3,4-Methylenedioxyphenethylamine

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MDPEA
Methylenedioxyphenethylamine.svg
Methylenedioxyphenethylamine.png
Clinical data
Other names1,3-benzodioxolyl-5-ethanamine;
3,4-methylenedioxy-2-phenylethylamine
Routes of
administration 		Various
Legal status
Legal status
Identifiers
  • 2-(1,3-benzodioxol-5-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.014.601 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C9H11NO2
Molar mass 165.192 g·mol−1
3D model (JSmol)
  • C1OC2=C(O1)C=C(C=C2)CCN
  • 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
   (verify)

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.

Contents

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.

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

Practical Uses

Homopiperonylamine was demonstrated to have application in the synthesis of Anonaine.

TDIQ is another application.

See also

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. Retrieved 17 June 2011.
  2. 1 2 Alles GA (1959). "Some Relations Between Chemical Structure and Physiological Action of Mescaline and Related Compounds / Structure and Action of Phenethylamines". In Abramson HA (ed.). Neuropharmacology: Transactions of the Fourth Conference, September 25, 26, and 27, 1957, Princeton, N. J. New York: Josiah Macy Foundation. pp. 181–268. OCLC   9802642. We studied the two compounds in Figure 38 and found that after intravenous injection into dogs, these compounds were about one-half or one-third as active in their peripheral activities as the unsubstituted compounds. [...] FIGURE 38. [...] 3,4-Methylenedioxyphenethylamine. Homopiperonylamine. [...] 3,4-Methylenedioxyphenisopropylamine. Methylenedioxy-amphetamine (MDA).
  3. 1 2 Alles GA (1959). "Subjective Reactions to Phenethylamine Hallucinogens". A Pharmacologic Approach to the Study of the Mind. Springfield: CC Thomas. pp. 238–250 (241–246). ISBN   978-0-398-04254-7.{{cite book}}: ISBN / Date incompatibility (help)
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