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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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Peng Zhang et al.
Acta pharmacologica Sinica, 27(8), 1097-1102 (2006-07-27)
To investigate the biotransformation of indomethacin, the first of the newer nonsteroidal anti-inflammatory drugs, by filamentous fungus and to compare the similarities between microbial transformation and mammalian metabolism of indomethacin. Five strains of Cunninghamella (C elegans AS 3.156, C elegans
H Alho et al.
Cell growth & differentiation : the molecular biology journal of the American Association for Cancer Research, 5(9), 1005-1014 (1994-09-01)
A recognition site for benzodiazepines structurally different from that linked to the gamma-aminobutyric acid receptor subtype A or the "central type" benzodiazepine receptor has been located mainly in the outer membranes of mitochondria and designated mitochondrial benzodiazepine receptor (MBR). A
E Kwong et al.
Journal of pharmaceutical sciences, 71(7), 828-830 (1982-07-01)
Indomethacin and its impurities in suppository and capsule formulations were quantitatively determined by HPLC using a reversed-phase, octadecyl column and a mobile phase of methanol-water-acetonitrile-acetic acid (55:35:10:1). Analysis of the suppository formulations provided a mean potency for indomethacin of 103.8%.
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)
Ina Petry et al.
International journal of pharmaceutics, 544(1), 172-180 (2018-04-19)
The use of co-amorphous systems for solubility enhancement of poorly water-soluble drugs has recently gained interest in the field of pharmaceutical technology. However, undesired co-amorphisation of a drug may lead to an alteration of the performance of the drug product
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