Chemical substance record

Metaraminol

54-49-9C₉H₁₃NO₂167.208 g/mol

Organic/Inorganic Small MoleculeChEBI source record

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. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	54-49-9	ChEBI ↗
Molecular formula	C₉H₁₃NO₂	ChEBI ↗
Molar mass	167.208 g/mol	ChEBI ↗
Monoisotopic mass	167.09463 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:6794	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	167.20 g/mol	PubChem ↗
Exact mass	167.094628657 Da	PubChem ↗
Computed XLogP	-0.4	PubChem ↗
Topological polar surface area (Å²)	66.5	PubChem ↗
H-bond donors	3	PubChem ↗
H-bond acceptors	3	PubChem ↗
Rotatable bonds	2	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

metaraminol

IUPAC name

3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol

InChIKey

WXFIGDLSSYIKKV-RCOVLWMOSA-N

SMILES

C[C@H](N)[C@H](O)c1cccc(O)c1

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

Names & synonyms

3-[(1R,2S)-2-amino-1-hydroxypropyl]phenolmetaraminolum

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

phenylethanolaminesChEBI parent class · 25990 ↗

alcohol organic molecular entity

Roles recorded in ChEBI

sympathomimetic agentcardiovascular drugalpha-adrenergic agonistvasoconstrictor agent

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00598058 mol

Uses 167.208 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 9 atoms

64.65%

O

Oxygen · 2 atoms

19.14%

N

Nitrogen · 1 atom

8.38%

H

Hydrogen · 13 atoms

7.84%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

RELEASE OF METARAMINOL (ARAMINE) FROM THE HEART BY SYMPATHETIC NERVE STIMULATION. ↗Science (New York, N.Y.) · 1964 Aug 21 · PMID 14163327

Prolonged Refractory Hypotension following Combined Amlodipine and Losartan Ingestion Responsive to Metaraminol. ↗Case reports in medicine · 2011 · PMID 21629799

CH162367 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

GB353361 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

GB396951 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:6794

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 5906 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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