ETAFEDRINE

US Previously Marketed

First approved in 1942

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H19NO
Molecular Weight	193.2854
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(C)[C@@H](C)[C@H](O)C1=CC=CC=C1

InChI

InChIKey=IRVLBORJKFZWMI-JQWIXIFHSA-N

InChI=1S/C12H19NO/c1-4-13(3)10(2)12(14)11-8-6-5-7-9-11/h5-10,12,14H,4H2,1-3H3/t10-,12-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C12H19NO
Molecular Weight	193.2854
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/793781 | https://www.ncbi.nlm.nih.gov/pubmed/4039586 | https://www.ncbi.nlm.nih.gov/pubmed/326265 | http://bodyandhealth.canada.com/drug/getdrug/dalmacol | http://home.intekom.com/pharm/adcock/neth-exp.html | http://www.tabletwise.com/southafrica/nethaprin-dospan-tablet

Etafedrine, a sympathomimetic agent that acts on the sympathetic receptors of the bronchial tree relaxing spasm in a manner similar to that of ephedrine, is a bronchodilator and a selective β2-adrenoreceptor agonist. Contraction of the guinea pig tracheal chain by acetylcholine or histamine was antagonized by etafedrine with a higher potency then ephedrine but with a lower potency than epinephrine (adrenaline). Etafedrine did not increase heart rate or force of contraction in guinea pig atria. Unlike ephedrine and tyramine, etafedrine did not induce the release of noradrenaline as was demonstrated in vitro in the perfused rabbit heart and instead acted as a selective β2 adrenoreceptor agonist. Etafedrine also belongs to the family of medications called decongestants. It works by narrowing blood vessels in the nasal passages, helping to relieve nasal stuffiness. Etafedrine has been used in pharmaceutical compositions, such as NETHAPRIN Expectorant, Nethaprin Dospan and Dalmacol, useful in the treatment of asthma and other respiratory disorders including chronic bronchitis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-2 adrenergic receptor 203 Target ID: P07550\|\|\|Q53GA6\|\|\|Q9UCZ3 Gene ID: 154.0 Gene Symbol: ADRB2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/4039586	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Chronic bronchitis 51 Sources: http://home.intekom.com/pharm/adcock/neth-exp.html https://www.ncbi.nlm.nih.gov/pubmed/326265	Palliative	Approved 8429	NETHAPRIN Expectorant Approved Use Conditions characterized by bronchial congestion and bronchospasm when an expectorant and bronchodilator action is desired, such as in acute bronchitis, acute episodes of chronic bronchitis and bronchial asthma.
Bronchial asthma 50 Sources: http://home.intekom.com/pharm/adcock/neth-exp.html	Palliative	Approved 8429	NETHAPRIN Expectorant Approved Use Conditions characterized by bronchial congestion and bronchospasm when an expectorant and bronchodilator action is desired, such as in acute bronchitis, acute episodes of chronic bronchitis and bronchial asthma.
Cough 106 Sources: http://bodyandhealth.canada.com/drug/getdrug/dalmacol	Palliative	Approved 8429	Dalmacol Approved Use To control cough associated with inflammation of the mouth and throat that is not helped by cough medications that are less strong.
Allergy 44 Sources: http://www.tabletwise.com/southafrica/nethaprin-dospan-tablet	Palliative	Approved 8429	Nethaprin Dospan Approved Use Used for Bronchodilator, Insomnia, Allergic Reactions, Morning Sickness In Pregnant Women, Cold, Allergic Symptoms and other symptoms
Common cold 58 Sources: http://www.tabletwise.com/southafrica/nethaprin-dospan-tablet	Palliative	Approved 8429	Nethaprin Dospan Approved Use Used for Bronchodilator, Insomnia, Allergic Reactions, Morning Sickness In Pregnant Women, Cold, Allergic Symptoms and other symptoms

