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

• ChemBase ID: 179689
• Molecular Formular: C20H23BrN2O4
• Molecular Mass: 435.31162
• Monoisotopic Mass: 434.08411923
• SMILES: C(=O)(/C=C\C(=O)O)O.[C@H](CCN(C)C)(c1ccc(cc1)Br)c1ncccc1
• 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-
• InChIKey: SRGKFVAASLQVBO-BTJKTKAUSA-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: (2Z)-but-2-enedioic acid; [(3S)-3-(4-bromophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
• Synonyms: Dexbrompheniramine maleate; Halin; Disomer; Brompheniramine Maleate

Database IDs

• CAS Number: 86-22-6
• PubChem SID: 164235599
• PubChem CID: 6433334

CALCULATED PROPERTIES

• 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
• H Acceptors: 2
• H Donor: 0

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Histamine H1 receptor antagonist

Product Information

• Salt Data: Maleate
• Application(s): Antihistamine drug; Has antidepressant properties

REFERENCES

• Saijo, S., Yakugaku Zasshi, 1952, 72, 1529; CA, 47, 8080i, (synth)
• Bruce, R.B. et al., J. Med. Chem., 1968, 11, 1031, (synth, tlc, metab)
• Shafi'ee, A. et al., J. Med. Chem., 1969, 12, 266, (abs config)
• James, M.N.G. et al., J. Med. Chem., 1971, 14, 670, (cryst struct)
• Fricke, F.L., J. Assoc. Off. Anal. Chem., 1972, 55, 1162, (glc)
• Berkoff, C.E. et al., Synth. Commun., 1980, 10, 939, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 4002
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 932
• Parvez, M. et al., Acta Cryst. C, 1996, 52, 901, (cryst struct, abs config)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BNE750; DNW759; DXG100