CHEBI:6794 - metaraminol

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ChEBI Name metaraminol
ChEBI ID CHEBI:6794
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C9H13NO2
Net Charge 0
Average Mass 167.20506
Monoisotopic Mass 167.09463
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
SMILES C[C@H](N)[C@H](O)c1cccc(O)c1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): alpha-adrenergic agonist
An agent that selectively binds to and activates alpha-adrenergic receptors.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
Application(s): alpha-adrenergic agonist
An agent that selectively binds to and activates alpha-adrenergic receptors.
vasoconstrictor agent
Drug used to cause constriction of the blood vessels.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing metaraminol (CHEBI:6794) has role α-adrenergic agonist (CHEBI:35569)
metaraminol (CHEBI:6794) has role sympathomimetic agent (CHEBI:35524)
metaraminol (CHEBI:6794) has role vasoconstrictor agent (CHEBI:50514)
metaraminol (CHEBI:6794) is a phenylethanolamines (CHEBI:25990)
IUPAC Name
3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol
INNs Sources
métaraminol ChEBI
metaraminol ChemIDplus
metaraminolum ChemIDplus
Synonyms Sources
(-)-Erythro-metaraminol ChemIDplus
1-(m-Hydroxyphenyl)-2-amino-1-propanol ChemIDplus
1-Metaraminol ChemIDplus
2-Amino-1-(m-hydroxyphenyl)-1-propanol ChemIDplus
3-Hydroxyphenylisopropanolamine ChemIDplus
alpha-(1-Aminoethyl)-3-hydroxybenzenemethanol ChemIDplus
alpha-(m-Hydroxyphenyl)-beta-aminopropanol ChemIDplus
Hydroxynorephedrine DrugBank
L-Metaraminol DrugBank
M-Hydroxy Norephedrine ChEBI
M-Hydroxyphenylpropanolamine DrugBank
m-Hydroxypropadrine ChemIDplus
Metaraminol KEGG COMPOUND
Manual Xrefs Databases
1721 DrugCentral
C07146 KEGG COMPOUND
CH162367 Patent
D08192 KEGG DRUG
DB00610 DrugBank
GB353361 Patent
GB396951 Patent
HMDB0014748 HMDB
LSM-6000 LINCS
Metaraminol Wikipedia
US1948162 Patent
US1951302 Patent
US1995709 Patent
View more database links
Registry Numbers Types Sources
3198820 Reaxys Registry Number Reaxys
3198820 Beilstein Registry Number Beilstein
54-49-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14163327 PubMed citation Europe PMC
21629799 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2014-05-08 Metaraminol can be found in blood and urine samples of individuals who have taken this drug.