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Details

Stereochemistry RACEMIC
Molecular Formula C8H11NO3
Molecular Weight 169.1778
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORADRENALINE, (±)-

SMILES

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

InChI

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

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 ( + / - )

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

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 Fri Dec 15 15:21:42 UTC 2023
Edited
by admin
on Fri Dec 15 15:21:42 UTC 2023
Record UNII
K294OAI79V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORADRENALINE, (±)-
Common Name English
NORADRENALINE DL FORM
Common Name English
1,2-BENZENEDIOL, 4-(2-AMINO-1-HYDROXYETHYL)-, (±)-
Systematic Name English
NSC-294898
Code English
NOREPINEPHRINE DL-FORM [MI]
Common Name English
(±)-NORADRENALINE
Common Name English
NOREPINEPHRINE, DL-
Common Name English
DL-NOREPINEPHRINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C87053
Created by admin on Fri Dec 15 15:21:42 UTC 2023 , Edited by admin on Fri Dec 15 15:21:42 UTC 2023
Code System Code Type Description
DAILYMED
K294OAI79V
Created by admin on Fri Dec 15 15:21:42 UTC 2023 , Edited by admin on Fri Dec 15 15:21:42 UTC 2023
PRIMARY
RXCUI
1657875
Created by admin on Fri Dec 15 15:21:42 UTC 2023 , Edited by admin on Fri Dec 15 15:21:42 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
205-337-9
Created by admin on Fri Dec 15 15:21:42 UTC 2023 , Edited by admin on Fri Dec 15 15:21:42 UTC 2023
PRIMARY
PUBCHEM
951
Created by admin on Fri Dec 15 15:21:42 UTC 2023 , Edited by admin on Fri Dec 15 15:21:42 UTC 2023
PRIMARY
FDA UNII
K294OAI79V
Created by admin on Fri Dec 15 15:21:42 UTC 2023 , Edited by admin on Fri Dec 15 15:21:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID20858964
Created by admin on Fri Dec 15 15:21:42 UTC 2023 , Edited by admin on Fri Dec 15 15:21:42 UTC 2023
PRIMARY
NCI_THESAURUS
C62098
Created by admin on Fri Dec 15 15:21:42 UTC 2023 , Edited by admin on Fri Dec 15 15:21:42 UTC 2023
PRIMARY
CAS
138-65-8
Created by admin on Fri Dec 15 15:21:42 UTC 2023 , Edited by admin on Fri Dec 15 15:21:42 UTC 2023
PRIMARY
MERCK INDEX
m8054
Created by admin on Fri Dec 15 15:21:42 UTC 2023 , Edited by admin on Fri Dec 15 15:21:42 UTC 2023
PRIMARY Merck Index
NSC
294898
Created by admin on Fri Dec 15 15:21:42 UTC 2023 , Edited by admin on Fri Dec 15 15:21:42 UTC 2023
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY