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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-04-12 19:07:12 UTC

Update Date

2023-02-21 17:17:11 UTC

HMDB ID

HMDB0005973

Secondary Accession Numbers

HMDB05973

Metabolite Identification

Common Name

Dimethyltryptamine

Description

Dimethyltryptamine is an N-methylated indoleamine derivative, a serotonergic hallucinogen found in several plants, especially Prestonia amazonica (Apocynaceae) and in mammalian brain, blood, and urine. It apparently acts as an agonist at some types of serotonin receptors and an antagonist at others. DMT is a derivative of tryptamine with two additional methyl groups at the amine nitrogen atom. DMT is often synthesized by the Speeter-Anthony synthesis from indole using oxalyl chloride, dimethylamine, and lithium aluminium hydride as reagents. DMT is usually used in its base form, but it is more stable as a salt, e.g. as a fumarate. In contrast to DMT's base, its salts are water-soluble. DMT in solution degrades relatively fast and should be stored protected from air and light in a freezer. Highly pure DMT crystals, when evaporated out of a solvent and depositing upon glass, often produce small but highly defined white crystalline needles which when viewed under intense light will sparkle, and appear colorless under high magnification. In labs, it has been known to be explosive under a certain degree of heat. DMT is a powerful psychoactive substance. If DMT is smoked, injected, or orally ingested with an MAOI, it can produce powerful entheogenic experiences including intense visual hallucinations, euphoria, even true hallucinations (perceived extensions of reality). A trip sitter is recommended to assist the drug user in staying physically and mentally healthy, and, in the case of smoked DMT, to catch the pipe if the user loses awareness of it. DMT is classified in the United States as a Schedule I drug. There are no drug tests that would show DMT usage. None of the basic NIDA 5 drug tests or any extended drug test will show a result for DMT. Dimethyltryptamine (DMT), also known as N,N-dimethyltryptamine, is a psychedelic tryptamine. It is not to be confused with 5-MeO-DMT and is similar in chemical structure to the neurotransmitter serotonin. DMT is created in small amounts by the human body during normal metabolism by the enzyme tryptamine-N-methyltransferase. Pure DMT at room temperature is a clear or white crystalline solid. DMT was first chemically synthesized in 1931. It also occurs naturally in many species of plants. DMT-containing plants are used in several South American shamanic practices. It is one of the main active constituents of snuffs like yopo and of the drink ayahuasca. Oral ingestion: DMT, which is broken down by the digestive enzyme monoamine oxidase, is practically inactive if taken orally, unless combined with a monoamine oxidase inhibitor (MAOI). The traditional South American ayahuasca, or yage, is a tea mixture containing DMT and a MAOI. There are a number of admixtures to this brew, but most commonly it is simply the leaves of Psychotria viridis (containing DMT), and the vine Banisteriopsis caapi (the source of MAOI). Other DMT containing plants, including Diplopterys cabrerana, are sometimes used in ayahuasca in different areas of South America. Two common sources in the western US are Reed canary grass (Phalaris arundinacea) and Harding grass (Phalaris aquatica). These invasive grasses contain low levels of DMT and other alkaloids. Taken orally with an appropriate MAOI, DMT produces a long lasting (over 3 hour), slow, but deep spiritual experience. MAOIs should be used with extreme caution as they can have lethal complications with some prescription drugs, such as SSRI antidepressants, and some over-the-counter drugs. Smoked: If DMT is smoked, the maximal effects last for a short period of time (5-30 minutes dose dependent). The onset after inhalation is very fast (less than 45 seconds) and maximal effects are reached within about a minute. The Business Man's lunch trip is a common name due to the relatively short duration of vaporized, insufflated, or injected DMT.

Structure

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

HMDB0005973
     RDKit          3D
Dimethyltryptamine
 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.4987   -1.3185   -0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -0.0514   -0.1725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7258    1.0077    0.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5901   -0.0471    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530   -0.6403   -0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -0.7726   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503   -1.9817    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6544   -1.7524    0.3651 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9331   -0.4479    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0807    0.3254    0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0835    1.6705    0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8665    2.2446   -0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    1.5351   -0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7469    0.1846   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0895   -1.8189   -1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5799   -1.1347   -0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5151   -1.9634    0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2648    0.8263    1.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0817    1.9176    0.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544    1.2749   -0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828   -0.5642    1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3617    1.0539    0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7469    0.0126   -1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0603   -1.6138   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -2.9427    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141   -2.4398    0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -0.1288    0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9916    2.2449    0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9060    3.3171   -0.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7997    2.0027   -0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  6  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
M  END

1488
  Mrv0541 02231215312D          

 14 15  0  0  0  0            999 V2000
    5.1796    1.4693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -1.5972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1160    0.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9233    0.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -0.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9869    1.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6286    2.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501   -0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501   -1.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  2  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  2  0  0  0  0
  6  7  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  2  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005973

