Metaraminol

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Description

Metaraminol ((-) -Metaraminol) is a sympathomimetic compound with activity that acts primarily at alpha-1 adrenergic receptors. Metaraminol is used to inhibit hypotension due to vasodilation, particularly in critically ill patients who do not respond well to volume resuscitation. Metaraminol may also be used as an adjunct to help improve cardiac contractility. The use of metaraminol may be supported by less evidence, but its effectiveness in specific situations remains of interest[1].

CAS Number

54-49-9

Product Name Alternative

(-) -Metaraminol; (-) -erythro-Metaraminol; (-) -m-Hydroxynorephedrine

UNSPSC

12352005

Hazard Statement

H302-H312-H332

Target

Adrenergic Receptor

Type

Reference compound

Related Pathways

GPCR/G Protein; Neuronal Signaling

Applications

Neuroscience-Neuromodulation

Field of Research

Neurological Disease

Assay Protocol

https://www.medchemexpress.com/metaraminol.html

Smiles

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

Molecular Formula

C9H13NO2

Molecular Weight

167.21

Precautions

P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363-P501

References & Citations

[1]Vasopressor therapy in critically ill patients with shock

Shipping Conditions

Room temperature

Scientific Category

Reference compound1

Clinical Information

Launched

Chemical Information

Metaraminol

Metaraminol is a member of the class of phenylethanolamines that is 2-amino-1-phenylethanol substituted by a methyl group at position 2 and a phenolic hydroxy group at position 1. A sympathomimetic agent , it is used in the treatment of hypotension. It has a role as a sympathomimetic agent, an alpha-adrenergic agonist and a vasoconstrictor agent.

CAS Number	54-49-9
PubChem CID	5906
IUPAC Name	3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol
Molecular Formula	C9H13NO2
Molecular Weight	167.20
XLogP	-0.4
Topological Polar Surface Area	66.5
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Heavy Atom Count	12
Formal Charge	0
Complexity	140

SMILES

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

InChI

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

InChIKey

WXFIGDLSSYIKKV-RCOVLWMOSA-N

Chemical Structure

2D Structure

CAS: 54-49-9

CID: 5906

Formula: C9H13NO2

MW: 167.20

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	167.20
XLogP3	-0.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	167.094628657
Monoisotopic Mass	167.094628657
Topological Polar Surface Area	66.5 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	140
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
AAA06159-01	(+) -Metaraminol
GTR19206793	Metaraminol
TRC-M321975-250MG	(+)-Metaraminol
MBS577103	Metaraminol bitartrate
GTR19176278-01	Metaraminol tartrate
FM183787-01	Metaraminol bitatrate
MBS5789784	Metaraminol hydrochloride
AR-E08950-01	Threo-Metaraminol
RG-H251801-01	Metaraminol Impurity A
RM-M201859-01	Metaraminol Impurity 59

Metaraminol

Chemical Information

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