• N&PD Moderators: Skorpio | someguyontheinternet

Cocaine derivative lasting 3 days

^...which is not the nicest of chems to handle.

PS: Nice to see that mods too are breaking the rules ;)
 
Hm, thats not so good, I imagine starting from atropine may be an idea, or better, hyoscyamine (or is it hyoscine that atropine is the racemate of, I can't remember offhand)

Is the product from a NaBH4 reduction going to contain any of the more active isomer? or might I as well flush the NaBH4 down the toilet (and run for cover before ducking the sharp porcelain shards flying in my direction=D) as make it from tropinone?
 
to be honest i hadn't really thought about the OH being endo until C6H6 mentioned it. You see Camphor is the exception because reduction with LAH gives over 90% exo alcohol. I guess I had just assumed that you must know what you are doing (well at least following a procedure of some description). Tropinone is not really something that you want on your hands I dont think. The shit costs a fortune and there is not alot you can do with it of the top of my head.
 
Limpet Chicken said:
Hm, thats not so good, I imagine starting from atropine may be an idea, or better, hyoscyamine (or is it hyoscine that atropine is the racemate of, I can't remember offhand)
Limpet Chicken, you're always boasting about all the compounds you're going to make, do you don't seem to have a clue of the most fundamental matters in organic chemistry. Be careful that you don't hurt yourself!

Atropine and all the atropa/datura/hyoscyamus alkaloids of course yield the undesired tropine upon hydrolysis and not the required pseudotropine.

And Smyth, the OH is exo in pseudotropine, not endo.
 
C6H6, I was unsure off the top of my head, that is all, I couldn't remember which was the racemate, thats all, stereochemistry isn't something I am an expert in, at more than a basic level.

I don't consider myself an expert organic chemist, like say, F&B, just a moderately-able one, I have only really been into organic chemistry within the last few years, previous to that, it was all inorganic stuff really I did, you know, the typical teenage bad smells and pyro stuff.

Could you perhaps explain the terms endo- and exo-, I haven't come accross them before, with regards to o-chem.

Thanks.
 
Alicyclic Chemistry by Martin Grossel goes into this in quite some detail but it is basically the type of thing that will be covered in most major textbooks.

When someone refers to axial and equatorial in the case of cyclohexane we basically know what is being talked about (1,3-diaxial interactions and tert-butyl conformational locking).

The terms endo and exo are 'derived' from the above terms but they are used in bicyclic compounds. So basically the two carbon bridge in the case of tropinone stops nucleophilic attack from the underside of the molecule occuring. So the hydride attacks predominantly from the "exo" direction giving the "endo" alcohol.
 
http://pubs3.acs.org/acs/journals/doilookup?in_doi=10.1021/jm010453u

If anybody can upload the above article, I feel it is on topic of super-powerful cocaine analogs. I already have it but I am too lazy to read it atm. It's 3 years old now so some other good stuff could have come out during that time.

jm010453un00001.gif
 
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Is that what they said? I had thought that the benztropine lacks the reinforcing behaviours associated with stimulant use even though it is active as a dopamine inhibitor. One hypotheses for this is anticholinergic and antihistaminic effects. Another explanation is simply that it lacks the ability to bind to the cocaine recognition site. I think the aryl ring pattern shown is also the one being used to develop the GBR compounds.
 
just curious, why don't people forget about the actual products and just produce these derivatives and such for street consumption ? Not just with coke but with all the morphine related drugs as well...
 
I wish I could go to uni with all you guys...the people that are in my chem class are all such a nerds...they don't even smoke sigs.
 
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