α-Methyltryptamine

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α-Methyltryptamine
IV[1]
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(1H-Indol-3-yl)propan-2-amine
JSmol)
  • NC(CC1=CNC2=C1C=CC=C2)C
  • 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 checkY
  • Key:QSQQQURBVYWZKJ-UHFFFAOYSA-N checkY
  (verify)

α-Methyltryptamine (abbreviated as αMT, AMT) is a

entactogen drug of the tryptamine class.[3][4] It was originally developed as an antidepressant by chemists at Upjohn in the 1960s,[5] and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.[6][7][8]

Chemistry

αMT is a tryptamine with a

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
.

Synthesis

The synthesis of αMT can be accomplished through several different routes, the two most widely known being the Nitroaldol Condensation between

Pharmacology

αMT acts as a relatively balanced

MAOI activity

αMT has been shown as a

In rats the potency of αMT as an MAO-A inhibitor in the brain was approximately equal to that of

5-hydroxytryptophan-induced rise of serotonin at any level.[15]

Metabolism

2-Oxo-αMT, 6-hydroxy-αMT,[16] 7-hydroxy-αMT and 1′-hydroxy-αMT were detected as metabolites of αMT in male Wistar rats .[17]

Dosage and effects

Under the trade name Indopan, 5-10 milligrams were used for an antidepressant effect.[medical citation needed]

With 20–30 milligrams,

form is smoked, with doses between and 2 and 5 milligrams.[1][unreliable source?][3]

Neurologic side effects of αMT include agitation, restlessness, confusion, and lethargy. Physical manifestations including

Side effects self-reported by recreational users include

pupil dilation, tachycardia, headaches, nausea, and vomiting, as well as psychedelic effects including visual hallucinations and an altered state of mind.[3][20]

Legality

Australia

The 5-Methoxy analogue,

schedule 9 in Australia and αMT would be controlled as an analogue of this.[21]

China

As of October 2015 αMT is a controlled substance in China.[22]

Denmark

In Denmark (2010), the Danish Minister for the Interior and Health placed αMT to their lists of controlled substances (List B).[23]

Canada

Canada has no mention of αMT in the Controlled Drugs and Substances Act.[24]

Germany

αMT is listed under the Narcotics Act in schedule 1 (narcotics not eligible for trade and medical prescriptions) in Germany.[23]

Austria

αMT is placed under Austrian law (NPSG) Group 6.[23]

Hungary

αMT was controlled on the Schedule C list in Hungary in 2013.[23]

Slovakia

αMT was placed in 2013 on the List of Hazardous Substances in Annex, § 2 in Slovakia.[23]

Slovenia

αMT appeared on the Decree on Classification of Illicit Drugs in Slovenia (2013).[23]

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.[23]

Spain

αMT is legal in Spain.[25]

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.[26]

United Kingdom

αMT was made illegal in the United Kingdom as of 7 January 2015, along with 5-MeO-DALT.[27] 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.[28]

United States

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).[29]

Finland

AMT, alfa-methyltryptamine is a controlled drug in Finland[30]

Reported deaths

αMT is capable of causing life-threatening side-effects including

Miami-Dade county and a British teenager, both who died after consuming 1 g of αMT.[33][19]

See also

Notes

  1. ^ MAOI potency was comparable at 7 μM/kg, equivalent to 1.5mg/kg of Harmaline and 1.2mg/kg of αMT. At 70μM/kg αMT was a much less effective MAOI than harmaline.[15]

References

  1. ^ a b c "Erowid AMT Vault : FAQ by Dialtonez".
  2. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  3. ^ a b c "Erowid Online Books : "TIHKAL" - #48 a-MT".
  4. ^ "Erowid AMT (alpha-methyltryptamine) Vault".
  5. ^ US Patent 3296072, Szmuszkovicz Jacob, "Method of Treating Mental Depression", published 1967-01-03, assigned to Upjohn Co 
  6. .
  7. .
  8. .
  9. ^ Anonymous. "TheHive". Retrieved 7 June 2023.
  10. ^ Shulgin A. "TIHKAL". Retrieved 18 May 2018.
  11. PMID 17223101
    .
  12. .
  13. .
  14. .
  15. ^ .
  16. .
  17. .
  18. .
  19. ^ .
  20. ^ "Erowid AMT Vault : Effects".
  21. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  22. ^ a b c d e f g "Reference at www.who.int" (PDF).
  23. ^ "CSDA". Archived from the original on 2011-09-28. Retrieved 2011-06-05.
  24. ^ "Medicamentos de Uso Humano - Estupefacientes y Psicótropos". Agencia Española de Medicamentos y Productos Sanitarios. Archived from the original on 2019-01-02. Retrieved 2019-01-01.
  25. ^ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor;" (PDF), Lagen om förbud mot vissa hälsofarliga varor - SFS 2005:26 (in Swedish), February 2005, archived from the original (PDF) on 2013-09-29, retrieved 2013-10-07
  26. ^ "The Misuse of Drugs (Amendment No. 3) (England, Wales and Scotland) Regulations 2014". www.legislation.gov.uk.
  27. ^ ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Retrieved 10 June 2014.
  28. ^ "Alpha-methyltryptamine" (PDF). DEA Office of Diversion Control. April 2013. Archived (PDF) from the original on 2013-10-17. Retrieved 2013-10-10.
  29. ^ "Reference at www.finlex.fi" (PDF).
  30. PMID 16051647
    . "drugs such as MDMA, ecstasy (3,4-methylenedioxymethamphetamine), if combined with MAOIs (including moclobemide) do also cause fatalities because they act as serotonin releasers"
  31. ^ "Call for ban on drug after reveller's death". Western Gazette. March 22, 2012. Archived from the original on 2013-10-16. Retrieved October 1, 2013.
  32. ^ "Southampton 'legal high' death deemed 'accidental'". BBC News. 2013-11-12. Retrieved 2013-11-19.

External links