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Revision as of 02:10, 21 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to watched fields - added verified revid - updated 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors o← Previous edit Latest revision as of 22:11, 11 January 2025 edit undoArthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix 
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{{Short description|Stimulant designer drug}}
{{redirects|NRG-2|the protein growth factor|Neuregulin 2}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 449584685 | verifiedrevid = 451605031
| IUPAC_name = (RS)-2-ethylamino-1-(4-methylphenyl)propan-1-one | IUPAC_name = (''R''/''S'')-2-Ethylamino-1-(4-methylphenyl)propan-1-one
| image = 4-MEC molecular structure.png | image = 4-MEC.svg
| image_class = skin-invert-image
| drug_name = 4-Methylethcathinone | drug_name =

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| legal_BR = F2
⚫ | legal_status = Class B (UK), I-P (Poland) <ref>{{cite web | title = Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 ) | url = http://isap.sejm.gov.pl/DetailsServlet?id = WDU20111050614 | publisher = Internetowy System Aktów Prawnych | accessdate = 17 June 2011}}</ref>
| 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>
⚫ | routes_of_administration =
| legal_DE = Anlage II
| legal_NZ = Class C
⚫ | legal_status = I-P (Poland)<ref>{{cite web | title = Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 ) | url = http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614 | publisher = Internetowy System Aktów Prawnych | access-date = 17 June 2011}}</ref>
| legal_US = Schedule I
| legal_UK = Class B
⚫ | routes_of_administration =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 1225617-18-4 | CAS_number = 1225617-18-4
| CAS_supplemental = <br /> 1266688-86-1 (hydrochloride)
| ATC_prefix = none
| PubChem = | ATC_prefix =
| PubChem = 52988258
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = | ChemSpiderID = 25630091
| synonyms = 4-methyl-''N''-ethylcathinone; 2-ethylamino-1-''p''-tolylpropan-1-one | synonyms = 4-Methyl-''N''-ethylcathinone; 2-Ethylamino-1-''p''-tolylpropan-1-one
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 9665W17SH3
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C22707


<!--Chemical data--> <!--Chemical data-->
| C=12 | H=17 | N=1 | O=1 | C=12 | H=17 | N=1 | O=1
| molecular_weight =
| smiles = Cc1ccc(cc1)C(=O)C(C)NCC | smiles = Cc1ccc(cc1)C(=O)C(C)NCC
| StdInChI = 1S/C12H17NO/c1-4-13-10(3)12(14)11-7-5-9(2)6-8-11/h5-8,10,13H,4H2,1-3H3
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZOXZWYWOECCBSH-UHFFFAOYSA-N
| StdInChI =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫ | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey =
}} }}


'''4-Methylethcathinone''' or '''4-MEC''' is a ] ] of the ], ], and ] ]es. The drug has been marketed alone or in mixtures with other ]s under the name "NRG-2", although other blends such as "NRG-1" may have been more ambiguous with their ingredients.<ref>{{cite doi|10.1136/bmj.c3564}}</ref><ref name="pmid20687197">{{cite journal |author=Brandt SD, Sumnall HR, Measham F, Cole J |title=Analyses of second-generation 'legal highs' in the UK: initial findings |journal=Drug Testing and Analysis |volume=2 |issue=8 |pages=377–82 |year=2010 |month=August |pmid=20687197 |doi=10.1002/dta.155 |url=}}</ref> '''4-Methylethcathinone''' or '''4-MEC''' is a chemical that bears a chemical resemblance to ].<ref>{{cite journal | vauthors = Ondra P, Válka I, Knob R, Ginterová P, Maier V | title = Analysis of Amphetamine-Derived Designer Drugs by Gas Chromatography with Mass Spectrometry | journal = Journal of Analytical Toxicology | volume = 40 | issue = 1 | pages = 78–85 | date = October 2015 | pmid = 26446487 | doi = 10.1093/jat/bkv113 | doi-access = free }}</ref> Due to its similarity to mephedrone, it is thought to be a ] and ] ] of the ], ], and ] ]es.<ref>{{cite journal | vauthors = Helfer AG, Turcant A, Boels D, Ferec S, Lelièvre B, Welter J, Meyer MR, Maurer HH | display-authors = 6 | title = Elucidation of the metabolites of the novel psychoactive substance 4-methyl-N-ethyl-cathinone (4-MEC) in human urine and pooled liver microsomes by GC-MS and LC-HR-MS/MS techniques and of its detectability by GC-MS or LC-MS(n) standard screening approaches | journal = Drug Testing and Analysis | volume = 7 | issue = 5 | pages = 368–75 | date = May 2015 | pmid = 24953431 | doi = 10.1002/dta.1682 }}</ref> It has been marketed alone or in mixtures with other ]s under the name "'''NRG-2'''", although other blends such as "]" may have been more ambiguous with their ingredients.<ref>{{cite journal | vauthors = Brandt SD, Sumnall HR, Measham F, Cole J | title = Second generation mephedrone. The confusing case of NRG-1 | journal = BMJ | volume = 341 | pages = c3564 | date = July 2010 | pmid = 20605894 | doi = 10.1136/bmj.c3564 | s2cid = 20354123 }}</ref>

4-MEC is reported to have been used as the active ingredient in fake "Ecstasy" pills in some countries such as ].<ref>{{Cite web|url=https://www.nzherald.co.nz/nz/news/article.cfm?c_id=1&objectid=10808308|title=Man in court after bust turns up drugs, cash|date=May 24, 2012|via=www.nzherald.co.nz}}</ref>

== Recreational use==

Some users have injected the drug intravenously. It requires heating the water/4-MEC solution in order for 4-MEC to dissolve. Injecting 4-MEC appears to be rough on veins and is sometimes accompanied by a burning sensation. Therefore, 4-MEC should be diluted as much as possible. Intravenous dosages are comparable to oral ones, although more care should be given to safety (with regard to possibility of overdose and long-term effects).<ref name="pmid20687197">{{cite journal | vauthors = Brandt SD, Sumnall HR, Measham F, Cole J | title = Analyses of second-generation 'legal highs' in the UK: initial findings | journal = Drug Testing and Analysis | volume = 2 | issue = 8 | pages = 377–82 | date = August 2010 | pmid = 20687197 | doi = 10.1002/dta.155 | citeseerx = 10.1.1.667.4728 }}</ref><ref>{{cite journal | vauthors = Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Palotás J, Koszegi-Szalai H | title = Identification and characterization of the new designer drug 4'-methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography-tandem mass spectrometry (LC-MS/MS) screening method for seven different methcathinone analogs | journal = Forensic Science International | volume = 210 | issue = 1–3 | pages = 213–20 | date = July 2011 | pmid = 21498012 | doi = 10.1016/j.forsciint.2011.03.019 }}</ref>

== Legality ==
In the United States 4-MEC is a schedule 1 controlled substance.<ref>{{cite web|url=https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf|title=Lists of Scheduling Actions, Controlled Substances, Regulated Chemicals|website=deadiversion.usdoj.gov|access-date=26 March 2023|date=February 2023}}</ref>


== See also == == See also ==
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* ]
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* ] * ]
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== References == == References ==
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{{Stimulants}} {{Stimulants}}
{{Neurotoxins}}
{{Adrenergics}} {{Adrenergics}}
{{Dopaminergics}} {{Dopaminergics}}
{{Phenethylamines}} {{Phenethylamines}}



{{DEFAULTSORT:Methylethcathinone, 4-}} {{DEFAULTSORT:Methylethcathinone, 4-}}

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{{nervous-system-drug-stub}}
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