EMDT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H22N2O
Molecular Weight	246.348
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=C(CCN(C)C)C2=CC(OC)=CC=C2N1

InChI

InChIKey=ZEYRDXUWJDGTLD-UHFFFAOYSA-N

InChI=1S/C15H22N2O/c1-5-14-12(8-9-17(2)3)13-10-11(18-4)6-7-15(13)16-14/h6-7,10,16H,5,8-9H2,1-4H3

HIDE SMILES / InChI

Molecular Formula	C15H22N2O
Molecular Weight	246.348
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10715164 | https://www.ncbi.nlm.nih.gov/pubmed/17428998

2-ethyl-5-methoxy-N, N-dimethyltryptamine (EMDT) represents the first and most selective 5-HT(6) receptor agonist. Based on its activity in tail suspension test was suggested, that EMDT could be an effective antidepressant

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 6 (5-HT6) receptor 45 Target ID: CHEMBL3371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10715164	Agonist 2678		16.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17428998	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
2-Substituted tryptamines: agents with selectivity for 5-HT(6) serotonin receptors.	2000 Mar 9	10715164
DARPP-32 mediates serotonergic neurotransmission in the forebrain.	2002 Mar 5	11880652
2-Alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles as novel 5-HT6 receptor agonists.	2005 Oct 1	16055331
Biochemical and behavioral evidence for antidepressant-like effects of 5-HT6 receptor stimulation.	2007 Apr 11	17428998
Binding of serotonin and N1-benzenesulfonyltryptamine-related analogs at human 5-HT6 serotonin receptors: receptor modeling studies.	2008 Feb 14	18201064

Patents

Sample Use Guides

In Vivo Use Guide

in mice: the day of the tail suspension test, experimental mice were transferred to the experiment room and allowed to acclimatize for 3–4 h. Mice were injected intraperitoneally with saline, EMDT (1, 2.5, 5, 10, or 15 mg/kg), fluoxetine (20 mg/kg), SB271046 (1, 5, or 10 mg/kg), or SB271046 (1, 5, or 10 mg/kg) combined with fluoxetine (20 mg/kg) 30 min before the tail suspension test trial.

Route of Administration: Intraperitoneal

In Vitro Use Guide

EMDT increases the phosphorylation state of Thr34-DARPP-32 (Dopamine- and cAMP-regulated phosphoprotein) both in brain slices and in the intact brain. In vitro regulation of Thr34-DARPP-32 and Ser845-GluR1 phosphorylation by EDMTA (100 uM) was investigated in slices of neostriatum from wild-type and D1 knock-out mice.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 15:46:15 GMT 2023` Edited by `admin` on `Sat Dec 16 15:46:15 GMT 2023`
Record UNII	GWM65988LJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EMDT

Common Name

English

2-Ethyl-5-methoxy-N,N-dimethyl-1H-indole-3-ethanamine

Systematic Name

English

2-(2-ETHYL-5-METHOXY-1H-INDOL-3-YL)-N,N-DIMETHYL-ETHANAMINE

Systematic Name

English

1H-Indole-3-ethanamine, 2-ethyl-5-methoxy-N,N-dimethyl-

Systematic Name

English

Code System Code Type Description

FDA UNII

GWM65988LJ