CHEBI:4604 - dimenhydrinate

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ChEBI Name dimenhydrinate
ChEBI ID CHEBI:4604
Definition The diphenhydramine salt of 8-chlorotheophylline. Its effects are similar to those of diphenhydramine, but it is less potent. It was thought that by combining the antiemetic effects of diphenhydramine with the mild stimulant effects of 8-chlorotheophyline, the extreme drowsiness induced by the former would be mitigated. However, the sedation caused by diphenhydramine is considerably stronger than the stimulation caused by 8-chlorotheophylline. Dimenhydrinate is used mainly as an antiemetic in the prevention and treatment of motion sickness.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H28ClN5O3
Net Charge 0
Average Mass 469.96400
Monoisotopic Mass 469.18807
InChI InChI=1S/C17H21NO.C7H7ClN4O2/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16;1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h3-12,17H,13-14H2,1-2H3;1-2H3,(H,9,10,13)
InChIKey DKHVTDUUNTVKOW-UHFFFAOYSA-N
SMILES Cn1c2nc(Cl)[n-]c2c(=O)n(C)c1=O.C[NH+](C)CCOC(c1ccccc1)c1ccccc1
Roles Classification
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.
Application(s): 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.
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.
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ChEBI Ontology
Outgoing dimenhydrinate (CHEBI:4604) has part 8-chlorotheophylline(1−) (CHEBI:59778)
dimenhydrinate (CHEBI:4604) has part diphenhydramine (CHEBI:4636)
dimenhydrinate (CHEBI:4604) has role antiemetic (CHEBI:50919)
dimenhydrinate (CHEBI:4604) has role H1-receptor antagonist (CHEBI:37955)
dimenhydrinate (CHEBI:4604) is a organic salt (CHEBI:24868)
IUPAC Name
2-(diphenylmethoxy)-N,N-dimethylethanaminium 8-chloro-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-ide
INNs Sources
dimenhidrinato ChemIDplus
dimenhydrinate ChemIDplus
dimenhydrinatum ChemIDplus
Synonyms Sources
(O-benzhydryl(dimethylamino)ethanol) 8-chlorotheophyllinate ChemIDplus
8-chloro-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione - 2-(diphenylmethoxy)-N,N-dimethylethanamine (1:1) IUPAC
Benzhydryl-β-dimethylaminoethylether 8-chlorotheophylline ChemIDplus
β-dimethylaminoethyl benzhydryl ether 1,3-dimethyl-8-chloroxanthine ChemIDplus
diphenhydramine 8-chlorotheophyllinate ChemIDplus
diphenhydramine 8-chlorotheophylline ChemIDplus
diphenhydramine theoclate ChEBI
N,N-dimethyl-2-diphenylmethoxyethylamine 8-chlorotheophyllinate ChemIDplus
O-benzhydryldimethylaminoethanol 8-chlorotheophyllinate ChemIDplus
Manual Xrefs Databases
D00520 KEGG DRUG
DB00985 DrugBank
US2499058 Patent
US2534813 Patent
View more database links
Registry Number Type Source
523-87-5 CAS Registry Number ChemIDplus
Last Modified
16 July 2010