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.

MDPEA

Clinical data
Other names	1,3-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	1484-85-1 Y
PubChem CID	73874
ChemSpider	66508
UNII	F2J2U8J2G5
CompTox Dashboard (EPA)	DTXSID00163982
ECHA InfoCard	100.014.601
Chemical and physical data
Formula	C9H11NO2
Molar mass	165.192 g·mol−1
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
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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.

MDPEA produces sympathomimetic effects when administered intravenously in dogs.^[2][3] It was about half as potent in this regard as PEA.^[2][3]

See also

• Substituted methylenedioxyphenethylamine