5-Methoxyindole-3-acetic acid
(Synonyms: 5-甲氧基吲哚-3-乙酸) 目录号 : GC46078
A methoxyindole
Cas No.:3471-31-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
5-Methoxyindole-3-acetic acid (5-MIAA) is a methoxyindole that is synthesized in rat pineal gland, retina, and harderian gland.1 Following conversion to a peroxyl radical by horseradish peroxidase (HRP), 5-MIAA increases the rate of formation of thiobarbituric acid reactive substances (TBARS) in liposomes and is cytotoxic to V79 hamster cells.2,3 In vivo, 5-MIAA (100 and 200 μg/animal) prolongs the estrous cycle and increases diestrous smears, uterine weight, the number of uterine follicles, and plasma levels of 17β-estradiol in female rats.1
|1. Ocal-Irez, T., Durmus, G., Sekerkiran, Y., et al. Effect of a pineal indolamine, 5-methoxyindole-3-acetic acid, on the estrous cycle and reproductive organs of female wistar albino rats. Brain Res. 493(1), 1-7 (1989).|2. Candeias, L.P., Folkes, L.K., Porssa, M., et al. Enhancement of lipid peroxidation by indole-3-acetic acid and derivatives: Substituent effects. Free Radic. Res. 23(5), 403-418 (1995).|3. Folkes, L.K., Candeias, L.P., and Wardman, P. Toward targeted "oxidation therapy" of cancer: Peroxidase-catalysed cytotoxicity of indole-3-acetic acids. Int. J. Radiat. Oncol. Biol. Phys. 42(4), 917-920 (1998).
| Cas No. | 3471-31-6 | SDF | |
| 别名 | 5-甲氧基吲哚-3-乙酸 | ||
| Canonical SMILES | OC(CC1=CNC2=CC=C(OC)C=C21)=O | ||
| 分子式 | C11H11NO3 | 分子量 | 205.2 |
| 溶解度 | DMF: 20 mg/ml,DMSO: 20 mg/ml,DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml,Ethanol: 10 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.8733 mL | 24.3665 mL | 48.7329 mL |
| 5 mM | 0.9747 mL | 4.8733 mL | 9.7466 mL |
| 10 mM | 0.4873 mL | 2.4366 mL | 4.8733 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Effect of light on 5-Methoxyindole-3-acetic acid in the rat
J Neural Transm (Vienna) 2001;108(5):503-11.PMID:11459072DOI:10.1007/s007020170052.
This study aims to determine the effects of light on the levels of 5-MIAA to provide further information on this indoleamine, using a sensitive and specific radioimmunoassay (RIA) for immunoreactive 5-Methoxyindole-3-acetic acid (5-MIAA) developed in our laboratories using a specific antibody and tritiated label. Significant differences were found in the immunoreactive 5-MIAA levels between mid-light and mid-dark pineal glands in rats adapted to 12/12 hrs light/dark and in constant darkness. Under constant light, the circadian rhythm was abolished. The rat serum displayed no diurnal variations in 5-MIAA levels under aux photic conditions. The persistence of rhythms found in constant darkness but abolished in constant light suggests that the pineal 5-MIAA is endogenous and uses light as an environmental cue. In addition to melatonin, 5-MIAA could possibly be another pineal photoperiodic signal in animals.
Identification and quantification of 5-Methoxyindole-3-acetic acid in human urine
Anal Biochem 1985 Jan;144(1):86-93.PMID:2580458DOI:10.1016/0003-2697(85)90087-9.
A putative pineal metabolite, 5-Methoxyindole-3-acetic acid, was quantified in human urine by a gas chromatographic-mass spectrometric method. Excretion of 4.77 +/- 2.25 microgram/day (mean +/- SD) was consistent from each of three normal subjects over 2-4 weeks. Excretion did not vary with regard to menstrual cycle. The daily pattern of excretion bore no relationship to that of 6-hydroxymelatonin, the major metabolite of melatonin, indicating that the major portion of urinary 5-Methoxyindole-3-acetic acid does not derive from melatonin.
