Methylenedioxyphenethylamine

3,4-Methylenedioxyphenethylamine

Clinical data
Synonyms	1,3-benzodioxolyl-5-ethanamine; 3,4-methylenedioxy-2-phenylethylamine
Routes of administration	Various
Legal status
Legal status	IV-P (Poland)
Identifiers
IUPAC name 2-(1,3-benzodioxol-5-yl)ethanamine
CAS Number	1484-85-1 Y
PubChem CID	73874
ChemSpider	66508
ECHA InfoCard	100.014.601
Chemical and physical data
Formula	C9H11NO2
Molar mass	165.18914 g/mol
3D model (JSmol)	Interactive image
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

3,4-Methylenedioxyphenethylamine ("3,4-MDPEA" or just "MDPEA"), also known as 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.

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 MAO_A inhibitors and selective MAO_B inhibitors in augmentation of dimethyltryptamine (DMT) and phenethylamine (PEA), respectively.

In one known use of homopiperonylamine, amidation with 1-Adamantanecarbonyl chloride gives a dopamantane analog (Ex7).