A7257

(−)-Norepinephrine

≥98% (TLC), crystalline, adrenergic neurotransmitter

• Synonym(s): (R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol, L-Arterenol, L-Noradrenaline, Levarterenol
• 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

Properties

• 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)

Description

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.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H300 + H310 + H330
• pcodes: P260 - P262 - P264 - P280 - P302 + P352 + P310 - P304 + P340 + P310
• 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