Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-13 11:42:12 UTC

Update Date

2023-02-21 17:28:59 UTC

HMDB ID

HMDB0041842

Secondary Accession Numbers

HMDB41842

Metabolite Identification

Common Name

Bufotenin

Description

A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic. Bufotenin (5-OH-DMT), is a tryptamine related to the neurotransmitter serotonin. It is an alkaloid found in the skin of some species of toads; in mushrooms, higher plants, and mammals. Bufotenin is a chemical constituent in the venom and eggs of several species of toads belonging to the Bufo genus, but most notably in the Colorado River toad (Bufo alvarius) as it is the only toad species in which bufotenin is present in large enough quantities for a psychoactive effect. Extracts of toad venom, containing bufotenin and other bioactive compounds, have been used in some traditional medicines (probably derived from Bufo gargarizans), which has been used medicinally for centuries in China. Bufotenin is a constituent of the seeds of Anadenanthera colubrina and Anadenanthera peregrina trees. Anadenanthera seeds have been used as an ingredient in psychedelic snuff preparations by indigenous cultures of the Caribbean, Central and South America.

Structure

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

HMDB0041842
     RDKit          3D
Bufotenin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.6372    0.3594    0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7772   -0.7742    0.6489 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183   -1.8396   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6785   -0.3176   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439    0.6383    0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273    1.1379   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4922    2.3067   -0.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7230    2.3096   -1.3867 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3944    1.1775   -1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703    0.7136   -1.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -0.5037   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -1.2403   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973   -2.4636    0.3943 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9899   -0.7808    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210    0.4466   -0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6578   -0.0174    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6317    1.0172    0.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825    0.8868    1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8336   -2.3883   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3408   -1.3429   -0.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8415   -2.5453    0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -1.1906   -0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0440    0.2098   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3947    1.5050    1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4915    0.0587    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2972    3.0624   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470    3.0562   -1.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3144    1.3027   -1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1296   -0.8606   -1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1719   -2.5779    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3033   -1.3456    0.8063 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
 12 14  1  0
 14 15  2  0
 15  6  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
M  END

1445
  Mrv1652304062013062D          

 15 16  0  0  0  0            999 V2000
    2.0930   -0.1082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3370    1.4693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -1.5972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734    0.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -0.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0807    0.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4986   -0.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1443    1.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860    2.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2  7  1  0  0  0  0
  2 13  1  0  0  0  0
  2 14  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  2  0  0  0  0
  6  8  2  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 15  2  0  0  0  0
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041842

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCC1=CNC2=C1C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3

> <INCHI_KEY>
VTTONGPRPXSUTJ-UHFFFAOYSA-N

> <FORMULA>
C12H16N2O

> <MOLECULAR_WEIGHT>
204.2682

> <EXACT_MASS>
204.126263144

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.290220670308504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2-(dimethylamino)ethyl]-1H-indol-5-ol

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
1.2922694904624674

> <ALOGPS_LOGS>
-1.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.218197203699578

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.232412171709068

> <JCHEM_PKA_STRONGEST_BASIC>
9.910793391467232

> <JCHEM_POLAR_SURFACE_AREA>
39.26

> <JCHEM_REFRACTIVITY>
62.423100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bufotenine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0041842
     RDKit          3D
Bufotenin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.6372    0.3594    0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7772   -0.7742    0.6489 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183   -1.8396   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6785   -0.3176   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439    0.6383    0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273    1.1379   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4922    2.3067   -0.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7230    2.3096   -1.3867 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3944    1.1775   -1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703    0.7136   -1.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -0.5037   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -1.2403   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973   -2.4636    0.3943 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9899   -0.7808    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210    0.4466   -0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6578   -0.0174    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6317    1.0172    0.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825    0.8868    1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8336   -2.3883   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3408   -1.3429   -0.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8415   -2.5453    0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -1.1906   -0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0440    0.2098   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3947    1.5050    1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4915    0.0587    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2972    3.0624   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470    3.0562   -1.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3144    1.3027   -1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1296   -0.8606   -1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1719   -2.5779    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3033   -1.3456    0.8063 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
 12 14  1  0
 14 15  2  0
 15  6  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1445                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  O   UNK     0       3.907  -0.202   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      11.829   2.743   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.365  -2.981   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       9.844   0.961   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.365  -0.503   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.908  -0.972   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.351   1.279   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.908  -2.512   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.264  -1.742   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574  -0.202   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574  -3.282   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.241  -0.972   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.336   3.060   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.801   3.889   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.241  -2.512   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2    7   13   14                                                  
CONECT    3    8    9                                                       
CONECT    4    5    7                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    8   10                                                  
CONECT    7    2    4                                                       
CONECT    8    3    6   11                                                  
CONECT    9    3    5                                                       
CONECT   10    6   12                                                       
CONECT   11    8   15                                                       
CONECT   12    1   10   15                                                  
CONECT   13    2                                                            
CONECT   14    2                                                            
CONECT   15   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0041842
HETATM    1  C1  UNL     1      -3.637   0.359   0.891  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.777  -0.774   0.649  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.518  -1.840  -0.047  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.678  -0.318  -0.184  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.844   0.638   0.613  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.327   1.138  -0.138  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.492   2.307  -0.847  1.00  0.00           C  
HETATM    8  N2  UNL     1       1.723   2.310  -1.387  1.00  0.00           N  
HETATM    9  C7  UNL     1       2.394   1.178  -1.062  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.670   0.714  -1.355  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.125  -0.504  -0.879  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.260  -1.240  -0.098  1.00  0.00           C  
HETATM   13  O1  UNL     1       3.697  -2.464   0.394  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.990  -0.781   0.195  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.521   0.447  -0.282  1.00  0.00           C  
HETATM   16  H1  UNL     1      -4.658  -0.017   1.107  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.632   1.017   0.021  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.182   0.887   1.771  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.834  -2.388  -0.725  1.00  0.00           H  
HETATM   20  H5  UNL     1      -4.341  -1.343  -0.574  1.00  0.00           H  
HETATM   21  H6  UNL     1      -3.842  -2.545   0.739  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.097  -1.191  -0.540  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.044   0.210  -1.101  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.395   1.505   1.020  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.491   0.059   1.521  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.297   3.062  -0.916  1.00  0.00           H  
HETATM   27  H12 UNL     1       2.147   3.056  -1.980  1.00  0.00           H  
HETATM   28  H13 UNL     1       4.314   1.303  -1.956  1.00  0.00           H  
HETATM   29  H14 UNL     1       5.130  -0.861  -1.108  1.00  0.00           H  
HETATM   30  H15 UNL     1       4.172  -2.578   1.282  1.00  0.00           H  
HETATM   31  H16 UNL     1       1.303  -1.346   0.806  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4
CONECT    3   19   20   21
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7    7   15
CONECT    7    8   26
CONECT    8    9   27
CONECT    9   10   10   15
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   12   13   14
CONECT   13   30
CONECT   14   15   15   31
END

