Chemistry:3,4-Methylenedioxy-N-ethylamphetamine

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Short description: Chemical compound


MDEA
Clinical data
Other namesMDEA; MDE; 3,4-Methylenedioxy-N-ethylamphetamine; N-Ethyl-MDA; Eve; EA-1304; EA1304; PAL-192; PAL192; ASR-1003; ASR1003
Routes of
administration		Oral, insufflation, injection, rectal[1]
Drug classSerotonin releasing agent; Entactogen
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
Duration of action3–5 hours[2][3]
ExcretionRenal
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
Chemical and physical data
FormulaC12H17NO2
Molar mass207.273 g·mol−1
3D model (JSmol)

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.[2][1][3]

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][4] Alexander Shulgin reported it to be stoning in high doses.[2] 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:

Interactions

Chemistry

Synthesis

The chemical synthesis of MDEA has been described.[2] It is typically synthesized from essential oils such as safrole or piperonal.[2]

Synthesis of MDA and related analogs from safrole

History

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.[5] Shulgin later characterized the substance in his book PiHKAL.[2]

Society and culture

United States

In the United States, MDEA was introduced recreationally in 1985 as a legal substitute to the newly banned MDMA.[4] MDEA was made a Schedule 1 substance in the United States on October 15, 1987.[6]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 "The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA)". CNS Drug Reviews 10 (2): 89–116. 2004. doi:10.1111/j.1527-3458.2004.tb00007.x. PMID 15179441. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 Shulgin, Alexander. "#106 MDE: MDEA; EVE; N-Ethyl-MDA; 3,4-Methylenedioxy-N-ethylamphetamine". Isomer Design. http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=106. 
  3. ↑ 3.0 3.1 "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol 35 (5): 512–536. May 2021. doi:10.1177/0269881120920420. PMID 32909493. 
  4. ↑ 4.00 4.01 4.02 4.03 4.04 4.05 4.06 4.07 4.08 4.09 4.10 "Hyperthermia associated with 3,4-methylenedioxyethamphetamine ('Eve')". Anaesthesia 48 (6): 507–10. June 1993. doi:10.1111/j.1365-2044.1993.tb07072.x. PMID 8322992. 
  5. ↑ "Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin". Addiction 105 (8): 1355–61. August 2010. doi:10.1111/j.1360-0443.2010.02948.x. PMID 20653618. 
  6. ↑ "Electronic Orange Book". U.S. Food and Drug Administration. https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf. 



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