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Details

Stereochemistry RACEMIC
Molecular Formula C11H16N2O3.ClH
Molecular Weight 260.717
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIFENALOL HYDROCHLORIDE

SMILES

Cl.CC(C)NCC(O)C1=CC=C(C=C1)[N+]([O-])=O

InChI

InChIKey=STGOXRVTUNXXLQ-UHFFFAOYSA-N
InChI=1S/C11H16N2O3.ClH/c1-8(2)12-7-11(14)9-3-5-10(6-4-9)13(15)16;/h3-6,8,11-12,14H,7H2,1-2H3;1H

HIDE SMILES / InChI
Nifenalol is the beta-receptor antagonist. It has optical isomers. The racemic mixture and the levo-isomer are active in antagonizing beta-receptors, but the dextro-isomer is inactive. The levo-isomer seems to be about twice as active in blocking beta-receptors as the racemate. Nifenalol is virtually devoid of local anesthetic properties in contrast to procaine, propranolol, and butidrine. Nifenalol exacerbated the fighting behavior in male mice by foot-shock. Nifenalol has been studied in patients with coronary artery disease. It afforded the coronary patient good protection against angina and ischemic changes in the EKG. It was further noted that nifenalol had no antiarrhythmic action and that it was devoid of evident side effects. Nifenalol possessed weak action against tremorine and oxotremorine induced tremor.

Approval Year

PubMed

PubMed

TitleDatePubMed
Blockade of epinephrine- and ouabain-induced cardiac arrhythmias in the dog heart-lung preparation.
1966 May
Tremorine-oxotremorine-induced tremor, hypothermia and analgesia, and physostigmine toxicity, in mice after pretreatment with beta-adrenoceptor antagonists.
1976 Apr
Cardiac action of carazolol and methypranol in comparison with other beta-receptor blockers.
1977
[Influence of the beta-receptor blocker nifenalol on insulin secretion in normal subjects and diabetic patients (author's transl)].
1977 Feb
Differentiation of beta-adrenoceptors in right atrium, diaphragm and adipose tissue of the rat, using stereoisomers of propranolol, alprenolol, nifenalol and practolol.
1977 Jul 1
Effect of (+) INPEA, (+) sotalol and deoxysotalol on the in vitro production of prostaglandins E and F by the rat uterus.
1980 Apr
Effects of 1-(4-nitrophenyl)-2-isopropylaminoethanol (INPEA) and propranolol and their dextro-isomers on hemodynamic and metabolic responses to isoproterenol in dogs.
1983 Aug
[Iatrogenic dermatoses caused by beta-blocking drugs].
1983 Nov-Dec
Effects of bucumolol, nadolol and nifenalol on maximum upstroke velocity of action potential in guinea pig papillary muscles.
1986 Mar
Resveratrol activity on guinea pig isolated trachea from normal and albumin-sensitized animals.
1988 Dec
Arrhythmogenic effect of beta-adrenoceptor-blocking drugs in Purkinje fibres of guinea-pig hearts.
1996 Jan-Feb
Patents

Sample Use Guides

Dog: 5 or 15 mg/kg
Route of Administration: Intravenous
In Vitro Use Guide
The effects of nifenalol (NIF) on contractile forces and on action potentials (APs) were investigated in isolated guinea pig atrial and papillary muscles, respectively. Log 1/ED40 values for the negative inotropic effects of this drug was 0.74 mmol/l in this order. NIF (0.2 mmol/l) produced about 20% reduction of Vmax at 1 Hz.
Name Type Language
NIFENALOL HYDROCHLORIDE
MI   WHO-DD  
Common Name English
DL-N-ISOPROPYL-P-NITROPHENYLETHANOLAMINE HYDROCHLORIDE
Common Name English
(±)-1-(4-NITROPHENYL)-2-ISOPROPYLAMINOETHANOL HYDROCHLORIDE
Systematic Name English
BENZENEMETHANOL, .ALPHA.-(((1-METHYLETHYL)AMINO)METHYL)-4-NITRO-, MONOHYDROCHLORIDE, (±)-
Common Name English
1-(4-NITROPHENYL)-2-(ISOPROPYLAMINO)ETHANOL HYDROCHLORIDE
Systematic Name English
(±)-NIFENALOL HYDROCHLORIDE
Common Name English
(±)-1-(4-NITROPHENYL)-2-(ISOPROPYLAMINO)ETHANOL HYDROCHLORIDE
Systematic Name English
INPEA
Common Name English
1-(P-NITROPHENYL)-2-(ISOPROPYLAMINO)ETHANOL HYDROCHLORIDE
Common Name English
BENZYL ALCOHOL, .ALPHA.-((ISOPROPYLAMINO)METHYL)-P-NITRO-, MONOHYDROCHLORIDE, (±)-
Common Name English
BENZENEMETHANOL, .ALPHA.-(((1-METHYLETHYL)AMINO)METHYL)-4-NITRO-, MONOHYDROCHLORIDE
Systematic Name English
(±)-INPEA HYDROCHLORIDE
Common Name English
1-(4-NITROPHENYL)-1-HYDROXY-2-ISOPROPYLAMINOETHANE HYDROCHLORIDE
Systematic Name English
NIFENALOL HYDROCHLORIDE [MI]
Common Name English
N-ISOPROPYL-P-NITROPHENYLETHANOLAMINE HYDROCHLORIDE
Common Name English
INPEA HYDROCHLORIDE
Common Name English
NIFENALOL HCL
Common Name English
Nifenalol hydrochloride [WHO-DD]
Common Name English
DL-INPEA HYDROCHLORIDE
Common Name English
DL-2-(ISOPROPYLAMINO)-1-(P-NITROPHENYL)ETHANOL HYDROCHLORIDE
Common Name English
Code System Code Type Description
FDA UNII
2KMT7J8EZC
Created by admin on Fri Dec 15 18:35:27 GMT 2023 , Edited by admin on Fri Dec 15 18:35:27 GMT 2023
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SMS_ID
100000085718
Created by admin on Fri Dec 15 18:35:27 GMT 2023 , Edited by admin on Fri Dec 15 18:35:27 GMT 2023
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EPA CompTox
DTXSID90972520
Created by admin on Fri Dec 15 18:35:27 GMT 2023 , Edited by admin on Fri Dec 15 18:35:27 GMT 2023
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CAS
5704-60-9
Created by admin on Fri Dec 15 18:35:27 GMT 2023 , Edited by admin on Fri Dec 15 18:35:27 GMT 2023
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EVMPD
SUB03433MIG
Created by admin on Fri Dec 15 18:35:27 GMT 2023 , Edited by admin on Fri Dec 15 18:35:27 GMT 2023
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MERCK INDEX
m1218
Created by admin on Fri Dec 15 18:35:27 GMT 2023 , Edited by admin on Fri Dec 15 18:35:27 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
227-194-1
Created by admin on Fri Dec 15 18:35:27 GMT 2023 , Edited by admin on Fri Dec 15 18:35:27 GMT 2023
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PUBCHEM
6316
Created by admin on Fri Dec 15 18:35:27 GMT 2023 , Edited by admin on Fri Dec 15 18:35:27 GMT 2023
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