Record Information
Version3.6
Creation Date2006-05-18 09:00:56 UTC
Update Date2013-02-09 00:11:03 UTC
HMDB IDHMDB01936
Secondary Accession NumbersNone
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
Thumb
Synonyms
  1. Doxylamine hydrogen succinate
  2. Alsadorm
  3. Decapryn
  4. Decapryn (TN)
  5. Decapryn succinate
  6. Doxylamine succinate
  7. Doxylamine succinate (1:1)
  8. Mereprine
Chemical FormulaC17H22N2O
Average Molecular Weight270.3694
Monoisotopic Molecular Weight270.173213336
IUPAC Namedimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine
Traditional IUPAC Namedoxylamine
CAS Registry Number562-10-7
SMILES
CN(C)CCOC(C)(C1=CC=CC=C1)C1=NC=CC=C1
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
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassBenzyl Alcohols and Derivatives
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • pyridines(ChEBI)
  • tertiary amine(ChEBI)
Substituents
  • Dialkyl Ether
  • Pyridine
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct ParentBenzyl Alcohols and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.151Not 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 area25.36ChemAxon
rotatable bond count6ChemAxon
refractivity82.24ChemAxon
polarizability31.23ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022751
KNApSAcK IDNot Available
Chemspider ID3050
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDoxylamine
NuGOwiki LinkHMDB01936
Metagene LinkHMDB01936
METLIN ID4004
PubChem Compound3162
PDB IDNot Available
ChEBI ID51380
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
HRH1
Uniprot ID:
P35367
Gene Name:
CHRM1
Uniprot ID:
P11229