5-Methoxytryptamine

Details

• Internal ID: 273b6a1f-d780-418e-8699-8bfebcef672c
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Tryptamines and derivatives
• IUPAC Name: 2-(5-methoxy-1H-indol-3-yl)ethanamine
• SMILES (Canonical): COC1=CC2=C(C=C1)NC=C2CCN
• SMILES (Isomeric): COC1=CC2=C(C=C1)NC=C2CCN
• InChI: InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3
• InChI Key: JTEJPPKMYBDEMY-UHFFFAOYSA-N
• Popularity: 1,629 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₄N₂O
• Molecular Weight: 190.24 g/mol
• Exact Mass: 190.110613074 g/mol
• Topological Polar Surface Area (TPSA): 51.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.68
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 608-07-1
• 2-(5-Methoxy-1H-indol-3-yl)ethanamine
• Mexamine
• 3-(2-Aminoethyl)-5-methoxyindole
• Methoxytryptamine
• O-Methylserotonin
• 1H-Indole-3-ethanamine, 5-methoxy-
• Mexamine base
• 5MOT
• 5-Mot
• Meksamin
• 2-(5-Methoxyindol-3-yl)ethylamine
• Meksamin (free base)
• 5-MeOT
• 5-MT
• 2-(5-Methoxy-1H-Indol-3-Yl)Ethan-1-Amine
• 5-methoxy-1H-indole-3-ethanamine
• NSC 56422
• INDOLE, 3-(2-AMINOETHYL)-5-METHOXY-
• Lopac-M-6628
• MFCD00005662
• CHEMBL8165
• 3VMW6141KC
• CHEBI:2089
• NSC56422
• NSC-56422
• C05659
• 5-Methoxytryptamine, free base
• DEACETYLMELATONIN
• 2-(5-Methoxy-1H-indol-3-yl)ethanamine (5-Methoxytryptamine)
• SMR000112269
• EINECS 210-153-7
• BRN 0145587
• UNII-3VMW6141KC
• o-methyl serotonin
• 2-(5-Methoxy-1H-indol-3-yl)ethanamine; 5-Methoxytryptamine; Melatonin Related Compound A (USP); Melatonin Related Compound A
• F5U
• 5-methoxy-tryptamine
• 5-Methoxy tryptamine
• tryptamine, 5-Methoxy
• Spectrum_000193
• 2-(5-Methoxy-1H-indol-3-yl)ethylamine
• Tryptamine, 5-methoxy-
• Spectrum2_001111
• Spectrum4_000602
• Spectrum5_001300
• CBMicro_004933
• Biomol-NT_000156
• bmse000626
• 5-Methoxytryptamine, 97%
• Lopac0_000789
• Oprea1_086738
• SCHEMBL41982
• GTPL107
• KBioGR_001124
• KBioSS_000673
• 5-22-12-00018 (Beilstein Handbook Reference)
• MLS000515795
• MLS001424170
• METHOXYTRYPTAMINE, 5-
• SPBio_001242
• BPBio1_000530
• BDBM82087
• KBio2_000673
• KBio2_003241
• KBio2_005809
• 5-METHOXYTRYPTAMINE [MI]
• DTXSID60209638
• HMS1607I12
• HMS2052G13
• HMS2267B16
• HMS3394G13
• HMS3886L09
• WLN: T56 BMJ D2Z GO1
• BCP31118
• SMSF0037571
• CCG-15123
• s6324
• AKOS000265074
• AB00463
• CB06924
• CS-W015885
• DS-1776
• Ethanamine,2-(5-methoxy-3-indolyl)-
• NC00364
• SDCCGSBI-0004824.P004
• CAS_66-83-1
• NCGC00015694-01
• NCGC00015694-02
• NCGC00015694-03
• NCGC00015694-04
• NCGC00015694-05
• NCGC00015694-11
• NCGC00162256-01
• NCGC00162256-02
• NCGC00162256-03
• AC-15796
• AM804127
• SY035541
• TS-02682
• 2-(5-Methoxy-1H-indol-3-yl)ethanamine #
• A8462
• BB 0253965
• EU-0033500
• FT-0620577
• M0131
• O-Methylserotonin, purum, >=98.0% (NT)
• EN300-75859
• M-3550
• M-3551
• 2-(5-METHOXY-1H-INDOL-3-YL)-ETHYLAMINE
• L000647
• Q4352011
• BRD-K30197592-001-01-5
• BRD-K30197592-003-02-9
• F0266-0466
• Z336079372
• 2901782C-4651-419E-81A0-8179F6F3AA3E
• Mexamine;2-(5-Methoxy-1H-indol-3-yl)ethanamine;3-(2-Aminoethyl)-5-methoxyindole

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7769	77.69%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.3976	39.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9531	95.31%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.6750	67.50%
BSEP inhibitior	-	0.6334	63.34%
P-glycoprotein inhibitior	-	0.9821	98.21%
P-glycoprotein substrate	+	0.5164	51.64%
CYP3A4 substrate	-	0.5832	58.32%
CYP2C9 substrate	-	0.8165	81.65%
CYP2D6 substrate	+	0.6752	67.52%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.5916	59.16%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.6902	69.02%
CYP inhibitory promiscuity	+	0.6501	65.01%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6031	60.31%
Eye corrosion	-	0.9738	97.38%
Eye irritation	-	0.9016	90.16%
Skin irritation	-	0.6674	66.74%
Skin corrosion	-	0.8047	80.47%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3913	39.13%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8908	89.08%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.8932	89.32%
Acute Oral Toxicity (c)	III	0.5503	55.03%
Estrogen receptor binding	-	0.5902	59.02%
Androgen receptor binding	-	0.8255	82.55%
Thyroid receptor binding	-	0.6198	61.98%
Glucocorticoid receptor binding	-	0.5422	54.22%
Aromatase binding	-	0.6897	68.97%
PPAR gamma	-	0.6614	66.14%
Honey bee toxicity	-	0.9517	95.17%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	-	0.9498	94.98%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	0.503 nM	EC50	via Super-PRED
CHEMBL1875	Q13639	Serotonin 4 (5-HT4) receptor	26.92 nM	Ki	via Super-PRED
CHEMBL3371	P50406	Serotonin 6 (5-HT6) receptor	50 nM	Ki	via Super-PRED
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	5.012 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.26%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.03%	96.09%
CHEMBL4581	P52732	Kinesin-like protein 1	94.71%	93.18%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.26%	89.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.87%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.09%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.48%	97.09%
CHEMBL3492	P49721	Proteasome Macropain subunit	88.40%	90.24%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	88.18%	82.86%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.57%	92.62%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	87.33%	95.48%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.15%	94.45%
CHEMBL4208	P20618	Proteasome component C5	86.92%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.88%	96.00%
CHEMBL2535	P11166	Glucose transporter	85.72%	98.75%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	85.37%	95.55%
CHEMBL1907	P15144	Aminopeptidase N	85.36%	93.31%
CHEMBL255	P29275	Adenosine A2b receptor	85.25%	98.59%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.02%	92.94%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.89%	91.71%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	83.14%	93.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.04%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.79%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.62%	93.99%
CHEMBL5443	O00311	Cell division cycle 7-related protein kinase	82.07%	96.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.98%	95.89%
CHEMBL3959	P16083	Quinone reductase 2	80.47%	89.49%

Plants that contains it

• Cinchona calisaya
• Mimosa somnians
• Virola peruviana

Cross-Links

• PubChem: 1833
• LOTUS: LTS0011527
• wikiData: Q4352011