{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | verifiedrevid = 434814715 | drug_name = MDPEA | image = MDPEA structure.svg | image_class = skin-invert-image | width = 225px | image2 = Methylenedioxyphenethylamine.png | image_class2 = bg-transparent | width2 = 225px
<!-- Clinical data --> | tradename = | pregnancy_category = | routes_of_administration = | class =
<!-- Legal status --> | legal_status = IV-P (Poland)<ref name="SEJM2011">{{cite web | title = Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 ) | url = http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614 | publisher = Internetowy System Aktów Prawnych | access-date = 17 June 2011}}</ref>
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | onset = | elimination_half-life = | duration_of_action = | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 1484-85-1 | UNII = F2J2U8J2G5 | PubChem = 73874 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChemSpiderID = 66508 | synonyms = 3,4-Methylenedioxyphenethylamine; Methyleneddioxyphenethylamine; 3,4-MDPEA; Homopiperonylamine; EA-1297
<!-- Chemical data --> | IUPAC_name = 2-(1,3-benzodioxol-5-yl)ethanamine | C=9 | H=11 | N=1 | O=2 | SMILES = C1OC2=C(O1)C=C(C=C2)CCN | StdInChI = 1S/C9H11NO2/c10-4-3-7-1-2-8-9(5-7)12-6-11-8/h1-2,5H,3-4,6,10H2 | StdInChIKey = RRIRDPSOCUCGBV-UHFFFAOYSA-N }}
'''MDPEA''', also known as '''3,4-methylenedioxyphenethylamine''' or as '''homopiperonylamine''', is a possible psychoactive drug of the phenethylamine and methylenedioxyphenethylamine families.<ref name="PiHKAL">{{CitePiHKAL}} https://www.erowid.org/library/books_online/pihkal/pihkal115.shtml</ref> It is the 3,4-methylenedioxy derivative of phenethylamine (PEA).<ref name="PiHKAL" /> The drug is structurally related to 3,4-methylenedioxyamphetamine (MDA), but lacks the methyl group at the α carbon.<ref name="PiHKAL" /> It is a key parent compound of a large group of compounds known as entactogens such as MDMA ("ecstasy").<ref name="PiHKAL" />
==Use and effects== According to Alexander Shulgin in his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved''), MDPEA was inactive at doses of up to 300{{nbsp}}mg orally.<ref name="PiHKAL" /> This is likely because of extensive first-pass metabolism by the enzyme monoamine oxidase (MAO).<ref name="PiHKAL" /> However, if MDPEA were either used in high enough of doses (e.g., 1–2{{nbsp}}grams), or in combination with a monoamine oxidase inhibitor (MAOI), it is probable that it would become active, though it would likely have a relatively short duration.{{Citation needed|date=October 2025}} This idea is similar in concept to the use of monoamine oxidase A (MAO-A) inhibitors to augment dimethyltryptamine (DMT) as in ayahuasca<ref name="EggerAicherCumming2024">{{cite journal | vauthors = Egger K, Aicher HD, Cumming P, Scheidegger M | title = Neurobiological research on N,N-dimethyltryptamine (DMT) and its potentiation by monoamine oxidase (MAO) inhibition: from ayahuasca to synthetic combinations of DMT and MAO inhibitors | journal = Cell Mol Life Sci | volume = 81 | issue = 1 | pages = 395 | date = September 2024 | pmid = 39254764 | pmc = 11387584 | doi = 10.1007/s00018-024-05353-6 | url = }}</ref> and of monoamine oxidase B (MAO-B) inhibitors to potentiate phenethylamine (PEA).<ref name="McKeanLeungDare2015">{{cite journal | vauthors = McKean AJ, Leung JG, Dare FY, Sola CL, Schak KM | title = The Perils of Illegitimate Online Pharmacies: Substance-Induced Panic Attacks and Mood Instability Associated With Selegiline and Phenylethylamine | journal = Psychosomatics | volume = 56 | issue = 5 | pages = 583–587 | date = 2015 | pmid = 26198572 | doi = 10.1016/j.psym.2015.05.003 | url = }}</ref><ref name="MonteithGlennBauer2016">{{cite journal | vauthors = Monteith S, Glenn T, Bauer R, Conell J, Bauer M | title = Availability of prescription drugs for bipolar disorder at online pharmacies | journal = J Affect Disord | volume = 193 | issue = | pages = 59–65 | date = March 2016 | pmid = 26766033 | doi = 10.1016/j.jad.2015.12.043 | url = }}</ref>
Besides being evaluated by Shulgin, MDPEA was studied at Edgewood Arsenal in the 1950s and was administered to humans at doses of up to 5.0{{nbsp}}mg/kg (350{{nbsp}}mg for a 70-kg person) by intravenous injection, although the results of these tests do not seem to have been released.<ref name="PassieBenzenhöfer2018" />
