Question Racemisation

Acab1312

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Hello,
I stumbled across an interesting article where the topic of racemisation of l-methamphetamine back to the racemic product is mentioned. Does anyone have experience in this regard?
 

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Evilcarrot2

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I also saw this and would like to know more.
Then all that left over l-amph or l-methamp could be regenerated to racemic and get anoth 25% more d-anpth or d-methamph with only 1 time recemitise.
If anyone has any experience on racemitisation it would be greatly received
 

Acab1312

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Yes would be very interesting, especially for larger product quantities. Unfortunately, I haven't found anything more precise, which leads me to assume that the process is very complex or unprofitable.
 

btcboss2022

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Seems interesting I'm trying to go deep in the process I will update if I find the correct way for it ;-)
 

btcboss2022

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Won't be a fast thing I don't have so much time now but I will make it I'm very stubborn hahahah ;-)
 

Acab1312

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I am pleased that things are now getting going, that they have found a way so quickly. I am very confident that we will find a way. Thank you Btcboss2022 for taking on this project :)
 

UWe9o12jkied91d

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letting your product in solvent in a dark room at room temp will cause it to racemise by itself after a long period of time.I get what this implies but it's an option
 

Acab1312

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.Thank you What does long time mean? I would just give it a try.
 

UWe9o12jkied91d

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I haven't done it myself, heard from a fellow insectoid who worked in a lab studying enantiomery, so I don't know precisely, maybe there is data about other compounds that you can extrapolate to get avery rough estimate.
 

Acab1312

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Then I'll find out more about this, maybe I'll find something. Many Thanks
 

UWe9o12jkied91d

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I think it does, I've since read up on the subject and it looks like heat and light drive racemization, it's a concept used to date certain sites by studying fossils of marine animals and such, the principle being looking at the % of enantiomers can tell you how much time has passed since the animal died, since you know most amino acids are used in biological systems as levorotary form,You then look how much dextrorotary amino acid has been formed and from there you can estimate the age of the site, this is very roughly explained, just as proof of concept.So I was wrong just with the light part :p. Here's some sources, one of them claims, direct quote: At 160 °C, a racemic mixture is reached within 10–20 h, whereas in Arctic regions (−10 °C) racemic equilibrium requires 1–2 Ma.
G.H. Miller, ... S.J. Clarke, in Encyclopedia of Quaternary Science (Second Edition), 2013
Rainer Grün, in Encyclopedia of Archaeology, 2008
 

Fenster

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Does some of the D need to be present as a catalyst I wonder?
 

UWe9o12jkied91d

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"Racemization is the chemical reaction that interconverts an amino acid into its alternative enantiomer or mirror-image form. The rate at which racemization proceeds varies between amino acids according to the ability of R groups to stabilize a carbanion intermediate. The carbanion intermediate is the molecule formed when the hydrogen side chain is abstracted from an amino acid. In an ideal system, upon readdition of the hydrogen atom to the carbanion intermediate, there is an equal probability of l- and d-amino acid formation, and the forward and reverse reaction rates are equal. Under these conditions, d/l progresses from values near zero in modern tissues until d/l reaches unity at racemic equilibrium. A consequence of these conditions is the slowing of the racemization rate as the extent of racemization increases—the characteristic curvilinear trend produced when d/l ratios are plotted against linear time."

This is from Miller, I take from this that no, it dosen't have to be present.D-amino acids are so rare in nature that people tought they didnt even exist, so most living things use only L-amino acids in 100% proportion and they still racemize over time.
 

Acab1312

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General Procedure for the Racemization Experiments. A
0.06 M solution of amine (100 mg) and thiol (1.2 or 0.2 equiv)
in benzene was refluxed for 2 h (stoichiometric condition) or 7
h (catalytic condition) in the presence of AIBN (an overall
quantity of 20 mol % of AIBN was divided into three equal
portions (when reaction time > 2 h) that were added succes￾sively each 2 h). After concentration, the residue was diluted
with HCl (1 M), and the solution was washed with Et2O. The
aqueous phase was basified with saturated sodium carbonate
and extracted with Et2O. The pure amine was isolated after
drying on MgSO4 and concentration.
 
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