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general/methylenedioxyphenethylamines

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3,4-Methylenedioxyphenethylamine

Chemical compound

Chemical compound

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MDPEA, also known as 3,4-methylenedioxyphenethylamine or as homopiperonylamine, is a possible psychoactive drug of the phenethylamine and methylenedioxyphenethylamine families. It is the 3,4-methylenedioxy derivative of phenethylamine (PEA). The drug is structurally related to 3,4-methylenedioxyamphetamine (MDA), but lacks the methyl group at the α carbon. It is a key parent compound of a large group of compounds known as entactogens such as MDMA ("ecstasy").

Use and effects

According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved), MDPEA was inactive at doses of up to 300mg orally. This is likely because of extensive first-pass metabolism by the enzyme monoamine oxidase (MAO). However, if MDPEA were either used in high enough of doses (e.g., 1–2grams), or in combination with a monoamine oxidase inhibitor (MAOI), it is probable that it would become active, though it would likely have a relatively short duration. This idea is similar in concept to the use of monoamine oxidase A (MAO-A) inhibitors to augment dimethyltryptamine (DMT) as in ayahuasca and of monoamine oxidase B (MAO-B) inhibitors to potentiate phenethylamine (PEA).

Besides being evaluated by Shulgin, MDPEA was studied at Edgewood Arsenal in the 1950s and was administered to humans at doses of up to 5.0mg/kg (350mg for a 70-kg person) by intravenous injection, although the results of these tests do not seem to have been released.

Interactions

Pharmacology

Pharmacodynamics

MDPEA produces sympathomimetic effects when administered intravenously at sufficiently high doses in dogs. It was about half as potent in this regard as PEA. The effects and toxicity of MDPEA in various animal species via intravenous injection have been studied and described.

Chemistry

Properties

The predicted log P of MDPEA is 1.2.

Analogues

Analogues of MDPEA include 3,4-methylenedioxy-N-methylphenethylamine (MDMPEA), lophophine (5-methoxy-MDPEA), mescaline (3,4,5-trimethoxyphenethylamine), 3,4-methylenedioxyamphetamine (MDA), and 3,4-methylenedioxy-N-methylamphetamine (MDMA), among others.

History

MDPEA was first described in the scientific literature by Gordon Alles by 1959. It was studied at Edgewood Arsenal under the code name EA-1297 in the 1950s, being administered by humans in 1952. The drug was described by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).

Society and culture

Poland

MDPEA is a controlled substance in Poland.

References

References

  1. "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych.
  2. {{CitePiHKAL https://www.erowid.org/library/books_online/pihkal/pihkal115.shtml
  3. (September 2024). "Neurobiological research on N,N-dimethyltryptamine (DMT) and its potentiation by monoamine oxidase (MAO) inhibition: from ayahuasca to synthetic combinations of DMT and MAO inhibitors". Cell Mol Life Sci.
  4. (2015). "The Perils of Illegitimate Online Pharmacies: Substance-Induced Panic Attacks and Mood Instability Associated With Selegiline and Phenylethylamine". Psychosomatics.
  5. (March 2016). "Availability of prescription drugs for bipolar disorder at online pharmacies". J Affect Disord.
  6. (1959). "Neuropharmacology: Transactions of the Fourth Conference, September 25, 26, and 27, 1957, Princeton, N. J.". Josiah Macy Foundation.
  7. (1959). "A Pharmacologic Approach to the Study of the Mind". CC Thomas.
  8. "1,3-Benzodioxole-5-ethanamine".
  9. (January 2018). "MDA, MDMA, and other "mescaline-like" substances in the US military's search for a truth drug (1940s to 1960s)". Drug Test Anal.
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