Product Name

  • Name

    Isoproterenol

  • EINECS 231-687-7
  • CAS No. 7683-59-2
  • Density 1.1240 (rough estimate)
  • Solubility Soluble
  • Hazard Symbols UN NO.
  • Synonyms Benzylalcohol, 3,4-dihydroxy-a-[(isopropylamino)methyl]- (8CI);1-(3,4-Dihydroxyphenyl)-2-(isopropylamino)ethanol;3,4-Dihydroxy-a-[(isopropylamino)methyl]benzylalcohol;A 21;Aludrin;Aludrine;Asiprenol;Asmalar;Assiprenol;Bellasthman;DL(?à)-Isoproterenol;DL-Isopropylnorepinephrine;DL-Isoproterenol;Epinephrine isopropyl homolog;ICI 46399;Isonorin;Isoprenalin;Isoprenaline;Isopropydrin;Isopropylaminomethyl(3,4-dihydroxyphenyl)carbinol;Isopropylarterenol;Isopropylnoradrenaline;Isopropylnorepinephrine;Isoproterenol;Isorenin;Isupren;Lomupren;N-Isopropyl-b-dihydroxyphenyl-b-hydroxyethylamine;N-Isopropylnoradrenaline;N-Isopropylnorepinephrine;NSC 33791;NSC 9975;Neo-Epinine;Neodrenal;Norisodrine;Racemic isoprenaline;Racemic isoproterenol;Respifral;Vapo-N-Iso;dl-Isadrine;dl-Isoprenaline;dl-Isopropylnoradrenaline;dl-Isoproterenol;dl-N-Isopropylnoradrenaline;
  • PSA 72.72000
  • LogP 1.52010

Synthetic 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%
...Expand
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

Isoproterenol Chemical Properties

Molecular Formula: C11H17NO3
Molecular Weight: 211.26
EINECS: 231-687-7
Density: 1.199 g/cm3 
Flash Point: 179.7 °C
Melting Point: 155.5°C
Index of Refraction: 1.579
Appearance: Off-color crystal
CAS Registry Number: 7683-59-2 
Enthalpy of Vaporization: 70.73 kJ/mol 
Boiling Point: 417.5 °C at 760 mmHg 
Vapour Pressure: 1.02E-07 mmHg at 25°C 
IUPAC Name: 4-[1-Hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol
Synonyms: 4-[1-Hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol ; Isoproterenol ; Isoprel ; Isoprenaline ; Saventrine ; 1,2-Benzenediol, 4-1-hydroxy-2-(1-methylethyl)aminoethyl- ; 1,2-Benzenediol, 4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]- (9CI) ; Dl-Isadrine
Following is the molecular structure of Isoproterenol (CAS NO.7683-59-2)

Isoproterenol Uses

Isoproterenol (CAS NO.7683-59-2)'s primary use is for bradycardia or heart block. By activating β1-receptors on the heart, it induces positive chronotropic, dromotropic, and inotropic effects.
It can be used as an inhaled aerosol to treat asthma, although this is currently a rare treatment.[1] Although it activates all beta adrenergic receptors, it works in a similar fashion to the more selective β2-adrenergic agonists e.g. salbutamol, by relaxing the airways to increase airflow.
It is also supplied in ampules under the brand name Isuprel for injection and in sublingual pill form for treatment of asthma, chronic bronchitis and emphysema.
Used with caution, Isoproterenol (CAS NO.7683-59-2) can also be used to treat torsades de pointes by congenital defect, in conjunction with overdrive pacing and magnesium.
Adipose tissue also has β-receptors that can be activated by isoproterenol. Once activated, adipocytes begin breaking down the fat stored inside them. This has caused isoproterenol to be used off-label in mesotherapy for body contouring and to help decrease fat. Two studies showed that it can cause a decrease in thigh size.


 
 

Isoproterenol Toxicity Data With Reference

1.    

oms-rat-par 100 mg/kg

     BEXBAN    Bulletin of Experimental Biology and Medicine. Translation of BEBMAE. 94 (1982),1458.
2.    

dns-mus-ipr 341 mg/kg

     JCLBA3    Journal of Cell Biology. 56 (1973),605.
3.    

ims-hmn TDLo:14 µg/kg:CVS

     KLWOAZ    Klinische Wochenscrift. 19 (1940),1303.
4.    

orl-rat LD50:355 mg/kg

     USXXAM    United States Patent Document. (Commissioner of Patents and Trademarks, Washington, DC 20231) #4026897 .
5.    

ipr-rat LDLo:100 mg/kg

     FCTXAV    Food and Cosmetics Toxicology. 3 (1965),597.
6.    

scu-rat LD50:600 µg/kg

     TOXID9    Toxicologist. 4 (1984),77.
7.    

ivn-rat LD50:57 mg/kg

     TXAPA9    Toxicology and Applied Pharmacology. 16 (1970),303.
8.    

orl-mus LD50:450 mg/kg

     27ZIAQ    Drug Dosages in Laboratory Animals-A Handbook C.D. Barnes andL.G. Eltherington,Berkeley, CA.: Univ. of California Press,1973,139.
9.    

ipr-mus LD50:440 mg/kg

     JPETAB    Journal of Pharmacology and Experimental Therapeutics. 164 (1968),290.
10.    

scu-mus LD50:400 mg/kg

     ARZNAD    Arznei

Isoproterenol 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 cardiac rate. A bronchodilator. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
 

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