Skip to content
Methylenedioxyphenethylamine

Structure via PubChem · Public domain (PubChem)

EntityQ6823987· pop 6· linked from 1,490 articles

Methylenedioxyphenethylamine

Sign in to save

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").

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 sections
Contents
  • 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.

Available in 5 languages

via Wikidata sitelinks · CC0