2-[3-(methylamino)propyl]tricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene-9,10-diol

• ChemBase ID: 167600
• Molecular Formular: C19H23NO2
• Molecular Mass: 297.39142
• Monoisotopic Mass: 297.17287898
• SMILES: C1(C(c2c(C(c3c1cccc3)CCCNC)cccc2)O)O
• Canonical SMILES: CNCCCC1c2ccccc2C(C(c2c1cccc2)O)O
• InChI: InChI=1S/C19H23NO2/c1-20-12-6-11-13-14-7-2-4-9-16(14)18(21)19(22)17-10-5-3-8-15(13)17/h2-5,7-10,13,18-22H,6,11-12H2,1H3
• InChIKey: KQWYQGRGZFSGCJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[3-(methylamino)propyl]tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-9,10-diol
• IUPAC Traditional name: 2-[3-(methylamino)propyl]tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-9,10-diol
• Synonyms: 10,11-Dihydro-5-[3-(methylamino)propyl]-5H-dibenzo[a,d]cycloheptene-10,11-diol; 10,11-Dihydroxy-N-methyl-5H-dibenzo[a,d]cycloheptane-5-propylamine; 10,11-Dihydro-10,11-dihydroxy Protriptyline

Database IDs

• CAS Number: 29785-65-7
• PubChem SID: 162261733
• PubChem CID: 46781304

CALCULATED PROPERTIES

• Acid pKa: 13.053203
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.691689
• LogD (pH = 7.4): -0.34557158
• Log P: 2.543526
• Molar Refractivity: 88.9098 cm^3
• Polarizability: 34.77678 Å^3
• Polar Surface Area: 52.49 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D449045

A metabolite of Protriptyline.

REFERENCES

• Sisenwine, S.F., et al.: J. Pharmacol. Exp. Ther., 175, 51 (1970)
• Rovei, V., et al.: J. Pharma. Sci., 65, 810 (1970)