N,N-Dimethyl-5-methoxytryptamine

Details

• Internal ID: fc5306c7-dc79-47e2-b45f-cf21bd7a348a
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Tryptamines and derivatives
• IUPAC Name: 2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
• SMILES (Canonical): CN(C)CCC1=CNC2=C1C=C(C=C2)OC
• SMILES (Isomeric): CN(C)CCC1=CNC2=C1C=C(C=C2)OC
• 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
• InChI Key: ZSTKHSQDNIGFLM-UHFFFAOYSA-N
• Popularity: 754 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₈N₂O
• Molecular Weight: 218.29 g/mol
• Exact Mass: 218.141913202 g/mol
• Topological Polar Surface Area (TPSA): 28.30 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.28
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 1019-45-0
• 5-Methoxy-N,N-dimethyltryptamine
• Methoxybufotenin
• O-Methylbufotenine
• 5-MeO-DMT
• 5-Methoxydimethyltryptamine
• MeODMT
• Methylbufotenine
• 3-(2-Dimethylaminoethyl)-5-methoxyindole
• Bufotenine, O-methyl-
• 2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
• 1H-Indole-3-ethanamine, 5-methoxy-N,N-dimethyl-
• Mebufotenin
• CT 4334
• 5-Methoxy-N,N-dimethyl-1H-indole-3-ethanamine
• NSC 88624
• INDOLE, 3-(2-(N,N-DIMETHYLAMINO)ETHYL)-5-METHOXY-
• EINECS 213-813-2
• UNII-X0MKX3GWU9
• 5-Methoxy-N,N-dimethyl-1H-indole-3-ethylamine
• NSC-88624
• X0MKX3GWU9
• 3-(2-(N,N-Dimethyl)aminoethyl)-5-methoxyindole
• BRN 0164771
• CHEMBL7257
• MLS000069438
• CHEBI:2086
• Indole, 3-(2-(dimethylamino)ethyl)-5-methoxy-
• Indole, 3-[2-(dimethylamino)ethyl]-5-methoxy-
• 3-[2-(N,N-Dimethylamino)ethyl]-5-methoxy-indole
• 5-METHOXY-N-DIMETHYLTRYPTAMINE
• SMR000059066
• 5-22-12-00027 (Beilstein Handbook Reference)
• 3-(2-(N,N-Dimethylamino)ethyl)-5-methoxyindole
• 3-[2-(N,N-Dimethylamino)ethyl]-5-methoxyindole
• 5-OMe-DMT
• mebufotenin [INN]
• Maybridge3_000045
• Lopac-M-2381
• DMT,5-Me
• D0C5XQ
• cid_1832
• Lopac0_000724
• Oprea1_596468
• GTPL145
• SCHEMBL132733
• 2-(5-methoxy-1H-indol-3-yl)-N,N-dimethyl-ethanamine
• BDBM30707
• 2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine
• DTXSID70144324
• [2-(5-METHOXY-1H-INDOL-3-YL)-ETHYL]-DIMETHYL-AMINE
• HMS1431C01
• HMS2235C20
• HMS3370M04
• N,N-Dimethyl-5-methoxy tryptamine
• NSC88624
• PDSP1_000032
• PDSP1_000447
• PDSP2_000032
• PDSP2_000445
• STK368074
• AKOS005203483
• Bufotenine, 5-Methoxydimethyltryptamine
• CCG-204809
• DB14010
• SDCCGMLS-0003129.P003
• IDI1_011432
• WLN: T56 BMJ D2N1&1 GO1
• NCGC00015654-01
• NCGC00015654-02
• NCGC00015654-03
• NCGC00015654-04
• NCGC00015654-05
• NCGC00015654-06
• NCGC00023288-03
• NCGC00023288-04
• Indole,N-dimethylamino)ethyl]-5-methoxy-
• LS-82935
• N,N-Dimethyl-5-methoxytryptamine, free base
• C08309
• D-5380
• [2-(5-methoxy-1H-indol-3-yl)ethyl]dimethylamine
• 2-(5-methoxy-1H-indol-3-yl)ethyl-dimethyl-amine
• 5-methoxyindole 3-(2-(N,N-Dimethylamino)ethyl)
• L000724
• Q570757
• 2-(5-methoxy-1H-indol-3-yl)-ethyl-dimethyl-amine
• BRD-K34224286-001-07-1
• 2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.8362	83.62%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6836	68.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9245	92.45%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	-	0.6342	63.42%
P-glycoprotein inhibitior	-	0.9672	96.72%
P-glycoprotein substrate	+	0.5557	55.57%
CYP3A4 substrate	+	0.5965	59.65%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	+	0.8005	80.05%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	+	0.5319	53.19%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.9295	92.95%
CYP inhibitory promiscuity	-	0.6555	65.55%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6572	65.72%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.7082	70.82%
Skin irritation	-	0.7063	70.63%
Skin corrosion	-	0.8099	80.99%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7844	78.44%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8722	87.22%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.9312	93.12%
Acute Oral Toxicity (c)	III	0.5490	54.90%
Estrogen receptor binding	-	0.5587	55.87%
Androgen receptor binding	-	0.8367	83.67%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.6012	60.12%
Aromatase binding	+	0.5542	55.42%
PPAR gamma	-	0.7692	76.92%
Honey bee toxicity	-	0.8867	88.67%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	-	0.4139	41.39%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3356	P05177	Cytochrome P450 1A2	15848.93 nM	AC50	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	39810.7 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	19952.6 nM	Potency	via CMAUP
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	31622.8 nM	Potency	via CMAUP
CHEMBL1945	P48039	Melatonin receptor 1A	210 nM; 210 nM	Ki; Ki	via Super-PRED; PMID: 26023814
CHEMBL1946	P49286	Melatonin receptor 1B	16 nM; 16 nM	Ki; Ki	via Super-PRED; PMID: 26023814
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	197 nM; 15 nM	EC50; IC50	via Super-PRED; PMID: 1447752
CHEMBL1898	P28222	Serotonin 1b (5-HT1b) receptor	550 nM	IC50	PMID: 1447752
CHEMBL1983	P28221	Serotonin 1d (5-HT1d) receptor	49 nM	IC50	PMID: 1433172
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	15 nM; 15 nM; 15 nM	Ki; Ki; Ki	PMID: 16392816; PMID: 8027974; via Super-PRED
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	52 nM; 52 nM	Ki; Ki	PMID: 16392816; via Super-PRED
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	42 nM; 250 nM	Ki; IC50	via Super-PRED; PMID: 1433172
CHEMBL3371	P50406	Serotonin 6 (5-HT6) receptor	13 nM; 13 nM; 16 nM; 16 nM	Ki; Ki; Ki; Ki	via Super-PRED; PMID: 16945532; PMID: 12825922; PMID: 11055342
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	30 nM	Ki	PMID: 12825922

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.43%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.78%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	96.60%	93.99%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	95.50%	90.71%
CHEMBL240	Q12809	HERG	94.39%	89.76%
CHEMBL2581	P07339	Cathepsin D	90.36%	98.95%
CHEMBL255	P29275	Adenosine A2b receptor	89.68%	98.59%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.67%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.60%	92.62%
CHEMBL2535	P11166	Glucose transporter	88.59%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.17%	94.00%
CHEMBL1907	P15144	Aminopeptidase N	87.40%	93.31%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	87.11%	85.49%
CHEMBL4208	P20618	Proteasome component C5	85.74%	90.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.35%	85.30%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	83.84%	93.24%
CHEMBL4581	P52732	Kinesin-like protein 1	82.49%	93.18%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	82.47%	89.44%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.15%	96.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	81.95%	80.96%
CHEMBL5443	O00311	Cell division cycle 7-related protein kinase	81.37%	96.11%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	81.11%	95.48%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.98%	96.67%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	80.82%	82.86%
CHEMBL3959	P16083	Quinone reductase 2	80.16%	89.49%

Plants that contains it

• Anadenanthera peregrina
• Arundo donax
• Horsfieldia superba
• Lespedeza bicolor
• Phalaris aquatica
• Phyllodium pulchellum
• Pleurolobus gangeticus
• Senna alexandrina
• Tetradium ruticarpum
• Virola peruviana

Cross-Links

• PubChem: 1832
• NPASS: NPC92111
• ChEMBL: CHEMBL7257
• LOTUS: LTS0217945
• wikiData: Q570757