N-Methyltryptamine

Details

• Internal ID: 0089c005-d610-4304-977a-dc00f72a8e84
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Tryptamines and derivatives
• IUPAC Name: 2-(1H-indol-3-yl)-N-methylethanamine
• SMILES (Canonical): CNCCC1=CNC2=CC=CC=C21
• SMILES (Isomeric): CNCCC1=CNC2=CC=CC=C21
• 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
• InChI Key: NCIKQJBVUNUXLW-UHFFFAOYSA-N
• Popularity: 215 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₄N₂
• Molecular Weight: 174.24 g/mol
• Exact Mass: 174.115698455 g/mol
• Topological Polar Surface Area (TPSA): 27.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.93
• H-Bond Acceptor: 1
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 61-49-4
• 3-(2-Methylaminoethyl)indole
• 2-(1H-Indol-3-yl)-N-methylethanamine
• Dipterine
• N-Monomethyltryptamine
• Methyltryptamine
• 1H-Indole-3-ethanamine, N-methyl-
• N-OMEGA-METHYLTRYPTAMINE
• 3-(2-(Methylamino)ethyl)indole
• (2-Indol-3-ylethyl)methylamine
• N-Methylindoleethylamine
• INDOLE, 3-(2-(METHYLAMINO)ETHYL)-
• N.omega.-methyltryptamine
• 6FRL4L3Z7V
• 2-(1H-indol-3-yl)-N-methyl-ethanamine
• MLS000069493
• CHEBI:28136
• N-methyl-1H-indole-3-ethanamine
• 1-Methyl-2-(3-indolyl)ethylamine
• SMR000059062
• EINECS 200-507-9
• UNII-6FRL4L3Z7V
• BRN 0134134
• N-Omega-Methyltryptamine(NMT)
• dl-Methyltryptamine
• n-methyl tryptamine
• N-methyl-tryptamine
• N-w-Methyltryptamine
• Maybridge3_003310
• N(omega)-methyltryptamine
• cid_6088
• Oprea1_433490
• 5-22-10-00047 (Beilstein Handbook Reference)
• BIDD:GT0662
• SCHEMBL379409
• 3-(2-methylaminoethyl)-indole
• CHEMBL348588
• 3-(2-Methylaminoethyl) Indole
• N-omega-Methyltryptamine, 99%
• BDBM30701
• DTXSID70209846
• HMS1440G10
• HMS2235A08
• HMS3372P09
• N-omega-Methyltryptamine, free base
• 3-(N-Methyl-2-amino-ethyl)-indole
• CCG-56495
• MFCD00005657
• AKOS005203036
• 2-(1H-indol-3-yl)ethyl-methyl-amine
• IDI1_014697
• 2-(1H-indol-3-yl)-ethyl-methyl-amine
• NCGC00018120-01
• NCGC00018120-02
• NCGC00018120-03
• [2-(1H-indol-3-yl)ethyl](methyl)amine
• AM20040845
• FT-0631273
• C06213
• M-4640
• Q308875
• SR-01000000029-2
• 1HU
• InChI=1/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	+	0.8801	88.01%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Lysosomes	0.7197	71.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9508	95.08%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	-	0.8762	87.62%
P-glycoprotein inhibitior	-	0.9873	98.73%
P-glycoprotein substrate	-	0.6294	62.94%
CYP3A4 substrate	-	0.5067	50.67%
CYP2C9 substrate	+	0.5374	53.74%
CYP2D6 substrate	+	0.6778	67.78%
CYP3A4 inhibition	-	0.7731	77.31%
CYP2C9 inhibition	-	0.9276	92.76%
CYP2C19 inhibition	-	0.8175	81.75%
CYP2D6 inhibition	-	0.8497	84.97%
CYP1A2 inhibition	-	0.6012	60.12%
CYP2C8 inhibition	-	0.8185	81.85%
CYP inhibitory promiscuity	-	0.8351	83.51%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7719	77.19%
Eye corrosion	-	0.9946	99.46%
Eye irritation	+	0.6377	63.77%
Skin irritation	-	0.6249	62.49%
Skin corrosion	-	0.6979	69.79%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4636	46.36%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8060	80.60%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7840	78.40%
Acute Oral Toxicity (c)	III	0.5015	50.15%
Estrogen receptor binding	-	0.7247	72.47%
Androgen receptor binding	-	0.8122	81.22%
Thyroid receptor binding	-	0.7334	73.34%
Glucocorticoid receptor binding	-	0.8474	84.74%
Aromatase binding	-	0.7736	77.36%
PPAR gamma	-	0.6873	68.73%
Honey bee toxicity	-	0.9185	91.85%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	-	0.6246	62.46%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	50.7 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.92%	91.11%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	93.22%	90.71%
CHEMBL1914	P06276	Butyrylcholinesterase	92.88%	95.00%
CHEMBL2581	P07339	Cathepsin D	92.56%	98.95%
CHEMBL255	P29275	Adenosine A2b receptor	91.26%	98.59%
CHEMBL222	P23975	Norepinephrine transporter	90.58%	96.06%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.14%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	86.92%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.44%	95.56%
CHEMBL3310	Q96DB2	Histone deacetylase 11	85.91%	88.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.99%	89.62%
CHEMBL3401	O75469	Pregnane X receptor	83.45%	94.73%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.13%	93.99%
CHEMBL1937	Q92769	Histone deacetylase 2	80.67%	94.75%
CHEMBL240	Q12809	HERG	80.65%	89.76%

Plants that contains it

• Acacia confusa
• Acacia maidenii
• Anadenanthera peregrina
• Mimosa ophthalmocentra
• Mimosa somnians
• Piptostigma fugax
• Prosopis nigra
• Tachigali paniculata
• Vachellia rigidula
• Virola elongata
• Virola sebifera
• Zanthoxylum arborescens

Cross-Links

• PubChem: 6088
• LOTUS: LTS0182964
• wikiData: Q308875