Jump To Section:

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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:52:26 UTC

Update Date

2023-02-21 17:29:05 UTC

HMDB ID

HMDB0042000

Secondary Accession Numbers

HMDB42000

Metabolite Identification

Common Name

Psilocin

Description

Psilocin (4-OH-DMT), an aromatic compound, sometimes also spelled psilocine, psilocyn, or psilotsin, is a psychedelic mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind-altering effects of psilocin are highly variable and subjective, but resemble those caused by LSD and mescaline. The effects typically last anywhere from three to eight hours depending on certain variables (such as metabolism, food interaction); however the effects can seem to last much longer due to psilocin's ability to distort the perception of time. Sulfur analogs are known with a benzothienyl replacement as well as 4-SH-DMT. N1-methylpsilocin is a functionally 5-HT2C receptor preferring agonists. 4-fluoro-N,N-dimethyltryptamine is known. O-Acetylpsilocin is an acetylized analog of psilocin, also known as 4-AcO-DMT. Additionally, substitution of a methyl group at the dimethylated nitrogen with an isopropyl or ethyl group yields 4-HO-MIPT (4-Hydroxy-N-Methyl-N-Isopropyltryptamine) and 4-HO-MET (4-Hydroxy-N-Methyl-N-Ethyltryptamine), respectively.

Structure

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

HMDB0042000
     RDKit          3D
Psilocin
 31 32  0  0  0  0  0  0  0  0999 V2000
    3.3973   -0.5124    1.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8197    0.3045    0.6013 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    0.3816   -0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379   -0.2460    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8387    0.6768   -0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5084    0.1050   -1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8140   -0.5861   -2.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110   -0.9554   -2.1766 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6774   -0.5179   -1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9658   -0.6359   -0.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2781   -0.0819    0.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2909    0.5807    1.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0029    0.6926    0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0091    1.3704    1.5693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.1445   -0.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5216   -0.8391    2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9952   -1.3373    1.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0001    0.1839    2.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3295    0.6779   -1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028    1.1914   -0.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3729   -0.5509   -0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9003   -0.4470    1.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6632   -1.2490   -0.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213    0.8182   -1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7107    1.6456   -0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069   -0.8038   -3.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5821   -1.4905   -2.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7133   -1.1636   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3022   -0.1670    1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5085    1.0319    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2482    1.7786    2.4773 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  1  0
 13 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
 12 30  1  0
 14 31  1  0
M  END


  Mrv0541 09051417112D          

 15 16  0  0  0  0            999 V2000
   -0.3440   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150   -2.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630   -1.9957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 12  9  1  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  1  0  0  0  0
 15 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0042000

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
SPCIYGNTAMCTRO-UHFFFAOYSA-N

> <FORMULA>
C12H16N2O

> <MOLECULAR_WEIGHT>
204.2682

> <EXACT_MASS>
204.126263144

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.10654590934275

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2-(dimethylamino)ethyl]-1H-indol-4-ol

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
1.1496978132675186

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.06786217937759

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.971078507865096

> <JCHEM_PKA_STRONGEST_BASIC>
9.776957339594496

> <JCHEM_POLAR_SURFACE_AREA>
39.260000000000005

> <JCHEM_REFRACTIVITY>
62.423100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
psilocin

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0042000
     RDKit          3D
Psilocin
 31 32  0  0  0  0  0  0  0  0999 V2000
    3.3973   -0.5124    1.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8197    0.3045    0.6013 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    0.3816   -0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379   -0.2460    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8387    0.6768   -0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5084    0.1050   -1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8140   -0.5861   -2.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110   -0.9554   -2.1766 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6774   -0.5179   -1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9658   -0.6359   -0.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2781   -0.0819    0.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2909    0.5807    1.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0029    0.6926    0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0091    1.3704    1.5693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.1445   -0.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5216   -0.8391    2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9952   -1.3373    1.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0001    0.1839    2.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3295    0.6779   -1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028    1.1914   -0.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3729   -0.5509   -0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9003   -0.4470    1.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6632   -1.2490   -0.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213    0.8182   -1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7107    1.6456   -0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069   -0.8038   -3.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5821   -1.4905   -2.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7133   -1.1636   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3022   -0.1670    1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5085    1.0319    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2482    1.7786    2.4773 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  1  0
 13 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
 12 30  1  0
 14 31  1  0
M  END

HEADER    PROTEIN                                 05-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-14         0                                  
HETATM    1  C   UNK     0      -0.642  -4.046   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.895  -4.870   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.340  -2.261   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       0.864  -3.725   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3    4    5                                                       
CONECT    4    3   10                                                       
CONECT    5    3   11                                                       
CONECT    6    7    9                                                       
CONECT    7    6   14                                                       
CONECT    8    9   13                                                       
CONECT    9    6    8   12                                                  
CONECT   10    4   12   13                                                  
CONECT   11    5   12   15                                                  
CONECT   12    9   10   11                                                  
CONECT   13    8   10                                                       
CONECT   14    1    2    7                                                  
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0042000
HETATM    1  C1  UNL     1       3.397  -0.512   1.693  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.820   0.305   0.601  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.778   0.382  -0.477  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.538  -0.246   0.220  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.839   0.677  -0.733  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.508   0.105  -1.083  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.814  -0.586  -2.219  1.00  0.00           C  
HETATM    8  N2  UNL     1      -2.111  -0.955  -2.177  1.00  0.00           N  
HETATM    9  C7  UNL     1      -2.677  -0.518  -1.023  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.966  -0.636  -0.522  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.278  -0.082   0.692  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.291   0.581   1.377  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.003   0.693   0.865  1.00  0.00           C  
HETATM   14  O1  UNL     1      -1.009   1.370   1.569  1.00  0.00           O  
HETATM   15  C12 UNL     1      -1.671   0.145  -0.344  1.00  0.00           C  
HETATM   16  H1  UNL     1       2.522  -0.839   2.295  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.995  -1.337   1.312  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.000   0.184   2.288  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.329   0.678  -1.412  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.503   1.191  -0.168  1.00  0.00           H  
HETATM   21  H6  UNL     1       4.373  -0.551  -0.594  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.900  -0.447   1.096  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.663  -1.249  -0.275  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.421   0.818  -1.660  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.711   1.646  -0.206  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.107  -0.804  -3.036  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.582  -1.490  -2.917  1.00  0.00           H  
HETATM   28  H13 UNL     1      -4.713  -1.164  -1.088  1.00  0.00           H  
HETATM   29  H14 UNL     1      -5.302  -0.167   1.110  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.509   1.032   2.336  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.248   1.779   2.477  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   30
CONECT   13   14   15   15
CONECT   14   31
END

HMDB0042000
     RDKit          3D
Psilocin
 31 32  0  0  0  0  0  0  0  0999 V2000
    3.3973   -0.5124    1.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8197    0.3045    0.6013 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    0.3816   -0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379   -0.2460    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8387    0.6768   -0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5084    0.1050   -1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8140   -0.5861   -2.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110   -0.9554   -2.1766 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6774   -0.5179   -1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9658   -0.6359   -0.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2781   -0.0819    0.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2909    0.5807    1.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0029    0.6926    0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0091    1.3704    1.5693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.1445   -0.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5216   -0.8391    2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9952   -1.3373    1.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0001    0.1839    2.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3295    0.6779   -1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028    1.1914   -0.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3729   -0.5509   -0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9003   -0.4470    1.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6632   -1.2490   -0.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213    0.8182   -1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7107    1.6456   -0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069   -0.8038   -3.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5821   -1.4905   -2.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7133   -1.1636   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3022   -0.1670    1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5085    1.0319    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2482    1.7786    2.4773 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  1  0
 13 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
 12 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)indol-4-ol	ChEBI
4-Hydroxy-N,N-dimethyltryptamine	ChEBI
4-OH-DMT	ChEBI
N,N-Dimethyl-4-hydroxytryptamine	ChEBI
Psilocine	ChEBI
Psilotsin	ChEBI
3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol	HMDB
3-[2-(Dimethylamino)ethyl]-indol-4-ol	HMDB
Psilocin tartrate (1:1)	HMDB
Psilocin hydrochloride	HMDB
(3-(2-Dimethylamino)ethyl)indol-4-ol	HMDB

Chemical Formula

C₁₂H₁₆N₂O

Average Molecular Weight

204.2682

Monoisotopic Molecular Weight

204.126263144

IUPAC Name

3-[2-(dimethylamino)ethyl]-1H-indol-4-ol

Traditional Name

psilocin

CAS Registry Number

520-53-6

SMILES

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

InChI Identifier

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

InChI Key

SPCIYGNTAMCTRO-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
Hydroxyindole
3-alkylindole
Indole
Alkaloid or derivatives
1-hydroxy-4-unsubstituted benzenoid
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 amino compound (CHEBI:8613 )
tryptamine alkaloid (CHEBI:8613 )
hydroxyindoles (CHEBI:8613 )
Alkaloids (C08312 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0042000)
Extracellular (HMDB: HMDB0042000)

Source

Endogenous

Endogenous (HMDB: HMDB0042000)

Process

Not Available

Role

Industrial application

Serotonergic agonist (HMDB: HMDB0042000)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Hallucinogen (HMDB: HMDB0042000)

