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HomeProduct name listALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID

ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID

Synonym(s):α-Methyl-p-(1-oxo-2-isoindolinyl)benzeneacetic acid

  • CAS NO.:31842-01-0
  • Empirical Formula: C17H15NO3
  • Molecular Weight: 281.31
  • MDL number: MFCD00057144
  • EINECS: 250-833-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-09 19:38:33
ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID Structural

What is ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID?

Chemical properties

ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID is Off-White Solid

Originator

Flosint,Carlo Erba,Italy,1976

The Uses of ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID

analgesic, antiinflammatory

The Uses of ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID

ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID is a non-steroidal anti-inflammatory agent used for treatment of pain and inflammation

Definition

ChEBI: A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(1-oxo-1,3-dihydroisoindol-2-yl)phenyl group. Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causi g severe gastrointestinal bleeding. It has been subsequently found to increase production of the survival motor neuron protein.

Manufacturing Process

The mixture of 7.9 g of ethyl α-(4-aminophenyl)propionate and 8.3 g of ethyl 2-chloromethylbenzoate is refluxed under nitrogen for one hour. The residue is recrystallized from hexane, to yield the ethyl α-[4-(1-oxo-isoindolino)-phenyl]- propionate of the formulamelting at 104° to 106°C. The mixture of 4.5 g thereof, 1.6 g of potassiumhydroxide, 2 ml of water and 250 ml of ethanol is refluxed under nitrogen for 2 hours and evaporated under reduced pressure. The residue is taken up in water, the solution washed with chloroform, acidified with hydrochloric acid and extracted with ethyl acetate. The extract is dried, evaporated and the residue recrystallized from ethyl acetate, to yield the corresponding free acid melting at 208° to 210°C. (Procedure reported in US Patent 3,767,805.)

brand name

Endyne;Fenint;Flogosan;Flosine;Flosyn;K 4277;Miantor.

Therapeutic Function

Antiinflammatory

World Health Organization (WHO)

Indoprofen, a nonsteroidal anti-inflammatory agent, was introduced in 1976 for the treatment of rheumatic disorders. By 1983 its use had been associated with serious adverse effects, some of which were fatal. This led to its withdrawal in the United Kingdom and Cyprus. In 1984 reports of intestinal tumours in rats led to the drug's temporary withdrawal in Germany and Italy. This was followed immediately by the suspension of marketing worldwide by the major manufacturer.

Properties of ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID

Melting point: 213-214°
Boiling point: 423.97°C (rough estimate)
Density  1.1302 (rough estimate)
refractive index  1.4500 (estimate)
storage temp.  2-8°C
solubility  Methanol (Slightly, Sonicated)
pka pKa 5.8 (Uncertain)
form  neat
form  Solid
color  White to off-white

Safety information for ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Health Hazard
GHS08
GHS Hazard Statements H301:Acute toxicity,oral
H351:Carcinogenicity
Precautionary Statement Codes P201:Obtain special instructions before use.

Computed Descriptors for ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID

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