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Details

Stereochemistry RACEMIC
Molecular Formula C8H11NO2
Molecular Weight 153.1784
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORFENEFRINE

SMILES

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

InChI

InChIKey=LRCXRAABFLIVAI-UHFFFAOYSA-N
InChI=1S/C8H11NO2/c9-5-8(11)6-2-1-3-7(10)4-6/h1-4,8,10-11H,5,9H2

HIDE SMILES / InChI

Molecular Formula C8H11NO2
Molecular Weight 153.1784
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: Description was created based on several sources, including http://www.kegg.jp/entry/D08286 and http://www.ncbi.nlm.nih.gov/pubmed/6351455

Norfenefrine or meta-octopamine, also known as 3,β-dihydroxyphenethylamine, is an adrenergic agent used as a sympathomimetic drug which is marketed in Europe, Japan, and Mexico. Along with its structural isomer p-octopamine and the tyramines, norfenefrine is a naturally occurring, endogenous trace amine and plays a role as a minor neurotransmitter in the brain. Norfenefrine controls blood pressure in acute hypotensive states eg pheochromocytomectomy, sympathectomy, poliomyelitis, spinal anesth, MI, septicemia, blood transfusion and drug reactions. Adjunct in treatment of cardiac arrest and hypotension.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Nevadral Retard

Approved Use

Indications: hypotension
PubMed

PubMed

TitleDatePubMed
Midodrine. A review of its pharmacological properties and therapeutic use in orthostatic hypotension and secondary hypotensive disorders.
1989 Nov
Effects of norepinephrine on the oxidative pentose phosphate pathway in the rat heart.
1992 Aug
In vivo alpha(1)-adrenergic lipolytic activity in subcutaneous adipose tissue of obese subjects.
2002 Apr
Early multiple organ failure after recurrent endotoxemia in the presence of vasoconstrictor-masked hypovolemia.
2003 Mar
Sympathetic regulation of glucose uptake by the alpha1-adrenoceptor in human obesity.
2004 Apr
Heat shock protein 72 and apoptosis indicate cardiac decompensation during early multiple organ failure in sheep.
2004 Jul
Roles of MMP-2/-9 in cardiac dysfunction during early multiple organ failure in an ovine animal model.
2005
[Efficacy and safety of a herbal drug containing hawthorn berries and D-camphor in hypotension and orthostatic circulatory disorders/results of a retrospective epidemiologic cohort study].
2005
Chiral separations on multichannel microfluidic chips.
2005 Dec
A new copper(I)-tetrahydrosalen-catalyzed asymmetric Henry reaction and its extension to the synthesis of (S)-norphenylephrine.
2007
A multichannel electrophoresis microchip platform for rapid chiral selector screening.
2008 May
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Can also be administered inramuscularly http://www.ncbi.nlm.nih.gov/pubmed/7197979
For the treatment of female stress incontinence 60 mg were given in slow-release tablets.
Route of Administration: Oral
In Vitro Use Guide
At 0.1 and 1 umol/l, norfenefrine caused contractions of the rabbit pulmonary artery strips
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:04:45 UTC 2023
Edited
by admin
on Fri Dec 15 16:04:45 UTC 2023
Record UNII
D2P3M6SRN5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORFENEFRINE
INN   MI   WHO-DD  
INN  
Official Name English
.ALPHA.-(AMINOMETHYL)-M-HYDROXYBENZYL ALCOHOL.
Common Name English
1-(M-HYDROXYPHENYL)-2-AMINOETHANOL
Systematic Name English
WV569 FREE BASE
Code English
.ALPHA.-(AMINOETHYL)-M-HYDROXYBENZYL ALCOHOL
Systematic Name English
NORPHENYLEPHRINE
Common Name English
M-HYDROXYPHENYLETHANOLAMINE
Systematic Name English
Norfenefrine [WHO-DD]
Common Name English
norfenefrine [INN]
Common Name English
.ALPHA.-(AMINOMETHYL)-3-HYDROXYBENZENE METHANOL
Common Name English
ETILEFRINE HYDROCHLORIDE IMPURITY C [EP IMPURITY]
Common Name English
(1RS)-2-amino-1-(3-hydroxyphenyl)ethanol
Systematic Name English
NORFENEFRINE [MI]
Common Name English
WV-569 FREE BASE
Code English
Classification Tree Code System Code
WHO-VATC QC01CA05
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
WHO-ATC C01CA05
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
NCI_THESAURUS C29709
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
Code System Code Type Description
CAS
536-21-0
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
ChEMBL
CHEMBL358040
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
SMS_ID
100000083615
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
MERCK INDEX
m8058
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
NORFENEFRINE
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
PUBCHEM
4538
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
RXCUI
31988
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID3048314
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
FDA UNII
D2P3M6SRN5
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
EVMPD
SUB09364MIG
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
NCI_THESAURUS
C84022
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
DRUG BANK
DB13378
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
INN
2140
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
DRUG CENTRAL
1966
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-626-8
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
MESH
C005310
Created by admin on Fri Dec 15 16:04:45 UTC 2023 , Edited by admin on Fri Dec 15 16:04:45 UTC 2023
PRIMARY
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SALT/SOLVATE -> PARENT
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CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY