Diphenylpyraline Hydrochloride Chemical Properties

Melting point:

203-205 °C(lit.)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

Solid

color 

White to Off-White

Merck 

13,3363

Stability:

Hygroscopic

EPA Substance Registry System

Diphenylpyraline hydrochloride (132-18-3)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

26-36

RIDADR 

3249

WGK Germany 

3

RTECS 

TM7823600

HazardClass 

6.1(b)

PackingGroup 

III

Toxicity

mouse,LD50,intramuscular,64300ug/kg (64.3mg/kg),Drugs in Japan Vol. 6, Pg. 333, 1982.

MSDS

• Language:English Provider:SigmaAldrich

Diphenylpyraline Hydrochloride Usage And Synthesis

Description

Diphenylpyraline is an antihistamine drug with anticholinergic and sedative action. It is intended for symptomatic treatment of seasonal allergies and allergic reactions as well as an adjuvant drug in anaphylactic reaction therapy. Synonyms of this drug are arbid, timpil, histryl, hispril, and others.

Originator

Diafen,Riker,US,1955

Uses

Antihistaminic;H1 antagonist

Uses

Diphenylpyraline Hydrochloride is a salt of Diphenylpyraline (D492110), an H1 receptor antagonist (an antihistamine) and is commonly prescribed to treat allergic and vasomotor rhinitis. There is also some research being conducted on diphenylpyraline derivatives to determine their antimycobacterial and antifungal activity.

Definition

ChEBI: The hydrochloride salt of diphenylpyraline. A sedating antihistamine, it is used as the hydrochloride for the symptomatic relief of allergic conditions including rhinitis and hay fever, and in pruritic skin disorders.

Manufacturing Process

A mixture of 46 grams of 1-methyl-4-piperidinol (0.4 mol), 49.4 grams of benzhydryl
omide (0.2 mol) and 100 ml of xylene was refluxed for approximately 24 hours. The reaction mixture separated into two phases with the upper phase containing the desired ether compound dissolved in xylene. The lower phase consisted of the hydro
omide salt of the excess 1-methyl-4- piperidinol. The upper phase was separated from the lower phase and the desired benzhydryl ether recovered in the crude state by distilling off the xylene under reduced pressure.
The crude benzhydryl ether was a clear reddish oil. It was dissolved in 75 ml of 20% hydrochloric acid and the aqueous acid solution then washed three times with 50 ml portions each of ethyl ether. The aqueous acid solution was then decolorized with activated carbon and thereafter slowly admixed with 75 ml of 28% aqueous ammonia. The benzhydryl ether separated as an oily material and was removed from the aqueous mixture by extraction with three 50 ml portions of ethyl ether.
On evaporation of the ethyl ether from the ethyl ether solution, the benzhydryl ether was recovered as a pale yellow oil. The benzhydryl ether was dissolved in 60 ml of isopropanol and the isopropanol solution acidified to a pH of 3 with dry hydrogen chloride-methanol solution. The acidic propanol solution was then diluted with ethyl ether until a faint turbidity was observed. In a short time, the crystalline hydrochloride salt of the benzhydryl ether separated from the propanol solution. The crystallized salt was recrystallized once from 75 ml of isopropanol with the aid of ethyl ether in order to further purify the material. A yield of the pure hydrochloride salt of 1-methylpiperidyl- 4-benzhydryl ether of 24.5 grams was obtained. This was 39% of the theoretical yield. The pure material had a melting point of 206°C.

Therapeutic Function

Antihistaminic

General Description

Diphenylpyr alinehydrochloride, 4-(diphenylmethoxy)-1-methylpiperidinehydrochloride (Hispril, Diafen) is a white or slightly offwhitecrystalline powder that is soluble in water or alcohol.Diphenylpyraline is structurally related to diphenhydraminewith the aminoalkyl side chain incorporated in a piperidinering. It is a potent antihistaminic, and the usual dose is 2 mg3 or 4 times daily.

Synthesis

Diphenylpyraline, 4-diphenylmethoxy-1-methylpiperidine (16.1.32), is synthesized by alkylating 4-hydroxy-1-methylpiperidine with benzhydrylbromide.

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