(1S,2R)-(+)-Norephedrine
Basic information
- CAS
14838-15-4- Standard SMILES
CC(N)C(O)c1ccccc1- InChIKey
DLNKOYKMWOXYQA-UHFFFAOYSA-N- Molecular formula
- C9H13NO
- Average molar mass
- 151.21 g/mol
- Monoisotopic mass
- 151.09971404
Overview
Phenylpropanolamine is a sympathomimetic agent that acts as a nonselective adrenergic receptor agonist and norepinephrine reuptake inhibitor. It has been used as a decongestant and appetite suppressant. Currently, it is withdrawn from the market in Canada and the United States due to the risk for hemorrahgic strokes.
Names & identifiers
- Preferred name
- (1S,2R)-(+)-Norephedrine
- IUPAC
- 2-amino-1-phenylpropan-1-ol
- English name
- Benzenemethanol, -alpha--(1-aminoethyl)-
- Molecular formula
- C9H13NO
- Molecular weight
- 151.21
Names & synonyms
2-Amino-1-phenyl-1-propanol(1S,2R)-(+)-NorephedrineDTXSID70859305RefChem:393928DTXCID00196755628-077-148115-38-4alpha-(1-aminoethyl)benzyl alcoholNSC-120735UNII-683H0R96592-Amino-2-methyl-1-phenylethanol2-Amino-1-hydroxy-1-phenylpropane
Show more names
α-(1-Aminoethyl)benzenemethanolBenzenemethanol, α-(1-aminoethyl)-Benzenemethanol, -alpha--(1-aminoethyl)-
beta-Hydroxy-alpha-methylphenethylamineBenzenemethanol, alpha-(1-aminoethyl)-Benzenemethanol, .alpha.-(1-aminoethyl)-683H0R965937577-28-9Dexatrim(-)-Pseudo NorephedrineNorpseudoephedrine, (+)-
Database identifiers
- CAS
14838-15-4、37577-28-9、48115-38-4- PubChem CID
- 4786
- DTXSID
DTXSID70859305- ChEMBL
CHEMBL61006- EC Number
- 628-077-1
- Nikkaji
- J136.573H
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 46.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 110
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Phenethylamines (Amphetamines) (S)
Pharmaceuticals
SolubilityFreely soluble
Melting Point190-194 °C
Dissociation Constants9.44 (at 20 °C)
Physicochemical properties
- Melting point
- 103 °C · 103 °C
- Boiling point
- 122 °C · 122 °C(Press: 4-5 Torr)
- Density
- 1.071 · 1.071±0.06 g/cm3(Predicted)
- pka
- 12.07 · 12.07±0.45(Predicted)
- FDA UNII
- 683 H0R9659 · 683H0R9659
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]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Chemistry & industry
Pharmacology
Pharmacodynamics
Phenylpropanolamine (PPA), a sympathomimetic agent structurally similar to pseudoephedrine, is used to treat nasal congestion. Phenylpropanolamine is found in appetite suppressant formulations and with guaifenesinin in cough-cold formulations. In 2000, the FDA requested that all drug companies discontinue marketing products containing phenylpropanolamine, due to an increased risk of hemorrhagic stroke in women who used phenylpropanolamine.
Mechanism of Action
Phenylpropanolamine acts directly on alpha- and, to a lesser degree, beta-adrenergic receptors in the mucosa of the respiratory tract. Stimulation of alpha-adrenergic receptors produces vasoconstriction, reduces tissue hyperemia, edema, and nasal congestion, and increases nasal airway patency. PPA indirectly stimulates beta-receptors, producing tachycardia and a positive inotropic effect.
Biological Half-Life2.1 to 3.4 hours.
Metabolism/MetabolitesHepatic
Absorption, Distribution and ExcretionReduced bioavailability (about 38%) from gastrointestinal tract because of first pass metabolism by monoamine oxidase in the stomach and liver.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >100
Upstream & downstream products
Downstream products
Related reactions
17 records
Compound notes
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