Metaraminol is a potent sympathomimetic amine

Sympathomimetic amine

Sympathomimetic drugs mimic the effects of transmitter substances of the sympathetic nervous system such as catecholamines, epinephrine , norepinephrine , dopamine, etc...

 used in the prevention and treatment of hypotension

Hypotension

In physiology and medicine, hypotension is abnormally low blood pressure, especially in the arteries of the systemic circulation. It is best understood as a physiologic state, rather than a disease. It is often associated with shock, though not necessarily indicative of it. Hypotension is the...

, particularly as a complication of anesthesia

Anesthesia

Anesthesia, or anaesthesia , traditionally meant the condition of having sensation blocked or temporarily taken away...

.
It is an α₁-adrenergic receptor

Adrenergic receptor

The adrenergic receptors are a class of metabotropic G protein-coupled receptors that are targets of the catecholamines, especially noradrenaline and adrenaline ....

 agonist

Agonist

An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...

 with some β effect.

Metaraminol is also used in the treatment of priapism

Priapism

Priapism is a potentially harmful and painful medical condition in which the erect penis or clitoris does not return to its flaccid state, despite the absence of both physical and psychological stimulation, within four hours. There are two types of priapism: low-flow and high-flow. Low-flow...

. Although not approved for this use, it appears to be effective.

Chemistry

Metaraminol, L-1-(3-hydroxyphenyl)-2-aminopropan-1-ol, is synthesized in two ways. The first way is synthetic

Synthetic

Synthesis, the combination of two or more parts, whether by design or by natural processes. Furthermore, it may imply being prepared or made artificially, in contrast to naturally.-In the sense of combination:* Synthetic position, a concept in finance...

, and it is from 3-hydroxypropiophenone. The hydroxyl group is protected by alkylation with benzyl chloride

Benzyl chloride

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colourless liquid is a reactive organochlorine compound that is a widely used chemical building block.-Preparation:...

, giving 3-benzyloxypropiophenone. Upon reaction with butyl nitrite

Butyl nitrite

Butyl nitrite is an alkyl nitrite made from n-butanol. Butyl nitrite is used recreationally as poppers.-Chemistry:Synonyms include N-butyl nitrite, 1-butyl nitrite and nitrous acid, butyl ester....

, it undergoes nitrosation into the isonitrosoketone, which by reduction using hydrogen

Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...

 over Raney nickel

Raney nickel

Raney nickel is a solid catalyst composed of fine grains of a nickel-aluminium alloy, used in many industrial processes. It was developed in 1926 by American]] engineer Murray Raney as an alternative catalyst for the hydrogenation of vegetable oils in industrial processes...

 turns into 1-(3-benzyloxyphenyl)-2-aminopropan-1-ol, the protecting benzyl group is removed by reduction using hydrogen over palladium catalyst, to give racemic metaraminol. The desired L-isomer is isolated with the help of (+)-tartaric acid.

• G. Erhart, L. Stein, (1930).
• E. W. Zeh, (1934).

The second way is semisynthetic

Semisynthetic

"Semisynthesis" or partial chemical synthesis is a type of chemical synthesis that uses compounds isolated from natural sources as starting materials. These natural biomolecules are usually large and complex molecules...

, consisting of fermentation

Fermentation

Fermentation may refer to:* Fermentation , the use of fermentation in food preparation* Fermentation , a metabolic process whereby electrons released from nutrients are ultimately transferred to molecules obtained from the breakdown of those same nutrients* Fermentation , the process of...

 of D-glucose

Glucose

Glucose is a simple sugar and an important carbohydrate in biology. Cells use it as the primary source of energy and a metabolic intermediate...

 in the presence of 3-acetoxybenzaldehyde, which forms (-)-1-hydroxy-1-(3-hydroxyphenyl)-acetone, the carbonyl

Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups....

 group of which is reduced by hydrogen over a palladium catalyst in the presence of ammonia

Ammonia

Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...

, giving metaraminol.

• G. Erhart, L. Stein, (1930).
• G. Erhart, L. Stein, (1934).
• W. H. Hartung, (1935).
• I. G. Farbenindustrie AG, (1932).