INDOPAN

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H14N2
Molecular Weight	174.2423
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(N)CC1=CNC2=CC=CC=C12

InChI

InChIKey=QSQQQURBVYWZKJ-UHFFFAOYSA-N

InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3

HIDE SMILES / InChI

Molecular Formula	C11H14N2
Molecular Weight	174.2423
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.etolen.com/index.php?option=com_content&view=article&id=2835&Itemid=101
Curator's Comment: description was created based on several sources, including https://legal-high-inhaltsstoffe.de/sites/default/files/uploads/amt.pdf

Alpha methyltryptamine (AMT) is a tryptamine (indole ethylamine) derivative, which was developed in the 1960's by Upjohn with the intention for use as an antidepressant. It was used in Russia under the trade name Indopan for the treatment of Bipolar disorder and some form of depression, but currently not being produced because of serious side effects. In the 1990's, alpha-methyltryptamine became regulated as a Schedule I controlled substance in the United States. Pharmacologically, AMT has high affinity for the serotonin (5-HT) transporter, a number of 5-HT receptors, and potently inhibits reuptake of monoamines dopamine, 5-HT, and norepinephrine reuptake. AMT is also a monoamine oxidase A inhibitor that conceivably could contribute to its pharmacological effect and this drug also the most potent inhibitor of semicarbazide-sensitive amine oxidase (SSAO).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Monoamine oxidase A 49 Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3747266	Inhibitor 8297		0.82 µM [IC50]
Amine oxidase, copper containing 9 Target ID: CHEMBL4592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3747266	Inhibitor 8297		60.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bipolar disorder 34 Sources: http://www.etolen.com/index.php?option=com_content&view=article&id=2835&Itemid=101	Primary		Withdrawn	Indopan Approved Use Unknown
Depression 235 Sources: http://www.etolen.com/index.php?option=com_content&view=article&id=2835&Itemid=101	Primary		Withdrawn	Indopan Approved Use Unknown

PubMed

Title	Date	PubMed
Schedules of controlled substances: temporary placement of alpha-methyltryptamine and 5-methoxy-N,N-diisopropyltryptamine into Schedule I. Final rule.	2003 Apr 4	12678045
Alpha-methyltryptamine revisited via easy Internet access.	2003 Jun	12776793
Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives.	2004 Jan	14697897
A general screening and confirmation approach to the analysis of designer tryptamines and phenethylamines in blood and urine using GC-EI-MS and HPLC-electrospray-MS.	2004 Sep	15516287
Schedules of controlled substances: placement of alpha-methyltryptamine and 5-methoxy-N,N-diisopropyltryptamine into schedule I of the Controlled Substances Act. Final rule.	2004 Sep 29	15455477
Sensitive determination of alpha-methyltryptamine (AMT) and 5-methoxy-N,N-diisopropyltryptamine (5MeO-DIPT) in whole blood and urine using gas chromatography-mass spectrometry.	2005 Aug 25	16055053
Fatality due to acute alpha-methyltryptamine intoxication.	2005 Jul-Aug	16105268
[Analysis of the chemical drugs among structural isomer].	2006 Sep	16946596
Substance use and sexual behaviours of Japanese men who have sex with men: a nationwide internet survey conducted in Japan.	2006 Sep 26	17002800
Differential impacts of smoke-free laws on indoor air quality.	2008 Apr	18468220
In vivo metabolism of alpha-methyltryptamine in rats: identification of urinary metabolites.	2008 Dec	18982537
Comparison of the separation of nine tryptamine standards based on gas chromatography, high performance liquid chromatography and capillary electrophoresis methods.	2008 Feb 15	18177659
A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation.	2008 Jan 15	18371669
Optimization of separation and online sample concentration of N,N-dimethyltryptamine and related compounds using MEKC.	2009 Feb	19137528
The hallucinogenic world of tryptamines: an updated review.	2015 Aug	25877327

Patents

Sample Use Guides

In Vivo Use Guide

Pills with concentration 0,005–0,010 g 2-3 times in first part of day. Depends on positive effect the dosage could be increased up to 0,02-0,04 g per day. Course of treatment 8–12 weeks

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:35:52 GMT 2023` Edited by `admin` on `Sat Dec 16 08:35:52 GMT 2023`
Record UNII	BIK35ACJ0Q
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

INDOPAN

Common Name

English

2-(1H-INDOL-3-YL)-1-METHYLETHYLAMINE

Systematic Name

English

3-(2-AMINOPROPYL)INDOLE

Systematic Name

English

1H-INDOLE-3-ETHANAMINE, .ALPHA.-METHYL-

Systematic Name

English

AMT-

Common Name

English

164 E

Code

English

.ALPHA.-METHYL-.BETA.-INDOLEETHYLAMINE

Common Name

English

INDOLE, 3-(2-AMINOPROPYL)-

Systematic Name

English

(±)-.ALPHA.-METHYLTRYPTAMINE

Systematic Name

English

DL-.ALPHA.-METHYLTRYPTAMINE

Common Name

English

DL-3-(2-AMINOPROPYL)INDOLE

Common Name

English

.ALPHA.-METHYLTRYPTAMINE

Systematic Name

English

U 14

Code

English

3-(2-AMINOPROPYL)-1H-INDOLE

Systematic Name

English

SPIRALS

Common Name

English

NSC-97069

Code

English

.ALPHA.-METHYLTRYPTAMINE [MI]

Common Name

English

AMT

Common Name

English

RO 3-0926

Code

English

.ALPHA.-METHYL-3-INDOLEETHANAMINE

Systematic Name

English

.ALPHA.-METHYLTRYPTAMINE-

Systematic Name

English

.ALPHA.MT

Common Name

English

Classification Tree Code System Code

DEA NO.

7432