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Showing NP-Card for Psilocin (NP0050695)

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Record Information
Version2.0
Created at2022-04-27 22:02:15 UTC
Updated at2022-04-27 22:02:15 UTC
NP-MRD IDNP0050695
Secondary Accession NumbersNone
Natural Product Identification
Common NamePsilocin
DescriptionPsilocin, also known as 4-OH-DMT or psilotsin, 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. Psilocin is a very strong basic compound (based on its pKa). Psilocin is found in Deconica montana, Gymnopilus purpuratus, Panaeolus cambodginiensis, Phaeolepiota aurea, Psilocybe arcana, Psilocybe azurescens, Psilocybe baeocystis, Psilocybe bohemica, Psilocybe caerulescens, Psilocybe cyanescens, Psilocybe mexicana, Psilocybe samuiensis, Psilocybe semilaceata, Psilocybe semilanceata and Psilocybe subcubensis. Psilocin was first documented in 2011 (PMID: 21148021). Psilocin is a potentially toxic compound (PMID: 21820980) (PMID: 22138681) (PMID: 23183899) (PMID: 23851905).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050695 (Psilocin)


  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
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3D MOL for NP0050695 (Psilocin)

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3D SDF for NP0050695 (Psilocin)

  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>
NP0050695

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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3D-SDF for NP0050695 (Psilocin)
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PDB for NP0050695 (Psilocin)
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

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3D PDB for NP0050695 (Psilocin)
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SMILES for NP0050695 (Psilocin)
CN(C)CCC1=CNC2=C1C(O)=CC=C2
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INCHI for NP0050695 (Psilocin)
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
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View in JSmol
Synonyms
ValueSource
3-(2-(Dimethylamino)ethyl)indol-4-olChEBI
4-Hydroxy-N,N-dimethyltryptamineChEBI
4-OH-DMTChEBI
N,N-Dimethyl-4-hydroxytryptamineChEBI
PsilocineChEBI
PsilotsinChEBI
3-[2-(Dimethylamino)ethyl]-1H-indol-4-olHMDB
3-[2-(Dimethylamino)ethyl]-indol-4-olHMDB
Psilocin tartrate (1:1)HMDB
Psilocin hydrochlorideHMDB
(3-(2-Dimethylamino)ethyl)indol-4-olHMDB
Chemical FormulaC12H16N2O
Average Mass204.2682 Da
Monoisotopic Mass204.12626 Da
IUPAC Name3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
Traditional Namepsilocin
CAS Registry NumberNot Available
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 KeySPCIYGNTAMCTRO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Deconica montanaLOTUS Database
Gymnopilus purpuratusLOTUS Database
Panaeolus cambodginiensisLOTUS Database
Phaeolepiota aureaLOTUS Database
Psilocybe arcanaFungi
Psilocybe azurescensFungi
Psilocybe baeocystisFungi
Psilocybe bohemicaFungi
Psilocybe caerulescensFungi
Psilocybe cyanescensFungi
Psilocybe mexicanaFungi
Psilocybe samuiensisLOTUS Database
Psilocybe semilaceataFungi
Psilocybe semilanceataFungi
Psilocybe subcubensisLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassTryptamines and derivatives  
Direct ParentTryptamines 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.98ALOGPS
logP1.15ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)8.97ChemAxon
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area39.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.42 m³·mol⁻¹ChemAxon
Polarizability23.11 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0042000  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001427  
Chemspider ID4807  
KEGG Compound IDC08312  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPsilocin  
METLIN IDNot Available
PubChem Compound4980  
PDB IDNot Available
ChEBI ID8613  
Good Scents IDNot Available
References
General References
  1. Halberstadt AL, Koedood L, Powell SB, Geyer MA: Differential contributions of serotonin receptors to the behavioral effects of indoleamine hallucinogens in mice. J Psychopharmacol. 2011 Nov;25(11):1548-61. doi: 10.1177/0269881110388326. Epub 2010 Dec 8. [PubMed:21148021  ] 
  2. Chen J, Li M, Yan X, Wu E, Zhu H, Lee KJ, Chu VM, Zhan L, Lee W, Kang JS: Determining the pharmacokinetics of psilocin in rat plasma using ultra-performance liquid chromatography coupled with a photodiode array detector after orally administering an extract of Gymnopilus spectabilis. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Sep 1;879(25):2669-72. doi: 10.1016/j.jchromb.2011.07.003. Epub 2011 Jul 18. [PubMed:21820980  ] 
  3. Martin R, Schurenkamp J, Pfeiffer H, Kohler H: A validated method for quantitation of psilocin in plasma by LC-MS/MS and study of stability. Int J Legal Med. 2012 Nov;126(6):845-9. doi: 10.1007/s00414-011-0652-8. Epub 2011 Dec 3. [PubMed:22138681  ] 
  4. Martin R, Schurenkamp J, Gasse A, Pfeiffer H, Kohler H: Determination of psilocin, bufotenine, LSD and its metabolites in serum, plasma and urine by SPE-LC-MS/MS. Int J Legal Med. 2013 May;127(3):593-601. doi: 10.1007/s00414-012-0796-1. Epub 2012 Nov 27. [PubMed:23183899  ] 
  5. Stebelska K: Fungal hallucinogens psilocin, ibotenic acid, and muscimol: analytical methods and biologic activities. Ther Drug Monit. 2013 Aug;35(4):420-42. doi: 10.1097/FTD.0b013e31828741a5. [PubMed:23851905  ]