Compound Detail

CHEMBL222287

IBOGAINE

🧪 Phase II

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🧪 Phase II

CC[C@H]1C[C@H]2C[C@H]3c4[nH]c5ccc(OC)cc5c4CCN(C2)[C@@H]13

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL222287
Name	IBOGAINE
Phase	Phase II
Structure Type	MOL
InChI Key	HSIBGVUMFOSJPD-NXWOVTFFSA-N

Known Names

(-)-ibogaine 10-methoxyibogamine 12-methoxyibogamine Ibogaine Ibogamine, 12-methoxy- NSC-249764

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

310.4

MW (Da)

3.94

ALogP

HBA

HBD

28.3

PSA (Å²)

0.91

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula	C20H26N2O
MW	310.44
Aromatic Rings	2
Heavy Atoms	23
NP-Likeness	1.00

Indications

Opioid-Related Disorders Substance-Related Disorders

Activity Summary

IC50 7 meas. best 6.23

Ki 4 meas. best 6.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	Ki	6.7	5.865	201.0	2
Sigma non-opioid intracellular receptor 1 CHEMBL4153	Ki	6.6	6.6	250.0	1
Sodium-dependent serotonin transporter CHEMBL313	IC50	6.23	5.6767	590.0	3
Mu-type opioid receptor CHEMBL270	IC50	5.42	5.42	3760.0	1
Sodium-dependent dopamine transporter CHEMBL338	IC50	5.39	5.39	4110.0	1
Glutamate NMDA receptor CHEMBL1907608	IC50	5.28	5.28	5200.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	5.07	5.07	8554.0	1
Kappa-type opioid receptor CHEMBL3614	IC50	4.6	4.6	25000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	Ki	=	201.0	nM	6.7	Binding affinity to sigma-2 opioid receptor (unknown origin)	23734634
Sigma non-opioid intracellular receptor 1	Ki	=	250.0	nM	6.6	Displacement of [3H](+)-pentazocine from guinea pig brain sigma 1 receptor	17328523
Sodium-dependent serotonin transporter	IC50	=	590.0	nM	6.23	relative affinity against serotonin transporter using RTI-55 as radioligand	9804688
Sodium-dependent serotonin transporter	IC50	=	2500.0	nM	5.6	Displacement of [125I]beta-CIT from rat SERT expressed in HeLa cells	17698848
Mu-type opioid receptor	IC50	=	3760.0	nM	5.42	Relative affinity against Opioid receptor mu 1 in thalamus using [3H]DAMGO as ra...	9804688
Sodium-dependent dopamine transporter	IC50	=	4110.0	nM	5.39	relative affinity against dopamine transporter using WIN-35428 as radioligand	9804688
Glutamate NMDA receptor	IC50	=	5200.0	nM	5.28	relative affinity against N-methyl-D-aspartate glutamate receptor in caudate usi...	9804688
Sodium-dependent serotonin transporter	IC50	=	6300.0	nM	5.2	Inhibition of [3H]5HT uptake at rat SERT expressed in HeLa cells	17698848
Sigma non-opioid intracellular receptor 1	Ki	=	8554.0	nM	5.07	Binding affinity to sigma-1 opioid receptor (unknown origin)	23734634
Unchecked	Ki	=	9310.0	nM	5.03	Displacement of [3H]DTG rom guinea pig brain sigma 2 receptor	17328523
Kappa-type opioid receptor	IC50	=	25000.0	nM	4.6	relative affinity against Opioid receptor kappa 1 in insular Ctx using [3H]U-695...	9804688

Literature References

PubMed	DOI	Target Context	# Activities
17698848	10.1074/jbc.m704456200	Sodium-dependent serotonin transporter	13
17328523	10.1021/jm0611197	Unchecked	6
17698848	10.1074/jbc.m704456200	Unchecked	4
23734634	10.1021/jm301545c	Unchecked	2
20684615	10.1021/jm100116p	Astrocyte	2
17328523	10.1021/jm0611197	Sigma non-opioid intracellular receptor 1	2
23734634	10.1021/jm301545c	Sigma non-opioid intracellular receptor 1	1
9804688	10.1021/jm980156y	Sodium-dependent dopamine transporter	1
-	10.1007/s00044-012-9977-1	Whole blood	1
20684615	10.1021/jm100116p	Molecular identity unknown	1
12713407	10.1021/np020548e	A2780	1
9804688	10.1021/jm980156y	Glutamate NMDA receptor	1
9804688	10.1021/jm980156y	Kappa-type opioid receptor	1
9804688	10.1021/jm980156y	Mu-type opioid receptor	1
9804688	10.1021/jm980156y	D(3) dopamine receptor	1
9804688	10.1021/jm980156y	D(2) dopamine receptor	1
9804688	10.1021/jm980156y	D(1A) dopamine receptor	1
9804688	10.1021/jm980156y	Sodium-dependent serotonin transporter	1

Data from ChEMBL 36 via Core Engine