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Methylenedioxyphenethylamine
Sign in to saveMDPEA, also known as 3,4-methylenedioxyphenethylamine or as homopiperonylamine, is a possible psychoactive drug of the phenethylamine and methylenedioxyphenethylamine families. It is the 3,4-methylenedioxy derivative of phenethylamine (PEA). The drug is structurally related to 3,4-methylenedioxyamphetamine (MDA), but lacks the methyl group at the α carbon. It is a key parent compound of a large group of compounds known as entactogens such as MDMA ("ecstasy").
Chemical data
- Formula
- C9H11NO2
- Molecular weight
- 165.19 g/mol
- IUPAC name
- 2-(1,3-benzodioxol-5-yl)ethanamine
- SMILES
- C1OC2=C(O1)C=C(C=C2)CCN
- InChIKey
- RRIRDPSOCUCGBV-UHFFFAOYSA-N
- XLogP
- 1.2
- Polar surface area
- 44.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 165.078979
Show 3 more facts
- chemical formula
- C₉H₁₁NO₂
- canonical SMILES
- C1OC2=C(O1)C=C(C=C2)CCN
- Commons category
- 3,4-Methylenedioxyphenethylamine
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
15 sectionsContents
- Use and effects
- Interactions
- Pharmacology
- Pharmacodynamics
- Chemistry
- Properties
- Synthesis
- Analogues
- History
- Society and culture
- Legal status
- Poland
- See also
- References
- External links
MDPEA, also known as 3,4-methylenedioxyphenethylamine or as homopiperonylamine, is a possible psychoactive drug of the phenethylamine and methylenedioxyphenethylamine families. It is the 3,4-methylenedioxy derivative of phenethylamine (PEA). The drug is structurally related to 3,4-methylenedioxyamphetamine (MDA), but lacks the methyl group at the α carbon. It is a key parent compound of a large group of compounds known as entactogens such as MDMA ("ecstasy").
==Use and effects== According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved), MDPEA was inactive at doses of up to 300mg orally. This is likely because of extensive first-pass metabolism by the enzyme monoamine oxidase (MAO). However, if MDPEA were either used in high enough of doses (e.g., 1–2grams), or in combination with a monoamine oxidase inhibitor (MAOI), it is probable that it would become active, though it would likely have a relatively short duration. This idea is similar in concept to the use of monoamine oxidase A (MAO-A) inhibitors to augment dimethyltryptamine (DMT) as in ayahuasca and of monoamine oxidase B (MAO-B) inhibitors to potentiate phenethylamine (PEA).
Excerpted from Wikipedia’s “Methylenedioxyphenethylamine” article, available under the CC BY-SA 4.0 licence.