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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-11-03 18:50:01 UTC
HMDB IDHMDB00087
Secondary Accession NumbersNone
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 ). 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.
Structure
Thumb
Synonyms
  1. Dimethylamine
  2. Dimethylamine anhydrous
  3. Dimethylamine anhydrous (dot)
  4. Dimethylamine aqueous solution
  5. Dimethylamine hydrobromide
  6. Dimethylamine solution
  7. N,N-Dimethylamine
  8. N-Methyl-Methanamine
  9. N-Methylmethanamine
  10. N-Methylmethanamine (ACD/Name 4.0)
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
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlkylamines
Sub ClassN/A
Other Descriptors
  • methylamines(ChEBI)
  • secondary aliphatic amine(ChEBI)
Substituents
  • N/A
Direct ParentAlkylamines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
Biofunction
  • Osmolyte
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateLiquid
Experimental 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)
Predicted Properties
PropertyValueSource
Water Solubility516.0ALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.69 m3·mol-1ChemAxon
Polarizability5.75 Å3ChemAxon
Spectra
SpectraMS/MSLC-MSMS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Fibroblasts
  • Neuron
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 uMNot SpecifiedBothNormal 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
    • Dame, ZT. et al. ...
details
SalivaDetected and Quantified136 (9.00-262) uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
UrineDetected and Quantified19.2 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal 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 ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
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
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
UrineDetected and Quantified25.4 (8.22-42.7) umol/mmol creatinineAdult (>18 years old)Both
Diabetes
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected and Quantified52 umol/mmol creatinineAdult (>18 years old)FemaleRhabdomyolysis 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
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
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
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
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012589
KNApSAcK IDNot Available
Chemspider ID654
KEGG Compound IDC00543
BioCyc IDDIMETHYLAMINE
BiGG IDNot Available
Wikipedia LinkDimethylamine
NuGOwiki LinkHMDB00087
Metagene LinkHMDB00087
METLIN ID3758
PubChem Compound674
PDB IDDMN
ChEBI ID17170
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. 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

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