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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:31 UTC

Update Date

2021-09-07 16:45:32 UTC

HMDB ID

HMDB0002004

Secondary Accession Numbers

HMDB02004

Metabolite Identification

Common Name

5-Methoxydimethyltryptamine

Description

5-Methoxydimethyltryptamine, like all methoxydimethyltryptamines is a compound that contain the biogenic monoamine tryptamine and is substituted with one methoxy group and two methyl groups. Members of this group include several potent serotonergic hallucinogens found in several unrelated plants, skins of certain toads, and in mammalian brains. They are possibly involved in the etiology of schizophrenia. They are formed as metabolites of serotonin (5-hydroxytryptamine) or tryptamine by the enzyme indolethylamine N-methyltransferase (INMT). The physiological significance of the N-methylating pathway of indoleamine metabolism, and of the methylated end products, is unknown. Because of the known psychotropic properties of the dimethylated amines, their possible involvement in the chemical pathogenesis of mental disorders has received wide interest. The hallucinogenic actions of the methylated indoleamines, like those of LSD, are believed to be mediated through the 5HT2 receptor. (PMID 11763413 ).

Structure

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

HMDB0002004
     RDKit          3D
5-Methoxydimethyltryptamine
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.4072    2.1654   -0.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0120    1.8800   -0.3624 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6114    0.5599   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096   -0.4496    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1064   -1.7579    0.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7569   -2.0435    0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0355   -3.1820    0.2439 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -2.9335   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223   -1.5796   -0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6637   -0.8496   -0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1902   -0.0387    0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3874    0.6376    0.1179 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    1.4389    1.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199    1.4923   -1.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8608   -1.0496   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760    0.2662   -0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7489    1.7913    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9218    1.5135   -0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6273    3.2280   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5421   -0.1793    0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7708   -2.5594    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4763   -4.1107    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430   -3.6740   -0.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5480   -0.2062   -1.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386   -1.6147   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    0.7070    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4864   -0.7662    1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2530    0.8345    2.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2800    2.2687    1.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8840    1.9111    0.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1564    2.1211   -1.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888    0.9451   -1.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3787    2.2162   -0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459    1.0177   -0.6134 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  9 15  1  0
 15 16  2  0
 16  3  1  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
M  END


  Mrv1652305271900002D          

 16 17  0  0  0  0            999 V2000
   14.7163   -7.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9317   -7.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3186   -7.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4048   -6.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0990   -6.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5115   -7.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0990   -8.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2740   -6.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8615   -7.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2740   -8.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6510   -6.0453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8615   -8.8018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0364   -8.8018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3295   -8.0505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1578   -8.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1140   -7.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11  5  1  0  0  0  0
  4 11  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
  1 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002004

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(NC=C2CCN(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3

> <INCHI_KEY>
ZSTKHSQDNIGFLM-UHFFFAOYSA-N

> <FORMULA>
C13H18N2O

> <MOLECULAR_WEIGHT>
218.2948

> <EXACT_MASS>
218.141913208

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.4656074086973

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[2-(5-methoxy-1H-indol-3-yl)ethyl]dimethylamine

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
2.1443945153333344

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.441282951700625

> <JCHEM_PKA_STRONGEST_BASIC>
9.584576430430719

> <JCHEM_POLAR_SURFACE_AREA>
28.259999999999998

> <JCHEM_REFRACTIVITY>
66.90540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-MeO-DMT

