Editing 5-MeO-AMT

{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Verifiedfields = verified
| verifiedrevid = 477224876
| drug_name = 5-MeO-AMT
| IUPAC_name = 1-(5-methoxy-1''H''-indol-3-yl)propan-2-amine
| image = 5-MeO-AMT.svg
| width = 
| image2 = 5-MeO-AMT-3d-sticks.png
| width2 =

<!--Clinical data-->
| tradename = 
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category = 
| routes_of_administration = [[Oral administration|Oral]]<ref name="TiHKAL" />
| class = [[Serotonin receptor agonist]]; [[Serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] [[agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]

<!--Legal status-->
| legal_AU = Schedule 9
| 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_DE = NpSG
| legal_UK = Class A
| legal_US = ''The [[Drug Enforcement Administration|DEA]] considers 5-MeO-AMT a controlled substance analogue.''<ref name="5-MeO-AMT; Fast Facts">{{Cite web |date=January 1, 2006 |title=5-MeO-AMT; Fast Facts |url=https://www.justice.gov/archive/ndic/pubs9/9576/index.htm |archive-url=https://web.archive.org/web/20230603154528/https://www.justice.gov/archive/ndic/pubs9/9576/index.htm#Top |archive-date=June 3, 2023 |access-date=July 5, 2023 |website=[[National Drug Intelligence Center]] |url-status=live }}</ref>
| legal_status = Illegal in Sweden and Florida

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| onset = 
| elimination_half-life = 
| duration_of_action = 12–18 hours<ref name="TiHKAL" />
| excretion = 

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 1137-04-8
| ATC_prefix = None
| ATC_suffix = 
| PubChem = 36906
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 33864
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 31115
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = U5XOB9AQ15
| ChEBI = 125422
| synonyms = 5-MeO-AMT; 5-Methoxy-α-methyltryptamine; α,''O''-Dimethylserotonin; α,''O''-DMS; Alpha-O

<!--Chemical data-->
| C = 12 | H = 16 | N = 2 | O = 1
| SMILES = N[C@@H](C)CC1=CNC(C=C2)=C1C=C2OC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H16N2O/c1-8(13)5-9-7-14-12-4-3-10(15-2)6-11(9)12/h3-4,6-8,14H,5,13H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OGNJZVNNKBZFRM-UHFFFAOYSA-N

<!--Physical data -->
| melting_point = 216
| melting_high = 218
}}

'''5-MeO-αMT''', also known as '''5-methoxy-α-methyltryptamine''' or as '''α,''O''-dimethylserotonin''' ('''α,''O''-DMS''' or '''Alpha-O'''), is a [[serotonergic psychedelic]] of the [[substituted tryptamine|tryptamine]], [[substituted α-alkyltryptamine|α-alkyltryptamine]], and [[substituted 5-methoxytryptamine|5-methoxytryptamine]] families.<ref name="TiHKAL" /> It is a [[chemical derivative|derivative]] of [[α-methyltryptamine]] (αMT) and an [[structural analog|analogue]] of [[5-MeO-DMT]].<ref name="TiHKAL" /> The drug is said to be the most [[potency (pharmacology)|potent]] psychedelic of the simple indolealkylamines (i.e., tryptamines).<ref name="Vangveravong1994">{{cite web | vauthors = Vangveravong S | title=Synthesis of trans-2-(indol-3-yl)cyclopropylamines: Rigid tryptamine analogues | date = 1994 | website=ProQuest | url=https://www.proquest.com/docview/304131663 | access-date=22 March 2025 | quote = Figure 5. Rigid Serotonin Receptor Ligands [...]}}</ref> It is active at [[oral administration|oral]] doses of 2 to 4{{nbsp}}mg.<ref name="Vangveravong1994" /><ref name="TiHKAL">{{CiteTiHKAL}}</ref>

==Use==
[[File:5meoamtcheck.jpg|thumb|200px|left|5-MeO-AMT blotters.]]

