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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:38:00 UTC

Update Date

2021-09-26 23:08:19 UTC

HMDB ID

HMDB0254369

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,4-Methylenedioxy-N-ethylamphetamine

Description

Methylenedioxyethamphetamine 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 a significant number of articles have been published on Methylenedioxyethamphetamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3,4-methylenedioxy-n-ethylamphetamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3,4-Methylenedioxy-N-ethylamphetamine 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

HMDB0259435
     RDKit          3D
(S)-Methylenedioxyethylamphetamine
 32 33  0  0  0  0  0  0  0  0999 V2000
    3.8144    1.1048    1.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8839    0.1060    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7901    0.2922   -0.8528 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5061   -0.0491   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4438   -1.5009    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364    0.4157   -1.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9246    0.1291   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5254   -1.0713   -1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7958   -1.4087   -0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5244   -0.5283    0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9369    0.6481    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6363    0.9920    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620    1.3466    1.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1234    0.7331    1.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8095   -0.5897    0.5972 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7184    1.7525    1.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9475    1.7984    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905    0.5821    2.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8104    0.3324   -0.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -0.9388    0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9838   -0.3995   -1.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3797    0.5203    0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9507   -2.1210   -0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4162   -1.8460    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0534   -1.6164    1.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5784   -0.0753   -2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5975    1.5112   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9687   -1.7555   -1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117   -2.3235   -1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959    1.9126    0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7255    0.7222    1.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6436    1.3249    0.2307 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
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 12  7  1  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
M  END

1566
  Mrv0541 02231215342D          

 15 16  0  0  1  0            999 V2000
    7.4321    0.4081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4321   -0.9196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9136   -0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 15  1  0  0  0  0
  2 12  1  0  0  0  0
  2 15  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  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 11  1  0  0  0  0
  9 14  1  0  0  0  0
 10 13  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254369

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H17NO2/c1-3-13-9(2)6-10-4-5-11-12(7-10)15-8-14-11/h4-5,7,9,13H,3,6,8H2,1-2H3

> <INCHI_KEY>
PVXVWWANJIWJOO-UHFFFAOYSA-N

> <FORMULA>
C12H17NO2

> <MOLECULAR_WEIGHT>
207.2689

> <EXACT_MASS>
207.125928793

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.41178982166382

> <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](ethyl)amine

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.2168722976666664

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.220089146751718

> <JCHEM_POLAR_SURFACE_AREA>
30.490000000000002

> <JCHEM_REFRACTIVITY>
58.995300000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylenedioxyethylamphetamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0259435
     RDKit          3D
(S)-Methylenedioxyethylamphetamine
 32 33  0  0  0  0  0  0  0  0999 V2000
    3.8144    1.1048    1.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8839    0.1060    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7901    0.2922   -0.8528 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5061   -0.0491   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4438   -1.5009    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364    0.4157   -1.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9246    0.1291   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5254   -1.0713   -1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7958   -1.4087   -0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5244   -0.5283    0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9369    0.6481    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6363    0.9920    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620    1.3466    1.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1234    0.7331    1.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8095   -0.5897    0.5972 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7184    1.7525    1.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9475    1.7984    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905    0.5821    2.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8104    0.3324   -0.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -0.9388    0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9838   -0.3995   -1.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3797    0.5203    0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9507   -2.1210   -0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4162   -1.8460    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0534   -1.6164    1.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5784   -0.0753   -2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5975    1.5112   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9687   -1.7555   -1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117   -2.3235   -1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959    1.9126    0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7255    0.7222    1.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6436    1.3249    0.2307 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
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 12  7  1  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1566                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      13.873   0.762   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.873  -1.717   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.748   1.063   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.081   0.293   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.415   1.063   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.748   0.293   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -1.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082   1.063   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   0.293   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748  -1.247   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.416   0.293   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.416  -1.247   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.082  -2.017   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   1.063   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.772  -0.477   0.000  0.00  0.00           C+0
CONECT    1   11   15                                                       
CONECT    2   12   15                                                       
CONECT    3    4    9                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    8   10                                                  
CONECT    7    4                                                            
CONECT    8    6   11                                                       
CONECT    9    3   14                                                       
CONECT   10    6   13                                                       
CONECT   11    1    8   12                                                  
CONECT   12    2   11   13                                                  
CONECT   13   10   12                                                       
CONECT   14    9                                                            
CONECT   15    1    2                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0259642
HETATM    1  C1  UNL     1      -4.136  -0.618  -0.750  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.737  -1.135  -0.918  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.783  -0.565  -0.076  1.00  0.00           N  
HETATM    4  C3  UNL     1      -1.409   0.758  -0.323  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.524   1.744  -0.120  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.274   1.236   0.585  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.959   0.447   0.437  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.200  -0.653   1.217  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.383  -1.384   1.060  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.342  -1.024   0.120  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.083   0.085  -0.656  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.920   0.806  -0.504  1.00  0.00           C  
HETATM   13  O1  UNL     1       4.200   0.219  -1.510  1.00  0.00           O  
HETATM   14  C12 UNL     1       5.250  -0.575  -0.930  1.00  0.00           C  
HETATM   15  O2  UNL     1       4.567  -1.584  -0.210  1.00  0.00           O  
HETATM   16  H1  UNL     1      -4.877  -1.495  -0.709  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.513  -0.049  -1.641  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.310  -0.062   0.186  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.795  -2.257  -0.816  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.412  -0.999  -2.013  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.669  -0.960   0.860  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.036   0.837  -1.399  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.276   1.760  -0.898  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.013   2.759  -0.161  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.924   1.642   0.918  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.665   1.248   1.626  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.021   2.286   0.309  1.00  0.00           H  
HETATM   28  H13 UNL     1       0.452  -0.937   1.954  1.00  0.00           H  
HETATM   29  H14 UNL     1       2.536  -2.239   1.689  1.00  0.00           H  
HETATM   30  H15 UNL     1       1.759   1.662  -1.129  1.00  0.00           H  
HETATM   31  H16 UNL     1       5.885   0.057  -0.256  1.00  0.00           H  
HETATM   32  H17 UNL     1       5.837  -1.012  -1.734  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4   21
CONECT    4    5    6   22
CONECT    5   23   24   25
CONECT    6    7   26   27
CONECT    7    8    8   12
CONECT    8    9   28
CONECT    9   10   10   29
CONECT   10   11   15
CONECT   11   12   12   13
CONECT   12   30
CONECT   13   14
CONECT   14   15   31   32
END

HMDB0259435
     RDKit          3D
(S)-Methylenedioxyethylamphetamine
 32 33  0  0  0  0  0  0  0  0999 V2000
    3.8144    1.1048    1.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8839    0.1060    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7901    0.2922   -0.8528 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5061   -0.0491   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4438   -1.5009    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364    0.4157   -1.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9246    0.1291   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5254   -1.0713   -1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7958   -1.4087   -0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5244   -0.5283    0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9369    0.6481    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6363    0.9920    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620    1.3466    1.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1234    0.7331    1.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8095   -0.5897    0.5972 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7184    1.7525    1.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9475    1.7984    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905    0.5821    2.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8104    0.3324   -0.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -0.9388    0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9838   -0.3995   -1.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3797    0.5203    0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9507   -2.1210   -0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4162   -1.8460    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0534   -1.6164    1.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5784   -0.0753   -2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5975    1.5112   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9687   -1.7555   -1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117   -2.3235   -1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959    1.9126    0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7255    0.7222    1.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6436    1.3249    0.2307 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
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 12  7  1  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R)-Isomer OF 3,4-methylenedioxyethamphetamine	MeSH
3,4-Methylenedioxyethamphetamine	MeSH
EVE (amphetamine)	MeSH
(S)-Isomer OF 3,4-methylenedioxyethamphetamine	MeSH
3,4-Methylenedioxyethylamphetamine	MeSH
N-Ethyl-3,4-methylenedioxyamphetamine	MeSH
MDEA	MeSH
N-MDE	MeSH
HCL OF 3,4-Methylenedioxyethamphetamine	MeSH
(R)-3,4-Methylenedioxyethylamphetamine	MeSH
(R,S)-N-Ethyl-3,4-methylenedioxyamphetamine	MeSH
1,3-Benzodioxole-5-ethanamine, N-ethyl-alpha-methyl-, hydrochloride (1:1)	MeSH
N-Ethyl-mda	MeSH
(+--)-N-Ethyl-alpha-methyl-3,4-(methylenedioxy)phenethylamine	MeSH
(S)-Methylenedioxyethylamphetamine	MeSH
3,4-Methylenedioxyethylamphetamine hydrochloride	MeSH
(R)-Methylenedioxyethylamphetamine	MeSH
(S)-3,4-Methylenedioxyethylamphetamine	MeSH
Methylenedioxyethamphetamine hydrochloride	MeSH
D-3,4-Methylenedioxyethylamphetamine	MeSH
MDE hydrochloride	MeSH
MDEA hydrochloride	MeSH
Methylenedioxyethamphetamine	MeSH

Chemical Formula

C₁₂H₁₇NO₂

Average Molecular Weight

207.2689

Monoisotopic Molecular Weight

207.125928793

IUPAC Name

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

Traditional Name

methylenedioxyethylamphetamine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H17NO2/c1-3-13-9(2)6-10-4-5-11-12(7-10)15-8-14-11/h4-5,7,9,13H,3,6,8H2,1-2H3

InChI Key

PVXVWWANJIWJOO-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

Not Available

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	2.25	ALOGPS
logP	2.22	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	10.22	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	4	ChemAxon
Refractivity	59 m³·mol⁻¹	ChemAxon
Polarizability	23.41 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]+	147.805	30932474
DeepCCS	[M-H]-	145.447	30932474
DeepCCS	[M-2H]-	180.54	30932474
DeepCCS	[M+Na]+	155.974	30932474
AllCCS	[M+H]+	147.4	32859911
AllCCS	[M+H-H2O]+	143.3	32859911
AllCCS	[M+NH4]+	151.2	32859911
AllCCS	[M+Na]+	152.3	32859911
AllCCS	[M-H]-	152.4	32859911
AllCCS	[M+Na-2H]-	152.8	32859911
AllCCS	[M+HCOO]-	153.3	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Methylenedioxy-N-ethylamphetamine,1TMS,isomer #1	CCN(C(C)CC1=CC=C2OCOC2=C1)[Si](C)(C)C	1775.0	Semi standard non polar	33892256
3,4-Methylenedioxy-N-ethylamphetamine,1TMS,isomer #1	CCN(C(C)CC1=CC=C2OCOC2=C1)[Si](C)(C)C	1805.6	Standard non polar	33892256
3,4-Methylenedioxy-N-ethylamphetamine,1TMS,isomer #1	CCN(C(C)CC1=CC=C2OCOC2=C1)[Si](C)(C)C	2410.0	Standard polar	33892256
3,4-Methylenedioxy-N-ethylamphetamine,1TBDMS,isomer #1	CCN(C(C)CC1=CC=C2OCOC2=C1)[Si](C)(C)C(C)(C)C	2012.8	Semi standard non polar	33892256
3,4-Methylenedioxy-N-ethylamphetamine,1TBDMS,isomer #1	CCN(C(C)CC1=CC=C2OCOC2=C1)[Si](C)(C)C(C)(C)C	2050.3	Standard non polar	33892256
3,4-Methylenedioxy-N-ethylamphetamine,1TBDMS,isomer #1	CCN(C(C)CC1=CC=C2OCOC2=C1)[Si](C)(C)C(C)(C)C	2531.2	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-Methylenedioxy-N-ethylamphetamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9300000000-b757a425f68a469c2fed	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 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-Methylenedioxy-N-ethylamphetamine LC-ESI-QFT , positive-QTOF	splash10-03di-0930000000-1c409c044a990269552d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine LC-ESI-QFT , positive-QTOF	splash10-03di-0910000000-b81cd94455fc636ec752	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine LC-ESI-QFT , positive-QTOF	splash10-03ei-0900000000-ea619bf2f0ed78a397ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine LC-ESI-QFT , positive-QTOF	splash10-0a5i-0900000000-f70ec61288348785c4d5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine LC-ESI-QFT , positive-QTOF	splash10-0a4r-1900000000-be25351a999d4b8a92aa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine LC-ESI-QFT , positive-QTOF	splash10-0a70-4900000000-1174b1509d424f5c6980	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine LC-ESI-QFT , positive-QTOF	splash10-056r-9500000000-0497c4c7b17f4e2e718e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine LC-ESI-QFT , positive-QTOF	splash10-0fba-9200000000-6e2343d7fe50220fbfcb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine LC-ESI-QFT , positive-QTOF	splash10-0udi-9100000000-34f0bb3383cddf0aec60	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 30V, Positive-QTOF	splash10-03di-0910000000-17281abf97e3b975235b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 60V, Positive-QTOF	splash10-0a5i-0900000000-0f4233c890e53f1d4a03	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 45V, Positive-QTOF	splash10-03ei-0900000000-932b846de0651cd786a6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 15V, Positive-QTOF	splash10-03di-0930000000-e1ed2f3e7dc9c52a6fea	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 75V, Positive-QTOF	splash10-0a4r-1900000000-c0449b1bac028cb39ab2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 90V, Positive-QTOF	splash10-0a70-4900000000-5df470324f8f89bddf2a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 35V, Positive-QTOF	splash10-08gr-0900000000-e0aa6f64f3db2b63e8ca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 120V, Positive-QTOF	splash10-056r-9500000000-92896aab3428d2bf4d19	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 10V, Positive-QTOF	splash10-0a4i-1290000000-69302f5568a450d045ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 20V, Positive-QTOF	splash10-0bt9-6950000000-61d8a21b2f1940847a91	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 40V, Positive-QTOF	splash10-017j-9600000000-4fa3169907ba0d820a29	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 10V, Negative-QTOF	splash10-0a4i-0190000000-14d768677003b69d8a77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 20V, Negative-QTOF	splash10-0a4i-2690000000-7e9f052116b5ab017730	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxy-N-ethylamphetamine 40V, Negative-QTOF	splash10-0006-9400000000-9ea67474af203fc1ec7c	2016-08-03	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

DB01566

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

94775

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3,4-Methylenedioxy-N-ethylamphetamine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

132234

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-Methylenedioxy-N-ethylamphetamine (HMDB0254369)

MOL for HMDB0254369 (3,4-Methylenedioxy-N-ethylamphetamine)

3D MOL for HMDB0254369 (3,4-Methylenedioxy-N-ethylamphetamine)

3D SDF for HMDB0254369 (3,4-Methylenedioxy-N-ethylamphetamine)

3D-SDF for HMDB0254369 (3,4-Methylenedioxy-N-ethylamphetamine)

PDB for HMDB0254369 (3,4-Methylenedioxy-N-ethylamphetamine)

3D PDB for HMDB0254369 (3,4-Methylenedioxy-N-ethylamphetamine)

SMILES for HMDB0254369 (3,4-Methylenedioxy-N-ethylamphetamine)

INCHI for HMDB0254369 (3,4-Methylenedioxy-N-ethylamphetamine)

Structure for HMDB0254369 (3,4-Methylenedioxy-N-ethylamphetamine)

3D Structure for HMDB0254369 (3,4-Methylenedioxy-N-ethylamphetamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra