Methoxetamine: Difference between revisions

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{{SubstanceBox/Methoxetamine}}
{{SubstanceBox/Methoxetamine}}


'''3-MeO-2'-Oxo-PCE''' (commonly known as '''Methoxetamine''', '''MXE''', '''Mexxy''', among others) is a [[psychoactive class::dissociative]] substance of the [[Chemical class::arylcyclohexylamine]] class that produces [[ketamine|ketamine-like]] [[dissociative]] effects when [[administered]]. It is structurally related to [[ketamine]], [[PCE]], and [[3-MeO-PCP]].<ref>MXE Binding profile | http://www.homeoffice.gov.uk/publications/agencies-public-bodies/acmd1/methoxetamine2012?view=Binary</ref>
'''3-MeO-2'-Oxo-PCE''' (commonly known as '''Methoxetamine''', '''MXE''', '''Mexxy''', among others) is a [[psychoactive class::dissociative]] substance of the [[Chemical class::arylcyclohexylamine]] class that produces [[ketamine|ketamine-like]] [[dissociative]] effects when [[administered]]. It is structurally related to [[ketamine]], [[PCE]], and [[3-MeO-PCP]].<ref name="ACMDMXE2012">{{Citation | title=Advisory Council on the Misuse of Drugs (ACMD) Methoxetamine report, 2012 | url=https://www.gov.uk/government/publications/advisory-council-on-the-misuse-of-drugs-acmd-methoxetamine-report-2012}}</ref>


MXE was originally developed through the use of intelligent drug design, as a potential treatment for [https://en.wikipedia.org/wiki/Phantom_pain Phantom Limb Syndrome] among other ailments.<ref>Interview with a ketamine chemist | https://www.vice.com/en_us/article/interview-with-ketamine-chemist-704-v18n2</ref>  
MXE was originally developed through the use of intelligent drug design, as a potential treatment for [https://en.wikipedia.org/wiki/Phantom_pain Phantom Limb Syndrome] among other ailments.<ref>{{Citation | vauthors=((Morris, H.)) | year=2011 | title=Interview with a Ketamine Chemist | url=https://www.vice.com/en/article/ppzgk9/interview-with-ketamine-chemist-704-v18n2}}</ref>  


MXE had no documented history of human usage until it was first identified by the European Monitoring Centre for Drugs and Drug Addiction in November 2010. By July 2011, they had identified 58 websites selling the compound at the cost of 145–195 euros for 10 grams.<ref>Online sales of new psychoactive substances/‘legal highs’ | http://www.emcdda.europa.eu/attachements.cfm/att_143801_EN_SnapshotSummary.pdf</ref> Once highly popular, it is now thought to be extinct on the online [[research chemical]] market due to the global ban of the drug.
MXE had no documented history of human usage until it was first identified by the European Monitoring Centre for Drugs and Drug Addiction in November 2010. By July 2011, they had identified 58 websites selling the compound at the cost of 145–195 euros for 10 grams.<ref>Online sales of new psychoactive substances/‘legal highs’ | http://www.emcdda.europa.eu/attachements.cfm/att_143801_EN_SnapshotSummary.pdf</ref> Once highly popular, it is now thought to be extinct on the online [[research chemical]] market due to the global ban of the drug.
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==Pharmacology==
==Pharmacology==
{{Further|NMDA receptor antagonist}}
{{Further|NMDA receptor antagonist}}
MXE acts as a non-competitive [[NMDA receptor antagonist]] and [[serotonin]]-[[Reuptake Inhibitor|reuptake inhibitor]].<ref name="MXE Binding Profile">[http://www.homeoffice.gov.uk/publications/agencies-public-bodies/acmd1/methoxetamine2012?view=Binary "ACMD Methoxetamine Report (2012)"]. Advisory Council on the Misuse of Drugs. October 2012. pp. 14–15. Retrieved 6 February 2013.</ref> NMDA receptors allow for electrical signals to pass between neurons in the brain and spinal column; for the signals to pass, the receptor must be open. Dissociatives close the NMDA receptors by blocking them. This disconnection of neurons leads to loss of feeling, difficulty moving, and eventually an almost identical equivalent of the famous “[http://en.wikipedia.org/wiki/K-hole k-hole].” MXE was reported to be similar to [[Ketamine|ketamine]] <ref>Kjellgren, A., & Jonsson, K. (2013). Methoxetamine (MXE)--a phenomenological study of experiences induced by a {\dq}legal high{\dq} from the internet. Journal of Psychoactive Drugs, 45(3), 276–286. https://doi.org/10.1080/02791072.2013.803647</ref>, despite being stronger and having a longer duration. <ref>Coppola, M., & Mondola, R. (2012). Methoxetamine: From drug of abuse to rapid-acting antidepressant. Medical Hypotheses, 79(4), 504–507. https://doi.org/10.1016/j.mehy.2012.07.002</ref>
MXE acts as a non-competitive [[NMDA receptor antagonist]] and [[serotonin]]-[[Reuptake Inhibitor|reuptake inhibitor]].<ref name="ACMDMXE2012" /> NMDA receptors allow for electrical signals to pass between neurons in the brain and spinal column; for the signals to pass, the receptor must be open. Dissociatives close the NMDA receptors by blocking them. This disconnection of neurons leads to loss of feeling, difficulty moving, and eventually an almost identical equivalent of the famous “[http://en.wikipedia.org/wiki/K-hole k-hole].” MXE was reported to be similar to [[Ketamine|ketamine]] <ref>{{cite journal | vauthors=((Kjellgren, A.)), ((Jonsson, K.)) | journal=Journal of Psychoactive Drugs | title=Methoxetamine (MXE) – A Phenomenological Study of Experiences Induced by a “Legal High” from the Internet | volume=45 | issue=3 | pages=276–286 | date=1 July 2013 | url=https://www.tandfonline.com/doi/full/10.1080/02791072.2013.803647 | issn=0279-1072 | doi=10.1080/02791072.2013.803647}}</ref>, despite being stronger and having a longer duration. <ref>{{cite journal | vauthors=((Coppola, M.)), ((Mondola, R.)) | journal=Medical Hypotheses | title=Methoxetamine: From drug of abuse to rapid-acting antidepressant | volume=79 | issue=4 | pages=504–507 | date= October 2012 | url=https://linkinghub.elsevier.com/retrieve/pii/S030698771200312X | issn=03069877 | doi=10.1016/j.mehy.2012.07.002}}</ref>


Because of its structural similarity to [https://en.wikipedia.org/wiki/3-HO-PCP 3-HO-PCP], it was falsely believed to carry [[opioid]] properties.<ref>Morris, H., & Wallach, J. (2014). From PCP to MXE: A comprehensive review of the non-medical use of dissociative drugs. Drug Testing and Analysis. https://doi.org/10.1002/dta.1620</ref> This claim cannot be supported by actual data, instead showing only insignificant affinity for the µ-opioid receptor by the substance itself, although in-vivo metabolites could yield different effects.<ref name="MXE Binding Profile" />
Because of its structural similarity to [https://en.wikipedia.org/wiki/3-HO-PCP 3-HO-PCP], it was falsely believed to carry [[opioid]] properties.<ref>{{cite journal | vauthors=((Morris, H.)), ((Wallach, J.)) | journal=Drug Testing and Analysis | title=From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs: PCP to MXE | volume=6 | issue=7–8 | pages=614–632 | date= July 2014 | url=https://onlinelibrary.wiley.com/doi/10.1002/dta.1620 | issn=19427603 | doi=10.1002/dta.1620}}</ref> This claim cannot be supported by actual data, instead showing only insignificant affinity for the µ-opioid receptor by the substance itself, although in-vivo metabolites could yield different effects.<ref name="ACMDMXE2012"/>


==Subjective effects==
==Subjective effects==
{{Preamble/SubjectiveEffects}}
{{Preamble/SubjectiveEffects}}
{{effects/base
{{effects/base


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*'''[[Effect::Nausea]]''' - High dose MXE experience can sometimes result in nausea and vomiting at the peak of the trip. For most people, this is surprisingly not as unpleasant as they would initially expect due to the accompanying detachment from the physical senses.
*'''[[Effect::Nausea]]''' - High dose MXE experience can sometimes result in nausea and vomiting at the peak of the trip. For most people, this is surprisingly not as unpleasant as they would initially expect due to the accompanying detachment from the physical senses.
*'''[[Effect::Optical sliding]]'''
*'''[[Effect::Optical sliding]]'''
*'''[[Effect::Orgasm suppression]]''' - Orgasm enhancement can also be present, even at higher doses.
*'''[[Effect::Orgasm suppression]]''' & '''[[Effect::Orgasm enhancement]]''' - Orgasm enhancement can sometimes also be present, even at higher doses, although this effect is not reliable.


}}
}}
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====[[Effect::Geometry]]====
====[[Effect::Geometry]]====
The visual geometry found within MXE can be described as very dark and bland when compared to that of [[ketamine]] or [[DXM]] and often consists of many tiny interlocking and woven lines. It does not extend beyond level 4 and can be comprehensively described through its [[Visual_effects:_Geometry#Variations|variations]] as simplistic in complexity, algorithmic in style, synthetic in feel, unstructured in organization, dimly lit in lighting, multicolored in scheme, glossy in shading, soft in edges, small in size, slow in speed, smooth in motion, equal in rounded and angular corners, immersive in-depth and consistent in intensity.
The visual geometry found within MXE can be described as very dark and bland when compared to that of [[ketamine]] or [[DXM]] and often consists of many tiny interlocking and woven lines. It does not extend beyond level 4 and can be comprehensively described through its [[Visual_effects:_Geometry#Variations|variations]] as simplistic in complexity, algorithmic in style, synthetic in feel, unstructured in organization, dimly lit in lighting, multicolored in scheme, glossy in shading, soft in edges, small in size, slow in speed, smooth in motion, equal in rounded and angular corners, immersive in-depth and consistent in intensity
 
High doses entering the "hole" can yield a white glow visual phenomena like ketamine.


====Hallucinatory states====
====Hallucinatory states====
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{{#ask: [[Category:MXE]][[Category:Experience]]|format=ul|Columns=1}}
{{#ask: [[Category:MXE]][[Category:Experience]]|format=ul|Columns=1}}
Additional experience reports can be found here:
Additional experience reports can be found here:
* [https://www.erowid.org/experiences/subs/exp_Methoxetamine_.shtml Erowid Experience Vaults: MXE]
 
*[https://www.erowid.org/experiences/subs/exp_Methoxetamine_.shtml Erowid Experience Vaults: MXE]


==Toxicity and harm potential==
==Toxicity and harm potential==
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It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.


===Tolerance and addiction potential===
===Dependence and abuse potential===
As with other NMDA receptor antagonists, the chronic use of MXE can be considered [[Addiction potential::moderately addictive with a high potential for abuse]] and is capable of producing psychological dependence among certain users.  
As with other NMDA receptor antagonists, the chronic use of MXE can be considered [[Addiction potential::moderately addictive with a high potential for abuse]] and is capable of producing psychological dependence among certain users.  
When addiction has developed, cravings and [[withdrawal effects]] may occur if a person suddenly stops their usage.
When addiction has developed, cravings and [[withdrawal effects]] may occur if a person suddenly stops their usage.
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Symptoms of ketamine-induced cystitis can become extremely serious and can be described as:
Symptoms of ketamine-induced cystitis can become extremely serious and can be described as:


*'''Urinary frequency''' - Urinary frequency is the need to empty the bladder every few minutes.  
*'''Urinary frequency''' - Urinary frequency is the need to empty the bladder every few minutes.
*'''Urinary urgency''' - This can be described as a sudden, compelling need to urinate.
*'''Urinary urgency''' - This can be described as a sudden, compelling need to urinate.
*'''Urinary pressure''' - This is experienced as a constant sensation of fullness in the bladder that is unrelieved by urination.
*'''Urinary pressure''' - This is experienced as a constant sensation of fullness in the bladder that is unrelieved by urination.
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*'''Austria''': Since June 26, 2019, MXE is illegal to possess, produce and sell under the SMG. (Suchtmittelgesetz Österreich)<ref>https://www.ris.bka.gv.at/Dokumente/BgblAuth/BGBLA_2019_II_167/BGBLA_2019_II_167.pdfsig</ref>
*'''Austria''': Since June 26, 2019, MXE is illegal to possess, produce and sell under the SMG. (Suchtmittelgesetz Österreich)<ref>https://www.ris.bka.gv.at/Dokumente/BgblAuth/BGBLA_2019_II_167/BGBLA_2019_II_167.pdfsig</ref>
*'''Brazil''': Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344 <ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref>
*'''Brazil''': Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344 <ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref>
*'''Canada''': Health Canada declared MXE a controlled substance, citing it as "considered an analogue of ketamine."<ref>"STATUS DECISION OF CONTROLLED AND NON-CONTROLLED SUBSTANCE(S)", https://web.archive.org/web/20160409135922/http://isomerdesign.com/Cdsa/HC/StatusDecisions/A-2013-00235%20-%20PDFs/C-Methoxetamine-2011-01-31.pdf. Retrieved January 24th, 2017.</ref> The possession, production, and sale are illegal.  
*'''Canada''': Health Canada declared MXE a controlled substance, citing it as "considered an analogue of ketamine."<ref>"STATUS DECISION OF CONTROLLED AND NON-CONTROLLED SUBSTANCE(S)", https://web.archive.org/web/20160409135922/http://isomerdesign.com/Cdsa/HC/StatusDecisions/A-2013-00235%20-%20PDFs/C-Methoxetamine-2011-01-31.pdf. Retrieved January 24th, 2017.</ref> The possession, production, and sale are illegal.
*'''Cyprus''': Methoxetamine was listed in the drug control law in 2012.<ref name="JointReport">{{cite journal|issn=1977-7868|isbn=978-92-9168-686-5|doi=10.2810/28543|pages=14-15|title=EMCDDA–Europol Joint Report on a new psychoactive substance: methoxetamine (2-(3-methoxyphenyl)-2-(ethylamino)cyclohexanone)|url=http://www.emcdda.europa.eu/system/files/publications/818/TDAS14004ENN-1_465208.pdf|date=January 2014|access-date=April 19, 2020|publisher=European Monitoring Centre for Drugs and Drug Addiction (EMCDDA), Europol}}</ref>
*'''Cyprus''': Methoxetamine was listed in the drug control law in 2012.<ref name="JointReport">{{cite journal|issn=1977-7868|isbn=978-92-9168-686-5|doi=10.2810/28543|pages=14-15|title=EMCDDA–Europol Joint Report on a new psychoactive substance: methoxetamine (2-(3-methoxyphenyl)-2-(ethylamino)cyclohexanone)|url=http://www.emcdda.europa.eu/system/files/publications/818/TDAS14004ENN-1_465208.pdf|date=January 2014|access-date=April 19, 2020|publisher=European Monitoring Centre for Drugs and Drug Addiction (EMCDDA), Europol}}</ref>
*'''Denmark''': Methoxetamine is covered by the Executive Order on Euphoriant Substances.<ref name="JointReport"/>
*'''Denmark''': Methoxetamine is covered by the Executive Order on Euphoriant Substances.<ref name="JointReport" />
*'''France''': Methoxetamine was added to the list of illicit substances on August 5, 2013.<ref name="JointReport"/>
*'''France''': Methoxetamine was added to the list of illicit substances on August 5, 2013.<ref name="JointReport" />
*'''Germany''': MXE is controlled under BtMG Anlage I, making it illegal to manufacture, import, possess, sell, or transfer it without a license.<ref>http://www.gesetze-im-internet.de/btmg_1981/anlage_i.html</ref>
*'''Germany''': MXE is controlled under BtMG Anlage I, making it illegal to manufacture, import, possess, sell, or transfer it without a license.<ref>{{Citation | title=Anlage I BtMG - Einzelnorm | url=http://www.gesetze-im-internet.de/btmg_1981/anlage_i.html}}</ref>
*'''Italy''': According to the table of drugs, MXE has been illegal in Italy since 2016.<ref>http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf</ref>
*'''Italy''': According to the table of drugs, MXE has been illegal in Italy since 2016.<ref>http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf</ref>
*'''Japan''': It is illegal to possess, produce, or sell MXE.{{citation needed}}
*'''Japan''': MXE is a narcotic drug in Japan effective June 26th, 2016.<ref>{{Citation | title=新たに指定薬物4物質を麻薬に指定します(注意喚起)|厚生労働省 | publisher=厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)] | url=https://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/oshirase/20160527-1.html}}</ref>
*'''Netherlands''': It is illegal to possess, produce, trasnport, import, export, or sell MXE.<ref>"Opiumwet lijst 1", http://wetten.overheid.nl/BWBR0001941/2017-05-25</ref>
*'''Netherlands''': It is illegal to possess, produce, trasnport, import, export, or sell MXE.<ref>{{Citation | vauthors=((Koninkrijksrelaties, M. van B. Z. en)) | title=Opiumwet | url=https://wetten.overheid.nl/BWBR0001941/2017-05-25}}</ref>
*'''Russia''': It is illegal to possess, produce, or sell MXE.{{citation needed}}
*'''Russia''': It is illegal to possess, produce, or sell MXE.{{citation needed}}
*'''Slovenia''': MXE is a controlled substance (Official Gazette of RS No. 62/2013).<ref name="JointReport"/>
*'''Slovenia''': MXE is a controlled substance (Official Gazette of RS No. 62/2013).<ref name="JointReport" />
*'''Sweden''': Methoxetamine is controlled under the Narcotic Drugs Control Act (SFS 1992-860) and the Narcotic Drugs Control Ordinance (SFS 1994:1554).<ref name="JointReport"/>
*'''Sweden''': Methoxetamine is controlled under the Narcotic Drugs Control Act (SFS 1992-860) and the Narcotic Drugs Control Ordinance (SFS 1994:1554).<ref name="JointReport" />
*'''Switzerland:''' MXE is a controlled substance specifically named under Verzeichnis D.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''Switzerland:''' MXE is a controlled substance specifically named under Verzeichnis D.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''Turkey''': Methoxetamine is regulated under the Law on Control of Narcotics no. 2313.<ref name="JointReport"/>
*'''Turkey''': Methoxetamine is regulated under the Law on Control of Narcotics no. 2313.<ref name="JointReport" />
*'''United Kingdom''': MXE is a Class B drug.{{citation needed}}
*'''United Kingdom''': MXE is a Class B drug.{{citation needed}}
*'''United States''': MXE is not illegal, however, if it is sold with the intention for human consumption (such as in capsules) it becomes illegal to possess under the Federal Analogue Act. This is avoided by placing the label "not for human consumption" on the container of the chemical.{{citation needed}}
*'''United States''': MXE is a schedule 1 controlled substance.<ref>https://www.federalregister.gov/documents/2022/06/06/2022-11933/schedules-of-controlled-substances-placement-of-methoxetamine-mxe-in-schedule-i</ref>


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Research chemical]]
*[[Research chemical]]
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==External links==
==External links==
*[http://en.wikipedia.org/wiki/Methoxetamine MXE (Wikipedia)]
*[http://en.wikipedia.org/wiki/Methoxetamine MXE (Wikipedia)]
*[https://www.erowid.org/chemicals/methoxetamine/ MXE (Erowid Vault)]
*[https://www.erowid.org/chemicals/methoxetamine/ MXE (Erowid Vault)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=689 MXE (Isomer Design)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=689 MXE (Isomer Design)]
===Discussion===
===Discussion===
*[http://www.bluelight.org/vb/threads/524290-The-Big-amp-Dandy-Methoxetamine(2-(3-methoxyphenyl)-2-(ethylamino)cyclohexanone)-Thread The Big & Dandy Methoxetamine Thread (Bluelight)]
*[http://www.bluelight.org/vb/threads/524290-The-Big-amp-Dandy-Methoxetamine(2-(3-methoxyphenyl)-2-(ethylamino)cyclohexanone)-Thread The Big & Dandy Methoxetamine Thread (Bluelight)]


==Literature==
==Literature==
* Morris, H., & Wallach, J. (2014). From PCP to MXE: A comprehensive review of the non-medical use of dissociative drugs. Drug Testing and Analysis, 6(7–8), 614–632. https://doi.org/10.1002/dta.1620
 
* Halberstadt, A. L., Slepak, N., Hyun, J., Buell, M. R., & Powell, S. B. (2016). The novel ketamine analog methoxetamine produces dissociative-like behavioral effects in rodents. Psychopharmacology, 233(7), 1215-1225. https://doi.org/10.1007/s00213-016-4203-3
*Morris, H., & Wallach, J. (2014). From PCP to MXE: A comprehensive review of the non-medical use of dissociative drugs. Drug Testing and Analysis, 6(7–8), 614–632. https://doi.org/10.1002/dta.1620
*Halberstadt, A. L., Slepak, N., Hyun, J., Buell, M. R., & Powell, S. B. (2016). The novel ketamine analog methoxetamine produces dissociative-like behavioral effects in rodents. Psychopharmacology, 233(7), 1215-1225. https://doi.org/10.1007/s00213-016-4203-3


==References==
==References==
<references />
<references />


[[Category:Substance]]
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Arylcyclohexylamine]]
[[Category:Dissociative]]
[[Category:Dissociative]]
[[Category:Hallucinogen]]
[[Category:Arylcyclohexylamine]]
[[Category:Research chemical]]
[[Category:Research chemical]]


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{{#set:Featured=true}}