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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

functional group

carboxylic acid

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF5171
BCCC4344
BCBZ4095
BCBS1196V
STBF4226V

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W I Rosenblum et al.
Prostaglandins, 21(4), 667-673 (1981-04-01)
Previous studies suggested that one of the hydrolysis products of indomethacin, either 4-chlorobenzoic acid or 5-methoxy-2-methyl-3-indole acetic acid, can inhibit platelet aggregation in vivo. If correct, this hypothesis explains the apparent action of indomethacin dissolved at high pH where hydrolysis
T B Vree et al.
Journal of chromatography, 616(2), 271-282 (1993-07-02)
Indomethacin is metabolized in humans by O-demethylation, and by acyl glucuronidation to the 1-O-glucuronide. Indomethacin, its metabolite O-desmethylindomethacin (DMI) and their conjugates can be measured directly by gradient high-performance liquid chromatographic analysis without enzymic deglucuronidation. The glucuronide conjugates were isolated
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
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
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%.
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