{"Abbreviation":"αET","Aliases":["Etryptamine","3-(2-Aminobutyl)indole","Ethyltryptamine","3-Indolylbutylamine","Etriptamina","Monase","Ro 3-1932","Indole, 3-(2-aminobutyl)-","-Etryptamine","Etryptaminum"],"CAS":"2235-90-7","ChEBI":"CHEBI:134838","ChEMBL":"CHEMBL1619758","ChemicalClasses":["α-alkyltryptamine"],"Chirality":"racemic","Classes":["Entactogen","Stimulant"],"DEA no":7249,"Drug Indication":"Developed in the 1960's for use as an antidepressant before market withdrawal in 1962.","DrugClasses":["antidepressant","depressant","psychedelic","stimulant"],"DurationOfAction":"6 – 8 hours (100 – 150 mg)","EliminationHalfLife":"~8 hours","Esters":["acetate"],"FullSalts":["α-Ethyltryptamine hydrochloride","α-Ethyltryptamine acetate"],"HeavyAtomCount":14,"IUPACName":"1-(1H-indol-3-yl)butan-2-amine","InChI":"InChI=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","InChIKey":"ZXUMUPVQYAFTLF-UHFFFAOYSA-N","MolecularFormula":"C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"188.27 g/mol","Opticalactivity":"( + / - )","Pharmacodynamics":"αET is a stimulant and psychedelic with MDMA like physiological effects. Like MDMA, increases in locomotor activity and mood elevation can be seen post administration. [2]","PrevSalts":["hydrochloride","acetate"],"PubChemId":8367,"Record Description":["Etryptamine is a member of indoles.","Alpha-ethyltryptamine is a DEA Schedule I controlled substance. Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse. It is a Hallucinogenic substances substance.","In the 1960's, alpha-ethyltryptamine (αET), a non hydrazine reversible monoamine oxidase inhibitor, was developed in the United States by the Upjohn chemical company for use as an antidepressant. αET was an FDA approved antidepressant under the name Monase. However, in 1962, after the discovery of an unacceptable incidence of agranulocytosis, the development of Monase was halted and the drug was withdrawn from potential market use.   In 1993, the US Drug Enforcement Administration added αET to Schedule I of its Schedules of Controlled Substances, after an increasing incidence of its use as a recreational drug in the 1980's. Currently, αET is an illegal substance; however, it's activity is still under scientific investigation.   αET is a stimulant and hallucinogen, but it is less stimulating and hallucinogenic than alpha-methyltryptamine, a closely related compound. Instead, the effects of αET, a tryptamine derivative, more closely resemble the amphetamine derived drug 3,4-methylenedioxy-N-methylamphetamine (MDMA). Similarly to MDMA, αET has been shown to release serotonin pre-synaptically, as well as lesser amounts of norepinephrine and dopamine. Like MDMA, increases in locomotor activity and mood elevation can be seen post administration.","See also: Etryptamine Acetate (annotation moved to).","Etryptamine is a member of indoles.","Wikipedia|TiHKAL|Tryptamines","\u0026#945;-Ethyltryptamine (\u0026#945;ET, AET), also known as etryptamine (INN, BAN, USAN), is a psychedelic, stimulant, and entactogenic drug of the tryptamine class. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s. \u0026#945;ET is structurally and pharmacologically related to \u0026#945;MT, \u0026#945;-methyltryptamine, and it is believed[4] its central stimulant activity is probably not due to its activity as an MAOI, but appears to stem from its structural relationship to the indolic psychedelics. In contrast to \u0026#945;MT, \u0026#945;ET is less stimulating and hallucinogenic, its effects resembling more those of entactogens like MDMA (\"Ecstasy\").","Wikipedia|List of designer drugs|Empathogens|Tryptamines"],"RefCount":4,"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/α-Ethyltryptamine","Name":"α-Ethyltryptamine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q2394183","Name":"α-Ethyltryptamine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB01546","Name":"α-Ethyltryptamine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/8367","Name":"α-Ethyltryptamine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1619758","Name":"α-Ethyltryptamine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:134838","Name":"α-Ethyltryptamine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=2235-90-7","Name":"α-Ethyltryptamine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/GR181O3R32","Name":"α-Ethyltryptamine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID1046764","Name":"α-Ethyltryptamine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 8367, α-Ethyltryptamine. Accessed July 3, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/8367\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/8367\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. α-Ethyltryptamine. UNII: GR181O3R32. Global Substance Registration System. Accessed July 3, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/GR181O3R32\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/GR181O3R32\u003c/a\u003e","Anvisa. RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial. Diário Oficial da União. July 24, 2023. Accessed July 3, 2025. \u003ca href=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451\u003ehttps://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451\u003c/a\u003e"],"SMILES":"CCC(CC1=CNC2=CC=CC=C21)N","Salts":["hydrochloride","acetate"],"SaltsAcidCount":[1,1],"SaltsAmineCount":[1,1],"SaltsUNII":["H52WH7M1B6","3RY07R55EE"],"Scheduling":[{"gov":"Brazil","ref":["3"],"schedule":"F2 substance"},{"gov":"Canada","ref":[],"schedule":"Schedule III substance"},{"act":"Controlled Substances Act (CSA)","gov":"United States","ref":[],"schedule":"Schedule I"},{"gov":"United Kingdom","ref":[],"schedule":"Class A substance"},{"gov":"Germany","ref":[],"schedule":"Anlage I substance"},{"act":"Convention on Psychotropic Substances 1971","gov":"United Nations","ref":[],"schedule":"Schedule I drug"}],"StereoisomerRacemic":"(RS)-α-Ethyltryptamine","StoreUNII":["GR181O3R32"],"StructureBase64":"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Effects":{"Cognitive Effects":["Empathy, effection, and sociability enhancement","Increased music appreciation","Disinhibition","Cognitive euphoria","Analysis enhancement","Ego inflation","Focus enhancement","Motivation enhancement","Thought acceleration","Wakefulness","Suggestibility suppression","Compulsive redosing","Mania"],"Physical Effects":["Increased libido","Restless legs","Shakiness","Teeth grinding","Stamina enhancement","Stimulation","Appetite suppression","Dehydration","Dry mouth","Abnormal heartbeat","Increased blood pressure","Increased heart rate","Vasoconstriction"],"Visual Effects":[]},"Title":"α-Ethyltryptamine","UNII":"GR181O3R32","Wikidata":"Q2394183","Wikipedia":"α-Ethyltryptamine","XLogP":2.5}