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N-Methyltryptamine 

AlkaPlorer ID: AK021585

Synonym: N-Methyl-1H-indole-3-ethanamine, 3-(2-Methylaminoethyl)indole, Dipterine 

IUPAC Name: 2-(1H-indol-3-yl)-N-methylethanamine

Structure

SMILES: CNCCC1=CNC2=C1C=CC=C2

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InChI: InChI=1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3

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InChIKey: NCIKQJBVUNUXLW-UHFFFAOYSA-N

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Properties Information

Molecule Weight: 174.247

TPSA？: 27.82

MolLogP？: 1.9298

Number of H-Donors: 2

Number of H-Acceptors: 1

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Electrophorus electricus Acetylcholinesterase Inhibition 49.8 % 10.1021/acs.jnatprod.7b00681
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 17782.8 nM None
Homo sapiens Glutaminase kidney isoform, mitochondrial Potency 15848.9 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 28183.8 nM None
Homo sapiens Huntingtin Potency 22387.2 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 39810.7 nM None
Homo sapiens Serotonin 1a (5-HT1a) receptor EC50 5100.0 nM None
Homo sapiens Serotonin 2a (5-HT2a) receptor EC50 50.7 nM 10.1016/j.bmcl.2014.07.062
Homo sapiens Serotonin 2a (5-HT2a) receptor Emax 96.0 % 10.1016/j.bmcl.2014.07.062
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 29092.9 nM None
Plasmodium falciparum Plasmodium falciparum Potency 9285.0 nM None
Rattus norvegicus Dopamine transporter EC50 321.0 nM 10.1016/j.bmcl.2014.07.062
Rattus norvegicus Norepinephrine transporter EC50 733.0 nM 10.1016/j.bmcl.2014.07.062
Rattus norvegicus Serotonin 2b (5-HT2b) receptor Kd 1071.52 nM 10.1021/jm00343a013
Rattus norvegicus Serotonin transporter EC50 22.4 nM 10.1016/j.bmcl.2014.07.062
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 56234.1 nM None
None Unchecked Potency 4610.9 nM None
None Unchecked Potency 35481.3 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT001902 C=C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC=O.CNCCc1c[nH]c2ccccc12>>C=C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1C[C@H]1c2[nH]c3ccccc3c2CCN1C enzymemap_85948
AKRT014563 C[SAH].CNCCc1c[nH]c2ccccc12>>CN(C)CCc1c[nH]c2ccccc12 enzymemap_27462
AKRT014656 C[SAH].NCCc1c[nH]c2ccccc12>>CNCCc1c[nH]c2ccccc12 R02174