General Information of the Compound
Compound ID
CP0071154
Compound Name
2-(5-methoxy-1H-indol-3-yl)-N,N-dimethyl-ethanamine
    Show/Hide
Synonyms
1019-45-0
1H-Indole-3-ethanamine, 5-methoxy-N,N-dimethyl-
2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
3-(2-Dimethylaminoethyl)-5-methoxyindole
5-MEO-DMT
5-MeO-DMT
5-Methoxy-N,N-dimethyl-1H-indole-3-ethanamine
5-Methoxy-N,N-dimethyltryptamine
5-Methoxydimethyltryptamine
5-OMe-DMT
Bufotenine, O-methyl-
CT 4334
INDOLE, 3-(2-(N,N-DIMETHYLAMINO)ETHYL)-5-METHOXY-
MeODMT
Methoxybufotenin
Methoxydimethyltryptamines
Methylbufotenine
N,N-Dimethyl-5-methoxytryptamine
NSC 88624
O-Methylbufotenine
UNII-X0MKX3GWU9
    Show/Hide
Structure
Formula
C13H18N2O
Molecular Weight
218.3
Canonical SMILES
COc1ccc2[nH]cc(CCN(C)C)c2c1
    Show/Hide
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
    Show/Hide
InChIKey
ZSTKHSQDNIGFLM-UHFFFAOYSA-N
CAS
1019-45-0
Physicochemical Property
logP
2.2806
Rotatable Bonds
4
Heavy Atom Count
16
Polar Areas
28.26
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Complexity
16

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

    Show/Hide
Click to Show/Hide the External Link(s) of This Compound
PubChem ID
CID: 1832
SID: 14773502
ChEMBL ID
CHEMBL7257
DrugBank ID
DB14010
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT01448, 5-hydroxytryptamine receptor 1A
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
Ki = 11 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 7.8 nM
2 Ki = 69 nM
Protein ID: PT00825, 5-hydroxytryptamine receptor 2A
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
EC50 = 1.76 nM
   TI
   LI
   LO
   TS
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
Ki = 15 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 15 nM
2 Ki = 620 nM
Protein ID: PT01492, 5-hydroxytryptamine receptor 2A
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000035 NIH 3T3 Mus musculus (Mouse)  1
1
Ki = 92 nM
   TI
   LI
   LO
   TS
Protein ID: PT01019, 5-hydroxytryptamine receptor 2B
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
Ki = 52 nM
   TI
   LI
   LO
   TS
Protein ID: PT01480, 5-hydroxytryptamine receptor 2C
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000035 NIH 3T3 Mus musculus (Mouse)  1
1
EC50 = 77.8 nM
   TI
   LI
   LO
   TS
CL000085 J1 Mus musculus (Mouse)  1
1
Ki = 960 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 250 nM
Protein ID: PT00939, 5-hydroxytryptamine receptor 2C
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
Ki = 42 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 250 nM
Protein ID: PT01354, 5-hydroxytryptamine receptor 6
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  3
1
Ki = 13 nM
   TI
   LI
   LO
   TS
2
Ki = 16 nM
   TI
   LI
   LO
   TS
3
Ki = 78 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 16 nM
2 Ki = 70 nM
Protein ID: PT01843, Melatonin receptor type 1A
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  2
1
EC50 = 257 nM
   TI
   LI
   LO
   TS
2
Ki = 210 nM
   TI
   LI
   LO
   TS
Protein ID: PT02174, Melatonin receptor type 1B
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  2
1
EC50 = 112 nM
   TI
   LI
   LO
   TS
2
Ki = 16 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( 5-MEO-DMT )
Drug Name 5-MEO-DMT
Target(s)
5-HT 2A receptor (HTR2A)
Inhibitor
5-HT 2B receptor (HTR2B)
Inhibitor
5-HT 2C receptor (HTR2C)
Inhibitor
5-HT 6 receptor (HTR6)
Inhibitor