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3,4-Methylenedioxy-N-ethylamphetamine

Chemical compound

Field	Value
drug_name	MDEA
image	MDEA.svg
image_class	skin-invert-image
width	235px
image2	MDEA molecule ball.png
image_class2	bg-transparent
width2	250px
routes_of_administration	Oral, insufflation, injection, rectal
class	Serotonin releasing agent; Entactogen
ATC_prefix	None
legal_AU	S9
legal_BR	F2
legal_BR_comment
legal_CA	Schedule I
legal_DE	Anlage I
legal_UK	Class A
legal_US	Schedule I
legal_UN	Psychotropic Schedule I
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
metabolism	Hepatic including CYP2D6 and CYP3A4
onset	20–85 minutes
elimination_half-life	(R)-MDEA: 7.5 ± 2.4 hours
(S)-MDEA: 4.2 ± 1.4 hours
duration_of_action	3–5 hours
excretion	Renal
IUPAC_name	1-(1,3-benzodioxol-5-yl)-N-ethylpropan-2-amine
C	12	H=17	N=1	O=2
SMILES	CCNC(C)Cc1ccc2OCOc2c1

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

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.

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:

Hyperthermia
Mydriasis
Loss of appetite

Overdose

Reported overdose symptoms of MDEA include the following:

Disseminated intravascular coagulation
Muscle rigidity
Rhabdomyolysis
Convulsions
Tachycardia
Hypotension
Sweating

Interactions

Chemistry

Synthesis

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

: [[File:MDA from safrole en.png|600px|class=skin-invert-image|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. Shulgin later characterized the substance in his book PiHKAL.

Society and culture

Legal status

United States

In the United States, MDEA was introduced recreationally in 1985 as a legal substitute to the newly banned MDMA.

References

Anvisa. (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
(2004). "The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA)". CNS Drug Reviews.
(May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol.
(June 1993). "Hyperthermia associated with 3,4-methylenedioxyethamphetamine ('Eve')". Anaesthesia.
(August 2010). "Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin". Addiction.
"#106 MDE: MDEA; EVE; N-Ethyl-MDA; 3,4-Methylenedioxy-N-ethylamphetamine". Isomer Design.
"Electronic Orange Book". U.S. Food and Drug Administration.

Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

designer-drugs entactogens euphoriants methylenedioxyphenethylamines partial-monoamine-releasing-agents pihkal serotonin-receptor-agonists serotonin-norepinephrine-dopamine-releasing-agents substituted-amphetamines

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