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Stimulants of the Future II

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Could anyone help me predicting the behaviour of this?
ImagesHandler.ashx


I found 2 patents on chemspider (5626860 Method for regulating metabolism with dopamine beta hydroxylase inhibitors) But none seem to mention anything about the exact substance.
Could be a DBHI, but i would like to know more abut this beta methylene analogue.
 
WTF... how come i cant find any info about simple beta methoxy amphetamine on chemspider or google.
This is absurd....i'm dissapointed.

Thank gof F&B always comes up with some info (gotta love that guy):

-From Stimulants of the Future I:
Beta-methoxyamphetamine is O-methylcathine (O-methylphenylpropanolamine) and beta-methoxy methamphetamine is O-methylephedrine. O-methylephedrine is like phenmetrazine with the ring cleaved between the ethylene bridge between the O and N atoms. Years ago it was on my to do list, but never got around to it. It looks very promising.

The beta-methyleneamphetamines (cathenine as Vanadium called it) is the basic structure I suggested would be possibly a more potent 5HT2a agonist when ring substituted than the corresponding amphetamines (see ;Acid, dragonflies & the 5HT2a receptor')
 
Cut down on your use of stimulants. For fucks sake, no one wants to see 18 posts in a row by the same idiot who can't control himself.

And why don't you both to do minimize them and compare in 3D to known stimulants. Jesus motherfuckingchrist, it's retarded simple and perhaps you wouldn't feel compelled to start a new post for every effing thing that enters you drug addled mind.
 
O__o' ......You okay man?

The idea of that cycloether compound came from looking at sibutramine and thinking of placing the C-O-C functional group inbetween S and R (like a beta keto, but with an ether)

ACD - 3D optimization (d enatiomer):
bbutoxyamphetamine.png


BTW i just had coffee and a bit of wine this past week.......
 
Hammilton said:
Cut down on your use of stimulants. For fucks sake, no one wants to see 18 posts in a row by the same idiot who can't control himself.

And why don't you both to do minimize them and compare in 3D to known stimulants. Jesus motherfuckingchrist, it's retarded simple and perhaps you wouldn't feel compelled to start a new post for every effing thing that enters you drug addled mind.
Click to expand...

Hammilton-do you talk to people like this in your real, day to day life, or only from behind a computer. You've always seemed a bit short on patience regarding people who ask "stupid questions" or make "annoying posts", but lately you are just TEARING into people with absolutely no restraint.

Of course I agree that navarone could edit himself a bit, but what is your goal wit these over the top attacks and insults?-DG
 
Yes, i agree that i should have re-edited all my posts in one or 2 posts instead of coming up with my curious suggestions every 30 mins.
I know i posted a lot today but it was not because of any drugs apart from some coffee but rather me being cold and staying home in front of the PC.

Anyway let's end this here please, no further tension. I'd hate to see this thread getting closed because of this.
 
^^^^^^^^^^
My point wasn't that Hammilton is clueless, it was that he (esp. recently) has been acting like an angry, bitter old man who needlessly lashes out at anyone who has the audacity to be less knowledgeable then he is.
I am the first to admit that he is a wealth of knowledge when it comes to psychoactive substances. Unfortunately, he seems to have no idea how to interact with people (at least online).

Anyway, this is far off topic and there is no need to waste more time on this. I probably should not have even mentioned it in this thread- it just bothered me to see him once again lash out and insult someone just because they were a bit over-enthusiastic in their postings. -DG
 
Stay on topic please! Any personal sentiments can be dealt out via PM.


I absolutely share Delic's concerns about a MPPP-like toxicity issue. The similarity between the proposed compound and MPPP is frighteningly high and pyrrol's basicity doesn't change a thing in this case. If the alcohol gets eliminated due a poorly made synth resp. purification protocol, there's already one double bond in the 5membered ring given, nicely conjugated with the phenyl-ring. Aromaticity is the driving force, and therefore, a MPTP-like metabolite quite likely. As pyrrols can act as bioisosters to pyridines, I'd be reluctant to touch this fucker.

- Murphy
 
^^^
I trust your word then, I wouldn't touch prodilidine either unless certified to be 99.9% purirty.
Had temporary parkinson symptoms once, not wishing for them again.

By the way, the O-methylepherdrine mentioned by F&B does really seem promising as a phenmetrazine substitute.
However it seems that its pretty tricky to make it as a pure enatiomer (R,R) and unlikely to come out from home labs.
Methylating ephedrine is not reccomended due to high chances of E2 Elimination. Shulgin used nitrostyrene to make such componds but separating the 4 different enatiomers would be another bitch.

Too bad..
 
What are the chances that this elimination of the carboxygroup happens in-vivo? One uses to think if the synth is done properly and the compound is pure, its okay. Methinks more and more that this kind of structures are a no go at all.

Btw I love Hammiltons rants, I collect them %)
 
Yo Hugo, look again plz: At the pyrrol there's no carboxy-group but an (esterified) alcohol. No idea how the chances are that this bugger goes off in vivo, but in vitro at acidic conditions and a bit of heat - pffffff, there he goes.

I really like Hammilton's rants, too. It's so refreshing. One shouldn't be so wimpy and take it personal... (no offense Hammi ;) )

- Murphy
 
I wouldn't worry so much about prodilidine myself. It's N-demethylated. MPTP becomes MPP+, which can't get back outside the BBB. Since this is N-demethylated, that's obviously not a problem.

MPPP isn't toxic, or at least it doesn't seem to be. Unless there was a similar issue of dehydration with higher temps in prodilidine synth, I don't see a reason to be particularly concerned.

That prodilidine has that 2-methyl group is certainly interesting. I'd be a little surprised if it doesn't release or block reuptake of dopamine to some degree. The reversed ester is on the beta carbon equivalent, similar to phacetoperane.
 
So you're saying that since it becomes demethylated, it won't be a problem? So why doesn't the same apply for MPTP? Why doesn't MPTP get demethylated?
 
I think it's a matter of which enzyme reaches the molecule first.
The oxidation of MPTP into MPP+ is caused by the MAO-B enzyme in glial cells (which is weird since its supposed to deaminate it).
PEA like N-Demethylase enzymes are found in the liver. I don't se why it could not be demethylated just like phendimetrazine or other methylated PEAs.
Obviously something goes wrong and I don't know if demethylating MTPT to TPT will prevent this phenomenon of 'failed MAO-B deamination'. Phenylpyridine could as well be neurotoxic. Murphy says the toxicity could be due to the aromaticity of the pyridine/pyridinium ring.
Prodilidine IS N-methylated, and the ester is hydrolysed in vivo giving again the spooky alcohol.

According to wiki:
the tertiary alcohol is liable to dehydration in acidic conditions if the reaction temperature rises above -30°C (minus? seems weird)

This confuses me, but a MAO-B inibitor could come in handy for sure.
 
Phenylpyridine could as well be neurotoxic. Murphy says the toxicity could be due to the aromaticity of the pyridine/pyridinium ring.
Click to expand...

Yes, but apparently the real shitty part is the quarternary amine of MPP+ which makes it not penetrate BBB so it stays in the brain, doing it's nasty thing...
 
Naahhhhh FnB! Ethylene oxide ("oxirane") is a 3membered ring, which is indeed very toxic. The depicted molecule contains a oxetane - or oxacyclobutane. For in vivo-related issues, it's stable enough and toxicity is far lower.

- Murphy
 
Hammilton said:
I wouldn't worry so much about prodilidine myself. It's N-demethylated.
Click to expand...

Looking at the structure that Wiki provides - it isn't! There's clearly a methyl an the pyrrols's nitrogen.

But I was wrong, too: Even when the pyrrolidine aromatizes to pyrrol, the ring won't be charged. So, the concerns about a MPTP-like derivative were not justified. Silly me :|

- Murphy
 
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