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DMMDA
DMMDA.png
DMMDA-3d-sticks.png
Legal status
Legal status
Identifiers
  • 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)
  • CC(N)Cc1cc(OC)c2OCOc2c1OC
  • 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]

Pharmacology

The mechanism behind DMMDA's hallucinogenic effects has not been specifically established, however Shulgin describes that a 75 milligram dose of DMMDA is equivalent to a 75–100 microgram dose of LSD. LSD is a known 5-HT2A partial agonist.[1] Thus, it's highly likely that the hallucinogenic effects of DMMDA result from action as a 5-HT2A serotonin receptor agonist or partial agonist in the brain.

Chemistry

Shulgin explains in his book that DMMDA has 6 isomers similar to TMA.[1] DMMDA-2 is the only other isomer that has been synthesized as of yet. A new isomer of DMMDA could be made from exalatacin or 1-allyl-2,6-dimethoxy-3,4-methylenedioxybenzene. Exalatacin can be found in the essential oil of both Crowea exalata and Crowea angustifolia var. angustifolia.[2] In other words, exalatacin is an isomer of both apiole and dillapiole, which can both be used to make DMMDA and DMMDA-2 respectively. Exalatacin is almost identical to apiole and dillapiole but differs from them in its positioning of its methoxy groups, which are in the 2 and 6 positions.[2] Additionally, yet another isomer of DMMDA could be made from pseudo-dillapiole or 4,5-dimethoxy-2,3-methylenedioxyallylbenzene.[3]

Exalatacin.png

Synthesis

Shulgin describes the synthesis of DMMDA from apiole in his book PiHKAL.[1] Apiole is subjected to an isomerisation reaction to yield isoapiole by adding to solution of ethanolic potassium hydroxide and holding the solution at a steam bath.[1] The isoapiole is then nitrated to 2-nitro-isoapiole or 1-(2,3-dimethoxy-3,4-methylenedioxyphenyl)-2-nitropropene by adding it to a stirred solution of acetone and pyridine at ice-bath temperatures and treating the solution with tetranitromethane. The pyridine acts as a catalyst in this reaction.[1] The 2-nitro-isoapiole is finally reduced to freebase DMMDA by adding it to a well-stirred and refluxing suspension of diethylether and lithium aluminum hydride under an inert atmosphere (e.g. helium).[1] Finally, the freebase DMMDA converted into its hydrochloride salt.[1]

Shulgin's synthesis of DMMDA is reasonably unsafe, since it involves the use of tetranitromethane, which is toxic, carcinogenic and prone to detonating.[4] DMMDA can be made from apiole via other safer methods. Among other methods, DMMDA can be synthesize from apiole via the intermediate chemical 2,5-dimethoxy-3,4-methylenedioxyphenylpropan-2-one or DMMDP2P in the same manner as MDA is made from safrole. DMMDP2P can be made from apiole via a Wacker oxidation with benzoquinone. DMMDP2P can be alternatively made by subjecting apiole to an isomerisation reaction to yield isoapiole followed by a Peracid oxidation and finally a hydrolytic dehydration.[5] Then the DMMDP2P can then be subjected to a reductive amination with ammonium chloride with sodium cyanoborohydride acting as a reducing agent to yield freebase DMMDA.[6]

References

  1. ^ a b c d e f g h i j k Shulgin A, Shulgin A (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5.
  2. ^ a b Brophy JJ, Goldsack RJ, Punruckvong A, Forster PI, Fookes CJ (July 1997). "Essential oils of the genus Crowea (Rutaceae)". Journal of Essential Oil Research. 9 (4): 401–409. doi:10.1080/10412905.1997.9700740.
  3. ^ US patent 4,876,277, Basil A. Burke, Muraleedharan G. Nair, "Antimicrobial/antifungal compositions", issued 1989-10-24, assigned to Plant Cell Research Institute, Inc., Dublin, Calif. 
  4. ^ National Toxicology Program (2011). "Tetranitromethane" (PDF). Report On Carcinogens (12th ed.). National Toxicology Program. Archived (PDF) from the original on 2013-01-31. Retrieved 2012-08-14.
  5. ^ Cox M, Klass G, Morey S, Pigou P (July 2008). "Chemical markers from the peracid oxidation of isosafrole". Forensic Science International. 179 (1): 44–53. doi:10.1016/j.forsciint.2008.04.009. PMID 18508215.
  6. ^ Braun U, Shulgin AT, Braun G (February 1980). "Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine)". Journal of Pharmaceutical Sciences. 69 (2): 192–195. doi:10.1002/jps.2600690220. PMID 6102141.