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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:48:59 UTC
HMDB IDHMDB0000087
Secondary Accession Numbers
  • HMDB00087
Metabolite Identification
Common NameDimethylamine
DescriptionDimethylamine (DMA) is an organic secondary amine. It is a colorless, liquefied and flammable gas with an ammonia and fish-like odor. Dimethylamine is abundantly present in human urine. Main sources of urinary DMA have been reported to include trimethylamine N-oxide, a common food component, 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 and whiting with cod, haddock, sardine, skate and swordfish (PMID: 18282650 ). It has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). As a pure chemical substance Dimethylamine is used as dehairing agent in tanning, in dyes, in rubber 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. Study has shown that DMA is a metabolite of Arthrobacter and Micrococcus (PMID: 11422368 ; PMID: 7191 ).
Structure
Data?1582752111
Synonyms
ValueSource
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
Chemical FormulaC2H7N
Average Molecular Weight45.0837
Monoisotopic Molecular Weight45.057849229
IUPAC Namedimethylamine
Traditional Namedimethylamine
CAS Registry Number124-40-3
SMILES
CNC
InChI Identifier
InChI=1S/C2H7N/c1-3-2/h3H,1-2H3
InChI KeyROSDSFDQCJNGOL-UHFFFAOYSA-N
Chemical Taxonomy
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

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-92.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1630 mg/mL at 40 °CNot Available
LogP-0.38HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+118.27530932474
DeepCCS[M-H]-116.3830932474
DeepCCS[M-2H]-151.95630932474
DeepCCS[M+Na]+126.34330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DimethylamineCNC621.1Standard polar33892256
DimethylamineCNC382.2Standard non polar33892256
DimethylamineCNC410.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dimethylamine,1TMS,isomer #1CN(C)[Si](C)(C)C667.3Semi standard non polar33892256
Dimethylamine,1TMS,isomer #1CN(C)[Si](C)(C)C661.6Standard non polar33892256
Dimethylamine,1TMS,isomer #1CN(C)[Si](C)(C)C754.3Standard polar33892256
Dimethylamine,1TBDMS,isomer #1CN(C)[Si](C)(C)C(C)(C)C884.0Semi standard non polar33892256
Dimethylamine,1TBDMS,isomer #1CN(C)[Si](C)(C)C(C)(C)C867.1Standard non polar33892256
Dimethylamine,1TBDMS,isomer #1CN(C)[Si](C)(C)C(C)(C)C912.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Dimethylamine EI-B (Non-derivatized)splash10-0006-9000000000-cfb8e10b3b28eba997932017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dimethylamine EI-B (Non-derivatized)splash10-0006-9000000000-cfb8e10b3b28eba997932018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dimethylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-398c710ba4ea34342a912017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dimethylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dimethylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-8ae4e0d1cb5c91c730c02014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylamine EI-B (HITACHI M-80B) , Positive-QTOFsplash10-0006-9000000000-8b085007dc085a4604222012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0002-9000000000-103f1d373ec0d015b8072012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0002-9000000000-df28f146170e28bfcb5e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0002-9000000000-cd82fdde4d83a74d83f12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-00wc-9100000000-aeb1521c62f5010e11aa2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-017i-9101000000-c269a0887eed5daf0e282012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylamine LC-ESI-QQ , positive-QTOFsplash10-0002-9000000000-103f1d373ec0d015b8072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylamine LC-ESI-QQ , positive-QTOFsplash10-0002-9000000000-df28f146170e28bfcb5e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylamine LC-ESI-QQ , positive-QTOFsplash10-0002-9000000000-17646ed4f7c44ba140452017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylamine LC-ESI-QQ , positive-QTOFsplash10-00wc-9100000000-aeb1521c62f5010e11aa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylamine LC-ESI-QQ , positive-QTOFsplash10-017i-9101000000-c269a0887eed5daf0e282017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylamine 10V, Negative-QTOFsplash10-0006-9000000000-32c57cc32d61a2feae232017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylamine 20V, Negative-QTOFsplash10-0006-9000000000-36fe99d2cc96e560f5092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylamine 40V, Negative-QTOFsplash10-0006-9000000000-8914e111239eacc363282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylamine 10V, Negative-QTOFsplash10-0006-9000000000-46fb6b0f3d2dcd71d1592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylamine 20V, Negative-QTOFsplash10-0006-9000000000-46fb6b0f3d2dcd71d1592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylamine 40V, Negative-QTOFsplash10-0006-9000000000-46fb6b0f3d2dcd71d1592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylamine 10V, Positive-QTOFsplash10-0002-9000000000-933c4b104db02265ac4a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylamine 20V, Positive-QTOFsplash10-0002-9000000000-e85cf853d2e7110d18c12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylamine 40V, Positive-QTOFsplash10-014j-9000000000-2032c41c4ca525ff4e1c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylamine 10V, Positive-QTOFsplash10-0002-9000000000-e97e92727205304cdb092021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylamine 20V, Positive-QTOFsplash10-0002-9000000000-e97e92727205304cdb092021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylamine 40V, Positive-QTOFsplash10-0006-9000000000-9cf36baccac69593c69f2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Fibroblasts
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified20.18 (3.33-53.22) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.43 +/- 0.23 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified3.3 +/- 1.5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified48.36 +/- 7.32 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.0 +/- 1.0 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected and Quantified13 (1-50) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified13 (1-44) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified16 (1-57) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified11 (2-27) uMAdult (>18 years old)Female
Normal
details
SalivaDetected and Quantified1-65 uMAdult (>18 years old)Male
normal
details
SalivaDetected and Quantified1-30 uMAdult (>18 years old)Male
normal
details
SalivaDetected and Quantified7.82 +/- 3.13 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified136 (9.00-262) uMAdult (>18 years old)BothNormal details
SweatDetected and Quantified< 10 uMAdult (60 years old)Male
Normal
details
SweatDetected and Quantified< 10 uMAdult (40 years old)Male
Normal
details
UrineDetected and Quantified17.059 +/- 6.3921 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.00050 +/- 0.00055 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified19.2 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.22 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified30.8 (20.3-59.2) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified36.13 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified34.4 +/- 9.3 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified39.3 +/- 8.3 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified25.2 +/- 1.2 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified56.97 +/- 42.793 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified48.1 +/- 47.6 umol/mmol creatinineChildren (1-13 years old)MaleNormal details
UrineDetected and Quantified30.35 (16.30 – 50.36) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Lorena Ivona ŞTEF...
details
UrineDetected and Quantified25.0 (22.0-28.0) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified20-60 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.5 (1.4) uMAdult (>18 years old)FemaleEarly preeclampsia details
BloodDetected and Quantified4.0 (2.7) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified228.46 +/- 35.49 uMAdult (>18 years old)Bothuremia details
BloodDetected and Quantified29.1 +/- 12.1 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified3.2 (1.7) uMAdult (>18 years old)FemaleLate-onset preeclampsia details
BloodDetected and Quantified4.4 (2.1) uMAdult (>18 years old)FemalePregnancy details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Pancreatic cancer
details
BloodDetected and Quantified33.6 (19.0) uMAdult (>18 years old)FemaleDown syndrome pregnancy details
BloodDetected and Quantified49.1 (30.6) uMAdult (>18 years old)FemalePregnancy details
UrineDetected and Quantified17.5908 +/- 6.4589 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified15.4394 +/- 7.28 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
details
UrineDetected and Quantified25.4 (8.22-42.7) umol/mmol creatinineAdult (>18 years old)Both
Diabetes
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected and Quantified52 umol/mmol creatinineAdult (>18 years old)FemaleRhabdomyolysis details
UrineDetected and Quantified56.531 +/- 42.872 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified78.9 +/- 29.2 umol/mmol creatinineChildren (1-13 years old)MaleDuchenne Muscular Dystrophy details
UrineDetected and Quantified35.268 (6.543 - 159.703) umol/mmol creatinineAdult (>18 years old)Both
Bladder infections
details
UrineDetected and Quantified32.42 (4.89 – 61.25) umol/mmol creatinineAdult (>18 years old)BothType 1 diabetes Mellitus
    • Lorena Ivona ŞTEF...
