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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13NO2.ClH
Molecular Weight 203.666
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METARAMINOL HYDROCHLORIDE

SMILES

Cl.C[C@H](N)[C@H](O)C1=CC(O)=CC=C1

InChI

InChIKey=PPRPRPMMKPXRKK-YDYUUSCQSA-N
InChI=1S/C9H13NO2.ClH/c1-6(10)9(12)7-3-2-4-8(11)5-7;/h2-6,9,11-12H,10H2,1H3;1H/t6-,9-;/m0./s1

HIDE SMILES / InChI
Metaraminol is a potent sympathomimetic amine that increases both systolic and diastolic blood pressure, is an adrenergic receptor alpha-1 agonist.. Metaraminol is indicated for prevention and treatment of the acute hypotensive state occurring with spinal anesthesia. It is also indicated as adjunctive treatment of hypotension due to hemorrhage, reactions to medications, surgical complications, and shock associated with brain damage due to trauma or tumor. Metaraminol is also used in the treatment of priapism, in spite of this application was not approved, it appears to be effective.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
METARAMINOL BITARTRATE

Approved Use

Metaraminol is indicated for prevention and treatment of the acute hypotensive state occurring with spinal anesthesia. It is also indicated as adjunctive treatment of hypotension due to hemorrhage, reactions to medications, surgical complications, and shock associated with brain damage due to trauma or tumor.
Palliative
METARAMINOL BITARTRATE

Approved Use

Metaraminol is indicated for prevention and treatment of the acute hypotensive state occurring with spinal anesthesia. It is also indicated as adjunctive treatment of hypotension due to hemorrhage, reactions to medications, surgical complications, and shock associated with brain damage due to trauma or tumor.
Palliative
METARAMINOL BITARTRATE

Approved Use

Metaraminol is indicated for prevention and treatment of the acute hypotensive state occurring with spinal anesthesia. It is also indicated as adjunctive treatment of hypotension due to hemorrhage, reactions to medications, surgical complications, and shock associated with brain damage due to trauma or tumor.
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
10 mg 4 times / hour single, intravenous
Dose: 10 mg, 4 times / hour
Route: intravenous
Route: single
Dose: 10 mg, 4 times / hour
Sources:
unhealthy, 38 years
n = 1
Health Status: unhealthy
Age Group: 38 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Bigeminal rhythm...
AEs leading to
discontinuation/dose reduction:
Bigeminal rhythm (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Bigeminal rhythm 1 patient
Disc. AE
10 mg 4 times / hour single, intravenous
Dose: 10 mg, 4 times / hour
Route: intravenous
Route: single
Dose: 10 mg, 4 times / hour
Sources:
unhealthy, 38 years
n = 1
Health Status: unhealthy
Age Group: 38 years
Sex: F
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >1000 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
yes
yes
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
Augmented natriuretic response to infusion of saline in dogs rendered acutely hypertensive with metaraminol.
1966 Jul
Myocardial infarction induced by metaraminol bitartrate (aramine).
1966 Oct
Pulmonary edema: a complication of metaraminol treatment of paroxysmal supraventricular tachycardia.
1974 May
[Prinzmetal's angina induced by dopamine and metaraminol. 2 cases].
1979 Mar
[Metaraminol--an antidote in corpus cavernosum autoinjection therapy-induced prolonged erection].
1986 May
Cerebral arteriovenous malformations, steal, and the hypertensive breakthrough threshold. An experimental study in rats.
1987 Apr
An extravascular hydraulic system to control blood pressure by a feedback regulation of the venous return.
1987 May
Assessment of the permeability of the blood-retinal barrier in hypertensive rats.
1987 Oct
[Metaraminol in therapy of various forms of priapism].
1988 Jul
The metaraminol test and adverse cardiac effects.
1989 Aug 1
[Papaverine-induced priapism. Experiences with a new urologic emergency].
1989 Feb 10
[Epilepsy and hypertensive crisis after intracavernous injection of metaraminol in the treatment of priapism secondary to a papaverine test].
1989 May 20
Post-traumatic priapism treated with metaraminol bitartrate: case report.
1990 Dec
[Familial Mediterranean fever. The metaraminol test as a cause of severe cephalalgia].
1990 Jun
The effect of intracarotid nonionic contrast media on the blood-brain barrier in acute hypertension.
1994 Jan
Reversible segmental left-ventricular dysfunction caused by accidental administration of sympathomimetic drug in human.
1997 Aug 29
Laparoscopic and open surgery for pheochromocytoma.
2001
Anaphylactic or anaphylactoid reactions in patients undergoing cardiac surgery.
2001 Dec
Prostaglandin synthesis inhibitor improves hypotension during normothermic cardiopulmonary bypass.
2001 Nov-Dec
Pharmacologic exposure of an occult atrial septal defect.
2001 Sep
Anesthesia for one-stage bilateral pheochromocytoma resection in a patient with MEN type IIa: attenuation of hypertensive crisis by magnesium sulfate.
2002 Jan
Drinking attenuates the noradrenaline release in the lateral hypothalamic area induced by angiotensin II activation of the subfornical organ in rats.
2003 Mar 18
[Preload during spinal anesthesia for cesarean section: comparison between crystalloid and colloid solutions.].
2004 Dec
Use of alpha-agonists for management of anaphylaxis occurring under anaesthesia: case studies and review.
2004 Dec
[Experimental study on prevention and treatment of focal segmental glomerulosclerosis with heparin].
2004 Jan
Inadvertent epidural administration of metaraminol.
2004 Jun
Cerebellar interpositus nuclear inputs impinge on paraventricular neurons of the hypothalamus in rats.
2004 Nov 3
Photostability of symphatomimetic agents in commonly used infusion media in the absence and presence of bisulfite.
2004 Nov-Dec
Cardiovascular aspects of anaphylaxis: implications for treatment and diagnosis.
2005 Aug
Metaraminol (Aramine) in the management of a significant amlodipine overdose.
2005 Jul
Use of metaraminol in patients with Familial Mediterranean Fever.
2006 Aug
[Diagnosis and treatment of priapism due to neoplasma of penis].
2006 Feb
The blood-brain barrier for catecholamines - revisited.
2007 Apr
"Orpheus" cardiopulmonary bypass simulation system.
2007 Dec
Pharmacokinetic study of three cardiovascular drugs by high-performance liquid chromatography using pre-column derivatization with 9,10-anthraquinone-2-sulfonyl chloride.
2007 Oct 15
[Diagnosis and treatment of priapism: a report of 15 cases].
2008 Sep
Transient transmural ischaemia during endobronchial laser treatment: possible coronary artery embolism.
2008 Sep
Ventricular arrhythmias and antioxidative medication: experimental study.
2008 Sep-Oct
Mollaret meningitis may be caused by reactivation of latent cerebral toxoplasmosis.
2009
Discovery of highly potent and selective biphenylacylsulfonamide-based beta3-adrenergic receptor agonists and molecular modeling based on the solved X-ray structure of the beta2-adrenergic receptor: part 6.
2009 Aug 15
Is propofol a safe and effective sedative for relocating hip prostheses?
2009 Jan
Myocardial infarction associated with the administration of intravenous ephedrine and metaraminol for spinal-induced hypotension.
2009 May
Impact of admixture time and diluent order on metaraminol concentration.
2009 Sep
Vasopressor choice for hypotension in elective Cesarean section: ephedrine or phenylephrine?
2010 Apr 30
Molecular imaging of cardiac sympathetic innervation by 11C-mHED and PET: from man to mouse?
2010 Aug
Cardiac arrest in intensive care unit: Case report and future recommendations.
2010 Jan
Clinical evaluation of the flotrac/Vigileo system for continuous cardiac output monitoring in patients undergoing regional anesthesia for elective cesarean section: a pilot study.
2010 Jun
Adenosine-induced cardiopulmonary arrest in a patient with paroxysmal supraventricular tachycardia--a response.
2010 May
Disparities of care for African-Americans and Caucasians with community-acquired pneumonia: a retrospective cohort study.
2010 May 27
[Determination of three adrenergic drugs using capillary electrophoresis with amperometric detection].
2010 Nov
Patents

