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MDEA: Difference between revisions
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{{SummarySheet}} | {{SummarySheet}} | ||
{{SubstanceBox/MDEA}} | {{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 | '''3,4-Methylenedioxy-N-ethylamphetamine''' (also known as '''MDEA''', '''MDE''', and colloquially as '''Eve''') is a lesser-known [[Psychoactive class::entactogen]] substance of the [[Chemical class::amphetamine]] class. MDEA is chemically similar to [[MDMA]] and [[MDA]].<ref name="Isomer Design">{{cite web|title=Read #22 2C-C {{!}} PiHKAL · info|url=http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=22|website=isomerdesign.com}}</ref> It produces its effects by increasing levels of [[serotonin]], [[norepinephrine]], and [[dopamine]] in the brain.<ref name="MDEApharm">{{cite journal | vauthors=((Freudenmann, R. W.)), ((Spitzer, M.)) | journal=CNS drug reviews | title=The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA) | volume=10 | issue=2 | pages=89–116 | date= 2004 | issn=1080-563X | doi=10.1111/j.1527-3458.2004.tb00007.x}}</ref> | ||
The first recorded human use of MDEA was in 1976 by [[Alexander Shulgin]], who noted its similarity to [[MDMA]] in both effects and potency, though faster to act and shorter in duration.<ref>Shulgin, Alexander. "Pharmacology Lab Notes #2". Lafayette, CA. (1976-1980). p206 (Erowid.org) | https://erowid.org/library/books_online/shulgin_labbooks/shulgin_labbook2_searchable.pdf</ref> The synthesis and pharmacological evaluation of MDEA and a series of related compounds were published in 1980.<ref>Braun U, Shulgin | The first recorded human use of MDEA was in 1976 by [[Alexander Shulgin]], who noted its similarity to [[MDMA]] in both effects and potency, though faster to act and shorter in duration.<ref>Shulgin, Alexander. "Pharmacology Lab Notes #2". Lafayette, CA. (1976-1980). p206 (Erowid.org) | https://erowid.org/library/books_online/shulgin_labbooks/shulgin_labbook2_searchable.pdf</ref> The synthesis and pharmacological evaluation of MDEA and a series of related compounds were published in 1980.<ref>{{cite journal | vauthors=((Braun, U.)), ((Shulgin, A. T.)), ((Braun, G.)) | journal=Journal of Pharmaceutical Sciences | title=Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine) | volume=69 | issue=2 | pages=192–195 | date= February 1980 | issn=0022-3549 | doi=10.1002/jps.2600690220}}</ref> MDEA is included in Shulgin's 1991 book "[[PiHKAL]]" ("[[Phenethylamine]]s I Have Known and Loved").<ref name="Isomer Design" /> | ||
In the United States, MDEA was introduced recreationally in 1985 as a legal substitute to the newly banned MDMA before it was made a Schedule I substance two years later.<ref> | 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" /> | ||
Very little data exists about the pharmacological properties, metabolism, and toxicity of MDEA,. As a result it is highly advised to approach this potentially habit-forming [[entactogenic]] substance with the proper amount of precaution and [[Responsible drug use#Hallucinogens|harm reduction practices]] if choosing to use it. | Very little data exists about the pharmacological properties, metabolism, and toxicity of MDEA,. 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. | ||
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==History and culture== | ==History and culture== | ||
{{historyStub}} | {{historyStub}} | ||
In the United States, MDEA was introduced recreationally in 1985 as a legal substitute to the newly banned MDMA before it was made a Schedule I substance two years later on August 13, 1987 under the Federal Analogue Act.<ref | In the United States, MDEA was introduced recreationally in 1985 as a legal substitute to the newly banned MDMA before it was made a Schedule I substance two years later on August 13, 1987 under the Federal Analogue Act.<ref name="MDEPiHKAL"/> Since then, MDEA has rarely been sold on its own and has largely been used as an occasional additive or substitute ingredient in pills of "Ecstasy" (for instance, studies conducted in the 1990s found MDEA present in approximately four percent of ecstasy tablets).<ref name="MDEApharm" /> | ||
While MDEA shares many of the core entactogenic properties of MDMA, it is slightly less potent and considered to be more "stoning", lacking the pro-socializing and energizing "magic" most party-goers seek in their MDMA experiences. As a result, it is largely considered by most people to be a less desirable variant of MDMA and is thus rarely produced and sold in the illicit drug market, typically showing up only in small batches synthesized and distributed by hobbyist clandestine chemists.{{citation needed}} | While MDEA shares many of the core entactogenic properties of MDMA, it is slightly less potent and considered to be more "stoning", lacking the pro-socializing and energizing "magic" most party-goers seek in their MDMA experiences. As a result, it is largely considered by most people to be a less desirable variant of MDMA and is thus rarely produced and sold in the illicit drug market, typically showing up only in small batches synthesized and distributed by hobbyist clandestine chemists.{{citation needed}} | ||
==Chemistry== | ==Chemistry== | ||
[[File:Phenethylamine.png|thumb|right|253px|thumb|right | [[File:Phenethylamine.png|thumb|right|253px|thumb|right||Generic structure of a phenethylamine molecule]] | ||
MDEA, also known as 3,4-Methylenedioxy-N-ethylamphetamine, is a synthetic molecule of the [[Substituted amphetamine|substituted amphetamine]] chemical class. Molecules of the amphetamine class contain a [[phenethylamine]] core featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain with an additional methyl substitution at R<sub>α</sub>. Additionally, MDEA contains an ethyl substitution on R<sub>N</sub>, which is a single carbon extension of the methyl group present in MDMA. MDEA also contains substitutions at R<sub>3</sub> and R<sub>4</sub> of the phenyl ring with oxygen groups that are incorporated into a methylenedioxy ring through a methylene bridge. MDEA shares this methylenedioxy ring with other [[entactogens]] like [[MDMA]], [[MDA]] and [[MDAI]]. | MDEA, also known as 3,4-Methylenedioxy-N-ethylamphetamine, is a synthetic molecule of the [[Substituted amphetamine|substituted amphetamine]] chemical class. Molecules of the amphetamine class contain a [[phenethylamine]] core featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain with an additional methyl substitution at R<sub>α</sub>. Additionally, MDEA contains an ethyl substitution on R<sub>N</sub>, which is a single carbon extension of the methyl group present in MDMA. MDEA also contains substitutions at R<sub>3</sub> and R<sub>4</sub> of the phenyl ring with oxygen groups that are incorporated into a methylenedioxy ring through a methylene bridge. MDEA shares this methylenedioxy ring with other [[entactogens]] like [[MDMA]], [[MDA]] and [[MDAI]]. | ||
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The "stoning" effects of MDEA are thought to arise from the higher relative activity MDEA has on releasing serotonin over dopamine compared to MDMA. | 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> Passie, | 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== | ||
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==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
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 | | |||
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. | ||
=== | ===Neurotoxicity=== | ||
As with MDMA, the neurotoxicity of MDEA use has long been the subject of debate. Scientific study has resulted in the general agreement that, although it is physically safe to try in a responsible context, the administration of repeated or high dosages of MDEA is likely to be neurotoxic and cardiotoxic in some form. | As with MDMA, the neurotoxicity of MDEA use has long been the subject of debate. Scientific study has resulted in the general agreement that, although it is physically safe to try in a responsible context, the administration of repeated or high dosages of MDEA is likely to be neurotoxic and cardiotoxic in some form. | ||
Like other powerful serotonin releasing agents, MDEA is thought to cause down-regulation of [[serotonin]] reuptake transporters in the brain. The rate at which the brain recovers from serotonergic changes is unclear. One study demonstrated lasting serotonergic changes in some animals exposed to MDMA, which likely applies to MDEA as well.<ref>Reorganization of ascending 5-HT axon projections in animals previously exposed to the recreational drug (+/-)3,4-methylenedioxymethamphetamine ( | Like other powerful serotonin releasing agents, MDEA is thought to cause down-regulation of [[serotonin]] reuptake transporters in the brain. The rate at which the brain recovers from serotonergic changes is unclear. One study demonstrated lasting serotonergic changes in some animals exposed to MDMA, which likely applies to MDEA as well.<ref>{{cite journal | vauthors=((Fischer, C.)), ((Hatzidimitriou, G.)), ((Wlos, J.)), ((Katz, J.)), ((Ricaurte, G.)) | journal=The Journal of Neuroscience: The Official Journal of the Society for Neuroscience | title=Reorganization of ascending 5-HT axon projections in animals previously exposed to the recreational drug (+/-)3,4-methylenedioxymethamphetamine (MDMA, “ecstasy”) | volume=15 | issue=8 | pages=5476–5485 | date= August 1995 | issn=0270-6474}}</ref> Other studies have suggested that the brain may recover from serotonergic damage.<ref>{{cite journal | vauthors=((Scheffel, U.)), ((Szabo, Z.)), ((Mathews, W. B.)), ((Finley, P. A.)), ((Dannals, R. F.)), ((Ravert, H. T.)), ((Szabo, K.)), ((Yuan, J.)), ((Ricaurte, G. A.)) | journal=Synapse (New York, N.Y.) | title=In vivo detection of short- and long-term MDMA neurotoxicity--a positron emission tomography study in the living baboon brain | volume=29 | issue=2 | pages=183–192 | date= June 1998 | issn=0887-4476 | doi=10.1002/(SICI)1098-2396(199806)29:2<183::AID-SYN9>3.0.CO;2-3}}</ref><ref>{{cite journal | vauthors=((Reneman, L.)), ((Lavalaye, J.)), ((Schmand, B.)), ((Wolff, F. A. de)), ((Brink, W. van den)), ((Heeten, G. J. den)), ((Booij, J.)) | journal=Archives of General Psychiatry | title=Cortical Serotonin Transporter Density and Verbal Memory in Individuals Who Stopped Using 3,4-Methylenedioxymethamphetamine (MDMA or “Ecstasy”): Preliminary Findings | volume=58 | issue=10 | pages=901 | date=1 October 2001 | url=http://archpsyc.jamanetwork.com/article.aspx?doi=10.1001/archpsyc.58.10.901 | issn=0003-990X | doi=10.1001/archpsyc.58.10.901}}</ref><ref>{{cite journal | vauthors=((Selvaraj, S.)), ((Hoshi, R.)), ((Bhagwagar, Z.)), ((Murthy, N. V.)), ((Hinz, R.)), ((Cowen, P.)), ((Curran, H. V.)), ((Grasby, P.)) | journal=The British Journal of Psychiatry: The Journal of Mental Science | title=Brain serotonin transporter binding in former users of MDMA ('ecstasy’) | volume=194 | issue=4 | pages=355–359 | date= April 2009 | issn=1472-1465 | doi=10.1192/bjp.bp.108.050344}}</ref> | ||
Like with MDMA, the long-term heavy use of MDEA is likely similarly cardiotoxic, leading to valvulopathy through its actions on the 5-HT<sub>2B</sub> receptor.<ref> Drug-induced Valvulopathy: An Update | | ===Cardiotoxicity=== | ||
Like with MDMA, the long-term heavy use of MDEA is likely similarly cardiotoxic, leading to valvulopathy through its actions on the 5-HT<sub>2B</sub> receptor.<ref>{{cite journal | vauthors=((Elangbam, C. S.)) | journal=Toxicologic Pathology | title=Drug-induced Valvulopathy: An Update | volume=38 | issue=6 | pages=837–848 | date= October 2010 | url=http://journals.sagepub.com/doi/10.1177/0192623310378027 | issn=0192-6233 | doi=10.1177/0192623310378027}}</ref> In one study, 28% of long-term MDMA users (2-3 doses per week for a mean of 6 years, mean of age 24.3 years) had developed clinically evident valvular heart disease.<ref>{{cite journal | vauthors=((Droogmans, S.)), ((Cosyns, B.)), ((D’haenen, H.)), ((Creeten, E.)), ((Weytjens, C.)), ((Franken, P. R.)), ((Scott, B.)), ((Schoors, D.)), ((Kemdem, A.)), ((Close, L.)), ((Vandenbossche, J.-L.)), ((Bechet, S.)), ((Van Camp, G.)) | journal=The American Journal of Cardiology | title=Possible association between 3,4-methylenedioxymethamphetamine abuse and valvular heart disease | volume=100 | issue=9 | pages=1442–1445 | date=1 November 2007 | issn=0002-9149 | doi=10.1016/j.amjcard.2007.06.045}}</ref> | |||
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance. | It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance. | ||
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==Legal status== | ==Legal status== | ||
{{LegalStub}} | {{LegalStub}} | ||
*'''Brazil | Internationally, MDEA is part of the the Convention on Psychotropic Substances of 1971 as a Schedule I substance.<ref>{{cite web|url=http://www.emcdda.europa.eu/system/files/attachments/10451/convention_1971_en.pdf|title=CONVENTION ON PSYCHOTROPIC SUBSTANCES 1971|publisher=United Nations|access-date=December 16, 2019}}</ref> (''MDE'') | ||
*'''United Kingdom | *'''Austria''': MDEA is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).{{citation needed}} | ||
*'''United States | *'''Brazil''': MDEA is illegal to possess, produce or sell as it is listed on Portaria SVS/MS nº 344 as "MDE".<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref> | ||
*'''Canada''': MDEA is listed on the CSDA in Schedule I.<ref>{{cite web|url=https://www.laws-lois.justice.gc.ca/eng/acts/C-38.8/page-13.html#docCont|title=Controlled Drugs and Substances Act - SCHEDULE I|publisher=Government of Canada|access-date=December 16, 2019}}</ref> | |||
*'''France''': MDEA is scheduled as a "stupéfiant", i.e. a recognized drug of abuse. It is illegal to possess, buy, sell or manufacture.<ref>{{Citation | title=Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants | url=https://www.legifrance.gouv.fr/loda/id/JORFTEXT000000533085/2020-11-20/}}</ref> | |||
*'''Germany''': MDEA is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of April 15, 1991.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?start=%2F%2F*%5B%40attr_id%3D%27bgbl191s0712.pdf%27%5D|title=Dritte Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|access-date=December 15, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Anlage I BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 15, 2019|language=de}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or to dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=§ 29 BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 15, 2019|language=de}}</ref> (''MDE'') | |||
*'''Switzerland''': MDEA is a controlled substance specifically named under Verzeichnis D.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | |||
*'''United Kingdom''': MDEA is a Class A drug.{{citation needed}} | |||
*'''United States''': MDEA is a Schedule I drug.{{citation needed}} | |||
==See also== | ==See also== | ||
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*[https://erowid.org/chemicals/mde/mde.shtml MDEA (Erowid Vault)] | *[https://erowid.org/chemicals/mde/mde.shtml MDEA (Erowid Vault)] | ||
*[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106 MDEA (PiHKAL / Isomer Design)] | *[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106 MDEA (PiHKAL / Isomer Design)] | ||
*[https://go.drugbank.com/drugs/DB01566 MDEA (DrugBank)] | |||
==Literature== | ==Literature== | ||
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==References== | ==References== | ||
<references/> | <references /> | ||
[[Category:Psychoactive substance]] | [[Category:Psychoactive substance]] | ||
[[Category:Amphetamine]] | [[Category:Amphetamine]] | ||
[[Category:Entactogen]] | [[Category:Entactogen]] | ||
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