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

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
[Influence of the beta-receptor blocker nifenalol on insulin secretion in normal subjects and diabetic patients (author's transl)].
1977 Feb
[Blood glucose concentration and insulin activity in serum after administration of the beta receptor blockader nifenalol-HC1 (INPEA). Studies in metabolically healthy people and diabetics].
1977 Jun
Effect of (+) INPEA, (+) sotalol and deoxysotalol on the in vitro production of prostaglandins E and F by the rat uterus.
1980 Apr
[Action of propranolol, nifenalol, and pindolol on the lipolytic effect of adrenaline in the rat epididymis].
1981 Apr
Sensitization by (+) Inpea of rat stomach strip contraction induced by PGE2 or pleural exudates.
1981 Jul
Potentiating effect of (+) INPEA on prostaglandin analogue evoked contractions of isolated rat uterus.
1983 Mar
Effects of bucumolol, nadolol and nifenalol on maximum upstroke velocity of action potential in guinea pig papillary muscles.
1986 Mar
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY