View source for EDMA

{{Short description|Chemical compound}}
{{about|a substituted amphetamine}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 443531339
| IUPAC_name = 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-''N''-methylpropan-2-amine
| image = Ethylenedioxymethamphetamine.svg
<!--Clinical data-->
| tradename =
| licence_EU = <!-- EMEA requires brand name -->
| licence_US = <!-- FDA may use generic name -->
| DailyMedID = <!-- preference to licence_US -->
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = Schedule III
| legal_DE = NpSG
| legal_UK = Class B
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| routes_of_administration = [[Mouth|Oral]]
<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 133787-66-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = UJ7UU2C6E6
| ATC_prefix = none
| ATC_suffix =
| PubChem = 24257269
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 23553090
| synonyms = EDMA
<!--Chemical data-->
| C = 12 | H = 17 | N = 1 | O = 2
| SMILES = CC(Cc1ccc2c(c1)OCCO2)NC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H17NO2/c1-9(13-2)7-10-3-4-11-12(8-10)15-6-5-14-11/h3-4,8-9,13H,5-7H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UJKWLAZYSLJTKA-UHFFFAOYSA-N
}}
'''3,4-Ethylenedioxy-''N''-methylamphetamine''' ('''EDMA''') is an [[entactogen]] [[drug]] of the [[substituted amphetamine|methamphetamine class]].<ref name="isbn0-9630096-0-5">{{cite book | vauthors = Shulgin A, Shulgin A | title = Pihkal: A Chemical Love Story | publisher = Transform Press | year = 1991 | isbn = 0-9630096-0-5 | url = http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=110}}</ref><ref name="pmid1829838">{{cite journal | vauthors = McKenna DJ, Guan XM, Shulgin AT | title = 3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine | journal = Pharmacology, Biochemistry, and Behavior | volume = 38 | issue = 3 | pages = 505–512 | date = March 1991 | pmid = 1829838 | doi = 10.1016/0091-3057(91)90005-M | s2cid = 2740262 | doi-access = free }}</ref> It is an [[structural analog|analogue]] of [[3,4-methylenedioxy-N-methylamphetamine|MDMA]] where the [[methylenedioxy]] [[functional group|ring]] has been replaced by an [[ethylenedioxy]] ring.<ref name="isbn0-9630096-0-5"/><ref name="pmid1829838"/> EDMA was first synthesized by [[Alexander Shulgin]].<ref name="isbn0-9630096-0-5"/> In his book ''[[PiHKAL]]'', the dosage is listed as 150–250&nbsp;mg, and the duration listed as 3–5&nbsp;hours.<ref name="isbn0-9630096-0-5"/> According to Shulgin, EDMA produces a bare threshold consisting of [[paresthesia]], [[nystagmus]], and [[hypnogogic]] [[mental imagery|imagery]], with few to no other effects.<ref name="isbn0-9630096-0-5"/>
It has been found that EDMA acts as a non-[[neurotoxic]] [[serotonin releasing agent]] with moderately diminished [[potency (pharmacology)|potency]] relative to MDMA, and with negligible effects on [[dopamine]] release.<ref name="pmid1829838"/> However, subsequent research found that EMDA is a [[serotonin–norepinephrine–dopamine releasing agent]] (SNDRA) with {{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} values of 117{{nbsp}}nM for serotonin release, 325{{nbsp}}nM for norepinephrine release, and 597{{nbsp}}nM for dopamine release.<ref name="DelBelloSaklothPartilla2015">{{cite journal | vauthors = Del Bello F, Sakloth F, Partilla JS, Baumann MH, Glennon RA | title = Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine | journal = Bioorg Med Chem | volume = 23 | issue = 17 | pages = 5574–5579 | date = September 2015 | pmid = 26233799 | pmc = 4562428 | doi = 10.1016/j.bmc.2015.07.035 | url = }}</ref> The activities of its individual [[enantiomer]]s have also been assessed.<ref name="DelBelloSaklothPartilla2015" />
== References ==
{{Reflist}}
== External links ==
* [http://www.erowid.org/library/books_online/pihkal/pihkal110.shtml EDMA entry in ''PiHKAL'']
* [http://pihkal.info/read.php?domain=pk&id=110 MDMC (EDMA) entry in PiHKAL • info]
{{Entactogens}}
{{Monoamine releasing agents}}
{{Phenethylamines}}
[[Category:Benzodioxans]]
[[Category:Designer drugs]]
[[Category:Methamphetamines]]
[[Category:Serotonin-norepinephrine-dopamine releasing agents]]
[[Category:Substituted amphetamines]]