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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 of INDOPAN

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
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 0.82 µM [IC50]
Inhibitor
8297
 60.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Withdrawn
Indopan

Approved Use

Unknown
Primary
Withdrawn
Indopan

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Schedules of controlled substances: temporary placement of alpha-methyltryptamine and 5-methoxy-N,N-diisopropyltryptamine into Schedule I. Final rule.
2003 Apr 4
Alpha-methyltryptamine revisited via easy Internet access.
2003 Jun
[Analysis of the chemical drugs among structural isomer].
2006 Sep
Differential impacts of smoke-free laws on indoor air quality.
2008 Apr
In vivo metabolism of alpha-methyltryptamine in rats: identification of urinary metabolites.
2008 Dec
Comparison of the separation of nine tryptamine standards based on gas chromatography, high performance liquid chromatography and capillary electrophoresis methods.
2008 Feb 15
A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation.
2008 Jan 15
Optimization of separation and online sample concentration of N,N-dimethyltryptamine and related compounds using MEKC.
2009 Feb
The hallucinogenic world of tryptamines: an updated review.
2015 Aug
Patents

Patents

US3296072
1

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 UTC 2023
Edited
by admin
on Sat Dec 16 08:35:52 UTC 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
MI  
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
Created by admin on Sat Dec 16 08:35:52 UTC 2023 , Edited by admin on Sat Dec 16 08:35:52 UTC 2023
WIKIPEDIA TiHKAL
Created by admin on Sat Dec 16 08:35:52 UTC 2023 , Edited by admin on Sat Dec 16 08:35:52 UTC 2023
WIKIPEDIA Designer-drugs-.alpha.-Methyltryptamine
Created by admin on Sat Dec 16 08:35:52 UTC 2023 , Edited by admin on Sat Dec 16 08:35:52 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID00861850
Created by admin on Sat Dec 16 08:35:52 UTC 2023 , Edited by admin on Sat Dec 16 08:35:52 UTC 2023
PRIMARY
MERCK INDEX
m7477
Created by admin on Sat Dec 16 08:35:52 UTC 2023 , Edited by admin on Sat Dec 16 08:35:52 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB01446
Created by admin on Sat Dec 16 08:35:52 UTC 2023 , Edited by admin on Sat Dec 16 08:35:52 UTC 2023
PRIMARY
FDA UNII
BIK35ACJ0Q
Created by admin on Sat Dec 16 08:35:52 UTC 2023 , Edited by admin on Sat Dec 16 08:35:52 UTC 2023
PRIMARY
WIKIPEDIA
alpha-Methyltryptamine
Created by admin on Sat Dec 16 08:35:52 UTC 2023 , Edited by admin on Sat Dec 16 08:35:52 UTC 2023
PRIMARY α-Methyltryptamine (abbreviated as αMT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by workers at Upjohn in the 1960s,[4] and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued. αMT has been shown as a reversible inhibitor of the enzyme monoamine oxidase (MAO) in-vitro and in-vivo. In rats the potency of αMT as an MAO-A inhibitor in the brain was approximately equal to that of harmaline at equimolar doses.[note 1] Dexamphetamine did not enhance the 5-hydroxytryptophan-induced rise of serotonin at any level.
NSC
97069
Created by admin on Sat Dec 16 08:35:52 UTC 2023 , Edited by admin on Sat Dec 16 08:35:52 UTC 2023
PRIMARY
CHEBI
59020
Created by admin on Sat Dec 16 08:35:52 UTC 2023 , Edited by admin on Sat Dec 16 08:35:52 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-073-7
Created by admin on Sat Dec 16 08:35:52 UTC 2023 , Edited by admin on Sat Dec 16 08:35:52 UTC 2023
PRIMARY
PUBCHEM
9287
Created by admin on Sat Dec 16 08:35:52 UTC 2023 , Edited by admin on Sat Dec 16 08:35:52 UTC 2023
PRIMARY
CAS
299-26-3
Created by admin on Sat Dec 16 08:35:52 UTC 2023 , Edited by admin on Sat Dec 16 08:35:52 UTC 2023
PRIMARY
Related Record Type Details
SODIUM-DEPENDENT NORADRENALINE TRANSPORTER
TARGET -> INHIBITOR
AMINE OXIDASE (FLAVIN-CONTAINING) A
TARGET -> INHIBITOR
SODIUM-DEPENDENT DOPAMINE TRANSPORTER
TARGET -> INHIBITOR
From Rat Membrane Studies
SODIUM-DEPENDENT SEROTONIN TRANSPORTER
TARGET -> INHIBITOR
From Rat Membrane Studies
Structure of 4-HYDROXY-.ALPHA.-METHYLTRYPTAMINE
DERIVATIVE -> PARENT
NIH
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