3,4-Methylenedioxy-N-ethylamphetamine

3,4-Methylenedioxy-N-ethylamphetamine
Clinical data
Other names	MDEA, MDE, Eve
Routes of; administration	Oral, insufflation, injection, rectal
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I; UN: Psychotropic Schedule I;
Pharmacokinetic data
Metabolism	Hepatic including CYP2D6 and CYP3A4
Onset of action	20–85 minutes
Elimination half-life	(R)-MDEA: 7.5 ± 2.4 hours; (S)-MDEA: 4.2 ± 1.4 hours
Excretion	Renal
Identifiers
	IUPAC name 1-(1,3-Benzodioxol-5-yl)-N-ethylpropan-2-amine;
CAS Number	82801-81-8;
PubChem CID	105039;
ChemSpider	94775;
UNII	ML1I4KK67B;
KEGG	C22717;
ChEBI	CHEBI:132237;
CompTox Dashboard (EPA)	DTXSID70860971 ;
ECHA InfoCard	100.231.031
Chemical and physical data
Formula	C12H17NO2
Molar mass	207.273 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCNC(C)Cc1ccc2OCOc2c1;

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

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]^[3] Alexander Shulgin reported it to be stoning in high doses.^[4] 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:

Disseminated intravascular coagulation^[3]
Muscle rigidity^[3]
Rhabdomyolysis^[3]
Convulsions^[3]
Tachycardia^[3]
Hypotension^[3]
Sweating^[3]

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.^[5] Shulgin later characterized the substance in his book PiHKAL.^[4]

In the United States, MDEA was introduced recreationally in 1985 as a legal substitute to the newly banned MDMA.^[3] MDEA was made a Schedule 1 substance in the United States on October 15, 1987.^[6]

References

^ ^a ^b ^c ^d ^e 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.
^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ ^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): 507–10. doi:10.1111/j.1365-2044.1993.tb07072.x. PMID 8322992. S2CID 40356638.
^ ^a ^b Shulgin A. "#106 MDE: MDEA; EVE; N-Ethyl-MDA; 3,4-Methylenedioxy-N-ethylamphetamine". Isomer Design. Retrieved 10 December 2014.
^ 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.
^ https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf ^{[bare URL PDF]}

[Neuropsychopharmacology-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] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[Hyperthermia-3] ^ ^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): 507–10. doi:10.1111/j.1365-2044.1993.tb07072.x. PMID 8322992. S2CID 40356638.

[PiKHAL-4] Shulgin A. "#106 MDE: MDEA; EVE; N-Ethyl-MDA; 3,4-Methylenedioxy-N-ethylamphetamine". Isomer Design. Retrieved 10 December 2014.

[5] 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.

[6] ttps://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf ^{[bare URL PDF]}

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