|Systematic (IUPAC) name|
|Oral, insufflation, injection, rectal|
|Metabolism||Hepatic including CYP2D6 and CYP3A4|
|Onset of action||20-85 minutes|
|Biological half-life||(R)-MDEA: 7.5 ± 2.4 hours
(S)-MDEA: 4.2 ± 1.4 hours
|CAS Registry Number|
|Synonyms||MDEA, MDE, Eve|
|Molecular mass||207.27 g/mol|
3,4-methylenedioxy-N-ethyl-amphetamine – abbreviated to Methylenedioxyethylamphetamine, MDEA, or MDE and known colloquially as "Eve" – is a psychoactive drug of the phenethylamine and amphetamine classes of drugs. It is consumed primarily for its euphoric and empathogenic effects. MDEA acts as a serotonin, norepinephrine, and dopamine releasing agent and reuptake inhibitor.
Possession of MDEA is illegal in most countries. Some limited exceptions exist for scientific and medical research.
MDEA currently has no accepted medical uses.
MDEA is used recreationally in a similar manner to MDMA, 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 ingredient of ecstasy. Studies conducted in the 1990s found MDEA present in approximately four percent of ecstasy tablets.
Reported adverse effects from MDEA include the following:
Reported overdose symptoms of MDEA include the following:
- Disseminated intravascular coagulation
- Muscle rigidity
Physical and chemical properties
MDEA is typically synthesized from essential oils such as safrole or piperonal.
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. Shulgin later characterized the substance in his book PiHKAL.
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 August 13, 1987 under the Federal Analog Act.
- Freudenmann RW, Spitzer M (2004). "The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA)". CNS Drug Reviews 10 (2): 89–116. doi:10.1111/j.1527-3458.2004.tb00007.x. PMID 15179441.
- Tehan, B.; Hardern, R.; Bodenham, A. (June 1993). "Hyperthermia associated with 3,4-methylenedioxyethamphetamine ('Eve')". Anaesthesia 48 (6): 507–510. doi:10.1111/j.1365-2044.1993.tb07072.x. Retrieved 10 December 2014.
- Shulgin, Alexander. "#106 MDE: MDEA; EVE; N-Ethyl-MDA; 3,4-Methylenedioxy-N-ethylamphetamine". http://isomerdesign.com. Isomer Design. Retrieved 10 December 2014.
- Benzenhöfer, Udo; Passie, Torsten (9 July 2010). "Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin". Addiction 105 (8): 1355–1361. doi:10.1111/j.1360-0443.2010.02948.x.