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7683-59-2

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7683-59-2 Usage

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.

Uses

Different sources of media describe the Uses of 7683-59-2 differently. You can refer to the following data:
1. Isoproterenol is used in bronchospasms, asthma, cardiac block, and shock.
2. 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.

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.

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.

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

Different sources of media describe the Clinical Use of 7683-59-2 differently. You can refer to the following data:
1. 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.
2. 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.

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 ω-chloro-3,4- dihydroxyacetophenone (chloroacetylpyrocatechol) with isopropylamine gives ω-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].

Check Digit Verification of cas no

The CAS Registry Mumber 7683-59-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,6,8 and 3 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 7683-59:
(6*7)+(5*6)+(4*8)+(3*3)+(2*5)+(1*9)=132
132 % 10 = 2
So 7683-59-2 is a valid CAS Registry Number.
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

7683-59-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name isoprenaline

1.2 Other means of identification

Product number -
Other names asmalar

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7683-59-2 SDS

7683-59-2Synthetic route

2-isopropylamino-1-<3.4-dihydroxy-phenyl>-ethanone-(1)-hydrochloride

2-isopropylamino-1-<3.4-dihydroxy-phenyl>-ethanone-(1)-hydrochloride

isoproterenol
7683-59-2

isoproterenol

Conditions
ConditionsYield
With water; palladium Hydrogenation;
2-isopropylamino-1-<3.4-dihydroxy-phenyl>-ethanone-(1)-sulfate

2-isopropylamino-1-<3.4-dihydroxy-phenyl>-ethanone-(1)-sulfate

isoproterenol
7683-59-2

isoproterenol

Conditions
ConditionsYield
With methanol; palladium Hydrogenation;
With methanol; palladium Hydrogenation;
isoproterenol
7683-59-2

isoproterenol

5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester
52600-52-9

5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

5-cyano-2-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid
101184-51-4

5-cyano-2-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride90%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride90%
methanol
67-56-1

methanol

isoproterenol
7683-59-2

isoproterenol

2-(3,4-dihydroxyphenyl)-2-[(methyl)oxy]-1-(isopropylamino)ethane hydrochloride
3868-81-3

2-(3,4-dihydroxyphenyl)-2-[(methyl)oxy]-1-(isopropylamino)ethane hydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 0.25h; Mechanism; other derivatives of 2-alkylamino-1-(4-hydroxyphenyl)-1-ethanol;85%
With hydrogenchloride for 0.25h;85%
With hydrogenchloride at 10℃;85%
ammonium vanadate(V)

ammonium vanadate(V)

isoproterenol
7683-59-2

isoproterenol

VOOH(C6H3O2HCHOHCH2NHC3H7)2*H2O

VOOH(C6H3O2HCHOHCH2NHC3H7)2*H2O

Conditions
ConditionsYield
With HNO3; NaOH In water (He); boiling (0.5 h, pH=6.6-6.7), gradual pptn.; washing (distd. water), drying (10E-3 mm Hg, 50°C, 3 h); elem. anal.;76%
isoproterenol
7683-59-2

isoproterenol

2-(chloromethyl)-2-oxo-2λ5-perhydro[1,3,2]oxazaphospholo[3,4-a]pyridine

2-(chloromethyl)-2-oxo-2λ5-perhydro[1,3,2]oxazaphospholo[3,4-a]pyridine

2-[[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl](isopropyl)amino]methyl-2-oxo-2λ5-perhydro[1,3,2]oxazaphospholo[3,4-a]pyridine

2-[[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl](isopropyl)amino]methyl-2-oxo-2λ5-perhydro[1,3,2]oxazaphospholo[3,4-a]pyridine

Conditions
ConditionsYield
With N,N'-dimethylpiperazine In tetrahydrofuran at 60 - 65℃; for 4h;70%
isoproterenol
7683-59-2

isoproterenol

C13H8Cl2N3O4P

C13H8Cl2N3O4P

4-chlorophenyl-N-2-(3,4-dihydroxyphenyl)-2-hydroxyethyl-N-isopropyl-P-(5-nitro-1H-indazol-1-yl) Phosphonamidate

4-chlorophenyl-N-2-(3,4-dihydroxyphenyl)-2-hydroxyethyl-N-isopropyl-P-(5-nitro-1H-indazol-1-yl) Phosphonamidate

Conditions
ConditionsYield
With N,N'-dimethylpiperazine In tetrahydrofuran at 50℃; for 4h;68%
ammonium vanadate(V)

ammonium vanadate(V)

isoproterenol
7683-59-2

isoproterenol

VO(C6H3O2COHCH2NHC3H7)2

VO(C6H3O2COHCH2NHC3H7)2

Conditions
ConditionsYield
With HNO3; NaOH In water boiling (0.5 h, pH=6.6-6.7), gradual pptn.; washing (distd. water), drying (10E-3 mm Hg, 50°C, 3 h); elem. anal.;61%
cis-dichlorobis(triphenylphosphine)platinum(II)
10199-34-5, 14056-88-3, 15604-36-1

cis-dichlorobis(triphenylphosphine)platinum(II)

isoproterenol
7683-59-2

isoproterenol

Pt(P(C6H5)3)2(O2C6H3CH(OH)CH2NHCH(CH3)2)
87405-03-6

Pt(P(C6H5)3)2(O2C6H3CH(OH)CH2NHCH(CH3)2)

Conditions
ConditionsYield
With potassium hydroxide In methanol; benzene to a suspn. of substituted catechol in benzene was added MeOH soln. of KOH; prepd. soln. was syringed into suspn. of Pt complex in benzene; stirring at room temp. for 3.5 h (Ar); filtration, evapn., washing with water, drying in vac., dissoln. in CH2Cl2, filtration, evapn., washing with ether, drying in vac., crystn. from ether/hexane; elem. anal.;50%
isoproterenol
7683-59-2

isoproterenol

N-Isopropyl-noradrenochrom
3736-31-0

N-Isopropyl-noradrenochrom

Conditions
ConditionsYield
With water; acetic acid; potassium hexacyanoferrate(III)
With water; silver(l) oxide
With riboflavin In water UV-irradiation;
isoproterenol
7683-59-2

isoproterenol

(S)-isoproterenol
2964-04-7

(S)-isoproterenol

Conditions
ConditionsYield
With L-Tartaric acid
isoproterenol
7683-59-2

isoproterenol

isoprenaline
51-31-0

isoprenaline

Conditions
ConditionsYield
With L-Tartaric acid
isoproterenol
7683-59-2

isoproterenol

air

air

N-Isopropyl-noradrenochrom
3736-31-0

N-Isopropyl-noradrenochrom

Conditions
ConditionsYield
mushroom tyrosinase Ambient temperature; phosphate buffer pH=6.8;
isoproterenol
7683-59-2

isoproterenol

A

(S)-isoproterenol
2964-04-7

(S)-isoproterenol

B

isoprenaline
51-31-0

isoprenaline

Conditions
ConditionsYield
With MCCD-HPS packed column In hydrogenchloride; methanol pH=8.6;
With diethylamine In acetonitrile Reagent/catalyst; Resolution of racemate;
With phase-transitioned bovine serum albumin film-coated capillary column In methanol pH=9; Resolution of racemate;
isoproterenol
7683-59-2

isoproterenol

C11H15NO3
14309-63-8

C11H15NO3

Conditions
ConditionsYield
With oxygen In phosphate buffer at 20℃; pH=6.8; Enzyme kinetics;
In aq. phosphate buffer pH=5; pH-value; Concentration; Electrochemical reaction;
isoproterenol
7683-59-2

isoproterenol

N-isopropyl-5,6-diacetoxyindole
22218-45-7

N-isopropyl-5,6-diacetoxyindole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Mushroom tyrosinase / Ambient temperature; phosphate buffer pH=6.8
2: 1) ascorbic acid, 2) dimethylaminopyridine / 2) Phosphate buffer, diethyl ether, 2) diethyl ether
View Scheme
isoproterenol
7683-59-2

isoproterenol

Divascan
81303-50-6

Divascan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: silver oxide; water
View Scheme
Multi-step reaction with 2 steps
1: potassium hexacyanoferrate(III); water; acetic acid
View Scheme
isoproterenol
7683-59-2

