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Metaxalone

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Metaxalone Basic information

Product Name:
Metaxalone
Synonyms:
  • 5-[(3,5-dimethylphenoxy)methyl]oxazolidin-2-one
  • 2-Oxazolidinone, 5-((3,5-xylyloxy)methyl)-
  • 2-Oxazolidinone, 5-[(3,5-dimethylphenoxy)methyl]-
  • 5-((3,5-dimethylphenoxy)methyl)-2-oxazolidinon
  • 5-((3,5-Dimethylphenoxy)methyl)-2-oxazolidinone
  • 5-((3,5-xylyloxy)methyl)-2-oxazolidinon
  • 5-((3,5-Xylyloxy)methyl)-2-oxazolidinone
  • 5-(3,5-Xyloloxymethyl)oxazolidin-2-one
CAS:
1665-48-1
MF:
C12H15NO3
MW:
221.25
EINECS:
216-777-6
Product Categories:
  • SKELAXON
  • Various Metabolites and Impurities
  • Metabolites & Impurities
  • Isotope Labeled Compounds
  • Isotope Labelled Compounds
Mol File:
1665-48-1.mol
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Metaxalone Chemical Properties

Melting point:
121-1230C
Boiling point:
225°C/1.5mmHg(lit.)
Density 
1.1514 (rough estimate)
refractive index 
1.5200 (estimate)
Flash point:
9 °C
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
DMSO: ≥2mg/mL (warmed to 60 °C)
pka
12.26±0.40(Predicted)
form 
powder
color 
white to tan
BCS Class
2
InChIKey
IMWZZHHPURKASS-UHFFFAOYSA-N
CAS DataBase Reference
1665-48-1(CAS DataBase Reference)
NIST Chemistry Reference
Metaxalone(1665-48-1)
EPA Substance Registry System
2-Oxazolidinone, 5-[(3,5-dimethylphenoxy)methyl]- (1665-48-1)
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Safety Information

Hazard Codes 
F,T
Risk Statements 
11-23/24/25-39/23/24/25
Safety Statements 
7-16-36/37-45
RIDADR 
UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 
3
RTECS 
RQ3850000
HS Code 
2934990002
Hazardous Substances Data
1665-48-1(Hazardous Substances Data)

MSDS

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Metaxalone Usage And Synthesis

Chemical Properties

White Crystalline Solid

Originator

Skelaxin,Robins,US,1962

Uses

It is a muscle relaxant used to relax muscles and relieve pain

Uses

muscle relaxant (skeletal)

Uses

For the treatment of painful peripheral musculoskeletal conditions and spasticity from upper motor neuron syndromes.

Uses

Metaxalone is a skeletal muscle relaxant that has applications in reducing muscle spasm, limitations in normal motion, and pain caused by musculoskeletal conditions. It is commonly used in combination with analgesics to address low back pain. The molecular or cellular actions of metaxalone is not known.[Cayman Chemical]

Definition

ChEBI: Metaxalone is an aromatic ether.

Manufacturing Process

Urea (118 g, 1.96 mols) was added to 192 g (0.98 mol) of 3-(3',5'- dimethylphenoxy)-1,2-propane-diol which had previously been heated to 150°C. The reaction mixture was then heated rapidly to 195° to 200°C and maintained at this temperature for 5 hours with constant stirring. The resulting mixture was partitioned between water and ethyl acetate and the ethyl acetate layer was dried over sodium sulfate and concentrated. The residue was distilled in vacuo and the fraction boiling at 220° to 225°C/1.5 mm was collected. Yield, 172 g (79%). The distillate was crystallized from dry ethyl acetate; MP, 121.5° to 123°C.

Therapeutic Function

Muscle relaxant

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