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| | 5-HYDROXYINDOLE-3-ACETIC ACID Basic information |
| Product Name: | 5-HYDROXYINDOLE-3-ACETIC ACID | | Synonyms: | TIMTEC-BB SBB003639;HYDROXYINDOLYL-3-ACETIC ACID, 5-;5-hydroxyindol-3-ylacetic acid;5-HYDROXYINDOLE-3-ACETIC ACID FREE ACID;5-Hydroxy-3-indolyl acetic acid;1H-Indole-3-acetic acid, 5-hydroxy-;Hydroxyindoleacetic Acid;5-HYDROXYINDOLE-3-ACETIC ACID | | CAS: | 54-16-0 | | MF: | C10H9NO3 | | MW: | 191.18 | | EINECS: | 200-195-4 | | Product Categories: | Indoles;Simple Indoles | | Mol File: | 54-16-0.mol |  |
| | 5-HYDROXYINDOLE-3-ACETIC ACID Chemical Properties |
| Melting point | 161-164 °C (dec.) (lit.) | | Boiling point | 326.92°C (rough estimate) | | density | 1.2722 (rough estimate) | | refractive index | 1.5310 (estimate) | | storage temp. | -20°C | | solubility | Soluble in ethanol (50 mg/ml). | | pka | 4.54±0.30(Predicted) | | form | crystalline | | color | off-white to purple | | Sensitive | Light Sensitive | | BRN | 168797 | | Stability: | Air Sensitive, Light Sensitive | | InChIKey | DUUGKQCEGZLZNO-UHFFFAOYSA-N | | CAS DataBase Reference | 54-16-0 |
| Safety Statements | 22-24/25 | | WGK Germany | 3 | | RTECS | NL3650000 | | F | 8-10-23 | | HS Code | 29339980 |
| | 5-HYDROXYINDOLE-3-ACETIC ACID Usage And Synthesis |
| Description | 5-hydroxy Indole-3-acetic acid (5-HIAA) is the primary metabolite of serotonin (5-HT; ). It is formed when 5-HT is metabolized by monamine oxidase and aldehyde dehydrogenase in the liver. 5-HIAA is excreted in urine and has been used as a biomarker for detection of neuroendocrine tumors and an internal standard for the quantification of serotonin metabolism in rat brain using mass spectrometry. 5-HIAA has also been associated with autism, insomnia, and chronic migraine. | | Chemical Properties | beige crystalline powder | | Uses | 5-Hydroxyindole-3-acetic acid is a major serotonin metabolite. | | Uses | 5-Hydroxyindole-3-acetic acid is an impurity of chlorpheniramine (C424300), an antihistaminic agent. | | Definition | ChEBI: A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5. | | General Description | 5-Hydroxyindole-3-acetic acid (5-HIAA) is the catabolic end product of serotonin pathway. 5-HIAA is present in body fluids like cerebrospinal fluid (CSF), blood and urine. The expression levels of 5-HIAA is different among the normal and cancer patients. Sepiapterin reductase deficiency results in low level of 5-HIAA in CSF. 5-HIAA level is low in CSF in patients with bipolar 1 disorder with childhood attention-deficit hyperactivity disorder (ADHD). | | Mechanism of action | The primary
product of the metabolism of serotonin. Formed by the oxidative
deamination of serotonin by monoamine oxidase, presumably
the A isozyme, 5-HIAA is subsequently cleared by an
active transport mechanism. Unlike serotonin, 5-HIAA is not a
neurotransmitter and thus its formation contributes to the termination
of the synaptic actions of serotonin. Inhibition of
monoamine oxidase activity enhances and prolongs the actions
of serotonin. |
| | 5-HYDROXYINDOLE-3-ACETIC ACID Preparation Products And Raw materials |
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