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Compound Detail

CHEMBL6467

4-METHYLTHIOAMPHETAMINE
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CSc1ccc(CC(C)N)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL6467
Name 4-METHYLTHIOAMPHETAMINE
Phase Preclinical
Structure Type MOL
InChI Key OLEWMKVPSUCNLG-UHFFFAOYSA-N
9
Targets
29
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

181.3
MW (Da)
2.30
ALogP
2
HBA
1
HBD
26.0
PSA (Ų)
0.72
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C10H15NS
MW 181.30
Aromatic Rings 1
Heavy Atoms 12
NP-Likeness -0.66

Activity Summary

EC50 17 meas. best 6.0
IC50 10 meas. best 7.13
Ki 2 meas. best 6.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 7.13 6.915 74.0 2
Sodium-dependent serotonin transporter
CHEMBL313
 IC50 7.13 6.98 74.0 3
Amine oxidase [flavin-containing] A
CHEMBL3358
 IC50 6.7 6.7 200.0 1
Amine oxidase [flavin-containing] A
CHEMBL3358
 Ki 6.6 6.6 250.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 6.35 6.35 450.0 1
SH-SY5Y
CHEMBL614910
 EC50 6.0 6.0 1000.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 5.62 5.62 2375.0 1
Norepinephrine transporter
CHEMBL304
 IC50 5.62 5.62 2375.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 5.51 5.51 3073.0 1
Rattus norvegicus
CHEMBL376
 IC50 5.51 5.51 3073.0 1
HEK293
CHEMBL614818
 EC50 4.73 4.6343 18620.9 7
Sodium-dependent serotonin transporter
CHEMBL228
 EC50 4.65 4.65 22387.2 1
Sodium-dependent dopamine transporter
CHEMBL238
 EC50 4.64 4.64 22908.7 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 EC50 4.46 4.46 34673.7 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent serotonin transporter IC50 = 74.0 nM 7.13 Inhibition of [3H]5-HT uptake at SERT in rat brain synaptosome 19717215
Sodium-dependent serotonin transporter IC50 = 74.0 nM 7.13 Inhibition of [3H]5-HT uptake at SERT 19717215
Sodium-dependent serotonin transporter IC50 = 74.0 nM 7.13 Activity towards Serotonin transporter was determined by the ability to inhibit ... 9526575
Sodium-dependent serotonin transporter IC50 = 200.0 nM 6.7 Inhibition of [3H]-serotonin reuptake at human SERT expressed in HEK293 cells af... 21227702
Amine oxidase [flavin-containing] A IC50 = 200.0 nM 6.7 Inhibitory concentration against monoamine oxidase A in rat brain mitochondrial ... 15801832
Sodium-dependent serotonin transporter IC50 = 207.0 nM 6.68 Inhibition of [3H]5-HT reuptake at rat SERT expressed in HEK293 cells after 2 mi... 19717215
Amine oxidase [flavin-containing] A Ki = 250.0 nM 6.6 Inhibition of MAOA in rat brain mitochondria 19243954
Sodium-dependent serotonin transporter Ki = 450.0 nM 6.35 Inhibition of [3H]5-HT uptake at human SERT expressed in HEK293 cells after 10 m... 19717215
SH-SY5Y EC50 = 1000.0 nM 6.0 Cytotoxicity against human SH-SY5Y cells after 48 hrs by neutral red assay 19717215
Norepinephrine transporter IC50 = 2375.0 nM 5.62 Compound was tested for the ability to inhibit [3H]norepinephrine binding to Nor... 9526575
Sodium-dependent noradrenaline transporter IC50 = 2375.0 nM 5.62 Inhibition of human noradrenaline transporter 19717215
Rattus norvegicus IC50 = 3073.0 nM 5.51 Compound was tested for its ability to inhibit [3H]dopamine uptake in rat synapt... 9526575
Sodium-dependent dopamine transporter IC50 = 3073.0 nM 5.51 Inhibition of human dopamine transporter 19717215
HEK293 EC50 = 18620.87 nM 4.73 Cytotoxicity against human HEK293 cells assessed as cell viability after 48 hrs ... 20466553
HEK293 EC50 = 18620.87 nM 4.73 Cytotoxicity against human HEK293 cells after 48 hrs by neutral red assay 19717215
HEK293 EC50 = 19952.62 nM 4.7 Cytotoxicity against human HEK293 cells assessed as decrease in cell viability a... 21227702
HEK293 EC50 = 22387.21 nM 4.65 Cytotoxicity against human HEK293 cells over expressing human NET assessed as ce... 20466553
HEK293 EC50 = 22387.21 nM 4.65 Cytotoxicity against human HEK293 cells over expressing human SERT assessed as c... 20466553
Sodium-dependent serotonin transporter EC50 = 22387.21 nM 4.65 Induction of human SERT-dependent cytotoxicity in SERT expressing HEK293 cells a... 19717215
Sodium-dependent dopamine transporter EC50 = 22908.68 nM 4.64 Induction of human DAT-dependent cytotoxicity in DAT expressing HEK293 cells aft... 19717215

Literature References

PubMed DOI Target Context # Activities
19717215 10.1016/j.ejmech.2009.07.027 Sodium-dependent serotonin transporter 7
20466553 10.1016/j.bmc.2010.04.022 HEK293 4
19717215 10.1016/j.ejmech.2009.07.027 Sodium-dependent noradrenaline transporter 2
21227702 10.1016/j.bmc.2010.11.054 HEK293 2
20466553 10.1016/j.bmc.2010.04.022 Unchecked 2
19717215 10.1016/j.ejmech.2009.07.027 Unchecked 2
19717215 10.1016/j.ejmech.2009.07.027 Sodium-dependent dopamine transporter 2
19717215 10.1016/j.ejmech.2009.07.027 SH-SY5Y 2
19717215 10.1016/j.ejmech.2009.07.027 HEK293 2
9526575 10.1021/jm9705925 Unchecked 2
19243954 10.1016/j.bmc.2009.01.074 Amine oxidase [flavin-containing] B 1
9526575 10.1021/jm9705925 Sodium-dependent serotonin transporter 1
19243954 10.1016/j.bmc.2009.01.074 Amine oxidase [flavin-containing] A 1
15801832 10.1021/jm0493109 Amine oxidase [flavin-containing] A 1
20466553 10.1016/j.bmc.2010.04.022 PC-12 1
20466553 10.1016/j.bmc.2010.04.022 SH-SY5Y 1
9526575 10.1021/jm9705925 Norepinephrine transporter 1
21227702 10.1016/j.bmc.2010.11.054 Sodium-dependent serotonin transporter 1
21227702 10.1016/j.bmc.2010.11.054 DG-75 1
21227702 10.1016/j.bmc.2010.11.054 SH-SY5Y 1

Data from ChEMBL 36 via Core Engine