Compound Detail

CHEMBL7257

MEBUFOTENIN

🧪 Phase II

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🧪 Phase II

COc1ccc2[nH]cc(CCN(C)C)c2c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL7257
Name	MEBUFOTENIN
Phase	Phase II
Structure Type	MOL
InChI Key	ZSTKHSQDNIGFLM-UHFFFAOYSA-N

Known Names

5-meo-dmt 5-methoxy-n-dimethyltryptamine 5-methoxydimethyltryptamine Mebufotenin Mebufotenina Mebufotenine NSC-88624

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

218.3

MW (Da)

2.28

ALogP

HBA

HBD

28.3

PSA (Å²)

0.85

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

Extended Properties

Molecular Formula	C13H18N2O
MW	218.30
Aromatic Rings	2
Heavy Atoms	16
NP-Likeness	-0.33

Indications

Depression Depressive Disorder, Treatment-Resistant

Activity Summary

Ki 33 meas. best 8.26

EC50 14 meas. best 8.75

IC50 13 meas. best 8.02

Kd 5 meas. best 7.1

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 2A CHEMBL224	EC50	8.75	8.72	1.8	4
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	8.26	7.865	5.5	6
5-hydroxytryptamine receptor 2B CHEMBL1833	EC50	8.23	8.16	5.9	2
5-hydroxytryptamine receptor 2A CHEMBL322	IC50	8.02	8.02	9.5	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	7.96	7.96	11.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	7.89	7.552	13.0	5
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	7.82	7.2833	15.0	3
5-hydroxytryptamine receptor 1A CHEMBL214	IC50	7.82	7.82	15.0	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	7.82	6.836	15.0	5
Melatonin receptor type 1B CHEMBL1946	Ki	7.8	7.8	16.0	1
5-hydroxytryptamine receptor 1D CHEMBL1983	Ki	7.7	7.7	20.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	7.55	7.55	28.0	1
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	7.52	7.52	30.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	EC50	7.51	7.475	30.7	2
5-hydroxytryptamine receptor 7 CHEMBL3223	Ki	7.4	7.4	39.8	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	7.38	7.38	42.0	1
5-hydroxytryptamine receptor 1D CHEMBL1983	IC50	7.31	7.31	49.0	1
5-hydroxytryptamine receptor 1D CHEMBL2304407	IC50	7.31	7.31	49.0	1
Serotonin 1 (5-HT1) receptor CHEMBL2095159	Ki	7.3	7.3	50.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	7.28	7.28	52.0	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	IC50	7.22	6.395	60.0	4
5-hydroxytryptamine receptor 2C CHEMBL324	EC50	7.11	7.11	77.8	1
Serotonin (5-HT) receptor CHEMBL2096904	Kd	7.1	7.1	79.4	1
Serotonin 1 (5-HT1) receptor CHEMBL2095159	Kd	7.08	7.08	83.2	1
Serotonin (5-HT) receptor CHEMBL2094123	Kd	7.08	7.08	83.2	1
Rattus norvegicus CHEMBL376	Kd	7.08	7.08	83.2	1
5-hydroxytryptamine receptor 2B CHEMBL323	Kd	7.08	7.08	83.2	1
5-hydroxytryptamine receptor 1B CHEMBL3459	Ki	7.05	6.755	90.0	2
5-hydroxytryptamine receptor 2A CHEMBL322	Ki	7.04	6.42	92.0	2
Melatonin receptor type 1B CHEMBL1946	EC50	6.95	6.95	112.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	EC50	6.71	6.71	197.0	1
Melatonin receptor type 1A CHEMBL1945	Ki	6.68	6.68	210.0	1
5-hydroxytryptamine receptor 2B CHEMBL323	EC50	6.62	6.62	240.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	6.6	6.6	250.0	1
5-hydroxytryptamine receptor 2C CHEMBL324	IC50	6.6	6.6	250.0	1
Melatonin receptor type 1A CHEMBL1945	EC50	6.59	6.59	257.0	1
5-hydroxytryptamine receptor 2A CHEMBL322	EC50	6.33	6.33	462.0	1
5-hydroxytryptamine receptor 1B CHEMBL1898	IC50	6.26	6.26	550.0	1
5-hydroxytryptamine receptor 2C CHEMBL324	Ki	6.02	6.02	960.0	1
Acetylcholinesterase CHEMBL4078	IC50	4.85	4.85	14000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	43.6	mL.min-1.g-1	Homo sapiens
T1/2	0.8817	hr	Homo sapiens
T1/2	0.24	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 2A	EC50	=	1.76	nM	8.75	Agonist activity at 5-HT2A receptor (unknown origin) by calcium flux assay	35450349
5-hydroxytryptamine receptor 2A	EC50	=	1.76	nM	8.75	Agonist activity at 5HT2A receptor (unknown origin) expressed in HEK293 cells by...	34917241
5-hydroxytryptamine receptor 2A	EC50	=	1.85	nM	8.73	Agonist activity at human 5-HT2A receptor expressed in CHO cells measured after ...	38352850
5-hydroxytryptamine receptor 2A	EC50	=	2.239	nM	8.65	Agonist activity at human 5-HT2A receptor expressed in CHO cells measured after ...	38352850
5-hydroxytryptamine receptor 1A	Ki	=	5.495	nM	8.26	Binding affinity of a compound to rat brain 5-hydroxytryptamine 1A (serotonin) r...	8568799
5-hydroxytryptamine receptor 2B	EC50	=	5.87	nM	8.23	Agonist activity at human 5-HT2B receptor expressed in Flp-In-T-REx-293 cells me...	38352850
5-hydroxytryptamine receptor 1A	Ki	=	7.8	nM	8.11	Binding affinity towards 5-hydroxytryptamine 1A receptor	2965244
5-hydroxytryptamine receptor 2B	EC50	=	8.128	nM	8.09	Agonist activity at human 5-HT2B receptor expressed in Flp-In-T-REx-293 cells me...	38352850
5-hydroxytryptamine receptor 2A	IC50	=	9.53	nM	8.02	Inhibition of [125I]DOI binding to 5HT2A receptor in rat cerebral cortex	16392816
5-hydroxytryptamine receptor 1A	Ki	=	10.0	nM	8.0	Binding affinity of compound towards 5-hydroxytryptamine 1A receptor in rat stri...	2754715
5-hydroxytryptamine receptor 1A	IC50	=	11.0	nM	7.96	Compound was evaluated for binding affinity towards 5-hydroxytryptamine 1A recep...	1433172
5-hydroxytryptamine receptor 1A	Ki	=	11.0	nM	7.96	Displacement of [3H]8-OH DPAT from rat 5HT1A receptor expressed in CHO cells aft...	26023814
5-hydroxytryptamine receptor 6	Ki	=	13.0	nM	7.89	Displacement of [3H]LSD from human 5HT6 receptor expressed in HEK293 cells	16945532
5-hydroxytryptamine receptor 1A	IC50	=	15.0	nM	7.82	Binding affinity against 5-hydroxytryptamine 1A receptor	1447752
Serotonin 2 (5-HT2) receptor	Ki	=	15.0	nM	7.82	Binding affinity towards 5-hydroxytryptamine 2 receptor using [3H]- 1-(4-bromo-2...	2965244
5-hydroxytryptamine receptor 2A	Ki	=	15.0	nM	7.82	Affinity against 5-hydroxytryptamine 2A receptor (D) labeled with [125I]DOI.	8027974
Serotonin 2 (5-HT2) receptor	Ki	=	15.0	nM	7.82	Affinity on 5-hydroxytryptamine 2 receptor labeled by [125I]DOI	1534585
5-hydroxytryptamine receptor 2A	Ki	=	15.0	nM	7.82	Displacement of [125I]DOI from cloned human 5HT2A receptor expressed in CHO cell...	16392816
Melatonin receptor type 1B	Ki	=	16.0	nM	7.8	Displacement of 2-[125I]-iodomelatonin from human melatonin receptor-2 transfect...	26023814
5-hydroxytryptamine receptor 6	Ki	=	16.0	nM	7.8	Binding affinity against human 5-hydroxytryptamine 6 receptor stably transfected...	11055342

