NORFENEFRINE

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 Search

SMILES

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

Description
Sources: http://www.ndrugs.com/?s=norfenefrine
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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-1 171 Target ID: CHEMBL2094251 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D08286	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Female urinary stress incontinence 2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2568712	Primary		Preclinical	Unknown Approved Use Unknown
Hypotension 29 Sources: http://www.ncbi.nlm.nih.gov/pubmed/6618400	Primary		Approved 8583	Nevadral Retard Approved Use Indications: hypotension

Doses

Dose	Population	Adverse events
30 mg 3 times / day multiple, oral Studied dose Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3287737/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3287737/	Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (4.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/3287737/
90 mg single, oral Studied dose Dose: 90 mg Route: oral Route: single Dose: 90 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2053226/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2053226/	Sources: https://pubmed.ncbi.nlm.nih.gov/2053226/

AEs

AE	Significance	Dose	Population
Headache	4.3% Disc. AE	30 mg 3 times / day multiple, oral Studied dose Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3287737/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3287737/

PubMed

Title	Date	PubMed
A multichannel electrophoresis microchip platform for rapid chiral selector screening.	2008-05	18384040
A new copper(I)-tetrahydrosalen-catalyzed asymmetric Henry reaction and its extension to the synthesis of (S)-norphenylephrine.	2007	17068834
Chiral separations on multichannel microfluidic chips.	2005-12	16278920
Roles of MMP-2/-9 in cardiac dysfunction during early multiple organ failure in an ovine animal model.	2005	16308106
[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	16149711
Heat shock protein 72 and apoptosis indicate cardiac decompensation during early multiple organ failure in sheep.	2004-07	14985962
Sympathetic regulation of glucose uptake by the alpha1-adrenoceptor in human obesity.	2004-04	15090628
Early multiple organ failure after recurrent endotoxemia in the presence of vasoconstrictor-masked hypovolemia.	2003-03	12627003
In vivo alpha(1)-adrenergic lipolytic activity in subcutaneous adipose tissue of obese subjects.	2002-04	11907178
Effects of norepinephrine on the oxidative pentose phosphate pathway in the rat heart.	1992-08	1378361
Midodrine. A review of its pharmacological properties and therapeutic use in orthostatic hypotension and secondary hypotensive disorders.	1989-11	2480881

Patents

Sample Use Guides

In Vivo Use Guide

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

Name

Type

Language

NORFENEFRINE

Official Name

English

WV-569 FREE BASE

Preferred 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

Classification Tree Code System Code

WHO-VATC

QC01CA05