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Compound Detail

CHEMBL43048

MIDOMAFETAMINE
🧪 Phase III
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🧪 Phase III
CNC(C)Cc1ccc2c(c1)OCO2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL43048
Name MIDOMAFETAMINE
Phase Phase III
Structure Type MOL
InChI Key SHXWCVYOXRDMCX-UHFFFAOYSA-N

Known Names

3,4-methylenedioxymetamphetamine 3,4-methylenedioxymethamphetamine Ecstasy Mandy Mdma Methylenedioxy methamphetamine Methylenedioxymetamphetamine Methylenedioxymethamfetamine Methylenedioxymethamphetamine Midomafetamina Midomafetamine Molly
10
Targets
42
Activities
4
Assay Types
0
PK Parameters
20
Publications
12
Known Names
13
Indications
3
Mechanisms

Molecular Properties

193.2
MW (Da)
1.57
ALogP
3
HBA
1
HBD
30.5
PSA (Ų)
0.79
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Racemic

Flags

Natural Product
USAN Stem -fetamine
USAN Year 2016

Extended Properties

Molecular Formula C11H15NO2
MW 193.25
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness 0.11

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Sodium-dependent dopamine transporter releasing agent RELEASING AGENT Sodium-dependent dopamine transporter ✓ ✓
Sodium-dependent serotonin transporter releasing agent RELEASING AGENT Sodium-dependent serotonin transporter ✓ ✓
Sodium-dependent noradrenaline transporter releasing agent RELEASING AGENT Sodium-dependent noradrenaline transporter ✓ ✓

Indications

Stress Disorders, Post-Traumatic Anorexia Nervosa Anxiety Feeding and Eating Disorders Phobia, Social Alcoholism Amphetamine-Related Disorders Liver Diseases Schizophrenia Substance-Related Disorders Child Development Disorders, Pervasive Fibromyalgia Social Behavior

Activity Summary

EC50 20 meas. best 7.21
IC50 12 meas. best 6.39
Ki 8 meas. best 9.14
Kd 2 meas. best 9.91

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Kd 9.91 9.81 0.1 2
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 9.14 7.95 0.7 3
Sodium-dependent serotonin transporter
CHEMBL313
 EC50 7.21 7.175 61.0 2
Unchecked
CHEMBL612545
 EC50 7.14 7.05 72.0 2
Sodium-dependent dopamine transporter
CHEMBL338
 EC50 7.12 6.84 75.0 2
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 6.4 6.4 398.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 6.39 6.16 405.0 3
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 6.37 6.065 425.0 4
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 6.05 6.05 897.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 EC50 6.0 6.0 1000.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 EC50 6.0 5.245 1000.0 2
Sodium-dependent noradrenaline transporter
CHEMBL222
 EC50 6.0 6.0 1000.0 1
Sodium-dependent serotonin transporter
CHEMBL313
 IC50 5.97 5.97 1060.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 5.84 5.7667 1442.0 3
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 Ki 5.84 5.84 1440.0 1
Trace amine-associated receptor 1
CHEMBL3833
 EC50 5.77 5.77 1700.0 1
Cytochrome P450 2D6
CHEMBL289
 Ki 4.89 4.765 12900.0 2
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 IC50 4.52 4.52 30400.0 1
DG-75
CHEMBL2366199
 EC50 4.5 4.5 31622.8 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Kd = 0.123 nM 9.91 Binding affinity was determined towards serotonin uptake site in presence of [3H... 1967651
Unchecked Kd = 0.195 nM 9.71 Binding affinity was determined towards serotonin uptake site in presence of [3H... 1967651
Sodium-dependent serotonin transporter Ki = 0.73 nM 9.14 Displacement of [3H]citalopram from human SERT expressed in HEK293 cells 18487050
Sodium-dependent serotonin transporter Ki = 2.03 nM 8.69 Displacement of [3H]paroxetine from human SERT expressed in HEK293 cells 18487050
Sodium-dependent serotonin transporter EC50 = 61.0 nM 7.21 Binding affinity to SERT in Sprague-Dawley rat brain synaptosomes assessed as in... 26233799
Unchecked EC50 = 72.0 nM 7.14 Binding affinity to NET in Sprague-Dawley rat brain synaptosomes assessed as ind... 26233799
Sodium-dependent serotonin transporter EC50 = 72.0 nM 7.14 Activity at SERT in rat synaptosomes assessed as release of [3H]HT after 5 mins ... 28244748
Sodium-dependent dopamine transporter EC50 = 75.0 nM 7.12 Binding affinity to DAT in Sprague-Dawley rat brain synaptosomes assessed as ind... 26233799
Unchecked EC50 = 110.0 nM 6.96 Activity at NET in rat synaptosomes assessed as release of [3H]NE after 30 mins ... 28244748
Sodium-dependent dopamine transporter EC50 = 278.0 nM 6.56 Activity at DAT in rat synaptosomes assessed as release of [3H]DA after 5 mins b... 28244748
Sodium-dependent noradrenaline transporter Ki = 398.0 nM 6.4 Inhibition of [3H]norepinephrine uptake at human NET expressed in HEK293 cells p... 23602445
Sodium-dependent noradrenaline transporter IC50 = 405.0 nM 6.39 Inhibition of human noradrenaline transporter 19717215
Sodium-dependent noradrenaline transporter IC50 = 405.0 nM 6.39 Binding affinity to human NET 20466553
Sodium-dependent serotonin transporter IC50 = 425.0 nM 6.37 Inhibition of [3H]5-HT uptake at SERT 19717215
Sodium-dependent serotonin transporter IC50 = 425.0 nM 6.37 Binding affinity to human SERT 20466553
Sodium-dependent dopamine transporter Ki = 897.0 nM 6.05 Inhibition of [3H]dopamine uptake at human DAT expressed in HEK293 cells preincu... 23602445
Sodium-dependent serotonin transporter Ki = 948.0 nM 6.02 Inhibition of [3H]5-HT uptake at human SERT expressed in HEK293 cells preincubat... 23602445
Sodium-dependent noradrenaline transporter EC50 = 1000.0 nM 6.0 Binding affinity to human NET expressed in HEK293 cells assessed as induction of... 26233799
Sodium-dependent dopamine transporter EC50 = 1000.0 nM 6.0 Binding affinity to human DAT expressed in HEK293 cells assessed as induction of... 26233799
Sodium-dependent serotonin transporter EC50 = 1000.0 nM 6.0 Binding affinity to human SERT expressed in HEK293 cells assessed as induction o... 26233799

Literature References

PubMed DOI Target Context # Activities
1967651 10.1021/jm00164a037 Rattus norvegicus 19
16162012 10.1021/jm050338+ Cytochrome P450 2D6 8
3761319 10.1021/jm00160a035 Rattus norvegicus 5
1967651 10.1021/jm00164a037 Unchecked 4
16248836 10.2174/138920005774330639 Cytochrome P450 2D6 4
19717215 10.1016/j.ejmech.2009.07.027 Sodium-dependent serotonin transporter 4
24942641 10.1016/j.ejmech.2014.04.044 Neuronal acetylcholine receptor; alpha4/beta2 4
20466553 10.1016/j.bmc.2010.04.022 HEK293 4
26233799 10.1016/j.bmc.2015.07.035 Sodium-dependent serotonin transporter 3
26233799 10.1016/j.bmc.2015.07.035 Sodium-dependent dopamine transporter 3
23602445 10.1016/j.bmcl.2013.03.066 Sodium-dependent serotonin transporter 2
23602445 10.1016/j.bmcl.2013.03.066 Sodium-dependent noradrenaline transporter 2
21227702 10.1016/j.bmc.2010.11.054 HEK293 2
23602445 10.1016/j.bmcl.2013.03.066 Sodium-dependent dopamine transporter 2
26233799 10.1016/j.bmc.2015.07.035 Unchecked 2
18487050 10.1016/j.bmc.2008.05.006 Sodium-dependent serotonin transporter 2
1674539 10.1021/jm00109a020 Rattus norvegicus 2
20466553 10.1016/j.bmc.2010.04.022 Sodium-dependent noradrenaline transporter 1
20466553 10.1016/j.bmc.2010.04.022 Sodium-dependent serotonin transporter 1
19717215 10.1016/j.ejmech.2009.07.027 Sodium-dependent dopamine transporter 1

Data from ChEMBL 36 via Core Engine