Tmic
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Record Information
Version1.0
Creation Date2014-10-14 21:18:14 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003933
Identification
Common NameIsoprenaline
ClassSmall Molecule
DescriptionIsopropyl analog of epinephrine; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant. [PubChem]
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Adrenergic beta-Agonist
  • Bronchodilator Agent
  • Cardiotonic Agent
  • Drug
  • Metabolite
  • Sympathomimetic
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
(+-)-IsoprenalineChEBI
(+-)-IsoproterenolChEBI
1-(3,4-Dihydroxyphenyl)-2-(isopropylamino)ethanolChEBI
1-(3,4-Dihydroxyphenyl)-2-isopropylaminoethanolChEBI
3,4-Dihydroxy-alpha-[(isopropylamino)methyl]benzyl alcoholChEBI
alpha-(Isopropylaminomethyl)protocatechuyl alcoholChEBI
IsoprenalinaChEBI
IsoprenalinumChEBI
Isopropyl noradrenalineChEBI
N-Isopropyl-beta-dihydroxyphenyl-beta-hydroxyethylamineChEBI
N-IsopropylnoradrenalineChEBI
N-IsopropylnorepinephrineChEBI
IsoprenalineKegg
3,4-Dihydroxy-a-[(isopropylamino)methyl]benzyl alcoholGenerator
3,4-Dihydroxy-α-[(isopropylamino)methyl]benzyl alcoholGenerator
a-(Isopropylaminomethyl)protocatechuyl alcoholGenerator
Α-(isopropylaminomethyl)protocatechuyl alcoholGenerator
N-Isopropyl-b-dihydroxyphenyl-b-hydroxyethylamineGenerator
N-Isopropyl-β-dihydroxyphenyl-β-hydroxyethylamineGenerator
Epinephrine isopropyl homologHMDB
IsoprenalinHMDB
IsopropydrinHMDB
IsopropyladrenalineHMDB
IsopropylarterenolHMDB
IsopropylnoradrenalineHMDB
IsopropylnorepinephrineHMDB
Isoproterenol chlorideHMDB
L-IsopropylnoradrenalineHMDB
L-IsoproterenolHMDB
EuspiranHMDB
IsuprelHMDB
IsadrinHMDB
4-(1-Hydroxy-2-((1-methylethyl)amino)ethyl)-1,2-benzenediolHMDB
NorisodrineHMDB
Hydrochloride, isoproterenolHMDB
IsadrineHMDB
Isoproterenol hydrochlorideHMDB
Isoproterenol sulfateHMDB
IzadrinHMDB
Noradrenaline, isopropylHMDB
NovodrinHMDB
Sulfate, isoproterenolHMDB
IsoproterenolChEBI
Chemical FormulaC11H17NO3
Average Molecular Mass211.258 g/mol
Monoisotopic Mass211.121 g/mol
CAS Registry Number7683-59-2
IUPAC Name4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol
Traditional Nameisoproterenol
SMILESCC(C)NCC(O)C1=CC(O)=C(O)C=C1
InChI IdentifierInChI=1S/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
InChI KeyJWZZKOKVBUJMES-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Aromatic alcohol
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point180 °C
Boiling PointNot Available
Solubility5.86e+00 g/L
Predicted Properties
PropertyValueSource
Water Solubility5.86 g/LALOGPS
logP-0.27ALOGPS
logP0.24ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.81ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity58.4 m³·mol⁻¹ChemAxon
Polarizability23.04 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-05gr-9700000000-1d8ddbb3b9ecf4bd4e41View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS)splash10-001i-4193300000-51704909fccedbd3a27fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1390000000-f9a4d1db36e6a6829da6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fu-4940000000-b4ce8517db087019ae02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8900000000-70b5626c51c5c776cac0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0940000000-a69543d0053d7699ab89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udu-0900000000-6d817d647f12c2387c5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zg3-7900000000-4048df303bf76bdeb169View in MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityThe pharmacologic effects of isoproterenol are at least in part attributable to stimulation through beta-adrenergic receptors of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic AMP. Increased cyclic AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of mild or transient episodes of heart block that do not require electric shock or pacemaker therapy also used in management of asthma and chronic bronchitis
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01064
HMDB IDHMDB0015197
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIsoprenaline
Chemspider ID3647
ChEBI ID64317
PubChem Compound ID3779
Kegg Compound IDC07056
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

U.S. Patent 2,308,232.
U.S. Patent 2,715,141.

MSDSNot Available
General ReferencesNot Available