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MDEA: Difference between revisions

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'''3,4-Methylenedioxy-N-ethylamphetamine''' (also known as, '''Methylenedioxyethylamphetamine''', '''MDEA''', '''MDE''', and colloquially as '''Eve''') is an obscure, synthetic [[Psychoactive class::entactogen]] of the [[Chemical class::amphetamines|substituted amphetamine]] class that produces modified [[MDMA|MDMA-like]] entactogenic effects when [[routes of administration|administered]]. It is a closely related structural analog of [[MDMA]] and [[MDA]]<ref>PiHKAL|http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106</ref> that acts via the same pharmacological mechanism as a [[serotonin]], [[norepinephrine]], and [[dopamine]] [[releasing agent]] and [[reuptake inhibitor]].<ref name="MDEApharm">Freudenmann RW, Spitzer M (2004). "The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA)". CNS Drug Reviews. 10 (2): 89–116. https://doi.org10.1111/j.1527-3458.2004.tb00007.x. PMID 15179441.</ref>
'''3,4-Methylenedioxy-N-ethylamphetamine''' (also known as '''MDEA''', '''MDE''', and colloquially as '''Eve''') is a lesser-known [[Psychoactive class::entactogen]] substance of the [[Chemical class::amphetamine]] class. MDEA is chemically similar to [[MDMA]] and [[MDA]].<ref name="Isomer Design">{{cite web|title=Read #22 2C-C {{!}} PiHKAL · info|url=http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=22|website=isomerdesign.com}}</ref> It produces its effects by increasing levels of [[serotonin]], [[norepinephrine]], and [[dopamine]] in the brain.<ref name="MDEApharm">{{cite journal | vauthors=((Freudenmann, R. W.)), ((Spitzer, M.)) | journal=CNS drug reviews | title=The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA) | volume=10 | issue=2 | pages=89–116 | date= 2004 | issn=1080-563X | doi=10.1111/j.1527-3458.2004.tb00007.x}}</ref>


The first recorded human use of MDEA was in 1976 by [[Alexander Shulgin]], who noted its similarity to [[MDMA]] in both effects and potency, though faster to act and shorter in duration.<ref>Shulgin, Alexander. "Pharmacology Lab Notes #2". Lafayette, CA. (1976-1980). p206 (Erowid.org) | https://erowid.org/library/books_online/shulgin_labbooks/shulgin_labbook2_searchable.pdf</ref>. The synthesis and pharmacological evaluation of MDEA and a series of related compounds were published in 1980.<ref>Braun U, Shulgin AT, Braun G. "Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine)." J Pharm Sci. 1980 Feb;69(2):192-5. | https://www.ncbi.nlm.nih.gov/pubmed/6102141</ref>. MDEA is included in Shulgin's 1991 book "[[PiHKAL]]" ("[[Phenethylamine]]s I Have Known and Loved").<ref>PiHKAL|http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106</ref>.
The first recorded human use of MDEA was in 1976 by [[Alexander Shulgin]], who noted its similarity to [[MDMA]] in both effects and potency, though faster to act and shorter in duration.<ref>Shulgin, Alexander. "Pharmacology Lab Notes #2". Lafayette, CA. (1976-1980). p206 (Erowid.org) | https://erowid.org/library/books_online/shulgin_labbooks/shulgin_labbook2_searchable.pdf</ref> The synthesis and pharmacological evaluation of MDEA and a series of related compounds were published in 1980.<ref>{{cite journal | vauthors=((Braun, U.)), ((Shulgin, A. T.)), ((Braun, G.)) | journal=Journal of Pharmaceutical Sciences | title=Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine) | volume=69 | issue=2 | pages=192–195 | date= February 1980 | issn=0022-3549 | doi=10.1002/jps.2600690220}}</ref> MDEA is included in Shulgin's 1991 book "[[PiHKAL]]" ("[[Phenethylamine]]s I Have Known and Loved").<ref name="Isomer Design" />


In the United States, MDEA was introduced recreationally in 1985 as a legal substitute to the newly banned MDMA before it was made a Schedule I substance two years later.<ref>PiHKAL|http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106</ref> Since then, MDEA has rarely been sold on its own and has largely been used as an occasional additive or substitute ingredient in pills of "Ecstasy".<ref name="MDEApharm" />
In the United States, MDEA was introduced recreationally in 1985 as a legal substitute to the newly banned MDMA before it was made a Schedule I substance two years later.<ref name="MDEPiHKAL">{{Citation | title=Read #106 MDE - PiHKAL · info | url=http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106}}</ref> Since then, MDEA has rarely been sold on its own and has largely been used as an occasional additive or substitute ingredient in pills of "Ecstasy".<ref name="MDEApharm" />


While MDEA shares many of the core entactogenic properties of MDMA, it is slightly less potent and considered to be more "stoning", lacking the pro-socializing and energizing "magic" most party-goers seek in their MDMA experiences. As a result, it is largely considered by most people to be a less desirable variant of MDMA and is thus rarely produced and sold in the illicit drug market, typically showing up only in small batches synthesized and distributed by hobbyist clandestine chemists.{{citation needed}}
Very little data exists about the pharmacological properties, metabolism, and toxicity of MDEA,. As a result it is highly advised to approach this potentially habit-forming [[entactogenic]] substance with the proper amount of precaution and [[Responsible drug use#Hallucinogens|harm reduction practices]] if choosing to use it.
 
Very little data exists about the pharmacological properties, metabolism, and toxicity of MDEA, and it has little history of human usage. As a result it is highly advised to approach this potentially habit-forming [[entactogenic]] substance with the proper amount of precaution and [[Responsible drug use#Hallucinogens|harm reduction practices]] if choosing to use it.


==History and culture==
==History and culture==
{{historyStub}}
{{historyStub}}
In the United States, MDEA was introduced recreationally in 1985 as a legal substitute to the newly banned MDMA before it was made a Schedule I substance two years later on August 13, 1987 under the Federal Analogue Act.<ref>PiHKAL|http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106</ref> Since then, MDEA has rarely been sold on its own and has largely been used as an occasional additive or substitute ingredient in pills of "Ecstasy" (for instance, studies conducted in the 1990s found MDEA present in approximately four percent of ecstasy tablets).<ref name="MDEApharm" />
In the United States, MDEA was introduced recreationally in 1985 as a legal substitute to the newly banned MDMA before it was made a Schedule I substance two years later on August 13, 1987 under the Federal Analogue Act.<ref name="MDEPiHKAL"/> Since then, MDEA has rarely been sold on its own and has largely been used as an occasional additive or substitute ingredient in pills of "Ecstasy" (for instance, studies conducted in the 1990s found MDEA present in approximately four percent of ecstasy tablets).<ref name="MDEApharm" />


While MDEA shares many of the core entactogenic properties of MDMA, it is slightly less potent and considered to be more "stoning", lacking the pro-socializing and energizing "magic" most party-goers seek in their MDMA experiences. As a result, it is largely considered by most people to be a less desirable variant of MDMA and is thus rarely produced and sold in the illicit drug market, typically showing up only in small batches synthesized and distributed by hobbyist clandestine chemists.{{citation needed}}
While MDEA shares many of the core entactogenic properties of MDMA, it is slightly less potent and considered to be more "stoning", lacking the pro-socializing and energizing "magic" most party-goers seek in their MDMA experiences. As a result, it is largely considered by most people to be a less desirable variant of MDMA and is thus rarely produced and sold in the illicit drug market, typically showing up only in small batches synthesized and distributed by hobbyist clandestine chemists.{{citation needed}}


==Chemistry==
==Chemistry==
[[File:Phenethylamine.png|thumb|right|253px|thumb|right|253px||Generic structure of a phenethylamine molecule]]
[[File:Phenethylamine.png|thumb|right|253px|thumb|right||Generic structure of a phenethylamine molecule]]
MDEA, also known as 3,4-Methylenedioxy-N-ethylamphetamine, is a synthetic molecule of the [[Substituted amphetamine|substituted amphetamine]] chemical class.  Molecules of the amphetamine class contain a [[phenethylamine]] core featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain with an additional methyl substitution at R<sub>α</sub>. Additionally, MDEA contains an ethyl substitution on R<sub>N</sub>, which is a single carbon extension of the methyl group present in MDMA. MDEA also contains substitutions at R<sub>3</sub> and R<sub>4</sub> of the phenyl ring with oxygen groups that are incorporated into a methylenedioxy ring through a methylene bridge. MDEA shares this methylenedioxy ring with other [[entactogens]] like [[MDMA]], [[MDA]] and [[MDAI]].
MDEA, also known as 3,4-Methylenedioxy-N-ethylamphetamine, is a synthetic molecule of the [[Substituted amphetamine|substituted amphetamine]] chemical class.  Molecules of the amphetamine class contain a [[phenethylamine]] core featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain with an additional methyl substitution at R<sub>α</sub>. Additionally, MDEA contains an ethyl substitution on R<sub>N</sub>, which is a single carbon extension of the methyl group present in MDMA. MDEA also contains substitutions at R<sub>3</sub> and R<sub>4</sub> of the phenyl ring with oxygen groups that are incorporated into a methylenedioxy ring through a methylene bridge. MDEA shares this methylenedioxy ring with other [[entactogens]] like [[MDMA]], [[MDA]] and [[MDAI]].


==Pharmacology==
==Pharmacology==
MDEA has been shown to act as a [[releasing agent]] and [[reuptake inhibitor]] of the key [[monoamine]] [[neurotransmitters]] [[serotonin]], [[dopamine]] and [[noradrenaline]]<ref name="MDEApharm" /> which are the [[neurotransmitters]] responsible for modulating focus, motivation, pleasure, and reward. This is done by inhibiting the reuptake and reabsorption of [[monoamine neurotransmitters]] after they have performed their function of transmitting a neural impulse, allowing them to accumulate in the [[synaptic cleft]] and be reused in a manner which causes physically stimulating, sedating, disinhibiting and euphoric effects.<ref>New Insights into the Mechanism of Action of Amphetamines | http://www.annualreviews.org/doi/abs/10.1146/annurev.pharmtox.47.120505.105140</ref> The often-reported "stoning" effects have been theorized to arise from the higher relative activity MDEA has on releasing serotonin over dopamine compared to MDMA.
MDEA acts as a [[releasing agent]] and [[reuptake inhibitor]] of the [[monoamine]] [[neurotransmitters]] [[serotonin]], [[dopamine]] and [[noradrenaline]]<ref name="MDEApharm" />. These neurotransmitters are responsible for modulating focus, motivation, pleasure, and reward.  
 
The "stoning" effects of MDEA are thought to arise from the higher relative activity MDEA has on releasing serotonin over dopamine compared to MDMA.


It has also been noted that MDEA, even at lower doses, stimulates the release of oxytocin and prolactin, two hormones that are currently being studied for their potential roles in modulating the feeling of trust and love.<ref> Passie, Torsten, MD. Healing with Entactogens. Santa Cruz: Multidisciplinary Association for Psychedelic Studies, n.d. Print. </ref>
MDEA stimulates the release of oxytocin and prolactin, two hormones that are currently being studied for their potential roles in modulating the feeling of trust and love.<ref>{{cite book | vauthors=((Passie, T.)) | date= 2012 | title=Healing with entactogens: therapist and patient perspectives on MDMA-assisted group psychotherapy | publisher=Multidisciplinary Association for Psychedelic Studies (MAPS) | isbn=9780979862274}}</ref>


==Subjective effects==
==Subjective effects==
{{effectStub}}
{{effectStub}}
{{Preamble/SubjectiveEffects}}
{{Preamble/SubjectiveEffects}}
===Physical effects===
{{effects/base
*'''[[Effect::Spontaneous physical sensations]]''' - The "body high" of MDEA can be characterized as a moderate to extreme euphoric relaxing sensation that encompasses the entire body. It is capable of becoming overwhelmingly pleasurable at higher doses to the point of "flooring" or immobilizing the user. This sensation maintains a consistent presence that steadily rises with the onset and hits its limit once the peak has been reached, before steadily dropping off.
|{{effects/physical|
*'''[[Effect::Stimulation]]''' & '''[[Effect::Sedation]]''' - In terms of its effects on the user's physical energy levels, MDEA is commonly regarded as significantly less stimulating and energizing than MDMA, while still retaining its core entactogenic effects. Unlike MDMA, which encourages activities such as running, climbing and dancing in a way that makes it a popular choice for musical events such as festivals and raves. The distinct style of stimulation which MDEA presents can be described as mildly to moderately forced, trending more towards sedation and relaxation. This means that at higher doses, it becomes difficult or impossible to keep still as jaw clenching, involuntarily body shakes and vibrations become present, resulting in an extreme unsteadiness of the hands and a general lack of motor control, though to a far lesser degree than with MDMA.
*'''[[Effect::Spontaneous bodily sensations]]''' - The "body high" of MDEA can be characterized as a moderate to extreme euphoric relaxing sensation that encompasses the entire body. It is capable of becoming overwhelmingly pleasurable at higher doses to the point of "flooring" or immobilizing the user. This sensation maintains a consistent presence that steadily rises with the onset and hits its limit once the peak has been reached, before steadily dropping off.
**'''[[Effect::Physical euphoria]]'''
**'''[[Effect::Physical euphoria]]'''
*'''[[Effect::Stimulation]]''' & '''[[Effect::Sedation]]''' - In terms of its effects on the user's physical energy levels, MDEA is commonly regarded as significantly less stimulating and energizing than MDMA, while still retaining its core entactogenic effects. Unlike MDMA, which encourages activities such as running, climbing and dancing in a way that makes it a popular choice for musical events such as festivals and raves. The distinct style of stimulation which MDEA presents can be described as mildly to moderately forced, trending more towards sedation and relaxation. This means that at higher doses, it becomes difficult or impossible to keep still as jaw clenching, involuntarily body shakes and vibrations become present, resulting in an extreme unsteadiness of the hands and a general lack of motor control, though to a far lesser degree than with MDMA.
**'''[[Effect::Perception of bodily heaviness]]''' - This effect, combined with sedation, is possibly the basis for why MDEA is frequently characterized as "stoning" relative to other [[entactogens]], which often have more pronounced [[stimulating]] effects.
**'''[[Effect::Perception of increased weight]]''' - This effect, combined with sedation, is possibly the basis for why MDEA is frequently characterized as "stoning" relative to other [[entactogens]], which often have more pronounced [[stimulating]] effects.
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Vibrating vision]]''' - At high doses, a person's eyeballs may begin to spontaneously wiggle back and forth in a rapid motion, causing the vision to become blurry and temporarily out of focus. This is a condition known as [http://en.wikipedia.org/wiki/Nystagmus nystagmus].
*'''[[Effect::Vibrating vision]]''' - At high doses, a person's eyeballs may begin to spontaneously wiggle back and forth in a rapid motion, causing the vision to become blurry and temporarily out of focus. This is a condition known as [http://en.wikipedia.org/wiki/Nystagmus nystagmus].
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*'''[[Effect::Temporary erectile dysfunction]]'''
*'''[[Effect::Temporary erectile dysfunction]]'''


===Cognitive effects===
}}
 
{{effects/visual|
 
====Enhancements====
MDEA presents an array of visual enhancements which are mild in comparison to traditional psychedelics, but still distinctively present. These generally include:
*'''[[Effect::Colour enhancement]]'''
*'''[[Effect::Pattern recognition enhancement]]'''
 
====Suppressions====
*'''[[Effect::Double vision]]'''
 
====Distortions====
*'''[[Effect::Tracers]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
 
====Hallucinatory states====
MDEA is capable of producing a unique range of low and high-level hallucinatory states in a fashion that is significantly less consistent and reproducible than that of many other commonly used [[psychedelics]]. These effects are far more common during the [[Duration#Offset|offset]] of the experience and commonly include:
*'''[[Effect::Peripheral information misinterpretation]]
 
}}
 
|{{effects/cognitive|
The cognitive effects of MDEA can be broken down into several components which progressively intensify proportional to dosage. The broad head space of MDEA is described by many as one of moderate mental stimulation, feelings of love, warmth or empathy and powerful relaxing euphoria. It contains a large number of typical [[Psychedelics|psychedelic]], [[Entactogens|entactogenic]] and [[Stimulants|stimulating]] cognitive effects.  
The cognitive effects of MDEA can be broken down into several components which progressively intensify proportional to dosage. The broad head space of MDEA is described by many as one of moderate mental stimulation, feelings of love, warmth or empathy and powerful relaxing euphoria. It contains a large number of typical [[Psychedelics|psychedelic]], [[Entactogens|entactogenic]] and [[Stimulants|stimulating]] cognitive effects.  


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*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Wakefulness]]'''


===Visual effects===
}}
 
====Enhancements====
MDEA presents an array of visual enhancements which are mild in comparison to traditional psychedelics, but still distinctively present. These generally include:
*'''[[Effect::Colour enhancement]]'''
*'''[[Effect::Pattern recognition enhancement]]'''
 
====Suppressions====
*'''[[Effect::Double vision]]'''
 
====Distortions====
*'''[[Effect::Tracers]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
 
====Hallucinatory states====
MDEA is capable of producing a unique range of low and high-level hallucinatory states in a fashion that is significantly less consistent and reproducible than that of many other commonly used [[psychedelics]]. These effects are far more common during the [[Duration#Offset|offset]] of the experience and commonly include:
*'''[[Effect::Peripheral information misinterpretation]]


===Auditory effects===
{{effects/auditory|
*'''[[Effect::Auditory enhancement|Enhancements]]'''
*'''[[Effect::Auditory enhancement|Enhancements]]'''
*'''[[Effect::Auditory hallucinations|Hallucinations]]'''
*'''[[Effect::Auditory hallucinations|Hallucinations]]'''
*'''[[Effect::Auditory distortion|Distortions]]'''
*'''[[Effect::Auditory distortion|Distortions]]'''


===[[Transpersonal]] effects===
}}
 
{{effects/transpersonal|
*'''[[Effect::Existential self-realization]]'''  
*'''[[Effect::Existential self-realization]]'''  
*'''[[Effect::Unity and interconnectedness]]''' - Experiences of unity, oneness and interconnectedness between level 1 - 2 are common within MDEA.{{citation needed}}
*'''[[Effect::Unity and interconnectedness]]''' - Experiences of unity, oneness and interconnectedness between level 1 - 2 are common within MDEA.{{citation needed}}


===After effects===
}}
 
{{effects/aftereffects|
The effects which occur during the [[offset]] of a [[stimulant]] experience generally feel negative and uncomfortable in comparison to the effects which occurred during its [[peak]]. This is often referred to as a "comedown" and occurs because of [[neurotransmitter]] depletion. Its effects commonly include:
The effects which occur during the [[offset]] of a [[stimulant]] experience generally feel negative and uncomfortable in comparison to the effects which occurred during its [[peak]]. This is often referred to as a "comedown" and occurs because of [[neurotransmitter]] depletion. Its effects commonly include:
*'''[[Effect::Anxiety]]'''
*'''[[Effect::Anxiety]]'''
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*'''[[Effect::Thought deceleration]]'''  
*'''[[Effect::Thought deceleration]]'''  
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Wakefulness]]'''
}}
}}
===Experience reports===
===Experience reports===
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:
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==Toxicity and harm potential==
==Toxicity and harm potential==
===Short-term health concerns===
Short-term physical health risks of MDEA consumption include [[dehydration]], [[insomnia]], [[hyperthermia]],<ref>{{cite journal | vauthors=((Nimmo, S. M.)), ((Kennedy, B. W.)), ((Tullett, W. M.)), ((Blyth, A. S.)), ((Dougall, J. R.)) | journal=Anaesthesia | title=Drug-induced hyperthermia | volume=48 | issue=10 | pages=892–895 | date= October 1993 | url=https://onlinelibrary.wiley.com/doi/10.1111/j.1365-2044.1993.tb07423.x | issn=0003-2409 | doi=10.1111/j.1365-2044.1993.tb07423.x}}</ref><ref>{{cite journal | vauthors=((Malberg, J. E.)), ((Seiden, L. S.)) | journal=The Journal of Neuroscience: The Official Journal of the Society for Neuroscience | title=Small changes in ambient temperature cause large changes in 3,4-methylenedioxymethamphetamine (MDMA)-induced serotonin neurotoxicity and core body temperature in the rat | volume=18 | issue=13 | pages=5086–5094 | date=1 July 1998 | issn=0270-6474}}</ref> and hyponatremia.<ref>{{cite journal | vauthors=((Wolff, K.)), ((Tsapakis, E. M.)), ((Winstock, A. R.)), ((Hartley, D.)), ((Holt, D.)), ((Forsling, M. L.)), ((Aitchison, K. J.)) | journal=Journal of Psychopharmacology | title=Vasopressin and oxytocin secretion in response to the consumption of ecstasy in a clubbing population | volume=20 | issue=3 | pages=400–410 | date= May 2006 | url=http://journals.sagepub.com/doi/10.1177/0269881106061514 | issn=0269-8811 | doi=10.1177/0269881106061514}}</ref> Continuous activity without sufficient rest or rehydration may cause body temperature to rise to dangerous levels, and loss of fluid via excessive perspiration puts the body at further risk as the stimulatory and euphoric qualities of the drug may render the user oblivious to their energy expenditure for quite some time. Diuretics such as alcohol may exacerbate these risks further.
Short-term physical health risks of MDEA consumption include [[dehydration]], [[insomnia]], [[hyperthermia]],<ref>Drug-induced hyperthermia | http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2044.1993.tb07423.x/abstract;jsessionid=FC30A9B157A2BAFC81048D8595714565.f02t03</ref><ref>Small changes in ambient temperature cause large changes in 3,4-methylenedioxymethamphetamine (MDMA)-induced serotonin neurotoxicity and core body temperature in the rat (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/9634574</ref> and hyponatremia.<ref>Vasopressin and oxytocin secretion in response to the consumption of ecstasy in a clubbing population | http://jop.sagepub.com/content/20/3/400</ref> Continuous activity without sufficient rest or rehydration may cause body temperature to rise to dangerous levels, and loss of fluid via excessive perspiration puts the body at further risk as the stimulatory and euphoric qualities of the drug may render the user oblivious to their energy expenditure for quite some time. Diuretics such as alcohol may exacerbate these risks further.


The [[Toxicity::exact toxic dosage is unknown]], but considered to be far greater than its active dose.
The [[Toxicity::exact toxic dosage is unknown]], but considered to be far greater than its active dose.


===Long-term health concerns===
===Neurotoxicity===
As with MDMA, the neurotoxicity of MDEA use has long been the subject of debate. Scientific study has resulted in the general agreement that, although it is physically safe to try in a responsible context, the administration of repeated or high dosages of MDEA is likely to be neurotoxic and cardiotoxic in some form.
As with MDMA, the neurotoxicity of MDEA use has long been the subject of debate. Scientific study has resulted in the general agreement that, although it is physically safe to try in a responsible context, the administration of repeated or high dosages of MDEA is likely to be neurotoxic and cardiotoxic in some form.


Like other powerful serotonin releasing agents, MDEA is thought to cause down-regulation of [[serotonin]] reuptake transporters in the brain. The rate at which the brain recovers from serotonergic changes is unclear. One study demonstrated lasting serotonergic changes in some animals exposed to MDMA, which likely applies to MDEA as well.<ref>Reorganization of ascending 5-HT axon projections in animals previously exposed to the recreational drug (+/-)3,4-methylenedioxymethamphetamine (MDEA, "ecstasy") (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/7643196</ref> Other studies have suggested that the brain may recover from serotonergic damage.<ref>In vivo detection of short- and long-term MDEA neurotoxicity--a positron emission tomography study in the living baboon brain (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/9593108</ref><ref>Reneman L, Lavalaye J, Schmand B, de Wolff FA, van den Brink W, den Heeten GJ, Booij J (2001). "Cortical serotonin transporter density and verbal memory in individuals who stopped using 3,4-methylenedioxymethamphetamine (MDEA or "ecstasy"): preliminary findings". Arch. Gen. Psychiatry 58 (10): 901–6. </ref><ref>Selvaraj, S. et al (2009) "Brain Serotonin transporter binding in former users of MDEA ("ecstasy")." British Journal of Psychiatry. 194: 355-359. | https://www.ncbi.nlm.nih.gov/pubmed/19336788</ref>
Like other powerful serotonin releasing agents, MDEA is thought to cause down-regulation of [[serotonin]] reuptake transporters in the brain. The rate at which the brain recovers from serotonergic changes is unclear. One study demonstrated lasting serotonergic changes in some animals exposed to MDMA, which likely applies to MDEA as well.<ref>{{cite journal | vauthors=((Fischer, C.)), ((Hatzidimitriou, G.)), ((Wlos, J.)), ((Katz, J.)), ((Ricaurte, G.)) | journal=The Journal of Neuroscience: The Official Journal of the Society for Neuroscience | title=Reorganization of ascending 5-HT axon projections in animals previously exposed to the recreational drug (+/-)3,4-methylenedioxymethamphetamine (MDMA, “ecstasy”) | volume=15 | issue=8 | pages=5476–5485 | date= August 1995 | issn=0270-6474}}</ref> Other studies have suggested that the brain may recover from serotonergic damage.<ref>{{cite journal | vauthors=((Scheffel, U.)), ((Szabo, Z.)), ((Mathews, W. B.)), ((Finley, P. A.)), ((Dannals, R. F.)), ((Ravert, H. T.)), ((Szabo, K.)), ((Yuan, J.)), ((Ricaurte, G. A.)) | journal=Synapse (New York, N.Y.) | title=In vivo detection of short- and long-term MDMA neurotoxicity--a positron emission tomography study in the living baboon brain | volume=29 | issue=2 | pages=183–192 | date= June 1998 | issn=0887-4476 | doi=10.1002/(SICI)1098-2396(199806)29:2<183::AID-SYN9>3.0.CO;2-3}}</ref><ref>{{cite journal | vauthors=((Reneman, L.)), ((Lavalaye, J.)), ((Schmand, B.)), ((Wolff, F. A. de)), ((Brink, W. van den)), ((Heeten, G. J. den)), ((Booij, J.)) | journal=Archives of General Psychiatry | title=Cortical Serotonin Transporter Density and Verbal Memory in Individuals Who Stopped Using 3,4-Methylenedioxymethamphetamine (MDMA or “Ecstasy”): Preliminary Findings | volume=58 | issue=10 | pages=901 | date=1 October 2001 | url=http://archpsyc.jamanetwork.com/article.aspx?doi=10.1001/archpsyc.58.10.901 | issn=0003-990X | doi=10.1001/archpsyc.58.10.901}}</ref><ref>{{cite journal | vauthors=((Selvaraj, S.)), ((Hoshi, R.)), ((Bhagwagar, Z.)), ((Murthy, N. V.)), ((Hinz, R.)), ((Cowen, P.)), ((Curran, H. V.)), ((Grasby, P.)) | journal=The British Journal of Psychiatry: The Journal of Mental Science | title=Brain serotonin transporter binding in former users of MDMA ('ecstasy’) | volume=194 | issue=4 | pages=355–359 | date= April 2009 | issn=1472-1465 | doi=10.1192/bjp.bp.108.050344}}</ref>


Like with MDMA, the long-term heavy use of MDEA is likely similarly cardiotoxic, leading to valvulopathy through its actions on the 5-HT<sub>2B</sub> receptor.<ref> Drug-induced Valvulopathy: An Update | tpx.sagepub.com/content/38/6/837.full</ref> In one study, 28% of long-term MDMA users (2-3 doses per week for a mean of 6 years, mean of age 24.3 years) had developed clinically evident valvular heart disease.<ref>Possible association between 3,4-methylenedioxymethamphetamine abuse and valvular heart disease. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/17950805</ref>
===Cardiotoxicity===
 
Like with MDMA, the long-term heavy use of MDEA is likely similarly cardiotoxic, leading to valvulopathy through its actions on the 5-HT<sub>2B</sub> receptor.<ref>{{cite journal | vauthors=((Elangbam, C. S.)) | journal=Toxicologic Pathology | title=Drug-induced Valvulopathy: An Update | volume=38 | issue=6 | pages=837–848 | date= October 2010 | url=http://journals.sagepub.com/doi/10.1177/0192623310378027 | issn=0192-6233 | doi=10.1177/0192623310378027}}</ref> In one study, 28% of long-term MDMA users (2-3 doses per week for a mean of 6 years, mean of age 24.3 years) had developed clinically evident valvular heart disease.<ref>{{cite journal | vauthors=((Droogmans, S.)), ((Cosyns, B.)), ((D’haenen, H.)), ((Creeten, E.)), ((Weytjens, C.)), ((Franken, P. R.)), ((Scott, B.)), ((Schoors, D.)), ((Kemdem, A.)), ((Close, L.)), ((Vandenbossche, J.-L.)), ((Bechet, S.)), ((Van Camp, G.)) | journal=The American Journal of Cardiology | title=Possible association between 3,4-methylenedioxymethamphetamine abuse and valvular heart disease | volume=100 | issue=9 | pages=1442–1445 | date=1 November 2007 | issn=0002-9149 | doi=10.1016/j.amjcard.2007.06.045}}</ref>


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.
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There is an increased risk of serotonin syndrome when MDEA is taken with many antidepressants, particularly selective serotonin reuptake inhibitors (SSRIs) and serotonin-norepinephrine reuptake inhibitors (SNRIs). Additionally, if MDEA is taken with SSRIs and SNRIs, the MDEA will be significantly less powerful or may have no distinguishable effects at all.
There is an increased risk of serotonin syndrome when MDEA is taken with many antidepressants, particularly selective serotonin reuptake inhibitors (SSRIs) and serotonin-norepinephrine reuptake inhibitors (SNRIs). Additionally, if MDEA is taken with SSRIs and SNRIs, the MDEA will be significantly less powerful or may have no distinguishable effects at all.


==Legality==
==Legal status==
{{LegalStub}}
{{LegalStub}}
*'''Brazil''' - Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344 as "MDE".<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref>
Internationally, MDEA is part of the the Convention on Psychotropic Substances of 1971 as a Schedule I substance.<ref>{{cite web|url=http://www.emcdda.europa.eu/system/files/attachments/10451/convention_1971_en.pdf|title=CONVENTION ON PSYCHOTROPIC SUBSTANCES 1971|publisher=United Nations|access-date=December 16, 2019}}</ref> (''MDE'')
*'''United Kingdom:''' MDEA is a Class A drug.
*'''Austria''': MDEA is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).{{citation needed}}
*'''United States:''' MDEA is a Schedule I drug.
*'''Brazil''': MDEA is illegal to possess, produce or sell as it is listed on Portaria SVS/MS nº 344 as "MDE".<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref>
*'''Canada''': MDEA  is listed on the CSDA in Schedule I.<ref>{{cite web|url=https://www.laws-lois.justice.gc.ca/eng/acts/C-38.8/page-13.html#docCont|title=Controlled Drugs and Substances Act - SCHEDULE I|publisher=Government of Canada|access-date=December 16, 2019}}</ref>
*'''France''': MDEA is scheduled as a "stupéfiant", i.e. a recognized drug of abuse. It is illegal to possess, buy, sell or manufacture.<ref>{{Citation | title=Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants  | url=https://www.legifrance.gouv.fr/loda/id/JORFTEXT000000533085/2020-11-20/}}</ref>
*'''Germany''': MDEA is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of April 15, 1991.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?start=%2F%2F*%5B%40attr_id%3D%27bgbl191s0712.pdf%27%5D|title=Dritte Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|access-date=December 15, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Anlage I BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 15, 2019|language=de}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or to dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=§ 29 BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 15, 2019|language=de}}</ref> (''MDE'') 
*'''Switzerland''': MDEA 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>
*'''United Kingdom''': MDEA is a Class A drug.{{citation needed}}
*'''United States''': MDEA is a Schedule I drug.{{citation needed}}


==See also==
==See also==
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==External links==
==External links==
*[https://en.wikipedia.org/wiki/3,4-Methylenedioxy-N-ethylamphetamine MDEA (Wikipedia)]
*[https://en.wikipedia.org/wiki/3,4-Methylenedioxy-N-ethylamphetamine MDEA (Wikipedia)]
*[https://erowid.org/chemicals/mde/mde.shtml MDEA (Erowid)]
*[https://erowid.org/chemicals/mde/mde.shtml MDEA (Erowid Vault)]
*[http://www.rollsafe.org/ RollSafe]
*[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106 MDEA (PiHKAL / Isomer Design)]
*[https://go.drugbank.com/drugs/DB01566 MDEA (DrugBank)]


==Literature==
==Literature==
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==References==
==References==
<references/>
<references />
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Amphetamine]]
[[Category:Amphetamine]]
[[Category:Phenethylamine]]
[[Category:Entactogen]]
[[Category:Entactogen]]
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