Diphenylpyraline

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Diphenylpyraline
Diphenylpyraline.svg
Systematic (IUPAC) name
4-benzhydryloxy-1-methyl-piperidine
Clinical data
AHFS/Drugs.com International Drug Names
Legal status Prescription only
Routes Oral, Topical
Pharmacokinetic data
Half-life 24-40 hours[1]
Identifiers
CAS number 147-20-6 YesY
ATC code R06AA07
PubChem CID 3103
DrugBank DB01146
ChemSpider 2992 YesY
UNII 33361OE3AV YesY
KEGG D07862 YesY
ChEBI CHEBI:59788 YesY
ChEMBL CHEMBL1492 YesY
Synonyms 4-(diphenylmethoxy)-1-methyl-piperidine
Chemical data
Formula C19H23NO 
Mol. mass 281.392 g/mol
 YesY (what is this?)  (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]

Chemistry[edit]

Diphenylpyraline, 4-diphenylmethoxy-1-methylpiperidine, is synthesized by alkylating 4-hydroxy-1-methylpiperidine with benzhydrylbromide. Diphenylpyraline synthesis.png

See also[edit]

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. 
  2. ^ a b Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0. 
  3. ^ a b Puhakka 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. PMID 14039. 
  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, Victor J.; Ruben Vardanyan; Vardanyan, ۊRuben (2006). 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.