| Identification | More | [Name]
Brompheniramine hydrogen maleate | [CAS]
980-71-2 | [Synonyms]
1-(n,n-dimethylamino)-3-(p-bromophenyl)-3-(alpha-pyridyl)propane maleate
1-p-bromophenyl-1-(2-pyridyl)-3-dimethylaminopropane maleate
BROMOPHENIRAMINE MALEATE
brompheniramine hydrogen maleate
BROMPHENIRAMINE MALEATE
(+/-)-BROMPHENIRAMINE MALEATE SALT
BROMPHENIRAMINE MALEATE SALT
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
dimotane
g-(4-bromophenyl)-N,N-dimethyl-2-pyridinepropanaminemaleate
gamma-(4-bromophenyl)-n,n-dimethyl-2-pyridinepropanamin(z)-2-butenedioate
gamma-(4-bromophenyl)-n,n-dimethyl-2-pyridinepropanamin(z)-butenedioate
ilvinmaleate
parabromdylaminemaleate
parabromodylaminemaleate
γ-(4-bromophenyl)-N,N-dimethyl-2-pyridinepropanaminemaleate | [EINECS(EC#)]
213-562-9 | [Molecular Formula]
C20H23BrN2O4 | [MDL Number]
MFCD00057367 | [Molecular Weight]
435.31 | [MOL File]
980-71-2.mol |
| Chemical Properties | Back Directory | [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 ]
neat | [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]
980-71-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36:Wear suitable protective clothing . | [RIDADR ]
3249 | [WGK Germany ]
3
| [RTECS ]
US4025000
| [TSCA ]
Yes | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
38220090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [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.1,2 | [Chemical Properties]
White Solid | [Originator]
Dimetane,Robins,US,1957 | [Uses]
Antihistaminic;H1 Antagonist | [Uses]
This drug is only available in combination with other
medications: Bromfed, Dimetane, Dimetapp, Drixomed, Histatab, Nasahist.
The only difference between this agent and chlorpheniramine is the substitution
of a bromine for a chlorine atom in brompheniramine. | [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 reacted
with sodium amide then dimethyl amino ethyl chloride to give 4-bromophenyldimethylaminoethyl-
pyridyl acetonitrile. This intermediate is then hydrolyzed
and decarboxylated to bromphenirame using 80% H2SO4 at 140°-150°C for
24 hours. The brompheniramine maleate may be made by reaction with
maleic 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 this
medication are similar to other classes of sedative antihistamines. Some medications
include parabens. Patients sensitive to parabens may develop a sensitivity
reaction. | [storage]
Store at -20°C | [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 |
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