DMMDA

DMMDA
Legal status
Legal status
Identifiers
IUPAC name
  • 1-(4,7-Dimethoxy-1,3-benzodioxol-5-yl)propan-2-amine
CAS Number
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H19NO4
Molar mass241.287 g·mol−1
3D model (JSmol)
SMILES
  • CC(N)Cc1cc(OC)c2OCOc2c1OC
InChI
  • InChI=1S/C12H17NO4/c1-7(13)4-8-5-9(14-2)11-12(10(8)15-3)17-6-16-11/h5,7H,4,6,13H2,1-3H3 checkY
  • Key:GRGRGLVMGTVCNZ-UHFFFAOYSA-N checkY
  (verify)

2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA) is a psychedelic drug of the phenethylamine and amphetamine chemical classes.[1] It was first synthesized by Alexander Shulgin and was described in his book PiHKAL.[1] Shulgin listed the dosage as 30–75 mg and the duration as 6–8 hours.[1] He reported DMMDA as producing LSD-like images, mydriasis, ataxia, and time dilation.[1]

Synthesis

According to Alexander Shulgin, DMMDA can be synthesized from apiole.[1] Apiole is added to solution of potassium hydroxide and ethanol and the solution is held at a steam bath turning the apiole into isoapiole.[1] The isoapiole is then nitrated by adding it to a stirred solution of acetone and pyridine at ice-bath temperatures and treating the solution with tetranitromethane to form 1-(2,3-dimethoxy-3,4-methylenedioxyphenyl)-2-nitropropene.[1] The 1-(2,3-dimethoxy-3,4-methylenedioxyphenyl)-2-nitropropene is reduced to freebase DMMDA by adding it to a well-stirred and refluxing suspension of diethylether and lithium aluminum hydride under an inert atmosphere.[1] The freebase DMMDA converted into its hydrocloride salt.[1]

References

  1. 1 2 3 4 5 6 7 8 9 Shulgin A, Shulgin A (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5.


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