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Showing NP-Card for Dimethylamine (NP0001256)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-01-19 19:36:31 UTC
NP-MRD IDNP0001256
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001256 (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 NP0001256 (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 NP0001256 (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>
NP0001256

> <DATABASE_NAME>
NP-MRD

> <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 NP0001256 (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
Download

PDB for NP0001256 (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 NP0001256 (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 NP0001256 (Dimethylamine)

CNC
Download

INCHI for NP0001256 (Dimethylamine)

InChI=1S/C2H7N/c1-3-2/h3H,1-2H3
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View in JSmol
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 Mass45.0837 Da
Monoisotopic Mass45.05785 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-19View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-02View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apium graveolensFooDB
Averrhoa carambolaKNApSAcK Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica oleracea L. ssp. BotrytisKNApSAcK Database
Brassica oleracea var. capitataFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
Cassia angustifoliaKNApSAcK Database
CervidaeFooDB
Cervus canadensisFooDB
Codonopsis canescensKNApSAcK Database
Codonopsis pilosulaKNApSAcK Database
Codonopsis subglobosaKNApSAcK Database
Codonopsis tangshenKNApSAcK Database
Codonopsis tubulosaKNApSAcK Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Glycine maxFooDB
Hordeum vulgareFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Medicago sativaKNApSAcK Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Musa x paradisiacaFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Oryza sativaKNApSAcK Database
Ovis ariesFooDB
Panax ginsengKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Polygonatum sibiricumKNApSAcK Database
Solanum tuberosumKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Triticum aestivumKNApSAcK Database
Vitis vinifera L.FooDB
Zea mays L.FooDB
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-92.2 °CNot Available
Boiling Point6.80 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1630 mg/mL at 40 °CNot Available
LogP-0.38Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
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
HMDB IDHMDB0000087
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012589
KNApSAcK IDC00050441
Chemspider ID654
KEGG Compound IDC00543
BioCyc IDDIMETHYLAMINE
BiGG IDNot Available
Wikipedia LinkDimethylamine
METLIN ID3758
PubChem Compound674
PDB IDNot Available
ChEBI ID17170
Good Scents IDrw1239751
References
General References
  1. 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 ]
  2. Lee L, Archer MC, Bruce WR: Absence of volatile nitrosamines in human feces. Cancer Res. 1981 Oct;41(10):3992-4. [PubMed:7285009 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. Zhang AQ, Mitchell SC, Smith RL: Dimethylamine in human urine. Clin Chim Acta. 1995 Jan 16;233(1-2):81-8. [PubMed:7758205 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. Gao Y, Zhang J, Chen H, Wang Z, Hou J, Wang L: Dimethylamine enhances platelet hyperactivity in chronic kidney disease model. J Bioenerg Biomembr. 2021 Oct;53(5):585-595. doi: 10.1007/s10863-021-09913-4. Epub 2021 Jul 30. [PubMed:34327565 ]