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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-18 08:39:36 UTC
Update Date2022-09-22 17:43:47 UTC
HMDB IDHMDB0001927
Secondary Accession Numbers
  • HMDB0004997
  • HMDB01927
  • HMDB04997
Metabolite Identification
Common NameDiphenhydramine
DescriptionDiphenhydramine is a 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 ;.
Structure
Data?1582752217
Synonyms
ValueSource
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
Chemical FormulaC17H21NO
Average Molecular Weight255.3547
Monoisotopic Molecular Weight255.162314299
IUPAC Name[2-(diphenylmethoxy)ethyl]dimethylamine
Traditional Namediphenhydramine
CAS Registry Number147-24-0
SMILES
CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=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
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
  • 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
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point168 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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 RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+161.17831661259
DarkChem[M+H]+161.17831661259
DarkChem[M-H]-159.00131661259
DarkChem[M-H]-159.00131661259
AllCCS[M+H]+159.75432859911
AllCCS[M-H]-167.06132859911
DeepCCS[M+H]+159.21730932474
DeepCCS[M-H]-156.85930932474
DeepCCS[M-2H]-189.74430932474
DeepCCS[M+Na]+165.3130932474
AllCCS[M+H]+159.832859911
AllCCS[M+H-H2O]+155.932859911
AllCCS[M+NH4]+163.432859911
AllCCS[M+Na]+164.432859911
AllCCS[M-H]-167.132859911
AllCCS[M+Na-2H]-167.032859911
AllCCS[M+HCOO]-167.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DiphenhydramineCN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C12546.2Standard polar33892256
DiphenhydramineCN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C11914.1Standard non polar33892256
DiphenhydramineCN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C11871.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Diphenhydramine EI-B (Non-derivatized)splash10-0a4i-9100000000-7b9eb1f702c76f6b60622017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diphenhydramine EI-B (Non-derivatized)splash10-0a4i-9100000000-7b9eb1f702c76f6b60622018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diphenhydramine GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-6900000000-84b4a2c53eae448ca1bd2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diphenhydramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diphenhydramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9200000000-b9014c8fc8ccbba241632014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-0006-0090000000-a71e531b49571f09ab252012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-00kk-0980000000-cce91896f34562beeffa2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-001i-1900000000-4c29bd5e0eab94596eaa2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine EI-B (Unknown) , Positive-QTOFsplash10-0a4i-9100000000-ab642e8f86de11af896c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , negative-QTOFsplash10-000t-0910000000-3576ca5ec77ab87354ec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-0ccd6de9ca58593fd4902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-3568aae4c27ffe333c0e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-22e0c745355c836f15352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-6bb69a66a343440c64f82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-1b87d83415d22bb17f1b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOFsplash10-0gb9-0900000000-50251362d768cd1b1c4f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOFsplash10-0gb9-0900000000-9f37a733a05f5b01d3132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-7d73b95ed09ea2d722602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOFsplash10-0gb9-2900000000-1666a8ab5a6d81c0bd012017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine LC-ESI-ITFT , positive-QTOFsplash10-014i-0900000000-3f31841d858381760f032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine LC-ESI-ITFT , positive-QTOFsplash10-014i-0900000000-de872e048c7e12cef4902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine LC-ESI-ITFT , positive-QTOFsplash10-014i-0900000000-de872e048c7e12cef4902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine , positive-QTOFsplash10-014i-0900000000-789a4a3fe118d5bf24562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenhydramine , positive-QTOFsplash10-014i-2900000000-8ef94659f614b9ff24ca2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenhydramine 10V, Positive-QTOFsplash10-0a4i-1190000000-b33f7871c289d81b86482017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenhydramine 20V, Positive-QTOFsplash10-0ab9-6690000000-814b7cb7faf094058c002017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenhydramine 40V, Positive-QTOFsplash10-00xr-9500000000-98351e9c274a79fda2d02017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenhydramine 10V, Negative-QTOFsplash10-0udi-1290000000-3911d08f3498d2ef857f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenhydramine 20V, Negative-QTOFsplash10-0ue9-4890000000-3d0fdfdee0fffe9f228f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenhydramine 40V, Negative-QTOFsplash10-0059-9500000000-41b5f1e1a6122e43b2852017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.30 (0.034-0.65) uMAdult (>18 years old)BothFatally injured drivers details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01075
Phenol Explorer Compound IDNot Available
FooDB IDFDB022744
KNApSAcK IDNot Available
Chemspider ID2989
KEGG Compound IDC06960
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiphenhydramine
METLIN ID2312
PubChem Compound3100
PDB IDNot Available
ChEBI ID4636
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
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