ethylone
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 447557117
| IUPAC_name = (RS)-1-(1,3-benzodioxol-5-yl)-2-(ethylamino)propan-1-one
| image = Bk-MDEA.svg
| width = 200px
| chirality = Racemic mixture
| tradename =
| pregnancy_category = N (US)
| legal_AU =
| legal_BR = F2
| legal_BR_comment = {{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}}
| legal_CA =
| legal_DE = Anlage I
| legal_NZ =
| legal_UK = Class B
| legal_US =
| legal_UN = P II
| legal_UN_comment = {{Cite web |title=Substance Details Ethylone |url=https://www.unodc.org/LSS/Substance/Details/2d91de8d-13b7-4c69-9a1b-b1b379c4223e |access-date=2024-01-22}}
| legal_EU =
| routes_of_administration = Oral, nasal, IV
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|changed|CAS}}
| CAS_number = 1112937-64-0
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = L91C78FW96
| ATC_prefix =
| ATC_suffix =
| PubChem = 57252245
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C22709
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 21106271
| 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
| C=12 | H=15 | N=1 | O=3
| smiles = CC(NCC)C(=O)c1ccc2OCOc2c1
}}
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. 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.{{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 }}
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.
Pharmacokinetics
Analysis of human and rat urine for the metabolites of bk-amphetamines suggested that ethylone was degraded in the following metabolic steps:{{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 }}
- N-deethylation to the primary amine.
- Reduction of the keto moiety to the respective alcohol.
Legal Status
As of October 2015 Ethylone is a controlled substance in China.{{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 }}
See also
References
{{Reflist}}
{{Entactogens}}
{{Stimulants}}
{{Monoamine releasing agents}}
{{Phenethylamines}}
Category:Methylenedioxyphenethylamines
Category:Serotonin-norepinephrine-dopamine releasing agents
{{nervous-system-drug-stub}}