Methoxamine, sold under the brand names Vasoxine, Vasoxyl, and Vasylox among others, is a sympathomimetic

medication Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, medicinal drug or simply drug) is a drug used to medical diagnosis, diagnose, cure, treat, or preventive medicine, prevent disease. Drug therapy (pharmaco ...

used as an

antihypotensive agent An antihypotensive, also known as a vasopressor, is an agent that raises blood pressure by constricting blood vessels, thereby increasing systemic vascular resistance. This is different from inotropes which increase the force of cardiac contra ...

. It has mostly or entirely been discontinued. The drug is an α₁- adrenergic receptor agonist.

Medical uses

The long

duration of action Pharmacodynamics (PD) is the study of the biochemical and physiologic effects of drugs (especially pharmaceutical drugs). The effects can include those manifested within animals (including humans), microorganisms, or combinations of organisms (fo ...

of methoxamine has been said to have rendered it obsolete in modern clinical practice.

Pharmacology

Methoxamine is an α₁-adrenergic receptor

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

. It is described as a long-acting α₁-adrenergic receptor agonist and this is contrasted with

phenylephrine Phenylephrine, sold under the brand names Neosynephrine and Sudafed PE among others, is a medication used as a decongestant for uncomplicated nasal congestion in the form of a nasal spray or oral tablet, to dilate the pupil, to increase bloo ...

which is said to be short-acting. Phenylephrine is 5 to 10times more potent than methoxamine and has a 3-fold higher maximal effect.

Chemistry

Methoxamine, also known as 2,6-dimethoxy-β-hydroxy-α-methylphenethylamine or as 2,6-dimethoxy-β-hydroxyamphetamine, is a

substituted phenethylamine Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative (chemistry), derivative compounds of phenethylamine ...

and

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

. It is somewhat similar in

chemical structure A chemical structure of a molecule is a spatial arrangement of its atoms and their chemical bonds. Its determination includes a chemist's specifying the molecular geometry and, when feasible and necessary, the electronic structure of the target m ...

to those of

desglymidodrine Desglymidodrine (developmental code name ST-1059) is the active metabolite of the prodrug antihypotensive agent midodrine. It acts as a binding selectivity, selective alpha-1 adrenergic receptor, α1-adrenergic receptor agonist. Desglymidodrine ...

(3,6-dimethoxy-β-hydroxyphenethylamine), dimetofrine (3,5-dimethoxy-4,β-dihydroxy-''N''-methylphenethylamine), 2,5-dimethoxyamphetamine (2,5-DMA), and butaxamine ((1''S'',2''S'')-3,6-dimethoxy-β-hydroxy-''N''-''tert''-butylamphetamine).

History

Methoxamine was synthesized by 1944. It was marketed in the

United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

by 1949.

Society and culture

Names

''Methoxamine'' is the generic name of the drug and its and , while ''méthoxamine'' is its and ''methoxamina'' is its . In the case of the hydrochloride

salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...

, its generic name is ''methoxamine hydrochloride'' and this is its , , and . A synonym of methoxamine is ''methoxamedrine''. The drug has been sold under brand names including ''Idasal'', ''Mexan'', ''Pressomin'', ''Vasosterol'', ''Vasoxine'', ''Vasoxyl'', and ''Vasylox''.

Availability

Methoxamine has been marketed in

Canada Canada is a country in North America. Its Provinces and territories of Canada, ten provinces and three territories extend from the Atlantic Ocean to the Pacific Ocean and northward into the Arctic Ocean, making it the world's List of coun ...

, the

Czech Republic The Czech Republic, also known as Czechia, and historically known as Bohemia, is a landlocked country in Central Europe. The country is bordered by Austria to the south, Germany to the west, Poland to the northeast, and Slovakia to the south ...

Ireland Ireland (, ; ; Ulster Scots dialect, Ulster-Scots: ) is an island in the North Atlantic Ocean, in Northwestern Europe. Geopolitically, the island is divided between the Republic of Ireland (officially Names of the Irish state, named Irelan ...

Japan Japan is an island country in East Asia. Located in the Pacific Ocean off the northeast coast of the Asia, Asian mainland, it is bordered on the west by the Sea of Japan and extends from the Sea of Okhotsk in the north to the East China Sea ...

Spain Spain, or the Kingdom of Spain, is a country in Southern Europe, Southern and Western Europe with territories in North Africa. Featuring the Punta de Tarifa, southernmost point of continental Europe, it is the largest country in Southern Eur ...

, the

United Kingdom The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom (UK) or Britain, is a country in Northwestern Europe, off the coast of European mainland, the continental mainland. It comprises England, Scotlan ...

, and the

and was available in these countries in 2000. However, it was discontinued in Canada and the United Kingdom by 2004. It has also been discontinued in the United States. By 2016, methoxamine appeared to remain available only in

References

{{Phenethylamines Alpha-1 adrenergic receptor agonists Antihypotensive agents Beta-Hydroxyamphetamines Methoxyphenethylamines Phenol ethers Sympathomimetics Vasoconstrictors