Mephentermine

Originator

Wyamine,Wyeth,US,1947

The Uses of Mephentermine

Mephentermine is an α-adrenergic agonist. Mephentermine is used as an antihypotensive.

The Uses of Mephentermine

Adrenergic (vasoconstrictor).

Indications

Used to maintain blood pressure in hypotensive states.

Background

A sympathomimetic agent with mainly indirect effects on adrenergic receptors. It is used to maintain blood pressure in hypotensive states, for example, following spinal anesthesia. Although the central stimulant effects of mephentermine are much less than those of amphetamine, its use may lead to amphetamine-type dependence. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1248)

Definition

ChEBI: Mephentermine is a member of amphetamines.

Manufacturing Process

0.5 g of 2-(N-methylamino)-2-methyl-1-phenyl-1-propanol was treated with 1 cc of thionyl chloride at room temperature. A vigorous reaction set in. The gummy material was stirred with a small amount of petroleum ether and allowed to stand overnight. The brown crystalline solid after washing with petroleum ether was recrystallized from a small amount of absolute alcohol with addition of charcoal followed by filtration. On dilution with several volumes of ether and refrigeration white granular crystals of 1-chloro-2-(Nmethamino)-2-methyl-1-phenyl propane hydrochloride were deposited.
250 mg of 1-chloro-2-(N-methylamino)-2-methyl-1-phenyl propane hydrochloride was dissolved in 2 cc of warm methanol and hydrogenated in the presence of 250 mg of palladium barium carbonate catalyst with provision for the absorption of the carbon-dioxide formed. When the theoretical amount of hydrogen had been taken up the mixture was filtered to remove the catalyst, concentrated to small volume and extracted with ether. After separating the ether the residue was further concentrated yielding a white crystalline solid. This solid on solution in water, strongly alkalizing, extraction with ether and removal of the ether yielded 2-(N-methylamino)-2-methyl-1- phenyl propane identified as the picrate by melting point 155°C to 156°C and mixed melting point 154.0°C to 154.5°C, with an authentic sample melting at 150°C to 153°C.

brand name

Wyamine Sulfate (Baxter Healthcare).

Therapeutic Function

Adrenergic (vasopressor)

Pharmacokinetics

Mephentermine is a sympathomimetic agent with mainly indirect effects on adrenergic receptors. It is used to maintain blood pressure in hypotensive states, for example, following spinal anesthesia. Although the central stimulant effects of mephentermine are much less than those of amphetamine, its use may lead to amphetamine-type dependence. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1248)

Metabolism

Hepatic, by N-demethylation and then p-hydroxylation.