Thought this article somewhat interesting, especially with respect to the use of HBr alone to promote demethylation of an Aryl ether.. What is more interesting is doing this, in acidic conditions with such a molecule. The work up appears to promote one of 2 predominate products, No 1 being the most sought after I believe due to its increased bioactivity.. I have also included the patent, which I found when Google searching the author.. There appears to be little difference, but perhaps I have missed some things, hence for a more thorough interpretation of this procedure, I thought i'd include both..

2b

PS, I hadn't seen this elsewhere either, but considering how old it is, perhaps I have missed, so my bad if I'm rehashing old and known stuff

I posted a link for the method in question for organic synthesis website over in the Demethylation threed.

right you have to strictly adhere to those rxn times ideally start with hot acid to minimize reaction time.
the solution gets really dark and a lot of product decomposes this minimizes it swij still thinks room temp demethylation is the winner.
ever try diluadid?
swij did'nt really like it much.

the diester would be a prodrug and the 3 ester would come off almost instantly in-vivo.
well in some cases reduction of the double bond increases activity by a factor of 2 but in the case of esters of 14-hydroxycodeinone  it's best left untouched and swij found this out through personal trials.

hydromorphones may have a good rush when injected but they are'nt very euphoric actually you feel dysphoric and doped out not much fun imho.
the cinnamoyl ester is the most lipophillic of the 14 ester series if you look at the other potent derivitaves like etorphine for example all they are really doing is tweaking the lipid solubility of the morphine skeleton in different positions 14-ethyl codeinone is 10,000 X the potency of morphine for example synthesized by means of claisen eschenmoser synthesis
one would have a difficult time titurating that so it's just not practical.

palfium is dextromoramide--it is a synthetic opiate with a cumulative affect--here in oz it was banned about 15years ago because when used regularly the LD can rapidly accumulate without the

user being aware of this--basically,,it caused "overdoses" due to compounding affects

great rush,,fairly short acting--oh the good ole days when drs were prepared to assist :'(--nowadays govt. controls have most of them running scared

the last prime minister was a prick---  he was on george w's mission :'(

hopefully this one is better

Taken from https://secure.wikimedia.org/wikipedia/en/wiki/Dextromoramide

"Dextromoramide is the right-handed isomer of the moramide molecule. The left-handed molecule is called levomoramide, and a mixture of the two is called racemoramide. Its full chemical name is (+)-1-(3-Methyl-4-morpholino-2,2-diphenylbutyryl)pyrrolidine, and its molecular formula: C25H32N2O2, with an atomic weight of ~392.5.

Dextromoramide was discovered during the course of research into a related family of compounds, the ?,?-Diphenyl-?-Dialkyamino-Butyramides, which show no analgesic activity, but are extremely active physiologically as inhibitors of gastric secretions in man. Other drugs from this series show antispasmodic and antihistamine effects, but most research was put into researching analgesics.

The structure-activity relationships of this family of drugs was investigated extensively, with dextromoramide representing the optimisation of several different structural features;

(i) at the 1-amide group only the pyrrolidine and dimethylamide substituents were active, with pyrrolidine being more potent

(ii) the alkyl chain was more potent when methylated, 3-methylation was more potent than 4-methylation, and in the 3-methyl analogues the dextro isomer was more active

(iii) while morpholine, dimethylamine, pyrrolidine and piperidine were all active at the 4-amine group, morpholine was the most active

(iv) any substitution on the phenyl rings reduces activity.

So dextromoramide, with a pyrrolidine ring on the 1-amide position, a dextro methyl group on the 3-position of the alkyl chain, a morpholine ring around the 4-amine group, and both phenyl rings unsubstituted, was by far the most potent out of all the compounds in this series and was the only one that became widely used in medicine (although the racemic mix racemoramide saw some limited use).[8]"

Reference: [8] ^ Paul A J Janssen. Synthetic Analgesics Part 1: Diphenylpropylamines. Pergamon Press 1960. p141-145.

According to wikipedia, (+)-1-(3-Methyl-4-dimethylamino-2,2-diphenylbutyryl)dimethylamide should have some kind of activity. It wouldn't be as potent as Dextromoramide but it might be worth looking into.

1-(2,2-Diphenylbutyryl)-2-methylpyrrolidine (CAS    34067-03-3) is listed as an insect repellent at http://chemicalland21.com/info/INSECT%20REPELLENTS.htm

This is making up images of the english language film Naked Lunch, where people ate bug powder to get high.