Record Information
Version1.0
Creation date2011-09-21 00:19:03 UTC
Update date2018-05-28 18:33:55 UTC
Primary IDFDB022751
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number562-10-7
Structure
Thumb
Synonyms
SynonymSource
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
2-(a-(2-(dimethylamino)Ethoxy)-a-methylbenzyl)pyridineGenerator
2-(alpha-(2-(dimethylamino)Ethoxy)-alpha-methylbenzyl)pyridineChEBI
2-(α-(2-(dimethylamino)ethoxy)-α-methylbenzyl)pyridineGenerator
Decapryn (TN)hmdb
Predicted 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
Chemical FormulaC17H22N2O
IUPAC namedimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine
InChI IdentifierInChI=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
Isomeric SMILESCN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=CC=N1
Average Molecular Weight270.3694
Monoisotopic Molecular Weight270.173213336
Classification
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
Disposition

Biological location:

Role

Industrial application:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0ab9-9200000000-5a71de62862f9881c2a12014-09-20View Spectrum
Predicted GC-MSDoxylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a59-7900000000-24e4f3f90dbbb5862928Spectrum
Predicted GC-MSDoxylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0040-0956300000-af11cf85a674e7db37352012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-0910000000-b3cb895f045d519f2bf32012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kb-5597500000-8495062a84b32e776f332012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0292-0940000000-f369442eba5344b3ecb42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-1920000000-07b98b36c7ef5d9ad0482017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0900000000-1ae1143763892a7aac222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0900000000-460d58a5bb6a5eb5f55b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0159-0900000000-34dc5c06413efae437da2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-8a5f15b863b7129c12882017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-072ffba5139b7324d27a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-0900000000-fdf3fc57eff19bfe8fd82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-0900000000-4bd3999ccd0a2246f1bf2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-001i-1920000000-1fbd7581ebf1730dac6d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0159-1900000000-37f4e915e528d2466b802021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-001i-0900000000-a056c64c9344a95599052021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0159-0900000000-0ab3cbbe5a34cba773132021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-014i-0900000000-1a3a34606ccd3aa3009c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-014i-0900000000-07c546b389aa80244f622021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1190000000-e7b1a3b0a0368fc310df2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-5790000000-7402b4fd77afe325c64b2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9510000000-b9439d5014a66b7857ec2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1290000000-1725573962a3041ca6172017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-1690000000-44de19831bffecc1c4122017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-009t-5900000000-caa39da176327be2a9c22017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-0960000000-a2cc3fcbeb38ca35de582021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID3050
ChEMBL IDCHEMBL1004
KEGG Compound IDNot Available
Pubchem Compound ID3162
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00366
HMDB IDHMDB01936
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDoxylamine
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
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference