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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:40:16 UTC

Update Date

2023-02-21 17:28:58 UTC

HMDB ID

HMDB0041808

Secondary Accession Numbers

HMDB41808

Metabolite Identification

Common Name

4,4'-Methylenedianiline

Description

4,4’-Methylenedianiline (MDA) is an industrial chemical that is produced and used industrially as a precursor to polyamides, epoxy resins, and polyurethane foams (PMID: 20621954 ). It is a primary aromatic amine, belonging to the family of compounds known as Diphenylmethanes. Diphenylmethanes are compounds consisting of methane with two of the hydrogen atoms replaced by phenyl groups. MDA is used mainly as a precursor to 4,4 ́-methylene diphenyl diisocyanate (MDI), which is a precursor to many polyurethane foams. To generate MDI, which is a highly reactive isocyanate, MDA is treated with phosgene. Workers exposed to MDI may develop sensitization, leading to occupational asthma. MDI is metabolized in the body and secreted in the urine as MDA, Therefore MDA is a urinary biomarker of MDI exposure. On its own, MDA is a known animal carcinogen, and human hepatotoxin. MDA produces genotoxic effects by forming DNA adducts in the liver and inducing DNA damage to hepatocytes (PMID: 32038824 ). The Occupational Safety and Health Administration has set a permissible exposure limit at 0.01 ppm over an eight-hour time-weighted average, and a short-term exposure limit at 0.10 ppm.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0041808
     RDKit          3D
4,4'-Methylenedianiline
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.6624   -1.1158    1.2649 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5321   -0.5257    0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -1.1033   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558   -0.5492   -1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    0.6034   -0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1008    1.2081   -1.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1724    0.6890   -0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8139    1.2787    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9988    0.7892    0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6031   -0.3289    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8183   -0.8622    0.8461 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9680   -0.9310   -0.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7768   -0.4238   -1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8510    1.1852    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9693    0.6233    1.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5771   -1.0541    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5909   -1.6062    2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4013   -2.0131   -0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4188   -1.0071   -1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865    1.0606   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449    2.3240   -1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3756    2.1630    0.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5090    1.2524    1.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9797   -0.9140    1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5578   -1.2055    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4356   -1.8120   -1.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115   -0.9318   -2.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3896    2.0983    0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3807    1.1088    2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  2  0
 15  2  1  0
 13  7  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  9 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
M  END


  Mrv1652305261923592D          

 15 16  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 10  9  1  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041808

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=CC=C(CC2=CC=C(N)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H2

> <INCHI_KEY>
YBRVSVVVWCFQMG-UHFFFAOYSA-N

> <FORMULA>
C13H14N2

> <MOLECULAR_WEIGHT>
198.2637

> <EXACT_MASS>
198.115698458

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.480621576245372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(4-aminophenyl)methyl]aniline

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
2.4071879349999996

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.8256718832674315

> <JCHEM_POLAR_SURFACE_AREA>
52.04

> <JCHEM_REFRACTIVITY>
65.19600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,4'-diaminodiphenylmethane

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041808
     RDKit          3D
4,4'-Methylenedianiline
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.6624   -1.1158    1.2649 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5321   -0.5257    0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -1.1033   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558   -0.5492   -1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    0.6034   -0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1008    1.2081   -1.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1724    0.6890   -0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8139    1.2787    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9988    0.7892    0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6031   -0.3289    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8183   -0.8622    0.8461 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9680   -0.9310   -0.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7768   -0.4238   -1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8510    1.1852    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9693    0.6233    1.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5771   -1.0541    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5909   -1.6062    2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4013   -2.0131   -0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4188   -1.0071   -1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865    1.0606   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449    2.3240   -1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3756    2.1630    0.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5090    1.2524    1.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9797   -0.9140    1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5578   -1.2055    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4356   -1.8120   -1.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115   -0.9318   -2.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3896    2.0983    0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3807    1.1088    2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  2  0
 15  2  1  0
 13  7  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  9 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.334   8.470   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
CONECT    1    5   10                                                       
CONECT    2    6   10                                                       
CONECT    3    7   11                                                       
CONECT    4    8   11                                                       
CONECT    5    1   12                                                       
CONECT    6    2   12                                                       
CONECT    7    3   13                                                       
CONECT    8    4   13                                                       
CONECT    9   10   11                                                       
CONECT   10    1    2    9                                                  
CONECT   11    3    4    9                                                  
CONECT   12    5    6   14                                                  
CONECT   13    7    8   15                                                  
CONECT   14   12                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0041808
HETATM    1  N1  UNL     1      -4.662  -1.116   1.265  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.532  -0.526   0.661  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.968  -1.103  -0.457  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.856  -0.549  -1.076  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.291   0.603  -0.574  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.101   1.208  -1.225  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.172   0.689  -0.673  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.814   1.279   0.397  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.999   0.789   0.905  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.603  -0.329   0.355  1.00  0.00           C  
HETATM   11  N2  UNL     1       4.818  -0.862   0.846  1.00  0.00           N  
HETATM   12  C10 UNL     1       2.968  -0.931  -0.722  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.777  -0.424  -1.218  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.851   1.185   0.544  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.969   0.623   1.162  1.00  0.00           C  
HETATM   16  H1  UNL     1      -5.577  -1.054   0.787  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.591  -1.606   2.172  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.401  -2.013  -0.866  1.00  0.00           H  
HETATM   19  H4  UNL     1      -1.419  -1.007  -1.952  1.00  0.00           H  
HETATM   20  H5  UNL     1      -0.187   1.061  -2.319  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.145   2.324  -1.063  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.376   2.163   0.864  1.00  0.00           H  
HETATM   23  H8  UNL     1       3.509   1.252   1.751  1.00  0.00           H  
HETATM   24  H9  UNL     1       4.980  -0.914   1.868  1.00  0.00           H  
HETATM   25  H10 UNL     1       5.558  -1.205   0.207  1.00  0.00           H  
HETATM   26  H11 UNL     1       3.436  -1.812  -1.162  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.311  -0.932  -2.069  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.390   2.098   0.928  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.381   1.109   2.038  1.00  0.00           H  
CONECT    1    2   16   17
CONECT    2    3    3   15
CONECT    3    4   18
CONECT    4    5    5   19
CONECT    5    6   14
CONECT    6    7   20   21
CONECT    7    8    8   13
CONECT    8    9   22
CONECT    9   10   10   23
CONECT   10   11   12
CONECT   11   24   25
CONECT   12   13   13   26
CONECT   13   27
CONECT   14   15   15   28
CONECT   15   29
END

HMDB0041808
     RDKit          3D
4,4'-Methylenedianiline
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.6624   -1.1158    1.2649 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5321   -0.5257    0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -1.1033   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558   -0.5492   -1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    0.6034   -0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1008    1.2081   -1.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1724    0.6890   -0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8139    1.2787    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9988    0.7892    0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6031   -0.3289    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8183   -0.8622    0.8461 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9680   -0.9310   -0.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7768   -0.4238   -1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8510    1.1852    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9693    0.6233    1.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5771   -1.0541    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5909   -1.6062    2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4013   -2.0131   -0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4188   -1.0071   -1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865    1.0606   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449    2.3240   -1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3756    2.1630    0.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5090    1.2524    1.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9797   -0.9140    1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5578   -1.2055    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4356   -1.8120   -1.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115   -0.9318   -2.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3896    2.0983    0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3807    1.1088    2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  2  0
 15  2  1  0
 13  7  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  9 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,4'-Diphenylmethanediamine	ChEBI
4,4'-Methylenebis(benzeneamine)	ChEBI
4-(4-Aminobenzyl)aniline	ChEBI
alpha-(p-Aminophenyl)-p-toluidine	ChEBI
Bis(4-aminophenyl)methane	ChEBI
Bis(p-aminophenyl)methane	ChEBI
Bis-p-aminophenylmethane	ChEBI
DADPM	ChEBI
DAPM	ChEBI
DDM	ChEBI
Di-(4-aminophenyl)methane	ChEBI
Di-(p-aminophenyl)methane	ChEBI
Dianilinomethane	ChEBI
p,P'-diaminodiphenylmethane	ChEBI
p,P'-methylenedianiline	ChEBI
4,4'-Diaminodiphenylmethane	Kegg
a-(p-Aminophenyl)-p-toluidine	Generator
Α-(p-aminophenyl)-p-toluidine	Generator
4, 4'-Diphenylmethanediamine	HMDB
4, 4'-Methylenebis(aniline)	HMDB
4,4'-Diaminodiphenylmethan	HMDB
4,4'-Methylene(bisaniline)	HMDB
4,4'-Methylene-dianiline	HMDB
4,4'-Methylenebis-benzenamine	HMDB
4,4'-Methylenebis[aniline]	HMDB
4,4'-Methylenedi-aniline	HMDB
4,4'-Methylenedibenzenamine	HMDB
4,4-Methylenedianiline	HMDB
4-(4-Aminobenzyl)phenylamine (acd/name 4.0)	HMDB
Ancamine TL	HMDB
Araldite hardener 972	HMDB
Bis(aminophenyl)methane	HMDB
Bis-p-aminofenylmethan	HMDB
Curithane	HMDB
Di(4-aminophenyl)methane	HMDB
Diaminodiphenylmethane	HMDB
Dianilinemethane	HMDB
Epicure DDM	HMDB
Epikure DDM	HMDB
Jeffamine ap-20	HMDB
MDA	HMDB
Methylenebis(aniline)	HMDB
Methylenebis[aniline]	HMDB
Methylenedianiline	HMDB
p, P'-methylenedianiline	HMDB
p,P'-diaminodifenylmethan	HMDB
Sumicure m	HMDB
Tonox	HMDB
4,4'-Diaminodiphenylmethane, sodium chloride (3:1)	HMDB
4,4'-Diaminodiphenylmethane dihydrochloride	HMDB
4,4'-Methylene dianiline	HMDB
4,4'-Methylenebisaniline	HMDB
4,4'-MDA	HMDB
4,4'-Methylenedianiline	ChEBI

Chemical Formula

C₁₃H₁₄N₂

Average Molecular Weight

198.2637

Monoisotopic Molecular Weight

198.115698458

IUPAC Name

4-[(4-aminophenyl)methyl]aniline

Traditional Name

4,4'-diaminodiphenylmethane

CAS Registry Number

101-77-9

SMILES

NC1=CC=C(CC2=CC=C(N)C=C2)C=C1

InChI Identifier

InChI=1S/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H2

InChI Key

YBRVSVVVWCFQMG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Aniline or substituted anilines
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic amine (CHEBI:32506 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041808)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	92.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1 mg/mL at 25 °C	Not Available
LogP	1.59	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.061 g/L	ALOGPS
logP	2.04	ALOGPS
logP	2.41	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	4.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.04 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.2 m³·mol⁻¹	ChemAxon
Polarizability	22.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	146.847	31661259
DarkChem	[M-H]-	146.26	31661259
DeepCCS	[M+H]+	148.923	30932474
DeepCCS	[M-H]-	146.544	30932474
DeepCCS	[M-2H]-	180.438	30932474
DeepCCS	[M+Na]+	155.164	30932474
AllCCS	[M+H]+	146.1	32859911
AllCCS	[M+H-H2O]+	141.8	32859911
AllCCS	[M+NH4]+	150.1	32859911
AllCCS	[M+Na]+	151.3	32859911
AllCCS	[M-H]-	149.0	32859911
AllCCS	[M+Na-2H]-	149.1	32859911
AllCCS	[M+HCOO]-	149.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4,4'-Methylenedianiline	NC1=CC=C(CC2=CC=C(N)C=C2)C=C1	3345.4	Standard polar	33892256
4,4'-Methylenedianiline	NC1=CC=C(CC2=CC=C(N)C=C2)C=C1	2076.3	Standard non polar	33892256
4,4'-Methylenedianiline	NC1=CC=C(CC2=CC=C(N)C=C2)C=C1	2132.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4,4'-Methylenedianiline,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C=C2)C=C1	2386.6	Semi standard non polar	33892256
4,4'-Methylenedianiline,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C=C2)C=C1	2226.9	Standard non polar	33892256
4,4'-Methylenedianiline,2TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C)C=C2)C=C1	2490.7	Semi standard non polar	33892256
4,4'-Methylenedianiline,2TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C)C=C2)C=C1	2262.0	Standard non polar	33892256
4,4'-Methylenedianiline,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C=C2)C=C1)[Si](C)(C)C	2322.0	Semi standard non polar	33892256
4,4'-Methylenedianiline,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C=C2)C=C1)[Si](C)(C)C	2256.0	Standard non polar	33892256
4,4'-Methylenedianiline,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	2470.4	Semi standard non polar	33892256
4,4'-Methylenedianiline,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	2254.6	Standard non polar	33892256
4,4'-Methylenedianiline,4TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1)[Si](C)(C)C	2414.2	Semi standard non polar	33892256
4,4'-Methylenedianiline,4TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1)[Si](C)(C)C	2342.2	Standard non polar	33892256
4,4'-Methylenedianiline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C=C2)C=C1	2630.6	Semi standard non polar	33892256
4,4'-Methylenedianiline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C=C2)C=C1	2448.2	Standard non polar	33892256
4,4'-Methylenedianiline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C=C1	2994.5	Semi standard non polar	33892256
4,4'-Methylenedianiline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C=C1	2715.4	Standard non polar	33892256
4,4'-Methylenedianiline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C=C2)C=C1)[Si](C)(C)C(C)(C)C	2795.4	Semi standard non polar	33892256
4,4'-Methylenedianiline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C=C2)C=C1)[Si](C)(C)C(C)(C)C	2678.3	Standard non polar	33892256
4,4'-Methylenedianiline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1	3151.5	Semi standard non polar	33892256
4,4'-Methylenedianiline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1	2848.9	Standard non polar	33892256
4,4'-Methylenedianiline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1)[Si](C)(C)C(C)(C)C	3272.8	Semi standard non polar	33892256
4,4'-Methylenedianiline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1)[Si](C)(C)C(C)(C)C	3044.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4,4'-Methylenedianiline GC-MS (Non-derivatized) - 70eV, Positive	splash10-052b-1900000000-a1316bc903c186c14318	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,4'-Methylenedianiline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-1900000000-3ade5e930b45bb46e746	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 10V, Positive-QTOF	splash10-000t-0900000000-4644a7dbb46f9d7b2ba1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 20V, Positive-QTOF	splash10-000t-0900000000-a4548ac0cc34b55b0737	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 40V, Positive-QTOF	splash10-0pe9-3900000000-4cb485ecb653179900c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 10V, Negative-QTOF	splash10-0002-0900000000-31a3645696c4f9d211ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 20V, Negative-QTOF	splash10-0002-0900000000-0e89f98c9bcf3071812e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 40V, Negative-QTOF	splash10-000w-4900000000-9cfc5d89ecd51b783c25	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 10V, Positive-QTOF	splash10-0002-0900000000-d89ea9976ffd35a15c71	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 20V, Positive-QTOF	splash10-0002-2900000000-5ccfe3083b2af59df353	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 40V, Positive-QTOF	splash10-004l-7900000000-07b5c14a9b509e0f3922	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 10V, Negative-QTOF	splash10-0002-0900000000-d2d648aa4423d0c7a455	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 20V, Negative-QTOF	splash10-0002-0900000000-d2d648aa4423d0c7a455	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 40V, Negative-QTOF	splash10-001i-1900000000-b08e84c052ca33f2d5b9	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7296

KEGG Compound ID

C14288

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4,4'-Methylenedianiline

METLIN ID

Not Available

PubChem Compound

7577

PDB ID

Not Available

ChEBI ID

32506

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1195131

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Pludro G, Karlowski K, Mankowska M, Woggon H, Uhde WJ: [Toxicological and chemical studies of some epoxy resins and hardeners. I. Study of acute and subacute toxicity of phthalic acid anhydride, 4,4'diaminodiphenylmethane and epoxy resin Epilox EG-34]. Acta Pol Pharm. 1969;26(4):353-8. [PubMed:5349261 ]
Yasuda SK: Determination of 3,3'-dichloro-4,4'-diaminodiphenylmethane in air. J Chromatogr. 1975 Feb 12;104(2):283-90. [PubMed:1150762 ]
Manis MO, Braselton WE Jr: Structure elucidation and in vitro reactivity of the major metabolite of 4,4'-methylenebis(2-chloroaniline) (MBOCA) in canine urine. Fundam Appl Toxicol. 1984 Dec;4(6):1000-8. [PubMed:6549168 ]
Giouleme O, Karabatsou S, Hytiroglou P, Xanthis A, Tsiaousi E, Katsaros M, Koliouskas D: 4,4'-Methylenedianiline-induced hepatitis in an industrial worker: case report and review of the literature. Hum Exp Toxicol. 2011 Jul;30(7):762-7. doi: 10.1177/0960327110376549. Epub 2010 Jul 9. [PubMed:20621954 ]
Oh JH, Yoon HJ, Lim JS, Park HJ, Cho JW, Kwon MS, Yoon S: Analysis of Gene Expression in 4,4'-Methylenedianiline-induced Acute Hepatotoxicity. Toxicol Res. 2009 Jun;25(2):85-92. doi: 10.5487/TR.2009.25.2.085. Epub 2009 Jun 1. [PubMed:32038824 ]

Showing metabocard for 4,4'-Methylenedianiline (HMDB0041808)

MOL for HMDB0041808 (4,4'-Methylenedianiline)

3D MOL for HMDB0041808 (4,4'-Methylenedianiline)

3D SDF for HMDB0041808 (4,4'-Methylenedianiline)

3D-SDF for HMDB0041808 (4,4'-Methylenedianiline)

PDB for HMDB0041808 (4,4'-Methylenedianiline)

3D PDB for HMDB0041808 (4,4'-Methylenedianiline)

SMILES for HMDB0041808 (4,4'-Methylenedianiline)

INCHI for HMDB0041808 (4,4'-Methylenedianiline)

Structure for HMDB0041808 (4,4'-Methylenedianiline)

3D Structure for HMDB0041808 (4,4'-Methylenedianiline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra