| 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
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
| Molecular Formula | C12H19NO |
| Molecular Weight | 193.2854 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
Sourcing
PubMed
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
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.
