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

• ChemBase ID: 73206
• Molecular Formular: C20H23BrN2O4
• Molecular Mass: 435.31162
• Monoisotopic Mass: 434.08411923
• SMILES: c1(C(CCN(C)C)c2ccccn2)ccc(cc1)Br.OC(=O)/C=C\C(=O)O
• Canonical SMILES: CN(CCC(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; [3-(4-bromophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
• IUPAC Traditional name: brompheniramine; maleic acid
• Synonyms: Brompheniramine; (±)-Brompheniramine maleate salt; γ-(4-Bromophenyl)-N,N-dimethyl-2-pyridinepropanamine Maleate; 2-[p-Βromo-α-[2-(dimethylamino)ethyl]benzyl]pyridine Maleate; (+/-)-Brompheniramine Maleate; Bromphen Maleate; Dimegan; Dimetane; Parabromdylamine Maleate; Parabromodylamine Maleate; Veltane; dl-Brompheniramine Maleate; Brompheniramine Maleate

Database IDs

• CAS Number: 980-71-2
• EC Number: 213-562-9
• MDL Number: MFCD00057367
• PubChem SID: 24278261; 162038126
• PubChem CID: 5281067

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• 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

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 134-135°C

Safety Information

• Storage Condition: -20°C; Refrigerator
• RTECS: US4025000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

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

Product Information

• Salt Data: maleate

DETAILS

Selleck Chemicals - S2585

Biological Activity:
Brompheniramine is a histamine H1 receptors antagonist. Brompheniramine also functions as a moderately effective anticholinergic agent, and is likely an antimuscarinic agent similar to other common antihistamines such as diphenhydramine. Brompheniramine is an antihistamine drug of the propylamine (alkylamine) class. Brompheniramine has antidepressant properties, inhibiting reuptake of the neurotransmitter serotonin.Brompheniramine also has analgesic-sparing (potentiating) effects on opioid analgesics, commonly reducing codeine, dihydrocodeine, and hydrocodone requirements by 10 to 35 percent. Brompheniramine is metabolised by cytochrome P450s. [1][2]

Sigma Aldrich - B2390

Biochem/physiol Actions
Antihistamine; H1 histamine receptor antagonist.

Toronto Research Chemicals - B686355

Antihistaminic.

REFERENCES

• Nosal R et al. Neuro Endocrinol Lett. 2009;30 Suppl 1:133-6.
• Walle, T., et al.: Biochem. Pharmacol., 37, 115 (1988)
• Yang, W., et al.: J. Pharm. Pharmacol., 56, 703 (1988)
• Xu, H., et al.: Anal. Sci., 20, 1409 (1988)