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 [1] [2] It is an analogue of MDMA where the methylenedioxy ring has been replaced by an ethylenedioxy ring.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 , the dose is listed as 150 to 250 mg 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

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. [3] 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. [3] The activities of the individual enantiomers of EDMA have also been assessed. [3]

See also

References

  1. 1 2 3 4 5 6 7 Shulgin A, Shulgin A (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN   0-9630096-0-5.
  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. 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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