3,4-Methylenedioxy-N-ethylamphetamine

Last updated
3,4-Methylenedioxy-N-ethylamphetamine
MDEA.svg
MDEA-3D-vdW.png
Clinical data
Other namesMDEA, MDE, Eve
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
Elimination half-life (R)-MDEA: 7.5 ± 2.4 hours
(S)-MDEA: 4.2 ± 1.4 hours
Excretion Renal
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard 100.231.031 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C12H17NO2
Molar mass 207.273 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. [1]

Contents

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] [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

Reported adverse effects from MDEA include the following:

Overdose

Reported overdose symptoms of MDEA include the following:

Chemistry

Synthesis

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

MDA from safrole en.png

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. [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

Related Research Articles

MDMA Psychoactive drug

3,4-Methyl​enedioxy​methamphetamine (MDMA), commonly known as ecstasy (E) or molly, is a psychoactive drug primarily used for recreational purposes. The desired effects include altered sensations, increased energy, empathy, as well as pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last 3 to 6 hours.

2C-B Chemical compound

2C-B (2,5-dimethoxy-4-bromophenethylamine) is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 12–24 mg. As a recreational drug, 2C-B is sold as a white or pale pink powder sometimes pressed in tablets or gel caps. It is also referred to by a number of street names, including cocaína rosada for its rosy color. The drug is usually taken orally, but can also be snorted (insufflated) or vaporized.

2,5-Dimethoxy-4-bromoamphetamine

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INN) and bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967. Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.

3,4-Methylenedioxyamphetamine Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylene​dioxy​amphetamine (MDA), is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In terms of pharmacology, MDA acts most importantly as a serotonin-norepinephrine-dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

<i>para</i>-Methoxyamphetamine

para-Methoxyamphetamine, also known as 4-methoxyamphetamine (4-MA), is a designer drug of the amphetamine class with serotonergic effects. Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogen effects, and behaves more like an antidepressant in comparison, though it does have some psychedelic properties.

Methylone Group of stereoisomers

Methylone is an empathogen and stimulant psychoactive drug. It is a member of the substituted amphetamine, substituted cathinone and substituted methylenedioxyphenethylamine classes.

2,5-Dimethoxy-4-ethylamphetamine

2,5-Dimethoxy-4-ethylamphetamine is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL.

Ethylone

Ethylone, also known as 3,4-methylenedioxy-N-ethylcathinone, is a recreational designer drug classified as an entactogen, stimulant, and psychedelic of the phenethylamine, amphetamine, and cathinone chemical classes. It is the β-keto analogue of MDEA ("Eve"). Ethylone has only a short history of human use and is reported to be less potent than its relative methylone. In the United States, it began to be found in cathinone products in late 2011.

Substituted methylenedioxyphenethylamine

Substituted methylenedioxy- phenethylamines (MDxx) are a large chemical class of derivatives of the phenethylamines, which includes many psychoactive drugs that act as entactogens, psychedelics, and/or stimulants, as well as entheogens. These agents are used as research chemicals, designer drugs and as recreational substances.

3,4-Methylenedioxy-<i>N</i>-hydroxy-<i>N</i>-methylamphetamine

3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes. It is the N-hydroxy homologue of MDMA ("Ecstasy"), and the N-methyl homologue of MDOH. MDHMA was first synthesized and assayed by Alexander Shulgin. In his book PiHKAL, Shulgin listed the dosage range as 100–160 mg, and the duration as approximately 4–8 hours. He describes MDHMA as causing entactogenic and open MDMA-like effects, easing communication, and increasing appreciation of the senses.

1,3-Benzodioxolylbutanamine

1,3-Benzodioxolylbutanamine is an entactogenic drug of the phenethylamine chemical class. It is the α-ethyl analog of MDPEA and MDA and the methylenedioxy analogue of α-ethylphenethylamine.

<i>para</i>-Methoxy-<i>N</i>-methylamphetamine

para-Methoxy-N-methylamphetamine, chemically known as methyl-MA, 4-methoxy-N-methylamphetamine, 4-MMA) or is a stimulant and psychedelic drug closely related to the amphetamine-class serotonergic drug para-methoxyamphetamine (PMA). PMMA is the 4-methoxy analog of methamphetamine. Little is known about the pharmacological properties, metabolism, and toxicity of PMMA; because of its structural similarity to PMA, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose. In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA.

Etilamfetamine

Etilamfetamine is a stimulant drug of the phenethylamine and amphetamine chemical classes. It was invented in the early 20th century and was subsequently used as an anorectic or appetite suppressant in the 1950s, but was not as commonly used as other amphetamines such as amphetamine, methamphetamine, and benzphetamine, and was largely discontinued once newer drugs such as phenmetrazine were introduced. It most likely acts primarily as a dopamine releasing agent. Its activity as a norepinephrine or serotonin releasing agent is not known.

5-Methyl-MDA

5-Methyl-3,4-methylenedioxyamphetamine (5-Methyl-MDA) is an entactogen and psychedelic designer drug of the amphetamine class. It is a ring-methylated homologue of MDA and a structural isomer of MDMA.

3-Methoxy-4-methylamphetamine

3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a street drug in Italy in the same decade. MMA was largely forgotten until being reassayed by David E. Nichols as a non-neurotoxic MDMA analogue in 1991, and has subsequently been sold as a designer drug on the internet since the late 2000s (decade).

A serotonin releasing agent (SRA) is a type of drug that induces the release of serotonin into the neuronal synaptic cleft. A selective serotonin releasing agent (SSRA) is an SRA with less significant or no efficacy in producing neurotransmitter efflux at other types of monoamine neurons.

Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, bupropion, methoxyphenamine, selegiline, amfepramone, pyrovalerone, MDMA (ecstasy), and DOM (STP).

6-Methyl-MDA

6-Methyl-3,4-methylenedioxyamphetamine (6-Methyl-MDA) is an entactogen and psychedelic drug of the amphetamine class. It was first synthesized in the late 1990s by a team including David E. Nichols at Purdue University while investigating derivatives of 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxy-N-methylamphetamine (MDMA).

4-Chlorophenylisobutylamine Entactogen

4-Chlorophenylisobutylamine, also known as 4-chloro-α-ethylphenethylamine, is an entactogen and stimulant drug of the phenethylamine class. It is an analogue of para-chloroamphetamine (PCA) where the alpha position methyl has been replaced with an ethyl group.

A drug precursor is a substance which can be used to make illicit drugs.

References

  1. 1 2 3 4 5 6 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. 1 2 3 4 5 6 7 8 9 10 11 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.
  3. 1 2 Shulgin A. "#106 MDE: MDEA; EVE; N-Ethyl-MDA; 3,4-Methylenedioxy-N-ethylamphetamine". Isomer Design. Retrieved 10 December 2014.
  4. 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.