Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-16 23:09:02 UTC
Update Date2022-03-07 03:18:13 UTC
HMDB IDHMDB0240218
Secondary Accession NumbersNone
Metabolite Identification
Common NameDexchlorpheniramine
DescriptionDexchlorpheniramine, also known as dapriton or polaramin, belongs to the class of organic compounds known as pheniramines. Pheniramines are compounds containing a pheniramine moiety, which is structurally characterized by the presence of a 2-benzylpyridine linked to an dimethyl(propyl)amine to form a dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine skeleton. In humans, dexchlorpheniramine is involved in the dexchlorpheniramine h1-antihistamine action pathway. Dexchlorpheniramine 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 Dexchlorpheniramine.
Structure
Data?1563892730
Synonyms
ValueSource
(+)-ChlorpheniramineChEBI
(S)-(+)-2-[p-Chloro-alpha-[2-(dimethylamino)ethyl]benzyl]pyridineChEBI
(S)-gamma-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamineChEBI
D-ChlorpheniramineChEBI
DapritonChEBI
DexchlorpheniraminumChEBI
DexclorfeniraminaChEBI
D-ChloropheniramineKegg
(S)-(+)-2-[p-Chloro-a-[2-(dimethylamino)ethyl]benzyl]pyridineGenerator
(S)-(+)-2-[p-Chloro-α-[2-(dimethylamino)ethyl]benzyl]pyridineGenerator
(S)-g-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamineGenerator
(S)-Γ-(4-chlorophenyl)-N,N-dimethyl-2-pyridinepropanamineGenerator
DexclorHMDB
Dexchlorpheniramine maleate (1:1), (R)-isomerHMDB
Dexchlorpheniramine, (+-)-isomerHMDB
DexclorfeniramineHMDB
PolaraminHMDB
Polargen TDHMDB
Dexchlorpheniramine maleate (1:1), (+-)-isomerHMDB
Dexchlorpheniramine, (R)-isomerHMDB
Dextrochlorpheniramine maleateHMDB
PolaronilHMDB
PolaramineHMDB
Dexchlorpheniramine maleateHMDB
Dexchlorpheniramine maleate (1:1), (S)-isomerHMDB
Dexchlorpheniramine monohydrochlorideHMDB
Dexchlorpheniramine sodium maleate (1:1)HMDB
Dexchlorpheniramine, monohydrochloride, (S)-isomerHMDB
Chemical FormulaC16H19ClN2
Average Molecular Weight274.79
Monoisotopic Molecular Weight274.1236763
IUPAC Name[(3S)-3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
Traditional Name(+)-chlorpheniramine
CAS Registry Number25523-97-1
SMILES
CN(C)CC[C@@H](C1=CC=C(Cl)C=C1)C1=NC=CC=C1
InChI Identifier
InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3/t15-/m0/s1
InChI KeySOYKEARSMXGVTM-HNNXBMFYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pheniramines. Pheniramines are compounds containing a pheniramine moiety, which is structurally characterized by the presence of a 2-benzylpyridine linked to an dimethyl(propyl)amine to form a dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine skeleton.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPheniramines
Direct ParentPheniramines
Alternative Parents
Substituents
  • Pheniramine
  • Chlorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl chloride
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
logP3.74ALOGPS
logP3.58ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)9.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.85 m³·mol⁻¹ChemAxon
Polarizability30.82 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
DeepCCS[M+H]+167.8630932474
DeepCCS[M-H]-165.50230932474
DeepCCS[M-2H]-198.38830932474
DeepCCS[M+Na]+173.95330932474
AllCCS[M+H]+162.032859911
AllCCS[M+H-H2O]+158.332859911
AllCCS[M+NH4]+165.632859911
AllCCS[M+Na]+166.632859911
AllCCS[M-H]-168.132859911
AllCCS[M+Na-2H]-168.232859911
AllCCS[M+HCOO]-168.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DexchlorpheniramineCN(C)CC[C@@H](C1=CC=C(Cl)C=C1)C1=NC=CC=C12913.1Standard polar33892256
DexchlorpheniramineCN(C)CC[C@@H](C1=CC=C(Cl)C=C1)C1=NC=CC=C12016.3Standard non polar33892256
DexchlorpheniramineCN(C)CC[C@@H](C1=CC=C(Cl)C=C1)C1=NC=CC=C12001.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dexchlorpheniramine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9380000000-f4a0f7b13adeafb1762d2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dexchlorpheniramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dexchlorpheniramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dexchlorpheniramine LC-ESI-qTof , Positive-QTOFsplash10-0uy0-0960000000-24a36e80af50293ed70d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dexchlorpheniramine , positive-QTOFsplash10-001i-0190000000-f6ef5e736260c9c22a162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dexchlorpheniramine , positive-QTOFsplash10-0uy0-0960000000-24a36e80af50293ed70d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dexchlorpheniramine 40V, Negative-QTOFsplash10-0006-9350000000-9779048010f442953f052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dexchlorpheniramine 20V, Negative-QTOFsplash10-020v-9760000000-7a2dde5051e33fb99e9b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dexchlorpheniramine 10V, Negative-QTOFsplash10-00di-1290000000-781890d92c473a549bee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dexchlorpheniramine 35V, Positive-QTOFsplash10-001i-0490000000-bd5f7072acbea14ac94b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dexchlorpheniramine 20V, Positive-QTOFsplash10-001i-0090000000-7bdad05e8a60c7e72e2a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dexchlorpheniramine 40V, Positive-QTOFsplash10-014i-0930000000-737ef0ba4ac30a71f3df2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dexchlorpheniramine 10V, Positive-QTOFsplash10-001i-0090000000-29b571daf91aa7b991432021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexchlorpheniramine 10V, Positive-QTOFsplash10-004i-0090000000-9b4d486e9c2c7712ca4d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexchlorpheniramine 20V, Positive-QTOFsplash10-0059-0190000000-2c96b165338a445b284d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexchlorpheniramine 40V, Positive-QTOFsplash10-0ue9-3960000000-73025748bd5a004599382017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexchlorpheniramine 10V, Negative-QTOFsplash10-00di-0090000000-90a6e640c735788d17ca2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexchlorpheniramine 20V, Negative-QTOFsplash10-00di-1090000000-89ac3cf688134ba8a50b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexchlorpheniramine 40V, Negative-QTOFsplash10-01tc-6490000000-4242ef7cec7b0b0a73932017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexchlorpheniramine 10V, Negative-QTOFsplash10-00di-0090000000-df52e539d08e1efa7d952021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexchlorpheniramine 20V, Negative-QTOFsplash10-00di-4190000000-96b9d2a99d0b210996622021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexchlorpheniramine 40V, Negative-QTOFsplash10-0ue9-7290000000-01c0916a8749a49cbb872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexchlorpheniramine 10V, Positive-QTOFsplash10-003r-0090000000-5f85b20ee35517cd81922021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexchlorpheniramine 20V, Positive-QTOFsplash10-001i-0090000000-2b9a28bfe8944378684a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexchlorpheniramine 40V, Positive-QTOFsplash10-0fsi-1590000000-38bfc333cd948f84c9292021-09-22Wishart 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 IDDB13679
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID30576
KEGG Compound IDC06946
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDexchlorpheniramine
METLIN IDNot Available
PubChem Compound33036
PDB IDNot Available
ChEBI ID4464
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. Theunissen EL, Vermeeren A, Ramaekers JG: Repeated-dose effects of mequitazine, cetirizine and dexchlorpheniramine on driving and psychomotor performance. Br J Clin Pharmacol. 2006 Jan;61(1):79-86. [PubMed:16390354 ]