304-84-7

antihypertensive, vasoconstrictor

Emivan,U.S.V.,US,1961

ChEBI:Etamivan is phenol substituted at C-2 and C-4 by a methoxy group and an N,N-diethylaminocarbonyl group respectively. A respiratory stimulant drug related to nikethamide, it has now fallen largely into disuse. It is a member of phenols and a member of methoxybenzenes.

4 g of vanillinic acid are mixed with 3.6 g of diethylamine, after cooling 2.2 g of phosphorus pentoxide and the same amount of glass powder are added, and then reacted with xylene until a thin paste has been formed. The latter is boiled for some hours in the reflux cooler, moisture being excluded. Decantation follows, and the residue is dissolved by means of a warm solution of potassium carbonate until only glass powder or small amount of impurities remain undissolved, and then the xylene solution is shaken up therewith, The xylene solution is then separated, the aqueous layer is again extracted with ether, and the ether extract is combined with the xylene solution. The mixture is then distilled under the lowest possible pressure, collecting the fraction between 170°C and 250°C (referred to 10 Torr), and purifying it by further fractionation. In this way a slightly yellowish oil is obtained, which crystallizes after some time. By dissolving in ligroin and crystallizing, pure vanillinic acid diethylamide is obtained in the form of white needles; MP 95°C to 95.5°C.

Vandid (3M Pharmaceuticals).

Central and respiratory stimulant

Etamivan is a central and respiratory stimulant.

Store at -20°C