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Pharmacology== ===Pharmacodynamics=== MDPEA produces sympathomimetic effects when administered intravenously at sufficiently high doses in dogs.<ref name="Alles1959a">{{cite book | vauthors = Alles GA | chapter = Some Relations Between Chemical Structure and Physiological Action of Mescaline and Related Compounds / Structure and Action of Phenethylamines | veditors = Abramson HA | title = Neuropharmacology: Transactions of the Fourth Conference, September 25, 26, and 27, 1957, Princeton, N. J. | location = New York | publisher = Josiah Macy Foundation | date = 1959 | pages = 181–268 | oclc = 9802642 | url = https://books.google.com/books?id=sDQLAQAAMAAJ&q=%22Some+relations+between+chemical+structure+and+physiological+action+of+mescaline+and+related+compounds%22 | chapter-url = https://web.archive.org/web/20250321230359/https://bitnest.netfirms.com/external/Books/NeuropharmacologyTrans.4.181#page=5 | quote = We studied the two compounds in Figure 38 and found that after intravenous injection into dogs, these compounds were about one-half or one-third as active in their peripheral activities as the unsubstituted compounds. [...] FIGURE 38. [...] 3,4-Methylenedioxyphenethylamine. Homopiperonylamine. [...] 3,4-Methylenedioxyphenisopropylamine. Methylenedioxy-amphetamine (MDA).}}</ref><ref name="Alles1959b">{{cite book | vauthors = Alles GA | chapter = Subjective Reactions to Phenethylamine Hallucinogens | title = A Pharmacologic Approach to the Study of the Mind | date = 1959 | publisher = CC Thomas | location = Springfield | pages = 238–250 (241–246) | isbn = 978-0-398-04254-7 | url = https://books.google.com/books?id=x45rAAAAMAAJ | chapter-url = https://archive.org/details/pharmacologicapp0000univ/page/238/mode/1up}}</ref> It was about half as potent in this regard as PEA.<ref name="Alles1959a" /><ref name="Alles1959b" /> The effects and toxicity of MDPEA in various animal species via intravenous injection have been studied and described.<ref name="PassieBenzenhöfer2018" />
==Chemistry== ===Properties=== The predicted log P of MDPEA is 1.2.<ref name="PubChem">{{cite web | title=1,3-Benzodioxole-5-ethanamine | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/73874 | access-date=22 October 2025}}</ref>
===Synthesis=== The chemical synthesis of MDPEA has been described.<ref name="PiHKAL" />
===Analogues=== Analogues of MDPEA include 3,4-methylenedioxy-''N''-methylphenethylamine (MDMPEA), lophophine (5-methoxy-MDPEA), mescaline (3,4,5-trimethoxyphenethylamine), 3,4-methylenedioxyamphetamine (MDA), and 3,4-methylenedioxy-''N''-methylamphetamine (MDMA), among others.<ref name="PiHKAL" />
==History== MDPEA was first described in the scientific literature by Gordon Alles by 1959.<ref name="Alles1959a" /><ref name="Alles1959b" /> It was studied at Edgewood Arsenal under the code name ''EA-1297'' in the 1950s, being administered by humans in 1952.<ref name="PiHKAL" /><ref name="PassieBenzenhöfer2018">{{cite journal | vauthors = Passie T, Benzenhöfer U | title = MDA, MDMA, and other "mescaline-like" substances in the US military's search for a truth drug (1940s to 1960s) | journal = Drug Test Anal | volume = 10 | issue = 1 | pages = 72–80 | date = January 2018 | pmid = 28851034 | doi = 10.1002/dta.2292 | url = }}</ref> The drug was described by Alexander Shulgin in his 1991 book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'').<ref name="PiHKAL" />
==Society and culture== ===Legal status=== ====Poland==== MDPEA is a controlled substance in Poland.<ref name="SEJM2011" />
== See also == * Substituted methylenedioxyphenethylamine
== References == {{Reflist}}
== External links == * [https://isomerdesign.com/pihkal/explore/115 MDPEA - Isomer Design] * [https://www.erowid.org/library/books_online/pihkal/pihkal115.shtml MDPEA - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/115 MDPEA - PiHKAL - Isomer Design]
{{Monoamine releasing agents}} {{Phenethylamines}}
{{DEFAULTSORT:Methylenedioxyphenethylamine, 3,4-}}
Category:Methylenedioxyphenethylamines Category:PiHKAL Category:Sympathomimetics