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3

> <INCHI_KEY>
DMULVCHRPCFFGV-UHFFFAOYSA-N

> <FORMULA>
C12H16N2

> <MOLECULAR_WEIGHT>
188.2688

> <EXACT_MASS>
188.131348522

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.317037319867836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.3020657809999996

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.16497386926707

> <JCHEM_PKA_STRONGEST_BASIC>
9.547277133939458

> <JCHEM_POLAR_SURFACE_AREA>
19.03

> <JCHEM_REFRACTIVITY>
60.442200000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(psychogenic)

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0005973
     RDKit          3D
Dimethyltryptamine
 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.4987   -1.3185   -0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -0.0514   -0.1725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7258    1.0077    0.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5901   -0.0471    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530   -0.6403   -0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -0.7726   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503   -1.9817    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6544   -1.7524    0.3651 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9331   -0.4479    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0807    0.3254    0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0835    1.6705    0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8665    2.2446   -0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    1.5351   -0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7469    0.1846   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0895   -1.8189   -1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5799   -1.1347   -0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5151   -1.9634    0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2648    0.8263    1.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0817    1.9176    0.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544    1.2749   -0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828   -0.5642    1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3617    1.0539    0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7469    0.0126   -1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0603   -1.6138   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -2.9427    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141   -2.4398    0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -0.1288    0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9916    2.2449    0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9060    3.3171   -0.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7997    2.0027   -0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  6  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1488                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       9.669   2.743   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       7.205  -2.981   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.683   0.961   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.205  -0.503   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.190   1.279   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748  -0.972   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -2.512   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.104  -1.742   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -0.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -3.282   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.176   3.060   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.640   3.889   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -0.972   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -2.512   0.000  0.00  0.00           C+0
CONECT    1    5   11   12                                                  
CONECT    2    7    8                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6    8                                                  
CONECT    5    1    3                                                       
CONECT    6    4    7    9                                                  
CONECT    7    2    6   10                                                  
CONECT    8    2    4                                                       
CONECT    9    6   13                                                       
CONECT   10    7   14                                                       
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13    9   14                                                       
CONECT   14   10   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0005973
HETATM    1  C1  UNL     1      -3.499  -1.318  -0.363  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.902  -0.051  -0.173  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.726   1.008   0.294  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.590  -0.047   0.435  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.653  -0.640  -0.546  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.741  -0.773  -0.221  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.350  -1.982   0.132  1.00  0.00           C  
HETATM    8  N2  UNL     1       2.654  -1.752   0.365  1.00  0.00           N  
HETATM    9  C7  UNL     1       2.933  -0.448   0.183  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.081   0.325   0.281  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.084   1.671   0.031  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.867   2.245  -0.332  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.720   1.535  -0.442  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.747   0.185  -0.185  1.00  0.00           C  
HETATM   15  H1  UNL     1      -3.089  -1.819  -1.257  1.00  0.00           H  
HETATM   16  H2  UNL     1      -4.580  -1.135  -0.606  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.515  -1.963   0.535  1.00  0.00           H  
HETATM   18  H4  UNL     1      -4.265   0.826   1.242  1.00  0.00           H  
HETATM   19  H5  UNL     1      -3.082   1.918   0.390  1.00  0.00           H  
HETATM   20  H6  UNL     1      -4.454   1.275  -0.515  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.683  -0.564   1.395  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.362   1.054   0.570  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.747   0.013  -1.472  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.060  -1.614  -0.886  1.00  0.00           H  
HETATM   25  H11 UNL     1       0.909  -2.943   0.213  1.00  0.00           H  
HETATM   26  H12 UNL     1       3.414  -2.440   0.650  1.00  0.00           H  
HETATM   27  H13 UNL     1       5.009  -0.129   0.561  1.00  0.00           H  
HETATM   28  H14 UNL     1       4.992   2.245   0.113  1.00  0.00           H  
HETATM   29  H15 UNL     1       2.906   3.317  -0.523  1.00  0.00           H  
HETATM   30  H16 UNL     1       0.800   2.003  -0.723  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    4
CONECT    3   18   19   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7    7   14
CONECT    7    8   25
CONECT    8    9   26
CONECT    9   10   10   14
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   13   29
CONECT   13   14   14   30
END

HMDB0005973
     RDKit          3D
Dimethyltryptamine
 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.4987   -1.3185   -0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -0.0514   -0.1725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7258    1.0077    0.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5901   -0.0471    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530   -0.6403   -0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -0.7726   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503   -1.9817    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6544   -1.7524    0.3651 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9331   -0.4479    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0807    0.3254    0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0835    1.6705    0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8665    2.2446   -0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    1.5351   -0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7469    0.1846   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0895   -1.8189   -1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5799   -1.1347   -0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5151   -1.9634    0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2648    0.8263    1.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0817    1.9176    0.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544    1.2749   -0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828   -0.5642    1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3617    1.0539    0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7469    0.0126   -1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0603   -1.6138   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -2.9427    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141   -2.4398    0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -0.1288    0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9916    2.2449    0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9060    3.3171   -0.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7997    2.0027   -0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  6  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3-Indolyl)ethyldimethylamine	ChEBI
3-(2-Dimethylaminoethyl)indole	ChEBI
3-[2-(Dimethylamino)ethyl]indole	ChEBI
DMT	ChEBI
N,N-Dimethyl-1H-indole-3-ethylamine	ChEBI
N,N Dimethyltryptamine	MeSH
(2-indol-3-Ylethyl)dimethylamine	HMDB
(Psychogenic)	HMDB
2-(1H-indol-3-yl)-N,N-Dimethylethanamine	HMDB
2-(1H-indol-3-yl)-N,N-Dimethylethanamine (acd/name 4.0)	HMDB
3-(2-(dimethylamino)Ethyl)-indole	HMDB
3-[2- (dimethylamino)Ethyl]-indole	HMDB
Dimethyltryptamine(DMT)	HMDB
Indolalkylamine der	HMDB
N,N-Dimethyl-1H-indole-3-ethanamine	HMDB
N,N-Dimethyl-1H-indole-3-ethanamine (9ci)	HMDB
N,N-Dimethyltryptamine	HMDB
N-(2-(1H-indol-3-yl)Ethyl)-N,N-dimethylamine (acd/name 4.0)	HMDB
Dimethyltryptamine	MeSH

Chemical Formula

C₁₂H₁₆N₂

Average Molecular Weight

188.2688

Monoisotopic Molecular Weight

188.131348522

IUPAC Name

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

Traditional Name

(psychogenic)

CAS Registry Number

61-50-7

SMILES

CN(C)CCC1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3

InChI Key

DMULVCHRPCFFGV-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
Aralkylamine
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Amine
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tryptamine alkaloid (CHEBI:28969 )
tryptamines (CHEBI:28969 )
Indole alkaloids (C08302 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	46 °C	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
Water Solubility	1.69 g/L	ALOGPS
logP	2.41	ALOGPS
logP	2.3	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	17.16	ChemAxon
pKa (Strongest Basic)	9.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	19.03 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.44 m³·mol⁻¹	ChemAxon
Polarizability	22.32 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]+	143.72	31661259
DarkChem	[M-H]-	140.073	31661259
DeepCCS	[M-2H]-	174.239	30932474
DeepCCS	[M+Na]+	149.778	30932474
AllCCS	[M+H]+	141.3	32859911
AllCCS	[M+H-H2O]+	137.0	32859911
AllCCS	[M+NH4]+	145.3	32859911
AllCCS	[M+Na]+	146.4	32859911
AllCCS	[M-H]-	147.2	32859911
AllCCS	[M+Na-2H]-	147.6	32859911
AllCCS	[M+HCOO]-	148.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.73 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8269 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.15 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	76.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	708.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	291.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	120.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	105.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	291.9 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	295.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	733.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	695.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	166.7 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	1010.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	204.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	260.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	635.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	419.1 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	46.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dimethyltryptamine	CN(C)CCC1=CNC2=CC=CC=C12	2790.3	Standard polar	33892256
Dimethyltryptamine	CN(C)CCC1=CNC2=CC=CC=C12	1777.6	Standard non polar	33892256
Dimethyltryptamine	CN(C)CCC1=CNC2=CC=CC=C12	1777.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dimethyltryptamine,1TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12	1838.1	Semi standard non polar	33892256
Dimethyltryptamine,1TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12	1840.7	Standard non polar	33892256
Dimethyltryptamine,1TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12	2057.9	Standard polar	33892256
Dimethyltryptamine,1TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2057.7	Semi standard non polar	33892256
Dimethyltryptamine,1TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2052.4	Standard non polar	33892256
Dimethyltryptamine,1TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2193.0	Standard polar	33892256

Spectra

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	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	0.015 +/- 0.0030 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.001 (0.000056-0.000097) umol/mmol creatinine	Adult (>18 years old)	Both	Surgical patients	11763413	details
Urine	Detected and Quantified	0.00069 (0.00014-0.00018) umol/mmol creatinine	Adult (>18 years old)	Both	Internal medical patients	11763413	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01488

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

N,N-Dimethyltryptamine

METLIN ID

Not Available

PubChem Compound

6089

PDB ID

Not Available

ChEBI ID

28969

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

Not Available

Showing metabocard for Dimethyltryptamine (HMDB0005973)

MOL for HMDB0005973 (Dimethyltryptamine)

3D MOL for HMDB0005973 (Dimethyltryptamine)

3D SDF for HMDB0005973 (Dimethyltryptamine)

3D-SDF for HMDB0005973 (Dimethyltryptamine)

PDB for HMDB0005973 (Dimethyltryptamine)

3D PDB for HMDB0005973 (Dimethyltryptamine)

SMILES for HMDB0005973 (Dimethyltryptamine)

INCHI for HMDB0005973 (Dimethyltryptamine)

Structure for HMDB0005973 (Dimethyltryptamine)

3D Structure for HMDB0005973 (Dimethyltryptamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized