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borohydride
12-12-2008, 11:36 AM
In the BNF (British National Formulatry) oxymorphone is described as 7-9 x morphine in potency. N-phenylethyl noroxymorphone is described in 'Current Medicinal Chemistry' page 435 says that it is stronger than the parent compound (I take this to be oxymorphone), but no figures.
n-Phenylethyl normorphine is listed a x8 all the way up to x18 depending upon where you need. Of course, getting normorphine is tricky and starting with morphine is messy. noroxymorphone is made & used a great deal to make antagonists.
I was looking at an interesting 1-pot route to making fentanyl in 1-pot (should work fine for 3 methyl) using 1,2, DCE as the solvent and STAB (sodium triacetoxy borohydride). iminium ion formed so N-phenylethyl is added. Alinine added forming imine reduced to amine then propenyl chloride forms the final amide.
I digress. Has anyone got more accurate data on different N substituants for the phenanthracine group of opioids?
Of course, swapping the 6 =O with =CH2 makes the compound VEERRRYY strong but is low yielding and messy. N-phenylethyl from noroxymorphone is quick and distilling off low BP materials and flash chromaophy of the result should produce seperate trans & cis isomers (cis(+)) x 6684 morphine), (trans (+-) 500 x morphone. Actually, it may be worth cutting the trans and selling it as 100% fentanyl, just selling the cis as 'theatre siege powder'.
How on earth to package it safely? Well, I would make a LOT of gelatine and put blue dye in one. First pour & dty that onto a large & flat surface. Then a logo (go through the greek alphabet maybe) on a rubberstamp would do it. Finally, to a prechilled blue layer, a clear layer. Then someone would have problems since if there is no stamt, it's a dud. If there arn't two layers, it's a dud.

Oh, last point, it's possible to get optically active oxiranes so for all the crazies out there. you can, at least, keep the number of ohmefentanyl isomers down (but who would be so mad/dangerous to make that!).

I am going to check out the Knaus compounds as well as that wacky sulfonimide stuff that is listed (well, W18 is) listed as 10,000 x morphine.

resorcinol
12-13-2008, 10:58 PM
The only thing I know for sure about it is that it would be extremely potent.

a -phenylethyl group is the only other substitution that always produces an agonist on the phenanthrene opioid's amine group. -methyl group there is necessary for activity pretty much.... loosing that methyl reduces potency DRAMATICALLY... it's a major metabolic pathway carried out by cyp3a4 for phenanthrene opioids... N demethylation, and the products are practically inactive.

Substitutions other than methyl at the amine group on phenanthrenes is dangerous. Most subs there other than methyl produce antagonists. Phenylethyl is the exception, and actually almost always results in a compound that is a more potent agonist of mu than the analog with a methyl there.

So for N substitution of phenanthrenes, methyl is good and phenylethyl is good... anything else usually creates an antagonist.

Ethyl doesn't create an antagonist, but has reduced potency compared to just methyl, so why bother -- that's why you don't see any opioids with ethyl subbed onto the N.

Shotalotofdopeamus
12-16-2008, 03:16 PM
I want to try some of these opiates I have a hard time pronouncing.