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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:
2804840
EC Number:
200-096-6
MDL number:
MFCD00025592
UNSPSC Code:
12352200
PubChem Substance ID:
24891196
NACRES:
NA.77

product name

(−)-Norepinephrine, ≥98%, crystalline

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Daina Economidou et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 37(9), 2057-2066 (2012-04-19)
Impulsive behavior is a hallmark of several neuropsychiatric disorders (eg, attention-deficit/hyperactivity disorder, ADHD). Although dopamine (DA) and norepinephrine (NE) have a significant role in the modulation of impulsivity their neural loci of action is not well understood. Here, we investigated
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
Mostafa El Mansari et al.
CNS neuroscience & therapeutics, 16(3), e1-17 (2010-04-22)
Central dopaminergic and noradrenergic systems play essential roles in controlling several forebrain functions. Consequently, perturbations of these neurotransmissions may contribute to the pathophysiology of neuropsychiatric disorders. For many years, there was a focus on the serotonin (5-HT) system because of
Junji Shibahara et al.
The American journal of surgical pathology, 28(6), 825-829 (2004-05-29)
We describe a case of primary pulmonary paraganglioma, a tumor that has not been reported in sufficient detail in previous literature. The patient was a 55-year-old woman with hypertension accompanied by an elevated serum norepinephrine level (2651 pg/mL; normal 100-450
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
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LC/MS/MS Analysis of Epinephrine, Metanephrine and Metabolites on Ascentis® Express OH5

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