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Flynalbarbital (Fluoromethylpentylal)

Flynnal

Bluelighter
Joined
Aug 14, 2012
Messages
940
UPDATE: New molecule image. I was able to find another image of this molecule on my PC. It appears to be more correct than the one initially used in the post. I don't understand why there were two separate images, but I was able to obtain some more information about the substance.

Not so long ago I found this designer barbiturate molecule that turned up out of nowhere. But soon after it disappeared, I tried to find the link again, but never succeeded, so gave up.

BIN: Flynalbarbitone INN: Flynalbarbital...also named under Fluoromethylpentylal or Flynalbital

But I thought I'd copy a picture of the molecule and keep it for posterity. This looks like a halogenated barbiturate derivative, and looks like secobarbital/pentobarbital in that it has a pentyl group for the R2 chain. The 3rd position of the pyrimidine ring looks interesting. It is a fluorinated methyl group.

Flynalbarbitone.png

This was the old molecule image, which appears to be wrong, even though the R2 side chain is a pentyl type chain.

structure.png

The molecule is supposed to look like this.

Again, these links are just my copies of these images, the original link had information about the barbiturate, including information about it's toxicity, half-life, effects, potency, and estimated MLD.

Half life: 60-100 hours
Toxicity: Extremely high, MLD is a mere 600mg (0.6g) for an average adult male (estimate only) - compare Nembutal/pentobarbital at 1000mg (proven).
Duration of action is anywhere from 10 to 30 hours, which means this is really a long-acting barbiturate, but it's sedative/depressant effect is said to be 2-3 times more potent than that of secobarbital in equivalent dosage (80mg secobarbital compared to 80mg flynalbarbital) - and this molecule reminds me of methohexital which is the most potent barbiturate to my knowledge, except clearly we're looking at a pentyl group here.

This active drug was called by the name of Flynnal Sodium and was to come in 10mg (pink), 20mg (green), 40mg (blue) and 80mg (white) tablets, with some umming and ahhing about the release of 80mg tablets due to the obvious suicide risks, and would come in small packets of 5 tablets and larger packets of 25 tablets. One group who tested the tablets for various things, including the taste, claimed that the tablets were laced with Bitrex (Denatonium). However, laboratory analysis were undertaken and the tablets contained no traces of denatonium. After that conclusion, they claimed this drug was significantly more bitter than the barbiturate Nembutal (3-4 times more bitter by memory), and assumed the bitterness was perhaps reflecting the alleged toxicity of the drug.

The effect was your classic barbiturate sedative-hypnotic effect, just much stronger than your typical barbiturate drug. After taking 80mg one subject claims he felt like his weight had gone from 100kg to 300kg and was so sedated he could barely move. He slept for 14 hours straight, according to the write up. One user took 40mg and claimed that after an hour he felt it had the same effect as 260mg of phenobarbital. Another user who took 120mg reported vertigo, effects on his "working" memory, and nausea ending with profuse vomiting. One female took 40mg and was "smashed after an hour", while another user took 40mg in total (20mg and another 20mg an hour later) and he felt it was similar to him being affected by alcohol. So, going by those texts, I would assume that the toxicity would at least be partially validated and that one of these users could have indeed died from ingesting 600mg.

Pentyl groups, at least it seems, tend to produce the most toxic of barbiturates, and because this drug appears to be fluorinated, thereby inhibiting it's metabolic mechanisms, its toxicity could increase, but a MLD of just 600mg seems a tad low for a barbiturate. Virtually all barbiturates start at ~1.5g for a MLD, with one notable exception - pentobarbital which is said to be ~1g.

Strangely enough, I used Flynnal as my pseudonym on this forum.

Tell me your thoughts. It looks like a very strange drug, and in this day and age, I'm beginning to wonder if barbiturates are being taken off the back burner and coming back on to the market. Flynnal would be the ideal anxiolytic in the context of panic attacks, and would, at least going by it's toxicity, make a damn fine implementation for physician assisted suicide, and would replace Nembutal if it were not for it's disgustingly bitter taste according to the texts - I would say that simply reducing the amount of the drug taken as a drink (a la Dignitas) with added strong sweeteners would make it more palatable for that application. We all know barbiturates are bitter, but I can't even imagine what something 3-4 times as bitter as pentobarbital would taste like, pentobarbital sodium tastes absolutely revolting! (going from memory of trying pentobarbital years ago, I emptied the capsule and took the powder for a laugh - the worst thing I'd ever tasted!)
 
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Well, as I'm a true believer in Murphy's Law, I never thought I'd ever get to find more about this stuff. But I did.

I would love to try it as well, but from the texts I'm certainly not going to chew any of those tablets, I would projectile vomit all over my screen!
It would be strictly quick swallow with a full glass of water...straight down, not even sucking on it for a second hehehe ;)

But getting them...t'is a pipe dream of mine. I've always been fond of the barbiturates, but the hangover is such a bitch though...
 
That looks like a disaster! Long acting barbs have never tickled me at all. Quite the contrary, more like getting hit with a blackjack. And I don't see how it would be "the ideal anxyiolytic in the context of panic attacks" with an 80-100 HR half life. Crikey! Cool structure though. Heaven help us if it ever gets into wide circulation. Curious for more details on the pharmacokinetics . .
 
jesus fucking christ I sure hope nobody puts this on the market. This is into the fenantyl-analogue territory of "you're going to kill ten to fifty people".

Given the amount of people who can find a way to kill themselves with things like 2c-e, we don't need another series of drugs with a milligram scale lethal dose.
And seriously, 25 count x 80mg tablets? Can you say death risk. Some people on these forums would wash the whole pack down with a colt45, then post asking if it's safe.

Given that phenobarbital is still ued for anticonvuslant meds, we don't really need more abusable seconal-type drugs to kill people...

& traditionally, halogenated ureas don't really make me think "these are liver friendly".
 
What's it speed of onset and protein binding? Fast onset barbs have more abuse potential. If it's slow-acting it'd probably just be like a more potent and toxic version of phenobarbital.

Wouldn't this be banned as a barbituric acid derivative in the US and many countries?
 
I'm pretty sure anything that resembles barbituric acid is controlled, esp. if it produces GABAergic effects. Too easy to just lump methyl/fluoro groups on everything til you find a legal compound.
 
They claimed that it would be listed under Schedule III of the US Controlled Substances Act.

It apparently has less abuse potential than barbiturates like secobarbital or pentobarbital because while it has a potentially very rapid onset of action (5 to 20 minutes), it's action is much longer than pentobarbital, and longer than say butabarbital which I consider medium acting. So it's basically a fast acting, long-acting barbiturate. Perfect for suicidal overdose (ie Dignitas) as it's toxicity and resulting respiratory depression quickly compounds due to the fluorinated group affecting it's metabolism and of course it's high lipid solubility and ionization rate. In my view it is useless for insomnia as it does not provide a quality sleep, neither do any of the other barbiturates for that matter.

It is said to have a blood plasma protein binding ratio of 15-30%, which seems strange, but the reason it is so potent is that it allegedly has an ionization rate of ~98% and 90%+ lipid solubility and very close to 100% bioavailability, the highest of any barbiturate I'm told...but I could be wrong on that. The fluorination of the methyl group at the 3rd position of the pyrmidine ring and it's low protein binding ratio is what gives it its long action and likely affects the onset as well, as 90%+ lipid solubility and 98% ionization rate would otherwise have you in the anesthetics league, and while Flynnal is extremely strong, it isn't as quick acting as the anaesthetics, and takes such a long time to get out of the system that it would be nonpractical for that use.

