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| Other names | 3,4-Methylenedioxyphenethylamine; Methyleneddioxyphenethylamine; 3,4-MDPEA; Homopiperonylamine; EA-1297 |
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| ECHA InfoCard | 100.014.601 |
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| Formula | C9H11NO2 |
| Molar mass | 165.192 g·mol−1 |
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MDPEA, also known as3,4-methylenedioxyphenethylamine or ashomopiperonylamine, is a possiblepsychoactive drug of thephenethylamine andmethylenedioxyphenethylamine families.[2] It is the 3,4-methylenedioxyderivative ofphenethylamine (PEA).[2] The drug isstructurally related to3,4-methylenedioxyamphetamine (MDA), but lacks themethyl group at theα carbon.[2] It is a keyparent compound of a large group of compounds known asentactogens such asMDMA ("ecstasy").[2]
According toAlexander Shulgin in his bookPiHKAL (Phenethylamines I Have Known and Loved), MDPEA was inactive at doses of up to 300 mgorally.[2] This is likely because of extensivefirst-passmetabolism by theenzymemonoamine oxidase (MAO).[2] However, if MDPEA were either used in high enough ofdoses (e.g., 1–2 grams), or incombination with amonoamine oxidase inhibitor (MAOI), it is probable that it would become active, though it would likely have a relatively shortduration.[citation needed] This idea is similar in concept to the use ofmonoamine oxidase A (MAO-A) inhibitors to augmentdimethyltryptamine (DMT) as inayahuasca[3] and ofmonoamine oxidase B (MAO-B) inhibitors to potentiatephenethylamine (PEA).[4][5]
Besides being evaluated by Shulgin, MDPEA was studied atEdgewood Arsenal in the 1950s and was administered to humans at doses of up to 5.0 mg/kg byintravenous injection, although the results of these tests do not seem to have been released.[6]
MDPEA producessympathomimetic effects when administeredintravenously at sufficiently high doses in dogs.[7][8] It was about half aspotent in this regard as PEA.[7][8] The effects andtoxicity of MDPEA in various animal species viaintravenous injection have been studied and described.[6]
The predictedlog P of MDPEA is 1.2.[9]
Analogues of MDPEA include3,4-methylenedioxy-N-methylphenethylamine (MDMPEA),lophophine (5-methoxy-MDPEA),mescaline (3,4,5-trimethoxyphenethylamine),3,4-methylenedioxyamphetamine (MDA), and3,4-methylenedioxy-N-methylamphetamine (MDMA), among others.[2]
MDPEA was first described in thescientific literature byGordon Alles by 1959.[7][8] It was studied atEdgewood Arsenal under the code nameEA-1297 in the 1950s, being administered by humans in 1952.[2][6] The drug was described byAlexander Shulgin in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).[2]
MDPEA is acontrolled substance inPoland.[1]
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).
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