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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)
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
R D Johnson et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 805(2), 223-234 (2004-05-12)
Toxicological examination of fatal aviation accident victims routinely includes analysis of ethanol levels. However, distinguishing between antemortem ingestion and postmortem microbial formation complicates all positive ethanol results. Development of a single analytical approach to determine concentrations of 5-hydroxytryptophol (5-HTOL) and
J Krzek et al.
Journal of AOAC International, 84(6), 1703-1707 (2002-01-05)
A densitometric method was developed for the identification and determination of indomethacin and its degradation products, 4-chlorobenzoic acid and 5-methoxy-2-methyl-3-indoleacetic acid, in pharmaceuticals. To separate these compounds, silica gel-coated thin-layer chromatography plates and the following mobile phase were used: 2-propanol-25%
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
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