Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 09:28, 28 August 2011 editBogBot (talk | contribs)Bots53,132 edits populated new fields in {{drugbox}} and reordered per bot approval. Report errors and suggestions to User_talk:BogBot← Previous edit		Latest revision as of 01:17, 14 November 2024 edit undo76.174.0.57 (talk) →Pharmacodynamics: Tweak.
(99 intermediate revisions by 48 users not shown)
Line 1:		Line 1:
			{{Short description|Chemical compound}}
	{{DISPLAYTITLE:''alpha''-Ethyltryptamine}}
			{{Lowercase title}}
	{{Drugbox
			{{cs1 config|name-list-style=vanc|display-authors=6}}
	| verifiedrevid = 443659095
			{{Infobox drug
	| IUPAC_name = 1-(1''H''-indol-3-yl)butan-2-amine
			| verifiedrevid = 447115140
			| drug_name = α-Ethyltryptamine
			| INN = Etryptamine
			| USAN = Etryptamine
	| image = AET.svg		| image = AET.svg
	| width = 150px		| width =
	| image2 = Alpha-Ethyltryptamine-3d-sticks.png		| image2 = Alpha-Ethyltryptamine-3d-sticks.png
	| width2 = 150px		| width2 =
	| drug_name = α-Ethyltryptamine
			<!-- Clinical data -->
			| tradename = Monase<ref name="GlennonDukat2023" />
			| routes_of_administration = ]<ref name="GlennonDukat2023" />
			| class = ]; ]; ]; ]; ]<ref name="GlennonDukat2023" />
	<!--Clinical data-->		<!-- Legal status -->
			| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
	| tradename =
			| 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=] |language=pt-BR |publication-date=2023-07-25}}</ref>
			| legal_CA = Schedule III
	| legal_US = Schedule I		| legal_US = Schedule I
			| legal_UK = Class A
			| legal_DE = Anlage I
			| legal_UN = P I
	<!--Identifiers-->		<!-- Pharmacokinetic data -->
			| bioavailability =
			| protein_bound =
			| metabolism = ]<ref name="Barceloux2012" />
			| metabolites = • 6-Hydroxy-αET (inactive)<ref name="GlennonDukat2023" /><ref name="Barceloux2012" />
			| onset = 0.5–1.5{{nbsp}}hours<ref name="Barceloux2012" />
			| elimination_half-life = ~8{{nbsp}}hours<ref name="Barceloux2012" />
			| duration_of_action = 6–8{{nbsp}}hours (100–150{{nbsp}}mg)<ref name="Oeri2021" /><ref name="Barceloux2012" />
			| excretion = ] (majority)<ref name="Barceloux2012" />
			<!-- Identifiers -->
			| CAS_number_Ref = {{cascite|correct|CAS}}
	| CAS_number = 2235-90-7		| CAS_number = 2235-90-7
	| CAS_supplemental = {{CAS|118-68-3}}		| CAS_supplemental = <br />{{CAS|118-68-3}} (])<br />{{CAS|26330-11-0}} (])
	| ATC_prefix = none		| ATC_prefix = None
			| ATC_suffix =
	| PubChem = 8367		| PubChem = 8367
			| PubChemSubstance = 46507084
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB01546		| DrugBank = DB01546
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 8064		| ChemSpiderID = 8064
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = GR181O3R32
			| ChEBI = 134838
			| ChEMBL = 1619758
			| KEGG = D04092
			| synonyms = alpha-Ethyltryptamine; αET; AET; α-ET; Etryptamine; PAL-125;<ref name="BloughLandavazo2014" /> 3-(2-Aminobutyl)indole; 3-Indolylbutylamine; U-17312E; U17312E; Ro 3-1932; NSC-63963; NSC-88061
	<!--Chemical data-->		<!-- Chemical data -->
			| IUPAC_name = 1-(1''H''-indol-3-yl)butan-2-amine
	| C=12 | H=16 | N=2		| C=12 | H=16 | N=2
			| SMILES = CCC(N)CC1=CNC2=CC=CC=C12
	| molecular_weight = 188.27 g/mol
	| smiles = c1cccc2c1c(c2)CC(N)CC
	| InChI = 1/C12H16N2/c1-2-10(13)7-9-8-14-12-6-4-3-5-11(9)12/h3-6,8,10,14H,2,7,13H2,1H3
	| InChIKey = ZXUMUPVQYAFTLF-UHFFFAOYAJ
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C12H16N2/c1-2-10(13)7-9-8-14-12-6-4-3-5-11(9)12/h3-6,8,10,14H,2,7,13H2,1H3		| StdInChI = 1S/C12H16N2/c1-2-10(13)7-9-8-14-12-6-4-3-5-11(9)12/h3-6,8,10,14H,2,7,13H2,1H3
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = ZXUMUPVQYAFTLF-UHFFFAOYSA-N		| StdInChIKey = ZXUMUPVQYAFTLF-UHFFFAOYSA-N
	| synonyms = 3-(2-aminobutyl)indole
			<!-- Physical data -->
	| melting_point = 222		| melting_point = 222
	| melting_high = 223		| melting_high = 223
	}}		}}
			<!-- Definition and medical uses -->
			'''α-Ethyltryptamine''' ('''αET''', '''AET'''), also known as '''etryptamine''', is an ] and ] ] of the ] family.<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="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="TiHKAL">{{cite book|title=''Tryptamines i Have Known and Loved: The Continuation,''|year=1997|publisher=Transform Press|location=Berkeley, CA|isbn=978-0-9630096-9-2|chapter-url=http://www.erowid.org/library/books_online/tihkal/tihkal11.shtml| vauthors = Shulgin A, Shulgin A |edition=First | author-link=Alexander Shulgin |author2-link=Ann Shulgin|access-date=15 November 2013|chapter-format=Book|chapter="''Part 2, The Chemistry Continues: #11, a-ET: Alpha-Ethyltryptamine; Indole,3-(2-Aminobutyl); Tryptamine,Alpha-Ethyl; 3-(2-Aminobutyl)Indole; Monase," part v, "EXTENSIONS AND COMMENTARY.''"|quote=This base, a-ET or etryptamine, was a promising anti-depressant, explored clinically as the acetate salt by Upjohn under the name of Monase. Its central stimulant activity is probably not due to its monoamineoxidase inhibition activity, but appears to stem from its structural relationship to the indolic psychedelics. It was withdrawn from potential commercial use with the appearance of an unacceptable incidence of a medical condition known as agranulocytosis, but the extra mural research into its action, among the lay population, goes on, }}</ref> It was originally developed and marketed as an ] under the brand name '''Monase''' by ] in the 1960s before being ] due to ].<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="US3296072">{{ cite patent | country = US | number = 3296072 | status = Patent | title = Method of Treating Mental Depression | pubdate = 1967-01-03 | gdate = 1967-01-03 | fdate = 1964-01-29 | pridate = 1962-06-11 | inventor = Szmuszkovicz J | invent1 = | invent2 = | assign1 = Upjohn Company | postscript = . | assign2 = | class = | url=http://www.google.com/patents/US3296072}}</ref>
			<!-- Side effects, mechanism of action, and chemistry -->
	'''α-ethyltryptamine''' ('''''αET''''', '''''AET''''', "'''''Monase'''''"), also known as '''etryptamine''', is a ], ] and ] of the ] ].
			]s of αET include ], ], ], ], ], ], and ], among others.<ref name="Barceloux2012" /> A rare ] of αET is ].<ref name="GlennonDukat2023" /><ref name="TiHKAL" /><ref name="Butin1962">{{cite journal | vauthors = Burtin JW | title = Agranulocytosis following Monase therapy | journal = J Kans Med Soc | volume = 63 | issue = | pages = 338–340 | date = August 1962 | pmid = 13875179 | doi = | url = }}</ref> αET acts as a ], as a weak ], and as a weak ].<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="BloughLandavazo2014" /> It may also produce ].<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="HuangJohnsonNichols1991" /> αET is a ] and is closely related to ] (αMT) and other ]s.<ref name="GlennonDukat2023" /><ref name="Oeri2021" />
	== History ==		<!-- History, society, and culture -->
			αET was first described in 1947.<ref name="GlennonDukat2023" /><ref name="SnyderKatz1947" /> It was used as an antidepressant for about a year around 1961.<ref name="GlennonDukat2023" /> The drug started being used ] in the 1980s and several deaths have been reported.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="VarìPichiniGiorgetti2019" /><ref name="Barceloux2012" /> αET is a ] in various countries, including the ] and ].<ref name="GlennonDukat2023" /><ref name="VarìPichiniGiorgetti2019" /> There has been renewed interest in αET, for instance as an alternative to ], with the development of ]s and entactogens as ]s in the 2020s.<ref name="GlennonDukat2023" /><ref name="Oeri2021" />
	Originally believed to exert its effects predominantly via ], alpha-ethyltryptamine was ] as an ] by ] in the ] under the name "'''''Monase'''''" but was withdrawn from potential commercial use due to an unacceptable incidence of ].<ref>].</ref>
			==Medical uses==
	αET gained limited recreational popularity as a ] in the ]s. Subsequently, in the ] it was added to the ] list of ]s in ].
			αET was previously used medically as an ] and "psychic energizer" to treat people with ].<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="Barceloux2012" /><ref name="TiHKAL" /> It was used for this indication under the brand name Monase.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="Barceloux2012" /><ref name="TiHKAL" />
			===Available forms===
	== Pharmacology ==
			αET was available ] as the ] ] under the brand name Monase in the form of 15{{nbsp}}mg ] ]s.<ref name="RockyMountainDruggist1961">{{cite book | title=Rocky Mountain Druggist | issue=v. 72 | year=1961 | url=https://books.google.com/books?id=gZd8lzHm9TYC | access-date=6 September 2024 | pages=12, 17 | quote = MONASE--Upjohn Monase 15 mg. Monase, brand of etryptamine acetate is 3-(2-aminobutyl) indole acetate, developed in the Research Laboratories of the Upjohn Company. Each tablet contains etryptamine acetate 15 mg. Monase is indicated in a variety of psychiatric and medical conditions in which mental depression is prominent and for which mood elevation and psychomotor stimulation are considered beneficial. ADMINISTRATION AND DOSAGE: 30 mg. daily in divided doses. SUPPLIED: As coated, compressed tablets, 15 mg., in bottles of 100 and is a prescription product. The catalog number is 3522.}}</ref><ref name="GlennonDukat2023" />
	αET is ] and ] related to ] (αMT), but its effects are slightly different. In contrast to αMT, αET is less ] and ], its effects resembling more those of ]s like ] ("Ecstasy").
			==Effects==
	Similarly to ], αET has been demonstrated to be a ] of ], ] and ] (with ] being the primary ] affected); in addition, it acts as a non-selective ] ]. Scientific research has shown that alpha-ethyltryptamine is a serotonergic ].<ref name="pmid1722753">{{cite journal | author = 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 | year = 1991 | month = July | pmid = 1722753 | doi = 10.1016/0014-2999(91)90686-K| url = }}</ref>
			αET is reported to have ] and weak ] effects.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="TiHKAL" /> ], ], ], and ] have been specifically reported.<ref name="Oeri2021" /><ref name="GlennonDukat2023" /><ref name="TiHKAL" /> Unlike αMT and other ]s, αET is not reported to have ] or ]ic effects.<ref name="Oeri2021" /><ref name="TiHKAL" /> The drug is described as less stimulating and intense than ] ("ecstasy") but as otherwise having entactogenic effects resembling those of MDMA.<ref name="Oeri2021" /><ref name="GlennonDukat2023" /> The dose of αET used ] has been reported to be 100 to 160{{nbsp}}mg, its ] has been reported to be 0.5 to 1.5{{nbsp}}hours, and its ] at the preceding doses is described as 6 to 8{{nbsp}}hours.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="Barceloux2012" /><ref name="TiHKAL" /> Rapid ] to repeated administration of αET has been described.<ref name="TiHKAL" />
			==Side effects==
			]s of αET at antidepressant doses have included ], ], ], ], ], and ].<ref name="Barceloux2012" /> Additional side effects of αET at ] doses have included ] and feelings of ].<ref name="Barceloux2012" /> Feelings of ] and ] can occur once the drug wears off.<ref name="Barceloux2012" />
			As with many other ]s, ], such as ], can occur when ] are taken or when combined with certain drugs such as ]s (MAOIs).<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 | quote = Drugs such as MDMA, ecstasy (3,4-methylenedioxymethamphetamine), if combined with MAOIs (including moclobemide) do also cause fatalities because they act as serotonin releasers | doi-access = free }}</ref> Several deaths have been associated with recreational use of αET.<ref name="GlennonDukat2023" /><ref name="VarìPichiniGiorgetti2019">{{cite journal | vauthors = Varì MR, Pichini S, Giorgetti R, Busardò FP | first4=Francesco P. | title=New psychoactive substances—Synthetic stimulants | journal=WIREs Forensic Science | volume=1 | issue=2 | date= March 2019 | issn=2573-9468 | doi=10.1002/wfs2.1197 | page=}}</ref><ref name="Barceloux2012" />
