Biology:Α-Methyltryptamine

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α-Methyltryptamine (αMT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine and α-alkyltryptamine families.[1][2] It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued.[3][4][5]

Side effects of αMT include agitation, restlessness, confusion, lethargy, pupil dilation, jaw clenching, and rapid heart rate, among others.[3][6] αMT acts as a releasing agent of serotonin, norepinephrine, and dopamine, as a serotonin receptor agonist, and as a weak monoamine oxidase inhibitor.[7] αMT is a substituted tryptamine and is closely related to α-ethyltryptamine (αET) and other α-alkylated tryptamines.[7][1]

αMT appears to have first been described by at least 1929.[8][9] It started being more studied in the late 1950s and was briefly used as an antidepressant in the Soviet Union in the 1960s.[3][10][6][11][12] The drug started being used recreationally in the 1960s, with use increasing in the 1990s, and cases of death have been reported.[3][11][6][10] αMT is a controlled substance in various countries, including the United States.[11][3]


Use and effects

Under the brand name Indopan or Indopane, αMT at doses of 5 to 10 mg was used for an antidepressant effect.[3][4][5]

At a dose of 20 mg, it produces euphoria, while doses above 30 mg result in strong hallucinogenic effects. At doses over 30 mg, the compound may cause several side effects, including anxiety, muscle tightness, vomiting, and hyperthermia.[13] A dose exceeding 40 mg is generally considered strong. In rare cases or extreme doses, the duration of effects might exceed 24 h. Users report that αMT may be smoked, with doses between and 2 and 20 mg.[14] [1]

A dose of 20 mg of αMT is said to be equivalent to 50 μg of LSD. However, its onset of action is delayed, with effects appearing after only 3 to 4 hours, and it is longer-lasting. In addition, αMT is described as unpleasant compared to LSD, with symptoms of nervousness, irritability, restlessness, and inability to relax.[15]

Side effects

Neurologic side effects of αMT include agitation, restlessness, confusion, and lethargy.[3][6][15] Physical manifestations including vomiting, mydriasis (pupillary dilation), jaw clenching, tachycardia, salivation, diaphoresis (sweating), and elevations in blood pressure, temperature, and respiratory rate.[3][6]

Side effects self-reported by recreational users include anxiety, muscle tension, jaw tightness, pupil dilation, tachycardia, headaches, nausea, and vomiting, as well as psychedelic effects including visual hallucinations and an altered state of mind.[1][16]

αMT is capable of causing life-threatening side effects including hyperthermia, hypertension, and tachycardia.[6][17] Fatalities have been reported in association with high doses or concomitant use of other drugs.[18]

Fatalities verified with toxicology and autopsy include those of a 22-year-old man in Miami-Dade County, Florida and a British teenager, both of whom died after consuming 1 g of αMT.[19][6]

Interactions

Pharmacology

Pharmacodynamics

αMT acts as a relatively balanced reuptake inhibitor and releasing agent of the main three monoamines; serotonin, norepinephrine, and dopamine,[20] and as a non-selective serotonin receptor agonist.[21] It has relatively weak psychedelic-like effects in animals compared to other psychedelic substituted tryptamines, for instance in terms of the head-twitch response in rodents.[15]

Activities of αMT and related compounds
Compound Monoamine release (EC50, nM) 5-HT2A receptor agonism
Serotonin Dopamine Norepinephrine EC50 (nM) Emax (%)
Tryptamine 33 164 716 7.4 104
Serotonin 44 >10,000 >10,000 ND ND
N,N-DMT 114 >10,000 4,166 38 83
αMT 22–68 79–112 79–180 23 103
αET 23 232 640 (Emax = 78%) >10,000 21
5-MeO-αMT 460 8,900 1,500 2.0–8.4 ND
MDMA 57 376 77 ND ND
Notes: The smaller the value, the more strongly the compound produces the effect. Refs:[22][7][23][24][25]

Monoamine oxidase inhibition

αMT has been shown as a reversible inhibitor of the enzyme monoamine oxidase (MAO) in vitro[26] and in vivo.[27] 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] Dextroamphetamine did not enhance the 5-hydroxytryptophan-induced rise of serotonin at any level.[28] The IC50 of αMT for inhibition of MAO-A has been found to be 380 nM.[29] This is similar to that of agents like para-methoxyamphetamine (PMA) and 4-methylthioamphetamine (4-MTA).[30]

Serotonergic neurotoxicity

A close analogue of αMT, α-ethyltryptamine (αET), is known to be a serotonergic neurotoxin similarly to MDMA and para-chloroamphetamine (PCA).[31][22][32]

Pharmacokinetics

2-Oxo-αMT, 6-hydroxy-αMT, 7-hydroxy-αMT, and 1′-hydroxy-αMT were detected as metabolites of αMT in male Wistar rats.[3][33][34]

Chemistry

αMT is a synthetic substituted tryptamine with a methyl substituent at the alpha carbon.[7][6] 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.[6] αMT is closely related to the neurotransmitter serotonin (5-hydroxytryptamine) which partially explains its mechanism of action.

Synthesis

The chemical synthesis of αMT has been described.[1] Its synthesis can be accomplished through several different routes, there's two "common" routes mainly via the Henry reaction aka Nitroadol condensation between indole-3-carboxaldehyde and nitroethane under amine salt or ionic liquid catalysis which produces 1-(3-indolyl)-2-nitropropene-1, 1-(3-indolyl)-2-nitropropene-1 can subsequently be reduced via a reducing agent such as lithium aluminum hydride[35] The alternative synthesis is the condensation between indole-3-acetone and hydroxylamine , followed by reduction of the obtained ketoxime with lithium aluminum hydride.[1]

Analogues

Many analogues of αMT are known, including α-ethyltryptamine (αET), α-propyltryptamine (αPT), 4-methyl-αMT, 5-chloro-αMT (PAL-542), 5-fluoro-αMT (PAL-544), 5-fluoro-αET (PAL-545), 5-methoxy-αMT (5-MeO-αMT), α,N-dimethyltryptamine (α,N-DMT; N-methyl-αMT), α,N,N-trimethyltryptamine (α,N,N-TMT; N-dimethyl-αMT), α-methylserotonin (α-methyl-5-HT; 5-hydroxy-αMT), and indolylpropylaminopentane (IPAP; α,N-dipropyltryptamine or α,N-DPT), among others.[7][1] Another analogue of αMT is the β-keto and N-methylated derivative BK-NM-AMT.[36][37][38]

α-Methyltryptophan, a prodrug of α-methylserotonin, also metabolizes into αMT, but only in small amounts.[39][40][41]

There are seven possible positional isomers of aminopropylindole (API; IT), wherein the side chain is located at different positions of the indole ring system.[42][1][43] These positional isomers include 1-API (α-methylisotryptamine; isoAMT; PAL-569), 2-API, 3-API (3-IT; α-methyltryptamine; AMT; PAL-17), 4-API, 5-API (5-IT; 3,4-pyrrolo[b]amphetamine; PAL-571), 6-API, and 7-API.[42][1][43] 3-API or AMT is an α-alkyltryptamine, 1-API or isoAMT is an isotryptamine, and 4-API, 5-API, 6-API, and 7-API are all phenethylamines and amphetamines.[42][1][43]

The analogue of AMT without the benzene part of the indole ring is 3-pyrrolylpropylamine.[44]

History

αMT has been said to have been first synthesized in 1947, alongside α-ethyltryptamine (αET).[10][22][45] However, other sources suggest that αMT was first described in the scientific literature by at least 1929.[8][9] It was specifically described as an antagonist of ergotamine at this time.[8][9]

αMT started to be more intensively studied, along with αET, in the late 1950s and early 1960s.[10][46][47][48][28][49][50][51][52][53] It was researched by Upjohn (code name U-14,164E) and Sandoz (code name IT-290) as a possible pharmaceutical drug and was simultaneously marketed in the Soviet Union as an antidepressant under the brand name Indopan or Indopane in the 1960s.[11][12][6][54] However, the drug was used clinically for only a short period of time before being withdrawn.[12]

αMT started being used as a recreational drug in the 1960s[6] and use as a designer drug increased in the 1990s.[11] It became a controlled substance in the United States in 2003.[11]

