Compound Detail

CHEMBL65547

PSILOCIN

🧪 Phase II

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🧪 Phase II

CN(C)CCc1c[nH]c2cccc(O)c12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL65547
Name	PSILOCIN
Phase	Phase II
Structure Type	MOL
InChI Key	SPCIYGNTAMCTRO-UHFFFAOYSA-N

Known Names

4-ho-dmt Psilocin Psilocyn

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

204.3

MW (Da)

1.98

ALogP

HBA

HBD

39.3

PSA (Å²)

0.80

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

USAN Stem

deu-

Extended Properties

Molecular Formula	C12H16N2O
MW	204.27
Aromatic Rings	2
Heavy Atoms	15
NP-Likeness	0.31

Activity Summary

Ki 19 meas. best 8.34

EC50 13 meas. best 8.37

IC50 5 meas. best 8.97

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	8.97	8.97	1.1	1
5-hydroxytryptamine receptor 2A CHEMBL224	EC50	8.37	7.9025	4.3	8
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	8.34	8.335	4.6	2
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	8.11	8.11	7.8	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	8.08	7.16	8.3	3
5-hydroxytryptamine receptor 2A CHEMBL5377	EC50	8.01	8.005	9.8	2
5-hydroxytryptamine receptor 1D CHEMBL1983	Ki	7.72	7.72	19.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	7.7	7.7	20.0	1
5-hydroxytryptamine receptor 2A CHEMBL322	Ki	7.6	6.8333	25.0	3
5-hydroxytryptamine receptor 2C CHEMBL225	EC50	7.52	7.52	30.0	1
5-hydroxytryptamine receptor 1E CHEMBL2182	Ki	7.36	7.36	44.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	EC50	7.24	7.24	58.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	7.2	7.2	63.0	1
5-hydroxytryptamine receptor 5A CHEMBL3426	Ki	7.16	7.16	70.0	1
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	7.14	7.14	72.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	7.14	7.14	72.0	1
D(3) dopamine receptor CHEMBL234	Ki	7.0	7.0	100.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.97	6.72	107.2	2
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.85	6.85	140.0	1
5-hydroxytryptamine receptor 1B CHEMBL1898	Ki	6.52	6.52	305.0	1
Adenosine receptor A2b CHEMBL255	Ki	5.89	5.89	1300.0	1
Adenosine receptor A2a CHEMBL251	Ki	5.7	5.7	2000.0	1
5-hydroxytryptamine receptor 2A CHEMBL322	EC50	5.64	5.64	2300.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	11.81	mL.min-1.g-1	Homo sapiens
CL	15.9	mL.min-1.g-1	Homo sapiens
T1/2	1.955	hr	Homo sapiens
T1/2	2.417	hr	Homo sapiens
T1/2	1.913	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 2B	IC50	=	1.07	nM	8.97	Modulation of human 5HT2B expressed in HEK293T cells co-transfected with Galphaq...	34917242
5-hydroxytryptamine receptor 2A	EC50	=	4.266	nM	8.37	Agonist activity at human 5-HT2A receptor expressed in Flp-In T-REx 293 cells as...	32077284
5-hydroxytryptamine receptor 2A	EC50	=	4.3	nM	8.37	Agonist activity at human 5-HT2A receptor expressed in Flp-In T-REx 293 cells as...	32077284
5-hydroxytryptamine receptor 2B	Ki	=	4.6	nM	8.34	Inhibition of 5-HT2BR (unknown origin ) assessed as inhibition constant	38516602
5-hydroxytryptamine receptor 2B	Ki	=	4.7	nM	8.33	Radioligand Binding Assay: The binding affinities shown in table 5 of psilocin a...	-
5-hydroxytryptamine receptor 2A	EC50	=	6.5	nM	8.19	Agonist activity at 5HT2A receptor (unknown origin) expressed in HEK293 cells by...	34917241
5-hydroxytryptamine receptor 2A	EC50	=	6.5	nM	8.19	Agonist activity at 5-HT2A receptor (unknown origin) by calcium flux assay	35450349
5-hydroxytryptamine receptor 2C	IC50	=	7.79	nM	8.11	Modulation of human 5HT2C expressed in HEK293T cells co-transfected with Galphaq...	34917242
5-hydroxytryptamine receptor 2A	IC50	=	8.34	nM	8.08	Modulation of human 5HT2A expressed in HEK293T cells co-transfected with Galphaq...	34917242
5-hydroxytryptamine receptor 2A	EC50	=	9.772	nM	8.01	Agonist activity at mouse 5-HT2A receptor expressed in Flp-In T-REx 293 cells as...	32077284
5-hydroxytryptamine receptor 2A	EC50	=	9.9	nM	8.0	Agonist activity at mouse 5-HT2A receptor expressed in Flp-In T-REx 293 cells as...	32077284
5-hydroxytryptamine receptor 1D	Ki	=	19.0	nM	7.72	Radioligand Binding Assay: The binding affinities shown in table 5 of psilocin a...	-
5-hydroxytryptamine receptor 2A	EC50	=	19.95	nM	7.7	Agonist activity at human smBiT-fused 5HT2A receptor expressed in CHO-K1 cells c...	38505858
D(1A) dopamine receptor	Ki	=	20.0	nM	7.7	Radioligand Binding Assay: The binding affinities shown in table 5 of psilocin a...	-
5-hydroxytryptamine receptor 2A	EC50	=	22.0	nM	7.66	Agonist activity at human smBiT-fused 5HT2A receptor expressed in CHO-K1 cells c...	38505858
5-hydroxytryptamine receptor 2A	EC50	=	24.0	nM	7.62	Effective concentration required for accumulation of [3H]inositol phosphate in c...	16061378
5-hydroxytryptamine receptor 2A	Ki	=	25.0	nM	7.6	In vitro binding to 5-hydroxytryptamine 2A receptor using [125 I]-DOI	12877591
5-hydroxytryptamine receptor 2C	EC50	=	30.0	nM	7.52	Effective concentration required for accumulation of [3H]inositol phosphate in c...	16061378
5-hydroxytryptamine receptor 1E	Ki	=	44.0	nM	7.36	Radioligand Binding Assay: The binding affinities shown in table 5 of psilocin a...	-
5-hydroxytryptamine receptor 2B	EC50	=	58.0	nM	7.24	Effective concentration required for accumulation of [3H]inositol phosphate in c...	16061378

Literature References

PubMed	DOI	Target Context	# Activities
32077284	10.1021/acs.jnatprod.9b01061	5-hydroxytryptamine receptor 2A	6
6259355	10.1021/jm00134a016	No relevant target	5
35450349	10.1021/acsmedchemlett.2c00129	ADMET	5
38505858	10.1021/acsmedchemlett.4c00058	5-hydroxytryptamine receptor 2A	3
10514296	10.1021/jm990325u	5-hydroxytryptamine receptor 2A	2
34917242	10.1021/acsmedchemlett.1c00578	5-hydroxytryptamine receptor 2C	2
34917242	10.1021/acsmedchemlett.1c00578	5-hydroxytryptamine receptor 2B	2
34917242	10.1021/acsmedchemlett.1c00578	5-hydroxytryptamine receptor 2A	2
34917241	10.1021/acsmedchemlett.1c00577	5-hydroxytryptamine receptor 2A	2
34676027	10.1021/acsmedchemlett.1c00467	ADMET	2
18296055	10.1016/j.bmc.2008.02.033	5-hydroxytryptamine receptor 2A	2
12877591	10.1021/jm030064v	5-hydroxytryptamine receptor 2A	2
18296055	10.1016/j.bmc.2008.02.033	No relevant target	1
592329	10.1021/jm00222a019	Homo sapiens	1
38516602	10.1039/d4md00043a	5-hydroxytryptamine receptor 2B	1
16061378	10.1016/j.bmcl.2005.06.104	5-hydroxytryptamine receptor 2C	1
16061378	10.1016/j.bmcl.2005.06.104	5-hydroxytryptamine receptor 2B	1
16061378	10.1016/j.bmcl.2005.06.104	5-hydroxytryptamine receptor 2A	1
12877591	10.1021/jm030064v	Rattus norvegicus	1
12877591	10.1021/jm030064v	5-hydroxytryptamine receptor 1A	1

Data from ChEMBL 36 via Core Engine