1-Methyl-1H-indole-3-ethylamine

Details

• Internal ID: 0ad7e48b-c160-4311-9980-a64e0fe734c5
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Tryptamines and derivatives
• IUPAC Name: 2-(1-methylindol-3-yl)ethanamine
• InChI: InChI=1S/C11H14N2/c1-13-8-9(6-7-12)10-4-2-3-5-11(10)13/h2-5,8H,6-7,12H2,1H3
• InChI Key: CAAGZPJPCKMFBD-UHFFFAOYSA-N
• Popularity: 53 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): 31.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.68
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 1-METHYLTRYPTAMINE
• 1-Methyl-1H-indole-3-ethylamine
• EINECS 231-377-1
• RefChem:433864
• 231-377-1
• 2-(1-methyl-1H-indol-3-yl)ethanamine
• 2-(1-methylindol-3-yl)ethanamine
• 1H-Indole-3-ethanamine,1-methyl-
• 2-(1-METHYL-1H-INDOL-3-YL)ETHAN-1-AMINE
• MFCD00057093
• 3-(2-AMINOETHYL)-1-METHYLINDOLE
• 2-(1-methyl-3-indolyl)ethanamine
• CHEMBL3330641
• 2-(1-methyl-1H-indol-3-yl)ethylamine
• 1-Methyltryptamine, free base
• N-Methylisotryptamine
• a-methyltryptamine
• 1H-Indole-2-ethanamine, 1-methyl-
• BRN 0473426
• 1-METHYL-1H-INDOLE-3-ETHANAMINE
• Tryptamine, 1-methyl-
• Oprea1_757922
• SCHEMBL332959
• SCHEMBL5598636
• DTXSID80991164
• CHEBI:125627
• 2-(1-methylindol-3-yl)ethylamine
• BBL036339
• BDBM50025215
• SBB081237
• STK367793
• VT1228
• AKOS000276207
• EBC-181821
• FM52291
• MB00487
• 1-Methyltryptamine, >=95.0% (GC)
• 2-(1-methyl-1H-indol-3-yl)-ethylamine
• AS-54752
• SY153596
• NS00047653
• EN300-139143
• M-4645
• 5-22-10-00042 (Beilstein Handbook Reference)
• AE-848/30742009
• F334308
• 2-(1-METHYL-1H-INDOL-3-YL)-1-ETHANAMINE
• BRD-K74773935-001-01-6
• Q27216239
• F2106-0181
• 55FC1B01-ABF5-490D-A277-3CF781E25C03
• 1ES

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9924	99.24%
Caco-2	+	0.9812	98.12%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Lysosomes	0.6281	62.81%
OATP2B1 inhibitior	-	0.8696	86.96%
OATP1B1 inhibitior	+	0.9453	94.53%
OATP1B3 inhibitior	+	0.9502	95.02%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	-	0.8983	89.83%
P-glycoprotein inhibitior	-	0.9883	98.83%
P-glycoprotein substrate	-	0.7388	73.88%
CYP3A4 substrate	-	0.6131	61.31%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	+	0.5732	57.32%
CYP3A4 inhibition	-	0.7779	77.79%
CYP2C9 inhibition	-	0.9236	92.36%
CYP2C19 inhibition	-	0.7114	71.14%
CYP2D6 inhibition	-	0.7632	76.32%
CYP1A2 inhibition	+	0.6941	69.41%
CYP2C8 inhibition	-	0.8567	85.67%
CYP inhibitory promiscuity	-	0.5998	59.98%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6238	62.38%
Eye corrosion	-	0.9020	90.20%
Eye irritation	-	0.8039	80.39%
Skin irritation	-	0.6501	65.01%
Skin corrosion	-	0.7052	70.52%
Ames mutagenesis	+	0.7063	70.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4640	46.40%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	+	0.7052	70.52%
skin sensitisation	-	0.8750	87.50%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.8499	84.99%
Acute Oral Toxicity (c)	III	0.5132	51.32%
Estrogen receptor binding	-	0.8719	87.19%
Androgen receptor binding	-	0.6123	61.23%
Thyroid receptor binding	-	0.6807	68.07%
Glucocorticoid receptor binding	-	0.6913	69.13%
Aromatase binding	-	0.7490	74.90%
PPAR gamma	-	0.7141	71.41%
Honey bee toxicity	-	0.9613	96.13%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	-	0.8947	89.47%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	209 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.23%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.13%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.23%	98.95%
CHEMBL5805	Q9NR97	Toll-like receptor 8	89.14%	96.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.72%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.88%	91.11%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	85.82%	90.71%
CHEMBL2885	P07451	Carbonic anhydrase III	85.36%	87.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.26%	82.69%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.80%	89.62%
CHEMBL3401	O75469	Pregnane X receptor	81.39%	94.73%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	81.31%	100.00%

Plants that contains it

• Piptostigma fugax

Cross-Links

• PubChem: 23492
• LOTUS: LTS0025956
• wikiData: Q27216239