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7683-59-2

Basic Information
CAS No.: 7683-59-2
Name: Isoproterenol
Molecular Structure:
Molecular Structure of 7683-59-2 (Isoproterenol)
Formula: C11H17 N O3
Molecular Weight: 211.261
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;
EINECS: 231-687-7
Density: 1.1240 (rough estimate)
Melting Point: 165 - 170 C
Boiling Point: 350.94°C (rough estimate)
Solubility: Soluble white crystalline powder
Hazard Symbols: UN NO.
Transport Information: HAZARD
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

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

7683-59-2

isoproterenol

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

isoproterenol

52600-52-9

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

107-91-5

cyanoacetic acid amide

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%
67-56-1

methanol

7683-59-2

isoproterenol

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)

7683-59-2

isoproterenol

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%
7683-59-2

isoproterenol

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

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

isoproterenol

C13H8Cl2N3O4P

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)

7683-59-2

isoproterenol

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%
10199-34-5, 14056-88-3, 15604-36-1

cis-dichlorobis(triphenylphosphine)platinum(II)

7683-59-2

isoproterenol

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%
7683-59-2

isoproterenol

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;
Downstream Products
101184-51-4
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Chemistry

Molecular Formula: C11H17NO3
Molecular Weight: 211.26
EINECS: 231-687-7
Density: 1.199 g/cm
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)

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.


 
 

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

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.