Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 18:49:47 UTC

Update Date

2023-02-21 17:30:09 UTC

HMDB ID

HMDB0060681

Secondary Accession Numbers

HMDB60681

Metabolite Identification

Common Name

4-Hydroxy-2,6-dimethylaniline

Description

4-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,3-Dimethyl-2-amino-5-xylenol	ChEBI
3,5-Dimethyl-4-aminophenol	ChEBI
4-Amino-3,5-dimethylphenol	ChEBI
4-Amino-3,5-xylenol	ChEBI

Chemical Formula

C₈H₁₁NO

Average Molecular Weight

137.179

Monoisotopic Molecular Weight

137.084063979

IUPAC Name

4-amino-3,5-dimethylphenol

Traditional Name

4-hydroxy-2,6-dimethylaniline

CAS Registry Number

Not 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 Key

GCWYXRHXGLFVFE-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

substituted aniline (CHEBI:55545 )
phenols (CHEBI:55545 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060681)

Organ

Liver (HMDB: HMDB0060681)
Kidney (HMDB: HMDB0060681)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060681)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Lidocaine (Antiarrhythmic) Action Pathway (PathBank: SMP0000328)
Lidocaine (Local Anaesthetic) Action Pathway (PathBank: SMP0000398)

Metabolic pathway

Lidocaine (Local Anaesthetic) Metabolism Pathway (PathBank: SMP0000620)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.5 g/L	ALOGPS
logP	1.4	ALOGPS
logP	1.87	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	10.62	ChemAxon
pKa (Strongest Basic)	5.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.82 m³·mol⁻¹	ChemAxon
Polarizability	15.29 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.988	31661259
DarkChem	[M-H]-	125.388	31661259
DeepCCS	[M+H]+	133.155	30932474
DeepCCS	[M-H]-	130.512	30932474
DeepCCS	[M-2H]-	166.96	30932474
DeepCCS	[M+Na]+	142.12	30932474
AllCCS	[M+H]+	128.1	32859911
AllCCS	[M+H-H2O]+	123.5	32859911
AllCCS	[M+NH4]+	132.5	32859911
AllCCS	[M+Na]+	133.7	32859911
AllCCS	[M-H]-	127.0	32859911
AllCCS	[M+Na-2H]-	128.8	32859911
AllCCS	[M+HCOO]-	130.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-2,6-dimethylaniline	CC1=CC(O)=CC(C)=C1N	2358.9	Standard polar	33892256
4-Hydroxy-2,6-dimethylaniline	CC1=CC(O)=CC(C)=C1N	1478.4	Standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline	CC1=CC(O)=CC(C)=C1N	1453.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-2,6-dimethylaniline,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)=C1N	1477.8	Semi standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,1TMS,isomer #2	CC1=CC(O)=CC(C)=C1N[Si](C)(C)C	1668.4	Semi standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)=C1N[Si](C)(C)C	1600.4	Semi standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)=C1N[Si](C)(C)C	1521.6	Standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)=C1N[Si](C)(C)C	1702.5	Standard polar	33892256
4-Hydroxy-2,6-dimethylaniline,2TMS,isomer #2	CC1=CC(O)=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C	1735.9	Semi standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,2TMS,isomer #2	CC1=CC(O)=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C	1755.7	Standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,2TMS,isomer #2	CC1=CC(O)=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C	1811.4	Standard polar	33892256
4-Hydroxy-2,6-dimethylaniline,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C	1618.3	Semi standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C	1687.7	Standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C	1612.1	Standard polar	33892256
4-Hydroxy-2,6-dimethylaniline,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1N	1706.4	Semi standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,1TBDMS,isomer #2	CC1=CC(O)=CC(C)=C1N[Si](C)(C)C(C)(C)C	1859.3	Semi standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1N[Si](C)(C)C(C)(C)C	2066.9	Semi standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1N[Si](C)(C)C(C)(C)C	1977.8	Standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1N[Si](C)(C)C(C)(C)C	1985.0	Standard polar	33892256
4-Hydroxy-2,6-dimethylaniline,2TBDMS,isomer #2	CC1=CC(O)=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2104.6	Semi standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,2TBDMS,isomer #2	CC1=CC(O)=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2144.0	Standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,2TBDMS,isomer #2	CC1=CC(O)=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2010.4	Standard polar	33892256
4-Hydroxy-2,6-dimethylaniline,3TBDMS,isomer #1	CC1=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)C	2342.4	Semi standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,3TBDMS,isomer #1	CC1=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)C	2290.4	Standard non polar	33892256
4-Hydroxy-2,6-dimethylaniline,3TBDMS,isomer #1	CC1=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)C	2024.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-2,6-dimethylaniline GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0900000000-97bc1ee3bebd1e44a09c	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-2,6-dimethylaniline GC-MS (1 TMS) - 70eV, Positive	splash10-0abl-7920000000-ec1ed05f00971265ac84	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-2,6-dimethylaniline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-2,6-dimethylaniline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,6-dimethylaniline 10V, Positive-QTOF	splash10-0079-0900000000-4f283f94d6b592e724f3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,6-dimethylaniline 20V, Positive-QTOF	splash10-0079-0900000000-0aa7572dd0deefc52154	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,6-dimethylaniline 40V, Positive-QTOF	splash10-00dl-9700000000-c691bd8b601dbaa199bf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,6-dimethylaniline 10V, Negative-QTOF	splash10-000i-0900000000-fc8da8f969d5d249e259	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,6-dimethylaniline 20V, Negative-QTOF	splash10-000i-0900000000-d6f73edc8e14d142cb37	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,6-dimethylaniline 40V, Negative-QTOF	splash10-05n3-6900000000-5038461e545083675eb9	2017-10-06	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Lidocaine (Local Anaesthetic) Action Pathway		Not Available
Lidocaine (Local Anaesthetic) Metabolism Pathway		Not Available
Lidocaine (Antiarrhythmic) Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16570

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76543

PDB ID

Not Available

ChEBI ID

55545

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 4-Hydroxy-2,6-dimethylaniline (HMDB0060681)

MOL for HMDB0060681 (4-Hydroxy-2,6-dimethylaniline)

3D MOL for HMDB0060681 (4-Hydroxy-2,6-dimethylaniline)

3D SDF for HMDB0060681 (4-Hydroxy-2,6-dimethylaniline)

3D-SDF for HMDB0060681 (4-Hydroxy-2,6-dimethylaniline)

PDB for HMDB0060681 (4-Hydroxy-2,6-dimethylaniline)

3D PDB for HMDB0060681 (4-Hydroxy-2,6-dimethylaniline)

SMILES for HMDB0060681 (4-Hydroxy-2,6-dimethylaniline)

INCHI for HMDB0060681 (4-Hydroxy-2,6-dimethylaniline)

Structure for HMDB0060681 (4-Hydroxy-2,6-dimethylaniline)

3D Structure for HMDB0060681 (4-Hydroxy-2,6-dimethylaniline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra