Diphenylpyraline

HCID 3103
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
147-20-6
Standard SMILES
CN1CCC(OC(c2ccccc2)c2ccccc2)CC1
InChIKey
OWQUZNMMYNAXSL-UHFFFAOYSA-N
Molecular formula
C19H23NO
Average molar mass
281.4 g/mol
Monoisotopic mass
281.17796436

Overview

Diphenylpyraline is a member of the class of piperidines that is the benzhydryl ether derivative of 1-methyl-4-hydroxypiperidine. A sedating antihistamine, it is used as the hydrochloride for the symptomatic relief of allergic conditions including rhinitis and hay fever, and in pruritic skin disorders. It is also used as the teoclate salt (piprinhydrinate) as an ingredient in compound preparations for the symptomatic relief of coughs and the common cold. It has a role as a H1-receptor antagonist and a cholinergic antagonist. It is a member of piperidines and a tertiary amine.

Names & identifiers

Preferred name
Diphenylpyraline
IUPAC
4-benzhydryloxy-1-methylpiperidine
English name
diphenylpyraline
Molecular formula
C19H23NO
Molecular weight
281.39202

Names & synonyms

diphenylpyraline147-20-6LyssipollMepibenNeargal4-(Benzhydryloxy)-1-methylpiperidine4-(Diphenylmethoxy)-1-methylpiperidineDiphenylpyralamineAllergenDifenilpiralinaDiphenylpyralinumAN 1041
Show more names
P-253DayfenAN1041HystrylHisprilBelfeneAN-1041Aids033087
1-Methyl-4-piperidyl benzhydryl ether4-(benzhydryloxy)-N-methylpiperidine33361OE3AV1-methyl-4-hydroxypiperidine benzhydryl ether4-DIPHENYLMETHOXY-1-METHYLPIPERIDINEDTXSID3022952CHEBI:59788RefChem:588945

Database identifiers

CAS
147-20-6
PubChem CID
3103
DTXSID
DTXSID3022952
ChEMBL
CHEMBL1492
ChEBI
CHEBI:59788
UNII
33361OE3AV
EC Number
205-686-7
Nikkaji
J5.838F

Properties

Computed structural properties

XLogP
3.9
Topological polar surface area
12.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
4
Heavy atoms
21

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP3.7
Solubility1.88e-02 g/L
Human DrugsPharmaceuticals
Physical DescriptionSolid
Collision Cross Section172.19 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Boiling point
424.06 °C · 424.06°C (rough estimate)
Density
1.0423 · 1.0423 (rough estimate)
refractive index
1.5 · 1.5000 (estimate)
storage temp.
-20 °C · Store at -20°C
solubility
30 mg/ml,DMSO: · DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,Ethanol:PBS (pH 7.2) (1:1): 0.5 mg/ml
form
A crystalline solid

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Safety data

ridadr
3249
Signal word
Warning
Symbol(GHS)
GHS07
hazard_class
6.1(b)
packing_group
III
Hazard statements
H302

Chemistry & industry

Pharmacology

ATC Code · 2 items

R - Respiratory system

QR - Respiratory system

Protein Binding> 99% in human serum albumin
Pharmacodynamics · 1 item

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.

Mechanism of ActionAntihistamines such as diphenylpyraline used in the treatment of allergy act by competing with histamine for H1-receptor sites on effector cells. This reduces the effects of histamine, leading to a temporary reduction of allergy symptoms.
Metabolism/MetabolitesHepatic
Absorption, Distribution and ExcretionWell absorbed after oral administration.

Uses & manufacturing

Use ClassificationPharmaceuticals
Applications · 1 item

UsesDiphenylpyraline is an H1 receptor antagonist (an antihistamine), and is commonly prescribed to treat allergic and vasomotor rhinitis. There is also some research being conducted on diphenylpyraline derivatives to determine their antimycobacterial and antifungal activity.

Preparation methods

PreparationDiphenylpyraline synthesis via coupling of 4-hydroxy-1-methylpiperidine with benzhydrylbromide.

Upstream & downstream products

Suppliers29 total

北京华美互利生物化工010-56205725 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
梯希爱（上海）化工贸易有限公司021-61109150 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Diphenylpyraline is a member of the class of piperidines that is the benzhydryl ether derivative of 1-methyl-4-hydroxypiperidine. A sedating antihistamine, it is used as the hydrochloride for the symptomatic relief of allergic conditions including rhinitis and hay fever, and in pruritic skin disorders. It is also used as the teoclate salt (piprinhydrinate) as an ingredient in compound preparations for the symptomatic relief of coughs and the common cold. It has a role as a H1-receptor antagonist and a cholinergic antagonist. It is a member of piperidines and a tertiary amine.

Related reactions

4 records
New reaction record

Compound notes

Loading…