[3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine

• ChemBase ID: 985
• Molecular Formular: C16H19ClN2
• Molecular Mass: 274.78846
• Monoisotopic Mass: 274.1236763
• SMILES: Clc1ccc(C(CCN(C)C)c2ncccc2)cc1
• Canonical SMILES: CN(CCC(c1ccccn1)c1ccc(cc1)Cl)C
• InChI: InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3
• InChIKey: SOYKEARSMXGVTM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
• IUPAC Traditional name: hayon
• Brand Name: Aller-Chlor; Allergican; Allergisan; Antagonate; Chlo-Amine; Chlor-Trimeton; Chlor-Trimeton Allergy; Chlor-Trimeton Repetabs; Chlor-Tripolon; Chlorate; Chloropiril; Cloropiril; Efidac 24 Chlorpheniramine Maleate; Gen-Allerate; Haynon; Histadur; Kloromin; Mylaramine; Novo-Pheniram; Pediacare Allergy Formula; Phenetron; Piriton; Polaramine; Polaronil; Pyridamal 100; Telachlor; Teldrin
• Synonyms: Chloropheniramine; Chlorophenylpyridamin; Chlorophenylpyridamine; Chloroprophenpyridamine; Chlorphenamine; Chlorpheniramine Maleate; Chlorprophenpyridamine; Clorfeniramina; Dexchlorpheniramine; Dexchlorpheniramine Maleate; Chlorpheniramine

Database IDs

• CAS Number: 132-22-9
• PubChem SID: 46508253; 160964448
• PubChem CID: 2725

CALCULATED PROPERTIES

JChem

• 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: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.74
• LOG S: -3.72
• Solubility (Water): 5.19e-02 g/l

PROPERTIES

Physical Property

• Solubility: 5.5 g/L
• Hydrophobicity(logP): 3.2

DETAILS

DrugBank - DB01114

• Drug Groups: approved
• Description: A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than promethazine. [PubChem]
• Indication: For the treatment of rhinitis, urticaria, allergy, common cold, asthma and hay fever.
• Pharmacology: In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H₁-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Chlorpheniramine, is a histamine H1 antagonist (or more correctly, an inverse histamine agonist) of the alkylamine class. It competes with histamine for the normal H₁-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.
• Toxicity: Oral LD50 (rat): 306 mg/kg; Oral LD50 (mice): 130 mg/kg; Oral LD50 (guinea pig): 198 mg/kg [Registry of Toxic Effects of Chemical Substances. Ed. D. Sweet, US Dept. of Health & Human Services: Cincinatti, 2010.] ; Also a mild reproductive toxin to women of childbearing age.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic via Cytochrome P450 (CYP450) enzymes.
• Absorption: Well absorbed in the gastrointestinal tract.
• Half Life: 21-27 hours
• Protein Binding: 72%
• References: * [MSDS]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• * MSDS