3,4-Methylenedioxyphenethylamine

3,4-Methylenedioxyphenethylamine, also known as 3,4-MDPEA, MDPEA, and homopiperonylamine, is a substituted phenethylamine formed by adding a methylenedioxy group to phenethylamine. It is structurally similar to MDA, but without the methyl group at the alpha position.

3,4-Methylenedioxyphenethylamine
Clinical data
Other names1,3-benzodioxolyl-5-ethanamine;
3,4-methylenedioxy-2-phenylethylamine
Routes of
administration		Various
Legal status
Legal status
  • IV-P (Poland)[1]
Identifiers
IUPAC name
  • 2-(1,3-benzodioxol-5-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.014.601
Chemical and physical data
FormulaC9H11NO2
Molar mass165.192 g·mol−1
3D model (JSmol)
SMILES
  • C1OC2=C(O1)C=C(C=C2)CCN
InChI
  • InChI=1S/C9H11NO2/c10-4-3-7-1-2-8-9(5-7)12-6-11-8/h1-2,5H,3-4,6,10H2
  • Key:RRIRDPSOCUCGBV-UHFFFAOYSA-N
  (verify)

According to Alexander Shulgin in his book PiHKAL, MDPEA appears to be biologically inactive. This is likely because of extensive first-pass metabolism by the enzyme monoamine oxidase. However, if MDPEA were either used in high enough of doses (e.g., 1-2 grams), or in combination with a monoamine oxidase inhibitor (MAOI), it is probable that it would become sufficiently active, though it would likely have a relatively short duration of action. This idea is similar in concept to the use of selective MAOA inhibitors and selective MAOB inhibitors in augmentation of dimethyltryptamine (DMT) and phenethylamine (PEA), respectively.

See also

References
  1. "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. Retrieved 17 June 2011.


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