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0002004
     RDKit          3D
5-Methoxydimethyltryptamine
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.4072    2.1654   -0.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0120    1.8800   -0.3624 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6114    0.5599   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096   -0.4496    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1064   -1.7579    0.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7569   -2.0435    0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0355   -3.1820    0.2439 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -2.9335   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223   -1.5796   -0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6637   -0.8496   -0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1902   -0.0387    0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3874    0.6376    0.1179 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    1.4389    1.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199    1.4923   -1.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8608   -1.0496   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760    0.2662   -0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7489    1.7913    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9218    1.5135   -0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6273    3.2280   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5421   -0.1793    0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7708   -2.5594    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4763   -4.1107    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430   -3.6740   -0.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5480   -0.2062   -1.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386   -1.6147   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    0.7070    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4864   -0.7662    1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2530    0.8345    2.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2800    2.2687    1.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8840    1.9111    0.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1564    2.1211   -1.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888    0.9451   -1.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3787    2.2162   -0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459    1.0177   -0.6134 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  9 15  1  0
 15 16  2  0
 16  3  1  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      27.470 -13.997   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.006 -14.473   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.861 -13.442   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.022 -11.911   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.585 -12.429   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.355 -13.763   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.585 -15.096   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.045 -12.429   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.275 -13.763   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.045 -15.096   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      23.615 -11.285   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      20.275 -16.430   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      18.735 -16.430   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      28.615 -15.028   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      28.295 -16.534   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.079 -14.552   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3   11                                                       
CONECT    5    6    8   11                                                  
CONECT    6    3    5    7                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    7    9   12                                                  
CONECT   11    5    4                                                       
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14   15   16    1                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0002004
HETATM    1  C1  UNL     1       4.407   2.165  -0.183  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.012   1.880  -0.362  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.611   0.560  -0.185  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.510  -0.450   0.151  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.106  -1.758   0.326  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.757  -2.043   0.154  1.00  0.00           C  
HETATM    7  N1  UNL     1       1.036  -3.182   0.244  1.00  0.00           N  
HETATM    8  C6  UNL     1      -0.260  -2.934  -0.018  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.422  -1.580  -0.295  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.664  -0.850  -0.637  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.190  -0.039   0.517  1.00  0.00           C  
HETATM   12  N2  UNL     1      -3.387   0.638   0.118  1.00  0.00           N  
HETATM   13  C10 UNL     1      -3.950   1.439   1.188  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.220   1.492  -1.031  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.861  -1.050  -0.179  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.276   0.266  -0.353  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.749   1.791   0.807  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.922   1.514  -0.944  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.627   3.228  -0.344  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.542  -0.179   0.272  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.771  -2.559   0.585  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.476  -4.111   0.489  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.043  -3.674  -0.011  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.548  -0.206  -1.531  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.439  -1.615  -0.888  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.458   0.707   0.876  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.486  -0.766   1.318  1.00  0.00           H  
HETATM   28  H12 UNL     1      -4.253   0.835   2.063  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.280   2.269   1.477  1.00  0.00           H  
HETATM   30  H14 UNL     1      -4.884   1.911   0.804  1.00  0.00           H  
HETATM   31  H15 UNL     1      -4.156   2.121  -1.087  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.189   0.945  -1.993  1.00  0.00           H  
HETATM   33  H17 UNL     1      -2.379   2.216  -0.921  1.00  0.00           H  
HETATM   34  H18 UNL     1       0.546   1.018  -0.613  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4   16
CONECT    4    5   20
CONECT    5    6    6   21
CONECT    6    7   15
CONECT    7    8   22
CONECT    8    9    9   23
CONECT    9   10   15
CONECT   10   11   24   25
CONECT   11   12   26   27
CONECT   12   13   14
CONECT   13   28   29   30
CONECT   14   31   32   33
CONECT   15   16   16
CONECT   16   34
END

HMDB0002004
     RDKit          3D
5-Methoxydimethyltryptamine
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.4072    2.1654   -0.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0120    1.8800   -0.3624 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6114    0.5599   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096   -0.4496    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1064   -1.7579    0.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7569   -2.0435    0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0355   -3.1820    0.2439 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -2.9335   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223   -1.5796   -0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6637   -0.8496   -0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1902   -0.0387    0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3874    0.6376    0.1179 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    1.4389    1.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199    1.4923   -1.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8608   -1.0496   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760    0.2662   -0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7489    1.7913    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9218    1.5135   -0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6273    3.2280   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5421   -0.1793    0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7708   -2.5594    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4763   -4.1107    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430   -3.6740   -0.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5480   -0.2062   -1.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386   -1.6147   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    0.7070    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4864   -0.7662    1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2530    0.8345    2.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2800    2.2687    1.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8840    1.9111    0.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1564    2.1211   -1.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888    0.9451   -1.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3787    2.2162   -0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459    1.0177   -0.6134 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  9 15  1  0
 15 16  2  0
 16  3  1  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(2-Dimethylaminoethyl)-5-methoxyindole	ChEBI
3-[2-(N,N-Dimethylamino)ethyl]-5-methoxy-indole	ChEBI
5-MeO-DMT	ChEBI
5-Methoxy-N,N-dimethyl-1H-indole-3-ethanamine	ChEBI
MeODMT	ChEBI
Methoxybufotenin	ChEBI
N,N-Dimethyl-5-methoxytryptamine	ChEBI
O-Methylbufotenine	ChEBI
5-Methoxy-N,N-dimethyltryptamine	Kegg
3-(2-(N,N-Dimethyl)aminoethyl)-5-methoxyindole	HMDB
5-Methoxy-N,N-dimethyl-1H-indole-3-ethylamine	HMDB
5-Methoxyindole 3-(2-(N,N-dimethylamino)ethyl)	HMDB
Bufotenine, 5-methoxydimethyltryptamine	HMDB
Methylbufotenine	HMDB
N,N-Dimethyl-5-methoxy tryptamine	HMDB
Methoxydimethyltryptamines	MeSH, HMDB
Methoxydimethyltryptamine	MeSH, HMDB
Methylbufotenin	MeSH, HMDB
5 Methoxy N,N dimethyltryptamine	MeSH, HMDB
N,N Dimethyl 5 methoxytryptamine	MeSH, HMDB

