Doxylamine succinate (CHEM016077)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:13:36 UTC
Update Date2016-11-09 01:15:19 UTC
Accession NumberCHEM016077
Identification
Common NameDoxylamine succinate
ClassSmall Molecule
DescriptionDoxylamine is a first-generation antihistamine used as a short-term sedative and hypnotic (sleep aid) or in combination formulations to provide night-time allergy and cold relief. It provides a calmative effect in preparations containing the analgesics paracetamol (acetaminophen) and codeine. It is prescribed in combination with vitamin B6 (pyridoxine) to prevent morning sickness in pregnant women. Its fetal safety rating is "A" (no evidence of risk) in Briggs' Reference Guide to Fetal and Neonatal Risk.It was first described in 1948.
Contaminant Sources
  • IARC Carcinogens Group 3
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DecaprynKegg
Doxylamine succinic acidGenerator
Butanedioate;n,N-dimethyl-2-(1-phenyl-1-pyridin-2-ylethoxy)ethanamineGenerator
Doxylamine succinateMeSH
Butanedioate
dimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine
Butanedioate; dimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amineGenerator
Chemical FormulaC21H28N2O5
Average Molecular Mass388.464 g/mol
Monoisotopic Mass388.200 g/mol
CAS Registry Number562-10-7
IUPAC Namebutanedioic acid; dimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine
Traditional Namedoxylamine; succinic acid
SMILESOC(=O)CCC(O)=O.CN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=CC=N1
InChI IdentifierInChI=1S/C17H22N2O.C4H6O4/c1-17(20-14-13-19(2)3,15-9-5-4-6-10-15)16-11-7-8-12-18-16;5-3(6)1-2-4(7)8/h4-12H,13-14H2,1-3H3;1-2H2,(H,5,6)(H,7,8)
InChI KeyKBAUFVUYFNWQFM-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
  • Dicarboxylic acid or derivatives
  • Pyridine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Amine
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkNot Available
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 Count9ChemAxon
Refractivity82.24 m³·mol⁻¹ChemAxon
Polarizability31.09 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-2900000000-d9e5f443082ac0c95936Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-6e2f4d754de5dc3ce871Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009000000-6e2f4d754de5dc3ce871Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0009000000-6e2f4d754de5dc3ce871Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-cef5bda617055f74476cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-cef5bda617055f74476cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0009000000-cef5bda617055f74476cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT001402
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDoxylamine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID11224
Kegg Compound IDC19414
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available