View source for Α-Methyltryptamine

{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Lowercase title}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 443378813
| drug_name = α-Methyltryptamine
| image = AMT.svg
| image_class = skin-invert-image
| width = 220px
| image2 = AMT 3D BS.png
| image_class2 = bg-transparent
| width2 = 220px

<!-- Clinical data -->
| tradename = Indopan; Indopane
| pregnancy_category = 
| routes_of_administration = [[Oral administration|Oral]], [[insufflation (medicine)|insufflation]], [[rectal administration|rectal]], [[vaporizer (inhalation device)|smoked]], [[intramuscular injection|IM]], [[intravenous administration|IV]]<ref name="urlErowid AMT Vault : FAQ by Dialtonez"/>
| class = [[Entactogen]]; [[Stimulant]]; [[Psychedelic drug|Psychedelic]]; [[Hallucinogen]]; [[Monoamine releasing agent]]; [[Serotonin receptor agonist]]; [[Monoamine oxidase inhibitor]]

<!-- Legal status -->
| legal_AU = Schedule 8
| legal_BR = F2
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>
| legal_CA = Unscheduled
| legal_UK = Class A
| legal_US = Schedule I
| legal_DE = Anlage I

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = 
| onset = 3–4{{nbsp}}hours<ref name="Barceloux2012" />
| elimination_half-life = 
| duration_of_action = 12–24{{nbsp}}hours<ref name="Barceloux2012" />
| excretion =

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 299-26-3
| ATC_prefix = None
| ATC_suffix = 
| PubChem = 9287
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01446
| KEGG = C20127
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8930
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BIK35ACJ0Q
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 59020
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 30713
| synonyms = ''alpha''-Methyltryptamine; αMT; α-ET; AMT; IT-290; IT-403 ((+)-αMT); NSC-97069; PAL-17;<ref name="BloughLandavazo2014" /> Ro 3-0926; U-14,164E; U-14,164-E; 3-(2-Aminopropyl)indole; 3-API; 3-IT; α-Methyl-3-indoleethanamine; Metryptamine; Amtryptamine

<!-- Chemical data -->
| IUPAC_name = 1-(1''H''-Indol-3-yl)propan-2-amine
| C=11 | H=14 | N=2
| SMILES = NC(CC1=CNC2=C1C=CC=C2)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QSQQQURBVYWZKJ-UHFFFAOYSA-N
}}
<!-- Definition and medical uses -->
'''α-Methyltryptamine''' ('''αMT''', '''AMT''') is a [[psychedelic drug|psychedelic]], [[stimulant]], and [[entactogen]] [[drug]] of the [[substituted tryptamine|tryptamine]] and [[substituted α-alkyltryptamine|α-alkyltryptamine]] families.<ref name="TiHKAL">{{cite web | url = http://www.erowid.org/library/books_online/tihkal/tihkal48.shtml | work = Erowid Online Books: TIHKAL | title = #48 a-MT }}</ref><ref name="urlErowid AMT (alpha-methyltryptamine) Vault">{{cite web | url = http://www.erowid.org/chemicals/amt/amt.shtml | work = Erowid Vault | title = AMT (alpha-methyltryptamine) }}</ref> 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.<ref name="Barceloux2012">{{cite book| vauthors = Barceloux DG |title=Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants|url=https://books.google.com/books?id=OWFiVaDZnkQC&pg=PA196|date=20 March 2012|publisher=John Wiley & Sons|isbn=978-0-471-72760-6|pages=196–199}}</ref><ref name="Iversen2013">{{cite book| vauthors = Iversen L |title=Handbook of Psychopharmacology: Volume 14 Affective Disorders: Drug Actions in Animals and Man|url=https://books.google.com/books?id=ogXrBwAAQBAJ&pg=PA132|date=11 November 2013|publisher=Springer Science & Business Media|isbn=978-1-4613-4045-4|pages=132–}}</ref><ref name="AcademicPress2013">{{cite book | vauthors = Halberstadt AL, Geyer MA | chapter = Neuropharmacology of lysergic acid diethylamide (LSD) and other hallucinogens. | veditors = Miller PM, Ball SA, Bates ME, Blume AW, Kampman KM, Kavanagh DJ, Larimer ME, Petry NM, De Witte P |title=Biological Research on Addiction: Comprehensive Addictive Behaviors and Disorders | volume = 2 | chapter-url=https://books.google.com/books?id=ZUeCgcrNjOUC&pg=PA632|date=17 May 2013|publisher=Academic Press|isbn=978-0-12-398360-2|pages= 625–635 (632) | doi = 10.1016/B978-0-12-398335-0.00061-3 }}</ref>

<!-- Side effects, mechanism of action, and chemistry -->
[[Side effect]]s of αMT include [[psychomotor agitation|agitation]], [[wikt:restlessness|restlessness]], [[confusion]], [[lethargy]], [[mydriasis|pupil dilation]], [[bruxism|jaw clenching]], and [[tachycardia|rapid heart rate]], among others.<ref name="Barceloux2012" /><ref name="BolandAndolloHime2005" /> αMT acts as a [[serotonin–norepinephrine–dopamine releasing agent|releasing agent of serotonin, norepinephrine, and dopamine]], as a [[serotonin receptor agonist]], and as a weak [[monoamine oxidase inhibitor]].<ref name="BloughLandavazo2014">{{cite journal | vauthors = Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB | title = Alpha-ethyltryptamines as dual dopamine-serotonin releasers | journal = Bioorganic & Medicinal Chemistry Letters | volume = 24 | issue = 19 | pages = 4754–4758 | date = October 2014 | pmid = 25193229 | pmc = 4211607 | doi = 10.1016/j.bmcl.2014.07.062 }}</ref> αMT is a [[substituted tryptamine]] and is closely related to [[α-ethyltryptamine]] (αET) and other [[α-alkyltryptamine|α-alkylated tryptamine]]s.<ref name="BloughLandavazo2014" /><ref name="TiHKAL" />

<!-- History, society, and culture -->
αMT appears to have first been described by at least 1929.<ref name="GaddumHameed1954" /><ref name="Seki1929" /> It started being more studied in the late 1950s and was briefly used as an [[antidepressant]] in the [[Soviet Union]] in the 1960s.<ref name="Barceloux2012" /><ref name="ElliottBrandtFreeman2013" /><ref name="BolandAndolloHime2005" /><ref name="AraújoCarvalhoBastos2015" /><ref name="TittarelliMannocchiPantano2015" /> The drug started being used [[recreational drug|recreationally]] in the 1960s, with use increasing in the 1990s, and cases of death have been reported.<ref name="Barceloux2012" /><ref name="AraújoCarvalhoBastos2015" /><ref name="BolandAndolloHime2005" /><ref name="ElliottBrandtFreeman2013" /> αMT is a [[controlled substance]] in various countries, including the [[United States]].<ref name="AraújoCarvalhoBastos2015" /><ref name="Barceloux2012" />

{{TOC limit|2}}

==Use and effects==
Under the brand name Indopan or Indopane, αMT at doses of 5 to 10{{nbsp}}mg was used for an [[antidepressant]] effect.<ref name="Barceloux2012" /><ref name="Iversen2013" /><ref name="AcademicPress2013" />

At a dose of 20 mg, it produces [[euphoria]], while doses above 30 mg result in strong [[Hallucination|hallucinogenic effects]]. At doses over 30 mg, the compound may cause several side effects, including [[anxiety]], muscle tightness, [[vomiting]], and [[hyperthermia]].<ref>{{cite journal | vauthors = Wilcox J | title = Psychoactive properties of alpha-methyltryptamine: analysis from self reports of users | journal = Journal of Psychoactive Drugs | volume = 44 | issue = 3 | pages = 274–276 | year = 2012 | pmid = 23061328 | doi = 10.1080/02791072.2012.704592 | s2cid = 38340985 }}</ref> A dose exceeding 40{{nbsp}}mg is generally considered strong. In rare cases or extreme doses, the duration of effects might exceed 24{{nbsp}}hours. Users report that αMT in [[freebase (chemistry)|freebase]] [[drug form|form]] is [[smoking|smoked]], with doses between and 2 and 5{{nbsp}}mg.<ref name="urlErowid AMT Vault : FAQ by Dialtonez">{{Cite web| url = http://www.erowid.org/chemicals/amt/amt_faq1.shtml | work = Erowid Vault | title = AMT FAQ | author = Dialtonez | date = 12 March 2003 }}</ref>{{unreliable source?|date=January 2019}}<ref name="TiHKAL"/>

A dose of 20{{nbsp}}mg of αMT is said to be equivalent to 50{{nbsp}}μg of [[LSD]].<ref name="BrimblecombePinder1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | pages = 98–144 | title = Hallucinogenic Agents | date = 1975 | publisher = Wright-Scientechnica | location = Bristol | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1 | quote = 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).}}</ref> However, its [[onset of action]] is delayed, with effects appearing after only 3 to 4{{nbsp}}hours, and it is longer-lasting.<ref name="BrimblecombePinder1975" /> In addition, αMT is described as unpleasant compared to LSD, with symptoms of nervousness, irritability, restlessness, and inability to relax.<ref name="BrimblecombePinder1975" /> It is also said to not have prominent [[psychedelic visuals|visual]] effects.<ref name="BrimblecombePinder1975" />

==Side effects==
Neurologic side effects of αMT include [[psychomotor agitation|agitation]], [[wikt:restlessness|restlessness]], [[confusion]], and [[lethargy]].<ref name="Barceloux2012" /><ref name="BolandAndolloHime2005" /><ref name="BrimblecombePinder1975" /> Physical manifestations including [[vomiting]], [[mydriasis]] (pupillary dilation), [[bruxism|jaw clenching]], [[tachycardia]], [[salivation]], [[diaphoresis]] (sweating), and [[hypertension|elevations in blood pressure]], [[hyperthermia|temperature]], and [[respiratory rate]].<ref name="Barceloux2012" /><ref name="BolandAndolloHime2005">{{cite journal | vauthors = Boland DM, Andollo W, Hime GW, Hearn WL | title = Fatality due to acute alpha-methyltryptamine intoxication | journal = Journal of Analytical Toxicology | volume = 29 | issue = 5 | pages = 394–397 | date = July–August 2005 | pmid = 16105268 | doi = 10.1093/jat/29.5.394 | quote = 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). | doi-access = free }}</ref>

Side effects self-reported by recreational users include [[anxiety]], [[muscle tension]], [[trisma|jaw tightness]], [[pupil dilation]], [[tachycardia]], [[headache]]s, [[nausea]], and [[vomiting]], as well as [[Psychedelic drug|psychedelic]] effects including visual hallucinations and an [[altered state of mind]].<ref name="TiHKAL" /><ref name="urlErowid AMT Vault : Effects">{{cite web | url = http://www.erowid.org/chemicals/amt/amt_effects.shtml | work = Erowid Vault | title = AMT Effects }}</ref>

αMT is capable of causing life-threatening side effects including [[hyperthermia]], [[hypertension]], and [[tachycardia]].<ref name="BolandAndolloHime2005" /><ref name="Gillman2005">{{cite journal | vauthors = Gillman PK | title = Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity | journal = British Journal of Anaesthesia | volume = 95 | issue = 4 | pages = 434–441 | date = October 2005 | pmid = 16051647 | doi = 10.1093/bja/aei210 | doi-access = free }} "drugs such as MDMA, ecstasy (3,4-methylenedioxymethamphetamine), if combined with MAOIs (including moclobemide) do also cause fatalities because they act as serotonin releasers"</ref> Fatalities have been reported in association with high doses or concomitant use of other drugs.<ref>{{cite news|title=Call for ban on drug after reveller's death |url=http://www.thisissomerset.co.uk/Torch-carriers-miles-home/story-15588409-detail/story.html#axzz2glqAXLdX | archive-url = https://web.archive.org/web/20131016101947/http://www.thisissomerset.co.uk/Torch-carriers-miles-home/story-15588409-detail/story.html#axzz2glqAXLdX | archive-date = 16 October 2013 |access-date= 1 October 2013 |newspaper=Western Gazette |date=22 March 2012 |url-status=dead }}</ref> 

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{{nbsp}}g of αMT.<ref>{{cite news | title = Southampton 'legal high' death deemed 'accidental' | date = 12 November 2013 | url = https://www.bbc.co.uk/news/uk-england-hampshire-24915409 | work = BBC News | access-date = 19 November 2013 }}</ref><ref name="BolandAndolloHime2005" />

==Interactions==
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

==Pharmacology==
===Pharmacodynamics===
αMT acts as a relatively balanced [[reuptake inhibitor]] and [[releasing agent]] of the main three [[monoamines]]; [[serotonin]], [[norepinephrine]], and [[dopamine]],<ref name="pmid17223101">{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = European Journal of Pharmacology | volume = 559 | issue = 2–3 | pages = 132–137 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 }}</ref> and as a non-[[binding selectivity|selective]] [[serotonin receptor]] [[agonist]].<ref name="pmid18057721">{{cite journal | vauthors = Nonaka R, Nagai F, Ogata A, Satoh K | title = In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes | journal = Biological & Pharmaceutical Bulletin | volume = 30 | issue = 12 | pages = 2328–2333 | date = December 2007 | pmid = 18057721 | doi = 10.1248/bpb.30.2328 | doi-access = free }}</ref> It has relatively weak [[psychedelic]]-like effects in animals compared to other psychedelic [[Tryptamines|substituted tryptamines]], for instance in terms of the [[head-twitch response]] in rodents.<ref name="BrimblecombePinder1975" />

{| class="wikitable floatright" style="font-size:small;"
|+ Activities of αMT and related compounds
|-
! rowspan="2" | Compound !! colspan="3" | [[Monoamine releasing agent|Monoamine release]] ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}}, nM) !! colspan="2" | [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] [[agonist|agonism]]
|-
! [[Serotonin releasing agent|Serotonin]] !! [[Dopamine releasing agent|Dopamine]] !! [[Norepinephrine releasing agent|Norepinephrine]] !! {{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} (nM) !! [[Intrinsic activity|E<sub>max</sub>]] (%)
|-
| [[Tryptamine]]<!-- T; PAL-235 --> || 33 || 164 || 716 || 7.4 || 104
|-
| [[5-Hydroxytryptamine|Serotonin]]<!-- 5-HT --> || 44 || >10,000 || >10,000 || {{Abbr|ND|No data}} || {{Abbr|ND|No data}}
|-
| [[N,N-Dimethyltryptamine|''N'',''N''-DMT]] || 114 || >10,000 || 4,166 || 38 || 83
|-
| αMT<!-- PAL-17 --> || 22–68 || 79–112 || 79–180 || 23 || 103
|-
| [[α-Ethyltryptamine|αET]]<!-- (±)-αET; (RS)-αET; PAL-125 --> || 23 || 232 || 640 ({{Abbrlink|E<sub>max</sub>|maximal efficacy}} = 78%) || >10,000 || 21
|-
| [[5-MeO-αMT]] || 460 || 8,900 || 1,500 || 2.0–8.4<!-- See 5-MeO-AMT page for sources --> || {{Abbr|ND|No data}}
|-
| [[3,4-Methylenedioxy-N-methylamphetamine|MDMA]] || 57 || 376 || 77 || {{Abbr|ND|No data}} || {{Abbr|ND|No data}}
|- class="sortbottom"
| colspan="6" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Notes:''' The smaller the value, the more strongly the compound produces the effect. '''Refs:'''<ref name="GlennonDukat2023" /><ref name="BloughLandavazo2014" /><ref name="BloughLandavazoDecker2014">{{cite journal | vauthors = Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB | title = Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes | journal = Psychopharmacology (Berl) | volume = 231 | issue = 21 | pages = 4135–4144 | date = October 2014 | pmid = 24800892 | pmc = 4194234 | doi = 10.1007/s00213-014-3557-7 | url = }}</ref><ref name="RothmanBaumann2003">{{cite journal | vauthors = Rothman RB, Baumann MH | title = Monoamine transporters and psychostimulant drugs | journal = Eur J Pharmacol | volume = 479 | issue = 1–3 | pages = 23–40 | date = October 2003 | pmid = 14612135 | doi = 10.1016/j.ejphar.2003.08.054 | url = }}</ref><ref name="NagaiNonakaSatohHisashiKamimura2007">{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = Eur J Pharmacol | volume = 559 | issue = 2–3 | pages = 132–137 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 | url = }}</ref>
|}

====Monoamine oxidase inhibition====
αMT has been shown as a [[reversible reaction|reversible]] [[enzyme inhibitor|inhibitor]] of the [[enzyme]] [[monoamine oxidase]] (MAO) ''[[in vitro]]''<ref>{{cite journal | vauthors = Arai Y, Toyoshima Y, Kinemuchi H | title = 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 | journal = Japanese Journal of Pharmacology | volume = 41 | issue = 2 | pages = 191–197 | date = June 1986 | pmid = 3747266 | doi = 10.1254/jjp.41.191 | doi-access = free }}</ref> and ''[[in vivo]]''.<ref>{{cite journal | vauthors = Greig ME, Walk RA, Gibbons AJ | title = The effect of three tryptamine derivatives on serotonin metabolism in vitro and in vivo | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 127 | pages = 110–115 | date = October 1959 | issue = 2 | doi = 10.1016/S0022-3565(25)25666-X | pmid = 13851725 | url = http://jpet.aspetjournals.org/content/127/2/110.short | url-access = subscription }}</ref> In rats, the potency of αMT as an MAO-A inhibitor in the brain was approximately equal to that of [[harmaline]] at equimolar doses.{{refn|group=note|MAOI potency was comparable at 7{{nbsp}}μM/kg, equivalent to 1.5{{nbsp}}mg/kg of Harmaline and 1.2{{nbsp}}mg/kg of αMT. At 70{{nbsp}}μM/kg αMT was a much less effective MAOI than harmaline.<ref name="GeyPletscher1961">{{cite journal | vauthors = Gey KF, Pletscher A | title = Effect of alpha-alkylated tryptamine derivatives on 5-hydroxytryptamine metabolism in vivo | journal = British Journal of Pharmacology and Chemotherapy | volume = 19 | issue = 1 | pages = 161–167 | date = August 1962 | pmid = 13898151 | pmc = 1482243 | doi = 10.1111/j.1476-5381.1962.tb01437.x }}</ref>}} Dextroamphetamine did not enhance the [[5-hydroxytryptophan]]-induced rise of serotonin at any level.<ref name="GeyPletscher1961"/> The {{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}} of αMT for inhibition of MAO-A has been found to be 380{{nbsp}}nM.<ref name="WagmannBrandtKavanagh2017">{{cite journal | vauthors = Wagmann L, Brandt SD, Kavanagh PV, Maurer HH, Meyer MR | title = In vitro monoamine oxidase inhibition potential of alpha-methyltryptamine analog new psychoactive substances for assessing possible toxic risks | journal = Toxicol Lett | volume = 272 | issue = | pages = 84–93 | date = April 2017 | pmid = 28302559 | doi = 10.1016/j.toxlet.2017.03.007 | url = https://researchonline.ljmu.ac.uk/id/eprint/5909/1/TOXLET-D-17-00086R1_accepted_uncorected.pdf}}</ref> This is similar to that of agents like [[para-methoxyamphetamine|''para''-methoxyamphetamine]] (PMA) and [[4-methylthioamphetamine]] (4-MTA).<ref name="Reyes-ParadaIturriaga-VasquezCassels2019">{{cite journal | vauthors = Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK | title = Amphetamine Derivatives as Monoamine Oxidase Inhibitors | journal = Front Pharmacol | volume = 10 | issue = | article-number = 1590 | date = 2019 | pmid = 32038257 | pmc = 6989591 | doi = 10.3389/fphar.2019.01590 | doi-access = free | url = }}</ref>

