Space_Milk
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L-Lysine Hydrochloride to Cadaverine (Stinky)
Hi there!
I'm trying to figure out a simple synthesis for Cadaverine with OTC chemicals.
To start off I'm going to use L-Lysine Hydrochloride (from the health store) as a starting material.
From the hydrochloride salt, use NaOH and solvent extraction to obtain the Lysine freebase. The next step is to decarboxylate it to cadaverine. The
most popular method for removing the carboxyl group from alpha amino acids seems to be intense heating in an exotic high boiling point solvent with
some kind of ketone catalyst. I have to say I'm not a fan of heating cadaverine to 200 degC as I'm sure the smell would become too much to bare  .
I think I read about another method with heating the solid amino acid with solid NaOH but I'm not sure what kind of temperature to use.
Would a metal like copper catylize this reaction?
Does anyone know of any methods for a more facile decarboxylation with OTC chems (I'm not looking for any biosynthesis using bacteria/enzymes)?
I would also be interested if anyone has ever made cadaverine. How bad does it actually smell?
Many Thanks!
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JohnWW
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Gosh, why do you want to make that stuff for? Are you going to use it as some sort of non-lethal chemical weapon? It is a bacterial degradation
product of certain amino-acids occurring in proteins, probably including L-lysine.
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Space_Milk
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No lol I just want to make it out of curiosity  .
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garage chemist
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Actually, it's useful, strong heating of the dihydrochloride converts it to piperidine hydrochloride with loss of NH4Cl.
But getting it from lysine- I don't know how that would be done best. I know about the decarboxylation of tryptophan to tryptamine by refluxing it in
acetophenone. That would be one thing to try.
Acetophenone has to be bought or made.
Putrescine (1,4-diaminobutane) can be obtained from adipic acid diamide and NaOCl by Hoffman degradation. The analogous dicarboxylic acid precursor to
cadaverine would be heptanedioic acid, pimelic acid.
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hissingnoise
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| Quote: | Originally posted by Space_Milk
No lol I just want to make it out of curiosity. |
Out of curiosity. . .
That's why the cops will say as they dig up your basement once your neighbours report the smell of dead bodies coming from your house.
Good luck with the synthesis. . .
[Edited on 4-3-2009 by hissingnoise]
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Ozonelabs
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Hi space_milk,
As a side project about a year ago ozonelabs successfully synthesised Cadaverine by the destructive distillation of Lysine freebase. From about
10grams of base we only managed to ditsill around 5ml. A brown sludge was left in the flask and no more would distill. Not to be too rude but the
cadaverine smells like nothing more than very strong semen. The disitillation was performed in a hood but the smell was very noticable upto around 10m
away from it. The real problem was actually removing the the sticky sludge from inside the flask as the smell was almost unbearable, i think lots of
acetone eventually removed it.
Definately good luck with it and the smell isnt as bad as they say!
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Paddywhacker
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I would suggest placing contaminated glassware and equipment in a bucket with dilute HCl, or acetic acid. The acid will protonate the amines to form
nonvolatile salts. Then you can just flush it all away ... but not with any alkali, please.
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jimmyboy
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IF... you can get hold of this catalyst and solvent - you can make tons of cadaverine.. GAG!!
http://www.erowid.org/archive/rhodium/chemistry/trp.decarbox...
Hint - Look at Table 2
GC: What kind of yield of piperidine does the dichloride give? low?
[Edited on 5-3-2009 by jimmyboy]
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Space_Milk
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Hi Thanks for the replies! Destructive distillation sounds like a good/easy/simple option but is gona stink to high heaven.!
I might give this a try when I get more free time with a SEALED apparatus (with an outlet to a chemical scrubber) using outside as my fume hood  .
[Edited on 8-3-2009 by Space_Milk]
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JohnWW
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I wonder what a good non-lethal chemical weapon, based on unbearable smell for its potency, as a substitute for tear-gas, would have as its main
constituents, besides cadaverine? You could mix the stuff with indole, skatole, and ethyl-1,2-dimercaptan, I suppose.
BTW cadaverine would probably attract blowflies, so you will need to have cans of fly spray handy, unless you make the stuff in a cold winter when
there are no flies around.
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kclo4
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When it starts to get cold for winter, all the flies seem to migrate inside. This could be used in a fly trap perhaps 
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Ebao-lu
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| Quote: | From the hydrochloride salt, use NaOH and solvent extraction to obtain the Lysine freebase.
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That will not work, because lysine is bese will deprotonate COOH, making it insuluble in solvents. And at normal pH you will still have an inner salt
NH3+-CH(R)COO- that is also insoluble. You can use hydrochloride directly, just add some base and heat with cyclohexenone.
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