4-Methylmethamphetamine (not PMMA!), some comments, possible SAR speculation?

[Jesusgreen]

So a long time ago, I remember seeing a couple of threads about this chemical popping up, questioning it as a possible Mephedrone alternative and wondering if it'd be a worthwhile drug. I couldn't remember why it was left unexplored in the end so I did a quick search today, and in the threads I could find, 4-Methylmethamphetamine was said to be PMMA.

This is not true, since PMMA is 4-Methoxymethamphetamine, not 4-Methylmethamphetamine. I suspect the confusion comes from PMMA sometimes being called 4-MMA, and PMA sometimes being called 4-MA, a name it shares with 4-Methylamphetamine, a different drug entirely. To give an example of just how big the difference is, you only have to look at the cathinone analogues. 4-Methylmethcathinone is the very popular and much loved Mephedrone, while 4-Methoxymethcathinone is Methedrone, less commonly used and more of a dirty-feeling stimulant, and as far as I know it functions as an MAOI similar to PMA/PMMA. This makes the difference between Mephedrone, a toxic but fun stimulant that can be used occasionally at regular doses without noticeable problems, and Methedrone, a potentially lethal drug at slightly over the recreational dosage similar to PMA/PMMA.

So the first goal of this topic, if people are going to refer to PMMA without using the para and using the 4- notation instead, could we call it 4-MeOMA and could we call PMA by the name 4-MeOA instead? The current naming is confusing and leads to misinformation. It has also read to posters and media outlets mistakenly calling PMA "4-methylamphetamine" in PMA death articles despite this not being the dangerous MDMA adulterant.

Now I'd like to get some speculation going about the kind of effects this drug would have since there's not much info online. Not knowing much about SAR like many of you guys here, my speculation is going to be based on the relationships between 4-MeOMC (aka bk-PMMA, Methedrone) and 4-MMC (aka Mephedrone) - and the relationships between 4-MeOA (PMA) and 4-MA (4-Methylamphetamine).

4-MMC (Mephedrone) vs 4-MeOMC (Methedrone):

4-MMC:

• Consistent euphoric and pleasant effects
• People have taken extremely large doses and survived
• Not an MAOI
• Cardiotoxic

4-MeOMC:

• Euphoria seems hit and miss with some reports describing it as amazing while others finding it unenjoyable and often even dysphoric - I suspect a lot of the positive reports are due to people misspelling Mephedrone as Methedrone though, rather than people talking about this drug.
• At doses only slightly above recreational levels hot flashes, nausea and other symptoms of excess serotonin have been reported similar to PMMA, suggesting this is likely an MAOI like its amphetamine-based cousin.
• Likely to also be similarly cardiotoxic

Comparing the two would suggest 4-Methylmethamphetamine would not be an MAOI like PMMA, euphoric effects would be much easier to achieve without any real danger - and this would have a much wider safe dose range. However, Mephedrone is known be quite toxic and as such regular use of this compound would likely carry similar risks, and this would definitely not be a very safe compound - but for those willing to consume toxic drugs like Mephedrone regularly anyway, or those who consume it sporadically to reduce/avoid the damage it could still be an option.

4-MeOA (PMA, 4-Methoxyamphetamine) vs 4-MA (4-Methylamphetamine):

4-MeOA:

• Euphoria and pleasant effects near impossible to achieve as the difference between a euphoric dose and a serotonin-syndrome inducing dose is tiny
• Is an MAOI and produces serotonin-syndrome at doses barely above the recreational range, leading to many deaths in ecstasy users sold this drug under the guise of being MDMA

4-MA:

• Developed as an appetite suppressant though development later stopped. Studies on rats and later experimentation by humans never showed any MAOI activity
• While its release values are selective towards norepinephrine it seems to show more serotonergic effects, possibly making it more empathogenic than released drugs like 4-FA
• Reports I found said the substance was empathogenic and euphoric
• Users reporting bad mental effects during the days/weeks after use seemingly as a result of serotonin depletion
• Quite possibly very neurotoxic due to its close relationship to halogenated amphetamines

From this I'd conclude once again that 4-Methylmethamphetamine shouldn't be an MAOI, and should have good recreational potential. However, again trends suggest that it is likely toxic - very serotonin depleting, and potentially even quite neurotoxic like most halogenated amphetamines?

It's also worth noting that by weight many of the beta-ketones are less potent than their amphetamine analogues, so maybe 4-Methylmethamphetamine would be more potent than Mephedrone?

----

I'm not interested in this from a "This might make a good alternative to Mephedrone" standpoint, but rather one that I feel it holds the potential to be a chemical worth exploring. Likely being quite toxic this is the kind of thing I'd approach like Mephedrone and maybe give it a couple of tries spaced very far apart and otherwise avoid it completely.

Anyway does anyone have any more information on this?

I've heard reports about this currently (or in the past) being used in Ukraine and Russia, but not knowing either language I'm unable to dig any up. Does anyone know what this substance is referred to in either language or speak/write the languages? It'd be great if someone could dig up some reports and stick them through a translator.

What about some SAR speculation? Or even some reports if anyone here has actually tried it?

 

[sekio]

afaict the cathinones have a much different sar than the amphetamines do - the b-keto reduces affinity for MAO and increases affinity for DAT/NET.

I have heard people refer to 4-meo-amph as a "very rough" empathogen/euphoriant. If people abuse that for kicks Im sure someone will find 4-me-amp euphoric. the word on the playground is that plain 4-substitution is much too dangerous after all the shit with 4-mta/"flatliners"... the only reason we got to see the b-ketones with such silly substitution patterns is because their sar leads them away from the path of the monoamine releaser+maoi.

millimole for millimole methcathinone is actually a "better" stimulant than methamphetamine, its just that the b-keto is a rather polar function and hence reduces transport to the brain. hence the more fat soluble amphetamines are "more potent". but ask anyone who has compared methcat vs methamp and they will probably tell you cat is a lot stronger effects wise.

sar wise this should be a sort of amt-like triple releasing agent. its probably filthy as hell...
if you walk this path much further you'll end up considering p-chloroamphetamine as a drug, too... i hear that brain damage is totally overstated in humans!

 

[Nephtys]

A few months ago the Netherlands and Belgium had 4-MA in some amphetamines samples, error in synthesis...
Both our governments gave an official warning: too many deads because of 4-MA...

4-Methylamphetamine is NOT recreational.

 

[Jesusgreen]

A few months ago the Netherlands and Belgium had 4-MA in some amphetamines samples, error in synthesis...
Both our governments gave an official warning: too many deads because of 4-MA...

4-Methylamphetamine is NOT recreational.

The warning was about PMA Nephtys, not 4-Methylamphetamine, this is what I meant in the thread about the problem with the naming - people writing in the media about PMA are seeing people abbreviating it to 4-MA, and assuming that means 4-Methylamphetamine, when PMA is actually 4-Methoxyamphetamine. This is why I suggested we use 4-MeOA and 4-MeOMA to describe PMA and PMMA respectively, since 4-MMA and 4-MA should be reserved for the 4-Methyls rather than the 4-Methoxys.

sar wise this should be a sort of amt-like triple releasing agent

You put me more and more off this one and then go and compare it to my favourite drug of all time. Now you've further added to the confusion!

I think the fact that this has a history of use in Russia and Ukraine without gaining a nasty reputation like PMA/PMMA/4-MTA/PCA/etc makes it seem odd that this hasn't really ever appeared elsewhere. It seems like at very least it would be one of the safer ones of the lot, particularly given that 4-Methylamphetamine has also been used in humans and animals without similar adverse effects to them - so I'd have at least expected it to pop up once or twice to cater for the more reckless people who have attempted to use drugs like PMA recreationally, or possibly also those who use the more sketchy research chemicals like 4-BMC.

