Chemical Properties
oily liquid
General Description
Oily liquid with an amine odor.
Air & Water Reactions
Water soluble.
Reactivity Profile
Tripelennamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Health Hazard
SYMPTOMS: Symptoms of exposure to Tripelennamine may include euphoria, aplastic anemia, excitement, hallucinations, ataxia, incoordination, athetosis, convulsions, postictal depression, dry mouth, fixed dilated pupils, flushing of the face, fever, central nervous system depression, drowsiness and coma.
Fire Hazard
Flash point data for Tripelennamine are not available. Tripelennamine is probably combustible.
Originator
Pyribenzamine,Ciba,US,1946
Definition
ChEBI: Tripelennamine is an aromatic amine.
Manufacturing Process
46 g of α-benzylaminopyridine in 50 cc of dry toluene are heated to 80°C [the
α-benzylaminopyridine may be obtained either according to the method of
Tchitchibabine and Knunjanz, Berichte, 64, 2839 (1931), which consists in
warming α-aminopyridine with benzaldehyde in formic acid, or alternatively by
the action of benzyl chloride on sodio-α-aminopyridine]. To the toluene
solution there are added gradually 9.5 g of 85% sodamide. After evolution of
ammonia, the major part of the toluene is distilled off; into the pasty mass
which remains there are poured 120 cc of an ethereal solution of 27 g of
dimethylaminochloroethane.
The mixture is heated until the temperature reaches 140°C, the ether distilling
out, then finally heated under reduced pressure (150 mm Hg) for 1/2 hour.
The mass is taken up with dilute hydrochloric acid and ether, neutralized at pH
7, and α-benzylaminopyridine separates. After making alkaline, using excess of potash, it is extracted with benzene, dried and distilled. The product
thereby obtained, dimethylamino-ethyl-N-benzyl-N-α-arninopyridine, boils at
135° to 190°C/1.7 mm, according to US Patent 2,502,151.
Brand name
PBZ (Novartis).
Therapeutic Function
Antihistaminic
Synthesis
Tripelennamine, N-benzyl-N??,N??-dimethyl-N-2-pyridylethylenediamine
(16.1.6), is synthesized by reacting 2-benzylaminopyrridine (16.1.5) with 2-dimethylaminoethylchloride
in the presence of sodium amide. 2-Benzylaminopyrridine, in turn,
can be easily synthesized by reduction of a Schiff base, synthesized by condensation of
2-aminopyrridine with benzaldehyde.
Metabolic pathway
When pyribenzamine is
incubated with rat liver microsomes, it is metabolized via N-oxide formation and
N-dealkylation which includes removal of the
dimethylamino moiety, the thiophenylmethyl moiety of
methaphenilene, and the benzyl moiety of
pyribenzamine.
