51-30-9

Basic information

• Product Name: Isoprenaline hydrochloride
• Synonyms: 2-benzenediol,4-(1-hydroxy-2-((1-methylethyl)amino)ethyl)-hydrochloride;3,4-dihydroxy-alpha-((isopropylamino)methyl)-benzylalcohohydrochloride;alpha-(isopropylaminomethyl)-3,4-dihydroxybenzylalcoholhydrochloride;euspiran;isadrine;isoprenalinechloride;isopropylnorepinephrine-hydrochloride;isoproterenolmonohydrochloride
• CAS NO: 51-30-9
• Molecular Formula: C₁₁H₁₈NO₃*Cl
• Molecular Weight: 247.72
• EINECS: 200-089-8
• Product Categories: Adrenoceptor;API;AEROLONE;Other APIs;Cardiovascular Series
• Mol File: 51-30-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 165-175 °C (dec.)(lit.)
• Boiling Point: 192°C (rough estimate)
• Flash Point: 179.7 °C
• Appearance: white crystalline powder
• Density: 1.2296 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Store at RT
• Solubility: Freely soluble in water, sparingly soluble in ethanol (96 per cent), practically insoluble in methylene chloride.
• Water Solubility: Soluble
• Stability: Stable, but may be air and light sensitive. Incompatible with strong oxidizing agents.
• BRN: 3917363
• CAS DataBase Reference: Isoprenaline hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Isoprenaline hydrochloride(51-30-9)
• EPA Substance Registry System: Isoprenaline hydrochloride(51-30-9)

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: 51-30-9(Hazardous Substances Data)

Usage

Chemical Properties

White or almost white, crystalline powder.

Uses

Different sources of media describe the Uses of 51-30-9 differently. You can refer to the following data:
1. Isoproterenol is a non-selective beta-adrenergic agonist. Isoproterenol is used in the treatment of bradycardia; bronchodilator.
2. Isoproterenol hydrochloride is used as a selective β-adrenergic agonist, increases cytosolic cAMP.

Brand name

Isuprel (Hospira); Isuprel (Sanofi Aventis); Vapo- ISO (Fisons).

General Description

Odorless white crystalline powder. Slightly bitter taste. Aqueous solutions turn brownish-pink upon prolonged exposure to air.

Air & Water Reactions

May be sensitive to exposure to air and light. . Water soluble.

Reactivity Profile

An acid organic salt. Materials in this group are generally soluble in water. The resulting solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible.

Health Hazard

SYMPTOMS: Symptoms of exposure to Isoprenaline hydrochloride may include tremors, nervous apprehension, palpitations of the heart, epigastric distress, cardiac arrhythmias, myocardial necrosis, cardiac arrest, tachycardia, headache, flushing of the skin, anginal pain, nausea, dizziness, weakness, and sweating.

Fire Hazard

Flash point data for Isoprenaline hydrochloride are not available. Isoprenaline hydrochloride is probably combustible.

Biological Activity

Standard selective β -adrenoceptor agonist; vasorelaxant and bronchodilator. Activation of β 2 receptors activates downstream PKA and ERK, and may stimulate NO-mediated endothelium-dependent smooth muscle relaxation. Active in vivo . Also available as part of the β -Adrenoceptor Agonist Tocriset? and Mixed Adrenergic Tocriset? .

Biochem/physiol Actions

β-adrenoceptor agonist; increases cytosolic cAMP.

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

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 
• 639007-20-8 isoprenaline glucuronide 
• 73635-69-5 tris(carboethoxy)isoproterenol 

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.