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labgurl
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[*] posted on 6-1-2005 at 02:16
synthetic cocaine q


What would be the simplest reactions to use here? Tropinone
to
2-Carbomethoxytropinone
to
Methylecgonine
to
Cocaine




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runlabrun
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[*] posted on 6-1-2005 at 02:39


like many natural plant alkaloids there is NO simple way to make them.... if any at all...

Although back at the hive there was a few threads about synthtic cocaine, dont have those on disk though.... dont think they were very viable and were therefore abandoned....

-rlr
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[*] posted on 6-1-2005 at 06:22
Ref. cocaine synthesis


Of course rhodium had this pdf's on the subject.....let me know which one is of your interest.....solo

cocaineanalogs.pdf
cocaine.piperidine-based.analogs.sar-2.pdf
cocaine.biosynthetic.pathway.pdf
cocaine.biosynth.n-methylputrescine.pdf
cocaine.analogs.clarke.pdf
cocaine.total.synthesis.html
cocaine.synthesis.txt

[Edited on 6-1-2005 by solo]




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guaguanco
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[*] posted on 6-1-2005 at 08:57


Quote:

Although back at the hive there was a few threads about synthtic cocaine, dont have those on disk though.... dont think they were very viable and were therefore abandoned....
-rlr


I actually knew of someone who tried this synthesis. They synthesized the tropanone ring structure (glutaraldehyde/methylamine/dimethyl acetonedicarboxylate) but abandoned the project. I still have the small amount of the product, isolated as the picrate.
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labgurl
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[*] posted on 6-1-2005 at 09:53


Once again the question is which REACTIONS would be most feasable?
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guaguanco
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[*] posted on 6-1-2005 at 10:07


Quote:
Originally posted by labgurl
Once again the question is which REACTIONS would be most feasable?


The classic synthesis is reacting glutaraldehyde, methylamine and acetone dicarboxlic acid (I misspoke in a previous post; the ester is not used)
You end up with 4 diastereoisomers that have to eventually seperated by chromatography (if you want to end up with pure cocaine).
Then you esterify the acid (diazomethane would work well), reduce the ketone, react with benzoyl chloride and trimethylamine in chloroform.


[Edited on 6-1-2005 by guaguanco]
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[*] posted on 6-1-2005 at 13:03


Diazomethane, CH2N2, is very dangerous to work with for esterification of carboxylic acids to methyl esters, being both highly toxic and explosive, like azide. The usual method of esterification is reaction of alcohols with carboxylic acids with a trace of a strong mineral acid as catalyst, heating under reflux (takes a few hours usually). This is an equilibrium reaction, the yield of which can be increased by removing water as it is formed. Anhydrides react similarly with alcohols in the absence of acid. Acyl chlorides similarly react with alcohols with evolution of HCl. A more powerful methyl esterification reagent is sodium methoxide.

[Edited on 6-1-2005 by JohnWW]
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guaguanco
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[*] posted on 6-1-2005 at 13:15


Sure, I just picked that as an example. There are a variety of reagents that could be used, although I would look for one that operated under mild conditions. I don't know what the ruggedness of the tropanone moiety is.
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labgurl
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[*] posted on 6-1-2005 at 17:29


What role does dimethylcarbonate play in the sodium methoxide/tropinone/ toluene/dimethylcarbonate reflux?



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[*] posted on 6-1-2005 at 20:05


In my opinion it would be better to synthesize the methyl ester of tropinone in one huge step instead of first tropinone and then 2-CMT. Reaction of succindialdehyde, methylamine, and the anhydride of acetonedicarboxylic acid yields 2-CMT. Acetone dicarboxylic acid anhydride is produced by reacting acetone dicarboxylic acid with acetic anhydride.

2-CMT is then reduced to methyl ecognine. This can be done by catalytic hydrogenation or sodium amalgam, both methods kind of suck in my opinion. Hydrogenation = assloads of equipment construction (welding together apressure vessel, hydrogen tanks and connections, shaker, catalyst, eeeek!). Sodium amalgam=expensive + hard.

Once you have your methyl ecognine, it is reacting with either the chloride or the anhydride of benzoic acid. This last step doesn't seem too difficult, just react benzoic anhydride with methyl ecognine in benzene, nothing too fancy. I think the difficulty of this synthesis lies in the resolution of racemic mixtures over and over.

[Edited on 7-1-2005 by Mendeleev]




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labgurl
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[*] posted on 6-1-2005 at 21:57


Darn, was hoping there was another reduction method besides those 2. Hmmm wonder how one could obtain cocoa seeds within the u.s.? lol



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[*] posted on 7-1-2005 at 17:17


You have confused cocoa (cacao) seeds with coca seeds. They are two quite different species, the active principles in cocoa being theobromine and caffeine. It is coca, from elevated forest areas in northwestern South America, that contains cocaine and some related alkaloid compounds. Coca should grow well in subtropical and warm temperate areas that do not have heavy frosts.
(Cocoa, however, is strictly tropical; most commercial cocoa plantations are within 10º of the equator, e.g. west Africa, and almost all are within 20º of the equator. This has to do with why cocoa butter is the vegetable oil with the highest melting point).
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[*] posted on 8-1-2005 at 01:26


Thanks for clearing that up, I shall retry my search.



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[*] posted on 8-1-2005 at 12:54


was looking into the same line of reactions and their viability OTC. it sounds something like this (if I remember correctly)

lactose > mucic acid > pyromucic acid >
pyrrole > succinaldehyde > &

at which point i concluded my study

further along tropinone et al would have been realized but my masochistic/curious side got tired and quit on me.

as has been said it seems cheaper down on the corner.
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[*] posted on 12-1-2005 at 19:28


that shit is to involved. Go with the analog N-methyl,4-para-chloro-Phenyl, 3 -carboxy methyl ester staring with Arecoline. or you could make tropacocaine by hydrolysis of atropine to tropine and then esterfication with benzoic acid.



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[*] posted on 17-1-2005 at 14:46


Quote:
Originally posted by solo
cocaine.piperidine-based.analogs.sar-2.pdf

Can you send me the file to warfox@gmx.de
Thanks
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[*] posted on 17-1-2005 at 15:48
analog clareify


Quote:
Originally posted by Nuke_Dukem
that shit is to involved. Go with the analog N-methyl,4-para-chloro-Phenyl, 3 -carboxy methyl ester staring with Arecoline.

Hi.
Ive looked into this compound and cant find it in the documents. Can u provide ref for this one? Chemdraw wont draw its structure either.
Can u please clarify Nuke_Dukem?

[Edited on 17-1-2005 by yogi]

[Edited on 17-1-2005 by yogi]
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[*] posted on 17-1-2005 at 17:39


hey sorry that name I gave is just the name of arecoline. Heres one write up from rhodium, the authors calls the analog Coke-lite.

http://web.archive.org/web/20040210013016/www.rhodium.ws/che...

[Edited on 18-1-2005 by Nuke_Dukem]




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[*] posted on 17-1-2005 at 18:05
Reference for Worfox




Attachment: cocaine.piperidine-based.analogs.sar-2 copy.pdf (256kB)
This file has been downloaded 898 times





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[*] posted on 18-1-2005 at 16:54
Ref: synthetic cocaine


The work on Piperidine analogs of Phenyltropanes was done by Kozikowski...that should give you a start for looking in chem abstracts or med line.....solo



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[*] posted on 19-1-2005 at 04:46


Can someone explain why benzocaine wouldn't be a viable starting material?
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[*] posted on 19-1-2005 at 07:04


Maybe that's because benzocaine is a derivative of PABA, not any of them two-ring heterocyclics that comprise cocaine. Same goes for most of the other "-caines" (check ChemFinder or the Merck Index if you want to verify my claims). Cocaine is quite unique among them.

Stick with the route from atropine. It isn't too hard to obtain, especially if nightshade/belladonna, bittersweet or henbane are common plants in your area.

Arecoline? Are areca/betel common plants there?
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[*] posted on 19-7-2009 at 20:48



benzylmethylecgonine can be achived via a nitrone synthesis.

look on rhodium....its a picture.

in littile letters is refrences.

get those. yeild is lower slightly.......but seems less involved...more like a short series of brutal grignards lol :)


but what about benzoylecgonine.....can this be selectivly remethylated?
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[*] posted on 19-7-2009 at 21:54


If it was practical to do this the Colombian drug lords wouldn't still be doing it the old fashion way.
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[*] posted on 19-7-2009 at 23:11


its not as profitable to do it if you happen to live where there is millions of coca plants
and can make peons pick em in order to not get shot........

but this is about chemistry, not profit.
any fool can make tweek,
make ecgonine takes real skill.

and the nitrone route benafits from uncommon reagents.....
not hard to get anhydride,methylamine, sodium metal, ect.
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