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Human Metabolome Database Version 3.5

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Showing metabocard for Dimethylamine (HMDB00087)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:52 -0700
HMDB ID HMDB00087
Secondary Accession Numbers None
Metabolite Identification
Common Name Dimethylamine
Description Dimethylamine (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 Link_out). 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C2H7N
Average Molecular Weight 45.0837
Monoisotopic Molecular Weight 45.057849229
IUPAC Name dimethylamine
Traditional IUPAC Name dimethylamine
CAS Registry Number 124-40-3
SMILES CNC
InChI Identifier InChI=1S/C2H7N/c1-3-2/h3H,1-2H3
InChI Key ROSDSFDQCJNGOL-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Alkylamines
Sub Class N/A
Other Descriptors
  • methylamines(ChEBI)
  • secondary aliphatic amine(ChEBI)
Substituents
  • N/A
Direct Parent Alkylamines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Osmolyte
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -92.2 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1630 mg/mL at 40 °C Not Available
LogP -0.38 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
LogP -0.53 ALOGPS
LogP -0.19 ChemAxon
LogS 1.06 ALOGPS
pKa (strongest basic) 10.52 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 12.03 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 14.69 ChemAxon
Polarizability 5.75 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
13C NMR Spectrum
MS/MS Spectrum EI-B (HITACHI M-80B)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Fibroblasts
  • Neuron
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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20.18 (3.33-53.22) uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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1.43 +/- 0.23 uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
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3.3 +/- 1.5 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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2.0 +/- 1.0 uM Not Specified Both Normal Not Available
Saliva Detected and Quantified
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1-65 uM Adult (>18 years old) Male normal At rest without stimulation
Saliva Detected and Quantified
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1-30 uM Adult (>18 years old) Male normal Salivary induction with a citric acid solution...
Saliva Detected and Quantified
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136 (9.00-262) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
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19.2 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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30.8 (20.3-59.2) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
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36.13 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
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34.4 +/- 9.3 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
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39.3 +/- 8.3 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
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25.2 +/- 1.2 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Male Normal After green tea sonsumption
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Male Normal After black tea sonsumption
Urine Detected and Quantified
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30.35 (16.30 – 50.36) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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25.0 (22.0-28.0) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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29.1 +/- 12.1 uM Adult (>18 years old) Both Kidney disease chronic renal failure with continuous...
Urine Detected and Quantified
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25.4 (8.22-42.7) umol/mmol creatinine Adult (>18 years old) Both Diabetes Diabetes mellitus with ketoacidosis
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Autosomal dominant polycystic kidney disease Not Available
Urine Detected and Quantified
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52 umol/mmol creatinine Adult (>18 years old) Female Rhabdomyolysis Not Available
Urine Detected and Quantified
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35.268 (6.543 - 159.703) umol/mmol creatinine Adult (>18 years old) Both Bladder infections Chronic bacterial infections of the urinary...
Urine Detected and Quantified
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32.42 (4.89 – 61.25) umol/mmol creatinine Adult (>18 years old) Both Type 1 diabetes Mellitus Not Available
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  • Zhang AQ, Mitchell SC, Smith RL: Dimethylamine in human urine. Clin Chim Acta. 1995 Jan 16;233(1-2):81-8. Pubmed: 7758205 Link_out
    Rhabdomyolysis
    • 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 Link_out
      Kidney disease
      • 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 Link_out
        Associated OMIM IDs
        • 125853 Link_out (Diabetes mellitus type 2)
        DrugBank ID Not Available
        Phenol Explorer Compound ID Not Available
        Phenol Explorer Metabolite ID Not Available
        FoodDB ID FDB012589
        KNApSAcK ID Not Available
        Chemspider ID 654 Link_out
        KEGG Compound ID C00543 Link_out
        BioCyc ID DIMETHYLAMINE Link_out
        BiGG ID Not Available
        Wikipedia Link Dimethylamine Link_out
        NuGOwiki Link HMDB00087 Link_out
        Metagene Link HMDB00087 Link_out
        METLIN ID 3758 Link_out
        PubChem Compound 674 Link_out
        PDB ID DMN Link_out
        ChEBI ID 17170 Link_out
        References
        Synthesis Reference Zones, 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. 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 Link_out
        2. 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 Link_out
        3. Lee L, Archer MC, Bruce WR: Absence of volatile nitrosamines in human feces. Cancer Res. 1981 Oct;41(10):3992-4. Pubmed: 7285009 Link_out
        4. 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 Link_out
        5. 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 Link_out
        6. 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 Link_out
        7. 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 Link_out
        8. 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 Link_out
        9. 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 Link_out
        10. 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 Link_out
        11. 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 Link_out
        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 Link_out
        13. Zhang AQ, Mitchell SC, Smith RL: Dimethylamine in human urine. Clin Chim Acta. 1995 Jan 16;233(1-2):81-8. Pubmed: 7758205 Link_out
        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 Link_out
        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 Link_out
        Enzymes
        Name: Amine oxidase [flavin-containing] B
        Reactions:
        • RCH2NHR' + H2O + O2 = RCHO + R'NH2 + H2O2 [RN:R01853]
        Gene Name: MAOB
        Uniprot ID: P27338 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Amine oxidase [flavin-containing] A
        Reactions:
        • RCH2NHR' + H2O + O2 = RCHO + R'NH2 + H2O2 [RN:R01853]
        Gene Name: MAOA
        Uniprot ID: P21397 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: N(G),N(G)-dimethylarginine dimethylaminohydrolase 1
        Reactions:
        • Nomega,Nomega'-dimethyl-L-arginine + H2O = dimethylamine + L-citrulline [RN:R02513]
        Gene Name: DDAH1
        Uniprot ID: O94760 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: N(G),N(G)-dimethylarginine dimethylaminohydrolase 2
        Reactions:
        • Nomega,Nomega'-dimethyl-L-arginine + H2O = dimethylamine + L-citrulline [RN:R02513]
        Gene Name: DDAH2
        Uniprot ID: O95865 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA