Diamorphine Hydrochloride Structure

3034 Words13 Pages
Systemic IUPAC name: 4, 5-Epoxy-17-methylmorphinan-3,6diyl diacetate hydrochloride monohydrate
Molecular Formula: C21H23NO5, HCL, H2O
Common Street Names: Aunty Hazel, Black Dragon, Boy, dope, H, Smack or more commonly ‘Heroin’
CAS: 1502-95-0
Chemical Structure of Diamorphine

Identification and Description of Structural Features3

The functional groups present in diamorphine hydrochloride are esters, ethers, alkenes, amine and an aromatic ring.
Esters
There are two esters present in diamorphine hydrochloride which are formed by acetylating morphine. Esters have the RCOOR’ functional group, as depicted in the diagram. Esters are formed by reacting an acid and an alcohol together. In the case of diamorphine hydrochloride, the two alcohol
…show more content…
R. Alder Wright in 1874. Wright worked in St. Mary’s Hospital Medical School in London and was observing the results of combining morphine with acids. Diamorphine hydrochloride was created by mixing morphine and acetic anhydride and leaving them to react for a number of hours. However, Wright’s work on diamorphine wasn’t acknowledged until Bayer Pharmaceuticals began to market their drug in the 1890’s. Originally marketed as a “morphine substitute that is non-addictive”, Diamorphine hydrochloride is actually metabolised into morphine in the…show more content…
In this step of the organic synthesis, Intermediate 3 has formed. However, there is a tendency for this intermediate to form ester 4, which is a more stable carbonyl derivative. This is the case here as chlorine, which is a good leaving group, is attached to the carbon atoms that could form the carbonyl. This leaves ester 4 to form.

4. The chloride ion that leaves is now electron rich. It readily donates two electrons to the H+ molecule lost from the oxygen in the preceding step, forming HCl as a by product of the reaction. Morphine has now been acetylated to 3-acetylmorphine.

5. In order to complete the synthesis, the other hydroxyl group present in morphine must also undergo the above steps. Diamorphine is then formed. The HCl that was made in the process reacts with the basic tertiary amine group on diamorphine to form its hydrochloride salt derivative.

This above reaction could also have been carried out with acetic anhydride instead of acetic chloride. This acetylation reaction would actually be faster an acetate counter ion forms. This is basic and helps the proton elimination in Step

More about Diamorphine Hydrochloride Structure

Open Document