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Activity of trans-4-methylaminorex intermediate

Ham-milton

Ham-milton

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Hey, I was going through the Microgram 2005:03 on the discovery of the clandestinely manufactured trans isomer of 4MAR. In the article which details the synthetic route the chemist used, they show the structure of the intermediate cis-4-Methyl-5-phenyl-1,3-oxazolidin-2-one.

journal_v3_num34_fg72.gif


This looks like a combination DARI/ GABA-ergic, the carbamate structure built into a pentagonal ring has been seen in other depressants, so it seems likely that it would be active here as well.

I've been unable to locate any pharmacological data. Does anyone have access to CrossFire or another database that might have data on it?
 
I should add that the reason I suspect it'll be a GABAergic depressant as well is because it bears structural similarity to two GABAergics- specifically these two.

Trimethadione
220px-Trimethadione.svg.png

(anti convulsant- not sure if it's an ion channel fucker or an actual gabaergic, though- a lot of very similar structures do one or the other, not sure how structure relates though)

Mephenoxalone
220px-Mephenoxalone.svg.png

(muscle relaxant and mild anxiolytic)
 
Damn you Hammilton, that ICF name of yours makes me giggle every time! If I ever end up in a serious conversation with someone about GABAergics and related drugs and break out in laughter, thus ruining my image of responsibility, I know who to blame =D ..!

ps. There is something very, very wrong about posting something worthwhile in ADD (or indeed, in ADD at all!) with the colour scheme as it is at the moment, so i'm not! Haha.

I will say that I will try pull you up some data soon though, so long as noone beats me to it, of course :) .
 
Can anyone tell me if this is legal in the UK? as far as I can tell only 4-methylaminorex is stipulated.
 
Hehe, amusing term Hammy, could you elucidate?

Ion channel fucker? are you referring to ligands that bind to voltage-gated channels and lock them open, such as the marine dinoflagellate polyether toxins, I.E maitotoxin, palytoxin, etc, and veratrine, as derived from the hellebores of the genus Veratrum?
 
I'm guessing that he's referring to calcium channel blockers similar in activity to gabapentin and lyrica... :P FUCK THE CHANNELS! :P

Limpet Chicken: given your sensitivity to stimulants' adrenergic activity, wouldn't this one likely be pretty cool for you?

ebola
 
Yeah, those ion channels piss me off, fuckers can get fucked and kiss my furry autistic arse=D

On a serious note, hm, interesting idea Mr.Filovirus, but I am not so confidant on the metabolites of that thing, if I remember right, and I did some looking into it, I still intend trying the 2-methyl-butan-2-ol carbamate-protected derivative of MDA, and the entire idea (aside from it being a legal prodrug in the UK) was that it should crack open once it hits stomach acid, to provide a slightly spaced-out release of both MDA and 2MTB, giving it a nice slow ride up and the long-acting GABAergic effects to smoothe it out.

My AMPAkine (sunifiram) synth is taking higher priority at the moment though, I need to get my memory/cognitive and executive function issues fixed and the sooner the better.

That bugger looks like it might release MeOH/HCOOH in vivo, and we all know what that does to one's optic nerves, I wouldn't touch the stuff without metabolic testing in a few paedophiles/rapists first to test and see if it makes people go blind.

As far as stimulants and my issues with anything poking around with my adrenergic neurotransmission, that isn't anything a good plugged dose of tizanidine or clonidine won't fix, 10mg of the former, the F&B way, and bye bye overstimulation.

I have been thinking of giving 5-MAR a taste though, it sounds pretty nice for occasional use.
 
Limpet_Chicken said:
Yeah, those ion channels piss me off, fuckers can get fucked and kiss my furry autistic arse=D
Click to expand...

Do you have the Asperger syndrome, like I do? (my ass is highly furry,too, lol)

If I remember correctly, aminorex was taken off the market after it had been shown to cause serious heart disease. I wouldn't take 4-methylaminorex either, because it could have the same side effect...
 
Pulmonary fibrosis IIRC, and heart valve abnormalities.

I would make an educated guess at 5HT2b agonism, and that is only an issue apparently with regular use, transient 5HT2b stimulation does not appear to cause heart valve hyperproliferation. Many psychedelics are 5HT2b agonists as well as activity at 5HT2a/2c/1a sites.

I did not mean I wanted to take 4-MAR regularly, but it is one on my list to give a try a few times.

And I was not being serious about the furry bit. No, I am not aspie, but vanilla autie, sadly not Kanner's, but I am no social beast put it that way, definately non-user friendly, unless you include my g/f, who is classically autie also. That, I think is where the neuropharmacology/O-chem/botany/mycology/microbiology interest comes from I think. Good to see a fellow spectrumite on the board :)
 
New test for Asperger`s: test for excess ass fur. :)

Limpet, I remember your carbamate pro-drug idea from a previous thread; I find it highly fascinating. Wouldn`t the resulting alcohol have to be equivalent potency or more to the other binded drug to have a useful effect? Is 2M2B significantly similar in potency to MDA?
 
Well here at least, it has one useful effect even if a completely inactive alcohol was used, the act of making it a carbamate, seeing as how the intended route is through the corresponding isocyanate and alcohol, flame-drying one's flasks, distillation of the alcohol over calcium carbide. in a current of N2, Ar, He, etc passed through conc. H2SO4 (I don't consider this synthesis discussion, as I am merely talking of drying agents, not actual 'recipes') will result in it no longer being a ring substituted derivative of (alpha-Me)phenethylamine (in the case of whatever one might choose to make), but a derivative of the corresponding isocyanate (or indeed if one were to be cheeky, EtOH=D)

Thus bypassing the misuse of drugs act in the UK, we do not have a US style analog law here, they do have widespreading bans on various classes of substance, but there are many things not covered, and nobody thought of this one before, when they wrote that steaming heap of shite.

Potency wise, bah, I am not so good when it comes to calculating actual weights from molar fractions, after having to convert the molar quantity in question in to a weight to begin with, I hate being dyscalculic, and besides, after a few shots of vodka, I am certainly not inclined to do it right now.

But I don't think its going to be an extremely significant dose of 2MTB at all, but the idea wasn't to get one pissed as a fart on the alcohol, but to smoothe the ride a bit by both the GABAergic effects of the alcohol in question, and by slowing release of the amine parent drug in the system, assuming formation of the alcohol in the acidic conditions of the stomach isn't damn quick anyway. If that is the case afterall, then its not a problem, seeing as how there would be little difference in speed of absorbtion to MDA in the first place!

But above all its about being able to keep as much of whatever one wants around at hand, without any illegality.

Potency wise, I wonder what the 1,1,1-trichloro-2-methyl-2-butanol derivative would be, given chloral hydrates large increase in potency over EtOH (and the fact that its rapidly metabolised to trichloroethanol, which I make the assumption, is the active drug, or certainly one of them.
 
this was kind of a stupid question to start with, seems like a decent chance of being a GABAergic, but stimulant? unlikely
 
The amine is not basic, so the chance of it binding to DAT is basically zero. If taken parenterally, it could be a cathine prodrug that crosses the BBB, but I can't imagine effects would be much different from cathinone itself, which was lame. Taken orally, it should hydrolyse to cathine in the stomach.

Also, it's not an intermediate, it's a side product: the reaction with cyanate only produces 4-MAR for the trans-cathine; the condensation of cyanate with cis-cathine gives the title compound.

(trans-cathine and cis-cathine are almost certainly abuses of nomenclature)
 
not disagreeing with the conclusion, but a basic amine isn't required for DAT binding.

O-2172 for instance (among dozens of others, including some cocaine analogues with an oxygen replacing the amine.
 
There are far more stupid answers, than there are questions, in my experience.

The truly stupid, tend not to question at all.
 
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