The dosage range of 5-MeO-AMT listed in ''[[TiHKAL]]'' is 2.5 to 4.5{{nbsp}}mg and its [[duration of action|duration]] is listed as 12 to 18{{nbsp}}hours.<ref name="TiHKAL" /> However, a wider [[recreational drug|recreational]] dosage range of 0.5 to 15{{nbsp}}mg has also been reported.<ref name="LuethiLiechti2018">{{cite journal | vauthors = Luethi D, Liechti ME | title = Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics | journal = Int J Neuropsychopharmacol | volume = 21 | issue = 10 | pages = 926–931 | date = October 2018 | pmid = 29850881 | pmc = 6165951 | doi = 10.1093/ijnp/pyy047 | url = https://bitnest.netfirms.com/external/10.1093/ijnp/pyy047}}</ref><ref name="HalberstadtChathaKlein2020">{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD | title = Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species | journal = Neuropharmacology | volume = 167 | issue = | pages = 107933 | date = May 2020 | pmid = 31917152 | pmc = 9191653 | doi = 10.1016/j.neuropharm.2019.107933 | url = http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf | quote = Table 4 Human potency data for selected hallucinogens. [...] }}</ref>

5-MeO-AMT has supposedly been sold as 4{{nbsp}}mg tablets by the street name Alpha-O and taken as a [[recreational drug]]. Since the [[Drug Enforcement Administration|DEA]] arrests of the [[William Leonard Pickard|makers]] of a huge percentage of the United States' [[Lysergic acid diethylamide|LSD]] in 2000, 5-MeO-AMT may have occasionally been sold under the guise of LSD in liquid, [[sugar cube]], or [[Blotting paper|blotter]] form, though this may be due to DEA reports of finding it on sugar cubes and blotters like LSD.<ref name="Zimmerman2003">{{Cite journal| vauthors = Zimmerman MM |title=The Identification of 5-Methoxy-alpha-methyltryptamine (5-MeO-AMT)|journal=Microgram Journal|publisher=[[Drug Enforcement Administration]] |date=January–June 2003 |volume=1 |url= https://www.justice.gov/dea/programs/forensicsci/microgram/journal071203/mj071203_pg1.html |access-date=2011-09-16|archive-url=https://web.archive.org/web/20110918044620/http://www.justice.gov/dea/programs/forensicsci/microgram/journal071203/mj071203_pg1.html|archive-date=2011-09-18|url-status=dead}}</ref><ref>{{cite web | url = http://www.erowid.org/chemicals/5meo_amt/5meo_amt_info2.shtml | work = Erowid Vault | title = Police Reports of 5-MeO-AMT }}</ref>

The most common route of administration for 5-MeO-AMT is orally. Anecdotal reports, however, have described snorting or smoking the substance. Intravenous (IV) and intramuscular (IM) routes are rarely, if ever, used outside research settings due to the high potency, powerful effects and quicker onset.

== Effects ==
[[File:5meo amt sample dea1.jpg|thumb|300px|right|Tabs of gelatin containing 5-MeO-AMT.]]

[[Erowid]] lists the following effects:<ref>{{cite web|url=http://www.erowid.org/chemicals/5meo_amt/5meo_amt_effects.shtml|title=5-MeO-AMT Vault: Effects| work = Erowid Vault }}</ref>

===Positive===
* Increased energy
* Improved mood heading into euphoria at higher doses
* Increased sociability, gregariousness
* Increased giggling and laughter
* Increased sense of [[creative thinking]]
* Increased pleasure from sense of touch
* Intensification of sex for some users

===Neutral===
* Lightheadedness
* Brightening of [[color]]s
* Visuals including [[Motion (physics)|motion]], [[wave]]s, breathing walls, etc. (usually at higher doses, over 4–5&nbsp;[[Milligram|mg]])
* Increased attention to detail
* Auditory distortions and/or hallucinations (usually at higher doses)

===Negative===
* [[Headache]]
* Body [[fatigue (medical)|fatigue]]
* Chills from elevated body temperature (potential dehydration)
* Stress and extreme fatigue from long duration of effects.
* [[Nausea]], [[diarrhea]]
* [[Vomiting]] 
* Difficulty [[sleep]]ing or resting for 12–24 hours after ingestion.
* [[Paranoia]], irritability, [[anxiety]] (increasing with dose).
* Delusional, aggressive, or dissociated behaviour at very high doses (20+ mg)
* Risk of death

==Dangers==
If misrepresented as LSD, 5-MeO-AMT can be extremely dangerous; users may take a number of "hits" of 5-MeO-AMT, assuming that it is LSD. Unlike LSD, which is very safe in overdose, 5-MeO-AMT can be very harmful or fatal. Particularly sensitive individuals can experience symptoms of overdose at dosages in the normal (for most users) range — as low as 20&nbsp;mg. This has led to at least a few hospitalizations and possibly more than one death.<ref>{{cite web |title=Reported LSD-Related death was not LSD |url=http://www.erowid.org/chemicals/lsd/lsd_media2.shtml |work = Erowid Vault |date=July 2007}}</ref><ref>{{cite web |title=5-MeO-AMT Hospitalizations & Possible Deaths |url=http://www.erowid.org/chemicals/5meo_amt/5meo_amt_info1.shtml |work = Erowid Vault |date=January 2007}}</ref> It is likely that the overdose potential of the compound is due to its [[sympathomimetic]] effects, as the side effects noted in overdose cases include [[cardiac arrhythmia]] and [[seizure]]. It also seems that oral consumption is safer than [[Insufflation (medicine)|insufflation]].{{Citation needed|date=March 2009}}

Gloria Discerni, 18, died after overdosing on a drug initially believed to be LSD. Authorities learned months later that the drug wasn't LSD but a "designer drug" identified as 5-MeO-AMT.<ref>{{Cite web | vauthors = Brodwater T | date = 13 December 2006 |url=http://www.spokesman.com/stories/2006/dec/13/charges-dropped-in-drug-death/|title=Charges dropped in drug death | work = The Spokesman-Review }}</ref>

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

==Pharmacology==
===Pharmacodynamics===
{| class="wikitable floatright" style="font-size:small;"
|+ 5-MeO-AMT activities
|-
! [[Biological target|Target]]
! [[Affinity (pharmacology)|Affinity]] (K<sub>i</sub>, nM)
|-
| [[5-HT1A receptor|5-HT<sub>1A</sub>]]
| 46–194 (K<sub>i</sub>)<br />680 ({{Abbrlink|EC<sub>50</sub>|Half-maximal effective concentration}})<br />101% ({{Abbrlink|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT1B receptor|5-HT<sub>1B</sub>]]
| 417 (rat)
|-
| [[5-HT2A receptor|5-HT<sub>2A</sub>]]
| 3.1–34 (K<sub>i</sub>)<br />2–8.4 ({{Abbr|EC<sub>50</sub>|Half-maximal effective concentration}})<br />84% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2B receptor|5-HT<sub>2B</sub>]]
| 4 ({{Abbr|EC<sub>50</sub>|Half-maximal effective concentration}})
|-
| [[5-HT2C receptor|5-HT<sub>2C</sub>]]
| 90
|-
| [[Alpha-1A adrenergic receptor|α<sub>1A</sub>]]
| >12,000
|-
| [[Alpha-2A adrenergic receptor|α<sub>2A</sub>]]
| 11,000
|-
| [[D1 receptor|D<sub>1</sub>]]
| >25,000
|-
| [[D2 receptor|D<sub>2</sub>]]
| >25,000
|-
| [[D3 receptor|D<sub>3</sub>]]
| >25,000
|-
| [[H1 receptor|H<sub>1</sub>]]
| >25,000
|-
| [[TAAR1|TAAR<sub>1</sub>]]
| 1,100 (K<sub>i</sub>) (rat)<br />4,800 (K<sub>i</sub>) (mouse)<br />>10,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (human)
|-
| {{Abbrlink|SERT|Serotonin transporter}}
| 8,270–12,000 (K<sub>i</sub>)<br />1,980–17,000 ({{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />460 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|NET|Norepinephrine transporter}}
| >22,000 (K<sub>i</sub>)<br />37,000–78,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />8,900 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|DAT|Dopamine transporter}}
| >26,000 (K<sub>i</sub>)<br />2,690–43,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />1,500 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|MAO-A|Monoamine oxidase A}}
| 31,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|- class="sortbottom"
| colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. '''Refs:''' <ref name="BindingDB">{{cite journal | vauthors = Liu T | title=BindingDB BDBM50227458 CHEMBL2093088 | journal=Journal of Medicinal Chemistry | date=1988 | volume=31 | issue=7 | pages=1406–1412 | doi=10.1021/jm00402a026 | pmid=3385733 | url=https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50227458 | access-date=29 November 2024| url-access=subscription }}</ref><ref name="RickliMoningHoener2016">{{cite journal | vauthors = Rickli A, Moning OD, Hoener MC, Liechti ME | title = Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens | journal = European Neuropsychopharmacology | volume = 26 | issue = 8 | pages = 1327–1337 | date = August 2016 | pmid = 27216487 | doi = 10.1016/j.euroneuro.2016.05.001 | s2cid = 6685927 | url = http://edoc.unibas.ch/53326/1/20170117174852_587e4af45b658.pdf }}</ref><ref name="GatchForsterJanowsky2011" /><ref name="NagaiNonakaKamimura2007" /><ref name="WangZhuPaudel2023">{{cite journal | vauthors = Wang S, Zhu A, Paudel S, Jang CG, Lee YS, Kim KM | title = Structure-Activity Relationship and Evaluation of Phenethylamine and Tryptamine Derivatives for Affinity towards 5-Hydroxytryptamine Type 2A Receptor | journal = Biomol Ther (Seoul) | volume = 31 | issue = 2 | pages = 176–182 | date = March 2023 | pmid = 36224112 | pmc = 9970836 | doi = 10.4062/biomolther.2022.096 | url = }}</ref><ref name="WagmannBrandtKavanagh2017" /><ref name="SimmlerBuchyChaboz2016">{{cite journal | vauthors = Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME | title = In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1 | journal = J Pharmacol Exp Ther | volume = 357 | issue = 1 | pages = 134–144 | date = April 2016 | pmid = 26791601 | doi = 10.1124/jpet.115.229765 | url = https://web.archive.org/web/20250509235235/https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA}}</ref>
|}

