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Compound Detail

CHEMBL405

AMPHETAMINE
💊 Approved Drug
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💊 Approved Drug
CC(N)Cc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL405
Name AMPHETAMINE
Phase Approved
Structure Type MOL
InChI Key KWTSXDURSIMDCE-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Adzenys er Adzenys xr-odt Amfetamin Amfetamine Amphetamine Amphetamine resin complex Amphetamine, dl- Anfetamina Dyanavel Dyanavel xr Mydayis (mixed salts of a single entity) Norephedrane +1 more
11
Targets
19
Activities
3
Assay Types
17
PK Parameters
20
Publications
13
Known Names
3
Indications
2
Mechanisms

Molecular Properties

135.2
MW (Da)
1.58
ALogP
1
HBA
1
HBD
26.0
PSA (Ų)
0.65
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1955
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

Extended Properties

Molecular Formula C9H13N
MW 135.21
Aromatic Rings 1
Heavy Atoms 10
NP-Likeness -0.02

Mechanism of Action

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

Indications

Attention Deficit Disorder with Hyperactivity Cognition Cocaine-Related Disorders

ATC Classification

N06BA01
amfetamine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Drug Warnings

Black Box Warning
misuse
Country: United States

Activity Summary

IC50 8 meas. best 6.7
Ki 7 meas. best 5.12
Kd 4 meas. best 5.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Transporter
CHEMBL6184
 IC50 6.7 6.7 200.0 1
Sodium-dependent dopamine transporter
CHEMBL338
 IC50 6.02 6.02 960.0 1
Sodium-dependent noradrenaline transporter
CHEMBL2370
 IC50 6.0 6.0 1000.0 1
Cytochrome P450 2A5
CHEMBL4085
 IC50 5.54 5.54 2850.0 1
Cytochrome P450 2A6
CHEMBL5282
 IC50 5.46 5.46 3500.0 1
Serotonin (5-HT) receptor
CHEMBL2094123
 Kd 5.27 5.27 5370.3 3
5-hydroxytryptamine receptor 2B
CHEMBL323
 Kd 5.27 5.27 5370.3 1
Serotonin 1 (5-HT1) receptor
CHEMBL2095159
 Ki 5.12 5.12 7660.0 2
Solute carrier family 22 member 3
CHEMBL1770033
 IC50 4.38 4.38 42000.0 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
 Ki 4.37 4.37 43000.0 2
Sodium-dependent serotonin transporter
CHEMBL4642
 IC50 4.35 4.35 45000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 9.7 mL.min-1.kg-1 Homo sapiens
Fu 0.8 - Homo sapiens
Ka 150.0 uM Homo sapiens
Ka 150.0 uM Homo sapiens
Ka 87.7 uM Homo sapiens
Ka 0.094 uM Homo sapiens
Ka 0.81 uM Homo sapiens
Ka 2.56 uM Homo sapiens
Ka 150.0 uM Homo sapiens
Ka 0.91 uM Homo sapiens
Ka 150.0 uM Homo sapiens
Ka 0.64 uM Homo sapiens
Ka 24.1 uM Homo sapiens
Ka 9.15 uM Homo sapiens
MRT 10.0 hr Homo sapiens
T1/2 7.3 hr Homo sapiens
T1/2 0.81 hr Oryctolagus cuniculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Transporter IC50 = 200.0 nM 6.7 Inhibition of [3H]norepinephrine uptake at NET expressed in rat hypothalamic hom... 1271416
Sodium-dependent dopamine transporter IC50 = 960.0 nM 6.02 Inhibition of [3H]dopamine uptake at dopamine transporter expressed in rat stria... 1271416
Sodium-dependent noradrenaline transporter IC50 = 1000.0 nM 6.0 Inhibition of noradrenaline transporter in NMRI albino mouse brain assessed as [... 22757
Cytochrome P450 2A5 IC50 = 2850.0 nM 5.54 Inhibitory concentration against mouse cytochrome P450 2A5 15658857
Cytochrome P450 2A6 IC50 = 3500.0 nM 5.46 Inhibitory concentration against human cytochrome P450 2A6 15658857
Serotonin (5-HT) receptor Kd = 5370.32 nM 5.27 Affinity against 5-hydroxytryptamine receptors in rat fundus model 7365744
Serotonin (5-HT) receptor Kd = 5370.32 nM 5.27 5-hydroxytryptamine receptor binding affinity was determined in rats 7143352
5-hydroxytryptamine receptor 2B Kd = 5370.32 nM 5.27 Affinity against serotonergic receptor in the isolated rat stomach fundus 7310818
Serotonin (5-HT) receptor Kd = 5370.32 nM 5.27 Affinity for 5-hydroxytryptamine receptor was determined using male Dawley rat f... 7069716
Serotonin 1 (5-HT1) receptor Ki = 7660.0 nM 5.12 Evaluated for binding affinity towards rat cortical membranes at 5-hydroxytrypta... 3543362
Serotonin 1 (5-HT1) receptor Ki = 7660.0 nM 5.12 Binding affinity for 5-hydroxytryptamine 1 receptor of rat prefrontal cortex 3950904
Solute carrier family 22 member 3 IC50 = 42000.0 nM 4.38 TP_TRANSPORTER: inhibition of MPP+ uptake (MPP+: 1 uM) in OCT3-expressing HRPE c... 9830022
Serotonin 2 (5-HT2) receptor Ki = 43000.0 nM 4.37 Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 (5-HT2) rece... 3543362
Serotonin 2 (5-HT2) receptor Ki = 43000.0 nM 4.37 Displacement of [3H]ketanserin from rat prefrontal cortex 5-hydroxytryptamine 2 ... 3950904
Sodium-dependent serotonin transporter IC50 = 45000.0 nM 4.35 Inhibition of 5-HT transporter in NMRI albino mouse brain assessed as [3H]5-HT a... 22757

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
7143352 10.1021/jm00352a013 Rattus norvegicus 8
22757 10.1021/jm00199a014 Mus musculus 7
7086822 10.1021/jm00343a010 Mus musculus 4
18426954 10.1124/dmd.108.020479 ADMET 4
7265121 10.1021/jm00135a020 Mus musculus 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
20014752 10.1021/tx900326k Hepatotoxicity 3
36244185 10.1016/j.ejmech.2022.114828 ADMET 3
25793650 10.1021/acs.jmedchem.5b00115 Mus musculus 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 3
6681842 10.1021/jm00355a012 Rattus norvegicus 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 3
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2

Data from ChEMBL 36 via Core Engine