alpha-Methyltryptamine

α-Methyltryptamine (abbreviated as αMT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine class.[2][3] 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.[5][6][7]

α-Methyltryptamine
Clinical data
Other namesIndopan; IT-290, IT-403, U-14,164E, 3-IT[1]
Routes of
administration		Oral, Insufflation, Rectal, Smoked, IM, IV[1]
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
ECHA InfoCard100.005.522
Chemical and physical data
FormulaC11H14N2
Molar mass174.247 g·mol−1
3D model (JSmol)
  (verify)

Chemistry

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.

Synthesis

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.[8]

Pharmacology

αMT acts as a relatively balanced reuptake inhibitor and releasing agent of the main three monoamines; serotonin, norepinephrine, and dopamine,[9] and as a non-selective serotonin receptor agonist.[10]

MAOI activity

αMT has been shown as a reversible inhibitor of the enzyme monoamine oxidase (MAO) in-vitro[11] and in-vivo.[12]

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.[13]

A typical dose of harmaline for MAO inhibition is 150 mg,[14] higher than any typical αMT dose[15] 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,[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.

With 20–30 milligrams, euphoria, empathy, and psychedelic effects become apparent and can last as long as 12 hours.[18] 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.[1][2]

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.[2][19]

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.[20] It is possible that αMT causes 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.[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]

UK

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]

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).[29]

Finland

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

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.[31] Most fatalities are not verified but those which are involve excessive doses[32] or coingestion with other drugs.[33] A British teenager died after consuming 1 g of αMT in August 2013.[34]

gollark: I've seen a bunch of libraries in many, many languages for terminal manipulation.
gollark: I guess it will work fast enough, unless you want to do... anything at all... fast.
gollark: Yes, but process execution is more horribly inefficient then lua.
gollark: Calling a new process for *every* terminal position/color change, that is.
gollark: Isn't that going to be horrendously inefficient?

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.[13]

References
  1. "Erowid AMT Vault : FAQ by Dialtonez".
  2. "Erowid Online Books : "TIHKAL" - #48 a-MT".
  3. "Erowid AMT (alpha-methyltryptamine) Vault".
  4. US Patent 3296072, Szmuszkovicz Jacob, "Method of Treating Mental Depression", published 1967-01-03, assigned to Upjohn Co
  5. Donald G. Barceloux (20 March 2012). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. John Wiley & Sons. pp. 196–. ISBN 978-0-471-72760-6.
  6. Leslie Iversen (11 November 2013). Handbook of Psychopharmacology: Volume 14 Affective Disorders: Drug Actions in Animals and Man. Springer Science & Business Media. pp. 132–. ISBN 978-1-4613-4045-4.
  7. Biological Research on Addiction: Comprehensive Addictive Behaviors and Disorders. Academic Press. 17 May 2013. pp. 632–. ISBN 978-0-12-398360-2.
  8. Shulgin, Alexander. "TIHKAL". Retrieved 18 May 2018.
  9. Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology. 559 (2–3): 132–7. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  10. Nonaka R, Nagai F, Ogata A, Satoh K (December 2007). "In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes". Biological & Pharmaceutical Bulletin. 30 (12): 2328–33. doi:10.1248/bpb.30.2328. PMID 18057721.
  11. Arai, Y.; Toyoshima, Y.; Kinemuchi, H. (1986). "Studies of monoamine oxidase and semicarbazide-sensitive amine oxidase. II. Inhibition by .ALPHA.-methylated substrate-analogue monoamines, .ALPHA.-methyltryptamine, .ALPHA.-methylbenzylamine and two enantiomers of .ALPHA.-methylbenzylamine". The Japanese Journal of Pharmacology. 41 (2): 191–197. doi:10.1254/jjp.41.191. PMID 3747266.
  12. Greig, M. E.; Walk, R. A.; Gibbons, A. J. (1959). "The effect of three tryptamine derivatives on serotonin metabolism in vitro and in vivo". The Journal of Pharmacology and Experimental Therapeutics. 127: 110–115. PMID 13851725.
  13. Gey, K. F.; Pletscher, A. (1962). "Effect of alpha-alkylated tryptamine derivatives on 5-hydroxytryptamine metabolism in vivo". British Journal of Pharmacology and Chemotherapy. 19 (1): 161–167. doi:10.1111/j.1476-5381.1962.tb01437.x. PMC 1482243. PMID 13898151.
  14. "Shulgin, A (1997) TIHKAL". Erowid.org. Retrieved 2013-10-16.
  15. "AMT Dosage". Erowid. 2011-02-02. Retrieved 2013-10-16.
  16. Szara, S. (1961). "6-Hydroxylation: An important metabolic route for α-methyltryptamine". Experientia. 17 (2): 76–7. doi:10.1007/BF02171429. PMID 13774483.
  17. Kanamori, T.; Kuwayama, K.; Tsujikawa, K.; Miyaguchi, H.; Iwata, Y. T.; Inoue, H. (2008). "In vivometabolism of α-methyltryptamine in rats: Identification of urinary metabolites". Xenobiotica. 38 (12): 1476–1486. doi:10.1080/00498250802491654. PMID 18982537.
  18. Wilcox, J. (2012). "Psychoactive Properties of Alpha-Methyltryptamine: Analysis from Self Reports of Users". Journal of Psychoactive Drugs. 44 (3): 274–276. doi:10.1080/02791072.2012.704592. PMID 23061328.
  19. "Erowid AMT Vault : Effects".
  20. Huang XM, Johnson MP, Nichols DE (July 1991). "Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase)". European Journal of Pharmacology. 200 (1): 187–90. doi:10.1016/0014-2999(91)90686-K. PMID 1722753.
  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. http://www.who.int/medicines/areas/quality_safety/4_20_Review.pdf
  23. "CSDA".
  24. "Medicamentos de Uso Humano - Estupefacientes y Psicótropos". Agencia Española de Medicamentos y Productos Sanitarios.
  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, 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 from the original on 2013-10-17. Retrieved 2013-10-10.CS1 maint: BOT: original-url status unknown (link)
  29. http://www.finlex.fi/data/sdliite/liite/6194.pdf
  30. Gillman, P. K. (2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity" (PDF). British Journal of Anaesthesia. 95 (4): 434–441. doi:10.1093/bja/aei210. 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. Boland, Diane M.; Andollo W; Hime GW; Hearn WL (July–August 2005). "Fatality Due to Acute Alpha-methyltryptamine Intoxication" (PDF). Journal of Analytical Toxicology. 29 (5): 394–397. doi:10.1093/jat/29.5.394. PMID 16105268. Retrieved October 1, 2013.
  32. "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.
  33. "Southampton 'legal high' death deemed 'accidental'". BBC News. 2013-11-12. Retrieved 2013-11-19.
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