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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H19NO
Molecular Weight 193.2858
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETAFEDRINE

SMILES

CCN(C)[C@@]([H])(C)[C@@]([H])(c1ccccc1)O

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
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

Curator's Comment:: Etafedrine was registered under the trade mark NETHAPRIN in 9/20/1966 as an antiasthmatic medicine.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P07550|||Q53GA6|||Q9UCZ3
Gene ID: 154.0
Gene Symbol: ADRB2
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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.
Palliative
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.
Palliative
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.
Palliative
Nethaprin Dospan

Approved Use

Used for Bronchodilator, Insomnia, Allergic Reactions, Morning Sickness In Pregnant Women, Cold, Allergic Symptoms and other symptoms
Palliative
Nethaprin Dospan

Approved Use

Used for Bronchodilator, Insomnia, Allergic Reactions, Morning Sickness In Pregnant Women, Cold, Allergic Symptoms and other symptoms
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.1 μg/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6 h
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
PubMed

PubMed

TitleDatePubMed
Double-blind trial of a long-acting bronchodilator preparation ("Nethaprin Dospan") in bronchospastic disease.
1976
On the mechanism of bronchodilatation by etafedrine.
1985
Patents

Sample Use Guides

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.
Name Type Language
ETAFEDRINE
INN   MI   WHO-DD  
INN  
Official Name English
ETAFEDRINE [INN]
Common Name English
ETAFEDRINE [WHO-DD]
Common Name English
(-)-ETAFEDRINE
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
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C76539
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
PRIMARY
CAS
7681-79-0
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
INN
1734
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
PRIMARY
MESH
C007636
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
PRIMARY
CAS
48141-64-6
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
PRIMARY
WIKIPEDIA
ETAFEDRINE
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
PRIMARY
MERCK INDEX
M5034
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
PRIMARY Merck Index
EVMPD
SUB07256MIG
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
PRIMARY
ECHA (EC/EINECS)
256-359-0
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
ALTERNATIVE
DRUG CENTRAL
3189
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
PRIMARY
FDA UNII
2Y6VQU63E8
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
PRIMARY
PUBCHEM
94532
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
PRIMARY
DRUG BANK
DB11587
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
PRIMARY
ECHA (EC/EINECS)
231-677-2
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
PRIMARY
ChEMBL
CHEMBL2110926
Created by admin on Sat Jun 26 10:55:05 UTC 2021 , Edited by admin on Sat Jun 26 10:55:05 UTC 2021
PRIMARY