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Details

Stereochemistry RACEMIC
Molecular Formula C8H11NO3.ClH
Molecular Weight 205.639
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NOREPINEPHRINE HYDROCHLORIDE, (±)-

SMILES

Cl.NCC(O)C1=CC=C(O)C(O)=C1

InChI

InChIKey=FQTFHMSZCSUVEU-UHFFFAOYSA-N
InChI=1S/C8H11NO3.ClH/c9-4-8(12)5-1-2-6(10)7(11)3-5;/h1-3,8,10-12H,4,9H2;1H

HIDE SMILES / InChI

Molecular Formula C8H11NO3
Molecular Weight 169.1778
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Norepinephrine hydrochloride, (±)- (DL-Norepinephrine Hydrochloride) is a vasoconstrictor, cardiac stimulant, α- and β-sympathomimetic agent. DL-Norepinephrine hydrochloride is an adrenergic drug. Norepinephrine is an endogenous catecholamine that is the neurotransmitter at sympathetic postganglionic fibers. It has potent beta1- and alpha-stimulating effects. In contrast to epinephrine, norepinephrine has only minor effects on beta2 receptors. The clinical effects of norepinephrine administration are mainly increased cardiac index and increased vascular (systemic and pulmonary) resistance. Several adult studies have suggested that norepinephrine is useful in increasing SVR in patients with hyperdynamic or vasodilatory septic shock that is not responsive to dopamine or epinephrine. Additionally, it can augment coronary blood flow by increasing systemic diastolic pressure, at the expense of increasing afterload.

Approval Year

PubMed

PubMed

TitleDatePubMed
Strategies for enantioseparations of catecholamines and structurally related compounds by capillary zone electrophoresis using sulfated beta-cyclodextrins as chiral selectors.
2006-09
Beta 2-adrenoceptor-mediated positive dromotropic effects on atrioventricular node of dogs.
1992-01
Properties of [3H]bunazosin binding in rat kidney.
1988
[Analysis of the vascular reactivity of isolated and blood-perfused rabbit thoracic aortas with support rabbits].
1987-10

Sample Use Guides

In Vitro Use Guide
Curator's Comment: The functional significance of beta 2-adrenoceptors in atrioventricular (AV) nodal conduction was investigated by using canine isolated blood-perfused AV node preparations. The dose-response curve for dl-norepinephrine (0.03-1 nmol) was shifted to the right by 1.0 log unit with atenolol only. https://www.ncbi.nlm.nih.gov/pubmed/1346356
The biogenic amines DL-epinephrine, DL-norepinephrine, tyramine, DL-phenylethanolamine, 2-phenylethylamine, and dopamine, applied at concentrations of 10(-8) or 10(-4) M, do not change the MFF (maximum following frequency, MFF).
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:52:03 GMT 2025
Edited
by admin
on Mon Mar 31 21:52:03 GMT 2025
Record UNII
7W3827X38V
Record Status Validated (UNII)
Record Version
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Name Type Language
NOREPINEPHRINE HYDROCHLORIDE, (±)-
Common Name English
D09794
Preferred Name English
4-(2-AMINO-1-HYDROXYETHYL)BENZENE-1,2-DIOL HYDROCHLORIDE (1:1)
Systematic Name English
NSC-7930
Code English
J277.870J
Code English
(±)-NORADRENALINE HYDROCHLORIDE
Common Name English
(±)-1-(3,4-DIHYDROXYPHENYL)-2-AMINOETHANOL HYDROCHLORIDE
Systematic Name English
DL-ARTERENOL HYDROCHLORIDE
Common Name English
DL-NOREPINEPHRINE HYDROCHLORIDE
Common Name English
1,2-BENZENEDIOL, 4-(2-AMINO-1-HYDROXYETHYL)-, HYDROCHLORIDE, (±)-
Systematic Name English
NORADRENALINE HYDROCHLORIDE, (±)-
Common Name English
(±)-4-(2-AMINO-1-HYDROXYETHYL)-1,2-BENZENEDIOL HYDROCHLORIDE
Systematic Name English
4-(2-AMINO-1-HYDROXYETHYL)-1,2-BENZENEDIOL HYDROCHLORIDE (1:1)
Systematic Name English
1,2-BENZENEDIOL, 4-(2-AMINO-1-HYDROXYETHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
NOREPINEPHRINE HYDROCHLORIDE [JAN]
Common Name English
(±)-NOREPINEPHRINE HYDROCHLORIDE
Common Name English
BENZYL ALCOHOL, .ALPHA.-(AMINOMETHYL)-3,4-DIHYDROXY-, HYDROCHLORIDE, (±)-
Systematic Name English
1,2-BENZENEDIOL, 4-(2-AMINO-1-HYDROXYETHYL)-, HYDROCHLORIDE
Systematic Name English
NOREPINEPHRINE HYDROCHLORIDE [JP]
Common Name English
Code System Code Type Description
CAS
55-27-6
Created by admin on Mon Mar 31 21:52:03 GMT 2025 , Edited by admin on Mon Mar 31 21:52:03 GMT 2025
PRIMARY
FDA UNII
7W3827X38V
Created by admin on Mon Mar 31 21:52:03 GMT 2025 , Edited by admin on Mon Mar 31 21:52:03 GMT 2025
PRIMARY
NSC
7930
Created by admin on Mon Mar 31 21:52:03 GMT 2025 , Edited by admin on Mon Mar 31 21:52:03 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-229-8
Created by admin on Mon Mar 31 21:52:03 GMT 2025 , Edited by admin on Mon Mar 31 21:52:03 GMT 2025
PRIMARY
PUBCHEM
5923
Created by admin on Mon Mar 31 21:52:03 GMT 2025 , Edited by admin on Mon Mar 31 21:52:03 GMT 2025
PRIMARY