Chemistry:Diphenylpyraline

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Short description: Chemical compound
Diphenylpyraline
Diphenylpyraline.svg
Clinical data
Other names4-(diphenylmethoxy)-1-methyl-piperidine
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral, Topical
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life24–40 hours[1]
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC19H23NO
Molar mass281.399 g·mol−1
3D model (JSmol)
  (verify)

Diphenylpyraline (DPP; sold as Allergen, Arbid, Belfene, Diafen, Hispril, Histyn, Lergobine, Lyssipol, Mepiben, Neargal) is a first-generation antihistamine with anticholinergic effects of the diphenylpiperidine class.[2][3][4] It is marketed in Europe for the treatment of allergies.[2][3][5] DPP has also been found to act as a dopamine reuptake inhibitor and produces hyperactivity in rodents.[6] It has been shown to be useful in the treatment of Parkinsonism.[7]

Synthesis

Diphenylpyraline synthesis via coupling of 4-hydroxy-1-methylpiperidine with benzhydrylbromide[8][9]

References

  1. ↑ "Half-life of diphenylpyraline in man". Journal of Pharmacokinetics and Biopharmaceutics 2 (3): 191–5. June 1974. doi:10.1007/BF01059761. PMID 4156058. 
  2. ↑ 2.0 2.1 Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0. https://books.google.com/books?id=5GpcTQD_L2oC&q=Diphenylpyraline&pg=PA358. 
  3. ↑ 3.0 3.1 "Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis". J Int Med Res 5 (1): 37–41. 1977. doi:10.1177/030006057700500106. PMID 14039. 
  4. ↑ "Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay". Japanese Journal of Pharmacology 43 (3): 277–82. March 1987. doi:10.1254/jjp.43.277. PMID 2884340. 
  5. ↑ "Antihistamine Drugs". Synthesis of Essential Drugs. Amsterdam: Elsevier. 2006. ISBN 0-444-52166-6. https://books.google.com/books?id=Jjc7KYWZdOYC&q=Diphenylpyraline&pg=PA230. 
  6. ↑ "Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties". Eur J Pharmacol 506 (3): 237–40. 2005. doi:10.1016/j.ejphar.2004.11.017. PMID 15627433. 
  7. ↑ "Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients". J Neurol Sci 182 (2): 95–7. 2001. doi:10.1016/S0022-510X(00)00441-X. PMID 11137513. 
  8. ↑ Knox LH, Kapp R, "1-Alkylpiperidyl-4-benzhydryl ethers, acid salts thereof and their preparation", US patent 2479843, issued 23 August 1949, assigned to Nopco Chemical Company.
  9. ↑ Schuler WA, "Verfahren zur Herstellung von basischen Benzhydryläthern [Process for the production of basic benzhydrylethers]", DE patent 934890, issued 10 November 1955.




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