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
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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:
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.
muscarinic antagonist  A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
oneirogen  Any substance that produces or enhances dream-like states of consciousness.
antipruritic drug  A drug, usually applied topically, that relieves pruritus (itching).
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.
anti-allergic agent  A drug used to treat allergic reactions.
antidyskinesia agent  Any compound which can be used to treat or alleviate the symptoms of dyskinesia.
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.
sedative  A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
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
β-dimethylaminoethanol diphenylmethyl etherChemIDplus
2-(benzhydryloxy)-N,N-dimethylethylamineChemIDplus
N-(2-(diphenylmethoxy)ethyl)-N,N-dimethylamineChemIDplus
α-(2-dimethylaminoethoxy)diphenylmethaneChemIDplus
β-dimethylaminoethyl benzhydryl etherChEBI
2-diphenylmethoxy-N,N-demthylethanamineChEBI
Manual XrefsDatabases
DB01075DrugBank
D00300KEGG DRUG
US2421714Patent
US2427878Patent
HMDB0001927HMDB
DiphenhydramineWikipedia
2PMPDBeChem
D02419KEGG DRUG
C14015KEGG COMPOUND
LSM-5581LINCS
2973VSDB
Registry NumbersSources
Beilstein:1914136Beilstein
CAS:58-73-1ChemIDplus
CAS:58-73-1NIST Chemistry WebBook