View source for Talk:DMXE

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{{Distinguish|Methoxetamine}}
{{SummarySheet}}
{{SubstanceBox/DMXE}}

== '''DMXE (Deoxymethoxetamine)''' ==

'''3-Me-2'-oxo-PCE''' (also known as '''Deoxymethoxetamine''', '''DMXE''') is a [[psychoactive class::dissociative]] substance in the [[Chemical class::arylcyclohexylamine]] class. It produces [[ketamine|ketamine-like]] [[dissociative]] effects and is structurally related to [[MXE]], [[ketamine]], [[PCE]], and [[3-MeO-PCP]].<ref>[https://pubchem.ncbi.nlm.nih.gov/compound/157010705 PubChem Entry]</ref>

DMXE emerged in October 2020, marketed as a legal replacement for MXE following MXE's global ban.<ref name="JPHS2022">Irie, T., Yanase, Y., Demizu, Y., Usami, M., & Kikura-Hanajiri, R. (2022). ''Derivatives of methoxetamine and major methoxetamine metabolites potently block NMDA receptors''. ''Journal of Pharmacological Sciences, 150(4)'', 233-243. [https://doi.org/10.1016/j.jphs.2022.09.005 DOI]</ref>

Due to its limited history of human use, little is known about its long-term effects, metabolism, or toxicity. '''Harm reduction practices''' are strongly advised.
== '''History and Culture''' ==

DMXE was first reported in 2020 and quickly gained popularity as an alternative to MXE.<ref>[https://erowid.org/experiences/subs/exp_DMXE.shtml Erowid Experience Reports]</ref> Alongside [[MXiPr]], it has been sold online as a research chemical dissociative since October 2020.<ref name="JPHS2022" /><ref>[https://ndews.org/?wysija-page=1&controller=email&action=view&email_id=125&wysijap=subscriptions NDEWS Web Monitoring Alert, 2021]</ref>

DMXE is rarely sold on the streets and is almost exclusively found in online research chemical markets.

== '''Chemistry''' ==

DMXE '''(Deoxymethoxetamine)''', or '''2-(ethylamino)-2-(3-methylphenyl)-cyclohexanone''', belongs to the '''arylcyclohexylamine''' family, which includes '''ketamine, PCP, and MXE'''.

=== '''Structural Differences from MXE''' ===

* DMXE lacks the '''3-methoxy (-OCH₃)''' group of MXE, replacing it with a '''methyl (-CH₃)''' group instead.
* This makes DMXE '''less bulky and more hydrophobic''', potentially altering its pharmacology.
=== '''Physical Properties''' ===

* DMXE is usually a '''light yellow-tan crystalline solid''', often '''sandy or flaky in texture'''.
* It is '''sparingly soluble''' (10 mg/mL in ethanol or DMSO).
* Stability: '''~5 years''' when stored at -20°C.<ref>[https://www.caymanchem.com/product/33962/deoxymethoxetamine-(hydrochloride) Cayman Chemical]</ref>
==== '''Comparison to 3D-MXE''' ====

* '''DMXE: Lighter (yellow-tan), more crystalline/sandy.'''
* '''3D-MXE: Darker (brown/gray), finer, more powdery.'''

==Pharmacology==
DMXE acts as a non-competitive [[NMDA receptor antagonist]]. NMDARs (N-methyl-D-aspartate receptors) are specific types of glutamate receptors which modulate the transmission of electrical signals between neurons in the brain and spinal cord; for the signals to pass, the receptor must be open.
The substance has shown a [https://en.wikipedia.org/wiki/IC50 IC<sub>50</sub>] (half-maximal inhibitory concentration), which measures the potency of DMXE and related compounds in blocking NMDARs, of 0.679mM, indicating significant potency. DMXE and related compounds bind to the phcyclidine (PCP) site of NMDARs, which was determined via in silico docking results. This binding is implicated in the antagonistic activity observed, which includes the blocking of NMDA-induced inward currents in a dose-dependent manner. DMXE shows a high affinity and potent inhibitory capacity comparable to that of other MXE analogs like MXiPr and O-desmethyl MXE, with some variations in potency explained by different interactions at the receptor site. Additionally, DMXE significantly reduces excitatory postsynaptic currents (EPSCs) evoked in the presence of NMDA.<ref>Irie, T., Yanase, Y., Demizu, Y., Usami, M., & Kikura-Hanajiri, R. (2022). Derivatives of methoxetamine and major methoxetamine metabolites potently block NMDA receptors. Journal of Pharmacological Sciences, 150(4), 233-243. https://doi.org/10.1016/j.jphs.2022.09.005</ref>

Dissociatives inhibit the normal functioning NMDA receptors by binding to and blocking them. This disruption of neural network activity leads to loss of normal cognitive and affective processing, psychomotor functioning, anesthesia and eventually the equivalent of a “[https://en.wikipedia.org/wiki/K-hole k-hole].”

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

|{{effects/physical|
*'''[[Effect::Stimulation]]''' and '''[[Effect::Sedation]]''' - DMXE has been compared to MXE which is known for its especially sedating and relaxing effects. However dissociatives are also able to induce stimulation, usually in lower doses. 
*'''[[Effect::Pain relief]]'''
*'''[[Effect::Motor control loss]]'''
*'''[[Effect::Tactile suppression]]'''
*'''[[Effect:: Physical euphoria]]'''

}}
{{effects/disconnective|
*'''[[Effect::Tactile disconnection]]'''
*'''[[Effect::Visual disconnection]]''' - This eventually results in DMXE's equivalent of the "k-hole" or more specifically, ''[[Visual disconnection#Holes, spaces and voids|holes, spaces and voids]]'' alongside of ''[[Visual disconnection#Structures|structures]]''.

}}
{{effects/visual|
====Suppression====
*'''[[Effect::Visual acuity suppression]]'''
*'''[[Effect::Double vision]]'''

====Distortions====
*'''[[Effect::Perspective distortions]]'''


====[[Effect::Geometry]]====
If applicable, a brief paragraph summary describing the visual geometry produced by the substance may be included here.
====Hallucinatory states====
If applicable, a brief summary of the substance's visual effects profile may be written here.

*'''[[Effect::Internal hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'')

*'''[[Effect::External hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'')

}}

|{{effects/cognitive|
The general head space of DMXE, like MXE, is often described as particularly euphoric and clear-headed in comparison to that of [[DXM]] and [[ketamine]].

*'''[[Effect::Amnesia]]'''
*'''[[Effect::Anxiety suppression]]'''
*'''[[Effect::Depersonalization]]
*'''[[Effect::Derealization]]
*'''[[Effect::Dream potentiation]]'''
*'''[[Effect::Ego death]]'''
*'''[[Effect::Immersion enhancement]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::analysis suppression]]
*'''[[Effect::Introspection]]'''
*'''[[Effect::Mania]]'''
*'''[[Effect::Memory suppression]]''' 
*'''[[Effect::Personal meaning enhancement]]'''
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Time distortion]]'''

}}
{{effects/auditory|

*'''[[Effect::Auditory distortion|Distortions]]'''
*'''[[Effect::Auditory hallucinations|Hallucinations]]'''
*'''[[Effect::Auditory suppression|Suppression]]'''

}}
}}

===Experience reports===
There are currently {{#ask:[[Category:DMXE]][[Category:Experience]] | format=count}} experience reports which describe the effects of this substance in our [[experience index]].
{{#ask: [[Category:DMXE]][[Category:Experience]]|format=ul|Columns=1}}
Additional experience reports can be found here:
* [https://www.erowid.org/experiences/subs/exp_DMXE.shtml Erowid Experience Vaults: DMXE]

==Toxicity and harm potential==
{{further|Research chemicals#Toxicity and harm potential|Responsible use}}
'''Due to its similarity to MXE, it is advised to use MXE's safety profile when taking this substance.'''
The toxicity and long-term health effects of recreational DMXE use specifically have not been researched. 

This is because DMXE is a research chemical with a very brief history of human usage. 

