3,4-Methylenedioxy-N-ethylamphetamine

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.[1]

3,4-Methylenedioxy-N-ethylamphetamine
Clinical data
Other namesMDEA, MDE, Eve
Routes of
administration		Oral, insufflation, injection, rectal[1]
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
MetabolismHepatic including CYP2D6 and CYP3A4
Onset of action20–85 minutes
Elimination half-life(R)-MDEA: 7.5 ± 2.4 hours
(S)-MDEA: 4.2 ± 1.4 hours
ExcretionRenal
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.231.031
Chemical and physical data
FormulaC12H17NO2
Molar mass207.273 g·mol−1
3D model (JSmol)

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.[1][2] Alexander Shulgin reported it to be stoning in high doses.[3] 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.[1]

Adverse effects

Reported adverse effects from MDEA include the following:

Overdose

Reported overdose symptoms of MDEA include the following:

Chemistry

Synthesis

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.[4] Shulgin later characterized the substance in his book PiHKAL.[3]

In the United States, MDEA was introduced recreationally in 1985 as a legal substitute to the newly banned MDMA.[2] MDEA was made a Schedule 1 substance in the United States on August 13, 1987 under the Federal Analog Act.[1]

gollark: I don't understand what ridiculous nonsense you did but stop doing it, retroactively.
gollark: Okay, so Kit was *not* bluffing?
gollark: ...
gollark: #6 is boring, I would never write that, I wrote #11.
gollark: Your code is broken, I didn't write #6.

See also

References
  1. 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. PMC 6741736. PMID 15179441.
  2. Tehan B, Hardern R, Bodenham A (June 1993). "Hyperthermia associated with 3,4-methylenedioxyethamphetamine ('Eve')". Anaesthesia. 48 (6): 507–10. doi:10.1111/j.1365-2044.1993.tb07072.x. PMID 8322992.
  3. Shulgin A. "#106 MDE: MDEA; EVE; N-Ethyl-MDA; 3,4-Methylenedioxy-N-ethylamphetamine". Isomer Design. Retrieved 10 December 2014.
  4. Benzenhöfer U, Passie T (August 2010). "Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin". Addiction. 105 (8): 1355–61. doi:10.1111/j.1360-0443.2010.02948.x. PMID 20653618.
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