Etafedrine
Basic information
- CAS
48141-64-6- Standard SMILES
CCN(C)[C@@H](C)[C@H](O)c1ccccc1- InChIKey
IRVLBORJKFZWMI-JQWIXIFHSA-N- Molecular formula
- C12H19NO
- Average molar mass
- 193.28 g/mol
- Monoisotopic mass
- 193.14666423
Overview
Etafedrine (INN) or ethylephedrine is a long-acting bronchodilator and has been an ingredient combined with other drugs in the brand names Nethaprin and Dalmacol. It was previously available as both the free base and as the hydrochloride salt manufactured by Sanofi-Aventis (now Sanofi) has been discontinued. Ethylephedrine is be formed by alkylating ephedrine with ethyl iodide. The hydrochloride is be prepared by passing hydrogen chloride through a solution of ethylephedrine in diethyl ether. This belongs to the family of medications called decongestants. It acts by narrowing blood vessels in the nasal passages, helping to relieve nasal congestion.
Names & identifiers
- Preferred name
- Etafedrine
- IUPAC
- (1R,2S)-2-[ethyl(methyl)amino]-1-phenylpropan-1-ol
- English name
- [R-(R*,S*)]-alpha-[1-(ethylmethylamino)ethyl]benzyl alcohol
- Molecular formula
- C12H19NO
- Molecular weight
- 193.29
Names & synonyms
ETAFEDRINE(-)-Etafedrine(1r,2s)-2-[ethyl(methyl)amino]-1-phenylpropan-1-olNovedrin2Y6VQU63E8Etafedrine, (-)-MenetrylDTXSID201016521alpha-(1-(Ethylmethylamino)ethyl)benzyl alcoholEtafedrinaEtafedrinumEtaphedrine
Show more names
Einecs 256-359-0(1R,2S)-1-Phenyl-2-(ethylmethylamino)-1-propanol(αR)-α-[(S)-1-(Ethylmethylamino)ethyl]benzenemethanolBenzenemethanol, α-[(1S)-1-(ethylmethylamino)ethyl]-, (αR)-[R-(R*,S*)]-alpha-[1-(ethylmethylamino)ethyl]benzyl alcohol
7681-79-0(1R,2S)-2-(ethyl(methyl)amino)-1-phenylpropan-1-oll-N-ethylephedrineBenzenemethanol, alpha-(1-(ethylmethylamino)ethyl)-RefChem:591346DTXCID101474712231-677-2256-359-0
Database identifiers
- CAS
48141-64-6、7681-79-0
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 23.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 4
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 154
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Human DrugsPharmaceuticals
Melting Point108-110
Physicochemical properties
- FDA UNII
- 2 Y6VQU63E8 · 2Y6VQU63E8
Chemistry & industry
Pharmacology
Pharmacodynamics
Etafedrine helps to control the cough which is associated with irritation of the mouth and throat that is not alleviated by cough medications that are less strong. The results of one study in 48 individuals showed that lung FEV1 (forced expiratory volume) and lung VC (vital capacity) were significantly improved with etafedrine, sleep improved, and patients showed improved appetite in addition to the suppression of cough.
Mechanism of Action
A sympathomimetic agent, etafedrine acts on the sympathetic receptors of the bronchial tree, relieving spasm in a manner similar to that of ephedrine. Etafedrine acts as a selective β adrenoreceptor agonist, thereby mediating its bronchodilator effects without increasing norepinephrine release. This is distinctly different from ephedrine and tyramine which trigger the release of epinephrine or norepinephrine. N-ethylation of ephedrine suppresses the indirect sympathomimetic activity and markedly enhances the efficacy on beta 2- adrenoceptors.
Biological Half-LifeIt has a plasma half-life ranging from 3 to 6 hours depending on urinary pH.
Absorption, Distribution and Excretion
Similar to its parent drug, ephedrine, it is readily and completely absorbed from the gastrointestinal tract; plasma peak concentrations are reached an hour after ingestion. A single oral dose of 24 mg produced an average peak plasma concentration of 0.10 mg/L.
Excreted mainly in the urine.
Similar to ephedrine, at about 3L/kg.
Uses & manufacturing
Use ClassificationPharmaceuticals
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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