====Serotonergic neurotoxicity====
A close [[structural analog|analogue]] of αMT, [[Alpha-Ethyltryptamine|α-ethyltryptamine]] (αET), is known to be a [[monoamine neurotoxin|serotonergic neurotoxin]] similarly to [[MDMA]] and [[para-chloroamphetamine|''para''-chloroamphetamine]] (PCA).<ref name="Oeri2021">{{cite journal | vauthors = Oeri HE | title = Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy | journal = Journal of Psychopharmacology | volume = 35 | issue = 5 | pages = 512–536 | date = May 2021 | pmid = 32909493 | pmc = 8155739 | doi = 10.1177/0269881120920420 }}</ref><ref name="GlennonDukat2023">{{cite journal | vauthors = Glennon RA, Dukat MG | title = α-Ethyltryptamine: A Ratiocinatory Review of a Forgotten Antidepressant | journal = ACS Pharmacology & Translational Science | volume = 6 | issue = 12 | pages = 1780–1789 | date = December 2023 | pmid = 38093842 | doi = 10.1021/acsptsci.3c00139 | pmc = 10714429 }}</ref><ref name="HuangJohnsonNichols1991">{{cite journal | vauthors = Huang XM, Johnson MP, Nichols DE | title = Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase) | journal = European Journal of Pharmacology | volume = 200 | issue = 1 | pages = 187–190 | date = July 1991 | pmid = 1722753 | doi = 10.1016/0014-2999(91)90686-k }}</ref>

===Pharmacokinetics===
2-Oxo-αMT, 6-hydroxy-αMT, 7-hydroxy-αMT, and 1′-hydroxy-αMT were detected as [[metabolite]]s of αMT in male [[Laboratory rat|Wistar rats]].<ref name="Barceloux2012" /><ref name="Szara1961">{{cite journal | vauthors = Szara S | title = 6-Hydroxylation: an important metabolic route for alpha-methyltryptamine | journal = Experientia | volume = 17 | issue = 2 | pages = 76–77 | date = February 1961 | pmid = 13774483 | doi = 10.1007/BF02171429 | s2cid = 27030395 | doi-access = free }}</ref><ref name="KanamoriKuwayamaTsujikawa2008">{{cite journal | vauthors = Kanamori T, Kuwayama K, Tsujikawa K, Miyaguchi H, Iwata YT, Inoue H | title = In vivo metabolism of alpha-methyltryptamine in rats: identification of urinary metabolites | journal = Xenobiotica; the Fate of Foreign Compounds in Biological Systems | volume = 38 | issue = 12 | pages = 1476–1486 | date = December 2008 | pmid = 18982537 | doi = 10.1080/00498250802491654 | s2cid = 20637936 }}</ref>

==Chemistry==
αMT is a [[synthetic compound|synthetic]] [[substituted tryptamine]] with a [[methyl]] [[substituent]] at the [[alpha carbon]].<ref name="BloughLandavazo2014" /><ref name="BolandAndolloHime2005" /> This alpha substitution makes it a relatively poor [[substrate (chemistry)#Biochemistry|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.<ref name="BolandAndolloHime2005" /> 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.<ref name="TiHKAL" /> 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]]<ref>{{cite web| vauthors = Anonymous |title= Synthesis of alpha-Methyltryptamine (IT-290/AMT) | work = TheHive |url=https://chemistry.mdma.ch/hiveboard/rhodium/it-290.html|access-date=7 June 2023}}</ref> The alternative synthesis is the condensation between indole-3-acetone and [[hydroxylamine]]{{Citation needed|date=June 2023}}, followed by reduction of the obtained ketoxime with [[lithium aluminum hydride]].<ref name="TiHKAL" />

