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A7257

Sigma-Aldrich

(−)-Norepinephrine

≥98% (TLC), crystalline, adrenergic neurotransmitter

Synonym(s):

(R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol, L-Arterenol, L-Noradrenaline, Levarterenol

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About This Item

Empirical Formula (Hill Notation):
C8H11NO3
CAS Number:
51-41-2
Molecular Weight:
169.18
Beilstein/REAXYS Number:
2804840
EC Number:
200-096-6
MDL number:
MFCD00025592
UNSPSC Code:
12352200
PubChem Substance ID:
24891196
NACRES:
NA.77

product name

(−)-Norepinephrine, ≥98%, crystalline

Quality Level

200

assay

≥98%

form

crystalline

color

off-white to tan

storage temp.

−20°C

SMILES string

NC[C@H](O)c1ccc(O)c(O)c1

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

Gene Information

human ... ADRA1A(148) , ADRA1B(147) , ADRA1D(146) , ADRA2A(150) , ADRA2B(151) , ADRA2C(152) , ADRB1(153) , ADRB2(154) , ADRB3(155)
rat ... Adra1a(29412) , Adra1d(29413) , Adra2a(25083) , Adrb1(24925) , Adrb2(24176) , Drd1a(24316) , Drd2(24318)

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General description

Norepinephrine is a neurotransmitter found in both the peripheral and central nervous systems. It triggers effects associated with the ′fight or flight′ response and is mediated by the family of adrenergic receptors. Structurally, it is a catecholamine due to the presence of the catechol moiety (consisting of two hydroxyl groups on a benzene ring) and an amine (NH2) group. Norepinephrine exhibits pharmacologic effects on α1 and β1 adrenoceptors. It does not elevate heart rate. The primary advantage of norepinephrine is to improve organ perfusion by increasing vascular tone. Compared to dopamine, norepinephrine is more effective at achieving targeted endpoints, less metabolically active than epinephrine, and reduces serum lactate levels. Moreover, it notably enhances renal perfusion and splanchnic blood flow in sepsis, especially when used alongside dobutamine. Norepinephrine is used in the treatment of hypotension, depression, schizophrenia, and attention deficit/hyperactivity disorders.

Application

(−)-Norepinephrine has been used:
  • as anαand β-AR agonist to stimulate mouse organoids to study the pathways that are activated upon intestinal epithelial adrenergic receptor (AR) stimulation,
  • to measure the monoamine levels in various limbic regions of mouse brains by high-performance liquid chromatography (HPLC) coupled with an electrochemical equipped with an auto-sampler,
  • as a dispersal agent in biofilm dispersion assay to study its effects on the dispersal of Mannheimia haemolytica biofilms

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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Skull and crossbones
GHS06

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Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Storage Class

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Anne S Ten Hove et al.
Scientific reports, 13(1), 17990-17990 (2023-10-21)
Innervation of the intestinal mucosa by the sympathetic nervous system is well described but the effects of adrenergic receptor stimulation on the intestinal epithelium remain equivocal. We therefore investigated the effect of sympathetic neuronal activation on intestinal cells in mouse
Mostafa M H Ibrahim et al.
ASN neuro, 12, 1759091420974134-1759091420974134 (2020-11-13)
Norepinephrine (NE) control of hypothalamic gluco-regulation involves astrocyte-derived energy fuel supply. In male rats, exogenous NE regulates astrocyte glycogen metabolic enzyme expression in vivo through 5'-AMP-activated protein kinase (AMPK)-dependent mechanisms. Current research utilized a rat hypothalamic astrocyte primary culture model
Ophiocordyceps formosana improves hyperglycemia and depression-like behavior in an STZ-induced diabetic mouse model
Huang CW, et al.
BMC Complementary and Alternative Medicine, 16, 1-11 (2016)
Role of the stress-associated chemicals norepinephrine, epinephrine and substance P in dispersal of Mannheimia haemolytica from biofilms
Pillai DK, et al.
Veterinary Microbiology, 215, 11-17 (2018)
Kelly Del Tredici et al.
Journal of neurology, neurosurgery, and psychiatry, 84(7), 774-783 (2012-10-16)
Although resting tremor, cogwheel rigidity, hypokinesia/bradykinesia and postural instability usually dominate the clinical picture of sporadic Parkinson's disease (PD), both clinical and epidemiological data reveal that a wide variety of additional symptoms impair patients' quality of life considerably, parallel to
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