Phenethylamines i Have Known and Loved
  
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#69 gamma-DOM; Z-7; 2,6-DIMETHOXY-4-METHYLAMPHETAMINE

   SYNTHESIS: To a solution of 2,6-dimethoxy-4-methylbenzaldehyde (mp
   92-93 °C from the lithiation of 3,5-dimethoxytoluene followed by
   reaction with N-methylformanilide) in 10 mL nitroethane, there was
   added 0.1 g anhydrous am-monium acetate and the mixture was heated on
   the steam bath for 16 h. Removal of the solvent under vacuum gave a
   slightly oily red-orange crystalline mass which was finely ground
   under 1 mL of MeOH. Filtration and a sparing wash with MeOH gave,
   after air drying, 0.8 g of a light yellow crystalline solid with a mp
   of 121-122.5 °C. Recrystallization from 4 mLdrochloride (gamma-DOM) with a mp of 203 °C. sharp.
   
   DOSAGE: 15 - 25 mg.
   
   DURATION: 6 - 8 h.
   
   QUALITATIVE COMMENTS: (with 14 mg) I am really quite spacey. I can go
   from a train of thought straight up into thin air. Then, to get to
   another one there must be a careful choice of words. Logic has nothing
   to do with any of it. There is no trace of the MDMA-like magic. This
   is an interpretive drug, not simply an ASC [altered state of
   consciousness] opening.
   
   (with 18 mg) There is a light-headedness, and a somewhat starry-eyed
   stoned state. Nothing visual, and no body concern except for what
   seems to be a very fine inner tremor. I think that with a little more,
   things might very well begin to move in the tion became an obvious positional isomer, the Pennzoil
   Oil Company's additive, Z-7, was a natural to have its name
   volunteered to the cause. There was one additional isomer possible,
   with the methyl in the 2-position and the methoxyl groups at the 4-
   and 6-positions. This followed the more conventional aldehyde made
   from 3,5-dimethoxytoluene via the Vilsmeier process, with POCl3 and
   N-methylformanilide. This material (2,4-dimethoxy-6-methylbenzaldehyde
   with mp 64-65 °C from cyclohexane or from MeOH) is completely distinct
   from the isomer used above (2,6-dimethoxy-4-methylbenzaldehyde with a
   mp of 92-93 °C from MeOH). The amphetamine from this isomer is
   2,4-dimethoxy-6-methylamphetamine, and had been christened by the
   chcould
   allow for the 2,4,6-things to also be active.
   
   How can one accommodate such blasphemy? The first and obvious approach
   was the simplest. Denial. The 2,4,6-things aren't really active at
   all. Placebo stuff. There is a commonly used phrase, "bad science"
   which is an in-famous term used to belittle findings that do not fit
   with one's theories or purposes. But that simply didn't wash, because
   I knew, as did a few others who chose not to identify themselves too
   publicly, that TMA-2 and TMA-6 were both fully active in the 40 to 50
   milligram area. And although not as potent as DOM, the compound of
   this recipe, gamma-DOM or Z-7, was certainly an active one. So, since
   approach number one didn't work, try approach number reduction gave rise to what I was assuming
   would be the target amphetamine, 4-methyl-2,3,6-trimethoxyamphetamine
   or Z-7.2. This formed a hydrochloride salt which, although
   analytically excellent, insisted in remaining as an ether and
   chloroform-soluble oil which had an excellent NMR spectrum. This was
   certainly MY target compound, but it was not THEIR target compound.
   The upper echelons who were running the show were serious about this
   hydroquinone thing. Therefore, this product Z-7.2, that should have
   been entered into human evaluation, was instead processed further by
   the substitution of a t-BOC on the amine group, oxidation to the
   quinone with ceric ammonium nitrate, reduction to the hydroquinone
   with dithionite, and finally deprotection of the blocking t-BOC group
   by hydrw not much more than
   a minor bit of history. And anyhow, it was just about this time that I
   had uncovered a slick way of getting a sulfur atom into the
   amphetamine molecule. I quickly lost interest in the pursuit of other
   people's hypotheses that didn't seem to lead anywhere. Maybe, someday,
   some single earth-shaking mechanism will emerge to explain everything.
   But in the meantime, the best contribution I can make to this "grand
   unified theory of psychedelic activity" is to continue to make new and
   unexpected things which, if they are active, will effectively destroy
   any hypothesis that just happens to be popular at the moment. It is a
   lot more exciting, too.
   
   
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