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mefruside

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mefruside Basic information

Product Name:
mefruside
Synonyms:
  • 1,3-Benzenedisulfonamide, 4-chloro-N1-methyl-N1-[(tetrahydro-2-methyl-2-furanyl)methyl]- (9CI)
  • 4-Chloro-N1-methyl-N1-(tetrahydro-2-methylfurfuryl)-m-benzenedisulfonamide
  • B 1500
  • BAY 1500
  • Baycaron
  • FBA 1500
  • FDA 1902
  • m-Benzenedisulfonamide, 4-chloro-N1-methyl-N1-(tetrahydro-2-methylfurfuryl)- (7CI, 8CI)
CAS:
7195-27-9
MF:
C13H19ClN2O5S2
MW:
382.88
EINECS:
2305624
Mol File:
7195-27-9.mol
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mefruside Chemical Properties

Melting point:
149.5°C
Boiling point:
565.2±60.0 °C(Predicted)
Density 
1.3150 (rough estimate)
refractive index 
1.6100 (estimate)
storage temp. 
Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility 
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form 
Solid
pka
9.26±0.60(Predicted)
color 
White to Pale Beige
Stability:
Hygroscopic
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Safety Information

Toxicity
LD50 oral in rabbit: > 3gm/kg
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mefruside Usage And Synthesis

Originator

Baycaron,Bayer,W. Germany,1967

Uses

Mefruside is a diuretic used for the treatment of edema and hypertension.

Definition

ChEBI: Mefruside is an organic molecular entity.

Manufacturing Process

By hydrogenation of α-methyl-α-cyanotetrahydrofuran with Raney nickel as catalyst, α-methyl-α-tetrahydrofurfuryl amine is obtained (BP 48°C/12 mm Hg) which is alkylated by dimethyl sulfate to give α-methyl-αtetrahydrofurfurylmethylamine (BP 70°C/40 mm Hg). The amine is then reacted with 4-chloro-3-sulfamyl benzene sulfochloride in the presence of an acid acceptor. The mixture is stirred overnight, the solvent (acetone or pyridine) is driven off under vacuum and the residue is recrystallized from alcohol.

Therapeutic Function

Diuretic

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