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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.013 g/LNot Available
LogP3.4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+167.22230932474
DeepCCS[M-H]-164.86430932474
DeepCCS[M-2H]-197.75130932474
DeepCCS[M+Na]+173.31630932474
AllCCS[M+H]+169.832859911
AllCCS[M+H-H2O]+166.232859911
AllCCS[M+NH4]+173.132859911
AllCCS[M+Na]+174.032859911
AllCCS[M-H]-171.032859911
AllCCS[M+Na-2H]-171.332859911
AllCCS[M+HCOO]-171.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DexbrompheniramineCN(C)CC[C@@H](C1=CC=C(Br)C=C1)C1=CC=CC=N12993.0Standard polar33892256
DexbrompheniramineCN(C)CC[C@@H](C1=CC=C(Br)C=C1)C1=CC=CC=N12074.1Standard non polar33892256
DexbrompheniramineCN(C)CC[C@@H](C1=CC=C(Br)C=C1)C1=CC=CC=N12104.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dexbrompheniramine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9050000000-d51445063b50de15bdcc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dexbrompheniramine 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 - Dexbrompheniramine LC-ESI-qTof , Positive-QTOFsplash10-0292-0940000000-f369442eba5344b3ecb42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dexbrompheniramine , positive-QTOFsplash10-0292-0940000000-f369442eba5344b3ecb42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dexbrompheniramine 35V, Positive-QTOFsplash10-00di-0390000000-82ba7f6766f236ef36042021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexbrompheniramine 10V, Positive-QTOFsplash10-014i-0029000000-fa060b2610f05fd6963a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexbrompheniramine 20V, Positive-QTOFsplash10-01b9-0197000000-90a5b62f5a9e47f958022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexbrompheniramine 40V, Positive-QTOFsplash10-0fef-3690000000-914dbc7e9fc6b1ce196a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexbrompheniramine 10V, Negative-QTOFsplash10-014i-0009000000-1bc9f3a3603646c315042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexbrompheniramine 20V, Negative-QTOFsplash10-014i-1019000000-14a32020bd62ee6fb3b72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexbrompheniramine 40V, Negative-QTOFsplash10-0fi4-7591000000-cd391d2ec4970c9e8b8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexbrompheniramine 10V, Negative-QTOFsplash10-014i-0009000000-615031c9863c28108e0f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexbrompheniramine 20V, Negative-QTOFsplash10-016r-6369000000-b40c997a38a0f9eb2fdb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexbrompheniramine 40V, Negative-QTOFsplash10-004j-9480000000-6c5bc7bd482fbd292a0c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexbrompheniramine 10V, Positive-QTOFsplash10-00di-0094000000-c8e61a4d45703ee2c9062021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexbrompheniramine 20V, Positive-QTOFsplash10-00di-0090000000-363f1320fc00a31daef82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexbrompheniramine 40V, Positive-QTOFsplash10-006t-1290000000-3b9b35511af51a9e3bb52021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00405 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
MarkerDB IDNot Available
Good Scents 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 ]