===Analogues===
Many [[structural analog|analogue]]s of αMT are known, including [[α-ethyltryptamine]] (αET), [[4-methyl-αMT]], [[5-chloro-αMT]] (PAL-542), [[5-fluoro-αMT]] (PAL-544), [[5-fluoro-αET]] (PAL-545), [[5-methoxy-αMT]] (5-MeO-αMT), [[alpha,N-DMT|α,''N''-dimethyltryptamine]] (α,''N''-DMT; ''N''-methyl-αMT), [[alpha-N,N-trimethyltryptamine|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.<ref name="BloughLandavazo2014" /><ref name="TiHKAL" /> Another analogue of αMT is the β-[[ketone|keto]] and ''N''-[[methyl group|methylated]] [[chemical derivative|derivative]] [[BK-NM-AMT]].<ref name="BloughDeckerLandavazo2019">{{cite journal | vauthors = Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB | title = The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes | journal = Psychopharmacology (Berl) | volume = 236 | issue = 3 | pages = 915–924 | date = March 2019 | pmid = 30341459 | pmc = 6475490 | doi = 10.1007/s00213-018-5063-9 | url = }}</ref><ref name="US20240335414A1">{{cite patent | country = US | number = 20240335414 | invent1 = [[Matthew J. Baggott]] | invent2 = Sean Dalziel | assign = [[Tactogen Inc.]] | title=Specialized combinations for mental disorders or mental enhancement | url=https://patents.google.com/patent/US20240335414A1/ | pubdate = 10 October 2024 }}</ref><ref name="WO2022061242A1">{{cite patent | country = WO | number = 2022061242 | inventor = [[Matthew J. Baggott|Matthew Baggott]] | status = | title = Advantageous tryptamine compositions for mental disorders or enhancement | pubdate = 2023 March 24 | gdate = | fdate = 2021 September 20 | pridate = 2021 September 20 | assign1 = [[Tactogen]] | url = https://patents.google.com/patent/WO2022061242A1/}}</ref>

[[α-Methyltryptophan]], a [[prodrug]] of [[α-methylserotonin]], also [[drug metabolism|metabolizes]] into αMT, but only in small amounts.<ref name="Sourkes1991">{{cite journal | vauthors = Sourkes TL | title = Alpha-methyltryptophan as a therapeutic agent | journal = Prog Neuropsychopharmacol Biol Psychiatry | volume = 15 | issue = 6 | pages = 935–938 | date = 1991 | pmid = 1763198 | doi = 10.1016/0278-5846(91)90020-2 | url = }}</ref><ref name="RobergeMissalaSourkes1972">{{cite journal | vauthors = Roberge AG, Missala K, Sourkes TL | title = Alpha-methyltryptophan: effects on synthesis and degradation of serotonin in the brain | journal = Neuropharmacology | volume = 11 | issue = 2 | pages = 197–209 | date = March 1972 | pmid = 4260268 | doi = 10.1016/0028-3908(72)90092-5 | url = }}</ref><ref name="MarsdenCurzon1977">{{cite journal | vauthors = Marsden CA, Curzon G | title = Effects of p-chlorophenylalanine and alpha-methyltryptophan on behaviour and brain 5-hydroxyindoles | journal = Neuropharmacology | volume = 16 | issue = 7–8 | pages = 489–494 | date = 1977 | pmid = 144245 | doi = 10.1016/0028-3908(77)90006-5 | url = }}</ref>

There are seven possible [[positional isomer]]s of [[aminopropylindole]] (API; IT), wherein the [[side chain]] is located at different positions of the [[indole]] [[ring system (chemistry)|ring system]].<ref name="ScottPowerMcDermott2014">{{cite journal | vauthors = Scott KR, Power JD, McDermott SD, O'Brien JE, Talbot BN, Barry MG, Kavanagh PV | title = Identification of (2-aminopropyl)indole positional isomers in forensic samples | journal = Drug Test Anal | volume = 6 | issue = 7-8 | pages = 598–606 | date = 2014 | pmid = 23836607 | doi = 10.1002/dta.1508 | url = }}</ref><ref name="TiHKAL" /><ref name="BanksBauerBlough2014">{{cite journal | vauthors = Banks ML, Bauer CT, Blough BE, Rothman RB, Partilla JS, Baumann MH, Negus SS | title = Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys | journal = Exp Clin Psychopharmacol | volume = 22 | issue = 3 | pages = 274–284 | date = June 2014 | pmid = 24796848 | pmc = 4067459 | doi = 10.1037/a0036595 | url = }}</ref> These positional isomers include [[1-(2-aminopropyl)indole|1-API]] (α-methylisotryptamine; isoAMT; PAL-569), [[2-(2-aminopropyl)indole|2-API]], 3-API (3-IT; α-methyltryptamine; AMT; PAL-17), [[4-(2-aminopropyl)indole|4-API]], [[5-(2-aminopropyl)indole|5-API]] (5-IT; 3,4-pyrrolo[b]amphetamine; PAL-571), [[6-(2-aminopropyl)indole|6-API]], and [[7-(2-aminopropyl)indole|7-API]].<ref name="ScottPowerMcDermott2014" /><ref name="TiHKAL" /><ref name="BanksBauerBlough2014" /> 3-API or AMT is an [[substituted α-alkyltryptamine|α-alkyltryptamine]], 1-API or isoAMT is an [[substituted isotryptamine|isotryptamine]], and 4-API, 5-API, 6-API, and 7-API are all [[substituted amphetamine|amphetamine]]s.<ref name="ScottPowerMcDermott2014" /><ref name="TiHKAL" /><ref name="BanksBauerBlough2014" />

The analogue of AMT without the [[benzene]] part of the [[indole]] [[ring (chemistry)|ring]] is [[3-pyrrolylpropylamine]].<ref name="GlennonChaurasiaTiteler1990">{{cite journal | vauthors = Glennon RA, Chaurasia C, Titeler M | title = Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region | journal = Journal of Medicinal Chemistry | volume = 33 | issue = 10 | pages = 2777–2784 | date = October 1990 | pmid = 2213830 | doi = 10.1021/jm00172a016 }}</ref>

