6-Methyl-MDA

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6-Methyl-MDA
6-methyl-MDA.svg
Clinical data
Routes of
administration 		Oral [1]
ATC code
  • None
Legal status
Legal status
Identifiers
  • 1-(6-Methyl-1,3-benzodioxol-5-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H15NO2
Molar mass 193.246 g·mol−1
3D model (JSmol)
  • O1c2cc(c(cc2OC1)CC(N)C)C
  • InChI=1S/C11H15NO2/c1-7-3-10-11(14-6-13-10)5-9(7)4-8(2)12/h3,5,8H,4,6,12H2,1-2H3 Yes check.svgY
  • Key:HCFHWXDIZOAUTQ-UHFFFAOYSA-N Yes check.svgY
   (verify)

6-Methyl-MDA, also known as 6-methyl-3,4-methylenedioxyamphetamine is an entactogen and psychedelic drug of the amphetamine and MDxx families. [2] It was first synthesized in the late 1990s by a team including David E. Nichols at Purdue University while investigating derivatives of 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxy-N-methylamphetamine (MDMA). [2]

Contents

6-Methyl-MDA has IC50 values of 783 nM, 28,300 nM, and 4,602 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine in rat synaptosomes. [2] In animal studies it substitutes for MBDB, MMAI, LSD, and 2,5-dimethoxy-4-iodoamphetamine (DOI), though not amphetamine, but only partially and at high doses. [2] Thus, while several-fold less potent than its analogues 2-methyl-MDA and 5-methyl-MDA, and approximately half as potent as MDA, 6-methyl-MDA is still significantly active. [2]

According to Daniel Trachsel and colleagues, 6-methyl-MDA is active at a dose of 160 mg orally and has a duration of 8 hours. [1]

See also

References

  1. 1 2 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 656–657, 746, 830. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on 21 August 2025.
  2. 1 2 3 4 5 Parker MA, Marona-Lewicka D, Kurrasch D, Shulgin AT, Nichols DE (March 1998). "Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA)". Journal of Medicinal Chemistry. 41 (6): 1001–5. CiteSeerX   10.1.1.688.9559 . doi:10.1021/jm9705925. PMID   9526575.
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