NP-MRD: Showing NP-Card for 5-Methoxydimethyltryptamine (NP0000370)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2006-05-22 14:17:31 UTC

Updated at

2021-06-29 00:47:18 UTC

NP-MRD ID

NP0000370

Secondary Accession Numbers

None

Natural Product 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>
NP0000370

> <DATABASE_NAME>
NP-MRD

> <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

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	HMDB
Methoxydimethyltryptamine	HMDB
Methylbufotenin	HMDB
5 Methoxy N,N dimethyltryptamine	HMDB
N,N Dimethyl 5 methoxytryptamine	HMDB

Chemical Formula

C₁₃H₁₈N₂O

Average Mass

218.2948 Da

Monoisotopic Mass

218.14191 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	varshavi.d26@gmail.com	Not Available	Not Available	2021-08-09	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Amanita citrina	LOTUS Database	35616633
Anadenanthera peregrina	LOTUS Database	35616633
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Arundo donax	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Desmodium pulchellum	KNApSAcK Database	22123792
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Lespedeza bicolor	LOTUS Database	35616633
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phalaris aquatica	KNApSAcK Database	22123792
Phalaris arundinacea	KNApSAcK Database	22123792
Phalaris canariensis	KNApSAcK Database	22123792
Phalaris minor	KNApSAcK Database	22123792
Phalaris tuberosa	KNApSAcK Database	22123792
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phragmites communis	KNApSAcK Database	22123792
Phyllodium pulchellum	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0002004

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]
Riga MS, Soria G, Tudela R, Artigas F, Celada P: The natural hallucinogen 5-MeO-DMT, component of Ayahuasca, disrupts cortical function in rats: reversal by antipsychotic drugs. Int J Neuropsychopharmacol. 2014 Aug;17(8):1269-82. doi: 10.1017/S1461145714000261. Epub 2014 Mar 20. [PubMed:24650558 ]
Jiang XL, Shen HW, Yu AM: Potentiation of 5-methoxy-N,N-dimethyltryptamine-induced hyperthermia by harmaline and the involvement of activation of 5-HT1A and 5-HT2A receptors. Neuropharmacology. 2015 Feb;89:342-51. doi: 10.1016/j.neuropharm.2014.10.013. [PubMed:25446678 ]
Duvvuri V, Risbrough VB, Kaye WH, Geyer MA: 5-HT1A receptor activation is necessary for 5-MeODMT-dependent potentiation of feeding inhibition. Pharmacol Biochem Behav. 2009 Sep;93(3):349-53. doi: 10.1016/j.pbb.2009.05.014. Epub 2009 May 31. [PubMed:19490926 ]
Riga MS, Bortolozzi A, Campa L, Artigas F, Celada P: The serotonergic hallucinogen 5-methoxy-N,N-dimethyltryptamine disrupts cortical activity in a regionally-selective manner via 5-HT(1A) and 5-HT(2A) receptors. Neuropharmacology. 2016 Feb;101:370-8. doi: 10.1016/j.neuropharm.2015.10.016. Epub 2015 Oct 23. [PubMed:26477571 ]
Dakic V, Minardi Nascimento J, Costa Sartore R, Maciel RM, de Araujo DB, Ribeiro S, Martins-de-Souza D, Rehen SK: Short term changes in the proteome of human cerebral organoids induced by 5-MeO-DMT. Sci Rep. 2017 Oct 9;7(1):12863. doi: 10.1038/s41598-017-12779-5. [PubMed:28993683 ]

Showing NP-Card for 5-Methoxydimethyltryptamine (NP0000370)

MOL for NP0000370 (5-Methoxydimethyltryptamine)

3D MOL for NP0000370 (5-Methoxydimethyltryptamine)

3D SDF for NP0000370 (5-Methoxydimethyltryptamine)

3D-SDF for NP0000370 (5-Methoxydimethyltryptamine)

PDB for NP0000370 (5-Methoxydimethyltryptamine)

3D PDB for NP0000370 (5-Methoxydimethyltryptamine)

SMILES for NP0000370 (5-Methoxydimethyltryptamine)

INCHI for NP0000370 (5-Methoxydimethyltryptamine)

Structure for NP0000370 (5-Methoxydimethyltryptamine)

3D Structure for NP0000370 (5-Methoxydimethyltryptamine)