Chemical substance record

(R)-adrenaline

51-43-4C₉H₁₃NO₃183.207 g/mol

Organic/Inorganic Small MoleculeChEBI source record

The R-enantiomer of adrenaline. It is a hormone secreted by the adrenal glands resulting in the 'fight-or-flight' response. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	51-43-4	ChEBI ↗
Molecular formula	C₉H₁₃NO₃	ChEBI ↗
Molar mass	183.207 g/mol	ChEBI ↗
Monoisotopic mass	183.08954 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:28918	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	183.20 g/mol	PubChem ↗
Exact mass	183.08954328 Da	PubChem ↗
Computed XLogP	-1.4	PubChem ↗
Topological polar surface area (Å²)	72.7	PubChem ↗
H-bond donors	4	PubChem ↗
H-bond acceptors	4	PubChem ↗
Rotatable bonds	3	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

(R)-adrenaline

IUPAC name

4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

InChIKey

UCTWMZQNUQWSLP-VIFPVBQESA-N

SMILES

CNC[C@H](O)c1ccc(O)c(O)c1

InChI

InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1

Names & synonyms

4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diolAdrenalinepinefrinaepinephrineepinephrinumEpipenEpipen JRPrimatene

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

Classification & relationships

ChEBI ontology

4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diolChEBI parent class · 194548 ↗

phenols organic molecular entity

Roles recorded in ChEBI

hormoneantiinfective agentantidepressantanalgesicbeta-adrenergic agonistbronchodilator agentsympathomimetic agenthypoglycemic agentcardiovascular drugalpha-adrenergic agonist

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

0.00545831 mol

Uses 183.207 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

59.00%

O

Oxygen · 3 atoms

26.20%

N

Nitrogen · 1 atom

7.65%

H

Hydrogen · 13 atoms

7.15%

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

Contribution of the sympathetic hormone epinephrine to the sensitizing effect of ethanol on LPS-induced liver damage in mice. ↗American journal of physiology. Gastrointestinal and liver physiology · 2008 May · PMID 18325983

Combination pharmacotherapy improves neurological outcome after asphyxial cardiac arrest. ↗Resuscitation · 2012 Apr · PMID 21963816

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:28918

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

Additional molecular descriptorsNCBI PubChem · CID 5816 · 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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