:3,4-Methylenedioxy-N-ethylamphetamine

{{Infobox drug

| drug_name = MDEA

| image = MDEA.svg

| image_class = skin-invert-image

| image2 = MDEA-3D-vdW.png

| image_class2 = bg-transparent

| IUPAC_name = 1-(1,3-Benzodioxol-5-yl)-N-ethylpropan-2-amine

| ATC_prefix = none

| CAS_number = 82801-81-8

| PubChem = 105039

| ChEBI = 132237

| ChemSpiderID = 94775

| UNII = ML1I4KK67B

| KEGG = C22717

| synonyms = MDEA; MDE; 3,4-Methylenedioxy-N-ethylamphetamine; N-Ethyl-MDA; Eve; EA-1304; EA1304; PAL-192; PAL192; ASR-1003; ASR1003

| tradename =

| legal_AU = S9

| legal_BR = F2

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}

| legal_CA = Schedule I

| legal_DE = Anlage I

| legal_UK =Class A

| legal_US = Schedule I

| legal_UN = Psychotropic Schedule I

| excretion = Renal

| routes_of_administration = Oral, insufflation, injection, rectal

| onset = 20–85 minutes

| metabolism = Hepatic including CYP2D6 and CYP3A4

| elimination_half-life = (R)-MDEA: 7.5 ± 2.4 hours
(S)-MDEA: 4.2 ± 1.4 hours

| C=12 | H=17 | N=1 | O=2

| smiles = CCNC(C)Cc1ccc2OCOc2c1

}}

3,4-Methylenedioxy-N-ethylamphetamine (MDEA; also called MDE and colloquially, Eve) is an empathogenic psychoactive drug. MDEA is a substituted amphetamine and a substituted methylenedioxyphenethylamine. MDEA acts as a serotonin, norepinephrine, and dopamine releasing agent and reuptake inhibitor.{{cite journal | vauthors = Freudenmann RW, Spitzer M | title = The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA) | journal = CNS Drug Reviews | volume = 10 | issue = 2 | pages = 89–116 | date = 2004 | pmid = 15179441 | pmc = 6741736 | doi = 10.1111/j.1527-3458.2004.tb00007.x }}

Possession of MDEA is illegal in most countries. Some limited exceptions exist for scientific and medical research.

Uses

=Medical=

MDEA currently has no accepted medical uses.

=Recreational=

MDEA is used recreationally in a similar manner to MDMA (also called ecstasy), however the subjective effects of MDEA are milder and shorter lasting. Alexander Shulgin reported it to be stoning in high doses. Most frequently consumed orally, recreational doses of MDEA are in the range 100 to 200 mg. Infrequently, MDEA is an adulterant of ecstasy pills. Studies conducted in the 1990s found MDEA present in approximately four percent of ecstasy tablets.

Adverse effects

Reported adverse effects from MDEA include the following:

Overdose

Reported overdose symptoms of MDEA include the following:

Disseminated intravascular coagulation{{cite journal | vauthors = Tehan B, Hardern R, Bodenham A | title = Hyperthermia associated with 3,4-methylenedioxyethamphetamine ('Eve') | journal = Anaesthesia | volume = 48 | issue = 6 | pages = 507–10 | date = June 1993 | pmid = 8322992 | doi = 10.1111/j.1365-2044.1993.tb07072.x | s2cid = 40356638 }}
Muscle rigidity
Rhabdomyolysis
Convulsions
Tachycardia
Hypotension
Sweating

Chemistry

=Synthesis=

MDEA is typically synthesized from essential oils such as safrole or piperonal.

:File:MDA from safrole en.png

History, society, and culture

Alexander Shulgin conducted research on methylenedioxy compounds in the 1960s. In a 1967 lab notebook entry, Shulgin briefly mentioned a colleague's report of no effect from the substance with a 100 mg dose.{{cite journal | vauthors = Benzenhöfer U, Passie T | title = Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin | journal = Addiction | volume = 105 | issue = 8 | pages = 1355–61 | date = August 2010 | pmid = 20653618 | doi = 10.1111/j.1360-0443.2010.02948.x }} Shulgin later characterized the substance in his book PiHKAL.{{cite web |last1=Shulgin |first1=Alexander | name-list-style = vanc |authorlink1=Alexander Shulgin |title=#106 MDE: MDEA; EVE; N-Ethyl-MDA; 3,4-Methylenedioxy-N-ethylamphetamine |url= http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106 |publisher=Isomer Design |access-date=10 December 2014 }}

In the United States, MDEA was introduced recreationally in 1985 as a legal substitute to the newly banned MDMA. MDEA was made a Schedule 1 substance in the United States on October 15, 1987.{{cite web |title=Electronic Orange Book|publisher=U.S. Food and Drug Administration |url=https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf |access-date=2024-04-12}}