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

• ChemBase ID: 133072
• Molecular Formular: C20H23ClN2O4
• Molecular Mass: 390.86062
• Monoisotopic Mass: 390.13463491
• SMILES: CN(C)CC[C@@H](c1ccc(cc1)Cl)c1ccccn1.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-;/m0./s1
• InChIKey: DBAKFASWICGISY-DASCVMRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; [(3S)-3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
• IUPAC Traditional name: (+)-chlorpheniramine; maleic acid
• Synonyms: (γS)-γ-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine (2Z)-2-Butenedioate; 2-[p-Chloro-α-[2-(dimethylamino)ethyl]benzyl]pyridine Maleate; (+)-Chlorpheniramine Maleate; Dexchloropheniramine Maleate; Dextrochlorpheniramine Maleate; Fortamine; Isomerine; Phenamin; Phendextro; Polamin; Polaramin; Polaramine; Polaronil; d-Chlorpheniramine Maleate; (S)-Chlorpheniramine Maleate Salt; (S)-γ-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine maleate salt; S-(+)-Chlorpheniramine maleate salt

Database IDs

• CAS Number: 2438-32-6
• EC Number: 219-450-6
• MDL Number: MFCD00079046
• PubChem SID: 24278317; 162227349
• PubChem CID: 5281070

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

PROPERTIES

Physical Property

• Solubility: Chloroform; DMF
• Apperance: White Solid
• Melting Point: 97-113°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: US6504000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... HRH1(3269)

DETAILS

Sigma Aldrich - C4915

Biochem/physiol Actions
H1 histamine receptor antagonist; active isomer.

Toronto Research Chemicals - C424305

The 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)