3,4-Methylenedioxyphenethylamine

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3,4-Methylenedioxyphenethylamine
Methylenedioxyphenethylamine.svg
Methylenedioxyphenethylamine-3D-balls.png
Clinical data
Pregnancy
category
  •  ?
Routes of
administration
Various
Legal status
Legal status
Pharmacokinetic data
Bioavailability ?
Metabolism ?
Biological half-life ?
Excretion ?
Identifiers
Synonyms 1,3-benzodioxolyl-5-ethanamine;
3,4-methylenedioxy-2-phenylethylamine
CAS Number 1484-85-1 YesY
PubChem (CID) 73874
DrugBank ? YesY
ChemSpider 66508
ECHA InfoCard 100.014.601
Chemical and physical data
Formula C9H11NO2
Molar mass 165.18914 g/mol
3D model (Jmol) Interactive image
  (verify)

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 MAOA inhibitors and selective MAOB 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).[2]

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