CHEBI:4636 - diphenhydramine

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ChEBI Name diphenhydramine
ChEBI ID CHEBI:4636
Definition An ether that is the benzhydryl ether of 2-(dimethylamino)ethanol. It is a H1-receptor antagonist used as a antipruritic and antitussive drug.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C17H21NO
Net Charge 0
Average Mass 255.35470
Monoisotopic Mass 255.162
InChI InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3
InChIKey ZZVUWRFHKOJYTH-UHFFFAOYSA-N
SMILES CN(C)CCOC(c1ccccc1)c1ccccc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
Application(s): H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
antiemetic
A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.
sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
anti-allergic agent
A drug used to treat allergic reactions.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
antiparkinson drug
A drug used in the treatment of Parkinson's disease.
antipruritic drug
A drug, usually applied topically, that relieves pruritus (itching).
local anaesthetic
Any member of a group of drugs that reversibly inhibit the propagation of signals along nerves. Wide variations in potency, stability, toxicity, water-solubility and duration of action determine the route used for administration, e.g. topical, intravenous, epidural or spinal block.
antidyskinesia agent
Any compound which can be used to treat or alleviate the symptoms of dyskinesia.
antitussive
An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.
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ChEBI Ontology
Outgoing diphenhydramine (CHEBI:4636) has role anti-allergic agent (CHEBI:50857)
diphenhydramine (CHEBI:4636) has role antidyskinesia agent (CHEBI:66956)
diphenhydramine (CHEBI:4636) has role antiemetic (CHEBI:50919)
diphenhydramine (CHEBI:4636) has role antiparkinson drug (CHEBI:48407)
diphenhydramine (CHEBI:4636) has role antipruritic drug (CHEBI:59683)
diphenhydramine (CHEBI:4636) has role antitussive (CHEBI:51177)
diphenhydramine (CHEBI:4636) has role H1-receptor antagonist (CHEBI:37955)
diphenhydramine (CHEBI:4636) has role local anaesthetic (CHEBI:36333)
diphenhydramine (CHEBI:4636) has role muscarinic antagonist (CHEBI:48876)
diphenhydramine (CHEBI:4636) has role sedative (CHEBI:35717)
diphenhydramine (CHEBI:4636) is a ether (CHEBI:25698)
diphenhydramine (CHEBI:4636) is a tertiary amino compound (CHEBI:50996)
Incoming dimenhydrinate (CHEBI:4604) has part diphenhydramine (CHEBI:4636)
diphenhydramine hydrochloride (CHEBI:4637) has part diphenhydramine (CHEBI:4636)
diphenhydramine salicylate (CHEBI:34720) has part diphenhydramine (CHEBI:4636)
IUPAC Name
2-(diphenylmethoxy)-N,N-dimethylethanamine
INNs Sources
difenhidramina ChemIDplus
diphenhydramine ChemIDplus
diphenhydraminum ChemIDplus
Synonyms Sources
2-(benzhydryloxy)-N,N-dimethylethylamine ChemIDplus
2-diphenylmethoxy-N,N-demthylethanamine ChEBI
α-(2-dimethylaminoethoxy)diphenylmethane ChemIDplus
β-dimethylaminoethanol diphenylmethyl ether ChemIDplus
β-dimethylaminoethyl benzhydryl ether ChEBI
N-(2-(diphenylmethoxy)ethyl)-N,N-dimethylamine ChemIDplus
O-benzhydryldimethylaminoethanol ChEBI
Manual Xrefs Databases
2973 VSDB
2PM PDBeChem
C14015 KEGG COMPOUND
D00300 KEGG DRUG
D02419 KEGG DRUG
DB01075 DrugBank
Diphenhydramine Wikipedia
HMDB0001927 HMDB
LSM-5581 LINCS
US2421714 Patent
US2427878 Patent
View more database links
Registry Numbers Types Sources
1914136 Beilstein Registry Number Beilstein
58-73-1 CAS Registry Number NIST Chemistry WebBook
58-73-1 CAS Registry Number ChemIDplus
Last Modified
25 February 2016
General Comment
2010-12-14 A sedating antihistamine with antimuscarinic properties, it is used for the symptomatic relief of allergic conditions including urticaria, rhinitis, and conjunctivitis, and in pruritic skin disorders. Its antiemetic properties are used in the treatment of nausea and vomiting, particularly for motion sickness, and in the treatment of vertigo. Its antimuscarinic properties are used in the control of parkinsonism, while its central sedative properties are used in the short-term management of insomnia. Diphenhydramine is a common ingredient of preparations for the symptomatic treatment of coughs and the common cold.