4-[(1R)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol hydrochloride

• ChemBase ID: 153276
• Molecular Formular: C13H22ClNO3
• Molecular Mass: 275.77168
• Monoisotopic Mass: 275.12882125
• SMILES: CC(C)(C)NC[C@@H](c1ccc(c(c1)CO)O)O.Cl
• Canonical SMILES: OCc1cc(ccc1O)[C@H](CNC(C)(C)C)O.Cl
• InChI: InChI=1S/C13H21NO3.ClH/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15;/h4-6,12,14-17H,7-8H2,1-3H3;1H/t12-;/m0./s1
• InChIKey: OWNWYCOLFIFTLK-YDALLXLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1R)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol hydrochloride
• IUPAC Traditional name: ventolin hydrochloride
• Synonyms: (R)-salbutamol hydrochloride; Levosalbutamol hydrochloride; Levalbuterol hydrochloride; (α1R)-α1-[[(1,1-Dimethylethyl)amino]methyl]-4-hydroxy-1,3-benzenedimethanol Hydrochloride; (-)-Salbutamol Hydrochloride; Levalbuterol Hydrochloride; Xopenex; (R)-Albuterol Hydrochloride

Database IDs

• CAS Number: 50293-90-8
• MDL Number: MFCD08067728
• PubChem SID: 162247415
• PubChem CID: 123601

CALCULATED PROPERTIES

• Acid pKa: 10.121162
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -2.306487
• LogD (pH = 7.4): -1.3223417
• Log P: 0.34441614
• Molar Refractivity: 67.8709 cm^3
• Polarizability: 26.575071 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥15 mg/mL; Methanol; Water
• Apperance: Off-White Solid; white to tan powder
• Melting Point: 169-171°C
• Optical Rotation: [α]/D -25 to -35°, c = 0.1 in H2O

Safety Information

• Storage Condition: -20°C Freezer; desiccated
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C13H21NO3 · HCl

DETAILS

Sigma Aldrich - SML0138

Biochem/physiol Actions
Levalbuterol (levosalbutamol) is the more active isomer of albuterol. Levalbuterol is a β-adrenergic agonist; a bronchodilator used clinically to treat asthma and COPD..

Toronto Research Chemicals - A514485

The R-enantiomer of Albuterol (A514500). A β2-adrenoceptor agonist. Bronchodilator; tocolytic.

REFERENCES

• Han, et al.: Bioorg. Med. Chem., 14, 6043 (2006)
• Liyou, H., et al.: Biochem., 46, 1432 (2006)
• Agrawal, D., et al.: J. Allergy Clin. Immunol., 113, 503 (2006)