Demonstration of antifungal and anti-human immunodeficiency virus reverse transcriptase activities of 6-methoxy-2-benzoxazolinone and antibacterial activity of the pineal indole 5-Methoxyindole-3-acetic acid
Comp Biochem Physiol C Toxicol Pharmacol 2002 Jun;132(2):261-8.PMID:12106902DOI:10.1016/s1532-0456(02)00071-6.
6-methoxy-2-benzoxazolinone (6-MBOA), a naturally occurring progonadal compound present in grasses with structural resemblance to melatonin, was tested for antifungal activity against Fusarium oxysporum, Rhizoctonia solani and Coprinus comatus. A variety of pineal products was also examined for the sake of comparison, including 5-methoxytryptamine, melatonin, 5-methoxytryptophol, 5-hydroxytryptamine, 5-Methoxyindole-3-acetic acid and 5-hydroxytryptophol. The assay for antifungal activity was carried out in Petri plates containing potato dextrose agar. It was found that 6-MBOA most potently inhibited the growth of C. comatus, R. solani and F. oxysporum. When 6-MBOA and pineal indoles were tested for antibacterial activity against the bacterium Agrobacterium tumefaciens, 5-Methoxyindole-3-acetic acid was found to be the most potent. 6-MBOA most potently inhibited human immunodeficiency virus-1 reverse transcriptase.
The pineal gland of the mole (Talpa europaea L.). VII. Activity of hydroxyindole-O-methyltransferase (HIOMT) in the formation of 5-methoxytryptophan, 5-methoxytryptamine, 5-Methoxyindole-3-acetic acid, 5-methoxytryptophol and melantonin in the eyes and the pineal gland
J Neural Transm 1981;51(3-4):271-82.PMID:6169801DOI:10.1007/BF01248958.
Using a method in which no substrate is added to the incubation medium, the capacity of HIOMT to synthesize 5-methoxytryptophan, 5-methoxytryptamine, 5-Methoxyindole-3-acetic acid, 5-methoxytryptophol and melatonin has been determined in the pineal and the eyes of the mole, a mammal having an atrophied visual system. The results demonstrate that the indoleamine metabolism in the retina is similar to the indoleamine metabolism in the pineal. Moreover, in all animals studied both eyes together synthesize 2 to 30 times more of 5-methoxyindoles than the pineal, a result which proves again that the pineal is not the only and not always the most important source of 5-methoxyindoles. With the exception of 5-Methoxyindole-3-acetic acid, the synthesis of which is practically neglectable, the production of all other 5-methoxyindoles in the pineal as well as in the retinae is always larger than that of melatonin. In the pineal, 5-methoxytryptophan, for example, is synthesized in a quantity which is 60 to 170 times larger than that of melatonin, while in the retinae the synthesized amount of 5-methoxytryptophan is even 60 to 1000 times larger than that of melatonin.
Retinal 5-methoxytryptamine and 5-Methoxyindole-3-acetic acid in the rat and quail: diurnal rhythms and interspecies differences
Biochem Biophys Res Commun 1997 Oct 9;239(1):353-6.PMID:9345324DOI:10.1006/bbrc.1997.7475.
Endogenous 5-methoxytryptamine (5MT) and its biosynthetic oxidation product, 5-Methoxyindole-3-acetic acid (5MIAA), were successfully identified and measured in the retina of the rat and quail by gas chromatography/electron-capture negative ion chemical ionization mass spectrometry (GC/EC-NICI-MS). In the rat retina, diurnal rhythms of 5MT and 5MIAA, with high levels at mid-light and opposite to that of melatonin, were observed. In the quail, high levels of retinal 5MT and 5MIAA were found at mid-dark, and in phase to that of melatonin. Biosynthetic pathways for retinal 5MT and 5MIAA in the rat and quail were discussed in relation to the diurnal rhythms observed. Our results indicate that the biosynthesis and physiological functions of retinal 5MT and 5MIAA could be species dependent.