CHEBI:4636 - diphenhydramine

ChEBI IDCHEBI:4636
ChEBI Namediphenhydramine
Stars
DefinitionAn ether that is the benzhydryl ether of 2-(dimethylamino)ethanol. It is a H1-receptor antagonist used as a antipruritic and antitussive drug.
Last Modified6 March 2020
DownloadsMolfile
FormulaC17H21NO
Net Charge0
Average Mass255.361
Monoisotopic Mass255.16231
SMILESCN(C)CCOC(c1ccccc1)c1ccccc1
InChIInChI=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
InChIKeyZZVUWRFHKOJYTH-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
muscarinic antagonist  A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
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.
Applications:
sedative  A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
muscarinic antagonist  A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
anti-allergic agent  A drug used to treat allergic reactions.
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.
antiparkinson drug  A drug used in the treatment of Parkinson's disease.
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.
antidyskinesia agent  Any compound which can be used to treat or alleviate the symptoms of dyskinesia.
oneirogen  Any substance that produces or enhances dream-like states of consciousness.
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.
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.
ChEBI Ontology
Outgoing Relation(s)
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 oneirogen (CHEBI:146270)
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 Relation(s)
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  Source
difenhidraminaChemIDplus
diphenhydramineChemIDplus
diphenhydraminumChemIDplus
Synonyms  Source
2-(benzhydryloxy)-N,N-dimethylethylamineChemIDplus
2-diphenylmethoxy-N,N-demthylethanamineChEBI
N-(2-(diphenylmethoxy)ethyl)-N,N-dimethylamineChemIDplus
O-benzhydryldimethylaminoethanolChEBI
α-(2-dimethylaminoethoxy)diphenylmethaneChemIDplus
β-dimethylaminoethanol diphenylmethyl etherChemIDplus
Manual XrefsDatabases
2973VSDB
2PMPDBeChem
C14015KEGG COMPOUND
D00300KEGG DRUG
D02419KEGG DRUG
DB01075DrugBank
DiphenhydramineWikipedia
HMDB0001927HMDB
LSM-5581LINCS
US2421714Patent
US2427878Patent
Registry NumbersSources
Beilstein:1914136Beilstein
CAS:58-73-1NIST Chemistry WebBook
CAS:58-73-1ChemIDplus