Literature References

PubMed	DOI	Target Context	# Activities
16392816	10.1021/jm050663x	MDCK	6
7120280	10.1021/jm00350a005	Rattus norvegicus	6
35450349	10.1021/acsmedchemlett.2c00129	ADMET	5
16392816	10.1021/jm050663x	5-hydroxytryptamine receptor 2A	4
38352850	10.1021/acsmedchemlett.3c00566	5-hydroxytryptamine receptor 2B	3
16392816	10.1021/jm050663x	Serotonin 2 (5-HT2) receptor	3
26023814	10.1021/acs.jmedchem.5b00245	Melatonin receptor type 1B	3
38352850	10.1021/acsmedchemlett.3c00566	5-hydroxytryptamine receptor 2C	3
26023814	10.1021/acs.jmedchem.5b00245	Melatonin receptor type 1A	3
16392816	10.1021/jm050663x	5-hydroxytryptamine receptor 2C	3
38352850	10.1021/acsmedchemlett.3c00566	5-hydroxytryptamine receptor 2A	3
31977208	10.1021/acs.jmedchem.9b01404	Danio rerio	2
1447752	10.1021/jm00101a032	Serotonin 2 (5-HT2) receptor	2
278843	10.1021/jm00206a022	Serotonin (5-HT) receptor	2
1433172	10.1021/jm00098a005	Serotonin 2 (5-HT2) receptor	2
8027974	10.1021/jm00039a004	5-hydroxytryptamine receptor 2A	2
8027974	10.1021/jm00039a004	5-hydroxytryptamine receptor 2C	2
3543362	10.1021/jm00384a001	Serotonin 2 (5-HT2) receptor	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
2965244	10.1021/jm00399a031	Serotonin 2 (5-HT2) receptor	2

Data from ChEMBL 36 via Core Engine