2-{3-[bis(propan-2-yl)amino]-1-phenylpropyl}-4-(hydroxymethyl)phenol

• ChemBase ID: 170912
• Molecular Formular: C22H31NO2
• Molecular Mass: 341.48704
• Monoisotopic Mass: 341.23547924
• SMILES: c1cc(cc(c1O)C(CCN(C(C)C)C(C)C)c1ccccc1)CO
• Canonical SMILES: OCc1ccc(c(c1)C(c1ccccc1)CCN(C(C)C)C(C)C)O
• InChI: InChI=1S/C22H31NO2/c1-16(2)23(17(3)4)13-12-20(19-8-6-5-7-9-19)21-14-18(15-24)10-11-22(21)25/h5-11,14,16-17,20,24-25H,12-13,15H2,1-4H3
• InChIKey: DUXZAXCGJSBGDW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{3-[bis(propan-2-yl)amino]-1-phenylpropyl}-4-(hydroxymethyl)phenol
• IUPAC Traditional name: 2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol
• Synonyms: 3-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxybenzenemethanol; rac 5-Hydroxymethyl Tolterodine, 90% by HPLC

Database IDs

• CAS Number: 200801-70-3
• PubChem SID: 164226822
• PubChem CID: 9927971

CALCULATED PROPERTIES

• Acid pKa: 9.5834055
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.0560644
• LogD (pH = 7.4): 1.572271
• Log P: 3.42528
• Molar Refractivity: 105.7319 cm^3
• Polarizability: 41.04398 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Off White to Pale Yellow Solid
• Melting Point: 44-46°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H948365

A metabolite of Tolterodine (T535800), a muscarinic receptor antagonist used in the treatment of urinary incontinence. Also, a degradation product of Fesoterodine (F321300) formed under stress conditions in tablet dosage forms.

REFERENCES

• Palmer, L., et al.: J. Pharm. Biomed. Anal., 16, 155 (1997)
• Hills, C., et al.: Drugs, 55, 813 (1997)
• Wefer, J., et al.: World J. Urol., 19, 312 (1997)