5-MeO-AMT acts as a [[binding selectivity|non-selective]] [[serotonin receptor agonist]], including of the [[serotonin]] [[5-HT1A receptor|5-HT<sub>1A</sub>]], [[5-HT2A receptor|5-HT<sub>2A</sub>]], and [[5-HT2B receptor|5-HT<sub>2B</sub> receptor]]s, among others.<ref name="GatchForsterJanowsky2011">{{cite journal | vauthors = Gatch MB, Forster MJ, Janowsky A, Eshleman AJ | title = Abuse liability profile of three substituted tryptamines | journal = J Pharmacol Exp Ther | volume = 338 | issue = 1 | pages = 280–289 | date = July 2011 | pmid = 21474568 | pmc = 3126641 | doi = 10.1124/jpet.111.179705 | url = }}</ref><ref name="RickliMoningHoener2016" /> Its {{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} at the serotonin 5-HT<sub>2A</sub> receptor has been found to be 2 to 8.4{{nbsp}}nM.<ref name="GatchForsterJanowsky2011" /><ref name="RickliMoningHoener2016" /> In relation to this, it is an extremely [[potency (pharmacology)|potent]] agonist of the serotonin 5-HT<sub>2A</sub> receptor ''[[in vitro]]'', showing the highest potency of any other tryptamine assessed in one study.<ref name="RickliMoningHoener2016" /> Its potency in activating the serotonin 5-HT<sub>2A</sub> receptor was 38-fold higher than that of [[dimethyltryptamine]] (DMT) and 361-fold higher than that of [[psilocin]] in the same study.<ref name="RickliMoningHoener2016" /> It is also a highly potent agonist of the serotonin 5-HT<sub>2B</sub> receptor, with an {{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} of 4{{nbsp}}nM.<ref name="RickliMoningHoener2016" />

Whereas [[tryptamine]], [[serotonin]] (5-hydroxytryptamine), and αMT show potent activity as [[monoamine releasing agent]]s, including of [[serotonin]], [[norepinephrine]], and/or [[dopamine]], the monoamine-releasing activity of 5-methoxylated tryptamine derivatives, like [[5-methoxytryptamine]], [[5-MeO-NMT]], and [[5-MeO-DMT]] among others, is dramatically reduced or abolished.<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="BloughLandavazoPartilla2014">{{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 = Bioorg Med Chem Lett | volume = 24 | issue = 19 | pages = 4754–4758 | date = October 2014 | pmid = 25193229 | pmc = 4211607 | doi = 10.1016/j.bmcl.2014.07.062 | url = }}</ref><ref name="RothmanBaumann2006">{{cite journal | vauthors = Rothman RB, Baumann MH | title = Therapeutic potential of monoamine transporter substrates | journal = Curr Top Med Chem | volume = 6 | issue = 17 | pages = 1845–1859 | date = 2006 | pmid = 17017961 | doi = 10.2174/156802606778249766 | url = }}</ref><ref name="NagaiNonakaKamimura2007">{{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><ref name="GatchForsterJanowsky2011" /> Accordingly, whereas the {{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} values of αMT for induction of monoamine release are 22 to 68{{nbsp}}nM for serotonin, 79 to 112{{nbsp}}nM for norepinephrine, and 79 to 180{{nbsp}}nM for dopamine, the {{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} values in the case of 5-MeO-AMT are 460{{nbsp}}nM for serotonin, 8,900{{nbsp}}nM for norepinephrine, and 1,500{{nbsp}}nM for dopamine.<ref name="NagaiNonakaKamimura2007" /><ref name="BloughLandavazoPartilla2014" /><ref name="RickliMoningHoener2016" /> Similarly, it is of very low potency as a [[monoamine reuptake inhibitor]] ({{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}} values >1,000{{nbsp}}nM).<ref name="NagaiNonakaKamimura2007" /><ref name="RickliMoningHoener2016" /> Considering the very high potency of 5-MeO-AMT in activating the serotonin 5-HT<sub>2A</sub> receptor, its weak activities as a monoamine releasing agent and reuptake inhibitor are of questionable significance.<ref name="NagaiNonakaKamimura2007" /><ref name="BloughLandavazoPartilla2014" /><ref name="RickliMoningHoener2016" /><ref name="GatchForsterJanowsky2011" />

5-MeO-AMT is a weak [[monoamine oxidase A]] (MAO-A) [[monoamine oxidase inhibitor|inhibitor]], with an {{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}} of 31,000{{nbsp}}nM.<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 = | pages = 1590 | date = 2019 | pmid = 32038257 | pmc = 6989591 | doi = 10.3389/fphar.2019.01590 | doi-access = free | url = }}</ref><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> For comparison, the {{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}} of AMT for MAO-A inhibition was 380{{nbsp}}nM (~82-fold more potent than 5-MeO-AMT)<ref name="Reyes-ParadaIturriaga-VasquezCassels2019" /><ref name="WagmannBrandtKavanagh2017" /> and the {{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}} values of [[amphetamine]] (and its [[enantiomer]]s) for MAO-A inhibition have been reported to be 11,000 to 70,000{{nbsp}}nM.<ref name="Reyes-ParadaIturriaga-VasquezCassels2019" />