	== See also ==
	* ]
	* ]
			Rarely, ] has occurred with prolonged administration of αET at antidepressant doses and has been said to have resulted in several cases and/or deaths.<ref name="GlennonDukat2023" /><ref name="Barceloux2012" /><ref name="Butin1962" />
	== References ==
	{{Reflist}}
			==Overdose==
	== External links ==
			αET has been administered in clinical studies at doses of up to 300{{nbsp}}mg per day.<ref name="GlennonDukat2023" /><ref name="Barceloux2012" /><ref name="TurnerMerlis1961">{{cite journal | vauthors = Turner WJ, Merlis S | title = Clinical studies with ethyltryptamine | journal = Journal of Neuropsychiatry | volume = 2(Suppl 1) | issue = | pages = 73–76 | date = February 1961 | pmid = 13778759 | doi = | url = }}</ref> An approximate but unconfirmed 700{{nbsp}}mg dose resulted in fatal ] and ] ] in one case.<ref name="GlennonDukat2023" /><ref name="Barceloux2012" /> ] doses of αET for various species have been studied and described.<ref name="GlennonDukat2023" /> Treatment of αET ] or ] is supportive.<ref name="Barceloux2012" /> Severe and potentially life-threatening ] may occur.<ref name="Barceloux2012" /> ] associated with serotonergic agents like αET can be managed with ]s and with the ] ].<ref name="SchifanoNapoletanoChiappini2019">{{cite journal | vauthors = Schifano F, Napoletano F, Chiappini S, Orsolini L, Guirguis A, Corkery JM, Bonaccorso S, Ricciardi A, Scherbaum N, Vento A | title=New Psychoactive Substances (NPS), Psychedelic Experiences and Dissociation: Clinical and Clinical Pharmacological Issues | journal=Current Addiction Reports | volume=6 | issue=2 | date=2019 | issn=2196-2952 | doi=10.1007/s40429-019-00249-z | pages=140–152}}</ref>
	* <cite id=erowidTihkal>{{cite web
	|author = Erowid.org
			==Pharmacology==
	|year = 2009
			===Pharmacodynamics===
	|title = TiHKAL #11. a-ET
			Similarly to αMT, αET is a ] of ], ] and ], with ] being the primary ] affected.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><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> It is about 10-fold more ] in inducing serotonin release than in inducing dopamine release and about 28-fold more potent in inducing serotonin release than in inducing norepinephrine release.<ref name="GlennonDukat2023" /><ref name="BloughLandavazo2014" /> The (+)-] of αET, (+)-αET, is a ] (SDRA) and is one of the few such agents known.<ref name="BloughLandavazo2014" /> It is about 1.7-fold more potent in inducing serotonin release than in inducing dopamine release, about 17-fold more potent in inducing serotonin release than in inducing norepinephrine release, and is about 10-fold more potent in inducing dopamine release than in inducing norepinephrine release.<ref name="BloughLandavazo2014" />
	|url = http://www.erowid.org/library/books_online/tihkal/tihkal11.shtml
	|accessdate = 2010-02-10
			In addition to acting as a ], αET acts as a ] ].<ref name="GlennonDukat2023" /> It is known to act as a weak ] of the serotonin ] ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} > 10,000{{nbsp}}nM; ] = 21%).<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="BloughLandavazo2014" /> (–)-αET is inactive as a 5-HT<sub>2A</sub> receptor agonist at concentrations of up to 10{{nbsp}}μM, whereas (+)-αET is a 5-HT<sub>2A</sub> receptor agonist with an EC<sub>50</sub> value of 1,250{{nbsp}}nM and an E<sub>max</sub> value of 61%.<ref name="BloughLandavazo2014" /> αET has also been found to have weak ] for the ], ], ], and ]s.<ref name="GlennonDukat2023" />
