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Pain pills made from real opium alkaloids?

TheTripDoctor

Bluelighter
Joined
Jan 3, 2001
Messages
792
Anyone know if pain killers like oxycodone and the like are made from alkaloids from real opium latex? or are they synthesized from the ground up if possible.
Thanks
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~The Recreational Pharmacist (Ketamike)
I have never belonged wholeheartedly to country or State, to my circle of friends or even to my own family...
Such isolation is sometimes bitter, but I do not regret being cut off from the understanding and sympathy of other men.
I lose something by it,to be sure, but I am compensated for it in being rendered independent of the customs,
opinions and prejudices of others, and am not tempted to rest my peace of mind upon such shifting foundations.
--Albert Einstein
My AIM: TheTripDoctor (always on)
 
Excellent question. If that be the case, then I'd sure like to hear from someone with a link to the synthesis.
 
I think it's safe to say that most opioids are synthetic; the predominant opium alkaloids are morphine, codeine, and thebaine (and maybe papaverine). Thebaine is the non-narcotic starting material for a number of opioids (which is probably why it's controlled). Morpine and codeine can also be used as precursors, of course.
 
I am P.O.I. (Posting under the influence) at the moment and suspect I may be mis-interperting the discussion, but none-the-less I'll jump in...
Here's what my research turned up...Is this what you're referring to?
opiate - narcotic analgesic derived from a natural source(opium poppy)
opioid - narcotic analgesic that is either semi or fully synthetic - also refers to entire family of both opiates and opioids
Morphine is isolated from crude opium, which is a resinous prep of the opium poppy, Papaver somniferum.
Codeine is found in opium in concentrations between %0.1 and %2. Because of the small concentration found in nature, most codeine found in medical products is synthesized from morphine via the methylation of the hydroxyl group found on the second non-aromatic ring.
Hydromorphone is synthetically produced from morphine.
Meperidine is completely synthetic and can be produced with dichlorodiethyl methylamine and benzyl cyanide.
Oxycodone is synthesized from codeine.
Propoxyphene is synthetically produced with similar structure to that of methadone.
Pentazocine is synthetically produced.
 
whatever you're under the influence of, i wanna be on that next time i got an exam...
this is my answer.. to clarify speedlimits (which is nice, really=)).. basically there are three classes here.
1. opium alkaloids: just morphine, cause like he said most codeine is derived from morphine
2. semi-synthetics (opiates, other than morphine): compounds based on the opium alkaloids. these begin with a very complex starting material which is very close to the final product. this includes heroin, codeine, hydrocodone, oxycodone, oxymorphine, dextromethorphan, levorphanol and basically anything else in Schedule I that has a IUPAC name I can't figure out.
3. synthetics (opioids): compounds which act in the same way as the opiates but have no structural relationship. these are mostly crude chemical approximations of the naturally occuring ligands for the opiate receptors (endorphins). *these* are made entirely in a lab from simple starting materials that are easily and cheaply obtained, ultimately from minerals or fossil fuels. this includes fentanyl, meperidine, propoxyphene, methadone and some others.
so... while it is possible to synthesize morphine 'from scratch' (a total synthesis), it's damned hard and more expensive than growing poppies (i think they import most of those). total synthesis is really just a chemical game people play to prove they run tings.
anyway, i found a total synthesis of morphine in 12 steps from 1997. it's scary. i'm not gonna say how much i understood...
 
hmmm...so if I had codeine I could synthesize Oxycodone? How hard would it be to do such a thing?
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"I could not/Speak, and my eyes failed, I was neither/Living nor dead, and I knew nothing" - T.S. Eliot, The Wasteland
 
Yeah, it's possible to make oxycodone from codeine fairly easily if you have some lab experience. It takes two oxidations (6 and 14 positions) and a reduction of the 7,8 double bond. Off the top of my head a simple but inefficient way of doing this would be to oxidise the 6 position by treatment of codeine with activated manganese dioxide to form codeinone (good yield, like 90%), then oxidise the 14 position by treatment of codeinone with Co(AcO)3 to form hydroxycodeinone (shitty yield, ~50%), and finally reduce the double bond over Pd/C or similar catalyst to form the product dihydrohydroxycodeinone (this rxn can be nearly quantitative). This certainly isn't the best route (owing to the poor yield in the second oxidation), it's just one particularly simple one that i happen to recall from my study of opiate chemistry some time ago. (Incidentally, prolonging the reaction time of the first oxidation will lead to oxidation of the 14 position as well, but the yield is poor, ~30%. Still, it's amusing to note that one could go from codeine to oxycodone in essentially two steps.)
It also happens that O-demethylation becomes much easier once you get the 14-OH group on the compound. D,L-methionine and methanesulfonic acid will convert oxycodone to oxymorphone in good yield.
If anyone is interested I can post references.
[This message has been edited by ppestle (edited 21 May 2001).]
 
Ever been to Tazmaina? Fields and Fields of poppies behind fences....they must be doing somthing with them, no? Poppies are so easy to grow....why bother with any other method?
 
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