| Revision as of 19:50, 20 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'DrugBank_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID|Chem/Dr← Previous edit |
Latest revision as of 19:35, 10 November 2024 edit undo76.174.0.57 (talk) Cat. |
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{{Short description|Designer drug of the cathinone class}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 424949322 |
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| Watchedfields = changed |
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| verifiedrevid = 451555065 |
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| IUPAC_name = (±)-1-(1,3-benzodioxol-5-yl)-2-(ethylamino)butan-1-one |
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| IUPAC_name = (±)-1-(1,3-benzodioxol-5-yl)-2-(ethylamino)butan-1-one |
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| image = Eutylone_structure.png |
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| image = Eutylone.svg |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled --> |
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| legal_BR = F2 |
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| 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> |
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| legal_CA = Schedule I |
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| legal_DE = Anlage II |
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| legal_UK = Class B |
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| legal_US = Schedule I |
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| legal_UN = P II |
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| legal_UN_comment = <ref>{{Cite web |title=Substance Details Eutylone |url=https://www.unodc.org/LSS/Substance/Details/29eff971-208a-4a67-98d6-71f53923862e |access-date=2024-01-22}}</ref> |
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| legal_status = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| metabolism = |
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| metabolism = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = |
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| CAS_number = 802855-66-9 |
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| index_label = |
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| index2_label = HCl |
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| CAS_number2_Ref = {{cascite|correct|CAS}} |
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| CAS_number2 = 17764-18-0 |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = 4FNX1J271X |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ATC_suffix = |
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| PubChem = |
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| PubChem = 57360686 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C22708 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = D6WQJ7NF96 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 26716427 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=13 | H=17 | N=1 | O=3 |
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| C=13 | H=17 | N=1 | O=3 |
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| smiles = CCC(C(=O)C1=CC2=C(C=C1)OCO2)NCC |
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| molecular_weight = 235.278 g/mol |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| smiles = c2c1OCOc1ccc2C(=O)C(CC)NCC |
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| StdInChI = 1S/C13H17NO3/c1-3-10(14-4-2)13(15)9-5-6-11-12(7-9)17-8-16-11/h5-7,10,14H,3-4,8H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = YERSNXHEOIYEGX-UHFFFAOYSA-N |
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}} |
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'''Eutylone''' (also known as '''β-keto-1,3-benzodioxolyl-''N''-ethylbutanamine''', '''bk-EBDB''', and '''''N''-ethylbutylone''') is a ] and ]ic ] of the ], ], ], and ] families which was developed in the 1960s,<ref>{{Cite patent|country=GB|number=108513|pubdate=1967-09-27|title=Aryl-α-aminoketone derivatives|assign1=]}}</ref><ref name="pmid33689284">{{cite journal | vauthors = Glatfelter GC, Walther D, Evans-Brown M, Baumann MH | title = Eutylone and Its Structural Isomers Interact with Monoamine Transporters and Induce Locomotor Stimulation | journal = ACS Chemical Neuroscience | volume = 12 | issue = 7 | pages = 1170–1177 | date = April 2021 | pmid = 33689284 | doi = 10.1021/acschemneuro.0c00797 | pmc = 9423000 | s2cid = 232192447 }}</ref> which is classified as a ].<ref>{{cite web | url=http://nsddb.eu/substance/413/ | title=Eutylone | date=12 November 2023 | publisher=New Synthetic Drugs Database}}</ref> It was first reported to the ] in 2014 and became widespread internationally in 2019-2020 following bans on the related compound ].<ref>{{cite journal | vauthors = Bade R, White JM, Nguyen L, Tscharke BJ, Mueller JF, O'Brien JW, Thomas KV, Gerber C | display-authors = 6 | title = Determining changes in new psychoactive substance use in Australia by wastewater analysis | journal = The Science of the Total Environment | volume = 731 | pages = 139209 | date = August 2020 | pmid = 32417485 | doi = 10.1016/j.scitotenv.2020.139209 | bibcode = 2020ScTEn.73139209B | s2cid = 218680033 | url = https://unisa.alma.exlibrisgroup.com/view/delivery/61USOUTHAUS_INST/12200648250001831 }}</ref><ref>{{cite journal | vauthors = Krotulski AJ, Papsun DM, Chronister CW, Homan J, Crosby MM, Hoyer J, Goldberger BA, Logan BK | display-authors = 6 | title = Eutylone Intoxications-An Emerging Synthetic Stimulant in Forensic Investigations | journal = Journal of Analytical Toxicology | date = August 2020 | volume = 45 | issue = 1 | pages = 8–20 | pmid = 33325503 | doi = 10.1093/jat/bkaa113 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Chen HY, Chien WC, Huang MN, Fang CC, Weng TI | title = Analytically confirmed eutylone (bk-EBDB) exposure in emergency department patients | journal = Clinical Toxicology | pages = 846–848 | date = January 2021 | volume = 59 | issue = 9 | pmid = 33448882 | doi = 10.1080/15563650.2020.1868491 | s2cid = 231611658 }}</ref><ref name="Nakamura2022">{{cite journal | vauthors = Nakamura M, Takaso M, Takeda A, Hitosugi M | title = A fatal case of intoxication from a single use of eutylone: Clinical symptoms and quantitative analysis results | journal = Leg Med (Tokyo) | volume = 58 | pages = 102085 | date = September 2022 | pmid = 35537301 | doi = 10.1016/j.legalmed.2022.102085 | s2cid = 248602483 }}</ref> It is a synthetic cathinone.<ref name="Nakamura2022"/> In 2021, eutylone was the most common cathinone identified by the Drug Enforcement Administration in the United States.<ref name=dea2021>{{cite web | url = https://cesar.umd.edu/sites/cesar.umd.edu/files/pubs/DEA-Emerging-Threat-Report-2021-Mid-Year.pdf | title = Emerging Threat Report | date = 2021 }}</ref> |
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'''β-Keto-Ethylbenzodioxolylbutanamine''' ('''Eutylone''', '''bk-EBDB''') is a ] compound developed in the 1960s,<ref>Substituted phenyl-α-amino ketones. British Patent {{Cite patent|GB|1085135}} (1969).</ref> which has been reported as a novel ].<!-- another obscure cathinone that has shown up, probably one of the last before they are all banned! -->{{Citation needed|date=March 2010}} |
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== See also == |
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== Legal status == |
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Sweden's public health agency suggested classifying eutylone as a hazardous substance, on September 25, 2019.<ref>{{cite web | url=https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/september/tretton-amnen-foreslas-klassas-som-narkotika-eller-halsofarlig-vara/ | title=Tretton ämnen föreslås klassas som narkotika eller hälsofarlig vara | publisher=Folkhälsomyndigheten | language=sv | date=25 September 2019 | access-date=11 November 2019 | archive-date=31 October 2019 | archive-url=https://web.archive.org/web/20191031144424/https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/september/tretton-amnen-foreslas-klassas-som-narkotika-eller-halsofarlig-vara/ | url-status=dead }}</ref> |
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In the United States Eutylone is considered a schedule 1 controlled substance as a ] of ].<ref></ref><ref>{{cite web | url=https://www.federalregister.gov/documents/2023/04/10/2023-07335/specific-listing-for-eutylone-a-currently-controlled-schedule-i-substance | title=Federal Register :: Request Access | date=10 April 2023 }}</ref> |
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==See also== |
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== References == |
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== References == |
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{{Reflist}} |
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{{Reflist}} |
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{{Entactogens|state=expanded}} |
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{{Stimulants}} |
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{{Monoamine releasing agents}} |
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{{Adrenergics}} |
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{{Serotonergics}} |
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{{Phenethylamines}} |
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{{Phenethylamines}} |
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