Introduction：Basic information about Brompheniramine hydrogen maleate CAS 980-71-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Brompheniramine hydrogen maleate Basic information
| Product Name: | Brompheniramine hydrogen maleate |
| Synonyms: | 2-(p-bromo-alpha-(2-(dimethylamino)ethyl)benzyl)pyridinemaleate(1:1);2-(p-bromo-alpha-(2-(dimethylamino)ethyl)benzyl)-pyridinmaleate(1:1);dimegan;dimetane;dimetanemaleate;RS-brompheniramine maleate;dimotane;g-(4-bromophenyl)-N,N-dimethyl-2-pyridinepropanaminemaleate |
| CAS: | 980-71-2 |
| MF: | C20H23BrN2O4 |
| MW: | 435.31 |
| EINECS: | 213-562-9 |
| Product Categories: | Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals |
| Mol File: | 980-71-2.mol |
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Brompheniramine hydrogen maleate Chemical Properties
| Melting point | 134-135°C |
| Fp | 9℃ |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Soluble in water, freely soluble in ethanol (96 per cent), in methanol and in methylene chloride. |
| form | Solid |
| color | White to Off-White |
| λmax | 261nm(lit.) |
| Merck | 14,1443 |
| Stability: | Hygroscopic |
| Major Application | pharmaceutical (small molecule) |
| 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 |
| SMILES | C(C1=CC=C(Br)C=C1)(C1=NC=CC=C1)CCN(C)C.C(O)(=O)/C=C\C(O)=O |
| LogP | 3.565 (est) |
| CAS DataBase Reference | 980-71-2(CAS DataBase Reference) |
| EPA Substance Registry System | 2-Pyridinepropanamine, .gamma.-(4-bromophenyl)-N,N-dimethyl-, (2Z)-2-butenedioate (1:1) (980-71-2) |
Safety Information
| Hazard Codes | Xn,Xi,T,F |
| Risk Statements | 22-39/23/24/25-23/24/25-11 |
| Safety Statements | 36-45-36/37-16-7 |
| RIDADR | 3249 |
| WGK Germany | 3 |
| RTECS | US4025000 |
| TSCA | TSCA listed |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 38220090 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
Brompheniramine hydrogen maleate Usage And Synthesis
| Description | Brompheniramine is a first generation antihistamine of the propylamine class. It antagonizes histamine H1 receptors (Ki = 6.06 nM) and also inhibits the reuptake of serotonin and norepinephrine. |
| Chemical Properties | White Solid |
| Originator | Dimetane,Robins,US,1957 |
| Uses | This drug is only available in combination with othermedications: Bromfed, Dimetane, Dimetapp, Drixomed, Histatab, Nasahist.The only difference between this agent and chlorpheniramine is the substitutionof a bromine for a chlorine atom in brompheniramine. |
| Uses | Antihistaminic;H1 Antagonist |
| Uses | An antihistamine and also an inhibitor of serotonin reuptake |
| Definition | ChEBI: The maleic acid salt of brompheniramine. A histamine H1 receptor antagonist, it is used for the symptomatic relief of allergic conditions, including rhinitis and conjunctivitis. |
| Manufacturing Process | Initially, 4-bromobenzyl-cyanide is reacted with sodium amide and 2-chloropyridine to give bromophenyl-pyridyl acetonitrile. This is then reactedwith sodium amide then dimethyl amino ethyl chloride to give 4-bromophenyldimethylaminoethyl-pyridyl acetonitrile. This intermediate is then hydrolyzedand decarboxylated to bromphenirame using 80% H2SO4 at 140°-150°C for24 hours. The brompheniramine maleate may be made by reaction withmaleic acid in ethanol followed by recrystallization from pentanol. |
| Brand name | Dimetane (Wyeth). |
| Therapeutic Function | Antihistaminic |
| General Description | Brompheniraminemaleate, (+)2-[p-bromo-α-[2-(dimethylamino)ethyl]benzyl]pyridine bimaleate (Dimetane), differs fromchlorpheniramine by the substitution of a bromine atom forthe chlorine atom. Its actions and uses are like those of chlorpheniramine.It has a half-life of 25 hours, which is almosttwice that of chlorpheniramine. |
| Side effects | The side effects of thismedication are similar to other classes of sedative antihistamines. Some medicationsinclude parabens. Patients sensitive to parabens may develop a sensitivityreaction. |
| References | [1] THOMAS HOEGBERG. Synthesis of pyridylallylamines related to zimelidine and their inhibition of neuronal monoamine uptake[J]. Journal of Medicinal Chemistry, 1981, 24 12: 1499-1507. DOI: 10.1021/jm00144a025 |
Brompheniramine hydrogen maleate Preparation Products And Raw materials
| Raw materials | 2-Chloropyridine-->Sulfuric acid-->Sodium amide-->N,N-DIMETHYLAMINOETHYL CHLORIDE-->Maleic acid-->4-Bromophenylacetonitrile |
