(2R,3R)-2,3-dihydroxybutanedioic acid; (2S)-2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one

• ChemBase ID: 163107
• Molecular Formular: C17H24ClNO7
• Molecular Mass: 389.82796
• Monoisotopic Mass: 389.12412979
• SMILES: c1c(cccc1C(=O)[C@@H](NC(C)(C)C)C)Cl.[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.Clc1cccc(c1)C(=O)[C@@H](NC(C)(C)C)C
• InChI: InChI=1S/C13H18ClNO.C4H6O6/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10;5-1(3(7)8)2(6)4(9)10/h5-9,15H,1-4H3;1-2,5-6H,(H,7,8)(H,9,10)/t9-;1-,2-/m01/s1
• InChIKey: OGRSKLGKZQBLSQ-NDAAPVSOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxybutanedioic acid; (2S)-2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
• IUPAC Traditional name: L(+)-tartaric acid; bupropion hcl
• Synonyms: (2S)-1-(3-Chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone L-Tartaric Acid Salt; (S)-Bupropion L-Tartaric Acid Salt

Database IDs

• PubChem SID: 162257242
• PubChem CID: 71314306

CALCULATED PROPERTIES

• Acid pKa: 18.286419
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.6626676
• LogD (pH = 7.4): 2.3901906
• Log P: 3.2661126
• Molar Refractivity: 67.6994 cm^3
• Polarizability: 26.657854 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 153-155°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B689620

A selective inhibitor of dopamine uptake. An antidepressant of the aminoketone class; aid in smoking cessation.

REFERENCES

• Soroko, F., et al.: J. Pharm. Pharmacol., 29, 769 (1977)
• Tucker, W.E., J. Clin. Psychiatry, 44, 60 (1977)
• Hsyu, P-H., et al.: J. Clin. Pharmacol., 37, 737 (1977)
• West, R., et al.: Expert Opin. Pharmacother., 4, 533 (1977)