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☛ Official ☚ The Big & Dandy 2C-TFM Thread

Due to all this fluoro-substitution that's going on, I wonder how all these play out against each other

4-fluoromethyl-2,5-dimethoxyphenethylamine
4-trifluoromethyl-2,5-dimethoxyphenethylamine (2C-TFM)
4-(2-fluoroethyl)-2,5-dimethoxyphenethylamine (2C-EF)
4-(2,2,2-trifluoroethyl)-2,5-dimethoxyphenethylamine
4-pentafluoroethyl-2,5-dimethoxyphenethylamine.

The potency of the 2C compound seems to be very dependant upon the strength of the electron withdrawing group on the 4 position of the benzene ring (the halogens also fit this pattern). The electron withdrawing power is dependant upon the number and position of the fluorine atoms on the carbon chain.

Using this logic, there are some good guesses you can makle about activity

4-(2,2,2-trifluoroethyl)-2,5-dimethoxyphenethylamine > 2C-EF

2C-TFM > 4-fluoromethyl-2,5-dimethoxyphenethylamine

and probably (pending the group not just being too fuckin' big), the pentafluoro compound will be the most potent.

So now we make a hunt for electron withdrawing groups that are stronger still in an effort to find what is optimum
 
Wow, fastandbulbous, I really appreciate your knowledge, actually great to read something like that. Other moderators care a shit about the topics.
yeah...sorry for offtopic...just wanted to say that a couple of times.

Can you say something about the possible stability of the molecule based on its structure? Get a bit more of that stuff soon and think about storing it or just keep it like the other 2c-x's.
 
It sounds absolutely spiffing!

Although you said it had the 4-halogen type feel to it, is there any one that it was most like (or any of the 2C-x's for that matter). DOTFM sounds like a really good prospect in light of your 2C-TFM trip report - and most probably active in the 500-1000ug (0.5-1mg) range!
 
It sounds absolutely spiffing!

Although you said it had the 4-halogen type feel to it, is there any one that it was most like (or any of the 2C-x's for that matter). DOTFM sounds like a really good prospect in light of your 2C-TFM trip report - and most probably active in the 500-1000ug (0.5-1mg) range!
Click to expand...

Well lesee, the halo's i've tried are 2c-b, 2c-c, 2c-i, i'd say most like 2c-b - ... but a lot fucking better!!!

Its got its own flavor, but such a nice one.. it felt so clean, and ... the colors.. best color enhancement by far outta all those. Yes, DOTFM does sound interesting now.. i've had DOB and DOI, and would take a guess DOTFM would.. just be better hehe.

Next time I take LSD i will probably throw some -TFM on top of it, i bet it will be a great combo.. the fucking colors from 2C-TFM are just.. beautiful hehe.


I *hope* to get to try DOM finally real soon.
 
wow...your report sounds nice.
Really comparable to 2cb?
Would you say closer to the other 2ct-x's or to the 2c-x's?
Is the dose you took (7mg's right?) preferable?
 
Another report - 8mg

Hi guys,

Ximot and myself tasted 2C-TFM at 8mg 10 days or so ago. Here is the trip report:

http://www.bluelight.ru/vb/showthread.php?s=&threadid=208997

Quick summary:

I got to a Plus 2, maybe plus 2.5.... it was a nice ride, but not the ass-kicking I expected. There could have been tolerance issues at play due to a medium dose of mescaline 3 days previous.

For me, TFM felt like something of a cross between 2C-I and 2C-D. Lots of clarity, music sounded good, some minor CEV's.... could be a nice clubbing ally.

Love 'n light,
Neo
 
^ Only problem with an NO2 group is that it's also quite polarized (unlike say CF3) and that part of the 5HT2a receptor requires a lipophillic/hydrophobic group, as well as reducing its BBB permeability (those factors being reflected in the dose required for activity). The ideal group would really need two opposite criteria - a strong electron withdrawing capacity, but low polarity (offhand I can't think of anything better suited than CF3 group). The best bet would be some sort of organic group with a lot of charge separation going on - maybe something like methoxycarbonyl (eq to a benzoic acid ester), but then the size of the group starts to come into play
 
In the name of truth and harmreduction:the batch I tasted (see my report on page1 2C-TFM thread) was about 94% pure,reminder 2C-I.I decided the Jodo to be well below threshold and gave it a try.I'm pretty sure to have been in or close to plus-three land with 5mg.It felt safe though.

The batch in question with its from 40-50% (hard to determine as the wavelenghts are totally out of sync) CI content had some other minor impurities.I'm not surprised that 8mg won't give even a +3 (whatever batch it was,the CI impurity is a general issue!)

Be careful with that one.Research chemical means research chemical
 
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!)
 
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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...
 
I always thought a F3C-CH2 would be an attractive group, considering the increase in potency form CH3 to CH3-CH2
Click to expand...

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)
 
" 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.
 
impure 2c-tfm LCMS results

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..
 
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.
 
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