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Details

Stereochemistry RACEMIC
Molecular Formula C11H16N2O3
Molecular Weight 224.2563
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIFENALOL

SMILES

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

InChI

InChIKey=UAORFCGRZIGNCI-UHFFFAOYSA-N
InChI=1S/C11H16N2O3/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

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
[Action of propranolol, nifenalol, and pindolol on the lipolytic effect of adrenaline in the rat epididymis].
1981 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
Potentiating effect of (+) INPEA on prostaglandin analogue evoked contractions of isolated rat uterus.
1983 Mar
[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
INN   MART.   MI   WHO-DD  
INN  
Official Name English
nifenalol [INN]
Common Name English
1-(4-NITROPHENYL)-2-(ISOPROPYLAMINO)ETHANOL
Systematic Name English
N-ISOPROPYL-1-(P-NITROPHENYL)ETHANOLAMINE
Common Name English
BENZENEMETHANOL, .ALPHA.-(((1-METHYLETHYL)AMINO)METHYL)-4-NITRO-, (±)-
Systematic Name English
DL-.ALPHA.-((ISOPROPYLAMINO)METHYL)-P-NITROBENZYL ALCOHOL
Common Name English
2-(P-NITROPHENYL)-1-ISOPROPYLAMINO-2-ETHANOL
Common Name English
(±)-.ALPHA.-((ISOPROPYLAMINO)METHYL)-P-NITROBENZYL ALCOHOL
Common Name English
Nifenalol [WHO-DD]
Common Name English
BENZENEMETHANOL, .ALPHA.-(((1-METHYLETHYL)AMINO)METHYL)-4-NITRO-
Systematic Name English
DL-INPEA
Code English
(±)-INPEA
Common Name English
(±)-NIFENALOL
Common Name English
(±)-1-(P-NITROPHENYL)-2-ISOPROPYLAMINOETHANOL
Common Name English
DL-N-ISOPROPYL-P-NITROPHENYLETHANOLAMINE
Common Name English
1-(P-NITROPHENYL)-1-HYDROXY-2-(ISOPROPYLAMINO)ETHANE
Common Name English
NIFENALOL [MART.]
Common Name English
(±)-2-ISOPROPYLAMINO-1-(4-NITROPHENYL)ETHANOL
Systematic Name English
NIFENALOL [MI]
Common Name English
BENZYL ALCOHOL, .ALPHA.-((ISOPROPYLAMINO)METHYL)-P-NITRO-
Common Name English
BENZYL ALCOHOL, .ALPHA.-((ISOPROPYLAMINO)METHYL)-P-NITRO-, (±)-
Common Name English
RACEMIC NIFENALOL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
Code System Code Type Description
FDA UNII
D1DE63830P
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MERCK INDEX
m1218
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PRIMARY Merck Index
EVMPD
SUB09255MIG
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CAS
7413-36-7
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SMS_ID
100000084402
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PUBCHEM
6317
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MESH
C100250
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NCI_THESAURUS
C76554
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DRUG CENTRAL
3380
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ECHA (EC/EINECS)
231-023-6
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EPA CompTox
DTXSID9048693
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WIKIPEDIA
Nifenalol
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
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ChEMBL
CHEMBL127349
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
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INN
2734
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