Record Information
Version1.0
Creation date2011-09-21 00:18:51 UTC
Update date2015-10-09 22:31:18 UTC
Primary IDFDB022738
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDextromethorphan
DescriptionDextromethorphan is an antitussive drug that is found in many over-the-counter cold and cough preparations, usually in the form of dextromethorphan hydrobromide. Dextromethorphan is a salt of the methyl ether dextrorotatory isomer of levorphanol, a narcotic analgesic. Dextromethorphan occurs as white crystals, is sparingly soluble in water, and freely soluble in alcohol. The drug is dextrorotatory in water (at 20 degrees Celsius, Sodium D-line) with a specific rotation of +27.6 degrees. Following oral administration, dextromethorphan is rapidly absorbed from the gastrointestinal tract, where it enters the bloodstream and crosses the blood-brain barrier. The first-pass through the hepatic portal vein results in some of the drug being metabolized into an active metabolite of dextromethorphan, dextrorphan, the 3-hydroxy derivative of dextromethorphan. The therapeutic activity of dextromethorphan is believed to be caused by both the drug and this metabolite. Dextromethorphan is predominantly metabolized by the liver, by various hepatic enzymes. Through various pathways, the drug undergoes (O-demethylation (which produces dextrorphan), N-demethylation, and partial conjugation with glucuronic acid and sulfate ions. The inactive metabolite (+)-3-hydroxy-N-methylmorphinan is formed as a product of DXM metabolism by these pathways. One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6. A significant portion of the population has a functional deficiency in this enzyme (and are known as poor CYP2D6 metabolizers). As CYP2D6 is the primary metabolic pathway in the inactivation of dextromethorphan, the duration of action and effects of dextromethorphan are significantly increased in such poor metabolizers. Deaths and hospitalizations have been reported in recreational use by poor CYP2D6 metabolizers. -- Wikipedia [HMDB]
CAS Number125-71-3
Structure
Thumb
Synonyms
SynonymSource
Bayer Select Flu Reliefhmdb
Bayer Select Head & Chest Coldhmdb
Bayer Select Night Time Coldhmdb
Benylin DMhmdb
Benylin DM (TN)hmdb
Cerose-DMhmdb
Chloraseptic DMhmdb
Contac Day & Night Cold/Flu Day Capletshmdb
Contac Jr. Non-drowsy Formulahmdb
Contac Nighttime Cold Medicinehmdb
Contac Severe Cold Formula Maximum Strengthhmdb
Contac Severe Cold Formula Non-Drowsyhmdb
Coricidin Syruphmdb
Cough-Xhmdb
D-MethorphanHMDB
D-Methorphan hydrobromideHMDB
delta-MethorphanHMDB
DemorphanHMDB
Demorphan hydrobromideHMDB
DemorphineHMDB
DestrometerfanoHMDB
Dextromethorphan bromhydrateHMDB
Dextromethorphan bromideHMDB
Dextromethorphan hydrobromideHMDB
Dextromethorphan hydrobromide [BAN:JAN]hmdb
Dextromethorphan hydrobromide monohydratehmdb
Dextromethorphan hydrobromide OROS Tabletshmdb
DextrometorphanHMDB
DextromorphanHMDB
DexyromethorphanHMDB
Dimacolhmdb
Dimetapp DMhmdb
Drixoral Coughhmdb
Drixoral Cough & Congestionhmdb
Drixoral Cough & Sore Throathmdb
Endotussin-NNhmdb
Endotussin-NN Pediatrichmdb
Holdhmdb
L-MethorphanHMDB
LevomethorphanHMDB
Methoratehmdb
Naldecon-DXhmdb
Ornex Severe Cold Formulahmdb
Orthoxicolhmdb
PediaCare 1hmdb
PediaCare Cough-Cold Formulahmdb
Prestwick_686hmdb
Robitussin CFhmdb
Robitussin Cold & Coughhmdb
Robitussin Cough Calmershmdb
Robitussin DMhmdb
Robitussin Maximum Strength Coughhmdb
Robitussin Pediatric Coughhmdb
Robitussin Pediatric Cough & Coldhmdb
Robitussin Pediatric Night Reliefhmdb
Romilarhmdb
Rondec dmhmdb
Ru-Tuss Expectoranthmdb
St. Joseph Cough Syruphmdb
Sudafed Cough Syruphmdb
Triaminichmdb
Trind-DMhmdb
Tussar DMhmdb
Tussi-Organidinhmdb
Tussi-Organidin DM NRhmdb
Tussi-Organidin DM-S NRhmdb
Tylenol Cold and Flu Multi-Symptomhmdb
Tylenol Cold and Flu No Drowsinesshmdb
Tylenol Cold No Drowsinesshmdb
Tylenol Cough + Decongestant Liquidhmdb
Tylenol Cough Liquidhmdb
Tylenol Flu No Drowsiness Gelcapshmdb
Viro-Medhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0085 g/LALOGPS
logP3.75ALOGPS
logP3.49ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)9.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity82.56 m³·mol⁻¹ChemAxon
Polarizability84.43 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H25NO
IUPAC name(1S,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene
InChI IdentifierInChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18-/m0/s1
InChI KeyMKXZASYAUGDDCJ-JQHSSLGASA-N
Isomeric SMILES[H][C@@]12CC3=C(C=C(OC)C=C3)[C@@]3(CCCC[C@@]13[H])CCN2C
Average Molecular Weight271.3972
Monoisotopic Molecular Weight271.193614427
Classification
Description belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • Phenanthrene
  • Benzazocine
  • Tetralin
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0006-2931000000-7ed39f5c12687bd18073JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001i-9450000000-484ef060149382ae3835JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-004i-0296000000-9cc5da1af6297bf41d6aJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID13109865
ChEMBL IDCHEMBL52440
KEGG Compound IDC06947
Pubchem Compound ID5360696
Pubchem Substance IDNot Available
ChEBI ID4470
Phenol-Explorer IDNot Available
DrugBank IDDB00514
HMDB IDHMDB01920
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
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References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference