Этафедрин

Description

Etafedrine (Etafedrine, synonyms Ethylephedrine, N-Ethylephedrine) is a synthetic sympathomimetic amine, a structural analogue of ephedrine with the replacement of one of the N-methyl substituents with an ethyl group. Chemical formula C12H19NO, English name Etafedrine, CAS number 7681-79-0. Chemical structure: 2-(ethylmethylamino)-1-phenylpropan-1-ol, also known as α-[1-(ethylmethylamino)ethyl]benzenemethanol.

Substance class

Belongs to the group of adrenergic amines of the phenylpropanolamine series, structurally related to ephedrine and pseudoephedrine. It was used as a bronchodilator - a drug that expands the lumen of the bronchi by stimulating adrenergic receptors in the smooth muscles of the respiratory tract. Currently withdrawn from circulation in most pharmaceutical markets.

Basic Attributes

• CAS No.: 7681-79-0
• Chemical formula: C12H19NO
• Molecular Weight: 193.288
• Exact weight: 193.29
• EU number: 231-677-2
• PSA specifications: 23.5
• XLogP3: 2.1

Physico-chemical characteristics

• Density: 0.995 ± 0.06 g/cm3 (predicted value)
• Melting point: 29–30 °C
• Boiling point: 135–136 °C at 15 torr pressure

Mechanism of action and application

Etafedrine acted as an indirect and partially direct stimulator of adrenergic receptors, causing relaxation of bronchial smooth muscles and easier breathing during bronchospasm. Produced under the trade names Menetyl, Nethaprin, Novedrine. Used in combination preparations for the treatment of bronchial asthma and other conditions accompanied by bronchospasm, and also in the form of a hydrochloride salt (CAS 5591-29-7) to increase solubility and ease of dosing.

Application status

Like a number of other sympathomimetics of the phenylpropanolamine series, ethaphedrine has been withdrawn from the pharmaceutical market. Today, the substance is of interest primarily as a reference compound and an object of analytical chemistry, as well as as an object for studying structure-activity relationships in the series of adrenergic amines related to ephedrine and norephedrine.

Storage and transportation

Store in an airtight container in a cool, dry place, protected from direct light; the substance melts already at room temperature just above 29 °C, so warehouse conditions should prevent overheating of the container above the melting point. Transport in compliance with the requirements for pharmaceutical substances and adrenergic amines, with protection from moisture and high temperatures.

Structural relationship

Etaphedrine is part of the broad group of phenylpropanolamine adrenergic amines, which includes ephedrine, pseudoephedrine, norephedrine (phenylpropanolamine) and cathine. All these compounds have a common structural motif - a phenyl ring connected to a propane chain bearing a hydroxyl group and an amino group with alkyl substituents of varying lengths. Variations in the substituents at the nitrogen atom and the position of the hydroxyl group determine differences in the strength of the bronchodilator, vasoconstrictor and central stimulant effects within this series of substances.