metaraminol

Also known as 1-(m-mydroxyphenyl)-2-amino-1-propanol, 2-amino-1-(m-hydroxyphenyl)-1-propanol, 1-metaraminol, metaradrine, m-hydroxy norephedrine, alpha-(1-aminoethyl)-3-hydroxybenzenemethanol, (-)-erythro-metaraminol, m-hydroxypropadrine

Metaraminol, also known as metaradrine and sold under the brand name Aramine among others, is a sympathomimetic medication which is used in the prevention and treatment of hypotension (low blood pressure), particularly as a complication of anesthesia. It is given by intramuscular or intravenous administration.

In the Vinony graph

Within Vinony's link graph, metaraminol is referenced by 1,865 other articles, and connects out to adrenergic receptor, intravenous infusion and defusion and propranolol.

It is catalogued under topics including 3-Hydroxyphenyl compounds, Alpha1-adrenergic agonists and Antihypotensive agents.

Its subject is documented across 11 Wikipedia language editions.

Key facts

Drug.Verifiedfields: verified
Drug.verifiedrevid: 462249333
Drug.image: Metaraminol structure.svg
Drug.image_class: skin-invert-image
Drug.width: 250px
Drug.tradename: Aramine, Metaramin, Pressonex, others
Drug.DailyMedID: Metaraminol
Drug.pregnancy_AU: C
Drug.routes_of_administration: Intramuscular injection, intravenous administration
Drug.class: Norepinephrine releasing agent; Adrenergic receptor agonist; Sympathomimetic; Antihypotensive
Drug.ATC_prefix: C01
Drug.ATC_suffix: CA09
Drug.legal_AU: S4
Drug.legal_UK: POM
Drug.legal_US: Rx-only
Drug.protein_bound: 45%
Drug.metabolism: Liver
Drug.CAS_number: 54-49-9

via Wikipedia infobox

Chemical data

Formula: C9H13NO2
Molecular weight: 167.2 g/mol
IUPAC name: 3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol
SMILES: C[C@@H]([C@@H](C1=CC(=CC=C1)O)O)N
InChIKey: WXFIGDLSSYIKKV-RCOVLWMOSA-N
XLogP: -0.4
Polar surface area: 66.5 Å²
H-bond donors: 3
H-bond acceptors: 3
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1954
Admin. routes: parenteral
Indications: cardiovascular disease, preeclampsia, hypotension

via ChEMBL · EBI

Research

1,206 papers

Metaraminol use during spinal anaesthesia for caesarean section: a meta-analysis of randomised controlled trials.International journal of obstetric anesthesia · 2019
BET 3: Peripheral metaraminol infusion in the emergency department.Emergency medicine journal : EMJ · 2017
Rational use of metaraminol can improve pharmaceutical care.European journal of hospital pharmacy : science and practice · 2023
Metaraminol-induced coronary vasospasm masquerading as ST-elevation myocardial infarction during general anaesthesia.British journal of anaesthesia · 2024
Dose equivalence for metaraminol and noradrenaline - A retrospective analysis.Journal of critical care · 2024

via PubMed

Wikidata facts

Subclass of: meta-hydroxynorephedrine
Mass: 167.094629
Has use: medication

Show 7 more facts

chemical formula: C₉H₁₃NO₂
defined daily dose: 50
medical condition treated: hypotension
canonical SMILES: CC(C(C1=CC(=CC=C1)O)O)N
isomeric SMILES: C[C@@H]([C@@H](C1=CC(=CC=C1)O)O)N
World Health Organisation international non-proprietary name: metaraminol
Commons category: Metaraminol

Sources (4)

via Wikidata · CC0

~3 min read

Encyclopedic overview

8 sections

Contents

Medical uses
Pharmacology
Pharmacodynamics
Chemistry
History
Society and culture
Names
References

Side effects of metaraminol include reflex bradycardia among others. Metaraminol is a norepinephrine releasing agent and at high doses a α1-adrenergic receptor agonist with some β-adrenergic effect. It is a substituted amphetamine and is closely related to phenylpropanolamine, ephedrine, and oxilofrine.

Excerpted from Wikipedia’s “metaraminol” article, available under the CC BY-SA 4.0 licence.