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Isoproterenol

CAS No.7683-59-2
Chemical Name:Isoproterenol
CBNumber:CB3854910
Molecular Formula:C11H17NO3
Formula Weight:211.26
MOL File:7683-59-2.mol

Isoproterenol Property

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℃)
FDA UNII L628TT009W
NIST Chemistry Reference 3,4-Dihydroxy-«alpha»-(isopropylaminomethyl)-benzyl alcohol(7683-59-2)
ATC code C01CA02,R03AB02,R03CB01,R03CB51

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Hazard statements
Precautionary statements

Isoproterenol Chemical Properties,Usage,Production

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
Uses Isoproterenol is used in bronchospasms, asthma, cardiac block, and shock.
Uses Isoprenaline is a potent β-agonist primarily acting at the β1-receptor. It is mainly used for the temporary emergency treatment of bradyarrhythmias. β2 effects lead to broncho- and vasodilatation, with a decrease in SVR. Isoprenaline is only available in the UK via specialist importing companies. It is administered by i.v. infusion at a dose range of 0.5–20 μg min–1.
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.
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.
brand name Medihaler-ISO (3M Pharmaceuticals);Aerolone;Aerotrol;Afdosa;Aldo asma;Aleudrina;Anthastmin;Asmadren;Asmastop;Atom-asma;Dey-dose;Dispos-a-med;Duo-autohaler;Duo-medihaler;Dyspnoesan;Erydin;Frenal composium;Imuprel;Ingelan;Intal compositum;Iso-autohaler;Isonorin;Isoprel-neomistometer;Isoprop;Isorenin;Katwilon n;Lenoprel;Luf-iso;Medihaler-duo;Meterdos-iso;Neo epinine;Nephenalin;Norisodrin aerotol;Norisodrin with calcium idodide;Norosodrine;Older;Orotenol;Prenomiser;Propynalin;Protenol;Sedantosol;Sooner.
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.
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
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].