noradrénaline

Also known as noradrenaline, (-)-norepinephrine, (-)-arterenol, (R)-norepinephrine, (R)-4-(2-amino-1-hydroxyethyl)-1,2-benzenediol, (R)-(-)-norepinephrine, (-)-noradrenaline, 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol

composé chimique

OverviewAI-generated

Norepinephrine is a chemical compound with the formula C₈H₁₁NO₃. Its IUPAC name is 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol. The substance has a mass of 169.073893212 and a weight of 169.18. It possesses a defined daily dose of 6.

The molecule exhibits a charge of 0, an xlogp value of -1.2, and a topological polar surface area of 86.7. It contains four hydrogen bond donors and four hydrogen bond acceptors. The isomeric SMILES notation for norepinephrine is C1=CC(=C(C=C1[C@H](CN)O)O)O, while its canonical SMILES is C1=CC(=C(C=C1C(CN)O)O)O.

Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.N: 1
Drug.O: 3
Drug.IUPAC_name: (R)-4-(2-amino-1-hydroxyethyl)benzene-1,2-diol
Drug.image: Norepinephrine.svg
Drug.image_class: skin-invert-image
Drug.caption: Skeletal formula of noradrenaline
Drug.image2: Noradrenaline-from-xtal-view-1-3D-bs-17.png
Drug.image_class2: bg-transparent
Drug.caption2: Ball-and-stick model of the zwitterionic form of noradrenaline found in the crystal structure
Drug.source_tissues: locus coeruleus; sympathetic nervous system; adrenal medulla
Drug.target_tissues: system-wide
Drug.receptors: α1, α2, β1, β3
Drug.agonists: sympathomimetic drugs, clonidine, isoprenaline
Drug.antagonists: Tricyclic antidepressants, beta blockers, antipsychotics
Drug.precursor: dopamine
Drug.biosynthesis: dopamine β-monooxygenase
Drug.metabolism: MAO-A; COMT
Drug.CAS_number: 51-41-2

via Wikipedia infobox

Chemical data

Formula: C8H11NO3
Molecular weight: 169.18 g/mol
IUPAC name: 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
SMILES: C1=CC(=C(C=C1[C@H](CN)O)O)O
InChIKey: SFLSHLFXELFNJZ-QMMMGPOBSA-N
XLogP: -1.2
Polar surface area: 86.7 Å²
H-bond donors: 4
H-bond acceptors: 4
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1950
Admin. routes: parenteral
Indications: cardiovascular disease, acute lung injury, hypotension, orthostatic hypotension

via ChEMBL · EBI

Research

135,671 papers

Norepinephrine Modulates Coding of Complex Vocalizations in the Songbird Auditory Cortex Independent of Local Neuroestrogen Synthesis.The Journal of neuroscience : the official journal of the Society for Neuroscience · 2015Ikeda MZ, Jeon SD, Cowell RA et al.DOI: 10.1523/JNEUROSCI.4445-14.2015
[Noradrenaline and behavior].ReviewCeskoslovenska fysiologie · 2010Prokopová I
Comparison of vasopressors for management of hypotension in high-risk caesarean section under neuraxial anesthesia: a systematic review and network meta-analysis.BMC anesthesiology · 2024Zhao S, Chen Q, Qin P et al.DOI: 10.1186/s12871-024-02819-9
[Adrenaline and noradrenaline].Lakartidningen · 1965von Euler US
Sex differences in noradrenergic regulation of the medial prefrontal cortex in mice.Biology of sex differences · 2025Scroger MV, Athanason AC, Paperny NM et al.DOI: 10.1186/s13293-025-00779-4
The alpha(1)-adrenoceptor subtype- and protein kinase C isoform-dependence of Norepinephrine's actions in cardiomyocytes.Journal of molecular and cellular cardiology · 2000Rohde S, Sabri A, Kamasamudran R et al.DOI: 10.1006/jmcc.2000.1153
Uptake and release of norepinephrine by slices of rat cerebral cortex: effect of agents that increase cyclic AMP levels.Neurology · 1978Walker JE, Goodman P, Jacobs D et al.DOI: 10.1212/wnl.28.9.900
A noradrenergic theory of cognitive reserve: implications for Alzheimer's disease.ReviewNeurobiology of aging · 2013Robertson IHDOI: 10.1016/j.neurobiolaging.2012.05.019

via PubMed

Wikidata facts

Has part: carbon
Mass: 169.073893212
Has use: medication

Show 13 more facts

used by: norepinephrine
chemical formula: C₈H₁₁NO₃
medical condition treated: neurogenic shock
topic's main category: Category:Norepinephrine
isomeric SMILES: C1=CC(=C(C=C1[C@H](CN)O)O)O
Commons category: Norepinephrine
canonical SMILES: C1=CC(=C(C=C1C(CN)O)O)O
World Health Organisation international non-proprietary name: norepinephrine
defined daily dose: 6
subject has role: neurotransmitter
found in taxon: broad bean
permanent duplicated item: norepinephrine
significant drug interaction: clomipramine

Sources (8)

via Wikidata · CC0

Article · Français

La noradrénaline ou norépinéphrine est un composé organique qui joue le rôle d'hormone adrénergique et de neurotransmetteur. C'est une catécholamine comme la dopamine ou l'adrénaline. Elle est principalement libérée au niveau du tronc cérébral et par les fibres nerveuses du système nerveux orthosympathique (ou sympathique) et agit comme neurotransmetteur au niveau des organes effecteurs. Elle est également le précurseur métabolique de l'adrénaline (NOR signifiant Nitrogen ohne Radikal en allemand, littéralement azote sans radical ou azote libre). Elle est aussi libérée en faible quantité (20 %) par les médullosurrénales et agit comme hormone. Elle joue alors un rôle dans l'excitation, l'orientation de nouveaux stimuli, l'attention sélective, la vigilance, les émotions, le réveil et le sommeil, le rêve et les cauchemars, l'apprentissage et le renforcement de certains circuits de la mémoire impliquant un stress chronique. Que ce soit en tant qu'hormone ou neurotransmetteur, la noradrénaline agit sur les mêmes récepteurs, dits récepteurs adrénergiques alpha et bêta, tous couplés aux protéines G trimériques.

Abstract from DBpedia / Wikipedia · CC BY-SA