5-Methoxy-2-methylindole-3-acetic acid (HCID 76151)

Overview

N-Deschlorobenzoyl indomethacin is a member of indole-3-acetic acids.

Names & identifiers

Preferred name: 5-Methoxy-2-methylindole-3-acetic acid
IUPAC: 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetic acid
English name: 5-Methoxy-2-methyl-3-indoleacetic acid
Molecular formula: C12H13NO3
Molecular weight: 219.24

Names & synonyms

2882-15-75-methoxy-2-methylindole-3-acetic acid5-Methoxy-methylindoleacetic acidKY9AD0AQM0Deschlorobenzoylindomethacin(des-4-chlorobenzoyl)indomethacinDTXSID00183009RefChem:913496DTXCID601055005-Methoxy-2-methyl-3-indoleacetic acid2-(5-methoxy-2-methyl-1H-indol-3-yl)acetic acidN-Deschlorobenzoyl indomethacin

Show more names

NSC 970265-MeO,2-Me-IAAVITAS-BB TBB000392TIMTEC-BB SBB003362Indomethacin USP RC AAcemetacin Impurity 3Indomethacin Impurity BIndomethacin Impurity 13Indomethacin EP Impurity B

(5-Methoxy-2-methyl-1H-indol-3-yl)acetic acid5 MIAA1H-Indole-3-acetic acid, 5-methoxy-2-methyl-MFCD00005618Indometacin EP Impurity BDESCHLOROBENZOYL INDOMETHACINNSC-970262-(5-methoxy-2-methylindol-3-yl)acetic acid

Database identifiers

CAS: 2882-15-7
PubChem CID: 76151
DTXSID: DTXSID00183009
ChEMBL: CHEMBL1058
ChEBI: CHEBI:172459
UNII: KY9AD0AQM0
EC Number: 220-734-7
Nikkaji: J306.806D

Properties

Computed structural properties

XLogP: 1.9
Topological polar surface area: 62.3 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 16
Formal charge: 0
Complexity: 269

Experimental & physicochemical properties

DrugsPharmaceuticals -> Metabolite of Acemetacin

Physicochemical properties

Melting point: 161 · 161-163 °C (lit.)
Boiling point: 360.05 °C · 360.05°C (rough estimate)
Density: 1.1825 · 1.1825 (rough estimate)
refractive index: 1.527 · 1.5270 (estimate)
storage temp.: 2 · 2-8°C
solubility: methanol: soluble
pka: 4.22 · 4.22±0.30(Predicted)
form: Crystalline Powder
color: Off-white to light yellow or light beige
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)
InChIKey: TXWGINUZLBAKDF-UHFFFAOYSA-N
SMILES: COc1ccc2[nH]c(C)c(CC(O)=O)c2c1
CAS DataBase Reference: 2882 · 2882-15-7(CAS DataBase Reference)
FDA UNII: 9 AD0AQM0 · KY9AD0AQM0
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 24 · 24/25
WGK Germany: 3 · 3
HS Code: 29349990 · 29349990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29349990
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Pharmacology

Tissue LocationsKidney

Cellular LocationsExtracellular

Applications · 4 items

UsesReactant for preparation of antimalarial agentsReactant for preparation of ndomethacin analogs as cyclooxygenase and lipoxygenase inhibitors with antiinflammatory activityReactant for preparation of [123I]-indomethacin derivatives as COX-2 targeted imaging agentsReactant for preparation of histone deacetylase inhibitorsReactant for preparation of 2,N6,5′-substituted adenosine derivatives as ligands for A2B adenosine receptorReactant for preparation of prostaglandin D2 receptor antagonist

Uses5-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.

UsesA metabolite of Indomethacin.

General Description5-Methoxy-2-methyl-3-indoleacetic acid is hydrolysis product of indomethacin.