Uncontrolled MDMA alternative?

[clubcard]

I did some work on the QSAR of ring-substituted aminorexs and found an interesting result. p-Me aminorex is a reuptake inhibitor 5HT>>Dopamine>Norepinephrine and for most people, 80mg of the hydrochloride addition salt has no discernible CNS effects. Now m-Me-aminorex is Dopamine>Norepinephrine>>5HT but for most people, 40mg of the hydrochloride addition salt has no discernible effect.

But 80mg of p-Me aminorex + 40mg of m-Me aminorex produces subjective effects as 125mg of MDMA. The aromatic methyls also provide the body for a convenient moiety to oxidize in a similar manner to mephedrone's metabolism. Thus duration is 5-6 hours, not the -12 hours+ of the parent compound (aminorex).

So, I don't know the letter of the law but 2 compounds, neither of which produce psychoactive effects alone combined in a single dose unit would appear to circumvent the UK's Psychoactive Substances Act. I hasten to add that I am not a legal expert and would not wish to test the law.

Synthesis from the appropriately ring-substituted benzaldehyde via nitro-alcohol, amino-alcohol and ring-formation using BrCN was the most attractive route. KOCN produced the substituted urea although it is possible that cyclization is possible.

 

[F.U.B.A.R.]

I did some work on the QSAR of ring-substituted aminorexs and found an interesting result. p-Me aminorex is a reuptake inhibitor 5HT>>Dopamine>Norepinephrine and for most people, 80mg of the hydrochloride addition salt has no discernible CNS effects. Now m-Me-aminorex is Dopamine>Norepinephrine>>5HT but for most people, 40mg of the hydrochloride addition salt has no discernible effect.

But 80mg of p-Me aminorex + 40mg of m-Me aminorex produces subjective effects as 125mg of MDMA. The aromatic methyls also provide the body for a convenient moiety to oxidize in a similar manner to mephedrone's metabolism. Thus duration is 5-6 hours, not the -12 hours+ of the parent compound (aminorex).

So, I don't know the letter of the law but 2 compounds, neither of which produce psychoactive effects alone combined in a single dose unit would appear to circumvent the UK's Psychoactive Substances Act. I hasten to add that I am not a legal expert and would not wish to test the law.

Synthesis from the appropriately ring-substituted benzaldehyde via nitro-alcohol, amino-alcohol and ring-formation using BrCN was the most attractive route. KOCN produced the substituted urea although it is possible that cyclization is possible.

I like your reasoning, and hope it is true.

Any other thoughts?

 

[clubcard]

I like your reasoning, and hope it is true.

Any other thoughts?

I use a simple metric for new designs which runs like this 'Would I be happy for my son to take this/these compound(s)?'. He is 29. If not, I dump it/them.

I am not gung ho about suggesting people try a new design. I have to presume some people will take 2 dose units (especially in areas with low quality MDMA) at once and IF it is going to harm someone, it's going to be me so I had to take 160mg + 80mg of powder in gelatin caps. I am not trying to take the moral high ground, just saying in my my defense that I take the health and well being of users seriously.

 

[Nagelfar]

How does the 3 place on one substitution and 4 on second, each wholly different, get decernable effect together in a way other than just mean uppage of dose? or are you not claiming anything like that Borohy.. I mean CC? Just undershoot metafailure and parafailure together and you got some synergy isn't that it?

 

[G_Chem]

I’d be interested in any more detailed bioassay information. How many times has this been tried? By how many people?

-GC

 

[sekio]

I think aminorexes (aminoreces?) are covered by the PEA ban in the UK MoDA.

Didn't Shulgin say 2C-D had a similar effect? Boring when taken alone but a useful extender for other 2C-x drugs, a "pharmacological tofu" I think he called it.

 

[clubcard]

I think aminorexes (aminoreces?) are covered by the PEA ban in the UK MoDA.

Didn't Shulgin say 2C-D had a similar effect? Boring when taken alone but a useful extender for other 2C-x drugs, a "pharmacological tofu" I think he called it.

Nope - because their is an cyclic ether function on the alpha carbon. The fact that it has a second ring (thus a cycloalkyl) AND that the parent is a class C all strongly suggest that they are NOT in fact covered. I didn't ask Rudi Fortson but I have his book on UK drug law.

I mean, just swapping the beta methyl of amphetamine with a betafluoromethyl makes it legal, does it not? I DID try the beta fluoromethyl analogue of mephedrone but it was less water soluble (or at least the HCl was) making snorting painful but more seriously, I suspected increased MAOI activity - hence it failed the metric & was thrown away.

But 2 or more compounds required for psycho activity is a classic oversight. The law is written by people who are not chemists. I mean, they ASK chemists but all laws are reactive, not proactive.

 

[S.J.B.]

I think aminorexes (aminoreces?) are covered by the PEA ban in the UK MoDA.

They don't appear to be.

I mean, just swapping the beta methyl of amphetamine with a betafluoromethyl makes it legal, does it not?

Yes, it appears that ring substitution for amphetamines is covered fairly broadly but substition elsewhere is not.

 

[Nagelfar]

Speaking of the betamethyl on amp., has there ever been a metal thrown on there? Like Ni or Cr?

 

[clubcard]

They don't appear to be.


Yes, it appears that ring substitution for amphetamines is covered fairly broadly but substition elsewhere is not.

As I said - the law is reactive. I suppose people tried making aminorex derivatives but gave up when it appeared to need BrCN (not healthy).

But I THINK their is a trick. I seem to recall NaHNCN (monosodium cyanamide) can replace BrCN. It was in a paper from the 1940s but I didn't pursue it.

There is also an East German patent that proceeds via the styrene oxide directly to the product. Again, not pursued. There was also a Polish paper I dug out but it yield a mixture of products that were hard to separate.


But, as I have mentioned, the beta fluoromethyl analogue of mephedrone and amphetamine are not covered. The HCl salt wasn't very soluble. The phosphate was better, the sulfate the best... but that was thrown out because it means the body has problems removing it. I suppose in many nations, the beta fluoromethyl derivatives of the 2,5-dimethoxy-4-<something> amphetamine would be OK. Speaking of which - those are chiral compounds and I am interested to know if anyone has resolved DON? I learned that the enantiomers of AMT have notably different actions.

 

[draculic acid69]

I'm pretty sure aminorex's were abandoned when it was found they caused pulmonary hypertension.
4mar used to pop up often round here
but it no longer appears.and I'm sure they other than a small very short lived appearance of sum 4mar analogs they're not being looked into or made anywhere anymore.

 

[draculic acid69]

Also the sub benzaldehyde+amino acid->amino alcohol+kocn-> product is the best way.brcn is unnecessary and produces the inferior cis form whereas
kocn- leads to the better trans forms.

 

[clubcard]

Also the sub benzaldehyde+amino acid->amino alcohol+kocn-> product is the best way.brcn is unnecessary and produces the inferior cis form whereas
kocn- leads to the better trans forms.

As I pointed out, KOCN does NOT form the 4,5-dihydro-1,3-oxazol-2-amine ring, it stops at the substituted urea. We DID try this several times. NaHNCN looks like a promising route and that East German patent (DE Patent 2101424) proceeds via the styrene oxide. Since chiral amino oxides can be produced, you can head for the isomers you want.
Don't forget that aminorexr interchanges between endo & exo forms so trans and cis are not applicable. 4-MAR does not appear to undergo this interconvention. When all said and done, if a 2:1 p-Me : m-Me, replaces MDMA, I do not see people paying over twice as much for the pure (R) or (S). If it isn't practical, nobody is going to do it.

I mean, the 2 isomers of MDMA are considered better than a single enantiomers as Shulgin discovered.

Don't get me wrong, it would be an interesting experiment BUT above bench-scale, who is going to go for all that extra work.

 

[Nagelfar]

Hey cc, what do you think of chelated compounds as drugs? (Me and sekio's conversation recently in the random article thread) you familiar with Singh's 1999 cocaine analog paper I presume, have you scrutinized the part with the aryl chelate phenyltropanes? (It gives two) do you think other MAT drugs could similarly be strengthened due to this, or are the variables likely to void traditional binding assays?

 

[dopamimetic]

I'm pretty sure aminorex's were abandoned when it was found they caused pulmonary hypertension.

Is this a serious issue even when using recreationally, e.g. no more than every 2 weeks and with longer breaks?

4mar used to pop up often round here
but it no longer appears.and I'm sure they other than a small very short lived appearance of sum 4mar analogs they're not being looked into or made anywhere anymore.

Which imho is a real pity, never managed to acquire 4mar but got some 4,4'-dmar when it was available for a brief amount of time in 2013 or so and it is one of the best substances I've had, for me personally. So much of serotoninergic bliss with a 12h+ duration, refreshing sleep and after effects consisting of just tiredness, no depression or other "weirdness". Also it worked on multiple following days with few decrease in effects (although this was not a full MDMA-esque experience, dosage used was 20-40mg) or potentiated hangover. I know of deaths from serotoni sample pills (and/or other reckless vendors selling them as ecstasy), yet do I wonder if it isn't "just" a substance that could be used safely as long as one strictly does not mix or use beyond some dose. Have to say that I probably had some remaining venlafaxine in my body and did re-dose (tiny amounts though, the dmar not venlafaxine!) on some occasions. This leads me to think that the maoi property isn't too strong and it's primarly interactions being responsible for negative effects...? [of course I didn't know either that it's a maoi nor about negative effects to others back then. Didn't do my homework, for once without repercussions..]

It didn't feel heavy. Strong, yes, in the sense of a powerful substance that has a good effects : side effects ratio but such ones might also tend to be dangerous when used without precaution. Of course, this is purely subjective.

4-mar always intrigued me due to its suggested "nootropic-like" effects, with the reports apparently confirming that more or less, and pemoline being somewhat related and also having interesting reviews.

The latest one, I don't remember its formula unfortunately, disappeared too soon for me to get it but also reviews weren't good. Never really read anything about dmar either though, besides about the incidents.

 

[draculic acid69]

I used 4mar everyday for four months in large quantities.no problems.but when aminorex first appeared there was a spike in deaths caused by heart problems due to aminorex use.maybe 4mar don't have the same effect as aminorex.

 

[dopamimetic]

Or it only affects part of the populations. Is a clear mechanism known for the damage ocurring? As we have plenty of chemicals activating 5ht2b without being so prone to pulmonary hypertension. Once guessed whether I did damage by overusing DXM (assumedly an agonist there) together with venlafaxine and methylphenidate but probably it just was too much NE and hypochondria as the dosages weren't really high..

As aminorex probably, never done it nor had access to, isn't recreational it will likely have a different profile - wikipedia states "release of catecholamines" but thought it's a serotonergic? Maybe a stimulant and 5ht agonist?
Ok and we have the levamisole/cocaine thing. But for that to work the substance doesn't have to be hugely recreational on its own, otherwise the so-adulterated coke would last for much longer i guess.

@draculic acid69: Guess it must be nice substance then is it more of a functional/cognitive stim, an euphorisant or an empathogenic? Still wonder how similar it is to 4,4'-dmar.. that one was, in lower dosages, somehow a balanced mix of all three if that makes sense. At higher dosages probably shifting more towards the right but very clear and huge difference to e.g. 4-mmc, not only the overall dirtiness but also its tendency to make one ... kinda manic. Don't like to admit that but had no difficulty driving on 4,4'-dmar, or having good conversations with sober people. Both things pretty impossible on 4-mmc (never done real mdma so can't compare here- yet the dmar lacked these effects I don't like to do mdma for- 5ht depletion/hangover depression, no wave-like effects / comeup being 2h+ but smooth, comedown sometimes even strangely abrupt but think of that as a plus I guess as it was just effects shut off at maybe T+10h, and no hint of psychedelia too yet crystal clear, fluid thoughts and emotions, also a robust antidepressant component present). Even think it could be used as a motivational study aid when one doesn't go too high. Maybe the make-everything-including-boring-tasks-fun kind of substance.

Did I say I loved it? xD

 

[draculic acid69]

It's like meth but more euphoric and more enjoyable and clear but on day two or three it gets a bit dreamy and everything starts to look bright and well lit like when somebody has a day dream or a flashback with the harps playing on a TV show but it's still clear-headed and focused without that can't sit still push too much meth can have.infact when it ran out and was replaced by meth I mixed my last quarter of it into the meth.i wished I hadn't done that.ruined it completely.ive been in love with analogs ever since.4mar ,4mmc,mdpv,a PvP, 5mapb all have so much more euphoria than there originals.analogs are where it's at.
I've found that once ppl know there smoking analogs they're converted forever.9 out of ten are happy and prefer the analogue but there's always that one that keeps trying to insist that
the old psuedoephedrine made meth is better.4mar is a bit gentler on the body and brain too it's equal potency wise but less tense and tweaky.

