(2R,3R)-2,3-dihydroxybutanedioic acid 3-[(1R)-1-(dimethylamino)ethyl]phenyl N-ethyl-N-methylcarbamate

• ChemBase ID: 177578
• Molecular Formular: C18H28N2O8
• Molecular Mass: 400.42352
• Monoisotopic Mass: 400.18456587
• SMILES: c1cc(cc(c1)[C@H](N(C)C)C)OC(=O)N(CC)C.[C@H]([C@@H](O)C(=O)O)(O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)O)O.CCN(C(=O)Oc1cccc(c1)[C@H](N(C)C)C)C
• InChI: InChI=1S/C14H22N2O2.C4H6O6/c1-6-16(5)14(17)18-13-9-7-8-12(10-13)11(2)15(3)4;5-1(3(7)8)2(6)4(9)10/h7-11H,6H2,1-5H3;1-2,5-6H,(H,7,8)(H,9,10)/t11-;1-,2-/m11/s1
• InChIKey: GWHQHAUAXRMMOT-VUAFVNRWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxybutanedioic acid 3-[(1R)-1-(dimethylamino)ethyl]phenyl N-ethyl-N-methylcarbamate
• IUPAC Traditional name: L(+)-tartaric acid 3-[(1R)-1-(dimethylamino)ethyl]phenyl N-ethyl-N-methylcarbamate
• Synonyms: N-Ethyl-N-methylcarbamic Acid 3-[(1R)-1-(Dimethylamino)ethyl]phenyl Ester (2R,3R)-2,3-Dihydroxybutanedioate; SDZ 212712 Tartrate; (R)-Rivastigmine Tartrate Salt

Database IDs

• PubChem SID: 164233488
• PubChem CID: 71296087

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.7295023
• LogD (pH = 7.4): 0.9140339
• Log P: 2.4090931
• Molar Refractivity: 73.3706 cm^3
• Polarizability: 28.459797 Å^3
• Polar Surface Area: 32.78 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R540990

The R-enantiomer of Rivastigmine (R541000) as an impurity.

REFERENCES

• Sussman, J., et al.: Science, 253, 872 (1991)
• Davies, P., et al.: Brain Res., 171, 319 (1991)
• Kawakami, Y., et al.: Bioorg. Med. Chem., 4, 1429 (1991)
• Sussman, J., et al.: J Mol. Biol., 1988, 203, 821 (1991)