Brompheniramine

Title: Brompheniramine
CAS Registry Number: 86-22-6
CAS Name: g-(4-Bromophenyl)-N,N-dimethyl-2-pyridinepropanamine
Additional Names: 2-[p-bromo-a-(2-dimethylaminoethyl)benzyl]pyridine; 1-(p-bromophenyl)-1-(2-pyridyl)-3-dimethylaminopropane; 3-(p-bromophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamine; parabromdylamine
Molecular Formula: C16H19BrN2
Molecular Weight: 319.24
Percent Composition: C 60.20%, H 6.00%, Br 25.03%, N 8.78%
Literature References: Prepn from a-(p-bromophenyl)-a-(b-dimethylaminoethyl)-2-pyridylacetonitrile: Sperber et al., US 2567245 (1951); US 2676964 (1954 to Schering). Prepn of d-form: L. A. Walter, US 3061517 (1962 to Schering).
Properties: Oily liquid. Slightly yellow color. Characteristic amine-like odor. bp0.5 147-152°. Soluble in dilute acids.
Boiling point: bp0.5 147-152°
Derivative Type: Maleate
CAS Registry Number: 980-71-2
Trademarks: Dimegan (Dexo); Dimetane (Robins); Dimotane (Robins); Ilvin (Merck KGaA); Nagemid (Dexo); Symptom 3 (Parke-Davis); Veltane (Lannett)
Molecular Formula: C16H19BrN2.C4H4O4
Molecular Weight: 435.31
Percent Composition: C 55.18%, H 5.33%, Br 18.36%, N 6.44%, O 14.70%
Properties: Crystals, mp 132-134°. Sol in water, somewhat less sol in alcohol. pH of a 2% aq soln about 5.
Melting point: mp 132-134°
Derivative Type: d-Form
CAS Registry Number: 132-21-8
Additional Names: Dexbrompheniramine; (+)-parabromdylamine
Properties: Oily liquid. [a]D25 +42.7° (c = 1 in DMF).
Optical Rotation: [a]D25 +42.7° (c = 1 in DMF)
Derivative Type: d-Form maleate
CAS Registry Number: 2391-03-9
Trademarks: Disomer (Schering); Ebalin (Allergopharma)
Molecular Formula: C16H19BrN2.C4H4O4
Molecular Weight: 435.31
Percent Composition: C 55.18%, H 5.33%, Br 18.36%, N 6.44%, O 14.70%
Properties: Crystals, mp 103-113°.
Melting point: mp 103-113°
Therap-Cat: Antihistaminic.
Keywords: Antihistaminic; Alkylamine Derivatives.
Bromphenol Blue Bromthymol Blue Bromuconazole Bronopol Broparoestrol

Brompheniramine
Brompheniramine structure.svg
Systematic (IUPAC) name
3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-2-yl-propan-1-amine
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682545
Pregnancy cat. C (USA)
Legal status Schedule 2-4 (depending on formulation and usage) (AU) Unscheduled, OTC
Routes Oral
Pharmacokinetic data
Bioavailability  ?
Metabolism Hepatic
Half-life 24.9 ± 9.3 hours[1]
Excretion Urine
Identifiers
CAS number 86-22-6 YesY
ATC code R06AB01
PubChem CID 6834
DrugBank DB00835
ChemSpider 6573 YesY
UNII H57G17P2FN YesY
KEGG D07543 YesY
ChEBI CHEBI:3183 YesY
ChEMBL CHEMBL811 YesY
Chemical data
Formula C16H19BrN2 
Mol. mass 319.24 g/mol
 YesY (what is this?)  (verify)

Brompheniramine (Bromfed, Dimetapp, Bromfenex, Dimetane, BPN, Lodrane), commonly marketed as its salt brompheniramine maleate, is an antihistamine drug of the propylamine (alkylamine) class. It is readily available over the counter and is indicated for the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing. It is a first-generation antihistamine.

Brompheniramine is part of a series of antihistamines including pheniramine (Naphcon) and its halogenated derivatives and others including fluorpheniramine, chlorpheniramine, dexchlorpheniramine (Polaramine), deschlorpheniramine, dipheniramine (also known as triprolidine with the trade name Actifed), and iodopheniramine.

The halogenated alkylamine antihistamines all exhibit optical isomerism and brompheniramine products contain racemic brompheniramine maleate whereas dexbrompheniramine (Drixoral) is the dextrorotary (right-handed) stereoisomer.

Brompheniramine has antidepressant properties, inhibiting reuptake of the neurotransmitter serotonin. Based on this knowledge, Arvid Carlsson and his colleagues, working at the Swedish company Astra AB, were able to derive the first marketed selective serotonin reuptake inhibitor, zimelidine, from brompheniramine.[2]

Like other agents of this type, brompheniramine also has analgesic-sparing (potentiating) effects on opioid analgesics, commonly reducing codeine, dihydrocodeine, and hydrocodone requirements by 10 to 35 percent.