ChemicalBook CAS DataBase List 7683-59-2

7683-59-2

Name	Isoproterenol
CAS	7683-59-2
EINECS(EC#)	231-687-7
Molecular Formula	C11H17NO3
Molecular Weight	211.26
MOL File	7683-59-2.mol

Chemical Properties

Melting point	170.5°C
Boiling point	350.94°C (rough estimate)
density	1.1240 (rough estimate)
refractive index	1.5718 (estimate)
pka	8.64(at 25℃)
NIST Chemistry Reference	3,4-Dihydroxy-«alpha»-(isopropylaminomethyl)-benzyl alcohol(7683-59-2)

Safety Data

Safety Profile

Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. Human systemic effects by intramuscular route: increased pulse and cardac rate. A bronchodilator. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx

Raw materials And Preparation Products

Hazard Information

Uses

Bronchodilator.

Definition

ChEBI: A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hy rochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.

Brand name

Medihaler-ISO (3M Pharmaceuticals).

Description

Isoproterenol is a representative of the sympathomimetic drugs with high selectivity to β- adrenoreceptors. As was already noted, the addition to compounds of a bulky iso-propyl or tert-butyl group at the nitrogen atom of the β-phenylethylamino skeleton is associated with higher affinity to β-adrenergic receptive regions than to α-adrenergic. Isoproterenol is devoid of significant α-adrenergic agonistic action. Activation of β1-adrenergic receptors in the heart increases positive chronotropic and ionotropic action. Peripheral vascular resistance is increased by the widening of blood vessels, primarily in skeletal muscle, but also in renal and mesenteric blood circulation, which is caused by the β2-adrenergic system.

Originator

Isonorin,Smith, Miller and Patch,US,1949

Indications

Isoproterenol is administered almost exclusively by inhalation from metered-dose inhalers or from nebulizers. The response to inhaled isoproterenol and other inhaled adrenomimetics is instantaneous. The action of isoproterenol is short-lived, although an objective measurement of pulmonary function has shown an effective duration of up to 3 hours. When it is administered by inhalation, the cardiac effects of isoproterenol are relatively mild, although in some cases a substantial increase in heart rate occurs.

Manufacturing Process

As described in US Patent 2,308,232, 100 g 3,4-dihydroxy-ω- chloroacetophenone, 200 cc ethyl alcohol and 200 cc of about 50% aqueous isopropylamine solution are boiled during 3 hours on the water bath with the use of a reflux condenser, whereupon neutralizing with diluted sulfuric acid is carried out and the sulfate, obtained upon cooling, from alcohol of 50% is recrystallized; its MP is 245°C.
21 g 3,4-dihydroxy-ω-isopropylaminoacetophenone sulfate are hydrogenated with 50 cc methyl alcohol and 50 cc water, 0.5 g carbon and 3 cc palladium chloride solution of 2%. After 2 hours the hydrogen absorption comes to a standstill, after the theoretical quantity of hydrogen has been absorbed. After concentrating, the isopropylaminomethyl-(3,4-dihydroxyphenyl)carbinolsulfate crystallizes out. It has a MP of 180°C after refining.

Therapeutic Function

Bronchodilator

World Health Organization (WHO)

Isoprenaline, a beta-adrenoreceptor agonist, was introduced in 1949 as treatment for a number of cardiac disorders and as a bronchial dilator for the symptomatic treatment of asthma. There is evidence that regular inhalation of bronchodilator drugs is associated, in some cases with exacerbation of the disease and with increased fatality rates. The underlying causes are disputed, but an increasing body of opinion now advocates regular maintenance therapy with inhaled, corticosteroids coupled with supplementary use as required of bronchial drugs to suppress exacerbations.

General Description

Isoproterenol is a nonselective and prototypical -agonist ( β2/ β1=1). After oral administration,the absorption of ISO is rather erratic and undependable.The principal reason for its poor absorption characteristicsand relatively short DOA is its facile metabolism by sulfateand glucuronide conjugation of the phenolic OH groupsand O-methylation by COMT. Because it is a catechol, it issensitive to light and air. Aqueous solutions become pinkon standing. Unlike E and NE, ISO does not appear to undergo oxidative deamination by MAO. The drug hasDOA of 1 to 3 hours after inhalation.

Clinical Use

Isoproterenol is used principally by inhalation for the management of bronchospasm. It is also used intravenously for asthma and as a stimulant in cardiac arrest.

Clinical Use

The cardiac stimulation caused by its 1-activity andits lack of oral activity have led to its diminished use infavor of more selective -agonists. The problems have beenovercome at least partially by the design and developmentof several noncatechol selective 2-agonists. These agentsrelax smooth muscle of the bronchi, uterus, and skeletalmuscle vascular supply. They find their primary use as bronchodilatorsin the treatment of acute and chronic bronchialasthma and other obstructive pulmonary diseases.

Synthesis

Isoproterenol, 1-(3,4-dihydroxyphenyl)-2-iso-propylaminoethanol (11.1.8), is synthesized by an analogous scheme of making epinephrine. Interaction of |?-chloro-3,4- dihydroxyacetophenone (chloroacetylpyrocatechol) with isopropylamine gives |?-isopropylamino-3,4-dihydroxyacetophenone (11.1.7), reduction of the carbonyl group of which by hydrogen using a palladium on carbon catalyst gives isoproterenol (11.1.8) [11,12].

Synthesis_7683-59-2

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