(2Z)-2-[3-(dimethylamino)propylidene]tricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-ol; oxalic acid

• ChemBase ID: 170247
• Molecular Formular: C22H25NO5
• Molecular Mass: 383.4376
• Monoisotopic Mass: 383.17327291
• SMILES: C1C(c2c(/C(=C\CCN(C)C)/c3c1cccc3)cccc2)O.C(=O)(O)C(=O)O
• Canonical SMILES: OC(=O)C(=O)O.CN(CC/C=C\1/c2ccccc2CC(c2c1cccc2)O)C
• InChI: InChI=1S/C20H23NO.C2H2O4/c1-21(2)13-7-12-17-16-9-4-3-8-15(16)14-20(22)19-11-6-5-10-18(17)19;3-1(4)2(5)6/h3-6,8-12,20,22H,7,13-14H2,1-2H3;(H,3,4)(H,5,6)/b17-12-
• InChIKey: QFIDJPMHGAQWEF-HBPAQXCTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-2-[3-(dimethylamino)propylidene]tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-ol; oxalic acid
• IUPAC Traditional name: (2Z)-2-[3-(dimethylamino)propylidene]tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-ol; oxalic acid
• Synonyms: 5-[3-(Dimethylamino)propylidene]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol Oxalate; 10-Hydroxy Amitriptyline Oxalate

Database IDs

• PubChem SID: 164226157
• PubChem CID: 71748894

CALCULATED PROPERTIES

• Acid pKa: 14.257287
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.14699037
• LogD (pH = 7.4): 1.2464269
• Log P: 3.578724
• Molar Refractivity: 103.0227 cm^3
• Polarizability: 35.88354 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H828100

A metabolite of Amitriptyline (A633350).

REFERENCES

• Iwasaki, M., et al.: J. Biol. Chem., 268, 759 (1993)
• Geertsen, S., et al.: Xenobiotica, 25, 895 (1993)
• Mautz, D., et al.: Drug Metab. Dispos., 23, 513 (1993)
• de Groot, M., et al.: J. Med. Chem., 42, 1515 (1993)