CAS： 1006-94-6
MF： C9H9NO
Appearance： white to light brownish crystalline powder
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Description |
5-Methoxyindole is an organic compound and biochemical reagent that is a core component of melatonin and is used in life science research. |
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Uses |
5-Methoxyindole-3-acetic acid (MIAA) is a precursor for Gli1 antitumor agents. It is also used to synthesize inhibitors of nitric oxide production. |
| Synthesis from 5-Methoxy-2-oxindole | Involves chlorination of 5-methoxy-2-oxindole with triphenylphosphine and carbontetrachloride in acetonitrile, followed by catalytic reduction, yielding 5-methoxyindole with 66% total yield. |
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Purification Methods |
Purified by crystallization from cyclohexane or petroleum ether, or a mix of petroleum ether and diethyl ether. |
InChI:InChI=1/C9H9NO/c1-11-8-3-2-7-4-5-10-9(7)6-8/h2-6,10H,1H3
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Monomers of 4-methoxyindole and 5-methoxyindole trapped in low-temperature xenon matrices (15–16 K) were characterized by IR spectroscopy, in separate experiments. Each compound was shown to adopt the most stable 1H-tautomeric form. The photochemistry of the matrix-isolated compounds was then investigated by exciting the matrices with narrowband UV light with λ ≤ 305 nm.
5-Methoxyindole-2-carboxylic acid (5MICA) has also shown beneficial neuroprotective action against ischemic stroke injury and functional improvements after stroke in rats [20]. 5MICA has reduced infarct size, improved oxidative stress status, and improved long-term potentiation [20]. 5MICA acts as an inhibitor of the mitochondrial dihydrolipoamide dehydrogenase (DLDH), which also contributes to the chemical preconditioning and neuroprotection against ischemic injury.
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