Tripelennamine Property

Melting point:

25°C

Boiling point:

bp0.1 138-142°; bp1.7 185-190°; bp20 193-205°

Density 

1.0683 (rough estimate)

refractive index 

nD25 1.5759-1.5765

pka

pKa 3.90±0.08(H2O t undefined I = 0.30 (NaCl)) (Uncertain);8.68±0.06(H2O t undefined I = 0.30 (NaCl)) (Uncertain)

Water Solubility 

587.3mg/L(30 ºC)

Stability:

Stable. Incompatible with strong oxidizing agents.

EPA Substance Registry System

Tripelennamine (91-81-6)

Safety

Hazardous Substances Data

91-81-6(Hazardous Substances Data)

Toxicity

LD50 oral in mouse: 152mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

H331Toxic if inhaled

H361Suspected of damaging fertility or the unborn child

H373May cause damage to organs through prolonged or repeated exposure

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P310Immediately call a POISON CENTER or doctor/physician.

P311Call a POISON CENTER or doctor/physician.

P314Get medical advice/attention if you feel unwell.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

Tripelennamine Chemical Properties,Usage,Production

Chemical Properties

White, bitter, crystalline powder. Solutions are acid to litmus.Soluble in water and alcohol; very slightly soluble in ether; practically insoluble in chloroform and benzene; 1% solution in water has a pH of 4.3.

Originator

Pyribenzamine,Ciba,US,1946

Uses

Medicine (antihistamine, sunburn treatment).

Uses

This drug lessens the allergic response of the organism caused by histamine. Tripelennamine is used for allergic symptoms, rhinitis, conjunctivitis, and for allergic and anaphylactic reactions. Synonyms of this drug are pelanin and pyribenzamine.

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

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.

Safety Profile

Poison by ingestion and intraperitoneal routes. Human mutation data reported. Has been implicated in aplastic anemia. Used as an antdustasnine. Addicts have added it to paregoric to make "blue velvet," whtch can cause euphoria by injection. When heated to decomposition it emits toxic fumes of NOx.

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.