==History==
αMT has been said to have been first [[chemical synthesis|synthesized]] in 1947, alongside [[α-ethyltryptamine]] (αET).<ref name="ElliottBrandtFreeman2013" /><ref name="GlennonDukat2023" /><ref name="SnyderKatz1947">{{cite journal | vauthors = Snyder HR, Katz L | title = The alkylation of aliphatic nitro compounds with gramine; a new synthesis of derivatives of tryptamine | journal = Journal of the American Chemical Society | volume = 69 | issue = 12 | pages = 3140–3142 | date = December 1947 | pmid = 18919717 | doi = 10.1021/ja01204a061 | bibcode = 1947JAChS..69.3140S }}</ref> However, other sources suggest that αMT was first described in the [[scientific literature]] by at least 1929.<ref name="GaddumHameed1954">{{cite journal | vauthors = Gaddum JH, Hameed KA | title = Drugs which antagonize 5-hydroxytryptamine | journal = British Journal of Pharmacology and Chemotherapy | volume = 9 | issue = 2 | pages = 240–248 | date = June 1954 | pmid = 13172437 | pmc = 1509436 | doi = 10.1111/j.1476-5381.1954.tb00848.x | quote = The antagonism of ergotoxine and tryptamine was described by Laidlaw (1911) and that of ergotamine and α-methyltryptamine by Seki (1929). }}</ref><ref name="Seki1929">{{cite journal | vauthors = Seki J | title = Pharmakologische Untersuchungen des α-Methyl-β-indoläthylamins | trans-title = Pharmacological studies of α-methyl-β-indoleethylamine | date = 1929 | journal = Japanese Journal of Medical Sciences. Part 4: Pharmacology | volume = 3 | pages = 235–285 | publisher=National Research Council of Japan | issn = 0368-3745 | oclc = 610325817 | url = https://books.google.com/books?id=rrZXAAAAMAAJ&q=%22Pharmakologische+Untersuchungen+des+a-Methyl-8-indol%C3%A4thylamins%22}}</ref> It was specifically described as an [[receptor antagonist|antagonist]] of [[ergotamine]] at this time.<ref name="GaddumHameed1954" /><ref name="Seki1929" />

αMT started to be more intensively studied, along with αET, in the late 1950s and early 1960s.<ref name="ElliottBrandtFreeman2013" /><ref name="GreigWalkGibbons1959">{{cite journal | vauthors = Greig ME, Walk RA, Gibbons AJ | title = The effect of three tryptamine derivatives on serotonin metabolism in vitro and in vivo | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 127 | issue =  2| pages = 110–115 | date = October 1959 | pmid = 13851725 | doi =  10.1016/S0022-3565(25)25666-X}}</ref><ref name="HeinzelmanAnthonyLyttle1960">{{cite journal | vauthors = Heinzelman RV, Anthony WC, Lyttle DA, Szmuszkovicz J | title=The Synthesis of α-Methyltryptophans and α-Alkyltryptamines | journal=The Journal of Organic Chemistry | volume=25 | issue=9 | date=1960 | issn=0022-3263 | doi=10.1021/jo01079a021 | pages=1548–1558}}</ref><ref name="MurphreeDippyJenney1961">{{cite journal | vauthors = Murphree HB, Dippy RH, Jenney EH, Pfeiffer CC | title = Effects in normal man of alpha-methyltryptamine and alpha-ethyltryptamine | journal = Clinical Pharmacology and Therapeutics | volume = 2 | issue =  6| pages = 722–726 | date = 1961 | pmid = 14477400 | doi = 10.1002/cpt196126722 }}</ref><ref name="GeyPletscher1961">{{cite journal | vauthors = Gey KF, Pletscher A | title = Effect of alpha-alkylated tryptamine derivatives on 5-hydroxytryptamine metabolism in vivo | journal = British Journal of Pharmacology and Chemotherapy | volume = 19 | issue = 1 | pages = 161–167 | date = August 1962 | pmid = 13898151 | pmc = 1482243 | doi = 10.1111/j.1476-5381.1962.tb01437.x }}</ref><ref name="Himwich1961">{{cite journal | vauthors = Himwich HE | title = Experiments with alpha-methyltryptamine | journal = Journal of Neuropsychiatry | volume = 2 | issue = Suppl 1 | pages = 136–140 | date = February 1961 | pmid = 13714418 | doi =  }}</ref><ref name="VaneCollierCorne1961">{{cite journal | vauthors = Vane JR, Collier HO, Corne SJ, Marley E, Bradley PB | title = Tryptamine receptors in the central nervous system | journal = Nature | volume = 191 | issue =  4793| pages = 1068–1069 | date = September 1961 | pmid = 13780152 | doi = 10.1038/1911068a0 | bibcode = 1961Natur.191.1068V }}</ref><ref name="KellerVigueraKundzins1962">{{cite journal | vauthors = Keller JG, Viguera C, Kundzins W | title = Studies on the toxicology of alpha-methyl- and alpha-ethyltryptamine acetates (Monase). II. Chronic studies | journal = Toxicology and Applied Pharmacology | volume = 4 | issue =  6| pages = 697–709 | date = November 1962 | pmid = 14031765 | doi = 10.1016/0041-008x(62)90099-6 | bibcode = 1962ToxAP...4..697K }}</ref><ref name="SzaraHearstPutney1962">{{cite journal | vauthors = Szara S, Hearst E, Putney F | title=Metabolism and behavioural action of psychotropic tryptamine homologues | journal=International Journal of Neuropharmacology | volume=1 | issue=1–3 | date=1962 | doi=10.1016/0028-3908(62)90015-1 | pages=111–117}}</ref><ref name="MashkovskiiTrubitsyna1963">{{cite journal | vauthors = Mashkovskii MD, Trubitsyna TK | title = [Pharmacological properties of indopane (alpha-methyltryptamine HCl)] | language = Russian | journal = Zhurnal Nevropatologii I Psikhiatrii imeni S.S. Korsakova | volume = 63 | issue =  | pages = 72–79 | date = 1963 | pmid = 13933321 | doi =  }}</ref> 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.<ref name="AraújoCarvalhoBastos2015">{{cite journal | vauthors = Araújo AM, Carvalho F, ((Bastos Md)), Guedes de Pinho P, Carvalho M | title = The hallucinogenic world of tryptamines: an updated review | journal = Archives of Toxicology | volume = 89 | issue = 8 | pages = 1151–1173 | date = August 2015 | pmid = 25877327 | doi = 10.1007/s00204-015-1513-x | bibcode = 2015ArTox..89.1151A }}</ref><ref name="TittarelliMannocchiPantano2015">{{cite journal | vauthors = Tittarelli R, Mannocchi G, Pantano F, Romolo FS | title = Recreational use, analysis and toxicity of tryptamines | journal = Current Neuropharmacology | volume = 13 | issue = 1 | pages = 26–46 | date = January 2015 | pmid = 26074742 | pmc = 4462041 | doi = 10.2174/1570159x13666141210222409 }}</ref><ref name="BolandAndolloHime2005" /><ref name="US3296072">{{ cite patent | country = US | number = 3296072 | status = Patent | title = Method of Treating Mental Depression | pubdate = 1967-01-03 | gdate = | fdate = 1964-01-29 | pridate = 1962-06-11 | inventor = Szmuszkovicz J | assign1 = Upjohn Co | class = | url=http://www.google.com/patents/US3296072 | postscript = . }}</ref> However, the drug was used clinically for only a short period of time before being [[withdrawn drug|withdrawn]].<ref name="TittarelliMannocchiPantano2015" />

αMT started being used as a [[recreational]] drug in the 1960s<ref name="BolandAndolloHime2005" /> and use as a [[designer drug]] increased in the 1990s.<ref name="AraújoCarvalhoBastos2015" /> It became a [[controlled substance]] in the [[United States]] in 2003.<ref name="AraújoCarvalhoBastos2015" />

==Society and culture==
===Names===
αMT never received a formal [[generic term|generic name]].<ref name="Elks2014">{{cite book | vauthors = Elks J | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ | access-date=7 September 2024 | page=}}</ref> In the [[scientific literature]], it has been referred to as ''α-methyltryptamine'' or ''alpha-methyltryptamine'' (abbreviated as ''α-MT'', ''αMT'', or ''AMT'').<ref name="AraújoCarvalhoBastos2015" /><ref name="TittarelliMannocchiPantano2015" /> αMT has also been referred to by developmental code names including ''IT-290'' ([[Sandoz]]),<ref name="HollisterPrusmackPaulsen1960">{{cite journal | vauthors = Hollister LE, Prusmack JJ, Paulsen A, Rosenquist N | title = Comparison of three psychotropic drugs (psilocybin, JB-329, and IT-290) in volunteer subjects | journal = The Journal of Nervous and Mental Disease | volume = 131 | issue =  5| pages = 428–434 | date = November 1960 | pmid = 13715375 | doi = 10.1097/00005053-196011000-00007 }}</ref> ''NSC-97069'',<ref name="ElliottBrandtFreeman2013">{{cite journal | vauthors = Elliott SP, Brandt SD, Freeman S, Archer RP | title = AMT (3-(2-aminopropyl)indole) and 5-IT (5-(2-aminopropyl)indole): an analytical challenge and implications for forensic analysis | journal = Drug Testing and Analysis | volume = 5 | issue = 3 | pages = 196–202 | date = March 2013 | pmid = 23042766 | doi = 10.1002/dta.1420 | quote = 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] [...] }}</ref> ''PAL-17'',<ref name="BloughLandavazo2014" /> ''Ro 3-0926'',<ref name="LessinLongParkes1966">{{cite journal | vauthors = Lessin AW, Long RF, Parkes MW | title = Conversion of indolylalkylhydroxylamines to stimulant amines in vivo | journal = Biochemical Pharmacology | volume = 15 | issue = 4 | pages = 481–487 | date = April 1966 | pmid = 5954980 | doi = 10.1016/0006-2952(66)90258-9 }}</ref><ref name="LessinLongParkes1967">{{cite journal | vauthors = Lessin AW, Long RF, Parkes MW | title = 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 | journal = British Journal of Pharmacology and Chemotherapy | volume = 29 | issue = 1 | pages = 70–79 | date = January 1967 | pmid = 19108241 | pmc = 1557188 | doi = 10.1111/j.1476-5381.1967.tb01940.x }}</ref> and ''U-14,164E'' ([[Upjohn]]).<ref name="BurninghamArimuraYunis1966">{{cite journal | vauthors = Burningham RA, Arimura GK, Yunis AA | title = Effect of Monase and related compounds on uptake of 5-hydroxytryptamine by platelets | journal = Proceedings of the Society for Experimental Biology and Medicine | volume = 122 | issue = 3 | pages = 711–714 | date = July 1966 | pmid = 5918937 | doi = 10.3181/00379727-122-31233 }}</ref><ref name="Offermeier1965">{{cite thesis | vauthors = Offermeier J | degree = Ph.D. | title=Serotonin and its derivatives: a study on structure-activity relations | publisher=Catholic University of Nijmegen | date=1965 | url=https://repository.ubn.ru.nl/handle/2066/107492 | access-date=7 September 2024}}</ref><ref name="ElliottBrandtFreeman2013" /><ref name="BolandAndolloHime2005" /> In the [[Soviet Union]], the drug was merely referred to by its brand name ''Indopan'' or ''Indopane''.<ref name="PubMed-Search-Indopan">{{cite web | title=("indopan"[title] OR "indopane"[title]) | work = PubMed | publisher = U.S. National Library of Medicine | url=https://pubmed.ncbi.nlm.nih.gov/?term=%28%22indopan%22%5Btitle%5D+OR+%22indopane%22%5Btitle%5D%29&sort=pubdate | access-date=7 September 2024}}</ref><ref name="BolandAndolloHime2005" /> Other synonyms of αMT include ''3-(2-aminopropyl)indole'' and ''3-IT''.<ref name="ElliottBrandtFreeman2013" /> (+)-αMT has been referred to by the code name ''IT-403''.<ref name="ElliottBrandtFreeman2013" /><ref name="BolandAndolloHime2005" />

===Legal status===
====Australia====
The 5-methoxy analogue, [[5-MeO-αMT]] is [[Standard for the Uniform Scheduling of Drugs and Poisons#Schedule 9 Prohibited Substance|schedule 9]] in Australia and αMT would be controlled as an analogue of this.<ref name="urlErowid 5-MeO-AMT Vault : Legal Status">{{cite web | url = http://www.erowid.org/chemicals/5meo_amt/5meo_amt_law.shtml | work = Erowid Vault | title = 5-MeO-AMT: Legal Status }}</ref>

====Austria====
αMT is placed under Austrian law (NPSG) Group 6.<ref name="who.int"/>

====Canada====
Canada has no mention of αMT in the [[Controlled Drugs and Substances Act]].<ref name="urlCDSA List">{{cite web | url = http://isomerdesign.com/Cdsa/schedule.php?structure=C | title = CSDA | access-date = 2011-06-05 | archive-date = 2011-09-28 | archive-url = https://web.archive.org/web/20110928152752/http://isomerdesign.com/Cdsa/schedule.php?structure=C | url-status = dead }}</ref>

====China====
As of October 2015 αMT is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | trans-title = Notice on the issuance of the "Regulations on the Listing of Non-Medicinal Narcotic Drugs and Psychotropic Drugs" | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref>

====Denmark====
In Denmark (2010), the Danish Minister for the Interior and Health placed αMT to their lists of controlled substances (List B).<ref name="who.int">{{cite web| url = https://www.who.int/medicines/areas/quality_safety/4_20_Review.pdf | archive-url = https://web.archive.org/web/20180916024447/https://www.who.int/medicines/areas/quality_safety/4_20_Review.pdf | archive-date = 16 September 2018 | title = Alpha-methyltryptamine (AMT) Critical Review Report Agenda item 4.20 | author = Expert Committee on Drug Dependence Thirty-sixth Meeting | location = Geneva | date = June 2014 | publisher = World Health Organization (WHO) }}</ref>

====Finland====
AMT, alfa-methyltryptamine, is a controlled drug in Finland.<ref>{{cite web | title = Lääkeluettelon Aineet, Liite 1, Bilaga 1.3 | trans-title = Substances of the drug list, Appendix 1. Attachment 1.3 | url = http://www.finlex.fi/data/sdliite/liite/6194.pdf | archive-url = https://web.archive.org/web/20150510154257/http://www.finlex.fi/data/sdliite/liite/6194.pdf | url-status = dead | archive-date = May 10, 2015 | work = Finlex Data Bank | publisher = Finnish Ministry of Justice }}</ref>

====Germany====
αMT is listed under the Narcotics Act in schedule 1 (narcotics not eligible for trade and medical prescriptions) in Germany.<ref name="who.int"/>

====Hungary====
αMT was controlled on the Schedule C list in Hungary in 2013.<ref name="who.int"/>

====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.<ref name="who.int"/>

====Slovakia====
αMT was placed in 2013 on the List of Hazardous Substances in Annex, § 2 in Slovakia.<ref name="who.int"/>

====Slovenia====
αMT appeared on the Decree on Classification of Illicit Drugs in Slovenia (2013).<ref name="who.int"/>

====Spain====
αMT is legal in Spain.<ref>{{cite web|url=https://www.aemps.gob.es/medicamentosUsoHumano/estupefacientesPsicotropos/home.htm|title=Medicamentos de Uso Humano - Estupefacientes y Psicótropos | trans-title = Medicines for Human Use - Narcotics and Psychotropic Substances |website=Agencia Española de Medicamentos y Productos Sanitarios [Spanish Agency for Medicines and Health Products] |access-date=2019-01-01|archive-date=2019-01-02|archive-url=https://web.archive.org/web/20190102002336/https://www.aemps.gob.es/medicamentosUsoHumano/estupefacientesPsicotropos/home.htm|url-status=dead}}</ref>

====Sweden====
[[Riksdag|''Sveriges riksdags'']] health ministry [[:sv:Statens folkhälsoinstitut|''Statens folkhälsoinstitut'']] classified αMT as "health hazard" under the act [[:sv:Lagen om förbud mot vissa hälsofarliga varor|''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.<ref name='Swedenlaw'>{{citation | contribution = 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] | title = Lagen om förbud mot vissa hälsofarliga varor - SFS 2005:26 | trans-title = The Act on the Prohibition of Certain Goods Hazardous to Health - SFS 2005:26 | date = February 2005 | contribution-url = http://www.notisum.se/rnp/sls/sfs/20050026.pdf | access-date = 2013-10-07 | language = sv | archive-date = 2013-09-29 | archive-url = https://web.archive.org/web/20130929063138/http://www.notisum.se/rnp/sls/sfs/20050026.pdf | url-status = dead }}</ref>

====United Kingdom====
αMT was made illegal in the United Kingdom as of 7 January 2015, along with [[5-MeO-DALT]].<ref>{{cite web|url=http://www.legislation.gov.uk/uksi/2014/3277/introduction/made/data.htm|title=The Misuse of Drugs (Amendment No. 3) (England, Wales and Scotland) Regulations 2014|website=www.legislation.gov.uk}}</ref>
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.<ref name="ACMD tryptamines">{{cite web | url=https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/318693/UpdateGenericDefinitionTryptamines.pdf | title=Update of the Generic Definition for Tryptamines | publisher=UK Home Office | date=10 June 2014 | access-date=10 June 2014 | author=ACMD|page=12}}</ref>

====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).<ref>{{cite news|title=Alpha-methyltryptamine |date=April 2013 |url=http://www.deadiversion.usdoj.gov/drug_chem_info/amt.pdf |work=DEA Office of Diversion Control |access-date=2013-10-10 |archive-url=https://web.archive.org/web/20131017084419/http://www.deadiversion.usdoj.gov/drug_chem_info/amt.pdf |archive-date=2013-10-17 |url-status=live }}</ref>

==Research==
Besides [[depression (mood)|depression]], αMT has been studied in people with [[schizophrenia]] and other conditions.<ref name="BloughLandavazo2014" />

==See also==
* [[Substituted α-alkyltryptamine]]
* [[List of Russian drugs]]

==Notes==
{{Reflist|group=note}}

==References==
{{Reflist}}

==External links==
* [https://isomerdesign.com/pihkal/explore/5048 AMT - Isomer Design]
* [https://psychonautwiki.org/wiki/AMT AMT - PsychonautWiki]
* [https://www.erowid.org/chemicals/amt/amt.shtml AMT - Erowid]
* [https://www.bluelight.org/xf/threads/270474 The Big & Dandy AMT Thread - Bluelight]
* [https://web.archive.org/web/20020823023455/http://leda.lycaeum.org/Chemicals/AMT.168.shtml AMT - Lycaeum]
* [http://www.erowid.org/library/books_online/tihkal/tihkal48.shtml α-MT - TiHKAL - Erowid]
* [https://isomerdesign.com/pihkal/read/tk/48 α-MT - TiHKAL - Isomer Design]

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