(2Z)-but-2-enedioic acid; [(3S)-3-(4-bromophenyl)-3-(pyridin-2-yl)propyl]dimethylamine

• ChemBase ID: 162997
• Molecular Formular: C20H23BrN2O4
• Molecular Mass: 435.31162
• Monoisotopic Mass: 434.08411923
• SMILES: c1c(ccc(c1)[C@@H](c1ncccc1)CCN(C)C)Br.C(=C\C(=O)O)\C(=O)O
• Canonical SMILES: CN(CC[C@H](c1ccccn1)c1ccc(cc1)Br)C.OC(=O)/C=C\C(=O)O
• InChI: InChI=1S/C16H19BrN2.C4H4O4/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13;5-3(6)1-2-4(7)8/h3-9,11,15H,10,12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t15-;/m0./s1
• InChIKey: SRGKFVAASLQVBO-DASCVMRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; [(3S)-3-(4-bromophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
• IUPAC Traditional name: dexbrompheniramine; maleic acid
• Synonyms: (γS)-γ-(4-bromophenyl)-N,N-dimethyl-2-pyridinepropanamine (2Z)-2-Butenedioate; (S)-2-[p-Bromo-α-[2-(dimethylamino)ethyl]benzyl]pyridine Maleate; 1-(p-Bromophenyl)-1-(2-pyridyl)-3-dimethylamine Propane Maleate; Dexbrompheniramine Maleate; Dimegan; Disomer; Disomer Maleate; Drixoral; d-2-[p-Bromo-α-(2-dimethylaminoethyl)benzyl]pyridine Maleate; (S)-Brompheniramine Maleate

Database IDs

• CAS Number: 2391-03-9
• PubChem SID: 162257132
• PubChem CID: 6433334

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.36835155
• LogD (pH = 7.4): 1.683695
• Log P: 3.7496588
• Molar Refractivity: 83.6683 cm^3
• Polarizability: 32.339294 Å^3
• Polar Surface Area: 16.13 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B686335

The S-enantimer of Brompheniramine maleate (B686355) as antihistaminic.

REFERENCES

• Walle, T., et al.: Biochem. Pharmacol., 37, 115 (1988)
• Yang, W., et al.: J. Pharm. Pharmacol., 56, 703 (1988)
• Xu, H., et al.: Anal. Sci., 20, 1409 (1988)