SynCED: Norepinephrine

Record Information

Version

1.0

Creation Date

2014-08-29 05:47:21 UTC

Update Date

2026-05-14 16:36:44 UTC

Accession Number

CHEM003114

Identification

Common Name

Norepinephrine

Class

Small Molecule

Description

Noradrenalin is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Precursor of epinephrine that is secreted by the adrenal medulla and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers and of the diffuse projection system in the brain arising from the locus ceruleus. It is also found in plants and is used pharmacologically as a sympathomimetic. [PubChem]

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Adrenergic alpha-Agonist
Amine
Drug
Food Toxin
Metabolite
Natural Compound
Organic Compound
Sympathomimetic
Uremic Toxin
Vasoconstrictor Agent

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Arterenol	ChEBI
(-)-Noradrenaline	ChEBI
(-)-Norepinephrine	ChEBI
(R)-(-)-Norepinephrine	ChEBI
(R)-4-(2-amino-1-Hydroxyethyl)-1,2-benzenediol	ChEBI
(R)-Norepinephrine	ChEBI
4-[(1R)-2-amino-1-Hydroxyethyl]-1,2-benzenediol	ChEBI
Arterenol	ChEBI
L-Noradrenaline	ChEBI
L-Norepinephrine	ChEBI
Noradrenaline	ChEBI
Norepinefrina	ChEBI
Norepinephrinum	ChEBI
(-)-(R)-Norepinephrine	HMDB
(-)-alpha-(Aminomethyl)protocatechuyl alcohol	HMDB
(R)-Noradrenaline	HMDB
4-(2-amino-1-Hydroxyethyl)-1,2-benzenediol	HMDB
Adrenor	HMDB
Aktamin	HMDB
L-2-amino-1-(3,4-Dihydroxyphenyl)ethanol	HMDB
L-3,4-Dihydroxyphenylethanolamine	HMDB
L-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcohol	HMDB
L-Arterenol	HMDB
Levarterenol	HMDB, MeSH
Levoarterenol	HMDB
Levonor	HMDB, MeSH
Levonoradrenaline	HMDB
Levonorepinephrine	HMDB, MeSH
Levophed	HMDB, MeSH
Nor-epirenan	HMDB
Noradrenalin	HMDB
Norartrinal	HMDB
Norepirenamine	HMDB
Sympathin E	HMDB

Chemical Formula

C₈H₁₁NO₃

Average Molecular Mass

169.178 g/mol

Monoisotopic Mass

169.074 g/mol

CAS Registry Number

51-41-2

IUPAC Name

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

Traditional Name

norepinephrine

SMILES

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

InChI Identifier

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

InChI Key

SFLSHLFXELFNJZ-QMMMGPOBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Monocyclic benzene moiety
1,2-aminoalcohol
Secondary alcohol
Organic nitrogen compound
Aromatic alcohol
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

noradrenaline (CHEBI:18357 )
Biogenic amines (C00547 )
Adrenalines (C00547 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Adrenal Medulla
Bladder
Brain
Central Nervous System
Epidermis
Fibroblasts
Gonads
Heart
Intestine
Kidney
Lymphocyte
Muscle
Nerve Cells
Neuron
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle

Pathways

Name	SMPDB Link	KEGG Link
Catecholamine Biosynthesis	SMP00012	map00350
Tyrosine Metabolism	SMP00006	map00350

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	217 dec°C
Boiling Point	Not Available
Solubility	849 mg/mL

Predicted Properties

Property	Value	Source
logP	-0.68	ChemAxon
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	8.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	86.71 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.46 m³·mol⁻¹	ChemAxon
Polarizability	16.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Endogenous, Ingestion, Dermal (contact)

Mechanism of Toxicity

Uremic toxins such as noradrenalin are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (2). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (3). Norepinephrine functions as a peripheral vasoconstrictor by acting on alpha-adrenergic receptors. It is also an inotropic stimulator of the heart and dilator of coronary arteries as a result of it's activity at the beta-adrenergic receptors.

Metabolism

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Mainly used to treat patients in vasodilatory shock states such as septic shock and neurogenic shock and has shown a survival benefit over dopamine. Also used as a vasopressor medication for patients with critical hypotension.

Minimum Risk Level

Not Available

Health Effects

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

Symptoms

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Treatment

Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

Concentrations

Not Available

External Links

DrugBank ID

DB00368

HMDB ID

HMDB0000216

FooDB ID

FDB016812

Phenol Explorer ID