5-MeO-AMT produces the [[head-twitch response]], a behavioral proxy of [[psychedelic drug|psychedelic]] effects, in rodents, and this is reversed by the serotonin 5-HT<sub>2A</sub> receptor [[receptor antagonist|antagonist]] [[ketanserin]].<ref name="AbieroBotanasSayson2019">{{cite journal | vauthors = Abiero A, Botanas CJ, Sayson LV, Custodio RJ, de la Peña JB, Kim M, Lee HJ, Seo JW, Ryu IS, Chang CM, Yang JS, Lee YS, Jang CG, Kim HJ, Cheong JH | title = 5-Methoxy-α-methyltryptamine (5-MeO-AMT), a tryptamine derivative, induces head-twitch responses in mice through the activation of serotonin receptor 2a in the prefrontal cortex | journal = Behav Brain Res | volume = 359 | issue = | pages = 828–835 | date = February 2019 | pmid = 30053461 | doi = 10.1016/j.bbr.2018.07.020 | url = }}</ref><ref name="HalberstadtChathaKlein2020" /><ref name="MayDantanarayanaZinke2006">{{cite journal | vauthors = May JA, Dantanarayana AP, Zinke PW, McLaughlin MA, Sharif NA | title = 1-((S)-2-aminopropyl)-1H-indazol-6-ol: a potent peripherally acting 5-HT2 receptor agonist with ocular hypotensive activity | journal = J Med Chem | volume = 49 | issue = 1 | pages = 318–328 | date = January 2006 | pmid = 16392816 | doi = 10.1021/jm050663x | url = }}</ref> It substitutes for other psychedelics such as [[DOM (drug)|DOM]] and [[LSD]] in animal [[drug discrimination]] tests, but does not substitute for [[entactogen]]s like [[MDMA]] or [[psychostimulant]]s like [[dextromethamphetamine]] or [[cocaine]].<ref name="GlennonJacynoYoung1983">{{cite journal | vauthors = Glennon RA, Jacyno JM, Young R | title = A comparison of the behavioral properties of (+/-)-, (-)-, and (+)-5-methoxy-alpha-methyltryptamine | journal = Biol Psychiatry | volume = 18 | issue = 4 | pages = 493–498 | date = April 1983 | pmid = 6860723 | doi = | url = }}</ref><ref name="GatchForsterJanowsky2011" /> In contrast to other psychedelics, 5-MeO-AMT has been found to not fully substitute for other psychedelics including DOM, LSD, and [[dimethyltryptamine]] (DMT), but did partially generalize to LSD (67% responding).<ref name="GatchForsterJanowsky2011" /> This is analogous to findings with [[5-MeO-DMT]], which has a major serotonin 5-HT<sub>2A</sub> receptor-mediated component to its discriminative stimulus properties.<ref name="ErmakovaDunbarRucker2022">{{cite journal | vauthors = Ermakova AO, Dunbar F, Rucker J, Johnson MW | title = A narrative synthesis of research with 5-MeO-DMT | journal = J Psychopharmacol | volume = 36 | issue = 3 | pages = 273–294 | date = March 2022 | pmid = 34666554 | pmc = 8902691 | doi = 10.1177/02698811211050543 | url = }}</ref><ref name="ShenJiangWinter2010">{{cite journal | vauthors = Shen HW, Jiang XL, Winter JC, Yu AM | title = Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions | journal = Curr Drug Metab | volume = 11 | issue = 8 | pages = 659–666 | date = October 2010 | pmid = 20942780 | pmc = 3028383 | doi = 10.2174/138920010794233495 | url = }}</ref><ref name="WinterFilipinkTimineri2000">{{cite journal | vauthors = Winter JC, Filipink RA, Timineri D, Helsley SE, Rabin RA | title = The paradox of 5-methoxy-N,N-dimethyltryptamine: an indoleamine hallucinogen that induces stimulus control via 5-HT1A receptors | journal = Pharmacol Biochem Behav | volume = 65 | issue = 1 | pages = 75–82 | date = January 2000 | pmid = 10638639 | doi = 10.1016/s0091-3057(99)00178-1 | url = }}</ref> 5-MeO-AMT does not produce [[locomotor hyperactivity]], [[behavioral sensitization]], [[conditioned place preference]], or [[self-administration]], further indicating a lack of psychostimulant-like effects as well as [[misuse potential]].<ref name="GatchForsterJanowsky2011" /><ref name="AbieroBotanasSayson2019" /> Instead, 5-MeO-AMT produces [[hypolocomotion]].<ref name="GatchForsterJanowsky2011" /> 5-MeO-AMT is known to produce [[sympathomimetic]] effects, but these effects likely depend on serotonin 5-HT<sub>2A</sub> receptor activation rather than on monoamine release or reuptake inhibition.<ref name="RickliMoningHoener2016" /> Other serotonergic psychedelics are also well known to produce sympathomimetic effects.<ref name="Wsół2023">{{cite journal | vauthors = Wsół A | title = Cardiovascular safety of psychedelic medicine: current status and future directions | journal = Pharmacol Rep | volume = 75 | issue = 6 | pages = 1362–1380 | date = December 2023 | pmid = 37874530 | pmc = 10661823 | doi = 10.1007/s43440-023-00539-4 | url = }}</ref><ref name="NeumannDheinKirchhefer2024">{{cite journal | vauthors = Neumann J, Dhein S, Kirchhefer U, Hofmann B, Gergs U | title = Effects of hallucinogenic drugs on the human heart | journal = Front Pharmacol | volume = 15 | issue = | pages = 1334218 | date = 2024 | pmid = 38370480 | pmc = 10869618 | doi = 10.3389/fphar.2024.1334218 | doi-access = free | url = }}</ref><ref name="LeyHolzeArikci2023">{{cite journal | vauthors = Ley L, Holze F, Arikci D, Becker AM, Straumann I, Klaiber A, Coviello F, Dierbach S, Thomann J, Duthaler U, Luethi D, Varghese N, Eckert A, Liechti ME | title = Comparative acute effects of mescaline, lysergic acid diethylamide, and psilocybin in a randomized, double-blind, placebo-controlled cross-over study in healthy participants | journal = Neuropsychopharmacology | volume = 48 | issue = 11 | pages = 1659–1667 | date = October 2023 | pmid = 37231080 | pmc = 10517157 | doi = 10.1038/s41386-023-01607-2 | url = }}</ref>

