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{{Short description|Chemical compound}} |
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{{about|a substituted amphetamine}} |
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{{Drugbox |
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{{Drugbox |
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| Watchedfields = changed |
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| verifiedrevid = 416555308 |
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| verifiedrevid = 443531339 |
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| IUPAC_name = 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-''N''-methylpropan-2-amine |
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| IUPAC_name = 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-''N''-methylpropan-2-amine |
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| image = Ethylenedioxymethamphetamine.svg |
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| image = EDMA.png |
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| InChI = 1/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 |
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<!--Clinical data--> |
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| InChIKey = UJKWLAZYSLJTKA-UHFFFAOYAV |
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| tradename = |
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| licence_EU = <!-- EMEA requires brand name --> |
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| licence_US = <!-- FDA may use generic name --> |
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| DailyMedID = <!-- preference to licence_US --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = Schedule III |
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| legal_DE = NpSG |
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| legal_UK = Class B |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = ] |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = 133787-66-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = UJ7UU2C6E6 |
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| ATC_prefix = none |
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| ATC_suffix = |
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| PubChem = 24257269 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 23553090 |
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| synonyms = EDMA |
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<!--Chemical data--> |
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| C = 12 | H = 17 | N = 1 | O = 2 |
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| SMILES = CC(Cc1ccc2c(c1)OCCO2)NC |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = UJKWLAZYSLJTKA-UHFFFAOYSA-N |
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| StdInChIKey = UJKWLAZYSLJTKA-UHFFFAOYSA-N |
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| CAS_number = |
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| ATC_prefix = none |
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| ATC_suffix = |
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| PubChem = 24257269 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 23553090 |
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| chemical_formula = C<sub>12</sub>H<sub>17</sub>NO<sub>2</sub> |
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| C= | H= | As= | Au= | Br= | Cl= | Co= | F= | Gd= | I= | Mn= |
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| N= | Na= | O= | P= | Pt= | S= | Se= | Sr= | Tc= | Zn= | charge= |
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| molecular_weight = 207.269 |
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| smiles = CC(Cc1ccc2c(c1)OCCO2)NC |
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| synonyms = |
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| density = |
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| solubility = |
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| specific_rotation = |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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| licence_EU = <!-- EMEA requires brand name --> |
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| licence_US = <!-- FDA may use generic name --> |
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| DailyMedID = <!-- preference to licence_US --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = Uncontrolled <small>(but may be covered under the ] in the ] and under similar bills in other countries)</small> |
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| routes_of_administration = ] |
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}} |
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'''3,4-Ethylenedioxy-''N''-methylamphetamine''' ('''EDMA''') is an ] ] of the ].<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 ] of ] where the ] ] has been replaced by an ] ring.<ref name="isbn0-9630096-0-5"/><ref name="pmid1829838"/> EDMA was first synthesized by ].<ref name="isbn0-9630096-0-5"/> In his book '']'', the dosage is listed as 150–250 mg, and the duration listed as 3–5 hours.<ref name="isbn0-9630096-0-5"/> According to Shulgin, EDMA produces a bare threshold consisting of ], ], and ] ], with few to no other effects.<ref name="isbn0-9630096-0-5"/> |
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{{about|the amphetamine}} |
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{{redirect|MDMC|the airport with that ICAO code|Osvaldo Virgil Airport}} |
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'''3,4-Ethylenedioxy-''N''-methylamphetamine''' ('''EDMA'''; '''MDMC''') is an ] ] of the ] class.<ref name="isbn0-9630096-0-5">{{cite book | author = Ann Shulgin; Alexander Shulgin | title = Pihkal: A Chemical Love Story | publisher = Transform Press | location = | year = 1991 | pages = | isbn = 0-9630096-0-5 | oclc = | doi = | url = http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=110}}</ref><ref name="pmid1829838">{{cite journal | author = 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 = 505–12 | year = 1991 | month = March | pmid = 1829838 | doi = 10.1016/0091-3057(91)90005-M| url = http://linkinghub.elsevier.com/retrieve/pii/0091-3057(91)90005-M}}</ref> It is an ] of ] where the ] ] has been replaced by an ] ring.<ref name="isbn0-9630096-0-5"/><ref name="pmid1829838"/> EDMA was first synthesized by ].<ref name="isbn0-9630096-0-5"/> In his book '']'', the dosage is listed as 150–250 mg, and the duration listed as 3–5 hours.<ref name="isbn0-9630096-0-5"/> According to Shulgin, EDMA produces a bare threshold consisting of ], ], and ] ], with few to no other effects.<ref name="isbn0-9630096-0-5"/> Scientific research has demonstrated that EDMA acts as a non-] ] with moderately diminished ] relative to MDMA, and with negligible effects on ] release.<ref name="pmid1829838"/> Based on Shulgin's reports of essential ] at 150–250 mg, it may be more ] at higher doses. |
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It has been found that EDMA acts as a non-] ] with moderately diminished ] relative to MDMA, and with negligible effects on ] release.<ref name="pmid1829838"/> However, subsequent research found that EMDA is a ] (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 ]s have also been assessed.<ref name="DelBelloSaklothPartilla2015" /> |
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== See also == |
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* ] |
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* ] |
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* ] |
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== References == |
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== References == |
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{{Entactogens}} |
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{{Entactogens}} |
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{{Monoamine releasing agents}} |
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{{Serotonergics}} |
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{{Phenethylamines}} |
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{{Phenethylamines}} |
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{{PiHKAL}} |
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] |
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