diphenylpyraline

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 460792611

| IUPAC_name = 4-benzhydryloxy-1-methyl-piperidine

| image = Diphenylpyraline.svg

| width = 180

| tradename =

| Drugs.com = {{drugs.com|international|diphenylpyraline}}

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = Oral, Topical

| bioavailability =

| metabolism =

| elimination_half-life = 24–40 hours{{cite journal | vauthors = Graham G, Bolt AG | title = Half-life of diphenylpyraline in man | journal = Journal of Pharmacokinetics and Biopharmaceutics | volume = 2 | issue = 3 | pages = 191–5 |date=June 1974 | pmid = 4156058 | doi = 10.1007/BF01059761 | s2cid = 38955052 }}

| excretion =

| IUPHAR_ligand = 7165

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 147-20-6

| ATC_prefix = R06

| ATC_suffix = AA07

| PubChem = 3103

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01146

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2992

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 33361OE3AV

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07862

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 59788

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1492

| C=19 | H=23 | N=1 | O=1

| smiles = O(C(c1ccccc1)c2ccccc2)C3CCN(C)CC3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OWQUZNMMYNAXSL-UHFFFAOYSA-N

| synonyms = 4-(diphenylmethoxy)-1-methyl-piperidine

}}

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.{{cite book | author = Swiss Pharmaceutical Society | title = Index Nominum 2000: International Drug Directory (Book with CD-ROM) | publisher = Medpharm Scientific Publishers | location = Boca Raton | year = 2000 | isbn = 3-88763-075-0 | url = https://books.google.com/books?id=5GpcTQD_L2oC&q=Diphenylpyraline&pg=PA358}}{{cite journal | vauthors = Puhakka H, Rantanen T, Virolainen E | title = Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis | journal = J Int Med Res | volume = 5 | issue = 1 | pages = 37–41 | year = 1977 | pmid = 14039| doi = 10.1177/030006057700500106 | s2cid = 19330175 }}{{cite journal | vauthors = Kubo N, Shirakawa O, Kuno T, Tanaka C | title = Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay | journal = Japanese Journal of Pharmacology | volume = 43 | issue = 3 | pages = 277–82 |date=March 1987 | pmid = 2884340 | doi = 10.1254/jjp.43.277| doi-access = free }} It is marketed in Europe for the treatment of allergies.{{cite book | vauthors = Hruby VJ, Vardanyan R, Vardanyan R | chapter = Antihistamine Drugs | title = Synthesis of Essential Drugs | publisher = Elsevier | location = Amsterdam | year = 2006 | isbn = 0-444-52166-6 | chapter-url = https://books.google.com/books?id=Jjc7KYWZdOYC&q=Diphenylpyraline&pg=PA230}} DPP has also been found to act as a dopamine reuptake inhibitor and produces hyperactivity in rodents.{{cite journal | vauthors = Lapa G, Mathews T, Harp J, Budygin E, Jones S | title = Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties | journal = Eur J Pharmacol | volume = 506 | issue = 3 | pages = 237–40 | year = 2005 | pmid = 15627433 | doi = 10.1016/j.ejphar.2004.11.017}} It has been shown to be useful in the treatment of Parkinsonism.{{cite journal | vauthors = Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I | title = Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients | journal = J Neurol Sci | volume = 182 | issue = 2 | pages = 95–7 | year = 2001 | pmid = 11137513 | doi = 10.1016/S0022-510X(00)00441-X| s2cid = 35946097 }}