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Compound Detail

CHEMBL12420

N,N-DIMETHYLTRYPTAMINE
🧪 Phase II
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🧪 Phase II
CN(C)CCc1c[nH]c2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL12420
Name N,N-DIMETHYLTRYPTAMINE
Phase Phase II
Structure Type MOL
InChI Key DMULVCHRPCFFGV-UHFFFAOYSA-N

Known Names

DEA NO. 7435 Dimethyltryptamine N,n-dimethyltryptamine NSC-63795
12
Targets
15
Activities
3
Assay Types
4
PK Parameters
20
Publications
4
Known Names
3
Indications

Molecular Properties

188.3
MW (Da)
2.27
ALogP
1
HBA
1
HBD
19.0
PSA (Ų)
0.78
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C12H16N2
MW 188.27
Aromatic Rings 2
Heavy Atoms 14
NP-Likeness -0.34

Indications

Depressive Disorder Depressive Disorder, Major Stroke

Activity Summary

Ki 8 meas. best 7.48
Kd 5 meas. best 6.0
EC50 2 meas. best 7.65

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
 EC50 7.65 7.65 22.2 2
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 7.48 7.48 33.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 7.19 7.19 65.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 7.0 7.0 101.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 6.59 6.59 259.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 6.39 6.39 410.0 1
Serotonin (5-HT) receptor
CHEMBL2094123
 Kd 6.0 6.0 1000.0 2
Serotonin 1 (5-HT1) receptor
CHEMBL2095159
 Kd 6.0 6.0 1000.0 1
5-hydroxytryptamine receptor 2B
CHEMBL323
 Kd 6.0 6.0 1000.0 1
Rattus norvegicus
CHEMBL376
 Kd 6.0 6.0 1000.0 1
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 5.79 5.79 1636.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL4153
 Ki 4.82 4.82 15000.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL3602
 Ki 4.81 4.81 15400.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 134.9 mL.min-1.g-1 Homo sapiens
T1/2 0.285 hr Homo sapiens
T1/2 0.085 hr Rattus norvegicus
T1/2 1.648 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A EC50 = 22.2 nM 7.65 Agonist activity at 5HT2A receptor (unknown origin) expressed in HEK293 cells by... 34917241
5-hydroxytryptamine receptor 2A EC50 = 22.2 nM 7.65 Agonist activity at 5-HT2A receptor (unknown origin) by calcium flux assay 35450349
5-hydroxytryptamine receptor 2C Ki = 33.0 nM 7.48 Compound was tested for the displacement of [125I]DOI from cloned human 5-hydrox... 10090793
5-hydroxytryptamine receptor 2A Ki = 65.0 nM 7.19 Compound was tested for the displacement of [125I]DOI from clone human 5-hydroxy... 10090793
5-hydroxytryptamine receptor 2B Ki = 101.0 nM 7.0 Compound was tested for the displacement of [3H]5-HT from clone human 5-hydroxyt... 10090793
5-hydroxytryptamine receptor 1A Ki = 259.0 nM 6.59 Compound was tested for the displacement of [3H]-8-OH- DPAT from rat brain 5-hyd... 10090793
5-hydroxytryptamine receptor 1A Ki = 410.0 nM 6.39 Displacement of [3H]8-OH-DPAT from 5HT1A receptor by vacuum filtration -
Rattus norvegicus Kd = 1000.0 nM 6.0 The ability to inhibit the 5-HT-induced contraction of isolated rat fundus muscl... 6815326
5-hydroxytryptamine receptor 2B Kd = 1000.0 nM 6.0 The binding affinity to 5-hydroxytryptamine 2B receptor of rat fundus 7086824
Serotonin (5-HT) receptor Kd = 1000.0 nM 6.0 Compound was evaluated for binding affinity towards 5-hydroxytryptamine receptor... 6779006
Serotonin 1 (5-HT1) receptor Kd = 1000.0 nM 6.0 Antagonist activity at 5-HT1 receptor in Sprague-Dawley rat assessed as inhibiti... 533890
Serotonin (5-HT) receptor Kd = 1000.0 nM 6.0 Competitive antagonist activity at 5-HT serotonin receptor in Sprague-Dawley rat... 278843
5-hydroxytryptamine receptor 2A Ki = 1636.0 nM 5.79 Displacement of [3H]MDL100907 from 5HT2A receptor in Sprague-Dawley rat brain by... 18296055
Sigma non-opioid intracellular receptor 1 Ki = 15000.0 nM 4.82 Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain by... 21531141
Sigma non-opioid intracellular receptor 1 Ki = 15400.0 nM 4.81 Displacement of [3H]-(+)-pentazocine from sigma 1 receptor in rat liver homogena... 23964901

Literature References

PubMed DOI Target Context # Activities
10090793 10.1021/jm980692q Rattus norvegicus 18
35450349 10.1021/acsmedchemlett.2c00129 ADMET 5
10090793 10.1021/jm980692q 5-hydroxytryptamine receptor 2A 3
31977208 10.1021/acs.jmedchem.9b01404 Cortical neurone 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
34917241 10.1021/acsmedchemlett.1c00577 5-hydroxytryptamine receptor 2A 2
18296055 10.1016/j.bmc.2008.02.033 5-hydroxytryptamine receptor 2A 2
36105328 10.1021/acsmedchemlett.2c00354 ADMET 2
18296055 10.1016/j.bmc.2008.02.033 No relevant target 1
533890 10.1021/jm00197a025 Serotonin 1 (5-HT1) receptor 1
23964901 10.1021/jm400660u Sigma non-opioid intracellular receptor 1 1
21531141 10.1016/j.bmc.2011.04.002 Sigma non-opioid intracellular receptor 1 1
21524588 10.1016/j.bmc.2011.04.004 ADMET 1
21524588 10.1016/j.bmc.2011.04.004 Hepatitis B virus 1
21524588 10.1016/j.bmc.2011.04.004 Unchecked 1
- 10.1021/np960678l 5-hydroxytryptamine receptor 1A 1
10090793 10.1021/jm980692q 5-hydroxytryptamine receptor 2B 1
38648167 10.1021/acs.jmedchem.3c01696 Cortical neurone 1
6779006 10.1021/jm00185a014 Serotonin (5-HT) receptor 1
7086824 10.1021/jm00343a013 5-hydroxytryptamine receptor 2B 1

Data from ChEMBL 36 via Core Engine