Record Information
Version1.0
Creation date2010-04-08 22:10:15 UTC
Update date2020-09-17 15:42:23 UTC
Primary IDFDB012589
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDimethylamine
DescriptionDimethylamine, also known as DMA or (CH3)2NH, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Dimethylamine is a very strong basic compound (based on its pKa). Dimethylamine (DMA) is also classified as a secondary amine. It is a colorless, liquefied and flammable gas with an ammonia and fish-like odor. Dimethylamine is abundantly present in human urine. The main sources of urinary DMA have been reported to include trimethylamine N-oxide, a common food component found in cold-water fish, and asymmetric dimethylarginine (ADMA), an endogenous inhibitor of nitric oxide (NO) synthesis. ADMA is excreted in the urine in part unmetabolized and in part after hydrolysis to DMA by dimethylarginine dimethylaminohydrolase (DDAH). Statistically significant increases in urinary DMA have been found in individuals after the consumption of fish and seafoods. The highest values were obtained for individuals that consumed coley, squid, whitting, cod, haddock, sardine, skate and swordfish (PMID: 18282650). DMA has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Industrially, DMA is used as dehairing agent in tanning, in dyes, in rubber polymerization accelerators, in soaps and cleaning compounds and as an agricultural fungicide. In the body, DMA also undergoes nitrosation under weak acid conditions to give dimethlynitrosamine. Recent studies have shown that DMA is a metabolite produced by several species of bacteria including Arthrobacter and Micrococcus (PMID: 11422368). Dimethylamine is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2).
CAS Number124-40-3
Structure
Thumb
Synonyms
SynonymSource
DMAChEBI
HNMe2ChEBI
Me2nhChEBI
N,N-DimethylamineChEBI
(CH3)2nhKegg
Dimethylamine anhydrousHMDB
Dimethylamine anhydrous (dot)HMDB
Dimethylamine aqueous solutionHMDB
Dimethylamine hydrobromideHMDB
Dimethylamine solutionHMDB
N-Methyl-methanamineHMDB
N-MethylmethanamineHMDB
N-Methylmethanamine (acd/name 4.0)HMDB
Dimethylamine nitrateHMDB
Dimethylamine perchlorateHMDB
Dimethylamine sulfateHMDB
Dimethylamine hydrochlorideHMDB
Dimethylamine phosphate (3:1)HMDB
Dimethylamine, conjugate acidHMDB
Dimethylammonium chlorideHMDB
Dimethylamine sulfate (1:1)HMDB
Dimethylammonium formateHMDB
Dimethylamine monosulfateHMDB
(CH3)2NHbiospider
Dimethylamine (anhydrous)biospider
Dimethylamine, anhydrous [UN1032] [Flammable gas]biospider
Dimethylammonium bromidebiospider
Me2NHbiospider
Methanamine, n-methyl-biospider
Methanamine, n-methyl-, hydrobromidebiospider
N-methyl-methanaminebiospider
N-methylmethanaminebiospider
N-Methylmethanamine, 9CIdb_source
N,n-dimethylaminebiospider
nchem.125-comp12biospider
Predicted Properties
PropertyValueSource
Water Solubility516 g/LALOGPS
logP-0.53ALOGPS
logP-0.19ChemAxon
logS1.06ALOGPS
pKa (Strongest Basic)10.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.69 m³·mol⁻¹ChemAxon
Polarizability5.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC2H7N
IUPAC namedimethylamine
InChI IdentifierInChI=1S/C2H7N/c1-3-2/h3H,1-2H3
InChI KeyROSDSFDQCJNGOL-UHFFFAOYSA-N
Isomeric SMILESCNC
Average Molecular Weight45.0837
Monoisotopic Molecular Weight45.057849229
Classification
Description Belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylamines
Alternative Parents
Substituents
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Environmental role:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 53.28%; H 15.65%; N 31.07%DFC
Melting PointMp -96°DFC
Boiling PointBp 7°DFC
Experimental Water Solubility1630 mg/mL at 40 oCSCHWEIZER,AE et al. (1978)
Experimental logP-0.38HANSCH,C ET AL. (1995)
Experimental pKapKa 3.28 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd04 0.68DFC
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-8ae4e0d1cb5c91c730c0Spectrum
GC-MSDimethylamine, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-cfb8e10b3b28eba99793Spectrum
GC-MSDimethylamine, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-cfb8e10b3b28eba99793Spectrum
Predicted GC-MSDimethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9000000000-398c710ba4ea34342a91Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-8b085007dc085a460422Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-9000000000-103f1d373ec0d015b807Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0002-9000000000-df28f146170e28bfcb5eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0002-9000000000-cd82fdde4d83a74d83f1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00wc-9100000000-aeb1521c62f5010e11aaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-017i-9101000000-c269a0887eed5daf0e28Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9000000000-103f1d373ec0d015b807Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9000000000-df28f146170e28bfcb5eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9000000000-17646ed4f7c44ba14045Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00wc-9100000000-aeb1521c62f5010e11aaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-017i-9101000000-c269a0887eed5daf0e28Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-32c57cc32d61a2feae23Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-36fe99d2cc96e560f509Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-8914e111239eacc36328Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-46fb6b0f3d2dcd71d159Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-46fb6b0f3d2dcd71d159Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-46fb6b0f3d2dcd71d159Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-933c4b104db02265ac4aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-e85cf853d2e7110d18c1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-9000000000-2032c41c4ca525ff4e1cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-e97e92727205304cdb09Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-e97e92727205304cdb09Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-9cf36baccac69593c69fSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID654
ChEMBL IDCHEMBL120433
KEGG Compound IDC00543
Pubchem Compound ID674
Pubchem Substance IDNot Available
ChEBI ID17170
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00087
CRC / DFC (Dictionary of Food Compounds) IDHJD48-Q:HJD48-Q
EAFUS ID963
Dr. Duke IDDIMETHYL-AMINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDDMN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDimethylamine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
coleoptophileDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
Enzymes
NameGene NameUniProt ID
N(G),N(G)-dimethylarginine dimethylaminohydrolase 2DDAH2O95865
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).