Ok, so I am from New Zealand- there is no heroin imported into New Zealand (well, if there is, no one I know can get it) so people here make 'homebake heroin' by extracting the morphine from pills (Ms-Contin, Ms-Eslon & Sevredol are the most common types) and 'turning' (acetating) the morphine with 'double' (acetic anhydride) to form diacetylmorphine. No one makes heroin from codeine anymore, people stopped doing that in the early '90s, I have however successfully demethylated dihydrocodeine into dihydromorphine.  As such, my chemistry experience is almost entirely practical- I read as much as I can, but I have no real background in chemistry so I'm quite ignorant when it comes to the theoretical side of chemistry.

I have successfully acetated a number of other substances, other than morphine, such as hydromorphone, dihydromorphine and THC. I currently have in my possession an amount of O-Desmethyltramadol and I am wondering, can I acetate this like I would morphine? Would it make it more potent? And if this would not work at all, can you explain why? Doing so would help me fill in the holes in my knowledge- I am genuinely eager to learn about chemistry, I now regret sticking to a BA type subjects during my education.

Thanks in advance, I hope this thread doesn't cause too much facepalming...

If you acylate willy-nilly, you will have a diacylated product. IIRC, you'd only want to acylate the phenol, if that. An ester at the other position lowers activity. You could try dehydrating the tertiary alcohol to make the product more potent, but the safety profile is lower.

the ref is:

K. Flick, E. Frankus, E. Friderichs
"Studies on Chemical Structure and Analgetic Activity of Phenyl Substituted Aminomethylcyclohexanoles"
Arzneimittelforschung (Drug Research) 1978, 28, p.107-113

if you dehydrate the tertiary alcohol with phosphoric acid it incorporates a double bond into the ring which sort of mimicks ring C on the morphine nucleus it has opiate analgesic qualitites it's about 1 & 1/3rd the potency of .
tramodol nothing to write home about.
there really is'nt much you can do to tramadol.

ok, i see i'm not the only junkie around, that's nice.

With acetic anhydride with some pyridine in dichloromethane the phenolic OH would get acylated according to:

Enzymatic resolution of analgesics: ?-hydroxytramadol, ?-hydroxytramadol and O-desmethyltramadol
by  Hans-Joachim Gais
Tetrahedron: Asymmetry Volume 11, Issue 4, 10 March 2000, Pages 917–928

A solution of sodium hydroxide (40%, 2 ml) was added at room temperature to a suspension of rac-O-desmethyltramadol·HCl (15 mmol) in water (8 ml). The aqueous layer was extracted twice with CH2Cl2 (15 ml). The combined organic phases were dried (Na2SO4) and concentrated in vacuo to give rac-O-desmethyltramadol.
Alcohol rac-O-desmethyltramadol (8 mmol) was mixed at room temperature with a solution of acetic anhydride (9.6 mmol) and pyridine (0.8 mmol) in CH2Cl2 (30 ml). After stirring the mixture at room temperature until the completion of the acylation (48 h), it was poured into saturated aqueous NaHCO3 and stirred for 12 h. The organic layer was separated, dried (Na2SO4) and concentrated in vacuo to give O-desmethyltramadol acetate .

And for last, here is something interesting:

At the image uploaded there is a molecular shape similarity between morphine and tramadol. Just think about it(:

    No one makes heroin from codeine anymore, people stopped doing that in the early '90s.


and why is that, btw?

 lack of access to pyridine I believe, plus the advent of much more available morphine...

its not the most effective rxn either(50-60%yeilds) and considering both codeine AND heroin are 'prodrugs' which are demethylated rapidly in vivo, I wonder why folks bother...

6-MAM is what your after, a simple acylation of M with GAA and and a catalyst

6-MAM is 3-4 times M's potency.....ch ch check it out!