Alpha Methyltryptamine

Chemistry

αMT is tryptamine with a methyl substituent at the alpha carbon. This alpha substitution makes it a poor substrate for Monoamine_oxidase_A, thereby greatly 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.

Pharmacology

αMT acts as a relatively balanced reuptake inhibitor and releasing agent of the main three monoamines; serotonin, norepinephrine, and dopamine, and as a non-selective serotonin receptor agonist.

MAOI activity

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. 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.

Metabolism

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

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 as strong. In rare cases or extreme doses the duration of effects might exceed 24 hours. αMT in freebase form is reported by users to have been smoked, with doses of between and 2–5 milligrams being cited.

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 analogue αET has been shown to produce long-lasting serotonergic neurotoxicity at very high doses. It is possible that αMT could cause the same neurotoxicity.

Australia

The 5-Methoxy analogue, 5-MeO-αMT is schedule 9 in Australia and αMT would be controlled as an analogue of this.

China

As of October 2015 αMT is a controlled substance in China.

Denmark

In Denmark (2010), the Danish Minister for the Interior and Health placed αMT to their lists of controlled substances(List B).

Canada

Canada has no mention of αMT in the Controlled Drugs and Substances Act. However, αMT is on the Registration, Evaluation, Authorisation and Restriction of Chemicals(REACH) list of pre-registered substances as of March 2009.

Germany

αMT is listed under the Narcotics Act in schedule 1 (narcotics not eligible for trade and medical prescriptions) in Germany.

Austria

αMT is placed under Austrian law (NPSG) Group 6.

Hungary

αMT was controlled on the Schedule C list in Hungary in 2013.

Slovakia

αMT was placed in 2013 on the List of Hazardous Substances in Annex, § 2 in Slovakia.

Slovenia

αMT appeared on the Decree on Classification of Illicit Drugs in Slovenia (2013).

Lithuania

In Lithuania (2012), αMT is controlled as a tryptamine derivative put under control in the 1st list of Narcotic Drugs and Psychotropic Substances which use is prohibited for medical purposes.

Spain

αMT is legal in Spain.

Sweden

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.

UK

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.

USA

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).

Finland

AMT, alfa-methyltryptamine is illegal in Finland

Reported Deaths

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.

Synthesis

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