 

[dopamimetic]

It's like meth but more euphoric and more enjoyable and clear but on day two or three it gets a bit dreamy and everything starts to look bright and well lit like when somebody has a day dream

Yeah, that! Forgot to mention, or how to describe but 4,4'-dmar had the exact same thing, and it became more apparent on following days with partial tolerance or something alike. Ok would say then they're pretty similar but dmar (obviously) being a stronger serotonergic, yet without, or with different, negatives usually associated with that.. What is the dose with 4-mar? 4,4'-dmar afaik was dosed 70 or 80mg as Serotoni, I took 3/4 and it was heavy but probably what users are looking after. There was an effect at just 5-10mg with the sweet spot for everyday* being at maybe 25-35mg. After 14 days, the empathogenic effects faded away to tolerance, also the push was gone but it still had pleasurable effects (note I did not increase dose as only thing I knew was structure formula) and possible depressive after-effects or brain-zaps were completely amoreliated by 75mg venlafaxine which I took before so it was just a measure of precaution, didn't wait if and for effects to appear.

The day-dream effect is serotonin I guess as DXM can have the same when used for multiple days at whats called as "plateau 1". Indeed there are some similarities to that but DXM is dirtier and supplies you with loads of NE and some dissociation instead of dopamine. [Note that DXM is a bad comparision as everybody gets different effects based on individual enzymatic differencies. But it's the nearest comparison I have, a bit further away is maybe MXE if you'd take the dissociation away and replace the clarity of mind with an illusion of that, but again a potent serotonergic of course. Both have the property of not inducing classical serotonergic hangover. I got that from 4-/3-MMC and it was horrible. Also their relative ephedrine metabolite causes me strong tachycardia, minus that they are enjoyable substances.]

Agree with you that many of the classic illicit drugs are overrated. Due to impurities, bad manufacturation, well illegality, but I like to think that also just the pure substances aren't that "good" as many think or, ok just the better ones out of a ton of random shit, the RCs not as bad as their reputation. That also not having to be the case on BL or in this subforum.. MXE/O-PCM (keta), 4(,4'-d)mar (mdma/meth- more the former and when having them, who needs meth?), maybe 4mmc (coke), even o-desmethyltramadol isn't too bad.

I've had conversations with some "deepnet chemists" and none of them was able to produce 4-mar. One said he tried some times and always failed with the routes found online so he stopped trying, others heard similar things and didn't bother trying themselves. RC people of course don't want to do 4-mar as it's illegal in many places sadly but for sure there will be an analog of the analog that'd be worthwile.. I apologize if this is already forbidden synthesis talk, then please delete or notify me.
Is the above true, that 4-mar is so much tougher to cook than meth or just people supplying the demand for more popular substances? What about the above mentioned p-Me (para-methyl?) / m-Me derivates, have they been available yet?

 

[clubcard]

Well, as I have noted elsewhere, swapping the terminal -CH3 of mephedrone, methylaone & (meth)amphetamine with a -CH2F places it outside MOST nations laws but the problem is that the terminal alkane is one of the spots the body uses to metabolize said drugs and the -CH2F homologues are much less water soluble. The solubility seems to be H2SO4>H3PO4>>HCl and none of them have convenient workups.

Likewise, diphenidine isn't that soluble in water as the HCl salt and isn't the best of the series in any case. the N-isopropyl homologue has higher affinity to NMDA receptors and the N being monosubstituted increases dopaminergic so it is much, much more like K.

I did touch on the fact that 4-methyl aminorex derivatives DO cyclize when reacted with KOCN but the appropriate styrene oxide (which may be chiral and the patent of which I have posted) react with NaHNCN as per patent works. The chiral styrene oxide IS expensive but I have never heard of people complaining because it was a mixture of (R)(S) & trans/cis.

One PLUS point of making plain aminorex is that their are several routes to the hydroxylamine moiety. Reduction of nitroalcohol was the most efficient but reacting the benzaldehyde with sodium bisulfite followed by NH3 & NaBH3CN also yields aminoalcohol and so on. It's such an old reaction that dozens of routes exist.

I SUPPOSE the chiral styrene oxide + NaHNCN is convenient because no suspect precursors are being ordered....

But if you just want an entactogem, (S) 6-methyl AMT works well. Don't forget, AMT has a chiral centre (try overlaying it with LSD) and while the (R) isomer is trippy, the (S), especially of the 6-methyl, is an entactogen.

You really do not want to mess with AET or 6-methyl AET as they have potent MAOI properties. Resolve & racemize (R) 6-methyl AMT.


But, there are still more entactogens out there. I'm just posting these because I PRESUME others have also tried them so know that they work...