نوراپی‌نفرین

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 Ų

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

• 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

via Wikidata · CC0