Editing 5-MeO-AMT (section)

{{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>