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5HT2a ligands and RC Tryptamines

ok sorry for posting all fucked up yesterday,
SWIM usually posts when on adderall to counter act the f'k'n ADD/ADHD disease instead of under the influence of ethanol... Anyone have any other thoughts?:)
 
The phosphate is natures protecting group (Psilocin-Psilocybin)

We know that the heteroaromatic acetoxy is not a particularly good idea since this stuff decomposes readily. We would like the phosphate ester but you would make a hash of it trying to stew up in a lab, so it's probably best left to nature.

All im saying is that if you wanted to protect the 4-OH against decomposition (occuring by that funky redox mechanism), then by preparing the 4-OMe derivative problem solved.
 
Calm down dondante. If you want people to avoid "story telling" perhaps you should set a good example, and only discuss relavent material. (though I get where you're coming from).
 
^^Yeah, I got a little over excited about this idea when I found it. :)

Smyth,

I hope to try some 4-meo-mipt sometime soon. It seems from Tihkal that the methoxy is very stable, but the molecule itself may make it a slightly better substrate for MAO enzymes, especially when there's the nitrogen is more accessible as in 4-meo-dmt. Shulgin's comment about the lack of activity of 4-meo-det up to 30mg smoked is odd. If MAO's are responsible, then maybe 4-meo-dmt would be inactive orally? This would support the idea that there is a conformational change responsible for protecting the 4-HOs.

The other option is that the 4-position oxygen needs to be exposed for stronger receptor binding. In that case 4-meo-det and 4-meo-dmt should have similar activity to 4-meo-mipt. Only time will tell.
 
Well what is created when 4-aco-dmt is oxidized?

I put 30mg 4-aco-dmt in a very small bit of water (... 1-2ml..) with more than enough NaOH in there to take care of the fumarate's and acetoxy, started to turn blue, i let it sit longer and it became a darkish blue/green solution.

I dumped it into some juice and drank it down, and whatever was created from being oxidized seems to be active, it felt like a much different trip, but more like psilocin + at least another (maybe couple) active compounds mixed together. Different colors visuals etc.
 
Dondante,

Sorry, that comment was harsh. There's no real answer as to why it (the 4-OH issue) is that way. The 4-MeO-tryptamines are just less active than their
4-OH counterparts.

yoyoman,

What you got was dmt-4-O-O-4-dmt, a dimer. That's what the purple color is sometimes seen staining magic mushrooms.
 
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So is the keto form the same as the quinonic product Shulgin is referring to? And is that any different from the internal salt C6H6 mentioned (other than being a tautomer)?
 
well if that was it... an O with a double bond like that, well, i think its active.. polar or whatever enough to get past the BBB? if not, well, something created , did :) heh..

:)

i'm very very curious about other things you can stick on the the 4 position, 4-whtever-DMT, amino... etc.. whatever should get into the brain and do something, ... keepin' that DMT part there... would be very interesting to find something, to stick ... on the 4...or somewhere else to keep MAO from eating it, yet have much closer pharmacology to DMT
 
4-MeO would be very interesting.

Um, if anyone has 4-HO-DMT (or 4-Acetoxy-DMT)... perhaps they could basify to form the alkoxide and then methylate with MeI or Me2SO4 to form 4-MeO-DMT. :)
 
"4-MeO-DET is completely without action either orally or by smoking at dosages up to 30mgs."

"4-MeO-MIPT:

"(with 26mg, orally) This is my first try with this drug, ever. First indication of effects in twenty minutes. Quiet onset, no remarkable visuals, in fact no visuals at all. To a +2 within about ten or fifteen minutes more. Body is comfortable, mind-set pretty much unchanged from baseline. No euphoria, no insights. But also, no discomfort. Erotic was extremely successful, and orgasm seemed easier than with other materials. Still no visuals but seemed to be a soft +3. Music fine. Hard to define exactly how we knew we were in an altered state, because of the lack of visual cues. Body aware more than mind. Would like to explore this further. Perhaps for writing? Nice material. Maybe higher next time?"

Conclusion:

4-MeO-DMT is worth trying, but I doubt that it's active. Maybe try 4-(CCl3)-DMT instead.

On second thought, 4-(CF3)-DMT is more like it. Those three chlorine atoms are probably too bulky.
 
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Smyth and Dondante,

No, you have 2 identical molecules after the hydrolysis. Namely, 4-OH-DMT and 4-OH-DMT. The two 3-dimethylaminoethyl side chains do not participate in the following reaction. The atoms that react are one oxygen from one molecule and the other oxygen from the other identical molecule to form a peroxide (R-O-O-R) bond linking the two former molecules into a new one.

The new molecule (R-O-O-R) is called a dimer because it consists of two identical subunits connected to each other to form a bigger molecule. The R's in the new molecule, R-O-O-R, can be rightly called
4-(3-dimethylaminoethylindolyl's).

If this doesn't help explain it right, I'll scan a Kekule structure for you if possible.
 
Why halogens? Sure, that arrnagement (TFM) works real nice at the para (4) position on PEA's , but I don't know about Tryptamines...
Never seen any papers detailing halogen substituents on the indole system.
 
Why halogens? It comes down to electronegativity--how much an atom draws electron density in towards itself.

Fluorine is the most electronegative atom in the Periodic Table, but in terms of size, fluorine is about the same size as tiny hydrogen. Thus, fluorine does not have as much electron density to withdraw and thus let the electron cloud work its magic. One trick, however, is to stick three fluorines on a carbon atom
(CH3-->CF3) and in that way the fluorines pull in electro density through the carbon atom.

The wonders of mdxx and 4-OH-DMT and so forth are brought to us because oxygen is the second most electronegative atom other than fluorine, but oxygen has the advantage of being substantially heavier than fluorine and thus has more electro density. Likewise, the halogens other than fluorine are both intrinsically highly electronegative and fairly heavy. After all, they have three lone pairs of electrons apiece.

So you see, a 4-CF3 is not all that different (in terms both of electronegativities and physical size) than a 4-OH. 4-CCl3 will be even better if it's not too much bigger than the -OH on this particular molecule.

Back to the Dondante and Smyth querie, I have submitted a Kekule structure to the Gallery of the dimer formed from from two 4-OH-DMT molecules in base.

I have already mentioned 4-chloro-DMT somewhere else.
 
Although I do have a physical copy of tihkal, i dont read it very often. Im more interested in plants extracts etc than synthesis in terms of the tryptamines. Therefore I guess my knowledge of this area is far less than some of the more experienced veterans who have excelled in this area.

However, since 5-MeO-AMT is described as horrible, and 4-MeO-DMT gets shredded by the MAOI enzymes, why not 4-MeO-AMT then?
 
Ah, excellent. Hadn't thought of it like that before.

Does anyone know whether conformationally restricted tryptamines have increased activity, like Dimethyl-[2-(5H-1-oxa-5-aza-s-indacen-7-yl)-ethyl]-amine (Oxygen off the -5, ring rebonded at -6 on the indole system, aromaticized)?

(Such as the difuran rings on 2C-B-DFLY)
 
MattPsy,

Do you mean a three ringed compound? If so, I don't predict activity, but that doesn't mean it's not worth an assay.

Smyth,

Give up. Just kidding. (?)
 
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