MDEA: Difference between revisions

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Summary - shulgin's initial tests, first published synthesis (the 1967 compound tested was methylenedioxyethanolamine not MDEA)
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'''3,4-Methylenedioxy-N-ethylamphetamine''' (also known as, '''Methylenedioxyethylamphetamine''', '''MDEA''', '''MDE''', and colloquially as '''Eve''') is an obscure, synthetic [[Psychoactive class::entactogen]] of the [[Chemical class::amphetamines|substituted amphetamine]] class that produces modified [[MDMA|MDMA-like]] entactogenic effects when [[routes of administration|administered]]. It is a closely related structural analog of [[MDMA]] and [[MDA]]<ref>PiHKAL|http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106</ref> that acts via the same pharmacological mechanism as a [[serotonin]], [[norepinephrine]], and [[dopamine]] [[releasing agent]] and [[reuptake inhibitor]].<ref name="MDEApharm">Freudenmann RW, Spitzer M (2004). "The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA)". CNS Drug Reviews. 10 (2): 89–116. https://doi.org10.1111/j.1527-3458.2004.tb00007.x. PMID 15179441.</ref>
'''3,4-Methylenedioxy-N-ethylamphetamine''' (also known as, '''Methylenedioxyethylamphetamine''', '''MDEA''', '''MDE''', and colloquially as '''Eve''') is an obscure, synthetic [[Psychoactive class::entactogen]] of the [[Chemical class::amphetamines|substituted amphetamine]] class that produces modified [[MDMA|MDMA-like]] entactogenic effects when [[routes of administration|administered]]. It is a closely related structural analog of [[MDMA]] and [[MDA]]<ref>PiHKAL|http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106</ref> that acts via the same pharmacological mechanism as a [[serotonin]], [[norepinephrine]], and [[dopamine]] [[releasing agent]] and [[reuptake inhibitor]].<ref name="MDEApharm">Freudenmann RW, Spitzer M (2004). "The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA)". CNS Drug Reviews. 10 (2): 89–116. https://doi.org10.1111/j.1527-3458.2004.tb00007.x. PMID 15179441.</ref>


In a 1967 lab notebook entry, [[Alexander Shulgin]] briefly mentions 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>
The first recorded human use of MDEA was in 1976 by [[Alexander Shulgin]], who noted its similarity to [[MDMA]] in both effects and potency, though faster to act and shorter in duration.<ref>Shulgin, Alexander. "Pharmacology Lab Notes #2". Lafayette, CA. (1976-1980). p206 (Erowid.org) | https://erowid.org/library/books_online/shulgin_labbooks/shulgin_labbook2_searchable.pdf</ref>. The synthesis and pharmacological evaluation of MDEA and a series of related compounds were published in 1980.<ref>Braun U, Shulgin AT, Braun G. "Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine)." J Pharm Sci. 1980 Feb;69(2):192-5. | https://www.ncbi.nlm.nih.gov/pubmed/6102141</ref>. MDEA is included in Shulgin's 1991 book "[[PiHKAL]]" ("[[Phenethylamine]]s I Have Known and Loved").<ref>PiHKAL|http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106</ref>.


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