Methylenedioxyethylamphetamine

Methylenedioxyethylamphetamine

Systematic (IUPAC) name
1-(1,3-Benzodioxol-5-yl)-N-ethyl-propan-2-amine
Clinical data
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) UK: Class A US: Schedule I UN: Psychotropic Schedule I
Routes of administration	Oral, insufflation, injection, rectal
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
CAS Number	82801-81-8
ATC code	none
PubChem	CID: 105039
ChemSpider	94775
UNII	ML1I4KK67B
Synonyms	MDEA, MDE, Eve
Chemical data
Formula	C12H17NO2
Molecular mass	207.27 g/mol
SMILES CCNC(C)Cc1ccc2OCOc2c1

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.

Uses

Medical

MDEA currently has no accepted medical uses.

Recreational

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.

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

Physical and chemical properties

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. 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.

See also

• 3-Fluoroethamphetamine
• 4-Methoxyethamphetamine
• Ethylone
• Fenfluramine

External links

• MDE entry in PiHKAL