details
Associated Disorders and Diseases
Disease References
Kidney disease
  1. Teerlink T, Hennekes MW, Mulder C, Brulez HF: Determination of dimethylamine in biological samples by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1997 Apr 11;691(2):269-76. [PubMed:9174262 ]
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Early preeclampsia
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
Pregnancy
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
  2. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
  3. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester Down syndrome prediction. Am J Obstet Gynecol. 2013 May;208(5):371.e1-8. doi: 10.1016/j.ajog.2012.12.035. Epub 2013 Jan 8. [PubMed:23313728 ]
Late-onset preeclampsia
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
Pancreatic cancer
  1. Zhang L, Jin H, Guo X, Yang Z, Zhao L, Tang S, Mo P, Wu K, Nie Y, Pan Y, Fan D: Distinguishing pancreatic cancer from chronic pancreatitis and healthy individuals by (1)H nuclear magnetic resonance-based metabonomic profiles. Clin Biochem. 2012 Sep;45(13-14):1064-9. doi: 10.1016/j.clinbiochem.2012.05.012. Epub 2012 May 19. [PubMed:22613268 ]
Diabetes mellitus type 2
  1. Zhang AQ, Mitchell SC, Smith RL: Dimethylamine in human urine. Clin Chim Acta. 1995 Jan 16;233(1-2):81-8. [PubMed:7758205 ]
Rhabdomyolysis
  1. Bairaktari E, Seferiadis K, Liamis G, Psihogios N, Tsolas O, Elisaf M: Rhabdomyolysis-related renal tubular damage studied by proton nuclear magnetic resonance spectroscopy of urine. Clin Chem. 2002 Jul;48(7):1106-9. [PubMed:12089184 ]
Diabetes mellitus type 1
  1. (). Lorena Ivona ŞTEFAN, Alina NICOLESCU, Simona POPA, Maria MOŢA, Eugenia KOVACS and Calin DELEANU. 1H-NMR URINE METABOLIC PROFILING IN TYPE 1 DIABETES MELLITUS. Rev. Roum. Chim., 2010, 55(11-12), 1033-1037 . .
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Bladder infections
  1. Tricker AR, Pfundstein B, Kalble T, Preussmann R: Secondary amine precursors to nitrosamines in human saliva, gastric juice, blood, urine and faeces. Carcinogenesis. 1992 Apr;13(4):563-8. [PubMed:1576707 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Duchenne Muscular Dystrophy
  1. Horster I, Weigt-Usinger K, Carmann C, Chobanyan-Jurgens K, Kohler C, Schara U, Kayacelebi AA, Beckmann B, Tsikas D, Lucke T: The L-arginine/NO pathway and homoarginine are altered in Duchenne muscular dystrophy and improved by glucocorticoids. Amino Acids. 2015 Sep;47(9):1853-63. doi: 10.1007/s00726-015-2018-x. Epub 2015 Jun 12. [PubMed:26066683 ]
Associated OMIM IDs
  • 260350 (Pancreatic cancer)
  • 125853 (Diabetes mellitus type 2)
  • 222100 (Diabetes mellitus type 1)
  • 601313 (Autosomal dominant polycystic kidney disease)
  • 610247 (Eosinophilic esophagitis)
  • 310200 (Duchenne Muscular Dystrophy)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012589
KNApSAcK IDNot Available
Chemspider ID654
KEGG Compound IDC00543
BioCyc IDDIMETHYLAMINE
BiGG IDNot Available
Wikipedia LinkDimethylamine
METLIN ID3758
PubChem Compound674
PDB IDNot Available
ChEBI ID17170
Food Biomarker OntologyNot Available
VMH IDDMA
MarkerDB IDMDB00000046
Good Scents IDNot Available
References
Synthesis ReferenceZones, Stacey I.; Burton, Allen W. Production of methylamine and dimethylamine using STI zeolite catalysts. U.S. Pat. Appl. Publ. (2007), 6pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. [PubMed:7762816 ]
  2. Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. [PubMed:8257730 ]
  3. Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. [PubMed:9869358 ]
  4. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
  5. Zeisel SH, daCosta KA, Youssef M, Hensey S: Conversion of dietary choline to trimethylamine and dimethylamine in rats: dose-response relationship. J Nutr. 1989 May;119(5):800-4. [PubMed:2723829 ]
