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105171

Sigma-Aldrich

5-Methoxy-2-methyl-3-indoleacetic acid

98%

Synonym(s):

N-Des(4-chlorobenzoyl)indomethacin, NSC 97026, 2-(5-Methoxy-2-methyl-1H-indol-3-yl)acetic acid

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About This Item

Empirical Formula (Hill Notation):
C12H13NO3
CAS Number:
2882-15-7
Molecular Weight:
219.24
EC Number:
220-734-7
MDL number:
MFCD00005618
UNSPSC Code:
12352100
PubChem Substance ID:
24846692
NACRES:
NA.22

Assay

98%

mp

161-163 °C (lit.)

solubility

methanol: soluble

SMILES string

COc1ccc2[nH]c(C)c(CC(O)=O)c2c1

InChI

1S/C12H13NO3/c1-7-9(6-12(14)15)10-5-8(16-2)3-4-11(10)13-7/h3-5,13H,6H2,1-2H3,(H,14,15)

InChI key

TXWGINUZLBAKDF-UHFFFAOYSA-N

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General description

5-Methoxy-2-methyl-3-indoleacetic acid is hydrolysis product of indomethacin.

Application

5-Methoxy-2-methyl-3-indoleacetic acid was used for quantitative determination of indomethacin and its major impurities in suppository and capsule formulations by HPLC. 5-Methoxy-2-methyl-3-indoleacetic acid was used in a study to develop fast, sensitive and simultaneous determination of metabolites of serotonin using liquid chromatography with mass spectrometric detection.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Cytostatic activity of pharmacological concentrations of indomethacin in cell cultures and inactivity of closely related compounds.
B M Bayer et al.
Biochemical pharmacology, 30(7), 807-809 (1981-04-01)
P C Smith et al.
Journal of chromatography, 306, 315-321 (1984-03-09)
Quantitation of total amounts (i.e., free compound plus glucuronide conjugate) of indomethacin (INDO) and its deschlorobenzoyl (DBI) and desmethyl (DMI) metabolites in human urine is described. An aliquot (0.4 ml) of urine is incubated with glucuronidase (1000 U, 2 h
Mariusz Stolarczyk et al.
Journal of AOAC International, 87(3), 592-595 (2004-08-04)
Derivative spectrophotometry was employed to develop a rapid and accurate method for simultaneous determination of indomethacin and 5-methoxy-2-methyl-3-indoleacetic acid as its possible impurity in Metindol injections. At the selected wavelengths, 233.04 and 284.65 nm, no interference between the components determined
W I Rosenblum et al.
Prostaglandins, leukotrienes, and medicine, 8(2), 125-132 (1982-02-01)
5-methoxy-2-methyl-3-indole acetic acid (5MIAA) is a metabolite and alkali hydrolysis product of indomethacin. This indole derivative was previously found to be an effective in vivo inhibitor of platelet aggregation in an experimental model of microvascular injury in the mouse. In
In vitro effect of endozepines on frog adrenocortical cells.
O Lesouhaitier et al.
Annals of the New York Academy of Sciences, 839, 596-597 (1998-06-18)
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