A methoxyindole
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5-Methoxyindole-3-acetic Acid

Item No. 14019

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-methoxy-1H-indole-3-acetic acid
CAS Number
3471-31-6
Synonyms
  • 5-methoxy IAA
  • 5-Methoxyindoleacetic Acid
  • 5-MIAA
Molecular Formula
C11H11NO3
Formula Weight
205.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 10 mg/ml
λmax
221, 276 nm
SMILES
OC(CC1=CNC2=CC=C(OC)C=C21)=O
InChi Code
InChI=1S/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14)
InChi Key
COCNDHOPIHDTHK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

    $44

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    500 mg

    $80

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    1 g

    $130

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    Product Description

    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 (Item No. 10006315) in female rats.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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).