Etafedrine hydrochlorideProduct ingredient for Etafedrine

Name
Etafedrine hydrochloride
Drug Entry
Etafedrine

Etafedrine (INN) or ethylephedrine is a long-acting bronchodilator and has been an ingredient combined with other drugs in the brand names Nethaprin 3 and Dalmacol 10. It was previously available as both the free base and as the hydrochloride salt manufactured by Sanofi-Aventis (now Sanofi) has been discontinued 7.

Ethylephedrine is be formed by alkylating ephedrine with ethyl iodide. The hydrochloride is be prepared by passing hydrogen chloride through a solution of ethylephedrine in diethyl ether 11.

This belongs to the family of medications called decongestants. It acts by narrowing blood vessels in the nasal passages, helping to relieve nasal congestion 11.

Accession Number
DBSALT001778
Structure
Synonyms
(-)-2-(ethylmethylamino)-1-phenylpropan-1-ol hydrochloride / (-)-ethylephedrine hydrochloride / alpha-(1-(ethylmethylamino)ethyl)benzyl alcohol hydrochloride / Etafedrin hydrochloride / Etafedrine HCl / Nethamine
UNII
Y134VQ304Y
CAS Number
530-35-8
Weight
Average: 229.75
Monoisotopic: 229.123342
Chemical Formula
C12H20ClNO
InChI Key
WRONACHIHQGZSD-JGAZGGJJSA-N
InChI
InChI=1S/C12H19NO.ClH/c1-4-13(3)10(2)12(14)11-8-6-5-7-9-11;/h5-10,12,14H,4H2,1-3H3;1H/t10-,12-;/m0./s1
IUPAC Name
(1R,2S)-2-[ethyl(methyl)amino]-1-phenylpropan-1-ol hydrochloride
SMILES
Cl.CCN(C)[C@@H](C)[C@H](O)C1=CC=CC=C1
ChemSpider
32701663
Predicted Properties
PropertyValueSource
Water Solubility9.44 mg/mLALOGPS
logP2.07ALOGPS
logP2.06Chemaxon
logS-1.3ALOGPS
pKa (Strongest Acidic)13.88Chemaxon
pKa (Strongest Basic)9.14Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area23.47 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity59.73 m3·mol-1Chemaxon
Polarizability22.51 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon