Molecule

4-Hydroxytryptamine; 2'-N-Di-Me

AlkaPlorer ID: AK017015

Synonym: 3-(2-Dimethylaminoethyl)-1H-indol-4-ol, 3-(2-Dimethylaminoethyl)-4-hydroxyindole, 4-Hydroxy-N,N-dimethyltryptamine, Psilocine, CX 59

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

Structure

SMILES: CN(C)CCC1=CNC2=CC=CC(O)=C12

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

InChIKey: SPCIYGNTAMCTRO-UHFFFAOYSA-N

Reference

Psilocybin in Finnish<i>Psilocybe semilanceata</i>

PubChem CID: 4980

CAS: 520-53-6

LOTUS: LTS0234550

COCONUT: CNP0142132

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NPAtlas: NPA009691

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
None	Conocybe	Bolbitiaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
None	Stropharia	Strophariaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
None	Chlorocystis	Chlorocystidaceae	Chlorocystidales	Ulvophyceae	Chlorophyta	Viridiplantae	Eukaryota
None	Psilocybe	Strophariaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota

Properties Information

Molecule Weight: 204.273

TPSA？: 39.260000000000005

MolLogP？: 1.9776

Number of H-Donors: 2

Number of H-Acceptors: 2

RingCount: 2

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	Homo sapiens	Ratio	32.0	None	10.1021/jm00222a019
Homo sapiens	Serotonin 1a (5-HT1a) receptor	Binding	nan	None	10.1021/jm030064v
Homo sapiens	Serotonin 2a (5-HT2a) receptor	EC50	4.266	nM	10.1021/acs.jnatprod.9b01061
Homo sapiens	Serotonin 2a (5-HT2a) receptor	EC50	4.3	nM	10.1021/acs.jnatprod.9b01061
Homo sapiens	Serotonin 2a (5-HT2a) receptor	EC50	6.5	nM	10.1021/acsmedchemlett.1c00577
Homo sapiens	Serotonin 2a (5-HT2a) receptor	EC50	6.5	nM	10.1021/acsmedchemlett.2c00129
Homo sapiens	Serotonin 2a (5-HT2a) receptor	EC50	24.0	nM	10.1016/j.bmcl.2005.06.104
Homo sapiens	Serotonin 2a (5-HT2a) receptor	EC50	75.2	nM	10.1021/acsmedchemlett.1c00467
Homo sapiens	Serotonin 2a (5-HT2a) receptor	EC50	1000.0	nM	10.1021/acsmedchemlett.2c00128
Homo sapiens	Serotonin 2a (5-HT2a) receptor	EC50	1000.0	nM	10.1021/acsmedchemlett.2c00352
Homo sapiens	Serotonin 2a (5-HT2a) receptor	Efficacy	82.0	%	10.1021/acsmedchemlett.1c00578
Homo sapiens	Serotonin 2a (5-HT2a) receptor	Emax	73.0	%	10.1021/acs.jnatprod.9b01061
Homo sapiens	Serotonin 2a (5-HT2a) receptor	Emax	95.6	%	10.1021/acsmedchemlett.1c00577
Homo sapiens	Serotonin 2a (5-HT2a) receptor	IC50	8.34	nM	10.1021/acsmedchemlett.1c00578
Homo sapiens	Serotonin 2b (5-HT2b) receptor	EC50	58.0	nM	10.1016/j.bmcl.2005.06.104
Homo sapiens	Serotonin 2b (5-HT2b) receptor	Efficacy	63.0	%	10.1021/acsmedchemlett.1c00578
Homo sapiens	Serotonin 2b (5-HT2b) receptor	IC50	1.07	nM	10.1021/acsmedchemlett.1c00578
Homo sapiens	Serotonin 2c (5-HT2c) receptor	EC50	30.0	nM	10.1016/j.bmcl.2005.06.104
Homo sapiens	Serotonin 2c (5-HT2c) receptor	Efficacy	95.0	%	10.1021/acsmedchemlett.1c00578
Homo sapiens	Serotonin 2c (5-HT2c) receptor	IC50	7.79	nM	10.1021/acsmedchemlett.1c00578
Homo sapiens	Tyrosyl-DNA phosphodiesterase 1	Potency	21469.6	nM	None
Homo sapiens	Tyrosyl-DNA phosphodiesterase 1	Potency	27028.6	nM	None
Mus musculus	Serotonin 2a (5-HT2a) receptor	EC50	9.772	nM	10.1021/acs.jnatprod.9b01061
Mus musculus	Serotonin 2a (5-HT2a) receptor	EC50	9.9	nM	10.1021/acs.jnatprod.9b01061
Mus musculus	Serotonin 2a (5-HT2a) receptor	Emax	72.0	%	10.1021/acs.jnatprod.9b01061
Rattus norvegicus	Rattus norvegicus	Max	46.0	%	10.1021/jm030064v
Rattus norvegicus	Serotonin 2a (5-HT2a) receptor	EC50	2300.0	nM	10.1021/jm030064v
Rattus norvegicus	Serotonin 2a (5-HT2a) receptor	Efficacy	nan	None	10.1016/j.bmc.2008.02.033
Rattus norvegicus	Serotonin 2a (5-HT2a) receptor	K0.5	6.0	nM	10.1021/jm990325u
Rattus norvegicus	Serotonin 2a (5-HT2a) receptor	Ki	25.0	nM	10.1021/jm030064v
Rattus norvegicus	Serotonin 2a (5-HT2a) receptor	Ki	323.0	nM	10.1016/j.bmc.2008.02.033
Rattus norvegicus	Serotonin 2a (5-HT2a) receptor	Ki	390.0	nM	10.1021/jm990325u
Rattus norvegicus	Serotonin 2c (5-HT2c) receptor	Binding	nan	None	10.1021/jm030064v
None	ADMET	CL	11.81	mL.min-1.g-1	10.1021/acsmedchemlett.1c00467
None	ADMET	CL	15.9	mL.min-1.g-1	10.1021/acsmedchemlett.2c00129
None	ADMET	Stability	46.1	%	10.1021/acsmedchemlett.2c00129
None	ADMET	Stability	112.1	%	10.1021/acsmedchemlett.2c00129
None	ADMET	T1/2	1.913	hr	10.1021/acsmedchemlett.2c00129
None	ADMET	T1/2	1.955	hr	10.1021/acsmedchemlett.1c00467
None	ADMET	T1/2	2.417	hr	10.1021/acsmedchemlett.2c00129
None	No relevant target	LogP	0.191	None	10.1016/j.bmc.2008.02.033
None	No relevant target	LogP	1.45	None	10.1021/jm00134a016
None	No relevant target	pKa	3.3	None	10.1021/jm00134a016
None	No relevant target	pKa	8.47	None	10.1021/jm00134a016
None	No relevant target	pKa	42.1	None	10.1021/jm00134a016
None	No relevant target	Poct	0.68	None	10.1021/jm00134a016
None	Unchecked	Ac50	15.85	uM	None
None	Unchecked	Ac50	35.48	uM	None
None	Unchecked	Ac50	39.81	uM	None
None	Unchecked	AC50	15848.9	nM	None
None	Unchecked	AC50	35481.3	nM	None
None	Unchecked	AC50	39810.7	nM	None
None	Unchecked	Potency	44668.4	nM	None

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT010392	CN(C)CCc1c[nH]c2cccc(O)c12.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>CN(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O	None
AKRT010393	CN(C)CCc1c[nH]c2cccc(O)c12>>CN(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12	R08480
AKRT010395	CN(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12>>CN(C)CCc1c[nH]c2cccc(O)c12	R12142
AKRT014597	C[SAH].C[SAH].NCCc1c[nH]c2ccccc12>>CN(C)CCc1c[nH]c2cccc(O)c12	MNXR112024