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Record Information
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-09-22 02:33:30 UTC
Secondary Accession Numbers
  • HMDB15120
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.
(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
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
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
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
Sub ClassBenzene and substituted derivatives
Direct ParentDiphenylmethanes
Alternative Parents
  • 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
StatusExpected but not Quantified
  • Drug
  • Antiemetics
  • Histamine H1 Antagonists
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
Experimental Properties
Melting Point204.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.25e-03 g/LNot Available
LogP-0.39Not Available
Predicted Properties
Water Solubility0.0013 mg/mLALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
No entries found
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00985 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00985 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 LinkHMDB0015120
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID4604
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. [PubMed: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. [PubMed: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. [PubMed:8447218 ]


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:
Uniprot ID:
Molecular weight:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed: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. [PubMed:11835984 ]