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

• ChemBase ID: 164696
• Molecular Formular: C20H23ClN2O4
• Molecular Mass: 390.86062
• Monoisotopic Mass: 390.13463491
• SMILES: c1c(ccc(c1)[C@H](c1ncccc1)CCN(C)C)Cl.C(=C\C(=O)O)\C(=O)O
• Canonical SMILES: CN(CC[C@@H](c1ccccn1)c1ccc(cc1)Cl)C.OC(=O)/C=C\C(=O)O
• InChI: InChI=1S/C16H19ClN2.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-;/m1./s1
• InChIKey: DBAKFASWICGISY-HFNHQGOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; [(3R)-3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
• IUPAC Traditional name: (-)-chlorpheniramine; maleic acid
• Synonyms: (γR)-γ-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine (2Z)-2-Butenedioate; 2-[p-Chloro-α-[2-(dimethylamino)ethyl]benzyl]pyridine Maleate; (-)-Chlorpheniramine Maleate; L-Chlorpheniramine Maleate; (R)-Chlorpheniramine Maleate Salt

Database IDs

• CAS Number: 23095-76-3
• PubChem SID: 162258831
• PubChem CID: 16667681

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.20455076
• LogD (pH = 7.4): 1.5225012
• Log P: 3.584951
• Molar Refractivity: 80.8503 cm^3
• Polarizability: 31.551079 Å^3
• Polar Surface Area: 16.13 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C424306

The R-enantiomer of Chlorpheniramine (C424300). Antihistaminic.

REFERENCES

• Ishida, M., et al.: Int. J. Pharm., 359, 46 (2008)
• Moreno, R., et al.: Biomed. Chromatog., 24, 774 (2008)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2008)