N-hydroxy/N-methyl 2-fluoroamphetamine?

[Imperial Tacohead]

I've been informed by a certain source that he intends to phase out his production of 2-fluoroamphetamine in favor of what he referred to as N-hydroxy-2-FA and N-methyl-2-FA. I'm a math major, not a chemist, but it's been my hobby lately to explore the major drug families and hunt down uncommon variants, and I've never heard of these. Do they even exist in the wild right now? 2-FA is relatively obscure enough to start with, but I have absolutely no idea what I might expect from these, or if it's worth the experiment. Useful information and/or wild speculation would be most appreciated.

Edit: Am I correct in assuming that by N-methyl he's referring to 2-fluoromethamphetamine?

 

[phase_dancer]

Edit: Am I correct in assuming that by N-methyl he's referring to 2-fluoromethamphetamine?

Along with phthalimidopropiophenone, 2-FMA was found in the Neorganics product, SC II a few years ago. We also have some subjective reports from a BL survey which will be published soon.

 

[Imperial Tacohead]

I found that in my search, although due to the cocktail nature of the product I couldn't learn anything about the drug's effects in a vacuum. I imagine the fact that it showed up in party pills at all suggests good recreational potential, although that's just a guess.

The 2-fluorohydroxyamphetamine (if I'm parsing what he said correctly) is probably the more interesting one, because I can't find reference to it anywhere. From what I gather 4-hydroxyamphetamine is one of the rubbish uninteresting ones. As a person almost entirely ignorant of biochemistry, I wonder if there's any reason to hope that 2-FHA might show some promise.

Basically I'm really hoping either of these will turn out to be worthwhile, to make up for the loss of 2-FA, which I've found to be a really remarkably clean, non-abusive, carefree stimulant. I honestly wonder why it hasn't found some sort of clinical use yet.

 

[fryingsquirrel]

My guess is n,hydroxy 2-fa should be pretty much identical to plain 2-fa. It should be metabi;ized to it.

 

[Phener]

This reminds me of my speculations in the discussion of both FLEA and the HOT compound where they also showed paired molecular structures with their prototypes that differ only by a single oxygen atom. Again, might there be some metabolic interconversion within the body? The immediate thought would be that the oxygen atom (the hydroxy group) might be metabolically removed, and the effects of either drug are due to the action of MDA. But the opposite direction is in many ways more appealing, the in vivo conversion of MDA to MDOH. Why more appealing? For one thing, oxidative changes are much more common in the body than reductive changes. For another, the conversion of amphetamine to N-hydroxyamphetamine is an intermediate in the conversion of amphetamine to phenylacetone, a known metabolic process in several animal species. And that intermediate, N-hydroxyamphetamine, is a material that gives the famous cytochrome P-450 complex that has fascinated biochemists studying the so-called NADPH-dependent metabolism.

I would put my money on the likelihood of MDA going to MDOH if it should turn out that the two drugs interconvert in the body. And in that case, it would be MDOH, or another metabolite on down the line that is common to both MDA and MDOH, that is the factor intrinsic to the intoxication that is produced. Human metabolic studies are needed, and they have not yet been done.

N-Hydroxy will tend to have identical effects to the parent molecule. I.e N-Hydroxy-2FA will be identical to 2-FA.

Not sure what country you are from but depending on the LAW, this may be a sneaky way around the legality of selling 2-FA (if that itself is illegal then depending on country the N-hydroxy may be legal. Of course this rules out any country with Analogue laws, UK PEA catch'all would likely grab it also).

N-Methyl substitutions will change the effects drastically. I.e 5-FA will become 5-FMA (The equivalent switch between amphetamine and METHamphetamine)

 

[tll]

Thank you guys,
a few days ago I've asked the same thing on the other source, but no one answered...

 

[fastandbulbous]

My guess is n,hydroxy 2-fa should be pretty much identical to plain 2-fa. It should be metabi;ized to it.

N-hydroxy-2-FA will slowly degrade to 2-FA anyway, soo phasing out 2-FA is a bit of a smokescreen - n-hydroxy-2-FA isn't covered by the UK phenethylamine derivatives law, but seeing it will contain some 2-FA it's a moot point. The N-methyl version is def illegal in the UK (as is the original 2-FA)

 

[hamhurricane]

Damn, 2-FA is a nice chemical. It really makes 4-FA look like poisonous garbage with all the ischuria and koro-esque penis shrinkage. I have felt bright eyed and bushy tailed all morning and if it is devoid of serotonergic activity I might say its one of the best stims I have ever tried. Those bupropion folks had it right all along - the action is in the ortho position.

 

[hamhurricane]

whoops forget uremia I ment ischuria! I need more trials before I can effectively compare it but I would say that it seems a bit more euphoric and potent than d-AMP, but do not quote me on that more trials are def needed.

 

[yoyoman]

*bump* So I see 2-fluoro-METHamphetamine is now out there in the market. I like 2-FA and i'm curious if its like going from amp to meth. Are doses smaller, the duration longer (i hope!).

