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{{drugbox
{{Drugbox
| verifiedrevid = 460792611
| IUPAC_name = 4-benzhydryloxy-1-methyl-piperidine
| IUPAC_name = 4-benzhydryloxy-1-methyl-piperidine
| image =
| image = Diphenylpyraline.png
| width=120
 
<!--Clinical data-->
| tradename = 
| Drugs.com = {{drugs.com|international|diphenylpyraline}}
| pregnancy_category = 
| legal_status = Rx-only
| routes_of_administration = [[Mouth|Oral]], [[Topical]]
 
<!--Pharmacokinetic data-->
| bioavailability = 
| metabolism = 
| elimination_half-life = 24-40 hours<ref name="pmid4156058">{{cite journal | author = 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 | url = }}</ref>
| excretion = 
 
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 147-20-6
| CAS_number = 147-20-6
| ATC_prefix = R06
| ATC_prefix = R06
| ATC_suffix = AA07
| ATC_suffix = AA07
| ATC_supplemental =
| PubChem = 3103
| PubChem = 3103
| DrugBank = APRD00719
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| C=19 | H=23 | N=1 | O=1
| 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
 
<!--Chemical data-->
| C=19 | H=23 | N=1 | O=1  
| molecular_weight = 281.392 g/mol
| molecular_weight = 281.392 g/mol
| bioavailability =  
| smiles = O(C(c1ccccc1)c2ccccc2)C3CCN(C)CC3
| protein_bound =  
| InChI = 1/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
| metabolism =  
| InChIKey = OWQUZNMMYNAXSL-UHFFFAOYAE
| elimination_half-life =  
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| excretion =
| 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
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_US = <!-- A / B / C / D / X -->
| StdInChIKey = OWQUZNMMYNAXSL-UHFFFAOYSA-N
| pregnancy_category =
| synonyms = 4-(diphenylmethoxy)-1-methyl-piperidine
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only -->
| legal_status =  
| routes_of_administration =  
}}
}}
__NOTOC__
{{SI}}
{{CMG}}
==Overview==
'''Diphenylpyraline''' ('''DPP'''; sold as '''Allergen''', '''Arbid''', '''Belfene''', '''Diafen''', '''Hispril''', '''Histyn''', '''Lergobine''', '''Lyssipol''', '''Mepiben''', '''Neargal''') is a [[first-generation antihistamine]] with [[anticholinergic]] effects of the [[benzhydryl|diphenyl]][[piperidine]] class.<ref name="isbn3-88763-075-0">{{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 | pages = | isbn = 3-88763-075-0 | oclc = | doi = | url = http://books.google.com/?id=5GpcTQD_L2oC&lpg=PA358&dq=Diphenylpyraline&pg=PA358#v=onepage&q}}</ref><ref name="pmid14039">{{cite journal | author = 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}}</ref><ref name="pmid2884340">{{cite journal | author = 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| url = }}</ref> It is marketed in [[Europe]] for the treatment of [[allergy|allergies]].<ref name="isbn3-88763-075-0" /><ref name="pmid14039" /><ref name="isbn0-444-52166-6">{{cite book | author = Hruby, Victor J.; Ruben Vardanyan; Vardanyan, ۊRuben | title = Synthesis of essential drugs | publisher = Elsevier | location = Amsterdam | year = 2006 | pages = | isbn = 0-444-52166-6 | oclc = | doi = | url = http://books.google.com/?id=Jjc7KYWZdOYC&lpg=PA230&dq=Diphenylpyraline&pg=PA230#v=onepage&q}}</ref> DPP has also been found to act as a [[dopamine reuptake inhibitor]] and produces [[hyperactivity]] in rodents.<ref name="pmid15627433">{{cite journal | author = 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}}</ref> It has been shown to be useful in the treatment of [[Parkinsonism]].<ref name="pmid11137513">{{cite journal | author = 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}}</ref>


{{SI}}
==Chemistry==
Diphenylpyraline, 4-diphenylmethoxy-1-methylpiperidine, is synthesized by alkylating 4-hydroxy-1-methylpiperidine with benzhydrylbromide.
[[File:Diphenylpyraline synthesis.png|none|left|500px]]


{{EH}}
== See also ==
==Overview==
* [[Benzatropine]]
'''Diphenylpyraline''' is an [[antihistamine]].
* [[Desoxypipradrol]]
* [[Pipradrol]]


==External links==
== References ==
* {{cite journal | author = 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 | id = PMID 15627433}}
{{Reflist|2}}
* {{cite journal | author = 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 | id = PMID 11137513}}
* {{cite journal | author = 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 | id = PMID 14039}}


{{Antihistamines}}
{{Antihistamines}}
 
{{Stimulants}}
{{SIB}}
[[th:ไดฟีนิลไพราลีน]]
[[Category:H1 receptor antagonists]]
[[Category:H1 receptor antagonists]]
 
[[Category:Piperidines]]
{{WH}}
[[Category:Ethers]]
 
[[Category:Stimulants]]
{{WS}}
[[Category:Drug]]

Latest revision as of 17:26, 10 April 2015

Diphenylpyraline
Clinical data
Synonyms4-(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
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC19H23NO
Molar mass281.392 g/mol
3D model (JSmol)
  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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

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

See also

References

  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. ↑ 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.
  3. ↑ 3.0 3.1 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.

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