Society and culture

Names

αMT never received a formal generic name.[55] In the scientific literature, it has been referred to as α-methyltryptamine or alpha-methyltryptamine (abbreviated as α-MT, αMT, or AMT).[11][12] αMT has also been referred to by developmental code names including IT-290 (Sandoz),[56] NSC-97069,[10] PAL-17,[7] Ro 3-0926,[57][58] and U-14,164E (Upjohn).[59][60][10][6] In the Soviet Union, the drug was merely referred to by its brand name Indopan or Indopane.[61][6] Other synonyms of αMT include 3-(2-aminopropyl)indole and 3-IT.[10] (+)-αMT has been referred to by the code name IT-403.[10][6]

Australia

The 5-methoxy analogue, 5-MeO-αMT is schedule 9 in Australia and αMT would be controlled as an analogue of this.[62]

Austria

αMT is placed under Austrian law (NPSG) Group 6.[63]

Canada

AMT is not an explicitly nor implicitly controlled substance in Canada as of 2025.[64]

China

As of October 2015 αMT is a controlled substance in China.[65]

Denmark

In Denmark (2010), the Danish Minister for the Interior and Health placed αMT to their lists of controlled substances (List B).[63]

Finland

AMT, alfa-methyltryptamine, is a controlled drug in Finland.[66]

Germany

αMT is listed under the Narcotics Act in schedule 1 (narcotics not eligible for trade and medical prescriptions) in Germany.[63]

Hungary

αMT was controlled on the Schedule C list in Hungary in 2013.[63]

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.[63]

Slovakia

αMT was placed in 2013 on the List of Hazardous Substances in Annex, § 2 in Slovakia.[63]

Slovenia

αMT appeared on the Decree on Classification of Illicit Drugs in Slovenia (2013).[63]

Spain

αMT is legal in Spain.[67]

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.[68]

United Kingdom

αMT was made illegal in the United Kingdom as of 7 January 2015, along with 5-MeO-DALT.[69] 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.[70]

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).[71]

Research

Besides depression, αMT has been studied in people with schizophrenia and other conditions.[7]

See also

Notes

  1. ↑ MAOI potency was comparable at 7 μM/kg, equivalent to 1.5 mg/kg of Harmaline and 1.2 mg/kg of αMT. At 70 μM/kg αMT was a much less effective MAOI than harmaline.[28]

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 "#48 a-MT". Erowid Online Books: TIHKAL. http://www.erowid.org/library/books_online/tihkal/tihkal48.shtml. 
  2. ↑ "AMT (alpha-methyltryptamine)". Erowid Vault. http://www.erowid.org/chemicals/amt/amt.shtml. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 3.7 3.8 Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. John Wiley & Sons. 20 March 2012. pp. 196–199. ISBN 978-0-471-72760-6. https://books.google.com/books?id=OWFiVaDZnkQC&pg=PA196. 
  4. ↑ 4.0 4.1 Handbook of Psychopharmacology: Volume 14 Affective Disorders: Drug Actions in Animals and Man. Springer Science & Business Media. 11 November 2013. pp. 132–. ISBN 978-1-4613-4045-4. https://books.google.com/books?id=ogXrBwAAQBAJ&pg=PA132. 
  5. ↑ 5.0 5.1 "Neuropharmacology of lysergic acid diethylamide (LSD) and other hallucinogens.". Biological Research on Addiction: Comprehensive Addictive Behaviors and Disorders. 2. Academic Press. 17 May 2013. pp. 625–635 (632). doi:10.1016/B978-0-12-398335-0.00061-3. ISBN 978-0-12-398360-2. https://books.google.com/books?id=ZUeCgcrNjOUC&pg=PA632. 
  6. ↑ 6.00 6.01 6.02 6.03 6.04 6.05 6.06 6.07 6.08 6.09 6.10 6.11 6.12 6.13 "Fatality due to acute alpha-methyltryptamine intoxication". Journal of Analytical Toxicology 29 (5): 394–397. July–August 2005. doi:10.1093/jat/29.5.394. PMID 16105268. "α-Methyltryptamine (AMT) is a synthetic drug of the tryptamine family. It is an indole analogue of amphetamine initially investigated as a monoamine oxidase inhibitor. In the 1960s, the Soviet Union marketed AMT as an antidepressant under the name of Indopan. During the same period, Sandoz (as IT-290 and IT-403) and the Upjohn Company (as [U-14,164E]) studied AMT and its commercial use as a stimulant, but found it to be of little medicinal value. Although clinical use of AMT is obsolete today, recreational use has gained popularity because of the intense hallucinogenic properties lasting up to 16 h. To illustrate recreational use of AMT in the 1960s, Alexander Shulgin, in his book TiHKAL, references the author Ken Kesey and his experiences with AMT and other hallucinogenic drugs (1).". 
  7. ↑ 7.0 7.1 7.2 7.3 7.4 7.5 7.6 "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters 24 (19): 4754–4758. October 2014. doi:10.1016/j.bmcl.2014.07.062. PMID 25193229. 
  8. ↑ 8.0 8.1 8.2 "Drugs which antagonize 5-hydroxytryptamine". British Journal of Pharmacology and Chemotherapy 9 (2): 240–248. June 1954. doi:10.1111/j.1476-5381.1954.tb00848.x. PMID 13172437. "The antagonism of ergotoxine and tryptamine was described by Laidlaw (1911) and that of ergotamine and α-methyltryptamine by Seki (1929).". 
  9. ↑ 9.0 9.1 9.2 "Pharmakologische Untersuchungen des α-Methyl-β-indoläthylamins". Japanese Journal of Medical Sciences. Part 4: Pharmacology (National Research Council of Japan) 3: 235–285. 1929. ISSN 0368-3745. OCLC 610325817. https://books.google.com/books?id=rrZXAAAAMAAJ&q=%22Pharmakologische+Untersuchungen+des+a-Methyl-8-indol%C3%A4thylamins%22. 
  10. ↑ 10.0 10.1 10.2 10.3 10.4 10.5 10.6 10.7 "AMT (3-(2-aminopropyl)indole) and 5-IT (5-(2-aminopropyl)indole): an analytical challenge and implications for forensic analysis". Drug Testing and Analysis 5 (3): 196–202. March 2013. doi:10.1002/dta.1420. PMID 23042766. "α-Methyltryptamine (2, 3-(2-aminopropyl)indole, AMT, α-MT, 3-IT, IT-290, IT-403, U-14, 162-E, Ro 3-0926, NSC 97069, Indopan; Figure 1), on the other hand, is a positional isomer of 5-IT that also shows long-lasting psychoactive effects in humans[1] although further studies are needed to determine the differences or similarities between both psychopharmacological profiles. Following its first synthesis in 1947,[5] the interest in AMT, and other α-alkylated tryptamines, began to develop in the late 1950s when it was discovered that some of these analogues also displayed monoamine oxidase (MAO) inhibiting properties.[6,7] [...]". 
  11. ↑ 11.0 11.1 11.2 11.3 11.4 11.5 11.6 "The hallucinogenic world of tryptamines: an updated review". Archives of Toxicology 89 (8): 1151–1173. August 2015. doi:10.1007/s00204-015-1513-x. PMID 25877327. Bibcode: 2015ArTox..89.1151A. 
