Diphenylpyraline

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Structural formula
Structural formula of diphenylpyraline
General
Non-proprietary name Diphenylpyraline
other names
  • 4-benzhydryloxy-1-methylpiperidine
  • 4- (Diphenylmethoxy) -1-methylpiperidine ( IUPAC )
Molecular formula C 19 H 23 NO
External identifiers / databases
CAS number
  • 147-20-6
  • 132-18-3 (hydrochloride)
PubChem 3103
DrugBank DB01146
Wikidata Q411150
Drug information
ATC code

R06 AA07 , R06 AA57

Drug class
properties
Molar mass 281.39 g · mol -1
Physical state

firmly

Melting point

30 ° C

boiling point

158-160 ° C (266 Pa)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances

Hydrochloride

07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Diphenylpyralin is a drug that is used as a systemic antiallergic agent .

It belongs to the class of antihistamines of the first generation or to the group of aminoalkyl ethers .

Diphenylpyralin was in Germany (as a flu remedy) and Switzerland (as an oral snuff remedy) in the form of combination preparations on the market.

In addition to the antiallergic effect, the drug is also said to have an anti-secretion effect.

Chemical synthesis

The compound can be prepared by alkylation ( Williamson ether synthesis ) of 4-hydroxy-1-methylpiperidine with benzhydryl bromide :

Trade names

Combination
preparations Perdiphen (D, excluding trade), Arbid drops (CH, formulation until 2011)

Diphenylpyraline synthesis

Individual evidence

  1. ↑ EW Neuhoff, H. Auterhoff : For the analysis of antihistamines. 4th communication . In: Archives of Pharmacy . tape 288 , no. 8-9 , 1955, pp. 400-407 , doi : 10.1002 / ardp.19552880811 .
  2. ↑ Patent DE934890 : Process for the production of basic benzhydryl ethers. Published on November 10, 1955 , applicant: Chem. Fabr. Promonta, inventor: Wilhelm Alfons Schuler. ‌
  3. ↑ a b Data sheet 4-Diphenylmethoxy-1-methylpiperidine hydrochloride from Sigma-Aldrich , accessed on January 5, 2012 ( PDF ).
  4. ↑ K. Langbein, H.-P. Martin, H. Weiss: Bitter Pills. Benefits and risks of the drugs. Kiepenheuer & Witsch, Cologne 2004, p. 241.
  5. ↑ a b Entry on Diphenylpyralin in Pharmawiki , accessed on January 28, 2017.
  6. ↑ LH Knox, R. Kapp: 1-Alkylpiperidyl-4-benzhydryl ethers, acid salts thereof and their preparation. Patented Aug. 23, 1949 (United States Patent 2,479,843; Google patents ).