There's some 3-FA going around now too, apparently.

 

[Twigs]

I would expect 2-fma to require a smaller dose and having a longer duration than 2-fa. I would definitely like to give it a go

Here is an old quote about 3-fma. Sounds pretty crazy.

I remember reading somewhere, many moons ago that 3-fluoromethamphetamine is supposed to be a 'what the fuck', monster of a CNS stimulant - even more potent than the parent meth. Sounds like it's just as well that 3-fluoro pseudoephedrine never found any pharmaceutical use or there'd be a crazier drug than meth doing the rounds!

 

[Torabora]

why should 2-fa-nhydroxy-amph degrade to normal 2-fa? I also thought that but after reading about the n-hydroxy-mda from shulgin I dont think that this is true, it can be a left over from the synthesis though.

So does anyone has any references for that degradation thing?


To the n-methyl thing:
4-FMA has a very short half-life time (about 1h), (" A Study of effects of fluoro-substituted amphetamine analogues on EEG power in rats and pharmacokinetics in serum." original: "Husso tikan anfetamin yuudotai no rat no noha ni oyobosu sayo oyobi kessyo tyu yakubutu nodo ni kansuru kenkyu") http://mhlw-grants.niph.go.jp/niph/...41&bunkenNo=200838013A&pdf=200838013A0006.pdf and http://mhlw-grants.niph.go.jp/niph/...41&bunkenNo=200838013A&pdf=200838013A0007.pdf)

a) 4-FA Pharmacokinetics:
tmax: 30 min at all concentrations
Cmax: 1 mg/kg-166, 2.5 mg/kg-325, 5 mg/kg-672 ng/ml
t1/2: 205, 210, 380 min, respectively.

b) 4-FMA Pharmacokinetics
tmax: 15 min at all concentrations
Cmax: 54, 127, 325 mg/kg, respectively, concentration is same as 4-FA
t1/2: 60, 90, 65 min, respectively.
and detected 4-FA at all concentrations, its tmax is 120 min at all, Cmax is 84, 196, 376 ng/kg, t1/2 is >360, 360, 370 min, respectively,

(this is just copied from http://www.bluelight.ru/vb/threads/356585-4-fluoromethamphetamine/page2 its not from me)

so it has mainly the effects of 4-fa dunno if this is true for 2-fma or 3-fma but it is not the same like with amph-->meth

 

[ebola?]

*bump* So I see 2-fluoro-METHamphetamine is now out there in the market.

Just a reminder that we should try to avoid announcing that things are offered by vendors. Mild as it is, it's still a way of hyping offerings by research chemical distributors.
...
If the typical SAR for n-methylation of amphetamines holds, 2-fluoro-n-methyl amphetamine should be more serotonergic and more selective than the parent compound. Subjective reports of 4fma vs. 4fa suggest that this type of SAR holds for similar ring-substitutions. I think that it is unclear whether 2fma will function as a near-prodrug for 2fa, as it is unclear why 4fma is so heavily subject to rapid demethylation while MA is not.

ebola

 

[sleepy]

i've plugged 4FA numerous times. maybe i'm retarded and can't figure out how to use my mg. scale, but i've always used pretty low doses. this, after a BAD experience w/Methiopropamine - also plugged, higher dose than i've ever come close to w/4FA. i have a lot of experience w/Meth, IV and smoking, years ago, and more recently plugging 20 mg of adderall at a time. i've found meth or even adderall cleaner, w/fewer, if any, noticeable side-effects or come down, but then again, i'm not doing a lot. i find 4FA disappointing. it may give me a high, but i always get cold and feel shitty after. i may not be doing a high enough dose, though don't want to risk another bad experience w/a research chem. i hope that is helpful.

 

[yoyoman]

bump Has anyone tried 2-FMA yet? the N-methyl version.... i hope it is at least more potent or makes it last longer like amp to meth.

 

[lenses]

bump Has anyone tried 2-FMA yet? the N-methyl version.... i hope it is at least more potent or makes it last longer like amp to meth.

2-FMA is everything you want in a stimulant, and nothing you don't. No sweating , tweakiness, just natural, relaxing (to a point) energy. It DOES have this strange anti-anxiety effect as well, it seems to either stop anxiety (I I'Ved 3-FA about 10 hours ago) and after that fun rush (which is a little more... tweaky) I dosed 2-FMA IV'd (around 70mgs) and it seemed to stop the anxiety caused by the 3-FA... I actually got some decent sleep about an hour after doing a shot.

It may be important to note I take xanax daily and take neurontin when I need to, when the xanax isn't working well enough.

Its smooth enough that you could either write a paper, or go to sleep. LIMITLESS lulz

Aghhh, better living through chemistry, thats for sure.

-lenses

 

[yoyoman]

2-FMA is everything you want in a stimulant, and nothing you don't. No sweating , tweakiness, just natural, relaxing (to a point) energy. It DOES have this strange anti-anxiety effect as well, it seems to either stop anxiety (I I'Ved 3-FA about 10 hours ago) and after that fun rush (which is a little more... tweaky) I dosed 2-FMA IV'd (around 70mgs) and it seemed to stop the anxiety caused by the 3-FA... I actually got some decent sleep about an hour after doing a shot.

It may be important to note I take xanax daily and take neurontin when I need to, when the xanax isn't working well enough.

Its smooth enough that you could either write a paper, or go to sleep. LIMITLESS lulz

Aghhh, better living through chemistry, thats for sure.

-lenses

What he said. Its what everyone says for the most part. 60mg oral seems like the sweet spot. No crash, comedown, and that anti-anxiety effect (everyone notices it) made me stop taking my scripts and now i just dose 2-fma daily. The duration/comedown do have similarities to meth but its not tweaky at all.

I also notice the no extra sweating... cause when i take vyvanse (my script) at work, or d-meth, i sweat a lot more. I don't sweat like that on 2-fma so its probably got less PNS effects than d-meth (which people always say is the cleanest/smoothest). Many samples have been taken with feedback, and without them knowing what the others said, the word "perfect" is prob the most common.

You take 3-FA when you wanna get high, 2-FMA when you go to work or school. Or need to cram etc. Same purposes as an Adderall but its more like an XR in that it can last all day depending on starting dose. I like one bigger dose in the morning then a little booster later on.

The anti anxiety effect is profound, when i'm anxious and pop a capsule of 2-fma, as it comes on my anxiety just fades, as if they snuck a benzo in or something. I dont think its serotonin related because i've been on celexa for a couple weeks (have tried 2-fma and 3-fa plenty before starting celexa, and a lot of 4-fa). The SSRI completely blocks 4-fa's 'roll' effect making it pretty useless (cause the stimulation sucks compared to the 2's or 3's) and it did seem to make 3-fa less fun.. yet i can't put my mind on why.. maybe its got some SERT release that is barely noticeable but adds something. The 2-fma is as it was before celexa so i doubt any serotonin dumping is going on.. whats the mechanism i wonder? I could literally use it in place of a xanax (but stimmed up a bit, more social, motivated etc normal amp effects).

I read (in some hard to read cell phone pics sent to me) in the Shulgin Index that 3-FA is an inhibitor of methyltransferase something to do with the body converting something into epinephrine etc like the flight/fight response. I couldn't catch much i just saw 2-fa and 2-fma listed, along with a ton of other 2-something-amphetamines or 3-... Maybe 2-fma happens to be a super super potent inhibitor of this but wasn't studied, or i just have to buy that book soon something might be in there about it.

 

[atrollappears]

I would expect 2-fma to require a smaller dose and having a longer duration than 2-fa. I would definitely like to give it a go

Nahh.

The only reason meth is more potent in vitro than amphetamine is that it crosses the BBB better. Amphetamine, when in the brain, is more potent than meth. I believe that 4-FA, with the extremely electronegative charge-redistributing fluorine, is actually better at crossing the BBB than 4-FMA.

And for the record, I've never had any sort of negative after-effects even after ridiculous doses of 4-FA... only positive, rewarding experiences of empathy and relaxation


Edit: Another thing... I urge caution with 2-FA and especially 3-FA (and variants) even more than with other RCs. It appears that the para-fluorine in 4-FA blocks para-hydroxylation, the major (maybe only) route to the formation of toxic, oxidative metabolites, but I see no reason why para-hydroxylation would not take place in the other ring substitutions. Further, para-chloroamphetamine is believed to exert its toxicity through the especially nasty 3-chloro-4-HO-amphetamine, which is formed when the body knocks over the chlorine during para-hydroxylation, so I fear that the other ring substitutions, especially 3-FA, may create some similarly nasty metabolites.
Does anyone know if any studies have been done on the DAergic toxicity of these compounds?

 

[thikal]

Another thing... I urge caution with 2-FA and especially 3-FA (and variants) even more than with other RCs. It appears that the para-fluorine in 4-FA blocks para-hydroxylation, the major (maybe only) route to the formation of toxic, oxidative metabolites, but I see no reason why para-hydroxylation would not take place in the other ring substitutions. Further, para-chloroamphetamine is believed to exert its toxicity through the especially nasty 3-chloro-4-HO-amphetamine, which is formed when the body knocks over the chlorine during para-hydroxylation, so I fear that the other ring substitutions, especially 3-FA, may create some similarly nasty metabolites.
Does anyone know if any studies have been done on the DAergic toxicity of these compounds?

Really interesting question, up!

 

[atrollappears]

Really interesting question, up!

I should clarify that I don't think 4-FA should be considered safe either, and as I mentioned in another thread I made on this subject, a lot of this is based on speculation.
Still, between this and its similarity to norfenfluramine, I wouldn't touch 3-FA.