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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:31:32 UTC
HMDB IDHMDB15120
Secondary Accession NumbersNone
Metabolite Identification
Common NameDimenhydrinate
DescriptionDimenhydrinate is only found in individuals that have used or taken this drug. It 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.The 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.
Structure
Thumb
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
(O-Benzhydryl(dimethylamino)ethanol) 8-chlorotheophyllinic acidGenerator
Dimenhydrinic 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
DiphenhydrinateHMDB
Chemical FormulaC24H28ClN5O3
Average Molecular Weight469.964
Monoisotopic Molecular Weight469.188067494
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
CAS Registry Number523-87-5
SMILES
CN1C2=C([N-]C(Cl)=N2)C(=O)N(C)C1=O.C[NH+](C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
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)
InChI KeyInChIKey=DKHVTDUUNTVKOW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These 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
  • Alkaloid or derivatives
  • Xanthine
  • Purinone
  • 6-oxopurine
  • Purine
  • Imidazopyrimidine
  • Benzylether
  • Pyrimidone
  • Pyrimidine
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Vinylogous amide
  • Quaternary ammonium salt
  • Imidazole
  • Azole
  • Urea
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Organic zwitterion
  • Aromatic homomonocyclic compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkNot Available
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antiemetics
  • Histamine H1 Antagonists
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point204.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.25e-03 g/LNot Available
LogP-0.39Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0013 mg/mLALOGPS
logP2.67ALOGPS
logP3.65ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area13.67 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.94 m3·mol-1ChemAxon
Polarizability30.28 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00985
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00985
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-2 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00985
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10468539
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDimenhydrinate
NuGOwiki LinkHMDB15120
Metagene LinkHMDB15120
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID4604
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. [11835984 ]
  2. Jaju BP, Wang SC: Effects of diphenhydramine and dimenhydrinate on vestibular neuronal activity of cat: a search for the locus of their antimotion sickness action. J Pharmacol Exp Ther. 1971 Mar;176(3):718-24. [4329456 ]
  3. Takeda N, Morita M, Hasegawa S, Horii A, Kubo T, Matsunaga T: Neuropharmacology of motion sickness and emesis. A review. Acta Otolaryngol Suppl. 1993;501:10-5. [8447218 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
  2. Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. [11835984 ]