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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:42 UTC
HMDB IDHMDB01020
Secondary Accession NumbersNone
Metabolite Identification
Common NameN,N-Dimethylaniline
DescriptionDimethylaniline (C8H11N) is an organic chemical compound which is a substituted derivative of aniline. It consists of a benzene ring and a substituted amino group, making it a tertiary aromatic amine. -- Wikipedia; the structural formula shown is also known as N,N-dimethylaniline -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
DimethylaminobenzeneChEBI
DimethylanilineChEBI
DimethylphenylamineChEBI
N,N-Dimethyl-N-phenylamineChEBI
N,N-DimethylbenzenamineChEBI
N,N-DimethylbenzeneamineChEBI
N,N-DimethylphenylamineChEBI
N,N-(dimethylamino)BenzeneHMDB
N,N-Dimethyl-benzenamineHMDB
Chemical FormulaC8H11N
Average Molecular Weight121.1796
Monoisotopic Molecular Weight121.089149357
IUPAC NameN,N-dimethylaniline
Traditional Namedimethylaniline
CAS Registry Number121-69-7
SMILES
CN(C)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H11N/c1-9(2)8-6-4-3-5-7-8/h3-7H,1-2H3
InChI KeyInChIKey=JLTDJTHDQAWBAV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassTertiary amines
Direct ParentDialkylarylamines
Alternative Parents
Substituents
  • Dialkylarylamine
  • Aniline
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point2.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.45 mg/mLNot Available
LogP2.31HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility14.4 mg/mLALOGPS
logP2.05ALOGPS
logP2.08ChemAxon
logS-0.92ALOGPS
pKa (Strongest Basic)5.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.49 m3·mol-1ChemAxon
Polarizability14.31 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-5b63cd88da62acd2d77fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-0900000000-31c3fe91c89abc5104e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9200000000-f36bb1867752d2b67e26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-00di-1900000000-544ffdcec51667ffcedcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-00di-5900000000-60173199ae4aeb84fe4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-00di-4900000000-7a8c56c9a1e904571576View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-3cec8f9949b4ca1fda59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a4i-0900000000-1402f1580a4bb8ce5135View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-0900000000-e2755a3a974bacd7cdf1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-1900000000-0c939551fc3df2940361View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-056r-9500000000-d7dca8a17ef3b18f33fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-b3487e6b57de233c5872View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-417b2289cb697ca4ac57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmi-9500000000-a5d45941d30346a15ebcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-cc4c1f59bd103642f74cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-9eceba6cab47009c7828View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0umi-6900000000-b85e09230bdd448d6ee5View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Intestine
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB005128
KNApSAcK IDNot Available
Chemspider ID924
KEGG Compound IDC02846
BioCyc IDNN-DIMETHYLANILINE
BiGG IDNot Available
Wikipedia LinkDimethylaniline
NuGOwiki LinkHMDB01020
Metagene LinkHMDB01020
METLIN ID5949
PubChem Compound949
PDB IDNot Available
ChEBI ID16269
References
Synthesis ReferenceLi, Guo-tao; Guan, Nai-jia; Zhang, Huai-bin; Liu, Shu-quan. Synthesis of N, N-dimethylaniline by aniline and methanol over b zeolite catalyst. Shiyou Huagong (2002), 31(2), 81-83.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. DeBruin LS, Josephy PD, Pawliszyn JB: Solid-phase microextraction of monocyclic aromatic amines from biological fluids. Anal Chem. 1998 May 1;70(9):1986-92. [9599591 ]
  2. Berckmans RJ, Boer P: An inexpensive method for sensitive enzymatic determination of oxalate in urine and plasma. Clin Chem. 1988 Jul;34(7):1451-5. [3390916 ]
  3. Raza H, Bhagwat SV, John A: Flavin-containing monooxygenase activity in camel tissues: comparison with rat and human liver enzymes. Comp Biochem Physiol C Toxicol Pharmacol. 2004 Dec;139(4):289-93. [15683840 ]
  4. Headley JV, Maxwell DB, Swyngedouw C, Purdy JR: Determination of combined residues of metalaxyl and 2,6-dimethylaniline metabolites in urine by gas chromatography/mass spectrometry. J AOAC Int. 1996 Jan-Feb;79(1):117-23. [8620103 ]

Enzymes

General function:
Involved in flavin-containing monooxygenase activity
Specific function:
In contrast with other forms of FMO it does not seem to be a drug-metabolizing enzyme.
Gene Name:
FMO5
Uniprot ID:
P49326
Molecular weight:
32480.04
Reactions
N,N-Dimethylaniline + NADPH + Oxygen → Dimethylaniline-N-oxide + NADP + Waterdetails
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
Catalyzes the N-oxidation of certain primary alkylamines to their oximes via an N-hydroxylamine intermediate. Inactive toward certain tertiary amines, such as imipramine or chloropromazine. Can catalyze the S-oxidation of methimazole. The truncated form is catalytically inactive.
Gene Name:
FMO2
Uniprot ID:
Q99518
Molecular weight:
53643.29
Reactions
N,N-Dimethylaniline + NADPH + Oxygen → Dimethylaniline-N-oxide + NADP + Waterdetails
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides.
Gene Name:
FMO4
Uniprot ID:
P31512
Molecular weight:
63342.055
Reactions
N,N-Dimethylaniline + NADPH + Oxygen → Dimethylaniline-N-oxide + NADP + Waterdetails
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds.
Gene Name:
FMO3
Uniprot ID:
P31513
Molecular weight:
60032.975
Reactions
N,N-Dimethylaniline + NADPH + Oxygen → Dimethylaniline-N-oxide + NADP + Waterdetails
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
Gene Name:
FMO1
Uniprot ID:
Q01740
Molecular weight:
60310.285
Reactions
N,N-Dimethylaniline + NADPH + Oxygen → Dimethylaniline-N-oxide + NADP + Waterdetails
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
It is probable that this protein is only produced in very small quantity or not at all as the gene coding for it seems to be unable to produce full length transcripts.
Gene Name:
FMO6P
Uniprot ID:
O60774
Molecular weight:
Not Available
Reactions
N,N-Dimethylaniline + NADPH + Oxygen → Dimethylaniline-N-oxide + NADP + Waterdetails