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Compound Detail

CHEMBL1546

HYDROXYAMPHETAMINE
💊 Approved Drug
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💊 Approved Drug
CC(N)Cc1ccc(O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1546
Name HYDROXYAMPHETAMINE
Phase Approved
Structure Type MOL
InChI Key GIKNHHRFLCDOEU-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Dl-4-hydroxyamphetamine Dl-p-hydroxyamphetamine Hidroxianfetamina Hydroxyamfetamine Norveritol NSC-170995 P-hydroxyamphetamine Phenol, p-(2-aminopropyl)- Pulsoton Racemic p-hydroxyamphetamine
2
Targets
3
Activities
2
Assay Types
0
PK Parameters
20
Publications
10
Known Names

Molecular Properties

151.2
MW (Da)
1.28
ALogP
2
HBA
2
HBD
46.2
PSA (Ų)
0.67
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1969
Availability Discontinued
Chirality Racemic

Routes of Administration

Topical

Flags

Natural Product

Extended Properties

Molecular Formula C9H13NO
MW 151.21
Aromatic Rings 1
Heavy Atoms 11
NP-Likeness 0.58

Activity Summary

EC50 2 meas. best 7.3
Kd 1 meas. best 3.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trace amine-associated receptor 1
CHEMBL3833
 EC50 7.3 7.295 50.0 2
Beta-secretase 1
CHEMBL4822
 Kd 3.1 3.1 800000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trace amine-associated receptor 1 EC50 = 50.0 nM 7.3 Activation of rat TAAR1 expressed in HEK293 cells assessed as accumulation of [3... 22037049
Trace amine-associated receptor 1 EC50 = 51.0 nM 7.29 Agonist activity at rat N-terminal FLAG-tagged TAAR1 expressed in HEK293 cells a... 28244748
Beta-secretase 1 Kd = 800000.0 nM 3.1 Binding affinity to BACE1 by surface plasmon resonance method 18226904

Literature References

PubMed DOI Target Context # Activities
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
18226904 10.1016/j.bmcl.2008.01.032 Beta-secretase 1 2
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 1
37468498 10.1038/s41467-023-40064-9 Vascular endothelial growth factor receptor 2 1
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 1
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 1
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent serotonin transporter 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent noradrenaline transporter 1
37468498 10.1038/s41467-023-40064-9 Acetylcholinesterase 1
37468498 10.1038/s41467-023-40064-9 Voltage-gated inwardly rectifying potassium channel KCNH2 1
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
28244748 10.1021/acs.jmedchem.7b00085 Trace amine-associated receptor 1 1
16133 10.1021/jm00215a011 Mus musculus 1

Data from ChEMBL 36 via Core Engine