4-(diphenylmethoxy)-1-methylpiperidine

• ChemBase ID: 1017
• Molecular Formular: C19H23NO
• Molecular Mass: 281.39202
• Monoisotopic Mass: 281.17796436
• SMILES: O(C1CCN(CC1)C)C(c1ccccc1)c1ccccc1
• Canonical SMILES: CN1CCC(CC1)OC(c1ccccc1)c1ccccc1
• 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
• InChIKey: OWQUZNMMYNAXSL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(diphenylmethoxy)-1-methylpiperidine
• IUPAC Traditional name: diphenylpyraline
• Brand Name: Allergen; Belfene; Dafen; Dayfen; Diafen; Hispril; Histryl; Histyn; Hystryl; Lyssipoll; Mepiben; Neargal
• Synonyms: Diphenylpyralamine; Diphenylpyraline Hydrochloride; Diphenylpyrilene; Diphenylpyraline; 4-(diphenylmethoxy)-1-methyl-piperidine

Database IDs

• CAS Number: 147-20-6
• PubChem SID: 160964480; 46504936
• PubChem CID: 3103
• CHEBI ID: 59788
• ATC CODE: R06AA07
• CHEMBL: 1492
• Chemspider ID: 2992
• DrugBank ID: DB01146
• KEGG ID: D07862
• Unique Ingredient Identifier: 33361OE3AV
• Wikipedia Title: Diphenylpyraline

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.52955604
• LogD (pH = 7.4): 2.1785989
• Log P: 3.6600688
• Molar Refractivity: 87.359 cm^3
• Polarizability: 34.356525 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.82
• LOG S: -4.18
• Solubility (Water): 1.88e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.7

Pharmacology Properties

• Admin Routes: Oral, Topical
• Half Life: 24-40 hours
• Legal Status: Rx-only

DETAILS

DrugBank - DB01146

• Drug Groups: approved
• Description: Diphenylpyraline is an antihistamine. Antihistamines used in the treatment of allergy act by competing with histamine for H 1-receptor sites on effector cells. Antihistamines prevent, but do not reverse, responses mediated by histamine alone. Antihistamines antagonize, in varying degrees, most of the pharmacological effects of histamine, including urticaria and pruritus.
• Indication: For use in the treatment of allergic rhinitis, hay fever, and allergic skin disorders.
• Pharmacology: Diphenylpyraline is an antihistamine that prevents, but does not reverse, responses mediated by histamine alone. Diphenylpyraline antagonizes most of the pharmacological effects of histamine, including urticaria and pruritus. Also, diphenylpyraline may exhibit anticholinergic actions (as do most of the antihistamines) and may thus provide a drying effect on the nasal mucosa.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Well absorbed after oral administration.
• Protein Binding: > 99% in human serum albumin
• References: Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR: Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. Epub 2004 Dec 8. [Pubmed] ; Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I: Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients. J Neurol Sci. 2001 Jan 1;182(2):95-7. [Pubmed] ; Puhakka H, Rantanen T, Virolainen E: Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis. J Int Med Res. 1977;5(1):37-41. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR: Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. Epub 2004 Dec 8. Pubmed
• Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I: Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients. J Neurol Sci. 2001 Jan 1;182(2):95-7. Pubmed
• Puhakka H, Rantanen T, Virolainen E: Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis. J Int Med Res. 1977;5(1):37-41. Pubmed