2-[(2R)-2-aminopropoxy]-1,3-dimethylbenzene hydrochloride

• ChemBase ID: 174429
• Molecular Formular: C11H18ClNO
• Molecular Mass: 215.71972
• Monoisotopic Mass: 215.10769188
• SMILES: c1(cccc(c1OC[C@H](N)C)C)C.Cl
• Canonical SMILES: C[C@H](COc1c(C)cccc1C)N.Cl
• InChI: InChI=1S/C11H17NO.ClH/c1-8-5-4-6-9(2)11(8)13-7-10(3)12;/h4-6,10H,7,12H2,1-3H3;1H/t10-;/m1./s1
• InChIKey: NFEIBWMZVIVJLQ-HNCPQSOCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2R)-2-aminopropoxy]-1,3-dimethylbenzene hydrochloride
• IUPAC Traditional name: mexiletine hcl hydrochloride
• Synonyms: (2R)-1-(2,6-Dimethylphenoxy)-2-propanamine Hydrochloride; (-)-(R)-Mexiletine Hydrochloride; (-)-Mexiletine Hydrochloride; R-(-)-Mexiletine Hydrochloride

Database IDs

• CAS Number: 81771-86-0
• PubChem SID: 164230339
• PubChem CID: 57149588

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.52837545
• LogD (pH = 7.4): 0.39041123
• Log P: 2.4620085
• Molar Refractivity: 54.9722 cm^3
• Polarizability: 21.605932 Å^3
• Polar Surface Area: 35.25 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M340790

The R-enantiomer of Mexiletine (M340800). Antiarrhythmic (class IB).

REFERENCES

• Singh, E.M., et al.: Br. J. Pharmacol., 44, 1 (1972)
• Scott, K.N., et al.: Drug Metab. Dispos., 1, 506 (1972)
• Chew, C.Y.C., et al.: Drugs, 17, 161 (1972)
• Abounassif, M.A., et al.: Anal. Profiles Drug Subs., 20, 433 (1972)