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-HT2Apartial agonist.[1]
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. DMMDA-3 could be made from
exalatacin (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 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]
Synthesis
Shulgin describes the synthesis of DMMDA from
apiole in his book
PiHKAL.[1]Apiole is subjected to an isomerization 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 aluminium hydride under an inert atmosphere (e.g.
helium).[1] Finally, the freebase DMMDA converted into its
hydrochloride salt.[1]
Alexander Shulgin's synthesis of DMMDA.
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] The Peracid oxidation can be accomplished by combining hydrogen peroxide with formic acid to create a peracid. The hydrolysis is usually acid-catalyzed with sulphuric acid because sulphuric acid will also result in the intermediary isoapiole monoformyl glycol being dehydrated to DMMDP2P. Then the DMMDP2P can then be subjected to a
reductive amination with a source of
nitrogen, such as
ammonium chloride, and a reducing agent, such as
sodium cyanoborohydride or an
amalgam of
mercury and
aluminium, to yield freebase DMMDA.[6]
^
abBrophy 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.
^US patent 4,876,277, Burke BA, Nair MG, "Antimicrobial/antifungal compositions", issued 1989-10-24, assigned to Plant Cell Research Institute, Inc., Dublin, Calif.
^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.
PMID18508215.
^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.
PMID6102141.