So, all in all, Flynnal is basically a super-strong anesthetic barbiturate that has had the brakes slammed on it with fluorination. I was told if the pyrimidine ring didn't have the methyl group fluorinated this drug would be 4 times stronger than Pentothal, and Pentothal is one damned strong drug.

Most people who would take this drug would use it as an anxiolytic in the most severe cases of insomnia, it would cure their anxiety and help them sleep...so they say..... In fact, the people researching this came up the mantra "Flynnal Sodium does what your garden variety sleeping pills won't." - that about sums it up - the hypnotic effect is of course by virtue of it's extremely potent sedative effect. I imagine the sleep quality on Flynnal would be utter shit, so that shouldn't come as any surprise...but any sleep is good, right? That's what the dyed-in-the-wool insomniac will tell you, and for what it's worth, I agree...but barbiturates affect sleep architecture and that doesn't bode well for your health, so I wouldn't bother using them.

The trouble is Flynnal is so damned strong that it will knock your pants and jacket off for potentially up to 30 hours, with a minimum duration of about 8-10 hours. So, for insomnia, 40mg would be the limit, in fact 20mg if I was to take it, 40mg making one "smashed" seems a bit heavy. God forbid 80mg, that's probably more suitable if I found myself in a concentration camp type ordeal. 200mg is considered by these researchers as an "anesthetic dose", and of course, as mentioned, above 500mg would be a suicidal dose.

In a concentration camp scenario Flynnal would be as valuable as gold to me because I could drop a few tablets and anesthetize myself, so that when my torturers have their way with me I wouldn't have to feel anything, but for most people it would be too damned strong for any practical day-to-day use potential, at that dose, anyway. 10mg maybe, take the edge off, 20mg for more sedation, but anything more than that and you're in la la land. 100mg+ causes vertigo and vomiting, if you're still awake that is, I was told, if you have no tolerance. 80mg is the maximum dose for someone with no tolerance. I suppose it's a bit like the 200mg Tuinals...

Less abuse potential...yes, maybe...depends...I think long-term alcoholics would quickly develop a love affair with Flynnal without much in the way of reservations. It is long acting yet very fast acting, so they can quickly get "drunk" and stay "drunk" for a couple of days, then redose...a couple of days...redose...but of course, with barbiturates tolerance develops, so first it's 40mg, then 80mg...then 160mg......getting closer and closer to the lethal dose. One day you walk in and...they took a little too much and ended up a corpse. It's the same old story with "barbiturics". In my view barbiturates are worse than alcohol and that doesn't say much.

Abusable? You bet your arse it is. There is no such thing as a barbiturate that is not abusable.
 
In a concentration camp scenario Flynnal would be as valuable as gold to me because I could drop a few tablets and anesthetize myself, so that when my torturers have their way with me I wouldn't have to feel anything, but for most people it would be too damned strong for any practical day-to-day use potential, at that dose, anyway. 10mg maybe, take the edge off, 20mg for more sedation, but anything more than that and you're in la la land. 100mg+ causes vertigo and vomiting, if you're still awake that is, I was told, if you have no tolerance. 80mg is the maximum dose for someone with no tolerance. I suppose it's a bit like the 200mg Tuinals...

Would the way it affects inhibitions, reaction time, etc. be worth it in the camp scenario? I'm actually curious, not trying to cut down what you're saying.
 
We need better euthanasia options, so I wouldn't mind this on the market.

We need an antagonist at the Christianity receptor site concomitant with it unfortunately for it to have any real value.

:\
 
Don't you think a Christianity agonist would actually be better? I mean you would actually see the light just before you go. I'd opt for that any time. And didn't that dickhead Dawkins conduct some experiment wherein certain parts of the brain were electrically stimulated and generated the feeling of a "higher being"? Ketamine does this too to some individuals. I know I want to be in a K-Hole when i die. 300mg intranasal ketamine followed by 2g heroin/phenobarbital in an IV drip. That's the way to go.


