14-hydroxy-dihydroheroin?

[dread]

William Burroughs wrote about this chemical "dihydro-oxy-heroin" which I assume would be dihydroheroin with a 14-hydroxy group.. Supposedly it's more potent than regular H.

I'm really interested, has anyone actually tried this? Does it exist, or is it just a product of the imagination of a dead junkie? What's it like?

 

[enoughorangejuice?]

he was just saying like with codeine if you had a di-hydro-oxy grounp to it and make dihydrooxycodiene = oxycodone... so his theory was you could get a PK so potent but continually synthesizing opiates by adding a di-hydro-oxy group to each new drug to infinity i guess...

 

[Hammilton]

If that's what he was saying, he was talking about paralaudin- ie: diacetylhydromorphone. It has the saturated bond a la hydromorphine (no double bond on the oxygen, of course, because of the acetyl group.

 

[dread]

Is that so?
Guess I'll have to read it in the original language..

and btw, dihydro-oxy-codeine wouldn't be oxycodone, it'd be 14-hydroxy-dihydrocodeine, with a hydroxy in the 6-position, where oxycodone has a ketone oxygen.

 

[johanneschimpo]

he was just saying like with codeine if you had a di-hydro-oxy grounp to it and make dihydrooxycodiene = oxycodone... so his theory was you could get a PK so potent but continually synthesizing opiates by adding a di-hydro-oxy group to each new drug to infinity i guess...

^ That doesn't make any sense.


14-hydroxy-dihydroheroin would be heroin without the 7,8 double bond (as is the difference from codeine ---> dihydrocodeine) and with the 14-hydroxyl group (as is the difference from hydrocodone ---> oxycodone).

Considering each of these parts increase potency on their own:
- hydrogenation of the 7,8 double bond (dihydrocodeine is stronger than codeine)
- hydroxylation of the carbon in the 14 position (oxycodone is stronger than hydrocodone)
- the addition of acetyl groups (heroin is stronger than morphine)

This should be a potent opiate.
But it doesn't always work out in this way. I don't know if anyone has ever made this compound before, but I'd like to see how it turns out.

 

[dread]

That's kinda what I figured too..
what about methylating or acetylating the 14-hydroxy group too, this would increase lipid solubility.. With the single bond between 7,8 it would probably be long lived too..

 

[johanneschimpo]

^ Looks like there is work to be done...

 

[Where Wolf?]

Burroughs tended to get a lot of things wrong - thought himself a bit of a doctor, even scientist, but he was a whacked-out secular mystic, and some of his drug-specific stuff is off the wall. No-one else seems to find apomorphine all that useful in detox, as he claimed it to be, and his comments on peyote suggest he just didn't 'get' the experience.

Don't get me wrong, I love some of his novels, but think he overestimated his own technical knowledge of drugs and pharmacology.

Off-topic, his son's first novel, 'Speed', should be required reading for all Bluelighters who use, or ever used, speed in any form. William S. Burroughs Jr, a much warmer and more human kind of voice. Haunting book: poor guy died of liver failure at the age of thirty-three.

And his dad didn't even make it the funeral. Real prince of a man...

 

[johanneschimpo]

I'm just going off what I hear.
Dread says that Burroughs mentioned "dihydro-oxy-heroin," and then he (dread) figured that would mean 14-hydroxy-dihydroheroin. And regardless of any crazy things Burroughs may have said (don't know what, haven't read any of his work), what we've extended this to sounds like a strong and delicious opiate, which should have the same familiar rush of heroin while being more potent and most likely longer-lasting.
[This is all if I'm thinking straight. I am very sleep deprived at the moment, but I don't think I'm making any mistakes with the nomenclature/chemistry.]

 

[Hammilton]

didn't I say this would be paralaudin and was that wrong?

it's just the diacetyl version of hydromorphone, no?

 

[fastandbulbous]

It's the diacetyl ester of oxymorphone, the 6 position being the ester of the enol tautomer of the usual keto group

 

[dread]

this is what the triacetylated compound would look like... (I drew it a bit sloppy)
If anyone ever made this, I'd want to try

 

[Hammilton]

It's the diacetyl ester of oxymorphone, the 6 position being the ester of the enol tautomer of the usual keto group

okay, I see now.

thanks

 

[haribo1]

If you could acetylate the 3 & 6 position and then place a cinnamyl ester group on the 14 then potency would be about 160x morphine. If you want to keep it simple, just add a propenyl ester to all 3. It's 6 times stronger than the parent. It should also be smokable...

 

[dread]

Propanoyl on all three sounds interesting... but if we just want to increase potency, we should tack on an N-furylethyl group.

 

[monotome]

^ N dealkylation and re-alkylation is a real pig. About the most promising route seems to be forming a quaternary amine using iodide of the desired substituant. Dequat will, in the right conditions, mostly remove the methyl.

Having said this, unless you have a lot of material, go for the propenyl ester.