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

• ChemBase ID: 177579
• 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-/m01/s1
• InChIKey: GWHQHAUAXRMMOT-MBANBULQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxybutanedioic acid 3-[(1S)-1-(dimethylamino)ethyl]phenyl N-ethyl-N-methylcarbamate; (2R,3R)-2,3-dihydroxybutanedioic acid; 3-[(1S)-1-(dimethylamino)ethyl]phenyl N-ethyl-N-methylcarbamate
• IUPAC Traditional name: L(+)-tartaric acid; exelon
• Synonyms: N-Ethyl-N-methylcarbamic Acid 3-[(1S)-1-(Dimethylamino)ethyl]phenyl Ester (2R,3R)-2,3-Dihydroxybutanedioate; (S)-Ethylmethylcarbamic Acid 3-[1-(Dimethylamino)ethyl]phenyl Ester [R-(R*,R*)]-2,3-Dihydroxybutanedioate; ENA 713; Rivastigmine Hydrogentartrate; SDZ-ENA 713; Rivastigmine Bitartrate; Rivastigmine Tartrate Salt; Rivastigmine tartrate (Exelon)

Database IDs

• CAS Number: 129101-54-8
• PubChem SID: 164233489
• PubChem CID: 6918078

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

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 123-125°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: AChR

Product Information

• Salt Data: Tartrate

DETAILS

Toronto Research Chemicals - R541000

A brain selective acetylcholinesterase inhibitor. Nootropic.

REFERENCES

• Rosler, M., et al.: Brit. Med. J., 318, 633 (1999)
• Enz, A., et al.: Prog. Brain Res., 98, 431 (1999)