Norepinephrine

Base Information

• Chemical Name: Norepinephrine
• CAS No.: 51-41-2
• Deprecated CAS: 66197-73-7,4899-05-2,4899-05-2
• Molecular Formula: C8H11NO3
• Molecular Weight: 169.18
• Hs Code.: 29225090
• European Community (EC) Number: 200-096-6
• NSC Number: 757246
• UNII: X4W3ENH1CV
• DSSTox Substance ID: DTXSID5023378
• Nikkaji Number: J9.223A
• Wikipedia: Norepinephrine
• Wikidata: Q186242
• RXCUI: 7512
• Pharos Ligand ID: NMF7HVW8US3U
• Metabolomics Workbench ID: 37141
• ChEMBL ID: CHEMBL1437
• Mol file: 51-41-2.mol

Synonyms:Arterenol;Levarterenol;Levonor;Levonorepinephrine;Levophed;Levophed Bitartrate;Noradrénaline tartrate renaudin;Noradrenaline;Noradrenaline Bitartrate;Norepinephrin d-Tartrate (1:1);Norepinephrine;Norepinephrine Bitartrate;Norepinephrine d-Tartrate (1:1);Norepinephrine Hydrochloride;Norepinephrine Hydrochloride, (+)-Isomer;Norepinephrine Hydrochloride, (+,-)-Isomer;Norepinephrine l-Tartrate (1:1);Norepinephrine l-Tartrate (1:1), (+,-)-Isomer;Norepinephrine l-Tartrate (1:1), Monohydrate;Norepinephrine l-Tartrate (1:1), Monohydrate, (+)-Isomer;Norepinephrine l-Tartrate (1:2);Norepinephrine l-Tartrate, (+)-Isomer;Norepinephrine, (+)-Isomer;Norepinephrine, (+,-)-Isomer

Chemical Property of Norepinephrine

Chemical Property:

• Appearance/Colour: Off-white to tan solid
• Vapor Pressure: 7.51E-07mmHg at 25°C
• Melting Point: 220-230 °C
• Refractive Index: 1.66
• Boiling Point: 442.6 °C at 760 mmHg
• PKA: 8.64(at 25℃)
• Flash Point: 221.5 °C
• PSA: 86.71000
• Density: 1.397 g/cm³
• LogP: 0.79020
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Water Solubility.: Soluble in alkali and dilute hydrochloric acid. Slightly soluble in water, ethanol and diethyl ether.
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 169.07389321
• Heavy Atom Count: 12
• Complexity: 142

Purity/Quality:

99% ^*data from raw suppliers

Noradrenaline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,C,F
• Hazard Codes: T+,C,F
• Statements: 26/27/28-34-11-28
• Safety Statements: 28-36/37-45-36/37/39-26-16-20

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C(CN)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1[C@H](CN)O)O)O
• Recent ClinicalTrials: Hot Flashes and Neurovascular Function in Women
• Recent EU Clinical Trials: Clinical Outcome and Cost-effectiveness of Reduced Noradrenaline by Using a Lower Blood Pressure Target in Patients with Cardiogenic Shock from Acute Myocardial Infarction: A Multicenter Randomized Trial
• Recent NIPH Clinical Trials: Trial for the safety of early discontinuation of low-dose steroids in patients with septic shock
• Uses: Vascular active drug resistance to shock An adrenergic neurotransmitter. Norepinephrine is used for increasing cardiac constriction and for the necessary elevation of blood pressure after sharp decline, which can result from surgical intervention or trauma.
• Biological Functions: Most central noradrenergic neurons are located in the nucleus locus ceruleus of the pons and in neurons of the reticular formation. Fibers from these nuclei innervate a large number of cortical, subcortical, and spinomedullary fields. Many functions have been ascribed to the central noradrenergic neurons, including a role in affective disorders (see Chapter 33), in learning and memory, and in sleep–wake cycle regulation.The mammalian CNS contains both α- and β-adrenoceptors.

Technology Process of Norepinephrine

There total 14 articles about Norepinephrine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.3%

arterenone (499-61-6) → norepinephrine (51-41-2)

Guidance literature:

arterenone; With (-)-diisopinocampheylboron chloride; In tert-butyl methyl ether; at -25 - -20 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In tert-butyl methyl ether; water; at 25 ℃; for 1.5h; Reagent/catalyst; Solvent; Temperature; Catalytic behavior; Inert atmosphere;

Reference yield: 51.4%

R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan (104819-57-0,104873-30-5,104873-31-6) → norepinephrine (51-41-2)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; for 6h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87372-5

Reference yield:

C14H21N4O3(1+)*Cl(1-) → norepinephrine (51-41-2)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 10h;

upstream raw materials:

Norepinephrine

R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan

glycine

3,4-dihydroxybenzaldehyde

Downstream raw materials:

(R)-N-salicylidenenorepinephrine

1,2,3,4-tetrahydro-4,6,7-isoquinolinetriol hydrochloride

(R)-3',4'-dihydroxyphenylglycol

(R)-(-)-2-amino-1-(3,4-dimethoxyphenyl)ethanol

Refernces

• 1、 -. "Method for asymmetrically synthesizing norepinephrine bitartrate". Paragraph 0017-0018; 0032; 0033; 0034. . Retrieved 2020/12/30.
• 2、 -. "A Method for Synthesizing a Catecholamine Using Plasma Polymerization". . . Retrieved 2017/01/02.