This is an unofficial archive of PsychonautWiki as of 2025-08-11T15:14:44Z. Content on this page may be outdated, incomplete, or inaccurate. Please refer to the original page for the most up-to-date information.
MDEA: Difference between revisions
>Kaylee m Text replacement - " drugs " to " substances " |
>Kenan |
||
| Line 12: | Line 12: | ||
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> | 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> | ||
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 | 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. | ||
==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 | 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]]. | ||
==Pharmacology== | ==Pharmacology== | ||
| Line 110: | Line 110: | ||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
===Short-term health concerns=== | ===Short-term health concerns=== | ||
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 | 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. | ||
| Line 117: | Line 117: | ||
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 most certainly neurotoxic 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 | 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 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> | ||
It is strongly recommended that one use [[responsible | 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=== | ||