This is an unofficial archive of PsychonautWiki as of 2025-08-11T15:14:44Z. Content on this page may be outdated, incomplete, or inaccurate. Please refer to the original page for the most up-to-date information.
'''Deoxymethoxetamine''' (also known as '''DMXE''') is a [[psychoactive class::dissociative]] substance of the [[Chemical class::arylcyclohexylamine]] class that produces [[ketamine|ketamine-like]] [[dissociative]] effects when [[administered]].
== '''DMXE (Deoxymethoxetamine)''' ==
DMXE has been sold online since around October 2022, marketed as a legal replacement for MXE. <ref>Alert from NDEWS Web Monitoring team: Increases in Reddit discussions of DMXE, October 2020–March 2021 | https://ndews.org/?wysija-page=1&controller=email&action=view&email_id=125&wysijap=subscriptions</ref>
'''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>
Limited data exists about the pharmacological properties, metabolism, and toxicity of DMXE in humans, and it has a limited history of human use. It is highly advised to use [[harm reduction practices]] if using this substance.
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>
==History and culture==
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.
{{historyStub}}
== '''History and Culture''' ==
The compound does not have a clear first synthesis date. DMXE was first reported as being used for recreational purposes in 2020,<ref>https://erowid.org/experiences/subs/exp_DMXE.shtml</ref> and has been increasing in popularity as an alternative to the now-banned MXE. It is rarely sold on the streets and is almost exclusively sold as a gray-area research chemical alternative to the more recognizable MXE for recreational and entheogenic purposes.
==Chemistry==
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>
{{chemistry}}
DMXE (Deoxymethoxetamine) is an arylcyclohexylamine, similar to PCP and ketamine. It is an analog of MXE (Methoxetamine), but instead of a methoxy in the 3 position it has only a methyl group, hence <u>Deoxy-</u>(without oxygen)-methoxetamine. DMXE lack of an oxygen results in a more hydrophobic and less bulky structure - causing the slight differences in pharmacology.
It is a white crystalline substance at room temperature that is sparingly soluble in ethanol (10mg/ml).<ref>https://www.caymanchem.com/product/33962/deoxymethoxetamine-(hydrochloride)</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==
==Pharmacology==
{{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.
DMXE acts as an NMDA receptor antagonist. A specific subtype of glutamate receptor, NMDA (N-Methyl-D-Aspartate), modulates 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 "k-hole".
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].”
An ''in silico'' study showed that DMXE binds to the same site of NMDARs as MXE and posseses comparable potency.
==Subjective effects==
==Subjective effects==
{{EffectStub}}
{{EffectStub}}
Line 101:
Line 116:
==Toxicity and harm potential==
==Toxicity and harm potential==
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}The toxicity and long-term health effects of recreational DMXE use do not seem to have been studied in any scientific context and the [[Toxicity::exact toxic dosage is unknown]].
{{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.
This is because DMXE is a research chemical with a very brief history of human usage.
Line 110:
Line 128:
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}
Due to similarities to other known and similar compounds, it is advised to use their safety profile when it comes to interactions:
*'''[[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]]'''
*'''Alcohol''' - Both substances cause ataxia and bring a very high risk of vomiting and unconsciousness. If the user falls unconscious while under the influence there is a severe risk of vomit aspiration if they are not placed in the recovery position.
==Legal status==
*'''GHB''' / '''GBL''' - Both substances cause ataxia and bring a risk of vomiting and unconsciousness. If the user falls unconscious while under the influence there is a severe risk of vomit aspiration if they are not placed in the recovery position.
*'''Opioids''' - Both substances bring a risk of vomiting and unconsciousness. If the user falls unconscious while under the influence there is a severe risk of vomit aspiration if they are not placed in the recovery position.
*'''Tramadol''' - Tramadol lowers the seizure threshold. Both substances increase the risk of vomiting and unconsciousness.
*'''Amphetamines''' - No unexpected interactions, though likely to increase blood pressure (likely not an issue with sensible doses). Moving around on high doses of this combination may be ill-advised due to risk of physical injury.
*'''Cocaine''' - No unexpected interactions, though likely to increase blood pressure (likely not an issue with sensible doses). Moving around on high doses of this combination may be ill-advised due to risk of physical injury.
*'''Benzodiazepines''' - Both substances potentiate the ataxia and sedation caused by the other and can lead to unexpected loss of consciousness at high doses. While unconscious, vomit aspiration is a risk if the user is not placed in the recovery position.
*'''Trazodone''' - When used as a sleep aid and taken close to that of a dose of ketamine, there is a risk of respiratory depression when high amounts of either are consumed.
*'''Grapefruit''' - Grapefruit juice might increase absorption of DMXE. This may result in the user having higher concentrations of DMXE in their system compared to normal. The DMXE may also have a longer duration of effect. This likely applies to oral, sublingual, and intranasal administration.
*'''MAOI''' - MAO-B is known to effect similar substances and their potency. MAOIs in general increase blood pressure, which could cause a spike if both are used.
==Legal status==
{{LegalStub}}
*'''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.
*'''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.
*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
Please see the [[citation formatting guide]] if you need assistance properly formatting citations.
It may contain incorrect information, particularly with respect to dosage, duration, subjective effects, toxicity and other risks. It may also not meet PW style and grammar standards.
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.
DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.
DMXE emerged in October 2020, marketed as a legal replacement for MXE following MXE's global ban.[2]
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.[3] Alongside MXiPr, it has been sold online as a research chemical dissociative since October 2020.[2][4]
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).
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 IC50 (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.[6]
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 “k-hole.”
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWikicontributors. As a result, they should be viewed with a healthy degree of skepticism.
It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.
Physical effects
Stimulation and 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.
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.
Warning:Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).
Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.
DOx - As an NMDA antagonist MXE potentiates DOx which can be unpleasantly intense.
25x-NBOMe - As an NMDA antagonist MXE potentiates NBOMes which can be unpleasantly intense.
2C-T-x
PCP - There are no reports available about this combination.
Amphetamines - Risk of tachycardia, hypertension, and manic states.
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.
Cocaine - Stimulants taken with MXE can lead to hypermanic states much more easily, especially if sleep is avoided.
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.
SSRIs - Depending on the SSRI this combination can be unpredictable.
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.
ΑMT
Alcohol - There is a high risk of memory loss, vomiting and severe ataxia from this combination.
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.
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.
Opioids - This combination can potentiate the effects of the opioid.
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.
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
↑ 2.02.1Irie, 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. DOI
↑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
