isoxsuprine
- CAS NO.:395-28-8
- Empirical Formula: C18H23NO3
- Molecular Weight: 301.39
- MDL number: MFCD00242894
- EINECS: 206-898-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-05-04 17:34:38
What is isoxsuprine?
Originator
Duvadilan,Duphar,France,1958
The Uses of isoxsuprine
Vasodilator.
Background
A beta-adrenergic agonist that causes direct relaxation of uterine and vascular smooth muscle. Its vasodilating actions are greater on the arteries supplying skeletal muscle than on those supplying skin. It is used in the treatment of peripheral vascular disease and in premature labor.
Definition
ChEBI: 4-[1-hydroxy-2-(1-phenoxypropan-2-ylamino)propyl]phenol is an alkylbenzene.
Manufacturing Process
To a solution of 30.7 g (0.203 mol) of 1-phenoxy-2-aminopropane in 150 ml
of ethanol there was added 31.9 g (0.100 mol) of 1-(4'-benzyloxyphenyl)-2-
bromopropanone-1. The mixture was heated to boiling temperature and the
solution was then refluxed in a reflux condenser for 3 hours. Most of the
ethanol was then distilled off in vacuo, Then to the residue there was addedabout 150 ml of diethyl ether. The hydrogen bromide salt of 1-phenoxy-2-
aminopropane was filtered off and washed with diethyl ether.
The collected ethereal filtrates were acidified with 50 ml of 4 N hydrochloric
acid and this solution was stirred vigorously. The hydrochloride of 1-(4'-
benzyloxyphenyl)-2-(1'-methyl-2-phenoxy-ethylamino)propanone-1
precipitated out, was filtered off, washed with water and then with diethyl
ether. Then this substance was dried in vacuo. The yield was 37.7 g, i.e., 89%
of the theoretically possible yield, calculated on 1-(4'-benzyloxyphenyl)-2-
bromine propanone-1. This substance had a light yellow color and melted at
197 to 198°C, while decomposing.
Then 21.89 g of the hydrochloride salt was dissolved in 600 ml of 80%
aqueous ethanol. With the addition of a palladium carbon catalyst, this
solution was hydrogenated at room temperature under a hydrogen pressure of
about 1.1 atmospheres. After 2 mols hydrogen had been absorbed, the
catalyst was filtered off and the filtrate was evaporated in vacuo until
crystallization occurred. Then the crystals were dissolved by heating in the
smallest possible quantity of water and after cooling, the crystallized
substance was filtered off, washed with water and dried in vacuo. The yield
was 6.80 g, i.e., 39% of the theoretically possible yield. The resultant product
recrystallized from water melted at 203° to 204°C.
brand name
Vasodilan (Apothecon).
Therapeutic Function
Vasodilator
Metabolism
Not Available
Properties of isoxsuprine
Melting point: | 102.5-103.5° |
Boiling point: | 442.51°C (rough estimate) |
Density | 1.1412 (rough estimate) |
refractive index | 1.5740 (estimate) |
pka | 9.96±0.26(Predicted) |
EPA Substance Registry System | Isoxsuprine (395-28-8) |
Safety information for isoxsuprine
Computed Descriptors for isoxsuprine
New Products
Tubulysin C Tubulysin H Tubulysin B Potassium HMDS (1.0 M in THF) Isoxazole, 3-[[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl]thio]-4,5-dihydro-5,5-dimethyl- CYCLOBUTYLAMINE HYDROCHLORIDE 3-METHYLAZETIDIN-3-OL HYDROCHLORIDE tetrahydro-4-methyl-2H-pyran 2-(azetidin-3-ylidene)acetonitrile (hydrochloride) 2,2-Difluoropropylamine hydrochloride 2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol ethanedioate 2-[2-[3(S)-3[2-(7-chloro-2-quinolinyl) ethenyl] phenyl-3- hydroxyl propyl] phenyl]-2-propanol Imeglimin Hydrochloride IH Fuel shell (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine Calcium Sodium Phosphosilicate IH 2,3-Dichloro-6- nitrobenzylamine Hydrochloride (1S,4S)-4- (3,4-dichlorophenyl) -N-methyl-1,2,3,4- tetrahydrona phthalen -1-amine .D-Mandelate Lubiprostone Latanoprostene Bunod Magnesium Trisilicate Flame Retardant Zinc Borate 1H-Imidazole-4-carbonitrile 7-Methoxyquinoline-4-carboxylic acidRelated products of tetrahydrofuran
You may like
-
Fuel shell 98%View Details
-
4,6-dichloro-2-propylthiopyrimidine-5-amine 145783-15-9 98%View Details
145783-15-9 -
109113-72-6 2-(Chloromethyl)-4-methylquinazoline (2-CMQ) 98%View Details
109113-72-6 -
Hydrogen Gas 98%View Details
-
590-17-0 Bromoacetonitrile 98%View Details
590-17-0 -
151767-02-1 Montelukast Sodium IP/USP 98%View Details
151767-02-1 -
Valacyclovir Hydrochloride IH 98%View Details
124832-27-5 -
2-[2-[3(S)-3[2-(7-chloro-2-quinolinyl) ethenyl] phenyl-3- hydroxyl propyl] phenyl]-2-propanol 98%View Details
142569-70-8