ChemicalBook > CAS DataBase List > alfa1-[[1,1-Dimethylethylamino]methyl]-4-hydroxy-1-(S),3-benzene dimethanol Hydrochlorid

alfa1-[[1,1-Dimethylethylamino]methyl]-4-hydroxy-1-(S),3-benzene dimethanol Hydrochlorid

alfa1-[[1,1-Dimethylethylamino]methyl]-4-hydroxy-1-(S),3-benzene dimethanol Hydrochlorid Structure
alfa1-[[1,1-Dimethylethylamino]methyl]-4-hydroxy-1-(S),3-benzene dimethanol Hydrochlorid
  • CAS No.50293-90-8
  • Chemical Name:alfa1-[[1,1-Dimethylethylamino]methyl]-4-hydroxy-1-(S),3-benzene dimethanol Hydrochlorid
  • CBNumber:CB4875349
  • Molecular Formula:C13H22ClNO3
  • Formula Weight:275.77168
  • MOL File:50293-90-8.mol
alfa1-[[1,1-Dimethylethylamino]methyl]-4-hydroxy-1-(S),3-benzene dimethanol Hydrochlorid Property
  • Melting point 169-171°C
  • alpha D20 -32.2° (c = 0.1 in water)
  • storage temp. 2-8°C
  • solubility H2O: ≥15mg/mL
  • form powder
  • color white to tan
  • optical activity [α]/D -25 to -35°, c = 0.1 in H2O
  • Water Solubility H2O: ≥15mg/mL
  • FDA UNII WDQ1526QJM
  • UNSPSC Code 12352200
  • NACRES NA.77
Safety
  • Hazard Codes  :Xn
  • Risk Statements  :22-37/38-41
  • Safety Statements  :26-39
  • WGK Germany  :3
  • HS Code  :2922504500
  • NFPA 704:
    0
    3 0
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H302-H315-H318-H335
  • Precautionary statements P261-P264-P280-P301+P312-P302+P352-P305+P351+P338
alfa1-[[1,1-Dimethylethylamino]methyl]-4-hydroxy-1-(S),3-benzene dimethanol Hydrochlorid Price More Price(2)
  • Brand: Sigma-Aldrich(India)
  • Product number: SML0138
  • Product name : Levalbuterol hydrochloride
  • Purity: ≥98% (HPLC)
  • Packaging: 10MG
  • Price: ₹11214.7
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: SML0138
  • Product name : Levalbuterol hydrochloride
  • Purity: ≥98% (HPLC)
  • Packaging: 50MG
  • Price: ₹45356.75
  • Updated: 2022/06/14
  • Buy: Buy

alfa1-[[1,1-Dimethylethylamino]methyl]-4-hydroxy-1-(S),3-benzene dimethanol Hydrochlorid Chemical Properties,Usage,Production

  • Description Salbutamol is an agonist of the β2-adrenergic receptor (β2-AR; Kd = 759 nM in a radioligand binding assay using CHO cells expressing the human receptor). It is selective for β2-ARs over β1- and β3-ARs (Kds = 46.8 and 21.9 μM, respectively). Salbutamol (25-50 μg/kg, i.v.) reduces acetylcholine-induced bronchospasm in anesthetized guinea pigs. It also reduces response of bronchial muscle to efferent vagal stimulation in anesthetized cats and dogs when administered at doses ranging from 1 to 2.5 and 10 to 20 μg/kg, respectively. Nebulized salbutamol reduces transpulmonary pressure in recurrent airway obstruction-affected horses (EC50 = 39.7 μg). Formulations containing salbutamol have been used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).
  • Chemical Properties Off-White Solid
  • Originator Xopenex,Sepracor Inc.,USA
  • Uses The R-enantiomer
  • Uses Antiasthmatic
  • Uses β2-agonist, bronchodilator
  • Uses bronchodilator, tocolytic
  • Manufacturing Process Preparation of 5-glyoxyloyl-salicylic acid methyl ester hydrate using aqueous HBr
    To a 3-neck flask immersed in an oil bath containing a solution of 40 g (0.206 mole) methyl 5-acetylsalicylate in 6 ml methylene chloride is charged with 82 ml of isopropanol. The solution is distilled to remove excess methylene chloride. When the internal temperature reaches 77°C, 126 ml (1.77 mole or 8.6 equivalents) of DMSO is added to the reaction mixture and the temperature of the mixture is increased to a temperature of 85° to 90°C. Then 33 ml (0.29 mole or 1.4 equivalents) of HBr (aqueous, 48%) is added to the mixture over a period of 20 minutes (exothermic), and the bath temperature is maintained at 95° to 100°C. As the addition of HBr nears completion distillation is initiated and dimethysulfide and isopropanol are distilled off. The mixture is stirred and the volume of the distillate monitored. After distillation of 82 ml of solvent, 20 ml of isopropanol is added slowly to maintain a steady rate of distillation. After the reaction completed asdetermined by high performance liquid chromatography (HPLC), the reaction mixture is quenched with 70 ml of 2.4 N H2SO4, the temperature of the reaction mixture is allowed to drop to 75°C and residual isopropanol is distilled off under vacuum. After a total of 165 ml distillate is collected, the title compound begins to precipitate. A mixture of 30 ml of acetonitrile and 70 ml of water is added slowly at 75°C with stirring. After 30 minutes of stirring, the reaction mixture is cooled to 15°C over a period of 90 minutes to complete the precipitation. The reaction mixture is filtered and the cake is washed with three 300 ml portions of water. The cake is dried in a draft oven at 50°C for 16 hours to give 39.5 g of the title compound (85% yield).
    Preparation of albuterol from 5-glyoxyloyl-salicylic acid methyl ester
    To a solution of 5-glyoxyloylsalicylic acid methyl ester hydrate (50 g, 0.221 mol) in ethylene glycol diethyl ether, 440 mL is added tertiary butylamine (16.2 g, 0.221 mol) at room temperature. The resulting light orange solution is stirred for 5 min until a clear solution is formed. The clear solution is then heated to reflux. Water and DME are distilled off azeotropically. After a total of 200 ml of distillate are collected, the solution is cooled to 25°C. The reaction mixture is slowly added to a solution containing 49 mL (0.49 mol) of 10.0 M borane-dimethyl sulfide in 220 mL of ethylene glycol diethyl ether (DME) at 70°C. The resulting reaction mixture is further refluxed for 2.5 hrs. After the reaction is completed as monitored by HPLC, excess DME is removed via vacuum distillation. The residue containing complexes of boron and arylethanolamine is subsequently cooled to 0°C. Quenching of the residue with 300 mL methanol gives the methylborate of arylethanolamine. The borate is then removed by azeotropic distillation as trimethylborate, leaving behind the desired arylethanolamine in the reaction mixture. An additional 300 ml of methanol and acetic acid (85 mL) are added to ensure the complete removal of trimethylborate via vacuum distillation to near dryness. The residue containing the boron-free arylethanolamine is cooled to 25°C and concentrated sulfuric acid (10.4 g, 0.221 mole) in water (64 mL) is added following by 570 ml of isopropyl alcohol. Albuterol sulfate is precipitated out as a white solid. After the reaction mixture is stirred at room temperature for 12 hrs and 0°C for 30 min the albuterol sulfate is filtered, washed with isopropyl alcohol (two 50 mL portions) and dried at 50°C for 12 hrs to give 49.75 g of the title compound (78% yield) as racemate.
    The optically pure albuterol may be prepared by resolving a mixture of enantiomers methyl benzoate albuterol precursors which prepared by procedures well known to persons skilled in the art. The starting material 4- benzyl albuterol is commercially available from Cipla (Bombay, India).
    (-)-D-Dibenzoyltartaric acid (D-DBTA) (32.2 g, 90 mmol, 1.0 eq) is added to a hot solution of racemic 4-benzyl albuterol (29.6 g, 90 mmol, 1.0 eq) in 180 mL of anhydrous denatured ethanol (type 3A, denatured with 5 vol % 2- propanol). The resulting solution is refluxed for 15 min and cooled to room temperature over 40 min and seeded with 99% ee (R)-4-benzyl albuterol DDBTA salt. The mixture is cooled to 5°-10°C and stirred for 1 hour. The white solid is collected by filtration and dried at 40°C and 28 inches of Hg for 1 hour to give (R)-4-benzyl albuterol D-DBTA salt (31.8 g, 50% yield, 83.6% ee). The solid is redissolved in 240 mL of ethanol at 55°-60°C and the solution is cooled to room temperature and stirred at room temperature for 2 hours and at 0°-5°C for 1 hour. The resulting solid is collected by filtration and dried at40°C and 28 inches of Hg for 2 hours as (R)-4-benzyl albuterol D-DBTA salt (22.9 g, 37.1% yield, 99.3% ee). The salt (22.9 g) is then treated with 204 mL of 5 wt % aq. Na2CO3 solution in 570 mL of ethyl acetate. The solid is worked-up, and recrystallization from 30 mL of ethyl acetate and 30 mL of nheptane gives optically pure (R)-4-benzyl albuterol free base as a white powder (10.1 g, 34.1% yield from racemic compound 99.6% ee and 99.8% purity).
    A mixture of (R)-4-benzyl albuterol as a free base (3.2 g, 9.73 mmol) and 10% Pd/C (0.64 g) in 24 mL of ethanol (denatured with 5 vol % 2-propanol) is shaken on a Parr-hydrogenator under 50 psi of hydrogen at room temperature for 3 hours. The catalyst is removed by filtration and the filtrate is concentrated to ca. 9 mL in volume containing crude (R)-albuterol and treated with anhydrous HCl in ether (1.0 M, 9.5 mL, 0.98 eq) at 0°-5°C. After 30 min at room temperature, 9 mL of methyl t-butyl ether (MTBE) is added, the resulting mixture is stirred at room temperature for 30 min and at 0°-5°C for 2 hours. The white solid (R)-albuterol hydrochloride is collected by filtration and recrystallized from 25 mL of ethanol and 12.5 mL of MTBE to give pure (R)-albuterol hydrochloride (2.17 g, 80.9% yield, 99.6% purity), white powder.
  • brand name Xopenex (Sepracor).
  • Therapeutic Function Bronchodilator
  • Biochem/physiol Actions Levalbuterol (levosalbutamol) is the more active isomer of albuterol. Levalbuterol is a β-adrenergic agonist; a bronchodilator used clinically to treat asthma and COPD..
alfa1-[[1,1-Dimethylethylamino]methyl]-4-hydroxy-1-(S),3-benzene dimethanol Hydrochlorid Preparation Products And Raw materials
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alfa1-[[1,1-Dimethylethylamino]methyl]-4-hydroxy-1-(S),3-benzene dimethanol Hydrochlorid Spectrum
50293-90-8, alfa1-[[1,1-Dimethylethylamino]methyl]-4-hydroxy-1-(S),3-benzene dimethanol HydrochloridRelated Search:
  • 50293-90-8
  • API
  • XOPENEX
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  • 杂质对照品
  • 医药原料
  • C13H21NO3ClH
  • C13H21NO3HCl
  • 左沙丁胺醇盐酸盐
  • 化合物 LEVOSALBUTAMOL HYDROCHLORIDE
  • 沙丁胺醇杂质14 盐酸盐
  • (R)-沙丁胺醇
  • 酸左旋沙丁胺
  • 沙丁胺醇杂质14(沙丁胺醇R异构体盐酸盐)
  • 沙丁胺醇杂质8 盐酸盐
  • 盐酸左旋沙丁胺醇 5级
  • (R) -盐酸沙丁胺醇(盐酸左旋布特罗)
  • 左旋沙丁胺醇 HCL
  • 盐酸左沙丁胺醇
  • (R)-沙丁胺醇((R)-盐酸沙丁胺醇)
  • 盐酸左沙丁醇
  • (R) -盐酸沙丁胺醇
  • 左沙丁胺醇盐酸盐 USP标准品
  • 盐酸左旋沙丁胺醇对照品1
  • (R)-丁胺盐酸盐
  • 盐酸左旋沙丁胺醇对照品
  • 盐酸左旋沙丁胺醇
  • 50293-90-8
  • Salbutamol Impurity 14 HCl
  • Levosalbutamol dihydrochloride
  • Salbutamol (R)-Isomer HCl / (R)-Salbutamol HCl / Levosalbutamol HCl / Levalbuterol HCl
  • Salbutamol Impurity 8 HCl
  • (R)-Salbutamol Hydrochloride(Levalbuterol Hydrochloride)
  • Levalbuterol Hydrochloride (1358784)
  • Levosalbutamol HCl (Levosalbutamol)
  • Salbutamol (R)-Isomer HCl
  • (R)-Salbutamol HCl ((R)-Albuterol HCl)
  • 2-(Hydroxymethyl)-4-{(1R)-1-hydroxy-2-[(2-methyl-2-propanyl)amino ]ethyl}phenol hydrochloride (1:1)
  • (R)-4-(2-(tert-butylamino)-1-hydroxyethyl)
  • Salbutamol Impurity 14（Salbutamol (R)-Isomer HCl）
  • SALBUTAMOL (HYDROCHLORIDE);LEVALBUTEROL;(-)-SALBUTAMOL;(R)-SALBUTAMOL
  • (R)-4-(2-(tert-butylamino)-1-hydroxyethyl)-2-(hydroxymethyl)phenol hydrochloride
  • 1,3-Benzenedimethanol, a1-[[(1,1-dimethylethyl)amino]methyl]-4-hydroxy-,hydrochloride (1:1), (a1R)-
  • Zopenex [common misspelling of xopenex]
  • Zopenex
  • Xopenex
  • Unii-wdq1526qjm

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