isoproterenol

copper dichloride

copper dichloride

Cu(2+)*2H(1+)*2(O2C6H3CH(OH)CH2NHCH(CH3)2)(2-) = Cu((CH3)2CHNHCH2CH(OH)C6H3(OH)(O))2

Cu(2+)*2H(1+)*2(O2C6H3CH(OH)CH2NHCH(CH3)2)(2-) = Cu((CH3)2CHNHCH2CH(OH)C6H3(OH)(O))2

Conditions
ConditionsYield
In not given reflux of soln. of metal salt and ligand in 1:2 molar ratio (slight excess of ligand) for 5 h; concd. on water bath, vac. drying in vac. desiccator, washing with abs.alc., alc. soln. dried in vac., elem. anal.;
isoproterenol
7683-59-2

isoproterenol

cobalt(II) chloride
7646-79-9

cobalt(II) chloride

Co(2+)*2H(1+)*2(O2C6H3CH(OH)CH2NHCH(CH3)2)(2-)*2H2O = Co((CH3)2CHNHCH2CH(OH)C6H3(OH)(O))2(H2O)2

Co(2+)*2H(1+)*2(O2C6H3CH(OH)CH2NHCH(CH3)2)(2-)*2H2O = Co((CH3)2CHNHCH2CH(OH)C6H3(OH)(O))2(H2O)2

Conditions
ConditionsYield
In not given reflux of soln. of metal salt and ligand in 1:2 molar ratio (slight excess of ligand) for 5 h; concd. on water bath, vac. drying in vac. desiccator, washing with abs.alc., alc. soln. dried in vac., elem. anal.;
isoproterenol
7683-59-2

isoproterenol

nickel dichloride

nickel dichloride

Ni(2+)*2H(1+)*2(O2C6H3CH(OH)CH2NHCH(CH3)2)(2-) = Ni((CH3)2CHNHCH2CH(OH)C6H3(OH)(O))2

Ni(2+)*2H(1+)*2(O2C6H3CH(OH)CH2NHCH(CH3)2)(2-) = Ni((CH3)2CHNHCH2CH(OH)C6H3(OH)(O))2

Conditions
ConditionsYield
In not given reflux of soln. of metal salt and ligand in 1:2 molar ratio (slight excess of ligand) for 5 h; concd. on water bath, vac. drying in vac. desiccator, washing with abs.alc., alc. soln. dried in vac., elem. anal.;
isoproterenol
7683-59-2

isoproterenol

VO(C6H3O2COHCH2NHC3H7)2*2H2O

VO(C6H3O2COHCH2NHC3H7)2*2H2O

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HNO3; NaOH / water
2: H2O / neat (no solvent, solid phase)
View Scheme

7683-59-2Upstream product

7683-59-2Relevant articles and documents

1,4-dihydropyridine derivative with a guaiacoxypropanolamine and/or phenoxypropanolamine moiety

-

, (2008/06/13)

The invention disclosed some 1,4-dihydropiridine derivative chemically with guaiacoxypropanolamine based phenoxypropanolamine moiety and pharmacologically with β-adrenoceptor blocking and partial β2-agonist activities, is now emerging. The compound of 1,4-dihydropiridine derivative wherein has the formula I, wherein R selected from four group as follow R1 selected from X, H, NO2 saturated C1-C6 alkyl chain, unsaturated C6-C6 alkyl chain, R2 selected from H, CH3 R3 and R4 are individually selected from saturated C1-C6 alkyl chain, unsaturated C1-C6 alkyl chain; R5 selected from OH, saturated C1-C6 alkyl chain, unsaturated C1-C6 alkyl chain.

Antiinflammatory salts of piroxicam

-

, (2008/06/13)

Improved antiinflammatory salts of piroxicam with antidepressant doxepin, with bronchodilator pirbuterol or isoproterenol, with H2 -antagonist inhibitor 2-guanidino-4-(2-methyl-4-imidazolyl)thiazole, with pyridoxine, a member of the vitamin B6 complex, or with antihypertensive trimazosin.

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