EDMA

Last updated
EDMA
Ethylenedioxymethamphetamine.svg
Clinical data
Other names3,4-Ethylenedioxy-N-methylamphetamine; EDMA; MDMC
Routes of
administration 		Oral [1]
Drug class Psychoactive drug
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action 3–5 hours [1]
Identifiers
  • 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H17NO2
Molar mass 207.273 g·mol−1
3D model (JSmol)
  • CC(Cc1ccc2c(c1)OCCO2)NC
  • InChI=1S/C12H17NO2/c1-9(13-2)7-10-3-4-11-12(8-10)15-6-5-14-11/h3-4,8-9,13H,5-7H2,1-2H3 Yes check.svgY
  • Key:UJKWLAZYSLJTKA-UHFFFAOYSA-N Yes check.svgY
   (verify)

3,4-Ethylenedioxy-N-methylamphetamine (EDMA) is a psychoactive drug of the phenethylamine, amphetamine, and EDxx families. [1] [2] It is an analogue of MDMA where the methylenedioxy ring has been replaced by an ethylenedioxy ring. [1] [2] EDMA was first synthesized by Alexander Shulgin. [1] In his book PiHKAL (Phenethylamines I Have Known and Loved), the dose is listed as 150 to 250 mg orally and the duration as 3 to 5 hours. [1] According to Shulgin, EDMA produces only mild effects that included paresthesia, nystagmus, a dozing state, hypnogogic imagery, and colored letters in the peripheral visual field. [1]

Contents

While commonly referred to as EDMA, Shulgin refers to this compound as both MDMC and EDMA in PiHKAL, 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-neurotoxic serotonin releasing agent with moderately diminished potency relative to MDMA, and with negligible effects on dopamine release. [2] However, subsequent research found that EMDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) with EC50 Tooltip half-maximal effective concentration values of 117 nM for serotonin release, 325 nM for norepinephrine release, and 597 nM for dopamine release in rat brain synaptosomes. [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 individual enantiomers of EDMA have also been assessed. [4]

See also

References

  1. 1 2 3 4 5 6 7 8 Shulgin A, Shulgin A (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN   0-9630096-0-5. 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.
  2. 1 2 3 McKenna DJ, Guan XM, Shulgin AT (March 1991). "3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine". Pharmacology, Biochemistry, and Behavior. 38 (3): 505–512. doi: 10.1016/0091-3057(91)90005-M . PMID   1829838. S2CID   2740262.
  3. ↑ Karila L, Billieux J, Benyamina A, Lançon C, Cottencin O (September 2016). "The effects and risks associated to mephedrone and methylone in humans: A review of the preliminary evidences". Brain Res Bull. 126 (Pt 1): 61–67. doi:10.1016/j.brainresbull.2016.03.005. PMID   26995278. 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).
  4. 1 2 3 Del Bello F, Sakloth F, Partilla JS, Baumann MH, Glennon RA (September 2015). "Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine". Bioorg Med Chem. 23 (17): 5574–5579. doi:10.1016/j.bmc.2015.07.035. PMC   4562428 . PMID   26233799.
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