Is there some obvious reason why sites that have been willing to sell dangerous chemicals like those have never gone down this route? Analogue laws? Confusion with PMA/PMMA? Or just a matter of coincidence? Given the relationship to the hit seller Mephedrone I'd have thought the more unscrupulous vendors looking for their Mephedrone alternatives would have jumped on it immediately, even if it is significantly more dangerous as you suggest.

Also would the dangers and toxicity differences between 4-Methylamphetamine and 4-Methylmethamphetamine not share a similar relationship to PMA and PMMA? Because 4-Methylamphetamine seems to be safe in humans at normal doses, at least suggesting it has no significant MAOI activity - of course there's the factor of neurotoxicity and cardiotoxicity which could be present, but given the amount of neurotoxic and cardiotoxic chemicals so many of us are happy to consume I'm surprised that that would stop people going ahead and making it. Now looking at PMA and PMMA, most would agree PMA is the worse of the two, so would that not suggest that 4-Methylmethamphetamine could potentially be the safer of the two?

Just speculation of course, I'm no expert on pharmacology.

Also I found this description of 4-Methylamphetamine's effects on another forum:

It is mostly like MDMA with pronounced dopaminergic effects for the majority of people, sometimes with the faint tones of anguish and hysteria breaking through euphoria and empathy. Some people feel almost nothing at all, and it's effects are generally more variable from one person to another than those of MDMA. They last 4 hours.

Though afterwards they said some unpleasant stuff:

It has noticeable after-effects that turn into long lasting insomnia of a very specific kind, mood disturbances, disturbances of memory and cognition upon repeated dosing, pointing at serotonin depletion and possibly marked neurotoxicity. They can include a depression so black, that only heavy cocaine use comes to mind to compare it with.

 

[doppelgänger1]

The warning was about PMA Nephtys, not 4-Methylamphetamine, this is what I meant in the thread about the problem with the naming - people writing in the media about PMA are seeing people abbreviating it to 4-MA, and assuming that means 4-Methylamphetamine, when PMA is actually 4-Methoxyamphetamine. This is why I suggested we use 4-MeOA and 4-MeOMA to describe PMA and PMMA respectively, since 4-MMA and 4-MA should be reserved for the 4-Methyls rather than the 4-Methoxys.

No, it was about 4-methylamphetamine and people in belgium and eastern europe have died from it.

However I think I read once it has similar km-values as mdma.

 

[ebola?]

Im sure someone will find 4-me-amp euphoric.

The compound has a history of use in Russia in the late nineties and early 2000s. Reports indicate a euphoric, stimulating roll followed by a severe crash, with a hangover far more protracted than that of MDMA. With severe overuse, the hangover is enduring enough to raise questions of permanent neurotoxicity.

Quite a while ago, I saw EC50 data on this compound (God I wish that I saved the article, but alas...). It is a balanced monoamine releaser, nearing a 1/3, 1/3, 1/3 split of EC50s for DA, NE, and SER.

We have no reason to believe that 4-Me-m-amp would be very different.

but ask anyone who has compared methcat vs methamp and they will probably tell you cat is a lot stronger effects wise.

What? No way! I have perused numerous anecdotes, and none of these have indicated such. In fact, all have claimed the converse. Many report that if you're used to amphetamine or methamphetamine, methcathinone likely simply won't be able to get you where you want to be. I will give you that methcathinone is more physically stimulating than non bk-amps, on account of greater direct adrenergic action.

sar wise this should be a sort of amt-like triple releasing agent.

AMT is actually a great deal more selective for SERT (well, yet not very selective...)

ebola

 

[pofacedhoe]

there was thread on this years back and a guy who abused 4 methyl amphetamine said it really messed him up. he felt something was broken since doing it. possible neurotoxicity. supposedly you cant tell that sort of thing, but i'd guess that if the change in overall everyday mood was big enough you would notice something wasn't right.