C_max

Value	Dose	Co-administered	Analyte	Population
0.1 μg/mL REVIEW http://www.inchem.org/documents/pims/pharm/pim209.htm	24 mg single, oral dose: 24 mg route of administration: Oral experiment type: SINGLE co-administered:		ETAFEDRINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6 h REVIEW http://www.inchem.org/documents/pims/pharm/pim209.htm	24 mg single, oral dose: 24 mg route of administration: Oral experiment type: SINGLE co-administered:		ETAFEDRINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	ACM48141646
Alfa Chemistry	ACM530358
Alfa Chemistry	ACM7681790
Aronis	BLOCK95319
BOC Sciences	5591-29-7
Chemspace	CSC009997986
Compound Cloud	10734
Compound Cloud	68646
Enamine	BBV-33440534
Enamine	BBV-56316782
Enamine	EN300-1608668
MolPort	MolPort-006-118-956
MuseChem	R055529
Toronto Research Chemicals	E889200
ZINC	ZINC000001846418	http://zinc15.docking.org/substances/ZINC000001846418
eMolecules	38570915
eMolecules	43550094
mcule	MCULE-8617221950

PubMed

Title	Date	PubMed
Double-blind trial of a long-acting bronchodilator preparation ("Nethaprin Dospan") in bronchospastic disease.	1976	793781

Patents

Sample Use Guides

In Vivo Use Guide

Dalmacol (each mL contains hydrocodone bitartrate 0.33 mg, etafedrine HCl 3.33 mg, sodium citrate 40 mg, and doxylamine succinate 1.2 mg) the recommended dose is 5 mL (1 teaspoonful) every 3 to 5 hours as needed, but not more than 30 mL in any 24-hour period for adults. For children 6 to 12 years of age, the recommended dose is 2.5 mL to 5 mL every 3 to 5 hours as needed, but not more than 15 mL in any 24-hour period. For children 1 to 6 years of age, the recommended dose is 1.25 mL to 2.5 mL every 3 to 5 hours as needed, but not more than 3 doses in any 24-hour period.

Route of Administration: Oral

In Vitro Use Guide

Effects of (-)-N-ethylephedrine (etafedrine) were studied on the tracheal chain preparation and the atria of the guinea pig and on the rabbit perfused heart. Contraction of the tracheal chain by acetylcholine or histamine was antagonized by etafedrine. Propranolol (5 X 10(-7) M) completely antagonized the bronchodilator effect of 10(-4) M etafedrine on the acetylcholine-evoked contraction. Etafedrine up to 3 X 10(-4) M did not increase heart rate or force of contraction in guinea pig atria. In contrast to tyramine and ephedrine (both 10(-5) M), etafedrine (10(-4) M) failed to release 3H-norepinephrine (noradrenaline) in the perfused rabbit heart. Moreover, the concentration-dependent positive chronotropic and inotropic effects of norepinephrine in isolated atria were slightly, but not significantly enhanced by etafedrine.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:50:45 UTC 2023` Edited by `admin` on `Fri Dec 15 15:50:45 UTC 2023`
Record UNII	2Y6VQU63E8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETAFEDRINE

Official Name

English

etafedrine [INN]

Common Name

English

(-)-ETAFEDRINE

Common Name

English

Etafedrine [WHO-DD]

Common Name

English

.ALPHA.-(1-(ETHYLMETHYLAMINO)ETHYL)BENZYL ALCOHOL

Systematic Name

English

ETAFEDRINE, (-)-

Common Name

English

MENETRYL

Brand Name

English

BENZENEMETHANOL, .ALPHA.-(1-(ETHYLMETHYLAMINO)ETHYL)-

Systematic Name

English

NOVEDRIN

Brand Name

English

ETAFEDRINE [MI]

Common Name

English

BENZENEMETHANOL, .ALPHA.-((1S)-1-(ETHYLMETHYLAMINO)ETHYL)-, (.ALPHA.R)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C48149