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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-16 23:09:02 UTC
Update Date2019-07-23 14:38:50 UTC
HMDB IDHMDB0240218
Secondary Accession NumbersNone
Metabolite Identification
Common NameDexchlorpheniramine
DescriptionDexchlorpheniramine, also known as dapriton, 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. Dexchlorpheniramine (trade name Polaramine) is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria. A study found that dexchlorpheniramine had a Ki value of 20 to 30 μM for the muscarinic acetylcholine receptors using rat brain tissue. Dexchlorpheniramine is an antihistamine, or an antagonist of the histamine H1 receptor. Dexchlorpheniramine is a very strong basic compound (based on its pKa). In humans, dexchlorpheniramine is involved in dexchlorpheniramine h1-antihistamine action. It is the pharmacologically active dextrorotatory isomer of chlorpheniramine. It was patented in 1962 and came into medical use in 1959.
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
DexclorMeSH, HMDB
Dexchlorpheniramine maleate (1:1), (R)-isomerMeSH, HMDB
Dexchlorpheniramine, (+-)-isomerMeSH, HMDB
DexclorfeniramineMeSH, HMDB
PolaraminMeSH, HMDB
Polargen TDMeSH, HMDB
Dexchlorpheniramine maleate (1:1), (+-)-isomerMeSH, HMDB
Dexchlorpheniramine, (R)-isomerMeSH, HMDB
Dextrochlorpheniramine maleateMeSH, HMDB
PolaronilMeSH, HMDB
PolaramineMeSH, HMDB
Dexchlorpheniramine maleateMeSH, HMDB
Dexchlorpheniramine maleate (1:1), (S)-isomerMeSH, HMDB
Dexchlorpheniramine monohydrochlorideMeSH, HMDB
Dexchlorpheniramine sodium maleate (1:1)MeSH, HMDB
Dexchlorpheniramine, monohydrochloride, (S)-isomerMeSH, HMDB
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 Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9380000000-f4a0f7b13adeafb1762dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0uy0-0960000000-24a36e80af50293ed70dSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0190000000-f6ef5e736260c9c22a16Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uy0-0960000000-24a36e80af50293ed70dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-9b4d486e9c2c7712ca4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0190000000-2c96b165338a445b284dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-3960000000-73025748bd5a00459938Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-90a6e640c735788d17caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1090000000-89ac3cf688134ba8a50bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01tc-6490000000-4242ef7cec7b0b0a7393Spectrum
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 IDNot Available
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
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 ]