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Dhc->dhm

haribo1

haribo1

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Nov 29, 2006
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Hi, I have a paper somewhere discussing conversion of dihydrocodeine to dihydromorphine using HBr in GAA. The yield is 97% of the acetyl ester of dihydromorphine. I wondered if a similar ploy would work with hydrocodone or would the stuff just rearrange under those conditions. Never mind, codeine ->DHC is simple enough and in many SEA conuntries it's OTC.
 
Cheers mate. Well, I cannot help but think that even in the US, DHC is easier to get than morphine. If you can make DHM then.... boing!
 
Do you mind posting the reference for this conversion you speak of :) ?
 
haribo1 said:
Cheers mate. Well, I cannot help but think that even in the US, DHC is easier to get than morphine. If you can make DHM then.... boing!
Click to expand...
I doubt it.

At least in Canada, I've found it much easier to find morphine than to find DHC. There is almost no demand for it, and no supply.

ps. indeed, nice to see you again :)
 
That reference & some more gibberish

Hello once again.

The reference you seek is JOC 'A practical High Yielding Synthesis of Dihydromorphine from Tetrahydrothebaine & Efficient Syntheses of of 8(S) 8 -Bromomorphide' by Anna K. Anna K. Przybyl, Judith L. Flippen-Anderson, Arthur E. Jacobson and Kenner C. Rice of NIH.

Basically, 15% by weight of HBr is dissolved in GAA. The DHC is added to this mixture and the whole lot in a Parr Hydrogenation vessel. The mixture is held at 100C (should be at about 20 psi) for 1 hour. Yield is 97% 6 acetyl dihydromorphine hydrobromide. Deacetylation & freebasing can be achieved simply by adding NaOH.

DHM is pretty good, but K t-butoxide yields Hydromorphone in similarly high yields.

I suggest that replacing the N-Methyl with an N-phenylethyl would produce an analogue 18x stronger than the parent compound. Phenylethyl Bromide & K2CO3 would add the phenylethyl, but I've not found a good, high-yielding way of chopping off the N-methyl in the first place. I mean, Cyanogen Bromide will do it, but I don't like using that stuff. Any comments?

Also, it's worth noting that noroxymorphone is not controlled in many places and if you added an N-phenylethyl to that (x18) and acetylating the 6 & 14 positions (x2.5) would produce a compound with a LOT of mu agonist activity (sort of in the hundreds of times morphine) OR one may make the hydromorphone and use a Wittig-Horner reaction the 6 =O with q 6 =CH2 which is 80x morphine (see nalmefene). Now, swap the N-methyl with N-phenylethyl and voila. Gentlemen, I give you the wheel...
 
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