{{Short description|Chemical compound}} {{Infobox drug | Verifiedfields = | verifiedrevid = | IUPAC_name = ''N''-Ethyl-1-(3-methoxyphenyl)cyclohexan-1-amine | image = 3-MeO-PCE.svg | image_class = skin-invert-image
<!--Clinical data--> | tradename = | legal_UK = Class B | legal_DE = NpSG | legal_status = Illegal in Sweden and Switzerland
<!--Identifiers--> | CAS_number = 1364933-80-1 | CAS_number_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = PX6CYK9I4H | CAS_supplemental = | ATC_prefix = | PubChem = 57461569 | ChemSpiderID_Ref = | ChemSpiderID = 58191438 | synonyms = 3-MeO-PCE; Methoxieticyclidine
<!--Chemical data--> | C=15 | H=23 | N=1 | O=1 | smiles = CCNC1(CCCCC1)C2=CC(=CC=C2)OC | StdInChI = 1S/C15H23NO/c1-3-16-15(10-5-4-6-11-15)13-8-7-9-14(12-13)17-2/h7-9,12,16H,3-6,10-11H2,1-2H3 | StdInChIKey = OFGOOZLOGUNDFS-UHFFFAOYSA-N }}
'''3-Methoxyeticyclidine''' ('''3-MeO-PCE'''), also known as '''methoxieticyclidine''',<ref name="pmid24678061" /> is a dissociative anesthetic that is qualitatively similar to PCE and PCP<ref name="pmid24678061">{{cite journal | vauthors = Morris H, Wallach J | title = From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs | journal = Drug Testing and Analysis | volume = 6 | issue = 7–8 | pages = 614–32 | date = July–August 2014 | pmid = 24678061 | doi = 10.1002/dta.1620 }}</ref> and has been sold online as a designer drug.<ref>{{cite journal | vauthors = De Paoli G, Brandt SD, Wallach J, Archer RP, Pounder DJ | title = From the street to the laboratory: analytical profiles of methoxetamine, 3-methoxyeticyclidine and 3-methoxyphencyclidine and their determination in three biological matrices | journal = Journal of Analytical Toxicology | volume = 37 | issue = 5 | pages = 277–83 | date = June 2013 | pmid = 23552616 | doi = 10.1093/jat/bkt023 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Wallach J, Colestock T, Cicali B, Elliott SP, Kavanagh PV, Adejare A, Dempster NM, Brandt SD | display-authors = 6 | title = Syntheses and analytical characterizations of N-alkyl-arylcyclohexylamines | journal = Drug Testing and Analysis | volume = 8 | issue = 8 | pages = 801–15 | date = August 2016 | pmid = 26360516 | doi = 10.1002/dta.1861 | s2cid = 1599386 | url = http://researchonline.ljmu.ac.uk/3240/1/%EF%BF%BC%EF%BF%BC%EF%BF%BCDTA-15-0185.R1.pdf }}</ref><ref>{{Cite web|title=3-MeO-PCE|work=New Synthetic Drugs Database|url=http://nsddb.eu/substance/296/|access-date=2016-08-27|archive-url=https://web.archive.org/web/20160729183729/http://nsddb.eu/substance/296/|archive-date=2016-07-29|url-status=dead}}</ref>
On October 18, 2012, the Advisory Council on the Misuse of Drugs in the United Kingdom released a report about methoxetamine, saying that the "harms of methoxetamine are commensurate with Class B of the Misuse of Drugs Act (1971)", despite the fact that the act does not classify drugs based on harm. The report went on to suggest that all analogues of methoxetamine should also become class B drugs and suggested a catch-all clause covering both existing and unresearched arylcyclohexamines, including 3-MeO-PCE.<ref name='ACMD MXE report'>{{cite web|url=https://www.gov.uk/government/publications/advisory-council-on-the-misuse-of-drugs-acmd-methoxetamine-report-2012|title=Advisory Council on the Misuse of Drugs (ACMD) Methoxetamine report, 2012|date=18 October 2012|work=UK Home Office}}</ref>
This report also described the receptor binding profile of methoxetamine and three additional dissociatives 3-MeO-PCP, 4-MeO-PCP, and 3-MeO-PCE, showing them to have significant affinity for the PCP site of the NMDA receptor (NMDAR) and was later published in more detail.<ref name="Roth">{{cite journal|author1-link=Bryan Roth | vauthors = Roth BL, Gibbons S, Arunotayanun W, Huang XP, Setola V, Treble R, Iversen L | title = The ketamine analogue methoxetamine and 3- and 4-methoxy analogues of phencyclidine are high affinity and selective ligands for the glutamate NMDA receptor | journal = PLOS ONE | volume = 8 | issue = 3 |article-number=e59334 | date = March 2013 | pmid = 23527166 | pmc = 3602154 | doi = 10.1371/journal.pone.0059334 | bibcode = 2013PLoSO...859334R | doi-access = free }}</ref>
3-MeO-PCE has K<sub>i</sub> values of 61 nM for the NMDAR, 743 nM for the dopamine transporter, 2097 nM for the histamine H2 receptor, 964 nM for the alpha-2A adrenergic receptor, 115 nM for the serotonin transporter, 4519 nM for the σ<sub>1</sub> receptor, and 525 nM for the σ<sub>2</sub> receptor.<ref name="Roth"/>
== Legal status ==
3-MeO-PCE is banned in Sweden<ref>{{cite web|title=Elva nya ämnen klassas som narkotika eller hälsofarlig vara|publisher=Folkhälsomyndigheten|url=https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2018/juni/elva-nya-amnen-klassas-som-narkotika-eller-halsofarlig-vara/|date=28 June 2018|language=sv|access-date=19 May 2020|archive-date=8 March 2021|archive-url=https://web.archive.org/web/20210308132454/https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2018/juni/elva-nya-amnen-klassas-som-narkotika-eller-halsofarlig-vara/|url-status=dead}}</ref><ref>{{cite web|last1=Riksdagsförvaltningen|title=Förordning (1992:1554) om kontroll av narkotika|url=https://riksdagen.se/sv/dokument-lagar/dokument/svensk-forfattningssamling/forordning-19921554-om-kontroll-av-narkotika_sfs-1992-1554|website=riksdagen.se|language=sv}}</ref> and Switzerland.<ref>{{cite web|title=Verordnung des EDI vom 30. Mai 2011 über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien (Betäubungsmittelverzeichnisverordnung, BetmVV-EDI)|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|publisher=Der Bundesrat|language=de}}</ref>
As per Chile's Ley de drogas, aka Ley 20000,<ref>{{cite web | url=https://www.leychile.cl/Navegar?idNorma=235507 | title=SUSTITUYE LA LEY Nº 19.366, QUE SANCIONA EL TRAFICO ILICITO DE ESTUPEFACIENTES Y SUSTANCIAS SICOTROPICAS | publisher=Bibloteca Del Congreso Nacional | date=22 October 2015 | language=es | access-date=6 February 2018}}</ref> all esters and ethers of PCE are illegal. As 3-MeO-PCE is an ether of PCE, it is thus illegal.
== See also == * 3-HO-PCP * 3-MeO-PCMo * Arylcyclohexylamine * Ketamine * Methoxyketamine * Eticyclidine
== References == {{Reflist}}
{{Dissociatives}} {{Ionotropic glutamate receptor modulators}} {{Sigma receptor modulators}}
Category:Arylcyclohexylamines Category:Dissociative drugs Category:3-Methoxyphenyl compounds Category:Designer drugs