Record Information
Version1.0
Creation date2010-04-08 22:06:51 UTC
Update date2019-11-26 03:00:46 UTC
Primary IDFDB005796
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSatiomem
DescriptionCarbinoxamine, also known as carbinoxamine maleate or clistin, is a member of the class of compounds known as benzylethers. Benzylethers are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene). Carbinoxamine is practically insoluble (in water) and a very strong basic compound (based on its pKa). Carbinoxamine can be found in barley and garden onion, which makes carbinoxamine a potential biomarker for the consumption of these food products. Carbinoxamine can be found primarily in blood and urine. In humans, carbinoxamine is involved in the carbinoxamine h1-antihistamine action. Carbinoxamine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Carbinoxamine is a drug which is used for symptomatic relief of seasonal and perennial allergic rhinitis and vasomotor rhinitis, as well as allergic conjunctivitis caused by foods and inhaled allergens. also for the relief of allergic reactions to blood or plasma, and the symptomatic management of mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Carbinoxamine (Clistin, Palgic, Rondec, Rhinopront) is a antihistamine and anticholinergic agent. It was first launched in the United States by the McNeil Corporation under the brand name Clistin. It is now available under the brand name Palgic as 4 mg tablets or 4 mg/5 mL liquid. It is approved by the U.S. Food and Drug Administration (FDA) (specifically at the 4 mg dose/strength) for hay fever (a.k.a. allergic rhinitis, SAR and PAR); vasomotor rhinitis; mild urticaria; angioedema, dermatographism and allergic conjunctivitis. Carbinoxamine is a histamine antagonist, specifically an H1-antagonist. The maleic acid salt of the levorotatory isomer is sold as the prescription drug rotoxamine . Carbinoxamine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding. Carbinoxamine's anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown (DrugBank). Carbinoxamine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding. Carbinoxamine's anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown (T3DB).
CAS Number486-16-8
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP3.03ALOGPS
logP3.27ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity82.13 m³·mol⁻¹ChemAxon
Polarizability31.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H19ClN2O
IUPAC name{2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]ethyl}dimethylamine
InChI IdentifierInChI=1S/C16H19ClN2O/c1-19(2)11-12-20-16(15-5-3-4-10-18-15)13-6-8-14(17)9-7-13/h3-10,16H,11-12H2,1-2H3
InChI KeyOJFSXZCBGQGRNV-UHFFFAOYSA-N
Isomeric SMILESCN(C)CCOC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1
Average Molecular Weight290.788
Monoisotopic Molecular Weight290.118590947
Classification
Description Belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzylethers
Direct ParentBenzylethers
Alternative Parents
Substituents
  • Benzylether
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organohalogen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0ab9-9200000000-c3abf61d5cdaa81de77d2014-09-20View Spectrum
GC-MSSatiomem, non-derivatized, GC-MS Spectrumsplash10-0ab9-9000000000-a413c068c7a879eb2068Spectrum
GC-MSSatiomem, non-derivatized, GC-MS Spectrumsplash10-0ab9-9000000000-a413c068c7a879eb2068Spectrum
Predicted GC-MSSatiomem, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pb9-9180000000-b7d95742727b1ef0a3c4Spectrum
Predicted GC-MSSatiomem, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , positivesplash10-0uxr-0490000000-9ece1371a4992f21aa522017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1090000000-eecfc1a96c21589df0232016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-4090000000-f55a8c538f446792b0842016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9210000000-cc26b029a0e987b184462016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-dbe5de39fc21f0c120882016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0190000000-757e5fdc2e3d83027d7a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-7890000000-70eeab9a0ba6cc4b24492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6x-0090000000-8e6319ead8805445ce4f2021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-b1b5900f97954c8ed4492021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-5090000000-c844f1f981eb3e25a3bf2021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-f8ccd79e440175ba372a2021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-2190000000-37dda60416c010f365ad2021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-4490000000-742d9da4f019f9a49ad22021-10-11View Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDSATIOMEM
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).