{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 447557117 | image = Ethylone.svg | image_class = skin-invert-image | width = 250px | chirality = Racemic mixture
<!-- Clinical data --> | tradename = | pregnancy_category = N (US) | routes_of_administration = Oral<ref name="Oeri2021" /> | class = Serotonin–norepinephrine–dopamine releasing agent; Entactogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled --> | 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 = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_DE = Anlage I | legal_NZ = <!-- Class A, B, C --> | legal_UK = Class B | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_UN = P II | legal_UN_comment = <ref>{{Cite web |title=Substance Details Ethylone |url=https://www.unodc.org/LSS/Substance/Details/2d91de8d-13b7-4c69-9a1b-b1b379c4223e |access-date=2024-01-22}}</ref> | legal_EU =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | onset = | elimination_half-life = | duration_of_action = 2–4 hours<ref name="Oeri2021">{{cite journal | vauthors = Oeri HE | title = Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy | journal = J Psychopharmacol | volume = 35 | issue = 5 | pages = 512–536 | date = May 2021 | pmid = 32909493 | pmc = 8155739 | doi = 10.1177/0269881120920420 | url = }}</ref> | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|changed|CAS}} | CAS_number = 1112937-64-0 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = L91C78FW96 | PubChem = 57252245 | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = C22709 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 21106271 | synonyms = 3,4-Methylenedioxy-''N''-ethylcathinone; MDEC; βk-MDEA
<!-- Chemical data --> | IUPAC_name = (''RS'')-1-(1,3-benzodioxol-5-yl)-2-(ethylamino)propan-1-one | C=12 | H=15 | N=1 | O=3 | SMILES = CC(NCC)C(=O)c1ccc2OCOc2c1 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C12H15NO3/c1-3-13-8(2)12(14)9-4-5-10-11(6-9)16-7-15-10/h4-6,8,13H,3,7H2,1-2H3 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = MJEMIOXXNCZZFK-UHFFFAOYSA-N }}
'''Ethylone''', also known as '''3,4-methylenedioxy-''N''-ethylcathinone''' ('''MDEC''', '''βk-MDEA'''), is a recreational designer drug of the phenethylamine, amphetamine, and cathinone chemical classes.<ref name="Oeri2021" /> It is the β-keto analogue of MDEA ("Eve"). Ethylone has only a short history of human use and is reported to be less potent than its relative methylone.{{citation needed|date=May 2015}} In the United States, it began to be found in cathinone products in late 2011.<ref name="jat">{{cite journal | vauthors = Lee D, Chronister CW, Hoyer J, Goldberger BA | title = Ethylone-Related Deaths: Toxicological Findings | journal = Journal of Analytical Toxicology | volume = 39 | issue = 7 | pages = 567–71 | date = September 2015 | pmid = 26025164 | doi = 10.1093/jat/bkv053 | doi-access = free }}</ref>
Very little data exists about the pharmacological properties, metabolism, and toxicity of ethylone, and although several ethylone-related deaths have been reported, the cause of death was not due to ingestion of ethylone.<ref name=jat/>
==Interactions== {{See also|MDMA#Interactions|Trip killer#Antidotes of other hallucinogens|MDMA/citalopram}}
==Pharmacology== ===Pharmacokinetics=== Analysis of human and rat urine for the metabolites of bk-amphetamines suggested that ethylone was degraded in the following metabolic steps:<ref>{{cite journal | vauthors = Meyer MR, Wilhelm J, Peters FT, Maurer HH | title = Beta-keto amphetamines: studies on the metabolism of the designer drug mephedrone and toxicological detection of mephedrone, butylone, and methylone in urine using gas chromatography-mass spectrometry | journal = Analytical and Bioanalytical Chemistry | volume = 397 | issue = 3 | pages = 1225–33 | date = June 2010 | pmid = 20333362 | doi = 10.1007/s00216-010-3636-5 | s2cid = 21471611 }}</ref>
# N-deethylation to the primary amine. # Reduction of the keto moiety to the respective alcohol.
==Society and culture== ===Legal status=== As of October 2015 Ethylone 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 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | access-date=1 October 2015 | archive-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | url-status=dead }}</ref>
==See also== * Substituted methylenedioxyphenethylamine * Substituted cathinone * 5-Methylethylone * Benzylone
== References == {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/2344 Ethylone - Isomer Design] * [https://psychonautwiki.org/wiki/Ethylone Ethylone - PsychonautWiki]
{{Entactogens}} {{Stimulants}} {{Monoamine releasing agents}} {{Phenethylamines}}
Category:Designer drugs Category:Entactogens Category:Methylenedioxycathinones Category:Serotonin-norepinephrine-dopamine releasing agents