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

| tradename =

| licence_EU =

| licence_US =

| DailyMedID =

| pregnancy_AU =

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| legal_AU =

| legal_CA = Schedule III

| legal_DE = NpSG

| legal_UK = Class B

| legal_US =

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| routes_of_administration = Oral

| bioavailability =

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| 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

| 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

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3,4-Ethylenedioxy-N-methylamphetamine (EDMA) is an entactogen drug of the methamphetamine class.{{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}}{{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| s2cid = 2740262 | doi-access = free }} It is an analogue of MDMA where the methylenedioxy ring has been replaced by an ethylenedioxy ring. EDMA was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage is listed as 150–250 mg, and the duration listed as 3–5 hours. According to Shulgin, EDMA produces only mild psychedelic effects consisting of paresthesia, nystagmus, and hypnogogic imagery, with few to no other symptoms.

It has been found that EDMA acts as a non-neurotoxic serotonin releasing agent with moderately diminished potency relative to MDMA, and with negligible effects on dopamine release. However, subsequent research found that EMDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) with {{Abbrlink|EC₅₀|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 in rat brain synaptosomes.{{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 = }} Compared to MDMA, EDMA was about half as potent as a serotonin releaser, 4.5-fold less potent as a norepinephrine releaser, and 8-fold less potent as a dopamine releaser. The activities of the individual enantiomers of EDMA have also been assessed.