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name Structure Reference Source Properties Activities Metabolism

5-Methoxytryptamine; Nb,Nb-Di-Me 

AlkaPlorer ID: AK002491

Synonym: 5-Methoxy-N,N-dimethyltryptamine, O-Methylbufotenine 

IUPAC Name: 2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine

Structure

SMILES: COC1=CC=C2NC=C(CCN(C)C)C2=C1

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InChI: InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3

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InChIKey: ZSTKHSQDNIGFLM-UHFFFAOYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
None Phalaris Poaceae Poales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 218.29999999999995

TPSA？: 28.26

MolLogP？: 2.2806000000000006

Number of H-Donors: 1

Number of H-Acceptors: 2

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Canis lupus familiaris MDCK Papp 141.0 nM/s 10.1021/jm050663x
Canis lupus familiaris MDCK Papp 144.0 nM/s 10.1021/jm050663x
Canis lupus familiaris MDCK Papp 161.0 nM/s 10.1021/jm050663x
Canis lupus familiaris MDCK Papp 200.0 nM/s 10.1021/jm050663x
Canis lupus familiaris MDCK Ratio 0.7 None 10.1021/jm050663x
Canis lupus familiaris MDCK Ratio 0.9 None 10.1021/jm050663x
Cavia porcellus Serotonin 1d (5-HT1d) receptor IC50 49.0 nM 10.1021/jm00101a032
Danio rerio Danio rerio Activity nan None 10.1021/acs.jmedchem.9b01404
Danio rerio Danio rerio ECmax 200.0 uM 10.1021/acs.jmedchem.9b01404
Electrophorus electricus Acetylcholinesterase IC50 14000.0 nM 10.1021/np401003p
Homo sapiens Cytochrome P450 1A2 AC50 15848.93 nM None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 Potency 39810.7 nM None
Homo sapiens Cytochrome P450 2D6 AC50 19952.62 nM None
Homo sapiens Cytochrome P450 2D6 Potency 19952.6 nM None
Homo sapiens Cytochrome P450 3A4 AC50 nan None None
Homo sapiens Lethal(3)malignant brain tumor-like protein 1 Potency 31622.8 nM None
Homo sapiens Melatonin receptor 1A EC50 257.0 nM 10.1021/acs.jmedchem.5b00245
Homo sapiens Melatonin receptor 1A Emax 62.0 % 10.1021/acs.jmedchem.5b00245
Homo sapiens Melatonin receptor 1A Ki 210.0 nM 10.1021/acs.jmedchem.5b00245
Homo sapiens Melatonin receptor 1B EC50 112.0 nM 10.1021/acs.jmedchem.5b00245
Homo sapiens Melatonin receptor 1B Emax 28.0 % 10.1021/acs.jmedchem.5b00245
Homo sapiens Melatonin receptor 1B Ki 16.0 nM 10.1021/acs.jmedchem.5b00245
Homo sapiens Serotonin 1a (5-HT1a) receptor EC50 197.0 nM None
Homo sapiens Serotonin 1a (5-HT1a) receptor IC50 15.0 nM 10.1021/jm00101a032
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki 28.0 nM 10.1021/np960678l
Homo sapiens Serotonin 1b (5-HT1b) receptor IC50 550.0 nM 10.1021/jm00101a032
Homo sapiens Serotonin 1d (5-HT1d) receptor IC50 49.0 nM 10.1021/jm00098a005
Homo sapiens Serotonin 1d (5-HT1d) receptor Ki 20.0 nM 10.1021/jm950498t
Homo sapiens Serotonin 2 (5-HT2) receptor Activity 12.0 % 10.1021/jm050663x
Homo sapiens Serotonin 2 (5-HT2) receptor Activity 25.4 % 10.1021/jm050663x