AVOID

 

[Nephtys]

The warning was about PMA Nephtys, not 4-Methylamphetamine, this is what I meant in the thread about the problem with the naming - people writing in the media about PMA are seeing people abbreviating it to 4-MA, and assuming that means 4-Methylamphetamine, when PMA is actually 4-Methoxyamphetamine. This is why I suggested we use 4-MeOA and 4-MeOMA to describe PMA and PMMA respectively, since 4-MMA and 4-MA should be reserved for the 4-Methyls rather than the 4-Methoxys.

Was there another warning on PMA?
I just looked it up, in Uk/Belgium/Netherlands it was definitely 4-methylamfetamine.
If you want the official source from Beglium I can always PM you.

 

[amanitadine]

The compound has a history of use in Russia in the late nineties and early 2000s. Reports indicate a euphoric, stimulating roll followed by a severe crash, with a hangover far more protracted than that of MDMA. With severe overuse, the hangover is enduring enough to raise questions of permanent neurotoxicity.
. .
. . . . .



What? No way! I have perused numerous anecdotes, and none of these have indicated such. In fact, all have claimed the converse. Many report that if you're used to amphetamine or methamphetamine, methcathinone likely simply won't be able to get you where you want to be. I will give you that methcathinone is more physically stimulating than non bk-amps, on account of greater direct adrenergic action.



AMT is actually a great deal more selective for SERT (well, yet not very selective...)

ebola

Yeah there were loads of reports on a certain Russian site, many with complaints of never feeling the same again. And not in a good way! I've taken PMA, underwhelming, but I read a first hand report years ago that said 4-MA had a much worse, hard to describe "hangover". No thanks.

* methcath/methamphet *
Having taken both (by iv mind you, many years ago..) I can say that MA is a finer deg with less peripheral side effects. But injected, methcathinone seems to be more compulsive, shorter, more of a rush, and that monkey pulling the lever until his poor monkey heart explodes. Bad effects on the circulation that one!

 

[sekio]

I think the anecdotal reports of severe & permanent damage after abusing 4-MeA is enough to make me not want to touch it with a barge pole. MDMA is bad enough as a serotonin depleter...

I have heard of some individuals describing 4-MeO-A as a "roller coaster". That is, it's one hell of a ride but safe enough if you know what you're doing and don't overstep your limits. Never have I heard it as anything but a curiosity though - nobody compares it to anything.

Never having used mcat or m-a, all I have to go on for the effects of methcathinone being "punchier" is the comparatively higher affinity for DAT over methamp. I totally believe that m-amp is much smoother though, because of greatly reduced adrenergic effects, increased BBB penetration due to increased fat solubility, and the fact it's not being converted to (pseudo)ephedrine in yer liver.

 

[Gaius]

[4-me-amp] has a history of use in Russia in the late nineties and early 2000s. Reports indicate a euphoric, stimulating roll followed by a severe crash, with a hangover far more protracted than that of MDMA. With severe overuse, the hangover is enduring enough to raise questions of permanent neurotoxicity.

Quite a while ago, I saw EC50 data on this compound (God I wish that I saved the article, but alas...). It is a balanced monoamine releaser, nearing a 1/3, 1/3, 1/3 split of EC50s for DA, NE, and SER.

This one?

Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs.

Compounds PAL 313 and 314 are para- and meta-methylamphetamine, respectively. PAL 303 and 353 are para- and meta-fluoroamphetamine, respectively. All compounds had similar potencies as in vitro releasers of dopamine (DA) and norepinephrine (NE) but differed in potency for 5-hydroxytryptamine (serotonin) (5-HT) release [EC(50) (nanomolar) PAL 313 = 53.4; PAL 314 = 218; PAL 303 = 939; PAL 353 = 1937]

Found via: Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA)

p-Methylamphetamine (para-methylamphetamine)
It is not in Sweetman (2007). This is not an isomer of metamphetamine, but a derivative of amphetamine (with the methyl substitution on the ring: what is commonly called methamphetamine is actually n-methylamphetamine with the methyl on the nitrogen). Unlike D-amphetamine, which is a potent releaser of NA and DA but not 5-HT, p-methylamphetamine is approximately equipotent at releasing all three amines and has lower potency as a reinforcer in an animal model (Wee et al., 2005).

