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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:36:33 UTC
Update Date2019-07-23 14:38:52 UTC
HMDB IDHMDB0240223
Secondary Accession NumbersNone
Metabolite Identification
Common NameChlorphenoxamine
DescriptionChlorphenoxamine, also known as systral or phenoxene, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Chlorphenoxamine is a very strong basic compound (based on its pKa). In humans, chlorphenoxamine is involved in chlorphenoxamine h1-antihistamine action. Chlorphenoxamine is marketed under the name Phenoxene.
Structure
Data?1563892731
Synonyms
ValueSource
Chlorphenoxamine hydrochlorideHMDB
SystralHMDB
PhenoxeneHMDB
p-Chloro-α-methyldiphenhydramineHMDB
p-Chloro-alpha-methyldiphenhydramineHMDB
ChlorphenoxamineHMDB
Chemical FormulaC18H22ClNO
Average Molecular Weight303.826
Monoisotopic Molecular Weight303.138992038
IUPAC Name{2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl}dimethylamine
Traditional Namesystral
CAS Registry Number77-38-3
SMILES
CN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C18H22ClNO/c1-18(21-14-13-20(2)3,15-7-5-4-6-8-15)16-9-11-17(19)12-10-16/h4-12H,13-14H2,1-3H3
InChI KeyKKHPNPMTPORSQE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Benzylether
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Dialkyl ether
  • Organochloride
  • Organohalogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.45ALOGPS
logP4.4ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.57 m³·mol⁻¹ChemAxon
Polarizability34.03 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-9270000000-0d583146e734001ab2deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1019000000-8bf961c8b305d3d2cd18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-6197000000-e3bac9734f5caf72ae3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-9330000000-4695fc77e61182f67db6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1029000000-4903b35120dfe8c709acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2289000000-24171bc1dfc4aff63337Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02w9-6790000000-ff8ef12e4f5540ab3a53Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09007
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorphenoxamine
METLIN IDNot Available
PubChem Compound6475
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. BAZEX A, DUPRE A, CHRISTOL B: [Trial treatment of urticaria with chlorphenoxamine]. Clinique (Paris). 1963 Jul-Aug;58:447-50. [PubMed:13967113 ]