(2Z)-but-2-enedioic acid; 2-[(1S)-1-(4-chlorophenyl)-4-(2H3)methyl(5,5,5-2H3)pentyl]pyridine

• ChemBase ID: 164697
• Molecular Formular: C21H24ClNO4
• Molecular Mass: 389.87256
• Monoisotopic Mass: 389.13938593
• SMILES: c1c(ccc(c1)[C@@H](c1ncccc1)CCC(C)C)Cl.C(=C\C(=O)O)\C(=O)O
• Canonical SMILES: CC(CC[C@H](c1ccccn1)c1ccc(cc1)Cl)C.OC(=O)/C=C\C(=O)O
• InChI: InChI=1S/C17H20ClN.C4H4O4/c1-13(2)6-11-16(17-5-3-4-12-19-17)14-7-9-15(18)10-8-14;5-3(6)1-2-4(7)8/h3-5,7-10,12-13,16H,6,11H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t16-;/m0./s1
• InChIKey: CFGSZIRHBOVJBT-ZSJYYTRTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; 2-[(1S)-1-(4-chlorophenyl)-4-(^2H₃)methyl(5,5,5-^2H₃)pentyl]pyridine
• IUPAC Traditional name: 2-[(1S)-1-(4-chlorophenyl)-4-(^2H₃)methyl(5,5,5-^2H₃)pentyl]pyridine; maleic acid
• Synonyms: (γS)-γ-(4-Chlorophenyl)-N,N-(dimethyl-d6)-2-pyridinepropanamine (2Z)-2-Butenedioate; 2-[p-Chloro-α-[2-(dimethylamino-d6)ethyl]benzyl]pyridine Maleate; (+)-Chlorpheniramine-d6 Maleate; Dexchloropheniramine-d6 Maleate; Dextrochlorpheniramine-d6 Maleate; Fortamine-d6; Isomerine-d6; Phenamin-d6; Phendextro-d6; Polamin-d6; Polaramin-d6; Polaramine-d6; Polaronil-d6; d-Chlorpheniramine-d6 Maleate; (S)-Chlorpheniramine-d6 Maleate Salt

Database IDs

• PubChem SID: 162258832
• PubChem CID: 71314828

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.4312816
• LogD (pH = 7.4): 5.4882584
• Log P: 5.4890394
• Molar Refractivity: 80.9454 cm^3
• Polarizability: 31.873663 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C424307

The labelled S-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)