3,4-Methylenedioxy-N-ethylamphetamine

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3,4-Methylenedioxy-N-ethylamphetamine
MDEA.svg
MDEA-3D-vdW.png
Clinical data
Routes of
administration
Oral, insufflation, injection, rectal[1]
ATC code none
Legal status
Legal status
Pharmacokinetic data
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
Excretion Renal
Identifiers
Synonyms MDEA, MDE, Eve
CAS Number 82801-81-8
PubChem (CID) 105039
ChemSpider 94775
UNII ML1I4KK67B
ChEBI CHEBI:132237
Chemical and physical data
Formula C12H17NO2
Molar mass 207.27 g/mol
3D model (Jmol) Interactive image

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]

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

Uses[edit]

Medical[edit]

MDEA currently has no accepted medical uses.

Recreational[edit]

MDEA is used recreationally in a similar manner to MDMA, 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[edit]

Reported adverse effects from MDEA include the following:

Overdose[edit]

Reported overdose symptoms of MDEA include the following:

Chemistry[edit]

Synthesis[edit]

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

Synthesis of MDA and related analogs from safrole

History, society, and culture[edit]

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]

See also[edit]

References[edit]

  1. ^ a b c d e f 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. 
  2. ^ a b c d e f g h i j k 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. 
  3. ^ a b Shulgin, Alexander. "#106 MDE: MDEA; EVE; N-Ethyl-MDA; 3,4-Methylenedioxy-N-ethylamphetamine". Isomer Design. Retrieved 10 December 2014. 
  4. ^ 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. 

External links[edit]