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

• ChemBase ID: 166502
• Molecular Formular: C16H19NO3
• Molecular Mass: 273.32696
• Monoisotopic Mass: 273.13649347
• SMILES: C1[C@H]2[C@@]3(C=C[C@@H]1O)c1c(CNCC3)ccc(c1O2)OC
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]3(CCNC2)C=C[C@@H](C1)O
• InChI: InChI=1S/C16H19NO3/c1-19-12-3-2-10-9-17-7-6-16-5-4-11(18)8-13(16)20-15(12)14(10)16/h2-5,11,13,17-18H,6-9H2,1H3/t11-,13-,16-/m0/s1
• InChIKey: AIXQQSTVOSFSMO-RBOXIYTFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,12S,14R)-9-methoxy-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: norgalanthamine
• Synonyms: (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol; (-)-N-Demethylgalanthamine; N-Norgalanthamine; Norgalantamine; N-Desmethyl Galanthamine

Database IDs

• CAS Number: 41303-74-6
• PubChem SID: 162260635
• PubChem CID: 9838394

CALCULATED PROPERTIES

• Acid pKa: 14.810379
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.4000103
• LogD (pH = 7.4): -1.3444526
• Log P: 0.77999485
• Molar Refractivity: 77.0102 cm^3
• Polarizability: 29.806732 Å^3
• Polar Surface Area: 50.72 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol,
• Apperance: Off-White Solid
• Melting Point: >135°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D292035

A metabolite of Galanthamine (G188500), a selective acetylcholinesterase inhibitor.

REFERENCES

• Bickel, U., et al.: Clin. Pharmacol. Ther., 50, 420 (1991)
• Mannens, G., et al.: Drug Metab. Dispos., 30, 553 (1991)
• Zhao, Q., et al.: J. Clin. Pharmacol., 42, 428 (1991)
• Geerts, H., et al.: Brain Res., 1033, 186 (1991)