2C-T family and MAOI properties

rikki_tikki

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It has been pointed out to me by the chemically savvy that Sulfur-Substituted alpha-alkyl-phenethylamines as selective and reversible MAO-A Inhibitors does not in fact mention any PEAs that have hydrogen in the R-7 position (the ones that would be of interest to us), but only those that have methyl or ethyl. What other articles have been published that support the "2C-T-7 is an MAOI" theory?
 

Filkins

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I was wondering about 2c-t-2 as well.
On one occasion I've eaten twenty mg's 2ct2 and a mda roll, and had the time of my life due to perfect spacing.
Now since then I've heard it doesn't mix with mdxx due to it being an maoi [I think thats the one?] at certain doses.

Would love to know so I can see about repeating it or not
 

fastandbulbous

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I'll try and find the paper that catalogued the MAOI properties of the 2C-T-xs & alephs (along with a few other weirdo compounds). 2C-T-2 doesn't reach the IC50 with an average dose, but 2C-T-7 does; obviously routes other than oral can produce much higher peak plasma concentrations, which I believe is where the whole thing turns ugly (esp for 2C-T-7).

The sulphur atom on the 4 position seems to get into the active site of MAO-A, but once in there it stops it from changing to the active conformation. That sounds right to me as sulphur is directly below oxygen in the periodic table, so will have a similar setup of electrons
 

Filkins

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Its my fav combo so far that I've tried

Oh wait its my only one.
but still was AMAZING <3
 

FrostyMcFailure

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wait u filkins, have you dropped 2c's with classic MAOI's or wut?
 

rikki_tikki

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I've skimmed through the abstracts of every single article that has "phenethylamine" as keyword -- bupkis... F&F, could you just point me to the article? I'll pay for it if I have to.
 

vecktor

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rikki_tikki said:
I've skimmed through the abstracts of every single article that has "phenethylamine" as keyword -- bupkis... F&F, could you just point me to the article? I'll pay for it if I have to.

Sulfur-Substituted -Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors: Biological Activities, CoMFA Analysis, and Active Site Modeling

Alejandra Gallardo-Godoy, Angélica Fierro, Thomas H. McLean, Mariano Castillo, Bruce K. Cassels, Miguel Reyes-Parada, and David E. Nichols*

J. Med. Chem., 48 (7), 2407 -2419, 2005
 

djfriendly

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Last edited:

djfriendly

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^ OK, so seeing that apparently no one disagrees with this, why are we claiming to know as fact that 2C-T-7 etc. are MAO inhibitors? Anyone have a different study which refers specifically to 2C-T-7?
 

5-HT2

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^^^This has been looked at, and it has been found that 2C-T-7 causes significant inhibition of MAO at doses that are highly likely to be recreationally relevant. Bilz0r once posted a table from that article in a thread on this topic, and over the past few year or so, I've been intermittently trying to find either his post or the reference cited therein with no success. Hopefully f&b will have better luck than I ;)
 

fastandbulbous

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^ It's one of those posts that are elusive little buggers. I know it was from the time when BilZ0r was an ADD mod, but that's about it. I did see another piece, which made me think it must be the sulphur atom looking like an oxygen, but not behaving the same at the 4 position on the phenyl ring must be the cause. Another indirect piece of evidence is the fact that 2C-T is active orally wheras 2,4,5-trimethoxyphenethylamine isn't. The fact that 2,4,5-trimethoxyamphetamine is active as well (and the alpha methyl group protects it from attack by MAO by it being a competetive inhibitor - albeit not a strong one) does sort of hint that all of the 2C-T-x compounds owe some of their activity to the 4-sulphur atom doing the same job as the alpha methyl group
 

mad_scientist

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The other reason that 2CT7 is thought to be a particularly strong MAOI is that the n-propyl derivative (i.e. ALEPH-7) was the strongest MAOI in the series that was tested, so assuming the same holds true for the phenethylamines, 2CT7 will be the strongest.

Not to mention the 2CT7 deaths are highly suggestive of MAOI activity being the cause (i.e. death occurring when it was administered by snorting but not when same dose was taken orally, and when it was combined with MDMA or ephedrine)
 

any major dude

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i've been interested in the 2c-t-x maoi thing for a while now... especially with regards to 2c-t-2. I haven't been able to find anything definitive on it, but I have read all the trip reports i could find, and the only ones that were negative or expressed obvious symptoms of serotonin syndrome were pretty high doses, and/or insufflated, and none were all that severe (no deaths or hospitalizations, unlike 2c-t-7). This would lead me to believe t-2 is a much weaker MAOI than 2c-t-7. What do you guys think?
 

Toast to the Spirits

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I was wondering about 2c-t-2 as well.
On one occasion I've eaten twenty mg's 2ct2 and a mda roll, and had the time of my life due to perfect spacing.
Now since then I've heard it doesn't mix with mdxx due to it being an maoi [I think thats the one?] at certain doses.

Would love to know so I can see about repeating it or not
Will you tell us about your timing?
 
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