Chemical Formula

C₁₃H₁₈N₂O

Average Molecular Weight

218.2948

Monoisotopic Molecular Weight

218.141913208

IUPAC Name

[2-(5-methoxy-1H-indol-3-yl)ethyl]dimethylamine

Traditional Name

5-MeO-DMT

CAS Registry Number

1019-45-0

SMILES

COC1=CC2=C(NC=C2CCN(C)C)C=C1

InChI Identifier

InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3

InChI Key

ZSTKHSQDNIGFLM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines and derivatives

Alternative Parents

Substituents

Tryptamine
3-alkylindole
Indole
Alkaloid or derivatives
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Azacycle
Ether
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:2086 )
aromatic ether (CHEBI:2086 )
tryptamine alkaloid (CHEBI:2086 )
Indole alkaloids (C08309 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0002004)

Biofluid or Excreta

Blood (HMDB: HMDB0002004)
Urine (HMDB: HMDB0002004)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0002004)

Excreta

Biofluid or Excreta

Urine (PMID: 11763413)

Cellular substructure

Membrane (HMDB: HMDB0002004)

Source

Endogenous

Endogenous (HMDB: HMDB0002004)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	153.759	30932474
[M+H]+	MetCCS_train_pos	151.522	30932474
[M-H]-	Not Available	153.759	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000351
[M+H]+	Not Available	151.702	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000351

