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Diphenylpyraline

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Diphenylpyraline
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
Eliminationhalf-life24–40 hours[1]
Identifiers
  • 4-benzhydryloxy-1-methyl-piperidine
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.005.170Edit this at Wikidata
Chemical and physical data
FormulaC19H23NO
Molar mass281.399 g·mol−1
3D model (JSmol)
  • O(C(c1ccccc1)c2ccccc2)C3CCN(C)CC3
  • InChI=1S/C19H23NO/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-19H,12-15H2,1H3 checkY
  • Key:OWQUZNMMYNAXSL-UHFFFAOYSA-N checkY
  (verify)

Diphenylpyraline (DPP; sold asAllergen,Arbid,Belfene,Diafen,Hispril,Histyn,Lergobine,Lyssipol,Mepiben,Neargal) is afirst-generation antihistamine withanticholinergic effects of thediphenylpiperidine class.[2][3][4] It is marketed inEurope for the treatment ofallergies.[2][3][5] DPP has also been found to act as adopamine reuptake inhibitor and produceshyperactivity in rodents.[6] It has been shown to be useful in the treatment ofParkinsonism.[7]

Synthesis

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

References

[edit]
  1. ^Graham G, Bolt AG (June 1974). "Half-life of diphenylpyraline in man".Journal of Pharmacokinetics and Biopharmaceutics.2 (3):191–5.doi:10.1007/BF01059761.PMID 4156058.S2CID 38955052.
  2. ^abSwiss Pharmaceutical Society (2000).Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers.ISBN 3-88763-075-0.
  3. ^abPuhakka H, Rantanen T, Virolainen E (1977). "Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis".J Int Med Res.5 (1):37–41.doi:10.1177/030006057700500106.PMID 14039.S2CID 19330175.
  4. ^Kubo N, Shirakawa O, Kuno T, Tanaka C (March 1987)."Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay".Japanese Journal of Pharmacology.43 (3):277–82.doi:10.1254/jjp.43.277.PMID 2884340.
  5. ^Hruby VJ, Vardanyan R, Vardanyan R (2006)."Antihistamine Drugs".Synthesis of Essential Drugs. Amsterdam: Elsevier.ISBN 0-444-52166-6.
  6. ^Lapa G, Mathews T, Harp J, Budygin E, Jones S (2005). "Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties".Eur J Pharmacol.506 (3):237–40.doi:10.1016/j.ejphar.2004.11.017.PMID 15627433.
  7. ^Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I (2001). "Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients".J Neurol Sci.182 (2):95–7.doi:10.1016/S0022-510X(00)00441-X.PMID 11137513.S2CID 35946097.
  8. ^US 2479843, Knox LH, Kapp R, "1-Alkylpiperidyl-4-benzhydryl ethers, acid salts thereof and their preparation", issued 23 August 1949, assigned to Nopco Chemical Company. 
  9. ^DE 934890, Schuler WA, "Verfahren zur Herstellung von basischen Benzhydryläthern [Process for the production of basic benzhydrylethers]", issued 10 November 1955, assigned to Chemische Fabrik Promonta LLC. 
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