ContaminantDB: Isoprenaline

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (7)XML

Record Information

Version

1.0

Creation Date

2014-10-14 21:18:14 UTC

Update Date

2016-11-09 01:09:15 UTC

Accession Number

CHEM003933

Identification

Common Name

Isoprenaline

Class

Small Molecule

Description

Isopropyl 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(+-)-Isoprenaline	ChEBI
(+-)-Isoproterenol	ChEBI
1-(3,4-Dihydroxyphenyl)-2-(isopropylamino)ethanol	ChEBI
1-(3,4-Dihydroxyphenyl)-2-isopropylaminoethanol	ChEBI
3,4-Dihydroxy-alpha-[(isopropylamino)methyl]benzyl alcohol	ChEBI
alpha-(Isopropylaminomethyl)protocatechuyl alcohol	ChEBI
Isoprenalina	ChEBI
Isoprenalinum	ChEBI
Isopropyl noradrenaline	ChEBI
N-Isopropyl-beta-dihydroxyphenyl-beta-hydroxyethylamine	ChEBI
N-Isopropylnoradrenaline	ChEBI
N-Isopropylnorepinephrine	ChEBI
Isoprenaline	Kegg
3,4-Dihydroxy-a-[(isopropylamino)methyl]benzyl alcohol	Generator
3,4-Dihydroxy-α-[(isopropylamino)methyl]benzyl alcohol	Generator
a-(Isopropylaminomethyl)protocatechuyl alcohol	Generator
Α-(isopropylaminomethyl)protocatechuyl alcohol	Generator
N-Isopropyl-b-dihydroxyphenyl-b-hydroxyethylamine	Generator
N-Isopropyl-β-dihydroxyphenyl-β-hydroxyethylamine	Generator
Epinephrine isopropyl homolog	HMDB
Isoprenalin	HMDB
Isopropydrin	HMDB
Isopropyladrenaline	HMDB
Isopropylarterenol	HMDB
Isopropylnoradrenaline	HMDB
Isopropylnorepinephrine	HMDB
Isoproterenol chloride	HMDB
L-Isopropylnoradrenaline	HMDB
L-Isoproterenol	HMDB
Euspiran	HMDB
Isuprel	HMDB
Isadrin	HMDB
4-(1-Hydroxy-2-((1-methylethyl)amino)ethyl)-1,2-benzenediol	HMDB
Norisodrine	HMDB
Hydrochloride, isoproterenol	HMDB
Isadrine	HMDB
Isoproterenol hydrochloride	HMDB
Isoproterenol sulfate	HMDB
Izadrin	HMDB
Noradrenaline, isopropyl	HMDB
Novodrin	HMDB
Sulfate, isoproterenol	HMDB
Isoproterenol	ChEBI

Chemical Formula

C₁₁H₁₇NO₃

Average Molecular Mass

211.258 g/mol

Monoisotopic Mass

211.121 g/mol

CAS Registry Number

7683-59-2

IUPAC Name

4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol

Traditional Name

isoproterenol

SMILES

CC(C)NCC(O)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=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 Key

JWZZKOKVBUJMES-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:64317 )
catechols (CHEBI:64317 )
secondary amino compound (CHEBI:64317 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	180 °C
Boiling Point	Not Available
Solubility	5.86e+00 g/L

Predicted Properties

Property	Value	Source
Water Solubility	5.86 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	0.24	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.81	ChemAxon
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	72.72 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	58.4 m³·mol⁻¹	ChemAxon
Polarizability	23.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05gr-9700000000-1d8ddbb3b9ecf4bd4e41	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-001i-4193300000-51704909fccedbd3a27f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-0940000000-a69543d0053d7699ab89	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udu-0900000000-6d817d647f12c2387c5b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zg3-7900000000-4048df303bf76bdeb169	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1390000000-f9a4d1db36e6a6829da6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fu-4940000000-b4ce8517db087019ae02	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-8900000000-70b5626c51c5c776cac0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0920000000-cf36ef242942ec87ce21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-4900000000-5b84f5f51437a459c629	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k9j-8900000000-1d0384f1f487a005b30c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0090000000-840d7dbcf79278e91a76	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01w0-0910000000-545a4d1a8047f492d874	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4u-5900000000-5b03f3b94e0d996de579	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

The 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.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For 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 Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01064

HMDB ID

HMDB0015197

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

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

MSDS

Not Available

General References

Not Available

Isoprenaline (CHEM003933)

Structure for CHEM003933: Isoprenaline