HMDB0041842
     RDKit          3D
Bufotenin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.6372    0.3594    0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7772   -0.7742    0.6489 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183   -1.8396   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6785   -0.3176   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439    0.6383    0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273    1.1379   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4922    2.3067   -0.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7230    2.3096   -1.3867 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3944    1.1775   -1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703    0.7136   -1.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -0.5037   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -1.2403   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973   -2.4636    0.3943 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9899   -0.7808    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210    0.4466   -0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6578   -0.0174    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6317    1.0172    0.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825    0.8868    1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8336   -2.3883   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3408   -1.3429   -0.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8415   -2.5453    0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -1.1906   -0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0440    0.2098   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3947    1.5050    1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4915    0.0587    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2972    3.0624   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470    3.0562   -1.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3144    1.3027   -1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1296   -0.8606   -1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1719   -2.5779    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3033   -1.3456    0.8063 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
 12 14  1  0
 14 15  2  0
 15  6  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-[2-(Dimethylamino)ethyl]-5-indolol	ChEBI
3-[2-(Dimethylamino)ethyl]indol-5-ol	ChEBI
3-[beta-(Dimethylamino)ethyl]-5-hydroxyindole	ChEBI
5-Hydroxy-N,N-dimethyltryptamine	ChEBI
Bufotenine	ChEBI
DM5-HT	ChEBI
N,N-Dimethylserotonin	ChEBI
3-[b-(Dimethylamino)ethyl]-5-hydroxyindole	Generator
3-[Β-(dimethylamino)ethyl]-5-hydroxyindole	Generator
1H-indol-5-Ol, {3-[2-(dimethylamino)ethyl]-}	HMDB
3-(2-(Dimethylamino)ethyl)-1H-indol-5-ol (acd/name 4.0)	HMDB
3-(2-Dimethylaminoethyl)-5-indolol	HMDB
3-(2-Dimethylaminoethyl)indol-5-ol	HMDB
3-(beta-Dimethylaminoethyl)-5-hydroxyindole	HMDB
3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol	HMDB
3-[2-(Dimethylamino)ethyl]-indol-5-ol	HMDB
5-Hydroxy-N, N-dimethyltryptamine	HMDB
Cinobufotenine	HMDB
Cohoba	HMDB
Dimethylserotonin	HMDB
indol-5-Ol, {3-[2-(dimethylamino)ethyl]-}	HMDB
Mapine	HMDB
Mappin	HMDB
Mappine	HMDB
N, N-Dimethylserotonin	HMDB
N,N-Dimethyl-5-hydroxytryptamine	HMDB
{3-[(2-dimethylamino)ethyl]-5-indolol}	HMDB
{3-[(beta-dimethylamino)ethyl]-5-hydroxyindole}	HMDB
N,N Dimethyl 5 hydroxytryptamine	HMDB
5 Hydroxy N,N dimethyltryptamine	HMDB
Bufotenin	KEGG

Chemical Formula

C₁₂H₁₆N₂O

Average Molecular Weight

204.2682

Monoisotopic Molecular Weight

204.126263144

IUPAC Name

3-[2-(dimethylamino)ethyl]-1H-indol-5-ol

Traditional Name

bufotenine

CAS Registry Number

487-93-4

SMILES

CN(C)CCC1=CNC2=C1C=C(O)C=C2

InChI Identifier

InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3

InChI Key

VTTONGPRPXSUTJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Serotonins

Alternative Parents

Substituents

Serotonin
Hydroxyindole
3-alkylindole
Indole
Alkaloid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amine (CHEBI:3210 )
tryptamine alkaloid (CHEBI:3210 )
Indole alkaloids (C08299 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0041842)
Extracellular (HMDB: HMDB0041842)

Excreta

Biofluid or Excreta

Feces (PMID: 25037050)

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Biological role

Metabolite (HMDB: HMDB0041842)

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Hallucinogen (HMDB: HMDB0041842)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	146.5 °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	3.2 g/L	ALOGPS
logP	2.04	ALOGPS
logP	1.29	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.23	ChemAxon
pKa (Strongest Basic)	9.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	39.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.42 m³·mol⁻¹	ChemAxon
Polarizability	23.29 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]+	148.656	31661259
DarkChem	[M-H]-	145.159	31661259
DeepCCS	[M+H]+	145.277	30932474
DeepCCS	[M-H]-	142.453	30932474
DeepCCS	[M-2H]-	178.697	30932474
DeepCCS	[M+Na]+	154.235	30932474
AllCCS	[M+H]+	145.5	32859911
AllCCS	[M+H-H2O]+	141.3	32859911
AllCCS	[M+NH4]+	149.3	32859911
AllCCS	[M+Na]+	150.4	32859911
AllCCS	[M-H]-	150.3	32859911
AllCCS	[M+Na-2H]-	150.6	32859911
AllCCS	[M+HCOO]-	151.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bufotenin	CN(C)CCC1=CNC2=C1C=C(O)C=C2	3022.6	Standard polar	33892256
Bufotenin	CN(C)CCC1=CNC2=C1C=C(O)C=C2	2032.6	Standard non polar	33892256
Bufotenin	CN(C)CCC1=CNC2=C1C=C(O)C=C2	2103.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bufotenin,1TMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12	2020.9	Semi standard non polar	33892256
Bufotenin,1TMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12	2090.1	Semi standard non polar	33892256
Bufotenin,2TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2070.4	Semi standard non polar	33892256
Bufotenin,2TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2130.4	Standard non polar	33892256
Bufotenin,1TBDMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2258.4	Semi standard non polar	33892256
Bufotenin,1TBDMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12	2311.8	Semi standard non polar	33892256
Bufotenin,2TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2514.5	Semi standard non polar	33892256
Bufotenin,2TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2570.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bufotenin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9200000000-0af816b35b1e16d258a1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bufotenin GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9130000000-7bbf336895ab1b156223	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bufotenin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bufotenin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9100000000-3e8c21621c306ca36dec	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotenin 10V, Positive-QTOF	splash10-0a4i-0390000000-af3dd65f76ad8654b621	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotenin 20V, Positive-QTOF	splash10-08fr-0940000000-8952400d2cb6d011de82	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotenin 40V, Positive-QTOF	splash10-01qa-1900000000-34b8e0879f296431d1e8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotenin 10V, Negative-QTOF	splash10-0udi-0090000000-59bc27deb381d771d0ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotenin 20V, Negative-QTOF	splash10-0udi-1290000000-c4aa46abeccd608387a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotenin 40V, Negative-QTOF	splash10-0536-5900000000-1b322d788e0c55bfa242	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotenin 10V, Negative-QTOF	splash10-0udi-0190000000-aa5796e407ec72620b1b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotenin 20V, Negative-QTOF	splash10-0ue9-0970000000-fa89d4528ce714421e8a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotenin 40V, Negative-QTOF	splash10-001i-1900000000-df031839bb432c50ef0d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotenin 10V, Positive-QTOF	splash10-0a4i-0190000000-7230690add489b3c18b9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotenin 20V, Positive-QTOF	splash10-0bt9-1950000000-42c05e07b418d453a0a8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotenin 40V, Positive-QTOF	splash10-0a4i-8900000000-cd0c40dcec1955a75dcb	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB01445

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

Bufotenin

METLIN ID

Not Available

PubChem Compound

10257

PDB ID

Not Available

ChEBI ID

3210

Food Biomarker Ontology

Not Available

VMH ID

M01408

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. [PubMed:8747157 ]
Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. [PubMed:1058643 ]
Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. [PubMed:9468359 ]
Pomilio AB, Vitale AA, Ciprian-Ollivier J, Cetkovich-Bakmas M, Gomez R, Vazquez G: Ayahoasca: an experimental psychosis that mirrors the transmethylation hypothesis of schizophrenia. J Ethnopharmacol. 1999 Apr;65(1):29-51. [PubMed:10350367 ]
Sponheim E, Myhre AM, Reichelt KL, Aalen OO: [Urine peptide patterns in children with milder types of autism]. Tidsskr Nor Laegeforen. 2006 May 25;126(11):1475-7. [PubMed:16732341 ]

Showing metabocard for Bufotenin (HMDB0041842)

MOL for HMDB0041842 (Bufotenin)

3D MOL for HMDB0041842 (Bufotenin)

3D SDF for HMDB0041842 (Bufotenin)

3D-SDF for HMDB0041842 (Bufotenin)

PDB for HMDB0041842 (Bufotenin)

3D PDB for HMDB0041842 (Bufotenin)

SMILES for HMDB0041842 (Bufotenin)

INCHI for HMDB0041842 (Bufotenin)

Structure for HMDB0041842 (Bufotenin)

3D Structure for HMDB0041842 (Bufotenin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra