U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11NO3
Molecular Weight 169.1778
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NOREPINEPHRINE

SMILES

NC[C@H](O)C1=CC(O)=C(O)C=C1

InChI

InChIKey=SFLSHLFXELFNJZ-QMMMGPOBSA-N
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

HIDE SMILES / InChI

Molecular Formula C8H11NO3
Molecular Weight 169.1778
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/?term=17214596; http://www.ncbi.nlm.nih.gov/pubmed/?term=18368304

Norepinephrine (l-arterenol/Levarterenol or l-norepinephrine) is a sympathomimetic catecholamine with multiple roles including as a hormone and a neurotransmitter. As a stress hormone, norepinephrine affects parts of the brain where attention and responding actions are controlled. Along with epinephrine, norepinephrine also underlies the fight-or-flight response, directly increasing heart rate, triggering the release of glucose from energy stores, and increasing blood flow to skeletal muscle. Norepinephrine can also suppress neuroinflammation when released diffusely in the brain from the locus ceruleus. Norepinephrine may be used for blood pressure control in certain acute hypotensive states (e.g., pheochromocytomectomy, sympathectomy, poliomyelitis, spinal anesthesia, myocardial infarction, septicemia, blood transfusion, and drug reactions) and as an adjunct in the treatment of cardiac arrest and profound hypotension. Norepinephrine performs its action by being released into the synaptic cleft, where it acts on adrenergic receptors, followed by the signal termination, either by degradation of norepinephrine, or by uptake by surrounding cells. Prolonged administration of any potent vasopressor may result in plasma volume depletion which should be continuously corrected by appropriate fluid and electrolyte replacement therapy.If plasma volumes are not corrected, hypotension may recur when Norepinephrine is discontinued, or blood pressure may be maintained at the risk of severe peripheral and visceral vasoconstriction (e.g., decreased renal perfusion)with diminution in blood flow and tissue perfusion with subsequent tissue hypoxia and lactic acidosis and possible ischemic injury. Gangrene of extremities has been rarely reported. Overdoses or conventional doses in hypersensitive persons (e.g., hyperthyroid patients) cause severe hypertension with violent headache, photophobia, stabbing retrosternal pain, pallor, intense sweating, and vomiting.

CNS Activity

Curator's Comment: In the brain, norepinephrine is produced in closely packed brain cell neurons or nuclei that are small yet exert powerful effects on other brain areas.

Originator

Sources: http://www.businesswire.com/news/home/20140218006891/en/Chelsea-Therapeutics-Announces-FDA-Accelerated-Approval-NORTHERA%E2%84%A2Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales (1932), 111, 884-6.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LEVOPHED

Approved Use

INDICATIONS: ​Temporary relief of sleep, emotional, nervous or memory disorders.

Launch Date

1950
Primary
LEVOPHED

Approved Use

INDICATIONS: ​Temporary relief of sleep, emotional, nervous or memory disorders.

Launch Date

1950
Primary
LEVOPHED

Approved Use

INDICATIONS: ​Temporary relief of sleep, emotional, nervous or memory disorders.

Launch Date

1950
Primary
NORTHERA

Approved Use

Indicated for the treatment of orthostatic dizziness, lightheadedness, or the “feeling that you are about to black out” in adult patients with symptomatic neurogenic orthostatic hypotension (NOH) caused by primary autonomic failure [Parkinson's disease (PD), multiple system atrophy and pure autonomic failure], dopamine beta-hydroxylase deficiency, and non-diabetic autonomic neuropathy.

Launch Date

2014
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.4 min
unknown, intravenous
NOREPINEPHRINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
75%
unknown, intravenous
NOREPINEPHRINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.6 ug/kg/min single, intravenous
Highest studied dose
Dose: 0.6 ug/kg/min
Route: intravenous
Route: single
Dose: 0.6 ug/kg/min
Sources:
unhealthy, mean 65.5 years
Health Status: unhealthy
Age Group: mean 65.5 years
Sex: M+F
Sources:
Other AEs: Mean arterial pressure high...
Other AEs:
Mean arterial pressure high (7.2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Mean arterial pressure high 7.2%
0.6 ug/kg/min single, intravenous
Highest studied dose
Dose: 0.6 ug/kg/min
Route: intravenous
Route: single
Dose: 0.6 ug/kg/min
Sources:
unhealthy, mean 65.5 years
Health Status: unhealthy
Age Group: mean 65.5 years
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Droxidopa, an oral norepinephrine precursor, improves hemodynamic and renal alterations of portal hypertensive rats.
2012-11
L-Dihydroxyphenylserine (L-DOPS): a norepinephrine prodrug.
2007-01-12
Involvement of noradrenaline transporters in S-nitrosocysteine-stimulated noradrenaline release from rat brain slices: existence of functional Na(+)-independent transporter activity.
2001-04
Effect of dexmedetomidine on the release of [3H]-noradrenaline from rat kidney cortex slices: characterization of alpha2-adrenoceptor.
2001-04
Estrogen modulates norepinephrine-induced accumulation of adenosine cyclic monophosphate in a subpopulation of immortalized luteinizing hormone-releasing hormone secreting neurons from the mouse hypothalamus.
2001-01-26
Upregulation of immunoreactive angiotensin II release and angiotensinogen mRNA expression by high-frequency preganglionic stimulation at the canine cardiac sympathetic ganglia.
2001-01-19
Nitric oxide synthase activity in peripheral polymorphonuclear leukocytes in patients with chronic congestive heart failure.
2001-01-15
A proposed pathological model in the hippocampus of subjects with schizophrenia.
2001-01-12
Effect of amlodipine on cardiopulmonary performance in volunteers.
2001-01-12
The effects of phosphodiesterase inhibition on cyclic GMP and cyclic AMP accumulation in the hippocampus of the rat.
2001-01-12
Changes in sensitivity of cholinoceptors and adrenoceptors during transhemispheric cortical reorganisation in rat SmI.
2001-01-12
Characterization of extracellular dopamine clearance in the medial prefrontal cortex: role of monoamine uptake and monoamine oxidase inhibition.
2001-01-01
Potentiation by aminoethylisothiourea of the extra-cellular Ca(2+) component of norepinephrine-induced contraction in rat femoral arteries.
2001-01-01
Dietary restriction in pregnant rats causes gender-related hypertension and vascular dysfunction in offspring.
2001-01-01
alpha(1B) adrenergic receptors in gonadotrophin-releasing hormone neurones: relation to Transport-P.
2001-01
Chronic treatment with reboxetine by osmotic pumps facilitates its effect on extracellular noradrenaline and may desensitize alpha(2)-adrenoceptors in the prefrontal cortex.
2001-01
Simvastatin inhibits noradrenaline-induced hypertrophy of cultured neonatal rat cardiomyocytes.
2001-01
Beta-adrenoceptor stimulation attenuates the hypertrophic effect of alpha-adrenoceptor stimulation in adult rat ventricular cardiomyocytes.
2001-01
Ambulatory norepinephrine treatment of severe autonomic orthostatic hypotension.
2001-01
Contrasting clinical properties and exercise responses in obese and lean hypertensive patients.
2001-01
Projections and pathways of VIP- and nNOS-containing airway neurons in ferret trachea.
2001-01
Arterial remodeling in chronic sinoaortic-denervated rats.
2001-01
Reversal of Haemorrhagic Shock in Rats by Tetrahydroaminoacridine.
2001-01
Modulatory effect of protein kinase C activator on contractility of rat vas deferens.
2001-01
Hormonal responses to exercise in chronic fatigue syndrome.
2001-01
Monoamine compounds in cerebrospinal fluid of healthy subjects punctured without preceding strict bed rest: a pilot study.
2001-01
Levels of circulating CD8(+) T lymphocytes, natural killer cells, and eosinophils increase upon acute psychosocial stress in patients with atopic dermatitis.
2001-01
Acute gastrointestinal manifestations associated with use of crack.
2001-01
N-methyl-D-aspartate receptors mediating hippocampal noradrenaline and striatal dopamine release display differential sensitivity to quinolinic acid, the HIV-1 envelope protein gp120, external pH and protein kinase C inhibition.
2001-01
Differences in central noradrenergic and behavioural responses of Maudsley non-reactive and Maudsley reactive inbred rats on exposure to an aversive novel environment.
2001-01
Autoregulation of cerebral blood flow in patients resuscitated from cardiac arrest.
2001-01
Antagonism of Rho-kinase stimulates rat penile erection via a nitric oxide-independent pathway.
2001-01
Efferent arteriole tubuloglomerular feedback in the renal nephron.
2001-01
Alteration of catecholamines in pheochromocytoma (PC12) cells in vitro by the metabolites of chlorotriazine herbicide.
2001-01
Effects of human pregnancy on cardiac autonomic function above and below the ventilatory threshold.
2001-01
Ventricular activation during sympathetic imbalance and its computational reconstruction.
2001-01
Dorsomedial medulla is more susceptible than rostral ventrolateral medulla to hypoxic insult in cats.
2001-01
Interaction of gender and exercise training: vasomotor reactivity of porcine skeletal muscle arteries.
2001-01
Catecholamine responses to alpha-adrenergic blockade during exercise in women acutely exposed to altitude.
2001-01
Alteration of humoral and peripheral vascular responses during graded exercise in heart failure.
2001-01
Effects of PKC isozyme inhibitors on constrictor responses in the feline pulmonary vascular bed.
2001-01
Neurotransmitter release from bovine adrenal chromaffin cells is modulated by capacitative Ca(2+)entry driven by depleted internal Ca(2+)stores.
2001-01
Reactive oxygen species mediate alpha-adrenergic receptor-stimulated hypertrophy in adult rat ventricular myocytes.
2001-01
Catecholaminergic regulation of Na-K-Cl cotransport in pigmented ciliary epithelium: differences between PE and NPE.
2001-01
The antidepressant-sensitive dopamine transporter in Drosophila melanogaster: a primordial carrier for catecholamines.
2001-01
Neonatal catecholamine levels and neurodevelopmental outcome: a cohort study.
2001-01
In vitro reconstitution of fish melanophore pigment aggregation.
2001-01
Differential alterations in cardiac adrenergic signaling in chronic hypoxia or norepinephrine infusion.
2001-01
A single bout of exercise induces beta-adrenergic desensitization in human adipose tissue.
2001-01
Substance P and NPY differentially potentiate ATP and adrenergic stimulated vasopressin and oxytocin release.
2001-01
Patents

Sample Use Guides

The recommended starting dose is 100 mg, taken orally three times daily: upon arising in the morning, at midday, and in the late afternoon at least 3 hours prior to bedtime (to reduce the potential for supine hypertension during sleep). Administer consistently, either with food or without food. Take capsule whole. Titrate to symptomatic response, in increments of 100 mg three times daily every 2448 hours up to a maximum dose of 600 mg three times daily (i.e., a maximum total daily dose of 1800 mg).
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:49:14 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:14 GMT 2025
Record UNII
X4W3ENH1CV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORADRENALINE
MART.  
Preferred Name English
NOREPINEPHRINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
NORADRENALINE [MART.]
Common Name English
NOREPINEPHRINE [USP IMPURITY]
Common Name English
NOREPINEPHRINE [MI]
Common Name English
(-)-NORADRENALINE
Common Name English
ADRENALINE IMPURITY B [EP IMPURITY]
Common Name English
NSC-757246
Code English
LEVARTERENOL
Common Name English
(-)-.ALPHA.-(AMINOMETHYL)-3,4-DIHYDROXYBENZYL ALCOHOL
Systematic Name English
(1R)-2-AMINO-1-(3,4-DIHYDROXYPHENYL)ETHANOL
Systematic Name English
Norepinephrine [WHO-DD]
Common Name English
NORADRENALINE [JAN]
Common Name English
norepinephrine [INN]
Common Name English
1,2-BENZENEDIOL, 4-(2-AMINO-1-HYDROXYETHYL)-, (R)-(R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE
Common Name English
NOR ADRENALIN
Brand Name English
ADRENALINE TARTRATE IMPURITY B [EP IMPURITY]
Common Name English
NOREPINEPHRINE [HSDB]
Common Name English
NOREPINEPHRINE [VANDF]
Common Name English
Classification Tree Code System Code
LOINC 13782-8
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
LOINC 44837-3
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LOINC 49552-3
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LOINC 14852-8
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WHO-VATC QC01CA03
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
LOINC 2666-6
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LOINC 27221-1
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LOINC 16111-7
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LOINC 44341-6
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LOINC 24523-3
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LOINC 13735-6
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LOINC 32549-8
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LOINC 2668-2
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NDF-RT N0000007715
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LOINC 25963-0
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LOINC 2667-4
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LOINC 27977-8
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LOINC 14854-4
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LOINC 14853-6
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WHO-ATC C01CA03
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
NDF-RT N0000175570
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
Code System Code Type Description
IUPHAR
505
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL1437
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
FDA UNII
X4W3ENH1CV
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
MESH
D009638
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID5023378
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
DAILYMED
X4W3ENH1CV
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
CHEBI
33569
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
CHEBI
18357
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
SMS_ID
100000083594
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
EVMPD
SUB09360MIG
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
HSDB
7772
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
WIKIPEDIA
Norepinephrine (medication)
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
NSC
757246
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
INN
33
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
DRUG CENTRAL
1960
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PRIMARY
CAS
51-41-2
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-096-6
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
WIKIPEDIA
NOREPINEPHRINE
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
DRUG BANK
DB00368
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
MERCK INDEX
m8054
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C2321
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
PUBCHEM
439260
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
LACTMED
Norepinephrine
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY
RXCUI
7512
Created by admin on Mon Mar 31 17:49:14 GMT 2025 , Edited by admin on Mon Mar 31 17:49:14 GMT 2025
PRIMARY RxNorm
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Ki
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