Diphenylpyraline

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Diphenylpyraline
Clinical data
Synonyms	4-(diphenylmethoxy)-1-methyl-piperidine
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral, Topical
ATC code	R06AA07 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Elimination half-life	24-40 hours
Identifiers
	IUPAC name 4-benzhydryloxy-1-methyl-piperidine;
CAS Number	147-20-6 ;
PubChem CID	3103;
DrugBank	DB01146 ;
ChemSpider	2992 ;
UNII	33361OE3AV;
KEGG	D07862 ;
ChEBI	CHEBI:59788 ;
ChEMBL	ChEMBL1492 ;
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
Formula	C19H23NO
Molar mass	281.392 g/mol
3D model (JSmol)	Interactive image;
	SMILES O(C(c1ccccc1)c2ccccc2)C3CCN(C)CC3;
	InChI 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 ; Key:OWQUZNMMYNAXSL-UHFFFAOYSA-N ;
(verify)

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 diphenyl piperidine 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.

References

↑ 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.
↑ ^2.0 ^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.
↑ ^3.0 ^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.
↑ 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.
↑ Hruby, Victor J.; Ruben Vardanyan; Vardanyan, ۊRuben (2006). Synthesis of essential drugs. Amsterdam: Elsevier. ISBN 0-444-52166-6.
↑ 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.
↑ 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.

Template:Stimulants

[pmid4156058-1] 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.

[isbn3-88763-075-0-2] 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.

[pmid14039-3] 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.

[pmid2884340-4] 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.

[isbn0-444-52166-6-5] Hruby, Victor J.; Ruben Vardanyan; Vardanyan, ۊRuben (2006). Synthesis of essential drugs. Amsterdam: Elsevier. ISBN 0-444-52166-6.

[pmid15627433-6] 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.

[pmid11137513-7] 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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v t e Antihistamines (R06)
Aminoalkyl ethers	Bromazine/Bromodiphenhydramine • Carbinoxamine • Clemastine • Chlorphenoxamine • Diphenylpyraline • Diphenhydramine • Doxylamine • Orphenadrine • Phenyltoloxamine
Substituted alkylamines	Brompheniramine • Chlorphenamine • Dexbrompheniramine • Dexchlorpheniramine • Dimetindene • Pheniramine • Talastine
Substituted ethylenediamines	Chloropyramine • Histapyrrodine • Mepyramine • Methapyrilene • Tripelennamine (Pyribenzamine)
Phenothiazine derivatives	Alimemazine • Hydroxyethylpromethazine • Isothipendyl • Mequitazine • Methdilazine • Oxomemazine • Promethazine
Piperazine derivatives	Buclizine • Cetirizine • Chlorcyclizine • Cinnarizine • Cyclizine • Hydroxyzine • Levocetirizine • Meclizine • Niaprazine • Oxatomide
Others for systemic use	Antazoline • Azatadine • Bamipine • Cyproheptadine • Deptropine • Dimebon • Ebastine • Epinastine • Ketotifen • Mebhydrolin • Mizolastine • Phenindamine • Pimethixene • Pyrrobutamine • Rupatadine • Triprolidine • selective (Acrivastine • Astemizole • Azelastine • Desloratadine • Fexofenadine • Loratadine • Terfenadine)
For topical use	Bamipine • Chloropyramine • Chlorphenoxamine • Clemastine • Dimetindene • Diphenhydramine • Isothipendyl • Mepyramine • Promethazine • Thenalidine
Antiallergic agents excluding corticosteroids	Antazoline • Azelastine
Other antiallergics	Emedastine • Epinastine • Ketotifen • Montelukast • Olopatadine

Diphenylpyraline

Overview

Chemistry

See also

References

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