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| Other names | 3,4-Ethylenedioxy-N-methylamphetamine; EDMA; MDMC |
| Routes of administration | Oral[1] |
| Drug class | Psychoactive drug |
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| Duration of action | 3–5 hours[1] |
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| Formula | C12H17NO2 |
| Molar mass | 207.273 g·mol−1 |
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3,4-Ethylenedioxy-N-methylamphetamine (EDMA) is apsychoactive drug of thephenethylamine,amphetamine, andEDxx families.[1][2] It is ananalogue ofMDMA where themethylenedioxyring has been replaced by anethylenedioxy ring.[1][2] EDMA was first synthesized byAlexander Shulgin.[1] In his bookPiHKAL (Phenethylamines I Have Known and Loved), the dose is listed as 150 to 250 mgorally and theduration as 3 to 5 hours.[1] According to Shulgin, EDMA produces only mild effects that includedparesthesia,nystagmus, adozing state,hypnogogicimagery, andcolored letters in the peripheral visual field.[1]
While commonly referred to as EDMA, Shulgin refers to this compound as both MDMC and EDMA inPiHKAL, calling the former a "Shulgin pet name" for the compound, and stating that the name "doesn't really make sense".[1] MDMC commonly refers to a different analogue of MDMA,methylone.[3]
It has been found that EDMA acts as a non-neurotoxicserotonin releasing agent with moderately diminishedpotency relative to MDMA, and with negligible effects ondopamine release.[2] However, subsequent research found that EMDA is aserotonin–norepinephrine–dopamine releasing agent (SNDRA) withEC50Tooltip half-maximal effective concentration values of 117 nM for serotonin release, 325 nM for norepinephrine release, and 597 nM for dopamine release in rat brainsynaptosomes.[4] Compared to MDMA, EDMA was about half as potent as a serotonin releaser, 4.5-fold less potent as a norepinephrine releaser, and 8-fold less potent as a dopamine releaser.[4] The activities of the individualenantiomers of EDMA have also been assessed.[4]
The original name that this compound got, during the several explorations of MDMA analogues, was based on the nickname for MDMA which was Adam. HAD'EM was mentioned with the hydroxy compound, MADAM with the 6-methyl homologue, and FLADAM with the 6-fluoro analogue. This compound got the sobriquet MACADAM from that horrible black gooey mess generated at the aldehyde stage. This was shortened to RCS and eventually the RCS was added to the MDMA parent name. Thus, MDMC. It doesn't really make sense; EDMA is more reasonable. But then there is no reason why MDMC should make sense.
Methylone (3,4-methylenedioxymethcathinone) is methylated on the amine group and α carbon of this β-ketophenethylamine backbone (figure 1). It has a methylenedioxy ring attached to the aromatic ring, forming a structure similar to MDMA (Meyer and Maurer, 2010). The substituted cathinone was first synthesized in 1996 as a potenital antidepressant and anti-Parkinsonian agent (Jacob and Shulgin, 1996). It however never resulted in a commercialized pharmaceutical product. Methylone is also named M1, MDMC and bk-MDMA (Karila and Reynaud, 2011).
