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Dimethylamine (FDB012589)

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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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)splash10-0006-9000000000-8ae4e0d1cb5c91c730c02014-09-20View Spectrum
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
Predicted GC-MSDimethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDimethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-8b085007dc085a4604222012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-9000000000-103f1d373ec0d015b8072012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0002-9000000000-df28f146170e28bfcb5e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0002-9000000000-cd82fdde4d83a74d83f12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00wc-9100000000-aeb1521c62f5010e11aa2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-017i-9101000000-c269a0887eed5daf0e282012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9000000000-103f1d373ec0d015b8072017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9000000000-df28f146170e28bfcb5e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9000000000-17646ed4f7c44ba140452017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00wc-9100000000-aeb1521c62f5010e11aa2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-017i-9101000000-c269a0887eed5daf0e282017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-933c4b104db02265ac4a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-e85cf853d2e7110d18c12017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-9000000000-2032c41c4ca525ff4e1c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-32c57cc32d61a2feae232017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-36fe99d2cc96e560f5092017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-8914e111239eacc363282017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-46fb6b0f3d2dcd71d1592021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-46fb6b0f3d2dcd71d1592021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-46fb6b0f3d2dcd71d1592021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-e97e92727205304cdb092021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-e97e92727205304cdb092021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-9cf36baccac69593c69f2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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).