Α-Methyltryptamine

α-Methyltryptamine (αMT, AMT, Indopan) is a psychedelic, stimulant, and entactogen drug of the tryptamine class.[1][2] It was originally developed as an antidepressant by workers at Upjohn in the 1960s.[3]

Chemistry

αMT is tryptamine with a methyl substituent at the alpha carbon. 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,[4] and as a non-selective serotonin receptor agonist.[5]

MAOI activity

αMT has been show as a reversible inhibitor of the enzyme monoamine oxidase (MAO) in-vitro[6] and in-vivo.[7]

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.[8]

A typical dose of harmaline for MAO inhibition is 150mg,[9] higher than any typical αMT dose[10] so aMT's MAOI activity at typical doses will be significant but not total. The danger rises exponentially as αMT doses approach 150mg due to increased monoamine release and increased MAO inhibition.

Metabolism

2-Oxo-AMT, 6-hydroxy-AMT,[11] 7-hydroxy-AMT and 1′-hydroxy-AMT were detected as metabolites of AMT in male Wistar rats.[12]

Dosage and effects

With 20–30 milligrams, euphoria, empathy, and psychedelic effects become apparent and can last as long as 12 hours.[13] 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.[14][1]

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 and MDMA, such as delusions and hallucinations.[1][15]

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.[16] It is possible that αMT could cause the same neurotoxicity.

Legality

Australia

The 5-Methoxy analogue, 5-MeO-αMT is schedule 9 in Australia and αMT would be controlled as an analogue of this.[17]

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.[18]

UK

It is legal in the United Kingdom, however, and does not fall under the tryptamine clause as its substituent is not on the nitrogen position. See "2001 Misuse of Drugs Act: Schedule 1, Regulation 3"[19] for more information. Similarly, Canada has no mention of this substance in the Controlled Drugs and Substances Act.[20]

USA

The Drug Enforcement Administration (DEA) placed MT 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, AMT was permanently controlled as a schedule I substance under the CSA (69FR 58050).[21]

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.[22] Most fatalities are not verified but those which are involve excessive doses[23] or coingestion with other drugs.[24]

See also

Notes

References

External links

  • entry
  • αMT Entry in TiHKAL • info
  • Erowid page on αMT
  • Lycaeum page on αMT

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