Norepinephrine Chemical Properties

Melting point:

220-230°C

alpha 

D25 -37.3° (c = 5 in water with 1 equiv HCl)

Boiling point:

298.46°C (rough estimate)

Density 

1.2435 (rough estimate)

refractive index 

1.5100 (estimate)

storage temp. 

2-8°C

solubility 

Aqueous Acid (Slightly), DMSO (Slightly)

pka

8.64(at 25℃)

form 

crystalline

color 

off-white to tan

optical activity

D +37.426 (c 5, H2O+HCl)L -37.1325 (c 5, H2O+HCl)

Water Solubility 

Soluble in alkali and dilute hydrochloric acid. Slightly soluble in water, ethanol and diethyl ether.

Sensitive 

Air & Light Sensitive

Merck 

14,6695

BRN 

4231961

Stability:

Stable, but may be light-sensitive. Incompatible with acids, bases, oxidizing agents. Store at -20℃.

CAS DataBase Reference

51-41-2(CAS DataBase Reference)

EPA Substance Registry System

Norepinephrine (51-41-2)

Safety Information

Hazard Codes 

T+,C,F

Risk Statements 

26/27/28-34-11-28

Safety Statements 

28-36/37-45-36/37/39-26-16-20

RIDADR 

UN 2811 6.1/PG 2

WGK Germany 

3

RTECS 

DN5950000

F 

8-10-23

HazardClass 

6.1

PackingGroup 

II

HS Code 

29225090

Hazardous Substances Data

51-41-2(Hazardous Substances Data)

Toxicity

dni-hmn:oth 5800 nmol/L CNREA8 40,1414,80

MSDS

• Language:English Provider:(R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Norepinephrine Usage And Synthesis

Chemical Properties

solid

Uses

Vascular active drug resistance to shock

Uses

An adrenergic neurotransmitter.

Uses

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.

Definition

ChEBI: The R-enantiomer of noradrenaline.

brand name

Levophed (Hospira);Noradrec;Xylotox.

World Health Organization (WHO)

Vasoconstrictor agents have been in use for many years to prolong duration of action of local anaesthetics, particularly in dentistry. Combination products containing epinephrine or levarterenol in concentrations of 1:80,000 or less remain widely available. See also WHO comment for epinephrine.

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.

General Description

Norepinephrine (NE, Levophed) differs from DA onlyby addition of a 1-OH substituent (β-OH-DA) and from Eonly by lacking the N-methyl group. Like DA, it is polar andrapidly metabolized by both COMT and MAO, resulting inpoor oral bioavailability and short DOA (1 or 2 minutes evenwhen given intravenously). It is a stimulant of α1-, α2-, andβ1-adrenoceptors (notice that lacking the N-methyl group resultsin lacking β2- and β3-activity). It is used to counteractvarious hypotensive crises, because its α-activity raisesblood pressure and as an adjunct treatment in cardiac arrestbecause its β-activity stimulates the heart. It has limitedclinical application caused by the nonselective nature of itsactivities.

Hazard

May cause local tissue necrosis, headache, bradycardia, hypertension; poison; teratogen; mutagen.

Biochem/physiol Actions

Adrenergic neurotransmitter

Pharmacology

Norepinephrine is the primary neurotransmitter produced and released by adrenergic neurons, and in literature it is also described as and called () noradrenaline or levarterenol. This vasopressor catecholamine reduces both the resistance and capacity of blood vessels by stimulating α-adrenoreceptors and having a direct cardiostimulatory effect, which is accomplished by activation of β1-adrenoreceptors. Norepinephrine exhibits significantly less activity than epinephrine as a drug for widening blood vessels through the activation of β2-adrenoreceptors. Elevation of both stylistic and diastolic blood pressure is a typical reaction to intravenous introduction of norepinephrine.

Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. A sympathomimetic vasopressor. When heated to decomposition it emits toxic fumes of NOx.

Synthesis

Norepinephrine, L-1-(3,4-dihydroxyphenyl)-2-aminoethanol (11.1.4), is synthesized by two methods starting from 3,4-dihydroxybenzaldehyde. According to the first method, the indicated aldehyde is transformed into the cyanohydrin (11.1.3) by reaction with hydrogen cyanide, which is then reduced into norepinephrine (11.1.5).

The second method consists of the condensation of diacetate of the same aldehyde with nitromethane, which forms (3,4-diacetoxyphenyl)-2-nitroethanol (11.1.5). Then the nitro group is reduced and the product (11.1.6) is hydrolyzed into the desired norepinephrine (11.1.4) [4,9,13,14].

Purification Methods

Recrystallise adrenor from EtOH and store it in the dark under N2. [pKa, Lewis Brit J Pharmacol Chemother 9 488 1954, UV: Bergstr.m et al. Acta Physiol Scand 20 101 1950, Fluorescence: Bowman et al. Science NY 122 32 1955, Tullar J Am Chem Soc 70 2067 1948.] The L-tartrate salt monohydrate has m 102-104.5o, [] D -11o (c 1.6, H2O), after recrystallisation from H2O or EtOH. [Beilstein 13 III 2382.]

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