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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-18 09:00:56 UTC
Update Date2022-09-22 18:34:16 UTC
HMDB IDHMDB0001936
Secondary Accession Numbers
  • HMDB01936
Metabolite Identification
Common NameDoxylamine
DescriptionDoxylamine is a sedating antihistamine that can be used by itself as a short-term sleep aid, in combination with other drugs as a night-time cold and allergy relief. It is a member of the ethanolamine class of antihistamines and has anti-allergy power superior to almost every other antihistamine on the market, with the exception of diphenhydramine (Benadryl). It is also the most effective over-the-counter sedative available in North America, and more sedating than some prescription hypnotics. In a study, it was found that doxylamine succinate is possibly more effective than the barbiturate, phenobarbital for use as a sedative. For this reason, doxylamine has sometimes been used off label in a manner similar to diphenhydramine for the reduction of anxiety symptoms; Doxylamine succinate is used by itself as a short-term sleep aid, in combination with other drugs as a night-time cold and allergy relief drug, and a preparation is prescribed in combination with Vitamin B6 (pyridoxine) to prevent morning sickness in pregnant women. In Commonwealth countries, doxylamine is available prepared with paracetamol/acetaminophen and codeine under the brand name Syndol or Mersyndol, as treatment for tension headache and other types of pain, or as a general OTC sleep-aid branded as Somnil, Donormyl, DSozile and Restavit containing Doxylamine Succinate only.
Structure
Data?1582752218
Synonyms
ValueSource
2-(alpha-(2-(Dimethylamino)ethoxy)-alpha-methylbenzyl)pyridineChEBI
2-Dimethylaminoethoxyphenylmethyl-2-picolineChEBI
DossilaminaChEBI
DoxilaminaChEBI
DoxilminioChEBI
DoxylaminumChEBI
N,N-Dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)ethanamineChEBI
Phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl etherChEBI
2-(a-(2-(Dimethylamino)ethoxy)-a-methylbenzyl)pyridineGenerator
2-(Α-(2-(dimethylamino)ethoxy)-α-methylbenzyl)pyridineGenerator
Phenyl-2-pyridylmethyl-b-N,N-dimethylaminoethyl etherGenerator
Phenyl-2-pyridylmethyl-β-N,N-dimethylaminoethyl etherGenerator
Doxylamine hydrogen succinateHMDB
AlsadormHMDB
DecaprynHMDB
Decapryn succinateHMDB
Doxylamine succinateHMDB
Doxylamine succinate (1:1)HMDB
MereprineHMDB
Chemical FormulaC17H22N2O
Average Molecular Weight270.3694
Monoisotopic Molecular Weight270.173213336
IUPAC Namedimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine
Traditional Namedoxylamine
CAS Registry Number562-10-7
SMILES
CN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=CC=N1
InChI Identifier
InChI=1S/C17H22N2O/c1-17(20-14-13-19(2)3,15-9-5-4-6-10-15)16-11-7-8-12-18-16/h4-12H,13-14H2,1-3H3
InChI KeyHCFDWZZGGLSKEP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzylethers
Direct ParentBenzylethers
Alternative Parents
Substituents
  • Benzylether
  • Pyridine
  • Heteroaromatic compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.151Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM161.930932474
[M+H]+Not Available162.643http://allccs.zhulab.cn/database/detail?ID=AllCCS00000821
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.54 g/LALOGPS
logP2.9ALOGPS
logP2.96ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity82.24 m³·mol⁻¹ChemAxon
Polarizability31.09 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]+164.09631661259
DarkChem[M-H]-163.02931661259
AllCCS[M+H]+162.13832859911
AllCCS[M-H]-171.59432859911
DeepCCS[M+H]+163.80530932474
DeepCCS[M-H]-161.44730932474
DeepCCS[M-2H]-194.33330932474
DeepCCS[M+Na]+169.89930932474
AllCCS[M+H]+162.132859911
AllCCS[M+H-H2O]+158.332859911
AllCCS[M+NH4]+165.732859911
AllCCS[M+Na]+166.732859911
AllCCS[M-H]-171.632859911
AllCCS[M+Na-2H]-171.732859911
AllCCS[M+HCOO]-171.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DoxylamineCN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=CC=N12473.0Standard polar33892256
DoxylamineCN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=CC=N11940.6Standard non polar33892256
DoxylamineCN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=CC=N11917.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Doxylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-7900000000-24e4f3f90dbbb58629282017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ab9-9200000000-5a71de62862f9881c2a12014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0040-0956300000-af11cf85a674e7db37352012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-0910000000-b3cb895f045d519f2bf32012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00kb-5597500000-8495062a84b32e776f332012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine LC-ESI-qTof , Positive-QTOFsplash10-0292-0940000000-f369442eba5344b3ecb42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine LC-ESI-QFT , positive-QTOFsplash10-001i-1920000000-07b98b36c7ef5d9ad0482017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine LC-ESI-QFT , positive-QTOFsplash10-001i-0900000000-1ae1143763892a7aac222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine LC-ESI-QFT , positive-QTOFsplash10-001i-0900000000-460d58a5bb6a5eb5f55b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine LC-ESI-QFT , positive-QTOFsplash10-0159-0900000000-34dc5c06413efae437da2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-8a5f15b863b7129c12882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-072ffba5139b7324d27a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine , positive-QTOFsplash10-00lr-0900000000-fdf3fc57eff19bfe8fd82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine 30V, Positive-QTOFsplash10-001i-0900000000-4bd3999ccd0a2246f1bf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine 15V, Positive-QTOFsplash10-001i-1920000000-1fbd7581ebf1730dac6d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine 35V, Positive-QTOFsplash10-0159-1900000000-37f4e915e528d2466b802021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine 45V, Positive-QTOFsplash10-001i-0900000000-a056c64c9344a95599052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine 60V, Positive-QTOFsplash10-0159-0900000000-0ab3cbbe5a34cba773132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine 90V, Positive-QTOFsplash10-014i-0900000000-1a3a34606ccd3aa3009c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxylamine 75V, Positive-QTOFsplash10-014i-0900000000-07c546b389aa80244f622021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxylamine 10V, Positive-QTOFsplash10-00di-1190000000-e7b1a3b0a0368fc310df2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxylamine 20V, Positive-QTOFsplash10-00e9-5790000000-7402b4fd77afe325c64b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxylamine 40V, Positive-QTOFsplash10-00di-9510000000-b9439d5014a66b7857ec2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxylamine 10V, Negative-QTOFsplash10-014i-1290000000-1725573962a3041ca6172017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxylamine 20V, Negative-QTOFsplash10-014j-1690000000-44de19831bffecc1c4122017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxylamine 40V, Negative-QTOFsplash10-009t-5900000000-caa39da176327be2a9c22017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxylamine 10V, Negative-QTOFsplash10-00kb-0960000000-a2cc3fcbeb38ca35de582021-09-22Wishart 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
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation 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 IDDB00366
Phenol Explorer Compound IDNot Available
FooDB IDFDB022751
KNApSAcK IDC00017814
Chemspider ID3050
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDoxylamine
METLIN ID4004
PubChem Compound3162
PDB IDNot Available
ChEBI ID51380
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 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
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular weight:
51420.4