Salbutamol

Base Information

• Chemical Name: Salbutamol
• CAS No.: 18559-94-9
• Deprecated CAS: 35763-26-9
• Molecular Formula: C13H21NO3
• Molecular Weight: 239.315
• Hs Code.: 2922504500
• European Community (EC) Number: 242-424-0
• NSC Number: 757417
• UNII: QF8SVZ843E
• DSSTox Substance ID: DTXSID5021255
• Nikkaji Number: J10.899E
• Wikipedia: Salbutamol
• Wikidata: Q93346928
• NCI Thesaurus Code: C215
• RXCUI: 435
• Pharos Ligand ID: RJYZJCG7HWL2
• ChEMBL ID: CHEMBL714
• Mol file: 18559-94-9.mol

Synonyms:2-t-Butylamino-1-(4-hydroxy-3-hydroxy-3-hydroxymethyl)phenylethanol;Albuterol;Albuterol Sulfate;Proventil;Salbutamol;Sultanol;Ventolin

Chemical Property of Salbutamol

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 2.78E-08mmHg at 25°C
• Melting Point: 151 °C
• Refractive Index: 1.566
• Boiling Point: 433.5 °C at 760 mmHg
• PKA: pKa 9.07(H2O t = 25.0±0.05 I = 0.10) (Uncertain);10.37(H2O t = 25.0±0.05 I = 0.10) (Uncertain)
• Flash Point: 159.5 °C
• PSA: 72.72000
• Density: 1.152 g/cm³
• LogP: 1.69690
• Storage Temp.: ?20°C
• Solubility.: Soluble in ethanol.
• Water Solubility.: 17.95g/L(25 oC)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 239.15214353
• Heavy Atom Count: 17
• Complexity: 227

Purity/Quality:

99% ^*data from raw suppliers

Salbutamol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn,T,F
• Statements: 22-39/23/24/25-23/24/25-11
• Safety Statements: 36-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)NCC(C1=CC(=C(C=C1)O)CO)O
• Recent ClinicalTrials: Effect of Salbutamol on Walking Capacity in Ambulatory ALS Patients
• Recent EU Clinical Trials: A Randomized, Double-Blind, Parallel Group, Multicenter 24 Week Study to Assess the Efficacy and Safety of Budesonide and Formoterol Fumarate Metered Dose Inhaler Relative to Budesonide Metered Dose Inhaler and Open-Label Symbicort? Turbuhaler? in Participants with Inadequately Controlled Asthma (VATHOS)
• Description: Salbutamol is a short-acting, selective β2-adrenergic receptor agonist. Like other β2-adrenergic receptor drugs that are breathed in through the mouth, salbutamol can relax the muscles in the lung and open the bronchial tubes to relieve breathing difficulty. They relieve cough, wheezing, shortness of breath, and troubled breathing by increasing the flow of air through the bronchial tubes. Salbutamol is generally used to treat or prevent bronchospasm caused by bronchial asthma, chronic bronchitis, and other chronic bronchopulmonary disorders such as chronic obstructive pulmonary disorder (COPD). It is also used prevent wheezing caused by exercise (exercise induced bronchospasm). It is marketed as Airomir?; AirSalb?; Asmasal Clickhaler?; Asmavent?; Easyhaler? Salbutamol; Pulvinal? Salbutamol; Salamol?; Salbulin?; Ventolin?. Albuterol is a β2-adrenergic sympathomimetic amine with pharmacological similarities to terbutaline. It has almost no effect on β1-adrenoreceptors of the heart. It has expressed broncholytic effects—prevention or relief of bronchi spasms, lowering respiratory tract resistance, and increasing the vital capacity of the lungs.
• Uses: Albuterol is widely used for severe and chronic bronchial asthma and other illnesses of the respiratory tract that result in a spastic condition of the bronchi. immune suppressant, antineoplastic, antiviral short-acting b2-adrenergic agonist, asthma therapeutic
• Therapeutic Function: Bronchodilator
• Biological Functions: Levalbuterol is the R-(–)-isomer of albuterol and is available only in solution to be administered via nebulizer. Because it is the active isomer, the dose is fourfold less than that of albuterol. Pirbuterol is the pyridine isostere of albuterol. It has pharmacokinetics similar to albuterol but is half as potent at the β2-receptor. Pirbuterol is only available as an inhaler, whereas albuterol comes in tablet, syrup, solution, and aerosol formulations.
• Clinical Use: Albuterol has the N-t-butyl and a salicyl alcohol phenyl ring, which gives it optimal β2-selectivity. It is resistant to COMT and slowly metabolized by MAO, giving it good oral bioavailability. Its onset by inhalation is within 5 minutes, with a duration of action between 4 and 8 hours. It currently is the drug of choice for relief of the acute bronchospasm of an asthmatic attack.

Technology Process of Salbutamol

There total 40 articles about Salbutamol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.9%

C13H17NO4 → Salbutamol (18559-94-9,34271-50-6)

Guidance literature:

With sodium tetrahydroborate; iron(II) sulfate; In methanol; at 5 - 20 ℃; for 1h; Reagent/catalyst; Temperature; Solvent;

Reference yield: 91.0%

2-(tert-butylamino)-1-(2,2-dimethyl-4H-benzo[d][1,3]dioxan-6-yl)ethanol (54208-72-9) → Salbutamol (18559-94-9,34271-50-6)

Guidance literature:

With hydrogenchloride; In water; pH=1; Cooling with ice;

Reference yield: 90.0%

α-[(benzyl-tert-butylamino)methyl]-m-xylene-4,α,α'-triol (24085-03-8) → Salbutamol (18559-94-9,34271-50-6)

Guidance literature:

With hydrogen; nickel; In isopropyl alcohol; at 60 ℃; under 3102.9 Torr; 20-24 h;

DOI:10.1080/00397919708004201

upstream raw materials:

5-(2-tert-Butylamino-acetyl)-2-hydroxy-benzaldehyde

α-[(benzyl-tert-butylamino)methyl]-m-xylene-4,α,α'-triol

salicylaldehyde

5-(Chloroacetyl)-2-hydroxybenzaldehyde

Downstream raw materials:

(R)-α1-[[(1,1-dimethylethyl)amino]methyl]-4-hydroxy-1,3-benzenedimethanol D-dibenzoyltartrate

2-(4-methoxybenzyloxy)-5-(2-(N-tert-butylamino)-1-(4-methoxybenzyloxy)ethyl)benzyl alcohol

N-(tert-butyl)-2-methoxy-2-(4-hydroxy-3-(hydroxymethyl)phen-1-yl)-ethanamine

C₁₅H₂₅NO₂

Refernces

• 1、 -. "Preparation method of salbutamol sulfate". . . Retrieved 2021/07/17.
• 2、 -. "Preparation method of salbutamol sulfate intermediate". Page/Page column 5-7. . Retrieved 2019/06/05.