4,5-dihydroxytryptamine | 42241-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4,5-dihydroxytryptamine
• 英文别名: 3-(2-aminoethyl)-1H-indole-4,5-diol
• CAS: 42241-03-2
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: HKPREGWFNPFQEA-UHFFFAOYSA-N

物化性质

• 沸点：
  471.9±40.0 °C(Predicted)
• 密度：
  1.421±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.3
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-羟基色胺 在 dipotassium hydrogenphosphate 作用下， 以 水 为溶剂， 生成 4,5-dihydroxytryptamine
  参考文献：
  名称：

  Electrochemical Oxidation of Histamine and Serotonin at Highly Boron-Doped Diamond Electrodes

  摘要：

  使用多晶掺硼金刚石薄膜电极研究了组胺和血清素在中性水介质（pH 值为 7.2）中的电化学反应。研究中使用了循环伏安法、流体动力伏安法和带有安培检测功能的流动注射分析法（FIA）来研究氧化反应。使用抛光玻璃碳（GC）电极进行了对比实验。在金刚石电极上，组胺的循环伏安图具有高度的重现性和清晰度，峰值电位为 1.40 V vs SCE。在分析物浓度达到或超过 100 μM 时，金刚石电极获得的伏安信号-背景比比 GC 电极高出 1 个数量级。伏安测量的线性动态范围为 3-4 个数量级，检测限为 1 μM。对于 5- 羟色胺（5-HT），也获得了清晰的扫描速率依赖性伏安图。伏安图的特征表明其表面没有吸附其氧化产物。在几个小时的实验时间内，没有观察到电极堵塞或失活现象。通过使用金刚石电极的 FIA 技术，组胺的检出限为 0.5 μM（信噪比为 13.8）。用同样的方法在金刚石电极上对 5-HT 的检测限也非常低（10 nM）。金刚石电极测定 5-HT 的线性动态范围为 10 nM 至 100 μM，测定组胺的线性动态范围为 0.5 至 100 μM。不同薄膜之间的 FIA 反应具有很高的重现性，在实际检测限内的反应变异性低于 7%。

  DOI：

  10.1021/ac9908748

文献信息

• Influence of L-Cysteine on the Oxidation Chemistry of Serotonin
  作者：M.Z. Wrona、S. Singh、G. Dryhurst

  DOI：10.1006/bioo.1994.1035

  日期：1994.12

  L-Cysteine (CySH) intervenes in the normal electrochemically driven oxidation of 5-hydroxytryptamine (5-HT; serotonin) at physiological pH by scavenging the quinone imine proximate oxidation product of this indolic neurotransmitter to give 4-S-cysteinyl-5-hydroxy-tryptamine (4-S-CyS-5-HT). The latter cysteinyl conjugate is more easily electro-oxidized than 5-HT and, in the presence of free CySH, undergoes a complex series of reactions leading to 8-(2-aminoethyl)-1,2,3,5,6,9-hexahydro-5,9-dioxo-pyrrolo [3, 2-g] [1, 4] benzothiazine-2-carboxylic acid (20) and N-[7-[(2-amino-2-carboxyethyl) thio]-3-(2-aminoethyl)-1,4-dihydro-4-oxo-5H-indol-5-ylidene]-L-cysteine (4). CySH also reacts with another normal oxidation product of 5-HT, tryptamine-4,5-dione, to give 4 and 20. There is evidence that aberrant oxidative metabolism of 5-HT occurs in the brains of Alzheimer's Disease patients. In the event that such reactions occur in the cytoplasm of serotonergic nerve terminals or axons they would necessarily expose electrophilic intermediates and products to the intraneuronal nucleophiles CySH and GSH. The results of this study indicate that 4 and 20 might represent aberrant oxidative metabolites formed in such reactions. However, the ease of oxidation of 4-S-CyS-5-HT compared to 5-HT suggest that this conjugate is likely to be only a transient species in vivo under conditions where the neurotransmitter is oxidized. (C) 1994 Academic Press, Inc.
• Electrochemical Oxidation of Histamine and Serotonin at Highly Boron-Doped Diamond Electrodes
  作者：B. V. Sarada、Tata N. Rao、D. A. Tryk、A. Fujishima

  DOI：10.1021/ac9908748

  日期：2000.4.1

  The electrochemistry of histamine and serotonin in neutral aqueous media (pH 7.2) was investigated using polycrystalline, boron-doped diamond thin-film electrodes. Cyclic voltammetry, hydrodynamic voltammetry, and flow injection analysis (FIA) with amperometric detection were used to study the oxidation reactions. Comparison experiments were carried out using polished glassy carbon (GC) electrodes. At diamond electrodes, highly reproducible and well-defined cyclic voltammograms were obtained for histamine with a peak potential at 1.40 V vs SCE. The voltammetric signal-to-background ratios obtained at diamond were 1 order of magnitude higher than those obtained for GC electrodes at and above 100 μM analyte concentrations. A linear dynamic range of 3−4 orders of magnitude and a detection limit of 1 μM were observed in the voltammetric measurements. Well-defined sweep rate-dependent voltammograms were also obtained for 5-hydroxytryptamine (5-HT). The characteristics of the voltammogram indicated lack of adsorption of its oxidation products on the surface. No fouling or deactivation of the electrode was observed within the experimental time of several hours. A detection limit of 0.5 μM (signal-to-noise ratio 13.8) for histamine was obtained by use of the FIA technique with a diamond electrode. A remarkably low detection limit (10 nM) was obtained for 5-HT on diamond by the same method. Diamond electrodes exhibited a linear dynamic range from 10 nM to 100 μM for 5-HT determination and a range of 0.5−100 μM for histamine determination. The FIA response was very reproducible from film to film, and the response variability was below 7% at the actual detection limits.

  使用多晶掺硼金刚石薄膜电极研究了组胺和血清素在中性水介质（pH 值为 7.2）中的电化学反应。研究中使用了循环伏安法、流体动力伏安法和带有安培检测功能的流动注射分析法（FIA）来研究氧化反应。使用抛光玻璃碳（GC）电极进行了对比实验。在金刚石电极上，组胺的循环伏安图具有高度的重现性和清晰度，峰值电位为 1.40 V vs SCE。在分析物浓度达到或超过 100 μM 时，金刚石电极获得的伏安信号-背景比比 GC 电极高出 1 个数量级。伏安测量的线性动态范围为 3-4 个数量级，检测限为 1 μM。对于 5- 羟色胺（5-HT），也获得了清晰的扫描速率依赖性伏安图。伏安图的特征表明其表面没有吸附其氧化产物。在几个小时的实验时间内，没有观察到电极堵塞或失活现象。通过使用金刚石电极的 FIA 技术，组胺的检出限为 0.5 μM（信噪比为 13.8）。用同样的方法在金刚石电极上对 5-HT 的检测限也非常低（10 nM）。金刚石电极测定 5-HT 的线性动态范围为 10 nM 至 100 μM，测定组胺的线性动态范围为 0.5 至 100 μM。不同薄膜之间的 FIA 反应具有很高的重现性，在实际检测限内的反应变异性低于 7%。