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Compound Detail

CHEMBL19393

LEVAMFETAMINE
💊 Approved Drug
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💊 Approved Drug
C[C@@H](N)Cc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL19393
Name LEVAMFETAMINE
Phase Approved
Structure Type MOL
InChI Key KWTSXDURSIMDCE-MRVPVSSYSA-N

Known Names

Amfetamine, (r)- Amphetamine l-form L-amphetamine Levamfetamine Levanfetamina
8
Targets
28
Activities
4
Assay Types
1
PK Parameters
14
Publications
5
Known Names

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
Availability Withdrawn
Chirality Single Enantiomer

Flags

Withdrawn Natural Product
USAN Stem -fetamine
USAN Year 1962

Extended Properties

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

Drug Warnings

Withdrawn
drug misuse
evidence of abuse and high risk of dependence
Country: United States   Year: 1973
Withdrawn
drug misuse
evidence of abuse and high risk of dependence
Country: United States   Year: 1973

Activity Summary

EC50 19 meas. best 7.47
Ki 7 meas. best 4.33
IC50 1 meas. best 6.3
Kd 1 meas. best 5.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trace amine-associated receptor 1
CHEMBL3833
 EC50 7.47 6.665 33.9 6
Trace amine-associated receptor 1
CHEMBL4908
 EC50 7.19 6.5 65.0 5
Trace amine-associated receptor 1
CHEMBL5857
 EC50 6.6 6.075 250.0 4
Rattus norvegicus
CHEMBL376
 IC50 6.3 6.3 500.0 1
Rattus norvegicus
CHEMBL376
 EC50 5.77 4.99 1700.0 2
Trace amine-associated receptor 1
CHEMBL1926495
 EC50 5.73 5.73 1860.0 1
Unchecked
CHEMBL612545
 EC50 5.51 5.51 3090.0 1
Serotonin (5-HT) receptor
CHEMBL2094123
 Kd 5.16 5.16 6918.3 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 4.33 4.33 46400.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 12.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trace amine-associated receptor 1 EC50 = 33.9 nM 7.47 Activation of rat wild type TAAR1 expressed in HEK293 cells assessed as stimulat... 24354319
Trace amine-associated receptor 1 EC50 = 65.0 nM 7.19 Activation of mouse TAAR1 expressed in human HEK293 cells assessed as accumulati... 22037049
Trace amine-associated receptor 1 EC50 = 104.5 nM 6.98 Activation of mouse TAAR1 transmembrane domain 7 Tyr287(7.39)Asn mutant expresse... 24354319
Trace amine-associated receptor 1 EC50 = 121.0 nM 6.92 Activation of mouse TAAR1 transmembrane domain 6 Thr268(6.55)Met mutant expresse... 24354319
Trace amine-associated receptor 1 EC50 = 169.9 nM 6.77 Activation of rat TAAR1 transmembrane domain 7 Asn287(7.39)Tyr mutant expressed ... 24354319
Trace amine-associated receptor 1 EC50 = 210.0 nM 6.68 Activation of rat TAAR1 expressed in HEK293 cells assessed as accumulation of [3... 22037049
Trace amine-associated receptor 1 EC50 = 214.4 nM 6.67 Activation of rat TAAR1 transmembrane domain 6 Met268(6.55)Thr mutant expressed ... 24354319
Trace amine-associated receptor 1 EC50 = 250.0 nM 6.6 Activation of human TAAR1 expressed in human HEK293T cells assessed as cAMP accu... 22037049
Trace amine-associated receptor 1 EC50 = 280.0 nM 6.55 Activation of rat TAAR1 expressed in HEK293 cells assessed as accumulation of [3... 22037049
Rattus norvegicus IC50 = 500.0 nM 6.3 Inhibitory concentration against uptake of [3H]NE into chopped cerebral cortical... 7392028
Trace amine-associated receptor 1 EC50 = 785.5 nM 6.11 Activation of mouse wild type TAAR1 expressed in HEK293 cells assessed as stimul... 24354319
Trace amine-associated receptor 1 EC50 = 920.0 nM 6.04 Agonist activity at human trace amine associated receptor 1 expressed in RD-HGA1... 18602830
Trace amine-associated receptor 1 EC50 = 1300.0 nM 5.89 Activation of C-terminal HA epitope tagged human TAAR1 expressed in RD-HGA16 cel... 22037049
Trace amine-associated receptor 1 EC50 = 1400.0 nM 5.85 Activation of rat TAAR1 expressed in Syrian hamster AV12-664 cells assessed as a... 22037049
Rattus norvegicus EC50 = 1700.0 nM 5.77 Effective concentration was measured for the release of accumulated [3H]NE from ... 7392028
Trace amine-associated receptor 1 EC50 = 1700.0 nM 5.77 Activation of human TAAR1 expressed in Syrian hamster AV12-664 cells co-expressi... 22037049
Trace amine-associated receptor 1 EC50 = 1860.0 nM 5.73 Activation of rhesus monkey TAAR1 expressed in RD-HGA16 cells co-expressing Gq p... 22037049
Unchecked EC50 = 3090.0 nM 5.51 Activation of chimeric rat-human expressed in human HEK293 cells assessed as acc... 22037049
Trace amine-associated receptor 1 EC50 = 4960.0 nM 5.3 Activation of mouse TAAR1 expressed in human HEK293 cells assessed as accumulati... 22037049
Serotonin (5-HT) receptor Kd = 6918.31 nM 5.16 Affinity against 5-hydroxytryptamine receptors in rat fundus model 7365744

Literature References

PubMed DOI Target Context # Activities
24354319 10.1021/jm401316v Trace amine-associated receptor 1 14
22037049 10.1016/j.bmc.2011.10.007 Trace amine-associated receptor 1 9
3397993 10.1021/jm00403a012 Amine oxidase [flavin-containing] B 3
7392028 10.1021/jm00180a006 Rattus norvegicus 3
18602830 10.1016/j.bmc.2008.06.009 Trace amine-associated receptor 1 2
19345586 10.1016/j.bmc.2009.03.025 Glutamate NMDA receptor 2
24354319 10.1021/jm401316v Unchecked 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
3172133 10.1021/jm00118a021 Phenylethanolamine N-methyltransferase 1
7365744 10.1021/jm00177a017 Serotonin (5-HT) receptor 1
7143366 10.1021/jm00352a031 Phenylethanolamine N-methyltransferase 1
1848295 10.1021/jm00107a033 Sigma non-opioid intracellular receptor 1 1
22037049 10.1016/j.bmc.2011.10.007 Unchecked 1
31307886 10.1016/j.bmcl.2019.06.043 ADMET 1

Data from ChEMBL 36 via Core Engine