NIFENALOL HYDROCHLORIDE

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 Search

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

Molecular Formula	C11H16N2O3
Molecular Weight	224.2563
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: Karow, A.M. et al. (1913) Progress in Drug Research, page 109, retrieved from: https://books.google.ru/books?id=4Jr5BwAAQBAJ | https://www.ncbi.nlm.nih.gov/pubmed/6688273 | https://www.ncbi.nlm.nih.gov/pubmed/6716

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor beta 89 Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6688273 \| https://www.ncbi.nlm.nih.gov/pubmed/577165 \| https://www.ncbi.nlm.nih.gov/pubmed/578017 \| Karow, A.M. et al. (1913) Progress in Drug Research, page 109, retrieved from: https://books.google.ru/books?id=4Jr5BwAAQBAJ	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Coronary artery disease 48 Sources: Karow, A.M. et al. (1913) Progress in Drug Research, page 109, retrieved from: https://books.google.ru/books?id=4Jr5BwAAQBAJ	Primary		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Arrhythmogenic effect of beta-adrenoceptor-blocking drugs in Purkinje fibres of guinea-pig hearts.	1996-01-01	8896710
Resveratrol activity on guinea pig isolated trachea from normal and albumin-sensitized animals.	1988-12	2907791
Effects of bucumolol, nadolol and nifenalol on maximum upstroke velocity of action potential in guinea pig papillary muscles.	1986-03	2872598
[Iatrogenic dermatoses caused by beta-blocking drugs].	1983-11-01	6143722
Effects of 1-(4-nitrophenyl)-2-isopropylaminoethanol (INPEA) and propranolol and their dextro-isomers on hemodynamic and metabolic responses to isoproterenol in dogs.	1983-08	6688273
Potentiating effect of (+) INPEA on prostaglandin analogue evoked contractions of isolated rat uterus.	1983-03	6688239
Sensitization by (+) Inpea of rat stomach strip contraction induced by PGE2 or pleural exudates.	1981-07	6944701
[Action of propranolol, nifenalol, and pindolol on the lipolytic effect of adrenaline in the rat epididymis].	1981-04	6895689
Effect of (+) INPEA, (+) sotalol and deoxysotalol on the in vitro production of prostaglandins E and F by the rat uterus.	1980-04	6893041
Differentiation of beta-adrenoceptors in right atrium, diaphragm and adipose tissue of the rat, using stereoisomers of propranolol, alprenolol, nifenalol and practolol.	1977-07-01	196150
[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].	1977-06	578017
[Influence of the beta-receptor blocker nifenalol on insulin secretion in normal subjects and diabetic patients (author's transl)].	1977-02	577165
Cardiac action of carazolol and methypranol in comparison with other beta-receptor blockers.	1977	18157
Tremorine-oxotremorine-induced tremor, hypothermia and analgesia, and physostigmine toxicity, in mice after pretreatment with beta-adrenoceptor antagonists.	1976-04	6716
Blockade of epinephrine- and ouabain-induced cardiac arrhythmias in the dog heart-lung preparation.	1966-05	4380269

Patents

Sample Use Guides

In Vivo Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:15:59 GMT 2025` Edited by `admin` on `Mon Mar 31 19:15:59 GMT 2025`
Record UNII	2KMT7J8EZC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NIFENALOL HYDROCHLORIDE

Common Name

English

(±)-INPEA HYDROCHLORIDE

Preferred 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

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