Metaraminol, also known as metaradrine and sold under the brand name Aramine 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 ...

which is used in the prevention and treatment of

hypotension Hypotension, also known as low blood pressure, is a cardiovascular condition characterized by abnormally reduced blood pressure. Blood pressure is the force of blood pushing against the walls of the arteries as the heart pumps out blood and is ...

(low blood pressure), particularly as a complication of

anesthesia Anesthesia (American English) or anaesthesia (British English) is a state of controlled, temporary loss of sensation or awareness that is induced for medical or veterinary purposes. It may include some or all of analgesia (relief from or prev ...

. It is given by

intramuscular Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles hav ...

intravenous administration Intravenous therapy (abbreviated as IV therapy) is a medical technique that administers fluids, medications and nutrients directly into a person's vein. The intravenous route of administration is commonly used for rehydration or to provide nutr ...

Side effect In medicine, a side effect is an effect of the use of a medicinal drug or other treatment, usually adverse but sometimes beneficial, that is unintended. Herbal and traditional medicines also have side effects. A drug or procedure usually use ...

s of metaraminol include reflex bradycardia among others. Metaraminol is a norepinephrine releasing agent and at high doses a 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 ...

with some β-adrenergic effect. It is a

substituted amphetamine Substituted amphetamines, or simply amphetamines, are a chemical class, class of compounds based upon the amphetamine structure; it includes all derivative (chemistry), derivative compounds which are formed by replacing, or substitution reacti ...

and is closely related to phenylpropanolamine,

ephedrine Ephedrine is a central nervous system (CNS) stimulant and sympathomimetic agent that is often used to prevent hypotension, low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred ...

, and oxilofrine. Metaraminol was approved for medical use in the United States in September 1954.

Medical uses

Metaraminol is given

intravenously Intravenous therapy (abbreviated as IV therapy) is a medical technique that administers fluids, medications and nutrients directly into a person's vein. The intravenous route of administration is commonly used for rehydration or to provide nutr ...

as either a bolus (often 0.5–1 mg doses) or as an infusion, usually via peripheral intravenous access. Metaraminol is commonly available as 10 mg in 1 mL, that requires dilution prior to administration (often made up to a 0.5 mg/mL solution), however pre-prepared syringes of metaraminol for bolus use for hypotension are also commonly available. Metaraminol is also used in the treatment of priapism.

Pharmacology

Pharmacodynamics

The dominant

mechanism of action In pharmacology, the term mechanism of action (MOA) refers to the specific biochemical Drug interaction, interaction through which a Medication, drug substance produces its pharmacological effect. A mechanism of action usually includes mention o ...

for the vasopressor action of metaraminol is indirect, with metaraminol displacing

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic compound, organic chemical in the catecholamine family that functions in the brain and human body, body as a hormone, neurotransmitter and neuromodulator. The ...

from neuronal vesicles in order for the noradrenaline to exert these effects. Metaraminol at higher doses may have direct α-adrenergic agonist and β₁-adrenergic agonist effects. However at doses common in clinical practice, the indirect α₁-adrenergic effects predominate, such that reflex bradycardia is a common side effect.

Chemistry

Metaraminol, also known as (1''R'',2''S'')-3,β-dihydroxy-α-methylphenethylamine or as (1''R'',2''S'')-3,β-dihydroxyamphetamine, 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 the (1''R'',2''S'')-

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

of ''meta''-hydroxynorephedrine (3,β-dihydroxyamphetamine). The drug is closely related to phenylpropanolamine ((1''RS'',2''SR'')-β-hydroxyamphetamine; norephedrine),

((1''R'',2''S'')-β-hydroxy-''N''-methylamphetamine), ''para''-hydroxynorephedrine (4,β-dihydroxyamphetamine), and oxilofrine (4,β-dihydroxy-''N''-methylamphetamine). The experimental log P of metaraminol is -0.27 and its predicted log P ranges from -0.59 to 0.07. Metaraminol is used pharmaceutically as the

bitartrate , Section2 = {{Chembox Properties , C=4 , H=5 , O=6 , Formula_Charge = − , ConjugateAcid = Tartaric acid , ConjugateBase = Tartrate Bitartrate is an anion which is the conjugate base of tartaric acid. It may also refer to any salt ...

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 ...

History

Metaraminol was approved for medical use in the United States in September 1954.

Society and culture

Names

Metaraminol is the generic name of the medication and its and , while its is métaraminol and its is metaraminolo. As the

, its generic name is metaraminol bitartrate and this is its and , while metaraminol tartrate is its . A synonym of metaraminol is metaradrine. Brand names of metaraminol include Aramin, Aramine, and Pressonex, among others.

References

{{Authority control Alpha-1 adrenergic receptor agonists Antihypotensive agents Beta-adrenergic agonists Beta-Hydroxyamphetamines Cardiac stimulants Norepinephrine releasing agents Peripherally selective drugs 3-Hydroxyphenyl compounds Sympathomimetics