Sample Use Guides

Intramuscular or Subcutaneous Injection: The recommended dose is 2 to 10 mg (0.2 to 1 mL). As with other agents given subcutaneously, only the preferred sites of injection, as set forth in standard texts, should be used. Intravenous Infusion: The recommended dose is 15 to 100 mg (1.5 to 10 mL) in 500 mL of Sodium Chloride Injection or 5% Dextrose Injection, adjusting the rate of infusion to maintain the blood pressure at the desired level. Higher concentrations of metaraminol, 150 to 500 mg per 500 mL of infusion fluid, have been used.
Route of Administration: Other
In Vitro Use Guide
Unknown
Name Type Language
METARAMINOL HYDROCHLORIDE
MI   WHO-DD  
Common Name English
BENZENEMETHANOL, .ALPHA.-((1S)-1-AMINOETHYL)-3-HYDROXY-, HYDROCHLORIDE (1:1), (.ALPHA.R)-
Systematic Name English
PRESSONEX BITARTRATE
Common Name English
METARAMINOL HYDROCHLORIDE, (-)-
Common Name English
METARAMINOL HYDROCHLORIDE [MI]
Common Name English
(.ALPHA.R)-.ALPHA.-((1S)-1-AMINOETHYL)-3-HYDROXYBENZENEMETHANOL HYDROCHLORIDE
Common Name English
Metaraminol hydrochloride [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
23618492
Created by admin on Sat Dec 16 08:53:13 GMT 2023 , Edited by admin on Sat Dec 16 08:53:13 GMT 2023
PRIMARY
CAS
5967-52-2
Created by admin on Sat Dec 16 08:53:13 GMT 2023 , Edited by admin on Sat Dec 16 08:53:13 GMT 2023
PRIMARY
EPA CompTox
DTXSID00975067
Created by admin on Sat Dec 16 08:53:13 GMT 2023 , Edited by admin on Sat Dec 16 08:53:13 GMT 2023
PRIMARY
MERCK INDEX
m7273
Created by admin on Sat Dec 16 08:53:13 GMT 2023 , Edited by admin on Sat Dec 16 08:53:13 GMT 2023
PRIMARY Merck Index
FDA UNII
90698QK27F
Created by admin on Sat Dec 16 08:53:13 GMT 2023 , Edited by admin on Sat Dec 16 08:53:13 GMT 2023
PRIMARY