Human Metabolome Database Version 3.5

Showing metabocard for Doxylamine (HMDB01936)

Record Information
Version 3.5
Creation Date 2006-05-18 03:00:56 -0600
Update Date 2013-02-08 17:11:03 -0700
HMDB ID HMDB01936
Secondary Accession Numbers None
Metabolite Identification
Common Name Doxylamine
Description Doxylamine 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C17H22N2O
Average Molecular Weight 270.3694
Monoisotopic Molecular Weight 270.173213336
IUPAC Name dimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine
Traditional IUPAC Name doxylamine
CAS Registry Number 562-10-7
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 Key HCFDWZZGGLSKEP-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Benzyl Alcohols and Derivatives
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • pyridines(ChEBI)
  • tertiary amine(ChEBI)
Substituents
  • Dialkyl Ether
  • Pyridine
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct Parent Benzyl Alcohols and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 2.151 Not Available
Predicted Properties
Property Value Source
LogP 2.90 ALOGPS
LogP 2.96 ChemAxon
LogS -2.70 ALOGPS
pKa (strongest basic) 8.87 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 25.36 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 82.24 ChemAxon
Polarizability 31.23 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022751
KNApSAcK ID Not Available
Chemspider ID 3050 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Doxylamine Link_out
NuGOwiki Link HMDB01936 Link_out
Metagene Link HMDB01936 Link_out
METLIN ID 4004 Link_out
PubChem Compound 3162 Link_out
PDB ID Not Available
ChEBI ID 51380 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available

Enzymes
Name: Histamine H1 receptor
Reactions: Not Available
Gene Name: HRH1
Uniprot ID: P35367 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Muscarinic acetylcholine receptor M1
Reactions: Not Available
Gene Name: CHRM1
Uniprot ID: P11229 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA