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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:52 UTC
HMDB IDHMDB0014549
Secondary Accession Numbers
  • HMDB14549
Metabolite Identification
Common NameDexbrompheniramine
DescriptionDexbrompheniramine, also known as parabromdylamine or disophrol, 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. Dexbrompheniramine is a histamine H1 antagonist (or more correctly, an inverse histamine agonist) of the alkylamine class. Signs of an overdose include fast or irregular heartbeat, mental or mood changes, tightness in the chest, and unusual tiredness or weakness. Dexbrompheniramine is a drug which is used for treatment and relief of symptoms of allergies, hay fever, and colds. Dexbrompheniramine is a very strong basic compound (based on its pKa). In humans, dexbrompheniramine is involved in brompheniramine h1-antihistamine action. In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine also increases vascular permeability and potentiates pain.
Structure
Data?1582753192
Synonyms
ValueSource
(+)-BrompheniraminumChEBI
(S)-(+)-BrompheniramineChEBI
(S)-BrompheniramineChEBI
D-BrompheniramineChEBI
DexbromfeniraminaChEBI
DexbrompheniraminumChEBI
ParabromdylamineHMDB
ParabromodylamineHMDB
DisophrolHMDB
Dexbrompheniramine maleateHMDB
Chemical FormulaC16H19BrN2
Average Molecular Weight319.239
Monoisotopic Molecular Weight318.073161265
IUPAC Name[(3S)-3-(4-bromophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
Traditional Namedexbrompheniramine
CAS Registry Number132-21-8
SMILES
CN(C)CC[C@@H](C1=CC=C(Br)C=C1)C1=CC=CC=N1
InChI Identifier
InChI=1S/C16H19BrN2/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 KeyZDIGNSYAACHWNL-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
  • Bromobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl bromide
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.013 g/LNot Available
LogP3.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP3.63ALOGPS
logP3.75ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.67 m³·mol⁻¹ChemAxon
Polarizability31.84 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-9050000000-d51445063b50de15bdccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0292-0940000000-f369442eba5344b3ecb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0292-0940000000-f369442eba5344b3ecb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0029000000-fa060b2610f05fd6963aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-0197000000-90a5b62f5a9e47f95802Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fef-3690000000-914dbc7e9fc6b1ce196aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-1bc9f3a3603646c31504Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1019000000-14a32020bd62ee6fb3b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fi4-7591000000-cd391d2ec4970c9e8b8aSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00405 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00405 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00405
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID16068
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDexbrompheniramine
METLIN IDNot Available
PubChem Compound16960
PDB IDNot Available
ChEBI ID59269
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. McLeod RL, Mingo G, O'Reilly S, Ruck LA, Bolser DC, Hey JA: Antitussive action of antihistamines is independent of sedative and ventilation activity in the guinea pig. Pharmacology. 1998 Aug;57(2):57-64. [PubMed:9691225 ]
  2. Bokesoy TA, Onaran HO: Atypical Schild plots with histamine H1 receptor agonists and antagonists in the rabbit aorta. Eur J Pharmacol. 1991 May 2;197(1):49-56. [PubMed:1680053 ]
  3. Onaran HO, Bokesoy TA: Kinetics of antagonism at histamine-H1 receptors in isolated rabbit arteries. Naunyn Schmiedebergs Arch Pharmacol. 1990 Apr;341(4):316-23. [PubMed:1970615 ]
  4. Yanni JM, Stephens DJ, Parnell DW, Spellman JM: Preclinical efficacy of emedastine, a potent, selective histamine H1 antagonist for topical ocular use. J Ocul Pharmacol. 1994 Winter;10(4):665-75. [PubMed:7714410 ]
  5. Sadofsky LR, Campi B, Trevisani M, Compton SJ, Morice AH: Transient receptor potential vanilloid-1-mediated calcium responses are inhibited by the alkylamine antihistamines dexbrompheniramine and chlorpheniramine. Exp Lung Res. 2008 Dec;34(10):681-93. doi: 10.1080/01902140802339623. [PubMed:19085565 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]