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Noradrenaline

Athanor · official

C8H11NO3 · 169.18 g/mol

IUPAC name: 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol

Also called norepinephrine, Levophed, catecholamine

Natural productsDrugs
Open in Athanor
The structure of Noradrenaline
Drawn from its SMILES with RDKit
Acute toxicityDangerFatal if swallowed · Fatal in contact with skin · Fatal if inhaled

Names and identifiers

IUPAC name
4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
Synonyms
norepinephrine, Levophed, catecholamine
+ 39 more

L-Noradrenaline, Levarterenol, Arterenol, L-Norepinephrine, (R)-Noradrenaline, (-)-Norepinephrine, (-)-NORADRENALINE, L-arterenol, (-)-Arterenol, (R)-Norepinephrine, 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol, Levonoradrenaline, Sympathin E, Levonorepinephrine, (R)-(-)-Norepinephrine, Norepirenamine, (R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol, Noradrenalin, norepinephrinum, Noradrenalinum, Norartrinal, Nor adrenalin, Nor-Epirenan, norepinefrina, Noradrenalina, L-3,4-dihydroxyphenylethanolamine, D-(-)-Noradrenaline, l-2-Amino-1-(3,4-dihydroxyphenyl)ethanol, (-)-alpha-(Aminomethyl)protocatechuyl alcohol, L-alpha-(aminomethyl)-3,4-dihydroxybenzyl alcohol, 4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediol, DTXSID5023378, X4W3ENH1CV, 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (R)-, NSC-757246, DTXCID203378, CHEBI:18357, 4-((1R)-2-Amino-1-hydroxyethyl)-1,2-benzenediol, 4-((1R)-2-amino-1-hydroxyethyl)benzene-1,2-diol

Molecular formula
C8H11NO3
Empirical formula
C8H11NO3
Molecular weight
169.18 g/mol
Exact mass
169.07389
CAS number
51-41-2
PubChem CID
439260
Canonical SMILES
C1=CC(=C(C=C1C(CN)O)O)O
Isomeric SMILES
C1=CC(=C(C=C1[C@H](CN)O)O)O
InChI
InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1
InChIKey
SFLSHLFXELFNJZ-QMMMGPOBSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Physical properties

Appearance
Colorless microcrystals[1]
log P
log Kow = -1.24[1]
pKa
pKa = 8.58 (conjugate acid)[1]

Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.

Calculated

Heavy atoms
12
Rings
1
Aromatic rings
1
Fraction sp³ carbons (Fsp3)
0.25
H-bond donors
4
H-bond acceptors
4
Rotatable bonds
2
TPSA (Ų)
86.7
Formal charge
0
XLogP3
-1.2 PubChem
Complexity
142 PubChem
Stereocenters
1 definedCIP: C3: R
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C56.80%
  • H6.55%
  • N8.28%
  • O28.37%

Isotope pattern

100%169.0749.3%170.0771.0%171.079

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
0.09 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-1.18 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
2.68 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 169.18
  • log P ≤ 5 (Crippen): 0.09
  • H-bond donors ≤ 5: 4
  • H-bond acceptors ≤ 10: 4

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Danger

Most widely reported: 47 company reports to ECHA. Source [2].

  • Acute toxicity
  • H300Fatal if swallowed (97.9% of reports)
  • H310Fatal in contact with skin (87.2% of reports)
  • H330Fatal if inhaled (89.4% of reports)

Precautionary statements: P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, P501

Storage

  • Store at 20 deg to 25 °C (68 deg to 77 °F). ... Protect from light.[1]

Safety data sheets on the supplier’s page: Sigma-Aldrich, ChemoSapiens, Thermo Fisher Scientific.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
  2. [2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  3. [3]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  5. [5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  6. [6]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  7. [7]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  8. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  9. ·Literature on PubChem

Data last updated 2026-10-14.