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Showing metabocard for Dimethylamine (HMDB0000087)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:56:02 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000087 (Dimethylamine)

Dimethylamine.mol
  Mrv1652303202019012D          

  3  2  0  0  0  0            999 V2000
    0.0000    0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
M  END
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3D MOL for HMDB0000087 (Dimethylamine)

HMDB0000087
     RDKit          3D
Dimethylamine
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.2048    0.1550   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0205    0.3768    0.5077 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1768   -0.2024   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0268   -0.6100   -0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9543   -0.2115    0.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5199    1.1311   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0242    0.3502    1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8965    0.6342   -0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6662   -0.8764    0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700   -0.7470   -1.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  1  5  1  0
  1  6  1  0
  2  7  1  0
  3  8  1  0
  3  9  1  0
  3 10  1  0
M  END
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3D SDF for HMDB0000087 (Dimethylamine)

Dimethylamine.mol
  Mrv1652303202019012D          

  3  2  0  0  0  0            999 V2000
    0.0000    0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000087

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC

> <INCHI_IDENTIFIER>
InChI=1S/C2H7N/c1-3-2/h3H,1-2H3

> <INCHI_KEY>
ROSDSFDQCJNGOL-UHFFFAOYSA-N

> <FORMULA>
C2H7N

> <MOLECULAR_WEIGHT>
45.0837

> <EXACT_MASS>
45.057849229

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
5.7548177246013354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
dimethylamine

> <ALOGPS_LOGP>
-0.53

> <JCHEM_LOGP>
-0.19287847166666677

> <ALOGPS_LOGS>
1.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.522579829086101

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
14.6934

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.16e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethylamine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0000087 (Dimethylamine)

HMDB0000087
     RDKit          3D
Dimethylamine
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.2048    0.1550   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0205    0.3768    0.5077 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1768   -0.2024   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0268   -0.6100   -0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9543   -0.2115    0.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5199    1.1311   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0242    0.3502    1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8965    0.6342   -0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6662   -0.8764    0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700   -0.7470   -1.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  1  5  1  0
  1  6  1  0
  2  7  1  0
  3  8  1  0
  3  9  1  0
  3 10  1  0
M  END
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PDB for HMDB0000087 (Dimethylamine)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Dimethylamine.mol                                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  N   UNK     0       0.000   0.385   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.334  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.385   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1                                                            
CONECT    3    1                                                            
MASTER        0    0    0    0    0    0    0    0    3    0    4    0
END
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3D PDB for HMDB0000087 (Dimethylamine)

COMPND    HMDB0000087
HETATM    1  C1  UNL     1      -1.205   0.155  -0.187  1.00  0.00           C  
HETATM    2  N1  UNL     1       0.020   0.377   0.508  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.177  -0.202  -0.093  1.00  0.00           C  
HETATM    4  H1  UNL     1      -1.027  -0.610  -0.988  1.00  0.00           H  
HETATM    5  H2  UNL     1      -1.954  -0.211   0.562  1.00  0.00           H  
HETATM    6  H3  UNL     1      -1.520   1.131  -0.635  1.00  0.00           H  
HETATM    7  H4  UNL     1      -0.024   0.350   1.528  1.00  0.00           H  
HETATM    8  H5  UNL     1       1.897   0.634  -0.303  1.00  0.00           H  
HETATM    9  H6  UNL     1       1.666  -0.876   0.652  1.00  0.00           H  
HETATM   10  H7  UNL     1       0.970  -0.747  -1.044  1.00  0.00           H  
CONECT    1    2    4    5    6
CONECT    2    3    7
CONECT    3    8    9   10
END
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SMILES for HMDB0000087 (Dimethylamine)

CNC
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INCHI for HMDB0000087 (Dimethylamine)

InChI=1S/C2H7N/c1-3-2/h3H,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
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
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Environmental roleIndustrial applicationBiological role
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Fibroblasts
  • Neuron
Pathways
Normal Concentrations
Abnormal Concentrations
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)Not Available
General References

Enzymes

Enzyme Details
1. Amine oxidase [flavin-containing] B
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
Enzyme Details
2. Amine oxidase [flavin-containing] A
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
Enzyme Details
3. N(G),N(G)-dimethylarginine dimethylaminohydrolase 1
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
Enzyme Details
4. N(G),N(G)-dimethylarginine dimethylaminohydrolase 2
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