	}}
	</cite>
			{| class="wikitable floatright" style="font-size:small;"
	*
			|+ Activities of αET, its enantiomers, and related compounds
	*
			|-
			! rowspan="2" | Compound !! colspan="3" | ] ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}}, nM) !! colspan="2" | ] ]
			|-
			! ] !! ] !! ] !! {{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} (nM) !! ] (%)
			|-
			| ]<!-- T; PAL-235 --> || 32.6 ± 2.6 || 164 ± 16 || 716 ± 46 || 7.36 ± 0.56 || 104 ± 4
			|-
			| ]<!-- 5-HT --> || 44.4 ± 5.3 || >10,000 || >10,000 || {{Abbr|ND|No data}} || {{Abbr|ND|No data}}
			|-
			| ] || 114 ± 15 || >10,000 || 4,166 ± 317 || 38.3 ± 0.81 || 83 ± 0.4
			|-
			| ]<!-- PAL-17 --> || 21.7 ± 1.0 || 78.6 ± 4.0 || 112 ± 6 || 23.1 ± 2.4 || 103 ± 3
			|-
			| αET<!-- (±)-αET; (RS)-αET; PAL-125 --> || 23.2 ± 1.7 || 232 ± 17 || 640 ± 76<sup>a</sup> || >10,000 || 21 ± 11
			|-
			| {{nbsp}}{{nbsp}}(–)-αET<!-- (R)-αET; PAL-640 --> || 54.9 ± 7.8 || 654 ± 50 || 3,670 ± 1,190<sup>a</sup> || >10,000 || –
			|-
			| {{nbsp}}{{nbsp}}(+)-αET<!-- (S)-αET; PAL-647 --> || 34.7 ± 4.9 || 57.6 ± 3.1 || 592 ± 97<sup>a</sup> || 1,250 ± 310 || 61 ± 8
			|-
			| ] || 56.6 ± 2.1 || 376 ± 16 || 77.4 ± 3.4 || {{Abbr|ND|No data}} || {{Abbr|ND|No data}}
			|- class="sortbottom"
			| colspan="6" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' The smaller the value, the more strongly the compound produces the effect. '''Footnotes:''' <sup>a</sup> = αET, (–)-αET, and (+)-αET were norepinephrine partial releasers with ] values of 78%, 75%, and 71%, respectively. '''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>
			|}
			αET is a weak ] (MAOI).<ref name="GlennonDukat2023" /><ref name="AskFagervallRoss1983">{{cite journal | vauthors = Ask AL, Fagervall I, Ross SB | title = Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 324 | issue = 2 | pages = 79–87 | date = September 1983 | pmid = 6646243 | doi = 10.1007/BF00497011 }}</ref> It is specifically a ] and ] ] of ] (MAO-A).<ref name="GlennonDukat2023" /><ref name="AskFagervallRoss1983" /> An {{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}} value of 260{{nbsp}}μM '']'' and 80 to 100% inhibition of MAO-A at a dose of 10{{nbsp}}mg/kg in rats '']'' have been reported.<ref name="GlennonDukat2023" /><ref name="Rényi1986">{{cite journal | vauthors = Rényi L | title = The effects of monoamine oxidase inhibitors on the ejaculatory response induced by 5-methoxy-N,N-dimethyltryptamine in the rat | journal = Br J Pharmacol | volume = 88 | issue = 4 | pages = 827–835 | date = August 1986 | pmid = 3091132 | pmc = 1917087 | doi = 10.1111/j.1476-5381.1986.tb16256.x | url = }}</ref> αET is described as slightly more potent as an MAOI than ].<ref name="GlennonDukat2023" /> Both enantiomers of αET have similar activity as MAOIs, whereas αET's major metabolite 6-hydroxy-αET is inactive.<ref name="GlennonDukat2023" /> The relatively weak MAOI actions of αET have been considered unlikely to be involved in its stimulant, antidepressant, and other psychoactive effects by certain sources.<ref name="GlennonDukat2023" /><ref name="TiHKAL" />
			The stimulant effects of αET have been said to lie primarily in (–)-αET, whereas hallucinogenic effects have been said to be present in (+)-αET.<ref name="GlennonDukat2023" /><ref name="Barceloux2012" /> However, these claims appear to be based on animal drug discrimination studies and are not necessarily in accordance with functional studies.<ref name="GlennonDukat2023" /><ref name="BloughLandavazo2014" /> Generalization to {{Abbrlink|DOM|2,5-dimethoxy-4-methylamphetamine}} may have been anomalous and due to the serotonin-releasing actions of αET rather than due to serotonin 5-HT<sub>2A</sub> receptor activation and associated psychedelic effects.<ref name="GlennonDukat2023" /> Accordingly, αET does not produce the ] in rodents, unlike known psychedelics.<ref name="GlennonDukat2023" /> In addition, clear hallucinogenic effects of αET have never been documented in humans even at high doses, although the individual enantiomers of αET have never been studied in humans.<ref name="GlennonDukat2023" />
			αET has been found to produce ] similar to that of MDMA and ] (PCA) in rats.<ref name="Oeri2021" /><ref name="GlennonDukat2023" /><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> This has included long-lasting reductions in ] levels, ] (5-HIAA) levels, and serotonin ] sites in the ] and ].<ref name="Oeri2021" /><ref name="HuangJohnsonNichols1991" /> The dosage of αET employed was 8{{nbsp}}doses of 30{{nbsp}}mg/kg by ] with doses spaced by 12-hour intervals.<ref name="Oeri2021" /><ref name="HuangJohnsonNichols1991" /> There are prominent species differences in the neurotoxicity of monoamine releasing agents.<ref name="CapelaCarmoRemião2009">{{cite journal | vauthors = Capela JP, Carmo H, Remião F, Bastos ML, Meisel A, Carvalho F | title = Molecular and cellular mechanisms of ecstasy-induced neurotoxicity: an overview | journal = Mol Neurobiol | volume = 39 | issue = 3 | pages = 210–271 | date = June 2009 | pmid = 19373443 | doi = 10.1007/s12035-009-8064-1 | url = }}</ref><ref name="MoratallaKhairnarSimola2017">{{cite journal | vauthors = Moratalla R, Khairnar A, Simola N, Granado N, García-Montes JR, Porceddu PF, Tizabi Y, Costa G, Morelli M | title = Amphetamine-related drugs neurotoxicity in humans and in experimental animals: Main mechanisms | journal = Prog Neurobiol | volume = 155 | issue = | pages = 149–170 | date = August 2017 | pmid = 26455459 | doi = 10.1016/j.pneurobio.2015.09.011 | url = | hdl = 10261/156486 | hdl-access = free }}</ref> Primates appear to be more susceptible to the damage caused by serotonergic neurotoxins like MDMA than rodents.<ref name="CapelaCarmoRemião2009" />
			===Pharmacokinetics===
			The ] of αET appears to be rapid.<ref name="Barceloux2012" /> It has a relatively large ].<ref name="Barceloux2012" /> The drug undergoes ] to form the major ] 6-hydroxy-αET (3-(2-aminobutyl)-6-hydroxyindole).<ref name="GlennonDukat2023" /><ref name="Barceloux2012" /> This metabolite is inactive.<ref name="Barceloux2012" /> αET is ] primarily in ] and a majority of a dose is ] in urine within 12 to 24{{nbsp}}hours.<ref name="Barceloux2012" /> Its ] is approximately 8{{nbsp}}hours.<ref name="Barceloux2012" />
			==Chemistry==
			αET, also known as 3-(2-aminobutyl)indole, is a ] and ] ].<ref name="GlennonDukat2023" /><ref name="Oeri2021" /> ]s of αET include ] (αMT) and other substituted α-alkylated tryptamines like ], ] (PAL-542), and ] (PAL-545).<ref name="BloughLandavazo2014" />
			==History==
			αET was first described in the ] in 1947.<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 }}</ref> The ]s of αET were first individually described in 1970.<ref name="GlennonDukat2023" />
			Originally believed to exert its effects predominantly via ], αET was ] during the 1960s as an ] by ] in the ] under the generic name etryptamine and the brand name Monase, but was withdrawn from potential commercial use due to incidence of ] ] in several patients.<ref name="GlennonDukat2023" /><ref name="TiHKAL" /><ref name="Butin1962" /> It was on the market for about a year, around 1961, and was given to more than 5,000{{nbsp}}patients, before being withdrawn.<ref name="GlennonDukat2023" /> αET was usually used as an antidepressant at doses of 30 to 40{{nbsp}}mg/day (but up to 75{{nbsp}}mg/day), which are lower than the doses that have been used ].<ref name="GlennonDukat2023" /><ref name="Oeri2021" />
			αET gained limited recreational popularity as a ] with MDMA-like effects in the 1980s.<ref name="GlennonDukat2023" /> Subsequently, in the ] it was added to the ] list of ]s in 1993 or 1994.<ref name="GlennonDukat2023" /><ref name="TiHKAL" />
			==Society and culture==
			===Names===
			''Etryptamine'' is the formal ] of the drug and its {{Abbrlink|INN|International Nonproprietary Name}} and {{Abbrlink|BAN|British Approved 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&pg=PA48 | access-date=2024-09-06 | page=48}}</ref> In the case of the ] ], its generic name is ''etryptamine acetate'' and this is its {{Abbrlink|USAN|United States Adopted Name}}.<ref name="Elks2014" /> Etryptamine was used ] as etryptamine acetate.<ref name="Elks2014" /><ref name="GlennonDukat2023" /><ref name="RockyMountainDruggist1961" /> Etryptamine is much more well-known as ''alpha-ethyltryptamine'' or ''α-ethyltryptamine'' (abbreviated as ''αET'', ''α-ET'', or ''AET'').<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="TiHKAL" /> Other synonyms of αET and/or its acetate salt include ''3-(2-aminobutyl)indole'', ''3-indolylbutylamine'', ''PAL-125'', ''U-17312E'', ''Ro 3-1932'', ''NSC-63963'', and ''NSC-88061'', as well as its former brand name ''Monase''.<ref name="Elks2014" /><ref name="CAS-αET">{{cite web | title=α-Ethyltryptamine | id = CAS Registry Number 2235-90-7 | website=CAS Common Chemistry | date=6 September 2024 | url=https://commonchemistry.cas.org/detail?cas_rn=2235-90-7 | access-date=6 September 2024}}</ref><ref name="CAS-αET-acetate">{{cite web | title=Etryptamine acetate | id = CAS Registry Number 118-68-3 | website=CAS Common Chemistry | date=6 September 2024 | url=https://commonchemistry.cas.org/detail?cas_rn=118-68-3 | access-date=6 September 2024}}</ref><ref name="BloughLandavazo2014" />
			===Recreational use===
			αET has been used as a ] since the 1980s.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="VarìPichiniGiorgetti2019" /><ref name="Barceloux2012">{{cite book | vauthors = Barceloux DG | title=Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants | publisher=Wiley | year=2012 | isbn=978-0-471-72760-6 | url=https://books.google.com/books?id=OWFiVaDZnkQC&pg=PA195 | access-date=6 September 2024 | page=195}}</ref> Purported street names include Trip, ET, Love Pearls, and Love Pills.<ref name="GlennonDukat2023" /><ref name="Barceloux2012" />
			===Legal status===
			αET is a ] ] in the ] and a ] controlled substance in the ].<ref name="GlennonDukat2023" /><ref name="VarìPichiniGiorgetti2019" />
			==Research==
			Besides ], αET has been studied in people with ] and other conditions.<ref name="GlennonDukat2023" />
			==References==
			{{Reflist}}
			==External links==
			*
			*
			*
	{{Entactogens}}		{{Entactogens|state=collapsed}}
	{{Hallucinogens}}
	{{Stimulants}}		{{Stimulants}}
			{{Navboxes
	{{Adrenergics}}
			| title = ]
	{{Dopaminergics}}
			| titlestyle = background:#ccccff
	{{Serotonergics}}
			| list1 =
			{{Monoamine releasing agents}}
			{{Serotonin receptor modulators}}
			{{Monoamine metabolism modulators}}
			{{Monoamine neurotoxins}}
			}}
	{{Tryptamines}}		{{Tryptamines}}
	{{Neurotoxins}}
	{{DEFAULTSORT:Ethyltryptamine, alpha-}}		{{DEFAULTSORT:Ethyltryptamine, alpha-}}
	]
	]
	]
			]
	]
			]
	]
			]
	]
			]
	]
			]
			]
			]
			]
			]
			]
			]