2-[ethyl(methyl)amino]-1-phenylpropan-1-ol hydrochloride

• ChemBase ID: 168281
• Molecular Formular: C12H20ClNO
• Molecular Mass: 229.7463
• Monoisotopic Mass: 229.12334195
• SMILES: c1cccc(c1)C(C(N(CC)C)C)O.Cl
• Canonical SMILES: CCN(C(C(c1ccccc1)O)C)C.Cl
• 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
• InChIKey: WRONACHIHQGZSD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[ethyl(methyl)amino]-1-phenylpropan-1-ol hydrochloride
• IUPAC Traditional name: menetyl hydrochloride
• Synonyms: Ethylephedrine Hydrochloride; α-[1-(Ethylmethylamino)ethyl]benzenemethanol Hydrochloride; α-[1-(Ethylmethylamino)ethyl]benzyl Alcohol Hydrochloride; Ditenate; Novedrine Hydrochloride; Etafedrine Hydrochloride (mixture of diastereomers)

Database IDs

• CAS Number: 5591-29-7
• PubChem SID: 162262413
• PubChem CID: 68646

CALCULATED PROPERTIES

• Acid pKa: 13.881725
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.2071488
• LogD (pH = 7.4): 0.31598404
• Log P: 2.0576906
• Molar Refractivity: 59.7306 cm^3
• Polarizability: 23.545218 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 108-110°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E889200

Etafedrine is the N-ethylated analogue of Ephedrine (E575000). Etafedrine is a long-acting bronchodilator that acts as a selective β-adrenergic receptor agonist.

REFERENCES

• Lindmar R. et al.: Arzneim.-Forsch., 35, 602 (1985)
• Ueda, T. et al.: Pharm. Bull., 3, 465 (1985)