N-2-(4-bromobenzhydryloxy)ethyldimethylamine

Absorption

Well absorbed in the digestive tract.

Toxicity

Signs of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, swelling of face, lips, tongue, or throat.

Originator

Bromazine,Shanghai Lansheng Corporation

The Uses of N-2-(4-bromobenzhydryloxy)ethyldimethylamine

Antihistaminic.

Indications

For management of symptoms related to hay fever and other types of allergy and used to help bring up phlegm, thin secretions, and make a cough productive.

Background

Bromodiphenhydramine is an ethanolamine antihistamine with antimicrobial property. Bromodiphenhydramine is used in the control of cutaneous allergies. Ethanolamine antihistamines produce marked sedation in most patients.

Definition

ChEBI: A tertiary amino compound that is the 4-bromobenzhydryl ether of 2-(dimethylamino)ethanol. An antihistamine with antimicrobial properties, it is used in the control of cutaneous allergies.

Manufacturing Process

28.1 parts of p-bromobenzhydrylbromide are heated to boiling, under reflux and with stirring, with 50 parts of ethylene chlorohydrin and 5.3 parts of calcined sodium carbonate. The reaction product is extracted with ether and the etheral solution washed with water and dilute hydrochloric acid. The residue from the solution in ether [p-bromobenzhydryl(β-chloroethyl)ether].
28.1 parts of this ether are heated with 12 parts of dimethylethylamine in a sealed tube for 4 hours at 110°C. The product of the reaction is extracted several time with dilute hydrochloric acid. The acid solution made alkaline, in the cold, with concentrated caustic soda solution, and the base which separates taken up in ether. The ether extract is washed with concentrated potassium carbonate solution, evaporated down, and the residue distilled in vacuo. Boiling point of p-bromo-α-phenylbenzyloxy)-N,N-dimethylethylamine 151-154°C under 0.3 mm.
p-Bromo-α-phenylbenzyloxy)-N,N-dimethylethylamine may be used as a hydrochloride.

brand name

Ambodryl.

Therapeutic Function

Antihistaminic

Pharmacokinetics

Bromodiphenhydramine is an antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, Bromodiphenhydramine competes with free histamine for binding at HA-receptor sites. Bromodiphenhydramine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of Bromodiphenhydramine. This anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.

Metabolism

Hepatic (cytochrome P-450 system); some renal.