The Big & Dandy 2C-TFM Thread

[fastandbulbous]

I'd guess that the degree to which the group attached at the 4 position is able to 'pull' the delocalized pi electrons of the aromatic ring will have a correlation to the potency. Obvious other factors (as mentioned above) are polarity and size. Polarity is important as any highly polar group will not fit into the space allowed by the receptor molecule, most probably because of electrostatic charge repulsion. Also it will severely hinder the ability of the molecule to cross the blood brain barrier. Size is a factor, as shown by Shulgin - the fact that the DOx compound with a pentyl group attached to the 4 position (DOAM) is inactive.

Attached is a jpeg showing the effect of the CF3 group on the delocalized pi electrons. All of the halogens (and some groups such as -CN and -CH2CH2F) have the same effect on said electrons, but to a lesser degree.

Possibly anything capable of doing this to a greater degree than CF3, but while remaining lipophillic (non-polar) would turn out to be even more potent (if anybody out there with a good understanding of mechanisms of org chemistry can suggest a better group, don't be shy!)

[C6H6]

I always thought a F3C-CH2 would be an attractive group, considering the increase in potency form CH3 to CH3-CH2. Another advantage is that it's probably chemically feasible.

If I remember correctly... DOAM has a very high affinity for the 5-HT2A receptor, but it has either very low intrinsic efficiacy, or is an antagonist.

An other compound, 1-(3,5-dimethoxy-4-(3-phenylpropyl)phenyl)propan-2-amine, with a group of even larger size than amyl in the 4-position, has a Ki of 4nM @ 5-HT2A and 109% efficiacy. In this series even compounds with only one methoxy are very active:
1-(2-methoxy-4-(3-phenylpropyl)phenyl)propan-2-amine: Ki 8nM, Emax 63% (which is still sufficient for psychedelic activity).
1-(3-methoxy-4-(3-phenylpropyl)phenyl)propan-2-amine: Ki 17nM, Emax 90%.
For comparison, the same paper gives a Ki of 16nM for 2C-B and 32nM for DOB (not, it's not a mistake).

Would be interesting to combine the 4-(3-phenylpropyl) with the dragonfly wings! Or to stick some fluorine on the tail phenyl...

[fastandbulbous]

I always thought a F3C-CH2 would be an attractive group, considering the increase in potency form CH3 to CH3-CH2

That's why I thought the pentafluoroethyl group (CF3CF2-) might also be a winner, as long as it's not too physically large. Other possible candidates would be methoxydifluoromethyl (CH3OCF2-) and trifluoromethoxydifluoromethyl (CF3OCF2-) as they'd both be quite strong electron withdrawing groups, but at the optimum 3 atoms long chain seen with the 4-propyl compounds (again pending steric considerations).

As for the large 4-substituent groups, I'm sure I've read somewhere that they're either partial antagonists or just ligands that bind and don't do much at all (other than prevent anything else binding)

[hugo24]

" Possibly anything capable of doing this to a greater degree than CF3, but while remaining lipophillic (non-polar) would turn out to be even more potent (if anybody out there with a good understanding of mechanisms of org chemistry can suggest a better group, don't be shy!)"

1-(2,5-Dimethoxy-4-(pentafluorsulfanyl)phenyl)-aminoethane.Yes,SF5.An extension of the highly effective TFM group,the sulfur is known and allowed at the 4 position.The thing might be a bit too big,but then,the weight is 127 like the jodo which is tolerated.There is a surprisingly sparse literature about the SF5 group (fertile ground I would say,fellow scientists!),it is stable like stone,not too difficult to make.I doubt this has ever been made into a pharmaceutical molecule.

[fastandbulbous]

Wondering whether the activity -f an SF5 would be like the 4-halogen, 4-alkylthio, or like that of 2C-T-21. If I had to place a bet, I'd think it's be most like 2C-T-21, but a sight more potent

[yaesutom]

That impure 2c-tfm that most people got, LC/MS,

-----
40.5% 2C-TFM, 42.2% 2C-I, and 4 other compounds present in 4.0, 4.4, 5.8 and 3.0 %'s

The masses I see are
207/208,
307/309 (2C-I),
250/251/264 (-TFM and I dunno whats up with the 264)
244
215
and also a peak in the "show me all masses present" of 182.1 which could be the M+1 for 2C-H
------

I don't have any of the images yet (analysed a buncha shit) but thats what my friend's got right now. Well shit 2c-tfm must be pretty fuckin' potent cause it doesn't take much of the above mix to work good, and it didn't really feel like 2c-i (i dont know whats the highest dose i've taken) it felt like the other "more pure" tfm I had a 1mg taste of.

I hope some pure 2C-TFM shows up again cause I definitely liked it, and i'd like to see how potent it really is and the effects at the higher levels without 2c-i. Also i bet DOTFM is ultra potent, and DOTFM-fly or dragonfly nfly fuck..

[nanobrain]

hugo24, any correspondence with your earlier data in re the nature of the contaminants?

[Smyth]

ultra strong compounds do not necessarily equate to agreeable effects. something like dob is vicious enough already (doberman),

OT, layout-distorting large pic of puppy removed. This is a serious forum --fizzacyst

so in my eyes dotfm does not look like a good idea. it would still be worth exploring for the purpose of research though

[fastandbulbous]

WTF has this to do with 2C-TFM?

[fizzacyst]

Offtopic BS cut out of thread. Talk about puppies elsewhere.

[hugo24]

What wavelength have your results been measured yaesutom (I guess 220nm)?2-CI and 2-TFM have very different absorption patterns (Trifuoromethyl is very elektronegative and distorts the aromat,plus iodo stuff often adds odd UV itensity),I found 230 the most accurate for those 2 because it corresponds the closest with NMR data.

The 220nm data says 46.8% 2C-TFM,49.7% 2C-I and 3.47% of an unknown polar compound XX (2smaller compounds present but unintegrated, I lost the HPLC data to reintegrate).

At 230nm: 57.9% 2C-TFM,37.7% 2C-I,2.08% imp.,1.84% imp. (ment. above),0.9% imp...I might do it again as there were doubts regarding baseline separation/slightly contaminated TFA,but it won't change the big picture.

The MS:Usually the phens show also a peak minus 17 (ammonia),264 might be that plus Methanol?
XX/with mass 215(217?) maybe 2C-C from the Jodmonochloride jodination?
On the others I have to pass.Maybe C6H6 has a good idea?In the halogenated you usually have some isomers/overreacted compounds present.

[Xorkoth]

I hadn't realized this thread existed. Since there is a wealth of information (compared to elsewhere) about 2C-TFM (and/or the impure batch), I have big and dandified it.

[hugo24]

The drawing is correct,a benzyl has an CH2 on the phenylring.

[wirreddreams]

anyone sample real 2ctfm that had no 2ci in it if so id like to here about it.I heard this stuff was really good im dieing to try it

[Delsyd]

it came and it went

now its a thing of legends.

(then again legends never die as has been shown with 2cb, 2ct7, 5 meo dipt, amt, DOM, psilocin and plethora of other substabces)

I await the return of this exotic phenethylamine

[Vanadium]

Wondering whether the activity -f an SF5 would be like the 4-halogen, 4-alkylthio, or like that of 2C-T-21. If I had to place a bet, I'd think it's be most like 2C-T-21, but a sight more potent

Are you sure that the 2C-SF5 is like other 2C-T-X ? In the pentafluorosulfanyl, the four fluor-atoms take two electron-pair of the sulfur-atom, not in the 2C-T-x ...

The SF5 has no similarity with thioethers. It is extremely lipophilic with very strong electron withdrawing due to flor-atoms. This is a sort of super pseudo halogen... bigger than iodine and more lipophilic than trifluoromethyl !

Does anyone know how the -SF5 group are eliminated out of the body ? ?

[hugo24]

That was the original rational for its designing,highly lipophilic yet strongly electron withdrawing,sort of an extension to the so far most potent groups beyond Jodine like Trifluoromethyl,2-Fluoroethylthio,2-Fluoroethyl and maybe the 2,2,2-Trifluoroethylthio/2,2,2-Trifluoroethyl (the latter two exist as well but human data is not public yet to my knowledge).Though your point about Sulfurs different oxidation state is valid.And chances that the SF5 is finally too big there are intact to formulate it positively.

As for the metabolism I would say it is stable like a stone (welcomed in the 2C series) as the SF5 is mostly inert (read up also on SF6:

http://de.wikipedia.org/wiki/Schwefelhexafluorid )

But as with all new things its expected to be a black box,ready to be enlightned!

Btw the problem with the 2C-J contaminant in 2C-TFM is hard to solve,some will be steered away by this potentially legal issue.

[IGNVS]

bump

[ODB]

Where would I be able to find info about 2c-tfm? I am very interested in this compound. I am curious how it would be synthesized and if there are any recipes available online? Could you start with another 2c to make 2c-tfm?

[yaesutom]

There's a method to go from 2C-I to 2C-TFM (thats why the impure stuff going around a few years ago had a buncha 2C-I in it, synth not done properly)

[ODB]

There's a method to go from 2C-I to 2C-TFM (thats why the impure stuff going around a few years ago had a buncha 2C-I in it, synth not done properly)

Would that be the same synth David Nichols used to make 2c-tfm? Or is there a different route of synthesis?

[planckunit]

Would that be the same synth David Nichols used to make 2c-tfm? Or is there a different route of synthesis?

As far as I know the only published synthesis of 2c-tfm is by nichols. And it involves 2c-i...

[hamhurricane]

i guess this borders on synth but, could anyone briefly describe why 2C-I would be used instead of 2,5-DMPEA as is the case for other halogens?

[tryp2fun]

i guess this borders on synth but, could anyone briefly describe why 2C-I would be used instead of 2,5-DMPEA as is the case for other halogens?

The trifluoromethyl group is added by nucleophilic aromatic substitution reactions, while the halogens are added by electrophilic substitution reactions. It is quite hard to make a CF3+ cation to do an electrophilic substitution! Thus, the usual way to make a CF3-substituted aromatic is to displace a halogen, preferably I, with a CF3- anion derived from a suitable source like trifluoroacetate in a high boiling solvent like DMF or NMP, using a copper catalyst.

[Chi-Blast]

I've recently come across some unknown 2c-x geltabs. Plenty of white powder imprinted in the gels, passed off as LSD. I took 3 of these tabs.

It is obviously a 2c-x, although it's hard to put my finger on exactly which one. Reading this thread leads me to believe it's possible that 2c-tfm was in the gels. I was thinking 2c-e/i, but the trip was ~6-7 hours, and not all that intense. Two hour come up, 2.5 hour peak, 2-3 hour comedown. No nausea, jaw clenching and quite a bit of muscle tension.

Not sure if 10-18mg of 2c-e/i can even fit on those 3 blotters, and seeing how 2c-tfm is active at such a low dose I'm leaning more toward that.

Sorry to bump an old thread, but I could use some insight from some knowledgeable members.