Homo sapiens Serotonin 2 (5-HT2) receptor Activity 26.1 % 10.1021/jm050663x
Homo sapiens Serotonin 2a (5-HT2a) receptor EC50 1.76 nM 10.1021/acsmedchemlett.1c00577
Homo sapiens Serotonin 2a (5-HT2a) receptor EC50 1.76 nM 10.1021/acsmedchemlett.2c00129
Homo sapiens Serotonin 2a (5-HT2a) receptor Emax 106.0 % 10.1021/acsmedchemlett.1c00577
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki 15.0 nM 10.1021/jm00039a004
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki 15.0 nM 10.1021/jm050663x
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki 620.0 nM 10.1021/jm00039a004
Homo sapiens Serotonin 2b (5-HT2b) receptor Ki 52.0 nM 10.1021/jm050663x
Homo sapiens Serotonin 2c (5-HT2c) receptor IC50 250.0 nM 10.1021/jm00098a005
Homo sapiens Serotonin 2c (5-HT2c) receptor Ki 42.0 nM 10.1021/jm050663x
Homo sapiens Serotonin 2c (5-HT2c) receptor Ratio 65.0 None 10.1021/jm00039a004
Homo sapiens Serotonin (5-HT) receptor Kd 79.43 nM 10.1021/jm00206a022
Homo sapiens Serotonin 6 (5-HT6) receptor Ki 13.0 nM 10.1016/j.bmcl.2006.08.068
Homo sapiens Serotonin 6 (5-HT6) receptor Ki 16.0 nM 10.1016/s0960-894x(00)00453-4
Homo sapiens Serotonin 6 (5-HT6) receptor Ki 16.0 nM 10.1021/jm030030n
Homo sapiens Serotonin 6 (5-HT6) receptor Ki 70.0 nM 10.1007/s00044-004-0121-8
Homo sapiens Serotonin 6 (5-HT6) receptor Ki 78.0 nM 10.1021/jm990550b
Homo sapiens Serotonin 7 (5-HT7) receptor Ki 30.0 nM 10.1021/jm030030n
Mus musculus Mus musculus Activity nan None 10.1021/acs.jmedchem.9b01404
Mus musculus Short transient receptor potential channel 4 EC50 670.0 nM None
Rattus norvegicus Cortical neurone Activity nan None 10.1021/acs.jmedchem.9b01404
Rattus norvegicus Rattus norvegicus Change in response 5.0 % 10.1021/jm00350a005
Rattus norvegicus Rattus norvegicus Change in response 6.0 % 10.1021/jm00350a005
Rattus norvegicus Rattus norvegicus Change in response 9.0 % 10.1021/jm00350a005
Rattus norvegicus Rattus norvegicus Change in response 11.0 % 10.1021/jm00350a005
Rattus norvegicus Rattus norvegicus Change in response 19.0 % 10.1021/jm00350a005
Rattus norvegicus Rattus norvegicus Change in response 26.0 % 10.1021/jm00350a005
Rattus norvegicus Rattus norvegicus ED50 1.43 mg.kg-1 10.1021/jm00399a031
Rattus norvegicus Rattus norvegicus Kd 83.18 nM 10.1021/jm00353a021
Rattus norvegicus Serotonin 1 (5-HT1) receptor Kd 83.18 nM 10.1021/jm00197a025
Rattus norvegicus Serotonin 1 (5-HT1) receptor Ki 50.0 nM 10.1021/jm00384a001
Rattus norvegicus Serotonin 1a (5-HT1a) receptor IC50 11.0 nM 10.1021/jm00098a005
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Ki 5.495 nM 10.1021/jm950410b
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Ki 7.8 nM 10.1021/jm00399a031
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Ki 10.0 nM 10.1021/jm00128a039
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Ki 11.0 nM 10.1021/acs.jmedchem.5b00245
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Ki 20.0 nM 10.1021/jm00384a001
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Ki 69.0 nM 10.1021/jm00089a017
Rattus norvegicus Serotonin 1b (5-HT1b) receptor Ki 90.0 nM 10.1021/jm00384a001
Rattus norvegicus Serotonin 1b (5-HT1b) receptor Ki 350.0 nM 10.1021/jm00399a031
Rattus norvegicus Serotonin 2 (5-HT2) receptor IC50 60.0 nM 10.1021/jm00101a032
Rattus norvegicus Serotonin 2 (5-HT2) receptor IC50 130.0 nM 10.1021/jm00098a005
Rattus norvegicus Serotonin 2 (5-HT2) receptor IC50 1800.0 nM 10.1021/jm00098a005
Rattus norvegicus Serotonin 2 (5-HT2) receptor IC50 1900.0 nM 10.1021/jm00101a032
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 15.0 nM 10.1021/jm00089a017
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 15.0 nM 10.1021/jm00399a031
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 390.0 nM 10.1021/jm00384a001
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 620.0 nM 10.1021/jm00399a031
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 1200.0 nM 10.1021/jm00384a001
Rattus norvegicus Serotonin 2a (5-HT2a) receptor EC50 462.0 nM 10.1021/jm050663x
Rattus norvegicus Serotonin 2a (5-HT2a) receptor Emax 70.0 % 10.1021/jm050663x
Rattus norvegicus Serotonin 2a (5-HT2a) receptor IC50 9.53 nM 10.1021/jm050663x
Rattus norvegicus Serotonin 2a (5-HT2a) receptor Inhibition nan % 10.1021/acs.jmedchem.9b01404
Rattus norvegicus Serotonin 2a (5-HT2a) receptor K0.5 21.0 nM 10.1021/jm990325u
Rattus norvegicus Serotonin 2a (5-HT2a) receptor Ki 92.0 nM 10.1021/acs.jmedchem.5b00245
Rattus norvegicus Serotonin 2a (5-HT2a) receptor Ki 1600.0 nM 10.1021/jm990325u
Rattus norvegicus Serotonin 2b (5-HT2b) receptor EC50 240.0 nM 10.1021/jm050663x
Rattus norvegicus Serotonin 2b (5-HT2b) receptor Kd 83.18 nM 10.1021/jm00343a013
Rattus norvegicus Serotonin 2c (5-HT2c) receptor EC50 77.8 nM 10.1021/jm050663x
Rattus norvegicus Serotonin 2c (5-HT2c) receptor Emax 89.0 % 10.1021/jm050663x
Rattus norvegicus Serotonin 2c (5-HT2c) receptor IC50 250.0 nM 10.1021/jm00101a032
Rattus norvegicus Serotonin 2c (5-HT2c) receptor Ki 960.0 nM 10.1021/jm00039a004
Rattus norvegicus Serotonin (5-HT) receptor Kd 83.18 nM 10.1021/jm00206a022
Rattus norvegicus Serotonin 7 (5-HT7) receptor Increase 92.0 % 10.1021/jm030826m
Rattus norvegicus Serotonin 7 (5-HT7) receptor Ki 39.81 nM 10.1021/jm030826m
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
None ADMET CL 43.6 mL.min-1.g-1 10.1021/acsmedchemlett.2c00129
None ADMET Stability 0.3 % 10.1021/acsmedchemlett.2c00129
None ADMET Stability 47.1 % 10.1021/acsmedchemlett.2c00129
None ADMET T1/2 0.24 hr 10.1021/acsmedchemlett.2c00129
None ADMET T1/2 0.8817 hr 10.1021/acsmedchemlett.2c00129
None No relevant target LogD 3.3 None 10.1021/jm050663x
None No relevant target LogP 3.3 None 10.1021/jm00197a025
None Unchecked Potency 3548.1 nM None
None Unchecked Potency 35481.3 nM None
None Unchecked Ratio 41.0 None 10.1021/jm00039a004
None Unchecked Ratio Ki 10.0 None 10.1021/acs.jmedchem.5b00245

Metabolism Information