Methylenedioxyphenethylamine

Methylenedioxyphenethylamine

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Systematic (IUPAC) name
2-(1,3-benzodioxol-5-yl)ethanamine
Clinical data
Pregnancy category	?
Legal status	IV-P (Poland)
Routes of administration	Various
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Biological half-life	?
Excretion	?
Identifiers
CAS Number	1484-85-1 Y
PubChem	CID: 73874
DrugBank	? Y
ChemSpider	66508
Synonyms	1,3-benzodioxolyl-5-ethanamine; 3,4-methylenedioxy-2-phenylethylamine
Chemical data
Formula	C9H11NO2
Molecular mass	165.18914 g/mol
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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3,4-Methylenedioxyphenethylamine (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.

See also

• Substituted methylenedioxyphenethylamine

External links

• PiHKAL: #115 MDPEA; 3,4-Methylenedioxyphenethylamine; Homopiperonylamine