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Home > Encyclopedia > (αR)-α-[(1S)-1-(Ethylmethylamino)ethyl]benzenemethanol

(αR)-α-[(1S)-1-(Ethylmethylamino)ethyl]benzenemethanol

(αR)-α-[(1S)-1-(Ethylmethylamino)ethyl]benzenemethanol structure

(αR)-α-[(1S)-1-(Ethylmethylamino)ethyl]benzenemethanol 

structure
  • CAS No:

    48141-64-6

  • Formula:

    C12H19NO

  • Chemical Name:

    (αR)-α-[(1S)-1-(Ethylmethylamino)ethyl]benzenemethanol

  • Synonyms:

    Benzenemethanol,α-[(1S)-1-(ethylmethylamino)ethyl]-,(αR)-;Benzenemethanol,α-[1-(ethylmethylamino)ethyl]-,[R-(R*,S*)]-;(αR)-α-[(1S)-1-(Ethylmethylamino)ethyl]benzenemethanol;Etafedrine;l-N-Ethylephedrine;l-α-[1-(Ethylmethylamino)ethyl]benzyl alcohol;(-)-Etafedrine;(1R,2S)-N-Ethylephedrine

Description

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.

(αR)-α-[(1S)-1-(Ethylmethylamino)ethyl]benzenemethanol Basic Attributes

193.28 g/mol

193.29

231-677-2

2Y6VQU63E8

Characteristics

23.5 Ų

108-110

Toxicity

This drug is a sympathomimetic, and therefore has the following adverse effects (in parallel with ephedrine): tremor, fear, anxiety, confusion, irritability, insomnia, and psychotic states. Paranoid psychosis, delusions, and hallucinations may also follow overdose. The adverse effects of ephedrine and similar drugs are believed to be related to coronary artery constriction, vasospasm, shortening of cardiac refractory periods allowing re-entrant cardiac arrhythmias, hypertension-induced subarachnoid hemorrhage, cerebral artery vasoconstriction as well as sympathomimetic-induced platelet activation.

Drug Information

Conditions characterized by bronchial congestion and bronchospasm when an expectorant or bronchodilator action is required, such as acute bronchitis, acute episodes of chronic bronchitis and bronchial asthma,.

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.

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.

It has a plasma half-life ranging from 3 to 6 hours depending on urinary pH.

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.

etafedrine

(αR)-α-[(1S)-1-(Ethylmethylamino)ethyl]benzenemethanol Use and Manufacturing

Pharmaceuticals

Computed Properties

Molecular Weight:193.28
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:193.146664230
Monoisotopic Mass:193.146664230
Topological Polar Surface Area:23.5
Heavy Atom Count:14
Complexity:154
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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