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Novel opioid 3-Methylbutyrfentanyl

roi

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N-[3-methyl-1-(2-phenylethyl)piperidin-4-yl]-N-phenylbutanamide

3-Methylfentanyl + Butyrfentanyl = This

3-MF is 10-15x more potent than Fentanyl, Butyrfentanyl is 4x less potent than Fentanyl.
 
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roi

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Isn't fentanyl 80-100x morphine? If 3-MF happens to be 10-15x more potent than fentanyl, shouldn't 3-MBF be 10-15x more potent than BF as well, making it 2.5-3.75x fentanyl or 200-375x morphine?
 

jammin83

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Sorry, I did realize my math was wrong...200-250x morphine. Way better.

C'mon man...you know this shit is going to kill people. Couple youngsters with some new killer nodding powder, recipe for disaster...
 

roi

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I guess stuff like that happens when previous fentanyl derivatives are banned in China (at least Acetylfentanyl is illegal now, not sure about Butyrfentanyl).
 

roi

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It's not like they actually enforce this law there, you won't see acetylfentanyl disappearing anytime soon. Not even methylone and mephedrone production has stopped, which has been illlegal for years now.
 

Keif' Richards

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Are any of these fentanyl analogs euphoric like the well-known opioids? Even fentanyl itself isn't euphoric in my opinion, so I'm not going to keep my hopes up...
 

roi

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Butyrfentanyl is supposed to be much more euphoric than fentanyl. No personal experience with it though.
 

Dresden

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I've never understood why fentanyl analogue chemists never seem to add a 3,4-methylenedioxy unit to the N-phenyl group. Maybe they have and it just wasn't any good?
 

Dresden

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Also, I feel fairly sure that getting rid of the N-(C=O)CH2CH2 group of fentanyl and replacing it with N-(C=O)-O-CH3, a carbamate, would be a short acting winner.
 

roi

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Bioassay from another place (not mine):

Finally got a chance to play with the 3-methyl-butyr-fentanyl. Product seems to be on point; it comes as a shiny white powder (similar to the powder butyr-fentanyl HCl) and is of high purity.

As for the chemical itself, it's almost exactly like butyr-fentanyl, but more potent. According to Wikipedia, adding a 3-methyl group to regular fentanyl makes it 10-15x stronger per dose, and I think a similar comparison can be made with its butyramide analogue. I would definitely say that 3-methyl-butyr-fentanyl is about 10x more potent, possibly a bit more than that, but from what I've gathered it is closer to 10x rather than 15x the potency. Obviously, one should start at a lower dose to play it safe. The subjective effects are pretty much indistinguishable from butyr-fentanyl, so it's still super euphoric, and so far I haven't noticed a difference in duration.

Just a note to anyone considering buying this: please be extremely cautious. Normal butyr-fentanyl is already quite potent and has killed plenty of people, so I can only imagine what will happen if this chemical gets into the hands of your average, idiotic teenager. On top of that, I think the increased binding affinity means it possibly is even more addictive, raises tolerance even more, or even is harder to reverse in case of overdose. Take it with a grain of salt, but I've read before that (non-butyramide) 3-methylfentanyl cannot be reversed by naloxone, and I'm pretty sure I've heard someone say the same thing about butyr-fentanyl too.
 

pr0d1gy

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Do we know which isomers are produced? I thought 3-methylfentanyl had at least 2 isomers.
Would be four I think if diastereomers are considered. It seems that the cis(+) isomer of 3-methylfentanyl is the most potent by fairly significant margins. Maybe these margins could be expected to be greater for 4-methylbutryfentanyl. Would increasing the amide chain length possibly bring sterics for the isomers into greater play and possibly result in a greater gap in potency?

Either way I'm kind of surprised cis(+) is the most potent. I may be looking at it wrong or more likely have no clue about how fentanyl fits into its binding site spatially.
 
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ralf2

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3-methylfentanyl is longer lasting than fentanyl, so it's interesting that this 3-methylbutyrfentanyl is not longer lasting than it's parent (according to the bioassay above). But butyrfentanyl is already longer lasting than plain fentanyl, so perhaps it doesn't make as large a difference in this case.

Offtopic: Does any one know why 3-methylfentanyl is longer lasting? I can understand why alpha-methylfentanyl should be longer lasting, as fentanyl is mainly metabolised at this position (the piperidine amine), but why the 3-methyl increases duration?
 

dopamimetic

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but I've read before that (non-butyramide) 3-methylfentanyl cannot be reversed by naloxone, and I'm pretty sure I've heard someone say the same thing about butyr-fentanyl too.
From my personal experience, butyr-fentanyl gets readily displaced by naloxone, even with nasal administration. But it was just a few mg too much if an overdose at all, so maybe its another thing when someone takes more.
 

Cronos

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Your math needs some work!

Isn't fentanyl 80-100x morphine? If 3-MF happens to be 10-15x more potent than fentanyl, shouldn't 3-MBF be 10-15x more potent than BF as well, making it 2.5-3.75x fentanyl or 200-375x morphine?
I pray to God you are not titrating powerful fentanyl analogues with those math skills! Fentanyl is general rated 100x Morphine, though I find that a separate topic for debate and would feel 80X is more accurate yet still a generous rating erring on the side of safety when converting which is never a bad thing when dealing with compounds with LD50's that make VX nerve agents LD50 seem somewhat tame in comparison... Carfentanyl for example weighing in at 10,000X morphine & is active at 1 nanogram. That stuff can kill you even if you know what you are doing! As for your math, Fentanyl is 100X and 3-MF is 10-15x that would have you dirt naping folks converting at 200-375X when it's 1000-1500x? The shit scares me, I've seen a few need air for 20min...
 

Solipsis

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Cronos: fent analogues scare me too and I don't touch them even though I'm into opioids or have been... but it seems like you are forgetting about the butyryl part here.
Yes your 1000-1500x would be correct for 3-methylfentanyl (3-MF), but this is 3-methylbutyrfentanyl (3-MBF), stepping down the potency ~4x compared to 3-MF... so roi's math seems fine.

As for VX type agents, I swear I once heard of a possible / hypothetical medical application or at least of a drug of its class... but that is still a far cry from calling it therapeutic let alone talk about the therapeutic index.

Surely handling these fent compounds pure requires the utmost care and precision, some of the even more potent ones require special labs to handle, so yes this is sort of chemical weapon territory... however once this is put into solution I would start to wonder why the potency would really matter anymore, why it would be different than a much less potent opioid at a much higher concentration?
I think technically the therapeutic index is mostly a bitch at that point, not to mention the possible (redosing, high dosing etc) behavior of addicts. Otherwise how do you explain incidents with these drugs? Potency issues alone can technically be solved by proper measurement techniques - it would have to be things like the therapeutic index or the kinetics getting people up and down too rapidly etc, correct?

Despite this sidenote, I do not trust highly potent agonists like these, the curious tendencies regarding OD or instant withdrawal symptoms really bother me, even U-47700 shows them - I personally think that ultrapotent agents can have unusual characteristics just like NBOMe compounds have unusually freaky tendencies. All this is still unclear to me now, but until it is clear I don't trust them.
 

Nagelfar

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Cronos: it seems like you are forgetting about the butyryl part here.
Yes your 1000-1500x would be correct for 3-methylfentanyl (3-MF), but this is 3-methylbutyrfentanyl (3-MBF), stepping down the potency ~4x compared to 3-MF... so roi's math seems fine.
I think Cronos was referencing jammin83's admitted error; 76× (as opposed to) — 250×, that roi corrected, and just happened to quote roi.
 
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