Substituted ethylenedioxyphenethylamine

{{Short description|Group of psychoactive drugs}} {{Distinguish|Substituted methylenedioxyphenethylamine}} [[File:Ethylenedioxymethamphetamine.svg|thumb|right|225px|class=skin-invert-image|EDMA, a notable psychoactive EDxx compound.<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" />]]

The '''substituted ethylenedioxyphenethylamines''' ('''EDxx''') are a small group of psychoactive drugs of the phenethylamine family related to the substituted methylenedioxyphenethylamines (MDxx).<ref name="PiHKAL">{{CitePiHKAL}}</ref><ref name="ShulginManningDaley2011">{{cite book | vauthors = Shulgin A, Manning T, Daley PF | chapter=#65. EDA | title=The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds | publisher=Transform Press | location=Berkeley | volume=1 | year=2011 | isbn=978-0-9630096-3-0 | pages=136–137 | chapter-url=https://archive.org/details/shulgin-index-vol-1/page/136/mode/1up?view=theater }}</ref><ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | veditors = Laing RR | chapter = Basic Pharmacology and Effects | title = Hallucinogens: A Forensic Drug Handbook | pages = 67–137 | year = 2003 | publisher = Elsevier Science | series = Forensic Drug Handbook Series | isbn = 978-0-12-433951-4 | url = https://books.google.com/books?id=l1DrqgobbcwC | chapter-url = https://bibliography.maps.org/resources/download/12634 | archive-url = https://web.archive.org/web/20250713013624/https://bibliography.maps.org/resources/download/12634 | archive-date = 13 July 2025 }}</ref> They include the amphetamines 3,4-ethylenedioxyamphetamine (EDA), 3,4-ethylenedioxy-''N''-methylamphetamine (EDMA; "MDMC"), and 3-methoxy-4,5-ethylenedioxyamphetamine (MEDA; 5-methoxy-EDA) and the cathinone 3,4-ethylenedioxymethcathinone (EDMC), among others.<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" /><ref name="Shulgin2003" />

EDxx compounds have been found act as monoamine releasing agents, including of serotonin, norepinephrine, and/or dopamine.<ref name="McKennaGuanShulgin1991">{{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><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 = Bioorganic & Medicinal Chemistry | volume = 23 | issue = 17 | pages = 5574–5579 | date = September 2015 | pmid = 26233799 | pmc = 4562428 | doi = 10.1016/j.bmc.2015.07.035 }}</ref><ref name="Sakloth2015">{{cite thesis | vauthors = Sakloth F | degree = Ph.D. | title=Psychoactive synthetic cathinones (or 'bath salts'): Investigation of mechanisms of action | publisher = Virginia Commonwealth University | via = VCU Scholars Compass | date=11 December 2015 | url=https://scholarscompass.vcu.edu/etd/4041/ | access-date=19 January 2025}}</ref><ref name="GlennonDukat2017">{{cite book | vauthors = Glennon RA, Dukat M | title = Neuropharmacology of New Psychoactive Substances (NPS) | chapter = Structure-Activity Relationships of Synthetic Cathinones | volume = 32 | pages = 19–47 | date = 2017 | pmid = 27830576 | pmc = 5818155 | doi = 10.1007/7854_2016_41 | isbn = 978-3-319-52442-9 | series = Current Topics in Behavioral Neurosciences| quote = Expansion of the methylenedioxy ring of methylone (24) to an ethylenedioxy ring (i.e., ethylenedioxymethcathinone, EDMC; 30; Figure 7) decreased its potency as a releasing agent at all three transporters by 2- to 3-fold (Del Bello et al., 2015). }}</ref><ref name="Yadav2019">{{cite thesis | vauthors = Yadav BJ | degree = Ph.D. | title=Understanding Structure–Activity Relationship of Synthetic Cathinones (Bath Salts) Utilizing Methylphenidate | work = Theses and Dissertations | publisher = Virginia Commonwealth University | via = VCU Scholars Compass | date=16 July 2019 | doi=10.25772/MJQW-8C64 | url=https://scholarscompass.vcu.edu/etd/5955/ | access-date=24 November 2024 | quote = 8 In another study conducted by Del Bello et al.89 it was found that expansion of the methylenedioxy ring of MDMC (27) to an ethylenedioxy ring (EDMC, 31, Figure 14) slightly reduced its potency as a releasing agent at all three transporters. }}</ref> However, they showed reduced potency in these assays compared to their MDxx counterparts like MDMA, MMDA (5-methoxy-MDA), and methylone (MDMC).<ref name="McKennaGuanShulgin1991" /><ref name="DelBelloSaklothPartilla2015" /><ref name="Sakloth2015" /><ref name="GlennonDukat2017" /><ref name="Yadav2019" /> Some, such as EDMA, have been assessed and variably found to produce psychoactive effects in humans.<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" /> These effects have included paresthesia, nystagmus, sedation, hypnagogic imagery, and/or mild visual effects.<ref name="PiHKAL" /> However, at assessed doses, there were no entactogenic or stimulant effects and no or only mild hallucinogenic effects at best, which led to conclusions that they were essentially inactive.<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" /><ref name="Shulgin2003" />

EDxx compounds were tested by Alexander Shulgin and described in his 1991 book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'').<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" /><ref name="Shulgin2003" /> They were first described in the scientific literature by Shulgin by 1964.<ref name="Shulgin1964">{{cite journal | vauthors = Shulgin AT | title = 3-Methoxy-4,5-methylenedioxy Amphetamine, a New Psychotomimetic Agent | journal = Nature | volume = 201 | issue = 4924| pages = 1120–1121 | date = March 1964 | pmid = 14152788 | doi = 10.1038/2011120a0 | bibcode = 1964Natur.201.1120S | url = https://bibliography.maps.org/resources/download/8861 | archive-url = https://web.archive.org/web/20250712211627/https://bibliography.maps.org/resources/download/8861 | archive-date = 2025-07-12| url-access = subscription }}</ref><ref name="ShulginSargentNaranjo1969">{{cite journal | vauthors = Shulgin AT, Sargent T, Naranjo C | title = Structure–activity relationships of one-ring psychotomimetics | journal = Nature | volume = 221 | issue = 5180 | pages = 537–541 | date = February 1969 | pmid = 5789297 | doi = 10.1038/221537a0 | bibcode = 1969Natur.221..537S | url = https://bibliography.maps.org/resources/download/11267 | archive-url = https://web.archive.org/web/20250712213646/https://bibliography.maps.org/resources/download/11267 | archive-date = 2025-07-12}}</ref><ref name="Shulgin1978">{{cite book | veditors = Iversen LL, Iversen SD, Snyder SH | last=Shulgin | first=Alexander T. | title=Stimulants | chapter=Psychotomimetic Drugs: Structure-Activity Relationships | publisher=Springer US | publication-place=Boston, MA | date=1978 | isbn=978-1-4757-0512-6 | doi=10.1007/978-1-4757-0510-2_6 | pages=243–333 | chapter-url=https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_6 | url=https://books.google.com/books?id=h0_uBwAAQBAJ&pg=PA261}}</ref>

==Use and effects== {{Sticky}} {| class="wikitable sortable sticky-header" style="font-size: 98%;" |+ {{Nowrap|Oral doses and durations of ethylenedioxyphenethylamines (EDxx)}} |- ! Compound !! Chemical name !! Dose !! Duration |- | EDPEA || 3,4-Ethylenedioxyphenethylamine || Unknown || Unknown |- | EDA || 3,4-Ethylenedioxyamphetamine || ≥150 mg || Unknown |- | EDMA || 3,4-Ethylenedioxy-''N''-methylamphetamine || ≥150–250 mg || 3–5 hours |- | MEDA || 3-Methoxy-4,5-ethylenedioxyamphetamine || >200 mg || Unknown |- | EDMC || 3,4-Ethylenedioxy-''N''-methylcathinone || Unknown || Unknown |- class="sortbottom" | colspan="5" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Refs:''' <ref name="PiHKAL" /><ref name="ShulginManningDaley2011" /><ref name="Shulgin2003" /> |}

==References== {{Reflist}}

==External links== * [https://isomerdesign.com/pihkal/show/6783,6787,110,120,8567 Selected Ethylenedioxyphenethylamines - Isomer Design]

Category:Alexander Shulgin Category:Chemical classes of psychoactive drugs Category:Ethylenedioxyphenethylamines