Levisoprenaline
Basic information
- CAS
51-31-0- Standard SMILES
CC(C)NC[C@H](O)c1ccc(O)c(O)c1- InChIKey
JWZZKOKVBUJMES-NSHDSACASA-N- Molecular formula
- C11H17NO3
- Average molar mass
- 211.26 g/mol
- Monoisotopic mass
- 211.1208434
Overview
L-isoprenaline is an optically active phenylethanolamine compound having an isopropyl substituent attached to the nitrogen atom. It has a role as a beta-adrenergic agonist and a sympathomimetic agent. It is a member of phenylethanolamines and a catecholamine.
Names & identifiers
- Preferred name
- Levisoprenaline
- IUPAC
- 4-[(1R)-1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol
- English name
- Levisoprenaline
- Molecular formula
- C11H17NO3
- Molecular weight
- 211.26
Names & synonyms
LEVISOPRENALINEl-Isoprenaline51-31-0(-)-Isoproterenoll-Isoproterenol(R)-IsoproterenolLevisoprenalina(-)-Isoprenaline(R)-IsoprenalineIsoproterenol, L-LevisoprenalinumL-(-)-Isoproterenol
Show more names
C11703Proternol LBRN 3203136BRN-3203136
Isopropyl norepinephrinel-Isopropylnoradrenaline(-)-N-IsopropylnoradrenalineL-IsopropylnorepinephrineIsoprenaline, (r)-Levisoprenaline [INN:DCF]Levisoprenalinum [INN-Latin]Isoproterenol l-form
Database identifiers
- CAS
51-31-0- PubChem CID
- 443372
- DTXSID
DTXSID2043878- ChEMBL
CHEMBL1160723- ChEBI
CHEBI:6257- UNII
- 588N0603CT
- EC Number
- 633-441-8
- Nikkaji
- J4.115G
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 72.7 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 187
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Boiling point
- 417.5 · 417.5±40.0 °C(Predicted)
- Density
- 1.199 · 1.199±0.06 g/cm3(Predicted)
- Melting point
- 157 · 157-158 °C
- pka
- 9.6 · 9.60±0.10(Predicted)
- FDA UNII
- 588 N0603CT · 588N0603CT
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Toxicity Summary
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.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Uses & manufacturing
UsesFor 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
Applications
Uses(-)-Isoproterenol (Levisoprenalinel) is a bioactive compound.
Additional notes
DefinitionChEBI: An optically active phenylethanolamine compound having an isopropyl substituent attached to the nitrogen atom.
Suppliers
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Compound notes
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