Author Topic: Unifiram synthesis?  (Read 152 times)

Bardo

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Unifiram synthesis?
« on: August 16, 2011, 01:44:50 AM »
Anybody got the synthesis for the nootropic unifiram? The Univeristy of Firenze in Italy tested it as being 1,000 times greater potency then piraractem (the strongest nootropic to date for most) and since unifiram is only a few years discovered nobody is making it yet. The synthesis comes up on a simple google search but they are from journals I don't have access to. It is suppose to be very similar to piraractem and you can buy bulk powder of that for not much so it would be nice if the synthesis somehow started from that.

Tsathoggua

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Re: Unifiram synthesis?
« Reply #1 on: August 16, 2011, 04:56:43 PM »
Working (slowly) on Sunifiram myself actually. Only thing holding me back is lack of analytical capacity, TLC plates in particular, as well as prep scale column chromatography, once those two are nailed, then the synthesis will go ahead and the product cleaned and isolated.

Precursors for that one, and its both similar or identical potency scale, to unifiram, just lacking the bicyclic ring structure which could be a pain in the arse..instead, just piperazine, acyl halides to donate the benzoyl group and propionyl moiety. There is of course the issue of a symmetrical, identically bonded diamine needing differing groups on each end.

Plan is to test the Rhodium archive synthesis out that gives a recipe for BZP...there is a nifty technique, IF the article is not full of shit and if its actually been done...for its both simple and inventive, guy claims to get stoichiometric yields, or close to that, of mono-substituted piperazine hydrochloride from the commonly available phosphate salts.

 (I am here, unusually, counting a salt counterion as a functional group, I wouldn't usually do so, but in this case it appears to be reliant on the fact that piperazine forms both mono and di-hydrochloride salts, the fact that its a functionally symmetrical secondary diamine working in its favour, rather than making things either obscenely complicated or impossible in this particular case and relying on less susceptibility to further acylation by the appropriate halides to a tertiary amine, simply swap that benzYL group for a benzOYL group, and thats 50% of the work for the actual synthesis done, at least, not counting workup and purification). Slightly less yield stated for production of the acylated amine (in that case BZP rather than n-monobenzoylpiperazine) but thats no big deal when we talk of a few percent, even for something as potent by weight as sunifiram.

Posted of this on blacklight, I have a thread started somewhere, feel free to search it there, and contribute to it also, the journal article request thread is useful also, I've scarcely looked at the one here really so far.

There are a few people there with GOOD journal access, and can reliably get most anything if its actually both online and assuming its not one of those bastard fuckwits at bentham who have it under their journals and of course, granted its not an old article from pre-web presence times for a given journal. Publishers don't seem to bother uploading older articles often. Damned frustrating, I found recently I have bugger all hope of getting a paper on Amanita gemmata poisoning in a regional district of chile and its clinical presentation within that particular area of chile because the paper is from before the journal in question started allowing access (paid of otherwise) to its papers.

(and where I am going to find THAT information in another journal, I do not know, well, yes, I do, I know I am going to find it bloody well nowhere thanks very much lazy journal publishing company)

Seems a better target than unifiram, from a point of view of where to get precursors from. Toady has no problems buying propionyl or benzoyl chloride, and piperazine is OTC here in the UK as a deworming treatment for humans)

Oh...where did the 'watched' tag under your user panel come from BTW?
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lugh

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Re: Unifiram synthesis?
« Reply #2 on: August 16, 2011, 05:22:29 PM »
Clearly the original poster's research skills need work, the patent in which the synthesis is mentioned is attached  ;)  It's truly amazing what one can find using various internet search engines  :-X  The end results from the effort applied  8)
« Last Edit: August 16, 2011, 06:37:16 PM by lugh »
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lugh

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Re: Unifiram synthesis?
« Reply #3 on: August 16, 2011, 09:59:12 PM »
This thread is being locked for obvious reasons  8)
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akcom

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Re: Unifiram synthesis?
« Reply #4 on: August 18, 2011, 09:14:08 PM »
Quote
Design, Synthesis, and Preliminary Pharmacological Evaluation of 1,4-Diazabicyclo[4.3.0]nonan-9-ones as a New Class of Highly Potent Nootropic Agents
Dina Manetti,† Carla Ghelardini, Alessandro Bartolini
J. Med. Chem. 2000, 43, 1969-1974

The original paper with synthesis and characterization