General Information of the Compound
Compound ID
CP0107635
Compound Name
3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
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Synonyms
1H-Indol-4-ol, 3-[2-(dimethylamino)ethyl]-
3-(2-(Dimethylamino)ethyl)-1H-indol-4-ol
3-(2-(Dimethylamino)ethyl)indol-4-ol
3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
4-Hydroxy-N,N-dimethyltryptamine
4-OH-DMT
520-53-6
AC1L1JCI
BRN 0160503
CHEBI:8613
CHEMBL65547
CMS88KUW0G
CX-59
DEA No. 7438
EINECS 208-296-5
INDOL-4-OL, 3-(2-(DIMETHYLAMINO)ETHYL)-
Indol-4-ol, 3-[2-(dimethylamino)ethyl]-
N,N-Dimethyl-4-Hydroxytryptamine
NCGC00247728-01
P-7800
PSILOCIN
Psilocin solution
Psilocine
Psilocyn
Psilotsin
UNII-CMS88KUW0G
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Structure
Formula
C12H16N2O
Molecular Weight
204.273
Canonical SMILES
CN(C)CCc1c[nH]c2cccc(O)c12
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InChI
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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InChIKey
SPCIYGNTAMCTRO-UHFFFAOYSA-N
CAS
520-53-6
Physicochemical Property
logP
1.9776
Rotatable Bonds
3
Heavy Atom Count
15
Polar Areas
39.26
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Complexity
15

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 4980
SID: 15195604
ChEMBL ID
CHEMBL65547
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT00825, 5-hydroxytryptamine receptor 2A
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
EC50 = 6.5 nM
   TI
   LI
   LO
   TS
CL000025 HEK-293T Homo sapiens (Human)  1
1
IC50 = 8.34 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 75.2 nM
Protein ID: PT01019, 5-hydroxytryptamine receptor 2B
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000025 HEK-293T Homo sapiens (Human)  1
1
IC50 = 1.07 nM
   TI
   LI
   LO
   TS
Protein ID: PT00939, 5-hydroxytryptamine receptor 2C
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000025 HEK-293T Homo sapiens (Human)  1
1
IC50 = 7.79 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( PSILOCIN )
Drug Name PSILOCIN
Target(s)
5-HT 2A receptor (HTR2A)
Inhibitor