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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 18:19:56 UTC
Update Date2019-07-23 14:38:57 UTC
HMDB IDHMDB0240250
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhenyltoloxamine
DescriptionPhenyltoloxamine belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Phenyltoloxamine is a very strong basic compound (based on its pKa). In this respect, it is similar to a closely related antihistamine, orphenadrine, and both drugs are very closely related to diphenhydramine and to doxylamine, the latter of which is the active ingredient in NyQuil and many other cough preparations. In humans, phenyltoloxamine is involved in phenyltoloxamine h1-antihistamine action. Some preparations contain opiates such as codeine or hydrocodone and are controlled. Phenyltoloxamine, like diphenhydramine and doxylamine, is an effective non-narcotic anti-tussive on its own but tends to be effective only for productive coughs as the anticholinergic action will exacerbate dry, unproductive coughs, so it is often combined with dextromethorphan, codeine, ethylmorphine, dihydrocodeine, or hydrocodone in cough suppressants both over the counter and prescription. Phenyltoloxamine is an antihistamine with sedative and analgesic effects. Phenyltoloxamine is widely used in preparations as an enhancing agent for some analgesics and antitussives (acetaminophen, dihydrocodeine, codeine, hydrocodone). It is widely used in certain parts of the world as cough suppressant usually with codeine, and sometimes by itself or in addition to dextromethorphan as it, like diphenhydramine, possesses antitussive action of its own and is particularly useful in semi-productive coughs because of its moderate drying action. Though it is rare in several Western countries, phenyltoloxamine is widely used on the global scale, particularly in the developing world. When used in preparations with acetaminophen it is generally over the counter. It is also used to discourage abuse in certain opiate analgesics due to its unpleasant side effects at high doses. Common adverse effects are those associated with most anticholinergics, with effects being more pronounced in children and the elderly.
Structure
Data?1563892737
Synonyms
ValueSource
AntinHMDB
BistriminHMDB
BristaminHMDB
C 5581HHMDB
HistionexHMDB
PRNHMDB
PhenoxadrinHMDB
PhenoxadrineHMDB
PhentoloxamineHMDB
PhenyltoxamineHMDB
PhenyltoloxamineHMDB
Phenyltoloxamine hydrochlorideMeSH, HMDB
N,N-Dimethyl-2-(alpha-phenyl-O-tolyloxy)ethylamineMeSH, HMDB
Chemical FormulaC17H21NO
Average Molecular Weight255.361
Monoisotopic Molecular Weight255.1623143
IUPAC Name[2-(2-benzylphenoxy)ethyl]dimethylamine
Traditional Namephenyltoloxamine
CAS Registry Number92-12-6
SMILES
CN(C)CCOC1=CC=CC=C1CC1=CC=CC=C1
InChI Identifier
InChI=1S/C17H21NO/c1-18(2)12-13-19-17-11-7-6-10-16(17)14-15-8-4-3-5-9-15/h3-11H,12-14H2,1-2H3
InChI KeyIZRPKIZLIFYYKR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
Predicted Molecular Properties
PropertyValueSource
logP3.51ALOGPS
logP3.93ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)8.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity80.28 m³·mol⁻¹ChemAxon
Polarizability29.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M-H]-PredictedNot Available167.5331661259
AllCCS[M+H]+PredictedNot Available159.80631661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-4846204db840aa67d3e12017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-4846204db840aa67d3e12018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9310000000-aca16420b31b994473372017-08-28View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2290000000-b209d33964c08b4cd6312017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9330000000-bf932229994788386be62017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-a8e2773be1f33eee8f512017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1390000000-a92340da8cccbb6ff2cf2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-3940000000-529ec6e73c0e19911b232017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9600000000-62cec0cdc570e1dc9b132017-07-26View 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 IDDB11160
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenyltoloxamine
METLIN IDNot Available
PubChem Compound7077
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. HOEKSTRA JB, TISCH DE, RAKIETEN N, DICKISON HL: Pharmacological properties of a new antihistaminic agent, phenyltoloxamine (Bristamin). J Am Pharm Assoc Am Pharm Assoc. 1953 Oct;42(10):587-93. [PubMed:13096396 ]