(2Z)-but-2-enedioic acid; 9-amino-1,2,3,4-tetrahydroacridin-1-ol

• ChemBase ID: 160489
• Molecular Formular: C17H18N2O5
• Molecular Mass: 330.33522
• Monoisotopic Mass: 330.12157169
• SMILES: c1ccc2c(c1)c(c1c(n2)CCCC1O)N.C(=C\C(=O)O)\C(=O)O
• Canonical SMILES: OC1CCCc2c1c(N)c1c(n2)cccc1.OC(=O)/C=C\C(=O)O
• InChI: InChI=1S/C13H14N2O.C4H4O4/c14-13-8-4-1-2-5-9(8)15-10-6-3-7-11(16)12(10)13;5-3(6)1-2-4(7)8/h1-2,4-5,11,16H,3,6-7H2,(H2,14,15);1-2H,(H,5,6)(H,7,8)/b;2-1-
• InChIKey: NEEKVKZFYBQFGT-BTJKTKAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; 9-amino-1,2,3,4-tetrahydroacridin-1-ol
• IUPAC Traditional name: 9-amino-1,2,3,4-tetrahydroacridin-1-ol; maleic acid
• Synonyms: 9-Amino-1,2,3,4-tetrahydro-1-acridinol (2Z)-2-Butenedioate; HP 029; Mentane; P 83-6029A; Velnacrine Hydrogen Maleate; Velnacrine Maleate; 1-hydroxy tacrine maleate; 9-Amino-1,2,3,4-tetrahydroacridin-1-ol Maleate

Database IDs

• CAS Number: 118909-22-1
• PubChem SID: 162254624
• PubChem CID: 5702293

CALCULATED PROPERTIES

• Acid pKa: 14.237208
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.3788231
• LogD (pH = 7.4): 0.39972323
• Log P: 1.3973336
• Molar Refractivity: 63.2536 cm^3
• Polarizability: 25.273125 Å^3
• Polar Surface Area: 59.14 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 171-173°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A629900

A potential Alzheimer's Disease therapeutic of low toxicity. Exhibits biochemical and pharmacological profile similar to THA except that it is far less toxic and without measurable liver toxicity in humans.

REFERENCES

• Alon, R., et al.: J. Cell Biol., 128, 1243 (1995)
• Min, W., et al.: J .Immunol., 159, 3508 (1995)
• Lum, A., et al.: J. Biol. Chem., 277, 20660 (1995)
• Carvalho, F., et al.: J. Appl. Toxicol., 24, 419 (1995)