Incunabula
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☛ Official ☚ The Small & Handy 2-Trifluoromethyldeschloroketamine (2-TFMDCK, TFM-K) Thread
- Thread starter roi
- Start date
Good thing the Soviets weren't so anal about drug nomenclature 
"Comrade Commissar, I synthesize new benzo for glory of Mother Russia. Is called 1-Desmethyl-2-Chloro-7-Deschloro-7-Bromo-Diazepam."
"Nyet, this will not do, is too long. Call it "Phenazepam" because it has phenyl ring, da?"
"But almost every other benzo has phe- ...I mean "Da, Comrade Commissar!""
"Comrade Commissar, I synthesize new benzo for glory of Mother Russia. Is called 1-Desmethyl-2-Chloro-7-Deschloro-7-Bromo-Diazepam."
"Nyet, this will not do, is too long. Call it "Phenazepam" because it has phenyl ring, da?"
"But almost every other benzo has phe- ...I mean "Da, Comrade Commissar!""
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This is the result of CYP analysis to calculate probable metabolic attack sites:
http://www75.zippyshare.com/v/7yMU3j6R/file.html
As expected, cleavage at the TFM (at the 'stem' as you put it) is low, at rank 11, and cleaving of fluorines is even lower, just doesn't happen. I personally also expect that equilibrium put above, although it is not related to enzymatic activity, to be negligible as far as actual fluoro dissociation but nevertheless it may stabilize the ring - I'd say it is just relatively stable and the ring hardly needs any extra stabilization - thats about it?
As for what DOES happen: we expect to see the same kind of metabolism of ketamine: N-demethylation, and hydroxylation on the cyclohexyl ring: next to the 2'-oxo, next to that or both - and IIRC glucoronidation.
It's always possible the TFM makes for slightly different interaction with the enzymes, but that site in itself is virtually impervious to metabolism as with K.
The size of TFM appears to be somewhere in between chloro and bromo depending on how you calculate it: it's more blunted instead of the spherical electron cloud of plain halogens. So like a squashed chloro?
Here is a simplified depiction of chloro (bright green) bromo (dark green) and TFM (dark sickly yellow) substituted on a phenyl ring:
http://imgur.com/a/JdR04
@ Phenazepam: haha yeah that always confuses me, sometimes I think phenazepam has basically no subsitutions because of the name - but that would just be the very weak plain benzodiazepine.
I vote against any sort of cyclidone name - while generally not bad for a drug that resembles say PCE such as what is among other things called O-PCE, it would be a shame to basically disregard how utterly close this TFM compound is to K not to mention the length of that cyclidone name - little is achieved. TFM-K would be fine with me, I don't see anything wrong with it for a trivial abbreviated name which definitely doesn't need specification as to where that TFM is unless there surface compounds where the TFM is atypically placed. At which point, just call that e.g. 3-TFM-K.
Leaving the deschloro out doesn't really imply anything about the chloro: the TFM can be an addition as much as a substitution - since substitutions are very natural in compounds bein mimicked it's not weird at all to assume that the TFM is taking the place of the chloro instead of being added somewhere.
Just not trifluoro-K cause it suggests very different things omitting the carbon.
Sorry if this belongs in that nomenclature thread. I respect your opinions, just have my own.
http://www75.zippyshare.com/v/7yMU3j6R/file.html
As expected, cleavage at the TFM (at the 'stem' as you put it) is low, at rank 11, and cleaving of fluorines is even lower, just doesn't happen. I personally also expect that equilibrium put above, although it is not related to enzymatic activity, to be negligible as far as actual fluoro dissociation but nevertheless it may stabilize the ring - I'd say it is just relatively stable and the ring hardly needs any extra stabilization - thats about it?
As for what DOES happen: we expect to see the same kind of metabolism of ketamine: N-demethylation, and hydroxylation on the cyclohexyl ring: next to the 2'-oxo, next to that or both - and IIRC glucoronidation.
It's always possible the TFM makes for slightly different interaction with the enzymes, but that site in itself is virtually impervious to metabolism as with K.
The size of TFM appears to be somewhere in between chloro and bromo depending on how you calculate it: it's more blunted instead of the spherical electron cloud of plain halogens. So like a squashed chloro?
Here is a simplified depiction of chloro (bright green) bromo (dark green) and TFM (dark sickly yellow) substituted on a phenyl ring:
http://imgur.com/a/JdR04
@ Phenazepam: haha yeah that always confuses me, sometimes I think phenazepam has basically no subsitutions because of the name - but that would just be the very weak plain benzodiazepine.
I vote against any sort of cyclidone name - while generally not bad for a drug that resembles say PCE such as what is among other things called O-PCE, it would be a shame to basically disregard how utterly close this TFM compound is to K not to mention the length of that cyclidone name - little is achieved. TFM-K would be fine with me, I don't see anything wrong with it for a trivial abbreviated name which definitely doesn't need specification as to where that TFM is unless there surface compounds where the TFM is atypically placed. At which point, just call that e.g. 3-TFM-K.
Leaving the deschloro out doesn't really imply anything about the chloro: the TFM can be an addition as much as a substitution - since substitutions are very natural in compounds bein mimicked it's not weird at all to assume that the TFM is taking the place of the chloro instead of being added somewhere.
Just not trifluoro-K cause it suggests very different things omitting the carbon.
Sorry if this belongs in that nomenclature thread. I respect your opinions, just have my own.
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Incunabula
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Optimally trivial names should give a general hint at the structure of the compound, and at least shouldn't be directly misleading. (I agree for instance, that trifluoro-K would be misleading.)
Think about how many trivial names are just more or less random codes assigned in the lab. Or think about how Shulgin named many of his compounds. (yes, I agree, sometimes he was a bit too sloppy or random with his naming
)
But there is one very important factor to trivial names that some people don't seem to get, and that is that they need to be simple! Both in writing and in speech. Shulgin did get that.
No one is calling methoxetamine methoxetamine, people call it MXE. Both written and in speech. Why? Should be obvious why.
The "nor" and "des" -something way of naming new compounds, isn't some kind of super correct nomenclature - it's just a handy way for a scientist working on labeling metabolic pathways, for instance, to quickly assign new names to metabolites. Using it to naming new research chemicals quickly makes for super silly long ass names.
I personally think, as usual, that 2-TFM-K would have been much better. it isn't missleading or nonsensical, it's simple, easy to pronounce. and easy to read and write,
(People could then omit the "2" if they feel like it, until we get TFM-K's with other orientations - which is probably never)
Like Solipsis, I'm sorry for not posting in the nomenclature thread, but it seems these debates are unavoidable in threads of new compounds. I disagree with the name chosen, but it doesn't matter. This compound has a name, so let's leave it at that. I mean, who cares what it's called right? (apparently I do
lol )
Yes, I agree. It was a mistake. I actually did mean for a methyl to have been in there. 2-trifluoromethyl-ketamine.
Think about how many trivial names are just more or less random codes assigned in the lab. Or think about how Shulgin named many of his compounds. (yes, I agree, sometimes he was a bit too sloppy or random with his naming
)But there is one very important factor to trivial names that some people don't seem to get, and that is that they need to be simple! Both in writing and in speech. Shulgin did get that.
No one is calling methoxetamine methoxetamine, people call it MXE. Both written and in speech. Why? Should be obvious why.
The "nor" and "des" -something way of naming new compounds, isn't some kind of super correct nomenclature - it's just a handy way for a scientist working on labeling metabolic pathways, for instance, to quickly assign new names to metabolites. Using it to naming new research chemicals quickly makes for super silly long ass names.
I personally think, as usual, that 2-TFM-K would have been much better. it isn't missleading or nonsensical, it's simple, easy to pronounce. and easy to read and write,
(People could then omit the "2" if they feel like it, until we get TFM-K's with other orientations - which is probably never)
Like Solipsis, I'm sorry for not posting in the nomenclature thread, but it seems these debates are unavoidable in threads of new compounds. I disagree with the name chosen, but it doesn't matter. This compound has a name, so let's leave it at that. I mean, who cares what it's called right? (apparently I do
lol )Yes, I agree. It was a mistake. I actually did mean for a methyl to have been in there. 2-trifluoromethyl-ketamine.
roi
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[MENTION=174933]Incunabula[/MENTION]
Actually it is exactly super correct nomenclature. If it has ketamine in the name, that implies a 2-chloro group present. This is not the case here!
Calling 2-Trifluoromethyldeschloroketamine "Trifluoromethylketamine" is like calling 4-FA "Fluoro-PMA". The latter feels very wrong to you, doesn't it?
[MENTION=91690]Solipsis[/MENTION]
PCP = Phencyclidine, 2'-Oxo-PCP = Phencyclidinone
PCE = Eticyclidine, 2'-Oxo-PCE = Eticyclidinone
PCM = Meticyclidine, 2'-Oxo-PCM = Meticyclidinone
Makes sense, doesn't it?
I'll stick with 2-Trifluoromethyldeschloroketamine, 2-TFMDCK, 2-TFM-2'-Oxo-PCM & Trifluoromethylmeticyclidinone. They basically just roll off the tongue!
PS: Methoxetamine is a garbage name that isn't really derived from the structure - causing our substance here to be Trifluoromethylmetamine, aka TFMM. Yeah right, that name fucking sucks.
Actually it is exactly super correct nomenclature. If it has ketamine in the name, that implies a 2-chloro group present. This is not the case here!
Calling 2-Trifluoromethyldeschloroketamine "Trifluoromethylketamine" is like calling 4-FA "Fluoro-PMA". The latter feels very wrong to you, doesn't it?
[MENTION=91690]Solipsis[/MENTION]
PCP = Phencyclidine, 2'-Oxo-PCP = Phencyclidinone
PCE = Eticyclidine, 2'-Oxo-PCE = Eticyclidinone
PCM = Meticyclidine, 2'-Oxo-PCM = Meticyclidinone
Makes sense, doesn't it?
I'll stick with 2-Trifluoromethyldeschloroketamine, 2-TFMDCK, 2-TFM-2'-Oxo-PCM & Trifluoromethylmeticyclidinone. They basically just roll off the tongue!
PS: Methoxetamine is a garbage name that isn't really derived from the structure - causing our substance here to be Trifluoromethylmetamine, aka TFMM. Yeah right, that name fucking sucks.
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Agreed that nor- and des- ... prefixes are specific since they specify what exactly is present, added, lost or substituted whether it be metabolism or by design. They DO make for silly long ass names, and long names just won't be used - and that is the whole point: a trivial name should give enough hints about what the drug is like or derived from or comparable to, while just not being wrong. If long names were okay people would use IUPAC or all talk like chemists instead of abbreviating until little more than a few letters are left.
Ketamine implying the chloro group present? I think you just made that up, that you feel that way because it is one of the major things singling out ketamine from other ACA's. I get why. To be more precise, ketamine is the best PCM drug we have according to a lot of people, previous attempts to modify it weren't really successful (mainly that 2-MeO version sucked hard). The NENK was unexpectedly found to be lame, and I'm not even sure it's qualitatively clear that it acts K-like.
I suggest that the name reflects chemistry, history and effect: how another drug has been modified, and especially if the effects turn out alike.
And as I already said: for a trivial name I don't see what the big deal is if deschloro is left out, if TFM is an isostere for chloro.
Your Fluoro-PMA example is a poor one because amphetamine itself is the grandparent compound in that family, and PMA while not uncommon isn't really a good or popular drug, or prevalent compared to 4-FA etc. That is the reason your example is convoluted. PCM is not really a used drug, so 2-TFM-2'-oxo-PCM even if it rolled off the tongue would - while being quite correct tell the average drug user nothing about what kind of drug they have.
