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Ring Substituted Pemolines

haribo1

haribo1

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Nov 29, 2006
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I just wondered if anyone had considered making the ring-substituted permoline series. Benzaldehyde+NaCN->mandonitrile+Guadinine->permoline seems easy enough. The substituted aldehydes can be produced by breaking up the propenyl benzenes so the MD, MM, DMM and so on would be obvious canidates. I don't know where to get 2,5 dimethoxy 4 methyl aldehyde, but I would wager that it would be fair trippy!

Just wondering out loud,
H-)

PS Similarly, the aminorex series could be substituted. In fact, I bet that they would be stronger. After all, aminorex is more active than dexedrine and both isomers are active...
 
I can't find the structure of a permoline. The spelling mistakes are crippling for trying to figure out what synthetic steps you're tying to do (for me, anyway).
Can you give an IUPAC name?
 
pemolines don't share the same ring substitutions as phenethylamines and the compounds you've stated some have been made and none seem to be as good as 4methylaminorex and none have any trippy fx, there may be the possibility that there could be compounds that have psychedelic potential they have yet to be discoverd, maybe it's as simple as different positions in the ring like the aminoindans or maybe like piperazines in that it's far too different altogether.
 
I had forgotten the ducky compounds! Now, does MDMA work on 5HT2 or not? I'm thinking that the pemolines, phenmetrazines & aminorex series might be most ameanable to a 3,4 methylenedioxy ring as a starting point... In all cases, the substituted benzaldehyde would be the start material and although watched, I don't think that they are in any way illegal to posess? Correct me as I'm usually wrong.

H-)
 
Pemoline is my favorite stimulant ! Very easy to make and does really good stimulation without amphetamines side effect !!! :D

_

structure of Pemoline ;)
 

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Well, if you put a 3,4 methylenedioxy ring onto it, maybe you got yourself a nice, new MDMA alternative...
 
3,4-methylenedioxy-aminorex was made in the original paper (compound XXXIII) and was an active anorectic although one of the weakest ones that still retained activity. But then all they were evaluating it for was anorectic activity in rats which doesn't say that much about what it would feel like for a human test subject...

Yeah i've always been curious about methylenedioxy-methylaminorex and methylenedioxy-phenmetrazine, an oxygen at the beta position clearly doesn't destroy activity what with the beta-ketone drugs being quite nice empathogens, and Shulgin reported beta-methoxy-3,4-MDPEA as being active in PIHKAL, so theres plenty of potential for more exploration.
 
I dont think this reaction would be very practical, but theres no telling for sure without going into the lab.

Im assuming you're speaking about guanine rather than guadenine.. Ive never heard of the latter.
 
guanidine the imino derivative of urea, I believe there is one correct spelling soemwhere in haribos post :)
 
Ahh that makes a bit more sense..

This seems feasible, you would be better off replacing your nitrile group with some sort of ester though.

Start with mandelonitrile and have the alcohol group react with the guanidine in basic solution to cleave off NH3. Hydrolyze your cyano group with an acid and add some sort of alcohol to create an ester. Heat the solution and pray!

There has got to be a better way to go about doing this, the first reaction with mandonitrile and guanidine to form the O-C-NH2 bond already puts some doubt in my mind.


BTW next time you ask for help make sure you get the names right :D
 
has anyone got data on the metabolism of pemoline?

there do appear to be better methods and routes but I don't want to have to warn myself for synth discussion, plus F and B would spank me
 
Sorry for my pathetic spelling. F&B loves phenmetrazine, if I remember rightly, so that would make an interesting one to substitute. It looks easier to make from PPA than 4MAR or amphetamine, but you don't see it about...
 
"FDA imposed a warning describing the risk of liver failure and the indication that pemoline should not ordinarily be considered as first-line therapy for attention deficit hyperactivity disorder. (WHO Drug Information 11/2: 71, 1997). The British Health Authorities withdrew pemoline because of its hepatic toxicity. (WHO Drug Information 12/1: 15, 1998)." -Psychotropics.dk

Hmm?
 
That ketone group on pemoline really seems to kick down it's activity. Aminorex is 1/2 way between dextroamphetamine & methamphetamine. And you can make it on your table-top... sigh... outbreak imminent I think.
 
the carbonyl c=o in pemoline is actually an amide or to be more precise a substituted ureide. which is why I wanted to know about the metabolism of pemoline, does the ring get opened and if so where is it opened?

aminorex wasn't much abused when it was readily available, before it was pulled due to links to heart problems, its an ok anorectic and mild stimulant with only limited abuse potential. Is aminorex now illegal in UK, I know that 4-MAR is class A and has been for at least 12 years.
phenmetrazine seems more likely to be popular, but all of these will remain much less common than plain vanilla amp or meth, economics calls the shots for street drugs.
 
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