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	2.38	ALOGPS
logP	2.14	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	17.44	ChemAxon
pKa (Strongest Basic)	9.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.26 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.91 m³·mol⁻¹	ChemAxon
Polarizability	25.47 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
DarkChem	[M+H]+	149.95	31661259
DarkChem	[M-H]-	149.628	31661259
DeepCCS	[M+H]+	152.23	30932474
DeepCCS	[M-H]-	149.872	30932474
DeepCCS	[M-2H]-	183.565	30932474
DeepCCS	[M+Na]+	158.487	30932474
AllCCS	[M+H]+	149.7	32859911
AllCCS	[M+H-H2O]+	145.7	32859911
AllCCS	[M+NH4]+	153.4	32859911
AllCCS	[M+Na]+	154.4	32859911
AllCCS	[M-H]-	156.1	32859911
AllCCS	[M+Na-2H]-	156.3	32859911
AllCCS	[M+HCOO]-	156.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Methoxydimethyltryptamine	COC1=CC2=C(NC=C2CCN(C)C)C=C1	2882.5	Standard polar	33892256
5-Methoxydimethyltryptamine	COC1=CC2=C(NC=C2CCN(C)C)C=C1	1981.7	Standard non polar	33892256
5-Methoxydimethyltryptamine	COC1=CC2=C(NC=C2CCN(C)C)C=C1	1988.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Methoxydimethyltryptamine,1TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C	2034.5	Semi standard non polar	33892256
5-Methoxydimethyltryptamine,1TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C	2102.8	Standard non polar	33892256
5-Methoxydimethyltryptamine,1TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C	2389.2	Standard polar	33892256
5-Methoxydimethyltryptamine,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C(C)(C)C	2234.7	Semi standard non polar	33892256
5-Methoxydimethyltryptamine,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C(C)(C)C	2307.8	Standard non polar	33892256
5-Methoxydimethyltryptamine,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C(C)(C)C	2499.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxydimethyltryptamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9310000000-095b611bc1d199502cb6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxydimethyltryptamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxydimethyltryptamine 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 - 5-Methoxydimethyltryptamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-014i-0090000000-81cb5c66bea4c4f559a7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-05fr-5910000000-e732961434e6f6d047c6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-0ab9-8900000000-4a1b4b925b663d3894ef	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-0a4i-8900000000-1febcb75852e631248d3	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-0a59-7900000000-dcdf4748d932c86ae91e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-00di-0900000000-60d541c0869cba86353f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0a4i-0900000000-2a00c789bf0a52b49304	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-qTof , Positive-QTOF	splash10-05ai-2900000000-8e19cf440ade1a459473	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ , positive-QTOF	splash10-014i-0090000000-81cb5c66bea4c4f559a7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ , positive-QTOF	splash10-05fr-5910000000-7d365fd4fa5aeedebef6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ , positive-QTOF	splash10-0ab9-8900000000-4a1b4b925b663d3894ef	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ , positive-QTOF	splash10-0a4i-8900000000-57e4ec6d746c4ef2bd66	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ , positive-QTOF	splash10-0a59-7900000000-995a794ee19726d9dad1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-IT , positive-QTOF	splash10-00di-0900000000-026ae917940e27f31556	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine , positive-QTOF	splash10-05ai-2900000000-8e19cf440ade1a459473	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 10V, Positive-QTOF	splash10-014i-0390000000-df235ce53bdd863a3080	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 20V, Positive-QTOF	splash10-0600-4950000000-458ffcc56b9f6180beb8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 40V, Positive-QTOF	splash10-0aou-3900000000-47db55905836c61c012e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 10V, Negative-QTOF	splash10-014i-0090000000-839bd41b21b5590a00e9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 20V, Negative-QTOF	splash10-014i-0190000000-37decac3777ccc04b4c0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 40V, Negative-QTOF	splash10-052f-2900000000-635297b98da106f6c0e5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 10V, Negative-QTOF	splash10-014i-0090000000-09dd32e79c2ea83c7941	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 20V, Negative-QTOF	splash10-014i-0290000000-05df1c62ff8d5cce80bd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 40V, Negative-QTOF	splash10-0a4l-0900000000-37c7f3dd2cc5915c3750	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 10V, Positive-QTOF	splash10-014i-0190000000-3c41a600694ff73dfe05	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.21 +/- 0.03 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.02 +/- 0.002 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.002 (0.00012-0.01) umol/mmol creatinine	Adult (>18 years old)	Both	Surgical patients	11763413	details
Urine	Detected and Quantified	0.0052 (0.0003-0.0094) umol/mmol creatinine	Adult (>18 years old)	Both	Psychiatric disorder	11763413	details
Urine	Detected and Quantified	0.00075 (0.00018-0.0027) umol/mmol creatinine	Adult (>18 years old)	Both	Internal medical patients	11763413	details

Associated Disorders and Diseases

Disease References

Major depressive disorder
Forsstrom T, Tuominen J, Karkkainen J: Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS. Scand J Clin Lab Invest. 2001;61(7):547-56. [PubMed:11763413 ]

Associated OMIM IDs

608516 (Major depressive disorder)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

5-MeO-DMT

METLIN ID

Not Available

PubChem Compound

1832

PDB ID

Not Available

ChEBI ID

2086

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Bertaccini, Giulio; Vitali, Tullo. Synthesis and pharmacological activity of some 5- methoxyindole derivatives occurring in nature. Farmaco, Edizione Scientifica (1967), 22(4), 229-44.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Uebelhack R, Franke L, Seidel K: [Methylated and unmethylated indolamine in the cisternal fluid in acute endogenous psychoses]. Biomed Biochim Acta. 1983;42(10):1343-6. [PubMed:6144308 ]
Forsstrom T, Tuominen J, Karkkainen J: Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS. Scand J Clin Lab Invest. 2001;61(7):547-56. [PubMed:11763413 ]

Showing metabocard for 5-Methoxydimethyltryptamine (HMDB0002004)

MOL for HMDB0002004 (5-Methoxydimethyltryptamine)

3D MOL for HMDB0002004 (5-Methoxydimethyltryptamine)

3D SDF for HMDB0002004 (5-Methoxydimethyltryptamine)

3D-SDF for HMDB0002004 (5-Methoxydimethyltryptamine)

PDB for HMDB0002004 (5-Methoxydimethyltryptamine)

3D PDB for HMDB0002004 (5-Methoxydimethyltryptamine)

SMILES for HMDB0002004 (5-Methoxydimethyltryptamine)

INCHI for HMDB0002004 (5-Methoxydimethyltryptamine)

Structure for HMDB0002004 (5-Methoxydimethyltryptamine)

3D Structure for HMDB0002004 (5-Methoxydimethyltryptamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra