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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:33:59 UTC

Update Date

2021-09-26 22:54:00 UTC

HMDB ID

HMDB0245501

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,5-Dimethoxy-4-methylamphetamine

Description

2,5-Dimethoxy-4-methylamphetamine, also known as DOM, belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. Based on a literature review very few articles have been published on 2,5-Dimethoxy-4-methylamphetamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,5-dimethoxy-4-methylamphetamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,5-Dimethoxy-4-methylamphetamine 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

HMDB0245501
     RDKit          3D
2,5-Dimethoxy-4-methylamphetamine
 34 34  0  0  0  0  0  0  0  0999 V2000
   -2.5086   -2.7392    1.8884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7154   -1.5824    1.1521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912   -0.6537    0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4491   -0.7604    1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4636    0.2068    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9039    0.1359    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7097   -0.3008   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557   -1.6901   -0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.4041    0.0180 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0044    1.2792   -0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761    2.2519   -0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282    3.3633   -1.3195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3424    1.4125   -0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2248    0.4285    0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6708    0.5326   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5602   -2.7094    2.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5230   -3.6771    1.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3150   -2.7751    2.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -1.5965    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1629   -0.5202    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744    1.1550    1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199    0.4383   -1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832   -2.1385   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0564   -2.2578    0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677   -1.6388   -1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4359    0.4591    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3111   -1.2009    0.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3050    4.0681   -1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038    3.8298   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1128    3.0374   -2.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7068    2.2708   -1.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3080    0.2174    0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9468    1.5879   -0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9170   -0.0296   -1.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  5 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 14  3  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
M  END

1528
  Mrv0541 02231215322D          

 15 15  0  0  1  0            999 V2000
    2.3645    0.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.5717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.1409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 14  1  0  0  0  0
  2 11  1  0  0  0  0
  2 15  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  9  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8 11  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245501

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CC(C)N)=C(OC)C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C12H19NO2/c1-8-5-12(15-4)10(6-9(2)13)7-11(8)14-3/h5,7,9H,6,13H2,1-4H3

> <INCHI_KEY>
NTJQREUGJKIARY-UHFFFAOYSA-N

> <FORMULA>
C12H19NO2

> <MOLECULAR_WEIGHT>
209.2848

> <EXACT_MASS>
209.141578857

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.088797730117523

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
2.002329339666667

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.936993631124006

> <JCHEM_POLAR_SURFACE_AREA>
44.480000000000004

> <JCHEM_REFRACTIVITY>
61.67280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(RS)-dom

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245501
     RDKit          3D
2,5-Dimethoxy-4-methylamphetamine
 34 34  0  0  0  0  0  0  0  0999 V2000
   -2.5086   -2.7392    1.8884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7154   -1.5824    1.1521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912   -0.6537    0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4491   -0.7604    1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4636    0.2068    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9039    0.1359    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7097   -0.3008   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557   -1.6901   -0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.4041    0.0180 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0044    1.2792   -0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761    2.2519   -0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282    3.3633   -1.3195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3424    1.4125   -0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2248    0.4285    0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6708    0.5326   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5602   -2.7094    2.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5230   -3.6771    1.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3150   -2.7751    2.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -1.5965    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1629   -0.5202    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744    1.1550    1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199    0.4383   -1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832   -2.1385   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0564   -2.2578    0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677   -1.6388   -1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4359    0.4591    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3111   -1.2009    0.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3050    4.0681   -1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038    3.8298   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1128    3.0374   -2.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7068    2.2708   -1.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3080    0.2174    0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9468    1.5879   -0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9170   -0.0296   -1.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  5 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 14  3  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1528                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.414   0.146   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.748  -2.934   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       8.415   3.996   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.081   1.686   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.415   2.456   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081   0.146   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -0.624   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415  -0.624   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748   1.686   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -2.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -2.164   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -2.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -4.474   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -0.624   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082  -2.164   0.000  0.00  0.00           C+0
CONECT    1    7   14                                                       
CONECT    2   11   15                                                       
CONECT    3    5                                                            
CONECT    4    5    6                                                       
CONECT    5    3    4    9                                                  
CONECT    6    4    7    8                                                  
CONECT    7    1    6   12                                                  
CONECT    8    6   11                                                       
CONECT    9    5                                                            
CONECT   10   11   12   13                                                  
CONECT   11    2    8   10                                                  
CONECT   12    7   10                                                       
CONECT   13   10                                                            
CONECT   14    1                                                            
CONECT   15    2                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0245501
HETATM    1  C1  UNL     1      -2.509  -2.739   1.888  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.715  -1.582   1.152  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.791  -0.654   0.744  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.449  -0.760   1.035  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.464   0.207   0.602  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.904   0.136   0.888  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.710  -0.301  -0.319  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.256  -1.690  -0.778  1.00  0.00           C  
HETATM    9  N1  UNL     1       4.116  -0.404   0.018  1.00  0.00           N  
HETATM   10  C8  UNL     1      -0.004   1.279  -0.128  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.876   2.252  -0.569  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.428   3.363  -1.320  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.342   1.413  -0.434  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.225   0.429   0.015  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.671   0.533  -0.293  1.00  0.00           C  
HETATM   16  H1  UNL     1      -1.560  -2.709   2.460  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.523  -3.677   1.294  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.315  -2.775   2.680  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.095  -1.597   1.601  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.163  -0.520   1.742  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.274   1.155   1.153  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.620   0.438  -1.144  1.00  0.00           H  
HETATM   23  H8  UNL     1       3.083  -2.139  -1.364  1.00  0.00           H  
HETATM   24  H9  UNL     1       2.056  -2.258   0.172  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.368  -1.639  -1.420  1.00  0.00           H  
HETATM   26  H11 UNL     1       4.436   0.459   0.507  1.00  0.00           H  
HETATM   27  H12 UNL     1       4.311  -1.201   0.661  1.00  0.00           H  
HETATM   28  H13 UNL     1       1.305   4.068  -1.380  1.00  0.00           H  
HETATM   29  H14 UNL     1      -0.404   3.830  -0.753  1.00  0.00           H  
HETATM   30  H15 UNL     1       0.113   3.037  -2.334  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.707   2.271  -1.016  1.00  0.00           H  
HETATM   32  H17 UNL     1      -4.308   0.217   0.547  1.00  0.00           H  
HETATM   33  H18 UNL     1      -3.947   1.588  -0.527  1.00  0.00           H  
HETATM   34  H19 UNL     1      -3.917  -0.030  -1.242  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4   14
CONECT    4    5   19
CONECT    5    6   10   10
CONECT    6    7   20   21
CONECT    7    8    9   22
CONECT    8   23   24   25
CONECT    9   26   27
CONECT   10   11   13
CONECT   11   12
CONECT   12   28   29   30
CONECT   13   14   14   31
CONECT   14   15
CONECT   15   32   33   34
END

HMDB0245501
     RDKit          3D
2,5-Dimethoxy-4-methylamphetamine
 34 34  0  0  0  0  0  0  0  0999 V2000
   -2.5086   -2.7392    1.8884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7154   -1.5824    1.1521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912   -0.6537    0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4491   -0.7604    1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4636    0.2068    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9039    0.1359    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7097   -0.3008   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557   -1.6901   -0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.4041    0.0180 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0044    1.2792   -0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761    2.2519   -0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282    3.3633   -1.3195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3424    1.4125   -0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2248    0.4285    0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6708    0.5326   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5602   -2.7094    2.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5230   -3.6771    1.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3150   -2.7751    2.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -1.5965    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1629   -0.5202    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744    1.1550    1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199    0.4383   -1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832   -2.1385   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0564   -2.2578    0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677   -1.6388   -1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4359    0.4591    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3111   -1.2009    0.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3050    4.0681   -1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038    3.8298   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1128    3.0374   -2.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7068    2.2708   -1.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3080    0.2174    0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9468    1.5879   -0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9170   -0.0296   -1.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  5 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 14  3  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(25-Dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine	HMDB
DOM	HMDB
2 5 DOM	HMDB
2,5 Dimethoxy 4 methylamphetamine	HMDB
2,5-Dimethoxy-4-methylamphetamine, (S)-isomer	HMDB
2,5-Dimethoxy-4-methylamphetamine hydrochloride, (R)-isomer	HMDB
2,5-Dimethoxy-4-methylamphetamine, hydrochloride	HMDB
2,5-Dimethoxy-4-methylamphetamine hydrochloride, (S)-isomer	HMDB
2,5-Dimethoxy-4-methylamphetamine, (+,-)-isomer	HMDB
2,5-Dimethoxy-4-methylamphetamine, (R)-isomer	HMDB
1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane	HMDB
2,5-Dimethoxy-4-methylamphetamine hydrochloride, (+,-)-isomer	HMDB
2,5-Dimethoxy-4-methylamphetamine	MeSH

Chemical Formula

C₁₂H₁₉NO₂

Average Molecular Weight

209.2848

Monoisotopic Molecular Weight

209.141578857

IUPAC Name

1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine

Traditional Name

(RS)-dom

CAS Registry Number

Not Available

SMILES

COC1=CC(CC(C)N)=C(OC)C=C1C

InChI Identifier

InChI=1S/C12H19NO2/c1-8-5-12(15-4)10(6-9(2)13)7-11(8)14-3/h5,7,9H,6,13H2,1-4H3

InChI Key

NTJQREUGJKIARY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Amphetamines and derivatives

Alternative Parents

Substituents

Amphetamine or derivatives
P-dimethoxybenzene
Dimethoxybenzene
Phenylpropane
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Aralkylamine
Toluene
Ether
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	2.02	ALOGPS
logP	2	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	9.94	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	44.48 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	61.67 m³·mol⁻¹	ChemAxon
Polarizability	24.09 Å³	ChemAxon
Number of Rings	1	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
DeepCCS	[M+H]+	149.808	30932474
DeepCCS	[M-H]-	147.45	30932474
DeepCCS	[M-2H]-	182.106	30932474
DeepCCS	[M+Na]+	156.937	30932474
AllCCS	[M+H]+	148.4	32859911
AllCCS	[M+H-H2O]+	144.4	32859911
AllCCS	[M+NH4]+	152.1	32859911
AllCCS	[M+Na]+	153.2	32859911
AllCCS	[M-H]-	151.6	32859911
AllCCS	[M+Na-2H]-	152.4	32859911
AllCCS	[M+HCOO]-	153.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.1701 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.44 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1181.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	302.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	91.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	372.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	375.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	159.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	921.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	347.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	942.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	278.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	341.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	293.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	18.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dimethoxy-4-methylamphetamine	COC1=CC(CC(C)N)=C(OC)C=C1C	2141.9	Standard polar	33892256
2,5-Dimethoxy-4-methylamphetamine	COC1=CC(CC(C)N)=C(OC)C=C1C	1664.2	Standard non polar	33892256
2,5-Dimethoxy-4-methylamphetamine	COC1=CC(CC(C)N)=C(OC)C=C1C	1647.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dimethoxy-4-methylamphetamine,1TMS,isomer #1	COC1=CC(CC(C)N[Si](C)(C)C)=C(OC)C=C1C	1792.1	Semi standard non polar	33892256
2,5-Dimethoxy-4-methylamphetamine,1TMS,isomer #1	COC1=CC(CC(C)N[Si](C)(C)C)=C(OC)C=C1C	1869.6	Standard non polar	33892256
2,5-Dimethoxy-4-methylamphetamine,1TMS,isomer #1	COC1=CC(CC(C)N[Si](C)(C)C)=C(OC)C=C1C	2260.0	Standard polar	33892256
2,5-Dimethoxy-4-methylamphetamine,2TMS,isomer #1	COC1=CC(CC(C)N([Si](C)(C)C)[Si](C)(C)C)=C(OC)C=C1C	1991.6	Semi standard non polar	33892256
2,5-Dimethoxy-4-methylamphetamine,2TMS,isomer #1	COC1=CC(CC(C)N([Si](C)(C)C)[Si](C)(C)C)=C(OC)C=C1C	2059.5	Standard non polar	33892256
2,5-Dimethoxy-4-methylamphetamine,2TMS,isomer #1	COC1=CC(CC(C)N([Si](C)(C)C)[Si](C)(C)C)=C(OC)C=C1C	2270.7	Standard polar	33892256
2,5-Dimethoxy-4-methylamphetamine,1TBDMS,isomer #1	COC1=CC(CC(C)N[Si](C)(C)C(C)(C)C)=C(OC)C=C1C	2048.4	Semi standard non polar	33892256
2,5-Dimethoxy-4-methylamphetamine,1TBDMS,isomer #1	COC1=CC(CC(C)N[Si](C)(C)C(C)(C)C)=C(OC)C=C1C	2085.4	Standard non polar	33892256
2,5-Dimethoxy-4-methylamphetamine,1TBDMS,isomer #1	COC1=CC(CC(C)N[Si](C)(C)C(C)(C)C)=C(OC)C=C1C	2373.7	Standard polar	33892256
2,5-Dimethoxy-4-methylamphetamine,2TBDMS,isomer #1	COC1=CC(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(OC)C=C1C	2477.9	Semi standard non polar	33892256
2,5-Dimethoxy-4-methylamphetamine,2TBDMS,isomer #1	COC1=CC(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(OC)C=C1C	2468.7	Standard non polar	33892256
2,5-Dimethoxy-4-methylamphetamine,2TBDMS,isomer #1	COC1=CC(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(OC)C=C1C	2437.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine EI-B (Non-derivatized)	splash10-0006-9100000000-466e6b5613c401a0fa96	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-6900000000-776d7576e097d8efa08b	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine 10V, Positive-QTOF	splash10-03dl-0980000000-d874c558243b20796dde	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine 20V, Positive-QTOF	splash10-01ox-2930000000-2c52c4614bb120efb5ce	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine 40V, Positive-QTOF	splash10-0ik9-4900000000-1fa2fbdf5cdc97ac738d	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine 10V, Negative-QTOF	splash10-0a4i-0290000000-fe950e9a3fb343078146	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine 20V, Negative-QTOF	splash10-0a4l-0960000000-433bb60470f3961f122c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine 40V, Negative-QTOF	splash10-03fu-2900000000-083d504731cf5c946a4d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine 10V, Positive-QTOF	splash10-01ox-0940000000-676d5eac9118e13eab4c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine 20V, Positive-QTOF	splash10-03xu-0940000000-db8f6661c8e1f052c18c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine 40V, Positive-QTOF	splash10-05o0-4910000000-f4d9ed4eccc36ec1adb3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine 10V, Negative-QTOF	splash10-0a4i-0190000000-2d34296744121f27404d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine 20V, Negative-QTOF	splash10-0a59-0950000000-e64fef2389f47938c739	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethoxy-4-methylamphetamine 40V, Negative-QTOF	splash10-0a4i-0960000000-68fe3fb78846a938d526	2021-10-12	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

DB01528

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

77462

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,5-Dimethoxy-4-methylamphetamine

METLIN ID

Not Available

PubChem Compound

85875

PDB ID

Not Available

ChEBI ID

Not Available

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 2,5-Dimethoxy-4-methylamphetamine (HMDB0245501)

MOL for HMDB0245501 (2,5-Dimethoxy-4-methylamphetamine)

3D MOL for HMDB0245501 (2,5-Dimethoxy-4-methylamphetamine)

3D SDF for HMDB0245501 (2,5-Dimethoxy-4-methylamphetamine)

3D-SDF for HMDB0245501 (2,5-Dimethoxy-4-methylamphetamine)

PDB for HMDB0245501 (2,5-Dimethoxy-4-methylamphetamine)

3D PDB for HMDB0245501 (2,5-Dimethoxy-4-methylamphetamine)

SMILES for HMDB0245501 (2,5-Dimethoxy-4-methylamphetamine)

INCHI for HMDB0245501 (2,5-Dimethoxy-4-methylamphetamine)

Structure for HMDB0245501 (2,5-Dimethoxy-4-methylamphetamine)

3D Structure for HMDB0245501 (2,5-Dimethoxy-4-methylamphetamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra