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

• ChemBase ID: 169560
• Molecular Formular: C17H19NO3
• Molecular Mass: 285.33766
• Monoisotopic Mass: 285.13649347
• SMILES: c12[C@@]34CCN(Cc1ccc(c2O[C@H]3CC(=O)C=C4)OC)C
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]3(CCN(C2)C)C=CC(=O)C1
• InChI: InChI=1S/C17H19NO3/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/h3-6,14H,7-10H2,1-2H3/t14-,17-/m0/s1
• InChIKey: QENVUHCAYXAROT-YOEHRIQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,12S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^1,^1^2.0^6,^1^7]heptadeca-6(17),7,9,15-tetraen-14-one
• IUPAC Traditional name: (1S,12S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^1,^1^2.0^6,^1^7]heptadeca-6(17),7,9,15-tetraen-14-one
• Synonyms: (4aS,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one; 3-Deoxy-3-oxo-galanthamine; Narwedine; Galanthaminone; (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol Hydrobromide; (-)-Galantamine Hydrobromide; Nivalin; Nivaline; Razadyne; Reminyl; Galanthamine Hydrobromide

Database IDs

• CAS Number: 510-77-0; 1953-04-4
• PubChem SID: 162263692
• PubChem CID: 10356588

CALCULATED PROPERTIES

• Acid pKa: 17.683346
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.6495724
• LogD (pH = 7.4): 1.112847
• Log P: 1.8030827
• Molar Refractivity: 81.2971 cm^3
• Polarizability: 31.101225 Å^3
• Polar Surface Area: 38.77 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol; Water
• Apperance: White to Off-White; White to Off-White Powder
• Melting Point: 182-184°C (dec.); 254-256°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G188550

A metabolite of Galanthamine, a selective acetylcholinesterase inhibitor.

Toronto Research Chemicals - G188500

A selective acetylcholinesterase inhibitor. A therapeutic agent for the treatment and prevention of Alzheimer's disease and other diseases resulting from reduced neuronal metabolism.

REFERENCES

• Bickel, U., et al.: Clin. Pharmacol. Ther., 50, 420 (1991)
• Friess, S.L., et al.: Toxicol. Appl. Pharmacol., 3, 347 (1961)
• Bickel, U., et al.: Clin. Pharmacol. Ther., 50, 420 (1961)
• Harvey, A.L., et al.: Pharmacol. Ther., 68, 113 (1961)