Dimenhydrinate (CHEM003519)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2014-08-30 21:04:18 UTC
Update Date2026-04-13 20:40:07 UTC
Accession NumberCHEM003519
Identification
Common NameDimenhydrinate
ClassSmall Molecule
DescriptionDimenhydrinate (Dramamine, Gravol and Vertirosan) is an over-the-counter drug used to prevent motion sickness. It is closely related to diphenhydramine HCl, or Benadryl. It is primarily a H1-antagonist, but also possesses an antimuscarinic effect.
Contaminant Sources
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Antiemetic
  • Drug
  • Histamine H1 Antagonist
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(O-Benzhydryl(dimethylamino)ethanol) 8-chlorotheophyllinateChEBI
8-Chloro-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione - 2-(diphenylmethoxy)-N,N-dimethylethanamine (1:1)ChEBI
Benzhydryl-beta-dimethylaminoethylether 8-chlorotheophyllineChEBI
beta-Dimethylaminoethyl benzhydryl ether 1,3-dimethyl-8-chloroxanthineChEBI
DimenhidrinatoChEBI
DimenhydrinatumChEBI
Diphenhydramine 8-chlorotheophyllinateChEBI
Diphenhydramine 8-chlorotheophyllineChEBI
Diphenhydramine theoclateChEBI
N,N-Dimethyl-2-diphenylmethoxyethylamine 8-chlorotheophyllinateChEBI
O-Benzhydryldimethylaminoethanol 8-chlorotheophyllinateChEBI
DramamineKegg
(O-Benzhydryl(dimethylamino)ethanol) 8-chlorotheophyllinic acidGenerator
Benzhydryl-b-dimethylaminoethylether 8-chlorotheophyllineGenerator
Benzhydryl-β-dimethylaminoethylether 8-chlorotheophyllineGenerator
b-Dimethylaminoethyl benzhydryl ether 1,3-dimethyl-8-chloroxanthineGenerator
Β-dimethylaminoethyl benzhydryl ether 1,3-dimethyl-8-chloroxanthineGenerator
Diphenhydramine 8-chlorotheophyllinic acidGenerator
Diphenhydramine theoclic acidGenerator
N,N-Dimethyl-2-diphenylmethoxyethylamine 8-chlorotheophyllinic acidGenerator
O-Benzhydryldimethylaminoethanol 8-chlorotheophyllinic acidGenerator
Dimenhydrinic acidGenerator
DiphenhydrinateHMDB
Chemical FormulaC24H28ClN5O3
Average Molecular Mass469.964 g/mol
Monoisotopic Mass469.188 g/mol
CAS Registry Number523-87-5
IUPAC Name8-chloro-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-ide; [2-(diphenylmethoxy)ethyl]dimethylazanium
Traditional Name8-chlorotheophylline(1-); [2-(diphenylmethoxy)ethyl]dimethylazanium
SMILESCN1C2=C([N-]C(Cl)=N2)C(=O)N(C)C1=O.C[NH+](C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=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)
InChI KeyDKHVTDUUNTVKOW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Purine
  • Benzylether
  • Alkaloid or derivatives
  • Imidazopyrimidine
  • Pyrimidone
  • Aryl chloride
  • Aryl halide
  • Pyrimidine
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Vinylogous amide
  • Lactam
  • Tertiary amine
  • Tertiary aliphatic amine
  • Urea
  • Dialkyl ether
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Organic salt
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkNot Available
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point102.5-104°C
Boiling PointNot Available
Solubility3000 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP2.67ALOGPS
logP3.65ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area13.67 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.94 m³·mol⁻¹ChemAxon
Polarizability30.28 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-11e9e35553571268ac33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000900000-11e9e35553571268ac33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0000900000-11e9e35553571268ac33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-be4852e0333de3302bbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000900000-be4852e0333de3302bbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0000900000-be4852e0333de3302bbdSpectrum
Toxicity Profile
Route of ExposureWell absorbed after oral administration.
Mechanism of ToxicityThe mechanism by which some antihistamines exert their antiemetic, anti–motion sickness, and antivertigo effects is not precisely known but may be related to their central anticholinergic actions. They diminish vestibular stimulation and depress labyrinthine function. An action on the medullary chemoreceptive trigger zone may also be involved in the antiemetic effect. Dimenhydrinate is a competitive antagonist at the histamine H1 receptor, which is widely distributed in the human brain. Dimenhydrinate's anti-emetic effect is probably due to H1 antagonism in the vestibular system in the brain.
MetabolismHepatic (cytochrome P-450 system). Half Life: 1 to 4 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed for treating vertigo, motion sickness, and nausea associated with pregnancy.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include delerium, hallucinations, and excitment. Patients may be violent and confused.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00985
HMDB IDHMDB0015120
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDimenhydrinate
Chemspider IDNot Available
ChEBI ID4604
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Cusic, J.W.; U.S. Patent 2,499,058; February 28,1950; assigned to G.D. Searle & Co.
Cusic, J.W.; U.S. Patent 2,534,813; December 19,1950; assigned to G.D. Searle & Co.

MSDSNot Available
General ReferencesNot Available