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

• ChemBase ID: 171236
• Molecular Formular: C19H21NO
• Molecular Mass: 279.37614
• Monoisotopic Mass: 279.1623143
• SMILES: C1=C(c2c(C(c3c1cccc3)CCCNC)cccc2)O
• Canonical SMILES: CNCCCC1c2ccccc2C=C(c2c1cccc2)O
• InChI: InChI=1S/C19H21NO/c1-20-12-6-11-16-15-8-3-2-7-14(15)13-19(21)18-10-5-4-9-17(16)18/h2-5,7-10,13,16,20-21H,6,11-12H2,1H3
• InChIKey: JJHKAPUZDMTRJA-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),4,6,9,12,14-heptaen-9-ol
• IUPAC Traditional name: 2-[3-(methylamino)propyl]tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-9-ol
• Synonyms: 5-[3-(Methylamino)propyl]-5H-dibenzo[a,d]cyclohepten-10-ol; 10-Hydroxy-N-methyl-5H-dibenzo[a,d]cycloheptene-5-propylamine; 10-Hydroxy Protriptyline

Database IDs

• CAS Number: 27462-57-3
• PubChem SID: 164227146
• PubChem CID: 46781886

CALCULATED PROPERTIES

• Acid pKa: 10.072686
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.50826526
• LogD (pH = 7.4): 0.8614753
• Log P: 2.9130077
• Molar Refractivity: 89.1957 cm^3
• Polarizability: 34.11476 Å^3
• Polar Surface Area: 32.26 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H952650

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)