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Compound Detail

CHEMBL26687

MESCALINE
Phase I
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Phase I
COc1cc(CCN)cc(OC)c1OC

Basic Information

ChEMBL ID CHEMBL26687
Name MESCALINE
Phase Phase I
Structure Type MOL
InChI Key RHCSKNNOAZULRK-UHFFFAOYSA-N

Known Names

2-(3,4,5-trimethoxyphenyl)ethanamine M (psychedelic) Mescaline NSC-30419
7
Targets
14
Activities
3
Assay Types
0
PK Parameters
20
Publications
4
Known Names

Molecular Properties

211.3
MW (Da)
1.21
ALogP
4
HBA
1
HBD
53.7
PSA (Ų)
0.80
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C11H17NO3
MW 211.26
Aromatic Rings 1
Heavy Atoms 15
NP-Likeness 0.52

Activity Summary

Ki 8 meas. best 6.52
EC50 4 meas. best 5.58
Kd 2 meas. best 5.65

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.52 6.52 302.8 1
5-hydroxytryptamine receptor 2A
CHEMBL322
Ki 6.44 5.6533 360.0 3
5-hydroxytryptamine receptor 2C
CHEMBL324
Ki 6.42 6.42 380.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.26 6.26 551.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.1 6.1 795.1 1
Serotonin (5-HT) receptor
CHEMBL2094123
Kd 5.65 5.65 2238.7 2
5-hydroxytryptamine receptor 2A
CHEMBL322
EC50 5.58 5.31 2600.0 3
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 5.16 5.16 6900.0 1
5-hydroxytryptamine receptor 2C
CHEMBL324
EC50 4.62 4.62 24000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2C Ki = 302.8 nM 6.52 Agonist activity at cloned human 5-hydroxytryptamine 2C receptor using [125I]DOI... 9301661
5-hydroxytryptamine receptor 2A Ki = 360.0 nM 6.44 Displacement of [125I]DOI from rat 5HT2A receptor 16821786
5-hydroxytryptamine receptor 2C Ki = 380.0 nM 6.42 Displacement of [125I]DOI from rat 5HT2C receptor 16821786
5-hydroxytryptamine receptor 2A Ki = 551.0 nM 6.26 Agonist activity at cloned human 5-hydroxytryptamine 2A receptor using [125I]DOI... 9301661
5-hydroxytryptamine receptor 2B Ki = 795.1 nM 6.1 Agonist activity at cloned human 5-hydroxytryptamine 2B receptor using [3H]5-HT ... 9301661
Serotonin (5-HT) receptor Kd = 2238.72 nM 5.65 Affinity against 5-hydroxytryptamine receptors in rat fundus model 7365744
Serotonin (5-HT) receptor Kd = 2238.72 nM 5.65 Competitive antagonist activity at 5-HT serotonin receptor in Sprague-Dawley rat... 278843
5-hydroxytryptamine receptor 2A EC50 = 2600.0 nM 5.58 Tested for its ability to activate phospholipase c by quantification of IP3 at c... 12877591
5-hydroxytryptamine receptor 2A EC50 = 4000.0 nM 5.4 Effect on phosphoinositide hydrolysis in NIH 3T3 fibroblast 5-hydroxytryptamine ... 9301661
5-hydroxytryptamine receptor 2A Ki = 5500.0 nM 5.26 Ability to displace [3H]ketanserin from rat cortical homogenate 5-hydroxytryptam... 9301661
5-hydroxytryptamine receptor 2A Ki = 5500.0 nM 5.26 Displacement of [3H]ketanserin from 5HT2A receptor in Sprague-Dawley rat brain b... 18296055
5-hydroxytryptamine receptor 1A Ki = 6900.0 nM 5.16 Ability to displace [3H]-8-OH-DPAT from rat hippocampal homogenate 5-hydroxytryp... 9301661
5-hydroxytryptamine receptor 2A EC50 = 11300.0 nM 4.95 Activity at rat 5HT2A receptor assessed as 5-HT-stimulated IP3 accumulation 16821786
5-hydroxytryptamine receptor 2C EC50 = 24000.0 nM 4.62 Effect on phosphoinositide hydrolysis in NIH 3T3 fibroblast 5-hydroxytryptamine ... 9301661

Literature References

PubMed DOI Target Context # Activities
9301661 10.1021/jm970219x 5-hydroxytryptamine receptor 2A 4
9301661 10.1021/jm970219x Rattus norvegicus 3
16821786 10.1021/jm060272y 5-hydroxytryptamine receptor 2A 3
9301661 10.1021/jm970219x 5-hydroxytryptamine receptor 2C 3
18296055 10.1016/j.bmc.2008.02.033 5-hydroxytryptamine receptor 2A 2
9301661 10.1021/jm970219x 5-hydroxytryptamine receptor 2B 2
2299636 10.1021/jm00164a036 Homo sapiens 2
7310812 10.1021/jm00143a017 Monoamine oxidase 2
836502 10.1021/jm00212a022 No relevant target 1
6094812 10.1021/jm00378a021 ADMET 1
16821786 10.1021/jm060272y 5-hydroxytryptamine receptor 2C 1
16821786 10.1021/jm060272y Rattus norvegicus 1
9748359 10.1021/jm980144c Homo sapiens 1
7310812 10.1021/jm00143a017 Homo sapiens 1
6737431 10.1021/jm00373a013 Homo sapiens 1
2299636 10.1021/jm00164a036 Rattus norvegicus 1
9301661 10.1021/jm970219x No relevant target 1
9301661 10.1021/jm970219x 5-hydroxytryptamine receptor 1A 1
7365744 10.1021/jm00177a017 Serotonin (5-HT) receptor 1
12877591 10.1021/jm030064v Rattus norvegicus 1

Data from ChEMBL 36 via Core Engine