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

Product Name
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
Synonyms
Xopenex;Zopenex;Unii-wdq1526qjm;Salbutamol (R)-Isomer HCl;Salbutamol Impurity 8 HCl;Levalbuterol hydrochloride;Salbutamol Impurity 14 HCl;(-)-Salbutamol hydrochloride;LevosalbutaMol Hydrochloride;(R)-Salbutamol hydrochloride
CBNumber
CB4875349
Molecular Formula
C13H22ClNO3
Formula Weight
275.77168
MOL File
50293-90-8.mol
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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
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Safety

Hazard Codes 
Xn
Risk Statements 
22-37/38-41
Safety Statements 
26-39
WGK Germany 
3
HS Code 
2922504500
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0138
Product name
Levalbuterol hydrochloride
Purity
≥98% (HPLC)
Packaging
10mg
Price
$116
Updated
2024/03/01
Sigma-Aldrich
Product number
1358784
Product name
Levalbuterol hydrochloride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
Cayman Chemical
Product number
23991
Product name
Salbutamol (hydrochloride)
Purity
≥98%
Packaging
5mg
Price
$49
Updated
2024/03/01
Cayman Chemical
Product number
23991
Product name
Salbutamol (hydrochloride)
Purity
≥98%
Packaging
10mg
Price
$92
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0138
Product name
Levalbuterol hydrochloride
Purity
≥98% (HPLC)
Packaging
50mg
Price
$363
Updated
2024/03/01
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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

bronchodilator, tocolytic

Uses

β2-agonist, bronchodilator

Uses

Antiasthmatic

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

Raw materials

Preparation Products

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

TEVA PHARMACEUTICAL INDUSTRIES LTD
Tel
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Fax
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Email
megan.carroll@tevapharm.com
Country
Israel
ProdList
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View Lastest Price from alfa1-[[1,1-Dimethylethylamino]methyl]-4-hydroxy-1-(S),3-benzene dimethanol Hydrochlorid manufacturers

Hebei Yanxi Chemical Co., Ltd.
Product
Levalbuterol hydrochloride 50293-90-8
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20tons
Release date
2023-10-07
Hebei Yanxi Chemical Co., Ltd.
Product
Levalbuterol hydrochloride 50293-90-8
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20tons
Release date
2023-10-07
Wuhan Senwayer Century Chemical Co.,Ltd
Product
Levalbuterol hydrochloride 50293-90-8
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20 TONS
Release date
2022-11-04

50293-90-8, alfa1-[[1,1-Dimethylethylamino]methyl]-4-hydroxy-1-(S),3-benzene dimethanol HydrochloridRelated Search:


  • Levalbuterol hydrochloride
  • LEVALBUTEROL HCL (SALBUTAMOL HCL)
  • Levalbuterol Hydrochloride (200 mg)
  • (α1R)-α1-[[(1,1-DiMethylethyl)aMino]Methyl]-4-hydroxy-1,3-benzenediMethanol Hydrochloride
  • LevosalbutaMol Hydrochloride
  • fa1-[[1,1-DiMethylethylaMino]Methyl]-4-hydroxy-1-(S),3-benzene diMethanol Hydrochlorid
  • 1,3-Benzenedimethanol, a1-[[(1,1-dimethylethyl)amino]methyl]-4-hydroxy-,hydrochloride (1:1), (a1R)-
  • (R)-4-(2-(tert-butylamino)-1-hydroxyethyl)-2-(hydroxymethyl)phenol hydrochloride
  • 4-[(1R)-2-(TERT-BUTYLAMINO)-1-HYDROXYETHYL]-2-(HYDROXYMETHYL)PHENOL HYDROCHLORIDE
  • 2-(hydroxymethyl)-4-[(1R)-1-hydroxy-2-(tert-butylamino)ethyl]phenol hydrochloride
  • (-)-Salbutamol hydrochloride
  • (R)-Salbutamol hydrochloride
  • 1,3-Benzenedimethanol, alpha1-(((1,1-dimethylethyl)amino)methyl)-4-hydroxy-, hydrochloride, (alpha1R)-
  • Unii-wdq1526qjm
  • Xopenex
  • Zopenex
  • Zopenex [common misspelling of xopenex]
  • SALBUTAMOL (HYDROCHLORIDE);LEVALBUTEROL;(-)-SALBUTAMOL;(R)-SALBUTAMOL
  • Salbutamol Impurity 14(Salbutamol (R)-Isomer HCl)
  • (R)-4-(2-(tert-butylamino)-1-hydroxyethyl)
  • 2-(Hydroxymethyl)-4-{(1R)-1-hydroxy-2-[(2-methyl-2-propanyl)amino ]ethyl}phenol hydrochloride (1:1)
  • (R)-Salbutamol HCl ((R)-Albuterol HCl)
  • Salbutamol (R)-Isomer HCl
  • Levosalbutamol HCl (Levosalbutamol)
  • Levalbuterol Hydrochloride (1358784)
  • (R)-Salbutamol Hydrochloride(Levalbuterol Hydrochloride)
  • Salbutamol Impurity 8 HCl
  • Salbutamol Impurity 14 HCl
  • Salbutamol (R)-Isomer HCl / (R)-Salbutamol HCl / Levosalbutamol HCl / Levalbuterol HCl
  • Levosalbutamol dihydrochloride
  • 50293-90-8
  • C13H21NO3HCl
  • C13H21NO3ClH
  • Amines
  • Aromatics
  • Chiral Reagents
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • XOPENEX
  • API
  • 50293-90-8