Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 18:49:47 UTC
Update Date2023-02-21 17:30:09 UTC
HMDB IDHMDB0060681
Secondary Accession Numbers
  • HMDB60681
Metabolite Identification
Common Name4-Hydroxy-2,6-dimethylaniline
Description4-Hydroxy-2,6-dimethylaniline, also known as 3,5-dimethyl-4-aminophenol or 4-amino-3,5-dimethylphenol, belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively. Lidocaine is used topically to relieve itching, burning and pain from skin inflammations, injected as a dental anesthetic or as a local anesthetic for minor surgery. 4-Hydroxy-2,6-dimethylaniline is a very strong basic compound (based on its pKa). 4-Hydroxy-2,6-dimethylaniline is a metabolite of lidocaine. In humans, 4-hydroxy-2,6-dimethylaniline is involved in lidocaine (local anaesthetic) metabolism pathway. Lidocaine, Xylocaine, or lignocaine is a common local anesthetic and antiarrhythmic drug.
Structure
Data?1677000609
Synonyms
ValueSource
1,3-Dimethyl-2-amino-5-xylenolChEBI
3,5-Dimethyl-4-aminophenolChEBI
4-Amino-3,5-dimethylphenolChEBI
4-Amino-3,5-xylenolChEBI
Chemical FormulaC8H11NO
Average Molecular Weight137.179
Monoisotopic Molecular Weight137.084063979
IUPAC Name4-amino-3,5-dimethylphenol
Traditional Name4-hydroxy-2,6-dimethylaniline
CAS Registry NumberNot Available
SMILES
CC1=CC(O)=CC(C)=C1N
InChI Identifier
InChI=1S/C8H11NO/c1-5-3-7(10)4-6(2)8(5)9/h3-4,10H,9H2,1-2H3
InChI KeyGCWYXRHXGLFVFE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassCresols
Direct ParentMeta cresols
Alternative Parents
Substituents
  • Aminophenol
  • M-cresol
  • Aniline or substituted anilines
  • Xylene
  • M-xylene
  • P-aminophenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility11.5 g/LALOGPS
logP1.4ALOGPS
logP1.87ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)10.62ChemAxon
pKa (Strongest Basic)5.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.82 m³·mol⁻¹ChemAxon
Polarizability15.29 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.98831661259
DarkChem[M-H]-125.38831661259
DeepCCS[M+H]+133.15530932474
DeepCCS[M-H]-130.51230932474
DeepCCS[M-2H]-166.9630932474
DeepCCS[M+Na]+142.1230932474
AllCCS[M+H]+128.132859911
AllCCS[M+H-H2O]+123.532859911
AllCCS[M+NH4]+132.532859911
AllCCS[M+Na]+133.732859911
AllCCS[M-H]-127.032859911
AllCCS[M+Na-2H]-128.832859911
AllCCS[M+HCOO]-130.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-2,6-dimethylanilineCC1=CC(O)=CC(C)=C1N2358.9Standard polar33892256
4-Hydroxy-2,6-dimethylanilineCC1=CC(O)=CC(C)=C1N1478.4Standard non polar33892256
4-Hydroxy-2,6-dimethylanilineCC1=CC(O)=CC(C)=C1N1453.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-2,6-dimethylaniline,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(C)=C1N1477.8Semi standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,1TMS,isomer #2CC1=CC(O)=CC(C)=C1N[Si](C)(C)C1668.4Semi standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,2TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(C)=C1N[Si](C)(C)C1600.4Semi standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,2TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(C)=C1N[Si](C)(C)C1521.6Standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,2TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(C)=C1N[Si](C)(C)C1702.5Standard polar33892256
4-Hydroxy-2,6-dimethylaniline,2TMS,isomer #2CC1=CC(O)=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C1735.9Semi standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,2TMS,isomer #2CC1=CC(O)=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C1755.7Standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,2TMS,isomer #2CC1=CC(O)=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C1811.4Standard polar33892256
4-Hydroxy-2,6-dimethylaniline,3TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C1618.3Semi standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,3TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C1687.7Standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,3TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C1612.1Standard polar33892256
4-Hydroxy-2,6-dimethylaniline,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1N1706.4Semi standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,1TBDMS,isomer #2CC1=CC(O)=CC(C)=C1N[Si](C)(C)C(C)(C)C1859.3Semi standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,2TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1N[Si](C)(C)C(C)(C)C2066.9Semi standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,2TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1N[Si](C)(C)C(C)(C)C1977.8Standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,2TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1N[Si](C)(C)C(C)(C)C1985.0Standard polar33892256
4-Hydroxy-2,6-dimethylaniline,2TBDMS,isomer #2CC1=CC(O)=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2104.6Semi standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,2TBDMS,isomer #2CC1=CC(O)=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2144.0Standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,2TBDMS,isomer #2CC1=CC(O)=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2010.4Standard polar33892256
4-Hydroxy-2,6-dimethylaniline,3TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2342.4Semi standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,3TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2290.4Standard non polar33892256
4-Hydroxy-2,6-dimethylaniline,3TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2024.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-2,6-dimethylaniline GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0900000000-97bc1ee3bebd1e44a09c2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-2,6-dimethylaniline GC-MS (1 TMS) - 70eV, Positivesplash10-0abl-7920000000-ec1ed05f00971265ac842017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-2,6-dimethylaniline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-2,6-dimethylaniline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,6-dimethylaniline 10V, Positive-QTOFsplash10-0079-0900000000-4f283f94d6b592e724f32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,6-dimethylaniline 20V, Positive-QTOFsplash10-0079-0900000000-0aa7572dd0deefc521542017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,6-dimethylaniline 40V, Positive-QTOFsplash10-00dl-9700000000-c691bd8b601dbaa199bf2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,6-dimethylaniline 10V, Negative-QTOFsplash10-000i-0900000000-fc8da8f969d5d249e2592017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,6-dimethylaniline 20V, Negative-QTOFsplash10-000i-0900000000-d6f73edc8e14d142cb372017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,6-dimethylaniline 40V, Negative-QTOFsplash10-05n3-6900000000-5038461e545083675eb92017-10-06Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16570
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76543
PDB IDNot Available
ChEBI ID55545
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