16899-81-3

Basic information

• Product Name: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride
• Synonyms: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride;U 12844A;Ethanone,1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino]-, hydrochloride (1:1);1-(3,4-Dihydroxyphenyl)-2-[(1-methylethyl)amino]ethanone hydrochloride;Isoprenaline impurity A
• CAS NO: 16899-81-3
• Molecular Formula: C₁₁H₁₅NO₃*ClH
• Molecular Weight: 245.704
• EINECS: 240-943-7
• Mol File: 16899-81-3.mol

Chemical Properties

• Melting Point: 255-257℃
• Boiling Point: 409.7°Cat760mmHg
• Flash Point: 201.6°C
• Appearance: /
• Density: 1.185g/cm³
• Vapor Pressure: 2.69E-07mmHg at 25°C
• CAS DataBase Reference: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride(16899-81-3)
• EPA Substance Registry System: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride(16899-81-3)

Safety Data

• Hazardous Substances Data: 16899-81-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride is used as an impurity in the production of Isoprenaline hydrochloride for the treatment of bradycardia. Its presence, although as an impurity, contributes to the overall effectiveness of the medication in addressing the specific medical condition.
Isoprenaline, the primary compound from which 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride is derived, is used as a non-selective beta-adrenergic agonist for the treatment of bradycardia. This application is based on its ability to stimulate the beta-adrenergic receptors, leading to an increase in heart rate and addressing the issue of bradycardia.

Preparation

Obtained by condensation of a-chloro-3,4- dihydroxy-acetophenone with isopropylamine in isopropanol at 65–70°. The amino ketone which separated was treated with concentrated hydrochloric acid (54%), (46%).

InChI:InChI=1/C11H15NO3.ClH/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8;/h3-5,7,12-14H,6H2,1-2H3;1H

Upstream product

• 99-40-1 2-chloro-3',4'-dihydroxyacetophenone 
• 75-31-0 isopropylamine 
• 75-29-6 isopropyl chloride 
• 499-61-6 arterenone 
• 120-80-9 benzene-1,2-diol 

Downstream Products

• 30416-00-3 3,4-Bis-(p-toluyloxy)phenylisopropylaminomethylketon 
• 30416-01-4 C₂₇H₂₇NO₅*C₂HF₃O₂ 
• 98634-90-3 3',4'-diacetoxy-2-(isopropylamino)acetophenone hydrochloride 
• 55508-67-3 3,4-O-diacetylisoproterenol hydrochloride 
• 18810-21-4 (+)-Isoproterenol hydrochloride 
• 51-30-9 isoproterenol hydrochloride 

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.

Hydrochloric acid isopropyl adrenergic preparation method

The invention discloses a hydrochloric acid isopropyl adrenergic preparation method, comprises the following steps: through the catechol with glycine in the role of the catalyst [...] reaction to obtain 2 - amino - 1 - (3, 4 - dihydroxy-phenyl) - ethyl ketone; through the 2 - amino - 1 - (3, 4 - dihydroxy-phenyl) - ethanone with 2 - chloro propane reaction preparation isopropyl adrenergic ketone bodies hydrochloride; through the isopropyl adrenergic ketone bodies hydrochloride in the catalytic reduction of the palladium-carbon under the action of hydrochloric acid isopropyl adrenergic. Selects the glycin, zinc chloride the reaction system, which not only reduces the costs of environmental protection, also improves the reaction yield, is favorable for industrial production; mild reaction conditions, less catalyst levels, the process is simple; it has obvious economic and environmental benefits.

Method for preparing isoproterenol hydrochloride

The invention relates to a method for preparing isoproterenol hydrochloride. The method comprises the following steps: (1) preparation of 2-amino-1-(3, 4-dihydroxy phenyl)-ethanone; (2) preparation of isoproterenol ketone hydrochloride; and (3) preparation of isoproterenol hydrochloride. The method disclosed by the invention adopts a reaction system of glycine and zinc chloride instead of a reaction system of monochloro acetic acid and phosphorus oxychloride, so that the method has the advantages that the environmental protection cost is reduced; the reaction yield is increased; the industrial production is benefited; the reaction condition is mild; the catalyst quantity is little; and the process is simple. Compared with conventional synthetic processes, the method disclosed by the invention has obvious economic benefit and environmental benefit.

Isolated perfused rabbit lung as a model for intravascular and intrabronchial administration of bronchodilator drugs II: isoproterenol prodrugs

The pulmonary disposition of two diester prodrugs of isoproterenol (di-p-toluoylisoproterenol and dipivaloylisoproterenol) was studied in the isolated perfused rabbit lung preparation. High-pressure liquid chromatographic methods were developed to measure diester, monoester, isoproterenol, and 3-O-methylisoproterenol from a single 1-ml perfusate sample. The prodrugs were administered directly into the circulating perfusion medium and by endotracheal instillation. Perfusate concentrations of diester, monoester, isoproterenol, and 3-O-methylisoproterenol were measured for 180 min. The diesters were rapidly eliminated from the perfusate with a subsequent increase in monoester concentrations. Isoproterenol levels were observed within minutes of prodrug administration, peaked at 60-80 min, and declined slowly thereafter. The prodrugs were rapidly absorbed following endotracheal administration with 30-50% of the diester being metabolized during the first pass through the lung.