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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:36:33 UTC
Update Date2022-03-07 03:18:13 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. In humans, chlorphenoxamine is involved in the chlorphenoxamine h1-antihistamine action pathway. Chlorphenoxamine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Chlorphenoxamine.
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 Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+168.9431661259
AllCCS[M-H]-175.76531661259
DeepCCS[M+H]+174.07130932474
DeepCCS[M-H]-171.71330932474
DeepCCS[M-2H]-204.59930932474
DeepCCS[M+Na]+180.16430932474
AllCCS[M+H]+168.932859911
AllCCS[M+H-H2O]+165.432859911
AllCCS[M+NH4]+172.232859911
AllCCS[M+Na]+173.132859911
AllCCS[M-H]-175.832859911
AllCCS[M+Na-2H]-175.632859911
AllCCS[M+HCOO]-175.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChlorphenoxamineCN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=C(Cl)C=C12800.8Standard polar33892256
ChlorphenoxamineCN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=C(Cl)C=C12154.4Standard non polar33892256
ChlorphenoxamineCN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=C(Cl)C=C12082.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chlorphenoxamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-9270000000-0d583146e734001ab2de2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorphenoxamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorphenoxamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorphenoxamine 10V, Positive-QTOFsplash10-0udi-1019000000-8bf961c8b305d3d2cd182017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorphenoxamine 20V, Positive-QTOFsplash10-0uk9-6197000000-e3bac9734f5caf72ae3f2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorphenoxamine 40V, Positive-QTOFsplash10-00xr-9330000000-4695fc77e61182f67db62017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorphenoxamine 10V, Negative-QTOFsplash10-0udi-1029000000-4903b35120dfe8c709ac2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorphenoxamine 20V, Negative-QTOFsplash10-0udi-2289000000-24171bc1dfc4aff633372017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorphenoxamine 40V, Negative-QTOFsplash10-02w9-6790000000-ff8ef12e4f5540ab3a532017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorphenoxamine 10V, Negative-QTOFsplash10-001i-0092000000-473936b9be1c1340c42e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorphenoxamine 20V, Negative-QTOFsplash10-0uxr-2930000000-c505b9c89407924457762021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorphenoxamine 40V, Negative-QTOFsplash10-014i-1790000000-c7003c2131a3eed98d972021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorphenoxamine 10V, Positive-QTOFsplash10-014i-0092000000-a380a0b11a2a9f81a5d92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorphenoxamine 20V, Positive-QTOFsplash10-014i-1190000000-bc07e4f6573ce6b175602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorphenoxamine 40V, Positive-QTOFsplash10-00di-9220000000-ca728e674e0edc2236ea2021-09-24Wishart LabView Spectrum
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 ID6230
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
MarkerDB IDNot Available
Good Scents 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 ]