N-{1-azabicyclo[2.2.2]octan-3-yl}-6-chloro-4-(13C,2H3)methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide hydrochloride

• ChemBase ID: 160944
• Molecular Formular: C17H21Cl2N3O3
• Molecular Mass: 387.26559484
• Monoisotopic Mass: 386.09935175
• SMILES: c1(cc(cc2c1OCC(=O)N2[13CH3])Cl)C(=O)NC1[C@H]2CCN(CC2)C1.Cl
• Canonical SMILES: Clc1cc2N([13CH3])C(=O)COc2c(c1)C(=O)NC1CN2CC[C@H]1CC2.Cl
• InChI: InChI=1S/C17H20ClN3O3.ClH/c1-20-14-7-11(18)6-12(16(14)24-9-15(20)22)17(23)19-13-8-21-4-2-10(13)3-5-21;/h6-7,10,13H,2-5,8-9H2,1H3,(H,19,23);1H/i1+1
• InChIKey: DBMKBKPJYAHLQP-YTBWXGASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{1-azabicyclo[2.2.2]octan-3-yl}-6-chloro-4-(^1^3C,^2H₃)methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide hydrochloride
• IUPAC Traditional name: 6-chloro-4-(^1^3C,^2H₃)methyl-3-oxo-N-[(1s,4s)-1-azabicyclo[2.2.2]octan-3-yl]-2H-1,4-benzoxazine-8-carboxamide hydrochloride
• Synonyms: N-1-Azabicyclo[2.2.2]-oct-3-yl-6-chloro-3,4-dihydro-4-(methyl-13C,d3)-3-oxo-2H-1,4-benzoxazine-8-carboxamide Hydrochloride; Azasetron-13C,D3 Hydrochloride

Database IDs

• PubChem SID: 162255079
• PubChem CID: 71313548

CALCULATED PROPERTIES

• Acid pKa: 13.510593
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.508944
• LogD (pH = 7.4): 0.19647563
• Log P: 0.67269003
• Molar Refractivity: 90.6912 cm^3
• Polarizability: 34.725365 Å^3
• Polar Surface Area: 61.88 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: 271-275°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A802803

A 5-HT3 receptor antagonist. Used as an antiemetic.

REFERENCES

• Sato, N., et al.: Japan J. Pharmacol., 59, 443 (1992)
• Haga, K., et al.: Japan J. Pharmacol., 63, 377 (1993)