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Methylenedioxyphenethylamine
Systematic (IUPAC) name
2-(1,3-benzodioxol-5-yl)ethanamine
Identifiers
CAS number 1484-85-1
ATC code  ?
PubChem 73874
DrugBank ?
Chemical data
Formula C 9H11NO2  
Mol. mass 165.18914 g/mol
SMILES eMolecules & PubChem
Synonyms 1,3-benzodioxolyl-5-ethanamine;
3,4-methylenedioxy-2-phenylethylamine
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Uncontrolled
Routes Various

3,4-Methylenedioxyphenethylamine (MDPEA), also known as homopiperonylamine, is an entactogen, psychedelic, and stimulant of the substituted phenethylamine and amphetamine chemical classes.

According to Alexander Shulgin in his book PiHKAL, MDPEA appears to be biologically inactive, likely on account 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

External links


MDPEA
IUPAC name
Identifiers
CAS number [1484-85-1]
SMILES
Properties
Molecular formula C9H11NO2
Molar mass 165.189 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox references

MDPEA, or 3,4-methylenedioxyphenethylamine, is a lesser-known psychedelic drug. MDPEA was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), the minimum dosage is listed as 300 mg, and the duration unknown. MDPEA produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDPEA.

Derivatives

MDPEA has many derivatives, the most well known being MDMA.

Substituted methylenedioxy-phenethylamines, tabulated by structure
Short Name Rα Rβ R2 R5 RN Full Name
MDA CH3 H H H H 3,4-methylenedioxyamphetamine
MDMA CH3 H H H CH3 3,4-methylenedioxy-N-methylamphetamine
MDMC CH3 =O H H CH3 3,4-methylenedioxy-N-methyl-β-ketoamphetamine
MDEA CH3 H H H CH2CH3 3,4-methylenedioxy-N-ethylamphetamine
MDOH CH3 H H H OH 3,4-methylenedioxy-N-hydroxyamphetamine
BOH H OCH3 H H H 3,4-methylenedioxy-β-methoxyphenethylamine

See also

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