(1S,12S,14R)-9-(2H3)methoxy-4-(2H3)methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol

• ChemBase ID: 169563
• Molecular Formular: C17H21NO3
• Molecular Mass: 287.35354
• Monoisotopic Mass: 287.15214354
• SMILES: c12c3CN(CC[C@@]41C=C[C@@H](C[C@@H]4Oc2c(cc3)OC)O)C
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]3(CCN(C2)C)C=C[C@@H](C1)O
• InChI: InChI=1S/C17H21NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m0/s1
• InChIKey: ASUTZQLVASHGKV-JDFRZJQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,12S,14R)-9-(^2H₃)methoxy-4-(^2H₃)methyl-11-oxa-4-azatetracyclo[8.6.1.0^1,^1^2.0^6,^1^7]heptadeca-6(17),7,9,15-tetraen-14-ol
• IUPAC Traditional name: (1S,12S,14R)-9-(^2H₃)methoxy-4-(^2H₃)methyl-11-oxa-4-azatetracyclo[8.6.1.0^1,^1^2.0^6,^1^7]heptadeca-6(17),7,9,15-tetraen-14-ol
• Synonyms: (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-(methoxy-d3)-11-(methyl-d3)-6H-benzofurol[3a,3,2,-ef][2]benzazepin-6-ol; BRN 0093736-d6; Galantamin-d6; Galantamina-d6; Galantamine-d6; (-)-Galanthamine-d6; Jilkon-d6; Lycoremin-d6; Lycoremine-d6; NSC 100058-d6; Galanthamine-O-(methyl-d3)-N-(methyl-d3)

Database IDs

• CAS Number: 1128109-00-1
• PubChem SID: 162263695
• PubChem CID: 46780421

CALCULATED PROPERTIES

• Acid pKa: 14.810377
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.9891269
• LogD (pH = 7.4): -0.35530484
• Log P: 1.1630428
• Molar Refractivity: 82.3049 cm^3
• Polarizability: 31.648527 Å^3
• Polar Surface Area: 41.93 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 121-122°C

Safety Information

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

DETAILS

Toronto Research Chemicals - G188503

A deuterated selective acetylcholinesterase inhibitor.

REFERENCES

• Bickel, U., et al.: Clin. Pharmacol. Ther., 50, 420 (1991)
• Maelicke, A., et al.: Drugs Dis Today, 1, 53 (1991)
• Sauvaltre, T., et al.: J. Med. Chem., 50, 5311 (1991)