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{{SubstanceBox/MDEA}}
 
'''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>{{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" />


{{SubstanceBox/MDEA}}
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" />
{|
|-
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| ''[[MDEA/Summary|Summary sheet: MDEA]]''
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'''MDEA''' (also known as '''3,4-methylenedioxy-N-ethylamphetamine''', '''MDE''' or '''Eve''') is a [[stimulant]] and [[Psychoactive class::entactogen]]ic drug of the [[phenethylamine]] and [[Chemical class::Substituted amphetamines|substituted amphetamine]] classes and a closely related structural analog of [[MDMA]] and [[MDA]].  


In a 1967 lab notebook entry, Alexander Shulgin briefly mentioned a colleague's report of no effect from the substance with a 100mg dose.<ref>Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin|doi=10.1111/j.1360-0443.2010.02948.x}}</ref> Shulgin later tested the compound at a range of higher doses and characterized the substance in his book [[PiHKAL]].<ref>PiHKAL|http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106</ref>
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.


MDEA is rarely sold on its own and has historically been used as an occasional additive or substitute ingredient in pills of "Ecstasy". 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 in on August 13, 1987 under the Federal Analog Act.<ref>PiHKAL|http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106</ref>
==History and culture==
{{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 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 same 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/ecstasy 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 in small batches synthesized and distributed by hobbyist clandestine chemists.
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||General formula 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]] family.  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 drugs 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 acts as a [[releasing agent]] of the key [[monoamine]] [[neurotransmitters]] known as [[serotonin]], [[dopamine]] and [[noradrenaline]]<ref>Effects of methylenedioxymethamphetamine on the release of monoamines from rat brain slices (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/001429999094150V</ref> which are the [[neurotransmitters]] in charge of pleasure, reward, motivation and focus. This is done by inhibiting the reuptake and reabsorption of [[monoamine neurotransmitter]]s after they have performed their function of transmitting a neural impulse, essentially allowing them to accumulate and be reused in a manner which causes physically stimulating 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 previously mentioned "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.  


It has also been noted that MDEA, even at lower doses, stimulates the release of oxytocin and prolactin, two hormones that have a role in the feeling of trust and love. <ref> Passie, Torsten, MD. Healing with Entactogens. Santa Cruz: Multidisciplinary Association for Psychedelic Studies, n.d. Print. </ref>
The "stoning" effects of MDEA are thought to arise from the higher relative activity MDEA has on releasing serotonin over dopamine compared to MDMA.
 
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==
The effects listed below are based upon the [[subjective effects index]] and personal experiences of [[PsychonautWiki]] [[Special:TopUsers|contributors]]. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.
{{effectStub}}
===Physical effects===
{{Preamble/SubjectiveEffects}}
*'''[[Effect::Spontaneous tactile 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.
{{effects/base
*'''[[Effect::Stimulation]]''' - 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.  
|{{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::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::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].
*'''[[Effect::Temperature regulation suppression]]''' - As MDEA is a serotonin releasing agent, rise in core body temperature tends to be high and consistent throughout the experience. Caution must be taken as too high of a dose results in [[serotonin syndrome]] which can be fatal if left untreated.
**'''[[Effect::Increased bodily temperature]]''' - As MDEA is a serotonin releasing agent, rise in core body temperature tends to be high and consistent throughout the experience. Caution must be taken as too high of a dose results in [[serotonin syndrome]] which can be fatal if left untreated.
*'''[[Effect::Dehydration]]''' - Like related entactogenic stimulants, feelings of dry mouth and dehydration are a universal experience with MDEA; this effect is a product of an [[increased heart rate]] and metabolism. While it is important to avoid becoming dehydrated (especially when out dancing in a hot environment) there have been a number of users who have suffered from [https://en.wikipedia.org/wiki/Water_intoxication water intoxication] through over-drinking, so it is advised that users simply sip at the water and never over-drink.
*'''[[Effect::Dehydration]]''' - Like related entactogenic stimulants, feelings of dry mouth and dehydration are a universal experience with MDEA; this effect is a product of an [[increased heart rate]] and metabolism. While it is important to avoid becoming dehydrated (especially when out dancing in a hot environment) there have been a number of users who have suffered from [https://en.wikipedia.org/wiki/Water_intoxication water intoxication] through over-drinking, so it is advised that users simply sip at the water and never over-drink.
*'''[[Effect::Difficulty urinating]]''' - Higher doses of MDEA result in an overall difficulty when it comes to urination. This is an effect that is completely temporary and harmless. It is caused by MDEA’s promotion of the release of anti-diuretic hormone (ADH); ADH is responsible for regulating urination. This effect can be lessened by simply relaxing, but can be significantly relieved by placing a hot flannel over the genitals to warm them up and encourage blood flow.
*'''[[Effect::Difficulty urinating]]''' - Higher doses of MDEA result in an overall difficulty when it comes to urination. This is an effect that is completely temporary and harmless. It is caused by MDEA’s promotion of the release of anti-diuretic hormone (ADH); ADH is responsible for regulating urination. This effect can be lessened by simply relaxing, but can be significantly relieved by placing a hot flannel over the genitals to warm them up and encourage blood flow.
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Bodily control enhancement]]'''
*'''[[Effect::Brain zaps]]'''
*'''[[Effect::Increased blood pressure]]'''
*'''[[Effect::Increased blood pressure]]'''
*'''[[Effect::Increased bodily temperature]]''' - As MDEA is a serotonin releasing agent, rise in core body temperature tends to be high and consistent throughout the experience. Caution must be taken as too high of a dose results in [[serotonin syndrome]] which can be fatal if left untreated.
*'''[[Effect::Increased heart rate]]'''
*'''[[Effect::Increased heart rate]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Perception of decreased weight]]'''
*'''[[Effect::Bodily control enhancement]]'''
*'''[[Effect::Physical euphoria]]'''
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Brain zaps]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Stamina enhancement]]'''
*'''[[Effect::Stamina enhancement]]'''
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Teeth grinding]]''' - This component is usually only present in the higher dose range, and to a lesser extent than the teeth grinding associated with MDMA.  
*'''[[Effect::Teeth grinding]]''' - This component is usually only present in the higher dose range, and to a lesser extent than the teeth grinding associated with MDMA.  
*'''[[Effect::Temporary erectile dysfunction]]'''
*'''[[Effect::Temporary erectile dysfunction]]'''


===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|stimulant]] cognitive effects.


The most prominent of these cognitive effects generally include:
{{effects/visual|
 
*'''[[Effect::Cognitive euphoria]]''' - Strong emotional euphoria and feelings of happiness are present within MDEA and are likely a direct result of serotonin and dopamine release.
*'''[[Effect::Empathy, love, and sociability enhancement]]''' - This particular effect is present, but not nearly as consistent, pronounced, powerful and therapeutic than one would experience with MDMA With time and repeated use, however, this effect becomes severely diminished as the perspective it instills becomes fully grounded and already in place, making people feel merely stimulated and euphoric with no new found urges to communicate, with others. Some users report that MDEA "loses its magic" with as few as 10 experiences, while others have reported hundreds of uses before the empathic qualities disappear. This does not appear to be valid for all users, however, with many users reporting that they have not experienced any decrease in quality of the experience despite dozens or even hundreds of uses.
*'''[[Effect::Time distortion]]''' - Strong feelings of time compression are common within MDEA and speed up the experience of time quite noticeably.
*'''[[Effect::Unity and interconnectedness]]''' - Experiences of unity, oneness and interconnectedness between level 1 - 2 are common within MDEA.
*'''[[Anxiety suppression|Effect::Anxiety suppression]]'''
*'''[[Effect::Compulsive redosing]]'''
*'''[[Effect::Creativity enhancement]]'''
*'''[[Effect::Dream suppression]]'''
*'''[[Effect::Existential self-realization]]''' - Although this effect is present, it is not quite as pronounced or as consistent when compared to other [[hallucinogen]]s such as [[mescaline]], [[Psilocin]], [[LSD]] or [[MXE]] or even other entactogens like MDMA.
*'''[[Effect::Focus enhancement]]''' - This component is most effective at low to moderate doses as anything higher will usually impair concentration.
*'''[[Effect::Immersion enhancement]]'''
*'''[[Effect::Increased libido]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Mindfulness]]'''
*'''[[Effect::Motivation enhancement]]'''
*'''[[Effect::Thought acceleration]]'''
 
===Visual effects===


====Enhancements====
====Enhancements====
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====Hallucinatory states====
====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 [[psychedelic]]s. These effects are far more common during the [[Duration#Offset|offset]] of the experience and commonly include:
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]]
*'''[[Effect::Peripheral information misinterpretation]]


===Auditory effects===
}}
 
|{{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 most prominent of these cognitive effects generally include:
 
*'''[[Effect::Anxiety suppression]]'''
*'''[[Effect::Empathy, affection, and sociability enhancement]]''' - This particular effect is present, but not nearly as consistent, pronounced, powerful and therapeutic than one would experience with MDMA With time and repeated use, however, this effect becomes severely diminished as the perspective it instills becomes fully grounded and already in place, making people feel merely stimulated and euphoric with no new found urges to communicate, with others. Some users report that MDEA "loses its magic" with as few as 10 experiences, while others have reported hundreds of uses before the empathic qualities disappear. This does not appear to be valid for all users, however, with many users reporting that they have not experienced any decrease in quality of the experience despite dozens or even hundreds of uses.
*'''[[Effect::Disinhibition]]'''
*'''[[Effect::Cognitive euphoria]]''' - Strong emotional euphoria and feelings of happiness are present within MDEA and are likely a direct result of serotonin and dopamine release.
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Time distortion]]''' - Strong feelings of time compression are common within MDEA and speed up the experience of time quite noticeably.
*'''[[Effect::Compulsive redosing]]'''
*'''[[Effect::Creativity enhancement]]'''
*'''[[Effect::Focus enhancement]]''' - This component is most effective at low to moderate doses of anything higher will usually impair concentration.
*'''[[Effect::Immersion enhancement]]'''
*'''[[Effect::Motivation enhancement]]'''
*'''[[Effect::Increased libido]]'''
*'''[[Effect::Mindfulness]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Wakefulness]]'''
 
}}
 
{{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]]'''


===After effects===
}}
 
{{effects/transpersonal|
*'''[[Effect::Existential self-realization]]'''
*'''[[Effect::Unity and interconnectedness]]''' - Experiences of unity, oneness and interconnectedness between level 1 - 2 are common within MDEA.{{citation needed}}
 
}}
 
{{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]]'''
Line 98: Line 117:
*'''[[Effect::Cognitive fatigue]]'''
*'''[[Effect::Cognitive fatigue]]'''
*'''[[Effect::Depression]]'''
*'''[[Effect::Depression]]'''
*'''[[Effect::Dream potentiation]]''' - Some users note extremely strange, vivid and sometimes rather scary dreams for several nights after taking large doses of MDEA.
*'''[[Effect::Dream potentiation]]''' & '''[[Effect::Dream suppression]]''' - Some users note extremely strange, vivid and sometimes rather scary dreams for several nights after taking large doses of MDEA.
*'''[[Sleep paralysis]]''' - Some users note sleep paralysis after consuming MDEA, particularly in high doses or in conjunction with other factors such as lack of sleep or physical fatigue.
*'''[[Sleep paralysis]]''' - Some users note sleep paralysis after consuming MDEA, particularly in high doses or in conjunction with other factors such as lack of sleep or physical fatigue.
*'''[[Effect::Irritability]]'''
*'''[[Effect::Irritability]]'''
Line 104: Line 123:
*'''[[Effect::Thought deceleration]]'''  
*'''[[Effect::Thought deceleration]]'''  
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Wakefulness]]'''
}}
}}
===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:
* [https://erowid.org/experiences/subs/exp_MDE.shtml Erowid Experience Vaults: MDEA]


==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 most certainly neurotoxic 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>{{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 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>
===Cardiotoxicity===


Like with MDMA, the long-term heavy use of MDEA is likely similarly cardiotoxic, leading to valvulopathy through its actions on the 5-HT2B receptor.<ref> Drug-induced Valvulopathy: An Update | tpx.sagepub.com/content/38/6/837.full</ref> In one study, 28% of long-term 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>
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 drug.
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.


===Tolerance and addiction potential===
===Tolerance and addiction potential===
As with other [[stimulant]]s, the chronic use of MDEA can be considered [[Addiction potential::moderately addictive with a high potential for abuse]] and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and [[withdrawal effects]] may occur if a person suddenly stops their usage.
As with other [[stimulant]]s, the chronic use of MDEA can be considered [[Addiction potential::moderately addictive with a high potential for abuse]] and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and [[withdrawal effects]] may occur if a person suddenly stops their usage.


Tolerance to many of the effects of MDEA develops [[Time to full tolerance::with prolonged and repeated use]]. This results in users having to administer increasingly larger doses to achieve the same effects. After that, it takes about [[Time to half tolerance::1 months]] for the tolerance to be reduced to half and [[Time to zero tolerance::2-3 months]] to be back at baseline (in the absence of further consumption). MDEA presents cross-tolerance with [[Cross-tolerance::all [[dopamine]]rgic and [[serotonin|serotonergic]] [[stimulant]]s and entactogens]], meaning that after the consumption of MDEA all of these will have a reduced effect.
Tolerance to many of the effects of MDEA develops [[Time to full tolerance::with prolonged and repeated use]]. This results in users having to administer increasingly larger doses to achieve the same effects. After that, it takes about [[Time to half tolerance::1-1.5 months]] for the tolerance to be reduced to half and [[Time to zero tolerance::2-3 months]] to be back at baseline (in the absence of further consumption). MDEA presents cross-tolerance with [[Cross-tolerance::all [[dopamine]]rgic and [[serotonin|serotonergic]] [[stimulant]]s and entactogens]], meaning that after the consumption of MDEA all of these will have a reduced effect.


===Dangerous interactions===
===Dangerous interactions===
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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.


==Legal issues==
==Legal status==
{{stub}}
{{LegalStub}}
*'''UK:''' MDEA is a Class A drug.
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'')
*'''USA:''' MDEA is a Schedule I drug.
*'''Austria''': MDEA is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).{{citation needed}}
 
*'''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>
==Experience reports==
*'''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>
Experience reports with this compound can be found here:
*'''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>
* [https://www.erowid.org/experiences/subs/exp_MDEA.shtml Erowid Experience Vaults: MDEA]
*'''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==
*[http://en.wikipedia.org/wiki/MDEA MDEA (Wikipedia)]
*[https://en.wikipedia.org/wiki/3,4-Methylenedioxy-N-ethylamphetamine MDEA (Wikipedia)]
*[http://www.erowid.org/chemicals/MDEA/MDEA.shtml MDEA (Erowid)]
*[https://erowid.org/chemicals/mde/mde.shtml MDEA (Erowid Vault)]
*[https://www.erowid.org/experiences/subs/exp_MDEA.shtml MDEA experiences (Erowid)]
*[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106 MDEA (PiHKAL / Isomer Design)]
*[http://www.rollsafe.org/ RollSafe]
*[https://go.drugbank.com/drugs/DB01566 MDEA (DrugBank)]
 
==Literature==
* 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.org/10.1111/j.1527-3458.2004.tb00007.x. PMID 15179441.


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