949-36-0

Basic information

• Product Name: ISOPROTERENOL HYDROCHLORIDE
• Synonyms: asthpul;dl-isadrinehydrochloride;dl-isoprenalinehydrochloride;dl-isopropylnoradrenalinehydrochloride;dl-isopropylnorepinephrinehydrochloride;dl-n-isopropylnoradrenalinehydrochloride;racemicisoprenalinehydrochloride;racemicisoproterenolhydrochloride
• CAS NO: 949-36-0
• Molecular Formula: C₁₁H₁₈NO₃*Cl
• Molecular Weight: 247.72
• EINECS: 200-089-8
• Mol File: 949-36-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 165-175 °C (dec.)(lit.)
• Boiling Point: 417.5°Cat760mmHg
• Flash Point: 179.7°C
• Appearance: /
• Density: 1.199g/cm³
• Vapor Pressure: 1.02E-07mmHg at 25°C
• CAS DataBase Reference: ISOPROTERENOL HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPROTERENOL HYDROCHLORIDE(949-36-0)
• EPA Substance Registry System: ISOPROTERENOL HYDROCHLORIDE(949-36-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: DO1925000
• F: 3-8-10
• Hazardous Substances Data: 949-36-0(Hazardous Substances Data)

Usage

General Description

Isoproterenol hydrochloride, also known as isoprenaline hydrochloride, is a synthetic catecholamine and a non-selective beta adrenergic agonist. It is a medication used as a bronchodilator and as a cardiac stimulant. Isoproterenol hydrochloride works by stimulating beta-adrenergic receptors in the heart, lungs, and blood vessels, leading to relaxation of smooth muscles in the airway and dilation of blood vessels. This drug is commonly used to treat bronchospasm and asthma, as well as to increase heart rate and cardiac output in certain medical conditions such as bradycardia and heart block. Additionally, isoproterenol hydrochloride may also be used as a positive inotropic agent in the management of heart failure.

InChI:InChI=1/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3/p+1/t11-/m1/s1

Upstream product

• 120-80-9 benzene-1,2-diol 
• 16899-81-3 Isoproterenone hydrochloride 
• 121-28-8 Isoproterenone 
• 51-30-9 (-)-isoproterenol hydrochloride 

Downstream Products

• 51-30-9 isoproterenol hydrochloride 
• 18810-21-4 (+)-Isoproterenol hydrochloride 
• 5984-95-2 (R)-(-)-isoproterenol hydrochloride 
• 73635-69-5 tris(carboethoxy)isoproterenol 
• 639007-20-8 isoprenaline glucuronide 

Relevant articles and documents

Preparation method of isoproterenol hydrochloride

The invention relates to the technical field of raw material medicine synthesis, in particular to a preparation method of isoproterenol hydrochloride. According to the preparation method, water, N, N-dimethylformamide or an aqueous solution of N, N-dimethylformamide is used as a solvent, borohydride is used as a reducing agent to carry out reduction reaction on isopropyladrenolone or salt thereof, the reaction conditions are mild, compared with a conventional hydrogenation reduction process, the production safety is remarkably improved, the production cost is greatly reduced, the usage amount of borohydride is small, and the environmental protection is improved to a certain extent. The product obtained by the preparation method is very high in purity, is suitable for industrial production of isoprenaline hydrochloride as a medicine raw material medicine product, and can effectively avoid toxic and side effects caused by impurities.

Method for preparing isoproterenol sulfate

The invention discloses a method for preparing isoproterenol sulfate. The method comprises the following steps: (1) performing hydrogenation reduction on isoproterenol ketone in a methanol solvent in the presence of sodium borohydride at room temperature, so as to obtain isoproterenol; (2) performing negative pressure concentration on the solvent methanol, adding water, extracting with ethyl acetate, regulating the pH value of the system to be acidic by using 60% of sulfuric acid, raising the temperature to reflux for 30 minutes, and clarifying; (3) freezing overnight to obtain a white powdered crystal; (4) filtering, washing, drying, and recrystallizing with ethanol, thereby obtaining the isoproterenol sulfate. According to the method disclosed by the invention, hidden danger of high-pressure hydrogenation is avoided, and the reaction is safe by adopting sodium borohydride for reduction; with the adoption of a normal pressure reaction, usage of a metal high-pressure reactor is avoided; the raw materials are readily available, and the process is simple and reasonable.

The acid-catalysed racemisation mechanism of catecholamines

The racemisation rates of (-)-adrenaline (1), ()-isoprenaline (2), (-)-2-(3,4-dimethoxyphenyl)-2-hydroxy-N-isopropylamine (3), (+)-2-(4-meethoxyphenyl)-2-hydroxy-N-isopropylethylamine (4), (+)-2-phenyl-2-hydroxy-N-isopropylehylamine (5), ()-phenylephrine(6), and (+)-1-phenylethanol(7) were compared. The racemisatton rates decreased in the following order: 7> 1 ≈ 2 > 3 ≈ 4 ? 5, 6. In general, the reactivity of the series of the phenylethanolamine compounds (1) - (6) was seen to increase sharply as the electron-releasing ability of the p-substituent of the aromatic nucleus increases. The results strengthen the notion that the acid-catalysed racemisation of catecholamines proceeds via a quinonoid-type intermediate.