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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:38:50 UTC

Update Date

2021-09-26 23:08:20 UTC

HMDB ID

HMDB0254382

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,4-Methylenedioxymethamphetamine

Description

Midomafetamine, also known as ecstasy or MDMA, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Based on a literature review very few articles have been published on Midomafetamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3,4-methylenedioxymethamphetamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3,4-Methylenedioxymethamphetamine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254382
     RDKit          3D
3,4-Methylenedioxymethamphetamine
 29 30  0  0  0  0  0  0  0  0999 V2000
   -3.7199    0.3279    0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884   -0.7610    0.0974 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9286   -0.5421   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9935    0.6606   -1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0268   -0.5166    0.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968   -0.3157    0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    0.9689    0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    1.2745    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784    0.2320    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6313   -1.0650    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978   -1.3322    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7265   -1.8746   -0.2362 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8420   -1.0760   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4410    0.2156   -0.1723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7986    0.5074    0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2173    1.3032    0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312    0.1156    2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.7748   -0.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7381   -1.4787   -1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304    1.1090   -1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7932    0.3510   -2.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    1.4816   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -1.4634    1.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3772    0.3199    1.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407    1.8294    0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5585    2.3026    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9143   -2.3341    0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0281   -1.0594   -1.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7534   -1.3592   -0.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 11  6  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
M  END

1454
  Mrv0541 02231215302D          

 14 15  0  0  1  0            999 V2000
    6.7171    0.4081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7171   -0.9195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7932    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5077    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2220    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9365    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5077   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9365   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2220   -1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1986   -0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 14  1  0  0  0  0
  2 11  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  2  0  0  0  0
  6 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254382

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC(C)CC1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3

> <INCHI_KEY>
SHXWCVYOXRDMCX-UHFFFAOYSA-N

> <FORMULA>
C11H15NO2

> <MOLECULAR_WEIGHT>
193.2423

> <EXACT_MASS>
193.110278729

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.49311255736862

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
1.8600643429999997

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.13837113850827

> <JCHEM_POLAR_SURFACE_AREA>
30.490000000000002

> <JCHEM_REFRACTIVITY>
54.246700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
MDMA

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254382
     RDKit          3D
3,4-Methylenedioxymethamphetamine
 29 30  0  0  0  0  0  0  0  0999 V2000
   -3.7199    0.3279    0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884   -0.7610    0.0974 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9286   -0.5421   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9935    0.6606   -1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0268   -0.5166    0.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968   -0.3157    0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    0.9689    0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    1.2745    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784    0.2320    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6313   -1.0650    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978   -1.3322    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7265   -1.8746   -0.2362 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8420   -1.0760   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4410    0.2156   -0.1723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7986    0.5074    0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2173    1.3032    0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312    0.1156    2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.7748   -0.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7381   -1.4787   -1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304    1.1090   -1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7932    0.3510   -2.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    1.4816   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -1.4634    1.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3772    0.3199    1.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407    1.8294    0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5585    2.3026    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9143   -2.3341    0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0281   -1.0594   -1.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7534   -1.3592   -0.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 11  6  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1454                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      12.539   0.762   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.539  -1.716   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.413   1.063   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.747   0.293   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081   1.063   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.414   0.293   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747  -1.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.748   1.063   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.082   0.293   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.414  -1.247   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.082  -1.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748  -2.017   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080   0.293   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.437  -0.477   0.000  0.00  0.00           C+0
CONECT    1    9   14                                                       
CONECT    2   11   14                                                       
CONECT    3    4   13                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    8   10                                                  
CONECT    7    4                                                            
CONECT    8    6    9                                                       
CONECT    9    1    8   11                                                  
CONECT   10    6   12                                                       
CONECT   11    2    9   12                                                  
CONECT   12   10   11                                                       
CONECT   13    3                                                            
CONECT   14    1    2                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0254382
HETATM    1  C1  UNL     1      -3.720   0.328   0.914  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.288  -0.761   0.097  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.929  -0.542  -0.433  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.993   0.661  -1.293  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.027  -0.517   0.737  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.397  -0.316   0.507  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.892   0.969   0.536  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.225   1.275   0.324  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.078   0.232   0.074  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.631  -1.065   0.035  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.298  -1.332   0.251  1.00  0.00           C  
HETATM   12  O1  UNL     1       3.726  -1.875  -0.236  1.00  0.00           O  
HETATM   13  C11 UNL     1       4.842  -1.076  -0.586  1.00  0.00           C  
HETATM   14  O2  UNL     1       4.441   0.216  -0.172  1.00  0.00           O  
HETATM   15  H1  UNL     1      -4.799   0.507   0.725  1.00  0.00           H  
HETATM   16  H2  UNL     1      -3.217   1.303   0.662  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.631   0.116   2.002  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.899  -0.775  -0.770  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.738  -1.479  -1.039  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.030   1.109  -1.359  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.793   0.351  -2.362  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.350   1.482  -0.978  1.00  0.00           H  
HETATM   23  H9  UNL     1      -1.233  -1.463   1.322  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.377   0.320   1.411  1.00  0.00           H  
HETATM   25  H11 UNL     1       0.241   1.829   0.738  1.00  0.00           H  
HETATM   26  H12 UNL     1       2.558   2.303   0.359  1.00  0.00           H  
HETATM   27  H13 UNL     1       0.914  -2.334   0.228  1.00  0.00           H  
HETATM   28  H14 UNL     1       5.028  -1.059  -1.680  1.00  0.00           H  
HETATM   29  H15 UNL     1       5.753  -1.359  -0.016  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   18
CONECT    3    4    5   19
CONECT    4   20   21   22
CONECT    5    6   23   24
CONECT    6    7    7   11
CONECT    7    8   25
CONECT    8    9    9   26
CONECT    9   10   14
CONECT   10   11   11   12
CONECT   11   27
CONECT   12   13
CONECT   13   14   28   29
END

HMDB0254382
     RDKit          3D
3,4-Methylenedioxymethamphetamine
 29 30  0  0  0  0  0  0  0  0999 V2000
   -3.7199    0.3279    0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884   -0.7610    0.0974 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9286   -0.5421   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9935    0.6606   -1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0268   -0.5166    0.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968   -0.3157    0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    0.9689    0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    1.2745    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784    0.2320    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6313   -1.0650    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978   -1.3322    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7265   -1.8746   -0.2362 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8420   -1.0760   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4410    0.2156   -0.1723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7986    0.5074    0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2173    1.3032    0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312    0.1156    2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.7748   -0.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7381   -1.4787   -1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304    1.1090   -1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7932    0.3510   -2.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    1.4816   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -1.4634    1.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3772    0.3199    1.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407    1.8294    0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5585    2.3026    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9143   -2.3341    0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0281   -1.0594   -1.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7534   -1.3592   -0.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 11  6  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(RS)-3,4-(Methylenedioxy)methamphetamine	ChEBI
1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamine	ChEBI
DL-(3,4-Methylenedioxy)methamphetamine	ChEBI
Ecstasy	ChEBI
MDMA	ChEBI
N,alpha-Dimethyl-1,3-benzodioxole-5-ethanamine	ChEBI
N-Methyl-3,4-methylenedioxyamphetamine	ChEBI
N,a-Dimethyl-1,3-benzodioxole-5-ethanamine	Generator
N,Α-dimethyl-1,3-benzodioxole-5-ethanamine	Generator
Ecstasy (drug)	MeSH
Hydrochloride, N-methyl-3,4-methylenedioxyamphetamine	MeSH
Methylenedioxymethamphetamine	MeSH
N Methyl 3,4 methylenedioxyamphetamine	MeSH
N Methyl 3,4 methylenedioxyamphetamine hydrochloride	MeSH
N-Methyl-3,4-methylenedioxyamphetamine hydrochloride	MeSH

Chemical Formula

C₁₁H₁₅NO₂

Average Molecular Weight

193.2423

Monoisotopic Molecular Weight

193.110278729

IUPAC Name

[1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine

Traditional Name

MDMA

CAS Registry Number

Not Available

SMILES

CNC(C)CC1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3

InChI Key

SHXWCVYOXRDMCX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Aralkylamine
Benzenoid
Oxacycle
Secondary amine
Secondary aliphatic amine
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:1391 )
amphetamines (CHEBI:1391 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.65	ALOGPS
logP	1.86	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	10.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	30.49 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.25 m³·mol⁻¹	ChemAxon
Polarizability	21.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	142.955	30932474
DeepCCS	[M-H]-	139.651	30932474
DeepCCS	[M-2H]-	176.586	30932474
DeepCCS	[M+Na]+	152.124	30932474
AllCCS	[M+H]+	143.5	32859911
AllCCS	[M+H-H2O]+	139.2	32859911
AllCCS	[M+NH4]+	147.4	32859911
AllCCS	[M+Na]+	148.6	32859911
AllCCS	[M-H]-	147.2	32859911
AllCCS	[M+Na-2H]-	147.7	32859911
AllCCS	[M+HCOO]-	148.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Methylenedioxymethamphetamine	CNC(C)CC1=CC2=C(OCO2)C=C1	2314.4	Standard polar	33892256
3,4-Methylenedioxymethamphetamine	CNC(C)CC1=CC2=C(OCO2)C=C1	1579.0	Standard non polar	33892256
3,4-Methylenedioxymethamphetamine	CNC(C)CC1=CC2=C(OCO2)C=C1	1534.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Methylenedioxymethamphetamine,1TMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N(C)[Si](C)(C)C	1714.0	Semi standard non polar	33892256
3,4-Methylenedioxymethamphetamine,1TMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N(C)[Si](C)(C)C	1694.8	Standard non polar	33892256
3,4-Methylenedioxymethamphetamine,1TMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N(C)[Si](C)(C)C	2294.6	Standard polar	33892256
3,4-Methylenedioxymethamphetamine,1TBDMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N(C)[Si](C)(C)C(C)(C)C	1949.2	Semi standard non polar	33892256
3,4-Methylenedioxymethamphetamine,1TBDMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N(C)[Si](C)(C)C(C)(C)C	1942.2	Standard non polar	33892256
3,4-Methylenedioxymethamphetamine,1TBDMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N(C)[Si](C)(C)C(C)(C)C	2431.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Methylenedioxymethamphetamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9400000000-360e5a8ee3bedf21b35d	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Methylenedioxymethamphetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine LC-ESI-QTOF , positive-QTOF	splash10-0bti-0900000000-1a28636828a7b4fba7a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine LC-ESI-QFT , positive-QTOF	splash10-03di-0900000000-9f6740a4cf53bb143e38	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine LC-ESI-QFT , positive-QTOF	splash10-03di-0900000000-ae25129bb130708d0a99	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine LC-ESI-QFT , positive-QTOF	splash10-03di-0900000000-d6f476419cc850f4c75b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine LC-ESI-QFT , positive-QTOF	splash10-0a5i-0900000000-856b4946fd17f215f5d6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine LC-ESI-QFT , positive-QTOF	splash10-0a4r-1900000000-a75796025d8746c75458	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine LC-ESI-QFT , positive-QTOF	splash10-0a6r-4900000000-9902e8afbb6b491db024	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine LC-ESI-QFT , positive-QTOF	splash10-056r-9500000000-45882ee03a98bc7eca6f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine LC-ESI-QFT , positive-QTOF	splash10-0fba-9200000000-e98cccad079b0b085d33	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine LC-ESI-QFT , positive-QTOF	splash10-0ufr-9100000000-2c72b7f5adc413801f6d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine -1V, Positive-QTOF	splash10-0bti-0900000000-92d1138e523510596cad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 15V, Positive-QTOF	splash10-03di-0900000000-ed05ade3a13a3c0598b2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 30V, Positive-QTOF	splash10-03di-0900000000-4ffef12351c79726e4cb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 60V, Positive-QTOF	splash10-0a5i-0900000000-d3bd66b90abe718c57bb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 45V, Positive-QTOF	splash10-03di-0900000000-fc956c92472ce3e31a0e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 75V, Positive-QTOF	splash10-0a4r-1900000000-0a0354c52bbf2f9d3de1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 90V, Positive-QTOF	splash10-0a6r-4900000000-f132002463b731553143	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 150V, Positive-QTOF	splash10-0fba-9200000000-1e6d77f9bfcb3d065b21	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 120V, Positive-QTOF	splash10-056r-9500000000-ea72a05738715da90779	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 10V, Positive-QTOF	splash10-0006-0900000000-07487895a15c2b4ef6d8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 20V, Positive-QTOF	splash10-01ox-2900000000-c688bbd5e3d8d7a70194	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 40V, Positive-QTOF	splash10-067i-7900000000-81c6af779e008bc5f06f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 10V, Negative-QTOF	splash10-0006-0900000000-ad82e5237b2c746a7f57	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 20V, Negative-QTOF	splash10-0006-0900000000-0b7aca4ca9e3a77e574e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxymethamphetamine 40V, Negative-QTOF	splash10-0r3a-6900000000-c992c8b9b1953ab2a344	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01454

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1556

KEGG Compound ID

C07577

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

MDMA

METLIN ID

Not Available

PubChem Compound

1615

PDB ID

Not Available

ChEBI ID

1391

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 3,4-Methylenedioxymethamphetamine (HMDB0254382)

MOL for HMDB0254382 (3,4-Methylenedioxymethamphetamine)

3D MOL for HMDB0254382 (3,4-Methylenedioxymethamphetamine)

3D SDF for HMDB0254382 (3,4-Methylenedioxymethamphetamine)

3D-SDF for HMDB0254382 (3,4-Methylenedioxymethamphetamine)

PDB for HMDB0254382 (3,4-Methylenedioxymethamphetamine)

3D PDB for HMDB0254382 (3,4-Methylenedioxymethamphetamine)

SMILES for HMDB0254382 (3,4-Methylenedioxymethamphetamine)

INCHI for HMDB0254382 (3,4-Methylenedioxymethamphetamine)

Structure for HMDB0254382 (3,4-Methylenedioxymethamphetamine)

3D Structure for HMDB0254382 (3,4-Methylenedioxymethamphetamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra