Record Information
Version1.0
Creation date2011-09-21 00:18:57 UTC
Update date2018-05-28 18:33:54 UTC
Primary IDFDB022744
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDiphenhydramine
DescriptionA histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects. -- Pubchem; Pseudoephedrine is a phenethylamine, and an isomer of ephedrine. Pseudoephedrine is the International Nonproprietary Name (INN) of the (1S,2S)- diastereomer of ephedrine (which has 1R,2S- configuration). Other names are (+)-pseudoephedrine and D-pseudoephedrine (Reynolds, 1989). The enantiomer (-)-(1R,2R)-Pseudoephedrine has fewer side-effects, fewer central nervous system (CNS) stimulatory effects, does not reduce to d-methamphetamine, yet retains its efficacy as a decongestant.[citation needed] However, the patent holder for (-)-Pseudoephedrine (Pfizer/Warner-Lambert) has not yet sought or received government approval for its sale to the public.(US Patent 6,495,529); Treatment for urinary incontinence is an unlabeled use for these medications. Unlabeled use means doctors can use the medication to treat a condition other than that for which it was first approved by the U.S. Food and Drug Administration (FDA). These medications are approved by the FDA for the treatment of nasal congestion caused by colds or allergies. However it has also been successful in treating stress incontinence by increasing the pressure (tension) exerted by the muscles of the bladder neck and the urethra, which helps retain the urine within the bladder.; Despite being one of the oldest antihistamines on the market, it is by and large the most effective antihistamine available, either by prescription or over-the-counter, and has been shown to exceed the effectiveness of even the latest prescription drugs. Consequently, it is frequently used when an allergic reaction requires fast, effective reversal of the (often dangerous) effects of a massive histamine release. However, it is not always the drug of choice for treating allergies. Like many other first generation antihistamines, is also a potent anticholinergic agent. This leads to profound drowsiness as a very common side-effect, along with the possibilities of motor impairment (ataxia), dry mouth and throat, flushed skin, rapid or irregular heartbeat (tachycardia), blurred vision at near point due to lack of accommodation (cycloplegia), abnormal sensitivity to bright light (photophobia), pupil dilatation, urinary retention, constipation, difficulty concentrating, short-term memory loss, visual disturbances, hallucinations, confusion, erectile dysfunction, and delirium. -- Wikipedia [HMDB]
CAS Number147-24-0
Structure
Thumb
Synonyms
SynonymSource
2-(Benzhydryloxy)-N,N-dimethylethylamineChEBI
2-Diphenylmethoxy-N,N-demthylethanamineChEBI
alpha-(2-Dimethylaminoethoxy)diphenylmethaneChEBI
beta-Dimethylaminoethanol diphenylmethyl etherChEBI
beta-Dimethylaminoethyl benzhydryl etherChEBI
DifenhidraminaChEBI
DiphenhydraminumChEBI
N-(2-(Diphenylmethoxy)ethyl)-N,N-dimethylamineChEBI
O-BenzhydryldimethylaminoethanolChEBI
RestaminKegg
a-(2-Dimethylaminoethoxy)diphenylmethaneGenerator
Α-(2-dimethylaminoethoxy)diphenylmethaneGenerator
b-Dimethylaminoethanol diphenylmethyl etherGenerator
Β-dimethylaminoethanol diphenylmethyl etherGenerator
b-Dimethylaminoethyl benzhydryl etherGenerator
Β-dimethylaminoethyl benzhydryl etherGenerator
BenadrylHMDB
DobacenHMDB
BendylateHMDB
DimedrolumHMDB
AlledrylHMDB
AllerganHMDB
AllerginaHMDB
BenzantinHMDB
DifenhydramineHMDB
DimedrolHMDB
Dimethylamine benzhydryl esterHMDB
DiphamineHMDB
DiphantineHMDB
AllerdrylHMDB
BenzhydramineHMDB
BenhydraminHMDB
Diphenhydramine citrate (1:1)HMDB
DiphenylhydramineHMDB
2-Diphenylmethoxy-N,N-dimethylethylamineHMDB
BenylinHMDB
DiphenylhydraminHMDB
Citrate, diphenhydramineHMDB
Diphenhydramine citrateHMDB
Diphenhydramine hydrochlorideHMDB
DorminHMDB
Hydrochloride, diphenhydramineHMDB
Diphenhydraminehmdb
α-(2-dimethylaminoethoxy)diphenylmethaneGenerator
β-dimethylaminoethanol diphenylmethyl etherGenerator
β-dimethylaminoethyl benzhydryl etherGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.075 g/LALOGPS
logP3.44ALOGPS
logP3.65ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity79.93 m³·mol⁻¹ChemAxon
Polarizability29.86 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC17H21NO
IUPAC name[2-(diphenylmethoxy)ethyl]dimethylamine
InChI IdentifierInChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3
InChI KeyZZVUWRFHKOJYTH-UHFFFAOYSA-N
Isomeric SMILESCN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1
Average Molecular Weight255.3547
Monoisotopic Molecular Weight255.162314299
Classification
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
  • Benzylether
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Dialkyl ether
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9100000000-7b9eb1f702c76f6b6062JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9100000000-7b9eb1f702c76f6b6062JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-6900000000-84b4a2c53eae448ca1bdJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0006-0090000000-a71e531b49571f09ab25JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-00kk-0980000000-cce91896f34562beeffaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-001i-1900000000-4c29bd5e0eab94596eaaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0a4i-9100000000-ab642e8f86de11af896cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000t-0910000000-3576ca5ec77ab87354ecJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-0ccd6de9ca58593fd490JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-3568aae4c27ffe333c0eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-22e0c745355c836f1535JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-6bb69a66a343440c64f8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-1b87d83415d22bb17f1bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gb9-0900000000-50251362d768cd1b1c4fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gb9-0900000000-9f37a733a05f5b01d313JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-7d73b95ed09ea2d72260JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gb9-2900000000-1666a8ab5a6d81c0bd01JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-3f31841d858381760f03JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-de872e048c7e12cef490JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-de872e048c7e12cef490JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0900000000-789a4a3fe118d5bf2456JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-2900000000-8ef94659f614b9ff24caJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1190000000-b33f7871c289d81b8648JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-6690000000-814b7cb7faf094058c00JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-9500000000-98351e9c274a79fda2d0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1290000000-3911d08f3498d2ef857fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-4890000000-3d0fdfdee0fffe9f228fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9500000000-41b5f1e1a6122e43b285JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0a4i-9200000000-b9014c8fc8ccbba24163JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID2989
ChEMBL IDCHEMBL657
KEGG Compound IDC06960
Pubchem Compound ID3100
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01075
HMDB IDHMDB01927
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID2PM
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDiphenhydramine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Histamine H1 receptorHRH1P35367
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
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References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference