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
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
DescriptionCurator's Comment: description was created based on several sources, including
https://legal-high-inhaltsstoffe.de/sites/default/files/uploads/amt.pdf
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Alpha-methyltryptamine revisited via easy Internet access. | 2003 Jun |
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| Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives. | 2004 Jan |
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| 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 |
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| 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 |
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| 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 |
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| Fatality due to acute alpha-methyltryptamine intoxication. | 2005 Jul-Aug |
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| [Analysis of the chemical drugs among structural isomer]. | 2006 Sep |
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| Substance use and sexual behaviours of Japanese men who have sex with men: a nationwide internet survey conducted in Japan. | 2006 Sep 26 |
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| Differential impacts of smoke-free laws on indoor air quality. | 2008 Apr |
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| In vivo metabolism of alpha-methyltryptamine in rats: identification of urinary metabolites. | 2008 Dec |
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| Comparison of the separation of nine tryptamine standards based on gas chromatography, high performance liquid chromatography and capillary electrophoresis methods. | 2008 Feb 15 |
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| A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. | 2008 Jan 15 |
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| Optimization of separation and online sample concentration of N,N-dimethyltryptamine and related compounds using MEKC. | 2009 Feb |
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| The hallucinogenic world of tryptamines: an updated review. | 2015 Aug |
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DEA NO. |
7432
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TiHKAL
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Designer-drugs-.alpha.-Methyltryptamine
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DTXSID00861850
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m7477
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DB01446
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alpha-Methyltryptamine
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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. | ||
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206-073-7
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9287
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299-26-3
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SUBSTANCE RECORD