==Chemistry==
5-MeO-AMT, also known as 5-methoxy-α-methyltryptamine, is a [[substituted tryptamine]] [[chemical derivative|derivative]]. It is a derivative of [[tryptamine]] (T), [[5-methoxytryptamine]] (5-MeO-T or 5-MT), and [[α-methyltryptamine]] (AMT or αMT) and is an [[structural analog|analogue]] of other tryptamines like [[α-methylserotonin]] (5-HO-AMT) and [[5-MeO-DMT]]. Some derivatives of 5-MeO-AMT include [[α,N,O-TMS|α,''N''-dimethyl-5-methoxytryptamine]] (5-MeO-α-Me-NMT or α,''N'',''O''-TMS) and [[α,N,N,O-TMS|α,''N'',''N''-trimethyl-5-methoxytryptamine]] (5-MeO-α-Me-DMT or α,''N'',''N'',''O''-TMS). As noted by [[Alexander Shulgin]], the α-methylated [[tryptamine]]s can be looked at as the tryptamine homologues of the [[substituted amphetamine|amphetamine]]s (α-methylated phenethylamines).

5-MeO-AMT is [[soluble]] in [[water]] and [[ethanol]] but not in [[ether]].<ref name="Shulgin1979" />

==History==
5-MeO-AMT was first [[chemical synthesis|synthesized]] and described in the [[scientific literature]] in 1958.<ref name="ShulginNichols1978" /><ref name="Shulgin1979" /><ref name="PietraTacconi1958">{{cite journal | vauthors = Pietra S, Tacconi G | title = Derivati indolici. III. Preparazione di alpha-alchil e alpha-ariltriptamine | trans-title = Indole derivatives. III. The preparation of alpha-alkyl and of alpha-aryltryptamines | language = Italian | journal = Farmaco Sci | volume = 13 | issue = 12 | pages = 893–910 | date = 1958 | pmid = 13619730 | doi = | url = }}</ref> Its psychedelic effects in humans were first observed in 1976 and were described by [[Alexander Shulgin]] and [[David E. Nichols]] and colleagues by 1978.<ref name="ShulginNichols1978">{{cite book | vauthors = Shulgin AT, Nichols DE | title=The Psychopharmacology of Hallucinogens | chapter=Characterization of Three New Psychotomimetics | publisher=Elsevier | date=1978 | isbn=978-0-08-021938-7 | doi=10.1016/b978-0-08-021938-7.50010-2 | page=74–83 | chapter-url=https://bitnest.netfirms.com/external/10.1016/B978-0-08-021938-7.50010-2}}</ref><ref name="Shulgin1979">{{cite journal | vauthors = Shulgin AT | title=Profiles of Psychedelic Drugs: α-O-DMS | journal=Journal of Psychedelic Drugs | volume=11 | issue=3 | date=1979 | issn=0022-393X | doi=10.1080/02791072.1979.10472112 | pages=247–247 | url=https://bitnest.netfirms.com/external/10.1080/02791072.1979.10472112| url-access=subscription }}</ref><ref name="KantorDudlettesShulgin1980">{{cite journal | vauthors = Kantor RE, Dudlettes SD, Shulgin AT | title = 5-Methoxy-α-Methyltryptamine (α,O-Dimethylserotonin), A Hallucinogenic Homolog of Serotonin | journal = Biol Psychiatry | volume = 15 | issue = 2 | pages = 349–352 | date = April 1980 | pmid = 7417623 | doi = | url = https://bitnest.netfirms.com/external/Biol.Psychiatry/15.2.349}}</ref>

==Society and culture==
===Legal status===
====Australia====
5-MeO-AMT is considered a Schedule 9 prohibited substance in Australia under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]] (October 2015).<ref name="Poisons Standard">{{cite web | title = Poisons Standard | work = Federal Register of Legislation | publisher = Australian Government | date = October 2015 | url = https://www.comlaw.gov.au/Details/F2015L01534 }}</ref> A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.<ref name="Poisons Standard" />

====Sweden====
[[Riksdag|''Sveriges riksdags'']] health ministry [[:sv:Statens folkhälsoinstitut|''Statens folkhälsoinstitut'']] classified 5-MeO-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 Oct 1, 2004, in their regulation SFS 2004:696 listed as 5-metoxi-alfametyltryptamin (5-MeO-AMT), making it illegal to sell or possess.<ref>{{cite web |title=Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor | trans-title = Ordinance amending the ordinance (1999: 58) on the prohibition of certain dangerous goods; |url=http://www.notisum.se/rnp/sls/sfs/20040696.pdf |language=Swedish | work = Swedish Code of Statutes |id=SFS 2004:696 |date=19 August 2004}}</ref>

====United Kingdom====
5-MeO-αMT was made illegal in the United Kingdom as of 7 January 2015, along with 5-MeO-DALT. This was following the events of 10 June 2014 when the Advisory Council on the Misuse of Drugs recommended that 5-MeO-αMT be scheduled as a class A drug by updating the blanket ban clause on tryptamines.

====United States====
5-MeO-AMT is unscheduled at the federal level in the [[United States]].<ref name="PART 1308 — SCHEDULES OF CONTROLLED SUBSTANCES - 1308.11 Schedule I">{{Cite web |url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |title=§1308.11 Schedule I. |access-date=2014-12-17 |archive-date=2009-08-27 |archive-url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |url-status=dead | work = Diversion Control Division | publisher = Drug Enforcement Administration, U.S. Department of Justice }}</ref> However, the DEA considers the chemical a controlled substance analogue.<ref name="5-MeO-AMT; Fast Facts"></ref> The agency's opinion on this matter may change at any time.

=====Florida=====
5-MeO-AMT is a [[Controlled Substances Act|Schedule I]] controlled substance in the state of [[Florida]], making it illegal to buy, sell, or possess.<ref name="Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL">{{cite web | url = http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html | work = Florida Statutes | title = Chapter 893 - Drug Abuse Prevention and Control }}</ref>

== See also ==
* [[5-Allyloxy-AMT]]
* [[5-Chloro-αMT]]
* [[5-EtO-AMT]]
* [[5-MeO-AET]]
* [[5-MeO-DMT]]
* [[5-MeO-DPT]]
* [[5-Methoxy-diisopropyltryptamine|5-MeO-DiPT]]
* [[alpha-Methyltryptamine|AMT]]
* [[O-Methyl-AL-34662|''O''-Methyl-AL-34662]]

== References ==
{{Reflist}}

== External links ==
* [https://web.archive.org/web/20060527232352/http://www.dea.gov/programs/forensicsci/microgram/journal071203/mj071203_pg1.html DEA forensic journal on 5-MeO-AMT]
* [http://www.erowid.org/chemicals/5meo_amt/5meo_amt.shtml Erowid 5-MeO-AMT vault]
* [https://web.archive.org/web/20060523174755/http://leda.lycaeum.org/Chemicals/alpha,O-DMS.3416.shtml Lycaeum 5-MeO-AMT page]
* [http://www.erowid.org/library/books_online/tihkal/tihkal05.shtml TiHKAL entry]
* [http://tihkal.info/read.php?domain=tk&id=5 5-MeO-AMT (α,''O''-DMS) entry in TiHKAL • info]

{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Monoamine releasing agents}}
{{Tryptamines}}

[[Category:5-HT1A agonists]]
[[Category:5-HT2A agonists]]
[[Category:5-HT2B agonists]]
[[Category:Alpha-Alkyltryptamines]]
[[Category:Designer drugs]]
[[Category:5-Methoxytryptamines]]
[[Category:Monoamine oxidase inhibitors]]
[[Category:Psychedelic tryptamines]]
[[Category:Serotonin-norepinephrine-dopamine releasing agents]]
[[Category:Serotonin receptor agonists]]