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Compound Detail

CHEMBL1201201

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

Basic Information

ChEMBL ID CHEMBL1201201
Name METHAMPHETAMINE
Phase Approved
Structure Type MOL
InChI Key MYWUZJCMWCOHBA-VIFPVBQESA-N
Therapeutic ✓ Yes

Known Names

(s)-phenylmethylaminopropane J6.362B Metamfetamine Metamphetamine Metanfetamina Methamphetamine NSC-25115
7
Targets
20
Activities
3
Assay Types
4
PK Parameters
20
Publications
7
Known Names
4
Indications

Molecular Properties

149.2
MW (Da)
1.84
ALogP
1
HBA
1
HBD
12.0
PSA (Ų)
0.69
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1943
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

Extended Properties

Molecular Formula C10H15N
MW 149.24
Aromatic Rings 1
Heavy Atoms 11
NP-Likeness -0.21

Indications

Attention Deficit Disorder with Hyperactivity Amphetamine-Related Disorders Obsessive-Compulsive Disorder Social Behavior

ATC Classification

N06BA03
metamfetamine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

EC50 13 meas. best 7.75
Ki 6 meas. best 5.61
IC50 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trace amine-associated receptor 1
CHEMBL4908
 EC50 7.75 6.648 17.8 5
Trace amine-associated receptor 1
CHEMBL3833
 EC50 6.88 6.33 133.3 4
Trace amine-associated receptor 1
CHEMBL5857
 EC50 5.89 5.855 1300.0 2
Synaptic vesicular amine transporter
CHEMBL4828
 Ki 5.61 5.1067 2460.0 3
Unchecked
CHEMBL612545
 EC50 5.35 5.35 4440.0 1
Trace amine-associated receptor 1
CHEMBL1926495
 EC50 5.28 5.28 5300.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 5.08 5.08 8320.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 4.4 mL.min-1.kg-1 Homo sapiens
Fu 0.85 - Homo sapiens
MRT 16.0 hr Homo sapiens
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 = 17.81 nM 7.75 Activation of mouse TAAR1 transmembrane domain 6 Thr268(6.55)Met mutant expresse... 24354319
Trace amine-associated receptor 1 EC50 = 70.0 nM 7.16 Activation of mouse TAAR1 expressed in human HEK293 cells assessed as accumulati... 22037049
Trace amine-associated receptor 1 EC50 = 133.3 nM 6.88 Activation of rat wild type TAAR1 expressed in HEK293 cells assessed as stimulat... 24354319
Trace amine-associated receptor 1 EC50 = 201.8 nM 6.7 Activation of rat TAAR1 transmembrane domain 7 Asn287(7.39)Tyr mutant expressed ... 24354319
Trace amine-associated receptor 1 EC50 = 278.9 nM 6.55 Activation of mouse wild type TAAR1 expressed in HEK293 cells assessed as stimul... 24354319
Trace amine-associated receptor 1 EC50 = 890.0 nM 6.05 Activation of rat TAAR1 expressed in HEK293 cells assessed as accumulation of [3... 22037049
Trace amine-associated receptor 1 EC50 = 920.0 nM 6.04 Activation of mouse TAAR1 expressed in human HEK293 cells assessed as accumulati... 22037049
Trace amine-associated receptor 1 EC50 = 1300.0 nM 5.89 Activation of human TAAR1 expressed in human HEK293T cells assessed as cAMP accu... 22037049
Trace amine-associated receptor 1 EC50 = 1500.0 nM 5.82 Activation of C-terminal HA epitope tagged human TAAR1 expressed in RD-HGA16 cel... 22037049
Trace amine-associated receptor 1 EC50 = 1822.0 nM 5.74 Activation of mouse TAAR1 transmembrane domain 7 Tyr287(7.39)Asn mutant expresse... 24354319
Trace amine-associated receptor 1 EC50 = 2044.0 nM 5.69 Activation of rat TAAR1 transmembrane domain 6 Met268(6.55)Thr mutant expressed ... 24354319
Synaptic vesicular amine transporter Ki = 2460.0 nM 5.61 Inhibition of VMAT2-mediated [3H]-dopamine uptake in rat striata isolated synapt... 23993667
Synaptic vesicular amine transporter Ki = 2460.0 nM 5.61 Inhibition of VMAT2-mediated [3H]DA uptake in rat brain synaptic vesicles by liq... 25991431
Unchecked EC50 = 4440.0 nM 5.35 Activation of chimeric rat-human expressed in human HEK293 cells assessed as acc... 22037049
Trace amine-associated receptor 1 EC50 = 5300.0 nM 5.28 Activation of rhesus monkey TAAR1 expressed in RD-HGA16 cells co-expressing Gq p... 22037049
Sigma non-opioid intracellular receptor 1 Ki = 8320.0 nM 5.08 Binding affinity towards sigma opioid receptor in guinea pig cerebral homogenate... 1848295
Synaptic vesicular amine transporter Ki = 80100.0 nM 4.1 Displacement of [3H]DTBZ from VMAT2 in rat whole brain by liquid scintillation s... 25991431

Literature References

PubMed DOI Target Context # Activities
24354319 10.1021/jm401316v Trace amine-associated receptor 1 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
22037049 10.1016/j.bmc.2011.10.007 Trace amine-associated receptor 1 6
18426954 10.1124/dmd.108.020479 ADMET 4
20014752 10.1021/tx900326k Hepatotoxicity 3
28244748 10.1021/acs.jmedchem.7b00085 Rattus norvegicus 3
25991431 10.1016/j.bmcl.2015.04.105 Synaptic vesicular amine transporter 3
3397993 10.1021/jm00403a012 Amine oxidase [flavin-containing] B 2
24354319 10.1021/jm401316v Unchecked 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
22931300 10.1021/tx300075j Liver microsomes 2
27687671 10.1016/j.bmcl.2016.09.009 CDGSH iron-sulfur domain-containing protein 1 2
1846917 10.1021/jm00105a025 Rattus norvegicus 2
22931300 10.1021/tx300075j Cytochrome P450 2C9 1
22931300 10.1021/tx300075j Cytochrome P450 2C19 1
22931300 10.1021/tx300075j Cytochrome P450 2D6 1
18426954 10.1124/dmd.108.020479 NON-PROTEIN TARGET 1
15857133 10.1021/jm048980b No relevant target 1

Data from ChEMBL 36 via Core Engine