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Thread: The Big & Dandy 2C-TFM Thread

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    The Big & Dandy 2C-TFM Thread 
    #1
    Bluelight
    right then, the compound in question is 2C-TFM aka
    1-(2,5-dimethoxy-4-(trifluoromethyl)phenyl)aminoethane.

    i have not been able to find any info besides the 1994 J. Med. Chem D.Nichols article, which mentions 2-(2,5-dimethoxy-4-(trifluoromethyl)phenyl)aminoethane, and 1 other reference on a different forum, quoting a German paper.

    supposedly, similar binding activity to iodo / bromo derivs, active at 3-5mg.

    any more info, anyone?
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    #2
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    interested in this one too..anyone?
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    #3
    Flask
    *bump*
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    #4
    Bluelight Crew fastandbulbous's Avatar
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    If I remember correctly, the trifluoromethyl group has a very similar effect to the cyanide group on the charge distribution on the benzene ring, and as the cyanide group is classed as a pseudohalogen, the trifluoromethyl group must be a psuedohalogen, at least in effect on aromatic systems. So you'd expect it to be like the other similar haloalkyl group, 2-fluoroethyl (and similar in pharmacology to the 2-fluoroethyl/halogen 2C compounds)

    Interesting to see it's at least twice the potency of the other halogenated 2C's
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    #5
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    it should be rather long-lasting as the body has a hard time metabolizing trifluoromethyl groups.
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    #6
    Bluelight Crew fastandbulbous's Avatar
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    ^ With the 2C compounds (DOx as well), the group on the 4 position isn't metabolized at all. The main metabolic routes are amine oxidation and demethylation of the methoxy groups (in a lot of cases, it's just removed by the kidneys and pissed out unchanged) that means the main effect of the 4 group is down to the influence on charge distribution of the delocalized aromatic electrons, and the size/lipophillic properties of the group
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    2C-TFM 
    #7
    A German paper?Would like to know the name of the paper.

    Those 3-5mg sounds like the human dose range as the threshold dose is at 0.6mg (pretty potent stuff-probably the most potent 2C!),1.2mg already gives a clear picture of the nature of effects.
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    #8
    Bluelight Crew fastandbulbous's Avatar
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    ^ I'd imagine that the amphetamine deriv (the DOx analogue) would be active in sub milligram dosages - I think that it takes the crown from DOB/DOI as the most active DOx compound
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    #9
    thanks f&b - informative though mindboggling.

    hugo, can you add more detail? the name of the Trachsel paper and the abstract below. the rest is in german, pm me for a .pdf - especially if you can translate.

    Helvetica Chimica Acta - Vol. 86 (2003)
    Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur - Aktivitasbeziehungen

    4-Thio-substituierte [2-(2,5-Dimethoxyphenyl)ethyl]amine (=2,5-Dimethoxybenzolethanamine)
    von Daniel Trachsel

    Synthesis of Novel (Phenylalkyl)amines for the Investigation of Structure- Activity Relationships. Part 2).
    4-Thio-Substituted [2-(2,5-Dimethoxyphenyl)ethyl]amines (=2,5-Dimethoxybenzeneethanamines)

    The 4-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines) and its a-methyl analogs are known to act as potent 5-HT2A/C ligands, which have, depending on their 4-substituent, agonistic or antagonistic character. Generally, compounds with a small lipophilic substituent typically are agonists and those with a larger lipophilic substituent predominantly antagonists or at least partial agonists.

    Since little is known about the transition and more information is needed about the structural requirements of the 4-substituent to control the functional activity, 12 novel 4-thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]-amines were synthesized and spectroscopically characterized. Thus 2,5-dimethoxybenzenethiol (7) was converted to the thioether derivatives 8a - l with several alkyl, fluoroalkyl, alkenyl, and benzyl halides.

    Subsequent Vilsmeier-formylation afforded the benzaldehydes 9a - l, condensation with MeNO2 the nitroethenyl derivatives 10a - l, and reduction with AlH3 the desired (2-phenylethyl)amines 11a - l.
    Last edited by nanobrain; 24-03-2005 at 01:04.
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    #10
    Bluelight Crew fastandbulbous's Avatar
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    Actually, it ocurred to me that with the trifluoromethyl group, you can do the same as Shulgin did with the 2-fluoroethyl group to create 2C-T-21, namely put a sulphur atom in between the trifluoromethyl group and the benzene ring to give 4-trifluoromethylthio-2,5-dimethoxyphenethylamine (as Shulgin just used numbers for this series, it's hard to derive a name for it). As a pseudohalogen like group, it should produce something similar to 2C-T-21, but I'd imagine with a greater potency.

    It's just like Lego with atoms!
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    re 2C-T-22 
    #11
    Bluelight Crew morninggloryseed's Avatar
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    Originally posted by fastandbulbous
    Actually, it ocurred to me that with the trifluoromethyl group, you can do the same as Shulgin did with the 2-fluoroethyl group to create 2C-T-21, namely put a sulphur atom in between the trifluoromethyl group and the benzene ring to give 4-trifluoromethylthio-2,5-dimethoxyphenethylamine (as Shulgin just used numbers for this series, it's hard to derive a name for it).
    He already named it.

    from the 2C-T-21 entry in PIHKAL....

    The 2,2,2-trifluoroethyl compound, which I have named 2C-T-22, has been taken to the benzaldehyde stage. Reaction between 2,5-dimethoxythiophenol and 2,2,2-trifluoroethyliodide with KOH gives 2,5-dimethoxyphenyl 2,2,2-trifluoroethyl sulfide as a very pale amber oil. This, with phosphorus oxychloride and N-methylformanilide provided 2,5-dimethoxy-4-(2,2,2-trifluoroethyl)benzaldehyde as crystals that proved to be exceedingly difficult to purify. Yellow solids can be obtained from several solvents, and they melt in the 70 C area. The initially isolated fraction melted at 69-72 C and showed three major spots by both TLC and GCMS. The largest GC peak was the correct product with a parent peak of 280 m/e, and cracking fragments at 154 and 234 m/e. A small sample was finally obtained from hexane with a melting point of 78-79 C but I am not sure that even it is particularly pure. Not surprisingly, the reaction of this crude benz-aldehyde with nitromethane and ammonium acetate gave a nitrostyrene product that was a complex mixture. And there that project also rests.
    He also named the 4-(2,2-difluoroethylthio) analogue.....he calls it 2C-T-21.5 .
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    #12
    Bluelight Crew fastandbulbous's Avatar
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    No, that's the 2,2,2-trifluoroethyl thioether, the one I was talking about was the trifluoromethyl thioether. Shulgin never made anything (mentioned in PIHKAL) with the trifluoromethyl group - seems like Nichols was the one to take credit for that
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    #13
    4-Trifluoromethylthioamphetamine would be another interesting one.
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    #14
    Bluelight Crew fastandbulbous's Avatar
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    Interesting in the academic sense - definitely; as to it being a useful psychedelic/empathogen - depends upon whether it turns out to be a MAOI like 4-thiomethylamphetamine
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    #15
    hm, there's the heavy 2C-T-31: 4-((4-(trifluoromethyl)benzyl)thio)-2,5-dimethoxy-phenethylamine

    source kudos to Murp
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    2C-TFM 
    #16
    Thanks nanobrain for the reference.Is this the same Trachsel who made the 2C-YN?

    I will review the publication(s) and see what compounds he actually made.I can translate the german and post a summary of the chemicals to the Forum (it might be appropriate to start new threads for some!?)

    Apropos,it seems from the abstract as it would be all Thiocompounds (2C-T's).To remove confusion I'd thought to list them:

    2C-T-21 : the existing 4-(2-Fluoroethylthio)...
    2C-T-21.5: the (Shulgin) proposed 4-(2,2-Difluoroethythio)..
    2C-T-22 : the 4-(2,2,2-Trifluoroethylthio)..being at him in unpure Nitrostyren...
    2C-T-23? :4-(Trifluoromethylthio)..Shulgin tried to make it,it was mentioned after the T22 so should have a 23,right?The Thiol just didn't react with with CF3J (Fluorochemistry is sometimes very difficult,but yet promising.CF3J is a gas btw and I have also found out it to be unreactive in other cases)
    2C-T-31 : 4-((4-(trifluoromethyl)benzyl)thio)..heard the first time of it from nanobrain here-there is a source?.Probably down in activity as the Phenylthio Aleph-6 was a bit a dissappointment.But the Benzyl comes in a sense closer to Isopropyl (the 4) which is rather active,hmm...

    And yes the Trifluoromethylthioamphetamin (C6H6) will be scientifically interesting-don't predict anything,f&b,especially if it has Fluoroatoms in it...

    But back to the original compound of this thread,2C-TFM which is a simple Alkyl (the 2C-D,or DOM) put Fluorine on it.A 2-Fluoroethyl is known in PIHKAL as DOEF (the 2C-EF was proposed as a probable winner at 20-30mg,it turned out to be much more active...).
    Nichols finally found a way to make the Trifluoromethylcompounds,the amphetamine probably rightfully will take the crown from the DoHalos regarding potency,but there is a mentioning of disruption of animals with
    it,so be careful.The 2C-TFM seems to feel like a winner though,but I have not seen human data besides my own few,as mentioned threshold at 0.6mg,1.2mg giving a clearer view of the nature and duration,3-5mg sounding like the right dosage.I think this belongs more in the trip reports!?

    Much food for thought for Eastern (I'm on vacation until Wednesday next week)
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    #17
    Bluelight Crew morninggloryseed's Avatar
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    Originally posted by fastandbulbous
    No, that's the 2,2,2-trifluoroethyl thioether, the one I was talking about was the trifluoromethyl thioether. Shulgin never made anything (mentioned in PIHKAL) with the trifluoromethyl group - seems like Nichols was the one to take credit for that
    Yeah, I guess this is why I need to wear my glasses more when I read.
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    Trachsel 
    #18
    What a rich paper from Trachsel,lots of new compounds!Not about human data though.Will study this more deeply the next days,but I have to go now...
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    Trachsel paper 
    #19
    Below is a somewhat modified translation of the Trachsel paper about new 2C-T's with some missing fluorinated compounds finally completed.The Trifluoroethyl might be the most potent one,but will it be still psychedelic?Maybe the Allyl could be a T7 followup.
    The TrifluoroMethyl is not in the paper though (I wrongly thought it to be 2C-T-23 but the cyclopentyl is #23)

    "Diseases like depression,phobies,schizophrenie and migraine are cured with drugs particularly acting through modulation/interaction on the serotonergic system,but often these drugs lead to adverse effects because of their unselective receptor interaction.This and to understand the function of all the subtypes requires new selective ligands.

    The distinct change of perception from these hallucinogenic phenalkylamines is primarly caused by 5-HT2a agonism,but all agents act also as potent 5-HT2c agonists (plus other mechanisms).SAR of hundreds of phenethylamines is known but none showed selectivity on these 2 receptors.Responsible is the sequence homology of these receptoors,especially the high homology (80percent) in the transmembran region where the binding of these agonists occurs.

    A short description of the most potent compounds and its structural features follows (the CF3 rest is also mentioned as are the fly's with their DD ED50)......Based on the parallelity of DD and human halucinogenic potency,the fly compounds are being forecasted as highly potent in human.

    A similar high 5-HT2a affinity showed compounds with large,lipohilic 4-Substituents (hexyl,octyl,benzyl).It got apparent that such compounds (for example the 4-(3-Phenylpropyl)-2,5-dimethoxiamphetamin) acted as antagonists or at least as partial agonists.Another study confirmed the typical antagonistic nature of ligands with a large 4 subsituent,and a 2,5 dimethoxi is not even essential for affinity on the receptor.For agonism,it is required though.

    Many of the known phenethylamines have a 4-alkylthio substitution (a reference to PIHKAL is also given btw),particularly because of the easy chemical diversification possible.So 12 new derivatives have been added to the list to investigate the border between agonist-antagonist,with different large/lipophilic substituents.Only the 2C's were made as the alpha Methyl analogs possess a complex pharmacological profile according to PIHKAL.

    Chemistry was "as usual",a few problems but could be solved.A list of the compounds:

    -2C-T-3 Methallyl
    -2C-T-16 Allyl
    -2C-T-19 Butyl
    -2C-T-21.5 2,2-Difluoroethyl
    -2C-T-22 2,2,2-Trifluoroethyl (these 5 have already been assigned by Shulgin)
    -2C-T-25 Isobutyl
    -2C-T-27 Benzyl
    -2C-T-28 3-Fluoropropyl
    -2C-T-30 4-Fluorobutyl
    -2C-T-31 (4-Trifluoromethyl)benzyl
    -2C-T-32 Pentafluorobenzyl
    -2C-T-33 3-Methoxibenzyl

    It would be interesting to have the functional activities tested.With 2C-T-21 it has been shown that the potency doubles but the hallucinogenic property is attenuated considerable.The reason for this is unclear at the moment,the higher fluorinated compounds will probably give a few clues.
    It is also speculated that the benzylthioethers might be antagonists.

    (experimental part,literature references)"
    Last edited by hugo24; 28-03-2005 at 10:28.
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    #20
    Bluelighter
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    Originally posted by fastandbulbous
    ^ With the 2C compounds (DOx as well), the group on the 4 position isn't metabolized at all. The main metabolic routes are amine oxidation and demethylation of the methoxy groups (in a lot of cases, it's just removed by the kidneys and pissed out unchanged) that means the main effect of the 4 group is down to the influence on charge distribution of the delocalized aromatic electrons, and the size/lipophillic properties of the group
    oops, that was what i meant, i was kinda distracted when i made that post.
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    #21
    filling in the blanks:

    2C-T-26: 2,5-dimethoxy-4-(1,3-difluoroprop-2-yl)thiophenethylamine (difluoro analogue of 2C-T-4)

    2C-T-29: 2,5-dimethoxy-4-(propyn-3-yl)thiophenethylamine

    don't know if these have been cooked yet.

    ibid.
    Last edited by nanobrain; 29-03-2005 at 02:12.
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    #22
    2ctfm is here , will probably start human trails in a few weeks , starting off piont at 1 mg.
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    #23
    ^be careful with your human and let us know the outcome.
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    #24
    ex-amine,1mg is probably a good starting point.If it helps,here is my data with the hydrochloride of 2C-TFM.Moderator might switch this to trip reports.

    A word of caution and a note regarding set and setting:I have a similar sensitivity as Shulgin and find the doses in PIHKAL very appropriate for me.I have experience in many rc's,traditionals,low to high doses.My threshold level for changes (in awareness,mood,body but also politics,economy etc) is low,the research opened my eyes to many things.The 2 low dose exp. below were done in a normal day work environment this year,the 5mg dose was tested in proper setting/set at home 7 years ago.

    About 6 years ago I had to stop all research because I got from all psychedelic chemicals idiosyncratic overdose reactions with even lowest doses (aka 10mg 2C-T-7) with cramping,panic,stiff neck/shoulder,anxiety,this started right at the moment when the drug should have started to drop.It was followed the day after with depression/psychotic reactions which didn't subside without treatment (SSRI).So be careful for early signs like HPPD,mood swings,trips not ending fully etc.I still don't know what exactly happened,but it certainly had a large toxic and only physical component.I know of someone else which developed the same reaction after mainly 2C-B use (the purity of the compounds is not in question).If someone can help in a diagnosis or had a similar happening please let me know (it was not just a bad trip).

    Earlier this year I started to take again small amounts of psychedelics,with usual response but the come down is still accompagnied by stiffness and an unease,but psychlogicallly I'm fully stable and I must say the few trips all have been a great success in regard of personal development,view of things etc..But I'm hesitating to take higher doses again (well,I have gotten to the highest levels,several +4's,even a +5 -I know its offscale-but what would you call full contact with God?,reached all my goals, so I think I can take it more lightly now :-)

    (with 0.6mg): "Alert in 15min,then nothing for a long time,at 48min something starts to develop,some mouth paresthesie,at 1h a clear threshold is reached climbing almost untraceable to a peak at around 3 hours.Mood is up considerable,there is some tactile enhancement but almost no visual component.It produced a stimulated,fresh feeling at the peak,maybe a +/- on the Shulgin scale.It started to drop probably at 5h,reaching baseline at 7-8h."

    (with 1.25mg): "alert in 7min,probably because it has been dissolved in a too little amount of water (6ml) and got absorbed partially by sublingually.At 30min something develops,tactile enhancement apparent at 40min,well,is this a +1 at 1h?there is some visual enhancment developing,at 1.5h a slight shifting of objects is observed,colors,particularly iceblues and greens seem more pronounced.2h,maybe a +1.5,coffee break (synergism with caffeine ?),interaction with people is fine,clear thinking.A plateau is reached at around 3h,slight tremor,a relaxed buzz through my body and soul,but no CEV observed.What pops up again is the term "fresh feeling",good tactile enhancement,somewhere similar as 5-MeO-MIPT.Appetite is okay,not overwhelming but food tastes good.Dropping evident already at 4h,5h back to +1 with lingering aftereffects reaching basline at 8h.Sleep was normal,the 2.day fine."

    (with 2mg,3mg,4mg,6.3mg): "like the preceding 2 new trials,planned experiments,in the proper way of running the compound up-I've gotten wiser (in 5 years without psychedelics...)"

    (with 5mg): "This is a 7 year old experiment,in my old and very adventurous psychedelic beginning I would take the "right" dose right on.Well,it was the right dose,but I lost somehow my notes and this comes from memory.The compound came on silently starting at 25-30min,developed to a +3 plateau at around the 2nd-3rd hour,started to subside at 5-6h.Total duration was 12h,somewhat into the night,but sleep was possible after that mark.I concluded this to be a winner (unlike the earlier tasted 2C-EF),most remarkable was its caused "fresh feeling".far from antierotic.The visuals were not so pronounced,I remember few CEV,OEV were in the vein of 2C-B.Particularly the comparation to 2C-B was highlighted,but longer lasting.Knowing the term "CB like",I concluded that if there is an archetype of this class,it will be 2C-TF (as i called it then).With the dose range I'm reminded of DOM,the 1mg trial in PIHKAL etc.
    And frankly,these 5mg felt safe that I intended to up it again. But a I had to take a long break from psychedelics"
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    #25
    hugo24, thanks for that feedback.

    BTW, i also went through the same hypersensitization period with psychs, where subthreshold (literature) doses led to full-fledged freakouts.

    i believe this may be caused in part by the reverse tolerance many of the 2C's seem to induce.
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