norepinephrine

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

Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic chemical in the catecholamine family that functions in the brain and body as a hormone, neurotransmitter and neuromodulator. The name "norepinephrine" (from Ancient Greek ἐπῐ́ (epí), "upon", and νεφρός (nephrós), "kidney") is usually preferred in the United States, whereas "noradrenaline" (from Latin ad, "near", and ren, "kidney") is more commonly used in the United Kingdom and the rest of the world. "Norepinephrine" is also the international nonproprietary name given to the drug. Regardless of which name is use

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

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

~30 min read

Encyclopedic overview

27 sections

Contents

Structure
Biochemical mechanisms
Biosynthesis
Degradation
Functions
Cellular effects
Storage, release, and reuptake
Sympathetic nervous system
Central nervous system
Skin
Pharmacology
Antagonists
Beta blockers
Alpha blockers
Alpha-2 agonists
Stimulants and antidepressants
Diseases and disorders
Sympathetic hyperactivation
Pheochromocytoma
Stress
ADHD
Autonomic failure
REM sleep deprivation
Comparative biology and evolution
History
References
External links

The general function of norepinephrine is to mobilize the brain and body for action. Norepinephrine release is lowest during sleep, rises during wakefulness, and reaches much higher levels during situations of stress or danger, in the so-called fight-or-flight response. In the brain, norepinephrine increases arousal and alertness, promotes vigilance, enhances formation and retrieval of memory, and focuses attention; it also increases restlessness and anxiety. In the rest of the body, norepinephrine increases heart rate and blood pressure, triggers the release of glucose from energy stores, increases blood flow to skeletal muscle, reduces blood flow to the gastrointestinal system, and inhibits voiding of the bladder and gastrointestinal motility.

Excerpted from Wikipedia’s “norepinephrine” article, available under the CC BY-SA 4.0 licence.