Hmdb loader

Showing metabocard for 3,4-Methylenedioxyamphetamine (HMDB0041931)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:48:34 UTC
Update Date2023-02-21 17:29:03 UTC
HMDB IDHMDB0041931
Secondary Accession Numbers
  • HMDB41931
Metabolite Identification
Common Name3,4-Methylenedioxyamphetamine
DescriptionAn amphetamine derivative that inhibits uptake of catecholamine neurotransmitters. It is a hallucinogen. It is less toxic than its methylated derivative but in sufficient doses may still destroy serotonergic neurons and has been used for that purpose experimentally. [PubChem]; In 1970, the Controlled Substances Act was enacted in the United States, placing MDA into Schedule I. It is similarly controlled in other nations. In Canada MDA is a Schedule III drug. Internationally, MDA is a Schedule I drug under the Convention on Psychotropic Substances. Many similar unscheduled MDxx chemicals can be prosecuted under the Federal Analog Act. MDA (3,4-methylenedioxyamphetamine), also known as tenamfetamine (INN), is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes. It is mainly used as a recreational drug, an entheogen, and a tool in use to supplement various types of practices for transcendence, including in meditation, psychonautics, and as an agent in psychedelic psychotherapy. It was first synthesized by G. Mannish and W. Jacobson in 1910. There are about 20 different synthetic routes described in the literature for its preparation.
Structure
Data?1677000543
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0041931 (3,4-Methylenedioxyamphetamine)

1509
  Mrv0541 02231215322D          

 13 14  0  0  1  0            999 V2000
    6.4461    0.4081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4461   -0.9196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9276   -0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 13  1  0  0  0  0
  2 10  1  0  0  0  0
  2 13  1  0  0  0  0
  3  5  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  2  0  0  0  0
  9 12  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
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3D MOL for HMDB0041931 (3,4-Methylenedioxyamphetamine)

HMDB0041931
     RDKit          3D
3,4-Methylenedioxyamphetamine
 26 27  0  0  0  0  0  0  0  0999 V2000
   -2.0667   -1.5918   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -0.2745    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9236    0.6753   -0.5314 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159    0.1940    1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2029    0.4443    0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857    1.6598    0.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4467    1.8015   -0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189    0.7489   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9671   -0.4853    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6981   -0.5997    0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355   -1.3777    0.1196 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1661   -0.6043   -0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6291    0.6178   -0.7035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9041   -2.2716    0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1291   -1.3854   -0.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8653   -1.9568   -0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4800   -0.5473    1.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9075    1.6354   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8950    0.4595   -0.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4193   -0.4974    2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8705    1.1667    1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4964    2.5103    0.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7360    2.7677   -0.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4439   -1.5935    1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7957   -0.4281    0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8150   -1.0678   -0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 10  5  1  0
 13  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
 10 24  1  0
 12 25  1  0
 12 26  1  0
M  END
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3D SDF for HMDB0041931 (3,4-Methylenedioxyamphetamine)

1509
  Mrv0541 02231215322D          

 13 14  0  0  1  0            999 V2000
    6.4461    0.4081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4461   -0.9196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9276   -0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 13  1  0  0  0  0
  2 10  1  0  0  0  0
  2 13  1  0  0  0  0
  3  5  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  2  0  0  0  0
  9 12  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041931

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(N)CC1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3

> <INCHI_KEY>
NGBBVGZWCFBOGO-UHFFFAOYSA-N

> <FORMULA>
C10H13NO2

> <MOLECULAR_WEIGHT>
179.2157

> <EXACT_MASS>
179.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.51322698241418

> <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-amine

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
1.4274839493333333

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.011411157347462

> <JCHEM_POLAR_SURFACE_AREA>
44.480000000000004

> <JCHEM_REFRACTIVITY>
49.472100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-methylenedioxyamphetamine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0041931 (3,4-Methylenedioxyamphetamine)

HMDB0041931
     RDKit          3D
3,4-Methylenedioxyamphetamine
 26 27  0  0  0  0  0  0  0  0999 V2000
   -2.0667   -1.5918   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -0.2745    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9236    0.6753   -0.5314 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159    0.1940    1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2029    0.4443    0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857    1.6598    0.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4467    1.8015   -0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189    0.7489   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9671   -0.4853    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6981   -0.5997    0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355   -1.3777    0.1196 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1661   -0.6043   -0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6291    0.6178   -0.7035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9041   -2.2716    0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1291   -1.3854   -0.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8653   -1.9568   -0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4800   -0.5473    1.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9075    1.6354   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8950    0.4595   -0.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4193   -0.4974    2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8705    1.1667    1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4964    2.5103    0.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7360    2.7677   -0.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4439   -1.5935    1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7957   -0.4281    0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8150   -1.0678   -0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 10  5  1  0
 13  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
 10 24  1  0
 12 25  1  0
 12 26  1  0
M  END
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PDB for HMDB0041931 (3,4-Methylenedioxyamphetamine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1509                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      12.033   0.762   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.033  -1.717   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       3.907   1.063   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.574   1.063   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.241   0.293   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.908   0.293   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.242   1.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.576   0.293   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908  -1.247   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.576  -1.247   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.241  -1.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.242  -2.017   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.932  -0.477   0.000  0.00  0.00           C+0
CONECT    1    8   13                                                       
CONECT    2   10   13                                                       
CONECT    3    5                                                            
CONECT    4    5    6                                                       
CONECT    5    3    4   11                                                  
CONECT    6    4    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    1    7   10                                                  
CONECT    9    6   12                                                       
CONECT   10    2    8   12                                                  
CONECT   11    5                                                            
CONECT   12    9   10                                                       
CONECT   13    1    2                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0041931 (3,4-Methylenedioxyamphetamine)

COMPND    HMDB0041931
HETATM    1  C1  UNL     1      -2.067  -1.592  -0.144  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.561  -0.275   0.469  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.924   0.675  -0.531  1.00  0.00           N  
HETATM    4  C3  UNL     1      -1.516   0.194   1.423  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.203   0.444   0.838  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.186   1.660   0.326  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.447   1.802  -0.206  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.319   0.749  -0.233  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.967  -0.485   0.270  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.698  -0.600   0.797  1.00  0.00           C  
HETATM   11  O1  UNL     1       3.036  -1.378   0.120  1.00  0.00           O  
HETATM   12  C10 UNL     1       4.166  -0.604  -0.196  1.00  0.00           C  
HETATM   13  O2  UNL     1       3.629   0.618  -0.704  1.00  0.00           O  
HETATM   14  H1  UNL     1      -1.904  -2.272   0.720  1.00  0.00           H  
HETATM   15  H2  UNL     1      -1.129  -1.385  -0.659  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.865  -1.957  -0.824  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.480  -0.547   1.029  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.907   1.635  -0.177  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.895   0.460  -0.851  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.419  -0.497   2.283  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.871   1.167   1.873  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.496   2.510   0.339  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.736   2.768  -0.606  1.00  0.00           H  
HETATM   24  H11 UNL     1       0.444  -1.594   1.191  1.00  0.00           H  
HETATM   25  H12 UNL     1       4.796  -0.428   0.709  1.00  0.00           H  
HETATM   26  H13 UNL     1       4.815  -1.068  -0.954  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    4   17
CONECT    3   18   19
CONECT    4    5   20   21
CONECT    5    6    6   10
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   13
CONECT    9   10   10   11
CONECT   10   24
CONECT   11   12
CONECT   12   13   25   26
END
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SMILES for HMDB0041931 (3,4-Methylenedioxyamphetamine)

CC(N)CC1=CC2=C(OCO2)C=C1
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INCHI for HMDB0041931 (3,4-Methylenedioxyamphetamine)

InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(RS)-3,4-(Methylenedioxy)methamphetamineHMDB
1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamineHMDB
1-(1,3-Benzodioxol-5-yl)-N-methylpropan-2-amineHMDB
3,4-MethylenedioxymethamphetamineHMDB
DL-(3,4-Methylenedioxy)methamphetamineHMDB
MDMAHMDB
N,alpha-Dimethyl-1,3-benzodioxole-5-ethanamineHMDB
N-Methyl-3,4-methylenedioxyamphetamineHMDB
3,4 MethylenedioxyamphetamineHMDB
3,4-MethylenedioxyamphetamineMeSH
Chemical FormulaC10H13NO2
Average Molecular Weight179.2157
Monoisotopic Molecular Weight179.094628665
IUPAC Name1-(2H-1,3-benzodioxol-5-yl)propan-2-amine
Traditional Name3,4-methylenedioxyamphetamine
CAS Registry Number4764-17-4
SMILES
CC(N)CC1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3
InChI KeyNGBBVGZWCFBOGO-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Aralkylamine
  • Benzenoid
  • Oxacycle
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.64Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.83 g/LALOGPS
logP1.15ALOGPS
logP1.43ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)10.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.48 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.47 m³·mol⁻¹ChemAxon
Polarizability19.51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.29231661259
DarkChem[M-H]-137.0331661259
DeepCCS[M+H]+138.71830932474
DeepCCS[M-H]-135.90830932474
DeepCCS[M-2H]-172.38530932474
DeepCCS[M+Na]+147.92430932474
AllCCS[M+H]+139.532859911
AllCCS[M+H-H2O]+135.132859911
AllCCS[M+NH4]+143.632859911
AllCCS[M+Na]+144.832859911
AllCCS[M-H]-141.432859911
AllCCS[M+Na-2H]-142.032859911
AllCCS[M+HCOO]-142.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. 2.53 minutes32390414
Predicted by Siyang on May 30, 202210.2315 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.38 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid104.7 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1071.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid316.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid125.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid184.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid76.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid312.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid350.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)299.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid825.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid319.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid902.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid231.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid264.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate448.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA337.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water104.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-MethylenedioxyamphetamineCC(N)CC1=CC2=C(OCO2)C=C12208.2Standard polar33892256
3,4-MethylenedioxyamphetamineCC(N)CC1=CC2=C(OCO2)C=C11505.8Standard non polar33892256
3,4-MethylenedioxyamphetamineCC(N)CC1=CC2=C(OCO2)C=C11480.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Methylenedioxyamphetamine,1TMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N[Si](C)(C)C1644.3Semi standard non polar33892256
3,4-Methylenedioxyamphetamine,1TMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N[Si](C)(C)C1639.3Standard non polar33892256
3,4-Methylenedioxyamphetamine,2TMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N([Si](C)(C)C)[Si](C)(C)C1853.0Semi standard non polar33892256
3,4-Methylenedioxyamphetamine,2TMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N([Si](C)(C)C)[Si](C)(C)C1860.6Standard non polar33892256
3,4-Methylenedioxyamphetamine,1TBDMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N[Si](C)(C)C(C)(C)C1887.9Semi standard non polar33892256
3,4-Methylenedioxyamphetamine,1TBDMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N[Si](C)(C)C(C)(C)C1859.3Standard non polar33892256
3,4-Methylenedioxyamphetamine,2TBDMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2289.7Semi standard non polar33892256
3,4-Methylenedioxyamphetamine,2TBDMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2331.2Standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01509
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1555
KEGG Compound IDC07577
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3,4-Methylenedioxyamphetamine
METLIN IDNot Available
PubChem Compound1614
PDB IDNot Available
ChEBI ID1391
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Aalberg L, Clark CR, Deruiter J: Chromatographic and mass spectral studies on isobaric and isomeric substances related to 3,4-methylenedioxymethamphetamine. J Chromatogr Sci. 2004 Oct;42(9):464-9. [PubMed:15693185 ]