These would also be useful but I'm having difficulty finding the full texts:

Substituted Amphetamine Derivatives. I. Effect on Uptake and Release of Biogenic Monoamines and on Monoamine Oxidase in the Mouse Brain
Substituted Amphetamine Derivatives. II. Behavioural Effects in Mice Related to Monoaminergic Neurones

 

[Coolio]

4-MMC (Mephedrone) vs 4-MeOMC (Methedrone):

4-MMC:

• Consistent euphoric and pleasant effects
• People have taken extremely large doses and survived
• Not an MAOI
• Cardiotoxic

4-MeOMC:

• Euphoria seems hit and miss with some reports describing it as amazing while others finding it unenjoyable and often even dysphoric - I suspect a lot of the positive reports are due to people misspelling Mephedrone as Methedrone though, rather than people talking about this drug.
• At doses only slightly above recreational levels hot flashes, nausea and other symptoms of excess serotonin have been reported similar to PMMA, suggesting this is likely an MAOI like its amphetamine-based cousin.
• Likely to also be similarly cardiotoxic

The first time I tried methedrone, 4-MeOMC, I found it to be MORE euphoric than MDMA or 4-MMC. Other trials I found it almost dysphoric, especially my IV trial which was an overdose.

 

[ebola?]

It's a good thing Koreans are largely drug free, as they can't pronounce the "ph" in mephedrone or the "th" in methedrone (resolving either compound to me-pe-deu-ron).

ebola

 

[MeDieViL]

It seems that (methylone) and perhaps other beta ketones dont bind to VMAT2 wich would make them reuptake inhibitors, not sure how they would have less affinity for MAO tough but anecdotes of pentedrone dont seem to indicate MAOI activity (wich can be explained with luck of not dosing too high.

millimole for millimole methcathinone is actually a "better" stimulant than methamphetamine, its just that the b-keto is a rather polar function and hence reduces transport to the brain. hence the more fat soluble amphetamines are "more potent". but ask anyone who has compared methcat vs methamp and they will probably tell you cat is a lot stronger effects wise.

Def not but substituted ones like mephedrone are far more effective at "fucking you up" compared to amphetamines. Most arent that much better tough.

 

[sekio]

Substituted ephedrines and cathinones turned out to be very poor MAO inhibitors, there was a thread I had posted in before detailing the comparison between amphetamines, norephedrines, and cathinones. Basically only the subst'd amphetamines are suitable MAO blockers.

 

[Tryptamite]

I recall seeing a poster in Switzerland warning about 4methylamphetamine being sold as base amphetamine (sticky putty a la uk base speed). Apparently it was causing problems for people who were using it in the same manner as their normal amphetamine.

 

[kokuro]

I saw one of my friends became very high after taking about 10mg 4-MethylMethamphetamine. He became very talkative and walking around in the room to find something to do. He did not so much change when he had taken other chemicals like A-PVP MPHP 3,4-CTMP,3-FA with about the same amount.

Because I am using these chemicals (except for A-PVP) every day within small amount for treatment of my depression not for party drugs.I can't tell anything exactly when taking large amount of 4-MMA,but I guess it may have good potential with a nice profile.

But I wonder why 4-MMA is very rare in the market.
I know only two dealers that are dealing with this.

 

[sekio]

But I wonder why 4-MMA is very rare in the market.

Probably because the "sister drug", 4-methylamphetamine, is considered neurotoxic... so 4-methyl-methamphetamine would be reasonably suspected to be as well.