Author Topic: 2,4,6-trimethoxyphenylethylamine from Apple trees?  (Read 1022 times)

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  • Guest
2,4,6-trimethoxyphenylethylamine from Apple trees?
« on: July 06, 2002, 08:34:00 AM »
I was perusing "the Book" last night and ran across Sasha's discussion of this compound under TMA-6, I believe. 

Obviously, being a positional isomer of mescaline,
psi-TMPEA wouldn't be a compound to brashly synthesize in the U.S. anyway, but Shulgin mentions that, although it has never been bioassayed before in mice or men, it has been found not to be a substrate of the monoamine oxidase enzyme in rabbits. 

Furthermore, 1,3,5-trihydroxybenzene is supposedly easily had from all parts of the apple tree except for in the actual fruit itself after doing some simple acid hydrolysis and acid-base extractions on its parent compound. 

Anyway, my biggest question then is would it be possible to formylate either 1,3,5-trihydroxybenzene or 1,3,5-trimethoxybenzene (which would be preferable?) with something other than N-methylanilidine, a List I chemical? 

What about that chemical Nichols (and later MaDMAx) used to formylate indan, wouldn't that work?  Why or why not?


  • Guest
N-Methyl-formanilide & Phloroglucinol
« Reply #1 on: July 06, 2002, 10:04:00 AM »
N-Methyl-formanilide (correct spelling) is not a List 1 chemical. What I believe you would have more problem with would be the aquisition of POCl3, as it can be used in the manufacture of Sarin/Tabun war gases.

What chemicals DO you have access to? You should be able to formylate 1,3,5-trihydroxybenzene with CHCl3/KOH (Reimer-Tiemann) or 1,3,5-trimethoxybenzene with dichloromethyl methyl ether and a medium Lewis acid like SnCl4 or TiCl4.

If you haven't already, read

- you'll find many formylation ideas there. Don't miss the Magnesium Methoxide/Paraformaldehyde method either.

Phytochemistry 37(3), 755-6 (1994)

Phloroglucinol glucoside was identified from shoot laticifer exudate of Cannabis sativa (marihuana) by TLC. Isolation of the aglycone from acid-heat hydrolysis or emulsin treatment yielded the free phenol, phloroglucinol (1,3,5-trihydroxybenzene), as identified by GC-MS and NMR. Phloroglucinol also was identified by TLC as a prominent component in glandular trichomes.

Entropy just isn't what it used to be.


  • Guest
CHCl3 is not a problem for me and neither is KOH.
« Reply #2 on: July 06, 2002, 10:52:00 AM »
CHCl3 is not a problem for me and neither is KOH.  I haven't read your link on formylation, but I will be sure to check it out.  If SnCl4 is stannous chloride, then that is no problem either, but I'm sure that I don't have access to that chloro methyl methyl ether stuff anyway.  My biggest problems are a lack of organic synthesis experience and an unwillingness to perform any reaction that has been specifically outlawed according to Shulgin's other book, "Controlled Substances."

Analogues, homologues and other issues supposedly covered by the Analogue Act do not intimidate me, because my lawyer has been before the Supreme Court before, and if the Supreme Court were to decide that it is ok to convict one of its citizens for something that s/he invented before they specifically outlawed it, then that is just wrong and I wouldn't mind going to jail for doing so just to set the precedent, although I'd rather not of course.  Furthermore, this is more of a religious issue to me, and the apple did supposedly come from the tree of knowledge.  The fact that cannabis sativa and apple trees both contain
1,3,5-trihydroxybenzene only strengths my resolve, but at any rate, I have said too much and have got to go.  Just to reiterate, I have never made an illegal drug before and have no intentions of doing so, although I have taken quite a few that others have made and am not sorry.  If 2,4,6-TMPEA were simply an analogue or homologue of some forbidden fruit, then that would be one thing, but as it stands, it's just too similar to mescaline (as a conformational isomer of mescaline) for me to commit myself to in today's legal environs.  Like I said, I'm mainly just curious.


  • Guest
« Reply #3 on: July 07, 2002, 06:55:00 AM »
The 'usual' formylation with POCl3 and DMF works greath on 1,3,5 trimethoxybenzen.
TMA-6 is one of the fun ones (have to start at 80mg), a bit loong but greath visuals. ;)


  • Guest
Have you then ever also tasted 2C-TMA-6 after ...
« Reply #4 on: July 07, 2002, 01:28:00 PM »
Have you then ever also tasted 2C-TMA-6 after substituting nitromethane for nitroethane?  If so, how does that compare to TMA-6?



  • Guest
« Reply #5 on: July 08, 2002, 12:31:00 AM »
Nope, I don't thgink there is enough power in the phenetylamine analog. Active dose for tmpea more than 300mg for mescalin 500mg. I don't like to ingest that much of product. (but doo it from time to time with mescalin :) )


  • Guest
Well if I had any, I would (after starting at a ...
« Reply #6 on: July 08, 2002, 03:17:00 PM »
Well if I had any, I would (after starting at a lower dose and working my way up), but I don't and probably never will.  C'est la vie....


  • Guest
Reply to 'Well if I had any, I would (after starti
« Reply #7 on: July 08, 2002, 10:53:00 PM »
I feel ya, Modulator.  I want to eat a large dose of DMMDEA-2, myself.  Probably won't do shit, but we'll see.