METARAMINOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H13NO2
Molecular Weight	167.205
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=WXFIGDLSSYIKKV-RCOVLWMOSA-N

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

HIDE SMILES / InChI

Molecular Formula	C9H13NO2
Molecular Weight	167.205
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.druginformation.com/RxDrugs/M/Metaraminol%20Bitartrate%20Injection.html | https://www.ncbi.nlm.nih.gov/pubmed/9663612 | https://www.ncbi.nlm.nih.gov/pubmed/15703094

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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-1 171 Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9663612	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Acute hypotensive state 3 Sources: http://www.druginformation.com/RxDrugs/M/Metaraminol%20Bitartrate%20Injection.html	Preventing	Approved 8583	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.
Hemorrhage 11 Sources: http://www.druginformation.com/RxDrugs/M/Metaraminol%20Bitartrate%20Injection.html	Palliative	Approved 8583	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.
Shock 9 Sources: http://www.druginformation.com/RxDrugs/M/Metaraminol%20Bitartrate%20Injection.html	Palliative	Approved 8583	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.
Priapism 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15703094	Primary	Not Provided 511	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/2751185	unhealthy, 38 years Health Status: unhealthy Age Group: 38 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/2751185	Disc. AE: Bigeminal rhythm... AEs leading to discontinuation/dose reduction: Bigeminal rhythm (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2751185

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/2751185	unhealthy, 38 years Health Status: unhealthy Age Group: 38 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/2751185

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BSEP 550 CYP1A2 2153 CYP2C19 2057 OATP1B1 1079 OATP1B3 961

Drug as perpetrator

Target	Modality	Activity
BSEP 554	inhibitor 4027 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50239972, https://pubmed.ncbi.nlm.nih.gov/22961681/	no [IC50 >1000 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIwNjIyNjIifX0%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIwNjIyNjIifX0%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzMTkifX0%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzMTkifX0%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzMTkifX0%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTIwMTMxOSJ9fQ%3D%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTIwMTMxOSJ9fQ%3D%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6794	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6794
ZINC	ZINC000000001695	http://zinc15.docking.org/substances/ZINC000000001695

PubMed

Title	Date	PubMed
[Determination of three adrenergic drugs using capillary electrophoresis with amperometric detection].	2010-11	21381427
Molecular imaging of cardiac sympathetic innervation by 11C-mHED and PET: from man to mouse?	2010-08	20679472
Clinical evaluation of the flotrac/Vigileo system for continuous cardiac output monitoring in patients undergoing regional anesthesia for elective cesarean section: a pilot study.	2010-06	20835557
Disparities of care for African-Americans and Caucasians with community-acquired pneumonia: a retrospective cohort study.	2010-05-27	20507628
Adenosine-induced cardiopulmonary arrest in a patient with paroxysmal supraventricular tachycardia--a response.	2010-05	20466244
Vasopressor choice for hypotension in elective Cesarean section: ephedrine or phenylephrine?	2010-04-30	22371756
Cardiac arrest in intensive care unit: Case report and future recommendations.	2010-01	20668565
Which vasopressor for caesarean section?	2009-12	20081625
Impact of admixture time and diluent order on metaraminol concentration.	2009-09	19777670
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.	2009-08-15	19608416
Myocardial infarction associated with the administration of intravenous ephedrine and metaraminol for spinal-induced hypotension.	2009-05	19413828
Amniotic fluid embolism during vaginal delivery under analgesia. Case report.	2009-04-22	19378589
Is propofol a safe and effective sedative for relocating hip prostheses?	2009-01	19104094
Mollaret meningitis may be caused by reactivation of latent cerebral toxoplasmosis.	2009	19922380
Sickle cell trait and priapism: a case report and review of the literature.	2008-12-30	19116025
Ventricular arrhythmias and antioxidative medication: experimental study.	2008-10-14	18846922
[Diagnosis and treatment of priapism: a report of 15 cases].	2008-09	18998470
Transient transmural ischaemia during endobronchial laser treatment: possible coronary artery embolism.	2008-09	18853597
[Anesthesia for cesarean section in a patient with familiar hypertrophic cardiomyopathy: case report.].	2007-12	19462143
"Orpheus" cardiopulmonary bypass simulation system.	2007-12	18293807
Pharmacokinetic study of three cardiovascular drugs by high-performance liquid chromatography using pre-column derivatization with 9,10-anthraquinone-2-sulfonyl chloride.	2007-10-15	17766197
Effect of dopamine and metaraminol on the renal function of patients with septic shock.	2007-04-20	17517184
The blood-brain barrier for catecholamines - revisited.	2007-04	17449463
A prospective comparison of vasopressor requirement and hemodynamic changes during spinal anesthesia for cesarean delivery in patients with multiple gestation versus singleton pregnancy.	2007-02	17242099
Effect of induction agent on vasopressor and steroid use, and outcome in patients with septic shock.	2007	17506873
Meningismus after metaraminol administration in a patient with Familial Mediterranean fever.	2006-10	16987863
[Effect of fluid resuscitation on adhesion molecule and hemodynamics in patients with severe sepsis].	2006-09	16959151
Use of metaraminol in patients with Familial Mediterranean Fever.	2006-08	16867110
Planar chromatographic analysis and quantification of short-lived radioactive metabolites from microdialysis fractions.	2006-03-03	16445924
[Diagnosis and treatment of priapism due to neoplasma of penis].	2006-02	16519158
Bench-to-bedside review: hyperinsulinaemia/euglycaemia therapy in the management of overdose of calcium-channel blockers.	2006	16732893
[Preload during spinal anesthesia for cesarean section: comparison between crystalloid and colloid solutions.].	2004-12	19471789
Fluid preload in obstetric patients. How to do it?	2004-02	19471706
Dynamic left ventricular outflow tract obstruction in critically ill patients.	2002-09	16573425
Reversible segmental left-ventricular dysfunction caused by accidental administration of sympathomimetic drug in human.	1997-08-29	9292339
The effect of intracarotid nonionic contrast media on the blood-brain barrier in acute hypertension.	1994-01	8141072
Post-traumatic priapism treated with metaraminol bitartrate: case report.	1990-12	2258979
[Familial Mediterranean fever. The metaraminol test as a cause of severe cephalalgia].	1990-06	2244064
The metaraminol test and adverse cardiac effects.	1989-08-01	2751185
[Epilepsy and hypertensive crisis after intracavernous injection of metaraminol in the treatment of priapism secondary to a papaverine test].	1989-05-20	2524805
[Papaverine-induced priapism. Experiences with a new urologic emergency].	1989-02-10	2917481
[Metaraminol in therapy of various forms of priapism].	1988-07	3140463
Assessment of the permeability of the blood-retinal barrier in hypertensive rats.	1987-10	3653967
An extravascular hydraulic system to control blood pressure by a feedback regulation of the venous return.	1987-05	3652100
Cerebral arteriovenous malformations, steal, and the hypertensive breakthrough threshold. An experimental study in rats.	1987-04	3559722
[Metaraminol--an antidote in corpus cavernosum autoinjection therapy-induced prolonged erection].	1986-05	2426857
[Prinzmetal's angina induced by dopamine and metaraminol. 2 cases].	1979-03	491823
Pulmonary edema: a complication of metaraminol treatment of paroxysmal supraventricular tachycardia.	1974-05	4415385
Myocardial infarction induced by metaraminol bitartrate (aramine).	1966-10	6009556
Augmented natriuretic response to infusion of saline in dogs rendered acutely hypertensive with metaraminol.	1966-07	5918955

Patents

Sample Use Guides

In Vivo Use Guide

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:22:56 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:56 GMT 2025`
Record UNII	818U2PZ2EH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METARAMINOL

Official Name

English

BENZENEMETHANOL, ALPHA-(1-AMINOETHYL)-3-HYDROXY-, (R-(R*,S*))-

Preferred Name

English

METARAMINOL [MI]

Common Name

English

METARAMINOL [HSDB]

Common Name

English

metaraminol [INN]

Common Name

English

METARAMINOL [VANDF]

Common Name

English

Metaraminol [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C01CA09