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

• ChemBase ID: 166503
• Molecular Formular: C16H19NO3
• Molecular Mass: 273.32696
• Monoisotopic Mass: 273.13649347
• SMILES: c12c3CNCC[C@@]41C=C[C@@H](C[C@@H]4Oc2c(cc3)OC)O
• 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-(^2H₃)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: (1S,12S,14R)-9-(^2H₃)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
• Synonyms: (8aS,10R,12aS)-1,2,3,4,8a,9-Hexahydro-7-(methoxy-d3)-10H-benzofuro[3a,3,2-ef][2]benzazepin-10-ol; (-)-N-Demethylgalanthamine-d3; N-Norgalanthamine-d3; Norgalantamine-d3; N-Desmethyl Galanthamine-O-methyl-d3

Database IDs

• PubChem SID: 162260636
• PubChem CID: 46781174

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: 29.807735 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: 142-145°C

DETAILS

Toronto Research Chemicals - D292037

A labelled 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)