Mephenoxalone Chemical Properties

Melting point:

143-145°

Boiling point:

364.51°C (rough estimate)

Density 

1.2446 (rough estimate)

refractive index 

1.4960 (estimate)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

12.24±0.40(Predicted)

color 

White to Off-White

NIST Chemistry Reference

2-Oxazolidinone, 5-[(o-methoxyphenoxy)methyl]-(70-07-5)

Safety Information

Toxicity

LD50 orally in rats: 3820 ±17 mg/kg (Goldenthal)

Mephenoxalone Usage And Synthesis

Originator

Trepidone,Lederle, ,1961

Uses

Muscle relaxant, also used as a mild tranquilizer.

Uses

Mephenoxalone is used as a muscle relaxant, also as a mild tranquilizer.

Uses

Prostaglandin F2á ethyl amide Lumigan (0.03% bimatoprost ophthalmic solution)

Definition

ChEBI: Mephenoxalone is a member of methoxybenzenes.

Manufacturing Process

A mixture of 24.1 g (0.10 mol) of 3-o-methoxyphenoxy-2-hydroxy-1-propyl carbamate and 6.0 g (0.10 mol) of urea was heated rapidly to the temperature range of 180°C to 200°C, and maintained there for five hours. The reaction melt was poured into 50% ethyl alcohol, from which the product crystallized as a white solid. The crude yield was 18.3 g (82%); melting point 131.5% to 137°C. Crystallization from water and 95% alcohol gave 9.0 g (40.3 %) of pure 5-o-methoxyphenoxymethyl-2-oxazolidone; melting point 141°C to 143°C. This melting point was not depressed when the material was mixed with an authentic sample. In additional runs acetone was used instead of ethyl alcohol with equivalent results.
It was found that when the heating time was reduced to three hours and a reaction temperature of 190°C to 200°C was maintained, equivalent yields (40 to 50%) were obtained, but that the yields were appreciably lowered when the heating time was further reduced to two hours. It was also found that when the temperature was lowered to the range of 170°C to 180°C the yield was significantly lowered.
When the material was isolated by extraction with chloroform and distillation, the yield of pure material was 58.5%.

brand name

MI. Lenetran (Marion Merrell Dow).

Therapeutic Function

Tranquilizer

Mephenoxalone(70-07-5)Related Product Information

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• Tribenuron methyl
• 4-Methoxybenzoic acid
• 3-(METHOXYMETHOXY)BENZALDEHYDE
• 2-Oxazolidone
• p-Anisaldehyde
• 3-Methoxyacetophenone
• Anisole
• o-Anisaldehyde
• METSULFURON METHYL
• Basic Violet 1
• (Trifluoromethoxy)benzene
• Kresoxim-methyl
• 4'-Methoxyacetophenone
• Methanol
• Methyl acrylate
• Methyl salicylate
• Methyl