Lol I think neither would do anything, since there is no Christianity receptor. :P But, forgoing that, I'd rather die with my current non-religious-book beliefs intact. I think I'd much rather die with IV DMT. And not for the feeling of a higher being or anything, just for the pure chaos and creative overflow of mangled concepts.

As for this drug, wow, sounds like someone went overboard making/coming up with it. Seems like more of a look into how changes in the structure will effect it's length and potency scientifically, more so than anything I(hopefully anyone) would try to market hahah(although from what you said, I am sadly wrong, but at least they mysteriously quit :P)..
 
Well I wouldn't put a halogenated amine in my body for any reason, ever. And any compound that I see with an N-X bond (especially alpha to an electron withdrawing functionality like a carbonyl), my first most immediate thought is: mmmk, not a drug (and in the case of everything but F its likely to be an explosive oxidizer *see trichloroisocyanuric acid for a textbook example).
 
The drug is defintiely not explosive, in fact this was one of the things discussed in the white paper, and it was cleverly designed so it would never be dangerous in that regard, but I don't think the 3rd position of the ring was charged as appeared in the first image I provided. In the second image, it's just the raw barbiturate we are looking at, not it's sodium salt, but the first image appears to be wrong according to the white paper specs, and the newer image appears to be the correct one, but for an image of the sodium salt, you'd simply write Na+ and pick either the 1st or 3rd position and negatively charge it which in the case of F would be F- and in the case of HN would be N-. I am not entirely sure if it is the 1st or 3rd position that is negatively charged, but someone with a deeper understanding of barbiturate molecular structures could help point out any obvious inadequacies in my explanation.

But, the latest image is the correct one.

It is basically a barbiturate analogue that closely resembles methohexital which was, to my knowledge, the very strongest barbiturate until the discovery of Flynalbarbital (also Fluoromethopental or fluoromethylpentylal sodium) which seems to have taken the crown.

The image, which I've updated and added, is in my first post, but here it is again:
structure.png


Fluoromethopental is basically in the same group as methohexital or hexobarbital but with R2 changed to a pentyl chain of the same general shape as per methohexital, and, like it and hexobarbital, sharing the same methyl group at the 3rd position of the pyrimidine ring, just that the methyl group has been fluorinated which seems to have a profound effect on the barbiturate action.

Hexobarbital was an EXTREMELY powerful barbiturate, in fact, so powerful that it was taken off the market and was no longer used, because it was too dangerous to use as an anesthetic as the dosages seemed to be erratic and were not really uniform across patients and weight calculations, and many patients died from respiratory collapse - which is a real problem with all barbiturates. Unlike hexobarbital, Flynnal seems to produce more uniform effects, and has noticeable psychoactive properties at a dose as low as 10 milligrams, which is unusual for a barbiturate, even with its relatively enormous strength. Flynnal, in their estimation, is roughly 4 to 5 times stronger than sodium Amytal and 2 to 3 times stronger than Seconal. As for Nembutal, I'm not sure, but easily twice as strong would be my guess. Nembutal has a more potent effect than Seconal to me, really we're splitting hairs at this point as both are very potent, but according to others Seconal is the stronger one. It is true that Seconal has a higher lipid solubility than Nembutal.

The biggest issue with Flynnal is potentially serious respiratory depression at doses higher than 120mg (120mg causes intoxication, inebriation, nausea/vomiting and vertigo to someone who is barbiturate naive). Doses at or higher than 200mg will, as a minimum induce stupor, with the maximum result being loss of consciousness and coma, and can potentially produce life threatening respiratory depression, so a person could theoretically die at the anesthetic dose of 200mg, but 600mg is quoted as the minimum lethal dose for an average adult. Secobarbital has a minimum lethal dose of 1.5 grams, but 500mg of secobarbital will in my experience cause stupor and likely lead to loss of consciousness for someone not tolerant to barbiturates or who has no cross-tolerance to, say alcohol, benzodiazepines or other GABAergic drugs.

If you took alcohol with this stuff you would literally be begging for the grim reaper. If anyone ever gets a hold of this stuff, which at this point appears to be a complete impossibility, let me know about your experiences. I for one would like to be able to validate the white paper - which isn't what I'd call a white paper, at least not on a serious note, but more like a presumptive study of individuals who simply participated in hobby chemistry <- the reason I say this is because I cannot validate it with any other references, and there is no proof of tablets, no images, and no way to contact the individuals. So, it is presumptive that I write this.

If I get more information I'll gladly pass it on. I doubt this drug will ever make it to market, it's just too damned dangerous, at least from what I have read.
 
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At the very least, this sounds like an interesting exploration of barbiturate SAR. Do you have a link to the original paper? The only reference to this compound other than this thread is an anonymous comment on a random blog.
 
The link disappeared and is no longer available. I only have sketchy information at best, but the basics are covered. I doubt this compound will ever see the mass market.

If my memory serves me correctly this was a custom synth that was being tested in vivo and turned out to be much stronger than the researchers had anticipated. If such drug were ever marketed, it would be best used for the purposes of euthanasia because I can't see how this drug would be useful for anything other than the very worst cases of insomnia. Michael Jackson with his obsession with Diprivan would have loved Flynnal as it would have done much the same thing but lasted a lot longer. Michael wanted to be unconscious at times, and this would have been very useful...

...But, as like most people, I don't have much in the way of respect for these types, I think to myself that they should just get it over and done with and take the whole lot...which is why I doubt we'll ever see Flynnal sodium on the market, at least not any time soon. I think Dignitas would love to get hold of this stuff, and perhaps even cut out the doctors so that Dignitas can control the supply themselves but that won't be possible under Switzerland's drug control legislation.

So, anxiety and insomnia, not really useful (very effective but tolerance develops rapidly).
For euthanasia, I'd say this would be much more lethal than Nembutal which is currently the gold standard.
 
I was joking.

I'm aware the drug isn't a bomb.

I certainly hope something like this doesn't appear in our overcrowded research chemical economy.
 
I certainly hope something like this doesn't appear in our overcrowded research chemical economy.

You can rest assured that it will appear. Maybe in 1-2 years or so. Don't quote me on it, but it is still classed as an initial phase-1 or 2 research chemical. What I don't understand is why it isn't listed in CHEMSPIDER. I looked every where for that thing and couldn't find it. Closest I got was...tadaaa! Methohexital, the closest structural match! ;)

I wonder if they fluorinated methohexital, what affect it would have, compared to Flynnal?

I hope it does appear, and for one reason - euthanasia

Having to swallow 15g of bitter pentobarbital powder diluted in water is not a pleasant experience, even though the patient laps into a coma and dies peacefully.
I think I'd rather swallow 4g of Flynnal powder and end up the same way. Less of the drug means it's less bitter, I know Flynnal is more than twice as bitter as Nembutal but even so it would be easier to drop 40mL of solution containing 4g of Flynnal than it would 100mL containing 15g of pentobarbital sodium ;)
 
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1-fluoro-5-(pent-3-yn-2-yl)-5-allyl-barbiturate

1-FLuoro-5-(pent-3-YN-2-yl)-5-Allyl-barbiturate which gives us FLYN

The extra N in Flynnal stands for Natrium, which is the sodium salt, and of course the AL being the common suffix for barbiturates, which gives us NAL.

BTW there is someone who managed to obtain half a gram of this most coveted poison. Apparently it is very potent, as this person claims it to be at least twice as potent as pentobarbital, this person appears to suffer from depression and anxiety among a few other issues going by their comments on that euthanasia blog, and I don't think barbiturates of any kind are going to help this person out, and will in fact make things worse for them.

Nice Irish name for a drug. Flynn stands for "Reddish" as in Red. In this case RED most certainly = POISON.
 
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