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, and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.
|Other names||Indopan; IT-290, IT-403, U-14,164E, 3-IT|
|Oral, Insufflation, Rectal, Smoked, IM, IV|
|ECHA InfoCard||100.005.522 |
|Chemical and physical data|
|Molar mass||174.24 g/mol g·mol−1|
|3D model (JSmol)|
αMT is tryptamine with a methyl substituent at the alpha carbon. This alpha substitution makes it a relatively poor substrate for monoamine oxidase A, thereby prolonging αMT's half-life, allowing it to reach the brain and enter the central nervous system. Its chemical relation to tryptamine is analogous to that of amphetamine to phenethylamine, amphetamine being α-methylphenethylamine. αMT is closely related to the neurotransmitter serotonin (5-hydroxytryptamine) which partially explains its mechanism of action.
The synthesis of αMT can be accomplished through several different routes, the two most widely known being the Nitroaldol Condensation between indole-3-carboxaldehyde and nitroethane under ammonium acetate catalysis and the condensation between indole-3-acetone and hydroxylamine followed by reduction of the obtained ketoxime with lithium aluminum hydride.
In rats the potency of αMT as an MAO-A inhibitor in the brain was approximately equal to that of harmaline at equimolar doses. Dexamphetamine did not enhance the 5-hydroxytryptophan-induced rise of serotonin at any level.
A typical dose of harmaline for MAO inhibition is 150 mg, higher than any typical αMT dose so αMT's MAOI activity at typical doses will be significant but not total. The danger rises exponentially as αMT doses approach 150 mg due to increased monoamine release and increased MAO inhibition.
2-Oxo-αMT, 6-hydroxy-αMT, 7-hydroxy-αMT and 1′-hydroxy-αMT were detected as metabolites of αMT in male Wistar rats .
Dosage and effects
Under the trade name Indopan, 5-10 milligrams were used for an antidepressant effect.
With 20–30 milligrams, euphoria, empathy, and psychedelic effects become apparent and can last as long as 12 hours. A dose exceeding 40 mg is generally considered strong. In rare cases or extreme doses, the duration of effects might exceed 24 hours. Users report that αMT in freebase form is smoked, with doses between and 2 and 5 milligrams.
Reported side effects include anxiety, restlessness, muscle tension, jaw tightness, pupil dilation, tachycardia, headaches, nausea, and vomiting, among other effects that might commonly be attributed to LSD, psilocybin, DMT, and MDMA, such as open-eye visuals, closed eye visuals and an altered state of mind.
In spite of some reported experiential similarities to MDMA, the chemicals are structurally unrelated; αMT is a tryptamine while MDMA is a phenethylamine.
Like many other serotonin releasing agents, αMT's analog α-ethyltryptamine (αET) has been shown to produce long-lasting serotonergic neurotoxicity at very high doses. It is possible that αMT causes the same neurotoxicity.
Canada has no mention of αMT in the Controlled Drugs and Substances Act.
Sveriges riksdags health ministry Statens folkhälsoinstitut classified αMT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as alfa-metyltryptamin (AMT), making it illegal to sell or possess.
αMT was made illegal in the United Kingdom as of 7 January 2015, along with 5-MeO-DALT. This was following the events of 10 June 2014 when the Advisory Council on the Misuse of Drugs recommended that αMT be scheduled as a class A drug by updating the blanket ban clause on tryptamines.
The Drug Enforcement Administration (DEA) placed αMT temporarily in schedule I of the Controlled Substances Act (CSA) on April 4, 2003, pursuant to the temporary scheduling provisions of the CSA (68 FR16427). On September 29, 2004, αMT was permanently controlled as a schedule I substance under the CSA (69FR 58050).
Deaths from αMT are rare but as a powerful monoamine releaser, injury can occur when excessive doses are taken or when taken with drugs such as MAOIs. Most fatalities are not verified but those which are involve excessive doses or coingestion with other drugs. A British teenager died after consuming 1 g of αMT in August 2013.
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