in the etiology of mental illnesses such as diseases of the Alzheimer's type. © 1990.

引用

页码：291 / 317

页数：27

共 45 条

[21]

Himwich H. E., 1967, AMINES SCHIZOPHRENIA

[22]

HUMPHRIES K, UNPUB

[23] ALTERED PLATELET SEROTONIN UPTAKE KINETICS IN SCHIZOPHRENIA AND DEPRESSION [J].