  6. Lee L, Archer MC, Bruce WR: Absence of volatile nitrosamines in human feces. Cancer Res. 1981 Oct;41(10):3992-4. [PubMed:7285009 ]
  7. Sharif NA, Crider JY, Davis TL: AL-3138 antagonizes FP prostanoid receptor-mediated inositol phosphates generation: comparison with some purported FP antagonists. J Pharm Pharmacol. 2000 Dec;52(12):1529-39. [PubMed:11197083 ]
  8. Hughes R, Dart J, Kilvington S: Activity of the amidoamine myristamidopropyl dimethylamine against keratitis pathogens. J Antimicrob Chemother. 2003 Jun;51(6):1415-8. Epub 2003 Apr 25. [PubMed:12716783 ]
  9. Le Moyec L, Racine S, Le Toumelin P, Adnet F, Larue V, Cohen Y, Leroux Y, Cupa M, Hantz E: Aminoglycoside and glycopeptide renal toxicity in intensive care patients studied by proton magnetic resonance spectroscopy of urine. Crit Care Med. 2002 Jun;30(6):1242-5. [PubMed:12072675 ]
  10. Mulder C, Wahlund LO, Blomberg M, de Jong S, van Kamp GJ, Scheltens P, Teerlink T: Alzheimer's disease is not associated with altered concentrations of the nitric oxide synthase inhibitor asymmetric dimethylarginine in cerebrospinal fluid. J Neural Transm (Vienna). 2002 Sep;109(9):1203-8. [PubMed:12203047 ]
  11. Messana I, Forni F, Ferrari F, Rossi C, Giardina B, Zuppi C: Proton nuclear magnetic resonance spectral profiles of urine in type II diabetic patients. Clin Chem. 1998 Jul;44(7):1529-34. [PubMed:9665433 ]
  12. Lichtenberger LM, Gardner JW, Barreto JC, Morriss FH Jr: Evidence for a role of volatile amines in the development of neonatal hypergastrinemia. J Pediatr Gastroenterol Nutr. 1991 Nov;13(4):342-6. [PubMed:1779307 ]
  13. Zhang AQ, Mitchell SC, Smith RL: Dimethylamine in human urine. Clin Chim Acta. 1995 Jan 16;233(1-2):81-8. [PubMed:7758205 ]
  14. Choi SY, Chung MJ, Sung NJ: Volatile N-nitrosamine inhibition after intake Korean green tea and Maesil (Prunus mume SIEB. et ZACC.) extracts with an amine-rich diet in subjects ingesting nitrate. Food Chem Toxicol. 2002 Jul;40(7):949-57. [PubMed:12065217 ]
  15. Kilvington S, Hughes R, Byas J, Dart J: Activities of therapeutic agents and myristamidopropyl dimethylamine against Acanthamoeba isolates. Antimicrob Agents Chemother. 2002 Jun;46(6):2007-9. [PubMed:12019127 ]
  16. Mitchell SC, Zhang AQ, Smith RL: Dimethylamine and diet. Food Chem Toxicol. 2008 May;46(5):1734-8. doi: 10.1016/j.fct.2008.01.010. Epub 2008 Jan 15. [PubMed:18282650 ]
  17. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  18. Meskys R, Harris RJ, Casaite V, Basran J, Scrutton NS: Organization of the genes involved in dimethylglycine and sarcosine degradation in Arthrobacter spp.: implications for glycine betaine catabolism. Eur J Biochem. 2001 Jun;268(12):3390-8. [PubMed:11422368 ]
  19. Tate RL 3rd, Alexander M: Microbial formation and degradation of dimethylamine. Appl Environ Microbiol. 1976 Mar;31(3):399-403. [PubMed:7191 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
Citalopram + Oxygen + Water → Citalopram aldehyde + Dimethylamine + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
Citalopram + Oxygen + Water → Citalopram aldehyde + Dimethylamine + Hydrogen peroxidedetails
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidines
Specific function:
Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
Gene Name:
DDAH1
Uniprot ID:
O94760
Molecular weight:
20189.135
Reactions
Asymmetric dimethylarginine + Water → Dimethylamine + Citrullinedetails
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidines
Specific function:
Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
Gene Name:
DDAH2
Uniprot ID:
O95865
Molecular weight:
29643.54
Reactions
Asymmetric dimethylarginine + Water → Dimethylamine + Citrullinedetails