  12. ↑ 12.0 12.1 12.2 12.3 "Recreational use, analysis and toxicity of tryptamines". Current Neuropharmacology 13 (1): 26–46. January 2015. doi:10.2174/1570159x13666141210222409. PMID 26074742. 
  13. ↑ "Psychoactive properties of alpha-methyltryptamine: analysis from self reports of users". Journal of Psychoactive Drugs 44 (3): 274–276. 2012. doi:10.1080/02791072.2012.704592. PMID 23061328. 
  14. ↑ Dialtonez (12 March 2003). "AMT FAQ". Erowid Vault. http://www.erowid.org/chemicals/amt/amt_faq1.shtml. 
  15. ↑ 15.0 15.1 15.2 "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. 1975. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. https://bitnest.netfirms.com/external/Books/978-0-85608-011-1. "α-Methyltryptamine produced a subjective LSD-like reaction in man, a dose of 20 mg being equivalent to 50 µg of LSD with effects appearing only after 3–4 hours following oral administration (Murphree, Jenney, and Pfeiffer, 1960). The majority of subjects in a larger study (Murphree, Dippy, Jenney, and Pfeiffer, 1961) reported that they were nervous, irritable, restless, and could not relax. Visual effects were not prominent and the experience was likened to an unpleasant, long-lasting LSD reaction. [...] Szara (1961a) reported that 20 mg of α-methyltryptamine was equivalent to 60 mg of DET in psychotomimetic activity with more perceptual distortions and less autonomic activity. Neither of the α-alkyltryptamines is particularly potent in behavioural studies in animals (Hoffer and Osmond, 1967) and their hallucinogenic potential is clearly limited in comparison to other tryptamines. In production of head twitches in mice, for example, α-ethyltryptamine was inactive while α-methyltryptamine was only slightly more active than mescaline with an ED50 of 7·9 mg/kg. (s.c.) (Corne and Pickering, 1967)." 
  16. ↑ "AMT Effects". Erowid Vault. http://www.erowid.org/chemicals/amt/amt_effects.shtml. 
  17. ↑ "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity". British Journal of Anaesthesia 95 (4): 434–441. October 2005. 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"
  18. ↑ "Call for ban on drug after reveller's death". Western Gazette. 22 March 2012. http://www.thisissomerset.co.uk/Torch-carriers-miles-home/story-15588409-detail/story.html#axzz2glqAXLdX. 
  19. ↑ "Southampton 'legal high' death deemed 'accidental'". BBC News. 12 November 2013. https://www.bbc.co.uk/news/uk-england-hampshire-24915409. 
  20. ↑ "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology 559 (2–3): 132–137. March 2007. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101. 
  21. ↑ "In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes". Biological & Pharmaceutical Bulletin 30 (12): 2328–2333. December 2007. doi:10.1248/bpb.30.2328. PMID 18057721. 
  22. ↑ 22.0 22.1 22.2 "α-Ethyltryptamine: A Ratiocinatory Review of a Forgotten Antidepressant". ACS Pharmacology & Translational Science 6 (12): 1780–1789. December 2023. doi:10.1021/acsptsci.3c00139. PMID 38093842. 
  23. ↑ "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl) 231 (21): 4135–4144. October 2014. doi:10.1007/s00213-014-3557-7. PMID 24800892. 
  24. ↑ "Monoamine transporters and psychostimulant drugs". Eur J Pharmacol 479 (1–3): 23–40. October 2003. doi:10.1016/j.ejphar.2003.08.054. PMID 14612135. 
  25. ↑ "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol 559 (2–3): 132–137. March 2007. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101. 
  26. ↑ "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". Japanese Journal of Pharmacology 41 (2): 191–197. June 1986. doi:10.1254/jjp.41.191. PMID 3747266. 
  27. ↑ "The effect of three tryptamine derivatives on serotonin metabolism in vitro and in vivo". The Journal of Pharmacology and Experimental Therapeutics 127 (2): 110–115. October 1959. doi:10.1016/S0022-3565(25)25666-X. PMID 13851725. http://jpet.aspetjournals.org/content/127/2/110.short. 
  28. ↑ 28.0 28.1 28.2 "Effect of alpha-alkylated tryptamine derivatives on 5-hydroxytryptamine metabolism in vivo". British Journal of Pharmacology and Chemotherapy 19 (1): 161–167. August 1962. doi:10.1111/j.1476-5381.1962.tb01437.x. PMID 13898151. 
  29. ↑ "In vitro monoamine oxidase inhibition potential of alpha-methyltryptamine analog new psychoactive substances for assessing possible toxic risks". Toxicol Lett 272: 84–93. April 2017. doi:10.1016/j.toxlet.2017.03.007. PMID 28302559. Bibcode: 2017ToxL..272...84W. https://researchonline.ljmu.ac.uk/id/eprint/5909/1/TOXLET-D-17-00086R1_accepted_uncorected.pdf. 
  30. ↑ "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol 10. 2019. doi:10.3389/fphar.2019.01590. PMID 32038257. 
  31. ↑ "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". Journal of Psychopharmacology 35 (5): 512–536. May 2021. doi:10.1177/0269881120920420. PMID 32909493. 
  32. ↑ "Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase)". European Journal of Pharmacology 200 (1): 187–190. July 1991. doi:10.1016/0014-2999(91)90686-k. PMID 1722753. 
  33. ↑ "6-Hydroxylation: an important metabolic route for alpha-methyltryptamine". Experientia 17 (2): 76–77. February 1961. doi:10.1007/BF02171429. PMID 13774483. 
  34. ↑ "In vivo metabolism of alpha-methyltryptamine in rats: identification of urinary metabolites". Xenobiotica; the Fate of Foreign Compounds in Biological Systems 38 (12): 1476–1486. December 2008. doi:10.1080/00498250802491654. PMID 18982537. 
  35. ↑ "Synthesis of alpha-Methyltryptamine (IT-290/AMT)". TheHive. https://chemistry.mdma.ch/hiveboard/rhodium/it-290.html. 
  36. ↑ "The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes". Psychopharmacology (Berl) 236 (3): 915–924. March 2019. doi:10.1007/s00213-018-5063-9. PMID 30341459. 
  37. ↑ & Sean Dalziel"Specialized combinations for mental disorders or mental enhancement" US patent 20240335414, published 10 October 2024
  38. ↑ Matthew Baggott, "Advantageous tryptamine compositions for mental disorders or enhancement", WO patent 2022061242, published 2023 March 24, assigned to Tactogen
  39. ↑ "Alpha-methyltryptophan as a therapeutic agent". Prog Neuropsychopharmacol Biol Psychiatry 15 (6): 935–938. 1991. doi:10.1016/0278-5846(91)90020-2. PMID 1763198. 
  40. ↑ "Alpha-methyltryptophan: effects on synthesis and degradation of serotonin in the brain". Neuropharmacology 11 (2): 197–209. March 1972. doi:10.1016/0028-3908(72)90092-5. PMID 4260268. 
  41. ↑ "Effects of p-chlorophenylalanine and alpha-methyltryptophan on behaviour and brain 5-hydroxyindoles". Neuropharmacology 16 (7–8): 489–494. 1977. doi:10.1016/0028-3908(77)90006-5. PMID 144245. 
  42. ↑ 42.0 42.1 42.2 "Identification of (2-aminopropyl)indole positional isomers in forensic samples". Drug Test Anal 6 (7–8): 598–606. 2014. doi:10.1002/dta.1508. PMID 23836607. http://funes.uniandes.edu.co/22343/1/Sanchez2016Algebra.pdf. 
  43. ↑ 43.0 43.1 43.2 "Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys". Exp Clin Psychopharmacol 22 (3): 274–284. June 2014. doi:10.1037/a0036595. PMID 24796848. 
  44. ↑ "Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region". Journal of Medicinal Chemistry 33 (10): 2777–2784. October 1990. doi:10.1021/jm00172a016. PMID 2213830. 
  45. ↑ "The alkylation of aliphatic nitro compounds with gramine; a new synthesis of derivatives of tryptamine". Journal of the American Chemical Society 69 (12): 3140–3142. December 1947. doi:10.1021/ja01204a061. PMID 18919717. Bibcode: 1947JAChS..69.3140S. 
  46. ↑ "The effect of three tryptamine derivatives on serotonin metabolism in vitro and in vivo". The Journal of Pharmacology and Experimental Therapeutics 127 (2): 110–115. October 1959. doi:10.1016/S0022-3565(25)25666-X. PMID 13851725. 
  47. ↑ "The Synthesis of α-Methyltryptophans and α-Alkyltryptamines". The Journal of Organic Chemistry 25 (9): 1548–1558. 1960. doi:10.1021/jo01079a021. ISSN 0022-3263. 
  48. ↑ "Effects in normal man of alpha-methyltryptamine and alpha-ethyltryptamine". Clinical Pharmacology and Therapeutics 2 (6): 722–726. 1961. doi:10.1002/cpt196126722. PMID 14477400. 
  49. ↑ "Experiments with alpha-methyltryptamine". Journal of Neuropsychiatry 2 (Suppl 1): 136–140. February 1961. PMID 13714418. 
  50. ↑ "Tryptamine receptors in the central nervous system". Nature 191 (4793): 1068–1069. September 1961. doi:10.1038/1911068a0. PMID 13780152. Bibcode: 1961Natur.191.1068V. 
  51. ↑ "Studies on the toxicology of alpha-methyl- and alpha-ethyltryptamine acetates (Monase). II. Chronic studies". Toxicology and Applied Pharmacology 4 (6): 697–709. November 1962. doi:10.1016/0041-008x(62)90099-6. PMID 14031765. Bibcode: 1962ToxAP...4..697K. 
  52. ↑ "Metabolism and behavioural action of psychotropic tryptamine homologues". International Journal of Neuropharmacology 1 (1–3): 111–117. 1962. doi:10.1016/0028-3908(62)90015-1. 
  53. ↑ "[Pharmacological properties of indopane (alpha-methyltryptamine HCl)]" (in Russian). Zhurnal Nevropatologii I Psikhiatrii imeni S.S. Korsakova 63: 72–79. 1963. PMID 13933321. 
  54. ↑ Szmuszkovicz J, "Method of Treating Mental Depression", US patent Patent 3296072, published 1967-01-03, assigned to Upjohn Co.
  55. ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. 2014. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ. Retrieved 7 September 2024. 
  56. ↑ "Comparison of three psychotropic drugs (psilocybin, JB-329, and IT-290) in volunteer subjects". The Journal of Nervous and Mental Disease 131 (5): 428–434. November 1960. doi:10.1097/00005053-196011000-00007. PMID 13715375. 
  57. ↑ "Conversion of indolylalkylhydroxylamines to stimulant amines in vivo". Biochemical Pharmacology 15 (4): 481–487. April 1966. doi:10.1016/0006-2952(66)90258-9. PMID 5954980. 
  58. ↑ "The central stimulant properties of some substituted indolylalkylamines and beta-carbolines and their activities as inhibitors of monoamine oxidase and the uptake of 5-hydroxytryptamine". British Journal of Pharmacology and Chemotherapy 29 (1): 70–79. January 1967. doi:10.1111/j.1476-5381.1967.tb01940.x. PMID 19108241. 
  59. ↑ "Effect of Monase and related compounds on uptake of 5-hydroxytryptamine by platelets". Proceedings of the Society for Experimental Biology and Medicine 122 (3): 711–714. July 1966. doi:10.3181/00379727-122-31233. PMID 5918937. 
  60. ↑ Offermeier J (1965). Serotonin and its derivatives: a study on structure-activity relations (Ph.D. thesis). Catholic University of Nijmegen. Retrieved 7 September 2024.
  61. ↑ "("indopan"[title OR "indopane"[title])"]. PubMed. U.S. National Library of Medicine. https://pubmed.ncbi.nlm.nih.gov/?term=%28%22indopan%22%5Btitle%5D+OR+%22indopane%22%5Btitle%5D%29&sort=pubdate. 
  62. ↑ 63.0 63.1 63.2 63.3 63.4 63.5 63.6 Expert Committee on Drug Dependence Thirty-sixth Meeting (June 2014). "Alpha-methyltryptamine (AMT) Critical Review Report Agenda item 4.20". Geneva: World Health Organization (WHO). https://www.who.int/medicines/areas/quality_safety/4_20_Review.pdf. 
  63. ↑ "Controlled Drugs and Substances Act". 5 December 2025. https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  64. ↑ "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 zh). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 
  65. ↑ "Lääkeluettelon Aineet, Liite 1, Bilaga 1.3". Finlex Data Bank. Finnish Ministry of Justice. http://www.finlex.fi/data/sdliite/liite/6194.pdf. 
  66. ↑ "Medicamentos de Uso Humano - Estupefacientes y Psicótropos". https://www.aemps.gob.es/medicamentosUsoHumano/estupefacientesPsicotropos/home.htm. 
  67. ↑ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor [Ordinance amending the Ordinance (1999:58) on the prohibition of certain goods hazardous to health"] (in sv), Lagen om förbud mot vissa hälsofarliga varor - SFS 2005:26, February 2005, http://www.notisum.se/rnp/sls/sfs/20050026.pdf, retrieved 2013-10-07 
  68. ↑ "The Misuse of Drugs (Amendment No. 3) (England, Wales and Scotland) Regulations 2014". http://www.legislation.gov.uk/uksi/2014/3277/introduction/made/data.htm. 
  69. ↑ ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines". UK Home Office. p. 12. https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/318693/UpdateGenericDefinitionTryptamines.pdf. 
  70. ↑ "Alpha-methyltryptamine". DEA Office of Diversion Control. April 2013. http://www.deadiversion.usdoj.gov/drug_chem_info/amt.pdf. 



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