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EDMA

From Wikipedia, the free encyclopedia
Chemical compound
This article is about a substituted amphetamine. For other uses, seeEDMA (disambiguation).
Pharmaceutical compound
EDMA
Clinical data
Other names3,4-Ethylenedioxy-N-methylamphetamine; EDMA; MDMC
Routes of
administration
Oral[1]
Drug classPsychoactive drug
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action3–5 hours[1]
Identifiers
  • 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-methylpropan-2-amine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC12H17NO2
Molar mass207.273 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 checkY
  • Key:UJKWLAZYSLJTKA-UHFFFAOYSA-N checkY
  (verify)

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drug of thephenethylamine,amphetamine, andEDxx families.[1][2] It is ananalogue ofMDMA where themethylenedioxyring has been replaced by anethylenedioxy ring.[1][2] EDMA was first synthesized byAlexander Shulgin.[1] In his bookPiHKAL, the dose is listed as 150 to 250 mg and the duration as 3 to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 includedparesthesia,nystagmus, adozing state,hypnogogicimagery, andcolored letters in the peripheral visual field.[1]

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.[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 individualenantiomers of EDMA have also been assessed.[3]

See also

[edit]

References

[edit]
  1. ^abcdefgShulgin A, Shulgin A (1991).Pihkal: A Chemical Love Story. Transform Press.ISBN 0-9630096-0-5.
  2. ^abcMcKenna 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. ^abcDel 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.

External links

[edit]
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
(and further-extended)
Catecholamines
(and close relatives)
Cyclized
phenethylamines
Phenylalkylpyrrolidines
2-Benzylpiperidines
(phenidates)
Phenylmorpholines
(phenmetrazines)
Phenyloxazolamines
(aminorexes)
Isoquinolines and
tetrahydroisoquinolines
2-Aminoindanes
2-Aminotetralins
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Related compounds
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