methoxamine

Chemical Properties

Its hydrochloride ([61-16-5]) is white crystalline powder. Melting point 212-216 ℃, soluble in water, 1g of the product can be dissolved in 2.5ml of water, solution 2ml ethanol. Insoluble in ether, benzene, chloroform. Odorless, bitter taste.

Originator

Vasoxyl ,Burroughs-Wellcome,US,1949

Uses

Methoxamine is used as sympathomimetic drug. Used to maintain or restore arterial blood pressure in cases of hypovolemic shock caused by bleeding, trauma, or surgery. Particularly suitable for cases of hypotension caused by spinal anesthesia.

Definition

ChEBI: Methoxamine is an amphetamine in which the parent 1-phenylpropan-2-amine skeleton is substituted at position 1 with an hydroxy group and the phenyl ring is 2- and 5-substituted with methoxy groups. It is an antihypotensive agent (pressor), an agonist acting directly at alpha-adrenoceptors with selectivity for the alpha-1 adrenoceptor subtype similar to phenylephrine. It has a role as an antihypotensive agent and an alpha-adrenergic agonist.

Manufacturing Process

2,5-Dimethoxypropiophenone is treated in absolute ether with methyl nitrite and hydrogen chloride. The hydrochloride of 2,5-dimethoxy-αisonitrosopropiophenone crystallizes out of the solution. It is removed, the base is liberated and crystallized from benzene-heptane forming yellow leaflets that melt at about 97° to 98°C. This isonitrosoketone is dissolved in absolute alcohol containing an excess of hydrogen chloride and is hydrogenated with palladized charcoal, yielding β-(2,5-dimethoxyphenyl)-βketoisopropylamine hydrochloride, a salt that melts at about 176°C with decomposition.
12.3 g (1/20 mol) of β-(2,5-dimethoxyphenyl)-β-ketoisopropylamine hydrochloride (MP 176°C) is dissolved in 50 cc of water and hydrogenated with platinum oxide platinum black in the customary Adams-Burgess Parr apparatus. About 1/20 mol of hydrogen is absorbed, after which the solution is filtered off from the catalyst, evaporated to dryness in vacuo and recrystallized from absolute alcohol, absolute ether being added to decrease solubility. The hydrochloride is thus obtained in substantially theoretical yield. It crystallizes in plates and melts at 215°C.

Therapeutic Function

Hypertensive