The problem you and i keep having roi is that imo you are unwilling to sacrifice 'correctness' in chemical nomenclature believing that alternate trivial names are too incorrect. Correct nomenclature is important to me, but trivial names are casual names - they don't have to be overly precise, just not overtly wrong. They serve the purpose of making clear to many people in an easy fashion what we are talking about.
The chloro doesn't have to be present to name something a K analogue! A bioisosteric group in stead of the chloro is about as analogous as they come.
I do like the eticyclidone type names when they are not too long or easy to mix up, and cover a number of the ACA dissociatives that aren't very close analogues to another very well known one. Like the trypts (metacetin etc) you can fill a whole table that way. But it would be a shame to confuse people with names unlike stuff they know, when it's really a super close bioisostere K analogue.
Just never leave out deschloro's casually in an article you write for some journal of Org Chem, thats a big no no - just realize the difference in strictness for trivial names.
When you chop off a chloro off a structure and don't replace it, then - as in deschloroetizolam it is the obvious and important way to clarify that.
Any chemist is welcome to chime and and reply, by the way, on whether they implicitly understand that something is substituted - e.g. that in 2-fluoro-K no chemist would be confused about the impossibility of two 2-position halogens present.
Ketamine implying the chloro group present? I think you just made that up, that you feel that way because it is one of the major things singling out ketamine from other ACA's. I get why. To be more precise, ketamine is the best PCM drug we have according to a lot of people, previous attempts to modify it weren't really successful (mainly that 2-MeO version sucked hard). The NENK was unexpectedly found to be lame, and I'm not even sure it's qualitatively clear that it acts K-like.
I suggest that the name reflects chemistry, history and effect: how another drug has been modified, and especially if the effects turn out alike.
And as I already said: for a trivial name I don't see what the big deal is if deschloro is left out, if TFM is an isostere for chloro.
Your Fluoro-PMA example is a poor one because amphetamine itself is the grandparent compound in that family, and PMA while not uncommon isn't really a good or popular drug, or prevalent compared to 4-FA etc. That is the reason your example is convoluted. PCM is not really a used drug, so 2-TFM-2'-oxo-PCM even if it rolled off the tongue would - while being quite correct tell the average drug user nothing about what kind of drug they have.
The problem you and i keep having roi is that imo you are unwilling to sacrifice 'correctness' in chemical nomenclature believing that alternate trivial names are too incorrect. Correct nomenclature is important to me, but trivial names are casual names - they don't have to be overly precise, just not overtly wrong. They serve the purpose of making clear to many people in an easy fashion what we are talking about.
The chloro doesn't have to be present to name something a K analogue! A bioisosteric group in stead of the chloro is about as analogous as they come.
I do like the eticyclidone type names when they are not too long or easy to mix up, and cover a number of the ACA dissociatives that aren't very close analogues to another very well known one. Like the trypts (metacetin etc) you can fill a whole table that way. But it would be a shame to confuse people with names unlike stuff they know, when it's really a super close bioisostere K analogue.
Just never leave out deschloro's casually in an article you write for some journal of Org Chem, thats a big no no - just realize the difference in strictness for trivial names.
When you chop off a chloro off a structure and don't replace it, then - as in deschloroetizolam it is the obvious and important way to clarify that.
Any chemist is welcome to chime and and reply, by the way, on whether they implicitly understand that something is substituted - e.g. that in 2-fluoro-K no chemist would be confused about the impossibility of two 2-position halogens present.
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Incunabula
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Roi. Did any one ever tell you that you're a stubborn old geezer who doesn't listen to what other people are saying. 
Solipsis said it all already, and so have I before: with trivial names, there's one thing that comes before correctness, and that's simplicity.
I don't know if you are aware, but MXE was not the name given by the vendor. It was chosen unanimously quite quickly here on bluelight, as the quick abbreviation of the monstrosity of a name: methoxetamine.
Why? Because people hate to read and type silly long ass names. And such is the fate of convoluted long names - they get chopped down in size superfast, to something that people feel like saying, reading or writing.
It's not about correctness because we are talking about a TRIVIAL NAME. It's not that correctness isn't important too, it's just not the most important thing. And if we wanted it to be super correct anyway, we'd just use IUPAC.
At least this one doesn't have 5-6 names (yet) like O-PCM/DCK/DXE/DesK/D-ketamine..
It's not out yet, so there's nothing else but the name to talk about.
Solipsis said it all already, and so have I before: with trivial names, there's one thing that comes before correctness, and that's simplicity.
I don't know if you are aware, but MXE was not the name given by the vendor. It was chosen unanimously quite quickly here on bluelight, as the quick abbreviation of the monstrosity of a name: methoxetamine.
Why? Because people hate to read and type silly long ass names. And such is the fate of convoluted long names - they get chopped down in size superfast, to something that people feel like saying, reading or writing.
It's not about correctness because we are talking about a TRIVIAL NAME. It's not that correctness isn't important too, it's just not the most important thing. And if we wanted it to be super correct anyway, we'd just use IUPAC.
At least this one doesn't have 5-6 names (yet) like O-PCM/DCK/DXE/DesK/D-ketamine..
It's not out yet, so there's nothing else but the name to talk about.
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roi
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Nah, this isn't 2-fluorodeschloroketamine, it's 2-trifluoromethyldeschloroketamine.
Xorkoth
Bluelight Crew
Well first of all ketamine isn't available to everyone. But it's probably the safest choice because of its much longer history.
I agree MXE is a special thing, but how would we find something special without trying? MXE was (is) a research chemical, without exploration of new structures it never would have been found. Ketamine was found by exploring new variations on known structures too, at some point. So was LSD.
Also I do consider ketamine kind of a waste of money because it's rather expensive and the dose is very high.
Well methoxetamine is hardly monstrous.
I actually have a friend who usually pronounces it fully. But yeah, MXE is easier and it's what I always call it. People have been using simple names forever that don't necessary fully mean anything chemically. Like LSD-25... the 25 is just because it was the 25th explored out of that research, it tells nothing about the structure at all. Even with ketamine, people cal, it K a lot of the time. Popular drugs get shorthand names, it's only natural.
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lysergamide
Bluelighter
I will be trying this one if it comes my way
I think ketamine is one of the safest, probably second to MXE. The latest ones and 3-MEO-PCP can very easily lead to manic behaviour and a decrease in cognitive functioning in heavy use that can continue into the sober mind for weeks after and triggered worse by other drugs after. They are currently only available to a small audience, if it was like ketamine and people were using it at parties there would be some bad cases.
Ketamine and MXE both have negative physical symptoms. But old BL posts from before 2010 discuss the chronic use of ketamine that was going on when it was available. As long as your exercising, putting lots of food in your stomach and drinking plenty of water when using ketamine and its pure you shouldn't run into too many issues. I've been taking it over 6-7 years now and would use minimum 3g a session more like 14g, I'll piss more often but if I take a break for a few months it calms down. I found MXE still had similar effects in daily use for extended periods (e.g. 2-3 weeks) also. The others I think you'd be loosing the plot a bit before being able to use that long.
I think ketamine is one of the safest, probably second to MXE. The latest ones and 3-MEO-PCP can very easily lead to manic behaviour and a decrease in cognitive functioning in heavy use that can continue into the sober mind for weeks after and triggered worse by other drugs after. They are currently only available to a small audience, if it was like ketamine and people were using it at parties there would be some bad cases.
Ketamine and MXE both have negative physical symptoms. But old BL posts from before 2010 discuss the chronic use of ketamine that was going on when it was available. As long as your exercising, putting lots of food in your stomach and drinking plenty of water when using ketamine and its pure you shouldn't run into too many issues. I've been taking it over 6-7 years now and would use minimum 3g a session more like 14g, I'll piss more often but if I take a break for a few months it calms down. I found MXE still had similar effects in daily use for extended periods (e.g. 2-3 weeks) also. The others I think you'd be loosing the plot a bit before being able to use that long.
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boselect
Greenlighter
Roi. Did any one ever tell you that you're a stubborn old geezer who doesn't listen to what other people are saying.
I released the IUPAC elsewhere then he posted his take on the naming and that damn dick pun doomed acronym and declared he'd rewrite it's wikipedia entry til the end of time (or until at least one vendor coined it) so I didn't fight it, mardy fucker with his wiki cred.
roi
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Did you seriously just call me old? You're fucking dead, kiddo.
Are you trying to find a trivial name that somewhat resembles the substance or not? If not (as with methoxetamine), I have no idea why you even would want to discuss the structure and nomenclature, just go call it FXK or something like that. Simply invent something that has no meaning but sounds good.
I guess people will call it by the vendor given name once it's out, which we can't really influence. However the ones I proposed are at least correct and make sense.
Are you trying to find a trivial name that somewhat resembles the substance or not? If not (as with methoxetamine), I have no idea why you even would want to discuss the structure and nomenclature, just go call it FXK or something like that. Simply invent something that has no meaning but sounds good.
I guess people will call it by the vendor given name once it's out, which we can't really influence. However the ones I proposed are at least correct and make sense.
I will be trying this one if it comes my way
I think ketamine is one of the safest, probably second to MXE. The latest ones and 3-MEO-PCP can very easily lead to manic behaviour and a decrease in cognitive functioning in heavy use that can continue into the sober mind for weeks after and triggered worse by other drugs after. They are currently only available to a small audience, if it was like ketamine and people were using it at parties there would be some bad cases.
Ketamine and MXE both have negative physical symptoms. But old BL posts from before 2010 discuss the chronic use of ketamine that was going on when it was available. As long as your exercising, putting lots of food in your stomach and drinking plenty of water when using ketamine and its pure you shouldn't run into too many issues. I've been taking it over 6-7 years now and would use minimum 3g a session more like 14g, I'll piss more often but if I take a break for a few months it calms down. I found MXE still had similar effects in daily use for extended periods (e.g. 2-3 weeks) also. The others I think you'd be loosing the plot a bit before being able to use that long.
Indeed, ketamine or MXE feel less toxic on the body than 3-MeO-PCP or o-PCE, but because of the long lasting effects of those ones. I feel myself more responsible and healthier with my 10-20mg once/twice a week 3-MeO-PCP/o-PCE oral doses than ever. With MXE or ketamine, binging was a daily and huge habit. I could easily snort 5g's of MXE or ketamine in a week... I think in the long term, this usage is more dangerous and toxic than my actual sparing of small mgs oral dosages.
boselect
Greenlighter
Coming months.
Incunabula
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Relax. I'm probably older than you
And TFM-K doesn't give a hint about the structure?
For what ever it's worth, pubchem actually calls Bromoketamine just that. I can't see why fluoro or trifluoromethyl substitutions should be any different. I'm assuming Pubchem is run by real chemists, no?
https://pubchem.ncbi.nlm.nih.gov/compound/71588007#section=Top
I'm done with this debate.
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Transform
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If pharma companies can come up with proprietary names, why can't we? Bluelight has a big influence on things like this.
How about "Triflukamine" or trifluktamine.
Please suggest some other names and we'll put them in a poll. They should distinguish from 2F-DCK (some indication of trifluoro) and I think it's good to get the letter k in there somewhere. The winning name will go in the title and we'll push it here and elsewhere
How about "Triflukamine" or trifluktamine.
Please suggest some other names and we'll put them in a poll. They should distinguish from 2F-DCK (some indication of trifluoro) and I think it's good to get the letter k in there somewhere. The winning name will go in the title and we'll push it here and elsewhere