It is strongly recommended that one use [[responsible use|harm reduction practices]] when using this substance.
===Lethal dosage===
===Tolerance and addiction potential===
===Dangerous interactions===
{{DangerousInteractions/Intro}}

*'''[[UncertainInteraction::DOx]]''' - As an NMDA antagonist MXE potentiates DOx which can be unpleasantly intense.
*'''[[UncertainInteraction::25x-NBOMe]]''' - As an NMDA antagonist MXE potentiates NBOMes which can be unpleasantly intense.
*'''[[UncertainInteraction::2C-T-x]]'''
*'''[[UncertainInteraction::PCP]]''' - There are no reports available about this combination.
*'''[[UncertainInteraction::Amphetamines]]''' - Risk of tachycardia, hypertension, and manic states.
*'''[[UncertainInteraction::MDMA]]''' - There have been reports of risky serotonergic interactions when the two are taken at the same time, but MXE taken to the end of an MDMA experience does not appear to cause the same issues.
*'''[[UncertainInteraction::Cocaine]]''' - Stimulants taken with MXE can lead to hypermanic states much more easily, especially if sleep is avoided.
*'''[[UncertainInteraction::Benzodiazepines]]''' - Both substances potentiate the ataxia and sedation caused by the other and can lead to unexpected loss of consciousness at high doses. Place affected patients in the recovery position to prevent vomit aspiration from excess.
*'''[[UncertainInteraction::SSRIs]]''' - Depending on the SSRI this combination can be unpredictable.
*'''[[UnsafeInteraction::MAOIs]]''' - MAO-B inhibitors appear to increase the potency of MXE. MAO-A inhbitors have some negative reports associated with the combination but there isn't much information available.
*'''[[DangerousInteraction::ΑMT]]'''
*'''[[DangerousInteraction::Alcohol]]''' - There is a high risk of memory loss, vomiting and severe ataxia from this combination.
*'''[[DangerousInteraction::GHB]]''' - Both substances cause ataxia and bring a risk of vomiting and unconsciousness. If the patient falls unconscious while under the influence there is a severe risk of vomit aspiration if they are not placed in the recovery position.
*'''[[DangerousInteraction::GBL]]''' - Both substances cause ataxia and bring a risk of vomiting and unconsciousness. If the patient falls unconscious while under the influence there is a severe risk of vomit aspiration if they are not placed in the recovery position.
*'''[[DangerousInteraction::Opioids]]''' - This combination can potentiate the effects of the opioid.
*'''[[DangerousInteraction::Tramadol]]'''

==Legal status==

*'''US:''' DMXE itself is not scheduled, but due to its similarities to now schedule I MXE, one can be prosecuted for under the Federal Analog Act, which states any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed in Schedule I, but only if intended for human consumption.
*'''CA:''' DMXE is on Schedule 1 in Canada.
*'''DE:''' DMXE is regulated under the NpSG in Germany.
*'''UK:''' DMXE is scheduled under Class B in the United Kingdom.

==See also==
*[[Responsible use]]
*[[Research chemical]]
*[[Dissociatives]]
*[[Arylcyclohexylamines]]
*[[MXE]]
*[[PCP]]
*[[Ketamine]]

==External links==
(List along order below)
* [https://en.wikipedia.org/wiki/Deoxymethoxetamine DMXE (Wikipedia)]
* [https://www.erowid.org/experiences/subs/exp_DMXE.shtml DMXE (Erowid Vault)]
* [https://isomerdesign.com/PiHKAL/explore.php?id=11315&name=DMXE DMXE (Isomer Design)]
* [https://pubchem.ncbi.nlm.nih.gov/compound/157010705 DMXE (PubChem)]

==Literature==
*Irie, T., Yanase, Y., Demizu, Y., Usami, M., & Kikura-Hanajiri, R. (2022). Derivatives of methoxetamine and major methoxetamine metabolites potently block NMDA receptors. Journal of Pharmacological Sciences, 150(4), 233-243. https://doi.org/10.1016/j.jphs.2022.09.005

==References==
<references />

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