Biological role

Human xenobiotic metabolite (HMDB: HMDB0042000)
Fungal metabolite (HMDB: HMDB0042000)
Drug metabolite (HMDB: HMDB0042000)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174.5 °C	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]+	CBM	144.8	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.08 g/L	ALOGPS
logP	1.98	ALOGPS
logP	1.15	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	8.97	ChemAxon
pKa (Strongest Basic)	9.78	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	23.11 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]+	148.038	31661259
DarkChem	[M-H]-	144.508	31661259
DeepCCS	[M+H]+	143.091	30932474
DeepCCS	[M-H]-	139.913	30932474
DeepCCS	[M-2H]-	176.472	30932474
DeepCCS	[M+Na]+	152.011	30932474
AllCCS	[M+H]+	145.5	32859911
AllCCS	[M+H-H2O]+	141.4	32859911
AllCCS	[M+NH4]+	149.3	32859911
AllCCS	[M+Na]+	150.5	32859911
AllCCS	[M-H]-	150.3	32859911
AllCCS	[M+Na-2H]-	150.6	32859911
AllCCS	[M+HCOO]-	151.0	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.	3.22 minutes	32390414
Predicted by Siyang on May 30, 2022	9.5078 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.9 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	100.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	579.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	257.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	103.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	281.5 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	289.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	817.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	661.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	51.3 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	962.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	180.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	228.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	701.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	498.7 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	103.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Psilocin	CN(C)CCC1=CNC2=C1C(O)=CC=C2	2951.4	Standard polar	33892256
Psilocin	CN(C)CCC1=CNC2=C1C(O)=CC=C2	1991.9	Standard non polar	33892256
Psilocin	CN(C)CCC1=CNC2=C1C(O)=CC=C2	2032.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Psilocin,1TMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(O[Si](C)(C)C)=C12	2000.4	Semi standard non polar	33892256
Psilocin,1TMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC(O)=C12	2068.5	Semi standard non polar	33892256
Psilocin,2TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C12	2080.6	Semi standard non polar	33892256
Psilocin,2TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C12	2048.2	Standard non polar	33892256
Psilocin,1TBDMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C12	2236.2	Semi standard non polar	33892256
Psilocin,1TBDMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(O)=C12	2294.0	Semi standard non polar	33892256
Psilocin,2TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C12	2492.8	Semi standard non polar	33892256
Psilocin,2TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C12	2479.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Psilocin EI-B (Non-derivatized)	splash10-0a4i-9000000000-62ea72268c3ac8349f99	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Psilocin EI-B (Non-derivatized)	splash10-0a4i-9000000000-62ea72268c3ac8349f99	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Psilocin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9200000000-4cca4e47c3bcf0ef37fc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Psilocin GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9030000000-8686b03317e1e073c475	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Psilocin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Psilocin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9110000000-58fd69735c607f0dbac4	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 - Psilocin 10V, Positive-QTOF	splash10-0a4i-0390000000-30b1cea064c20727c677	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilocin 20V, Positive-QTOF	splash10-08fr-0940000000-3d03cc820b34ad7de95c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilocin 40V, Positive-QTOF	splash10-01qa-2900000000-6a888d817b451f311e43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilocin 10V, Negative-QTOF	splash10-0udi-0090000000-b5141a6d394f0df7c3ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilocin 20V, Negative-QTOF	splash10-0udi-1290000000-19a265b5ec7903ebc866	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilocin 40V, Negative-QTOF	splash10-052f-5900000000-47f31324e343d436c5c1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilocin 10V, Positive-QTOF	splash10-0a4i-0190000000-f79ac11f836485a9a33e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilocin 20V, Positive-QTOF	splash10-0bt9-3960000000-13e401841c5ab05a231a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilocin 40V, Positive-QTOF	splash10-0a4i-9300000000-3a3674a946d2718b7443	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilocin 10V, Negative-QTOF	splash10-0udi-0090000000-32999cb59116f2b8b325	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilocin 20V, Negative-QTOF	splash10-0udi-0890000000-c3fa63e2f7ddbfec26ec	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilocin 40V, Negative-QTOF	splash10-0006-0900000000-f18009588fc5bfaa3db9	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

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001427

Chemspider ID

4807

KEGG Compound ID

C08312

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Psilocin

METLIN ID

Not Available

PubChem Compound

4980

PDB ID

Not Available

ChEBI ID

8613

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 Psilocin (HMDB0042000)

MOL for HMDB0042000 (Psilocin)

3D MOL for HMDB0042000 (Psilocin)

3D SDF for HMDB0042000 (Psilocin)

3D-SDF for HMDB0042000 (Psilocin)

PDB for HMDB0042000 (Psilocin)

3D PDB for HMDB0042000 (Psilocin)

SMILES for HMDB0042000 (Psilocin)

INCHI for HMDB0042000 (Psilocin)

Structure for HMDB0042000 (Psilocin)

3D Structure for HMDB0042000 (Psilocin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra