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'''MMDA''' ('''3-Methoxy-4,5-methylenedioxyamphetamine'''; also known as '''5-Methoxy-MDA''') is an obscure psychoactive [[Chemical class::Substituted amphetamines|substituted amphetamine]] with [[Psychoactive class::entactogen]]ic and [[Psychoactive class::psychedelic] properties. It is a closely related structural analog of [[mescaline]] and [[MDA]].<ref>PiHKAL | https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=132</ref>
'''MMDA''' ('''3-Methoxy-4,5-methylenedioxyamphetamine'''; also known as '''5-Methoxy-MDA''') is an obscure psychoactive [[Chemical class::Substituted amphetamines|substituted amphetamine]] with [[Psychoactive class::entactogen]]ic and [[Psychoactive class::psychedelic]] properties. It is a closely related structural analog of [[mescaline]] and [[MDA]].<ref>PiHKAL | https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=132</ref>
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]]" ("[[Phenethylamine]]s I Have Known and Loved").<ref>PiHKAL|http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106</ref>
MMDA is described by [[Alexander Shulgin]] to induce 'eyelid movies' – "completely realistic innervisions". In [[PiHKAL]], one user has reported: "Upon closing eyes hallucinations appear to be quite real in 3D, like watching a movie. First these dreams appear in black and white, but later colors start appearing. Chartreuse and magenta first appear, then blue and finally red. First I had visions of large numbers on gaming tables, then people."<ref>https://mixmag.net/read/the-12-most-important-drugs-shulgin-designed-synthesised-and-took-blog/</ref><ref>https://erowid.org/library/books_online/pihkal/pihkal132.shtml</ref>{{citation needed}}
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 Analog 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> The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA) | http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3458.2004.tb00007.x/pdf</ref>
Shulgin noted that he had synthesized MMDA in 1962 while simultaneously Dr. Gordon A also synthesized MMDA in 1962 and named it accordingly.<ref>https://erowid.org/library/books_online/pihkal/pihkal132.shtml</ref>
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.
It is strongly advised to use [[harm reduction]] practises when choosing to use this drug.
==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|253px||General formula 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]].
MMDA, also known as 5-methoxy-3,4-methylenedioxyamphetamine, 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, MMDA 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. In addition, it contains a methoxy group at R<sub>5</sub>. MMDA shares this methylenedioxy ring with other drugs like [[MDA]] and [[MDMA]] but differs with its additional methoxy substitution.
It is chemically related to its [[precursor]] compound, [[myristicin]]. It is believed that MMDA plays a role in the effects and pharmacology of myristicin.<ref>https://erowid.org/library/books_online/pihkal/pihkal132.shtml</ref>
==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> The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA) | http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3458.2004.tb00007.x/pdf</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.
{{pharmacology}}
MMDA likely acts as a [[releasing agent]] and [[reuptake inhibitor]] of the key [[monoamine]] [[neurotransmitters]] [[serotonin]], [[dopamine]] and [[noradrenaline]].
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>
It is also theorized to act as a 5-HT<sub>2</sub>A receptor agonist. However, how the [[psychedelic]] and [[hallucinogenic]] effects work is currently not entirely known.
[[Alexander Shulgin]] notes that MMDA is responsible for some of the effects of [[myristicin]].<ref>https://erowid.org/library/books_online/pihkal/pihkal132.shtml</ref>
==Subjective effects==
==Subjective effects==
{{effectStub}}
{{effectStub}}
{{Preamble/SubjectiveEffects}}
{{Preamble/SubjectiveEffects}}
===Physical effects===
{{effects/base
*'''[[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/physical|
*'''[[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.
*'''[[Effect::Spontaneous tactile sensations]]''' - The "body high" of MMDA 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.
*'''[[Effect::Stimulation]]'''<!-- - In terms of its effects on the user's physical energy levels, MMDA is commonly regarded as significantly less stimulating and energizing than MDMA, 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 MMDA 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::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::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 MMDA; this effect is a product of an [[increased heart rate]] and metabolism. While it is important to avoid becoming dehydrated 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 MMDA result in an overall difficulty when it comes to urination. This is an effect that is completely temporary and harmless. It is caused by MMDA’s promotion of the release of anti-diuretic hormone (ADH);{{citation needed}} 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::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 bodily temperature]]'''{{citation needed}} - As MMDA 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::Physical euphoria]]''' - This effect is not as reliably induced with substances such as [[MDMA]] or [[MDA]] and higher dosages may result in physical dysphoria.
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Stamina enhancement]]'''
*'''[[Effect::Stamina enhancement]]'''
*'''[[Effect::Tactile 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 is a typical effect of [[entactogens]] such as MDMA and MDA.
*'''[[Effect::Temporary erectile dysfunction]]'''
*'''[[Effect::Temporary erectile dysfunction]]'''
}}
===Cognitive effects===
{{effects/visual|
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:
MMDA has pronounced imagery within its closed-eye visuals with scenes and stories.
*'''[[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.
*'''[[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====
MDEA presents an array of visual enhancements which are mild in comparison to traditional psychedelics, but still distinctively present. These generally include:
MMDA presents an array of visual enhancements which at appropriately high doses produce a full spectrum of open-eye and closed-eye visuals. These generally 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 [[psychedelic]]s. These effects are far more common during the [[Duration#Offset|offset]] of the experience and commonly include:
MMDA is capable of producing a unique range of high level hallucinatory states in a fashion that is significantly more consistent and reproducible than that other [[entactogens]] but less that of many other commonly used [[psychedelic]]s. These effects are consistent at high dosages and commonly include:
*'''[[Effect::Peripheral information misinterpretation]]
*'''[[Effect::Peripheral information misinterpretation]]
*'''[[Effect::Internal hallucination]]'''
}}
|{{effects/cognitive|
The cognitive effects of MMDA can be broken down into several components which progressively intensify proportional to dosage. It contains a large number of typical [[Psychedelics|psychedelic]], [[Entactogens|entactogenic]] and [[Stimulants|stimulant]] cognitive effects.
===Auditory effects===
MMDA's headspace at lower dosages is relaxing with feelings of euphoria and happiness. Higher dosages however result in increasingly deep and vivid "dreams" reminiscent of distinct hallucinogenic and [[deliriant]] effects.
The most prominent of these cognitive effects generally include:
*'''[[Effect::Cognitive euphoria]]''' - At low to common dosages, strong emotional euphoria and feelings of happiness are present within MMDA and are likely a direct result of serotonin and dopamine release. At higher dosages, the [[deliriant]] effects typically result in cognitive dysphoria.
*'''[[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 MMDA "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]]'''
*'''[[Effect::Unity and interconnectedness]]''' <!-- Experiences of unity, oneness and interconnectedness between level 1 - 2 are common within MMDA. -->
*'''[[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. -->
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 95:
Line 109:
*'''[[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]]''' - Some users note extremely strange, vivid and sometimes rather scary dreams for several nights after taking large doses of MMDA.
*'''[[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 MMDA, particularly in high doses or in conjunction with other factors such as lack of sleep or physical fatigue.
*'''[[Effect::Irritability]]'''
*'''[[Effect::Irritability]]'''
*'''[[Effect::Motivation suppression]]'''
*'''[[Effect::Motivation suppression]]'''
*'''[[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 {{#ask: [[Category:MMDA]][[Category:Experience]]|format=ul|Columns=1}} anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:
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.
Short-term physical health risks of MMDA 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]]. It is advised to avoid very large doses of this compound.
===Long-term health concerns===
===Long-term health concerns===
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.
The neurotoxicity of MMDA is currently not known, but it can be assumed to posess a similar or greater neurotoxicity than [[MDMA]] and more compareable to [[MDA]]. 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 MMDA is most likely neurotoxic in some form.
Like other powerful serotonin releasing agents, MMDA 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 MMDA as well.<ref>Reorganization of ascending 5-HT axon projections in animals previously exposed to the recreational drug (+/-)3,4-methylenedioxymethamphetamine (MDMA, "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 MDMA 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 (MDMA 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 MDMA ("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>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 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 MMDA is likely similarly or even more 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>
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 drug.
===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 MMDA 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 MMDA 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). MMDA presents cross-tolerance with [[Cross-tolerance::all [[dopamine]]rgic and [[serotonin|serotonergic]] [[stimulant]]s and entactogens]], meaning that after the consumption of MMDA all of these will have a reduced effect.
===Dangerous interactions===
===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Stimulants|self=MDEA}}
{{DangerousInteractions/Stimulants|self=MMDA}}
{{DangerousInteractions/MAOI|nt=dopamine}}
{{DangerousInteractions/MAOI|nt=dopamine}}
*'''[[DangerousInteraction::Stimulants]]''' - The neurotoxic effects of MDEA may be increased when combined with other stimulants.
*'''[[DangerousInteraction::Stimulants]]''' - The neurotoxic effects of MMDA may be increased when combined with other stimulants.
*'''[[DangerousInteraction::Cocaine]]''' - This combination may increase strain on the heart.
*'''[[DangerousInteraction::Cocaine]]''' - This combination may increase strain on the heart.
====[[Serotonin syndrome]] risk====
====[[Serotonin syndrome]] risk====
{{DangerousInteractions/SerotoninSyndrome}}
{{DangerousInteractions/SerotoninSyndrome}}
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 MMDA is taken with many antidepressants, particularly selective serotonin reuptake inhibitors (SSRIs) and serotonin-norepinephrine reuptake inhibitors (SNRIs). Additionally, if MMDA is taken with SSRIs and SNRIs, the MMDA will be significantly less powerful or may have no distinguishable effects at all.
==Legal issues==
==Legal status==
{{LegalStub}}
{{LegalStub}}
*'''UK:''' MDEA is a Class A drug.
*'''UK:''' MMDA is a Class A drug.{{citation needed}}
*'''USA:''' MDEA is a Schedule I drug.
*'''China:'''MMDA is a Schedule I controlled substance
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.
MMDA is described by Alexander Shulgin to induce 'eyelid movies' – "completely realistic innervisions". In PiHKAL, one user has reported: "Upon closing eyes hallucinations appear to be quite real in 3D, like watching a movie. First these dreams appear in black and white, but later colors start appearing. Chartreuse and magenta first appear, then blue and finally red. First I had visions of large numbers on gaming tables, then people."[2][3][citation needed]
Shulgin noted that he had synthesized MMDA in 1962 while simultaneously Dr. Gordon A also synthesized MMDA in 1962 and named it accordingly.[4]
It is strongly advised to use harm reduction practises when choosing to use this drug.
MMDA, also known as 5-methoxy-3,4-methylenedioxyamphetamine, is a synthetic molecule of the substituted amphetamine family. Molecules of the amphetamine class contain a phenethylamine core featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain with an additional methyl substitution at Rα. Additionally, MMDA contains substitutions at R3 and R4 of the phenyl ring with oxygen groups that are incorporated into a methylenedioxy ring through a methylene bridge. In addition, it contains a methoxy group at R5. MMDA shares this methylenedioxy ring with other drugs like MDA and MDMA but differs with its additional methoxy substitution.
It is chemically related to its precursor compound, myristicin. It is believed that MMDA plays a role in the effects and pharmacology of myristicin.[5]
It is also theorized to act as a 5-HT2A receptor agonist. However, how the psychedelic and hallucinogenic effects work is currently not entirely known.
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
Spontaneous tactile sensations - The "body high" of MMDA 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.
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 nystagmus.
Dehydration - Like related entactogenic stimulants, feelings of dry mouth and dehydration are a universal experience with MMDA; this effect is a product of an increased heart rate and metabolism. While it is important to avoid becoming dehydrated there have been a number of users who have suffered from water intoxication through over-drinking, so it is advised that users simply sip at the water and never over-drink.
Difficulty urinating - Higher doses of MMDA result in an overall difficulty when it comes to urination. This is an effect that is completely temporary and harmless. It is caused by MMDA’s promotion of the release of anti-diuretic hormone (ADH);[citation needed] 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.
Increased bodily temperature[citation needed] - As MMDA 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.
MMDA has pronounced imagery within its closed-eye visuals with scenes and stories.
Enhancements
MMDA presents an array of visual enhancements which at appropriately high doses produce a full spectrum of open-eye and closed-eye visuals. These generally include:
MMDA is capable of producing a unique range of high level hallucinatory states in a fashion that is significantly more consistent and reproducible than that other entactogens but less that of many other commonly used psychedelics. These effects are consistent at high dosages and commonly include:
The cognitive effects of MMDA can be broken down into several components which progressively intensify proportional to dosage. It contains a large number of typical psychedelic, entactogenic and stimulant cognitive effects.
MMDA's headspace at lower dosages is relaxing with feelings of euphoria and happiness. Higher dosages however result in increasingly deep and vivid "dreams" reminiscent of distinct hallucinogenic and deliriant effects.
The most prominent of these cognitive effects generally include:
Cognitive euphoria - At low to common dosages, strong emotional euphoria and feelings of happiness are present within MMDA and are likely a direct result of serotonin and dopamine release. At higher dosages, the deliriant effects typically result in cognitive dysphoria.
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 MMDA "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.
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:
Dream potentiation - Some users note extremely strange, vivid and sometimes rather scary dreams for several nights after taking large doses of MMDA.
Sleep paralysis - Some users note sleep paralysis after consuming MMDA, particularly in high doses or in conjunction with other factors such as lack of sleep or physical fatigue.
There are currently anecdotal reports which describe the effects of this compound within our experience index. Additional experience reports can be found here:
Short-term physical health risks of MMDA consumption include dehydration, insomnia, hyperthermia,[7][8] and hyponatremia.[9] 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 exact toxic dosage is unknown. It is advised to avoid very large doses of this compound.
Long-term health concerns
The neurotoxicity of MMDA is currently not known, but it can be assumed to posess a similar or greater neurotoxicity than MDMA and more compareable to MDA. 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 MMDA is most likely neurotoxic in some form.
Like other powerful serotonin releasing agents, MMDA 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 MMDA as well.[10]
Like with MDMA, the long-term heavy use of MMDA is likely similarly or even more cardiotoxic, leading to valvulopathy through its actions on the 5-HT2B receptor.[11] 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.[12]
As with other stimulants, the chronic use of MMDA can be considered 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 MMDA develops 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 1 months for the tolerance to be reduced to half and 2-3 months to be back at baseline (in the absence of further consumption). MMDA presents cross-tolerance with [[Cross-tolerance::all dopaminergic and serotonergicstimulants and entactogens]], meaning that after the consumption of MMDA all of these will have a reduced effect.
Dangerous interactions
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.
]] & ]] - 25x compounds are highly stimulating and physically straining. Combinations with MMDA should be strictly avoided due to the risk of excessive stimulation and heart strain. This can result in increased blood pressure, vasoconstriction, panic attacks, thought loops, seizures, and heart failure in extreme cases.
]] - Combining alcohol with stimulants can be dangerous due to the risk of accidental over-intoxication. Stimulants mask alcohol's depressant effects, which is what most people use to assess their degree of intoxication. Once the stimulant wears off, the depressant effects will be left unopposed, which can result in blackouts and severe respiratory depression. If mixing, the user should strictly limit themselves to only drinking a certain amount of alcohol per hour.
]] - Combinations with DXM should be avoided due to its inhibiting effects on serotonin and norepinephrine reuptake. There is an increased risk of panic attacks and hypertensive crisis, or serotonin syndrome with serotonin releasers (MDMA, methylone, mephedrone, etc.). Monitor blood pressure carefully and avoid strenuous physical activity.
]] - Any neurotoxic effects of MDMA are likely to be increased when other stimulants are present. There is also a risk of excessive blood pressure and heart strain (cardiotoxicity).
]] - Some reports suggest combinations with MXE may dangerously increase blood pressure and increase the risk of mania and psychosis.
]] - Both classes carry a risk of delusions, mania and psychosis, and these risk may be multiplied when combined.
]] - Tramadol is known to lower the seizure threshold[13] and combinations with stimulants may further increase this risk.
]] - This combination may increase the amount of neurotransmitters such as dopamine to dangerous or even fatal levels. Examples include syrian rue, banisteriopsis caapi, and some antidepressants.[14]
Stimulants - The neurotoxic effects of MMDA may be increased when combined with other stimulants.
Cocaine - This combination may increase strain on the heart.
Combinations with the following substances can cause dangerously high serotonin levels. Serotonin syndrome requires immediate medical attention and can be fatal if left untreated.
There is an increased risk of serotonin syndrome when MMDA is taken with many antidepressants, particularly selective serotonin reuptake inhibitors (SSRIs) and serotonin-norepinephrine reuptake inhibitors (SNRIs). Additionally, if MMDA is taken with SSRIs and SNRIs, the MMDA will be significantly less powerful or may have no distinguishable effects at all.
↑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
↑Reorganization of ascending 5-HT axon projections in animals previously exposed to the recreational drug (+/-)3,4-methylenedioxymethamphetamine (MDMA, "ecstasy") (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/7643196
↑ Drug-induced Valvulopathy: An Update | tpx.sagepub.com/content/38/6/837.full
↑Talaie, H.; Panahandeh, R.; Fayaznouri, M. R.; Asadi, Z.; Abdollahi, M. (2009). "Dose-independent occurrence of seizure with tramadol". Journal of Medical Toxicology. 5 (2): 63–67. doi:10.1007/BF03161089. eISSN1937-6995. ISSN1556-9039. OCLC163567183.
. eISSN 1471-6771. ISSN 0007-0912. OCLC 01537271. PMID 16051647.