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Dimenhydrinate

July 24, 2017
Common Name

Dimenhydrinate Description

Dimenhydrinate 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 vestibliar stimliation and depress labyrinthine function. An action on the medlilary 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. Dimenhydrinates anti-emetic effect is probably due to H1 antagonism in the vestibliar system in the brain. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source (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 Formlia

C24H28ClN5O3 Average Molecliar Weight

469.964 Monoisotopic Molecliar Weight

469.188067494 IUPAC Name

8-chloro-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-ide; [2-(diphenylmethoxy)ethyl]dimethylazanium Traditional Name

8-chlorotheophylline(1-); [2-(diphenylmethoxy)ethyl]dimethylazanium CAS Registry Number

523-87-5 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 Key

DKHVTDUUNTVKOW-UHFFFAOYSA-N Chemical Taxonomy Description

This 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. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Diphenylmethanes Alternative Parents

  • Xanthines
  • 6-oxopurines
  • Alkaloids and derivatives
  • Benzylethers
  • Pyrimidones
  • Aryl chlorides
  • Vinylogous amides
  • Heteroaromatic compounds
  • Imidazoles
  • Ureas
  • Trialkylamines
  • Lactams
  • Dialkyl ethers
  • Azacyclic compounds
  • Organic salts
  • Organochlorides
  • Hydrocarbon derivatives
  • Organic oxides
  • Organopnictogen compounds

    • 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

    • Molecliar Framework

    Not Available External Descriptors

  • organic salt (CHEBI:4604 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antiemetics
  • Histamine H1 Antagonists

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point204.5 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.25e-03 g/LNot Available LogP-0.39Not Available

    Predicted Properties

    Property Value Source 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00985

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00985

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-2 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-1 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00985 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    10468539 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Dimenhydrinate NuGOwiki Link

    HMDB15120 Metagene Link

    HMDB15120 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    4604

    Product: 8-Epi-docetaxel

    References Synthesis Reference Not 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 ]

    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. [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 ]

    PMID: 10389847

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